############################################################################## # # # This CIF contains the data in a paper accepted for publication in # # Acta Crystallographica Section E. It conforms to the requirements of # # Notes for Authors for Acta Crystallographica Section E, and has been # # peer reviewed under the auspices of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. # # # # Software is freely available for graphical display of the structure(s) # # in this CIF. For information consult the CIF software page # # http://www.iucr.org/resources/cif/software. # # # # This file may be used for bona fide research purposes within the # # scientific community so long as proper attribution is given to the journal # # article from which it was obtained. # # # ############################################################################## data_global _audit_creation_method 'form.cif (version 2.0)' _journal_data_validation_number ? _journal_date_recd_electronic 2013-03-04 _journal_date_accepted 2013-03-08 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2013 _journal_volume 69 _journal_issue 4 _journal_page_first o541 _journal_page_last o541 _journal_paper_category QO _journal_paper_doi 10.1107/S1600536813006739 _journal_coeditor_code RZ5051 _publ_contact_author_name 'Dr. Gurbanov, Atash V.' _publ_contact_author_address ; Department of Organic Chemistry, Baku State University, Baku, Azerbaijan ; _publ_contact_author_email 'organik10@hotmail.com, zsrkk@yahoo.com' _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_section_title ;\ Ethyl 4-(5-bromo-2-hydroxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-\ hexahydroquinoline-3-carboxylate ; loop_ _publ_author_name _publ_author_address 'Kurbanova, Malahat M.' ; Department of Organic Chemistry, Baku State University, Baku, Azerbaijan ; 'Huseynov, Elnur Z.' ; Department of Organic Chemistry, Baku State University, Baku, Azerbaijan ; 'Gurbanov, Atash V.' ; Department of Organic Chemistry, Baku State University, Baku, Azerbaijan ; 'Maharramov, Abel M.' ; Department of Organic Chemistry, Baku State University, Baku, Azerbaijan ; 'Kia, Reza' ; Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran Structural Dynamics of (Bio)Chemical Systems, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11 37077 G\"ottingen, Germany ; data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ;\ Ethyl 4-(5-bromo-2-hydroxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-\ hexahydroquinoline-3-carboxylate ; _chemical_name_common ? _chemical_formula_moiety 'C21 H24 Br N O4' _chemical_formula_sum 'C21 H24 Br N O4' _chemical_formula_iupac 