# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_IDP-DPI
_database_code_depnum_ccdc_archive 'CCDC 1849062'
_audit_update_record             
;
2018-06-13 deposited with the CCDC.
2018-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
4-chloro-N-(2-methyl-2,3-dihydroindol-1-yl)-3-sulfamoylbenzamide-4-pyridin-4-ylpyridine
_chemical_name_common            "Indapamide-4,4'-Bipyridine cocrystal"
_chemical_melting_point          473K
_chemical_formula_moiety         'C16 H16 Cl N3 O3 S, C10 H8 N2'
_chemical_formula_sum            'C26 H24 Cl N5 O3 S'
_chemical_formula_weight         522.01

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/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                   7.2851(14)
_cell_length_b                   9.0281(17)
_cell_length_c                   38.510(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.230(3)
_cell_angle_gamma                90
_cell_volume                     2522.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5158
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      24.92

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.273
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23382
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         2.124
_diffrn_reflns_theta_max         25.087
_diffrn_reflns_theta_full        25.087
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4477
_reflns_number_gt                3965
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0490P)²+0.9512P] 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         4477
_refine_ls_number_parameters     346
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.002

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
H8 H 0.913(3) 0.557(2) 0.3191(5) 0.054(6) Uiso 1 1 d . . . . .
H12 H 0.405(3) 0.507(3) 0.2573(7) 0.071(7) Uiso 1 1 d . . . . .
C1 C 0.8225(3) 0.6389(2) 0.19983(5) 0.0432(4) Uani 1 1 d . . . . .
C2 C 0.7487(3) 0.6826(2) 0.16691(5) 0.0429(4) Uani 1 1 d . . . . .
H2 H 0.6444 0.7425 0.1648 0.052 Uiso 1 1 calc R U . . .
C3 C 0.8277(3) 0.6386(2) 0.13728(5) 0.0442(4) Uani 1 1 d . . . . .
C4 C 0.9866(3) 0.5526(2) 0.14086(5) 0.0534(5) Uani 1 1 d . . . . .
C5 C 1.0589(3) 0.5067(3) 0.17325(6) 0.0685(7) Uani 1 1 d . . . . .
H5 H 1.1633 0.4470 0.1754 0.082 Uiso 1 1 calc R U . . .
C6 C 0.9772(3) 0.5488(3) 0.20256(5) 0.0614(6) Uani 1 1 d . . . . .
H6 H 1.0264 0.5166 0.2244 0.074 Uiso 1 1 calc R U . . .
C7 C 0.7333(3) 0.6955(2) 0.23068(5) 0.0419(4) Uani 1 1 d . . . . .
C8 C 0.8415(3) 0.6528(3) 0.32034(5) 0.0582(5) Uani 1 1 d . . . . .
C9 C 0.7290(4) 0.6459(3) 0.35182(6) 0.0729(7) Uani 1 1 d . . . . .
H9A H 0.7935 0.5908 0.3708 0.088 Uiso 1 1 calc R U . . .
H9B H 0.7012 0.7444 0.3599 0.088 Uiso 1 1 calc R U . . .
C10 C 0.5588(3) 0.5676(3) 0.33768(6) 0.0637(6) Uani 1 1 d . . . . .
C11 C 0.5459(3) 0.5723(2) 0.30146(5) 0.0541(5) Uani 1 1 d . . . . .
C12 C 0.4054(3) 0.5055(3) 0.28129(8) 0.0748(7) Uani 1 1 d . . . . .
C13 C 0.2746(4) 0.4290(4) 0.29818(11) 0.1044(11) Uani 1 1 d . . . . .
H13 H 0.1781 0.3817 0.2851 0.125 Uiso 1 1 calc R U . . .
C14 C 0.2858(4) 0.4222(4) 0.33418(11) 0.1054(12) Uani 1 1 d . . . . .
H14 H 0.1969 0.3702 0.3451 0.126 Uiso 1 1 calc R U . . .
C15 C 0.4265(4) 0.4913(4) 0.35397(8) 0.0880(9) Uani 1 1 d . . . . .
H15 H 0.4329 0.4868 0.3782 0.106 Uiso 1 1 calc R U . . .
C16 C 0.9727(4) 0.7807(3) 0.31870(7) 0.0878(8) Uani 1 1 d . . . . .
H16A H 1.0253 0.7794 0.2967 0.132 Uiso 1 1 calc R U . . .
H16B H 1.0692 0.7724 0.3373 0.132 Uiso 1 1 calc R U . . .
H16C H 0.9074 0.8720 0.3210 0.132 Uiso 1 1 calc R U . . .
C17 C 0.2869(2) 0.0565(2) 0.02566(5) 0.0422(4) Uani 1 1 d . . . . .
C18 C 0.3185(3) 0.1845(2) 0.00756(6) 0.0555(5) Uani 1 1 d . . . . .
H18 H 0.3011 0.1854 -0.0167 0.067 Uiso 1 1 calc R U . . .
C19 C 0.3757(3) 0.3106(2) 0.02535(6) 0.0635(6) Uani 1 1 d . . . . .
H19 H 0.3973 0.3945 0.0123 0.076 Uiso 1 1 calc R U . . .
C20 C 0.3715(3) 0.1982(3) 0.07699(6) 0.0676(6) Uani 1 1 d . . . . .
H20 H 0.3875 0.2014 0.1012 0.081 Uiso 1 1 calc R U . . .
C21 C 0.3174(3) 0.0654(3) 0.06151(5) 0.0588(5) Uani 1 1 d . . . . .
H21 H 0.3017 -0.0178 0.0752 0.071 Uiso 1 1 calc R U . . .
C22 C 0.2276(2) -0.0837(2) 0.00766(5) 0.0419(4) Uani 1 1 d . . . . .
C23 C 0.1985(3) -0.0921(2) -0.02834(5) 0.0507(5) Uani 1 1 d . . . . .
H23 H 0.2120 -0.0084 -0.0419 0.061 Uiso 1 1 calc R U . . .
C24 C 0.1494(3) -0.2259(2) -0.04391(6) 0.0590(5) Uani 1 1 d . . . . .
H24 H 0.1317 -0.2285 -0.0681 0.071 Uiso 1 1 calc R U . . .
C25 C 0.1473(3) -0.3403(2) 0.00782(6) 0.0655(6) Uani 1 1 d . . . . .
H25 H 0.1267 -0.4247 0.0207 0.079 Uiso 1 1 calc R U . . .
C26 C 0.1981(3) -0.2130(2) 0.02570(6) 0.0571(5) Uani 1 1 d . . . . .
H26 H 0.2129 -0.2136 0.0499 0.069 Uiso 1 1 calc R U . . .
N1 N 0.6940(2) 0.65635(19) 0.29061(4) 0.0509(4) Uani 1 1 d . . . . .
N2 N 0.7587(3) 0.6109(2) 0.25925(4) 0.0517(4) Uani 1 1 d . . . . .
N3 N 0.6763(4) 0.5643(2) 0.07154(5) 0.0630(5) Uani 1 1 d . . . . .
N4 N 0.4023(3) 0.3213(2) 0.05982(5) 0.0645(5) Uani 1 1 d . . . . .
N5 N 0.1255(3) -0.3508(2) -0.02678(5) 0.0615(5) Uani 1 1 d . . . . .
O1 O 0.8565(3) 0.78908(18) 0.08089(4) 0.0773(5) Uani 1 1 d . . . . .
O2 O 0.5520(3) 0.7680(2) 0.10362(4) 0.0786(5) Uani 1 1 d . . . . .
O3 O 0.64599(19) 0.81160(15) 0.22922(3) 0.0518(3) Uani 1 1 d . . . . .
S1 S 0.72232(8) 0.70221(6) 0.09629(2) 0.05462(17) Uani 1 1 d . . . . .
Cl Cl 1.10041(9) 0.49897(8) 0.10529(2) 0.0773(2) Uani 1 1 d . . . . .
H2A H 0.793(3) 0.521(3) 0.2577(6) 0.055(6) Uiso 1 1 d . . . . .
H3A H 0.585(4) 0.507(3) 0.0751(6) 0.071(8) Uiso 1 1 d . . . . .
H3B H 0.761(4) 0.528(3) 0.0633(7) 0.067(8) 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
C1 C6 1.386(3) . ?
C1 C2 1.389(3) . ?
C1 C7 1.495(3) . ?
C2 C3 1.382(3) . ?
C3 C4 1.391(3) . ?
C3 S1 1.7859(19) . ?
C4 C5 1.373(3) . ?
C4 Cl 1.733(2) . ?
C5 C6 1.376(3) . ?
C7 O3 1.225(2) . ?
C7 N2 1.338(2) . ?
C8 N1 1.497(3) . ?
C8 C16 1.504(3) . ?
C8 C9 1.525(3) . ?
C9 C10 1.487(4) . ?
C10 C15 1.381(4) . ?
C10 C11 1.390(3) . ?
C11 C12 1.367(3) . ?
C11 N1 1.413(3) . ?
C12 C13 1.386(4) . ?
C13 C14 1.383(5) . ?
C14 C15 1.371(5) . ?
C17 C18 1.380(3) . ?
C17 C21 1.381(3) . ?
C17 C22 1.488(3) . ?
C18 C19 1.373(3) . ?
C19 N4 1.328(3) . ?
C20 N4 1.322(3) . ?
C20 C21 1.381(3) . ?
C22 C26 1.385(3) . ?
C22 C23 1.385(3) . ?
C23 C24 1.380(3) . ?
C24 N5 1.326(3) . ?
C25 N5 1.331(3) . ?
C25 C26 1.373(3) . ?
N1 N2 1.398(2) . ?
N3 S1 1.585(2) . ?
O1 S1 1.4241(17) . ?
O2 S1 1.4264(18) . ?

