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#$Date: 2022-06-10 11:53:47 +0300 (Fri, 10 Jun 2022) $
#$Revision: 275960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/53/8105381.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8105381
loop_
_publ_author_name
'Shi, Xiao-Ming'
'Xiao, Li-Na'
'Peng, Peng'
_publ_section_title
;
 Crystal structure of 2-methyl-1H-perimidine, C12H10N2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1069
_journal_page_last               1071
_journal_paper_doi               10.1515/ncrs-2020-0175
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                102.375(3)
_cell_angle_beta                 109.641(3)
_cell_angle_gamma                99.834(2)
_cell_formula_units_Z            4
_cell_length_a                   9.0431(18)
_cell_length_b                   9.9770(19)
_cell_length_c                   11.623(2)
_cell_measurement_reflns_used    2904
_cell_measurement_temperature    128.15
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     930.5(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      128.15
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11583
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.546
_diffrn_reflns_theta_min         3.245
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_correction_T_min  0.9844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0536P)²+0.3063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3655
_reflns_number_total             4129
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0175_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105381
_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.
;
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16),
  C18(H18), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.47567(11) 0.79112(9) 0.41471(8) 0.01860(19) Uani 1 1 d . . . . .
N2 N 0.19452(11) 0.74922(9) 0.36651(9) 0.01859(19) Uani 1 1 d . . . . .
H2 H 0.105(2) 0.6926(17) 0.3691(15) 0.034(4) Uiso 1 1 d . . . . .
C1 C 0.46889(13) 0.90076(11) 0.35596(9) 0.0178(2) Uani 1 1 d . . . . .
C2 C 0.60712(13) 0.97563(12) 0.34877(10) 0.0222(2) Uani 1 1 d . . . . .
H2A H 0.708129 0.954224 0.384625 0.027 Uiso 1 1 calc R . . . .
C3 C 0.59822(14) 1.08382(12) 0.28818(11) 0.0258(2) Uani 1 1 d . . . . .
H3 H 0.693966 1.134447 0.283438 0.031 Uiso 1 1 calc R . . . .
C4 C 0.45440(15) 1.11772(12) 0.23586(11) 0.0252(2) Uani 1 1 d . . . . .
H4 H 0.452071 1.191731 0.196228 0.030 Uiso 1 1 calc R . . . .
C5 C 0.30924(14) 1.04322(11) 0.24047(10) 0.0210(2) Uani 1 1 d . . . . .
C6 C 0.15502(15) 1.06923(12) 0.18508(11) 0.0254(2) Uani 1 1 d . . . . .
H6 H 0.146099 1.141607 0.143652 0.030 Uiso 1 1 calc R . . . .
C7 C 0.01917(15) 0.99095(13) 0.19086(11) 0.0260(2) Uani 1 1 d . . . . .
H7 H -0.082871 1.009787 0.152929 0.031 Uiso 1 1 calc R . . . .
C8 C 0.02735(13) 0.88293(12) 0.25189(11) 0.0224(2) Uani 1 1 d . . . . .
H8 H -0.067824 0.829972 0.255730 0.027 Uiso 1 1 calc R . . . .
C9 C 0.17581(13) 0.85537(11) 0.30597(10) 0.0179(2) Uani 1 1 d . . . . .
C10 C 0.31836(12) 0.93411(10) 0.30143(9) 0.0173(2) Uani 1 1 d . . . . .
C11 C 0.34102(13) 0.72292(11) 0.41697(10) 0.0183(2) Uani 1 1 d . . . . .
C12 C 0.34184(14) 0.60271(12) 0.47545(11) 0.0242(2) Uani 1 1 d . . . . .
H12A H 0.326148 0.514357 0.411061 0.036 Uiso 1 1 calc GR . . . .
H12B H 0.253531 0.592306 0.506503 0.036 Uiso 1 1 calc GR . . . .
H12C H 0.446388 0.622931 0.546989 0.036 Uiso 1 1 calc GR . . . .
