# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_GBA
_database_code_depnum_ccdc_archive 'CCDC 1513733'
_audit_update_record             
;
2016-11-01 deposited with the CCDC.
2017-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
 5-chloro-N-(4-[N-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-2-methoxybenzamide 
;
_chemical_name_common            Glibenclamide
_chemical_melting_point          447K
_chemical_formula_moiety         'C23 H28 Cl N3 O5 S'
_chemical_formula_sum            'C23 H28 Cl N3 O5 S'
_chemical_formula_weight         493.99

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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'

_cell_length_a                   9.45444(13)
_cell_length_b                   17.6795(3)
_cell_length_c                   14.4839(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.4373(13)
_cell_angle_gamma                90
_cell_volume                     2416.63(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5428
_cell_measurement_theta_min      5.0010
_cell_measurement_theta_max      71.6090

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    2.538
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.18499
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10406
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.950
_diffrn_reflns_theta_max         71.844
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4613
_reflns_number_gt                4082
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0952P)²+0.6386P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4613
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1458
_refine_ls_wR_factor_gt          0.1387
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.85690(6) 0.23546(3) 0.85674(3) 0.04519(17) Uani 1 1 d . . . . .
Cl1 Cl 1.32823(6) 0.46509(4) 0.03400(4) 0.0643(2) Uani 1 1 d . . . . .
O2 O 0.77406(15) 0.38737(9) 0.16860(10) 0.0511(4) Uani 1 1 d . . . . .
O5 O 1.07360(15) 0.11897(9) 0.82138(12) 0.0548(4) Uani 1 1 d . . . . .
O1 O 1.10670(15) 0.45130(10) 0.35162(10) 0.0517(4) Uani 1 1 d . . . . .
N1 N 0.87486(18) 0.42501(11) 0.33817(12) 0.0461(4) Uani 1 1 d . . . . .
N2 N 0.84656(18) 0.14335(10) 0.85834(12) 0.0443(4) Uani 1 1 d . . . . .
N3 N 0.92548(19) 0.02195(10) 0.84868(14) 0.0495(4) Uani 1 1 d . . . . .
C1 C 1.1625(2) 0.44320(11) 0.07311(14) 0.0433(4) Uani 1 1 d . . . . .
C7 C 0.99785(19) 0.43803(10) 0.30192(13) 0.0393(4) Uani 1 1 d . . . . .
O3 O 0.9827(2) 0.25952(10) 0.90665(11) 0.0620(4) Uani 1 1 d . . . . .
C4 C 0.90097(19) 0.40482(10) 0.13566(13) 0.0389(4) Uani 1 1 d . . . . .
O4 O 0.7225(2) 0.25934(10) 0.88605(12) 0.0642(5) Uani 1 1 d . . . . .
C16 C 0.95933(19) 0.09507(11) 0.84045(13) 0.0406(4) Uani 1 1 d . . . . .
C13 C 0.8694(2) 0.26125(10) 0.73988(13) 0.0398(4) Uani 1 1 d . . . . .
C3 C 1.00641(19) 0.43424(10) 0.19830(13) 0.0380(4) Uani 1 1 d . . . . .
C2 C 1.1366(2) 0.45448(11) 0.16461(14) 0.0415(4) Uani 1 1 d . . . . .
H2 H 1.2065 0.4758 0.2044 0.050 Uiso 1 1 calc R U . . .
C5 C 0.9305(2) 0.39364(11) 0.04374(14) 0.0448(4) Uani 1 1 d . . . . .
H5 H 0.8612 0.3734 0.0027 0.054 Uiso 1 1 calc R U . . .
C6 C 1.0609(2) 0.41217(11) 0.01269(14) 0.0455(4) Uani 1 1 d . . . . .
H6 H 1.0801 0.4037 -0.0487 0.055 Uiso 1 1 calc R U . . .
C17 C 1.0266(2) -0.03865(12) 0.83262(16) 0.0476(5) Uani 1 1 d . . . . .
H17 H 1.1205 -0.0220 0.8568 0.057 Uiso 1 1 calc R U . . .
C9 C 0.8933(3) 0.32735(14) 0.45650(16) 0.0598(6) Uani 1 1 d . . . . .
H9B H 0.9871 0.3147 0.4376 0.072 Uiso 1 1 calc R U . . .
H9A H 0.8254 0.2975 0.4192 0.072 Uiso 1 1 calc R U . . .
C8 C 0.8657(2) 0.41016(13) 0.43689(14) 0.0471(5) Uani 1 1 d . . . . .
H8A H 0.7722 0.4237 0.4556 0.057 Uiso 1 1 calc R U . . .
H8B H 0.9349 0.4407 0.4722 0.057 Uiso 1 1 calc R U . . .
C10 C 0.8836(2) 0.30559(12) 0.55687(15) 0.0482(5) Uani 1 1 d . . . . .
C12 C 0.7776(3) 0.23085(12) 0.67243(15) 0.0525(5) Uani 1 1 d . . . . .
H12 H 0.7101 0.1956 0.6880 0.063 Uiso 1 1 calc R U . . .
C23 C 0.6678(2) 0.35236(14) 0.10906(17) 0.0543(5) Uani 1 1 d . . . . .
H23A H 0.6405 0.3861 0.0592 0.081 Uiso 1 1 calc R U . . .
H23B H 0.5867 0.3409 0.1434 0.081 Uiso 1 1 calc R U . . .
H23C H 0.7046 0.3065 0.0845 0.081 Uiso 1 1 calc R U . . .
C14 C 0.9671(3) 0.31469(17) 0.71725(17) 0.0652(7) Uani 1 1 d . . . . .
H14 H 1.0286 0.3357 0.7628 0.078 Uiso 1 1 calc R U . . .
C20 C 1.1045(4) -0.19066(16) 0.7720(2) 0.0762(8) Uani 1 1 d . . . . .
H20A H 1.0159 -0.2112 0.7455 0.091 Uiso 1 1 calc R U . . .
H20B H 1.1775 -0.2287 0.7663 0.091 Uiso 1 1 calc R U . . .
C11 C 0.7863(3) 0.25306(13) 0.58134(15) 0.0545(5) Uani 1 1 d . . . . .
H11 H 0.7248 0.2319 0.5359 0.065 Uiso 1 1 calc R U . . .
C22 C 0.9868(3) -0.10839(14) 0.88628(18) 0.0614(6) Uani 1 1 d . . . . .
H22A H 0.8917 -0.1242 0.8659 0.074 Uiso 1 1 calc R U . . .
H22B H 0.9870 -0.0961 0.9516 0.074 Uiso 1 1 calc R U . . .
C15 C 0.9728(3) 0.33687(17) 0.62621(19) 0.0679(7) Uani 1 1 d . . . . .
H15 H 1.0379 0.3736 0.6110 0.082 Uiso 1 1 calc R U . . .
C18 C 1.0356(4) -0.05671(16) 0.73221(18) 0.0718(8) Uani 1 1 d . . . . .
H18B H 1.0640 -0.0118 0.6995 0.086 Uiso 1 1 calc R U . . .
H18A H 0.9431 -0.0721 0.7063 0.086 Uiso 1 1 calc R U . . .
C19 C 1.1428(4) -0.12024(19) 0.7188(2) 0.0887(10) Uani 1 1 d . . . . .
H19A H 1.1444 -0.1322 0.6536 0.106 Uiso 1 1 calc R U . . .
H19B H 1.2367 -0.1033 0.7402 0.106 Uiso 1 1 calc R U . . .
C21 C 1.0898(3) -0.17326(16) 0.8725(2) 0.0724(7) Uani 1 1 d . . . . .
H21B H 1.1820 -0.1601 0.9010 0.087 Uiso 1 1 calc R U . . .
H21A H 1.0568 -0.2181 0.9032 0.087 Uiso 1 1 calc R U . . .
H2A H 0.764(3) 0.1281(15) 0.8634(17) 0.050(6) Uiso 1 1 d . . . . .
H3A H 0.843(3) 0.0092(14) 0.8600(16) 0.046(6) Uiso 1 1 d . . . . .
H1A H 0.806(3) 0.4084(16) 0.3016(19) 0.061(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4193(18) . ?
S1 O4 1.4273(17) . ?
S1 N2 1.6316(18) . ?
S1 C13 1.764(2) . ?
Cl1 C1 1.7413(19) . ?
O2 C4 1.353(2) . ?
O2 C23 1.426(3) . ?
O5 C16 1.207(2) . ?
O1 C7 1.242(2) . ?
N1 C7 1.324(3) . ?
N1 C8 1.461(3) . ?
N1 H1A 0.87(3) . ?
N2 C16 1.402(2) . ?
N2 H2A 0.83(3) . ?
N3 C16 1.339(3) . ?
N3 C17 1.464(3) . ?
N3 H3A 0.84(3) . ?
C1 C6 1.374(3) . ?
C1 C2 1.376(3) . ?
C7 C3 1.509(3) . ?
C4 C5 1.391(3) . ?
C4 C3 1.407(3) . ?
C13 C14 1.374(3) . ?
C13 C12 1.377(3) . ?
C3 C2 1.398(3) . ?
C2 H2 0.9300 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C17 C18 1.496(3) . ?
C17 C22 1.517(3) . ?
C17 H17 0.9800 . ?
C9 C8 1.511(3) . ?
C9 C10 1.512(3) . ?
C9 H9B 0.9700 . ?
C9 H9A 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C11 1.369(3) . ?
C10 C15 1.387(3) . ?
C12 C11 1.384(3) . ?
C12 H12 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C14 C15 1.380(4) . ?
C14 H14 0.9300 . ?
C20 C21 1.502(4) . ?
C20 C19 1.519(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C11 H11 0.9300 . ?
C22 C21 1.526(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C15 H15 0.9300 . ?
C18 C19 1.532(4) . ?
C18 H18B 0.9700 . ?
C18 H18A 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21A 0.9700 . ?