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
C6 C1 C2 118.74(17) . . ?
C6 C1 C7 123.35(17) . . ?
C2 C1 C7 117.89(16) . . ?
C3 C2 C1 121.08(18) . . ?
C2 C3 C4 118.95(17) . . ?
C2 C3 S1 117.37(14) . . ?
C4 C3 S1 123.64(15) . . ?
C5 C4 C3 120.34(18) . . ?
C5 C4 Cl 117.56(17) . . ?
C3 C4 Cl 122.10(15) . . ?
C4 C5 C6 120.2(2) . . ?
C5 C6 C1 120.59(19) . . ?
O3 C7 N2 123.94(18) . . ?
O3 C7 C1 121.19(16) . . ?
N2 C7 C1 114.87(16) . . ?
N1 C8 C16 111.46(19) . . ?
N1 C8 C9 102.04(18) . . ?
C16 C8 C9 117.0(2) . . ?
C10 C9 C8 102.62(18) . . ?
C15 C10 C11 119.0(3) . . ?
C15 C10 C9 131.6(2) . . ?
C11 C10 C9 109.3(2) . . ?
C12 C11 C10 122.4(2) . . ?
C12 C11 N1 128.4(2) . . ?
C10 C11 N1 109.2(2) . . ?
C11 C12 C13 117.7(3) . . ?
C14 C13 C12 120.8(3) . . ?
C15 C14 C13 120.7(3) . . ?
C14 C15 C10 119.5(3) . . ?
C18 C17 C21 115.96(19) . . ?
C18 C17 C22 122.13(17) . . ?
C21 C17 C22 121.90(18) . . ?
C19 C18 C17 119.9(2) . . ?
N4 C19 C18 124.7(2) . . ?
N4 C20 C21 124.7(2) . . ?
C17 C21 C20 119.7(2) . . ?
C26 C22 C23 116.04(18) . . ?
C26 C22 C17 122.33(17) . . ?
C23 C22 C17 121.63(17) . . ?
C24 C23 C22 119.52(19) . . ?
N5 C24 C23 124.6(2) . . ?
N5 C25 C26 124.3(2) . . ?
C25 C26 C22 120.0(2) . . ?
N2 N1 C11 115.16(17) . . ?
N2 N1 C8 112.28(16) . . ?
C11 N1 C8 106.06(16) . . ?
C7 N2 N1 120.72(17) . . ?
C20 N4 C19 115.00(19) . . ?
C24 N5 C25 115.37(19) . . ?
O1 S1 O2 119.71(12) . . ?
O1 S1 N3 107.33(12) . . ?
O2 S1 N3 107.81(13) . . ?
O1 S1 C3 106.79(10) . . ?
O2 S1 C3 105.67(9) . . ?
N3 S1 C3 109.23(10) . . ?

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_IDP-BIP
_database_code_depnum_ccdc_archive 'CCDC 1849065'
_audit_update_record             
;
2018-06-13 deposited with the CCDC.
2018-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
4-chloro-N-(2-methyl-2,3-dihydroindol-1-yl)-3-sulfamoylbenzamide-2-pyridin-2-ylpyridine
_chemical_name_common            "Indapamide-2,2'-Bipyridine cocrystal"
_chemical_melting_point          407K
_chemical_formula_moiety         'C16 H16 Cl N3 O3 S, C10 H8 N2'
_chemical_formula_sum            'C26 H24 Cl N5 O3 S'
_chemical_formula_weight         522.01

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                   7.3151(2)
_cell_length_b                   8.9370(3)
_cell_length_c                   38.9526(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.702(2)
_cell_angle_gamma                90
_cell_volume                     2541.21(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5345
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      25.71

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.23
_exptl_absorpt_coefficient_mu    0.271
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_correction_T_min  0.8657
_exptl_absorpt_correction_T_max  1.2051
_exptl_absorpt_process_details   
'Parkin S,Moezzi B & Hope H, (1995) J. Appl. Cryst. 28, 53-56 Cubic fit to sin(theta)/lambda - 24 parameters'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47789
_diffrn_reflns_av_unetI/netI     0.1082
_diffrn_reflns_av_R_equivalents  0.1597
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         2.096
_diffrn_reflns_theta_max         25.736
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4804
_reflns_number_gt                2630
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0483P)²+1.9700P] 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         4804
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1741
_refine_ls_R_factor_gt           0.0798
_refine_ls_wR_factor_ref         0.1536
_refine_ls_wR_factor_gt          0.1289
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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 0.58335(19) 0.78222(12) 0.39925(3) 0.0525(4) Uani 1 1 d . . . . .
Cl1 Cl 0.94745(18) 0.57392(15) 0.39012(3) 0.0652(4) Uani 1 1 d . . . . .
O3 O 0.4043(4) 0.9082(3) 0.26813(6) 0.0398(7) Uani 1 1 d . . . . .
N2 N 0.5001(5) 0.7096(4) 0.23835(8) 0.0386(9) Uani 1 1 d . . . . .
C7 C 0.4954(5) 0.7937(4) 0.26656(9) 0.0305(9) Uani 1 1 d . . . . .
O1 O 0.4195(5) 0.8648(4) 0.39163(8) 0.0808(12) Uani 1 1 d . . . . .
N1 N 0.4108(5) 0.7543(3) 0.20696(8) 0.0369(9) Uani 1 1 d . . . . .
C1 C 0.6099(5) 0.7375(4) 0.29689(9) 0.0305(9) Uani 1 1 d . . . . .
N3 N 0.5298(8) 0.6296(5) 0.41691(10) 0.0559(12) Uani 1 1 d . . . . .
O2 O 0.7316(5) 0.8487(4) 0.41918(8) 0.0780(11) Uani 1 1 d . . . . .
C2 C 0.5629(6) 0.7791(4) 0.32926(9) 0.0356(10) Uani 1 1 d . . . . .
H2 H 0.4625 0.8415 0.3314 0.043 Uiso 1 1 calc R U . . .
C3 C 0.6617(6) 0.7301(4) 0.35868(9) 0.0349(10) Uani 1 1 d . . . . .
N4 N 0.7310(5) 0.4467(4) 0.47076(8) 0.0433(9) Uani 1 1 d . . . . .
C4 C 0.8143(6) 0.6415(4) 0.35483(10) 0.0402(11) Uani 1 1 d . . . . .
N5 N 0.7734(5) 0.5815(4) 0.55779(8) 0.0470(9) Uani 1 1 d . . . . .
C5 C 0.8625(6) 0.6001(5) 0.32285(11) 0.0534(12) Uani 1 1 d . . . . .
H5 H 0.9649 0.5400 0.3207 0.064 Uiso 1 1 calc R U . . .
C6 C 0.7607(6) 0.6466(5) 0.29388(10) 0.0456(11) Uani 1 1 d . . . . .
H6 H 0.7935 0.6168 0.2722 0.055 Uiso 1 1 calc R U . . .
C11 C 0.2553(6) 0.6704(4) 0.19588(11) 0.0393(11) Uani 1 1 d . . . . .
C12 C 0.1310(7) 0.6027(5) 0.21561(13) 0.0619(14) Uani 1 1 d . . . . .
H12 H 0.1425 0.6072 0.2395 0.074 Uiso 1 1 calc R U . . .
C13 C -0.0145(7) 0.5264(7) 0.19819(18) 0.0841(18) Uani 1 1 d . . . . .
H13 H -0.1014 0.4781 0.2106 0.101 Uiso 1 1 calc R U . . .
C14 C -0.0294(8) 0.5225(7) 0.16265(18) 0.0851(19) Uani 1 1 d . . . . .
H14 H -0.1271 0.4719 0.1515 0.102 Uiso 1 1 calc R U . . .
C15 C 0.0968(8) 0.5915(6) 0.14359(14) 0.0733(16) Uani 1 1 d . . . . .
H15 H 0.0852 0.5882 0.1197 0.088 Uiso 1 1 calc R U . . .
C10 C 0.2412(6) 0.6660(5) 0.16040(11) 0.0470(12) Uani 1 1 d . . . . .
C9 C 0.4005(7) 0.7452(5) 0.14727(11) 0.0595(14) Uani 1 1 d . . . . .
H9A H 0.3665 0.8442 0.1389 0.071 Uiso 1 1 calc R U . . .
H9B H 0.4524 0.6892 0.1289 0.071 Uiso 1 1 calc R U . . .
C8 C 0.5321(6) 0.7540(5) 0.17843(10) 0.0508(12) Uani 1 1 d . . . . .
H8 H 0.6021 0.6604 0.1797 0.061 Uiso 1 1 calc R U . . .
C16 C 0.6673(7) 0.8810(5) 0.18028(13) 0.0717(15) Uani 1 1 d . . . . .
H16A H 0.6037 0.9737 0.1759 0.108 Uiso 1 1 calc R U . . .
H16B H 0.7553 0.8665 0.1633 0.108 Uiso 1 1 calc R U . . .
H16C H 0.7291 0.8839 0.2028 0.108 Uiso 1 1 calc R U . . .
C17 C 0.7727(5) 0.4469(4) 0.50501(10) 0.0324(9) Uani 1 1 d . . . . .
C18 C 0.8399(6) 0.3208(4) 0.52165(11) 0.0443(11) Uani 1 1 d . . . . .
H18 H 0.8676 0.3228 0.5453 0.053 Uiso 1 1 calc R U . . .
C19 C 0.8661(6) 0.1913(5) 0.50338(12) 0.0529(12) Uani 1 1 d . . . . .
H19 H 0.9136 0.1060 0.5143 0.063 Uiso 1 1 calc R U . . .
C20 C 0.8208(6) 0.1910(5) 0.46865(13) 0.0542(13) Uani 1 1 d . . . . .
H20 H 0.8341 0.1049 0.4556 0.065 Uiso 1 1 calc R U . . .
C21 C 0.7558(7) 0.3196(5) 0.45365(12) 0.0548(13) Uani 1 1 d . . . . .
H21 H 0.7270 0.3189 0.4300 0.066 Uiso 1 1 calc R U . . .
C22 C 0.7423(5) 0.5879(4) 0.52378(10) 0.0326(9) Uani 1 1 d . . . . .
C23 C 0.6879(6) 0.7188(5) 0.50711(11) 0.0466(11) Uani 1 1 d . . . . .
H23 H 0.6673 0.7216 0.4833 0.056 Uiso 1 1 calc R U . . .
C24 C 0.6649(6) 0.8453(5) 0.52680(14) 0.0562(13) Uani 1 1 d . . . . .
H24 H 0.6257 0.9345 0.5164 0.067 Uiso 1 1 calc R U . . .
C25 C 0.7001(7) 0.8380(5) 0.56144(13) 0.0593(14) Uani 1 1 d . . . . .
H25 H 0.6872 0.9223 0.5751 0.071 Uiso 1 1 calc R U . . .
C26 C 0.7545(7) 0.7057(5) 0.57587(12) 0.0580(13) Uani 1 1 d . . . . .
H26 H 0.7797 0.7020 0.5996 0.070 Uiso 1 1 calc R U . . .
H2A H 0.536(5) 0.622(4) 0.2381(9) 0.027(11) Uiso 1 1 d . . . . .
H3A H 0.618(7) 0.588(5) 0.4321(13) 0.084(18) Uiso 1 1 d . . . . .
H3B H 0.420(7) 0.595(5) 0.4179(12) 0.07(2) 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 O2 1.422(3) . ?
S1 O1 1.423(3) . ?
S1 N3 1.588(4) . ?
S1 C3 1.777(4) . ?
Cl1 C4 1.741(4) . ?
O3 C7 1.225(4) . ?
N2 C7 1.333(5) . ?
N2 N1 1.407(4) . ?
N2 H2A 0.83(3) . ?
C7 C1 1.491(5) . ?
N1 C11 1.407(5) . ?
N1 C8 1.466(5) . ?
C1 C2 1.379(5) . ?
C1 C6 1.381(5) . ?
N3 H3A 0.92(5) . ?
N3 H3B 0.86(5) . ?
C2 C3 1.386(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(5) . ?
N4 C21 1.335(5) . ?
N4 C17 1.350(5) . ?
C4 C5 1.367(5) . ?
N5 C26 1.326(5) . ?
N5 C22 1.331(5) . ?
C5 C6 1.376(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C11 C12 1.369(6) . ?
C11 C10 1.380(6) . ?
C12 C13 1.402(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(7) . ?
C14 H14 0.9300 . ?
C15 C10 1.378(6) . ?
C15 H15 0.9300 . ?
C10 C9 1.482(6) . ?
C9 C8 1.502(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C8 C16 1.504(6) . ?
C8 H8 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.374(5) . ?
C17 C22 1.481(5) . ?
C18 C19 1.378(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.361(6) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.384(5) . ?
C23 C24 1.383(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.359(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.358(6) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

