# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_ETRADA
_database_code_depnum_ccdc_archive 'CCDC 1444654'
_audit_update_record             
;
2015-12-29 deposited with the CCDC.
2016-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
"5-Chloro-6'-methyl-3-[4-(methylsulfonyl)phenyl]-2,3'-bipyridine-hexane-1,6-dicarboxylic acid"
_chemical_name_common            'etoricoxib-adipic acid cocrystal'
_chemical_melting_point          414.3
_chemical_formula_moiety         'C18 H15 Cl N2 O2 S, 0.5(C6 H10 O4)'
_chemical_formula_sum            'C21 H20 Cl N2 O4 S'
_chemical_formula_weight         431.90

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                   16.6417(18)
_cell_length_b                   5.4913(6)
_cell_length_c                   23.838(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.603(2)
_cell_angle_gamma                90
_cell_volume                     2153.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3765
_cell_measurement_theta_min      1.40
_cell_measurement_theta_max      26.38

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             900
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.303
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_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  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21794
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.399
_diffrn_reflns_theta_max         26.379
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4406
_reflns_number_gt                3765
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0778P)²+1.1976P] 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         4406
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1516
_refine_ls_wR_factor_gt          0.1444
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.72748(3) 0.18883(10) 0.11762(2) 0.04763(18) Uani 1 1 d . . . . .
Cl1 Cl 0.59101(6) 0.1853(3) 0.47912(3) 0.1167(4) Uani 1 1 d . . . . .
C13 C 0.39355(13) 0.2931(4) 0.25289(9) 0.0462(5) Uani 1 1 d . . . . .
C5 C 0.57714(12) 0.1967(4) 0.26136(9) 0.0443(5) Uani 1 1 d . . . . .
C2 C 0.66762(13) 0.1881(4) 0.17295(9) 0.0428(5) Uani 1 1 d . . . . .
C17 C 0.28253(13) 0.3051(5) 0.15532(9) 0.0498(5) Uani 1 1 d . . . . .
O3 O 0.34483(12) 0.7813(4) 0.08420(9) 0.0698(5) Uani 1 1 d . . . . .
O1 O 0.72374(11) 0.4286(3) 0.09373(8) 0.0648(5) Uani 1 1 d . . . . .
C7 C 0.61383(13) 0.3778(4) 0.17694(9) 0.0450(5) Uani 1 1 d . . . . .
H7 H 0.6079 0.5015 0.1500 0.054 Uiso 1 1 calc R U . . .
N1 N 0.33794(11) 0.1279(4) 0.16220(8) 0.0494(4) Uani 1 1 d . . . . .
N2 N 0.41391(13) 0.3100(5) 0.35316(9) 0.0681(6) Uani 1 1 d . . . . .
O2 O 0.80531(10) 0.0900(4) 0.13944(8) 0.0686(5) Uani 1 1 d . . . . .
C8 C 0.53265(13) 0.2103(4) 0.31105(9) 0.0483(5) Uani 1 1 d . . . . .
C3 C 0.67650(14) 0.0029(4) 0.21268(10) 0.0508(5) Uani 1 1 d . . . . .
H3 H 0.7127 -0.1241 0.2098 0.061 Uiso 1 1 calc R U . . .
C6 C 0.56924(13) 0.3815(4) 0.22117(9) 0.0461(5) Uani 1 1 d . . . . .
H6 H 0.5334 0.5092 0.2241 0.055 Uiso 1 1 calc R U . . .
C10 C 0.57606(15) 0.1773(5) 0.36503(10) 0.0590(6) Uani 1 1 d . . . . .
H10 H 0.6304 0.1308 0.3696 0.071 Uiso 1 1 calc R U . . .
C19 C 0.41742(17) 0.6897(5) 0.08379(11) 0.0602(6) Uani 1 1 d . . . . .
C4 C 0.63127(14) 0.0083(4) 0.25647(10) 0.0518(5) Uani 1 1 d . . . . .
H4 H 0.6370 -0.1163 0.2832 0.062 Uiso 1 1 calc R U . . .
C15 C 0.33665(14) 0.4778(5) 0.24464(10) 0.0539(6) Uani 1 1 d . . . . .
H15 H 0.3359 0.5976 0.2721 0.065 Uiso 1 1 calc R U . . .
C16 C 0.28108(14) 0.4844(5) 0.19569(10) 0.0557(6) Uani 1 1 d . . . . .
H16 H 0.2428 0.6088 0.1899 0.067 Uiso 1 1 calc R U . . .
C9 C 0.45014(14) 0.2714(5) 0.30735(9) 0.0504(5) Uani 1 1 d . . . . .
C14 C 0.39214(13) 0.1243(4) 0.20963(9) 0.0485(5) Uani 1 1 d . . . . .
H14 H 0.4311 0.0014 0.2138 0.058 Uiso 1 1 calc R U . . .
C1 C 0.67840(17) -0.0121(5) 0.06629(11) 0.0634(7) Uani 1 1 d . . . . .
H1A H 0.7034 -0.0023 0.0326 0.095 Uiso 1 1 calc R U . . .
H1B H 0.6221 0.0316 0.0574 0.095 Uiso 1 1 calc R U . . .
H1C H 0.6829 -0.1754 0.0808 0.095 Uiso 1 1 calc R U . . .
O4 O 0.47767(14) 0.7759(5) 0.10978(12) 0.1029(9) Uani 1 1 d . . . . .
C21 C 0.49358(17) 0.4132(5) 0.02290(11) 0.0647(7) Uani 1 1 d . . . . .
H21A H 0.5397 0.4216 0.0530 0.078 Uiso 1 1 calc R U . . .
H21B H 0.4909 0.2489 0.0078 0.078 Uiso 1 1 calc R U . . .
C18 C 0.22127(16) 0.2981(6) 0.10218(11) 0.0697(8) Uani 1 1 d . . . . .
H18A H 0.2274 0.4402 0.0798 0.105 Uiso 1 1 calc R U . . .
H18B H 0.1674 0.2947 0.1121 0.105 Uiso 1 1 calc R U . . .
H18C H 0.2298 0.1548 0.0808 0.105 Uiso 1 1 calc R U . . .
C12 C 0.45766(19) 0.2841(7) 0.40415(11) 0.0799(9) Uani 1 1 d . . . . .
H12 H 0.4333 0.3142 0.4361 0.096 Uiso 1 1 calc R U . . .
C11 C 0.53807(17) 0.2140(6) 0.41116(10) 0.0726(8) Uani 1 1 d . . . . .
C20 C 0.41606(19) 0.4667(6) 0.04747(13) 0.0724(8) Uani 1 1 d . . . . .
H20A H 0.3717 0.4826 0.0163 0.087 Uiso 1 1 calc R U . . .
H20B H 0.4042 0.3274 0.0699 0.087 Uiso 1 1 calc R U . . .
H3A H 0.3466(16) 0.896(5) 0.1069(12) 0.062(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 1.4287(18) . ?
S1 O1 1.4323(18) . ?
S1 C1 1.756(2) . ?
S1 C2 1.768(2) . ?
Cl1 C11 1.732(2) . ?
C13 C15 1.381(3) . ?
C13 C14 1.384(3) . ?
C13 C9 1.490(3) . ?
C5 C6 1.388(3) . ?
C5 C4 1.388(3) . ?
C5 C8 1.490(3) . ?
C2 C3 1.383(3) . ?
C2 C7 1.386(3) . ?
C17 N1 1.334(3) . ?
C17 C16 1.380(3) . ?
C17 C18 1.503(3) . ?
O3 C19 1.310(3) . ?
C7 C6 1.377(3) . ?
N1 C14 1.337(3) . ?
N2 C12 1.328(3) . ?
N2 C9 1.341(3) . ?
C8 C10 1.390(3) . ?
C8 C9 1.403(3) . ?
C3 C4 1.376(3) . ?
C10 C11 1.363(4) . ?
C19 O4 1.195(3) . ?
C19 C20 1.498(4) . ?
C15 C16 1.377(3) . ?
C21 C21 1.489(5) 3_665 ?
C21 C20 1.523(4) . ?
C12 C11 1.378(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 118.49(12) . . ?
O2 S1 C1 108.48(12) . . ?
O1 S1 C1 108.22(12) . . ?
O2 S1 C2 107.99(11) . . ?
O1 S1 C2 107.63(10) . . ?
C1 S1 C2 105.27(12) . . ?
C15 C13 C14 116.8(2) . . ?
C15 C13 C9 120.9(2) . . ?
C14 C13 C9 122.2(2) . . ?
C6 C5 C4 118.8(2) . . ?
C6 C5 C8 120.4(2) . . ?
C4 C5 C8 120.7(2) . . ?
C3 C2 C7 120.7(2) . . ?
C3 C2 S1 119.89(17) . . ?
C7 C2 S1 119.43(16) . . ?
N1 C17 C16 121.3(2) . . ?
N1 C17 C18 117.0(2) . . ?
C16 C17 C18 121.7(2) . . ?
C6 C7 C2 119.4(2) . . ?
C17 N1 C14 118.8(2) . . ?
C12 N2 C9 118.5(2) . . ?
C10 C8 C9 117.2(2) . . ?
C10 C8 C5 118.6(2) . . ?
C9 C8 C5 124.05(19) . . ?
C4 C3 C2 119.3(2) . . ?
C7 C6 C5 120.8(2) . . ?
C11 C10 C8 119.2(2) . . ?
O4 C19 O3 123.2(3) . . ?
O4 C19 C20 124.2(3) . . ?
O3 C19 C20 112.6(2) . . ?
C3 C4 C5 121.0(2) . . ?
C16 C15 C13 120.0(2) . . ?
C15 C16 C17 119.5(2) . . ?
N2 C9 C8 122.8(2) . . ?
N2 C9 C13 113.2(2) . . ?
C8 C9 C13 124.0(2) . . ?
N1 C14 C13 123.7(2) . . ?
C21 C21 C20 112.4(3) 3_665 . ?
N2 C12 C11 122.0(3) . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 Cl1 120.6(2) . . ?
C12 C11 Cl1 119.2(2) . . ?
C19 C20 C21 116.1(3) . . ?

