#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/73/2227321.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_2227321
loop_
_publ_author_name
'Shen, Shi-De'
'Feng, Xiao-Dong'
'Yang, Wei-Hua'
'Yao, Chang-Sheng'
_publ_section_title
;
 Ethyl
 7-(4-bromophenyl)-5-trifluoromethyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
;
_journal_coeditor_code           CI5159
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2421
_journal_paper_doi               10.1107/S1600536810033842
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H11 Br F3 N5 O2'
_chemical_formula_moiety         'C14 H11 Br F3 N5 O2'
_chemical_formula_sum            'C14 H11 Br F3 N5 O2'
_chemical_formula_weight         418.19
_chemical_name_systematic
;
Ethyl 7-(4-bromophenyl)-5-trifluoromethyl-4,7-
dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
;
_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                 92.27(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.773(2)
_cell_length_b                   10.4716(11)
_cell_length_c                   7.8700(8)
_cell_measurement_reflns_used    4823
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      2.2
_cell_volume                     1545.9(3)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2002)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2002)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_sigmaI/netI    0.0609
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18785
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.713
_exptl_absorpt_correction_T_max  0.6409
_exptl_absorpt_correction_T_min  0.4772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.823
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0321P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0714
_reflns_number_gt                2547
_reflns_number_total             3681
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5159.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227321
_cod_database_fobs_code          2227321
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
Br Br1 0.468171(12) 0.24266(2) -0.00430(3) 0.02485(8) Uani d . 1 . .
F F1 0.04617(6) 0.09175(12) 0.60550(15) 0.0283(3) Uani d . 1 . .
F F2 0.00359(6) 0.18117(13) 0.37917(16) 0.0312(3) Uani d . 1 . .
F F3 0.10127(7) 0.25030(10) 0.49390(17) 0.0279(3) Uani d . 1 . .
H H1 0.0275(12) 0.055(2) 0.176(3) 0.033(7) Uiso d . 1 . .
N N1 0.06837(9) 0.02879(16) 0.1959(2) 0.0142(4) Uani d . 1 . .
N N2 0.16300(9) -0.09820(15) 0.1113(2) 0.0139(4) Uani d . 1 . .
N N3 0.17768(9) -0.17880(16) -0.0190(2) 0.0195(4) Uani d . 1 . .
N N4 0.12129(9) -0.17855(17) -0.1192(2) 0.0196(4) Uani d . 1 . .
N N5 0.06960(9) -0.09971(15) -0.0596(2) 0.0163(4) Uani d . 1 . .
O O1 0.18713(8) 0.08260(14) 0.67228(18) 0.0266(4) Uani d . 1 . .
O O2 0.27052(7) -0.04022(14) 0.55633(17) 0.0209(3) Uani d . 1 . .
C C1 0.09759(10) -0.05253(18) 0.0835(2) 0.0134(4) Uani d . 1 . .
C C2 0.21318(10) -0.06715(18) 0.2535(2) 0.0143(4) Uani d . 1 . .
H H2 0.2315 -0.1483 0.3062 0.017 Uiso calc R 1 . .
C C3 0.17113(10) 0.00649(18) 0.3842(2) 0.0147(4) Uani d . 1 . .
C C4 0.10521(11) 0.05403(18) 0.3465(2) 0.0141(4) Uani d . 1 . .
C C5 0.27570(10) 0.00933(19) 0.1898(2) 0.0143(4) Uani d . 1 . .
C C6 0.26514(11) 0.12937(19) 0.1182(3) 0.0185(5) Uani d . 1 . .
H H6 0.2184 0.1642 0.1091 0.022 Uiso calc R 1 . .
C C7 0.32231(11) 0.1991(2) 0.0599(3) 0.0187(5) Uani d . 1 . .
H H7 0.3150 0.2809 0.0097 0.022 Uiso calc R 1 . .
C C8 0.39009(11) 0.14732(19) 0.0761(2) 0.0172(5) Uani d . 1 . .
C C9 0.40180(11) 0.02870(19) 0.1482(3) 0.0196(5) Uani d . 1 . .
H H9 0.4487 -0.0054 0.1587 0.024 Uiso calc R 1 . .
C C10 0.34446(11) -0.03993(19) 0.2049(3) 0.0185(5) Uani d . 1 . .
H H10 0.3521 -0.1216 0.2548 0.022 Uiso calc R 1 . .