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
_geom_angle_publ_flag
O3 S1 O4 119.56(11) . . ?
O3 S1 N2 109.93(10) . . ?
O4 S1 N2 103.64(10) . . ?
O3 S1 C13 108.00(10) . . ?
O4 S1 C13 108.72(10) . . ?
N2 S1 C13 106.22(9) . . ?
C4 O2 C23 119.56(16) . . ?
C7 N1 C8 121.61(17) . . ?
C7 N1 H1A 117.6(19) . . ?
C8 N1 H1A 116.8(19) . . ?
C16 N2 S1 123.92(15) . . ?
C16 N2 H2A 123.1(18) . . ?
S1 N2 H2A 112.4(18) . . ?
C16 N3 C17 122.06(18) . . ?
C16 N3 H3A 120.5(18) . . ?
C17 N3 H3A 117.3(18) . . ?
C6 C1 C2 120.89(18) . . ?
C6 C1 Cl1 119.31(16) . . ?
C2 C1 Cl1 119.76(16) . . ?
O1 C7 N1 121.30(18) . . ?
O1 C7 C3 119.51(17) . . ?
N1 C7 C3 119.16(17) . . ?
O2 C4 C5 122.58(17) . . ?
O2 C4 C3 117.77(17) . . ?
C5 C4 C3 119.64(17) . . ?
O5 C16 N3 125.46(19) . . ?
O5 C16 N2 122.01(19) . . ?
N3 C16 N2 112.52(17) . . ?
C14 C13 C12 120.22(19) . . ?
C14 C13 S1 119.42(16) . . ?
C12 C13 S1 120.29(16) . . ?
C2 C3 C4 118.32(17) . . ?
C2 C3 C7 115.89(17) . . ?
C4 C3 C7 125.42(17) . . ?
C1 C2 C3 120.67(18) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C6 C5 C4 120.94(19) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C1 C6 C5 119.48(18) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
N3 C17 C18 112.73(18) . . ?
N3 C17 C22 109.20(18) . . ?
C18 C17 C22 110.8(2) . . ?
N3 C17 H17 108.0 . . ?
C18 C17 H17 108.0 . . ?
C22 C17 H17 108.0 . . ?
C8 C9 C10 114.05(18) . . ?
C8 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
H9B C9 H9A 107.6 . . ?
N1 C8 C9 109.77(18) . . ?
N1 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
N1 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C11 C10 C15 118.2(2) . . ?
C11 C10 C9 120.1(2) . . ?
C15 C10 C9 121.7(2) . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
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 . . ?
C13 C14 C15 119.3(2) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C21 C20 C19 111.2(3) . . ?
C21 C20 H20A 109.4 . . ?
C19 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C10 C11 C12 121.2(2) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C17 C22 C21 111.3(2) . . ?
C17 C22 H22A 109.4 . . ?
C21 C22 H22A 109.4 . . ?
C17 C22 H22B 109.4 . . ?
C21 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C14 C15 C10 121.4(2) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
C17 C18 C19 110.8(2) . . ?
C17 C18 H18B 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18A 109.5 . . ?
H18B C18 H18A 108.1 . . ?
C20 C19 C18 110.9(3) . . ?
C20 C19 H19A 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 108.0 . . ?
C20 C21 C22 112.2(2) . . ?
C20 C21 H21B 109.2 . . ?
C22 C21 H21B 109.2 . . ?
C20 C21 H21A 109.2 . . ?
C22 C21 H21A 109.2 . . ?
H21B C21 H21A 107.9 . . ?

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.072


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_preparation       ', Pharmaceutical'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_GBA-Na-Form-III
_database_code_depnum_ccdc_archive 'CCDC 1513738'
_audit_update_record             
;
2016-11-01 deposited with the CCDC.
2017-01-04 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_GBA-Na-Form-III     
;
RESPONSE: This needle shape crystal quality was not good and shown weak diffraction. Additionally water molecule hydrogens non hydrogen bonding in the crystal lattice and its oxygen exhibited big thermal elipsoids. 
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
 5-chloro-N-(4-[N-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-2-methoxybenzamide-sodium-hydrate 
;
_chemical_name_common            'Glibenclamide-sodiumhydrate salt'
_chemical_melting_point          ?
_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

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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'

_cell_length_a                   19.5991(16)
_cell_length_b                   5.8086(3)
_cell_length_c                   23.4722(17)
_cell_angle_alpha                90
_cell_angle_beta                 108.746(8)
_cell_angle_gamma                90
_cell_volume                     2530.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3202
_cell_measurement_theta_min      3.5880
_cell_measurement_theta_max      69.2630

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    2.652
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.40149
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20762
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_av_R_equivalents  0.0756
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.559
_diffrn_reflns_theta_max         72.221
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4906
_reflns_number_gt                3105
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_structure_solution    
;
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_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ', Pharmaceutical'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1643P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4906
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0844
_refine_ls_wR_factor_ref         0.2750
_refine_ls_wR_factor_gt          0.2244
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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 . ?

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
_geom_angle_publ_flag
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 . . ?

_refine_diff_density_max         0.973
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.104


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol+Water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_GBA-NH4
_database_code_depnum_ccdc_archive 'CCDC 1513737'
_audit_update_record             
;
2016-11-01 deposited with the CCDC.
2017-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
 5-chloro-N-(4-[N-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-2-methoxybenzamide-ammonium
;
_chemical_name_common            'Glibenclamide-ammonium salt'
_chemical_melting_point          395K
_chemical_formula_moiety         'C23 H31 Cl N4 O5 S'
_chemical_formula_sum            'C23 H31 Cl N4 O5 S'
_chemical_formula_weight         511.03

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.718(4)
_cell_length_b                   6.1475(11)
_cell_length_c                   21.732(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.25(2)
_cell_angle_gamma                90
_cell_volume                     2487.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    993
_cell_measurement_theta_min      2.8085
_cell_measurement_theta_max      26.3150