_refine_diff_density_max         0.635
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.055


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc-MeOH'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_ETRCPR_dihydrate
_database_code_depnum_ccdc_archive 'CCDC 1444655'
_audit_update_record             
;
2015-12-29 deposited with the CCDC.
2016-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'5-Chloro-6-methyl-3-[4-(methylsulfonyl)phenyl]-2,3-bipyridine-Azepan-2-one dihydrate'
_chemical_name_common            'etoricoxib-caprolactam dihydrate'
_chemical_melting_point          326.56
_chemical_formula_moiety         '2(C18 H15 Cl N2 O2 S), C6 H11 N O, 2(H2 O)'
_chemical_formula_sum            'C42 H45 Cl2 N5 O7 S2'
_chemical_formula_weight         866.85

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                   12.552(3)
_cell_length_b                   12.574(3)
_cell_length_c                   14.989(3)
_cell_angle_alpha                96.690(3)
_cell_angle_beta                 114.553(2)
_cell_angle_gamma                90.099(3)
_cell_volume                     2133.7(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    278(2)
_cell_measurement_reflns_used    7183
_cell_measurement_theta_min      1.506
_cell_measurement_theta_max      26.455

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             908
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.305
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      278(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22864
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.506
_diffrn_reflns_theta_max         26.455
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8692
_reflns_number_gt                7183
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0727P)²+0.5250P] 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         8692
_refine_ls_number_parameters     547
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.002
_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 0.93879(4) 1.17018(3) 0.17947(3) 0.04679(13) Uani 1 1 d . . . . .
Cl1 Cl 1.15094(5) 0.46841(4) 0.21309(4) 0.05946(15) Uani 1 1 d . . . . .
O2 O 0.83453(14) 1.19879(11) 0.19154(12) 0.0660(4) Uani 1 1 d . . . . .
C5 C 0.92514(15) 0.80856(13) 0.10710(12) 0.0382(4) Uani 1 1 d . . . . .
N2 N 0.83167(15) 0.51513(12) 0.01908(12) 0.0506(4) Uani 1 1 d . . . . .
C10 C 1.02834(17) 0.64147(14) 0.14965(13) 0.0431(4) Uani 1 1 d . . . . .
H10 H 1.0948 0.6831 0.1935 0.052 Uiso 1 1 calc R U . . .
C9 C 0.83180(17) 0.62246(13) 0.02369(13) 0.0421(4) Uani 1 1 d . . . . .
C7 C 0.84307(17) 0.96722(14) 0.15337(13) 0.0439(4) Uani 1 1 d . . . . .
H7 H 0.7857 0.9993 0.1696 0.053 Uiso 1 1 calc R U . . .
N1 N 0.63741(15) 0.78258(13) -0.17150(12) 0.0529(4) Uani 1 1 d . . . . .
C2 C 0.93344(16) 1.02882(13) 0.15253(13) 0.0415(4) Uani 1 1 d . . . . .
O1 O 0.96238(17) 1.21460(11) 0.10560(11) 0.0702(5) Uani 1 1 d . . . . .
C6 C 0.83864(16) 0.85676(14) 0.12971(13) 0.0424(4) Uani 1 1 d . . . . .
H6 H 0.7772 0.8148 0.1290 0.051 Uiso 1 1 calc R U . . .
C8 C 0.92794(16) 0.68933(13) 0.09104(12) 0.0393(4) Uani 1 1 d . . . . .
C3 C 1.01951(18) 0.98251(14) 0.12865(15) 0.0493(4) Uani 1 1 d . . . . .
H3 H 1.0796 1.0249 0.1275 0.059 Uiso 1 1 calc R U . . .
C14 C 0.73070(17) 0.74093(14) -0.10600(14) 0.0466(4) Uani 1 1 d . . . . .
H14 H 0.8046 0.7643 -0.0987 0.056 Uiso 1 1 calc R U . . .
C13 C 0.72456(16) 0.66522(13) -0.04818(13) 0.0430(4) Uani 1 1 d . . . . .
C4 C 1.01525(17) 0.87238(14) 0.10653(15) 0.0464(4) Uani 1 1 d . . . . .
H4 H 1.0734 0.8406 0.0911 0.056 Uiso 1 1 calc R U . . .
C12 C 0.92738(19) 0.47128(14) 0.07746(15) 0.0517(5) Uani 1 1 d . . . . .
H12 H 0.9269 0.3970 0.0751 0.062 Uiso 1 1 calc R U . . .
C11 C 1.02756(17) 0.53120(14) 0.14158(13) 0.0449(4) Uani 1 1 d . . . . .
C1 C 1.0586(2) 1.20216(16) 0.29319(16) 0.0579(5) Uani 1 1 d . . . . .
H1A H 1.1287 1.1787 0.2879 0.087 Uiso 1 1 calc R U . . .
H1B H 1.0471 1.1670 0.3423 0.087 Uiso 1 1 calc R U . . .
H1C H 1.0659 1.2784 0.3120 0.087 Uiso 1 1 calc R U . . .
C15 C 0.61341(19) 0.62872(17) -0.06305(15) 0.0555(5) Uani 1 1 d . . . . .
H15 H 0.6044 0.5747 -0.0289 0.067 Uiso 1 1 calc R U . . .
C17 C 0.53073(18) 0.75019(17) -0.18144(15) 0.0545(5) Uani 1 1 d . . . . .
C16 C 0.51679(19) 0.67301(18) -0.12857(16) 0.0601(5) Uani 1 1 d . . . . .
H16 H 0.4420 0.6509 -0.1372 0.072 Uiso 1 1 calc R U . . .
S2 S 0.74939(4) -0.07980(4) 0.40780(4) 0.05016(14) Uani 1 1 d . . . . .
Cl2 Cl 1.32547(5) 0.43481(5) 0.81682(4) 0.06919(17) Uani 1 1 d . . . . .
N3 N 1.01860(14) 0.53719(12) 0.64824(12) 0.0493(4) Uani 1 1 d . . . . .
C26 C 1.00226(16) 0.34524(14) 0.61663(13) 0.0405(4) Uani 1 1 d . . . . .
C25 C 0.84108(16) 0.11991(14) 0.41317(13) 0.0430(4) Uani 1 1 d . . . . .
H25 H 0.8128 0.1050 0.3448 0.052 Uiso 1 1 calc R U . . .
C23 C 0.93921(15) 0.24085(13) 0.56296(13) 0.0409(4) Uani 1 1 d . . . . .
C27 C 0.95387(16) 0.44620(14) 0.60171(13) 0.0416(4) Uani 1 1 d . . . . .
C31 C 0.82953(16) 0.46133(14) 0.53699(13) 0.0428(4) Uani 1 1 d . . . . .