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 O1 120.0(2) . . ?
O2 S1 N3 108.9(2) . . ?
O1 S1 N3 107.9(3) . . ?
O2 S1 C3 108.5(2) . . ?
O1 S1 C3 105.43(19) . . ?
N3 S1 C3 105.2(2) . . ?
C7 N2 N1 121.4(3) . . ?
C7 N2 H2A 125(2) . . ?
N1 N2 H2A 113(2) . . ?
O3 C7 N2 123.7(4) . . ?
O3 C7 C1 121.4(3) . . ?
N2 C7 C1 114.8(3) . . ?
C11 N1 N2 115.9(3) . . ?
C11 N1 C8 106.5(3) . . ?
N2 N1 C8 112.8(3) . . ?
C2 C1 C6 119.0(4) . . ?
C2 C1 C7 118.2(4) . . ?
C6 C1 C7 122.8(4) . . ?
S1 N3 H3A 116(3) . . ?
S1 N3 H3B 126(3) . . ?
H3A N3 H3B 116(5) . . ?
C1 C2 C3 121.6(4) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 118.2(4) . . ?
C4 C3 S1 123.7(3) . . ?
C2 C3 S1 118.1(3) . . ?
C21 N4 C17 117.7(4) . . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 Cl1 117.5(3) . . ?
C3 C4 Cl1 121.8(3) . . ?
C26 N5 C22 118.4(4) . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.1(4) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C12 C11 C10 122.7(4) . . ?
C12 C11 N1 128.1(4) . . ?
C10 C11 N1 109.2(4) . . ?
C11 C12 C13 117.0(5) . . ?
C11 C12 H12 121.5 . . ?
C13 C12 H12 121.5 . . ?
C14 C13 C12 120.4(5) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 121.3(5) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C10 118.9(5) . . ?
C14 C15 H15 120.5 . . ?
C10 C15 H15 120.5 . . ?
C15 C10 C11 119.7(5) . . ?
C15 C10 C9 131.5(5) . . ?
C11 C10 C9 108.8(4) . . ?
C10 C9 C8 102.9(3) . . ?
C10 C9 H9A 111.2 . . ?
C8 C9 H9A 111.2 . . ?
C10 C9 H9B 111.2 . . ?
C8 C9 H9B 111.2 . . ?
H9A C9 H9B 109.1 . . ?
N1 C8 C9 103.0(4) . . ?
N1 C8 C16 113.0(4) . . ?
C9 C8 C16 117.6(4) . . ?
N1 C8 H8 107.6 . . ?
C9 C8 H8 107.6 . . ?
C16 C8 H8 107.6 . . ?
C8 C16 H16A 109.5 . . ?
C8 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C8 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N4 C17 C18 121.1(4) . . ?
N4 C17 C22 117.2(3) . . ?
C18 C17 C22 121.7(4) . . ?
C17 C18 C19 120.1(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 118.6(4) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C21 C20 C19 118.5(4) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
N4 C21 C20 124.0(4) . . ?
N4 C21 H21 118.0 . . ?
C20 C21 H21 118.0 . . ?
N5 C22 C23 121.9(4) . . ?
N5 C22 C17 115.7(3) . . ?
C23 C22 C17 122.4(4) . . ?
C24 C23 C22 118.2(4) . . ?
C24 C23 H23 120.9 . . ?
C22 C23 H23 120.9 . . ?
C25 C24 C23 119.3(4) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C26 C25 C24 119.0(4) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
N5 C26 C25 123.1(4) . . ?
N5 C26 H26 118.4 . . ?
C25 C26 H26 118.4 . . ?

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_IDP-MeHP
_database_code_depnum_ccdc_archive 'CCDC 1849064'
_audit_update_record             
;
2018-06-13 deposited with the CCDC.
2018-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
4-chloro-N-(2-methyl-2,3-dihydroindol-1-yl)-3-sulfamoylbenzamide-6-methyl-2-pyridone
_chemical_name_common            'Indapamide-methylpyridone cocrystal'
_chemical_melting_point          449K
_chemical_formula_moiety         'C16 H16 Cl N3 O3 S, C6 H7 N O'
_chemical_formula_sum            'C22 H23 Cl N4 O4 S'
_chemical_formula_weight         474.95

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                   7.765(7)
_cell_length_b                   8.741(8)
_cell_length_c                   34.52(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.96(4)
_cell_angle_gamma                90
_cell_volume                     2338(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9941
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      26.38

