# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_WH20190409-2
_database_code_depnum_ccdc_archive 'CCDC 1914999'
loop_
_audit_author_name
_audit_author_address
'difluoromethyl nitro aniline'
;Jiangxi normal university
China
;
_audit_update_record             
;
2019-05-09 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C8H8F2N2O2
_chemical_formula_sum            'C8 H8 F2 N2 O2'
_chemical_formula_weight         202.16

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.3061(18)
_cell_length_b                   7.8603(8)
_cell_length_c                   15.960(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.346(13)
_cell_angle_gamma                90
_cell_volume                     1770.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4466
_cell_measurement_theta_min      3.8920
_cell_measurement_theta_max      26.9420

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   0.6382
_exptl_transmission_factor_max   0.7215
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.137
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13915
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.329
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3297
_reflns_number_gt                2401
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0896P)²+0.8043P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3297
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.1827
_refine_ls_wR_factor_gt          0.1652
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C12 C 0.46779(16) 0.6995(3) 0.04121(15) 0.0415(5) Uani 1 1 d . . . . .
C9 C 0.29058(17) 0.5943(3) -0.03777(16) 0.0461(6) Uani 1 1 d . . . . .
C10 C 0.32505(17) 0.5392(3) 0.04368(16) 0.0472(6) Uani 1 1 d . . . . .
H10 H 0.2892 0.4664 0.0717 0.057 Uiso 1 1 calc R U . . .
N4 N 0.55574(15) 0.7526(3) 0.07750(13) 0.0520(6) Uani 1 1 d . . . . .
H4 H 0.5849 0.8212 0.0486 0.062 Uiso 1 1 calc R U . . .
C14 C 0.34379(19) 0.7018(3) -0.08022(16) 0.0535(7) Uani 1 1 d . . . . .
H14 H 0.3199 0.7385 -0.1349 0.064 Uiso 1 1 calc R U . . .
N3 N 0.19822(16) 0.5405(3) -0.07750(17) 0.0621(6) Uani 1 1 d . . . . .
C6 C 0.76470(19) 0.1302(4) 0.8645(2) 0.0612(8) Uani 1 1 d . . . . .
H6 H 0.7065 0.0943 0.8351 0.073 Uiso 1 1 calc R U . . .
C4 C 0.90503(17) 0.3026(3) 0.87162(16) 0.0474(6) Uani 1 1 d . . . . .
C11 C 0.41206(18) 0.5926(3) 0.08246(16) 0.0476(6) Uani 1 1 d . . . . .
H11 H 0.4347 0.5571 0.1376 0.057 Uiso 1 1 calc R U . . .
N2 N 0.95979(15) 0.4205(3) 0.83989(15) 0.0594(6) Uani 1 1 d . . . . .
H1 H 1.0161 0.4351 0.8674 0.071 Uiso 1 1 calc R U . . .
C13 C 0.43114(18) 0.7536(3) -0.04171(16) 0.0491(6) Uani 1 1 d . . . . .
H13 H 0.4669 0.8252 -0.0705 0.059 Uiso 1 1 calc R U . . .
F4 F 0.49323(14) 0.8334(3) 0.23440(12) 0.0910(7) Uani 1 1 d . . . . .
C3 C 0.93834(18) 0.2285(3) 0.95085(18) 0.0551(7) Uani 1 1 d . . . . .
H3 H 0.9977 0.2593 0.9798 0.066 Uiso 1 1 calc R U . . .
C1 C 0.79869(19) 0.0631(3) 0.9433(2) 0.0565(7) Uani 1 1 d . . . . .
F3 F 0.61527(17) 0.9797(2) 0.21528(12) 0.0918(7) Uani 1 1 d . . . . .
C2 C 0.8856(2) 0.1125(4) 0.98623(19) 0.0604(7) Uani 1 1 d . . . . .
H2 H 0.9085 0.0667 1.0394 0.072 Uiso 1 1 calc R U . . .
C5 C 0.81650(18) 0.2498(4) 0.82932(18) 0.0568(7) Uani 1 1 d . . . . .
H5 H 0.7924 0.2963 0.7767 0.068 Uiso 1 1 calc R U . . .
O3 O 0.15166(14) 0.4482(3) -0.03840(15) 0.0772(6) Uani 1 1 d . . . . .
C15 C 0.60339(18) 0.7038(4) 0.15945(17) 0.0549(7) Uani 1 1 d . . . . .
H15A H 0.6709 0.6994 0.1582 0.066 Uiso 1 1 calc R U . . .
H15B H 0.5831 0.5900 0.1718 0.066 Uiso 1 1 calc R U . . .
N1 N 0.7402(2) -0.0523(3) 0.9826(2) 0.0754(8) Uani 1 1 d . . . . .
O4 O 0.16778(18) 0.5896(4) -0.14935(16) 0.1126(11) Uani 1 1 d . . . . .
O2 O 0.6655(2) -0.1033(3) 0.9407(2) 0.0986(9) Uani 1 1 d . . . . .
F2 F 0.80504(15) 0.6627(3) 0.80943(18) 0.1126(8) Uani 1 1 d . . . . .
C7 C 0.9333(2) 0.5225(4) 0.76552(18) 0.0626(8) Uani 1 1 d . . . . .
H7A H 0.8908 0.4570 0.7241 0.075 Uiso 1 1 calc R U . . .
H7B H 0.9896 0.5472 0.7411 0.075 Uiso 1 1 calc R U . . .
F1 F 0.94149(17) 0.7795(3) 0.84086(15) 0.1048(7) Uani 1 1 d . . . . .
O1 O 0.7658(2) -0.0930(3) 1.0574(2) 0.1027(9) Uani 1 1 d . . . . .
C16 C 0.5865(2) 0.8194(4) 0.22947(18) 0.0622(7) Uani 1 1 d . . . . .
H16 H 0.6210 0.7775 0.2836 0.075 Uiso 1 1 calc R U . . .
C8 C 0.8858(2) 0.6878(5) 0.7809(2) 0.0755(9) Uani 1 1 d . . . . .
H8 H 0.8737 0.7531 0.7279 0.091 Uiso 1 1 calc R U . . .


