#------------------------------------------------------------------------------
#$Date: 2017-03-05 06:59:13 +0200 (Sun, 05 Mar 2017) $
#$Revision: 193758 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/73/7227371.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_7227371
loop_
_publ_author_name
'Suresh, Kuthuru'
'Khandavilli, U. B. Rao'
'Gunnam, Anilkumar'
'Nangia, Ashwini'
_publ_section_title
;
 Polymorphism, isostructurality and physicochemical properties of
 glibenclamide salts
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              918
_journal_paper_doi               10.1039/C6CE02295B
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C23 H27 Cl N3 Na O6 S'
_chemical_formula_sum            'C23 H27 Cl N3 Na O6 S'
_chemical_formula_weight         531.97
_chemical_name_common            'Glibenclamide-sodiumhydrate salt'
_chemical_name_systematic
; 
 5-chloro-N-(4-[N-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-2-methoxybenzamide-sodium-hydrate 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-11-01 deposited with the CCDC.
2017-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.746(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.5991(16)
_cell_length_b                   5.8086(3)
_cell_length_c                   23.4722(17)
_cell_measurement_reflns_used    3202
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      69.2630
_cell_measurement_theta_min      3.5880
_cell_volume                     2530.4(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0756
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20762
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.221
_diffrn_reflns_theta_min         3.559
_exptl_absorpt_coefficient_mu    2.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1112
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol+Water'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.973
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4906
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0844
_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)+(0.1643P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2244
_refine_ls_wR_factor_ref         0.2750
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3105
_reflns_number_total             4906
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce02295b2.cif
_cod_data_source_block           GBA-Na-Form-III
_cod_depositor_comments
'Adding full bibliography for 7227370--7227375.cif.'
_cod_database_code               7227371
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
S1 S 0.60730(6) 0.13635(17) 0.05166(5) 0.0469(3) Uani 1 1 d . .
Cl1 Cl 1.06964(9) 1.4510(3) 0.10704(8) 0.0890(5) Uani 1 1 d . .
Na1 Na 0.57019(10) -0.3383(3) -0.01878(9) 0.0573(5) Uani 1 1 d . .
O4 O 0.55811(16) 0.3282(5) 0.03750(15) 0.0527(7) Uani 1 1 d . .
O5 O 0.66286(19) 0.4100(6) -0.02590(17) 0.0627(9) Uani 1 1 d . .
O3 O 0.58206(19) -0.0608(6) 0.07575(16) 0.0617(9) Uani 1 1 d . .
C10 C 0.8031(2) 0.3717(8) 0.20616(19) 0.0500(10) Uani 1 1 d . .
C13 C 0.6853(2) 0.2366(7) 0.10931(19) 0.0453(9) Uani 1 1 d . .
O2 O 0.8657(2) 0.6963(7) 0.08755(17) 0.0801(12) Uani 1 1 d . .
C11 C 0.7451(3) 0.5154(8) 0.1836(2) 0.0579(11) Uani 1 1 d . .
H11 H 0.7456 0.6602 0.2006 0.069 Uiso 1 1 calc R U
C2 C 1.0123(3) 1.0955(8) 0.1501(2) 0.0577(11) Uani 1 1 d . .
H2 H 1.0466 1.1284 0.1870 0.069 Uiso 1 1 calc R U
O1 O 1.0071(3) 0.8754(8) 0.25184(17) 0.0903(14) Uani 1 1 d . .
N2 N 0.6295(2) 0.0451(6) -0.00285(17) 0.0543(9) Uani 1 1 d . .
N1 N 0.9389(3) 0.5884(8) 0.1999(2) 0.0701(12) Uani 1 1 d . .
H1A H 0.9165 0.5377 0.1643 0.084 Uiso 1 1 calc R U
C3 C 0.9643(2) 0.9148(9) 0.1458(2) 0.0539(11) Uani 1 1 d . .
C15 C 0.8023(2) 0.1588(9) 0.1788(2) 0.0600(12) Uani 1 1 d . .
H15 H 0.8414 0.0599 0.1932 0.072 Uiso 1 1 calc R U
N3 N 0.6617(3) 0.1111(8) -0.0863(2) 0.0763(14) Uani 1 1 d . .
H3A H 0.6554 -0.0346 -0.0922 0.092 Uiso 1 1 calc R U
C4 C 0.9125(3) 0.8682(10) 0.0901(2) 0.0642(13) Uani 1 1 d . .