C24 C 0.89674(16) 0.21828(14) 0.46088(13) 0.0431(4) Uani 1 1 d . . . . .
H24 H 0.9058 0.2697 0.4244 0.052 Uiso 1 1 calc R U . . .
N4 N 0.62580(14) 0.40136(14) 0.46617(13) 0.0541(4) Uani 1 1 d . . . . .
C28 C 1.11762(17) 0.34214(15) 0.68464(13) 0.0457(4) Uani 1 1 d . . . . .
H28 H 1.1519 0.2769 0.6975 0.055 Uiso 1 1 calc R U . . .
C29 C 1.18054(16) 0.43687(16) 0.73277(14) 0.0472(4) Uani 1 1 d . . . . .
C20 C 0.82766(16) 0.04366(14) 0.46762(13) 0.0423(4) Uani 1 1 d . . . . .
C21 C 0.8705(2) 0.06444(15) 0.56922(14) 0.0553(5) Uani 1 1 d . . . . .
H21 H 0.8614 0.0128 0.6056 0.066 Uiso 1 1 calc R U . . .
C33 C 0.79801(19) 0.55377(16) 0.49104(15) 0.0533(5) Uani 1 1 d . . . . .
H33 H 0.8551 0.6063 0.4999 0.064 Uiso 1 1 calc R U . . .
C32 C 0.73894(17) 0.38993(15) 0.52420(15) 0.0487(4) Uani 1 1 d . . . . .
H32 H 0.7577 0.3302 0.5580 0.058 Uiso 1 1 calc R U . . .
C30 C 1.12906(18) 0.53262(15) 0.71191(15) 0.0517(5) Uani 1 1 d . . . . .
H30 H 1.1733 0.5963 0.7436 0.062 Uiso 1 1 calc R U . . .
C22 C 0.9267(2) 0.16232(15) 0.61622(14) 0.0540(5) Uani 1 1 d . . . . .
H22 H 0.9569 0.1761 0.6848 0.065 Uiso 1 1 calc R U . . .
O4 O 0.72921(16) -0.09006(13) 0.30617(12) 0.0737(5) Uani 1 1 d . . . . .
C35 C 0.59752(18) 0.48818(18) 0.41927(14) 0.0531(5) Uani 1 1 d . . . . .
O3 O 0.80754(15) -0.16329(11) 0.46413(13) 0.0731(5) Uani 1 1 d . . . . .
C34 C 0.6819(2) 0.56672(18) 0.43242(16) 0.0603(5) Uani 1 1 d . . . . .
H34 H 0.6601 0.6283 0.4017 0.072 Uiso 1 1 calc R U . . .
C36 C 0.4695(2) 0.4959(2) 0.35261(18) 0.0739(7) Uani 1 1 d . . . . .
H36A H 0.4595 0.4911 0.2852 0.111 Uiso 1 1 calc R U . . .
H36B H 0.4432 0.5632 0.3707 0.111 Uiso 1 1 calc R U . . .
H36C H 0.4244 0.4382 0.3595 0.111 Uiso 1 1 calc R U . . .
C19 C 0.6146(2) -0.0646(2) 0.4153(2) 0.0738(7) Uani 1 1 d . . . . .
H19A H 0.5773 -0.0048 0.3826 0.111 Uiso 1 1 calc R U . . .
H19B H 0.6274 -0.0521 0.4835 0.111 Uiso 1 1 calc R U . . .
H19C H 0.5652 -0.1286 0.3839 0.111 Uiso 1 1 calc R U . . .
N5 N 0.32203(18) 0.90280(17) 0.20519(16) 0.0674(5) Uani 1 1 d . . . . .
C44 C 0.3193(2) 0.8032(2) 0.2272(2) 0.0786(7) Uani 1 1 d . . . . .
O7 O 0.3222(3) 0.7885(2) 0.30776(18) 0.1289(10) Uani 1 1 d . . . . .
C43 C 0.3164(3) 0.9326(2) 0.1132(2) 0.0815(7) Uani 1 1 d . . . . .
H43A H 0.3084 1.0094 0.1140 0.098 Uiso 1 1 calc R U . . .
H43B H 0.2469 0.8974 0.0593 0.098 Uiso 1 1 calc R U . . .
C40 C 0.4172(4) 0.7081(4) 0.1310(4) 0.1423(19) Uani 1 1 d . . . . .
H40A H 0.4211 0.6354 0.1031 0.171 Uiso 1 1 calc R U . . .
H40B H 0.4853 0.7231 0.1937 0.171 Uiso 1 1 calc R U . . .
C42 C 0.4225(3) 0.9039(4) 0.0938(3) 0.1230(14) Uani 1 1 d . . . . .
H42A H 0.4929 0.9257 0.1534 0.148 Uiso 1 1 calc R U . . .
H42B H 0.4239 0.9439 0.0426 0.148 Uiso 1 1 calc R U . . .
C41 C 0.4246(4) 0.7847(5) 0.0617(4) 0.148(2) Uani 1 1 d . . . . .
H41A H 0.4965 0.7728 0.0533 0.178 Uiso 1 1 calc R U . . .
H41B H 0.3597 0.7658 -0.0025 0.178 Uiso 1 1 calc R U . . .
C45 C 0.3123(3) 0.7134(2) 0.1499(3) 0.1063(11) Uani 1 1 d . . . . .
H45A H 0.2994 0.6461 0.1707 0.128 Uiso 1 1 calc R U . . .
H45B H 0.2452 0.7218 0.0888 0.128 Uiso 1 1 calc R U . . .
C18 C 0.4270(2) 0.8014(2) -0.2529(2) 0.0806(7) Uani 1 1 d . . . . .
H18A H 0.4318 0.8768 -0.2310 0.121 Uiso 1 1 calc R U . . .
H18B H 0.3559 0.7693 -0.2560 0.121 Uiso 1 1 calc R U . . .
H18C H 0.4271 0.7909 -0.3174 0.121 Uiso 1 1 calc R U . . .
O5 O 0.66629(18) 0.88925(15) 0.67835(16) 0.0759(5) Uani 1 1 d . . . . .
O6 O 0.4751(3) 0.7915(3) 0.51041(19) 0.1208(11) Uani 1 1 d . . . . .
H5A H 0.652(3) 0.856(3) 0.720(3) 0.112(12) Uiso 1 1 d . . . . .
H6B H 0.432(3) 0.799(3) 0.457(3) 0.111(13) Uiso 1 1 d . . . . .
H5B H 0.604(3) 0.861(3) 0.619(3) 0.101(10) Uiso 1 1 d . . . . .
H6A H 0.468(4) 0.719(4) 0.515(4) 0.173(19) Uiso 1 1 d . . . . .
H51 H 0.333(3) 0.960(3) 0.258(2) 0.099(10) 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 1.4288(16) . ?
S1 O2 1.4345(16) . ?
S1 C1 1.743(2) . ?
S1 C2 1.7711(17) . ?
Cl1 C11 1.7298(18) . ?
C5 C6 1.386(2) . ?
C5 C4 1.389(3) . ?
C5 C8 1.493(2) . ?
N2 C12 1.324(3) . ?
N2 C9 1.343(2) . ?
C10 C11 1.377(2) . ?
C10 C8 1.388(2) . ?
C9 C8 1.403(3) . ?
C9 C13 1.481(3) . ?
C7 C2 1.378(3) . ?
C7 C6 1.388(2) . ?
N1 C14 1.333(2) . ?
N1 C17 1.341(3) . ?
C2 C3 1.382(3) . ?
C3 C4 1.381(2) . ?
C14 C13 1.382(3) . ?
C13 C15 1.387(3) . ?
C12 C11 1.377(3) . ?
C15 C16 1.373(3) . ?
C17 C16 1.376(3) . ?
C17 C18 1.504(3) . ?
S2 O4 1.4265(17) . ?
S2 O3 1.4299(16) . ?
S2 C19 1.751(2) . ?
S2 C20 1.7656(18) . ?
Cl2 C29 1.732(2) . ?
N3 C30 1.323(3) . ?
N3 C27 1.340(2) . ?
C26 C28 1.386(3) . ?
C26 C27 1.409(2) . ?
C26 C23 1.489(2) . ?
C25 C24 1.380(3) . ?
C25 C20 1.382(3) . ?
C23 C22 1.387(3) . ?
C23 C24 1.388(2) . ?
C27 C31 1.483(3) . ?
C31 C32 1.382(3) . ?
C31 C33 1.394(3) . ?
N4 C35 1.336(3) . ?
N4 C32 1.341(3) . ?
C28 C29 1.373(3) . ?
C29 C30 1.374(3) . ?
C20 C21 1.379(3) . ?
C21 C22 1.375(3) . ?
C33 C34 1.376(3) . ?
C35 C34 1.383(3) . ?
C35 C36 1.509(3) . ?
N5 C44 1.335(3) . ?
N5 C43 1.444(3) . ?
C44 O7 1.229(4) . ?
C44 C45 1.494(4) . ?
C43 C42 1.513(5) . ?
C40 C45 1.458(6) . ?
C40 C41 1.525(7) . ?
C42 C41 1.524(7) . ?

