data_mn265 _publ_contact_author_name 'Klaas A. Zachariasse' _publ_contact_author_address ; MPI fuer biophysikalische Chemie D-37070 Goettingen Bundesrepublik Deutschland ; loop_ _publ_author_name _publ_author_address 'Sergey I. Druzhinin' ; MPI fuer biophysikalische Chemie D-37070 Goettingen Bundesrepublik Deutschland ; 'Victor A. Galievsky' ; MPI fuer biophysikalische Chemie D-37070 Goettingen Bundesrepublik Deutschland ; 'Attila Demeter' ; Institute of Materials and Environmental Chemistry Research Centre for Natural Sciences Hungarian Academy of Sciences 1519 Budapest P.O.Box 286 Hungary ; 'Sergey A. Kovalenko' ; Institut fuer Chemie Humboldt Universitaet zu Berlin Brook-Taylor-Str. 2 D-12489 Berlin Bundesrepublik Deutschland ; 'Tamara Senyushkina' ; MPI fuer biophysikalische Chemie D-37070 Goettingen Bundesrepublik Deutschland ; 'Srinivas R. Dubbaka' ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstra\&se 5-13 (Haus F) D-81377 M\"unchen Bundesrepublik Deutschland ; 'Paul Knochel' ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstra\&se 5-13 (Haus F) D-81377 M\"unchen Bundesrepublik Deutschland ; 'Peter Mayer' ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstra\&se 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; 'Christian Grosse' ; Institut fuer Anorganische Chemie Georg-August Universitaet Tammannstrasse 4 37077 Goettingen Germany ; 'Dietmar Stalke' ; Institut fuer Anorganische Chemie Georg-August Universitaet Tammannstrasse 4 37077 Goettingen Germany ; 'Klaas A. Zachariasse' ; MPI fuer biophysikalische Chemie D-37070 Goettingen Bundesrepublik Deutschland ; _publ_contact_author_email 'kzachar@gwdg.de' _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_requested_journal 'J. Phys. Chem. A' _publ_section_title ; Two-State Intramolecular Charge Transfer (ICT) with 3,5-Dimethyl-4-(Dimethylamino)benzonitrile (MMD) and Its Meta-Isomer mMMD. Ground State Amino Twist Not Essential for ICT ; _publ_section_abstract ? _publ_section_comment ? _vrf_PLAT031_mn265 ; PROBLEM: Refined Extinction Parameter within Range ...... 2.000 Sigma RESPONSE: extinction parameter does not cause any structure problems ; _audit_update_record 18-Jul-08 _chemical_name_common ? #?# use for preliminary identification _chemical_compound_source ? _exptl_crystal_description platelet #?# _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 #?# in millimeters _exptl_crystal_size_mid 0.13 #?# in millimeters _exptl_crystal_size_min 0.07 #?# in millimeters _exptl_crystal_density_method 'not measured' _exptl_crystal_density_meas ? _exptl_special_details ? _audit_author_name 'Mayer, P.' #?# X-ray operator _audit_creation_date 18-Jul-08 #?# style: 18-Aug-1998 _diffrn_ambient_temperature 200(2) #?# in K _diffrn_source_type 'FR 591 generator' _diffrn_source_power 3.025 #?# in kW _diffrn_source_voltage 55.00 #?# in kV _diffrn_source_current 55.00 #?