# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_k08017
_database_code_depnum_ccdc_archive 'CCDC 1957482'
loop_
_audit_author_name
_audit_author_address
'Sean Parkin'
;University of Kentucky
United States of America
;
_audit_update_record             
;
2019-10-04 deposited with the CCDC.	2019-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H11 F3 N2 O2'
_chemical_formula_sum            'C14 H11 F3 N2 O2'
_chemical_formula_weight         296.25

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5380(1)
_cell_length_b                   14.0607(2)
_cell_length_c                   12.3766(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.3203(5)
_cell_angle_gamma                90.00
_cell_volume                     1276.50(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    23071
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9362
_exptl_absorpt_correction_T_max  0.9610
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 18
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20862
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.98
_reflns_number_total             2464
_reflns_number_gt                2157
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_cell_refinement       'DENZO-SMN (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Nonius, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Bruker, 1995)'
_computing_publication_material  'SHELX-97 and local procedures'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0503P)²+0.5741P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2464
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0971
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.97559(15) 0.56836(8) 0.29346(9) 0.0162(3) Uani 1 1 d . . .
C2 C 0.95689(17) 0.48377(10) 0.24073(11) 0.0146(3) Uani 1 1 d . . .
C3 C 1.06011(18) 0.40307(9) 0.28704(11) 0.0156(3) Uani 1 1 d . . .
C4 C 1.18239(19) 0.41403(10) 0.38733(12) 0.0189(3) Uani 1 1 d . . .
H4 H 1.2536 0.3614 0.4205 0.023 Uiso 1 1 calc R . .
F1 F 0.17316(11) 0.63730(7) 0.11754(7) 0.0311(3) Uani 1 1 d . . .
F2 F 0.25542(13) 0.78056(7) 0.09206(7) 0.0296(3) Uani 1 1 d . . .
F3 F 0.36452(13) 0.70994(7) 0.24534(7) 0.0315(3) Uani 1 1 d . . .
C5 C 1.2022(2) 0.50139(10) 0.44019(12) 0.0216(3) Uani 1 1 d . . .
H5 H 1.2875 0.5098 0.5091 0.026 Uiso 1 1 calc R . .
C6 C 1.09557(19) 0.57560(10) 0.39048(11) 0.0190(3) Uani 1 1 d . . .
H6 H 1.1081 0.6353 0.4274 0.023 Uiso 1 1 calc R . .
N7 N 0.83715(15) 0.47777(8) 0.14202(9) 0.0171(3) Uani 1 1 d . . .
H7 H 0.8311 0.4237 0.1055 0.021 Uiso 1 1 calc R . .
C8 C 0.71966(18) 0.55264(9) 0.09261(11) 0.0153(3) Uani 1 1 d . . .
C9 C 0.57609(18) 0.58243(9) 0.14004(11) 0.0153(3) Uani 1 1 d . . .
C10 C 0.46967(18) 0.65811(10) 0.08754(11) 0.0160(3) Uani 1 1 d . . .
C11 C 0.49845(19) 0.69803(10) -0.01011(11) 0.0174(3) Uani 1 1 d . . .
H11 H 0.4228 0.7486 -0.0449 0.021 Uiso 1 1 calc R . .
C12 C 0.63729(19) 0.66434(10) -0.05701(11) 0.0197(3) Uani 1 1 d . . .
H12 H 0.6549 0.6907 -0.1244 0.024 Uiso 1 1 calc R . .
C13 C 0.74898(18) 0.59240(10) -0.00487(11) 0.0187(3) Uani 1 1 d . . .
H13 H 0.8459 0.5699 -0.0354 0.022 Uiso 1 1 calc R . .
C14 C 0.54119(19) 0.53447(11) 0.24249(12) 0.0217(3) Uani 1 1 d . . .
H14A H 0.5920 0.4700 0.2483 0.033 Uiso 1 1 calc R . .
H14B H 0.4096 0.5312 0.2371 0.033 Uiso 1 1 calc R . .
H14C H 0.5994 0.5711 0.3085 0.033 Uiso 1 1 calc R . .
C15 C 0.3169(2) 0.69619(11) 0.13504(11) 0.0212(3) Uani 1 1 d . . .
