#------------------------------------------------------------------------------
#$Date: 2016-05-06 03:56:43 +0300 (Fri, 06 May 2016) $
#$Revision: 182654 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/43/7224395.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7224395
loop_
_publ_author_name
'Mittapalli, Sudhir'
'Bolla, Geetha'
'Perumalla, Sravankumar'
'Nangia, Ashwini'
_publ_section_title
;
 Can we exchange water in a hydrate structure: a case study of etoricoxib
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              2825
_journal_paper_doi               10.1039/C6CE00003G
_journal_volume                  18
_journal_year                    2016
_chemical_compound_source        synthetic
_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
_chemical_melting_point          388.2
_chemical_name_common            'etoricoxib-suberic acid cocrystal hydrate'
_chemical_name_systematic
'5-Chloro-6-methyl-3-[4-(methylsulfonyl)phenyl]-2,3-bipyridine-octanedioic acid trihydrate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-12-29 deposited with the CCDC.
2016-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                95.187(8)
_cell_angle_beta                 113.754(12)
_cell_angle_gamma                91.242(8)
_cell_formula_units_Z            2
_cell_length_a                   12.2796(15)
_cell_length_b                   12.4817(10)
_cell_length_c                   14.8713(18)
_cell_measurement_reflns_used    7303
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.026
_cell_measurement_theta_min      2.790
_cell_volume                     2073.5(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_unetI/netI     0.1651
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13766
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.790
_exptl_absorpt_coefficient_mu    0.316
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             894
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: wet Methanol'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         7303
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.1562
_refine_ls_R_factor_gt           0.0649
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0168P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.1307
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3338
_reflns_number_total             7303
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce00003g2.cif
_cod_data_source_block           ETRSBA_trihydrate
_cod_depositor_comments
'Adding full bibliography for 7224391--7224395.cif.'
_cod_database_code               7224395
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
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 .
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'
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_3
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) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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