'C21 H24 Br N O4' _chemical_formula_weight 434.32 _chemical_melting_point 520 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.5969(3) _cell_length_b 19.0805(5) _cell_length_c 11.0678(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.3870(10) _cell_angle_gamma 90.00 _cell_volume 2009.84(10) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2045 _cell_measurement_theta_min 3.27 _cell_measurement_theta_max 27.50 _cell_measurement_temperature 294(2) _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 2.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2005)' _exptl_absorpt_correction_T_min 0.6363 _exptl_absorpt_correction_T_max 0.7069 _exptl_special_details ; ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker SMART APEXII CCD area-detector ; _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 23241 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0184 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 28.32 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 5008 _reflns_number_gt 3604 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0724 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_gt 0.1245 _refine_ls_wR_factor_ref 0.1362 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.052 _refine_ls_number_reflns 5008 _refine_ls_number_parameters 266 _refine_ls_number_restraints 3 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0542P)^2^+1.4854P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 1.103 _refine_diff_density_min -1.020 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT (Bruker, 2005)' _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_disorder_assembly _atom_site_disorder_group Br Br1 0.91668(4) 0.11235(2) 0.50601(4) 0.09330(19) Uani d . 1 1 A . O O1 0.4895(3) 0.41833(11) 0.5435(2) 0.0719(6) Uani d . 1 1 . . O O2 0.3062(2) 0.18500(11) 0.61555(16) 0.0577(5) Uani d . 1 1 . . O O3 0.3634(2) 0.13165(11) 0.79229(19) 0.0597(5) Uani d D 1 1 . . O O4 0.4398(2) 0.31539(12) 0.38649(17) 0.0657(6) Uani d . 1 1 . . H H4 0.4496 0.3478 0.4434 0.099 Uiso d R 1 1 . . N N1 0.6847(2) 0.28211(11) 0.87199(18) 0.0436(5) Uani d . 1 1 . . H H1 0.7348 0.2820 0.9422 0.052 Uiso d R 1 1 . . C C1 0.6826(2) 0.34138(12) 0.8040(2) 0.0392(5) Uani d . 1 1 . . C C2 0.7744(3) 0.40011(14) 0.8550(2) 0.0487(6) Uani d . 1 1 . . H H2A 0.8640 0.3812 0.8910 0.058 Uiso calc R 1 1 . . H H2B 0.7312 0.4228 0.9193 0.058 Uiso calc R 1 1 . . C C3 0.8001(3) 0.45464(14) 0.7599(3) 0.0507(6) Uani d . 1 1 . . C C4 0.6576(3) 0.47395(14) 0.6893(3) 0.0584(7) Uani d . 1 1 . . H H4A 0.6025 0.4986 0.7434 0.070 Uiso calc R 1 1 . . H H4B 0.6726 0.5057 0.6238 0.070 Uiso calc R 1 1 . . C C5 0.5754(3) 0.41168(14) 0.6362(3) 0.0494(6) Uani d . 