C16 C 1.03569(18) 0.30925(9) 0.23087(11) 0.0154(3) Uani 1 1 d . . .
O17 O 1.13267(13) 0.24100(7) 0.28811(8) 0.0209(3) Uani 1 1 d . . .
H17 H 1.0997 0.1884 0.2579 0.031 Uiso 1 1 calc R . .
O18 O 0.93574(13) 0.29659(7) 0.14008(8) 0.0196(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0178(6) 0.0137(6) 0.0160(6) 0.0002(4) 0.0013(5) -0.0012(4)
C2 0.0139(6) 0.0151(7) 0.0143(6) 0.0009(5) 0.0022(5) -0.0025(5)
C3 0.0153(6) 0.0139(7) 0.0167(6) 0.0020(5) 0.0020(5) -0.0020(5)
C4 0.0199(7) 0.0160(7) 0.0187(7) 0.0033(5) 0.0001(5) -0.0003(5)
F1 0.0183(4) 0.0430(6) 0.0327(5) 0.0017(4) 0.0074(4) 0.0000(4)
F2 0.0330(5) 0.0295(5) 0.0256(5) 0.0023(4) 0.0051(4) 0.0167(4)
F3 0.0352(5) 0.0432(6) 0.0148(4) -0.0032(4) 0.0032(4) 0.0146(4)
C5 0.0248(7) 0.0197(7) 0.0165(7) 0.0010(5) -0.0032(6) -0.0026(6)
C6 0.0229(7) 0.0160(7) 0.0166(7) -0.0012(5) 0.0012(6) -0.0031(6)
N7 0.0189(6) 0.0127(6) 0.0167(6) -0.0021(4) -0.0023(5) 0.0019(5)
C8 0.0158(6) 0.0118(7) 0.0157(7) -0.0014(5) -0.0022(5) -0.0020(5)
C9 0.0165(6) 0.0134(7) 0.0137(6) -0.0013(5) -0.0014(5) -0.0037(5)
C10 0.0154(6) 0.0162(7) 0.0141(6) -0.0020(5) -0.0014(5) -0.0019(5)
C11 0.0167(6) 0.0148(7) 0.0174(7) 0.0016(5) -0.0028(5) 0.0006(5)
C12 0.0204(7) 0.0225(8) 0.0158(7) 0.0043(5) 0.0031(5) -0.0001(6)
C13 0.0161(7) 0.0214(7) 0.0179(7) -0.0017(5) 0.0022(5) 0.0014(6)
C14 0.0221(7) 0.0243(8) 0.0183(7) 0.0058(6) 0.0036(6) 0.0007(6)
C15 0.0218(7) 0.0254(8) 0.0144(7) 0.0008(5) 0.0004(6) 0.0053(6)
C16 0.0140(6) 0.0149(7) 0.0174(7) 0.0032(5) 0.0037(5) -0.0005(5)
O17 0.0231(5) 0.0112(5) 0.0237(5) 0.0010(4) -0.0042(4) 0.0011(4)
O18 0.0226(5) 0.0149(5) 0.0182(5) -0.0012(4) -0.0017(4) 0.0012(4)

_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
N1 C6 1.3303(18) . ?
N1 C2 1.3485(18) . ?
C2 N7 1.3439(17) . ?
C2 C3 1.4198(18) . ?
C3 C4 1.3737(19) . ?
C3 C16 1.4827(19) . ?
C4 C5 1.383(2) . ?
C4 H4 0.9500 . ?
F1 C15 1.3409(18) . ?
F2 C15 1.3384(17) . ?
F3 C15 1.3431(16) . ?
C5 C6 1.373(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N7 C8 1.4203(17) . ?
N7 H7 0.8800 . ?
C8 C13 1.3928(19) . ?
C8 C9 1.4085(19) . ?
C9 C10 1.3993(19) . ?
C9 C14 1.5118(19) . ?
C10 C11 1.394(2) . ?
C10 C15 1.507(2) . ?
C11 C12 1.392(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 O18 1.2132(16) . ?
C16 O17 1.3109(16) . ?
O17 H17 0.8400 . ?

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
C6 N1 C2 118.55(12) . . ?
