# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_p18ccw46
_database_code_depnum_ccdc_archive 'CCDC 2011326'
loop_
_audit_author_name
_audit_author_address
'Lauren E. Hatcher'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2020-06-22 deposited with the CCDC.	2020-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            
;
flufenamic acid 2,2'-bipyridine (2:1) co-crystal
;
_chemical_melting_point          321
_chemical_formula_moiety         'C14 H10 F3 N1 O2, 0.5(C10 H8 N2)'
_chemical_formula_sum            'C19 H14 F3 N2 O2'
_chemical_formula_weight         359.32

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.6550(8)
_cell_length_b                   7.8337(4)
_cell_length_c                   21.8957(16)
_cell_angle_alpha                90
_cell_angle_beta                 100.355(7)
_cell_angle_gamma                90
_cell_volume                     1629.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1062
_cell_measurement_theta_min      3.2100
_cell_measurement_theta_max      22.4170

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             740
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.119
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_T_min  0.93042
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3795
_diffrn_reflns_number            7063
_diffrn_reflns_av_unetI/netI     0.1083
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.104
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_full        25.000
_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             3095
_reflns_number_gt                1646
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'MERCURY (Macrae et al., 2008)'
_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)+(0.0230P)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         3095
_refine_ls_number_parameters     256
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.1393
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.015
_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
O1 O 0.4785(2) 0.5572(3) 0.58570(10) 0.0405(6) Uani 1 1 d . . . . .
O2 O 0.6116(2) 0.7214(2) 0.65591(9) 0.0381(6) Uani 1 1 d . . . . .
N1 N 0.7655(3) 0.5689(3) 0.75342(11) 0.0333(7) Uani 1 1 d . . . . .
C1 C 0.5644(3) 0.5803(4) 0.63972(13) 0.0298(8) Uani 1 1 d . . . . .
C2 C 0.5955(3) 0.4214(3) 0.67645(13) 0.0257(7) Uani 1 1 d . . . . .
C3 C 0.5207(3) 0.2732(3) 0.65628(14) 0.0315(8) Uani 1 1 d . . . . .
H3 H 0.452477 0.276017 0.619174 0.038 Uiso 1 1 calc R U . . .
C4 C 0.5442(3) 0.1229(3) 0.68927(15) 0.0365(8) Uani 1 1 d . . . . .
H4 H 0.494560 0.021905 0.674646 0.044 Uiso 1 1 calc R U . . .
C5 C 0.6410(3) 0.1217(4) 0.74380(15) 0.0364(8) Uani 1 1 d . . . . .
H5 H 0.657493 0.018795 0.766929 0.044 Uiso 1 1 calc R U . . .
C6 C 0.7142(3) 0.2667(3) 0.76541(13) 0.0325(8) Uani 1 1 d . . . . .
H6 H 0.778653 0.262775 0.803653 0.039 Uiso 1 1 calc R U . . .
C7 C 0.6952(3) 0.4200(3) 0.73195(13) 0.0285(7) Uani 1 1 d . . . . .
C8 C 0.8895(3) 0.5891(3) 0.79671(13) 0.0281(7) Uani 1 1 d . . . . .
C9 C 0.9967(3) 0.4681(3) 0.80862(13) 0.0290(7) Uani 1 1 d . . . . .
H9 H 0.985485 0.361151 0.787894 0.035 Uiso 1 1 calc R U . . .
C10 C 1.1189(3) 0.5017(3) 0.85005(13) 0.0310(8) Uani 1 1 d . . . . .
H10 H 1.190181 0.416919 0.858174 0.037 Uiso 1 1 calc R U . . .
C11 C 1.1386(3) 0.6580(3) 0.87999(13) 0.0304(8) Uani 1 1 d . . . . .
H11 H 1.222670 0.681382 0.908623 0.036 Uiso 1 1 calc R U . . .
C12 C 1.0333(3) 0.7792(3) 0.86729(13) 0.0279(7) Uani 1 1 d D . . . .
C13 C 0.9100(3) 0.7461(3) 0.82658(13) 0.0293(8) Uani 1 1 d . . . . .
H13 H 0.838726 0.830970 0.818875 0.035 Uiso 1 1 calc R U . . .
