#------------------------------------------------------------------------------
#$Date: 2019-11-17 08:43:33 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228918 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/15/7231588.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_7231588
loop_
_publ_author_name
'Zheng, Qixuan'
'Rood, Samantha L.'
'Unruh, Daniel K.'
'Hutchins, Kristin M.'
_publ_section_title
;
 Co-crystallization of anti-inflammatory pharmaceutical contaminants and
 rare carboxylic acid--pyridine supramolecular synthon breakdown
;
_journal_issue                   41
_journal_name_full               CrystEngComm
_journal_page_first              6377
_journal_paper_doi               10.1039/C8CE01492B
_journal_volume                  20
_journal_year                    2018
_chemical_formula_sum            'C21 H20 N2 O2'
_chemical_formula_weight         332.39
_chemical_name_systematic
'co-crystal of mefenamic acid and 1,2-Bis(4-pyridyl)ethylene'
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-02-12T16:41:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2018-08-30 deposited with the CCDC.
2018-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                98.216(2)
_cell_angle_beta                 99.515(2)
_cell_angle_gamma                90.024(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8199(14)
_cell_length_b                   8.6152(15)
_cell_length_c                   12.900(2)
_cell_measurement_reflns_used    3310
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.96
_cell_measurement_theta_min      2.68
_cell_volume                     848.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9598
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.071
_diffrn_reflns_theta_min         1.618
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene'
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0535P)²+0.2761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1162
_reflns_number_gt                2901
_reflns_number_total             3684
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01492b2.cif
_cod_data_source_block           mefenamicaicdBPE
_cod_depositor_comments
'Adding full bibliography for 7231588--7231594.cif.'
_cod_original_cell_volume        848.0(3)
_cod_database_code               7231588
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.995
loop_
_symmetry_equiv_pos_as_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_calc_flag
O1 O 0.87448(13) -0.20288(11) 0.09389(8) 0.0232(2) Uani 1 d
H1 H 0.8295 -0.2934 0.0774 0.035 Uiso 1 calc
O2 O 0.72577(14) -0.19910(12) 0.22778(8) 0.0271(3) Uani 1 d
N1 N 0.76467(16) 0.05139(15) 0.37823(9) 0.0218(3) Uani 1 d
H1A H 0.7399(6) -0.042(2) 0.3647(3) 0.026 Uiso 1 d
N2 N 0.75358(15) 0.50490(13) 0.04220(9) 0.0199(3) Uani 1 d
C1 C 0.89080(17) 0.02924(15) 0.21647(10) 0.0172(3) Uani 1 d
C2 C 0.85497(17) 0.11718(16) 0.31190(11) 0.0181(3) Uani 1 d
C3 C 0.91718(18) 0.27388(16) 0.33773(11) 0.0211(3) Uani 1 d
H3 H 0.8937 0.3353 0.4008 0.025 Uiso 1 calc
C4 C 1.01115(19) 0.33906(17) 0.27321(12) 0.0231(3) Uani 1 d
H4 H 1.0503 0.4453 0.2919 0.028 Uiso 1 calc
C5 C 1.05015(19) 0.25220(17) 0.18080(11) 0.0229(3) Uani 1 d
H5 H 1.1173 0.2976 0.1374 0.027 Uiso 1 calc
C6 C 0.98943(18) 0.09908(16) 0.15358(11) 0.0200(3) Uani 1 d
H6 H 1.0152 0.0394 0.0905 0.024 Uiso 1 calc
C7 C 0.82251(18) -0.13314(16) 0.18112(11) 0.0187(3) Uani 1 d
C8 C 0.71227(18) 0.13960(16) 0.46997(11) 0.0197(3) Uani 1 d
C9 C 0.54542(18) 0.19984(16) 0.46361(11) 0.0207(3) Uani 1 d
C10 C 0.49683(19) 0.28432(16) 0.55545(11) 0.0213(3) Uani 1 d
C11 C 0.61580(19) 0.30588(17) 0.64958(11) 0.0234(3) Uani 1 d
H11 H 0.5829 0.3623 0.7118 0.028 Uiso 1 calc
C12 C 0.78125(19) 0.24669(17) 0.65450(11) 0.0247(3) Uani 1 d
H12 H 0.8611 0.2635 0.7193 0.03 Uiso 1 calc
C13 C 0.82967(19) 0.16291(17) 0.56453(11) 0.0230(3) Uani 1 d
H13 H 0.9427 0.1215 0.5674 0.028 Uiso 1 calc
C14 C 0.4201(2) 0.1780(2) 0.36041(12) 0.0294(4) Uani 1 d
H14A H 0.3862 0.2808 0.3408 0.044 Uiso 1 calc
H14B H 0.3169 0.1194 0.3686 0.044 Uiso 1 calc
H14C H 0.4756 0.1195 0.3046 0.044 Uiso 1 calc
C15 C 0.3194(2) 0.3540(2) 0.55150(13) 0.0298(4) Uani 1 d
H15A H 0.3069 0.4331 0.5034 0.045 Uiso 1 calc
H15B H 0.3055 0.4031 0.6229 0.045 Uiso 1 calc
H15C H 0.2306 0.271 0.5257 0.045 Uiso 1 calc
C16 C 0.78319(19) 0.40572(16) -0.04247(11) 0.0215(3) Uani 1 d
H16 H 0.8537 0.4415 -0.088 0.026 Uiso 1 calc
C17 C 0.71630(19) 0.25407(16) -0.06692(11) 0.0221(3) Uani 1 d
H17 H 0.7403 0.1883 -0.1282 0.026 Uiso 1 calc
C18 C 0.61420(18) 0.19834(16) -0.00163(11) 0.0208(3) Uani 1 d
C19 C 0.58278(19) 0.30141(17) 0.08683(12) 0.0234(3) Uani 1 d
H19 H 0.5128 0.2686 0.1337 0.028 Uiso 1 calc
C20 C 0.65467(18) 0.45175(17) 0.10548(11) 0.0219(3) Uani 1 d
H20 H 0.6327 0.5204 0.1661 0.026 Uiso 1 calc
C21 C 0.54806(18) 0.03498(16) -0.02773(11) 0.0230(3) Uani 1 d
H21 H 0.5771 -0.0252 -0.0898 0.028 Uiso 1 calc
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 0 '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 0.006 '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_1
C7 O1 H1 109.5 .