# in mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator 'MONTEL, graded multilayered X-ray optics' _diffrn_radiation_collimation 0.20 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'KappaCCD' _diffrn_measurement_method 'CCD, rotation images, thick slices, phi/omega-scan' _diffrn_detector_area_resol_mean 9 _diffrn_special_details ? _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_UB_11 -0.0511404 _diffrn_orient_matrix_UB_12 0.0317310 _diffrn_orient_matrix_UB_13 -0.0580957 _diffrn_orient_matrix_UB_21 -0.1072521 _diffrn_orient_matrix_UB_22 0.0375169 _diffrn_orient_matrix_UB_23 0.0311896 _diffrn_orient_matrix_UB_31 0.0560126 _diffrn_orient_matrix_UB_32 0.1008078 _diffrn_orient_matrix_UB_33 0.0066791 loop_ _reflns_scale_group_code _reflns_scale_meas_F 1 1.0 _cell_length_a 8.9170(4) _cell_length_b 7.6126(3) _cell_length_c 15.0884(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1024.22(7) _cell_measurement_temperature 200(2) #?# in K _cell_measurement_reflns_used 7754 _cell_measurement_theta_min 3.134 _cell_measurement_theta_max 27.485 _cell_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.001000 0 0 -1 0.070000 8 -1 0 0.078000 -1 0 0 0.050000 1 5 0 0.120000 -1 -6 0 0.181000 -4 -3 0 0.074000 -4 -1 0 0.043000 1 0 -3 0.082000 1 3 -7 0.111000 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_reflns_number 6109 #xl _diffrn_reflns_av_R_equivalents 0.0256 #xl _diffrn_reflns_av_sigmaI/netI 0.0166 #xl _diffrn_reflns_limit_h_min -10 #xl _diffrn_reflns_limit_h_max 10 #xl _diffrn_reflns_limit_k_min -9 #xl _diffrn_reflns_limit_k_max 9 #xl _diffrn_reflns_limit_l_min -18 #xl _diffrn_reflns_limit_l_max 18 #xl _diffrn_reflns_theta_min 3.54 #xl _diffrn_reflns_theta_max 25.23 #xl _diffrn_measured_fraction_theta_max 0.991 #xl _diffrn_reflns_theta_full 25.23 #xl _diffrn_measured_fraction_theta_full 0.991 #xl _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n m a' _symmetry_Int_Tables_number 62 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' 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' _reflns_number_total 992 #xl _reflns_number_gt 782 #xl _reflns_threshold_expression >2sigma(I) #xl _reflns_special_details ? _refine_ls_structure_factor_coef Fsqd #xl _refine_ls_matrix_type full #xl _refine_ls_weighting_scheme calc #xl _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0730P)^2^+0.4534P] where P=(Fo^2^+2Fc^2^)/3' #xl _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr #?# mixed --> _refine_special_details _refine_ls_extinction_method SHELXL #xl _refine_ls_extinction_coef 0.04(2) #xl _refine_ls_abs_structure_details ? #xl _refine_ls_abs_structure_Flack ? #xl _refine_ls_number_reflns 992 #xl _refine_ls_number_parameters 80 #xl _refine_ls_number_restraints 0 #xl _refine_ls_R_factor_all 0.0770 #xl _refine_ls_R_factor_gt 0.0641 #xl _refine_ls_wR_factor_ref 0.1785 #xl _refine_ls_wR_factor_gt 0.1708 #xl _refine_ls_goodness_of_fit_ref 1.071 #xl _refine_ls_restrained_S_all 1.071 #xl _refine_ls_shift/su_max 0.000 #xl _refine_ls_shift/su_mean 0.000 #xl _refine_diff_density_max 0.254 #xl _refine_diff_density_min -0.225 #xl _refine_diff_density_rms 0.034 #xl _refine_special_details ? _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution ; A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for crystal structure determination and refinement; J. Appl. Crystallogr. 