# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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. 
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data_TRFL-BA
_database_code_depnum_ccdc_archive 'CCDC 1421380'
_audit_update_record             
;
2015-08-31 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;
_audit_creation_date             2015-07-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        'Triflusal-BA cocrystal'
_chemical_formula_moiety         'C10 H7 F3 O4, C7 H7 N O'
_chemical_formula_sum            'C17 H14 F3 N O5'
_chemical_formula_weight         369.29
_chemical_melting_point          359.7
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   5.1765(10)
_cell_length_b                   15.228(3)
_cell_length_c                   21.041(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.91(3)
_cell_angle_gamma                90
_cell_volume                     1654.7(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4684
_cell_measurement_temperature    110.1500
_cell_measurement_theta_max      31.0862
_cell_measurement_theta_min      2.3567
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.945
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.9718
_exptl_absorpt_correction_T_min  0.9447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'R. H. Blessing, Acta Cryst. 1995 A51, 33-38'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0264
_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       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12960
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.675
_diffrn_ambient_temperature      110.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
scan:
	Number of images: 330
	           Slice: -110.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 270.0000
	             XTD: 45.0276
	          2theta: -20.0759
scan:
	Number of images: 172
	           Slice: -38.7500 - 47.2500
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 270.0000
	             XTD: 45.0276
	          2theta: -20.0759
scan:
	Number of images: 180
	           Slice: -87.5000 - 2.5000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 45.0276
	          2theta: -20.0759
;
_diffrn_measurement_device       
;
Saturn70 (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_number_total             4944
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.1137
_diffrn_orient_matrix_UB_12      -0.0850
_diffrn_orient_matrix_UB_13      -0.1317
_diffrn_orient_matrix_UB_21      0.0521
_diffrn_orient_matrix_UB_22      0.0315
_diffrn_orient_matrix_UB_23      0.0247
_diffrn_orient_matrix_UB_31      0.0096
_diffrn_orient_matrix_UB_32      -0.0376
_diffrn_orient_matrix_UB_33      0.0277
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0000
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3711
_reflns_number_total             4077
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4077
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0651
_refine_ls_restrained_S_all      1.179
_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)+(0.0634P)²+0.7655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1552
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(F2A)=Sof(F1A)=Sof(F3A)=1-FVAR(1)
 Sof(F3)=Sof(F1)=Sof(F2)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C6(H6), C5(H5), C13(H13), C15(H15), C16(H16), C17(H17), C14(H14)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O4 O -0.0086(3) 0.36631(10) 0.39730(6) 0.0325(3) Uani 1 1 d . . . . .
O2 O 0.3051(2) 0.28234(9) 0.48300(6) 0.0280(3) Uani 1 1 d . . . . .
O3 O -0.3537(3) 0.43661(10) 0.42955(6) 0.0336(3) Uani 1 1 d . . . . .
O1 O -0.0028(3) 0.18156(9) 0.45672(7) 0.0345(3) Uani 1 1 d . . . . .
C4 C -0.0601(3) 0.37448(11) 0.50892(8) 0.0255(4) Uani 1 1 d . . . . .
C9 C -0.1557(3) 0.39528(12) 0.44152(8) 0.0258(4) Uani 1 1 d . . . . .
C8 C 0.2255(3) 0.30665(12) 0.59076(9) 0.0282(4) Uani 1 1 d . . . . .
H8 H 0.3695 0.2700 0.6025 0.034 Uiso 1 1 calc R . . . .
C6 C -0.1224(4) 0.40052(12) 0.62049(9) 0.0303(4) Uani 1 1 d . . . . .
H6 H -0.2150 0.4280 0.6525 0.036 Uiso 1 1 calc R . . . .
F3 F 0.2383(9) 0.2522(2) 0.71958(13) 0.0554(13) Uani 0.789(14) 1 d . . P A 1
C3 C 0.1495(3) 0.32051(12) 0.52703(8) 0.0259(4) Uani 1 1 d . . . . .
C2 C 0.1997(3) 0.21512(12) 0.44639(8) 0.0280(4) Uani 1 1 d . . . . .
C5 C -0.1964(4) 0.41338(12) 0.55664(9) 0.0289(4) Uani 1 1 d . . . . .
H5 H -0.3423 0.4493 0.5451 0.035 Uiso 1 1 calc R . . . .
C7 C 0.0885(4) 0.34702(12) 0.63727(8) 0.0283(4) Uani 1 1 d . . . . .
F1 F -0.0050(6) 0.3571(4) 0.74534(11) 0.0698(18) Uani 0.789(14) 1 d . . P A 1
F2 F 0.3800(8) 0.3817(2) 0.72370(11) 0.0558(14) Uani 0.789(14) 1 d . . P A 1
C10 C 0.1755(4) 0.33375(13) 0.70634(9) 0.0329(4) Uani 1 1 d . . . . .
C1 C 0.3724(4) 0.19144(15) 0.39526(10) 0.0365(4) Uani 1 1 d . . . . .
H1A H 0.3184 0.1348 0.3766 0.055 Uiso 1 1 calc GR . . . .
H1B H 0.5514 0.1871 0.4134 0.055 Uiso 1 1 calc GR . . . .
H1C H 0.3610 0.2368 0.3621 0.055 Uiso 1 1 calc GR . . . .
O11 O 0.8471(2) 0.40992(9) 0.28220(6) 0.0312(3) Uani 1 1 d . . . . .
N11 N 0.4219(3) 0.42085(11) 0.29820(8) 0.0290(3) Uani 1 1 d . . . . .
C12 C 0.5552(3) 0.42262(12) 0.19051(8) 0.0263(4) Uani 1 1 d . . . . .
C11 C 0.6173(3) 0.41753(12) 0.26059(8) 0.0258(4) Uani 1 1 d . . . . .
C13 C 0.7164(4) 0.38007(14) 0.15042(9) 0.0332(4) Uani 1 1 d . . . . .
H13 H 0.8651 0.3497 0.1679 0.040 Uiso 1 1 calc R . . . .
C15 C 0.4482(5) 0.42783(15) 0.05964(10) 0.0427(5) Uani 1 1 d . . . . .
H15 H 0.4101 0.4291 0.0148 0.051 Uiso 1 1 calc R . . . .
C16 C 0.2900(4) 0.47220(15) 0.09899(10) 0.0407(5) Uani 1 1 d . . . . .
H16 H 0.1456 0.5045 0.0812 0.049 Uiso 1 1 calc R . . . .
C17 C 0.3418(4) 0.46969(13) 0.16466(9) 0.0336(4) Uani 1 1 d . . . . .
H17 H 0.2324 0.4999 0.1918 0.040 Uiso 1 1 calc R . . . .
C14 C 0.6616(5) 0.38154(15) 0.08468(10) 0.0415(5) Uani 1 1 d . . . . .
H14 H 0.7696 0.3511 0.0573 0.050 Uiso 1 1 calc R . . . .
H11A H 0.254(5) 0.4212(15) 0.2811(11) 0.038(6) Uiso 1 1 d . . . . .
H11B H 0.457(5) 0.4209(17) 0.3396(14) 0.047(7) Uiso 1 1 d . . . . .
H4 H -0.084(6) 0.384(2) 0.3573(16) 0.065(9) Uiso 1 1 d . . . . .
F2A F 0.4370(19) 0.321(2) 0.7164(5) 0.103(11) Uani 0.211(14) 1 d . . P A 2
F1A F 0.140(5) 0.3966(7) 0.7432(5) 0.082(9) Uani 0.211(14) 1 d . . P A 2
F3A F 0.077(6) 0.2656(16) 0.7319(6) 0.111(12) Uani 0.211(14) 1 d . . P A 2


_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
O4 C9 1.318(2) . ?
O4 H4 0.95(3) . ?
O2 C3 1.395(2) . ?
O2 C2 1.371(2) . ?
O3 C9 1.214(2) . ?
O1 C2 1.200(2) . ?
C4 C9 1.504(2) . ?
C4 C3 1.393(2) . ?
C4 C5 1.398(3) . ?
C8 H8 0.9500 . ?
C8 C3 1.388(2) . ?
C8 C7 1.390(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.386(3) . ?
C6 C7 1.388(3) . ?
F3 C10 1.308(3) . ?
C2 C1 1.489(3) . ?
C5 H5 0.9500 . ?
C7 C10 1.505(3) . ?
F1 C10 1.333(3) . ?
F2 C10 1.317(3) . ?
C10 F2A 1.370(10) . ?
C10 F1A 1.253(9) . ?
C10 F3A 1.290(10) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
O11 C11 1.250(2) . ?
N11 C11 1.327(2) . ?
N11 H11A 0.92(2) . ?
N11 H11B 0.88(3) . ?
C12 C11 1.490(2) . ?
C12 C13 1.387(3) . ?
C12 C17 1.396(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.393(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.380(3) . ?
C15 C14 1.384(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(3) . ?
C17 H17 0.9500 . ?
C14 H14 0.9500 . ?

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
C9 O4 H4 107.8(19) . . ?
C2 O2 C3 117.29(14) . . ?
C3 C4 C9 125.62(16) . . ?
C3 C4 C5 118.38(16) . . ?
C5 C4 C9 116.00(16) . . ?
O4 C9 C4 115.24(15) . . ?
O3 C9 O4 123.18(16) . . ?
O3 C9 C4 121.58(16) . . ?
C3 C8 H8 120.4 . . ?
C3 C8 C7 119.22(17) . . ?
C7 C8 H8 120.4 . . ?
C5 C6 H6 120.3 . . ?
C5 C6 C7 119.35(18) . . ?
C7 C6 H6 120.3 . . ?
C4 C3 O2 122.55(16) . . ?
C8 C3 O2 116.09(15) . . ?
C8 C3 C4 121.22(17) . . ?
O2 C2 C1 110.57(16) . . ?
O1 C2 O2 122.36(17) . . ?
O1 C2 C1 127.06(18) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.12(17) . . ?
C6 C5 H5 119.4 . . ?
C8 C7 C10 119.13(17) . . ?
C6 C7 C8 120.69(17) . . ?
C6 C7 C10 120.16(17) . . ?
F3 C10 C7 112.74(19) . . ?
F3 C10 F1 107.3(2) . . ?
F3 C10 F2 106.5(2) . . ?
F1 C10 C7 112.48(18) . . ?
F2 C10 C7 112.04(18) . . ?
F2 C10 F1 105.4(3) . . ?
F2A C10 C7 113.3(4) . . ?
F1A C10 C7 116.7(4) . . ?
F1A C10 F2A 101.2(9) . . ?
F1A C10 F3A 106.2(10) . . ?
F3A C10 C7 114.2(5) . . ?
F3A C10 F2A 103.7(11) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C11 N11 H11A 120.4(15) . . ?
C11 N11 H11B 118.6(17) . . ?
H11A N11 H11B 121(2) . . ?
C13 C12 C11 118.68(16) . . ?
C13 C12 C17 119.74(17) . . ?
C17 C12 C11 121.58(17) . . ?
O11 C11 N11 122.13(17) . . ?
O11 C11 C12 120.03(16) . . ?
N11 C11 C12 117.83(16) . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C16 C15 H15 119.6 . . ?
C16 C15 C14 120.79(19) . . ?
C14 C15 H15 119.6 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.1(2) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 H17 120.2 . . ?
C16 C17 C12 119.7(2) . . ?
C16 C17 H17 120.2 . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 H14 120.4 . . ?

