data_cbq
_audit_creation_method 'SHELXL-2014/7'
_shelx_SHELXL_version_number '2014/7'
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum
'C12 H12 N2'
_chemical_formula_weight 184.24
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'
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 6.5750(13)
_cell_length_b 7.9560(16)
_cell_length_c 9.875(2)
_cell_angle_alpha 90.42(3)
_cell_angle_beta 107.21(3)
_cell_angle_gamma 101.99(3)
_cell_volume 481.35(19)
_cell_formula_units_Z 2
_cell_measurement_temperature 223(2)
_cell_measurement_reflns_used ?
_cell_measurement_theta_min 2.33
_cell_measurement_theta_max 24.98
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.271
_exptl_crystal_F_000 196
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.33
_exptl_crystal_size_min 0.30
_exptl_absorpt_coefficient_mu 0.077
_shelx_estimated_absorpt_T_min ?
_shelx_estimated_absorpt_T_max ?
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_absorpt_special_details ?
_diffrn_ambient_temperature 223(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source 'fine-focus sealed tube'
_diffrn_measurement_device_type 'Enraf-nonius-CAD4 diffractometer'
_diffrn_measurement_method ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 1710
_diffrn_reflns_av_unetI/netI 0.0137
_diffrn_reflns_av_R_equivalents 0.0362
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_l_min -8
_diffrn_reflns_limit_l_max 11
_diffrn_reflns_theta_min 4.333
_diffrn_reflns_theta_max 24.985
_diffrn_reflns_theta_full 24.985
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total 1676
_reflns_number_gt 1462
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_max .
_reflns_Friedel_fraction_full .
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+0.1451P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_number_reflns 1676
_refine_ls_number_parameters 127
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0437
_refine_ls_R_factor_gt 0.0379
_refine_ls_wR_factor_ref 0.1012
_refine_ls_wR_factor_gt 0.0966
_refine_ls_goodness_of_fit_ref 1.031
_refine_ls_restrained_S_all 1.031
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.16466(17) 0.83326(14) 0.16160(12) 0.0266(3) Uani 1 1 d . . . . .
C3 C 0.7615(2) 0.99422(16) 0.30402(13) 0.0233(3) Uani 1 1 d . . . . .
H3 H 0.8886 0.9575 0.3045 0.028 Uiso 1 1 calc R U . . .
C6 C 0.3837(2) 1.10440(17) 0.30525(14) 0.0275(3) Uani 1 1 d . . . . .
H6 H 0.2562 1.1401 0.3055 0.033 Uiso 1 1 calc R U . . .
C2 C 0.5575(2) 0.89109(16) 0.23814(13) 0.0227(3) Uani 1 1 d . . . . .
N2 N 1.15451(19) 1.35850(15) 0.48148(13) 0.0347(3) Uani 1 1 d . . . . .
C7 C 0.9863(2) 1.26788(16) 0.43343(14) 0.0257(3) Uani 1 1 d . . . . .
C1 C 0.3699(2) 0.94706(16) 0.23855(13) 0.0233(3) Uani 1 1 d . . . . .
C5 C 0.5870(2) 1.20900(17) 0.37168(14) 0.0270(3) Uani 1 1 d . . . . .
H5 H 0.5984 1.3160 0.4176 0.032 Uiso 1 1 calc R U . . .
C4 C 0.7751(2) 1.15438(16) 0.37006(13) 0.0232(3) Uani 1 1 d . . . . .
C8 C 0.1592(2) 0.66215(17) 0.22249(15) 0.0318(3) Uani 1 1 d . . . . .
H8A H 0.0267 0.5805 0.1666 0.038 Uiso 1 1 calc R U . . .
H8B H 0.1528 0.6730 0.3200 0.038 Uiso 1 1 calc R U . . .
C9 C 0.1676(2) 0.80975(18) 0.01207(14) 0.0320(3) Uani 1 1 d . . . . .
H9A H 0.1711 0.9206 -0.0308 0.038 Uiso 1 1 calc R U . . .
H9B H 0.0331 0.7294 -0.0428 0.038 Uiso 1 1 calc R U . . .
C11 C 0.3665(2) 0.73977(18) 0.00314(15) 0.0332(3) Uani 1 1 d . . . . .
H11A H 0.3170 0.6283 -0.0524 0.040 Uiso 1 1 calc R U . . .