F1 F 0.9464(3) 0.9969(3) 0.92441(18) 0.0810(12) Uani 0.871(4) 1 d D . P A 1
F2 F 1.0625(4) 1.0746(3) 0.85688(13) 0.0767(11) Uani 0.871(4) 1 d D . P A 1
F3 F 1.1687(4) 0.9661(3) 0.93953(15) 0.0865(13) Uani 0.871(4) 1 d D . P A 1
C14 C 1.0530(5) 0.9495(5) 0.8974(2) 0.0375(8) Uani 0.871(4) 1 d D . P A 1
F1A F 0.942(2) 1.055(2) 0.8845(11) 0.0810(12) Uani 0.129(4) 1 d D . P A 2
F2A F 1.150(2) 1.047(2) 0.8873(10) 0.0767(11) Uani 0.129(4) 1 d D . P A 2
F3A F 1.067(3) 0.931(2) 0.9581(9) 0.0865(13) Uani 0.129(4) 1 d D . P A 2
C14A C 1.047(3) 0.9510(18) 0.8989(11) 0.0375(8) Uani 0.129(4) 1 d D . P A 2
N2 N 0.3863(3) 0.8614(3) 0.53493(10) 0.0294(6) Uani 1 1 d . . . . .
C15 C 0.2602(4) 0.8650(4) 0.55230(13) 0.0369(8) Uani 1 1 d . . . . .
H15 H 0.229706 0.764819 0.570452 0.044 Uiso 1 1 calc R U . . .
C16 C 0.1723(4) 1.0041(4) 0.54553(13) 0.0382(8) Uani 1 1 d . . . . .
H16 H 0.084403 1.001230 0.559282 0.046 Uiso 1 1 calc R U . . .
C17 C 0.2157(3) 1.1479(4) 0.51817(14) 0.0393(8) Uani 1 1 d . . . . .
H17 H 0.157283 1.246171 0.512003 0.047 Uiso 1 1 calc R U . . .
C18 C 0.3448(3) 1.1477(4) 0.49984(13) 0.0322(8) Uani 1 1 d . . . . .
H18 H 0.376117 1.246328 0.481079 0.039 Uiso 1 1 calc R U . . .
C19 C 0.4291(3) 1.0029(3) 0.50879(12) 0.0259(7) Uani 1 1 d . . . . .
H1A H 0.724(3) 0.666(4) 0.7296(13) 0.051(10) Uiso 1 1 d . . . . .
H1 H 0.459(4) 0.662(4) 0.5661(15) 0.073(12) 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
O1 C1 1.330(3) . ?
O1 H1 0.93(3) . ?
O2 C1 1.224(3) . ?
N1 C7 1.389(3) . ?
N1 C8 1.396(4) . ?
N1 H1A 0.97(3) . ?
C1 C2 1.483(4) . ?
C2 C3 1.396(4) . ?
C2 C7 1.408(4) . ?
C3 C4 1.379(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.376(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.402(4) . ?
C6 H6 0.9500 . ?
C8 C13 1.390(4) . ?
C8 C9 1.393(4) . ?
C9 C10 1.378(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(4) . ?
C12 C14 1.486(5) . ?
C12 C14A 1.508(10) . ?
C13 H13 0.9500 . ?
F1 C14 1.328(5) . ?
F2 C14 1.336(5) . ?
F3 C14 1.320(5) . ?
F1A C14A 1.295(18) . ?
F2A C14A 1.302(18) . ?
F3A C14A 1.287(18) . ?
N2 C15 1.339(4) . ?
N2 C19 1.346(3) . ?
C15 C16 1.374(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.376(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(4) . ?
C18 H18 0.9500 . ?
C19 C19 1.488(6) 3_676 ?

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
C1 O1 H1 110(2) . . ?
C7 N1 C8 129.3(2) . . ?
C7 N1 H1A 110.5(18) . . ?
C8 N1 H1A 119.7(18) . . ?
O2 C1 O1 121.4(3) . . ?
O2 C1 C2 125.0(3) . . ?
O1 C1 C2 113.7(3) . . ?
C3 C2 C7 120.0(3) . . ?
C3 C2 C1 118.9(3) . . ?
C7 C2 C1 121.0(3) . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 121.1(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
N1 C7 C6 122.2(3) . . ?
N1 C7 C2 120.2(2) . . ?
C6 C7 C2 117.6(3) . . ?
C13 C8 C9 118.4(3) . . ?
C13 C8 N1 116.9(3) . . ?
C9 C8 N1 124.6(3) . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.6(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 118.6(3) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 C14 118.9(3) . . ?
C11 C12 C14 119.8(3) . . ?