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 118.43(10) . . ?
O1 S1 C1 108.65(11) . . ?
O2 S1 C1 108.20(10) . . ?
O1 S1 C2 107.21(9) . . ?
O2 S1 C2 108.09(9) . . ?
C1 S1 C2 105.55(9) . . ?
C6 C5 C4 119.17(15) . . ?
C6 C5 C8 121.08(16) . . ?
C4 C5 C8 119.59(15) . . ?
C12 N2 C9 118.63(17) . . ?
C11 C10 C8 118.73(17) . . ?
N2 C9 C8 122.15(16) . . ?
N2 C9 C13 115.49(16) . . ?
C8 C9 C13 122.34(15) . . ?
C2 C7 C6 119.26(16) . . ?
C14 N1 C17 118.21(17) . . ?
C7 C2 C3 121.14(16) . . ?
C7 C2 S1 120.01(14) . . ?
C3 C2 S1 118.83(14) . . ?
C5 C6 C7 120.50(17) . . ?
C10 C8 C9 118.07(15) . . ?
C10 C8 C5 118.46(15) . . ?
C9 C8 C5 123.37(15) . . ?
C4 C3 C2 119.17(17) . . ?
N1 C14 C13 124.10(18) . . ?
C14 C13 C15 116.86(18) . . ?
C14 C13 C9 121.42(17) . . ?
C15 C13 C9 121.68(17) . . ?
C3 C4 C5 120.75(17) . . ?
N2 C12 C11 122.65(17) . . ?
C12 C11 C10 119.61(17) . . ?
C12 C11 Cl1 120.20(14) . . ?
C10 C11 Cl1 120.18(15) . . ?
C16 C15 C13 119.45(19) . . ?
N1 C17 C16 121.33(19) . . ?
N1 C17 C18 117.3(2) . . ?
C16 C17 C18 121.4(2) . . ?
C15 C16 C17 119.9(2) . . ?
O4 S2 O3 118.03(11) . . ?
O4 S2 C19 108.47(13) . . ?
O3 S2 C19 108.38(12) . . ?
O4 S2 C20 108.73(9) . . ?
O3 S2 C20 108.84(9) . . ?
C19 S2 C20 103.40(11) . . ?
C30 N3 C27 119.66(16) . . ?
C28 C26 C27 118.11(16) . . ?
C28 C26 C23 117.10(15) . . ?
C27 C26 C23 124.78(16) . . ?
C24 C25 C20 119.63(16) . . ?
C22 C23 C24 118.92(16) . . ?
C22 C23 C26 119.46(16) . . ?
C24 C23 C26 121.56(16) . . ?
N3 C27 C26 121.28(17) . . ?
N3 C27 C31 114.71(16) . . ?
C26 C27 C31 123.99(16) . . ?
C32 C31 C33 116.61(18) . . ?
C32 C31 C27 122.72(16) . . ?
C33 C31 C27 120.53(17) . . ?
C25 C24 C23 120.41(17) . . ?
C35 N4 C32 118.50(18) . . ?
C29 C28 C26 119.00(17) . . ?
C28 C29 C30 119.75(18) . . ?
C28 C29 Cl2 119.73(15) . . ?
C30 C29 Cl2 120.49(15) . . ?
C21 C20 C25 120.66(17) . . ?
C21 C20 S2 118.78(14) . . ?
C25 C20 S2 120.49(14) . . ?
C22 C21 C20 119.31(18) . . ?
C34 C33 C31 119.5(2) . . ?
N4 C32 C31 124.08(18) . . ?
N3 C30 C29 122.11(17) . . ?
C21 C22 C23 121.05(18) . . ?
N4 C35 C34 121.18(19) . . ?
N4 C35 C36 116.5(2) . . ?
C34 C35 C36 122.3(2) . . ?
C33 C34 C35 119.97(19) . . ?
C44 N5 C43 126.5(2) . . ?
O7 C44 N5 120.1(3) . . ?
O7 C44 C45 122.9(3) . . ?
N5 C44 C45 117.0(3) . . ?
N5 C43 C42 113.8(3) . . ?
C45 C40 C41 115.5(4) . . ?
C43 C42 C41 113.5(3) . . ?
C42 C41 C40 116.5(3) . . ?
C40 C45 C44 113.4(3) . . ?

_refine_diff_density_max         0.467
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.047


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_ETRGA
_database_code_depnum_ccdc_archive 'CCDC 1444656'
_audit_update_record             
;
2016-02-25 deposited with the CCDC.
2016-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
"5-Chloro-6'-methyl-3-[4-(methylsulfonyl)phenyl]-2,3'-bipyridine-pentanedioic acid"
_chemical_name_common            'etoricoxib-gluraric acid cocrystal'
_chemical_melting_point          401.7K
_chemical_formula_moiety         'C23 H23 Cl N2 O6 S'
_chemical_formula_sum            'C23 H23 Cl N2 O6 S'
_chemical_formula_weight         490.94

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                   11.8317(15)
_cell_length_b                   12.7266(16)
_cell_length_c                   15.772(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.203(2)
_cell_angle_gamma                90
_cell_volume                     2375.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4098
_cell_measurement_theta_min      2.056
_cell_measurement_theta_max      26.403

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    0.290
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24676
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.056
_diffrn_reflns_theta_max         26.403
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4862
_reflns_number_gt                4098
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0731P)²+0.5318P] 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         4862
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1281
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.93557(4) -0.05541(3) 0.17515(3) 0.05117(15) Uani 1 1 d . . . . .
Cl1 Cl 0.95717(5) 0.65176(4) 0.29111(4) 0.07680(19) Uani 1 1 d . . . . .
C2 C 0.92233(14) 0.08176(12) 0.16037(11) 0.0432(4) Uani 1 1 d . . . . .
N2 N 0.86115(14) 0.57454(11) 0.05961(10) 0.0552(4) Uani 1 1 d . . . . .
C6 C 0.96725(15) 0.23875(13) 0.08571(11) 0.0475(4) Uani 1 1 d . . . . .
H6 H 1.0049 0.2728 0.0420 0.057 Uiso 1 1 calc R U . . .
C9 C 0.85701(14) 0.46901(12) 0.06265(11) 0.0449(4) Uani 1 1 d . . . . .
C13 C 0.81297(14) 0.41941(13) -0.01589(11) 0.0466(4) Uani 1 1 d . . . . .
C8 C 0.89103(13) 0.41302(12) 0.13514(11) 0.0433(4) Uani 1 1 d . . . . .
C5 C 0.90030(13) 0.29632(12) 0.14096(10) 0.0418(3) Uani 1 1 d . . . . .
C10 C 0.92060(15) 0.47045(13) 0.20675(12) 0.0496(4) Uani 1 1 d . . . . .
H10 H 0.9401 0.4362 0.2568 0.060 Uiso 1 1 calc R U . . .
C3 C 0.85559(15) 0.13733(13) 0.21612(12) 0.0506(4) Uani 1 1 d . . . . .
H3 H 0.8185 0.1029 0.2600 0.061 Uiso 1 1 calc R U . . .
C7 C 0.97839(16) 0.13148(13) 0.09511(11) 0.0488(4) Uani 1 1 d . . . . .
H7 H 1.0231 0.0931 0.0579 0.059 Uiso 1 1 calc R U . . .
C4 C 0.84454(15) 0.24449(13) 0.20613(11) 0.0497(4) Uani 1 1 d . . . . .
H4 H 0.7994 0.2824 0.2433 0.060 Uiso 1 1 calc R U . . .
N1 N 0.71129(14) 0.28051(13) -0.08543(11) 0.0607(4) Uani 1 1 d . . . . .
C11 C 0.92079(15) 0.57858(14) 0.20312(12) 0.0528(4) Uani 1 1 d . . . . .
C15 C 0.82934(16) 0.46570(15) -0.09473(12) 0.0549(4) Uani 1 1 d . . . . .
H15 H 0.8680 0.5291 -0.0987 0.066 Uiso 1 1 calc R U . . .
O2 O 0.94755(18) -0.10443(11) 0.09444(10) 0.0863(5) Uani 1 1 d . . . . .
C12 C 0.89343(17) 0.62745(14) 0.12799(14) 0.0589(5) Uani 1 1 d . . . . .
H12 H 0.8977 0.7003 0.1250 0.071 Uiso 1 1 calc R U . . .
C14 C 0.75069(16) 0.32703(14) -0.01562(12) 0.0555(4) Uani 1 1 d . . . . .
H14 H 0.7355 0.2957 0.0364 0.067 Uiso 1 1 calc R U . . .
C19 C 0.17756(19) 0.49507(16) 0.45372(14) 0.0632(5) Uani 1 1 d . . . . .
O1 O 0.84507(13) -0.08900(11) 0.22785(12) 0.0815(5) Uani 1 1 d . . . . .
O6 O 0.0545(2) 0.93382(14) 0.58842(11) 0.0990(7) Uani 1 1 d . . . . .
C17 C 0.73073(16) 0.32428(16) -0.16072(12) 0.0577(5) Uani 1 1 d . . . . .
C16 C 0.78890(16) 0.41852(17) -0.16648(13) 0.0606(5) Uani 1 1 d . . . . .
H16 H 0.8004 0.4496 -0.2191 0.073 Uiso 1 1 calc R U . . .
O3 O 0.1508(2) 0.40237(14) 0.48287(13) 0.0981(6) Uani 1 1 d . . . . .
C23 C 0.0655(2) 0.86681(16) 0.52738(14) 0.0684(5) Uani 1 1 d . . . . .
O5 O 0.0398(2) 0.88644(14) 0.45443(10) 0.0987(7) Uani 1 1 d . . . . .
C21 C 0.1343(2) 0.68597(17) 0.48509(14) 0.0733(6) Uani 1 1 d . . . . .
H21A H 0.0711 0.6834 0.4458 0.088 Uiso 1 1 calc R U . . .
H21B H 0.2001 0.7100 0.4542 0.088 Uiso 1 1 calc R U . . .
C1 C 1.06246(18) -0.07087(16) 0.23112(16) 0.0683(6) Uani 1 1 d . . . . .
H1A H 1.0585 -0.0327 0.2835 0.102 Uiso 1 1 calc R U . . .
H1B H 1.1239 -0.0443 0.1978 0.102 Uiso 1 1 calc R U . . .
H1C H 1.0746 -0.1440 0.2428 0.102 Uiso 1 1 calc R U . . .
C20 C 0.1563(2) 0.57837(17) 0.51872(14) 0.0721(6) Uani 1 1 d . . . . .
H20B H 0.0918 0.5572 0.5525 0.087 Uiso 1 1 calc R U . . .
H20A H 0.2212 0.5817 0.5563 0.087 Uiso 1 1 calc R U . . .
C22 C 0.1082(2) 0.76291(16) 0.55493(14) 0.0674(5) Uani 1 1 d . . . . .
H22A H 0.0525 0.7314 0.5921 0.081 Uiso 1 1 calc R U . . .
H22B H 0.1765 0.7737 0.5881 0.081 Uiso 1 1 calc R U . . .
O4 O 0.2125(2) 0.50928(15) 0.38464(13) 0.1103(7) Uani 1 1 d . . . . .
C18 C 0.6842(2) 0.2688(2) -0.23749(15) 0.0820(7) Uani 1 1 d . . . . .
H18A H 0.6971 0.1946 -0.2321 0.123 Uiso 1 1 calc R U . . .
H18B H 0.7214 0.2944 -0.2874 0.123 Uiso 1 1 calc R U . . .
H18C H 0.6045 0.2820 -0.2420 0.123 Uiso 1 1 calc R U . . .
H6A H 0.021(3) 0.999(3) 0.567(2) 0.115 Uiso 1 1 d . U . . .
H3A H 0.167(3) 0.354(3) 0.445(2) 0.113(11) 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 1.4236(15) . ?
S1 O2 1.4251(15) . ?
S1 C1 1.750(2) . ?
S1 C2 1.7680(16) . ?
Cl1 C11 1.7247(19) . ?
C2 C3 1.379(2) . ?
C2 C7 1.380(2) . ?
N2 C12 1.326(2) . ?
N2 C9 1.345(2) . ?
C6 C7 1.380(2) . ?
C6 C5 1.389(2) . ?
C9 C8 1.405(2) . ?
C9 C13 1.483(2) . ?
C13 C14 1.387(2) . ?
C13 C15 1.390(2) . ?
C8 C10 1.389(2) . ?
C8 C5 1.492(2) . ?
C5 C4 1.390(2) . ?
C10 C11 1.377(2) . ?
C3 C4 1.379(2) . ?
N1 C17 1.332(3) . ?
N1 C14 1.333(2) . ?
C11 C12 1.376(3) . ?
C15 C16 1.366(3) . ?
C19 O4 1.181(3) . ?
C19 O3 1.305(3) . ?
C19 C20 1.497(3) . ?
O6 C23 1.293(3) . ?
C17 C16 1.386(3) . ?
C17 C18 1.504(3) . ?
C23 O5 1.215(3) . ?
C23 C22 1.480(3) . ?
C21 C20 1.491(3) . ?
C21 C22 1.506(3) . ?

