#------------------------------------------------------------------------------
#$Date: 2016-05-06 03:56:43 +0300 (Fri, 06 May 2016) $
#$Revision: 182654 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/43/7224394.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_7224394
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         'C18 H15 Cl N2 O2 S, C8 H14 O4'
_chemical_formula_sum            'C26 H29 Cl N2 O6 S'
_chemical_formula_weight         533.02
_chemical_melting_point          390.4
_chemical_name_common            'etoricoxib-suberic acid cocrystal'
_chemical_name_systematic
'5-Chloro-6-methyl-3-[4-(methylsulfonyl)phenyl]-2,3-bipyridine-octanedioic acid'
_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   geom
_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                82.766(5)
_cell_angle_beta                 77.640(4)
_cell_angle_gamma                85.386(4)
_cell_formula_units_Z            2
_cell_length_a                   9.0238(3)
_cell_length_b                   10.1284(5)
_cell_length_c                   14.8544(9)
_cell_measurement_reflns_used    3886
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      66.59
_cell_measurement_theta_min      3.06
_cell_volume                     1313.61(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7910
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.589
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_min         3.065
_exptl_absorpt_coefficient_mu    2.396
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dry MeOH'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4615
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0424
_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)+(0.0688P)²+0.1934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1219
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3886
_reflns_number_total             4615
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce00003g2.cif
_cod_data_source_block           ETRSBA
_cod_depositor_comments
'Adding full bibliography for 7224391--7224395.cif.'
_cod_database_code               7224394
_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
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
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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)