C13 C12 C14A 117.4(10) . . ?
C11 C12 C14A 121.2(10) . . ?
C12 C13 C8 120.3(3) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
F3 C14 F1 106.8(4) . . ?
F3 C14 F2 103.9(4) . . ?
F1 C14 F2 104.0(3) . . ?
F3 C14 C12 115.0(3) . . ?
F1 C14 C12 113.7(4) . . ?
F2 C14 C12 112.4(3) . . ?
F3A C14A F1A 106.8(18) . . ?
F3A C14A F2A 106.9(18) . . ?
F1A C14A F2A 100.4(17) . . ?
F3A C14A C12 109.6(15) . . ?
F1A C14A C12 116.6(17) . . ?
F2A C14A C12 115.6(16) . . ?
C15 N2 C19 117.9(2) . . ?
N2 C15 C16 124.2(3) . . ?
N2 C15 H15 117.9 . . ?
C16 C15 H15 117.9 . . ?
C15 C16 C17 117.7(3) . . ?
C15 C16 H16 121.1 . . ?
C17 C16 H16 121.1 . . ?
C18 C17 C16 119.3(3) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C19 119.9(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
N2 C19 C18 121.0(3) . . ?
N2 C19 C19 116.8(3) . 3_676 ?
C18 C19 C19 122.1(3) . 3_676 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 171.8(3) . . . . ?
O1 C1 C2 C3 -8.3(4) . . . . ?
O2 C1 C2 C7 -6.1(5) . . . . ?
O1 C1 C2 C7 173.8(3) . . . . ?
C7 C2 C3 C4 -1.1(5) . . . . ?
C1 C2 C3 C4 -179.1(3) . . . . ?
C2 C3 C4 C5 1.6(5) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C7 -1.5(5) . . . . ?
C8 N1 C7 C6 21.3(5) . . . . ?
C8 N1 C7 C2 -162.1(3) . . . . ?
C5 C6 C7 N1 178.6(3) . . . . ?
C5 C6 C7 C2 1.9(4) . . . . ?
C3 C2 C7 N1 -177.4(3) . . . . ?
C1 C2 C7 N1 0.5(4) . . . . ?
C3 C2 C7 C6 -0.6(4) . . . . ?
C1 C2 C7 C6 177.3(3) . . . . ?
C7 N1 C8 C13 -157.0(3) . . . . ?
C7 N1 C8 C9 27.5(5) . . . . ?
C13 C8 C9 C10 1.5(4) . . . . ?
N1 C8 C9 C10 176.9(3) . . . . ?
C8 C9 C10 C11 -1.1(4) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C10 C11 C12 C13 1.0(4) . . . . ?
C10 C11 C12 C14 -178.5(3) . . . . ?
C10 C11 C12 C14A 179.2(11) . . . . ?
C11 C12 C13 C8 -0.6(4) . . . . ?
C14 C12 C13 C8 178.8(3) . . . . ?
C14A C12 C13 C8 -178.9(11) . . . . ?
C9 C8 C13 C12 -0.6(4) . . . . ?
N1 C8 C13 C12 -176.3(3) . . . . ?
C13 C12 C14 F3 174.7(4) . . . . ?
C11 C12 C14 F3 -5.9(6) . . . . ?
C13 C12 C14 F1 51.2(5) . . . . ?
C11 C12 C14 F1 -129.3(4) . . . . ?
C13 C12 C14 F2 -66.6(5) . . . . ?
C11 C12 C14 F2 112.8(4) . . . . ?
C13 C12 C14A F3A 120.7(18) . . . . ?
C11 C12 C14A F3A -58(2) . . . . ?
C13 C12 C14A F1A -1(2) . . . . ?
C11 C12 C14A F1A -179.0(16) . . . . ?
C13 C12 C14A F2A -118.4(18) . . . . ?
C11 C12 C14A F2A 63(2) . . . . ?
C19 N2 C15 C16 -0.5(4) . . . . ?
N2 C15 C16 C17 1.2(5) . . . . ?
C15 C16 C17 C18 -1.1(4) . . . . ?
C16 C17 C18 C19 0.3(5) . . . . ?
C15 N2 C19 C18 -0.3(4) . . . . ?
C15 N2 C19 C19 178.7(3) . . . 3_676 ?
C17 C18 C19 N2 0.4(4) . . . . ?
C17 C18 C19 C19 -178.5(3) . . . 3_676 ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.053


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'