_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
C12 N4 1.362(3) . ?
C12 C11 1.395(3) . ?
C12 C13 1.408(3) . ?
C9 C10 1.383(4) . ?
C9 C14 1.386(4) . ?
C9 N3 1.433(3) . ?
C10 C11 1.363(3) . ?
C10 H10 0.9300 . ?
N4 C15 1.426(3) . ?
N4 H4 0.8600 . ?
C14 C13 1.362(4) . ?
C14 H14 0.9300 . ?
N3 O4 1.221(3) . ?
N3 O3 1.223(3) . ?
C6 C5 1.372(4) . ?
C6 C1 1.378(4) . ?
C6 H6 0.9300 . ?
C4 N2 1.363(3) . ?
C4 C5 1.398(3) . ?
C4 C3 1.403(4) . ?
C11 H11 0.9300 . ?
N2 C7 1.432(4) . ?
N2 H1 0.8600 . ?
C13 H13 0.9300 . ?
F4 C16 1.354(3) . ?
C3 C2 1.363(4) . ?
C3 H3 0.9300 . ?
C1 C2 1.375(4) . ?
C1 N1 1.445(4) . ?
F3 C16 1.356(3) . ?
C2 H2 0.9300 . ?
C5 H5 0.9300 . ?
C15 C16 1.490(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
N1 O1 1.232(4) . ?
N1 O2 1.232(4) . ?
F2 C8 1.324(4) . ?
C7 C8 1.505(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
F1 C8 1.350(4) . ?
C16 H16 0.9800 . ?
C8 H8 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
N4 C12 C11 122.9(2) . . ?
N4 C12 C13 119.0(2) . . ?
C11 C12 C13 118.1(2) . . ?
C10 C9 C14 120.7(2) . . ?
C10 C9 N3 119.1(2) . . ?
C14 C9 N3 120.2(2) . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 N4 C15 125.3(2) . . ?
C12 N4 H4 117.3 . . ?
C15 N4 H4 117.3 . . ?
C13 C14 C9 119.9(2) . . ?
C13 C14 H14 120.1 . . ?
C9 C14 H14 120.1 . . ?
O4 N3 O3 121.7(3) . . ?
O4 N3 C9 119.0(3) . . ?
O3 N3 C9 119.3(3) . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
N2 C4 C5 123.6(2) . . ?
N2 C4 C3 119.0(2) . . ?
C5 C4 C3 117.4(2) . . ?
C10 C11 C12 121.4(2) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C4 N2 C7 126.8(2) . . ?
C4 N2 H1 116.6 . . ?
C7 N2 H1 116.6 . . ?
C14 C13 C12 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C2 C1 C6 120.2(3) . . ?
C2 C1 N1 120.1(3) . . ?
C6 C1 N1 119.6(3) . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
N4 C15 C16 114.3(2) . . ?
N4 C15 H15A 108.7 . . ?
C16 C15 H15A 108.7 . . ?
N4 C15 H15B 108.7 . . ?
C16 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
O1 N1 O2 122.5(3) . . ?
O1 N1 C1 118.8(3) . . ?
O2 N1 C1 118.7(3) . . ?
N2 C7 C8 114.5(3) . . ?
N2 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
N2 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
F4 C16 F3 105.2(3) . . ?
F4 C16 C15 112.0(2) . . ?
F3 C16 C15 110.6(2) . . ?
F4 C16 H16 109.7 . . ?
F3 C16 H16 109.7 . . ?
C15 C16 H16 109.7 . . ?
F2 C8 F1 106.5(3) . . ?
F2 C8 C7 111.7(3) . . ?
F1 C8 C7 110.2(3) . . ?
F2 C8 H8 109.5 . . ?
F1 C8 H8 109.5 . . ?
C7 C8 H8 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
C14 C9 C10 C11 0.5(4) . . . . ?
N3 C9 C10 C11 -178.7(2) . . . . ?
C11 C12 N4 C15 2.0(4) . . . . ?
C13 C12 N4 C15 -177.6(2) . . . . ?
C10 C9 C14 C13 0.2(4) . . . . ?
N3 C9 C14 C13 179.4(2) . . . . ?
C10 C9 N3 O4 179.8(3) . . . . ?
C14 C9 N3 O4 0.7(4) . . . . ?
C10 C9 N3 O3 0.5(4) . . . . ?
C14 C9 N3 O3 -178.6(2) . . . . ?
C9 C10 C11 C12 -1.1(4) . . . . ?
N4 C12 C11 C10 -178.7(2) . . . . ?
C13 C12 C11 C10 1.0(4) . . . . ?
C5 C4 N2 C7 7.7(4) . . . . ?
C3 C4 N2 C7 -172.5(3) . . . . ?
C9 C14 C13 C12 -0.4(4) . . . . ?
N4 C12 C13 C14 179.4(2) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
N2 C4 C3 C2 178.7(2) . . . . ?
C5 C4 C3 C2 -1.5(4) . . . . ?
C5 C6 C1 C2 -1.6(4) . . . . ?
C5 C6 C1 N1 175.0(2) . . . . ?
C4 C3 C2 C1 1.4(4) . . . . ?
C6 C1 C2 C3 0.2(4) . . . . ?
N1 C1 C2 C3 -176.4(2) . . . . ?
C1 C6 C5 C4 1.4(4) . . . . ?
N2 C4 C5 C6 179.9(2) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C12 N4 C15 C16 -91.3(3) . . . . ?
C2 C1 N1 O1 6.4(4) . . . . ?
C6 C1 N1 O1 -170.2(3) . . . . ?
C2 C1 N1 O2 -175.2(3) . . . . ?
C6 C1 N1 O2 8.2(4) . . . . ?
C4 N2 C7 C8 88.1(3) . . . . ?
N4 C15 C16 F4 57.7(3) . . . . ?
N4 C15 C16 F3 -59.3(3) . . . . ?
N2 C7 C8 F2 -62.2(4) . . . . ?
N2 C7 C8 F1 55.9(3) . . . . ?