N7 C2 N1 117.95(12) . . ?
N7 C2 C3 120.51(12) . . ?
N1 C2 C3 121.54(12) . . ?
C4 C3 C2 117.80(12) . . ?
C4 C3 C16 120.56(12) . . ?
C2 C3 C16 121.63(12) . . ?
C3 C4 C5 120.25(13) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 118.33(13) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
N1 C6 C5 123.52(13) . . ?
N1 C6 H6 118.2 . . ?
C5 C6 H6 118.2 . . ?
C2 N7 C8 124.51(11) . . ?
C2 N7 H7 117.7 . . ?
C8 N7 H7 117.7 . . ?
C13 C8 C9 122.15(12) . . ?
C13 C8 N7 117.57(12) . . ?
C9 C8 N7 120.25(12) . . ?
C10 C9 C8 116.49(12) . . ?
C10 C9 C14 122.46(12) . . ?
C8 C9 C14 121.05(12) . . ?
C11 C10 C9 121.44(13) . . ?
C11 C10 C15 118.73(12) . . ?
C9 C10 C15 119.80(12) . . ?
C12 C11 C10 120.45(13) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 119.45(13) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C8 119.91(13) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
F2 C15 F1 106.88(11) . . ?
F2 C15 F3 105.28(11) . . ?
F1 C15 F3 105.66(12) . . ?
F2 C15 C10 112.67(12) . . ?
F1 C15 C10 112.29(12) . . ?
F3 C15 C10 113.46(11) . . ?
O18 C16 O17 122.89(12) . . ?
O18 C16 C3 123.25(12) . . ?
O17 C16 C3 113.85(11) . . ?
C16 O17 H17 109.5 . . ?

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
C6 N1 C2 N7 -179.05(12) . . . . ?
C6 N1 C2 C3 0.77(19) . . . . ?
N7 C2 C3 C4 178.99(12) . . . . ?
N1 C2 C3 C4 -0.83(19) . . . . ?
N7 C2 C3 C16 -2.10(19) . . . . ?
N1 C2 C3 C16 178.09(12) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C16 C3 C4 C5 -178.89(13) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C2 N1 C6 C5 0.1(2) . . . . ?
C4 C5 C6 N1 -0.8(2) . . . . ?
N1 C2 N7 C8 -4.5(2) . . . . ?
C3 C2 N7 C8 175.70(12) . . . . ?
C2 N7 C8 C13 113.62(15) . . . . ?
C2 N7 C8 C9 -68.30(17) . . . . ?
C13 C8 C9 C10 -3.48(19) . . . . ?
N7 C8 C9 C10 178.53(11) . . . . ?
C13 C8 C9 C14 176.69(12) . . . . ?
N7 C8 C9 C14 -1.30(19) . . . . ?
C8 C9 C10 C11 3.53(19) . . . . ?
C14 C9 C10 C11 -176.65(13) . . . . ?
C8 C9 C10 C15 -178.18(12) . . . . ?
C14 C9 C10 C15 1.65(19) . . . . ?
C9 C10 C11 C12 -1.2(2) . . . . ?
C15 C10 C11 C12 -179.52(13) . . . . ?
C10 C11 C12 C13 -1.4(2) . . . . ?
C11 C12 C13 C8 1.4(2) . . . . ?
C9 C8 C13 C12 1.1(2) . . . . ?
N7 C8 C13 C12 179.10(12) . . . . ?
C11 C10 C15 F2 -15.93(18) . . . . ?
C9 C10 C15 F2 165.73(11) . . . . ?
C11 C10 C15 F1 104.82(14) . . . . ?
C9 C10 C15 F1 -73.52(15) . . . . ?
C11 C10 C15 F3 -135.45(13) . . . . ?
C9 C10 C15 F3 46.21(18) . . . . ?
C4 C3 C16 O18 -176.61(13) . . . . ?
C2 C3 C16 O18 4.5(2) . . . . ?
C4 C3 C16 O17 3.13(18) . . . . ?
C2 C3 C16 O17 -175.76(11) . . . . ?

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
O17 H17 N1 0.84 1.85 2.6829(15) 173.8 2_745
N7 H7 O18 0.88 1.96 2.6554(15) 134.8 .