N3 N 0.09574(11) 0.43295(10) 0.65427(9) 0.0208(2) Uani 1 1 d . . . . .
N4 N 0.34695(11) 0.38962(10) 0.66561(9) 0.0192(2) Uani 1 1 d . . . . .
H4A H 0.3992(19) 0.3351(17) 0.6310(15) 0.034(4) Uiso 1 1 d . . . . .
C13 C 0.17641(13) 0.54173(11) 0.77109(10) 0.0194(2) Uani 1 1 d . . . . .
C14 C 0.08926(14) 0.61650(13) 0.82518(12) 0.0260(2) Uani 1 1 d . . . . .
H14 H -0.025748 0.594951 0.783640 0.031 Uiso 1 1 calc R . . . .
C15 C 0.17132(15) 0.72493(13) 0.94221(12) 0.0290(3) Uani 1 1 d . . . . .
H15 H 0.110424 0.776124 0.978543 0.035 Uiso 1 1 calc R . . . .
C16 C 0.33691(15) 0.75807(12) 1.00467(11) 0.0260(2) Uani 1 1 d . . . . .
H16 H 0.389252 0.832299 1.082967 0.031 Uiso 1 1 calc R . . . .
C17 C 0.43077(13) 0.68264(11) 0.95356(10) 0.0206(2) Uani 1 1 d . . . . .
C18 C 0.60210(14) 0.70862(12) 1.01469(10) 0.0240(2) Uani 1 1 d . . . . .
H18 H 0.659672 0.780872 1.093826 0.029 Uiso 1 1 calc R . . . .
C19 C 0.68507(14) 0.63030(13) 0.96045(11) 0.0246(2) Uani 1 1 d . . . . .
H19 H 0.799601 0.648881 1.003043 0.029 Uiso 1 1 calc R . . . .
C20 C 0.60407(13) 0.52274(12) 0.84277(11) 0.0219(2) Uani 1 1 d . . . . .
H20 H 0.663328 0.469668 0.806145 0.026 Uiso 1 1 calc R . . . .
C21 C 0.43777(13) 0.49559(11) 0.78156(10) 0.0178(2) Uani 1 1 d . . . . .
C22 C 0.34844(13) 0.57442(11) 0.83522(10) 0.0176(2) Uani 1 1 d . . . . .
C23 C 0.18353(13) 0.36408(11) 0.60892(10) 0.0191(2) Uani 1 1 d . . . . .
C24 C 0.10078(14) 0.24749(13) 0.48458(11) 0.0271(3) Uani 1 1 d . . . . .
H24A H 0.030598 0.168855 0.495444 0.041 Uiso 1 1 calc GR . . . .
H24B H 0.183048 0.213269 0.458115 0.041 Uiso 1 1 calc GR . . . .
H24C H 0.034692 0.284287 0.419083 0.041 Uiso 1 1 calc GR . . . .
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'
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
C11 N1 C1 117.72(9) . .
C9 N2 H2 119.7(10) . .
C11 N2 H2 118.7(10) . .
C11 N2 C9 121.56(9) . .
N1 C1 C10 120.23(9) . .
C2 C1 N1 120.49(10) . .
C2 C1 C10 119.28(10) . .
C1 C2 H2A 120.0 . .
C1 C2 C3 119.92(10) . .
C3 C2 H2A 120.0 . .
C2 C3 H3 119.3 . .
C4 C3 C2 121.49(10) . .
C4 C3 H3 119.3 . .
C3 C4 H4 119.7 . .
C3 C4 C5 120.54(10) . .
C5 C4 H4 119.7 . .
C4 C5 C6 123.78(10) . .
C4 C5 C10 117.90(10) . .
C10 C5 C6 118.30(10) . .
C5 C6 H6 119.7 . .
C7 C6 C5 120.59(10) . .
C7 C6 H6 119.7 . .
C6 C7 H7 119.3 . .