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
C16 H16 F2 0.98 2.64 3.182(4) 115.1 4_575
N2 H1 O4 0.86 2.54 3.238(3) 139.1 1_656
N2 H1 O3 0.86 2.26 3.102(3) 168.3 1_656
C11 H11 F3 0.93 2.63 3.431(3) 144.0 2_645
N4 H4 O1 0.86 2.66 3.304(3) 133.2 1_564
N4 H4 O2 0.86 2.30 3.103(3) 155.3 1_564
N4 H4 O2 0.86 2.30 3.103(3) 155.3 1_564
N4 H4 O1 0.86 2.66 3.304(3) 133.2 1_564
C11 H11 F3 0.93 2.63 3.431(3) 144.0 2_645
N2 H1 O3 0.86 2.26 3.102(3) 168.3 1_656
N2 H1 O4 0.86 2.54 3.238(3) 139.1 1_656
C16 H16 F2 0.98 2.64 3.182(4) 115.1 4_575

_refine_diff_density_max         0.701
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_WH20190409-1
_database_code_depnum_ccdc_archive 'CCDC 1915000'
loop_
_audit_author_name
_audit_author_address
quinoline
;Jiangxi normal university
China
;
_audit_update_record             
;
2019-05-09 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C11H9F3N2
_chemical_formula_sum            'C11 H9 F3 N2'
_chemical_formula_weight         226.20

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_H-M_alt        'R 3 :H'
_space_group_name_Hall           'R 3'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'

_cell_length_a                   23.510(2)
_cell_length_b                   23.510(2)
_cell_length_c                   4.8517(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2322.4(5)
_cell_formula_units_Z            9
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3024
_cell_measurement_theta_min      4.5410
_cell_measurement_theta_max      28.5920