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.98
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_flunixin
_database_code_depnum_ccdc_archive 'CCDC 1957486'
loop_
_audit_author_name
_audit_author_address
'Sean Parkin'
;University of Kentucky
United States of America
;
_audit_update_record             
;
2019-10-04 deposited with the CCDC.	2019-11-22 downloaded from the CCDC.
;
_audit_creation_date             2018-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H11 F3 N2 O2'
_chemical_formula_sum            'C14 H11 F3 N2 O2'
_chemical_formula_weight         296.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 N1 O1 F1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.68546(13)
_cell_length_b                   14.1282(2)
_cell_length_c                   12.49862(17)
_cell_angle_alpha                90
_cell_angle_beta                 102.1605(15)
_cell_angle_gamma                90
_cell_volume                     1326.67(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6019
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.4980
_cell_measurement_theta_min      4.7710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11795
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.494
_diffrn_reflns_theta_min         4.785
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4674
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -130.00 -57.00   1.00    1.00    --  -41.55-178.00 -60.00   73
  2  ω     17.00 116.00   1.00    1.00    --   41.55  38.00   0.00   99
  3  ω    -33.00  66.00   1.00    1.00    --   41.55 -38.00  60.00   99
  4  ω     67.00 166.00   1.00    1.00    --   92.50  45.00  90.00   99
  5  ω      9.00 130.00   1.00    1.00    --   92.50 -91.00  42.95  121
  6  ω     60.00 169.00   1.00    1.00    --   92.50  77.00  90.00  109
  7  ω     67.00 166.00   1.00    1.00    --   92.50  45.00  60.00   99
  8  ω      9.00 129.00   1.00    1.00    --   92.50 -89.00 -93.75  120
  9  ω     73.00 166.00   1.00    1.00    --   92.50 125.00   0.00   93
 10  ω     11.00 145.00   1.00    1.00    --   92.50 -15.00 -30.00  134
 11  ω     73.00 166.00   1.00    1.00    --   92.50 125.00-150.00   93
 12  ω     63.00 165.00   1.00    1.00    --   92.50  61.00 -30.00  102
 13  ω     10.00  84.00   1.00    1.00    --   92.50 -95.00-120.00   74
 14  ω   -114.00 -37.00   1.00    1.00    --  -41.55 -57.00-180.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0000374000
_diffrn_orient_matrix_UB_12      0.1036376000
_diffrn_orient_matrix_UB_13      -0.0384413000
_diffrn_orient_matrix_UB_21      0.0377950000
_diffrn_orient_matrix_UB_22      0.0333698000
_diffrn_orient_matrix_UB_23      0.1200471000
_diffrn_orient_matrix_UB_31      0.2014434000
_diffrn_orient_matrix_UB_32      -0.0062335000
_diffrn_orient_matrix_UB_33      0.0045361000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2037
_reflns_number_total             2318
_reflns_odcompleteness_completeness 98.02
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0178(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.034
_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)+(0.0554P)²+0.4247P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1074
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N7(H7), C13(H13), C4(H4), C6(H6), C11(H11), C12(H12), C5(H5)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
2.c Idealised tetrahedral OH refined as rotating group:
 O15(H15)
;
_atom_sites_solution_hydrogens   geom
_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
O16 O 0.92762(18) 0.29600(8) 0.14489(10) 0.0558(4) Uani 1 1 d . . . . .
O15 O 1.12430(17) 0.24161(8) 0.28798(11) 0.0560(4) Uani 1 1 d . . . . .
H15 H 1.0948 0.1905 0.2586 0.084 Uiso 1 1 calc GR . . . .
C9 C 0.95615(19) 0.48331(10) 0.24191(12) 0.0364(4) Uani 1 1 d . . . . .
N7 N 0.83578(19) 0.47712(9) 0.14562(11) 0.0469(4) Uani 1 1 d . . . . .
H7 H 0.8268 0.4237 0.1119 0.056 Uiso 1 1 calc R . . . .
C1 C 0.7229(2) 0.55231(10) 0.09594(12) 0.0383(4) Uani 1 1 d . . . . .