C6 C7 C8 121.46(10) . .
C8 C7 H7 119.3 . .
C7 C8 H8 120.5 . .
C9 C8 C7 118.97(10) . .
C9 C8 H8 120.5 . .
N2 C9 C10 116.27(9) . .
C8 C9 N2 122.77(10) . .
C8 C9 C10 120.96(10) . .
C5 C10 C1 120.87(10) . .
C9 C10 C1 119.41(9) . .
C9 C10 C5 119.71(10) . .
N1 C11 N2 124.80(10) . .
N1 C11 C12 119.48(10) . .
N2 C11 C12 115.69(9) . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C23 N3 C13 117.78(9) . .
C21 N4 H4A 118.2(10) . .
C23 N4 H4A 120.0(10) . .
C23 N4 C21 121.72(9) . .
N3 C13 C22 120.27(9) . .
C14 C13 N3 120.38(10) . .
C14 C13 C22 119.35(10) . .
C13 C14 H14 120.1 . .
C13 C14 C15 119.85(11) . .
C15 C14 H14 120.1 . .
C14 C15 H15 119.3 . .
C16 C15 C14 121.45(11) . .
C16 C15 H15 119.3 . .
C15 C16 H16 119.7 . .
C15 C16 C17 120.57(10) . .
C17 C16 H16 119.7 . .
C16 C17 C18 123.64(10) . .
C16 C17 C22 118.00(10) . .
C22 C17 C18 118.37(10) . .
C17 C18 H18 119.7 . .
C19 C18 C17 120.54(10) . .
C19 C18 H18 119.7 . .
C18 C19 H19 119.3 . .
C18 C19 C20 121.40(10) . .
C20 C19 H19 119.3 . .
C19 C20 H20 120.4 . .
C21 C20 C19 119.14(10) . .
C21 C20 H20 120.4 . .
N4 C21 C22 116.03(9) . .
C20 C21 N4 123.12(10) . .
C20 C21 C22 120.84(10) . .
C17 C22 C13 120.78(10) . .
C21 C22 C13 119.50(10) . .
C21 C22 C17 119.71(10) . .
N3 C23 N4 124.71(10) . .
N3 C23 C24 118.94(10) . .
N4 C23 C24 116.36(9) . .
C23 C24 H24A 109.5 . .
C23 C24 H24B 109.5 . .
C23 C24 H24C 109.5 . .
H24A C24 H24B 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.4077(13) .
N1 C11 1.3009(14) .
N2 H2 0.918(16) .
N2 C9 1.3950(13) .
N2 C11 1.3530(14) .
C1 C2 1.3805(15) .
C1 C10 1.4249(15) .
C2 H2A 0.9500 .
C2 C3 1.4089(16) .
C3 H3 0.9500 .
C3 C4 1.3720(17) .
C4 H4 0.9500 .
C4 C5 1.4175(16) .
C5 C6 1.4207(16) .
C5 C10 1.4198(14) .
C6 H6 0.9500 .
C6 C7 1.3690(17) .
C7 H7 0.9500 .
C7 C8 1.4106(16) .
C8 H8 0.9500 .
C8 C9 1.3806(15) .
C9 C10 1.4140(15) .
C11 C12 1.4998(14) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
N3 C13 1.4091(14) .
N3 C23 1.3010(14) .
N4 H4A 0.896(16) .
N4 C21 1.3990(14) .
N4 C23 1.3519(14) .
C13 C14 1.3805(15) .
C13 C22 1.4231(15) .
C14 H14 0.9500 .
C14 C15 1.4098(17) .
C15 H15 0.9500 .
C15 C16 1.3696(18) .
C16 H16 0.9500 .
C16 C17 1.4161(16) .
C17 C18 1.4199(16) .
C17 C22 1.4186(15) .
C18 H18 0.9500 .
C18 C19 1.3704(17) .
C19 H19 0.9500 .
C19 C20 1.4099(16) .
C20 H20 0.9500 .
