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#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/83/2228356.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_2228356
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Yeap, Chin Sing'
'Gowda, J.'
'Khader, A. M. A.'
'Kalluraya, Balakrishna'
_publ_section_title
;
 8-Chloro-5,5-dimethyl-5,6-dihydrotetrazolo[1,5-c]quinazoline
;
_journal_coeditor_code           HB5733
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3219
_journal_paper_doi               10.1107/S160053681004688X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C10 H10 Cl N5'
_chemical_formula_moiety         'C10 H10 Cl N5'
_chemical_formula_sum            'C10 H10 Cl N5'
_chemical_formula_weight         235.68
_chemical_name_systematic
;
8-Chloro-5,5-dimethyl-5,6-dihydrotetrazolo[1,5-c]quinazoline
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 130.823(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8324(16)
_cell_length_b                   21.532(5)
_cell_length_c                   9.4337(16)
_cell_measurement_reflns_used    1888
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.90
_cell_measurement_theta_min      3.01
_cell_volume                     1050.2(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9660
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_correction_T_min  0.9477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.308
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2412
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0533
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0361P)²+1.9098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1374
_reflns_number_gt                1777
_reflns_number_total             2412
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb5733.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228356
_cod_database_fobs_code          2228356
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.68351(15) 0.62515(4) 0.46138(11) 0.0285(2) Uani d . 1 . .
N N1 0.0252(5) 0.85800(13) -0.2050(3) 0.0225(6) Uani d . 1 . .
N N2 0.0079(5) 0.92121(14) -0.2261(3) 0.0276(6) Uani d . 1 . .
N N3 0.1672(5) 0.94937(13) -0.0661(3) 0.0248(6) Uani d . 1 . .
N N4 0.2938(4) 0.90385(12) 0.0634(3) 0.0192(5) Uani d . 1 . .
N N5 0.6368(5) 0.85848(12) 0.3484(3) 0.0210(6) Uani d . 1 . .
C C1 0.2056(5) 0.84885(14) -0.0218(4) 0.0190(6) Uani d . 1 . .
C C2 0.3106(5) 0.79248(14) 0.0880(4) 0.0185(6) Uani d . 1 . .
C C3 0.2129(6) 0.73316(15) 0.0145(4) 0.0216(7) Uani d . 1 . .
H H3A 0.0704 0.7285 -0.1122 0.026 Uiso calc R 1 . .
C C4 0.3259(6) 0.68153(15) 0.1280(4) 0.0234(7) Uani d . 1 . .
H H4A 0.2613 0.6420 0.0797 0.028 Uiso calc R 1 . .
C C5 0.5397(6) 0.69013(15) 0.3174(4) 0.0213(6) Uani d . 1 . .
C C6 0.6402(6) 0.74777(15) 0.3947(4) 0.0209(6) Uani d . 1 . .
H H6A 0.7816 0.7518 0.5218 0.025 Uiso calc R 1 . .
C C7 0.5276(5) 0.80012(14) 0.2800(4) 0.0176(6) Uani d . 1 . .
C C8 0.4845(5) 0.91539(14) 0.2689(4) 0.0189(6) Uani d . 1 . .
C C9 0.6573(6) 0.96910(15) 0.3100(4) 0.0271(7) Uani d . 1 . .
H H9A 0.7358 0.9608 0.2569 0.041 Uiso calc R 1 . .
H H9B 0.7896 0.9742 0.4431 0.041 Uiso calc R 1 . .
H H9C 0.5561 1.0064 0.2561 0.041 Uiso calc R 1 . .
C C10 0.3352(6) 0.92761(16) 0.3348(4) 0.0254(7) Uani d . 1 . .
H H10A 0.2294 0.8923 0.3065 0.038 Uiso calc R 1 . .
H H10B 0.2275 0.9635 0.2718 0.038 Uiso calc R 1 . .
H H10C 0.4549 0.9347 0.4675 0.038 Uiso calc R 1 . .
H H1N5 0.751(8) 0.8595(18) 0.467(6) 0.039(11) Uiso d . 1 . .
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 N2 . . 104.8(2) ?
N3 N2 N1 . . 111.6(2) ?
N2 N3 N4 . . 105.5(3) ?
C1 N4 N3 . . 109.3(2) ?
C1 N4 C8 . . 126.8(2) ?
N3 N4 C8 . . 123.7(2) ?
C7 N5 C8 . . 122.4(2) ?
C7 N5 H1N5 . . 113(3) ?
C8 N5 H1N5 . . 113(3) ?
N1 C1 N4 . . 108.8(3) ?
N1 C1 C2 . . 131.4(3) ?
N4 C1 C2 . . 119.8(2) ?
C3 C2 C7 . . 120.2(3) ?