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
N11 H11A O11 0.92(2) 2.11(2) 2.976(2) 156(2) 1_455
N11 H11B O3 0.88(3) 2.08(3) 2.934(2) 162(2) 1_655
O4 H4 O11 0.95(3) 1.64(3) 2.5723(19) 167(3) 1_455

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
C9 C4 C3 O2 3.3(3) . . . . ?
C9 C4 C3 C8 178.82(17) . . . . ?
C9 C4 C5 C6 -178.55(17) . . . . ?
C8 C7 C10 F3 -43.0(3) . . . . ?
C8 C7 C10 F1 -164.5(4) . . . . ?
C8 C7 C10 F2 77.0(3) . . . . ?
C8 C7 C10 F2A 30.4(16) . . . . ?
C8 C7 C10 F1A 147.4(15) . . . . ?
C8 C7 C10 F3A -88.1(19) . . . . ?
C6 C7 C10 F3 138.4(3) . . . . ?
C6 C7 C10 F1 17.0(4) . . . . ?
C6 C7 C10 F2 -101.5(3) . . . . ?
C6 C7 C10 F2A -148.2(16) . . . . ?
C6 C7 C10 F1A -31.2(15) . . . . ?
C6 C7 C10 F3A 93.4(19) . . . . ?
C3 O2 C2 O1 -9.9(2) . . . . ?
C3 O2 C2 C1 170.93(15) . . . . ?
C3 C4 C9 O4 -7.3(3) . . . . ?
C3 C4 C9 O3 173.33(18) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C3 C8 C7 C6 0.1(3) . . . . ?
C3 C8 C7 C10 -178.45(17) . . . . ?
C2 O2 C3 C4 -71.9(2) . . . . ?
C2 O2 C3 C8 112.33(18) . . . . ?
C5 C4 C9 O4 172.71(16) . . . . ?
C5 C4 C9 O3 -6.7(3) . . . . ?
C5 C4 C3 O2 -176.74(16) . . . . ?
C5 C4 C3 C8 -1.2(3) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C5 C6 C7 C10 178.69(18) . . . . ?
C7 C8 C3 O2 176.24(16) . . . . ?
C7 C8 C3 C4 0.4(3) . . . . ?
C7 C6 C5 C4 -1.0(3) . . . . ?
C12 C13 C14 C15 1.6(3) . . . . ?
C11 C12 C13 C14 178.49(18) . . . . ?
C11 C12 C17 C16 -179.55(17) . . . . ?
C13 C12 C11 O11 29.8(3) . . . . ?
C13 C12 C11 N11 -149.87(18) . . . . ?
C13 C12 C17 C16 1.1(3) . . . . ?
C15 C16 C17 C12 0.4(3) . . . . ?
C16 C15 C14 C13 -0.1(3) . . . . ?
C17 C12 C11 O11 -149.57(18) . . . . ?
C17 C12 C11 N11 30.8(3) . . . . ?
C17 C12 C13 C14 -2.2(3) . . . . ?
C14 C15 C16 C17 -1.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Tetrahydrofuran'
####################################################################### 
# 
# 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_TRFL-INA
_database_code_depnum_ccdc_archive 'CCDC 1421381'
_audit_update_record             
;
2015-08-31 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;
_audit_creation_date             2015-08-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        'Triflusal-Isonicotinamide cocrystal'
_chemical_formula_moiety         'C10 H7 F3 O4, C6 H6 N2 O'
_chemical_formula_sum            'C16 H13 F3 N2 O5'
_chemical_formula_weight         370.28
_chemical_melting_point          406.1
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   17.345(7)
_cell_length_b                   5.1415(17)
_cell_length_c                   19.447(7)
_cell_angle_alpha                90
_cell_angle_beta                 112.506(5)
_cell_angle_gamma                90
_cell_volume                     1602.2(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4030
_cell_measurement_temperature    110
_cell_measurement_theta_max      30.9493
_cell_measurement_theta_min      2.2683
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'R. H. Blessing, Acta Cryst. 1995 A51, 33-38'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10874
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.463
_diffrn_reflns_theta_min         2.994
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
scan:
	Number of images: 300
	           Slice: -110.0000 - 40.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 90.0000
	             XTD: 45.0292
	          2theta: -20.2668
scan:
	Number of images: 202
	           Slice: -110.0000 - -9.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -70.0000
	             Phi: 0.0000
	             XTD: 45.0292
	          2theta: -20.2668
scan:
	Number of images: 182
	           Slice: -61.0000 - 30.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 90.0000
	             XTD: 45.0292
	          2theta: -20.2668
;
_diffrn_measurement_device       
;
Saturn70 (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             5004
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0105
_diffrn_orient_matrix_UB_12      0.0469
_diffrn_orient_matrix_UB_13      -0.0398
_diffrn_orient_matrix_UB_21      -0.0361
_diffrn_orient_matrix_UB_22      -0.1188
_diffrn_orient_matrix_UB_23      -0.1497
_diffrn_orient_matrix_UB_31      -0.0462
_diffrn_orient_matrix_UB_32      0.0288
_diffrn_orient_matrix_UB_33      -0.0117
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0000
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3078
_reflns_number_total             3648
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3648
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0559
_refine_ls_restrained_S_all      1.108
_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)+(0.1010P)²+0.2281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.1782
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Restrained distances
 O4-H4
 0.84 with sigma of 0.02
3. Others
 Sof(H1BD)=Sof(H1BE)=Sof(H1BF)=Sof(O1A)=Sof(O2A)=Sof(C2A)=Sof(C3A)=Sof(C8A)=
 Sof(H8A)=1-FVAR(1)
 Sof(O2)=Sof(C8)=Sof(H8)=Sof(C3)=Sof(O1)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C2)=
 FVAR(1)
4.a Me refined with riding coordinates:
 C1(H1AA,H1AB,H1AC), C1(H1BD,H1BE,H1BF)
4.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C14(H14), C15(H15), C13(H13), C6(H6), C5(H5), C8(H8), C8A(H8A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O3 O 0.62965(7) 0.6879(2) 0.34541(7) 0.0321(3) Uani 1 1 d . . . . .
N12 N 0.33881(9) 0.0748(3) 0.27788(8) 0.0283(3) Uani 1 1 d . . . . .
O4 O 0.73753(8) 0.7058(3) 0.31023(8) 0.0354(3) Uani 1 1 d D . . . .
O11 O 0.42027(8) 0.7683(2) 0.46920(7) 0.0341(3) Uani 1 1 d . . . . .
N11 N 0.52582(9) 0.8037(3) 0.42908(9) 0.0290(3) Uani 1 1 d . . . . .
F3 F 0.83129(8) -0.3281(2) 0.58580(7) 0.0500(4) Uani 1 1 d . . . . .
F2 F 0.94761(9) -0.2053(3) 0.58215(8) 0.0604(4) Uani 1 1 d . . . . .
C12 C 0.41740(10) 0.4776(3) 0.37385(9) 0.0258(4) Uani 1 1 d . . . . .
F1 F 0.89395(9) -0.0006(2) 0.64864(7) 0.0529(4) Uani 1 1 d . . . . .
C4 C 0.74687(11) 0.4152(4) 0.40757(10) 0.0306(4) Uani 1 1 d . . . . .
C16 C 0.34441(11) 0.3684(4) 0.37453(10) 0.0316(4) Uani 1 1 d . . . . .
H16 H 0.3207 0.4299 0.4082 0.038 Uiso 1 1 calc R . . . .
C14 C 0.40888(10) 0.1804(3) 0.27690(10) 0.0300(4) Uani 1 1 d . . . . .
H14 H 0.4314 0.1149 0.2428 0.036 Uiso 1 1 calc R . . . .
C11 C 0.45581(10) 0.6962(3) 0.42812(9) 0.0255(4) Uani 1 1 d . . . . .
C15 C 0.30674(12) 0.1687(4) 0.32546(10) 0.0339(4) Uani 1 1 d . . . . .
H15 H 0.2564 0.0958 0.3255 0.041 Uiso 1 1 calc R . . . .
C9 C 0.69936(10) 0.6171(3) 0.35078(10) 0.0283(4) Uani 1 1 d . . . . .
C13 C 0.44972(10) 0.3824(4) 0.32405(10) 0.0295(4) Uani 1 1 d . . . . .
H13 H 0.4993 0.4543 0.3221 0.035 Uiso 1 1 calc R . . . .
C6 C 0.74842(11) 0.1212(4) 0.50468(11) 0.0357(4) Uani 1 1 d . . . . .
H6 H 0.7198 0.0422 0.5323 0.043 Uiso 1 1 calc R . . . .
C5 C 0.70774(11) 0.3002(4) 0.44930(11) 0.0342(4) Uani 1 1 d . . . . .
H5 H 0.6515 0.3445 0.4400 0.041 Uiso 1 1 calc R . . . .
C7 C 0.83020(11) 0.0586(3) 0.51949(10) 0.0319(4) Uani 1 1 d . . . . .
C10 C 0.87641(12) -0.1193(4) 0.58321(11) 0.0339(4) Uani 1 1 d . . . . .
O2 O 0.88459(13) 0.5197(4) 0.40213(14) 0.0301(6) Uani 0.614(4) 1 d . . P A 1
C8 C 0.8779(2) 0.1999(8) 0.4875(2) 0.0300(8) Uani 0.614(4) 1 d . . P A 1
H8 H 0.9364 0.1745 0.5037 0.036 Uiso 0.614(4) 1 calc R . P A 1
C3 C 0.8366(2) 0.3771(7) 0.4318(2) 0.0268(7) Uani 0.614(4) 1 d . . P A 1
O1 O 0.85013(15) 0.2412(5) 0.30547(13) 0.0412(7) Uani 0.614(4) 1 d . . P A 1
C1 C 0.92296(15) 0.6210(5) 0.30132(14) 0.0531(6) Uani 1 1 d . . . . .
H1AA H 0.9448 0.7693 0.3348 0.080 Uiso 0.614(4) 1 calc R . P A 1
H1AB H 0.8824 0.6827 0.2535 0.080 Uiso 0.614(4) 1 calc R . P A 1
H1AC H 0.9690 0.5328 0.2935 0.080 Uiso 0.614(4) 1 calc R . P A 1
H1BD H 0.8971 0.5002 0.2599 0.080 Uiso 0.386(4) 1 calc R . P A 2
H1BE H 0.9838 0.6133 0.3173 0.080 Uiso 0.386(4) 1 calc R . P A 2
H1BF H 0.9037 0.7982 0.2852 0.080 Uiso 0.386(4) 1 calc R . P A 2
C2 C 0.8824(2) 0.4401(9) 0.3343(2) 0.0321(8) Uani 0.614(4) 1 d . . P A 1
O1A O 0.9235(2) 0.6667(8) 0.4205(2) 0.0440(11) Uani 0.386(4) 1 d . . P A 2
O2A O 0.8485(2) 0.3315(7) 0.3535(2) 0.0316(10) Uani 0.386(4) 1 d . . P A 2
C2A C 0.8996(4) 0.5481(14) 0.3635(5) 0.0390(14) Uani 0.386(4) 1 d . . P A 2
C3A C 0.8156(3) 0.2888(12) 0.4066(3) 0.0264(10) Uani 0.386(4) 1 d . . P A 2
C8A C 0.8589(4) 0.1144(13) 0.4637(3) 0.0286(12) Uani 0.386(4) 1 d . . P A 2
H8A H 0.9084 0.0337 0.4641 0.034 Uiso 0.386(4) 1 calc R . P A 2
H11A H 0.5526(14) 0.749(4) 0.3993(12) 0.034(5) Uiso 1 1 d . . . . .
H11B H 0.5450(14) 0.934(5) 0.4598(13) 0.042(6) Uiso 1 1 d . . . . .
H4 H 0.708(2) 0.830(6) 0.2809(19) 0.120(14) Uiso 1 1 d 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
O3 C9 1.228(2) . ?
N12 C14 1.338(2) . ?
N12 C15 1.339(2) . ?
O4 C9 1.292(2) . ?
O4 H4 0.877(19) . ?
O11 C11 1.238(2) . ?
N11 C11 1.328(2) . ?
N11 H11A 0.91(2) . ?
N11 H11B 0.87(3) . ?
F3 C10 1.341(2) . ?
F2 C10 1.319(2) . ?
C12 C16 1.390(2) . ?
C12 C11 1.511(2) . ?
C12 C13 1.381(2) . ?
F1 C10 1.337(2) . ?
C4 C9 1.510(2) . ?
C4 C5 1.375(2) . ?
C4 C3 1.456(4) . ?
C4 C3A 1.364(5) . ?
C16 H16 0.9500 . ?
C16 C15 1.384(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.387(2) . ?
C15 H15 0.9500 . ?
C13 H13 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.387(3) . ?
C6 C7 1.373(3) . ?
C5 H5 0.9500 . ?
C7 C10 1.501(2) . ?
C7 C8 1.411(4) . ?
C7 C8A 1.386(6) . ?
O2 C3 1.389(4) . ?
O2 C2 1.368(5) . ?
C8 H8 0.9500 . ?
C8 C3 1.388(5) . ?
O1 C2 1.197(5) . ?
C1 H1AA 0.9800 . ?
C1 H1AB 0.9800 . ?
C1 H1AC 0.9800 . ?
C1 H1BD 0.9800 . ?
C1 H1BE 0.9800 . ?
C1 H1BF 0.9800 . ?
C1 C2 1.455(5) . ?
C1 C2A 1.465(8) . ?
O1A C2A 1.192(10) . ?
O2A C2A 1.389(8) . ?
O2A C3A 1.374(6) . ?
C3A C8A 1.401(7) . ?
C8A H8A 0.9500 . ?