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.288
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32668
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.365
_diffrn_reflns_theta_max         26.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4763
_reflns_number_gt                3740
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0518P)²+1.6388P] 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         4763
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1436
_refine_ls_wR_factor_gt          0.1354
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.001
_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
Cl1 Cl 0.07510(13) 0.50471(18) 0.40504(3) 0.1151(5) Uani 1 1 d . . . . .
S1 S 0.42338(11) 0.71333(8) 0.42200(2) 0.0572(2) Uani 1 1 d . . . . .
O4 O 0.7788(2) 0.4663(2) 0.48560(5) 0.0491(4) Uani 1 1 d . . . . .
O3 O 0.5958(2) 0.8019(2) 0.27905(5) 0.0523(5) Uani 1 1 d . . . . .
O2 O 0.5878(4) 0.7810(3) 0.41733(6) 0.0943(9) Uani 1 1 d . . . . .
O1 O 0.2864(4) 0.8028(3) 0.43535(7) 0.1069(11) Uani 1 1 d . . . . .
N3 N 0.4500(4) 0.5682(3) 0.44938(7) 0.0493(6) Uani 1 1 d . . . . .
N1 N 0.5674(3) 0.6528(3) 0.20952(6) 0.0584(6) Uani 1 1 d . . . . .
N4 N 1.0038(3) 0.3037(2) 0.48151(6) 0.0377(4) Uani 1 1 d . . . . .
N2 N 0.4837(3) 0.6072(3) 0.24220(6) 0.0552(6) Uani 1 1 d . . . . .
C3 C 0.3529(3) 0.6423(3) 0.37538(7) 0.0446(6) Uani 1 1 d . . . . .
C4 C 0.2047(4) 0.5549(4) 0.36848(8) 0.0629(8) Uani 1 1 d . . . . .
C5 C 0.1565(4) 0.5050(5) 0.33144(9) 0.0842(12) Uani 1 1 d . . . . .
H5 H 0.0589 0.4441 0.3270 0.101 Uiso 1 1 calc R U . . .
C6 C 0.2530(4) 0.5453(4) 0.30114(8) 0.0701(9) Uani 1 1 d . . . . .
H6 H 0.2195 0.5118 0.2762 0.084 Uiso 1 1 calc R U . . .
C1 C 0.3983(3) 0.6343(3) 0.30718(7) 0.0448(6) Uani 1 1 d . . . . .
C2 C 0.4474(3) 0.6817(3) 0.34454(7) 0.0414(6) Uani 1 1 d . . . . .
H2 H 0.5461 0.7413 0.3489 0.050 Uiso 1 1 calc R U . . .
C7 C 0.5028(3) 0.6891(3) 0.27504(7) 0.0435(6) Uani 1 1 d . . . . .
C11 C 0.7176(4) 0.5687(4) 0.20241(8) 0.0613(8) Uani 1 1 d . . . . .
C12 C 0.8336(5) 0.4997(5) 0.22874(11) 0.0808(10) Uani 1 1 d . . . . .
H12 H 0.8195 0.5037 0.2553 0.097 Uiso 1 1 calc R U . . .
C13 C 0.9720(5) 0.4240(6) 0.21434(16) 0.1159(18) Uani 1 1 d . . . . .
H13 H 1.0509 0.3745 0.2315 0.139 Uiso 1 1 calc R U . . .
C14 C 0.9959(6) 0.4200(7) 0.17562(18) 0.132(2) Uani 1 1 d . . . . .
H14 H 1.0915 0.3703 0.1668 0.159 Uiso 1 1 calc R U . . .
C15 C 0.8781(7) 0.4898(7) 0.14956(14) 0.120(2) Uani 1 1 d . . . . .
H15 H 0.8934 0.4859 0.1231 0.143 Uiso 1 1 calc R U . . .
C10 C 0.7376(5) 0.5653(5) 0.16289(9) 0.0792(11) Uani 1 1 d . . . . .
C9 C 0.5860(6) 0.6436(5) 0.14256(9) 0.0960(13) Uani 1 1 d . . . . .
H9A H 0.5438 0.5869 0.1197 0.115 Uiso 1 1 calc R U . . .
H9B H 0.6157 0.7466 0.1349 0.115 Uiso 1 1 calc R U . . .
C8 C 0.4520(5) 0.6463(4) 0.17289(8) 0.0714(9) Uani 1 1 d . . . . .
H8 H 0.3900 0.5486 0.1720 0.086 Uiso 1 1 calc R U . . .
C16 C 0.3221(6) 0.7749(5) 0.17035(13) 0.1056(14) Uani 1 1 d . . . . .
H16A H 0.2478 0.7664 0.1914 0.158 Uiso 1 1 calc R U . . .
H16B H 0.2543 0.7688 0.1461 0.158 Uiso 1 1 calc R U . . .
H16C H 0.3815 0.8712 0.1720 0.158 Uiso 1 1 calc R U . . .
C17 C 0.8347(3) 0.3387(3) 0.47391(7) 0.0401(5) Uani 1 1 d . . . . .
C18 C 0.7350(4) 0.2288(3) 0.45282(9) 0.0589(7) Uani 1 1 d . . . . .
H18 H 0.6188 0.2473 0.4462 0.071 Uiso 1 1 calc R U . . .
C19 C 0.8081(4) 0.0960(3) 0.44211(9) 0.0625(8) Uani 1 1 d . . . . .
H19 H 0.7401 0.0233 0.4287 0.075 Uiso 1 1 calc R U . . .
C20 C 0.9822(4) 0.0659(3) 0.45071(8) 0.0513(6) Uani 1 1 d . . . . .
H20 H 1.0303 -0.0258 0.4431 0.062 Uiso 1 1 calc R U . . .
C21 C 1.0803(3) 0.1715(3) 0.47023(7) 0.0424(6) Uani 1 1 d . . . . .
C22 C 1.2705(4) 0.1593(4) 0.48009(10) 0.0673(9) Uani 1 1 d . . . . .
H22A H 1.3105 0.0609 0.4722 0.101 Uiso 1 1 calc R U . . .
H22B H 1.2938 0.1710 0.5076 0.101 Uiso 1 1 calc R U . . .
H22C H 1.3291 0.2381 0.4668 0.101 Uiso 1 1 calc R U . . .
H4A H 1.067(3) 0.373(3) 0.4935(8) 0.047(7) Uiso 1 1 d . . . . .
H2A H 0.433(4) 0.513(4) 0.2419(9) 0.063(9) Uiso 1 1 d . . . . .
H3A H 0.373(4) 0.559(4) 0.4655(9) 0.065(10) Uiso 1 1 d . . . . .
H3B H 0.551(4) 0.550(4) 0.4563(8) 0.059(9) 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
Cl1 C4 1.724(3) . ?
S1 O1 1.422(3) . ?
S1 O2 1.426(3) . ?
S1 N3 1.587(3) . ?
S1 C3 1.776(3) . ?
O4 C17 1.272(3) . ?
O3 C7 1.224(3) . ?
N3 H3A 0.85(3) . ?
N3 H3B 0.82(3) . ?
N1 N2 1.399(3) . ?
N1 C11 1.414(4) . ?
N1 C8 1.500(4) . ?
N4 C17 1.356(3) . ?
N4 C21 1.368(3) . ?
N4 H4A 0.87(3) . ?
N2 C7 1.341(3) . ?
N2 H2A 0.91(3) . ?
C3 C2 1.378(4) . ?
C3 C4 1.388(4) . ?
C4 C5 1.379(4) . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C6 C1 1.375(4) . ?
C6 H6 0.9300 . ?
C1 C2 1.383(3) . ?
C1 C7 1.498(4) . ?
C2 H2 0.9300 . ?
C11 C12 1.374(5) . ?
C11 C10 1.384(4) . ?
C12 C13 1.384(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.363(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(8) . ?
C14 H14 0.9300 . ?
C15 C10 1.381(6) . ?
C15 H15 0.9300 . ?
C10 C9 1.495(6) . ?
C9 C8 1.526(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C8 C16 1.509(5) . ?
C8 H8 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.405(4) . ?
C18 C19 1.355(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.389(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.348(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.496(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
O1 S1 O2 120.3(2) . . ?
O1 S1 N3 108.42(16) . . ?
O2 S1 N3 108.52(16) . . ?
O1 S1 C3 107.18(15) . . ?
O2 S1 C3 105.37(13) . . ?
N3 S1 C3 106.24(14) . . ?
S1 N3 H3A 113(2) . . ?
S1 N3 H3B 114(2) . . ?
H3A N3 H3B 120(3) . . ?
N2 N1 C11 115.2(2) . . ?
N2 N1 C8 112.7(2) . . ?
C11 N1 C8 106.6(2) . . ?
C17 N4 C21 124.7(2) . . ?
C17 N4 H4A 116.5(18) . . ?
C21 N4 H4A 118.7(18) . . ?
C7 N2 N1 120.0(2) . . ?
C7 N2 H2A 120.9(19) . . ?
N1 N2 H2A 118.3(19) . . ?
C2 C3 C4 119.0(2) . . ?
C2 C3 S1 117.7(2) . . ?
C4 C3 S1 123.2(2) . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 Cl1 117.6(2) . . ?
C3 C4 Cl1 122.2(2) . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C6 C1 C2 118.8(2) . . ?
C6 C1 C7 123.4(2) . . ?
C2 C1 C7 117.8(2) . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
O3 C7 N2 123.8(2) . . ?
O3 C7 C1 121.3(2) . . ?
N2 C7 C1 114.9(2) . . ?
C12 C11 C10 122.0(4) . . ?
C12 C11 N1 128.6(3) . . ?
C10 C11 N1 109.4(3) . . ?
C11 C12 C13 117.5(4) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 H12 121.2 . . ?
C14 C13 C12 121.7(5) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 120.0(5) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 119.8(4) . . ?
C14 C15 H15 120.1 . . ?
C10 C15 H15 120.1 . . ?
C15 C10 C11 118.9(4) . . ?
C15 C10 C9 132.6(4) . . ?
C11 C10 C9 108.3(3) . . ?
C10 C9 C8 103.7(3) . . ?
C10 C9 H9A 111.0 . . ?
C8 C9 H9A 111.0 . . ?
C10 C9 H9B 111.0 . . ?
C8 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
N1 C8 C16 112.3(3) . . ?
N1 C8 C9 100.6(3) . . ?
C16 C8 C9 117.1(3) . . ?
N1 C8 H8 108.8 . . ?
C16 C8 H8 108.8 . . ?
C9 C8 H8 108.8 . . ?
C8 C16 H16A 109.5 . . ?
C8 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C8 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 N4 118.9(2) . . ?
O4 C17 C18 125.1(2) . . ?
N4 C17 C18 115.9(2) . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 121.6(3) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C21 C20 C19 119.0(3) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C20 C21 N4 118.7(2) . . ?
C20 C21 C22 125.4(2) . . ?
N4 C21 C22 115.9(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.453
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_IDP-PHE
_database_code_depnum_ccdc_archive 'CCDC 1849063'
_audit_update_record             
;
2018-06-13 deposited with the CCDC.
2018-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
4-chloro-N-(2-methyl-2,3-dihydroindol-1-yl)-3-sulfamoylbenzamide-phenazine
_chemical_name_common            'Indapamide-Phenazine cocrystal'
_chemical_melting_point          478K
_chemical_formula_moiety         'C16 H16 Cl N3 O3 S, C12 H8 N2'
_chemical_formula_sum            'C28 H24 Cl N5 O3 S'
_chemical_formula_weight         546.03

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                   7.1759(3)
_cell_length_b                   9.4074(4)
_cell_length_c                   39.0523(17)
_cell_angle_alpha                90
_cell_angle_beta                 93.389(2)
_cell_angle_gamma                90
_cell_volume                     2631.68(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      28.30