C C11 0.20751(11) 0.02294(19) 0.5533(3) 0.0174(4) Uani d . 1 . .
C C12 0.31205(11) -0.0374(2) 0.7163(3) 0.0251(5) Uani d . 1 . .
H H12A 0.2901 -0.0933 0.8012 0.030 Uiso calc R 1 . .
H H12B 0.3145 0.0506 0.7620 0.030 Uiso calc R 1 . .
C C13 0.38555(12) -0.0847(2) 0.6780(3) 0.0290(6) Uani d . 1 . .
H H13A 0.3820 -0.1701 0.6276 0.043 Uiso calc R 1 . .
H H13B 0.4150 -0.0884 0.7835 0.043 Uiso calc R 1 . .
H H13C 0.4074 -0.0262 0.5979 0.043 Uiso calc R 1 . .
C C14 0.06429(11) 0.1435(2) 0.4593(3) 0.0205(5) Uani 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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 C4 . . 118.68(17) ?
C1 N1 H1 . . 119.1(17) ?
C4 N1 H1 . . 121.9(16) ?
C1 N2 N3 . . 108.16(16) ?
C1 N2 C2 . . 127.32(16) ?
N3 N2 C2 . . 124.50(16) ?
N4 N3 N2 . . 105.79(16) ?
N3 N4 N5 . . 111.43(16) ?
C1 N5 N4 . . 104.74(16) ?
C11 O2 C12 . . 116.29(15) ?
N5 C1 N2 . . 109.88(17) ?
N5 C1 N1 . . 129.27(18) ?
N2 C1 N1 . . 120.84(18) ?
N2 C2 C5 . . 110.17(15) ?
N2 C2 C3 . . 106.92(15) ?
C5 C2 C3 . . 112.42(16) ?
N2 C2 H2 . . 109.1 ?
C5 C2 H2 . . 109.1 ?
C3 C2 H2 . . 109.1 ?
C4 C3 C11 . . 122.55(18) ?
C4 C3 C2 . . 121.92(18) ?
C11 C3 C2 . . 115.53(17) ?
C3 C4 N1 . . 122.81(17) ?
C3 C4 C14 . . 125.21(18) ?
N1 C4 C14 . . 111.95(17) ?
C6 C5 C10 . . 119.19(18) ?
C6 C5 C2 . . 120.69(18) ?
C10 C5 C2 . . 120.11(18) ?
C5 C6 C7 . . 120.64(19) ?
C5 C6 H6 . . 119.7 ?
C7 C6 H6 . . 119.7 ?
C8 C7 C6 . . 118.80(19) ?
C8 C7 H7 . . 120.6 ?
C6 C7 H7 . . 120.6 ?
C9 C8 C7 . . 121.45(19) ?
C9 C8 Br1 . . 119.80(15) ?
C7 C8 Br1 . . 118.75(15) ?
C8 C9 C10 . . 119.16(19) ?
C8 C9 H9 . . 120.4 ?
C10 C9 H9 . . 120.4 ?
C9 C10 C5 . . 120.74(19) ?
C9 C10 H10 . . 119.6 ?
C5 C10 H10 . . 119.6 ?
O1 C11 O2 . . 123.05(19) ?
O1 C11 C3 . . 127.68(19) ?
O2 C11 C3 . . 109.27(17) ?
O2 C12 C13 . . 106.47(17) ?
O2 C12 H12A . . 110.4 ?
C13 C12 H12A . . 110.4 ?
O2 C12 H12B . . 110.4 ?
C13 C12 H12B . . 110.4 ?
H12A C12 H12B . . 108.6 ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
F1 C14 F3 . . 108.26(17) ?
F1 C14 F2 . . 106.58(17) ?
F3 C14 F2 . . 105.95(17) ?
F1 C14 C4 . . 114.01(17) ?
F3 C14 C4 . . 111.34(17) ?
F2 C14 C4 . . 110.28(17) ?
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
Br1 C8 . 1.9025(19) ?
F1 C14 . 1.328(2) ?
F2 C14 . 1.340(2) ?
F3 C14 . 1.338(2) ?
N1 C1 . 1.359(2) ?
N1 C4 . 1.374(3) ?
N1 H1 . 0.83(2) ?
N2 C1 . 1.328(2) ?
N2 N3 . 1.365(2) ?
N2 C2 . 1.470(2) ?
N3 N4 . 1.295(2) ?
N4 N5 . 1.371(2) ?
N5 C1 . 1.320(2) ?