C14 C 0.7437(3) 0.0932(8) 0.1305(2) 0.0580(11) Uani 1 1 d . .
H14 H 0.7439 -0.0487 0.1122 0.070 Uiso 1 1 calc R U
C8 C 0.9379(3) 0.4457(10) 0.2502(2) 0.0679(14) Uani 1 1 d . .
H8A H 0.9745 0.4998 0.2863 0.082 Uiso 1 1 calc R U
H8B H 0.9498 0.2886 0.2429 0.082 Uiso 1 1 calc R U
C7 C 0.9709(3) 0.7876(9) 0.2040(2) 0.0561(11) Uani 1 1 d . .
C9 C 0.8662(3) 0.4490(10) 0.2600(2) 0.0635(13) Uani 1 1 d . .
H9A H 0.8568 0.6043 0.2707 0.076 Uiso 1 1 calc R U
H9B H 0.8686 0.3500 0.2939 0.076 Uiso 1 1 calc R U
C12 C 0.6851(2) 0.4473(8) 0.1352(2) 0.0521(10) Uani 1 1 d . .
H12 H 0.6455 0.5446 0.1209 0.062 Uiso 1 1 calc R U
C1 C 1.0095(3) 1.2266(10) 0.1005(3) 0.0653(13) Uani 1 1 d . .
C16 C 0.6519(2) 0.2038(8) -0.0366(2) 0.0545(11) Uani 1 1 d . .
C6 C 0.9591(3) 1.1801(12) 0.0463(3) 0.0809(17) Uani 1 1 d . .
H6 H 0.9572 1.2691 0.0129 0.097 Uiso 1 1 calc R U
C5 C 0.9111(4) 1.0031(13) 0.0407(3) 0.0838(18) Uani 1 1 d . .
H5 H 0.8772 0.9726 0.0034 0.101 Uiso 1 1 calc R U
C17 C 0.6826(4) 0.2474(11) -0.1308(3) 0.0791(17) Uani 1 1 d . .
H27 H 0.6652 0.4054 -0.1303 0.095 Uiso 1 1 calc R U
C21 C 0.7945(4) 0.0348(14) -0.1247(3) 0.093(2) Uani 1 1 d . .
H21A H 0.7878 -0.0763 -0.0961 0.111 Uiso 1 1 calc R U
H21B H 0.8459 0.0540 -0.1167 0.111 Uiso 1 1 calc R U
C20 C 0.7619(4) -0.0587(13) -0.1868(3) 0.0885(19) Uani 1 1 d . .
H20B H 0.7819 -0.2097 -0.1893 0.106 Uiso 1 1 calc R U
H20A H 0.7737 0.0415 -0.2153 0.106 Uiso 1 1 calc R U
C18 C 0.6480(4) 0.1472(17) -0.1932(3) 0.105(3) Uani 1 1 d . .
H18A H 0.5972 0.1223 -0.1996 0.126 Uiso 1 1 calc R U
H18B H 0.6521 0.2578 -0.2229 0.126 Uiso 1 1 calc R U
C19 C 0.6817(4) -0.0769(14) -0.2026(3) 0.096(2) Uani 1 1 d . .
H19A H 0.6701 -0.1954 -0.1781 0.116 Uiso 1 1 calc R U
H19B H 0.6613 -0.1228 -0.2444 0.116 Uiso 1 1 calc R U
C23 C 0.8097(4) 0.6486(13) 0.0328(3) 0.092(2) Uani 1 1 d . .
H23A H 0.8298 0.5770 0.0050 0.138 Uiso 1 1 calc R U
H23B H 0.7864 0.7898 0.0160 0.138 Uiso 1 1 calc R U
H23C H 0.7752 0.5470 0.0407 0.138 Uiso 1 1 calc R U
C22 C 0.7640(4) 0.2529(13) -0.1154(3) 0.094(2) Uani 1 1 d . .
H22B H 0.7766 0.3692 -0.1400 0.113 Uiso 1 1 calc R U
H22A H 0.7853 0.2979 -0.0737 0.113 Uiso 1 1 calc R U
O6 O 0.5376(5) -0.3016(17) -0.1244(3) 0.186(4) Uani 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
O3 S1 O4 114.7(2) . .
O3 S1 N2 105.8(2) . .
O4 S1 N2 114.4(2) . .
O3 S1 C13 106.4(2) . .