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 117.87(11) . . ?
O1 S1 C1 108.50(11) . . ?
O2 S1 C1 108.27(12) . . ?
O1 S1 C2 107.88(8) . . ?
O2 S1 C2 108.88(9) . . ?
C1 S1 C2 104.66(9) . . ?
C3 C2 C7 121.22(15) . . ?
C3 C2 S1 118.23(12) . . ?
C7 C2 S1 120.56(13) . . ?
C12 N2 C9 119.23(16) . . ?
C7 C6 C5 120.60(15) . . ?
N2 C9 C8 121.69(16) . . ?
N2 C9 C13 114.08(15) . . ?
C8 C9 C13 124.23(15) . . ?
C14 C13 C15 115.94(16) . . ?
C14 C13 C9 122.89(15) . . ?
C15 C13 C9 121.14(15) . . ?
C10 C8 C9 117.73(15) . . ?
C10 C8 C5 117.10(14) . . ?
C9 C8 C5 125.15(15) . . ?
C6 C5 C4 119.15(15) . . ?
C6 C5 C8 121.90(14) . . ?
C4 C5 C8 118.87(14) . . ?
C11 C10 C8 119.49(16) . . ?
C2 C3 C4 119.25(16) . . ?
C6 C7 C2 119.20(15) . . ?
C3 C4 C5 120.58(16) . . ?
C17 N1 C14 119.30(16) . . ?
C12 C11 C10 119.15(17) . . ?
C12 C11 Cl1 120.41(14) . . ?
C10 C11 Cl1 120.43(15) . . ?
C16 C15 C13 120.35(17) . . ?
N2 C12 C11 122.48(16) . . ?
N1 C14 C13 123.92(17) . . ?
O4 C19 O3 123.3(2) . . ?
O4 C19 C20 125.7(2) . . ?
O3 C19 C20 110.9(2) . . ?
N1 C17 C16 120.51(18) . . ?
N1 C17 C18 117.22(19) . . ?
C16 C17 C18 122.3(2) . . ?
C15 C16 C17 119.91(18) . . ?
O5 C23 O6 123.0(2) . . ?
O5 C23 C22 123.08(19) . . ?
O6 C23 C22 113.92(19) . . ?
C20 C21 C22 111.88(18) . . ?
C21 C20 C19 115.88(19) . . ?
C23 C22 C21 115.88(18) . . ?

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.051


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOAc'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_ETRSBA
_database_code_depnum_ccdc_archive 'CCDC 1444657'
_audit_update_record             
;
2015-12-29 deposited with the CCDC.
2016-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'5-Chloro-6-methyl-3-[4-(methylsulfonyl)phenyl]-2,3-bipyridine-octanedioic acid'
_chemical_name_common            'etoricoxib-suberic acid cocrystal'
_chemical_melting_point          390.4
_chemical_formula_moiety         'C18 H15 Cl N2 O2 S, C8 H14 O4'
_chemical_formula_sum            'C26 H29 Cl N2 O6 S'
_chemical_formula_weight         533.02

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'
Cl Cl 0.3639 0.7018 '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'

_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                   9.0238(3)
_cell_length_b                   10.1284(5)
_cell_length_c                   14.8544(9)
_cell_angle_alpha                82.766(5)
_cell_angle_beta                 77.640(4)
_cell_angle_gamma                85.386(4)
_cell_volume                     1313.61(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3886
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      66.59