O1 C11 . 1.201(2) ?
O2 C11 . 1.355(2) ?
O2 C12 . 1.455(2) ?
C2 C5 . 1.522(2) ?
C2 C3 . 1.530(3) ?
C2 H2 . 1.00 ?
C3 C4 . 1.356(3) ?
C3 C11 . 1.482(3) ?
C4 C14 . 1.520(3) ?
C5 C6 . 1.388(3) ?
C5 C10 . 1.391(3) ?
C6 C7 . 1.392(3) ?
C6 H6 . 0.95 ?
C7 C8 . 1.385(3) ?
C7 H7 . 0.95 ?
C8 C9 . 1.379(3) ?
C9 C10 . 1.383(3) ?
C9 H9 . 0.95 ?
C10 H10 . 0.95 ?
C12 C13 . 1.508(3) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
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
N1 H1 N5 3 0.83(2) 2.06(2) 2.862(2) 163(2)
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 N2 N3 N4 . . . . 0.1(2) ?
C2 N2 N3 N4 . . . . -178.49(17) ?
N2 N3 N4 N5 . . . . 0.2(2) ?
N3 N4 N5 C1 . . . . -0.4(2) ?
N4 N5 C1 N2 . . . . 0.4(2) ?
N4 N5 C1 N1 . . . . -178.44(19) ?
N3 N2 C1 N5 . . . . -0.3(2) ?
C2 N2 C1 N5 . . . . 178.17(17) ?
N3 N2 C1 N1 . . . . 178.65(16) ?
C2 N2 C1 N1 . . . . -2.8(3) ?
C4 N1 C1 N5 . . . . 172.99(19) ?
C4 N1 C1 N2 . . . . -5.8(3) ?
C1 N2 C2 C5 . . . . -111.0(2) ?
N3 N2 C2 C5 . . . . 67.3(2) ?
C1 N2 C2 C3 . . . . 11.5(2) ?
N3 N2 C2 C3 . . . . -170.26(16) ?
N2 C2 C3 C4 . . . . -13.1(2) ?
C5 C2 C3 C4 . . . . 108.0(2) ?
N2 C2 C3 C11 . . . . 167.39(16) ?
C5 C2 C3 C11 . . . . -71.6(2) ?
C11 C3 C4 N1 . . . . -173.55(17) ?
C2 C3 C4 N1 . . . . 6.9(3) ?
C11 C3 C4 C14 . . . . 8.6(3) ?
C2 C3 C4 C14 . . . . -170.92(18) ?
C1 N1 C4 C3 . . . . 3.5(3) ?
C1 N1 C4 C14 . . . . -178.41(17) ?
N2 C2 C5 C6 . . . . 63.4(2) ?
C3 C2 C5 C6 . . . . -55.7(2) ?
N2 C2 C5 C10 . . . . -117.49(19) ?
C3 C2 C5 C10 . . . . 123.4(2) ?
C10 C5 C6 C7 . . . . 1.0(3) ?
C2 C5 C6 C7 . . . . -179.92(18) ?
C5 C6 C7 C8 . . . . -0.7(3) ?
C6 C7 C8 C9 . . . . 0.2(3) ?
C6 C7 C8 Br1 . . . . 179.84(15) ?
C7 C8 C9 C10 . . . . 0.2(3) ?
Br1 C8 C9 C10 . . . . -179.52(15) ?
C8 C9 C10 C5 . . . . 0.1(3) ?
C6 C5 C10 C9 . . . . -0.7(3) ?
C2 C5 C10 C9 . . . . -179.76(18) ?
C12 O2 C11 O1 . . . . 2.7(3) ?
C12 O2 C11 C3 . . . . -177.93(16) ?
C4 C3 C11 O1 . . . . -4.0(3) ?
C2 C3 C11 O1 . . . . 175.58(19) ?
C4 C3 C11 O2 . . . . 176.71(17) ?
C2 C3 C11 O2 . . . . -3.7(2) ?
C11 O2 C12 C13 . . . . -166.71(17) ?
C3 C4 C14 F1 . . . . -65.4(3) ?
N1 C4 C14 F1 . . . . 116.58(19) ?
C3 C4 C14 F3 . . . . 57.5(3) ?
N1 C4 C14 F3 . . . . -120.58(19) ?
C3 C4 C14 F2 . . . . 174.78(18) ?
N1 C4 C14 F2 . . . . -3.3(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4813751