C2 C 0.5831(2) 0.58376(11) 0.14178(12) 0.0392(4) Uani 1 1 d . . . . .
N8 N 0.97889(18) 0.56776(9) 0.29237(10) 0.0423(3) Uani 1 1 d . . . . .
C14 C 1.0282(2) 0.30914(10) 0.23280(13) 0.0393(4) Uani 1 1 d . . . . .
C10 C 1.0551(2) 0.40260(10) 0.28715(12) 0.0380(4) Uani 1 1 d . . . . .
C13 C 1.0981(3) 0.57482(12) 0.38709(14) 0.0516(5) Uani 1 1 d . . . . .
H13 H 1.1125 0.6334 0.4219 0.062 Uiso 1 1 calc R . . . .
F18 F 0.2711(2) 0.78112(11) 0.08797(11) 0.0943(5) Uani 1 1 d . . . . .
C3 C 0.4806(2) 0.65892(11) 0.08877(12) 0.0403(4) Uani 1 1 d . . . . .
F19 F 0.3798(2) 0.71757(13) 0.24130(10) 0.1030(6) Uani 1 1 d . . . . .
C4 C 0.5109(2) 0.69640(12) -0.00820(13) 0.0463(4) Uani 1 1 d . . . . .
H4 H 0.4395 0.7453 -0.0428 0.056 Uiso 1 1 calc R . . . .
C6 C 0.7536(2) 0.59024(13) -0.00016(13) 0.0501(4) Uani 1 1 d . . . . .
H6 H 0.8472 0.5676 -0.0294 0.060 Uiso 1 1 calc R . . . .
C11 C 1.1768(2) 0.41357(12) 0.38500(14) 0.0506(5) Uani 1 1 d . . . . .
H11 H 1.2431 0.3619 0.4167 0.061 Uiso 1 1 calc R . . . .
C12 C 1.2004(3) 0.50056(13) 0.43584(15) 0.0587(5) Uani 1 1 d . . . . .
H12 H 1.2831 0.5088 0.5011 0.070 Uiso 1 1 calc R . . . .
F20 F 0.19187(17) 0.64198(13) 0.12152(13) 0.1015(5) Uani 1 1 d . . . . .
C5 C 0.6459(2) 0.66163(14) -0.05312(14) 0.0552(5) Uani 1 1 d . . . . .
H5 H 0.6649 0.6859 -0.1189 0.066 Uiso 1 1 calc R . . . .
C17 C 0.3330(3) 0.70006(16) 0.13479(15) 0.0624(5) Uani 1 1 d . . . . .
C21 C 0.5467(3) 0.53731(16) 0.24323(15) 0.0633(5) Uani 1 1 d . . . . .
H21A H 0.6026 0.5731 0.3064 0.095 Uiso 1 1 calc GR . . . .
H21B H 0.5938 0.4741 0.2489 0.095 Uiso 1 1 calc GR . . . .
H21C H 0.4207 0.5351 0.2391 0.095 Uiso 1 1 calc GR . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O16 0.0701(8) 0.0333(6) 0.0538(7) -0.0035(5) -0.0105(6) 0.0067(5)
O15 0.0588(8) 0.0282(6) 0.0691(8) 0.0037(5) -0.0134(6) 0.0044(5)
C9 0.0374(8) 0.0296(7) 0.0391(7) 0.0011(6) 0.0015(6) -0.0026(6)
N7 0.0527(8) 0.0294(6) 0.0487(7) -0.0046(5) -0.0116(6) 0.0075(6)
C1 0.0396(8) 0.0298(7) 0.0395(8) -0.0020(6) -0.0054(6) 0.0006(6)
C2 0.0395(8) 0.0385(8) 0.0345(7) 0.0009(6) -0.0035(6) -0.0044(6)
N8 0.0486(8) 0.0297(7) 0.0436(7) 0.0005(5) -0.0016(6) -0.0015(5)
C14 0.0377(8) 0.0309(7) 0.0470(9) 0.0059(6) 0.0037(7) 0.0010(6)
C10 0.0377(8) 0.0308(8) 0.0428(8) 0.0050(6) 0.0024(6) -0.0019(6)
C13 0.0645(11) 0.0360(8) 0.0461(9) -0.0031(7) -0.0066(8) -0.0050(8)