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_exptl_absorpt_coefficient_mu    2.396
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_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     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            7910
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.065
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_full        66.589
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4615
_reflns_number_gt                3886
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0688P)²+0.1934P] 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         4615
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1154
_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 1.28822(6) 1.00616(6) 0.60966(4) 0.05446(16) Uani 1 1 d . . . . .
Cl1 Cl 0.27804(7) 1.17203(6) 0.90949(5) 0.0724(2) Uani 1 1 d . . . . .
N1 N 0.85474(18) 0.53976(15) 0.75865(11) 0.0432(4) Uani 1 1 d . . . . .
O4 O 0.05393(19) 0.66114(15) 0.93102(11) 0.0618(4) Uani 1 1 d . . . . .
H4A H -0.0011 0.6281 0.9785 0.093 Uiso 1 1 calc R U . . .
O3 O 0.12389(17) 0.44871(15) 0.91590(11) 0.0570(4) Uani 1 1 d . . . . .
N2 N 0.45372(19) 0.80201(17) 0.91936(12) 0.0479(4) Uani 1 1 d . . . . .
O5 O 0.92151(18) 0.47087(16) 0.39438(11) 0.0611(4) Uani 1 1 d . . . . .
H5A H 0.9961 0.4721 0.3516 0.092 Uiso 1 1 calc R U . . .
C5 C 0.8044(2) 0.95927(16) 0.77154(13) 0.0392(4) Uani 1 1 d . . . . .
C8 C 0.6467(2) 0.93910(18) 0.82516(13) 0.0399(4) Uani 1 1 d . . . . .
O6 O 1.0315(2) 0.27674(17) 0.43806(13) 0.0697(5) Uani 1 1 d . . . . .
C14 C 0.7818(2) 0.65891(18) 0.77187(13) 0.0416(4) Uani 1 1 d . . . . .
H14 H 0.7997 0.7278 0.7239 0.050 Uiso 1 1 calc R U . . .
C17 C 0.8276(2) 0.43823(18) 0.82637(14) 0.0436(4) Uani 1 1 d . . . . .
C6 C 0.8304(2) 1.01057(18) 0.67856(14) 0.0443(4) Uani 1 1 d . . . . .
H6 H 0.7488 1.0330 0.6495 0.053 Uiso 1 1 calc R U . . .
C9 C 0.5936(2) 0.81403(18) 0.86586(12) 0.0392(4) Uani 1 1 d . . . . .
C15 C 0.6567(2) 0.57919(19) 0.92299(14) 0.0450(4) Uani 1 1 d . . . . .
H15 H 0.5919 0.5919 0.9794 0.054 Uiso 1 1 calc R U . . .
C7 C 0.9771(2) 1.02845(19) 0.62905(14) 0.0465(4) Uani 1 1 d . . . . .
H7 H 0.9945 1.0616 0.5666 0.056 Uiso 1 1 calc R U . . .
C2 C 1.0979(2) 0.99638(18) 0.67340(14) 0.0438(4) Uani 1 1 d . . . . .
C13 C 0.6813(2) 0.68462(17) 0.85311(13) 0.0384(4) Uani 1 1 d . . . . .
C3 C 1.0736(2) 0.9496(2) 0.76636(15) 0.0478(4) Uani 1 1 d . . . . .
H3 H 1.1551 0.9314 0.7960 0.057 Uiso 1 1 calc R U . . .
C4 C 0.9267(2) 0.93008(19) 0.81515(14) 0.0456(4) Uani 1 1 d . . . . .
H4 H 0.9097 0.8971 0.8776 0.055 Uiso 1 1 calc R U . . .
C19 C 0.1355(2) 0.5659(2) 0.88731(14) 0.0470(4) Uani 1 1 d . . . . .
C10 C 0.5474(2) 1.04965(19) 0.83827(15) 0.0481(4) Uani 1 1 d . . . . .
H10 H 0.5773 1.1335 0.8107 0.058 Uiso 1 1 calc R U . . .
C24 C 0.6979(2) 0.4705(2) 0.55716(14) 0.0486(4) Uani 1 1 d . . . . .
H24A H 0.6513 0.5035 0.5050 0.058 Uiso 1 1 calc R U . . .
H24B H 0.7572 0.5403 0.5683 0.058 Uiso 1 1 calc R U . . .
C11 C 0.4042(2) 1.0352(2) 0.89222(15) 0.0495(5) Uani 1 1 d . . . . .
C12 C 0.3625(2) 0.9103(2) 0.93260(15) 0.0513(5) Uani 1 1 d . . . . .
H12 H 0.2667 0.9013 0.9706 0.062 Uiso 1 1 calc R U . . .
C16 C 0.7280(2) 0.45582(19) 0.90899(14) 0.0468(4) Uani 1 1 d . . . . .
H16 H 0.7091 0.3846 0.9551 0.056 Uiso 1 1 calc R U . . .
C20 C 0.2430(2) 0.6150(2) 0.80036(15) 0.0529(5) Uani 1 1 d . . . . .
H20A H 0.2994 0.6857 0.8131 0.063 Uiso 1 1 calc R U . . .
H20B H 0.1853 0.6523 0.7541 0.063 Uiso 1 1 calc R U . . .
C23 C 0.5750(2) 0.4367(2) 0.64246(15) 0.0531(5) Uani 1 1 d . . . . .
H23A H 0.5158 0.3682 0.6296 0.064 Uiso 1 1 calc R U . . .
H23B H 0.6237 0.3992 0.6929 0.064 Uiso 1 1 calc R U . . .
O1 O 1.3048(2) 0.9322(2) 0.53266(15) 0.0875(6) Uani 1 1 d . . . . .
C26 C 0.9296(2) 0.3607(2) 0.45145(14) 0.0487(5) Uani 1 1 d . . . . .
C22 C 0.4676(2) 0.5513(2) 0.67483(15) 0.0515(5) Uani 1 1 d . . . . .
H22A H 0.4143 0.5875 0.6262 0.062 Uiso 1 1 calc R U . . .
H22B H 0.5251 0.6213 0.6874 0.062 Uiso 1 1 calc R U . . .
C21 C 0.3536(3) 0.5059(2) 0.76167(16) 0.0575(5) Uani 1 1 d . . . . .
H21A H 0.2965 0.4364 0.7480 0.069 Uiso 1 1 calc R U . . .
H21B H 0.4084 0.4671 0.8090 0.069 Uiso 1 1 calc R U . . .
C25 C 0.8013(3) 0.3488(2) 0.53414(16) 0.0568(5) Uani 1 1 d . . . . .
H25A H 0.8444 0.3173 0.5879 0.068 Uiso 1 1 calc R U . . .
H25B H 0.7383 0.2799 0.5260 0.068 Uiso 1 1 calc R U . . .
C18 C 0.9105(3) 0.3066(2) 0.80686(18) 0.0601(6) Uani 1 1 d . . . . .
H18A H 0.8710 0.2701 0.7608 0.090 Uiso 1 1 calc R U . . .
H18B H 0.8966 0.2461 0.8628 0.090 Uiso 1 1 calc R U . . .
H18C H 1.0169 0.3196 0.7845 0.090 Uiso 1 1 calc R U . . .
O2 O 1.3864(2) 0.9707(3) 0.67243(16) 0.1056(9) Uani 1 1 d . . . . .
C1 C 1.3070(3) 1.1731(3) 0.5659(3) 0.0957(11) Uani 1 1 d . . . . .
H1A H 1.2973 1.2261 0.6163 0.144 Uiso 1 1 calc R U . . .
H1B H 1.2292 1.2016 0.5315 0.144 Uiso 1 1 calc R U . . .
H1C H 1.4050 1.1835 0.5258 0.144 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 1.414(2) . ?
S1 O1 1.420(2) . ?
S1 C1 1.741(3) . ?
S1 C2 1.7788(19) . ?
Cl1 C11 1.7300(19) . ?
N1 C17 1.343(2) . ?
N1 C14 1.343(2) . ?
O4 C19 1.316(2) . ?
O3 C19 1.215(3) . ?
N2 C12 1.326(3) . ?
N2 C9 1.346(2) . ?
O5 C26 1.321(3) . ?
C5 C4 1.389(3) . ?
C5 C6 1.390(3) . ?
C5 C8 1.491(3) . ?
C8 C10 1.383(3) . ?
C8 C9 1.407(3) . ?
O6 C26 1.203(3) . ?
C14 C13 1.385(3) . ?
C17 C16 1.379(3) . ?
C17 C18 1.505(3) . ?
C6 C7 1.383(3) . ?
C9 C13 1.487(2) . ?
C15 C16 1.378(3) . ?
C15 C13 1.388(3) . ?
C7 C2 1.387(3) . ?
C2 C3 1.379(3) . ?
C3 C4 1.384(3) . ?
C19 C20 1.495(3) . ?
C10 C11 1.375(3) . ?
C24 C25 1.513(3) . ?
C24 C23 1.517(3) . ?
C11 C12 1.375(3) . ?
C20 C21 1.512(3) . ?
C23 C22 1.509(3) . ?
C26 C25 1.497(3) . ?
C22 C21 1.514(3) . ?

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 118.12(16) . . ?
O2 S1 C1 109.16(19) . . ?
O1 S1 C1 107.20(17) . . ?
O2 S1 C2 108.02(11) . . ?
O1 S1 C2 108.16(10) . . ?
C1 S1 C2 105.47(12) . . ?
C17 N1 C14 119.05(16) . . ?
C12 N2 C9 119.28(17) . . ?
C4 C5 C6 119.42(17) . . ?
C4 C5 C8 119.95(17) . . ?
C6 C5 C8 120.60(17) . . ?
C10 C8 C9 117.70(17) . . ?
C10 C8 C5 118.49(16) . . ?
C9 C8 C5 123.78(16) . . ?
N1 C14 C13 123.53(17) . . ?
N1 C17 C16 120.78(17) . . ?
N1 C17 C18 116.61(18) . . ?
C16 C17 C18 122.61(18) . . ?
C7 C6 C5 120.35(18) . . ?
N2 C9 C8 121.58(17) . . ?
N2 C9 C13 113.79(15) . . ?
C8 C9 C13 124.62(16) . . ?
C16 C15 C13 120.13(18) . . ?
C6 C7 C2 119.35(18) . . ?
C3 C2 C7 120.96(18) . . ?
C3 C2 S1 118.55(16) . . ?
C7 C2 S1 120.40(15) . . ?
C14 C13 C15 116.64(17) . . ?
C14 C13 C9 123.59(16) . . ?
C15 C13 C9 119.65(17) . . ?
C2 C3 C4 119.36(18) . . ?
C3 C4 C5 120.51(18) . . ?
O3 C19 O4 122.41(19) . . ?
O3 C19 C20 123.43(18) . . ?
O4 C19 C20 114.16(18) . . ?
C11 C10 C8 119.83(18) . . ?
C25 C24 C23 110.65(17) . . ?
C10 C11 C12 119.08(18) . . ?
C10 C11 Cl1 120.62(16) . . ?
C12 C11 Cl1 120.30(16) . . ?
N2 C12 C11 122.45(18) . . ?
C15 C16 C17 119.84(17) . . ?
C19 C20 C21 112.44(18) . . ?
C22 C23 C24 115.84(18) . . ?
O6 C26 O5 122.80(19) . . ?
O6 C26 C25 122.8(2) . . ?
O5 C26 C25 114.43(18) . . ?
C23 C22 C21 110.79(18) . . ?
C20 C21 C22 114.51(19) . . ?
C26 C25 C24 119.12(18) . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.047


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dry MeOH'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_ETRSBA_trihydrate
_database_code_depnum_ccdc_archive 'CCDC 1444658'
_audit_update_record             
;
2015-12-29 deposited with the CCDC.
2016-02-25 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT306_ETRSBA              
;
RESPONSE: The hydrogen atoms could not be located on this water molecule.
;
_vrf_PLAT430_ETRSBA              
;
RESPONSE: The presence of strong O-H....N
hydrogen bonds bring all components of the structure in close proximity.  
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'5-Chloro-6-methyl-3-[4-(methylsulfonyl)phenyl]-2,3-bipyridine-octanedioic acid trihydrate'
_chemical_name_common            'etoricoxib-suberic acid cocrystal hydrate'
_chemical_melting_point          388.2
_chemical_formula_moiety         
'2(C18 H15 Cl N2 O2 S), 0.5(C8 H14 O4), 2(H2 O), O'
_chemical_formula_sum            'C40 H41 Cl2 N4 O9 S2'
_chemical_formula_weight         856.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   12.2796(15)
_cell_length_b                   12.4817(10)
_cell_length_c                   14.8713(18)
_cell_angle_alpha                95.187(8)
_cell_angle_beta                 113.754(12)
_cell_angle_gamma                91.242(8)
_cell_volume                     2073.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7303
_cell_measurement_theta_min      2.790
_cell_measurement_theta_max      25.026