H11B H 0.4538 0.8201 -0.0436 0.040 Uiso 1 1 calc R U . . .
C10 C 0.3606(2) 0.59034(17) 0.22355(16) 0.0331(3) Uani 1 1 d . . . . .
H10A H 0.4430 0.5751 0.3214 0.040 Uiso 1 1 calc R U . . .
H10B H 0.3141 0.4781 0.1693 0.040 Uiso 1 1 calc R U . . .
C12 C 0.5050(2) 0.71922(16) 0.15608(14) 0.0280(3) Uani 1 1 d . . . . .
H12 H 0.6391 0.6807 0.1569 0.034 Uiso 1 1 calc R U . . .
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
N1 0.0219(6) 0.0256(6) 0.0294(6) 0.0007(5) 0.0059(5) 0.0018(4)
C3 0.0224(6) 0.0225(6) 0.0257(7) 0.0032(5) 0.0078(5) 0.0060(5)
C6 0.0245(7) 0.0285(7) 0.0317(7) 0.0003(5) 0.0103(6) 0.0085(5)
C2 0.0236(6) 0.0213(6) 0.0235(6) 0.0031(5) 0.0078(5) 0.0050(5)
N2 0.0294(7) 0.0275(6) 0.0428(7) -0.0039(5) 0.0068(5) 0.0027(5)
C7 0.0292(7) 0.0214(6) 0.0269(7) 0.0009(5) 0.0083(6) 0.0073(6)
C1 0.0227(6) 0.0241(6) 0.0225(6) 0.0032(5) 0.0075(5) 0.0033(5)
C5 0.0315(7) 0.0233(7) 0.0270(7) -0.0014(5) 0.0094(6) 0.0069(5)
C4 0.0242(7) 0.0221(6) 0.0215(6) 0.0028(5) 0.0056(5) 0.0029(5)
C8 0.0280(7) 0.0277(7) 0.0359(8) 0.0031(6) 0.0097(6) -0.0018(6)
C9 0.0299(7) 0.0331(7) 0.0268(7) 0.0002(6) 0.0022(6) 0.0028(6)
C11 0.0349(8) 0.0315(7) 0.0307(7) -0.0069(6) 0.0107(6) 0.0006(6)
C10 0.0307(7) 0.0223(7) 0.0403(8) 0.0031(6) 0.0043(6) 0.0021(6)
C12 0.0246(7) 0.0229(7) 0.0355(8) -0.0029(5) 0.0082(6) 0.0044(5)
_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.4469(17) . ?
N1 C8 1.4902(18) . ?
N1 C9 1.4933(18) . ?
C3 C2 1.3832(18) . ?
C3 C4 1.4009(18) . ?
C3 H3 0.9400 . ?
C6 C1 1.3836(19) . ?
C6 C5 1.3860(19) . ?
C6 H6 0.9400 . ?
C2 C1 1.3970(18) . ?
C2 C12 1.5058(18) . ?
N2 C7 1.1494(18) . ?
C7 C4 1.4460(19) . ?
C5 C4 1.3978(19) . ?
C5 H5 0.9400 . ?
C8 C10 1.545(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C11 1.548(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C11 C12 1.546(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C10 C12 1.542(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C12 H12 0.9900 . ?
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
C1 N1 C8 107.94(10) . . ?
C1 N1 C9 106.68(10) . . ?
C8 N1 C9 107.33(11) . . ?
C2 C3 C4 118.81(12) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C1 C6 C5 119.46(12) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C3 C2 C1 120.01(12) . . ?
C3 C2 C12 127.68(12) . . ?
C1 C2 C12 112.26(11) . . ?
N2 C7 C4 178.81(14) . . ?
C6 C1 C2 121.12(12) . . ?
C6 C1 N1 123.10(12) . . ?
C2 C1 N1 115.75(11) . . ?
C6 C5 C4 119.59(12) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C4 C3 121.00(12) . . ?
C5 C4 C7 119.25(11) . . ?
C3 C4 C7 119.72(11) . . ?
N1 C8 C10 112.31(11) . . ?
N1 C8 H8A 109.1 . . ?
C10 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
C10 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
N1 C9 C11 112.33(11) . . ?
N1 C9 H9A 109.1 . . ?
C11 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C11 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C12 C11 C9 108.11(11) . . ?