1 1 . . C C6 0.5958(2) 0.34543(12) 0.6974(2) 0.0385(5) Uani d . 1 1 . . C C7 0.5182(2) 0.28168(12) 0.64397(19) 0.0372(5) Uani d . 1 1 A . H H7A 0.4239 0.2969 0.6095 0.045 Uiso calc R 1 1 . . C C8 0.5009(2) 0.22835(12) 0.74306(19) 0.0350(5) Uani d . 1 1 . . C C9 0.5861(2) 0.22942(13) 0.85029(19) 0.0379(5) Uani d . 1 1 A . C C10 0.5868(3) 0.17973(17) 0.9557(2) 0.0576(7) Uani d . 1 1 . . H H10A 0.5907 0.1324 0.9270 0.086 Uiso calc R 1 1 A . H H10B 0.5028 0.1862 0.9930 0.086 Uiso calc R 1 1 . . H H10C 0.6674 0.1889 1.0144 0.086 Uiso calc R 1 1 . . C C11 0.8970(3) 0.42483(18) 0.6729(3) 0.0673(8) Uani d . 1 1 . . H H11A 0.8543 0.3841 0.6329 0.101 Uiso calc R 1 1 . . H H11B 0.9855 0.4121 0.7182 0.101 Uiso calc R 1 1 . . H H11C 0.9120 0.4596 0.6132 0.101 Uiso calc R 1 1 . . C C12 0.8689(4) 0.51939(17) 0.8232(4) 0.0734(9) Uani d . 1 1 . . H H12A 0.8085 0.5383 0.8779 0.110 Uiso calc R 1 1 . . H H12B 0.8840 0.5540 0.7633 0.110 Uiso calc R 1 1 . . H H12C 0.9574 0.5065 0.8684 0.110 Uiso calc R 1 1 . . C C13 0.3830(2) 0.18055(13) 0.7107(2) 0.0407(5) Uani d . 1 1 A . C C14 0.2502(7) 0.0825(4) 0.7444(6) 0.0617(18) Uani d PD 0.633(10) 1 A 1 H H14A 0.2704 0.0612 0.6690 0.074 Uiso calc PR 0.633(10) 1 A 1 H H14B 0.1606 0.1066 0.7295 0.074 Uiso calc PR 0.633(10) 1 A 1 C C15 0.2477(6) 0.0278(4) 0.8428(7) 0.080(2) Uani d PD 0.633(10) 1 A 1 H H15A 0.1797 -0.0076 0.8157 0.120 Uiso calc PR 0.633(10) 1 A 1 H H15B 0.2229 0.0495 0.9154 0.120 Uiso calc PR 0.633(10) 1 A 1 H H15C 0.3389 0.0067 0.8599 0.120 Uiso calc PR 0.633(10) 1 A 1 C C14' 0.2263(8) 0.0963(5) 0.7967(10) 0.051(3) Uani d PD 0.367(10) 1 A 2 H H14C 0.1501 0.1219 0.7502 0.061 Uiso calc PR 0.367(10) 1 A 2 H H14D 0.2062 0.0910 0.8799 0.061 Uiso calc PR 0.367(10) 1 A 2 C C15' 0.2497(11) 0.0255(6) 0.7387(15) 0.094(5) Uani d PD 0.367(10) 1 A 2 H H15D 0.1635 -0.0007 0.7296 0.141 Uiso calc PR 0.367(10) 1 A 2 H H15E 0.3205 -0.0001 0.7899 0.141 Uiso calc PR 0.367(10) 1 A 2 H H15F 0.2798 0.0326 0.6602 0.141 Uiso calc PR 0.367(10) 1 A 2 C C16 0.5888(3) 0.25025(13) 0.5398(2) 0.0407(5) Uani d . 1 1 . . C C17 0.6996(3) 0.20358(14) 0.5642(2) 0.0459(6) Uani d . 1 1 A . H H17A 0.7331 0.1922 0.6444 0.055 Uiso calc R 1 1 . . C C18 0.7603(3) 0.17389(15) 0.4702(3) 0.0561(7) Uani d . 1 1 . . C C19 0.7115(4) 0.18797(18) 0.3507(3) 0.0662(9) Uani d . 1 1 A . H H19A 0.7507 0.1661 0.2881 0.079 Uiso calc R 1 1 . . C C20 0.6038(4) 0.23495(18) 0.3256(2) 0.0643(9) Uani d . 1 1 . . H H20A 0.5706 0.2451 0.2448 0.077 Uiso calc R 1 1 A . C C21 0.5431(3) 0.26783(15) 0.4182(2) 0.0499(6) Uani d . 1 1 A . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br1 0.0748(3) 0.1056(3) 0.1086(4) 0.0222(2) 0.0469(2) 0.0037(2) O1 0.0849(15) 0.0519(12) 0.0703(14) 0.0074(11) -0.0226(12) 0.0177(10) O2 0.0550(11) 0.0705(13) 0.0419(10) -0.0123(9) -0.0152(8) 0.0044(9) O3 0.0498(11) 0.0594(11) 0.0645(12) -0.0181(9) -0.0140(9) 0.0208(10) O4 0.0744(14) 0.0777(14) 0.0404(10) -0.0011(11) -0.0102(9) 0.0150(10) N1 0.0421(10) 0.0523(12) 0.0332(9) -0.0084(9) -0.0066(8) 0.0074(9) C1 0.0378(11) 0.0429(12) 0.0373(11) -0.0015(9) 0.0062(9) 0.0009(10) C2 0.0483(14) 0.0512(15) 0.0459(14) -0.0081(11) 0.0028(11) -0.0035(11) C3 0.0509(14) 0.0430(14) 0.0595(16) -0.0037(11) 0.0123(12) -0.0006(12) C4 0.0626(17) 0.0386(14) 0.0738(19) 0.0055(12) 0.0078(14) 0.0038(13) C5 0.0514(15) 0.0432(14) 0.0526(15) 0.0085(11) 0.0036(12) 0.0053(11) C6 0.0399(12) 0.0405(12) 0.0349(11) 0.0032(9) 0.0040(9) 0.0039(9) C7 0.0373(11) 0.0447(13) 0.0280(10) 0.0021(9) -0.0024(8) 0.0054(9) C8 0.0337(10) 0.0426(12) 0.0284(10) 0.0016(9) 0.0032(8) 0.0042(9) C9 0.0373(11) 0.0463(13) 0.0298(10) -0.0021(10) 0.0031(8) 0.0047(9) C10 0.0631(17) 0.0708(18) 0.0352(12) -0.0208(14) -0.0084(11) 0.0165(12) C11 0.0628(18) 0.070(2) 0.074(2) -0.0017(15) 0.0281(16) 0.0055(16) C12 0.075(2) 0.0544(18) 0.092(2) -0.0175(16) 0.0133(18) -0.0061(17) C13 0.0382(11) 0.0438(13) 0.0388(12) 0.0019(10) 0.0002(9) 0.0021(10) C14 0.061(3) 0.065(4) 0.055(4) -0.022(3) -0.004(3) 0.005(3) C15 0.065(3) 0.084(4) 0.093(5) -0.018(3) 0.012(3) 0.028(4) C14' 0.047(4) 0.062(6) 0.044(6) -0.012(4) 0.003(4) 0.006(4) C15' 0.053(5) 0.064(7) 0.169(16) -0.009(5) 0.025(7) -0.002(8) C16 0.0462(13) 0.0448(13) 0.0311(11) -0.0106(10) 0.0046(9) 0.0024(10) C17 0.0461(13) 0.0529(14) 0.0398(12) -0.0080(11) 0.0102(10) 0.0020(11) C18 0.0559(15) 0.0575(16) 0.0594(17) -0.0096(13) 0.0248(13) -0.0029(13) C19 0.081(2) 0.073(2) 0.0509(16) -0.0240(18) 0.0309(15) -0.0138(15) C20 0.081(2) 0.083(2) 0.0298(12) -0.0262(18) 0.0102(13) -0.0010(13) C21 0.0578(15) 0.0581(16) 0.0328(12) -0.0163(13) 0.0022(10) 0.0049(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br1 C18 . 1.907(3) ? O1 C5 . 1.238(3) ? O2 C13 . 1.208(3) ? O3 C13 . 1.329(3) ? O3 C14 . 1.481(5) ? O3 C14' . 1.485(7) ? O4 C21 . 1.357(4) ? O4 H4 . 0.8798 ? N1 C1 . 1.357(3) ? N1 C9 . 1.381(3) ? N1 H1 . 0.8600 ? C1 C6 . 1.356(3) ? C1 C2 . 1.491(3) ? C2 C3 . 1.523(4) ? C2 H2A . 0.9700 ? C2 H2B . 0.9700 ? C3 C12 . 1.528(4) ? C3 C4 . 1.530(4) ? C3 C11 . 1.531(4) ? C4 C5 . 1.503(4) ? C4 H4A . 0.9700 ? C4 H4B . 0.9700 ? C5 C6 . 1.436(3) ? C6 C7 . 1.507(3) ? C7 C8 . 1.521(3) ? C7 C16 . 1.532(3) ? C7 H7A . 0.9800 ? C8 C9 . 1.352(3) ? C8 C13 . 1.461(3) ? C9 C10 . 