F18 0.1041(11) 0.0974(10) 0.0794(8) 0.0054(7) 0.0151(8) 0.0615(9)
C3 0.0377(8) 0.0423(8) 0.0360(7) -0.0031(6) -0.0037(6) 0.0015(6)
F19 0.1079(11) 0.1503(14) 0.0468(6) -0.0201(7) 0.0075(7) 0.0574(10)
C4 0.0464(9) 0.0432(9) 0.0433(8) 0.0082(7) -0.0041(7) 0.0073(7)
C6 0.0463(9) 0.0579(10) 0.0458(9) 0.0041(8) 0.0091(7) 0.0098(8)
C11 0.0552(10) 0.0374(8) 0.0506(9) 0.0096(7) -0.0082(8) 0.0016(7)
C12 0.0697(12) 0.0444(9) 0.0483(9) 0.0024(7) -0.0185(8) -0.0038(9)
F20 0.0504(7) 0.1461(14) 0.1133(11) 0.0014(10) 0.0290(7) 0.0052(8)
C5 0.0554(11) 0.0658(12) 0.0439(9) 0.0182(8) 0.0096(8) 0.0081(9)
C17 0.0583(12) 0.0811(14) 0.0437(9) -0.0027(9) 0.0014(8) 0.0234(10)
C21 0.0626(12) 0.0752(13) 0.0517(10) 0.0215(9) 0.0108(9) 0.0046(10)

_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
O16 C14 1.2173(19) . ?
O15 C14 1.3102(18) . ?
C9 N7 1.3575(19) . ?
C9 N8 1.3436(19) . ?
C9 C10 1.420(2) . ?
N7 C1 1.4282(19) . ?
C1 C2 1.393(2) . ?
C1 C6 1.380(2) . ?
C2 C3 1.402(2) . ?
C2 C21 1.505(2) . ?
N8 C13 1.339(2) . ?
C14 C10 1.479(2) . ?
C10 C11 1.383(2) . ?
C13 C12 1.374(2) . ?
F18 C17 1.328(2) . ?
C3 C4 1.387(2) . ?
C3 C17 1.493(2) . ?
F19 C17 1.327(2) . ?
C4 C5 1.370(3) . ?
C6 C5 1.382(2) . ?
C11 C12 1.378(2) . ?
F20 C17 1.342(3) . ?

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
N7 C9 C10 120.60(13) . . ?
N8 C9 N7 118.05(13) . . ?
N8 C9 C10 121.35(13) . . ?
C9 N7 C1 125.15(12) . . ?
C2 C1 N7 120.60(14) . . ?
C6 C1 N7 117.89(15) . . ?
C6 C1 C2 121.47(14) . . ?
C1 C2 C3 116.90(14) . . ?
C1 C2 C21 120.24(15) . . ?
C3 C2 C21 122.86(16) . . ?
C13 N8 C9 118.56(13) . . ?
O16 C14 O15 122.99(14) . . ?
O16 C14 C10 123.46(13) . . ?
O15 C14 C10 113.55(13) . . ?
C9 C10 C14 121.49(13) . . ?
C11 C10 C9 117.89(14) . . ?
C11 C10 C14 120.61(14) . . ?
N8 C13 C12 123.79(15) . . ?
C2 C3 C17 120.62(15) . . ?
C4 C3 C2 121.41(15) . . ?
C4 C3 C17 117.97(15) . . ?
C5 C4 C3 120.14(15) . . ?
C1 C6 C5 120.36(16) . . ?
C12 C11 C10 120.45(15) . . ?
C13 C12 C11 117.96(15) . . ?
C4 C5 C6 119.61(16) . . ?
F18 C17 C3 113.39(17) . . ?
F18 C17 F20 105.51(17) . . ?
F19 C17 F18 106.11(17) . . ?
F19 C17 C3 113.05(15) . . ?
F19 C17 F20 106.20(19) . . ?
F20 C17 C3 111.97(17) . . ?

_olex2_date_sample_data_collection 2018-03-22
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.509
_oxdiff_exptl_absorpt_empirical_full_min 0.828
