#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/15/7231591.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_7231591
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            'C20 H19 N3 O2'
_chemical_formula_weight         333.38
_chemical_name_systematic
'co-crystal of mefenamic acid and 4,4'-azopyridine'
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-02-22T13:49:51-00:00
_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                100.617(10)
_cell_angle_beta                 99.729(9)
_cell_angle_gamma                93.918(9)
_cell_formula_units_Z            2
_cell_length_a                   7.549(5)
_cell_length_b                   8.736(6)
_cell_length_c                   13.095(8)
_cell_measurement_reflns_used    2243
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      2.38
_cell_volume                     832.2(9)
_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 0.998
_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  0.0320
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.998
_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       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9970
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.292
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.33
_exptl_crystal_description       prism
_exptl_crystal_F_000             352
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0415
_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)+(0.0483P)²+0.0716P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                2666
_reflns_number_total             3726
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01492b2.cif
_cod_data_source_block           mefenamicacidAzo
_cod_depositor_comments
'Adding full bibliography for 7231588--7231594.cif.'
_cod_database_code               7231591
_shelx_estimated_absorpt_t_min   0.979
_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 0.86840(14) -0.19859(12) 0.08852(8) 0.0233(3) Uani 1 d
H1 H 0.8298 -0.294 0.0733 0.035 Uiso 1 calc
O2 O 0.73683(15) -0.20794(12) 0.22755(8) 0.0259(3) Uani 1 d
N1 N 0.75863(17) 0.05133(14) 0.37421(9) 0.0218(3) Uani 1 d
H1A H 0.7309 -0.0508 0.3573 0.026 Uiso 1 calc
N2 N 0.75021(16) 0.49538(14) 0.03929(9) 0.0198(3) Uani 1 d
N3 N 0.53142(16) 0.02467(14) -0.03567(9) 0.0210(3) Uani 1 d
C1 C 0.84911(19) 0.12134(17) 0.30996(11) 0.0174(3) Uani 1 d
C2 C 0.88791(18) 0.03488(16) 0.21496(11) 0.0169(3) Uani 1 d
C3 C 0.98748(19) 0.11041(17) 0.15425(11) 0.0190(3) Uani 1 d
H3 H 1.0151 0.0518 0.0913 0.023 Uiso 1 calc
C4 C 1.0464(2) 0.26795(18) 0.18362(12) 0.0223(3) Uani 1 d
H4 H 1.1148 0.3174 0.1419 0.027 Uiso 1 calc
C5 C 1.0041(2) 0.35286(17) 0.27528(12) 0.0222(3) Uani 1 d
H5 H 1.0422 0.4618 0.2955 0.027 Uiso 1 calc
C6 C 0.9082(2) 0.28241(17) 0.33724(11) 0.0204(3) Uani 1 d
H6 H 0.8812 0.3434 0.3996 0.025 Uiso 1 calc
C7 C 0.82356(19) -0.13312(17) 0.17911(11) 0.0185(3) Uani 1 d
C8 C 0.7067(2) 0.13524(16) 0.46732(11) 0.0197(3) Uani 1 d
C9 C 0.5435(2) 0.20208(17) 0.46060(11) 0.0194(3) Uani 1 d
C10 C 0.4950(2) 0.28026(17) 0.55421(11) 0.0198(3) Uani 1 d
C11 C 0.6108(2) 0.28986(17) 0.64995(12) 0.0226(3) Uani 1 d
H11 H 0.5778 0.342 0.7132 0.027 Uiso 1 calc
C12 C 0.7736(2) 0.22484(18) 0.65513(12) 0.0245(4) Uani 1 d
H12 H 0.852 0.234 0.7213 0.029 Uiso 1 calc
C13 C 0.8215(2) 0.14679(18) 0.56389(12) 0.0228(3) Uani 1 d
H13 H 0.9324 0.1011 0.5671 0.027 Uiso 1 calc
C14 C 0.4216(2) 0.1942(2) 0.35584(12) 0.0270(4) Uani 1 d
H14A H 0.4148 0.3 0.3414 0.041 Uiso 1 calc
H14B H 0.3005 0.1484 0.358 0.041 Uiso 1 calc
H14C H 0.4702 0.1292 0.2999 0.041 Uiso 1 calc
C15 C 0.3202(2) 0.3542(2) 0.55066(13) 0.0288(4) Uani 1 d
H15A H 0.3075 0.4015 0.6226 0.043 Uiso 1 calc
H15B H 0.2188 0.274 0.5191 0.043 Uiso 1 calc
H15C H 0.3204 0.4352 0.5079 0.043 Uiso 1 calc
C16 C 0.7757(2) 0.39476(17) -0.04624(12) 0.0224(3) Uani 1 d
H16 H 0.8473 0.4316 -0.0915 0.027 Uiso 1 calc
C17 C 0.7031(2) 0.24062(17) -0.07165(12) 0.0216(3) Uani 1 d
H17 H 0.7228 0.1731 -0.1335 0.026 Uiso 1 calc
C18 C 0.60126(19) 0.18678(16) -0.00520(11) 0.0184(3) Uani 1 d
C19 C 0.5724(2) 0.28855(17) 0.08400(12) 0.0213(3) Uani 1 d
H19 H 0.5017 0.2542 0.1306 0.026 Uiso 1 calc
C20 C 0.6497(2) 0.44073(17) 0.10254(12) 0.0213(3) Uani 1 d
H20 H 0.6309 0.5109 0.1635 0.026 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 .
