#------------------------------------------------------------------------------
#$Date: 2018-08-15 05:23:53 +0300 (Wed, 15 Aug 2018) $
#$Revision: 209717 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/97/1549793.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1549793
loop_
_publ_author_name
'El-Hiti, Gamal A.'
'Abdel-Wahab, Bakr F.'
'Alotaibi, Mohammad Hayal'
'Yousif, Emad'
'Hegazy, Amany S.'
'Kariuki, Benson M.'
_publ_section_title
;
 Sodium 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate
;
_journal_coeditor_code           HB4252
_journal_issue                   8
_journal_name_full               IUCrData
_journal_page_first              x181127
_journal_paper_doi               10.1107/S2414314618011276
_journal_volume                  3
_journal_year                    2018
_chemical_formula_iupac          'Na +, C10 H7 Cl N3 O2 -'
_chemical_formula_moiety         'Na +, C10 H7 Cl N3 O2 -'
_chemical_formula_sum            'C10 H7 Cl N3 Na O2'
_chemical_formula_weight         259.63
_chemical_name_systematic
;
Sodium 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate
;
_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'
_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
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 92.711(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6462(8)
_cell_length_b                   6.3754(4)
_cell_length_c                   14.7003(9)
_cell_measurement_reflns_used    2649
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2160
_cell_measurement_theta_min      3.4650
_cell_volume                     1090.26(12)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and WinGX (Farrugia, 2012)
;
_computing_publication_material
;
ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and
CHEMDRAW Ultra (Cambridge Soft, 2001)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measurement_device_type
'Rigaku OD SuperNova Dual source diffractometer with an Atlas detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8333
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.667
_diffrn_reflns_theta_min         3.210
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.381
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.467
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.401
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0445
_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)+(0.0446P)²+0.2829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1152
_reflns_number_gt                1875
_reflns_number_total             2665
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4252sup1.cif
_cod_data_source_block           I
_cod_database_code               1549793
_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_min   0.856
_shelx_estimated_absorpt_t_max   0.972
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_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_occupancy
C C1 0.08988(16) 0.5137(3) 0.64261(13) 0.0306(4) Uani d 1
C C2 0.12619(15) 0.6087(3) 0.55520(12) 0.0277(4) Uani d 1
C C3 0.19398(17) 0.5260(3) 0.48997(13) 0.0304(4) Uani d 1
C C4 0.2601(2) 0.3285(3) 0.48670(17) 0.0597(8) Uani d 1
H H4A 0.209664 0.215967 0.467891 0.090 Uiso calc 1
H H4B 0.294116 0.298547 0.546045 0.090 Uiso calc 1
H H4C 0.319562 0.342836 0.444051 0.090 Uiso calc 1
C C5 0.25655(16) 0.6837(3) 0.34347(13) 0.0302(4) Uani d 1
C C6 0.24624(18) 0.5191(3) 0.28293(14) 0.0378(5) Uani d 1
H H6 0.201366 0.403343 0.296042 0.045 Uiso calc 1
C C7 0.30294(19) 0.5273(4) 0.20265(14) 0.0448(6) Uani d 1
H H7 0.297119 0.416527 0.161513 0.054 Uiso calc 1
C C8 0.36800(18) 0.7002(4) 0.18405(14) 0.0421(5) Uani d 1