1.503(3) ? C10 H10A . 0.9600 ? C10 H10B . 0.9600 ? C10 H10C . 0.9600 ? C11 H11A . 0.9600 ? C11 H11B . 0.9600 ? C11 H11C . 0.9600 ? C12 H12A . 0.9600 ? C12 H12B . 0.9600 ? C12 H12C . 0.9600 ? C14 C15 . 1.512(4) ? C14 H14A . 0.9700 ? C14 H14B . 0.9700 ? C15 H15A . 0.9600 ? C15 H15B . 0.9600 ? C15 H15C . 0.9600 ? C14' C15' . 1.526(5) ? C14' H14C . 0.9700 ? C14' H14D . 0.9700 ? C15' H15D . 0.9600 ? C15' H15E . 0.9600 ? C15' H15F . 0.9600 ? C16 C17 . 1.386(4) ? C16 C21 . 1.402(3) ? C17 C18 . 1.378(4) ? C17 H17A . 0.9300 ? C18 C19 . 1.371(4) ? C19 C20 . 1.369(5) ? C19 H19A . 0.9300 ? C20 C21 . 1.392(4) ? C20 H20A . 0.9300 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C13 O3 C14 . . 111.3(3) ? C13 O3 C14' . . 123.0(5) ? C21 O4 H4 . . 106.1 ? C1 N1 C9 . . 123.33(19) ? C1 N1 H1 . . 118.0 ? C9 N1 H1 . . 116.5 ? C6 C1 N1 . . 119.6(2) ? C6 C1 C2 . . 123.6(2) ? N1 C1 C2 . . 116.8(2) ? C1 C2 C3 . . 113.1(2) ? C1 C2 H2A . . 109.0 ? C3 C2 H2A . . 109.0 ? C1 C2 H2B . . 109.0 ? C3 C2 H2B . . 109.0 ? H2A C2 H2B . . 107.8 ? C2 C3 C12 . . 109.5(2) ? C2 C3 C4 . . 107.7(2) ? C12 C3 C4 . . 110.2(2) ? C2 C3 C11 . . 110.2(2) ? C12 C3 C11 . . 109.1(3) ? C4 C3 C11 . . 110.1(3) ? C5 C4 C3 . . 113.5(2) ? C5 C4 H4A . . 108.9 ? C3 C4 H4A . . 108.9 ? C5 C4 H4B . . 108.9 ? C3 C4 H4B . . 108.9 ? H4A C4 H4B . . 107.7 ? O1 C5 C6 . . 121.2(3) ? O1 C5 C4 . . 120.2(2) ? C6 C5 C4 . . 118.6(2) ? C1 C6 C5 . . 119.5(2) ? C1 C6 C7 . . 120.9(2) ? C5 C6 C7 . . 119.7(2) ? C6 C7 C8 . . 110.56(18) ? C6 C7 C16 . . 111.54(19) ? C8 C7 C16 . . 112.36(19) ? C6 C7 H7A . . 107.4 ? C8 C7 H7A . . 107.4 ? C16 C7 H7A . . 107.4 ? C9 C8 C13 . . 125.9(2) ? C9 C8 C7 . . 120.9(2) ? C13 C8 C7 . . 113.17(18) ? C8 C9 N1 . . 119.2(2) ? C8 C9 C10 . . 127.9(2) ? N1 C9 C10 . . 112.93(19) ? C9 C10 H10A . . 109.5 ? C9 C10 H10B . . 109.5 ? H10A C10 H10B . . 109.5 ? C9 C10 H10C . . 109.5 ? H10A C10 H10C . . 109.5 ? H10B C10 H10C . . 109.5 ? C3 C11 H11A . . 109.5 ? C3 C11 H11B . . 109.5 ? H11A C11 H11B . . 109.5 ? C3 C11 H11C . . 109.5 ? H11A C11 H11C . . 109.5 ? H11B C11 H11C . . 109.5 ? C3 C12 H12A . . 109.5 ? C3 C12 H12B . . 109.5 ? H12A C12 H12B . . 109.5 ? C3 C12 H12C . . 109.5 ? H12A C12 H12C . . 109.5 ? H12B C12 H12C . . 109.5 ? O2 C13 O3 . . 121.2(2) ? O2 C13 C8 . . 122.4(2) ? O3 C13 C8 . . 116.37(19) ? O3 C14 C15 . . 105.0(4) ? O3 C14 H14A . . 110.8 ? C15 C14 H14A . . 110.8 ? O3 C14 H14B . . 110.8 ? C15 C14 H14B . . 110.8 ? H14A C14 H14B . . 108.8 ? O3 C14' C15' . . 102.1(6) ? O3 C14' H14C . . 111.4 ? C15' C14' H14C . . 111.4 ? O3 C14' H14D . . 111.4 ? C15' C14' H14D . . 111.4 ? H14C C14' H14D . . 109.2 ? C14' C15' H15D . . 109.5 ? C14' C15' H15E . . 