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             1080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.279
_shelx_estimated_absorpt_T_min   0.878
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80185
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8765
_diffrn_reflns_av_unetI/netI     0.3097
_diffrn_reflns_av_R_equivalents  0.1174
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.228
_diffrn_reflns_theta_max         24.713
_diffrn_reflns_theta_full        24.713
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4237
_reflns_number_gt                1284
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ', Pharmaceutical'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0138P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4237
_refine_ls_number_parameters     324
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.2463
_refine_ls_R_factor_gt           0.0644
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0682
_refine_ls_goodness_of_fit_ref   0.770
_refine_ls_restrained_S_all      0.770
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S3 S 0.07218(9) 0.8034(3) 0.11465(8) 0.0486(5) Uani 1 1 d . . . . .
Cl1 Cl 0.41978(9) -0.3597(3) 0.45300(8) 0.0947(7) Uani 1 1 d . . . . .
O3 O 0.01464(17) 0.6571(6) 0.07932(16) 0.0560(11) Uani 1 1 d . . . . .
O1 O 0.23065(19) 0.1844(6) 0.48494(18) 0.0516(11) Uani 1 1 d . . . . .
O2 O 0.05726(18) 1.0326(6) 0.10376(18) 0.0618(12) Uani 1 1 d . . . . .
N2 N 0.1410(2) 0.7181(6) 0.09957(19) 0.0438(13) Uani 1 1 d . . . . .
N3 N 0.2596(2) 0.7198(6) 0.11481(19) 0.0481(13) Uani 1 1 d . . . . .
H3A H 0.2497 0.6050 0.0909 0.058 Uiso 1 1 calc R U . . .
O5 O 0.2550(2) 0.3853(6) 0.31398(18) 0.0649(13) Uani 1 1 d . . . . .
C16 C 0.2047(3) 0.8300(10) 0.1264(3) 0.0418(15) Uani 1 1 d . . . . .
C4 C 0.2931(3) 0.2099(10) 0.3441(3) 0.0438(16) Uani 1 1 d . . . . .
O4 O 0.2160(2) 0.9943(6) 0.15838(19) 0.0658(14) Uani 1 1 d . . . . .
C3 C 0.2912(3) 0.1597(9) 0.4062(3) 0.0353(15) Uani 1 1 d . . . . .
C5 C 0.3316(3) 0.0774(10) 0.3161(3) 0.0530(18) Uani 1 1 d . . . . .
H5 H 0.3305 0.1041 0.2737 0.064 Uiso 1 1 calc R U . . .
C13 C 0.0856(3) 0.7586(9) 0.1991(2) 0.0339(15) Uani 1 1 d . . . . .
C7 C 0.2458(3) 0.2717(10) 0.4398(3) 0.0452(17) Uani 1 1 d . . . . .
C17 C 0.3336(3) 0.7893(8) 0.1413(3) 0.0432(15) Uani 1 1 d . . . . .
H17 H 0.3406 0.8519 0.1844 0.052 Uiso 1 1 calc R U . . .
C12 C 0.0661(3) 0.5609(10) 0.2172(3) 0.0497(17) Uani 1 1 d . . . . .
H12 H 0.0471 0.4528 0.1864 0.060 Uiso 1 1 calc R U . . .
C2 C 0.3300(3) -0.0173(9) 0.4388(3) 0.0474(17) Uani 1 1 d . . . . .
H2 H 0.3286 -0.0534 0.4800 0.057 Uiso 1 1 calc R U . . .
C10 C 0.1000(3) 0.6823(12) 0.3284(3) 0.0530(18) Uani 1 1 d . . . . .
C23 C 0.2575(3) 0.4506(8) 0.2514(3) 0.070(2) Uani 1 1 d . . . . .
H23A H 0.2337 0.3436 0.2194 0.105 Uiso 1 1 calc R U . . .
H23C H 0.3067 0.4633 0.2533 0.105 Uiso 1 1 calc R U . . .
H23B H 0.2339 0.5884 0.2397 0.105 Uiso 1 1 calc R U . . .
N1 N 0.2243(2) 0.4723(8) 0.4196(2) 0.0625(16) Uani 1 1 d . . . . .
H1A H 0.2402 0.5279 0.3907 0.075 Uiso 1 1 calc R U . . .
C1 C 0.3699(3) -0.1390(9) 0.4114(3) 0.0530(18) Uani 1 1 d . . . . .
C18 C 0.3838(3) 0.5969(8) 0.1505(3) 0.0573(18) Uani 1 1 d . . . . .
H18A H 0.3777 0.5299 0.1086 0.069 Uiso 1 1 calc R U . . .
H18B H 0.3719 0.4896 0.1781 0.069 Uiso 1 1 calc R U . . .
C8 C 0.1761(4) 0.6061(11) 0.4421(3) 0.093(3) Uani 1 1 d . . . . .
H8B H 0.1719 0.5395 0.4811 0.112 Uiso 1 1 calc R U . . .
H8A H 0.1987 0.7469 0.4545 0.112 Uiso 1 1 calc R U . . .
C22 C 0.3532(3) 0.9637(8) 0.1002(3) 0.0547(17) Uani 1 1 d . . . . .
H22A H 0.3446 0.9081 0.0565 0.066 Uiso 1 1 calc R U . . .
H22B H 0.3226 1.0895 0.0970 0.066 Uiso 1 1 calc R U . . .
C11 C 0.0751(3) 0.5259(10) 0.2817(3) 0.0569(19) Uani 1 1 d . . . . .
H11 H 0.0637 0.3898 0.2942 0.068 Uiso 1 1 calc R U . . .
C15 C 0.1194(3) 0.8814(10) 0.3086(3) 0.0566(19) Uani 1 1 d . . . . .
H15 H 0.1380 0.9899 0.3394 0.068 Uiso 1 1 calc R U . . .
C6 C 0.3714(3) -0.0926(10) 0.3502(3) 0.0607(19) Uani 1 1 d . . . . .
H6 H 0.3992 -0.1759 0.3320 0.073 Uiso 1 1 calc R U . . .
C19 C 0.4617(3) 0.6684(9) 0.1817(3) 0.0657(19) Uani 1 1 d . . . . .
H19B H 0.4685 0.7253 0.2250 0.079 Uiso 1 1 calc R U . . .
H19A H 0.4930 0.5436 0.1861 0.079 Uiso 1 1 calc R U . . .
C14 C 0.1115(3) 0.9205(9) 0.2440(3) 0.0512(17) Uani 1 1 d . . . . .
H14 H 0.1237 1.0552 0.2312 0.061 Uiso 1 1 calc R U . . .
C21 C 0.4315(3) 1.0328(9) 0.1291(3) 0.072(2) Uani 1 1 d . . . . .
H21A H 0.4429 1.1330 0.0995 0.086 Uiso 1 1 calc R U . . .
H21B H 0.4384 1.1086 0.1699 0.086 Uiso 1 1 calc R U . . .
C9 C 0.1077(3) 0.6408(12) 0.3994(3) 0.105(3) Uani 1 1 d . . . . .
H9B H 0.0875 0.7644 0.4150 0.125 Uiso 1 1 calc R U . . .
H9A H 0.0787 0.5149 0.4010 0.125 Uiso 1 1 calc R U . . .
C20 C 0.4818(3) 0.8408(9) 0.1413(3) 0.073(2) Uani 1 1 d . . . . .
H20B H 0.5305 0.8896 0.1637 0.087 Uiso 1 1 calc R U . . .
H20A H 0.4805 0.7786 0.0999 0.087 Uiso 1 1 calc R U . . .
N4 N 0.1105(3) 0.3190(9) 0.0318(3) 0.0455(13) Uani 1 1 d D . . . .
H4A H 0.072(3) 0.347(14) -0.010(2) 0.24(5) Uiso 1 1 d D . . . .
H4B H 0.149(2) 0.290(8) 0.015(2) 0.09(3) Uiso 1 1 d D . . . .
H4C H 0.111(4) 0.208(8) 0.063(2) 0.16(3) Uiso 1 1 d D . . . .
H4D H 0.120(3) 0.461(5) 0.053(2) 0.09(2) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S3 O2 1.443(3) . ?
S3 O3 1.453(3) . ?
S3 N2 1.587(4) . ?
S3 C13 1.786(5) . ?
Cl1 C1 1.743(5) . ?
O1 C7 1.238(6) . ?
N2 C16 1.380(6) . ?
N3 C16 1.369(6) . ?
N3 C17 1.446(5) . ?
N3 H3A 0.8600 . ?
O5 C4 1.353(6) . ?
O5 C23 1.434(5) . ?
C16 O4 1.205(5) . ?
C4 C5 1.382(6) . ?
C4 C3 1.397(6) . ?
C3 C2 1.383(6) . ?
C3 C7 1.497(7) . ?
C5 C6 1.369(6) . ?
C5 H5 0.9300 . ?
C13 C14 1.369(6) . ?
C13 C12 1.372(6) . ?
C7 N1 1.331(6) . ?
C17 C18 1.512(6) . ?
C17 C22 1.525(6) . ?
C17 H17 0.9800 . ?
C12 C11 1.370(6) . ?
C12 H12 0.9300 . ?
C2 C1 1.359(6) . ?
C2 H2 0.9300 . ?
C10 C11 1.367(7) . ?
C10 C15 1.392(7) . ?
C10 C9 1.520(7) . ?
C23 H23A 0.9600 . ?
C23 H23C 0.9600 . ?
C23 H23B 0.9600 . ?
N1 C8 1.457(6) . ?
N1 H1A 0.8600 . ?
C1 C6 1.369(6) . ?
C18 C19 1.525(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C8 C9 1.379(6) . ?
C8 H8B 0.9700 . ?
C8 H8A 0.9700 . ?
C22 C21 1.522(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C11 H11 0.9300 . ?
C15 C14 1.383(6) . ?
C15 H15 0.9300 . ?
C6 H6 0.9300 . ?
C19 C20 1.510(6) . ?
C19 H19B 0.9700 . ?
C19 H19A 0.9700 . ?
C14 H14 0.9300 . ?
C21 C20 1.508(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20A 0.9700 . ?
N4 H4A 0.98(2) . ?
N4 H4B 0.959(19) . ?
N4 H4C 0.96(2) . ?
N4 H4D 0.972(19) . ?

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
_geom_angle_publ_flag
O2 S3 O3 115.9(2) . . ?
O2 S3 N2 115.5(2) . . ?
O3 S3 N2 105.0(2) . . ?
O2 S3 C13 105.8(2) . . ?
O3 S3 C13 105.9(2) . . ?
N2 S3 C13 108.3(2) . . ?
C16 N2 S3 118.0(4) . . ?
C16 N3 C17 122.5(5) . . ?
C16 N3 H3A 118.8 . . ?
C17 N3 H3A 118.8 . . ?
C4 O5 C23 119.6(4) . . ?
O4 C16 N3 120.9(6) . . ?
O4 C16 N2 129.2(6) . . ?
N3 C16 N2 109.9(5) . . ?
O5 C4 C5 123.7(6) . . ?
O5 C4 C3 117.1(5) . . ?
C5 C4 C3 119.2(6) . . ?
C2 C3 C4 118.9(5) . . ?
C2 C3 C7 115.4(6) . . ?
C4 C3 C7 125.5(6) . . ?
C6 C5 C4 120.8(6) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C14 C13 C12 120.9(5) . . ?
C14 C13 S3 121.0(5) . . ?
C12 C13 S3 118.1(5) . . ?
O1 C7 N1 122.0(6) . . ?
O1 C7 C3 121.8(6) . . ?
N1 C7 C3 116.2(6) . . ?
N3 C17 C18 110.6(4) . . ?
N3 C17 C22 113.1(4) . . ?
C18 C17 C22 110.3(5) . . ?
N3 C17 H17 107.5 . . ?
C18 C17 H17 107.5 . . ?
C22 C17 H17 107.5 . . ?
C11 C12 C13 118.6(6) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C1 C2 C3 120.6(6) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C11 C10 C15 117.2(6) . . ?
C11 C10 C9 121.8(7) . . ?
C15 C10 C9 121.0(7) . . ?
O5 C23 H23A 109.5 . . ?
O5 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
O5 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23C C23 H23B 109.5 . . ?
C7 N1 C8 125.8(5) . . ?
C7 N1 H1A 117.1 . . ?
C8 N1 H1A 117.1 . . ?
C2 C1 C6 120.8(6) . . ?
C2 C1 Cl1 120.7(6) . . ?
C6 C1 Cl1 118.5(5) . . ?
C17 C18 C19 110.6(5) . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C9 C8 N1 117.6(6) . . ?
C9 C8 H8B 107.9 . . ?
N1 C8 H8B 107.9 . . ?
C9 C8 H8A 107.9 . . ?
N1 C8 H8A 107.9 . . ?
H8B C8 H8A 107.2 . . ?
C21 C22 C17 111.9(5) . . ?
C21 C22 H22A 109.2 . . ?
C17 C22 H22A 109.2 . . ?
C21 C22 H22B 109.2 . . ?
C17 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C10 C11 C12 122.9(6) . . ?
C10 C11 H11 118.6 . . ?
C12 C11 H11 118.6 . . ?
C14 C15 C10 121.1(6) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C5 C6 C1 119.5(6) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C20 C19 C18 111.3(5) . . ?
C20 C19 H19B 109.4 . . ?
C18 C19 H19B 109.4 . . ?
C20 C19 H19A 109.4 . . ?
C18 C19 H19A 109.4 . . ?
H19B C19 H19A 108.0 . . ?
C13 C14 C15 119.2(5) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C20 C21 C22 111.9(5) . . ?
C20 C21 H21A 109.2 . . ?
C22 C21 H21A 109.2 . . ?
C20 C21 H21B 109.2 . . ?
C22 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C8 C9 C10 117.2(6) . . ?
C8 C9 H9B 108.0 . . ?
C10 C9 H9B 108.0 . . ?
C8 C9 H9A 108.0 . . ?
C10 C9 H9A 108.0 . . ?
H9B C9 H9A 107.3 . . ?
C21 C20 C19 111.5(5) . . ?
C21 C20 H20B 109.3 . . ?
C19 C20 H20B 109.3 . . ?
C21 C20 H20A 109.3 . . ?
C19 C20 H20A 109.3 . . ?
H20B C20 H20A 108.0 . . ?
H4A N4 H4B 99(5) . . ?
H4A N4 H4C 127(6) . . ?
H4B N4 H4C 107(5) . . ?
H4A N4 H4D 104(5) . . ?
H4B N4 H4D 107(4) . . ?
H4C N4 H4D 111(5) . . ?