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
C14 N12 C15 118.92(15) . . ?
C9 O4 H4 111(3) . . ?
C11 N11 H11A 123.3(14) . . ?
C11 N11 H11B 115.8(14) . . ?
H11A N11 H11B 121(2) . . ?
C16 C12 C11 116.98(15) . . ?
C13 C12 C16 118.65(16) . . ?
C13 C12 C11 124.37(15) . . ?
C5 C4 C9 118.22(15) . . ?
C5 C4 C3 117.3(2) . . ?
C3 C4 C9 123.05(19) . . ?
C3A C4 C9 123.5(3) . . ?
C3A C4 C5 115.8(3) . . ?
C12 C16 H16 120.5 . . ?
C15 C16 C12 118.98(16) . . ?
C15 C16 H16 120.5 . . ?
N12 C14 H14 119.0 . . ?
N12 C14 C13 122.08(16) . . ?
C13 C14 H14 119.0 . . ?
O11 C11 N11 123.02(16) . . ?
O11 C11 C12 118.56(15) . . ?
N11 C11 C12 118.42(15) . . ?
N12 C15 C16 122.20(16) . . ?
N12 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
O3 C9 O4 124.15(16) . . ?
O3 C9 C4 120.66(15) . . ?
O4 C9 C4 115.19(14) . . ?
C12 C13 C14 119.16(15) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C7 C6 C5 119.74(17) . . ?
C4 C5 C6 121.63(16) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C6 C7 C10 119.87(16) . . ?
C6 C7 C8 121.3(2) . . ?
C6 C7 C8A 116.0(3) . . ?
C8 C7 C10 117.3(2) . . ?
C8A C7 C10 122.3(3) . . ?
F3 C10 C7 112.57(16) . . ?
F2 C10 F3 107.18(16) . . ?
F2 C10 F1 107.13(16) . . ?
F2 C10 C7 113.48(15) . . ?
F1 C10 F3 104.67(15) . . ?
F1 C10 C7 111.27(16) . . ?
C2 O2 C3 116.2(3) . . ?
C7 C8 H8 121.1 . . ?
C3 C8 C7 117.9(3) . . ?
C3 C8 H8 121.1 . . ?
O2 C3 C4 122.1(3) . . ?
C8 C3 C4 120.6(3) . . ?
C8 C3 O2 117.3(3) . . ?
H1AA C1 H1AB 109.5 . . ?
H1AA C1 H1AC 109.5 . . ?
H1AB C1 H1AC 109.5 . . ?
H1BD C1 H1BE 109.5 . . ?
H1BD C1 H1BF 109.5 . . ?
H1BE C1 H1BF 109.5 . . ?
C2 C1 H1AA 109.5 . . ?
C2 C1 H1AB 109.5 . . ?
C2 C1 H1AC 109.5 . . ?
C2A C1 H1BD 109.5 . . ?
C2A C1 H1BE 109.5 . . ?
C2A C1 H1BF 109.5 . . ?
O2 C2 C1 113.2(4) . . ?
O1 C2 O2 122.9(3) . . ?
O1 C2 C1 123.9(4) . . ?
C3A O2A C2A 116.7(6) . . ?
O1A C2A C1 122.0(6) . . ?
O1A C2A O2A 121.1(7) . . ?
O2A C2A C1 116.9(7) . . ?
C4 C3A O2A 123.4(4) . . ?
C4 C3A C8A 120.0(4) . . ?
O2A C3A C8A 116.5(4) . . ?
C7 C8A C3A 120.6(5) . . ?
C7 C8A H8A 119.7 . . ?
C3A C8A H8A 119.7 . . ?

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
N11 H11A O3 0.91(2) 2.01(2) 2.914(2) 168(2) .
N11 H11B O11 0.87(3) 1.99(3) 2.866(2) 175(2) 3_676
O4 H4 N12 0.877(19) 1.686(19) 2.5596(19) 174(4) 2_665

