#------------------------------------------------------------------------------
#$Date: 2022-03-10 10:20:16 +0200 (Thu, 10 Mar 2022) $
#$Revision: 273585 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/47/8104708.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_8104708
loop_
_publ_author_name
'Wang, Wenxiang'
_publ_section_title
;
 The crystal structure of
 4-(6-acetyl-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidin-7-yl)benzonitrile,
 C14H12N6O
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              777
_journal_page_last               778
_journal_paper_doi               10.1515/ncrs-2021-0106
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C14 H12 N6 O'
_chemical_formula_sum            'C14 H12 N6 O'
_chemical_formula_weight         280.30
_chemical_name_systematic
;
4-(6-acetyl-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidin-7-yl)benzonitrile 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 100.59(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.827(4)
_cell_length_b                   11.021(2)
_cell_length_c                   7.0936(14)
_cell_measurement_reflns_used    3114
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.6110
_cell_measurement_theta_min      2.9770
_cell_volume                     1370.0(5)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)[1]'
_computing_data_collection       'CrystalClear (Rigaku, 2005)[1]'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)[1]'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)[2]'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)[2, 5]'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)[4]'
_computing_structure_solution    'SHELXS 2018/3 (Sheldrick, 2015)[3]'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13141
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         3.458
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.0824
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0950P)²+1.0146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2008
_refine_ls_wR_factor_ref         0.2208
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2098
_reflns_number_total             3109
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0106_suppl.cif
_cod_data_source_block           2
_cod_database_code               8104708
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Me refined with riding coordinates:
 C2(H2A,H2B,H2C), C6(H6A,H6B,H6C)
2.c Aromatic/amide H refined with riding coordinates:
 N5(H5), C9(H9), C11(H11), C12(H12), C28(H28)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O1 O 0.18894(17) 0.1203(3) 0.3687(4) 0.0760(9) Uani 1 1 d . . . . .
N1 N 0.07279(14) -0.1021(3) 1.0839(4) 0.0456(7) Uani 1 1 d . . . . .
N2 N 0.12557(15) -0.1869(3) 1.1583(4) 0.0500(7) Uani 1 1 d . . . . .
N3 N 0.18428(14) -0.1836(2) 1.0767(4) 0.0442(7) Uani 1 1 d . . . . .
N4 N 0.17045(13) -0.0947(2) 0.9432(3) 0.0337(5) Uani 1 1 d . . . . .
N5 N 0.07367(14) 0.0416(2) 0.8264(4) 0.0443(7) Uani 1 1 d . . . . .
H5 H 0.033314 0.079874 0.842575 0.053 Uiso 1 1 calc R U . . .
N6 N 0.5348(2) 0.1756(3) 1.4104(6) 0.0848(12) Uani 1 1 d . . . . .
C1 C 0.10313(15) -0.0473(3) 0.9500(4) 0.0349(6) Uani 1 1 d . . . . .
C2 C 0.0623(2) 0.1581(4) 0.5385(5) 0.0603(10) Uani 1 1 d . . . . .
H2A H 0.015992 0.176678 0.583528 0.090 Uiso 1 1 calc R U . . .
H2B H 0.090935 0.231224 0.532208 0.090 Uiso 1 1 calc R U . . .
H2C H 0.050041 0.122390 0.413105 0.090 Uiso 1 1 calc R U . . .
C3 C 0.10891(17) 0.0703(3) 0.6738(4) 0.0406(7) Uani 1 1 d . . . . .
C4 C 0.17748(16) 0.0227(3) 0.6597(4) 0.0367(7) Uani 1 1 d . . . . .
C5 C 0.21355(19) 0.0453(3) 0.4905(4) 0.0468(8) Uani 1 1 d . . . . .
C6 C 0.2827(2) -0.0262(4) 0.4709(5) 0.0621(10) Uani 1 1 d . . . . .