C20 C21 1.3784(15) .
C21 C22 1.4162(14) .
C23 C24 1.5023(15) .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
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
N1 C1 C2 C3 179.14(9) . . . .
N1 C1 C10 C5 -179.21(9) . . . .
N1 C1 C10 C9 -0.51(14) . . . .
N2 C9 C10 C1 0.73(14) . . . .
N2 C9 C10 C5 179.46(9) . . . .
C1 N1 C11 N2 0.27(15) . . . .
C1 N1 C11 C12 178.35(9) . . . .
C1 C2 C3 C4 0.25(17) . . . .
C2 C1 C10 C5 -0.19(15) . . . .
C2 C1 C10 C9 178.51(9) . . . .
C2 C3 C4 C5 -0.55(17) . . . .
C3 C4 C5 C6 -178.00(11) . . . .
C3 C4 C5 C10 0.47(16) . . . .
C4 C5 C6 C7 178.59(11) . . . .
C4 C5 C10 C1 -0.10(15) . . . .
C4 C5 C10 C9 -178.80(9) . . . .
C5 C6 C7 C8 0.24(18) . . . .
C6 C5 C10 C1 178.45(9) . . . .
C6 C5 C10 C9 -0.25(15) . . . .
C6 C7 C8 C9 -0.49(17) . . . .
C7 C8 C9 N2 -179.06(10) . . . .
C7 C8 C9 C10 0.36(16) . . . .
C8 C9 C10 C1 -178.72(9) . . . .
C8 C9 C10 C5 0.00(15) . . . .
C9 N2 C11 N1 -0.01(16) . . . .
C9 N2 C11 C12 -178.15(9) . . . .
C10 C1 C2 C3 0.12(15) . . . .
C10 C5 C6 C7 0.13(16) . . . .
C11 N1 C1 C2 -179.01(9) . . . .
C11 N1 C1 C10 -0.01(14) . . . .
C11 N2 C9 C8 178.94(10) . . . .
C11 N2 C9 C10 -0.50(14) . . . .
N3 C13 C14 C15 179.88(10) . . . .
N3 C13 C22 C17 -179.31(9) . . . .
N3 C13 C22 C21 -0.79(15) . . . .
N4 C21 C22 C13 0.62(14) . . . .
N4 C21 C22 C17 179.16(9) . . . .
C13 N3 C23 N4 -0.23(16) . . . .
C13 N3 C23 C24 179.96(9) . . . .
C13 C14 C15 C16 -0.28(19) . . . .
C14 C13 C22 C17 -0.05(16) . . . .
C14 C13 C22 C21 178.47(10) . . . .
C14 C15 C16 C17 -0.66(19) . . . .
C15 C16 C17 C18 -178.26(11) . . . .
C15 C16 C17 C22 1.20(17) . . . .
C16 C17 C18 C19 179.20(11) . . . .
C16 C17 C22 C13 -0.86(15) . . . .
C16 C17 C22 C21 -179.37(9) . . . .
C17 C18 C19 C20 0.37(17) . . . .
C18 C17 C22 C13 178.63(9) . . . .
C18 C17 C22 C21 0.12(15) . . . .
C18 C19 C20 C21 -0.33(17) . . . .
C19 C20 C21 N4 -179.00(9) . . . .
C19 C20 C21 C22 0.18(16) . . . .
C20 C21 C22 C13 -178.62(9) . . . .
C20 C21 C22 C17 -0.08(15) . . . .
C21 N4 C23 N3 0.08(16) . . . .
C21 N4 C23 C24 179.91(9) . . . .
C22 C13 C14 C15 0.62(17) . . . .
C22 C17 C18 C19 -0.26(16) . . . .
C23 N3 C13 C14 -178.68(10) . . . .
C23 N3 C13 C22 0.57(15) . . . .
C23 N4 C21 C20 178.94(10) . . . .
C23 N4 C21 C22 -0.28(14) . . . .