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
N12 C14 C13 C12 0.2(3) . . . . ?
C12 C16 C15 N12 0.8(3) . . . . ?
C4 C3A C8A C7 3.3(9) . . . . ?
C16 C12 C11 O11 -0.9(2) . . . . ?
C16 C12 C11 N11 179.66(15) . . . . ?
C16 C12 C13 C14 -0.5(3) . . . . ?
C14 N12 C15 C16 -1.1(3) . . . . ?
C11 C12 C16 C15 179.59(16) . . . . ?
C11 C12 C13 C14 179.95(15) . . . . ?
C15 N12 C14 C13 0.6(3) . . . . ?
C9 C4 C5 C6 -177.26(17) . . . . ?
C9 C4 C3 O2 -2.2(5) . . . . ?
C9 C4 C3 C8 175.9(3) . . . . ?
C9 C4 C3A O2A -0.3(8) . . . . ?
C9 C4 C3A C8A 176.5(4) . . . . ?
C13 C12 C16 C15 0.0(3) . . . . ?
C13 C12 C11 O11 178.67(16) . . . . ?
C13 C12 C11 N11 -0.8(2) . . . . ?
C6 C7 C10 F3 45.0(3) . . . . ?
C6 C7 C10 F2 166.93(18) . . . . ?
C6 C7 C10 F1 -72.2(2) . . . . ?
C6 C7 C8 C3 -10.0(5) . . . . ?
C6 C7 C8A C3A 17.7(7) . . . . ?
C5 C4 C9 O3 4.4(3) . . . . ?
C5 C4 C9 O4 -175.86(16) . . . . ?
C5 C4 C3 O2 -168.4(3) . . . . ?
C5 C4 C3 C8 9.6(5) . . . . ?
C5 C4 C3A O2A 161.5(5) . . . . ?
C5 C4 C3A C8A -21.7(7) . . . . ?
C5 C6 C7 C10 175.30(18) . . . . ?
C5 C6 C7 C8 9.6(4) . . . . ?
C5 C6 C7 C8A -19.7(4) . . . . ?
C7 C6 C5 C4 1.0(3) . . . . ?
C7 C8 C3 C4 0.2(5) . . . . ?
C7 C8 C3 O2 178.4(3) . . . . ?
C10 C7 C8 C3 -176.0(3) . . . . ?
C10 C7 C8A C3A -177.7(4) . . . . ?
C8 C7 C10 F3 -148.8(2) . . . . ?
C8 C7 C10 F2 -26.8(3) . . . . ?
C8 C7 C10 F1 94.1(3) . . . . ?
C8 C7 C8A C3A -90.8(9) . . . . ?
C3 C4 C9 O3 -161.7(2) . . . . ?
C3 C4 C9 O4 18.0(3) . . . . ?
C3 C4 C5 C6 -10.3(3) . . . . ?
C3 C4 C3A O2A -98.3(9) . . . . ?
C3 C4 C3A C8A 78.4(7) . . . . ?
C3 O2 C2 O1 -9.2(4) . . . . ?
C3 O2 C2 C1 170.7(2) . . . . ?
C2 O2 C3 C4 -79.5(4) . . . . ?
C2 O2 C3 C8 102.3(4) . . . . ?
C2 C1 C2A O1A 173.5(9) . . . . ?
C2 C1 C2A O2A -5.8(3) . . . . ?
O2A C3A C8A C7 -179.8(6) . . . . ?
C2A C1 C2 O2 2.3(4) . . . . ?
C2A C1 C2 O1 -177.8(7) . . . . ?
C2A O2A C3A C4 80.9(7) . . . . ?
C2A O2A C3A C8A -95.9(6) . . . . ?
C3A C4 C9 O3 165.8(4) . . . . ?
C3A C4 C9 O4 -14.5(4) . . . . ?
C3A C4 C5 C6 19.9(4) . . . . ?
C3A C4 C3 O2 97.9(7) . . . . ?
C3A C4 C3 C8 -84.0(7) . . . . ?
C3A O2A C2A C1 -169.6(4) . . . . ?
C3A O2A C2A O1A 11.0(7) . . . . ?
C8A C7 C10 F3 -119.1(4) . . . . ?
C8A C7 C10 F2 2.9(4) . . . . ?
C8A C7 C10 F1 123.8(4) . . . . ?
C8A C7 C8 C3 75.8(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Tetrahydrofuran'
####################################################################### 
# 
# 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_TRFL-PA
_database_code_depnum_ccdc_archive 'CCDC 1421382'
_audit_update_record             
;
2015-08-31 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;
_audit_creation_date             2015-07-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        'Triflusal-2-Picoliniamide cocrystal'
_chemical_formula_moiety         'C10 H7 F3 O4, C6 H6 N2 O'
_chemical_formula_sum            'C16 H13 F3 N2 O5'
_chemical_formula_weight         370.28
_chemical_melting_point          377.9
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5536(11)
_cell_length_b                   11.950(2)
_cell_length_c                   12.200(2)
_cell_angle_alpha                96.01(3)
_cell_angle_beta                 94.85(3)
_cell_angle_gamma                95.99(3)
_cell_volume                     797.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2262
_cell_measurement_temperature    110.1500
_cell_measurement_theta_max      30.9124
_cell_measurement_theta_min      2.5471
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.9704
_exptl_absorpt_correction_T_min  0.9419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'R. H. Blessing, Acta Cryst. 1995 A51, 33-38'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11062
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         3.374
_diffrn_ambient_temperature      110.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
scan:
	Number of images: 300
	           Slice: -110.0000 - 40.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 180.0000
	             XTD: 44.9843
	          2theta: -20.2556
scan:
	Number of images: 262
	           Slice: -110.0000 - 21.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -70.0000
	             Phi: 90.0000
	             XTD: 44.9843
	          2theta: -20.2556
scan:
	Number of images: 262
	           Slice: -110.0000 - 21.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -70.0000
	             Phi: 270.0000
	             XTD: 44.9843
	          2theta: -20.2556
scan:
	Number of images: 210
	           Slice: -110.0000 - -5.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 90.0000
	             XTD: 44.9843
	          2theta: -20.2556
scan:
	Number of images: 208
	           Slice: -110.0000 - -6.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -70.0000
	             Phi: 180.0000
	             XTD: 44.9843
	          2theta: -20.2556
;
_diffrn_measurement_device       
;
Saturn70 (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             4471
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0876
_diffrn_orient_matrix_UB_12      0.0630
_diffrn_orient_matrix_UB_13      -0.1464
_diffrn_orient_matrix_UB_21      0.0076
_diffrn_orient_matrix_UB_22      0.0799
_diffrn_orient_matrix_UB_23      0.0269
_diffrn_orient_matrix_UB_31      0.0759
_diffrn_orient_matrix_UB_32      -0.0080
_diffrn_orient_matrix_UB_33      0.0321
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0000
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3720
_reflns_number_total             3873
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3873
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.086
_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)+(0.0626P)²+0.2857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1198
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C6(H6), C13(H13), C16(H16), C15(H15), C14(H14)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O3 O 1.12533(19) 0.36076(8) 0.62241(8) 0.0325(2) Uani 1 1 d . . . . .
O1 O 0.96157(16) 0.09987(8) 0.59388(8) 0.0274(2) Uani 1 1 d . . . . .
O2 O 1.16844(15) 0.18475(8) 0.46831(7) 0.0254(2) Uani 1 1 d . . . . .
O4 O 0.81085(19) 0.45965(8) 0.59382(8) 0.0322(2) Uani 1 1 d . . . . .
F2 F 0.51881(19) 0.16226(8) 0.07252(7) 0.0416(2) Uani 1 1 d . . . . .
C4 C 0.8455(2) 0.30801(10) 0.45949(9) 0.0226(2) Uani 1 1 d . . . . .
F3 F 0.3186(2) 0.05750(11) 0.17020(9) 0.0702(4) Uani 1 1 d . . . . .
F1 F 0.6694(3) 0.02064(10) 0.13016(9) 0.0706(4) Uani 1 1 d . . . . .
C8 C 0.8594(2) 0.14880(10) 0.31997(10) 0.0251(2) Uani 1 1 d . . . . .
H8 H 0.9354 0.0854 0.2926 0.030 Uiso 1 1 calc R . . . .
C2 C 1.1518(2) 0.13242(10) 0.56156(10) 0.0240(2) Uani 1 1 d . . . . .
C5 C 0.6387(2) 0.33528(10) 0.39927(10) 0.0247(2) Uani 1 1 d . . . . .
H5 H 0.5632 0.3992 0.4259 0.030 Uiso 1 1 calc R . . . .
C6 C 0.5413(2) 0.27070(10) 0.30123(10) 0.0255(2) Uani 1 1 d . . . . .
H6 H 0.4006 0.2901 0.2610 0.031 Uiso 1 1 calc R . . . .
C7 C 0.6527(2) 0.17724(10) 0.26277(10) 0.0248(2) Uani 1 1 d . . . . .
C3 C 0.9539(2) 0.21395(10) 0.41758(10) 0.0230(2) Uani 1 1 d . . . . .
C9 C 0.9440(2) 0.37803(10) 0.56640(10) 0.0241(2) Uani 1 1 d . . . . .
C10 C 0.5416(3) 0.10403(11) 0.15905(10) 0.0290(3) Uani 1 1 d . . . . .
C1 C 1.3994(3) 0.12111(14) 0.61355(13) 0.0363(3) Uani 1 1 d . . . . .
H1A H 1.3927 0.1160 0.6929 0.055 Uiso 1 1 calc GR . . . .
H1B H 1.5110 0.1874 0.6031 0.055 Uiso 1 1 calc GR . . . .
H1C H 1.4572 0.0525 0.5789 0.055 Uiso 1 1 calc GR . . . .
O11 O 1.06604(17) 0.42436(8) 0.21692(7) 0.0283(2) Uani 1 1 d . . . . .
N12 N 0.70786(19) 0.38110(9) -0.04272(9) 0.0250(2) Uani 1 1 d . . . . .
N11 N 0.7323(2) 0.50444(9) 0.16006(9) 0.0275(2) Uani 1 1 d . . . . .
C13 C 1.0543(3) 0.29034(12) 0.01694(11) 0.0313(3) Uani 1 1 d . . . . .
H13 H 1.1786 0.2838 0.0736 0.038 Uiso 1 1 calc R . . . .
C16 C 0.6980(2) 0.31709(11) -0.14016(11) 0.0289(3) Uani 1 1 d . . . . .
H16 H 0.5748 0.3266 -0.1962 0.035 Uiso 1 1 calc R . . . .
C15 C 0.8567(2) 0.23776(11) -0.16433(11) 0.0297(3) Uani 1 1 d . . . . .
H15 H 0.8401 0.1936 -0.2345 0.036 Uiso 1 1 calc R . . . .
C11 C 0.9002(2) 0.43523(10) 0.14487(10) 0.0231(2) Uani 1 1 d . . . . .
C12 C 0.8852(2) 0.36598(10) 0.03390(9) 0.0224(2) Uani 1 1 d . . . . .
C14 C 1.0388(3) 0.22416(12) -0.08457(11) 0.0337(3) Uani 1 1 d . . . . .
H14 H 1.1511 0.1708 -0.0986 0.040 Uiso 1 1 calc R . . . .
H11A H 0.623(3) 0.5107(16) 0.1084(16) 0.038(5) Uiso 1 1 d . . . . .
H11B H 0.742(4) 0.5463(17) 0.2229(17) 0.045(5) Uiso 1 1 d . . . . .
H4 H 0.871(5) 0.497(2) 0.664(2) 0.075(7) 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
O3 C9 1.2168(16) . ?
O1 C2 1.2000(16) . ?
O2 C2 1.3595(15) . ?
O2 C3 1.3901(15) . ?
O4 C9 1.3167(16) . ?
O4 H4 0.94(3) . ?
F2 C10 1.3282(16) . ?
C4 C5 1.3968(18) . ?
C4 C3 1.3998(17) . ?
C4 C9 1.5019(17) . ?
F3 C10 1.3272(18) . ?
F1 C10 1.3184(16) . ?
C8 H8 0.9500 . ?
C8 C7 1.3840(18) . ?
C8 C3 1.3836(17) . ?
C2 C1 1.4898(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3889(17) . ?
C6 H6 0.9500 . ?
C6 C7 1.3906(18) . ?
C7 C10 1.5071(17) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
O11 C11 1.2448(15) . ?
N12 C16 1.3383(16) . ?
N12 C12 1.3393(16) . ?
N11 C11 1.3215(16) . ?
N11 H11A 0.85(2) . ?
N11 H11B 0.86(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.3830(17) . ?
C13 C14 1.3888(18) . ?
C16 H16 0.9500 . ?
C16 C15 1.3863(18) . ?
C15 H15 0.9500 . ?
C15 C14 1.3775(19) . ?
C11 C12 1.5021(16) . ?
C14 H14 0.9500 . ?

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
C2 O2 C3 117.04(9) . . ?
C9 O4 H4 109.3(16) . . ?
C5 C4 C3 118.01(11) . . ?
C5 C4 C9 120.07(11) . . ?
C3 C4 C9 121.92(11) . . ?
C7 C8 H8 120.4 . . ?
C3 C8 H8 120.4 . . ?
C3 C8 C7 119.15(11) . . ?
O1 C2 O2 123.20(11) . . ?
O1 C2 C1 126.63(12) . . ?
O2 C2 C1 110.16(11) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.24(12) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C7 119.08(12) . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 121.02(11) . . ?
C8 C7 C10 119.70(11) . . ?
C6 C7 C10 119.25(12) . . ?
O2 C3 C4 121.91(11) . . ?
C8 C3 O2 116.51(11) . . ?
C8 C3 C4 121.49(12) . . ?
O3 C9 O4 123.50(11) . . ?
O3 C9 C4 123.87(11) . . ?
O4 C9 C4 112.63(11) . . ?
F2 C10 C7 112.48(10) . . ?
F3 C10 F2 105.53(12) . . ?
F3 C10 C7 111.82(11) . . ?
F1 C10 F2 106.62(12) . . ?
F1 C10 F3 107.02(13) . . ?
F1 C10 C7 112.90(12) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C16 N12 C12 116.29(11) . . ?
C11 N11 H11A 121.2(13) . . ?
C11 N11 H11B 117.9(13) . . ?
H11A N11 H11B 120.8(18) . . ?
C12 C13 H13 120.7 . . ?
C12 C13 C14 118.69(12) . . ?
C14 C13 H13 120.7 . . ?
N12 C16 H16 118.0 . . ?
N12 C16 C15 124.02(12) . . ?
C15 C16 H16 118.0 . . ?
C16 C15 H15 120.6 . . ?
C14 C15 C16 118.72(12) . . ?
C14 C15 H15 120.6 . . ?
O11 C11 N11 123.76(11) . . ?
O11 C11 C12 119.18(11) . . ?
N11 C11 C12 117.06(11) . . ?
N12 C12 C13 123.90(11) . . ?
N12 C12 C11 117.86(11) . . ?
C13 C12 C11 118.24(11) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 C13 118.37(12) . . ?
C15 C14 H14 120.8 . . ?