C2 N1 C8 122.94(12) .
C2 N1 H1A 118.5(3) .
C8 N1 H1A 118.6(3) .
C20 N2 C16 117.32(12) .
C6 C1 C2 119.26(12) .
C6 C1 C7 119.49(12) .
C2 C1 C7 121.23(12) .
N1 C2 C3 120.76(12) .
N1 C2 C1 121.24(12) .
C3 C2 C1 117.99(12) .
C4 C3 C2 121.05(13) .
C4 C3 H3 119.5 .
C2 C3 H3 119.5 .
C3 C4 C5 121.18(13) .
C3 C4 H4 119.4 .
C5 C4 H4 119.4 .
C6 C5 C4 118.73(13) .
C6 C5 H5 120.6 .
C4 C5 H5 120.6 .
C5 C6 C1 121.75(13) .
C5 C6 H6 119.1 .
C1 C6 H6 119.1 .
O2 C7 O1 122.17(12) .
O2 C7 C1 123.58(12) .
O1 C7 C1 114.26(12) .
C13 C8 C9 121.19(13) .
C13 C8 N1 118.73(12) .
C9 C8 N1 120.07(13) .
C8 C9 C10 118.79(13) .
C8 C9 C14 121.07(13) .
C10 C9 C14 120.13(13) .
C11 C10 C9 119.24(13) .
C11 C10 C15 120.27(13) .
C9 C10 C15 120.48(13) .
C12 C11 C10 121.35(13) .
C12 C11 H11 119.3 .
C10 C11 H11 119.3 .
C13 C12 C11 119.71(13) .
C13 C12 H12 120.1 .
C11 C12 H12 120.1 .
C12 C13 C8 119.72(13) .
C12 C13 H13 120.1 .
C8 C13 H13 120.1 .
C9 C14 H14A 109.5 .
C9 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
C9 C14 H14C 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
C10 C15 H15A 109.5 .
C10 C15 H15B 109.5 .
H15A C15 H15B 109.5 .
C10 C15 H15C 109.5 .
H15A C15 H15C 109.5 .
H15B C15 H15C 109.5 .
N2 C16 C17 123.28(13) .
N2 C16 H16 118.4 .
C17 C16 H16 118.4 .
C16 C17 C18 119.65(13) .
C16 C17 H17 120.2 .
C18 C17 H17 120.2 .
C17 C18 C19 117.31(13) .
C17 C18 C21 118.70(13) .
C19 C18 C21 123.99(13) .
C20 C19 C18 119.34(13) .
C20 C19 H19 120.3 .
C18 C19 H19 120.3 .
N2 C20 C19 123.10(13) .
N2 C20 H20 118.4 .
C19 C20 H20 118.4 .
C21 C21 C18 125.56(17) 2_655
C21 C21 H21 117.2 2_655
C18 C21 H21 117.2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.3231(16) .
O1 H1 0.84 .
O2 C7 1.2269(16) .
N1 C2 1.3748(18) .
N1 C8 1.4316(17) .
N1 H1A 0.815(17) .
N2 C20 1.3377(18) .
N2 C16 1.3392(18) .
C1 C6 1.4004(19) .
C1 C2 1.4198(18) .
C1 C7 1.4788(19) .
C2 C3 1.4097(19) .
C3 C4 1.372(2) .
C3 H3 0.95 .
C4 C5 1.393(2) .
C4 H4 0.95 .
C5 C6 1.379(2) .
C5 H5 0.95 .
C6 H6 0.95 .
C8 C13 1.389(2) .
C8 C9 1.399(2) .
C9 C10 1.4072(19) .
C9 C14 1.505(2) .
C10 C11 1.392(2) .
C10 C15 1.508(2) .
C11 C12 1.386(2) .
C11 H11 0.95 .
C12 C13 1.385(2) .
C12 H12 0.95 .
C13 H13 0.95 .
C14 H14A 0.98 .
C14 H14B 0.98 .
C14 H14C 0.98 .
C15 H15A 0.98 .
C15 H15B 0.98 .
C15 H15C 0.98 .
C16 C17 1.381(2) .
C16 H16 0.95 .
C17 C18 1.384(2) .
C17 H17 0.95 .
C18 C19 1.398(2) .
C18 C21 1.472(2) .
C19 C20 1.385(2) .
C19 H19 0.95 .
C20 H20 0.95 .
C21 C21 1.319(3) 2_655
C21 H21 0.95 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O2 0.815(17) 2.053(10) 2.6690(16) 132.1(7) .
O1 H1 N2 0.84 1.81 2.6432(16) 174.5 1_545