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             894
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.316
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_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  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13766
_diffrn_reflns_av_unetI/netI     0.1651
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.790
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7303
_reflns_number_gt                3338
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0168P)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         7303
_refine_ls_number_parameters     523
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1562
_refine_ls_R_factor_gt           0.0649
_refine_ls_wR_factor_ref         0.1307
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      0.962
_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
S2 S 0.74508(12) 0.57982(9) 1.09392(10) 0.0428(4) Uani 1 1 d . . . . .
S1 S 0.54574(13) 0.32248(8) 0.31877(10) 0.0408(4) Uani 1 1 d . . . . .
Cl1 Cl 0.34081(12) 1.02744(9) 0.29062(10) 0.0532(4) Uani 1 1 d . . . . .
Cl2 Cl 0.16327(13) 0.06440(10) 0.68441(10) 0.0608(5) Uani 1 1 d . . . . .
O1 O 0.6533(3) 0.2953(2) 0.3073(3) 0.0538(10) Uani 1 1 d . . . . .
O2 O 0.5186(3) 0.2750(2) 0.3923(2) 0.0554(11) Uani 1 1 d . . . . .
C28 C 0.5417(5) 0.0524(3) 0.8940(3) 0.0374(13) Uani 1 1 d . . . . .
N2 N 0.6677(4) 0.9773(3) 0.4769(3) 0.0376(11) Uani 1 1 d . . . . .
C5 C 0.5632(4) 0.6850(3) 0.3943(3) 0.0300(12) Uani 1 1 d . . . . .
N4 N 0.4764(4) -0.0395(3) 0.8465(3) 0.0442(12) Uani 1 1 d . . . . .
N1 N 0.8613(4) 0.7047(3) 0.6687(3) 0.0445(12) Uani 1 1 d . . . . .
O3 O 0.7603(3) 0.5869(2) 1.1953(2) 0.0619(12) Uani 1 1 d . . . . .
C8 C 0.5648(4) 0.8041(3) 0.4111(3) 0.0310(12) Uani 1 1 d . . . . .
C7 C 0.6452(4) 0.5266(3) 0.3463(3) 0.0338(12) Uani 1 1 d . . . . .
H7 H 0.7041 0.4955 0.3303 0.041 Uiso 1 1 calc R U . . .
C9 C 0.6661(4) 0.8690(3) 0.4748(3) 0.0334(12) Uani 1 1 d . . . . .
C24 C 0.5560(4) 0.2581(3) 0.9350(3) 0.0335(12) Uani 1 1 d . . . . .
C25 C 0.5964(4) 0.2781(3) 1.0365(3) 0.0362(13) Uani 1 1 d . . . . .
H25 H 0.5869 0.2241 1.0724 0.043 Uiso 1 1 calc R U . . .
O4 O 0.6891(3) 0.6648(2) 1.0370(3) 0.0612(12) Uani 1 1 d . . . . .
C10 C 0.4638(4) 0.8537(3) 0.3556(3) 0.0367(13) Uani 1 1 d . . . . .
H10 H 0.3945 0.8124 0.3151 0.044 Uiso 1 1 calc R U . . .
C27 C 0.3763(5) 0.1581(3) 0.8131(3) 0.0394(13) Uani 1 1 d . . . . .
H27 H 0.3421 0.2239 0.8008 0.047 Uiso 1 1 calc R U . . .
C20 C 0.6665(4) 0.4560(3) 1.0321(3) 0.0322(12) Uani 1 1 d . . . . .
C2 C 0.5510(5) 0.4641(3) 0.3461(3) 0.0345(12) Uani 1 1 d . . . . .
C26 C 0.4926(5) 0.1534(3) 0.8799(3) 0.0377(13) Uani 1 1 d . . . . .
C13 C 0.7742(4) 0.8255(3) 0.5442(3) 0.0326(12) Uani 1 1 d . . . . .
C11 C 0.4658(4) 0.9640(3) 0.3602(3) 0.0347(12) Uani 1 1 d . . . . .
C22 C 0.6506(4) 0.3770(3) 1.0856(3) 0.0368(13) Uani 1 1 d . . . . .
H22 H 0.6759 0.3901 1.1538 0.044 Uiso 1 1 calc R U . . .
C29 C 0.3119(4) 0.0630(4) 0.7649(3) 0.0395(13) Uani 1 1 d . . . . .
C3 C 0.4633(5) 0.5094(3) 0.3693(3) 0.0428(14) Uani 1 1 d . . . . .
H3 H 0.4003 0.4663 0.3690 0.051 Uiso 1 1 calc R U . . .
C4 C 0.4695(4) 0.6204(3) 0.3934(3) 0.0391(13) Uani 1 1 d . . . . .
H4 H 0.4103 0.6515 0.4091 0.047 Uiso 1 1 calc R U . . .
C14 C 0.7659(5) 0.7487(3) 0.6038(3) 0.0394(13) Uani 1 1 d . . . . .
H14 H 0.6906 0.7265 0.5986 0.047 Uiso 1 1 calc R U . . .
N3 N 0.8739(4) 0.1022(3) 1.0344(3) 0.0527(13) Uani 1 1 d . . . . .
C23 C 0.5714(5) 0.3395(3) 0.8825(3) 0.0462(15) Uani 1 1 d . . . . .
H23 H 0.5433 0.3277 0.8140 0.055 Uiso 1 1 calc R U . . .
C16 C 0.9842(5) 0.8160(3) 0.6221(4) 0.0481(15) Uani 1 1 d . . . . .
H16 H 1.0602 0.8378 0.6287 0.058 Uiso 1 1 calc R U . . .
C35 C 0.9024(5) 0.0126(4) 1.0804(4) 0.0484(14) Uani 1 1 d . . . . .
C33 C 0.6990(5) -0.0562(4) 1.0038(4) 0.0456(14) Uani 1 1 d . . . . .
H33 H 0.6411 -0.1107 0.9934 0.055 Uiso 1 1 calc R U . . .
C6 C 0.6498(4) 0.6365(3) 0.3709(3) 0.0363(13) Uani 1 1 d . . . . .
H6 H 0.7133 0.6792 0.3717 0.044 Uiso 1 1 calc R U . . .
C30 C 0.3647(5) -0.0338(4) 0.7852(4) 0.0488(15) Uani 1 1 d . . . . .
H30 H 0.3192 -0.0975 0.7541 0.059 Uiso 1 1 calc R U . . .
C12 C 0.5694(5) 1.0225(3) 0.4197(4) 0.0426(14) Uani 1 1 d . . . . .
H12 H 0.5716 1.0971 0.4204 0.051 Uiso 1 1 calc R U . . .
C31 C 0.6671(5) 0.0378(3) 0.9587(3) 0.0386(13) Uani 1 1 d . . . . .
C17 C 0.9702(5) 0.7392(4) 0.6773(4) 0.0442(14) Uani 1 1 d . . . . .
C15 C 0.8868(5) 0.8608(3) 0.5572(4) 0.0443(14) Uani 1 1 d . . . . .
H15 H 0.8968 0.9152 0.5219 0.053 Uiso 1 1 calc R U . . .
C21 C 0.6284(5) 0.4386(3) 0.9313(3) 0.0471(15) Uani 1 1 d . . . . .
H21 H 0.6405 0.4923 0.8962 0.057 Uiso 1 1 calc R U . . .
C32 C 0.7606(5) 0.1124(4) 0.9756(4) 0.0463(14) Uani 1 1 d . . . . .
H32 H 0.7426 0.1742 0.9432 0.056 Uiso 1 1 calc R U . . .
C34 C 0.8152(5) -0.0685(4) 1.0634(4) 0.0554(16) Uani 1 1 d . . . . .
H34 H 0.8362 -0.1319 1.0929 0.066 Uiso 1 1 calc R U . . .
C1 C 0.4256(5) 0.2916(3) 0.2043(3) 0.0537(16) Uani 1 1 d . . . . .
H1A H 0.4176 0.2152 0.1860 0.081 Uiso 1 1 calc R U . . .
H1B H 0.4396 0.3278 0.1552 0.081 Uiso 1 1 calc R U . . .
H1C H 0.3538 0.3150 0.2087 0.081 Uiso 1 1 calc R U . . .
C18 C 1.0742(5) 0.6874(4) 0.7497(4) 0.0679(19) Uani 1 1 d . . . . .
H18A H 1.0796 0.7063 0.8154 0.102 Uiso 1 1 calc R U . . .
H18B H 1.1464 0.7123 0.7455 0.102 Uiso 1 1 calc R U . . .
H18C H 1.0631 0.6105 0.7344 0.102 Uiso 1 1 calc R U . . .
C36 C 1.0303(5) 0.0053(4) 1.1490(4) 0.0712(19) Uani 1 1 d . . . . .
H36A H 1.0805 0.0475 1.1282 0.107 Uiso 1 1 calc R U . . .
H36B H 1.0504 -0.0685 1.1478 0.107 Uiso 1 1 calc R U . . .
H36C H 1.0419 0.0324 1.2149 0.107 Uiso 1 1 calc R U . . .
C19 C 0.8842(5) 0.5674(4) 1.0906(4) 0.0690(18) Uani 1 1 d . . . . .
H19A H 0.8752 0.5580 1.0231 0.103 Uiso 1 1 calc R U . . .
H19B H 0.9200 0.5060 1.1229 0.103 Uiso 1 1 calc R U . . .
H19C H 0.9343 0.6313 1.1239 0.103 Uiso 1 1 calc R U . . .
O9 O 0.1422(4) 0.8670(3) 0.4624(3) 0.0738(13) Uani 1 1 d . . . . .
H9A H 0.1891 0.9118 0.4578 0.111 Uiso 1 1 calc R U . . .
O8 O 0.1999(5) 0.7678(3) 0.3620(4) 0.1041(18) Uani 1 1 d . . . . .
C39 C 0.0395(5) 0.7003(4) 0.3950(4) 0.069(2) Uani 1 1 d . . . . .
H39A H 0.0046 0.6646 0.3280 0.082 Uiso 1 1 calc R U . . .
H39B H -0.0228 0.7376 0.4068 0.082 Uiso 1 1 calc R U . . .
C38 C 0.0822(5) 0.6167(4) 0.4654(4) 0.0624(18) Uani 1 1 d . . . . .
H38A H 0.1269 0.6522 0.5315 0.075 Uiso 1 1 calc R U . . .
H38B H 0.1358 0.5722 0.4475 0.075 Uiso 1 1 calc R U . . .
C37 C -0.0200(5) 0.5447(3) 0.4655(4) 0.0658(19) Uani 1 1 d . . . . .
H37A H -0.0660 0.5116 0.3987 0.079 Uiso 1 1 calc R U . . .
H37B H -0.0721 0.5894 0.4850 0.079 Uiso 1 1 calc R U . . .
C40 C 0.1331(6) 0.7797(5) 0.4030(5) 0.0591(17) Uani 1 1 d . . . . .
O6 O 0.1802(5) 0.6444(4) 0.1806(4) 0.0875(9) Uani 1 1 d D . . . .
O7 O 0.0244(4) 0.7025(3) 0.9888(3) 0.0875(9) Uani 1 1 d . . . . .
O5 O 0.1605(5) 0.4169(4) 0.1781(4) 0.0875(9) Uani 1 1 d D . . . .
H6A H 0.170(7) 0.642(5) 0.238(3) 0.16(3) Uiso 1 1 d D . . . .
H6B H 0.143(9) 0.669(7) 0.120(4) 0.32(6) Uiso 1 1 d D . . . .
H5B H 0.154(5) 0.400(4) 0.231(2) 0.09(2) Uiso 1 1 d D . . . .
H5A H 0.098(5) 0.382(5) 0.129(4) 0.18(4) 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
S2 O4 1.428(3) . ?
S2 O3 1.437(3) . ?
S2 C19 1.739(6) . ?
S2 C20 1.769(4) . ?
S1 O2 1.436(3) . ?
S1 O1 1.442(4) . ?
S1 C1 1.748(5) . ?
S1 C2 1.771(4) . ?
Cl1 C11 1.724(5) . ?
Cl2 C29 1.735(5) . ?
C28 N4 1.348(5) . ?
C28 C26 1.405(6) . ?
C28 C31 1.476(6) . ?
N2 C12 1.338(6) . ?
N2 C9 1.349(5) . ?
C5 C6 1.382(6) . ?
C5 C4 1.385(6) . ?
C5 C8 1.484(5) . ?
N4 C30 1.315(6) . ?
N1 C17 1.347(6) . ?
N1 C14 1.348(6) . ?
C8 C10 1.379(6) . ?
C8 C9 1.403(6) . ?
C7 C2 1.380(6) . ?
C7 C6 1.380(5) . ?
C9 C13 1.467(6) . ?
C24 C25 1.382(6) . ?
C24 C23 1.391(5) . ?
C24 C26 1.494(5) . ?
C25 C22 1.381(5) . ?
C10 C11 1.372(5) . ?
C27 C29 1.377(5) . ?
C27 C26 1.379(6) . ?
C20 C21 1.373(6) . ?
C20 C22 1.379(5) . ?
C2 C3 1.376(7) . ?
C13 C15 1.373(6) . ?
C13 C14 1.392(5) . ?
C11 C12 1.367(6) . ?
C29 C30 1.383(6) . ?
C3 C4 1.392(5) . ?
N3 C32 1.328(6) . ?
N3 C35 1.343(5) . ?
C23 C21 1.392(5) . ?
C16 C15 1.368(6) . ?
C16 C17 1.368(6) . ?
C35 C34 1.387(6) . ?
C35 C36 1.499(7) . ?
C33 C34 1.364(7) . ?
C33 C31 1.390(5) . ?
C31 C32 1.389(6) . ?
C17 C18 1.504(6) . ?
O9 C40 1.312(6) . ?
O8 C40 1.208(7) . ?
C39 C40 1.462(7) . ?
C39 C38 1.497(6) . ?
C38 C37 1.528(6) . ?
C37 C37 1.536(8) 2_566 ?