109.5 ? H15D C15' H15E . . 109.5 ? C14' C15' H15F . . 109.5 ? H15D C15' H15F . . 109.5 ? H15E C15' H15F . . 109.5 ? C17 C16 C21 . . 118.5(2) ? C17 C16 C7 . . 120.5(2) ? C21 C16 C7 . . 121.0(2) ? C18 C17 C16 . . 120.4(2) ? C18 C17 H17A . . 119.8 ? C16 C17 H17A . . 119.8 ? C19 C18 C17 . . 121.5(3) ? C19 C18 Br1 . . 118.9(2) ? C17 C18 Br1 . . 119.6(2) ? C20 C19 C18 . . 118.7(3) ? C20 C19 H19A . . 120.7 ? C18 C19 H19A . . 120.7 ? C19 C20 C21 . . 121.5(3) ? C19 C20 H20A . . 119.3 ? C21 C20 H20A . . 119.3 ? O4 C21 C20 . . 118.2(2) ? O4 C21 C16 . . 122.4(2) ? C20 C21 C16 . . 119.4(3) ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C9 N1 C1 C6 . . . . -11.6(4) ? C9 N1 C1 C2 . . . . 166.2(2) ? C6 C1 C2 C3 . . . . -19.6(4) ? N1 C1 C2 C3 . . . . 162.7(2) ? C1 C2 C3 C12 . . . . 168.6(2) ? C1 C2 C3 C4 . . . . 48.8(3) ? C1 C2 C3 C11 . . . . -71.4(3) ? C2 C3 C4 C5 . . . . -53.9(3) ? C12 C3 C4 C5 . . . . -173.3(3) ? C11 C3 C4 C5 . . . . 66.4(3) ? C3 C4 C5 O1 . . . . -152.6(3) ? C3 C4 C5 C6 . . . . 29.2(4) ? N1 C1 C6 C5 . . . . 169.3(2) ? C2 C1 C6 C5 . . . . -8.3(4) ? N1 C1 C6 C7 . . . . -9.4(3) ? C2 C1 C6 C7 . . . . 173.0(2) ? O1 C5 C6 C1 . . . . -174.8(3) ? C4 C5 C6 C1 . . . . 3.3(4) ? O1 C5 C6 C7 . . . . 3.9(4) ? C4 C5 C6 C7 . . . . -178.0(2) ? C1 C6 C7 C8 . . . . 24.1(3) ? C5 C6 C7 C8 . . . . -154.6(2) ? C1 C6 C7 C16 . . . . -101.7(2) ? C5 C6 C7 C16 . . . . 79.6(3) ? C6 C7 C8 C9 . . . . -21.1(3) ? C16 C7 C8 C9 . . . . 104.2(2) ? C6 C7 C8 C13 . . . . 156.56(19) ? C16 C7 C8 C13 . . . . -78.1(2) ? C13 C8 C9 N1 . . . . -173.8(2) ? C7 C8 C9 N1 . . . . 3.6(3) ? C13 C8 C9 C10 . . . . 4.8(4) ? C7 C8 C9 C10 . . . . -177.8(3) ? C1 N1 C9 C8 . . . . 14.5(4) ? C1 N1 C9 C10 . . . . -164.2(2) ? C14 O3 C13 O2 . . . . 6.0(5) ? C14' O3 C13 O2 . . . . -21.9(6) ? C14 O3 C13 C8 . . . . -174.5(4) ? C14' O3 C13 C8 . . . . 157.6(5) ? C9 C8 C13 O2 . . . . 175.8(2) ? C7 C8 C13 O2 . . . . -1.8(3) ? C9 C8 C13 O3 . . . . -3.7(4) ? C7 C8 C13 O3 . . . . 178.8(2) ? C13 O3 C14 C15 . . . . 176.1(5) ? C14' O3 C14 C15 . . . . -62.6(10) ? C13 O3 C14' C15' . . . . 102.7(10) ? C14 O3 C14' C15' . . . . 31.1(9) ? C6 C7 C16 C17 . . . . 84.8(3) ? C8 C7 C16 C17 . . . . -40.0(3) ? C6 C7 C16 C21 . . . . -95.2(3) ? C8 C7 C16 C21 . . . . 140.0(2) ? C21 C16 C17 C18 . . . . -1.8(4) ? C7 C16 C17 C18 . . . . 178.2(2) ? C16 C17 C18 C19 . . . . -1.6(4) ? C16 C17 C18 Br1 . . . . 177.85(19) ? C17 C18 C19 C20 . . . . 2.8(4) ? Br1 C18 C19 C20 . . . . -176.7(2) ? C18 C19 C20 C21 . . . . -0.5(5) ? C19 C20 C21 O4 . . . . 178.0(3) ? C19 C20 C21 C16 . . . . -2.8(4) ? C17 C16 C21 O4 . . . . -177.0(2) ? C7 C16 C21 O4 . . . . 3.1(4) ? C17 C16 C21 C20 . . . . 