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.265
_shelx_estimated_absorpt_T_min   0.901
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25417
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_theta_min         3.010
_diffrn_reflns_theta_max         28.297
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             6467
_reflns_number_gt                5826
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0360P)²+1.7835P] 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         6467
_refine_ls_number_parameters     356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1282
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_refine_ls_shift/su_max          0.001
_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 0.42043(9) 0.16064(6) 0.60258(2) 0.05006(16) Uani 1 1 d . . . . .
Cl1 Cl 0.05355(9) 0.36472(7) 0.60855(2) 0.05965(18) Uani 1 1 d . . . . .
O1 O 0.5738(2) 0.04862(14) 0.73434(3) 0.0427(3) Uani 1 1 d . . . . .
N4 N 0.1976(2) 0.55269(17) 0.45625(4) 0.0377(3) Uani 1 1 d . . . . .
N5 N 0.2953(2) 0.41582(16) 0.51925(4) 0.0343(3) Uani 1 1 d . . . . .
N1 N 0.4984(2) 0.24968(18) 0.76211(4) 0.0393(4) Uani 1 1 d . . . . .
N2 N 0.5963(2) 0.21069(19) 0.79266(4) 0.0409(4) Uani 1 1 d . . . . .
O2 O 0.2690(3) 0.09718(19) 0.58281(4) 0.0743(6) Uani 1 1 d . . . . .
O3 O 0.5847(3) 0.0799(2) 0.61160(4) 0.0867(7) Uani 1 1 d . . . . .
N3 N 0.4809(4) 0.3017(3) 0.58344(5) 0.0562(5) Uani 1 1 d . . . . .
C7 C 0.4935(2) 0.16328(18) 0.73480(4) 0.0311(3) Uani 1 1 d . . . . .
C22 C 0.2411(2) 0.4140(2) 0.45759(4) 0.0335(4) Uani 1 1 d . . . . .
C23 C 0.2501(2) 0.55453(19) 0.51797(4) 0.0319(3) Uani 1 1 d . . . . .
C1 C 0.3822(2) 0.21827(18) 0.70394(4) 0.0319(3) Uani 1 1 d . . . . .
C28 C 0.2000(2) 0.62305(19) 0.48612(5) 0.0331(4) Uani 1 1 d . . . . .
C6 C 0.4330(3) 0.17265(18) 0.67200(4) 0.0332(4) Uani 1 1 d . . . . .
H6 H 0.5327 0.1102 0.6706 0.040 Uiso 1 1 calc R U . . .
C5 C 0.3376(3) 0.21870(19) 0.64213(4) 0.0355(4) Uani 1 1 d . . . . .
C17 C 0.2899(2) 0.34459(19) 0.48958(4) 0.0321(3) Uani 1 1 d . . . . .
C24 C 0.2546(3) 0.6351(2) 0.54879(5) 0.0428(4) Uani 1 1 d . . . . .
H24 H 0.2873 0.5917 0.5697 0.051 Uiso 1 1 calc R U . . .
C18 C 0.3352(3) 0.1973(2) 0.48930(5) 0.0430(4) Uani 1 1 d . . . . .
H18 H 0.3674 0.1505 0.5098 0.052 Uiso 1 1 calc R U . . .
C4 C 0.1839(3) 0.3079(2) 0.64461(5) 0.0407(4) Uani 1 1 d . . . . .
C27 C 0.1521(3) 0.7699(2) 0.48638(6) 0.0461(5) Uani 1 1 d . . . . .
H27 H 0.1161 0.8159 0.4660 0.055 Uiso 1 1 calc R U . . .
C11 C 0.7520(3) 0.2963(2) 0.80194(5) 0.0439(5) Uani 1 1 d . . . . .
C25 C 0.2112(3) 0.7750(2) 0.54774(6) 0.0474(5) Uani 1 1 d . . . . .
H25 H 0.2159 0.8274 0.5680 0.057 Uiso 1 1 calc R U . . .
C19 C 0.3313(3) 0.1255(2) 0.45931(6) 0.0491(5) Uani 1 1 d . . . . .
H19 H 0.3618 0.0294 0.4594 0.059 Uiso 1 1 calc R U . . .
C26 C 0.1589(3) 0.8425(2) 0.51631(6) 0.0488(5) Uani 1 1 d . . . . .
H26 H 0.1286 0.9386 0.5162 0.059 Uiso 1 1 calc R U . . .
C2 C 0.2328(3) 0.3104(3) 0.70585(5) 0.0486(5) Uani 1 1 d . . . . .
H2 H 0.1995 0.3433 0.7271 0.058 Uiso 1 1 calc R U . . .
C21 C 0.2384(3) 0.3333(2) 0.42684(5) 0.0471(5) Uani 1 1 d . . . . .
H21 H 0.2067 0.3768 0.4059 0.056 Uiso 1 1 calc R U . . .
C20 C 0.2819(3) 0.1935(3) 0.42782(6) 0.0510(5) Uani 1 1 d . . . . .
H20 H 0.2792 0.1414 0.4075 0.061 Uiso 1 1 calc R U . . .
C3 C 0.1333(3) 0.3536(3) 0.67640(6) 0.0545(6) Uani 1 1 d . . . . .
H3 H 0.0313 0.4138 0.6779 0.065 Uiso 1 1 calc R U . . .
C10 C 0.7760(3) 0.3036(3) 0.83760(6) 0.0540(6) Uani 1 1 d . . . . .
C8 C 0.4770(3) 0.2102(3) 0.82271(5) 0.0501(5) Uani 1 1 d . . . . .
H8 H 0.4001 0.2964 0.8221 0.060 Uiso 1 1 calc R U . . .
C12 C 0.8701(3) 0.3642(3) 0.78084(7) 0.0605(6) Uani 1 1 d . . . . .
H12 H 0.8533 0.3575 0.7571 0.073 Uiso 1 1 calc R U . . .
C9 C 0.6230(4) 0.2207(3) 0.85279(5) 0.0625(7) Uani 1 1 d . . . . .
H9A H 0.5739 0.2706 0.8720 0.075 Uiso 1 1 calc R U . . .
H9B H 0.6659 0.1273 0.8603 0.075 Uiso 1 1 calc R U . . .
C15 C 0.9215(4) 0.3821(4) 0.85238(7) 0.0729(9) Uani 1 1 d . . . . .
H15 H 0.9396 0.3881 0.8761 0.087 Uiso 1 1 calc R U . . .
C13 C 1.0152(4) 0.4432(4) 0.79620(9) 0.0802(9) Uani 1 1 d . . . . .
H13 H 1.0969 0.4910 0.7826 0.096 Uiso 1 1 calc R U . . .
C16 C 0.3511(5) 0.0822(4) 0.82249(8) 0.0832(9) Uani 1 1 d . . . . .
H16A H 0.2743 0.0804 0.8015 0.125 Uiso 1 1 calc R U . . .
H16B H 0.2732 0.0872 0.8416 0.125 Uiso 1 1 calc R U . . .
H16C H 0.4255 -0.0026 0.8242 0.125 Uiso 1 1 calc R U . . .
C14 C 1.0397(4) 0.4516(4) 0.83147(9) 0.0849(10) Uani 1 1 d . . . . .
H14 H 1.1378 0.5052 0.8413 0.102 Uiso 1 1 calc R U . . .
H1A H 0.463(3) 0.336(3) 0.7600(6) 0.042(6) Uiso 1 1 d . . . . .
H3B H 0.597(4) 0.315(3) 0.5838(7) 0.067(9) Uiso 1 1 d . . . . .
H3A H 0.408(4) 0.323(3) 0.5668(7) 0.059(8) 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 O2 1.426(2) . ?
S1 O3 1.4287(19) . ?
S1 N3 1.596(2) . ?
S1 C5 1.7736(18) . ?
Cl1 C4 1.7286(18) . ?
O1 C7 1.224(2) . ?
N4 C28 1.340(2) . ?
N4 C22 1.341(2) . ?
N5 C17 1.337(2) . ?
N5 C23 1.345(2) . ?
N1 C7 1.340(2) . ?
N1 N2 1.397(2) . ?
N1 H1A 0.85(2) . ?
N2 C11 1.407(3) . ?
N2 C8 1.493(3) . ?
N3 H3B 0.84(3) . ?
N3 H3A 0.83(3) . ?
C7 C1 1.498(2) . ?
C22 C21 1.420(3) . ?
C22 C17 1.435(2) . ?
C23 C24 1.421(3) . ?
C23 C28 1.428(2) . ?
C1 C2 1.384(3) . ?
C1 C6 1.388(2) . ?
C28 C27 1.424(3) . ?
C6 C5 1.387(2) . ?
C6 H6 0.9300 . ?
C5 C4 1.394(3) . ?
C17 C18 1.423(3) . ?
C24 C25 1.352(3) . ?
C24 H24 0.9300 . ?
C18 C19 1.351(3) . ?
C18 H18 0.9300 . ?
C4 C3 1.382(3) . ?
C27 C26 1.352(3) . ?
C27 H27 0.9300 . ?
C11 C12 1.374(3) . ?
C11 C10 1.395(3) . ?
C25 C26 1.413(3) . ?
C25 H25 0.9300 . ?
C19 C20 1.412(3) . ?
C19 H19 0.9300 . ?
C26 H26 0.9300 . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C21 C20 1.352(3) . ?
C21 H21 0.9300 . ?
C20 H20 0.9300 . ?
C3 H3 0.9300 . ?
C10 C15 1.377(4) . ?
C10 C9 1.498(4) . ?
C8 C16 1.505(4) . ?
C8 C9 1.530(3) . ?
C8 H8 0.9800 . ?
C12 C13 1.387(4) . ?
C12 H12 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C15 C14 1.377(5) . ?
C15 H15 0.9300 . ?
C13 C14 1.380(4) . ?
C13 H13 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C14 H14 0.9300 . ?

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 120.14(14) . . ?
O2 S1 N3 108.31(12) . . ?
O3 S1 N3 108.31(15) . . ?
O2 S1 C5 108.44(11) . . ?
O3 S1 C5 105.27(9) . . ?
N3 S1 C5 105.44(10) . . ?
C28 N4 C22 117.09(15) . . ?
C17 N5 C23 117.36(15) . . ?
C7 N1 N2 120.58(16) . . ?
C7 N1 H1A 120.4(15) . . ?
N2 N1 H1A 117.6(15) . . ?
N1 N2 C11 114.89(17) . . ?
N1 N2 C8 112.91(16) . . ?
C11 N2 C8 106.43(15) . . ?
S1 N3 H3B 114(2) . . ?
S1 N3 H3A 113.2(19) . . ?
H3B N3 H3A 123(3) . . ?
O1 C7 N1 123.79(16) . . ?
O1 C7 C1 121.46(15) . . ?
N1 C7 C1 114.75(15) . . ?
N4 C22 C21 119.72(17) . . ?
N4 C22 C17 121.39(16) . . ?
C21 C22 C17 118.89(17) . . ?
N5 C23 C24 119.54(17) . . ?
N5 C23 C28 121.21(16) . . ?
C24 C23 C28 119.24(17) . . ?
C2 C1 C6 119.16(16) . . ?
C2 C1 C7 123.43(16) . . ?
C6 C1 C7 117.40(15) . . ?
N4 C28 C27 119.67(17) . . ?
N4 C28 C23 121.64(16) . . ?
C27 C28 C23 118.70(17) . . ?
C5 C6 C1 121.10(16) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C6 C5 C4 118.88(16) . . ?
C6 C5 S1 117.52(14) . . ?
C4 C5 S1 123.59(13) . . ?
N5 C17 C18 119.99(17) . . ?
N5 C17 C22 121.30(16) . . ?
C18 C17 C22 118.71(17) . . ?
C25 C24 C23 120.01(19) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C19 C18 C17 120.04(19) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C3 C4 C5 120.04(17) . . ?
C3 C4 Cl1 118.50(15) . . ?
C5 C4 Cl1 121.46(15) . . ?
C26 C27 C28 120.0(2) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C12 C11 C10 122.1(2) . . ?
C12 C11 N2 128.33(19) . . ?
C10 C11 N2 109.5(2) . . ?
C24 C25 C26 120.82(19) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C18 C19 C20 121.3(2) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C27 C26 C25 121.22(19) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C3 C2 C1 120.30(18) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C20 C21 C22 120.3(2) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C20 C19 120.7(2) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C2 C3 C4 120.44(19) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C15 C10 C11 119.4(3) . . ?
C15 C10 C9 132.0(2) . . ?
C11 C10 C9 108.6(2) . . ?
N2 C8 C16 111.7(2) . . ?
N2 C8 C9 101.82(18) . . ?
C16 C8 C9 116.1(2) . . ?
N2 C8 H8 109.0 . . ?
C16 C8 H8 109.0 . . ?
C9 C8 H8 109.0 . . ?
C11 C12 C13 117.6(2) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 H12 121.2 . . ?
C10 C9 C8 102.38(18) . . ?
C10 C9 H9A 111.3 . . ?
C8 C9 H9A 111.3 . . ?
C10 C9 H9B 111.3 . . ?
C8 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
C14 C15 C10 119.0(3) . . ?
C14 C15 H15 120.5 . . ?
C10 C15 H15 120.5 . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C8 C16 H16A 109.5 . . ?
C8 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C8 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C14 C13 121.2(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_IDP-DPE-H2O
_database_code_depnum_ccdc_archive 'CCDC 1849066'
_audit_update_record             
;
2018-06-13 deposited with the CCDC.
2018-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
4-chloro-N-(2-methyl-2,3-dihydroindol-1-yl)-3-sulfamoylbenzamide-4-[(E)-2-pyridin-4-ylethenyl]pyridine-hydrate
_chemical_name_common            
'Indapamide-1,2-Bis(4-pyridyl)ethylene cocrystal monohydrate'
_chemical_melting_point          363K
_chemical_formula_moiety         'C16 H16 Cl N3 O3 S, C12 H10 N2, H2 O'
_chemical_formula_sum            'C28 H28 Cl N5 O4 S'
_chemical_formula_weight         566.06