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 S2 O3 118.2(2) . . ?
O4 S2 C19 108.3(2) . . ?
O3 S2 C19 108.3(3) . . ?
O4 S2 C20 108.8(2) . . ?
O3 S2 C20 108.8(2) . . ?
C19 S2 C20 103.5(2) . . ?
O2 S1 O1 118.6(2) . . ?
O2 S1 C1 108.5(2) . . ?
O1 S1 C1 108.0(2) . . ?
O2 S1 C2 106.9(2) . . ?
O1 S1 C2 108.4(2) . . ?
C1 S1 C2 105.7(2) . . ?
N4 C28 C26 121.5(5) . . ?
N4 C28 C31 114.7(4) . . ?
C26 C28 C31 123.8(4) . . ?
C12 N2 C9 118.9(4) . . ?
C6 C5 C4 118.4(4) . . ?
C6 C5 C8 120.6(4) . . ?
C4 C5 C8 120.7(5) . . ?
C30 N4 C28 118.8(4) . . ?
C17 N1 C14 117.9(4) . . ?
C10 C8 C9 118.5(4) . . ?
C10 C8 C5 117.9(4) . . ?
C9 C8 C5 123.4(4) . . ?
C2 C7 C6 118.4(5) . . ?
N2 C9 C8 120.9(4) . . ?
N2 C9 C13 115.8(4) . . ?
C8 C9 C13 123.3(3) . . ?
C25 C24 C23 118.7(4) . . ?
C25 C24 C26 122.1(4) . . ?
C23 C24 C26 119.1(4) . . ?
C22 C25 C24 121.2(4) . . ?
C11 C10 C8 119.9(4) . . ?
C29 C27 C26 118.4(4) . . ?
C21 C20 C22 121.3(4) . . ?
C21 C20 S2 118.5(3) . . ?
C22 C20 S2 120.0(4) . . ?
C3 C2 C7 121.2(4) . . ?
C3 C2 S1 119.6(4) . . ?
C7 C2 S1 119.2(4) . . ?
C27 C26 C28 118.9(4) . . ?
C27 C26 C24 116.3(4) . . ?
C28 C26 C24 124.8(4) . . ?
C15 C13 C14 117.0(4) . . ?
C15 C13 C9 122.8(4) . . ?
C14 C13 C9 120.2(4) . . ?
C12 C11 C10 118.7(4) . . ?
C12 C11 Cl1 120.8(3) . . ?
C10 C11 Cl1 120.6(4) . . ?
C20 C22 C25 119.1(4) . . ?
C27 C29 C30 119.5(5) . . ?
C27 C29 Cl2 120.1(4) . . ?
C30 C29 Cl2 120.3(4) . . ?
C2 C3 C4 119.4(4) . . ?
C5 C4 C3 120.5(5) . . ?
N1 C14 C13 123.4(5) . . ?
C32 N3 C35 118.6(4) . . ?
C24 C23 C21 120.6(4) . . ?
C15 C16 C17 120.2(5) . . ?
N3 C35 C34 120.1(5) . . ?
N3 C35 C36 117.2(5) . . ?
C34 C35 C36 122.7(5) . . ?
C34 C33 C31 120.1(5) . . ?
C7 C6 C5 122.0(4) . . ?
N4 C30 C29 122.8(4) . . ?
N2 C12 C11 123.0(4) . . ?
C32 C31 C33 115.5(5) . . ?
C32 C31 C28 123.7(4) . . ?
C33 C31 C28 120.7(4) . . ?
N1 C17 C16 121.4(5) . . ?
N1 C17 C18 116.2(4) . . ?
C16 C17 C18 122.4(5) . . ?
C16 C15 C13 120.0(4) . . ?
C20 C21 C23 119.0(4) . . ?
N3 C32 C31 125.0(4) . . ?
C33 C34 C35 120.6(5) . . ?
C40 C39 C38 113.8(5) . . ?
C39 C38 C37 112.6(5) . . ?
C38 C37 C37 114.4(6) . 2_566 ?
O8 C40 O9 121.2(6) . . ?
O8 C40 C39 124.8(6) . . ?
O9 C40 C39 114.0(6) . . ?

_refine_diff_density_max         0.447
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.062


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: wet Methanol'
_chemical_compound_source        synthetic