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
N11 H11A N12 0.85(2) 2.48(2) 3.2269(18) 146.6(17) 2_665
N11 H11B O3 0.86(2) 2.12(2) 2.9575(17) 162.8(18) 2_766
O4 H4 O11 0.94(3) 1.64(3) 2.5661(15) 169(2) 2_766

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
C4 C5 C6 C7 0.01(18) . . . . ?
C8 C7 C10 F2 -124.53(13) . . . . ?
C8 C7 C10 F3 116.93(15) . . . . ?
C8 C7 C10 F1 -3.82(18) . . . . ?
C2 O2 C3 C4 76.96(14) . . . . ?
C2 O2 C3 C8 -106.41(12) . . . . ?
C5 C4 C3 O2 175.96(10) . . . . ?
C5 C4 C3 C8 -0.50(17) . . . . ?
C5 C4 C9 O3 -178.69(12) . . . . ?
C5 C4 C9 O4 2.05(16) . . . . ?
C5 C6 C7 C8 -0.71(18) . . . . ?
C5 C6 C7 C10 177.40(11) . . . . ?
C6 C7 C10 F2 57.33(16) . . . . ?
C6 C7 C10 F3 -61.21(16) . . . . ?
C6 C7 C10 F1 178.04(13) . . . . ?
C7 C8 C3 O2 -176.82(10) . . . . ?
C7 C8 C3 C4 -0.18(18) . . . . ?
C3 O2 C2 O1 8.50(17) . . . . ?
C3 O2 C2 C1 -172.41(11) . . . . ?
C3 C4 C5 C6 0.59(18) . . . . ?
C3 C4 C9 O3 1.96(19) . . . . ?
C3 C4 C9 O4 -177.31(11) . . . . ?
C3 C8 C7 C6 0.79(18) . . . . ?
C3 C8 C7 C10 -177.31(11) . . . . ?
C9 C4 C5 C6 -178.80(11) . . . . ?
C9 C4 C3 O2 -4.67(17) . . . . ?
C9 C4 C3 C8 178.87(11) . . . . ?
O11 C11 C12 N12 -178.70(11) . . . . ?
O11 C11 C12 C13 1.48(18) . . . . ?
N12 C16 C15 C14 -1.0(2) . . . . ?
N11 C11 C12 N12 1.75(17) . . . . ?
N11 C11 C12 C13 -178.06(12) . . . . ?
C16 N12 C12 C13 0.57(19) . . . . ?
C16 N12 C12 C11 -179.23(11) . . . . ?
C16 C15 C14 C13 0.4(2) . . . . ?
C12 N12 C16 C15 0.5(2) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C14 C13 C12 N12 -1.2(2) . . . . ?
C14 C13 C12 C11 178.64(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Tetrahydrofuran'
####################################################################### 
# 
# 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_TRFL-PRA
_database_code_depnum_ccdc_archive 'CCDC 1421383'
_audit_update_record             
;
2015-08-31 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;
_audit_creation_date             2015-07-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        'Triflusal-Propionamide cocrystal'
_chemical_formula_moiety         'C10 H7 F3 O4, C3 H7 N O'
_chemical_formula_sum            'C13 H14 F3 N O5'
_chemical_formula_weight         321.25
_chemical_melting_point          333.5
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   18.729(6)
_cell_length_b                   9.921(3)
_cell_length_c                   8.067(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.605(4)
_cell_angle_gamma                90
_cell_volume                     1485.7(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3936
_cell_measurement_temperature    110
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'R. H. Blessing, Acta Cryst. 1995 A51, 33-38'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             664
_exptl_crystal_preparation       Fiber
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10698
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_min         3.005
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
scan:
	Number of images: 300
	           Slice: -110.0000 - 40.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 90.0000
	             XTD: 45.0311
	          2theta: -20.1220
scan:
	Number of images: 196
	           Slice: -34.7500 - 63.2500
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 90.0000
	             XTD: 45.0311
	          2theta: -20.1220
scan:
	Number of images: 204
	           Slice: -85.2500 - 16.7500
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -70.0000
	             Phi: 0.0000
	             XTD: 45.0311
	          2theta: -20.1220
;
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   ?
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3086
_reflns_number_total             3391
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3391
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.061
_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)+(0.0635P)²+0.3449P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1157
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H11C-H11D
 1.5 with sigma of 0.02
 N11A-H11D = N11A-H11C
 0.88 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C11A, O11A, N11A, C12A, H11C, H11D, H12C, H12D, C13A, H13D, H13E, H13F, C11,
 O11, N11, C12, H11A, H11B, H12A, H12B, C13, H13A, H13B, H13C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O11A)=Sof(C11A)=Sof(N11A)=Sof(H11C)=Sof(H11D)=Sof(C12A)=Sof(H12C)=
 Sof(H12D)=Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=1-FVAR(1)
 Sof(O11)=Sof(C11)=Sof(N11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C12A(H12C,H12D)
5.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C6(H6)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C), C13A(H13D,H13E,H13F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
F1 F -0.04334(4) 0.69191(8) 0.38325(11) 0.0356(2) Uani 1 1 d . . . . .
F2 F 0.00039(5) 0.87078(8) 0.28392(10) 0.0352(2) Uani 1 1 d . . . . .
O2 O 0.17303(5) 0.41479(8) 0.48332(11) 0.0240(2) Uani 1 1 d . . . . .
F3 F -0.01671(5) 0.86380(8) 0.54205(10) 0.0357(2) Uani 1 1 d . . . . .
O3 O 0.31269(5) 0.47366(10) 0.60902(14) 0.0371(3) Uani 1 1 d . . . . .
C8 C 0.09434(6) 0.60093(12) 0.44925(14) 0.0231(2) Uani 1 1 d . . . . .
H8 H 0.0566 0.5405 0.4097 0.028 Uiso 1 1 calc R . . . .
O11 O 0.4768(4) 0.6319(7) 0.7150(10) 0.0391(8) Uani 0.801(6) 1 d . U P A 1
C3 C 0.16403(6) 0.55359(12) 0.49195(14) 0.0219(2) Uani 1 1 d . . . . .
O4 O 0.34219(6) 0.69035(11) 0.63126(19) 0.0526(4) Uani 1 1 d . . . . .
O1 O 0.22796(8) 0.43697(11) 0.25319(13) 0.0481(3) Uani 1 1 d . . . . .
C4 C 0.22029(7) 0.64064(12) 0.54988(16) 0.0253(3) Uani 1 1 d . . . . .
C10 C 0.00531(7) 0.78957(13) 0.41901(16) 0.0264(3) Uani 1 1 d . . . . .
C7 C 0.08029(6) 0.73711(12) 0.46477(14) 0.0234(3) Uani 1 1 d . . . . .
C2 C 0.20779(7) 0.36590(13) 0.35749(15) 0.0280(3) Uani 1 1 d . . . . .
C5 C 0.20460(7) 0.77750(13) 0.56478(18) 0.0306(3) Uani 1 1 d . . . . .
H5 H 0.2422 0.8383 0.6045 0.037 Uiso 1 1 calc R . . . .
C6 C 0.13524(7) 0.82619(13) 0.52273(17) 0.0289(3) Uani 1 1 d . . . . .
H6 H 0.1253 0.9195 0.5334 0.035 Uiso 1 1 calc R . . . .
C1 C 0.21476(8) 0.21671(13) 0.37101(17) 0.0343(3) Uani 1 1 d . . . . .
H1A H 0.2351 0.1924 0.4853 0.051 Uiso 1 1 calc GR . . . .
H1B H 0.2466 0.1844 0.2924 0.051 Uiso 1 1 calc GR . . . .
H1C H 0.1672 0.1752 0.3442 0.051 Uiso 1 1 calc GR . . . .
C9 C 0.29573(7) 0.59155(13) 0.59906(17) 0.0283(3) Uani 1 1 d . . . . .
C11 C 0.5059(2) 0.5185(4) 0.7157(6) 0.0311(8) Uani 0.801(6) 1 d . U P A 1
N11 N 0.4660(2) 0.4078(4) 0.6861(6) 0.0344(8) Uani 0.801(6) 1 d . U P A 1
H11A H 0.4187(15) 0.412(3) 0.665(3) 0.041 Uiso 0.801(6) 1 d R U P A 1
H11B H 0.4841(14) 0.327(3) 0.702(3) 0.041 Uiso 0.801(6) 1 d R U P A 1
C12 C 0.58544(19) 0.5032(4) 0.7523(4) 0.0340(7) Uani 0.801(6) 1 d . U P A 1
H12A H 0.6092 0.5711 0.6883 0.041 Uiso 0.801(6) 1 calc R U P A 1
H12B H 0.5996 0.4126 0.7169 0.041 Uiso 0.801(6) 1 calc R U P A 1
C13 C 0.61014(11) 0.5215(2) 0.9389(3) 0.0450(7) Uani 0.801(6) 1 d . U P A 1
H13A H 0.5899 0.4493 1.0014 0.067 Uiso 0.801(6) 1 calc GR U P A 1
H13B H 0.5935 0.6090 0.9753 0.067 Uiso 0.801(6) 1 calc GR U P A 1
H13C H 0.6629 0.5179 0.9599 0.067 Uiso 0.801(6) 1 calc GR U P A 1
H4 H 0.3914(19) 0.660(3) 0.671(4) 0.113(10) Uiso 1 1 d . . . . .
O11A O 0.4699(17) 0.621(3) 0.738(5) 0.058(8) Uani 0.199(6) 1 d . U P A 2
C11A C 0.4963(9) 0.502(2) 0.747(3) 0.042(5) Uani 0.199(6) 1 d . U P A 2
N11A N 0.4605(12) 0.392(2) 0.725(3) 0.060(6) Uani 0.199(6) 1 d D U P A 2
H11C H 0.414(3) 0.413(13) 0.714(16) 0.072 Uiso 0.199(6) 1 d DR U P A 2
H11D H 0.472(6) 0.319(8) 0.787(14) 0.072 Uiso 0.199(6) 1 d DR U P A 2
C12A C 0.5794(8) 0.4876(16) 0.810(2) 0.048(4) Uani 0.199(6) 1 d . U P A 2
H12C H 0.5848 0.4333 0.9139 0.057 Uiso 0.199(6) 1 calc R U P A 2
H12D H 0.6016 0.4358 0.7253 0.057 Uiso 0.199(6) 1 calc R U P A 2
C13A C 0.6207(5) 0.6125(11) 0.8441(19) 0.070(4) Uani 0.199(6) 1 d . U P A 2
H13D H 0.6057 0.6572 0.9421 0.106 Uiso 0.199(6) 1 calc GR U P A 2
H13E H 0.6118 0.6724 0.7470 0.106 Uiso 0.199(6) 1 calc GR U P A 2
H13F H 0.6722 0.5912 0.8659 0.106 Uiso 0.199(6) 1 calc GR U P A 2


_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
F1 C10 1.3351(15) . ?
F2 C10 1.3485(15) . ?
O2 C3 1.3902(15) . ?
O2 C2 1.3654(16) . ?
F3 C10 1.3439(15) . ?
O3 C9 1.2118(17) . ?
C8 H8 0.9500 . ?
C8 C3 1.3870(17) . ?
C8 C7 1.3852(17) . ?
O11 C11 1.250(7) . ?
C3 C4 1.3944(17) . ?
O4 C9 1.3136(17) . ?
O4 H4 0.98(3) . ?
O1 C2 1.1966(17) . ?
C4 C5 1.3978(18) . ?
C4 C9 1.4975(18) . ?
C10 C7 1.4974(17) . ?
C7 C6 1.3897(18) . ?
C2 C1 1.4886(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3854(19) . ?
C6 H6 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C11 N11 1.332(5) . ?
C11 C12 1.487(5) . ?
N11 H11A 0.88(3) . ?
N11 H11B 0.87(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.526(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O11A C11A 1.28(3) . ?
C11A N11A 1.28(2) . ?
C11A C12A 1.58(2) . ?
N11A H11C 0.89(2) . ?
N11A H11D 0.89(2) . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C12A C13A 1.467(19) . ?
C13A H13D 0.9800 . ?
C13A H13E 0.9800 . ?
C13A H13F 0.9800 . ?