_refine_diff_density_max         0.394
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_GBA-Na-Form-I
_database_code_depnum_ccdc_archive 'CCDC 1513736'
_audit_update_record             
;
2016-11-01 deposited with the CCDC.
2017-01-04 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_GBA-Na-Form-I       
;
RESPONSE: The crystal quality was not good and due thermal viabrations of carbons in benzene ring are high at RT.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
 5-chloro-N-(4-[N-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-2-methoxybenzamide-sodium
;
_chemical_name_common            'Glibenclamidesodium salt'
_chemical_melting_point          528K
_chemical_formula_moiety         'C23 H27 Cl N3 Na O5 S'
_chemical_formula_sum            'C23 H27 Cl N3 Na O5 S'
_chemical_formula_weight         515.97

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   10.9425(10)
_cell_length_b                   10.1583(7)
_cell_length_c                   11.5023(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.164(9)
_cell_angle_gamma                90
_cell_volume                     1278.31(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2241
_cell_measurement_theta_min      5.6030
_cell_measurement_theta_max      70.8660

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             540
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    2.578
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  multi-scan
_diffrn_measurement_method       'not measured'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10750
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.844
_diffrn_reflns_theta_max         72.678
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.789
_diffrn_reflns_point_group_measured_fraction_full 0.817
_reflns_number_total             4011
_reflns_number_gt                2956
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.520
_reflns_Friedel_fraction_max     0.574
_reflns_Friedel_fraction_full    0.611

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0653P)²+0.3360P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 708 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4011
_refine_ls_number_parameters     308
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.1569
_refine_ls_wR_factor_gt          0.1366
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.44372(14) 0.29430(15) 0.40370(13) 0.0417(4) Uani 1 1 d . . . . .
Na1 Na 0.4103(2) 0.5937(2) 0.3994(2) 0.0487(6) Uani 1 1 d . . . . .
O4 O 0.5437(4) 0.2019(4) 0.4218(4) 0.0474(11) Uani 1 1 d . . . . .
O5 O 0.4341(4) 0.2272(4) 0.6537(4) 0.0497(12) Uani 1 1 d . . . . .
O3 O 0.4540(4) 0.3802(4) 0.3043(4) 0.0532(12) Uani 1 1 d . . . . .
C16 C 0.4232(6) 0.3414(6) 0.6230(6) 0.0436(16) Uani 1 1 d . . . . .
N2 N 0.4226(5) 0.3887(5) 0.5093(5) 0.0434(13) Uani 1 1 d . . . . .
C13 C 0.3107(6) 0.1984(6) 0.3789(5) 0.0420(15) Uani 1 1 d . . . . .
N3 N 0.4048(6) 0.4402(6) 0.6983(5) 0.0567(15) Uani 1 1 d . . . . .
H3A H 0.3859 0.5162 0.6703 0.068 Uiso 1 1 calc R U . . .
C11 C 0.1974(7) -0.0009(7) 0.3918(7) 0.0590(19) Uani 1 1 d . . . . .
H11 H 0.1951 -0.0895 0.4117 0.071 Uiso 1 1 calc R U . . .
O2 O 0.1400(5) -0.0028(6) 0.6810(5) 0.0745(17) Uani 1 1 d . . . . .
Cl1 Cl -0.0801(4) 0.3245(6) 1.0378(4) 0.195(2) Uani 1 1 d . . . . .
O1 O -0.2123(5) 0.1384(6) 0.6381(5) 0.0750(17) Uani 1 1 d . . . . .
C3 C -0.0269(6) 0.1231(7) 0.7455(7) 0.0560(18) Uani 1 1 d . . . . .
C7 C -0.1057(6) 0.1009(7) 0.6398(7) 0.0571(19) Uani 1 1 d . . . . .
C15 C 0.0994(7) 0.1898(9) 0.3176(7) 0.071(2) Uani 1 1 d . . . . .
H15 H 0.0300 0.2317 0.2876 0.085 Uiso 1 1 calc R U . . .
C12 C 0.3061(6) 0.0681(7) 0.4061(6) 0.0513(17) Uani 1 1 d . . . . .
H12 H 0.3758 0.0253 0.4343 0.062 Uiso 1 1 calc R U . . .
N1 N -0.0548(6) 0.0497(8) 0.5473(6) 0.073(2) Uani 1 1 d . . . . .
H1A H 0.0189 0.0210 0.5540 0.088 Uiso 1 1 calc R U . . .
C10 C 0.0920(6) 0.0593(8) 0.3484(6) 0.057(2) Uani 1 1 d . . . . .
C9 C -0.0283(7) -0.0129(9) 0.3439(8) 0.074(3) Uani 1 1 d . . . . .
H9A H -0.0140 -0.1059 0.3573 0.088 Uiso 1 1 calc R U . . .
H9B H -0.0654 -0.0030 0.2671 0.088 Uiso 1 1 calc R U . . .
C17 C 0.4146(7) 0.4272(7) 0.8244(6) 0.0560(19) Uani 1 1 d . . . . .
H17 H 0.3956 0.3356 0.8438 0.067 Uiso 1 1 calc R U . . .
C14 C 0.2075(7) 0.2610(7) 0.3298(7) 0.061(2) Uani 1 1 d . . . . .
H14 H 0.2113 0.3483 0.3058 0.073 Uiso 1 1 calc R U . . .
C4 C 0.0927(7) 0.0776(8) 0.7639(7) 0.061(2) Uani 1 1 d . . . . .
C2 C -0.0771(8) 0.1997(9) 0.8318(8) 0.074(2) Uani 1 1 d . . . . .
H2 H -0.1567 0.2308 0.8229 0.089 Uiso 1 1 calc R U . . .
C1 C -0.0106(12) 0.2300(12) 0.9301(10) 0.106(4) Uani 1 1 d . . . . .
C5 C 0.1595(9) 0.1163(10) 0.8623(9) 0.086(3) Uani 1 1 d . . . . .
H5 H 0.2408 0.0908 0.8710 0.103 Uiso 1 1 calc R U . . .
C23 C 0.2617(7) -0.0540(10) 0.6982(8) 0.080(3) Uani 1 1 d . . . . .
H23A H 0.2808 -0.1120 0.6352 0.120 Uiso 1 1 calc R U . . .
H23B H 0.2664 -0.1017 0.7702 0.120 Uiso 1 1 calc R U . . .
H23C H 0.3191 0.0174 0.7006 0.120 Uiso 1 1 calc R U . . .
C6 C 0.1068(10) 0.1916(12) 0.9468(11) 0.111(4) Uani 1 1 d . . . . .
H6 H 0.1507 0.2155 1.0136 0.134 Uiso 1 1 calc R U . . .
C20 C 0.4834(18) 0.5419(11) 1.0401(10) 0.144(7) Uani 1 1 d D . . . .
H20A H 0.5049 0.6217 0.9990 0.172 Uiso 1 1 calc R U . . .
H20B H 0.5008 0.5554 1.1222 0.172 Uiso 1 1 calc R U . . .
C19 C 0.5564(14) 0.4321(19) 0.9977(12) 0.186(8) Uani 1 1 d D . . . .
H19B H 0.5239 0.3479 1.0222 0.223 Uiso 1 1 calc R U . . .
H19A H 0.6413 0.4392 1.0229 0.223 Uiso 1 1 calc R U . . .
C18 C 0.5406(11) 0.453(2) 0.8628(9) 0.201(10) Uani 1 1 d . . . . .
H18A H 0.5626 0.5423 0.8431 0.242 Uiso 1 1 calc R U . . .
H18B H 0.5952 0.3937 0.8226 0.242 Uiso 1 1 calc R U . . .
C21 C 0.3431(15) 0.512(2) 1.0207(11) 0.213(11) Uani 1 1 d . . . . .
H21A H 0.2934 0.5813 1.0539 0.256 Uiso 1 1 calc R U . . .
H21B H 0.3210 0.4286 1.0550 0.256 Uiso 1 1 calc R U . . .
C22 C 0.3265(13) 0.508(2) 0.8781(9) 0.211(11) Uani 1 1 d . . . . .
H22B H 0.2454 0.4757 0.8582 0.253 Uiso 1 1 calc R U . . .
H22A H 0.3332 0.5970 0.8479 0.253 Uiso 1 1 calc R U . . .
C8 C -0.1163(7) 0.0392(11) 0.4350(8) 0.081(3) Uani 1 1 d . . . . .
H8A H -0.1468 0.1249 0.4113 0.098 Uiso 1 1 calc R U . . .
H8B H -0.1855 -0.0200 0.4407 0.098 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.445(5) . ?
S1 O4 1.453(4) . ?
S1 N2 1.568(5) . ?
S1 C13 1.769(6) . ?
S1 Na1 3.064(3) . ?
Na1 O1 2.246(6) 2_556 ?
Na1 O5 2.270(5) 2_656 ?
Na1 O4 2.376(5) 2_656 ?
Na1 N2 2.438(6) . ?
Na1 O3 2.481(5) . ?
Na1 C16 3.120(7) 2_656 ?
O4 Na1 2.376(5) 2_646 ?
O5 C16 1.218(7) . ?
O5 Na1 2.270(5) 2_646 ?
C16 N3 1.344(8) . ?
C16 N2 1.393(8) . ?
C16 Na1 3.120(7) 2_646 ?
C13 C12 1.362(9) . ?
C13 C14 1.405(9) . ?
N3 C17 1.458(8) . ?
C11 C12 1.387(10) . ?
C11 C10 1.389(10) . ?
O2 C4 1.365(9) . ?
O2 C23 1.440(8) . ?
Cl1 C1 1.753(11) . ?
O1 C7 1.227(8) . ?
O1 Na1 2.246(6) 2_546 ?
C3 C2 1.383(11) . ?
C3 C4 1.400(9) . ?
C3 C7 1.493(10) . ?
C7 N1 1.318(10) . ?
C15 C10 1.375(11) . ?
C15 C14 1.391(10) . ?
N1 C8 1.448(10) . ?
C10 C9 1.507(9) . ?
C9 C8 1.531(12) . ?
C17 C22 1.419(13) . ?
C17 C18 1.462(12) . ?
C4 C5 1.392(11) . ?
C2 C1 1.367(13) . ?
C1 C6 1.353(14) . ?
C5 C6 1.372(13) . ?
C20 C19 1.461(17) . ?
C20 C21 1.58(2) . ?
C19 C18 1.571(16) . ?
C21 C22 1.647(15) . ?