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   12.2238(2)
_cell_length_b                   14.8267(3)
_cell_length_c                   16.2328(3)
_cell_angle_alpha                93.2280(10)
_cell_angle_beta                 107.2640(10)
_cell_angle_gamma                90.1220(10)
_cell_volume                     2804.46(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9890
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      26.74

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    0.254
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            76699
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.633
_diffrn_reflns_theta_max         28.391
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             14012
_reflns_number_gt                8799
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0628P)²+1.8898P] 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         14012
_refine_ls_number_parameters     745
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1217
_refine_ls_R_factor_gt           0.0717
_refine_ls_wR_factor_ref         0.1793
_refine_ls_wR_factor_gt          0.1596
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.001
_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 0.50484(6) 0.58091(5) -0.24224(5) 0.04382(18) Uani 1 1 d . . . . .
Cl1 Cl 0.67969(7) 0.45993(5) -0.09787(6) 0.0559(2) Uani 1 1 d . . . . .
S2 S 0.03688(7) 1.15638(5) 0.71732(6) 0.0582(2) Uani 1 1 d . . . . .
Cl2 Cl 0.25784(9) 1.20270(6) 0.88873(8) 0.0846(3) Uani 1 1 d . . . . .
O3 O 0.31920(19) 0.77893(15) -0.05004(15) 0.0596(6) Uani 1 1 d . . . . .
O1 O 0.43324(19) 0.65340(16) -0.27914(13) 0.0600(6) Uani 1 1 d . . . . .
O2 O 0.46142(18) 0.49025(14) -0.26533(15) 0.0599(6) Uani 1 1 d . . . . .
O7 O 0.7149(3) 0.7440(2) 0.6809(2) 0.0774(8) Uani 1 1 d . . . . .
O6 O -0.08953(19) 0.84082(16) 0.78540(18) 0.0751(7) Uani 1 1 d . . . . .
O5 O -0.0620(2) 1.11249(16) 0.65919(17) 0.0730(7) Uani 1 1 d . . . . .
N2 N 0.4180(3) 0.77761(17) 0.09076(18) 0.0505(6) Uani 1 1 d . . . . .
N3 N 0.6248(2) 0.5886(2) -0.25995(19) 0.0524(7) Uani 1 1 d . . . . .
O4 O 0.0266(2) 1.24429(16) 0.7533(2) 0.0815(8) Uani 1 1 d . . . . .
C2 C 0.4656(2) 0.66361(17) -0.10005(17) 0.0362(6) Uani 1 1 d . . . . .
H2 H 0.4141 0.6970 -0.1405 0.043 Uiso 1 1 calc R U . . .
N5 N 0.0634(2) 0.77523(18) 0.8749(2) 0.0572(7) Uani 1 1 d . . . . .
N1 N 0.3494(3) 0.84600(17) 0.11137(19) 0.0621(8) Uani 1 1 d . . . . .
C1 C 0.4759(2) 0.68009(16) -0.01337(17) 0.0356(6) Uani 1 1 d . . . . .
C3 C 0.5296(2) 0.59883(16) -0.12838(17) 0.0356(6) Uani 1 1 d . . . . .
N4 N 0.0096(2) 0.69024(18) 0.8583(2) 0.0606(7) Uani 1 1 d . . . . .
C4 C 0.6048(2) 0.54836(16) -0.06758(19) 0.0375(6) Uani 1 1 d . . . . .
N9 N 0.6656(3) 0.42828(19) 0.6473(2) 0.0660(8) Uani 1 1 d . . . . .
C5 C 0.6187(2) 0.56532(18) 0.01919(18) 0.0413(6) Uani 1 1 d . . . . .
H5 H 0.6712 0.5325 0.0595 0.050 Uiso 1 1 calc R U . . .
C6 C 0.5552(2) 0.63086(18) 0.04682(18) 0.0399(6) Uani 1 1 d . . . . .
H6 H 0.5653 0.6422 0.1056 0.048 Uiso 1 1 calc R U . . .
O8 O 0.5739(4) 0.7073(2) 0.2526(2) 0.1023(13) Uani 1 1 d . . . . .
C7 C 0.3977(2) 0.74940(18) 0.00768(19) 0.0420(6) Uani 1 1 d . . . . .
C18 C 0.0334(2) 0.99931(19) 0.7937(2) 0.0447(7) Uani 1 1 d . . . . .
H18 H -0.0300 0.9859 0.7460 0.054 Uiso 1 1 calc R U . . .
C11 C 0.3965(3) 0.93357(18) 0.12958(18) 0.0445(7) Uani 1 1 d . . . . .
N10 N 0.6237(3) -0.1601(2) 0.3921(2) 0.0705(8) Uani 1 1 d . . . . .
C17 C 0.0714(2) 0.93498(19) 0.8541(2) 0.0444(6) Uani 1 1 d . . . . .
C19 C 0.0871(2) 1.08241(18) 0.8027(2) 0.0455(7) Uani 1 1 d . . . . .
C23 C 0.0076(3) 0.8464(2) 0.8348(2) 0.0522(7) Uani 1 1 d . . . . .
N6 N 0.1328(4) 1.1600(3) 0.6687(3) 0.0804(11) Uani 1 1 d . . . . .
C27 C 0.0700(3) 0.6188(2) 0.8336(2) 0.0527(8) Uani 1 1 d . . . . .
N8 N 0.8667(4) 0.0402(2) 0.3682(3) 0.0842(10) Uani 1 1 d . . . . .
N7 N 0.8014(3) 0.6409(2) 0.5584(2) 0.0810(10) Uani 1 1 d . . . . .
C01 C 0.3325(3) 0.9826(2) 0.1728(2) 0.0587(8) Uani 1 1 d . . . . .
C47 C 0.6314(3) 0.2613(2) 0.5520(2) 0.0576(8) Uani 1 1 d . . . . .
C20 C 0.1808(3) 1.1018(2) 0.8745(2) 0.0547(8) Uani 1 1 d . . . . .
C22 C 0.1633(3) 0.9564(2) 0.9257(2) 0.0578(8) Uani 1 1 d . . . . .
H22 H 0.1891 0.9143 0.9672 0.069 Uiso 1 1 calc R U . . .
C21 C 0.2173(3) 1.0397(2) 0.9363(2) 0.0638(9) Uani 1 1 d . . . . .
H21 H 0.2785 1.0540 0.9854 0.077 Uiso 1 1 calc R U . . .
C35 C 0.8568(3) 0.4657(3) 0.5105(2) 0.0628(9) Uani 1 1 d . . . . .
C52 C 0.6461(3) 0.0106(2) 0.4797(2) 0.0582(8) Uani 1 1 d . . . . .
C28 C 0.1545(3) 0.6200(2) 0.7950(2) 0.0619(9) Uani 1 1 d . . . . .
H28 H 0.1845 0.6742 0.7842 0.074 Uiso 1 1 calc R U . . .
C12 C 0.4850(3) 0.9721(2) 0.1076(2) 0.0562(8) Uani 1 1 d . . . . .
H12 H 0.5279 0.9381 0.0789 0.067 Uiso 1 1 calc R U . . .
C26 C 0.0257(3) 0.5371(2) 0.8506(2) 0.0615(9) Uani 1 1 d . . . . .
C40 C 0.8452(3) 0.2253(3) 0.4041(2) 0.0644(9) Uani 1 1 d . . . . .
C50 C 0.6087(3) 0.1733(2) 0.5033(2) 0.0648(9) Uani 1 1 d . . . . .
H50 H 0.5487 0.1694 0.4520 0.078 Uiso 1 1 calc R U . . .
C46 C 0.7286(3) 0.2802(2) 0.6205(3) 0.0719(10) Uani 1 1 d . . . . .
H46 H 0.7846 0.2369 0.6368 0.086 Uiso 1 1 calc R U . . .
C8 C 0.2758(3) 0.8269(2) 0.1614(3) 0.0657(9) Uani 1 1 d . . . . .
H8 H 0.3249 0.8034 0.2149 0.079 Uiso 1 1 calc R U . . .
C39 C 0.8245(3) 0.3209(3) 0.4246(2) 0.0686(10) Uani 1 1 d . . . . .
H39 H 0.7612 0.3468 0.3871 0.082 Uiso 1 1 calc R U . . .
C31 C 0.0681(4) 0.4567(2) 0.8275(3) 0.0761(12) Uani 1 1 d . . . . .
H31 H 0.0395 0.4022 0.8390 0.091 Uiso 1 1 calc R U . . .
C48 C 0.5530(3) 0.3293(3) 0.5321(3) 0.0741(10) Uani 1 1 d . . . . .
H48 H 0.4864 0.3208 0.4861 0.089 Uiso 1 1 calc R U . . .
C41 C 0.7634(4) 0.1766(3) 0.3414(3) 0.0740(10) Uani 1 1 d . . . . .
H41 H 0.6984 0.2051 0.3090 0.089 Uiso 1 1 calc R U . . .
C53 C 0.7083(3) -0.0620(2) 0.5155(2) 0.0714(10) Uani 1 1 d . . . . .
H53 H 0.7598 -0.0551 0.5707 0.086 Uiso 1 1 calc R U . . .
C45 C 0.7423(3) 0.3638(2) 0.6648(3) 0.0722(10) Uani 1 1 d . . . . .
H45 H 0.8095 0.3755 0.7096 0.087 Uiso 1 1 calc R U . . .
C51 C 0.6659(3) 0.1003(2) 0.5262(2) 0.0634(9) Uani 1 1 d . . . . .
H51 H 0.7257 0.1052 0.5775 0.076 Uiso 1 1 calc R U . . .
C54 C 0.6953(4) -0.1446(3) 0.4710(3) 0.0745(11) Uani 1 1 d . . . . .
H54 H 0.7390 -0.1921 0.4974 0.089 Uiso 1 1 calc R U . . .
C30 C 0.1521(4) 0.4570(3) 0.7876(3) 0.0790(12) Uani 1 1 d . . . . .