C3 C2 C1 . . 124.0(3) ?
C7 C2 C1 . . 115.7(3) ?
C4 C3 C2 . . 120.6(3) ?
C4 C3 H3A . . 119.7 ?
C2 C3 H3A . . 119.7 ?
C3 C4 C5 . . 118.3(3) ?
C3 C4 H4A . . 120.9 ?
C5 C4 H4A . . 120.9 ?
C6 C5 C4 . . 122.7(3) ?
C6 C5 Cl1 . . 118.8(2) ?
C4 C5 Cl1 . . 118.5(2) ?
C5 C6 C7 . . 119.2(3) ?
C5 C6 H6A . . 120.4 ?
C7 C6 H6A . . 120.4 ?
N5 C7 C6 . . 121.0(3) ?
N5 C7 C2 . . 119.8(3) ?
C6 C7 C2 . . 119.0(3) ?
N5 C8 N4 . . 104.6(2) ?
N5 C8 C9 . . 109.6(2) ?
N4 C8 C9 . . 109.5(2) ?
N5 C8 C10 . . 112.2(2) ?
N4 C8 C10 . . 108.1(2) ?
C9 C8 C10 . . 112.4(3) ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C8 C10 H10A . . 109.5 ?
C8 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C8 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
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
Cl1 C5 . 1.739(3) ?
N1 C1 . 1.326(4) ?
N1 N2 . 1.369(4) ?
N2 N3 . 1.297(4) ?
N3 N4 . 1.349(3) ?
N4 C1 . 1.334(4) ?
N4 C8 . 1.489(3) ?
N5 C7 . 1.386(4) ?
N5 C8 . 1.458(4) ?
N5 H1N5 . 0.85(4) ?
C1 C2 . 1.445(4) ?
C2 C3 . 1.397(4) ?
C2 C7 . 1.413(4) ?
C3 C4 . 1.378(4) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.396(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.374(4) ?
C6 C7 . 1.394(4) ?
C6 H6A . 0.9300 ?
C8 C9 . 1.511(4) ?
C8 C10 . 1.525(4) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
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
N5 H1N5 N1 1_656 0.85(4) 2.35(4) 3.190(3) 173(6) yes
N5 H1N5 N2 1_656 0.85(4) 2.57(4) 3.326(3) 150(4) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 N2 N3 . . . . -0.1(3) ?
N1 N2 N3 N4 . . . . 0.4(3) ?
N2 N3 N4 C1 . . . . -0.7(3) ?
N2 N3 N4 C8 . . . . -175.8(2) ?
N2 N1 C1 N4 . . . . -0.3(3) ?
N2 N1 C1 C2 . . . . 179.9(3) ?
N3 N4 C1 N1 . . . . 0.6(3) ?
C8 N4 C1 N1 . . . . 175.6(2) ?
N3 N4 C1 C2 . . . . -179.6(2) ?
C8 N4 C1 C2 . . . . -4.6(4) ?
N1 C1 C2 C3 . . . . -7.2(5) ?
N4 C1 C2 C3 . . . . 173.0(3) ?
N1 C1 C2 C7 . . . . 171.7(3) ?
N4 C1 C2 C7 . . . . -8.0(4) ?
C7 C2 C3 C4 . . . . 0.2(4) ?
C1 C2 C3 C4 . . . . 179.2(3) ?
C2 C3 C4 C5 . . . . -0.1(4) ?
C3 C4 C5 C6 . . . . 0.4(4) ?
C3 C4 C5 Cl1 . . . . -179.9(2) ?
C4 C5 C6 C7 . . . . -0.8(4) ?
Cl1 C5 C6 C7 . . . . 179.5(2) ?
C8 N5 C7 C6 . . . . -153.7(3) ?
C8 N5 C7 C2 . . . . 31.3(4) ?
C5 C6 C7 N5 . . . . -174.1(3) ?
C5 C6 C7 C2 . . . . 1.0(4) ?
C3 C2 C7 N5 . . . . 174.4(3) ?
C1 C2 C7 N5 . . . . -4.6(4) ?
C3 C2 C7 C6 . . . . -0.7(4) ?
C1 C2 C7 C6 . . . . -179.7(2) ?
C7 N5 C8 N4 . . . . -38.5(3) ?
C7 N5 C8 C9 . . . . -155.9(3) ?
C7 N5 C8 C10 . . . . 78.4(3) ?
C1 N4 C8 N5 . . . . 25.7(4) ?
N3 N4 C8 N5 . . . . -159.9(2) ?
C1 N4 C8 C9 . . . . 143.2(3) ?
N3 N4 C8 C9 . . . . -42.5(4) ?
C1 N4 C8 C10 . . . . -94.0(3) ?
N3 N4 C8 C10 . . . . 80.3(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656354