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
_geom_angle_publ_flag
O3 S1 O4 115.7(3) . . ?
O3 S1 N2 105.0(3) . . ?
O4 S1 N2 114.0(3) . . ?
O3 S1 C13 106.4(3) . . ?
O4 S1 C13 106.4(3) . . ?
N2 S1 C13 109.1(3) . . ?
O3 S1 Na1 53.0(2) . . ?
O4 S1 Na1 137.13(19) . . ?
N2 S1 Na1 52.1(2) . . ?
C13 S1 Na1 116.5(2) . . ?
O1 Na1 O5 123.6(2) 2_556 2_656 ?
O1 Na1 O4 105.0(2) 2_556 2_656 ?
O5 Na1 O4 79.02(17) 2_656 2_656 ?
O1 Na1 N2 108.4(2) 2_556 . ?
O5 Na1 N2 128.0(2) 2_656 . ?
O4 Na1 N2 86.43(18) 2_656 . ?
O1 Na1 O3 106.6(2) 2_556 . ?
O5 Na1 O3 104.55(19) 2_656 . ?
O4 Na1 O3 138.29(18) 2_656 . ?
N2 Na1 O3 58.16(17) . . ?
O1 Na1 S1 108.53(17) 2_556 . ?
O5 Na1 S1 120.48(15) 2_656 . ?
O4 Na1 S1 114.95(14) 2_656 . ?
N2 Na1 S1 30.50(13) . . ?
O3 Na1 S1 27.74(11) . . ?
O1 Na1 C16 112.6(2) 2_556 2_656 ?
O5 Na1 C16 18.86(17) 2_656 2_656 ?
O4 Na1 C16 65.46(17) 2_656 2_656 ?
N2 Na1 C16 134.83(19) . 2_656 ?
O3 Na1 C16 123.41(19) . 2_656 ?
S1 Na1 C16 137.06(15) . 2_656 ?
S1 O4 Na1 124.6(3) . 2_646 ?
C16 O5 Na1 124.1(5) . 2_646 ?
S1 O3 Na1 99.2(2) . . ?
O5 C16 N3 122.7(7) . . ?
O5 C16 N2 126.8(6) . . ?
N3 C16 N2 110.5(6) . . ?
O5 C16 Na1 37.0(3) . 2_646 ?
N3 C16 Na1 138.7(5) . 2_646 ?
N2 C16 Na1 101.1(4) . 2_646 ?
C16 N2 S1 121.2(4) . . ?
C16 N2 Na1 141.3(4) . . ?
S1 N2 Na1 97.4(3) . . ?
C12 C13 C14 119.9(6) . . ?
C12 C13 S1 122.2(5) . . ?
C14 C13 S1 117.9(5) . . ?
C16 N3 C17 124.4(6) . . ?
C12 C11 C10 121.6(7) . . ?
C4 O2 C23 118.9(6) . . ?
C7 O1 Na1 148.6(5) . 2_546 ?
C2 C3 C4 117.4(7) . . ?
C2 C3 C7 116.0(7) . . ?
C4 C3 C7 126.5(7) . . ?
O1 C7 N1 121.8(7) . . ?
O1 C7 C3 119.9(7) . . ?
N1 C7 C3 118.1(6) . . ?
C10 C15 C14 122.0(7) . . ?
C13 C12 C11 120.0(7) . . ?
C7 N1 C8 123.6(7) . . ?
C15 C10 C11 117.7(7) . . ?
C15 C10 C9 121.1(7) . . ?
C11 C10 C9 121.1(7) . . ?
C10 C9 C8 111.7(7) . . ?
C22 C17 N3 110.1(7) . . ?
C22 C17 C18 114.2(12) . . ?
N3 C17 C18 109.6(7) . . ?
C15 C14 C13 118.7(7) . . ?
O2 C4 C5 122.5(7) . . ?
O2 C4 C3 117.3(7) . . ?
C5 C4 C3 120.2(8) . . ?
C1 C2 C3 120.5(9) . . ?
C6 C1 C2 122.7(11) . . ?
C6 C1 Cl1 118.8(9) . . ?
C2 C1 Cl1 118.5(9) . . ?
C6 C5 C4 120.8(9) . . ?
C1 C6 C5 118.1(10) . . ?
C19 C20 C21 110.2(12) . . ?
C20 C19 C18 100.3(13) . . ?
C17 C18 C19 111.1(10) . . ?
C20 C21 C22 103.5(11) . . ?
C17 C22 C21 112.7(9) . . ?
N1 C8 C9 110.4(7) . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.056


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_preparation       ', Pharmaceutical'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_GBA-K-Form-I
_database_code_depnum_ccdc_archive 'CCDC 1513734'
_audit_update_record             
;
2016-11-01 deposited with the CCDC.
2017-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
 5-chloro-N-(4-[N-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-2-methoxybenzamide-potassium 
;
_chemical_name_common            'Glibenclamide-potassium salt'
_chemical_melting_point          523K
_chemical_formula_moiety         'C23 H27 Cl K N3 O5 S'
_chemical_formula_sum            'C23 H27 Cl K N3 O5 S'
_chemical_formula_weight         532.08

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'
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'
Na Na 0.0362 0.0249 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.819(4)
_cell_length_b                   6.2006(9)
_cell_length_c                   21.636(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.69(2)
_cell_angle_gamma                90
_cell_volume                     2503.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2479
_cell_measurement_theta_min      2.8199
_cell_measurement_theta_max      28.8948