3.9(4) ? C7 C16 C21 C20 . . . . -176.0(2) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O4 H4 O1 . 0.88 1.75 2.625(3) 171 y N1 H1 O2 4_666 0.86 2.05 2.866(3) 158 y _iucr_refine_instructions_details ; TITL a in P2(1)/n CELL 0.71073 9.5969 19.0805 11.0678 90.000 97.387 90.000 ZERR 4.00 0.0003 0.0005 0.0003 0.000 0.001 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O Br UNIT 84 96 4 16 4 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 HTAB O4 O1 HTAB N1 O2_$1 EQIV $1 x+1/2,-y+1/2,z+1/2 SADI 0.01 O3 C14 O3 C14' CONF SIZE 0.24 0.22 0.18 DFIX 1.54 0.005 C14 C15 C14' C15' TEMP 23.000 WGHT 0.054200 1.485400 FVAR 0.16940 0.63266 BR1 5 0.916680 0.112350 0.506011 11.00000 0.07482 0.10564 = 0.10864 0.00366 0.04689 0.02216 O1 4 0.489479 0.418328 0.543495 11.00000 0.08492 0.05192 = 0.07034 0.01774 -0.02262 0.00743 O2 4 0.306174 0.184997 0.615546 11.00000 0.05498 0.07053 = 0.04192 0.00438 -0.01524 -0.01227 O3 4 0.363427 0.131653 0.792286 11.00000 0.04978 0.05935 = 0.06448 0.02078 -0.01396 -0.01814 O4 4 0.439789 0.315390 0.386494 11.00000 0.07437 0.07774 = 0.04041 0.01501 -0.01022 -0.00113 AFIX 3 H4 2 0.449649 0.347830 0.443444 11.00000 -1.50000 AFIX 0 N1 3 0.684687 0.282110 0.871991 11.00000 0.04208 0.05234 = 0.03325 0.00737 -0.00658 -0.00843 AFIX 3 H1 2 0.734807 0.282000 0.942231 11.00000 -1.20000 AFIX 0 C1 1 0.682591 0.341381 0.803997 11.00000 0.03780 0.04287 = 0.03727 0.00092 0.00619 -0.00148 C2 1 0.774427 0.400107 0.855037 11.00000 0.04828 0.05117 = 0.04588 -0.00347 0.00282 -0.00809 AFIX 23 H2A 2 0.864034 0.381154 0.891033 11.00000 -1.20000 H2B 2 0.731196 0.422766 0.919306 11.00000 -1.20000 AFIX 0 C3 1 0.800100 0.454642 0.759885 11.00000 0.05088 0.04303 = 0.05947 -0.00061 0.01228 -0.00365 C4 1 0.657605 0.473945 0.689260 11.00000 0.06259 0.03865 = 0.07378 0.00376 0.00785 0.00548 AFIX 23 H4A 2 0.602492 0.498552 0.743411 11.00000 -1.20000 H4B 2 0.672619 0.505735 0.623771 11.00000 -1.20000 AFIX 0 C5 1 0.575391 0.411679 0.636218 11.00000 0.05145 0.04321 = 0.05260 0.00530 0.00365 0.00847 C6 1 0.595784 0.345433 0.697431 11.00000 0.03992 0.04051 = 0.03494 0.00391 0.00397 0.00324 C7 1 0.518166 0.281675 0.643969 11.00000 0.03727 0.04469 = 0.02799 0.00543 -0.00238 0.00209 AFIX 13 H7A 2 0.423869 0.296910 0.609468 11.00000 -1.20000 AFIX 0 C8 1 0.500877 0.228351 0.743056 11.00000 0.03368 0.04262 = 0.02837 0.00417 0.00319 0.00157 C9 1 0.586057 0.229415 0.850286 11.00000 0.03733 0.04626 = 0.02982 0.00467 0.00310 -0.00208 C10 1 0.586817 0.179729 0.955687 11.00000 0.06306 0.07081 = 0.03520 0.01653 -0.00838 -0.02077 AFIX 137 H10A 2 0.590719 0.132380 0.926980 11.00000 -1.50000 