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
C2 O2 C3 117.52(10) . . ?
C3 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C7 C8 C3 119.44(11) . . ?
O2 C3 C4 122.61(11) . . ?
C8 C3 O2 116.06(10) . . ?
C8 C3 C4 121.20(11) . . ?
C9 O4 H4 113.9(19) . . ?
C3 C4 C5 118.18(12) . . ?
C3 C4 C9 122.14(11) . . ?
C5 C4 C9 119.66(11) . . ?
F1 C10 F2 106.70(10) . . ?
F1 C10 F3 106.85(10) . . ?
F1 C10 C7 113.08(10) . . ?
F2 C10 C7 111.62(10) . . ?
F3 C10 F2 105.94(10) . . ?
F3 C10 C7 112.20(10) . . ?
C8 C7 C10 119.99(11) . . ?
C8 C7 C6 120.64(11) . . ?
C6 C7 C10 119.37(11) . . ?
O2 C2 C1 110.15(11) . . ?
O1 C2 O2 122.64(12) . . ?
O1 C2 C1 127.20(12) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.24(12) . . ?
C6 C5 H5 119.4 . . ?
C7 C6 H6 120.4 . . ?
C5 C6 C7 119.29(12) . . ?
C5 C6 H6 120.4 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O3 C9 O4 123.10(13) . . ?
O3 C9 C4 124.15(12) . . ?
O4 C9 C4 112.75(11) . . ?
O11 C11 N11 120.4(5) . . ?
O11 C11 C12 121.2(5) . . ?
N11 C11 C12 118.3(4) . . ?
C11 N11 H11A 122(2) . . ?
C11 N11 H11B 122.1(17) . . ?
H11A N11 H11B 116(3) . . ?
C11 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C11 C12 C13 110.4(3) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O11A C11A N11A 126(2) . . ?
O11A C11A C12A 117(2) . . ?
N11A C11A C12A 116.5(16) . . ?
C11A N11A H11C 108(10) . . ?
C11A N11A H11D 122(8) . . ?
H11C N11A H11D 113(4) . . ?
C11A C12A H12C 108.0 . . ?
C11A C12A H12D 108.0 . . ?
H12C C12A H12D 107.2 . . ?
C13A C12A C11A 117.3(13) . . ?
C13A C12A H12C 108.0 . . ?
C13A C12A H12D 108.0 . . ?
C12A C13A H13D 109.5 . . ?
C12A C13A H13E 109.5 . . ?
C12A C13A H13F 109.5 . . ?
H13D C13A H13E 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?

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
N11 H11A O3 0.88(3) 2.07(3) 2.931(5) 165(3) .
N11 H11B O11 0.87(3) 2.15(3) 3.009(8) 170(2) 2_646
O4 H4 O11 0.98(3) 1.62(4) 2.587(8) 170(3) .
O4 H4 O11A 0.98(3) 1.55(5) 2.53(3) 176(3) .
N11A H11C O3 0.89(2) 2.06(5) 2.92(2) 161(11) .
N11A H11D O11A 0.89(2) 2.28(9) 2.99(4) 137(11) 2_646

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
F1 C10 C7 C8 6.98(16) . . . . ?
F1 C10 C7 C6 -172.98(11) . . . . ?
F2 C10 C7 C8 -113.34(13) . . . . ?
F2 C10 C7 C6 66.70(15) . . . . ?
O2 C3 C4 C5 -175.57(11) . . . . ?
O2 C3 C4 C9 3.20(18) . . . . ?
F3 C10 C7 C8 127.93(12) . . . . ?
F3 C10 C7 C6 -52.04(15) . . . . ?
C8 C3 C4 C5 0.33(18) . . . . ?
C8 C3 C4 C9 179.09(11) . . . . ?
C8 C7 C6 C5 0.13(19) . . . . ?
O11 C11 C12 C13 75.0(7) . . . . ?
C3 O2 C2 O1 -2.73(19) . . . . ?
C3 O2 C2 C1 178.05(10) . . . . ?
C3 C8 C7 C10 179.96(11) . . . . ?
C3 C8 C7 C6 -0.08(18) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C3 C4 C9 O3 -7.8(2) . . . . ?
C3 C4 C9 O4 172.47(13) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C10 C7 C6 C5 -179.91(12) . . . . ?
C7 C8 C3 O2 175.99(10) . . . . ?
C7 C8 C3 C4 -0.16(18) . . . . ?
C2 O2 C3 C8 108.92(12) . . . . ?
C2 O2 C3 C4 -74.99(15) . . . . ?
C5 C4 C9 O3 171.00(14) . . . . ?
C5 C4 C9 O4 -8.78(19) . . . . ?
C9 C4 C5 C6 -179.07(13) . . . . ?
N11 C11 C12 C13 -104.0(5) . . . . ?
O11A C11A C12A C13A -4(3) . . . . ?
N11A C11A C12A C13A -177(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1,4-Dioxane'
####################################################################### 
# 
# 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_TRFL-Urea
_database_code_depnum_ccdc_archive 'CCDC 1421384'
_audit_update_record             
;
2015-08-31 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;
_audit_creation_date             2015-07-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        'Triflusal-urea cocrystal'
_chemical_formula_moiety         'C H4 N2 O, 2(C10 H7 F3 O4)'
_chemical_formula_sum            'C21 H18 F6 N2 O9'
_chemical_formula_weight         556.37
_chemical_melting_point          356.4
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.601(3)
_cell_length_b                   10.920(2)
_cell_length_c                   15.342(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.49(3)
_cell_angle_gamma                90
_cell_volume                     2388.2(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3920
_cell_measurement_temperature    110.1500
_cell_measurement_theta_max      30.9639
_cell_measurement_theta_min      2.3495
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.937
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.9495
_exptl_absorpt_correction_T_min  .9371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'R. H. Blessing, Acta Cryst. 1995 A51, 33-38'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.35
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15825
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_min         2.555
_diffrn_ambient_temperature      110.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
scan:
	Number of images: 330
	           Slice: -110.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 270.0000
	             XTD: 45.0093
	          2theta: -20.0682
scan:
	Number of images: 262
	           Slice: -110.0000 - 21.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -70.0000
	             Phi: 270.0000
	             XTD: 45.0093
	          2theta: -20.0682
scan:
	Number of images: 262
	           Slice: -110.0000 - 21.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -70.0000
	             Phi: 90.0000
	             XTD: 45.0093
	          2theta: -20.0682
scan:
	Number of images: 246
	           Slice: -110.0000 - 13.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -70.0000
	             Phi: 0.0000
	             XTD: 45.0093
	          2theta: -20.0682
scan:
	Number of images: 120
	           Slice: -95.0000 - -35.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 45.0093
	          2theta: -20.0682
;
_diffrn_measurement_device       
;
Saturn70 (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             3682
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0583
_diffrn_orient_matrix_UB_12      -0.0359
_diffrn_orient_matrix_UB_13      0.0152
_diffrn_orient_matrix_UB_21      0.0231
_diffrn_orient_matrix_UB_22      -0.0637
_diffrn_orient_matrix_UB_23      -0.0616
_diffrn_orient_matrix_UB_31      0.0203
_diffrn_orient_matrix_UB_32      -0.0403
_diffrn_orient_matrix_UB_33      0.0492
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0000
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2913
_reflns_number_total             2944
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2944
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²+2.0078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1079
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C8(H8)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O11 O 0.0000 0.62178(10) 0.2500 0.0227(2) Uani 1 2 d S T P . .
N11 N 0.05970(7) 0.44407(9) 0.21111(7) 0.0198(2) Uani 1 1 d . . . . .
C11 C 0.0000 0.50581(14) 0.2500 0.0176(3) Uani 1 2 d S T P . .
F3 F 0.14171(6) 0.74390(7) 0.43768(6) 0.0314(2) Uani 1 1 d . . . . .
F2 F 0.16438(6) 0.64215(7) 0.56017(5) 0.0311(2) Uani 1 1 d . . . . .
F1 F 0.03745(5) 0.61597(7) 0.46101(6) 0.0318(2) Uani 1 1 d . . . . .
O2 O 0.15891(6) 0.20218(7) 0.41330(5) 0.01963(18) Uani 1 1 d . . . . .
O3 O 0.31217(6) 0.13231(8) 0.34740(6) 0.0247(2) Uani 1 1 d . . . . .
O1 O 0.10733(6) 0.17886(8) 0.26425(6) 0.0250(2) Uani 1 1 d . . . . .
O4 O 0.38922(7) 0.28132(9) 0.29439(8) 0.0350(3) Uani 1 1 d . . . . .
C6 C 0.25091(8) 0.55942(10) 0.38986(8) 0.0209(2) Uani 1 1 d . . . . .
H6 H 0.2700 0.6417 0.3842 0.025 Uiso 1 1 calc R . . . .
C3 C 0.19161(7) 0.31945(10) 0.40219(7) 0.0168(2) Uani 1 1 d . . . . .
C5 C 0.29651(8) 0.46344(10) 0.35758(8) 0.0204(2) Uani 1 1 d . . . . .
H5 H 0.3477 0.4809 0.3304 0.024 Uiso 1 1 calc R . . . .
C2 C 0.12157(8) 0.13631(10) 0.33824(8) 0.0207(2) Uani 1 1 d . . . . .
C8 C 0.14649(7) 0.41367(10) 0.43635(7) 0.0176(2) Uani 1 1 d . . . . .
H8 H 0.0952 0.3967 0.4635 0.021 Uiso 1 1 calc R . . . .
C4 C 0.26886(7) 0.34179(10) 0.36414(7) 0.0177(2) Uani 1 1 d . . . . .
C7 C 0.17694(7) 0.53336(10) 0.43055(7) 0.0183(2) Uani 1 1 d . . . . .
C9 C 0.32423(8) 0.24040(10) 0.33442(7) 0.0193(2) Uani 1 1 d . . . . .
C10 C 0.12992(8) 0.63384(10) 0.47157(8) 0.0214(2) Uani 1 1 d . . . . .
C1 C 0.10159(10) 0.00835(11) 0.36284(9) 0.0311(3) Uani 1 1 d . . . . .
H1A H 0.0555 -0.0288 0.3140 0.047 Uiso 1 1 calc GR . . . .
H1B H 0.0764 0.0094 0.4171 0.047 Uiso 1 1 calc GR . . . .
H1C H 0.1597 -0.0396 0.3736 0.047 Uiso 1 1 calc GR . . . .
H11A H 0.1002(12) 0.4872(16) 0.1903(11) 0.030(4) Uiso 1 1 d . . . . .
H11B H 0.0674(12) 0.3667(16) 0.2197(11) 0.029(4) Uiso 1 1 d . . . . .
H4 H 0.4257(16) 0.221(2) 0.2805(15) 0.060(6) 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
O11 C11 1.2664(19) . ?
N11 C11 1.3399(12) . ?
N11 H11A 0.869(18) . ?
N11 H11B 0.859(18) . ?
C11 N11 1.3399(12) 2 ?
F3 C10 1.3353(13) . ?
F2 C10 1.3466(14) . ?
F1 C10 1.3388(14) . ?
O2 C3 1.3901(13) . ?
O2 C2 1.3672(14) . ?
O3 C9 1.2162(14) . ?
O1 C2 1.2024(15) . ?
O4 C9 1.3151(14) . ?
O4 H4 0.90(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.3891(15) . ?
C6 C7 1.3887(15) . ?
C3 C8 1.3844(15) . ?
C3 C4 1.3989(15) . ?
C5 H5 0.9500 . ?
C5 C4 1.3984(15) . ?
C2 C1 1.4925(16) . ?
C8 H8 0.9500 . ?
C8 C7 1.3896(15) . ?
C4 C9 1.4989(15) . ?
C7 C10 1.5027(15) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