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.441
_shelx_estimated_absorpt_T_min   0.857
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8573
_exptl_absorpt_correction_T_max  0.9489
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9605
_diffrn_reflns_av_unetI/netI     0.0948
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.211
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5104
_reflns_number_gt                2515
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1428P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5104
_refine_ls_number_parameters     312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1575
_refine_ls_R_factor_gt           0.0832
_refine_ls_wR_factor_ref         0.2568
_refine_ls_wR_factor_gt          0.2247
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.06792(7) 0.8151(2) 0.10605(6) 0.0379(4) Uani 1 1 d . . . . .
K1 K -0.10668(8) 0.6662(2) -0.03667(8) 0.0670(5) Uani 1 1 d . . . . .
Cl1 Cl 0.42196(15) -0.3238(4) 0.45795(14) 0.1279(11) Uani 1 1 d . . . . .
O3 O 0.01595(18) 0.6510(6) 0.07369(17) 0.0482(10) Uani 1 1 d . . . . .
O1 O 0.2186(2) 0.1697(6) 0.48116(18) 0.0472(9) Uani 1 1 d . . . . .
O4 O 0.0456(2) 1.0360(6) 0.0890(2) 0.0529(10) Uani 1 1 d . . . . .
C13 C 0.0812(2) 0.7884(7) 0.1911(2) 0.0313(11) Uani 1 1 d . . . . .
C16 C 0.2005(3) 0.8735(9) 0.1192(3) 0.0411(13) Uani 1 1 d . . . . .
C7 C 0.2335(3) 0.2691(9) 0.4384(3) 0.0409(13) Uani 1 1 d . . . . .
C3 C 0.2872(3) 0.1783(8) 0.4086(3) 0.0379(12) Uani 1 1 d . . . . .
O5 O 0.20467(19) 1.0533(6) 0.1440(2) 0.0557(11) Uani 1 1 d . . . . .
C12 C 0.0628(3) 0.5978(8) 0.2143(2) 0.0386(12) Uani 1 1 d . . . . .
H12 H 0.0440 0.4834 0.1859 0.046 Uiso 1 1 calc R U . . .
N2 N 0.1394(2) 0.7462(7) 0.0947(2) 0.0396(10) Uani 1 1 d . . . . .
N3 N 0.2585(2) 0.7745(7) 0.1122(3) 0.0529(13) Uani 1 1 d . . . . .
H3A H 0.2523 0.6562 0.0902 0.063 Uiso 1 1 calc R U . . .
C15 C 0.1187(3) 0.9353(9) 0.2992(3) 0.0500(14) Uani 1 1 d . . . . .
H15 H 0.1383 1.0497 0.3273 0.060 Uiso 1 1 calc R U . . .
O2 O 0.2552(2) 0.4151(7) 0.3176(2) 0.0687(12) Uani 1 1 d . . . . .
C10 C 0.1010(3) 0.7482(9) 0.3247(3) 0.0431(13) Uani 1 1 d . . . . .
N1 N 0.2013(3) 0.4523(9) 0.4137(2) 0.0564(14) Uani 1 1 d . . . . .
C4 C 0.2954(3) 0.2464(9) 0.3499(3) 0.0477(14) Uani 1 1 d . . . . .
C11 C 0.0727(3) 0.5796(9) 0.2812(3) 0.0483(14) Uani 1 1 d . . . . .
H11 H 0.0602 0.4516 0.2970 0.058 Uiso 1 1 calc R U . . .
C14 C 0.1081(3) 0.9571(8) 0.2331(3) 0.0435(13) Uani 1 1 d . . . . .
H14 H 0.1192 1.0865 0.2171 0.052 Uiso 1 1 calc R U . . .
C2 C 0.3262(3) 0.0063(10) 0.4408(3) 0.0544(15) Uani 1 1 d . . . . .
H2 H 0.3210 -0.0406 0.4798 0.065 Uiso 1 1 calc R U . . .
C18 C 0.3839(3) 0.6771(9) 0.1549(3) 0.0551(16) Uani 1 1 d . . . . .
H18A H 0.3803 0.6025 0.1145 0.066 Uiso 1 1 calc R U . . .
H18B H 0.3727 0.5747 0.1840 0.066 Uiso 1 1 calc R U . . .
C8 C 0.1367(4) 0.5365(11) 0.4287(3) 0.072(2) Uani 1 1 d . . . . .
H8A H 0.0986 0.4302 0.4150 0.087 Uiso 1 1 calc R U . . .
H8B H 0.1495 0.5554 0.4758 0.087 Uiso 1 1 calc R U . . .
C17 C 0.3305(3) 0.8592(9) 0.1400(3) 0.0445(13) Uani 1 1 d . . . . .
H17 H 0.3343 0.9294 0.1816 0.053 Uiso 1 1 calc R U . . .
C22 C 0.3487(3) 1.0262(9) 0.0964(3) 0.0559(16) Uani 1 1 d . . . . .
H22A H 0.3444 0.9608 0.0546 0.067 Uiso 1 1 calc R U . . .
H22B H 0.3145 1.1439 0.0882 0.067 Uiso 1 1 calc R U . . .
C9 C 0.1110(3) 0.7345(11) 0.3972(3) 0.0625(17) Uani 1 1 d . . . . .
H9B H 0.1440 0.8473 0.4198 0.075 Uiso 1 1 calc R U . . .
H9A H 0.0653 0.7651 0.4026 0.075 Uiso 1 1 calc R U . . .
C5 C 0.3427(3) 0.1385(10) 0.3262(3) 0.0629(18) Uani 1 1 d . . . . .
H5 H 0.3481 0.1827 0.2871 0.076 Uiso 1 1 calc R U . . .
C19 C 0.4609(3) 0.7610(11) 0.1874(3) 0.0638(17) Uani 1 1 d . . . . .
H19B H 0.4657 0.8237 0.2298 0.077 Uiso 1 1 calc R U . . .
H19A H 0.4943 0.6416 0.1947 0.077 Uiso 1 1 calc R U . . .
C23 C 0.2595(4) 0.4889(11) 0.2558(3) 0.0720(19) Uani 1 1 d . . . . .
H23A H 0.2483 0.3720 0.2249 0.108 Uiso 1 1 calc R U . . .
H23C H 0.3072 0.5396 0.2622 0.108 Uiso 1 1 calc R U . . .
H23B H 0.2260 0.6042 0.2392 0.108 Uiso 1 1 calc R U . . .
C20 C 0.4792(3) 0.9294(11) 0.1447(4) 0.0691(19) Uani 1 1 d . . . . .
H20A H 0.4804 0.8622 0.1046 0.083 Uiso 1 1 calc R U . . .
H20B H 0.5265 0.9878 0.1677 0.083 Uiso 1 1 calc R U . . .
C6 C 0.3818(4) -0.0339(11) 0.3601(4) 0.074(2) Uani 1 1 d . . . . .
H6 H 0.4139 -0.1047 0.3441 0.089 Uiso 1 1 calc R U . . .
C1 C 0.3735(3) -0.1000(11) 0.4164(4) 0.0680(19) Uani 1 1 d . . . . .
C21 C 0.4236(3) 1.1144(10) 0.1275(4) 0.070(2) Uani 1 1 d . . . . .
H21B H 0.4266 1.1932 0.1671 0.084 Uiso 1 1 calc R U . . .
H21A H 0.4343 1.2137 0.0974 0.084 Uiso 1 1 calc R U . . .
H1A H 0.237(2) 0.536(7) 0.419(2) 0.020(13) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O4 1.448(4) . ?
S1 O3 1.450(4) . ?
S1 N2 1.576(4) . ?
S1 C13 1.778(5) . ?
S1 K1 3.540(2) 3_565 ?
S1 K1 3.737(2) 3_575 ?
K1 O4 2.660(4) 3_575 ?
K1 O3 2.776(4) . ?
K1 N2 2.826(4) 3_565 ?
K1 O1 2.855(4) 2 ?
K1 O3 2.952(4) 3_565 ?
K1 O5 3.025(4) 3_575 ?
K1 C8 3.466(7) 2 ?
K1 S1 3.540(2) 3_565 ?
K1 S1 3.737(2) 3_575 ?
K1 K1 4.486(3) 3_565 ?
Cl1 C1 1.753(7) . ?
O3 K1 2.952(4) 3_565 ?
O1 C7 1.228(6) . ?
O1 K1 2.855(4) 2_545 ?
O4 K1 2.660(4) 3_575 ?
C13 C14 1.370(7) . ?
C13 C12 1.380(6) . ?
C16 O5 1.228(6) . ?
C16 N3 1.356(6) . ?
C16 N2 1.391(7) . ?
C7 N1 1.324(7) . ?
C7 C3 1.527(7) . ?
C3 C2 1.363(7) . ?
C3 C4 1.398(7) . ?
O5 K1 3.025(4) 3_575 ?
C12 C11 1.397(7) . ?
C12 H12 0.9300 . ?
N2 K1 2.826(4) 3_565 ?
N3 C17 1.446(7) . ?
N3 H3A 0.8600 . ?
C15 C14 1.379(7) . ?
C15 C10 1.380(8) . ?
C15 H15 0.9300 . ?
O2 C4 1.358(7) . ?
O2 C23 1.441(7) . ?
C10 C11 1.392(8) . ?
C10 C9 1.516(8) . ?
N1 C8 1.515(8) . ?
N1 H1A 0.85(4) . ?
C4 C5 1.382(8) . ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C2 C1 1.387(8) . ?
C2 H2 0.9300 . ?
C18 C17 1.506(7) . ?
C18 C19 1.541(8) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C8 C9 1.413(9) . ?
C8 K1 3.466(7) 2_545 ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C17 C22 1.523(8) . ?
C17 H17 0.9800 . ?
C22 C21 1.511(8) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9A 0.9700 . ?
C5 C6 1.378(8) . ?
C5 H5 0.9300 . ?
C19 C20 1.517(9) . ?
C19 H19B 0.9700 . ?
C19 H19A 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23C 0.9600 . ?
C23 H23B 0.9600 . ?
C20 C21 1.547(9) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C6 C1 1.347(9) . ?
C6 H6 0.9300 . ?
C21 H21B 0.9700 . ?
C21 H21A 0.9700 . ?