H30 H 0.1800 0.4028 0.7712 0.095 Uiso 1 1 calc R U . . .
C49 C 0.5741(4) 0.4100(3) 0.5809(3) 0.0769(11) Uani 1 1 d . . . . .
H49 H 0.5199 0.4549 0.5659 0.092 Uiso 1 1 calc R U . . .
C34 C 0.7703(3) 0.5136(3) 0.4566(2) 0.0740(11) Uani 1 1 d . . . . .
H34 H 0.7277 0.4880 0.4031 0.089 Uiso 1 1 calc R U . . .
C38 C 0.8854(3) 0.3729(3) 0.4895(2) 0.0722(10) Uani 1 1 d . . . . .
H38 H 0.9521 0.3494 0.5251 0.087 Uiso 1 1 calc R U . . .
C33 C 0.7480(4) 0.5993(3) 0.4830(3) 0.0807(12) Uani 1 1 d . . . . .
H33 H 0.6907 0.6305 0.4448 0.097 Uiso 1 1 calc R U . . .
C56 C 0.5692(4) -0.0057(3) 0.3985(2) 0.0725(10) Uani 1 1 d . . . . .
H56 H 0.5227 0.0401 0.3713 0.087 Uiso 1 1 calc R U . . .
C13 C 0.5089(3) 1.0633(2) 0.1292(2) 0.0689(10) Uani 1 1 d . . . . .
H13 H 0.5679 1.0912 0.1142 0.083 Uiso 1 1 calc R U . . .
C29 C 0.1946(3) 0.5371(3) 0.7722(3) 0.0728(10) Uani 1 1 d . . . . .
H29 H 0.2523 0.5365 0.7455 0.087 Uiso 1 1 calc R U . . .
C9 C 0.2422(3) 0.9217(2) 0.1864(3) 0.0726(10) Uani 1 1 d . . . . .
H9A H 0.1668 0.9366 0.1499 0.087 Uiso 1 1 calc R U . . .
H9B H 0.2423 0.9263 0.2463 0.087 Uiso 1 1 calc R U . . .
C55 C 0.5625(4) -0.0911(3) 0.3584(2) 0.0778(11) Uani 1 1 d . . . . .
H55 H 0.5109 -0.1005 0.3034 0.093 Uiso 1 1 calc R U . . .
C36 C 0.9155(3) 0.5106(3) 0.5889(3) 0.0834(12) Uani 1 1 d . . . . .
H36 H 0.9762 0.4831 0.6277 0.100 Uiso 1 1 calc R U . . .
C15 C 0.3583(4) 1.0729(3) 0.1956(3) 0.0937(14) Uani 1 1 d . . . . .
H15 H 0.3171 1.1065 0.2259 0.112 Uiso 1 1 calc R U . . .
C25 C -0.0660(3) 0.5594(3) 0.8918(3) 0.0811(12) Uani 1 1 d . . . . .
H25A H -0.0613 0.5215 0.9396 0.097 Uiso 1 1 calc R U . . .
H25B H -0.1415 0.5518 0.8502 0.097 Uiso 1 1 calc R U . . .
C42 C 0.7767(4) 0.0860(3) 0.3259(3) 0.0808(11) Uani 1 1 d . . . . .
H42 H 0.7189 0.0549 0.2832 0.097 Uiso 1 1 calc R U . . .
C24 C -0.0410(4) 0.6575(3) 0.9233(3) 0.0793(11) Uani 1 1 d . . . . .
H24 H 0.0203 0.6585 0.9784 0.095 Uiso 1 1 calc R U . . .
C14 C 0.4468(4) 1.1127(3) 0.1724(3) 0.0879(13) Uani 1 1 d . . . . .
H14 H 0.4640 1.1739 0.1864 0.105 Uiso 1 1 calc R U . . .
C43 C 0.9482(4) 0.0893(4) 0.4266(3) 0.0971(15) Uani 1 1 d . . . . .
H43 H 1.0143 0.0600 0.4561 0.117 Uiso 1 1 calc R U . . .
C37 C 0.8833(4) 0.5955(3) 0.6085(3) 0.0863(13) Uani 1 1 d . . . . .
H37 H 0.9231 0.6231 0.6620 0.104 Uiso 1 1 calc R U . . .
C44 C 0.9412(4) 0.1798(3) 0.4461(3) 0.0840(12) Uani 1 1 d . . . . .
H44 H 1.0012 0.2102 0.4876 0.101 Uiso 1 1 calc R U . . .
C16 C 0.1822(4) 0.7611(3) 0.1279(4) 0.1042(16) Uani 1 1 d . . . . .
H16A H 0.1278 0.7831 0.0777 0.156 Uiso 1 1 calc R U . . .
H16B H 0.1452 0.7520 0.1714 0.156 Uiso 1 1 calc R U . . .
H16C H 0.2120 0.7048 0.1125 0.156 Uiso 1 1 calc R U . . .
C32 C -0.1342(5) 0.7093(4) 0.9382(4) 0.1197(19) Uani 1 1 d . . . . .
H32A H -0.1088 0.7706 0.9555 0.180 Uiso 1 1 calc R U . . .
H32B H -0.1585 0.6836 0.9830 0.180 Uiso 1 1 calc R U . . .
H32C H -0.1971 0.7079 0.8860 0.180 Uiso 1 1 calc R U . . .
H2A H 0.474(2) 0.7603(18) 0.1326(19) 0.035(8) Uiso 1 1 d . . . . .
H5A H 0.127(2) 0.7795(17) 0.9044(17) 0.028(7) Uiso 1 1 d . . . . .
H3A H 0.643(3) 0.547(2) -0.284(2) 0.043(9) Uiso 1 1 d . . . . .
H3B H 0.645(3) 0.642(2) -0.273(2) 0.049(9) Uiso 1 1 d . . . . .
H7A H 0.740(4) 0.723(3) 0.642(3) 0.106(18) Uiso 1 1 d . . . . .
H7B H 0.769(4) 0.774(3) 0.703(3) 0.089(16) Uiso 1 1 d . . . . .
H8B H 0.591(4) 0.736(3) 0.296(3) 0.103(17) Uiso 1 1 d . . . . .
H8A H 0.567(4) 0.659(3) 0.260(3) 0.097(18) Uiso 1 1 d . . . . .
H6A H 0.142(4) 1.110(3) 0.652(3) 0.076(14) Uiso 1 1 d . . . . .
H6B H 0.191(5) 1.196(4) 0.689(4) 0.12(2) 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 O1 1.430(2) . ?
S1 O2 1.432(2) . ?
S1 N3 1.580(3) . ?
S1 C3 1.786(3) . ?
Cl1 C4 1.732(3) . ?
S2 O4 1.419(3) . ?
S2 O5 1.423(3) . ?
S2 N6 1.598(4) . ?
S2 C19 1.780(3) . ?
Cl2 C20 1.733(3) . ?
O3 C7 1.226(3) . ?
O7 H7A 0.83(5) . ?
O7 H7B 0.77(5) . ?
O6 C23 1.219(4) . ?
N2 C7 1.339(4) . ?
N2 N1 1.405(3) . ?
N2 H2A 0.86(3) . ?
N3 H3A 0.78(3) . ?
N3 H3B 0.88(3) . ?
C2 C1 1.382(4) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
N5 C23 1.349(4) . ?
N5 N4 1.395(4) . ?
N5 H5A 0.78(3) . ?
N1 C11 1.399(4) . ?
N1 C8 1.417(4) . ?
C1 C6 1.396(4) . ?
C1 C7 1.499(4) . ?
C3 C4 1.388(4) . ?
N4 C27 1.400(4) . ?
N4 C24 1.476(5) . ?
C4 C5 1.376(4) . ?
N9 C49 1.317(5) . ?
N9 C45 1.323(4) . ?
C5 C6 1.382(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
O8 H8B 0.78(5) . ?
O8 H8A 0.74(5) . ?
C18 C19 1.375(4) . ?
C18 C17 1.387(4) . ?
C18 H18 0.9300 . ?
C11 C12 1.369(4) . ?
C11 C01 1.379(4) . ?
N10 C55 1.315(5) . ?
N10 C54 1.326(5) . ?
C17 C22 1.376(4) . ?
C17 C23 1.496(4) . ?
C19 C20 1.387(4) . ?
N6 H6A 0.80(4) . ?
N6 H6B 0.86(6) . ?
C27 C28 1.358(5) . ?
C27 C26 1.400(4) . ?
N8 C42 1.323(5) . ?
N8 C43 1.334(6) . ?
N7 C37 1.304(5) . ?
N7 C33 1.320(5) . ?
C01 C15 1.379(5) . ?
C01 C9 1.499(5) . ?
C47 C48 1.377(5) . ?
C47 C46 1.381(5) . ?
C47 C50 1.468(5) . ?
C20 C21 1.377(5) . ?
C22 C21 1.377(5) . ?
C22 H22 0.9300 . ?
C21 H21 0.9300 . ?
C35 C34 1.383(5) . ?
C35 C36 1.392(5) . ?
C35 C38 1.467(5) . ?
C52 C53 1.374(5) . ?
C52 C56 1.381(5) . ?
C52 C51 1.475(4) . ?
C28 C29 1.396(5) . ?
C28 H28 0.9300 . ?
C12 C13 1.386(5) . ?
C12 H12 0.9300 . ?
C26 C31 1.378(5) . ?
C26 C25 1.494(6) . ?
C40 C41 1.367(5) . ?
C40 C44 1.370(5) . ?
C40 C39 1.478(5) . ?
C50 C51 1.300(5) . ?
C50 H50 0.9300 . ?
C46 C45 1.381(5) . ?
C46 H46 0.9300 . ?
C8 C16 1.457(5) . ?
C8 C9 1.533(5) . ?
C8 H8 0.9800 . ?
C39 C38 1.303(5) . ?
C39 H39 0.9300 . ?
C31 C30 1.367(6) . ?
C31 H31 0.9300 . ?
C48 C49 1.378(5) . ?
C48 H48 0.9300 . ?
C41 C42 1.372(5) . ?
C41 H41 0.9300 . ?
C53 C54 1.370(5) . ?
C53 H53 0.9300 . ?
C45 H45 0.9300 . ?
C51 H51 0.9300 . ?
C54 H54 0.9300 . ?
C30 C29 1.360(6) . ?
C30 H30 0.9300 . ?
C49 H49 0.9300 . ?
C34 C33 1.371(5) . ?
C34 H34 0.9300 . ?
C38 H38 0.9300 . ?
C33 H33 0.9300 . ?
C56 C55 1.383(5) . ?
C56 H56 0.9300 . ?
C13 C14 1.366(6) . ?
C13 H13 0.9300 . ?
C29 H29 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C55 H55 0.9300 . ?
C36 C37 1.368(6) . ?
C36 H36 0.9300 . ?
C15 C14 1.388(6) . ?
C15 H15 0.9300 . ?
C25 C24 1.514(6) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C42 H42 0.9300 . ?
C24 C32 1.446(6) . ?
C24 H24 0.9800 . ?
C14 H14 0.9300 . ?
C43 C44 1.371(6) . ?
C43 H43 0.9300 . ?
C37 H37 0.9300 . ?
C44 H44 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