1999, 32, 115-119. ; _computing_structure_refinement 'SHELXL-97 (G. M. Sheldrick. University of G\"ottingen, 97-2 version)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N7 N 0.8098(3) 0.2500 0.16068(15) 0.0635(8) Uani 1 2 d S . . N9 N 0.4309(4) 0.2500 -0.1578(2) 0.0958(12) Uani 1 2 d S . . C3 C 0.8175(3) 0.2500 0.06571(16) 0.0452(7) Uani 1 2 d S . . C2 C 0.6793(3) 0.2500 0.02112(15) 0.0419(7) Uani 1 2 d S . . C1 C 0.6802(3) 0.2500 -0.07183(16) 0.0478(7) Uani 1 2 d S . . C6 C 0.8138(4) 0.2500 -0.11922(19) 0.0638(9) Uani 1 2 d S . . H6 H 0.8131 0.2500 -0.1822 0.077 Uiso 1 2 calc SR . . C5 C 0.9463(3) 0.2500 -0.0737(2) 0.0689(10) Uani 1 2 d S . . H5 H 1.0378 0.2500 -0.1059 0.083 Uiso 1 2 calc SR . . C4 C 0.9515(3) 0.2500 0.0181(2) 0.0572(8) Uani 1 2 d S . . C13 C 0.5344(3) 0.2500 0.07080(18) 0.0604(8) Uani 1 2 d S . . H13A H 0.5073 0.3709 0.0863 0.091 Uiso 0.50 1 calc PR . . H13B H 0.5453 0.1803 0.1250 0.091 Uiso 0.50 1 calc PR . . H13C H 0.4556 0.1988 0.0336 0.091 Uiso 0.50 1 calc PR . . C8 C 0.5403(4) 0.2500 -0.11888(19) 0.0651(9) Uani 1 2 d S . . C12 C 1.1034(3) 0.2500 0.0633(3) 0.0870(12) Uani 1 2 d S . . H12A H 1.1782 0.3021 0.0236 0.131 Uiso 0.50 1 calc PR . . H12B H 1.1324 0.1290 0.0774 0.131 Uiso 0.50 1 calc PR . . H12C H 1.0978 0.3189 0.1180 0.131 Uiso 0.50 1 calc PR . . C10 C 0.8443(3) 0.0914(3) 0.20650(14) 0.0846(9) Uani 1 1 d . . . H10A H 0.9534 0.0764 0.2092 0.127 Uiso 1 1 calc R . . H10B H 0.7996 -0.0083 0.1750 0.127 Uiso 1 1 calc R . . H10C H 0.8037 0.0970 0.2668 0.127 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N7 0.0892(19) 0.0548(15) 0.0465(13) 0.000 -0.0218(11) 0.000 N9 0.111(2) 0.088(2) 0.089(2) 0.000 -0.0558(19) 0.000 C3 0.0465(14) 0.0431(14) 0.0460(14) 0.000 -0.0062(10) 0.000 C2 0.0440(14) 0.0439(14) 0.0377(13) 0.000 -0.0002(9) 0.000 C1 0.0586(16) 0.0459(14) 0.0388(13) 0.000 -0.0043(11) 0.000 C6 0.096(2) 0.0529(17) 0.0430(15) 0.000 0.0200(15) 0.000 C5 0.0606(19) 0.0607(18) 0.085(2) 0.000 0.0326(17) 0.000 C4 0.0442(16) 0.0453(15) 0.082(2) 0.000 0.0008(13) 0.000 C13 0.0462(15) 0.082(2) 0.0528(16) 0.000 0.0053(12) 0.000 C8 0.088(2) 0.0565(17) 0.0504(16) 0.000 -0.0225(16) 0.000 C12 0.0423(17) 0.072(2) 0.147(3) 0.000 -0.0107(19) 0.000 C10 0.137(2) 0.0631(15) 0.0537(13) 0.0047(10) -0.0068(13) 0.0076(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N7 C10 1.425(2) . ? N7 C10 1.425(2) 8_565 ? N7 C3 1.435(3) . ? N9 C8 1.139(4) . ? C3 C4 1.394(4) . ? C3 C2 1.404(3) . ? C2 C1 1.402(3) . ? C2 C13 1.494(3) . ? C1 C6 1.390(4) . ? C1 C8 1.435(4) . ? C6 C5 1.367(4) . ? C6 H6 0.9500 . ? C5 C4 1.386(5) . ? C5 H5 0.9500 . ? C4 C12 1.516(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 N7 C10 115.9(2) . 8_565 ? C10 N7 C3 118.31(14) . . ? C10 N7 C3 118.31(14) 8_565 . ? C4 C3 C2 120.4(2) . . ? C4 C3 N7 123.8(2) . . ? C2 C3 N7 115.9(2) . . ? C1 C2 C3 118.3(2) . . ? C1 C2 C13 120.4(2) . . ? C3 C2 C13 121.2(2) . . ? C6 C1 C2 121.3(2) . . ? C6 C1 C8 119.4(2) . . ? C2 C1 C8 119.3(2) . . ? C5 C6 C1 118.8(3) . . ? C5 C6 H6 120.6 . . ? C1 C6 H6 120.6 . . ? C6 C5 C4 122.1(3) . . ? C6 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? C5 C4 C3 119.1(3) . . ? C5 C4 C12 118.6(3) . . ? C3 C4 C12 122.3(3) . . ? C2 C13 H13A 109.5 . . ? C2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N9 C8 C1 178.6(4) . . ? C4 C12 H12A 109.5 . . ? C4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N7 C10 H10A 109.5 . . ? N7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 N7 C3 C4 -74.3(2) . . . . ? C10 N7 C3 C4 74.3(2) 8_565 . . . ? C10 N7 C3 C2 105.7(2) . . . . ? C10 N7 C3 C2 -105.7(2) 8_565 . . . ? C4 C3 C2 C1 0.0 . . . . ? N7 C3 C2 C1 180.0 . . . . ? C4 C3 C2 C13 180.0 . . . . ? N7 C3 C2 C13 0.0 . . . . ? C3 C2 C1 C6 0.0 . . . . ? C13 C2 C1 C6 180.0 . . . . ? C3 C2 C1 C8 180.0 . . . . ? C13 C2 C1 C8 0.0 . . . . ? C2 C1 C6 C5 0.0 . . . . ? C8 C1 C6 C5 180.0 . . . . ? C1 C6 C5 C4 0.0 . . . . ? C6 C5 C4 C3 0.0 . . . . ? C6 C5 C4 C12 180.