C1 N1 C8 123.55(13) .
C1 N1 H1A 118.2 .
C8 N1 H1A 118.2 .
C16 N2 C20 117.43(13) .
N3 N3 C18 112.66(15) 2_655
N1 C1 C6 120.57(13) .
N1 C1 C2 121.55(13) .
C6 C1 C2 117.87(13) .
C3 C2 C1 119.40(14) .
C3 C2 C7 119.76(13) .
C1 C2 C7 120.84(13) .
C4 C3 C2 121.59(14) .
C4 C3 H3 119.2 .
C2 C3 H3 119.2 .
C3 C4 C5 118.75(14) .
C3 C4 H4 120.6 .
C5 C4 H4 120.6 .
C6 C5 C4 121.24(14) .
C6 C5 H5 119.4 .
C4 C5 H5 119.4 .
C5 C6 C1 121.11(14) .
C5 C6 H6 119.4 .
C1 C6 H6 119.4 .
O2 C7 O1 121.79(13) .
O2 C7 C2 123.92(13) .
O1 C7 C2 114.28(12) .
C13 C8 C9 121.19(13) .
C13 C8 N1 118.45(14) .
C9 C8 N1 120.36(13) .
C8 C9 C10 118.72(13) .
C8 C9 C14 121.36(13) .
C10 C9 C14 119.92(14) .
C11 C10 C9 119.28(14) .
C11 C10 C15 120.21(13) .
C9 C10 C15 120.51(14) .
C12 C11 C10 121.31(14) .
C12 C11 H11 119.3 .
C10 C11 H11 119.3 .
C13 C12 C11 119.78(15) .
C13 C12 H12 120.1 .
C11 C12 H12 120.1 .
C12 C13 C8 119.72(14) .
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 123.21(14) .
N2 C16 H16 118.4 .
C17 C16 H16 118.4 .
C16 C17 C18 118.36(14) .
C16 C17 H17 120.8 .
C18 C17 H17 120.8 .
C17 C18 C19 119.68(14) .
C17 C18 N3 115.48(13) .
C19 C18 N3 124.84(13) .
C20 C19 C18 117.75(14) .
C20 C19 H19 121.1 .
C18 C19 H19 121.1 .
N2 C20 C19 123.57(14) .
N2 C20 H20 118.2 .
C19 C20 H20 118.2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.3271(18) .
O1 H1 0.84 .
O2 C7 1.2219(17) .
N1 C1 1.3694(18) .
N1 C8 1.4315(18) .
N1 H1A 0.88 .
N2 C16 1.3406(19) .
N2 C20 1.3409(19) .
N3 N3 1.247(2) 2_655
N3 C18 1.436(2) .
C1 C6 1.408(2) .
C1 C2 1.418(2) .
C2 C3 1.400(2) .
C2 C7 1.477(2) .
C3 C4 1.380(2) .
C3 H3 0.95 .
C4 C5 1.388(2) .
C4 H4 0.95 .
C5 C6 1.372(2) .
C5 H5 0.95 .
C6 H6 0.95 .
C8 C13 1.390(2) .
C8 C9 1.395(2) .
C9 C10 1.408(2) .
C9 C14 1.504(2) .
C10 C11 1.387(2) .
C10 C15 1.506(2) .
C11 C12 1.386(2) .
C11 H11 0.95 .
C12 C13 1.379(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 1.377(2) .
C16 H16 0.95 .
C17 C18 1.377(2) .
C17 H17 0.95 .
C18 C19 1.390(2) .
C19 C20 1.376(2) .
C19 H19 0.95 .
C20 H20 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
O1 H1 N2 0.84 1.84 2.684(2) 178.6 1_545
N1 H1A O2 0.88 1.99 2.662(2) 132.4 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139205085