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
C11 N11 H11A 116.8(11) . . ?
C11 N11 H11B 120.2(12) . . ?
H11A N11 H11B 120.8(16) . . ?
O11 C11 N11 120.21(7) . 2 ?
O11 C11 N11 120.21(7) . . ?
N11 C11 N11 119.58(15) 2 . ?
C2 O2 C3 117.80(9) . . ?
C9 O4 H4 112.7(15) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C7 C6 C5 119.01(10) . . ?
O2 C3 C4 122.76(10) . . ?
C8 C3 O2 115.72(9) . . ?
C8 C3 C4 121.40(10) . . ?
C6 C5 H5 119.2 . . ?
C6 C5 C4 121.53(10) . . ?
C4 C5 H5 119.2 . . ?
O2 C2 C1 110.10(10) . . ?
O1 C2 O2 123.22(10) . . ?
O1 C2 C1 126.67(11) . . ?
C3 C8 H8 120.3 . . ?
C3 C8 C7 119.32(10) . . ?
C7 C8 H8 120.3 . . ?
C3 C4 C9 122.32(10) . . ?
C5 C4 C3 117.85(10) . . ?
C5 C4 C9 119.78(10) . . ?
C6 C7 C8 120.81(10) . . ?
C6 C7 C10 120.58(10) . . ?
C8 C7 C10 118.59(10) . . ?
O3 C9 O4 123.43(10) . . ?
O3 C9 C4 124.08(10) . . ?
O4 C9 C4 112.47(10) . . ?
F3 C10 F2 106.31(9) . . ?
F3 C10 F1 107.19(10) . . ?
F3 C10 C7 112.65(10) . . ?
F2 C10 C7 111.54(10) . . ?
F1 C10 F2 106.19(10) . . ?
F1 C10 C7 112.52(9) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

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
N11 H11A O3 0.869(18) 2.192(18) 3.0426(14) 166.3(16) 4
N11 H11B O1 0.859(18) 2.200(18) 3.0480(14) 169.1(15) .
O4 H4 O11 0.90(2) 1.67(2) 2.5673(12) 174(2) 3_545

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 C3 C8 C7 177.94(9) . . . . ?
O2 C3 C4 C5 -178.99(9) . . . . ?
O2 C3 C4 C9 -1.65(16) . . . . ?
C6 C5 C4 C3 1.77(17) . . . . ?
C6 C5 C4 C9 -175.64(10) . . . . ?
C6 C7 C10 F3 22.58(15) . . . . ?
C6 C7 C10 F2 -96.89(13) . . . . ?
C6 C7 C10 F1 143.89(11) . . . . ?
C3 O2 C2 O1 -7.57(16) . . . . ?
C3 O2 C2 C1 172.90(9) . . . . ?
C3 C8 C7 C6 0.95(16) . . . . ?
C3 C8 C7 C10 -177.33(10) . . . . ?
C3 C4 C9 O3 -6.43(18) . . . . ?
C3 C4 C9 O4 175.12(11) . . . . ?
C5 C6 C7 C8 -2.23(17) . . . . ?
C5 C6 C7 C10 176.02(10) . . . . ?
C5 C4 C9 O3 170.86(11) . . . . ?
C5 C4 C9 O4 -7.60(15) . . . . ?
C2 O2 C3 C8 117.80(11) . . . . ?
C2 O2 C3 C4 -66.09(14) . . . . ?
C8 C3 C4 C5 -3.09(16) . . . . ?
C8 C3 C4 C9 174.25(10) . . . . ?
C8 C7 C10 F3 -159.13(10) . . . . ?
C8 C7 C10 F2 81.40(13) . . . . ?
C8 C7 C10 F1 -37.81(15) . . . . ?
C4 C3 C8 C7 1.77(16) . . . . ?
C7 C6 C5 C4 0.83(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Tetrahydrofuran'
####################################################################### 
# 
# 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_TRFL-VA
_database_code_depnum_ccdc_archive 'CCDC 1421385'
_audit_update_record             
;
2015-08-31 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;
_audit_creation_date             2015-07-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        'Triflusal-valpromide cocrystal'
_chemical_formula_moiety         'C10 H7 F3 O4, C8 H17 N O'
_chemical_formula_sum            'C18 H24 F3 N O5'
_chemical_formula_weight         391.38
_chemical_melting_point          346.7
_chemical_oxdiff_formula         'c18 h24 f3 n o5'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   19.8545(8)
_cell_length_b                   5.06409(17)
_cell_length_c                   21.8530(11)
_cell_angle_alpha                90
_cell_angle_beta                 114.362(6)
_cell_angle_gamma                90
_cell_volume                     2001.57(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12537
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.1150
_cell_measurement_theta_min      3.6210
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            35996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_min         2.712
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2945
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   46.00  105.00   1.0000   17.8500
omega____ theta____ kappa____ phi______ frames
    -       21.1986  165.0000  -41.0000 59

#__ type_ start__ end____ width___ exp.time_
  2 omega   24.00  105.00   1.0000   17.8500
omega____ theta____ kappa____ phi______ frames
    -       21.1986 -165.0000  -63.0000 81

#__ type_ start__ end____ width___ exp.time_
  3 omega   -6.00   57.00   1.0000   17.8500
omega____ theta____ kappa____ phi______ frames
    -       21.1986 -116.0000   83.0000 63

#__ type_ start__ end____ width___ exp.time_
  4 omega  -75.00  -18.00   1.0000   17.8500
omega____ theta____ kappa____ phi______ frames
    -      -22.1361  116.0000  171.0000 57

#__ type_ start__ end____ width___ exp.time_
  5 omega -100.00  -74.00   1.0000   17.8500
omega____ theta____ kappa____ phi______ frames
    -      -22.1361  165.0000  -41.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega  -51.00   50.00   1.0000   17.8500
omega____ theta____ kappa____ phi______ frames
    -       21.1986  -38.0000  150.0000 101

#__ type_ start__ end____ width___ exp.time_
  7 omega   -7.00   87.00   1.0000   17.8500
omega____ theta____ kappa____ phi______ frames
    -       21.1986   77.0000   90.0000 94

#__ type_ start__ end____ width___ exp.time_
  8 omega  -58.00    1.00   1.0000   17.8500
omega____ theta____ kappa____ phi______ frames
    -       21.1986  -77.0000  -60.0000 59

#__ type_ start__ end____ width___ exp.time_
  9 omega   -1.00  100.00   1.0000   17.8500
omega____ theta____ kappa____ phi______ frames
    -       21.1986   77.0000  -30.0000 101

#__ type_ start__ end____ width___ exp.time_
 10 omega -112.00  -81.00   1.0000   17.8500
omega____ theta____ kappa____ phi______ frames
    -      -22.1361 -178.0000   60.0000 31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0188416000
_diffrn_orient_matrix_UB_12      0.0016422000
_diffrn_orient_matrix_UB_13      -0.0214021000
_diffrn_orient_matrix_UB_21      0.0338464000
_diffrn_orient_matrix_UB_22      -0.0256135000
_diffrn_orient_matrix_UB_23      0.0279763000
_diffrn_orient_matrix_UB_31      -0.0061166000
_diffrn_orient_matrix_UB_32      -0.1376528000
_diffrn_orient_matrix_UB_33      -0.0054665000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5109
_reflns_number_total             6106
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         6106
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0424P)²+1.1125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1167
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 F1, F1A, F3, F3A, C10, F2A, F2, C7, C8, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(F3A)=Sof(F1A)=Sof(F2A)=1-FVAR(1)
 Sof(F1)=Sof(F3)=Sof(F2)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C22(H22)
4.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C26(H26A,H26B), C27(H27A,H27B), C24(H24A,H24B)
4.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C6(H6)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C28(H28A,H28B,H28C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O2 O -0.04528(4) 0.72225(16) 0.32733(4) 0.01715(16) Uani 1 1 d . . . . .
O4 O -0.14040(5) 1.06937(18) 0.33810(5) 0.0245(2) Uani 1 1 d . . . . .
O3 O -0.10001(5) 1.38489(17) 0.41604(4) 0.02152(18) Uani 1 1 d . . . . .
O21 O 0.27597(4) 0.71305(16) 0.18927(4) 0.02090(18) Uani 1 1 d . . . . .
C4 C -0.01106(6) 1.0920(2) 0.40661(5) 0.0152(2) Uani 1 1 d . . . . .
O1 O -0.05334(5) 1.02277(18) 0.24831(4) 0.02413(19) Uani 1 1 d . . . . .
C22 C 0.37635(6) 1.0254(2) 0.22639(6) 0.0188(2) Uani 1 1 d . . . . .
H22 H 0.3799 1.2224 0.2282 0.023 Uiso 1 1 calc R . . . .
C9 C -0.08782(6) 1.1969(2) 0.38756(5) 0.0158(2) Uani 1 1 d . . . . .
N21 N 0.24699(6) 1.1403(2) 0.16257(6) 0.0220(2) Uani 1 1 d . . . . .
C3 C 0.00758(6) 0.8761(2) 0.37654(5) 0.0156(2) Uani 1 1 d . . . . .
C5 C 0.04585(6) 1.2228(2) 0.45891(6) 0.0184(2) Uani 1 1 d . . . . .
H5 H 0.0342 1.3692 0.4799 0.022 Uiso 1 1 calc R . . . .
C8 C 0.08069(6) 0.7953(2) 0.39766(6) 0.0183(2) Uani 1 1 d . U . . .
H8 H 0.0928 0.6496 0.3767 0.022 Uiso 1 1 calc R . . . .
C7 C 0.13582(6) 0.9297(2) 0.44967(6) 0.0193(2) Uani 1 1 d . U . . .
C6 C 0.11886(6) 1.1436(2) 0.48071(6) 0.0205(2) Uani 1 1 d . U . . .
H6 H 0.1569 1.2342 0.5164 0.025 Uiso 1 1 calc R . . . .
C23 C 0.40806(6) 0.9196(3) 0.29838(6) 0.0235(2) Uani 1 1 d . . . . .
H23A H 0.4036 0.7247 0.2969 0.028 Uiso 1 1 calc R . . . .
H23B H 0.4614 0.9635 0.3202 0.028 Uiso 1 1 calc R . . . .
C21 C 0.29528(6) 0.9491(2) 0.19090(6) 0.0168(2) Uani 1 1 d . . . . .
C2 C -0.07460(6) 0.8217(2) 0.26332(6) 0.0181(2) Uani 1 1 d . . . . .
C26 C 0.41790(6) 0.9219(2) 0.18544(6) 0.0222(2) Uani 1 1 d . . . . .
H26A H 0.4717 0.9442 0.2123 0.027 Uiso 1 1 calc R . . . .
H26B H 0.4080 0.7305 0.1775 0.027 Uiso 1 1 calc R . . . .
C1 C -0.13502(7) 0.6454(3) 0.21844(6) 0.0259(3) Uani 1 1 d . . . . .
H1A H -0.1164 0.4642 0.2221 0.039 Uiso 1 1 calc GR . . . .
H1B H -0.1519 0.7060 0.1719 0.039 Uiso 1 1 calc GR . . . .
H1C H -0.1764 0.6503 0.2319 0.039 Uiso 1 1 calc GR . . . .
C10 C 0.21515(7) 0.8488(3) 0.47252(7) 0.0269(3) Uani 1 1 d . U . . .
C27 C 0.39674(7) 1.0594(3) 0.11802(7) 0.0269(3) Uani 1 1 d . . . . .
H27A H 0.3424 1.0513 0.0926 0.032 Uiso 1 1 calc R . . . .
H27B H 0.4110 1.2478 0.1260 0.032 Uiso 1 1 calc R . . . .
F1 F 0.22548(17) 0.6135(5) 0.4562(3) 0.0633(13) Uani 0.644(10) 1 d . U P A 1
C24 C 0.37014(7) 1.0291(3) 0.34124(7) 0.0312(3) Uani 1 1 d . . . . .
H24A H 0.3731 1.2243 0.3417 0.037 Uiso 1 1 calc R . . . .
H24B H 0.3172 0.9796 0.3205 0.037 Uiso 1 1 calc R . . . .
F3 F 0.2520(2) 1.0143(10) 0.4503(2) 0.0698(13) Uani 0.644(10) 1 d . U P A 1
C28 C 0.43335(9) 0.9368(4) 0.07587(8) 0.0390(3) Uani 1 1 d . . . . .
H28A H 0.4186 1.0344 0.0336 0.058 Uiso 1 1 calc GR . . . .
H28B H 0.4178 0.7521 0.0662 0.058 Uiso 1 1 calc GR . . . .
H28C H 0.4872 0.9449 0.1006 0.058 Uiso 1 1 calc GR . . . .
C25 C 0.40440(9) 0.9282(4) 0.41314(8) 0.0454(4) Uani 1 1 d . . . . .
H25A H 0.3979 0.7364 0.4133 0.068 Uiso 1 1 calc GR . . . .
H25B H 0.3801 1.0125 0.4390 0.068 Uiso 1 1 calc GR . . . .
H25C H 0.4573 0.9707 0.4334 0.068 Uiso 1 1 calc GR . . . .
F2 F 0.25312(17) 0.8686(11) 0.54004(11) 0.0616(12) Uani 0.644(10) 1 d . U P A 1
H21A H 0.1992(9) 1.102(3) 0.1390(8) 0.025(4) Uiso 1 1 d . . . . .
H21B H 0.2615(9) 1.308(4) 0.1679(8) 0.030(4) Uiso 1 1 d . . . . .
H4 H -0.1843(11) 1.141(4) 0.3312(10) 0.048(5) Uiso 1 1 d . . . . .
F3A F 0.2595(4) 1.0325(12) 0.4797(6) 0.075(3) Uani 0.356(10) 1 d . U P A 2
F1A F 0.2245(4) 0.686(2) 0.4275(4) 0.077(2) Uani 0.356(10) 1 d . U P A 2
F2A F 0.2362(3) 0.708(2) 0.5269(4) 0.075(3) Uani 0.356(10) 1 d . U P A 2