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
O1 S1 O2 118.31(14) . . ?
O1 S1 N3 110.31(16) . . ?
O2 S1 N3 108.56(15) . . ?
O1 S1 C3 104.87(12) . . ?
O2 S1 C3 106.80(13) . . ?
N3 S1 C3 107.39(14) . . ?
O4 S2 O5 119.00(16) . . ?
O4 S2 N6 108.4(2) . . ?
O5 S2 N6 107.6(2) . . ?
O4 S2 C19 108.95(16) . . ?
O5 S2 C19 105.49(14) . . ?
N6 S2 C19 106.79(16) . . ?
H7A O7 H7B 95(4) . . ?
C7 N2 N1 118.4(3) . . ?
C7 N2 H2A 124.8(19) . . ?
N1 N2 H2A 116.7(19) . . ?
S1 N3 H3A 116(2) . . ?
S1 N3 H3B 117(2) . . ?
H3A N3 H3B 116(3) . . ?
C1 C2 C3 121.9(2) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C23 N5 N4 119.2(3) . . ?
C23 N5 H5A 122(2) . . ?
N4 N5 H5A 119(2) . . ?
C11 N1 N2 117.6(3) . . ?
C11 N1 C8 112.5(2) . . ?
N2 N1 C8 119.8(3) . . ?
C2 C1 C6 118.5(2) . . ?
C2 C1 C7 116.1(2) . . ?
C6 C1 C7 125.4(2) . . ?
C2 C3 C4 118.5(2) . . ?
C2 C3 S1 117.7(2) . . ?
C4 C3 S1 123.65(19) . . ?
N5 N4 C27 117.2(2) . . ?
N5 N4 C24 117.7(3) . . ?
C27 N4 C24 107.4(3) . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 Cl1 117.9(2) . . ?
C3 C4 Cl1 121.6(2) . . ?
C49 N9 C45 115.8(3) . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
H8B O8 H8A 110(5) . . ?
O3 C7 N2 122.3(3) . . ?
O3 C7 C1 120.3(3) . . ?
N2 C7 C1 117.4(3) . . ?
C19 C18 C17 121.6(3) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C12 C11 C01 121.9(3) . . ?
C12 C11 N1 130.3(3) . . ?
C01 C11 N1 107.7(3) . . ?
C55 N10 C54 115.9(3) . . ?
C22 C17 C18 118.7(3) . . ?
C22 C17 C23 125.3(3) . . ?
C18 C17 C23 115.9(3) . . ?
C18 C19 C20 118.6(3) . . ?
C18 C19 S2 117.5(2) . . ?
C20 C19 S2 123.8(2) . . ?
O6 C23 N5 123.2(3) . . ?
O6 C23 C17 120.5(3) . . ?
N5 C23 C17 116.3(3) . . ?
S2 N6 H6A 108(3) . . ?
S2 N6 H6B 120(4) . . ?
H6A N6 H6B 119(5) . . ?
C28 C27 N4 129.9(3) . . ?
C28 C27 C26 121.0(3) . . ?
N4 C27 C26 109.0(3) . . ?
C42 N8 C43 115.1(4) . . ?
C37 N7 C33 115.1(4) . . ?
C15 C01 C11 119.6(3) . . ?
C15 C01 C9 131.4(3) . . ?
C11 C01 C9 109.0(3) . . ?
C48 C47 C46 116.3(3) . . ?
C48 C47 C50 120.6(3) . . ?
C46 C47 C50 123.1(3) . . ?
C21 C20 C19 120.5(3) . . ?
C21 C20 Cl2 117.7(2) . . ?
C19 C20 Cl2 121.8(3) . . ?
C17 C22 C21 120.5(3) . . ?
C17 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C20 C21 C22 120.1(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C34 C35 C36 115.6(4) . . ?
C34 C35 C38 123.6(3) . . ?
C36 C35 C38 120.8(3) . . ?
C53 C52 C56 116.2(3) . . ?
C53 C52 C51 120.2(3) . . ?
C56 C52 C51 123.6(3) . . ?
C27 C28 C29 117.8(3) . . ?
C27 C28 H28 121.1 . . ?
C29 C28 H28 121.1 . . ?
C11 C12 C13 118.1(3) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C31 C26 C27 119.5(4) . . ?
C31 C26 C25 133.0(3) . . ?
C27 C26 C25 107.5(3) . . ?
C41 C40 C44 116.5(4) . . ?
C41 C40 C39 119.3(3) . . ?
C44 C40 C39 124.2(4) . . ?
C51 C50 C47 125.1(3) . . ?
C51 C50 H50 117.4 . . ?
C47 C50 H50 117.4 . . ?
C47 C46 C45 119.8(3) . . ?
C47 C46 H46 120.1 . . ?
C45 C46 H46 120.1 . . ?
N1 C8 C16 119.9(3) . . ?
N1 C8 C9 102.1(3) . . ?
C16 C8 C9 116.1(3) . . ?
N1 C8 H8 105.9 . . ?
C16 C8 H8 105.9 . . ?
C9 C8 H8 105.9 . . ?
C38 C39 C40 127.1(4) . . ?
C38 C39 H39 116.5 . . ?
C40 C39 H39 116.5 . . ?
C30 C31 C26 120.0(4) . . ?
C30 C31 H31 120.0 . . ?
C26 C31 H31 120.0 . . ?
C47 C48 C49 119.5(4) . . ?
C47 C48 H48 120.2 . . ?
C49 C48 H48 120.2 . . ?
C40 C41 C42 120.4(4) . . ?
C40 C41 H41 119.8 . . ?
C42 C41 H41 119.8 . . ?
C54 C53 C52 120.8(4) . . ?
C54 C53 H53 119.6 . . ?
C52 C53 H53 119.6 . . ?
N9 C45 C46 123.9(4) . . ?
N9 C45 H45 118.0 . . ?
C46 C45 H45 118.0 . . ?
C50 C51 C52 127.1(3) . . ?
C50 C51 H51 116.5 . . ?
C52 C51 H51 116.5 . . ?
N10 C54 C53 123.3(4) . . ?
N10 C54 H54 118.3 . . ?
C53 C54 H54 118.3 . . ?
C29 C30 C31 119.7(4) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
N9 C49 C48 124.7(3) . . ?
N9 C49 H49 117.7 . . ?
C48 C49 H49 117.7 . . ?
C33 C34 C35 119.3(3) . . ?
C33 C34 H34 120.3 . . ?
C35 C34 H34 120.3 . . ?
C39 C38 C35 125.0(3) . . ?
C39 C38 H38 117.5 . . ?
C35 C38 H38 117.5 . . ?
N7 C33 C34 125.2(4) . . ?
N7 C33 H33 117.4 . . ?
C34 C33 H33 117.4 . . ?
C52 C56 C55 118.9(4) . . ?
C52 C56 H56 120.6 . . ?
C55 C56 H56 120.6 . . ?
C14 C13 C12 120.7(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C30 C29 C28 122.1(4) . . ?
C30 C29 H29 119.0 . . ?
C28 C29 H29 119.0 . . ?
C01 C9 C8 104.1(3) . . ?
C01 C9 H9A 110.9 . . ?
C8 C9 H9A 110.9 . . ?
C01 C9 H9B 110.9 . . ?
C8 C9 H9B 110.9 . . ?
H9A C9 H9B 109.0 . . ?
N10 C55 C56 124.9(4) . . ?
N10 C55 H55 117.6 . . ?
C56 C55 H55 117.6 . . ?
C37 C36 C35 119.5(4) . . ?
C37 C36 H36 120.3 . . ?
C35 C36 H36 120.3 . . ?
C01 C15 C14 118.8(4) . . ?
C01 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C26 C25 C24 103.5(3) . . ?
C26 C25 H25A 111.1 . . ?
C24 C25 H25A 111.1 . . ?
C26 C25 H25B 111.1 . . ?
C24 C25 H25B 111.1 . . ?
H25A C25 H25B 109.0 . . ?
N8 C42 C41 123.9(4) . . ?
N8 C42 H42 118.0 . . ?
C41 C42 H42 118.0 . . ?
C32 C24 N4 116.4(4) . . ?
C32 C24 C25 117.3(4) . . ?
N4 C24 C25 101.0(3) . . ?
C32 C24 H24 107.1 . . ?
N4 C24 H24 107.1 . . ?
C25 C24 H24 107.1 . . ?
C13 C14 C15 120.8(4) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
N8 C43 C44 124.5(4) . . ?
N8 C43 H43 117.8 . . ?
C44 C43 H43 117.8 . . ?
N7 C37 C36 125.3(4) . . ?
N7 C37 H37 117.3 . . ?
C36 C37 H37 117.3 . . ?
C40 C44 C43 119.5(4) . . ?
C40 C44 H44 120.2 . . ?
C43 C44 H44 120.2 . . ?
C8 C16 H16A 109.5 . . ?
C8 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C8 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C24 C32 H32A 109.5 . . ?
C24 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C24 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

_refine_diff_density_max         0.794
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.061