H6A H 0.294985 -0.081117 0.577068 0.093 Uiso 1 1 calc R U . . .
H6B H 0.272841 -0.071417 0.353251 0.093 Uiso 1 1 calc R U . . .
H6C H 0.324780 0.027977 0.469608 0.093 Uiso 1 1 calc R U . . .
C7 C 0.22207(15) -0.0593(3) 0.8137(4) 0.0340(6) Uani 1 1 d . . . . .
H7 H 0.237281 -0.132504 0.751895 0.041 Uiso 1 1 calc R U . . .
C8 C 0.29329(15) -0.0017(3) 0.9321(4) 0.0345(6) Uani 1 1 d . . . . .
C9 C 0.35549(16) -0.0746(3) 0.9999(4) 0.0421(7) Uani 1 1 d . . . . .
H9 H 0.355020 -0.155924 0.964883 0.051 Uiso 1 1 calc R U . . .
C10 C 0.41976(17) 0.0936(3) 1.1697(4) 0.0439(8) Uani 1 1 d . . . . .
C11 C 0.35837(18) 0.1682(3) 1.0986(5) 0.0486(8) Uani 1 1 d . . . . .
H11 H 0.359683 0.250051 1.130835 0.058 Uiso 1 1 calc R U . . .
C12 C 0.29525(17) 0.1201(3) 0.9795(4) 0.0434(7) Uani 1 1 d . . . . .
H12 H 0.254017 0.169791 0.931190 0.052 Uiso 1 1 calc R U . . .
C13 C 0.4846(2) 0.1418(4) 1.3034(5) 0.0597(10) Uani 1 1 d . . . . .
C28 C 0.41855(17) -0.0265(3) 1.1201(5) 0.0469(8) Uani 1 1 d . . . . .
H28 H 0.460099 -0.075830 1.167074 0.056 Uiso 1 1 calc R U . . .
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'
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
C1 N1 N2 104.3(2) . .
N3 N2 N1 111.5(2) . .
N2 N3 N4 106.1(2) . .
N3 N4 C7 125.1(2) . .
C1 N4 N3 108.2(2) . .
C1 N4 C7 126.7(2) . .
C1 N5 H5 120.2 . .
C1 N5 C3 119.6(2) . .
C3 N5 H5 120.2 . .
N1 C1 N5 129.3(3) . .
N4 C1 N1 109.9(2) . .
N4 C1 N5 120.7(2) . .
H2A C2 H2B 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
C3 C2 H2A 109.5 . .
C3 C2 H2B 109.5 . .
C3 C2 H2C 109.5 . .
N5 C3 C2 111.7(3) . .
C4 C3 N5 121.1(3) . .
C4 C3 C2 127.2(3) . .
C3 C4 C5 121.8(3) . .
C3 C4 C7 122.5(3) . .
C5 C4 C7 115.7(3) . .
O1 C5 C4 122.3(3) . .
O1 C5 C6 119.3(3) . .
C4 C5 C6 118.4(3) . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6B 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
N4 C7 C4 107.6(2) . .
N4 C7 H7 108.6 . .
N4 C7 C8 108.6(2) . .
C4 C7 H7 108.6 . .
C4 C7 C8 114.8(2) . .
C8 C7 H7 108.6 . .
C9 C8 C7 118.9(3) . .
C9 C8 C12 119.8(3) . .
C12 C8 C7 121.3(3) . .
C8 C9 H9 120.0 . .
C8 C9 C28 120.0(3) . .
C28 C9 H9 120.0 . .
C11 C10 C13 120.0(3) . .
C28 C10 C11 120.4(3) . .
C28 C10 C13 119.6(3) . .
C10 C11 H11 120.2 . .
C12 C11 C10 119.6(3) . .
C12 C11 H11 120.2 . .
C8 C12 H12 119.9 . .
C11 C12 C8 120.1(3) . .
C11 C12 H12 119.9 . .
N6 C13 C10 177.6(4) . .