_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
O2 C3 1.3906(13) . ?
O2 C2 1.3702(14) . ?
O4 C9 1.3207(14) . ?
O4 H4 0.90(2) . ?
O3 C9 1.2154(14) . ?
O21 C21 1.2512(14) . ?
C4 C9 1.5014(15) . ?
C4 C3 1.4017(15) . ?
C4 C5 1.3987(15) . ?
O1 C2 1.1987(15) . ?
C22 H22 1.0000 . ?
C22 C23 1.5302(17) . ?
C22 C21 1.5205(15) . ?
C22 C26 1.5379(16) . ?
N21 C21 1.3229(15) . ?
N21 H21A 0.894(16) . ?
N21 H21B 0.890(18) . ?
C3 C8 1.3910(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.3854(16) . ?
C8 H8 0.9500 . ?
C8 C7 1.3880(17) . ?
C7 C6 1.3913(17) . ?
C7 C10 1.4998(16) . ?
C6 H6 0.9500 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.5277(18) . ?
C2 C1 1.4922(17) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.5237(18) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C10 F1 1.284(3) . ?
C10 F3 1.328(3) . ?
C10 F2 1.356(2) . ?
C10 F3A 1.245(6) . ?
C10 F1A 1.355(6) . ?
C10 F2A 1.297(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.521(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.520(2) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

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
C2 O2 C3 116.81(9) . . ?
C9 O4 H4 109.0(13) . . ?
C3 C4 C9 125.44(10) . . ?
C5 C4 C9 116.39(10) . . ?
C5 C4 C3 118.17(10) . . ?
C23 C22 H22 108.5 . . ?
C23 C22 C26 112.76(10) . . ?
C21 C22 H22 108.5 . . ?
C21 C22 C23 109.60(9) . . ?
C21 C22 C26 109.00(9) . . ?
C26 C22 H22 108.5 . . ?
O4 C9 C4 115.05(9) . . ?
O3 C9 O4 123.02(10) . . ?
O3 C9 C4 121.93(10) . . ?
C21 N21 H21A 120.1(11) . . ?
C21 N21 H21B 120.3(11) . . ?
H21A N21 H21B 119.5(15) . . ?
O2 C3 C4 122.59(9) . . ?
O2 C3 C8 116.30(10) . . ?
C8 C3 C4 121.00(10) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.46(11) . . ?
C6 C5 H5 119.3 . . ?
C3 C8 H8 120.3 . . ?
C7 C8 C3 119.34(10) . . ?
C7 C8 H8 120.3 . . ?
C8 C7 C6 120.89(10) . . ?
C8 C7 C10 120.26(11) . . ?
C6 C7 C10 118.85(11) . . ?
C5 C6 C7 119.14(11) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C22 C23 H23A 108.8 . . ?
C22 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C24 C23 C22 113.91(10) . . ?
C24 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
O21 C21 C22 120.32(10) . . ?
O21 C21 N21 122.10(10) . . ?
N21 C21 C22 117.58(10) . . ?
O2 C2 C1 109.81(10) . . ?
O1 C2 O2 122.84(11) . . ?
O1 C2 C1 127.35(11) . . ?
C22 C26 H26A 108.8 . . ?
C22 C26 H26B 108.8 . . ?
H26A C26 H26B 107.6 . . ?
C27 C26 C22 114.00(10) . . ?
C27 C26 H26A 108.8 . . ?
C27 C26 H26B 108.8 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
F1 C10 C7 115.28(18) . . ?
F1 C10 F3 108.0(3) . . ?
F1 C10 F2 106.9(2) . . ?
F3 C10 C7 111.5(2) . . ?
F3 C10 F2 102.0(2) . . ?
F2 C10 C7 112.24(14) . . ?
F3A C10 C7 115.4(3) . . ?
F3A C10 F1A 104.1(5) . . ?
F3A C10 F2A 110.6(4) . . ?
F1A C10 C7 111.4(3) . . ?
F2A C10 C7 110.6(2) . . ?
F2A C10 F1A 104.0(4) . . ?
C26 C27 H27A 109.0 . . ?
C26 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
C28 C27 C26 112.89(12) . . ?
C28 C27 H27A 109.0 . . ?
C28 C27 H27B 109.0 . . ?
C23 C24 H24A 109.0 . . ?
C23 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C25 C24 C23 112.83(12) . . ?
C25 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
N21 H21A O3 0.894(16) 2.140(17) 3.0006(13) 161.3(15) 2_545
N21 H21B O21 0.890(18) 2.097(18) 2.9679(13) 166.1(15) 1_565
O4 H4 O21 0.90(2) 1.72(2) 2.6084(12) 168(2) 2

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 C3 C8 C7 -175.88(10) . . . . ?
C4 C3 C8 C7 0.53(17) . . . . ?
C4 C5 C6 C7 0.21(18) . . . . ?
C22 C23 C24 C25 -178.02(13) . . . . ?
C22 C26 C27 C28 -174.78(11) . . . . ?
C9 C4 C3 O2 -4.23(17) . . . . ?
C9 C4 C3 C8 179.58(10) . . . . ?
C9 C4 C5 C6 -179.94(10) . . . . ?
C3 O2 C2 O1 4.68(15) . . . . ?
C3 O2 C2 C1 -174.68(9) . . . . ?
C3 C4 C9 O4 -0.09(16) . . . . ?
C3 C4 C9 O3 179.71(11) . . . . ?
C3 C4 C5 C6 0.20(17) . . . . ?
C3 C8 C7 C6 -0.10(17) . . . . ?
C3 C8 C7 C10 -179.03(11) . . . . ?
C5 C4 C9 O4 -179.93(10) . . . . ?
C5 C4 C9 O3 -0.13(16) . . . . ?
C5 C4 C3 O2 175.61(10) . . . . ?
C5 C4 C3 C8 -0.58(16) . . . . ?
C8 C7 C6 C5 -0.26(18) . . . . ?
C8 C7 C10 F1 -19.7(4) . . . . ?
C8 C7 C10 F3 103.9(3) . . . . ?
C8 C7 C10 F2 -142.4(3) . . . . ?
C8 C7 C10 F3A 132.9(7) . . . . ?
C8 C7 C10 F1A 14.5(6) . . . . ?
C8 C7 C10 F2A -100.7(7) . . . . ?
C6 C7 C10 F1 161.3(3) . . . . ?
C6 C7 C10 F3 -75.1(3) . . . . ?
C6 C7 C10 F2 38.7(3) . . . . ?
C6 C7 C10 F3A -46.1(7) . . . . ?
C6 C7 C10 F1A -164.5(6) . . . . ?
C6 C7 C10 F2A 80.4(7) . . . . ?
C23 C22 C21 O21 -53.54(14) . . . . ?
C23 C22 C21 N21 126.23(12) . . . . ?
C23 C22 C26 C27 -169.87(10) . . . . ?
C21 C22 C23 C24 -61.06(14) . . . . ?
C21 C22 C26 C27 68.18(13) . . . . ?
C2 O2 C3 C4 79.71(13) . . . . ?
C2 O2 C3 C8 -103.93(11) . . . . ?
C26 C22 C23 C24 177.32(11) . . . . ?
C26 C22 C21 O21 70.31(14) . . . . ?
C26 C22 C21 N21 -109.92(12) . . . . ?
C10 C7 C6 C5 178.68(11) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
13 0 -31 0.1524 13.0585 -0.0016 -30.9360 0.9081 -0.4234 0.0895
-13 0 31 0.1813 -13.0585 0.0016 30.9360 -0.9081 0.4234 -0.0895
-4 -7 1 0.2910 -3.9863 -6.9946 1.0214 -0.1085 0.0728 0.9816
-25 1 -2 0.0628 -24.9313 1.0027 -2.1041 -0.4231 -0.9284 0.0260
25 0 2 0.1420 24.9304 -0.0034 2.0987 0.4248 0.9026 -0.1635
2 7 3 0.3231 1.9796 6.9948 2.9690 -0.0148 -0.0291 -0.9912
0 -7 -3 0.3015 0.0153 -6.9951 -2.9611 0.0522 0.0968 0.9790
24 2 2 0.1285 23.9311 1.9953 2.0840 0.4096 0.8172 -0.4324

_olex2_exptl_crystal_mounting_method 'MiTeGen Micromesh'
_olex2_submission_special_instructions 'No special instructions were received'

#====END_exptl_crystal_recrystallization_method 