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
_geom_angle_publ_flag
O4 S1 O3 115.8(2) . . ?
O4 S1 N2 115.5(2) . . ?
O3 S1 N2 105.3(2) . . ?
O4 S1 C13 106.1(2) . . ?
O3 S1 C13 105.5(2) . . ?
N2 S1 C13 108.0(2) . . ?
O4 S1 K1 141.34(17) . 3_565 ?
O3 S1 K1 54.79(15) . 3_565 ?
N2 S1 K1 50.99(15) . 3_565 ?
C13 S1 K1 112.52(16) . 3_565 ?
O4 S1 K1 33.92(15) . 3_575 ?
O3 S1 K1 128.25(16) . 3_575 ?
N2 S1 K1 81.60(16) . 3_575 ?
C13 S1 K1 121.18(16) . 3_575 ?
K1 S1 K1 116.87(5) 3_565 3_575 ?
O4 K1 O3 89.88(12) 3_575 . ?
O4 K1 N2 120.52(13) 3_575 3_565 ?
O3 K1 N2 110.79(13) . 3_565 ?
O4 K1 O1 134.64(12) 3_575 2 ?
O3 K1 O1 102.55(12) . 2 ?
N2 K1 O1 95.70(11) 3_565 2 ?
O4 K1 O3 86.61(11) 3_575 3_565 ?
O3 K1 O3 76.93(12) . 3_565 ?
N2 K1 O3 49.17(11) 3_565 3_565 ?
O1 K1 O3 138.55(11) 2 3_565 ?
O4 K1 O5 62.65(11) 3_575 3_575 ?
O3 K1 O5 146.04(11) . 3_575 ?
N2 K1 O5 100.78(12) 3_565 3_575 ?
O1 K1 O5 85.98(11) 2 3_575 ?
O3 K1 O5 117.84(11) 3_565 3_575 ?
O4 K1 C8 91.89(14) 3_575 2 ?
O3 K1 C8 75.07(16) . 2 ?
N2 K1 C8 146.40(13) 3_565 2 ?
O1 K1 C8 51.52(13) 2 2 ?
O3 K1 C8 151.96(16) 3_565 2 ?
O5 K1 C8 85.69(15) 3_575 2 ?
O4 K1 S1 102.11(10) 3_575 3_565 ?
O3 K1 S1 94.81(9) . 3_565 ?
N2 K1 S1 25.68(8) 3_565 3_565 ?
O1 K1 S1 119.67(8) 2 3_565 ?
O3 K1 S1 23.65(7) 3_565 3_565 ?
O5 K1 S1 109.53(9) 3_575 3_565 ?
C8 K1 S1 162.80(12) 2 3_565 ?
O4 K1 S1 17.68(8) 3_575 3_575 ?
O3 K1 S1 97.81(9) . 3_575 ?
N2 K1 S1 130.36(10) 3_565 3_575 ?
O1 K1 S1 117.15(8) 2 3_575 ?
O3 K1 S1 103.77(8) 3_565 3_575 ?
O5 K1 S1 50.39(7) 3_575 3_575 ?
C8 K1 S1 78.80(11) 2 3_575 ?
S1 K1 S1 116.87(5) 3_565 3_575 ?
O4 K1 K1 87.70(9) 3_575 3_565 ?
O3 K1 K1 39.86(8) . 3_565 ?
N2 K1 K1 77.84(9) 3_565 3_565 ?
O1 K1 K1 128.88(10) 2 3_565 ?
O3 K1 K1 37.07(7) 3_565 3_565 ?
O5 K1 K1 145.14(9) 3_575 3_565 ?
C8 K1 K1 114.92(14) 2 3_565 ?
S1 K1 K1 56.58(4) 3_565 3_565 ?
S1 K1 K1 103.93(5) 3_575 3_565 ?
S1 O3 K1 131.7(2) . . ?
S1 O3 K1 101.56(18) . 3_565 ?
K1 O3 K1 103.07(12) . 3_565 ?
C7 O1 K1 137.6(3) . 2_545 ?
S1 O4 K1 128.4(2) . 3_575 ?
C14 C13 C12 120.3(5) . . ?
C14 C13 S1 120.3(4) . . ?
C12 C13 S1 119.4(4) . . ?
O5 C16 N3 121.6(5) . . ?
O5 C16 N2 127.1(5) . . ?
N3 C16 N2 111.3(5) . . ?
O1 C7 N1 121.9(5) . . ?
O1 C7 C3 120.8(5) . . ?
N1 C7 C3 117.2(5) . . ?
C2 C3 C4 118.7(5) . . ?
C2 C3 C7 115.4(5) . . ?
C4 C3 C7 125.7(5) . . ?
C16 O5 K1 104.8(3) . 3_575 ?
C13 C12 C11 118.9(5) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C16 N2 S1 120.0(3) . . ?
C16 N2 K1 136.2(3) . 3_565 ?
S1 N2 K1 103.33(19) . 3_565 ?
C16 N3 C17 122.9(5) . . ?
C16 N3 H3A 118.5 . . ?
C17 N3 H3A 118.5 . . ?
C14 C15 C10 121.8(5) . . ?
C14 C15 H15 119.1 . . ?
C10 C15 H15 119.1 . . ?
C4 O2 C23 120.9(4) . . ?
C15 C10 C11 117.3(5) . . ?
C15 C10 C9 119.9(5) . . ?
C11 C10 C9 122.7(5) . . ?
C7 N1 C8 122.5(5) . . ?
C7 N1 H1A 102(3) . . ?
C8 N1 H1A 119(3) . . ?
O2 C4 C5 122.4(5) . . ?
O2 C4 C3 118.2(5) . . ?
C5 C4 C3 119.4(5) . . ?
C10 C11 C12 121.6(5) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C13 C14 C15 120.1(5) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C3 C2 C1 121.2(5) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C17 C18 C19 111.2(5) . . ?
C17 C18 H18A 109.4 . . ?
C19 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
C19 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C9 C8 N1 112.9(5) . . ?
C9 C8 K1 141.7(4) . 2_545 ?
N1 C8 K1 105.4(4) . 2_545 ?
C9 C8 H8A 109.0 . . ?
N1 C8 H8A 109.0 . . ?
K1 C8 H8A 57.6 2_545 . ?
C9 C8 H8B 109.0 . . ?
N1 C8 H8B 109.0 . . ?
K1 C8 H8B 54.3 2_545 . ?
H8A C8 H8B 107.8 . . ?
N3 C17 C18 109.9(4) . . ?
N3 C17 C22 113.3(5) . . ?
C18 C17 C22 110.3(4) . . ?
N3 C17 H17 107.7 . . ?
C18 C17 H17 107.7 . . ?
C22 C17 H17 107.7 . . ?
C21 C22 C17 111.9(5) . . ?
C21 C22 H22A 109.2 . . ?
C17 C22 H22A 109.2 . . ?
C21 C22 H22B 109.2 . . ?
C17 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C8 C9 C10 116.6(5) . . ?
C8 C9 H9B 108.1 . . ?
C10 C9 H9B 108.1 . . ?
C8 C9 H9A 108.1 . . ?
C10 C9 H9A 108.1 . . ?
H9B C9 H9A 107.3 . . ?
C6 C5 C4 120.6(6) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C20 C19 C18 111.0(5) . . ?
C20 C19 H19B 109.4 . . ?
C18 C19 H19B 109.4 . . ?
C20 C19 H19A 109.4 . . ?
C18 C19 H19A 109.4 . . ?
H19B C19 H19A 108.0 . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23C C23 H23B 109.5 . . ?
C19 C20 C21 111.0(5) . . ?
C19 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C1 C6 C5 120.0(6) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C1 C2 120.2(6) . . ?
C6 C1 Cl1 119.5(5) . . ?
C2 C1 Cl1 120.3(5) . . ?
C22 C21 C20 110.7(5) . . ?
C22 C21 H21B 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C22 C21 H21A 109.5 . . ?
C20 C21 H21A 109.5 . . ?
H21B C21 H21A 108.1 . . ?

_refine_diff_density_max         0.898
_refine_diff_density_min         -0.858
_refine_diff_density_rms         0.090


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_preparation       ', Pharmaceutical'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_GBA-Na-Form-II
_database_code_depnum_ccdc_archive 'CCDC 1513735'
_audit_update_record             
;
2016-11-01 deposited with the CCDC.
2017-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
 5-chloro-N-(4-[N-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-2-methoxybenzamide-sodium 
;
_chemical_name_common            'Glibenclamidesodium salt'
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H27 Cl N3 Na O5 S'
_chemical_formula_sum            'C23 H27 Cl N3 Na O5 S'
_chemical_formula_weight         515.97

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'
Na Na 0.0362 0.0249 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.7594(13)
_cell_length_b                   6.1759(3)
_cell_length_c                   21.5560(15)
_cell_angle_alpha                90
_cell_angle_beta                 109.627(7)
_cell_angle_gamma                90
_cell_volume                     2477.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2004
_cell_measurement_theta_min      2.8303
_cell_measurement_theta_max      26.3099