C12 C11 H11A 110.1 . . ?
C9 C11 H11A 110.1 . . ?
C12 C11 H11B 110.1 . . ?
C9 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
C12 C10 C8 108.36(11) . . ?
C12 C10 H10A 110.0 . . ?
C8 C10 H10A 110.0 . . ?
C12 C10 H10B 110.0 . . ?
C8 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C2 C12 C10 107.24(11) . . ?
C2 C12 C11 107.01(11) . . ?
C10 C12 C11 107.79(11) . . ?
C2 C12 H12 111.5 . . ?
C10 C12 H12 111.5 . . ?
C11 C12 H12 111.5 . . ?
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
C4 C3 C2 C1 -0.16(18) . . . . ?
C4 C3 C2 C12 177.16(12) . . . . ?
C5 C6 C1 C2 0.60(19) . . . . ?
C5 C6 C1 N1 -177.30(11) . . . . ?
C3 C2 C1 C6 -0.61(19) . . . . ?
C12 C2 C1 C6 -178.32(11) . . . . ?
C3 C2 C1 N1 177.43(10) . . . . ?
C12 C2 C1 N1 -0.27(16) . . . . ?
C8 N1 C1 C6 -124.79(13) . . . . ?
C9 N1 C1 C6 120.13(13) . . . . ?
C8 N1 C1 C2 57.21(14) . . . . ?
C9 N1 C1 C2 -57.87(14) . . . . ?
C1 C6 C5 C4 0.17(19) . . . . ?
C6 C5 C4 C3 -0.94(19) . . . . ?
C6 C5 C4 C7 176.94(11) . . . . ?
C2 C3 C4 C5 0.93(18) . . . . ?
C2 C3 C4 C7 -176.95(11) . . . . ?
C1 N1 C8 C10 -54.17(14) . . . . ?
C9 N1 C8 C10 60.48(14) . . . . ?
C1 N1 C9 C11 56.60(14) . . . . ?
C8 N1 C9 C11 -58.89(14) . . . . ?
N1 C9 C11 C12 -1.11(15) . . . . ?
N1 C8 C10 C12 -1.47(15) . . . . ?
C3 C2 C12 C10 125.14(13) . . . . ?
C1 C2 C12 C10 -57.37(14) . . . . ?
C3 C2 C12 C11 -119.42(14) . . . . ?
C1 C2 C12 C11 58.07(14) . . . . ?
C8 C10 C12 C2 55.88(14) . . . . ?
C8 C10 C12 C11 -59.04(14) . . . . ?
C9 C11 C12 C2 -54.69(14) . . . . ?
C9 C11 C12 C10 60.38(14) . . . . ?
_refine_diff_density_max 0.162
_refine_diff_density_min -0.192
_refine_diff_density_rms 0.041
_shelx_res_file
;
cbq.res created by SHELXL-2014/7
TITL cbq in P-1
CELL 0.71073 6.5750 7.9560 9.8750 90.423 107.213 101.993
ZERR 2.00 0.0013 0.0016 0.0020 0.030 0.030 0.030
LATT 1
SFAC C H N
UNIT 24 24 4
L.S. 4
ACTA
LIST 4
BOND $H
CONF
FMAP 2
PLAN 5
TEMP -50
WGHT 0.053800 0.145100
FVAR 0.74502
N1 3 0.164658 0.833265 0.161602 11.00000 0.02191 0.02560 =
0.02936 0.00070 0.00591 0.00183
C3 1 0.761494 0.994218 0.304025 11.00000 0.02241 0.02252 =
0.02574 0.00320 0.00775 0.00600
AFIX 43
H3 2 0.888645 0.957494 0.304485 11.00000 -1.20000
AFIX 0
C6 1 0.383687 1.104397 0.305250 11.00000 0.02453 0.02848 =
0.03174 0.00033 0.01029 0.00845
AFIX 43
H6 2 0.256167 1.140057 0.305510 11.00000 -1.20000
AFIX 0
C2 1 0.557548 0.891093 0.238141 11.00000 0.02359 0.02131 =
0.02354 0.00311 0.00780 0.00499
N2 3 1.154514 1.358498 0.481484 11.00000 0.02937 0.02748 =
0.04277 -0.00392 0.00678 0.00270