C C9 0.3785(2) 0.8660(4) 0.24377(15) 0.0481(6) Uani d 1
H H9 0.422407 0.982653 0.230039 0.058 Uiso calc 1
C C10 0.32262(19) 0.8562(3) 0.32453(15) 0.0429(5) Uani d 1
H H10 0.329600 0.965933 0.366091 0.052 Uiso calc 1
N N1 0.09199(14) 0.8041(2) 0.52889(11) 0.0337(4) Uani d 1
N N2 0.13405(15) 0.8474(2) 0.45008(11) 0.0355(4) Uani d 1
N N3 0.19683(13) 0.6783(2) 0.42611(10) 0.0292(4) Uani d 1
O O1 0.11449(14) 0.3261(2) 0.65583(10) 0.0469(4) Uani d 1
O O2 0.03699(12) 0.6316(2) 0.69418(9) 0.0406(4) Uani d 1
Cl Cl1 0.43802(6) 0.70889(13) 0.08201(4) 0.0687(3) Uani d 1
Na Na1 -0.01461(7) 0.49886(11) 0.83416(5) 0.0360(2) 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 '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
O1 C1 O2 . . 126.89(17)
O1 C1 C2 . . 116.76(16)
O2 C1 C2 . . 116.34(16)
O1 C1 Na1 . . 85.80(11)
O2 C1 Na1 . . 41.15(9)
C2 C1 Na1 . . 157.39(12)
N1 C2 C3 . . 108.84(15)
N1 C2 C1 . . 121.58(15)
C3 C2 C1 . . 129.59(17)
N3 C3 C2 . . 104.06(15)
N3 C3 C4 . . 124.00(16)
C2 C3 C4 . . 131.76(18)
C3 C4 H4A . . 109.5
C3 C4 H4B . . 109.5
H4A C4 H4B . . 109.5
C3 C4 H4C . . 109.5
H4A C4 H4C . . 109.5
H4B C4 H4C . . 109.5
C6 C5 C10 . . 120.64(17)
C6 C5 N3 . . 120.01(16)
C10 C5 N3 . . 119.33(16)
C5 C6 C7 . . 119.56(18)
C5 C6 H6 . . 120.2
C7 C6 H6 . . 120.2
C8 C7 C6 . . 119.43(19)
C8 C7 H7 . . 120.3
C6 C7 H7 . . 120.3
C7 C8 C9 . . 121.55(18)
C7 C8 Cl1 . . 118.84(17)
C9 C8 Cl1 . . 119.61(17)
C8 C9 C10 . . 118.82(19)
C8 C9 H9 . . 120.6
C10 C9 H9 . . 120.6
C5 C10 C9 . . 119.99(19)
C5 C10 H10 . . 120.0
C9 C10 H10 . . 120.0
N2 N1 C2 . . 109.17(14)
N2 N1 Na1 . 2_556 138.87(11)
C2 N1 Na1 . 2_556 109.24(11)
N1 N2 N3 . . 106.93(14)
N1 N2 Na1 . 4_575 113.55(12)
N3 N2 Na1 . 4_575 119.04(12)
C3 N3 N2 . . 111.00(14)
C3 N3 C5 . . 129.55(15)
N2 N3 C5 . . 119.42(14)
C1 O1 Na1 . 2_546 137.58(14)
C1 O2 Na1 . . 118.17(12)
C1 O2 Na1 . 2_556 122.42(11)
Na1 O2 Na1 . 2_556 118.64(6)
O2 Na1 O2 . 2_546 103.44(4)
O2 Na1 O1 . 2_556 83.35(5)
O2 Na1 O1 2_546 2_556 144.50(7)
O2 Na1 N1 . 2_546 169.72(6)
O2 Na1 N1 2_546 2_546 67.86(5)
O1 Na1 N1 2_556 2_546 100.58(5)
O2 Na1 N2 . 4_576 104.69(6)
O2 Na1 N2 2_546 4_576 123.69(6)
O1 Na1 N2 2_556 4_576 86.61(6)
N1 Na1 N2 2_546 4_576 85.11(5)
O2 Na1 C1 . . 20.68(5)
O2 Na1 C1 2_546 . 85.20(5)
O1 Na1 C1 2_556 . 103.90(5)
N1 Na1 C1 2_546 . 152.77(5)
N2 Na1 C1 4_576 . 107.94(5)
O2 Na1 Na1 . 2_546 73.40(4)
O2 Na1 Na1 2_546 2_546 30.25(3)
O1 Na1 Na1 2_556 2_546 140.89(6)
N1 Na1 Na1 2_546 2_546 98.11(4)
N2 Na1 Na1 4_576 2_546 129.16(5)
C1 Na1 Na1 . 2_546 55.00(4)
O2 Na1 Na1 . 2_556 31.12(4)
O2 Na1 Na1 2_546 2_556 132.42(5)
O1 Na1 Na1 2_556 2_556 53.76(3)
N1 Na1 Na1 2_546 2_556 154.32(4)
N2 Na1 Na1 4_576 2_556 91.80(4)
C1 Na1 Na1 . 2_556 51.60(4)
Na1 Na1 Na1 2_546 2_556 103.49(3)
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
Na1 N1 2_546 2.5649(16) y
Na1 N2 4_576 2.5658(19) y
Na1 O1 2_556 2.3964(16) y
Na1 O2 . 2.3299(14) y
Na1 O2 2_546 2.3902(15) y
Na1 Na1 2_546 4.0595(9) ?
Na1 Na1 2_556 4.0595(9) ?
C1 O1 . 1.243(2) ?
C1 O2 . 1.250(2) ?
C1 C2 . 1.499(2) ?
C2 N1 . 1.359(2) ?
C2 C3 . 1.375(2) ?
C3 N3 . 1.352(2) ?
C3 C4 . 1.478(3) ?
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
C5 C6 . 1.377(3) ?
C5 C10 . 1.378(3) ?
C5 N3 . 1.429(2) ?
C6 C7 . 1.380(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.373(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.376(3) ?
C8 Cl1 . 1.742(2) ?
C9 C10 . 1.382(3) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
N1 N2 . 1.308(2) ?
N2 N3 . 1.358(2) ?
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
C4 H4A N2 1_545 0.96 2.52 3.432(3) 159 yes

_cod_database_fobs_code 1549793