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             1080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.295
_shelx_estimated_absorpt_T_min   0.901
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9012
_exptl_absorpt_correction_T_max  0.9654
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3291
_diffrn_reflns_number            9608
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.222
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5057
_reflns_number_gt                3454
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1201P)²+3.4577P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5057
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1174
_refine_ls_R_factor_gt           0.0834
_refine_ls_wR_factor_ref         0.2495
_refine_ls_wR_factor_gt          0.2207
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.06789(6) 0.18528(18) 0.10637(5) 0.0440(3) Uani 1 1 d . . . . .
Na1 Na 0.10673(7) 0.6671(2) 0.03670(6) 0.0297(4) Uani 1 1 d . . . . .
Cl1 Cl 0.42156(14) 1.3263(4) 0.45708(12) 0.1335(10) Uani 1 1 d . . . . .
O3 O 0.01557(17) 0.3482(6) 0.07340(15) 0.0569(9) Uani 1 1 d . . . . .
O1 O 0.21936(19) 0.8291(6) 0.48134(16) 0.0589(9) Uani 1 1 d . . . . .
C13 C 0.0808(2) 0.2125(6) 0.19158(19) 0.0381(9) Uani 1 1 d . . . . .
O2 O 0.04580(19) -0.0341(6) 0.08944(18) 0.0632(9) Uani 1 1 d . . . . .
C16 C 0.2000(2) 0.1299(7) 0.1194(2) 0.0436(10) Uani 1 1 d . . . . .
C7 C 0.2341(2) 0.7291(8) 0.4380(2) 0.0477(11) Uani 1 1 d . . . . .
N2 N 0.13976(19) 0.2542(6) 0.09513(18) 0.0474(9) Uani 1 1 d . . . . .
O4 O 0.20494(18) -0.0506(6) 0.14456(19) 0.0633(10) Uani 1 1 d . . . . .
C3 C 0.2869(2) 0.8227(7) 0.4087(2) 0.0455(10) Uani 1 1 d . . . . .
C10 C 0.1009(2) 0.2503(9) 0.3248(2) 0.0508(11) Uani 1 1 d . . . . .
C14 C 0.0631(2) 0.4044(7) 0.2148(2) 0.0453(10) Uani 1 1 d . . . . .
H14 H 0.0448 0.5196 0.1863 0.054 Uiso 1 1 calc R U . . .
N1 N 0.2023(3) 0.5440(8) 0.4148(2) 0.0673(12) Uani 1 1 d . . . . .
H1A H 0.2189 0.4671 0.3899 0.081 Uiso 1 1 calc R U . . .
O5 O 0.2554(2) 0.5838(7) 0.31772(18) 0.0767(12) Uani 1 1 d . . . . .
N3 N 0.2586(2) 0.2276(7) 0.1123(2) 0.0610(11) Uani 1 1 d . . . . .
H3A H 0.2525 0.3464 0.0903 0.073 Uiso 1 1 calc R U . . .
C11 C 0.1184(3) 0.0646(8) 0.2997(2) 0.0548(12) Uani 1 1 d . . . . .
H11 H 0.1377 -0.0506 0.3278 0.066 Uiso 1 1 calc R U . . .
C17 C 0.3309(2) 0.1418(8) 0.1400(2) 0.0496(11) Uani 1 1 d . . . . .
H17 H 0.3353 0.0708 0.1818 0.060 Uiso 1 1 calc R U . . .
C12 C 0.1083(3) 0.0435(8) 0.2342(2) 0.0520(11) Uani 1 1 d . . . . .
H12 H 0.1202 -0.0858 0.2182 0.062 Uiso 1 1 calc R U . . .
C15 C 0.0729(3) 0.4235(9) 0.2816(2) 0.0569(13) Uani 1 1 d . . . . .
H15 H 0.0608 0.5522 0.2977 0.068 Uiso 1 1 calc R U . . .
C4 C 0.2951(3) 0.7555(8) 0.3492(2) 0.0530(11) Uani 1 1 d . . . . .
C8 C 0.1392(4) 0.4647(11) 0.4299(3) 0.0802(18) Uani 1 1 d . . . . .
H8B H 0.1524 0.4448 0.4771 0.096 Uiso 1 1 calc R U . . .
H8A H 0.1016 0.5734 0.4167 0.096 Uiso 1 1 calc R U . . .
C18 C 0.3483(3) -0.0212(9) 0.0961(3) 0.0639(14) Uani 1 1 d . . . . .
H18B H 0.3434 0.0451 0.0541 0.077 Uiso 1 1 calc R U . . .
H18A H 0.3146 -0.1408 0.0883 0.077 Uiso 1 1 calc R U . . .
C2 C 0.3264(3) 0.9975(9) 0.4409(3) 0.0603(13) Uani 1 1 d . . . . .
H2 H 0.3216 1.0447 0.4802 0.072 Uiso 1 1 calc R U . . .
C22 C 0.3849(3) 0.3274(9) 0.1542(3) 0.0656(14) Uani 1 1 d . . . . .
H22A H 0.3812 0.4011 0.1135 0.079 Uiso 1 1 calc R U . . .
H22B H 0.3742 0.4310 0.1834 0.079 Uiso 1 1 calc R U . . .
C5 C 0.3423(3) 0.8641(10) 0.3251(3) 0.0702(15) Uani 1 1 d . . . . .
H5 H 0.3478 0.8186 0.2859 0.084 Uiso 1 1 calc R U . . .
C21 C 0.4608(3) 0.2408(10) 0.1861(3) 0.0690(15) Uani 1 1 d . . . . .
H21B H 0.4948 0.3595 0.1934 0.083 Uiso 1 1 calc R U . . .
H21A H 0.4654 0.1781 0.2285 0.083 Uiso 1 1 calc R U . . .
C9 C 0.1115(3) 0.2638(11) 0.3975(2) 0.0698(15) Uani 1 1 d . . . . .
H9A H 0.0656 0.2359 0.4032 0.084 Uiso 1 1 calc R U . . .
H9B H 0.1440 0.1487 0.4198 0.084 Uiso 1 1 calc R U . . .
C6 C 0.3816(3) 1.0386(11) 0.3584(3) 0.0789(17) Uani 1 1 d . . . . .
H6 H 0.4133 1.1104 0.3419 0.095 Uiso 1 1 calc R U . . .
C20 C 0.4785(3) 0.0749(10) 0.1444(3) 0.0747(16) Uani 1 1 d . . . . .
H20B H 0.5259 0.0166 0.1675 0.090 Uiso 1 1 calc R U . . .
H20A H 0.4798 0.1420 0.1041 0.090 Uiso 1 1 calc R U . . .
C1 C 0.3731(3) 1.1043(11) 0.4157(3) 0.0755(16) Uani 1 1 d . . . . .
C23 C 0.2599(4) 0.5141(11) 0.2566(3) 0.0812(18) Uani 1 1 d . . . . .
H23B H 0.2462 0.6305 0.2253 0.122 Uiso 1 1 calc R U . . .
H23A H 0.2282 0.3934 0.2406 0.122 Uiso 1 1 calc R U . . .
H23C H 0.3083 0.4711 0.2624 0.122 Uiso 1 1 calc R U . . .
C19 C 0.4248(3) -0.1064(10) 0.1275(4) 0.0807(18) Uani 1 1 d . . . . .
H19A H 0.4282 -0.1864 0.1672 0.097 Uiso 1 1 calc R U . . .
H19B H 0.4358 -0.2052 0.0972 0.097 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.432(3) . ?
S1 O3 1.447(3) . ?
S1 N2 1.577(4) . ?
S1 C13 1.775(4) . ?
Na1 O2 2.659(3) 1_565 ?
Na1 O3 2.762(3) 3_565 ?
Na1 N2 2.822(4) . ?
Na1 O1 2.857(3) 4_575 ?
Na1 O3 2.951(4) . ?
Cl1 C1 1.737(6) . ?
O3 Na1 2.762(3) 3_565 ?
O1 C7 1.233(5) . ?
O1 Na1 2.857(3) 4_576 ?
C13 C12 1.376(6) . ?
C13 C14 1.376(6) . ?
O2 Na1 2.659(3) 1_545 ?
C16 O4 1.229(5) . ?
C16 N3 1.358(6) . ?
C16 N2 1.365(6) . ?
C7 N1 1.320(6) . ?
C7 C3 1.505(6) . ?
C3 C2 1.375(7) . ?
C3 C4 1.409(6) . ?
C10 C11 1.362(7) . ?
C10 C15 1.405(7) . ?
C10 C9 1.511(6) . ?
C14 C15 1.391(6) . ?
C14 H14 0.9300 . ?
N1 C8 1.474(7) . ?
N1 H1A 0.8600 . ?
O5 C4 1.357(6) . ?
O5 C23 1.418(6) . ?
N3 C17 1.452(6) . ?
N3 H3A 0.8600 . ?
C11 C12 1.365(7) . ?
C11 H11 0.9300 . ?
C17 C18 1.497(7) . ?
C17 C22 1.525(7) . ?
C17 H17 0.9800 . ?
C12 H12 0.9300 . ?
C15 H15 0.9300 . ?
C4 C5 1.385(7) . ?
C8 C9 1.439(8) . ?
C8 H8B 0.9700 . ?
C8 H8A 0.9700 . ?
C18 C19 1.527(7) . ?
C18 H18B 0.9700 . ?
C18 H18A 0.9700 . ?
C2 C1 1.387(7) . ?
C2 H2 0.9300 . ?
C22 C21 1.522(8) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C5 C6 1.380(8) . ?
C5 H5 0.9300 . ?
C21 C20 1.480(8) . ?
C21 H21B 0.9700 . ?
C21 H21A 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C6 C1 1.362(8) . ?
C6 H6 0.9300 . ?
C20 C19 1.502(8) . ?
C20 H20B 0.9700 . ?
C20 H20A 0.9700 . ?
C23 H23B 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?

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
_geom_angle_publ_flag
O2 S1 O3 115.2(2) . . ?
O2 S1 N2 115.4(2) . . ?
O3 S1 N2 105.6(2) . . ?
O2 S1 C13 106.2(2) . . ?
O3 S1 C13 105.84(19) . . ?
N2 S1 C13 108.04(19) . . ?
O2 Na1 O3 90.00(11) 1_565 3_565 ?
O2 Na1 N2 120.43(12) 1_565 . ?
O3 Na1 N2 110.92(12) 3_565 . ?
O2 Na1 O1 134.52(11) 1_565 4_575 ?
O3 Na1 O1 102.76(10) 3_565 4_575 ?
N2 Na1 O1 95.63(11) . 4_575 ?
O2 Na1 O3 86.77(11) 1_565 . ?
O3 Na1 O3 76.76(11) 3_565 . ?
N2 Na1 O3 49.28(9) . . ?
O1 Na1 O3 138.49(11) 4_575 . ?
S1 O3 Na1 132.3(2) . 3_565 ?
S1 O3 Na1 101.30(16) . . ?
Na1 O3 Na1 103.24(11) 3_565 . ?
C7 O1 Na1 137.4(3) . 4_576 ?
C12 C13 C14 120.2(4) . . ?
C12 C13 S1 120.4(3) . . ?
C14 C13 S1 119.5(3) . . ?
S1 O2 Na1 128.5(2) . 1_545 ?
O4 C16 N3 120.6(4) . . ?
O4 C16 N2 127.5(4) . . ?
N3 C16 N2 111.9(4) . . ?
O1 C7 N1 121.2(4) . . ?
O1 C7 C3 119.9(4) . . ?
N1 C7 C3 118.8(4) . . ?
C16 N2 S1 120.3(3) . . ?
C16 N2 Na1 136.1(3) . . ?
S1 N2 Na1 103.14(17) . . ?
C2 C3 C4 118.2(4) . . ?
C2 C3 C7 116.4(4) . . ?
C4 C3 C7 125.3(4) . . ?
C11 C10 C15 118.2(4) . . ?
C11 C10 C9 119.6(5) . . ?
C15 C10 C9 122.2(5) . . ?
C13 C14 C15 119.0(4) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C7 N1 C8 122.3(5) . . ?
C7 N1 H1A 118.9 . . ?
C8 N1 H1A 118.9 . . ?
C4 O5 C23 119.8(4) . . ?
C16 N3 C17 123.4(4) . . ?
C16 N3 H3A 118.3 . . ?
C17 N3 H3A 118.3 . . ?
C10 C11 C12 121.6(4) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
N3 C17 C18 112.9(4) . . ?
N3 C17 C22 109.5(4) . . ?
C18 C17 C22 109.8(4) . . ?
N3 C17 H17 108.1 . . ?
C18 C17 H17 108.1 . . ?
C22 C17 H17 108.1 . . ?
C11 C12 C13 120.4(4) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C15 C10 120.6(4) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
O5 C4 C5 122.7(4) . . ?
O5 C4 C3 117.5(4) . . ?
C5 C4 C3 119.8(5) . . ?
C9 C8 N1 113.0(5) . . ?
C9 C8 H8B 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N1 C8 H8A 109.0 . . ?
H8B C8 H8A 107.8 . . ?
C17 C18 C19 110.8(4) . . ?
C17 C18 H18B 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18A 109.5 . . ?
H18B C18 H18A 108.1 . . ?
C3 C2 C1 120.9(5) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C21 C22 C17 110.1(5) . . ?
C21 C22 H22A 109.6 . . ?
C17 C22 H22A 109.6 . . ?
C21 C22 H22B 109.6 . . ?
C17 C22 H22B 109.6 . . ?
H22A C22 H22B 108.2 . . ?
C6 C5 C4 121.0(5) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C20 C21 C22 111.5(4) . . ?
C20 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
C20 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
H21B C21 H21A 108.0 . . ?
C8 C9 C10 116.7(5) . . ?
C8 C9 H9A 108.1 . . ?
C10 C9 H9A 108.1 . . ?
C8 C9 H9B 108.1 . . ?
C10 C9 H9B 108.1 . . ?
H9A C9 H9B 107.3 . . ?
C1 C6 C5 119.1(5) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C21 C20 C19 111.8(5) . . ?
C21 C20 H20B 109.3 . . ?
C19 C20 H20B 109.3 . . ?
C21 C20 H20A 109.3 . . ?
C19 C20 H20A 109.3 . . ?
H20B C20 H20A 107.9 . . ?
C6 C1 C2 121.0(5) . . ?
C6 C1 Cl1 119.2(4) . . ?
C2 C1 Cl1 119.9(4) . . ?
O5 C23 H23B 109.5 . . ?
O5 C23 H23A 109.5 . . ?
H23B C23 H23A 109.5 . . ?
O5 C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
C20 C19 C18 111.4(5) . . ?
C20 C19 H19A 109.4 . . ?
C18 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
C18 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?

_refine_diff_density_max         0.884
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.080


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol-Ammonia '
_exptl_crystal_preparation       ', Pharmaceutical'