O4 S1 C13 105.63(19) . .
N2 S1 C13 109.5(2) . .
O3 S1 Na1 57.44(15) . .
O4 S1 Na1 121.80(14) . .
N2 S1 Na1 50.20(15) . .
C13 S1 Na1 132.51(15) . .
O6 Na1 O5 86.4(2) . 1_545
O6 Na1 O4 127.6(3) . 1_545
O5 Na1 O4 75.82(13) 1_545 1_545
O6 Na1 O4 83.8(2) . 3_655
O5 Na1 O4 141.04(14) 1_545 3_655
O4 Na1 O4 80.70(12) 1_545 3_655
O6 Na1 N2 91.9(3) . .
O5 Na1 N2 103.33(14) 1_545 .
O4 Na1 N2 139.93(14) 1_545 .
O4 Na1 N2 114.57(14) 3_655 .
O6 Na1 O3 137.2(3) . .
O5 Na1 O3 124.07(14) 1_545 .
O4 Na1 O3 91.57(12) 1_545 .
O4 Na1 O3 86.81(12) 3_655 .
N2 Na1 O3 55.02(12) . .
O6 Na1 S1 114.0(3) . .
O5 Na1 S1 121.17(11) 1_545 .
O4 Na1 S1 117.44(10) 1_545 .
O4 Na1 S1 97.16(9) 3_655 .
N2 Na1 S1 29.05(10) . .
O3 Na1 S1 26.68(8) . .
O6 Na1 Na1 109.2(3) . 3_645
O5 Na1 Na1 110.55(12) 1_545 3_645
O4 Na1 Na1 40.46(8) 1_545 3_645
O4 Na1 Na1 40.24(8) 3_655 3_645
N2 Na1 Na1 140.74(13) . 3_645
O3 Na1 Na1 88.93(10) . 3_645
S1 Na1 Na1 112.56(8) . 3_645
S1 O4 Na1 125.1(2) . 1_565
S1 O4 Na1 129.98(19) . 3_655
Na1 O4 Na1 99.30(12) 1_565 3_655
C16 O5 Na1 121.8(3) . 1_565
S1 O3 Na1 95.89(19) . .
C11 C10 C15 118.5(4) . .
C11 C10 C9 119.5(4) . .
C15 C10 C9 122.0(4) . .
C12 C13 C14 120.2(4) . .
C12 C13 S1 120.4(3) . .
C14 C13 S1 119.3(3) . .
C4 O2 C23 120.1(5) . .
C10 C11 C12 121.1(4) . .
C10 C11 H11 119.5 . .
C12 C11 H11 119.5 . .
C1 C2 C3 120.9(5) . .
C1 C2 H2 119.6 . .
C3 C2 H2 119.6 . .
C16 N2 S1 117.8(3) . .
C16 N2 Na1 137.2(3) . .
S1 N2 Na1 100.8(2) . .
C7 N1 C8 125.3(5) . .
C7 N1 H1A 117.3 . .
C8 N1 H1A 117.3 . .
C2 C3 C4 119.0(5) . .
C2 C3 C7 116.1(4) . .
C4 C3 C7 124.8(5) . .
C14 C15 C10 120.5(4) . .
C14 C15 H15 119.8 . .
C10 C15 H15 119.8 . .
C16 N3 C17 123.2(5) . .
C16 N3 H3A 118.4 . .
C17 N3 H3A 118.4 . .
O2 C4 C5 123.4(5) . .
O2 C4 C3 117.7(5) . .
C5 C4 C3 118.9(5) . .
C13 C14 C15 120.4(4) . .
C13 C14 H14 119.8 . .
C15 C14 H14 119.8 . .
N1 C8 C9 112.2(5) . .
N1 C8 H8A 109.2 . .
C9 C8 H8A 109.2 . .
N1 C8 H8B 109.2 . .
C9 C8 H8B 109.2 . .
H8A C8 H8B 107.9 . .
O1 C7 N1 123.9(5) . .
O1 C7 C3 118.4(5) . .
N1 C7 C3 117.6(4) . .
C8 C9 C10 114.9(4) . .
C8 C9 H9A 108.5 . .
C10 C9 H9A 108.5 . .
C8 C9 H9B 108.5 . .
C10 C9 H9B 108.5 . .
H9A C9 H9B 107.5 . .
C13 C12 C11 119.3(4) . .