C9 C28 H28 120.0 . .
C10 C28 C9 120.1(3) . .
C10 C28 H28 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C5 1.218(4) .
N1 N2 1.362(4) .
N1 C1 1.322(4) .
N2 N3 1.286(4) .
N3 N4 1.354(3) .
N4 C1 1.318(3) .
N4 C7 1.468(3) .
N5 H5 0.8600 .
N5 C1 1.354(4) .
N5 C3 1.384(4) .
N6 C13 1.126(4) .
C2 H2A 0.9600 .
C2 H2B 0.9600 .
C2 H2C 0.9600 .
C2 C3 1.502(4) .
C3 C4 1.351(4) .
C4 C5 1.483(4) .
C4 C7 1.524(4) .
C5 C6 1.491(5) .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 H7 0.9800 .
C7 C8 1.526(4) .
C8 C9 1.382(4) .
C8 C12 1.383(4) .
C9 H9 0.9300 .
C9 C28 1.385(4) .
C10 C11 1.387(5) .
C10 C13 1.454(4) .
C10 C28 1.368(5) .
C11 H11 0.9300 .
C11 C12 1.382(4) .
C12 H12 0.9300 .
C28 H28 0.9300 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5 N1 0.86 2.07 2.877(4) 156.7 3_557 yes
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 N2 N3 N4 -0.3(3) . . . .
N2 N1 C1 N4 -0.4(3) . . . .
N2 N1 C1 N5 177.4(3) . . . .
N2 N3 N4 C1 0.0(3) . . . .
N2 N3 N4 C7 -179.5(3) . . . .
N3 N4 C1 N1 0.3(3) . . . .
N3 N4 C1 N5 -177.8(3) . . . .
N3 N4 C7 C4 167.4(2) . . . .
N3 N4 C7 C8 -67.7(3) . . . .
N4 C7 C8 C9 92.0(3) . . . .
N4 C7 C8 C12 -85.1(3) . . . .
N5 C3 C4 C5 175.5(3) . . . .
N5 C3 C4 C7 -3.4(4) . . . .
C1 N1 N2 N3 0.4(4) . . . .
C1 N4 C7 C4 -12.0(4) . . . .
C1 N4 C7 C8 112.9(3) . . . .
C1 N5 C3 C2 172.1(3) . . . .
C1 N5 C3 C4 -8.7(4) . . . .
C2 C3 C4 C5 -5.4(5) . . . .
C2 C3 C4 C7 175.8(3) . . . .
C3 N5 C1 N1 -167.9(3) . . . .
C3 N5 C1 N4 9.7(4) . . . .
C3 C4 C5 O1 10.2(5) . . . .
C3 C4 C5 C6 -170.2(3) . . . .
C3 C4 C7 N4 12.4(4) . . . .
C3 C4 C7 C8 -108.6(3) . . . .
C4 C7 C8 C9 -147.6(3) . . . .
C4 C7 C8 C12 35.4(4) . . . .
C5 C4 C7 N4 -166.5(2) . . . .
C5 C4 C7 C8 72.4(3) . . . .
C7 N4 C1 N1 179.8(2) . . . .
C7 N4 C1 N5 1.7(4) . . . .
C7 C4 C5 O1 -170.8(3) . . . .
C7 C4 C5 C6 8.7(4) . . . .
C7 C8 C9 C28 -175.0(3) . . . .
C7 C8 C12 C11 175.3(3) . . . .
C8 C9 C28 C10 -0.9(5) . . . .
C9 C8 C12 C11 -1.8(5) . . . .
C10 C11 C12 C8 0.2(5) . . . .
C11 C10 C28 C9 -0.7(5) . . . .
C12 C8 C9 C28 2.1(5) . . . .
C13 C10 C11 C12 -176.6(3) . . . .
C13 C10 C28 C9 177.0(3) . . . .
C28 C10 C11 C12 1.1(5) . . . .
