#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/94/2209488.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_2209488
loop_
_publ_author_name
'Zhou, Hua'
'Hu, Ning-Hai'
'Li, Zhi-Gang'
'Dou, Yan-Li'
'Xu, Jing-Wei'
_publ_section_title
;
 Methyclothiazide: a hydrogen-bonded layer structure
;
_journal_coeditor_code           EZ2002
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3009
_journal_page_last               o3010
_journal_paper_doi               10.1107/S1600536806016977
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C9 H11 Cl2 N3 O4 S2'
_chemical_formula_moiety         'C9 H11 Cl2 N3 O4 S2'
_chemical_formula_sum            'C9 H11 Cl2 N3 O4 S2'
_chemical_formula_weight         360.23
_chemical_name_common            methyclothiazide
_chemical_name_systematic
;
6-chloro-3-chloromethyl-3,4-dihydro-2-methyl-7-sulfamoyl-1,2,4-benzo-
thiadiazine 1,1-dioxide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.5251(5)
_cell_length_b                   15.4476(8)
_cell_length_c                   19.3226(11)
_cell_measurement_reflns_used    8375
_cell_measurement_temperature    187(2)
_cell_measurement_theta_max      26.01
_cell_measurement_theta_min      2.64
_cell_volume                     2843.1(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      187.0(10)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.021
_diffrn_reflns_av_sigmaI/netI    0.015
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14885
_diffrn_reflns_theta_full        26.0
_diffrn_reflns_theta_max         26.0
_diffrn_reflns_theta_min         2.6
_exptl_absorpt_coefficient_mu    0.765
_exptl_absorpt_correction_T_max  0.8491
_exptl_absorpt_correction_T_min  0.7464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SAINT; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.62
_refine_diff_density_min         -0.52
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2794
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.09
_refine_ls_R_factor_all          0.037
_refine_ls_R_factor_gt           0.035
_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)+(0.0457P)²+2.8362P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.091
_refine_ls_wR_factor_ref         0.092
_reflns_number_gt                2624
_reflns_number_total             2794
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ez2002.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 2ac 2ab '
_cod_database_code               2209488
_cod_database_fobs_code          2209488
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
C C1 0.7656(2) 0.82837(12) 0.38950(10) 0.0197(4) Uani d . 1
C C2 0.7237(2) 0.74982(13) 0.41979(10) 0.0196(4) Uani d . 1
C C3 0.8117(2) 0.67988(13) 0.42417(10) 0.0211(4) Uani d . 1
H H3 0.7788 0.6272 0.4437 0.025 Uiso calc R 1
C C4 0.9510(2) 0.68579(13) 0.39979(10) 0.0192(4) Uani d . 1
C C5 0.9928(2) 0.76498(13) 0.36990(10) 0.0196(4) Uani d . 1
C C6 0.9009(2) 0.83446(13) 0.36407(10) 0.0212(4) Uani d . 1
H H6 0.9313 0.8865 0.3425 0.025 Uiso calc R 1
C C7 1.1880(2) 0.62354(14) 0.39110(12) 0.0281(5) Uani d . 1
H H7 1.2332 0.6535 0.4312 0.034 Uiso calc R 1