C13 C12 H12 120.3 . .
C11 C12 H12 120.3 . .
C6 C1 C2 119.9(5) . .
C6 C1 Cl1 120.1(4) . .
C2 C1 Cl1 120.0(4) . .
O5 C16 N3 120.1(5) . .
O5 C16 N2 127.0(5) . .
N3 C16 N2 113.0(4) . .
C1 C6 C5 120.5(5) . .
C1 C6 H6 119.8 . .
C5 C6 H6 119.8 . .
C6 C5 C4 120.9(5) . .
C6 C5 H5 119.6 . .
C4 C5 H5 119.6 . .
N3 C17 C18 109.8(6) . .
N3 C17 C22 110.8(6) . .
C18 C17 C22 110.2(5) . .
N3 C17 H27 108.7 . .
C18 C17 H27 108.7 . .
C22 C17 H27 108.7 . .
C22 C21 C20 113.5(6) . .
C22 C21 H21A 108.9 . .
C20 C21 H21A 108.9 . .
C22 C21 H21B 108.9 . .
C20 C21 H21B 108.9 . .
H21A C21 H21B 107.7 . .
C21 C20 C19 110.7(6) . .
C21 C20 H20B 109.5 . .
C19 C20 H20B 109.5 . .
C21 C20 H20A 109.5 . .
C19 C20 H20A 109.5 . .
H20B C20 H20A 108.1 . .
C19 C18 C17 113.1(6) . .
C19 C18 H18A 109.0 . .
C17 C18 H18A 109.0 . .
C19 C18 H18B 109.0 . .
C17 C18 H18B 109.0 . .
H18A C18 H18B 107.8 . .
C20 C19 C18 112.1(6) . .
C20 C19 H19A 109.2 . .
C18 C19 H19A 109.2 . .
C20 C19 H19B 109.2 . .
C18 C19 H19B 109.2 . .
H19A C19 H19B 107.9 . .
O2 C23 H23A 109.5 . .
O2 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
O2 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C21 C22 C17 113.5(6) . .
C21 C22 H22B 108.9 . .
C17 C22 H22B 108.9 . .
C21 C22 H22A 108.9 . .
C17 C22 H22A 108.9 . .
H22B C22 H22A 107.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O3 1.434(3) .
S1 O4 1.441(3) .
S1 N2 1.570(4) .
S1 C13 1.782(4) .
S1 Na1 3.177(2) .
Cl1 C1 1.730(6) .
Na1 O6 2.363(6) .
Na1 O5 2.379(4) 1_545
Na1 O4 2.399(4) 1_545
Na1 O4 2.410(4) 3_655
Na1 N2 2.484(4) .
Na1 O3 2.692(4) .
Na1 Na1 3.665(4) 3_645
O4 Na1 2.399(4) 1_565
O4 Na1 2.410(4) 3_655
O5 C16 1.229(6) .
O5 Na1 2.379(4) 1_565
C10 C11 1.372(7) .
C10 C15 1.391(7) .
C10 C9 1.524(6) .
C13 C12 1.367(6) .
C13 C14 1.374(6) .
O2 C4 1.344(6) .
O2 C23 1.423(6) .
C11 C12 1.405(6) .
C11 H11 0.9300 .
C2 C1 1.379(7) .
C2 C3 1.390(7) .
C2 H2 0.9300 .
O1 C7 1.230(6) .
N2 C16 1.377(6) .
N1 C7 1.305(6) .
N1 C8 1.448(6) .
N1 H1A 0.8600 .
C3 C4 1.401(6) .
C3 C7 1.522(6) .
C15 C14 1.383(7) .
C15 H15 0.9300 .
N3 C16 1.353(6) .
N3 C17 1.468(7) .
N3 H3A 0.8600 .
C4 C5 1.393(8) .
C14 H14 0.9300 .
C8 C9 1.496(8) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C12 H12 0.9300 .
C1 C6 1.364(8) .
C6 C5 1.371(9) .
C6 H6 0.9300 .
C5 H5 0.9300 .
C17 C18 1.518(10) .
C17 C22 1.519(10) .
C17 H27 0.9800 .
C21 C22 1.448(10) .
C21 C20 1.491(9) .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C20 C19 1.499(10) .
C20 H20B 0.9700 .
C20 H20A 0.9700 .
C18 C19 1.507(11) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
C22 H22B 0.9700 .
C22 H22A 0.9700 .