C7 1 0.986309 1.267879 0.433426 11.00000 0.02925 0.02143 =
0.02691 0.00094 0.00825 0.00733
C1 1 0.369908 0.947058 0.238548 11.00000 0.02272 0.02414 =
0.02250 0.00319 0.00753 0.00326
C5 1 0.587040 1.209002 0.371683 11.00000 0.03153 0.02327 =
0.02704 -0.00142 0.00944 0.00688
AFIX 43
H5 2 0.598386 1.316022 0.417550 11.00000 -1.20000
AFIX 0
C4 1 0.775149 1.154378 0.370055 11.00000 0.02419 0.02209 =
0.02154 0.00275 0.00560 0.00287
C8 1 0.159176 0.662148 0.222485 11.00000 0.02799 0.02774 =
0.03591 0.00308 0.00971 -0.00180
AFIX 23
H8A 2 0.026674 0.580517 0.166591 11.00000 -1.20000
H8B 2 0.152804 0.672982 0.319988 11.00000 -1.20000
AFIX 0
C9 1 0.167599 0.809749 0.012072 11.00000 0.02993 0.03310 =
0.02682 0.00025 0.00221 0.00278
AFIX 23
H9A 2 0.171056 0.920579 -0.030830 11.00000 -1.20000
H9B 2 0.033102 0.729435 -0.042804 11.00000 -1.20000
AFIX 0
C11 1 0.366462 0.739765 0.003140 11.00000 0.03485 0.03146 =
0.03070 -0.00693 0.01073 0.00058
AFIX 23
H11A 2 0.316982 0.628279 -0.052368 11.00000 -1.20000
H11B 2 0.453839 0.820103 -0.043607 11.00000 -1.20000
AFIX 0
C10 1 0.360565 0.590335 0.223554 11.00000 0.03073 0.02233 =
0.04026 0.00313 0.00435 0.00212
AFIX 23
H10A 2 0.442965 0.575113 0.321364 11.00000 -1.20000
H10B 2 0.314125 0.478102 0.169299 11.00000 -1.20000
AFIX 0
C12 1 0.504970 0.719217 0.156084 11.00000 0.02459 0.02290 =
0.03548 -0.00294 0.00823 0.00441
AFIX 13
H12 2 0.639118 0.680668 0.156948 11.00000 -1.20000
AFIX 0
HKLF 4
REM cbq in P-1
REM R1 = 0.0379 for 1462 Fo > 4sig(Fo) and 0.0437 for all 1676 data
REM 127 parameters refined using 0 restraints
END
WGHT 0.0532 0.1516
REM Highest difference peak 0.162, deepest hole -0.192, 1-sigma level 0.041
Q1 1 0.4635 0.8968 0.2817 11.00000 0.05 0.16
Q2 1 0.4635 0.9460 0.2063 11.00000 0.05 0.15
Q3 1 0.4681 0.9420 -0.0020 11.00000 0.05 0.13
Q4 1 0.5329 0.8205 0.1889 11.00000 0.05 0.12
Q5 1 0.5467 1.1335 0.5276 11.00000 0.05 0.12
;
_shelx_res_checksum 49513
_shelx_hkl_file
;
-7 5 5 0.77 0.24
-7 5 4 2.55 0.31
-7 5 3 0.05 0.18
-7 5 2 0.75 0.23
-7 5 1 6.47 0.42
-7 5 0 2.14 0.30
-7 4 0 1.63 0.26
-7 4 1 0.90 0.23
-7 4 2 0.99 0.22
-7 4 3 13.22 0.64
-7 4 4 8.82 0.44
-7 4 5 5.05 0.38
-7 4 6 0.26 0.18
-7 4 7 -0.11 0.22
-7 3 7 6.52 0.58
-7 3 6 42.77 0.98
-7 3 5 0.90 0.22
-7 3 4 13.27 0.62
-7 3 3 8.68 0.57
-7 3 2 -0.43 0.17
-7 3 1 2.12 0.27
-7 3 0 1.18 0.25
-7 2 0 17.87 0.75
-7 2 1 12.61 0.53
-7 2 2 0.33 0.19
-7 2 3 0.56 0.21
-7 2 4 2.91 0.31
-7 2 5 5.58 0.38
-7 2 6 24.15 0.79
-7 2 7 0.57 0.21
-7 2 8 20.93 0.79
-7 1 8 23.95 0.82
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