C C8 1.2479(3) 0.53292(15) 0.38511(16) 0.0399(6) Uani d . 1
H H8A 1.2049 0.5028 0.3451 0.048 Uiso calc R 1
H H8B 1.2257 0.4995 0.4275 0.048 Uiso calc R 1
C C9 1.1568(3) 0.63932(19) 0.26241(14) 0.0495(7) Uani d . 1
H H9A 1.2091 0.5868 0.2505 0.074 Uiso calc R 1
H H9B 1.1673 0.6820 0.2253 0.074 Uiso calc R 1
H H9C 1.0572 0.6251 0.2681 0.074 Uiso calc R 1
Cl Cl1 0.55442(5) 0.73820(3) 0.45138(3) 0.02725(15) Uani d . 1
Cl Cl2 1.43385(7) 0.53842(4) 0.37383(5) 0.0560(2) Uani d . 1
N N1 0.51817(19) 0.89465(12) 0.33766(10) 0.0281(4) Uani d . 1
H H1A 0.5387 0.8769 0.2931 0.034 Uiso d . 1
H H1B 0.4554 0.8620 0.3606 0.034 Uiso d . 1
N N2 1.2120(2) 0.67555(12) 0.32766(10) 0.0289(4) Uani d . 1
N N3 1.03804(18) 0.61601(11) 0.40418(9) 0.0240(4) Uani d . 1
H H3A 1.0086 0.5697 0.4275 0.029 Uiso d . 1
O O1 0.73376(16) 0.98181(10) 0.34085(8) 0.0311(4) Uani d . 1
O O2 0.60838(18) 0.94607(10) 0.44876(8) 0.0323(4) Uani d . 1
O O3 1.17323(17) 0.82416(11) 0.27971(9) 0.0355(4) Uani d . 1
O O4 1.25153(16) 0.80704(10) 0.39927(8) 0.0302(4) Uani d . 1
S S1 0.65637(5) 0.92061(3) 0.38113(3) 0.02248(14) Uani d . 1
S S2 1.16733(5) 0.77609(3) 0.34291(3) 0.02285(14) 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'
S S 0.1246 0.1234 '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
C6 C1 C2 118.11(18)
C6 C1 S1 117.40(15)
C2 C1 S1 124.49(15)
C3 C2 C1 122.23(18)
C3 C2 Cl1 117.76(15)
C1 C2 Cl1 120.00(15)
C2 C3 C4 120.24(18)
C2 C3 H3 119.9
C4 C3 H3 119.9
N3 C4 C3 120.02(18)
N3 C4 C5 122.65(18)
C3 C4 C5 117.31(18)
C6 C5 C4 121.67(18)
C6 C5 S2 119.88(15)
C4 C5 S2 118.40(15)
C1 C6 C5 120.40(18)
C1 C6 H6 119.8
C5 C6 H6 119.8
N3 C7 N2 109.75(17)
N3 C7 C8 107.97(18)
N2 C7 C8 112.3(2)
N3 C7 H7 108.9
N2 C7 H7 108.9
C8 C7 H7 108.9
C7 C8 Cl2 109.76(17)
C7 C8 H8A 109.7
Cl2 C8 H8A 109.7
C7 C8 H8B 109.7
Cl2 C8 H8B 109.7
H8A C8 H8B 108.2
N2 C9 H9A 109.5
N2 C9 H9B 109.5
H9A C9 H9B 109.5
N2 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
S1 N1 H1A 112.7
S1 N1 H1B 115.2
H1A N1 H1B 115.7
C9 N2 C7 116.5(2)
C9 N2 S2 114.87(17)
C7 N2 S2 108.97(14)
C4 N3 C7 121.56(17)
C4 N3 H3A 118.4
C7 N3 H3A 117.5
O1 S1 O2 118.52(10)
O1 S1 N1 107.58(10)
O2 S1 N1 106.36(10)
O1 S1 C1 106.20(9)
O2 S1 C1 108.87(9)
N1 S1 C1 109.08(10)
O3 S2 O4 116.95(10)
O3 S2 N2 109.19(10)
O4 S2 N2 107.91(10)
O3 S2 C5 110.03(10)
O4 S2 C5 109.72(9)
N2 S2 C5 101.97(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.383(3)
C1 C2 1.405(3)
C1 S1 1.771(2)
C2 C3 1.370(3)
C2 Cl1 1.7334(19)
C3 C4 1.411(3)
C3 H3 0.9500
C4 N3 1.363(3)
C4 C5 1.410(3)
C5 C6 1.390(3)
C5 S2 1.750(2)
C6 H6 0.9500
C7 N3 1.456(3)
C7 N2 1.483(3)
C7 C8 1.516(3)
C7 H7 1.0000
C8 Cl2 1.787(3)
C8 H8A 0.9900
C8 H8B 0.9900
C9 N2 1.477(3)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
N1 S1 1.6122(19)
N1 H1A 0.9246
N1 H1B 0.8990
N2 S2 1.6370(19)
N3 H3A 0.8907
O1 S1 1.4293(16)
O2 S1 1.4394(16)
O3 S2 1.4305(16)
O4 S2 1.4346(16)
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
N1 H1A O3 6_556 0.92 2.07 2.917(2) 152 y
N1 H1B O4 1_455 0.90 2.25 3.114(2) 162 y
N3 H3A O2 8_755 0.89 2.25 3.095(2) 158 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3978