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? N7 C3 C4 C5 180.0 . . . . ? C2 C3 C4 C12 180.0 . . . . ? N7 C3 C4 C12 0.0 . . . . ? _audit_block_code C11H14N2_mn265_zachariasse _audit_creation_method 'form98_non/compatible with shelxl97-2' _chemical_name_systematic ? _chemical_formula_moiety 'C11 H14 N2' _chemical_formula_sum 'C11 H14 N2' _chemical_formula_weight 174.242 _chemical_melting_point ? #?# in K! _cell_formula_units_Z 4 #?# adjust to _chemical_formula_[] _exptl_crystal_density_diffrn 1.12999(8) _exptl_crystal_F_000 376 _iucr_refine_instructions_details ; TITL mn265 in (62) sir97 Pnma CELL 0.71073 8.9170 7.6126 15.0884 90.000 90.000 90.000 ZERR 4 0.0004 0.0003 0.0006 0.000 0.000 0.000 LATT 1 SYMM 0.50000 - X , - Y , 0.50000 + Z SYMM 0.50000 + X , 0.50000 - Y , 0.50000 - Z SYMM - X , 0.50000 + Y , - Z SFAC C H N UNIT 44 56 8 LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!! OMIT 0 50.5 OMIT 0 6 6 TEMP -73 L.S. 20 CONF FMAP 2 PLAN -20 ACTA BOND $H WGHT 0.073000 0.453400 EXTI 0.044362 FVAR 1.35557 N7 3 0.809820 0.250000 0.160682 10.50000 0.08923 0.05477 = 0.04654 0.00000 -0.02177 0.00000 N9 3 0.430938 0.250000 -0.157828 10.50000 0.11074 0.08804 = 0.08875 0.00000 -0.05581 0.00000 C3 1 0.817541 0.250000 0.065714 10.50000 0.04650 0.04312 = 0.04602 0.00000 -0.00615 0.00000 C2 1 0.679304 0.250000 0.021118 10.50000 0.04398 0.04394 = 0.03775 0.00000 -0.00017 0.00000 C1 1 0.680155 0.250000 -0.071832 10.50000 0.05865 0.04595 = 0.03882 0.00000 -0.00429 0.00000 C6 1 0.813786 0.250000 -0.119220 10.50000 0.09569 0.05287 = 0.04296 0.00000 0.02004 0.00000 AFIX 43 H6 2 0.813069 0.250000 -0.182181 10.50000 -1.20000 AFIX 0 C5 1 0.946298 0.250000 -0.073651 10.50000 0.06058 0.06070 = 0.08531 0.00000 0.03263 0.00000 AFIX 43 H5 2 1.037753 0.250000 -0.105947 10.50000 -1.20000 AFIX 0 C4 1 0.951488 0.250000 0.018129 10.50000 0.04416 0.04533 = 0.08221 0.00000 0.00076 0.00000 C13 1 0.534436 0.250000 0.070795 10.50000 0.04618 0.08221 = 0.05280 0.00000 0.00531 0.00000 AFIX 137 H13A 2 0.507345 0.370897 0.086341 10.50000 -1.50000 H13B 2 0.545312 0.180263 0.125011 10.50000 -1.50000 H13C 2 0.455593 0.198840 0.033631 10.50000 -1.50000 AFIX 0 C8 1 0.540345 0.250000 -0.118876 10.50000 0.08837 0.05653 = 0.05037 0.00000 -0.02252 0.00000 C12 1 1.103384 0.250000 0.063262 10.50000 0.04226 0.07198 = 0.14682 0.00000 -0.01066 0.00000 AFIX 137 H12A 2 1.178156 0.302079 0.023570 10.50000 -1.50000 H12B 2 1.132390 0.129018 0.077366 10.50000 -1.50000 H12C 2 1.097797 0.318903 0.118027 10.50000 -1.50000 AFIX 0 C10 1 0.844311 0.091379 0.206497 11.00000 0.13690 0.06309 = 0.05371 0.00472 -0.00676 0.00757 AFIX 137 H10A 2 0.953365 0.076352 0.209208 11.00000 -1.50000 H10B 2 0.799621 -0.008314 0.175015 11.00000 -1.50000 H10C 2 0.803666 0.097010 0.266776 11.00000 -1.50000 HKLF 4 1 0.0000 -1.0000 0.0000 1.0000 0.0000 0.0000 0.0000 0.0000 1.0000 REM mn265 in (62) sir97 Pnma REM R1 = 0.0641 for 782 Fo > 4sig(Fo) and 0.0770 for all 992 data REM 80 parameters refined using 0 restraints END ;