H10B 2 0.502814 0.186151 0.993045 11.00000 -1.50000 H10C 2 0.667403 0.188908 1.014381 11.00000 -1.50000 AFIX 0 C11 1 0.897028 0.424825 0.672925 11.00000 0.06277 0.06974 = 0.07437 0.00546 0.02806 -0.00171 AFIX 33 H11A 2 0.854348 0.384092 0.632877 11.00000 -1.50000 H11B 2 0.985512 0.412142 0.718232 11.00000 -1.50000 H11C 2 0.911984 0.459551 0.613158 11.00000 -1.50000 AFIX 0 C12 1 0.868870 0.519394 0.823244 11.00000 0.07487 0.05444 = 0.09157 -0.00609 0.01328 -0.01747 AFIX 33 H12A 2 0.808514 0.538328 0.877869 11.00000 -1.50000 H12B 2 0.883951 0.553987 0.763291 11.00000 -1.50000 H12C 2 0.957353 0.506549 0.868378 11.00000 -1.50000 AFIX 0 C13 1 0.383002 0.180548 0.710672 11.00000 0.03817 0.04379 = 0.03879 0.00212 0.00024 0.00188 PART 1 C14 1 0.250159 0.082504 0.744383 21.00000 0.06137 0.06524 = 0.05528 0.00456 -0.00429 -0.02222 AFIX 23 H14A 2 0.270367 0.061221 0.668964 21.00000 -1.20000 H14B 2 0.160591 0.106594 0.729477 21.00000 -1.20000 AFIX 0 C15 1 0.247698 0.027756 0.842843 21.00000 0.06467 0.08393 = 0.09280 0.02849 0.01213 -0.01755 AFIX 137 H15A 2 0.179669 -0.007619 0.815709 21.00000 -1.50000 H15B 2 0.222936 0.049455 0.915387 21.00000 -1.50000 H15C 2 0.338927 0.006671 0.859949 21.00000 -1.50000 PART 2 AFIX 0 C14' 1 0.226271 0.096320 0.796726 -21.00000 0.04669 0.06195 = 0.04432 0.00572 0.00337 -0.01226 AFIX 23 H14C 2 0.150139 0.121909 0.750170 -21.00000 -1.20000 H14D 2 0.206205 0.090966 0.879918 -21.00000 -1.20000 AFIX 0 C15' 1 0.249701 0.025465 0.738710 -21.00000 0.05294 0.06353 = 0.16881 -0.00208 0.02529 -0.00884 AFIX 137 H15D 2 0.163522 -0.000681 0.729552 -21.00000 -1.50000 H15E 2 0.320528 -0.000094 0.789880 -21.00000 -1.50000 H15F 2 0.279794 0.032586 0.660192 -21.00000 -1.50000 PART 0 AFIX 0 C16 1 0.588788 0.250248 0.539834 11.00000 0.04615 0.04476 = 0.03111 0.00242 0.00463 -0.01062 C17 1 0.699571 0.203578 0.564158 11.00000 0.04609 0.05291 = 0.03984 0.00196 0.01020 -0.00797 AFIX 43 H17A 2 0.733101 0.192249 0.644368 11.00000 -1.20000 AFIX 0 C18 1 0.760269 0.173890 0.470156 11.00000 0.05589 0.05749 = 0.05945 -0.00289 0.02478 -0.00965 C19 1 0.711475 0.187975 0.350734 11.00000 0.08072 0.07284 = 0.05088 -0.01379 0.03087 -0.02400 AFIX 43 H19A 2 0.750709 0.166054 0.288069 11.00000 -1.20000 AFIX 0 C20 1 0.603847 0.234951 0.325570 11.00000 0.08138 0.08255 = 0.02982 -0.00099 0.01024 -0.02620 AFIX 43 H20A 2 0.570576 0.245118 0.244823 11.00000 -1.20000 AFIX 0 C21 1 0.543112 0.267831 0.418155 11.00000 0.05778 0.05813 = 0.03284 0.00494 0.00225 -0.01633 HKLF 4 REM a in P2(1)/n REM R1 = 0.0497 for 3604 Fo > 4sig(Fo) and 0.0724 for all 5008 data REM 266 parameters refined using 3 restraints END ;