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_F_000             1044
_exptl_transmission_factor_min   0.6345
_exptl_transmission_factor_max   0.7143
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.126
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4751
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.466
_diffrn_reflns_theta_max         25.464
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1914
_reflns_number_gt                1728
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0848P)²+0.3143P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 734 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1914
_refine_ls_number_parameters     145
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.04377(16) 0.22772(16) 0.2238(8) 0.0422(8) Uani 1 1 d . . . . .
C2 C 0.04847(19) 0.28440(17) 0.3510(8) 0.0492(9) Uani 1 1 d . . . . .
H2 H 0.0181 0.2967 0.2980 0.059 Uiso 1 1 calc R U . . .
C3 C 0.13673(17) 0.30220(17) 0.6162(8) 0.0465(9) Uani 1 1 d . . . . .
C4 C 0.13725(16) 0.24806(16) 0.4973(7) 0.0416(8) Uani 1 1 d . . . . .
C5 C 0.08921(17) 0.21036(17) 0.2964(7) 0.0418(8) Uani 1 1 d . . . . .
H5 H 0.0886 0.1742 0.2151 0.050 Uiso 1 1 calc R U . . .
C6 C 0.18460(19) 0.2317(2) 0.5863(9) 0.0547(9) Uani 1 1 d . . . . .
H6 H 0.1854 0.1959 0.5092 0.066 Uiso 1 1 calc R U . . .
C7 C 0.2292(2) 0.2683(2) 0.7848(9) 0.0632(11) Uani 1 1 d . . . . .
H7 H 0.2606 0.2577 0.8407 0.076 Uiso 1 1 calc R U . . .
C8 C 0.2275(2) 0.3218(2) 0.9042(9) 0.0663(13) Uani 1 1 d . . . . .
H8 H 0.2576 0.3460 1.0414 0.080 Uiso 1 1 calc R U . . .
C9 C 0.1828(2) 0.3388(2) 0.8235(9) 0.0606(11) Uani 1 1 d . . . . .
H9 H 0.1826 0.3745 0.9046 0.073 Uiso 1 1 calc R U . . .
C10 C -0.0141(2) 0.1407(2) -0.1275(8) 0.0527(9) Uani 1 1 d . . . . .
H10A H 0.0293 0.1474 -0.1668 0.063 Uiso 1 1 calc R U . . .
H10B H -0.0338 0.1419 -0.3016 0.063 Uiso 1 1 calc R U . . .
C11 C -0.0545(2) 0.0746(2) -0.0034(10) 0.0620(11) Uani 1 1 d . . . . .
F1 F -0.0281(2) 0.06731(15) 0.2276(6) 0.0977(12) Uani 1 1 d . . . . .
F2 F -0.06164(18) 0.02691(15) -0.1689(7) 0.0880(10) Uani 1 1 d . . . . .
F3 F -0.11494(17) 0.06042(16) 0.0618(12) 0.1180(16) Uani 1 1 d . . . . .
N1 N 0.09171(17) 0.32049(15) 0.5350(8) 0.0536(8) Uani 1 1 d . . . . .
N2 N -0.00736(16) 0.19345(17) 0.0408(8) 0.0547(9) Uani 1 1 d . . . . .
H2A H -0.0369 0.2047 0.0276 0.066 Uiso 1 1 calc R U . . .


_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
C1 C5 1.367(5) . ?
C1 N2 1.384(5) . ?
C1 C2 1.422(5) . ?
C2 N1 1.299(5) . ?
C2 H2 0.9300 . ?
C3 N1 1.384(5) . ?
C3 C4 1.403(5) . ?
C3 C9 1.412(6) . ?
C4 C6 1.415(5) . ?
C4 C5 1.418(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.365(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.403(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.354(7) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 N2 1.426(6) . ?
C10 C11 1.484(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 F2 1.319(6) . ?
C11 F3 1.326(5) . ?
C11 F1 1.333(6) . ?
N2 H2A 0.8600 . ?

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
C5 C1 N2 124.9(3) . . ?
C5 C1 C2 117.5(3) . . ?
N2 C1 C2 117.5(3) . . ?
N1 C2 C1 125.4(3) . . ?
N1 C2 H2 117.3 . . ?
C1 C2 H2 117.3 . . ?
N1 C3 C4 121.3(3) . . ?
N1 C3 C9 119.1(4) . . ?
C4 C3 C9 119.6(4) . . ?
C3 C4 C6 119.1(3) . . ?
C3 C4 C5 119.0(3) . . ?
C6 C4 C5 122.0(3) . . ?
C1 C5 C4 119.2(3) . . ?
C1 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C7 C6 C4 120.3(4) . . ?
C7 C6 H6 119.8 . . ?
C4 C6 H6 119.8 . . ?
C6 C7 C8 119.9(4) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 121.3(4) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C3 119.9(4) . . ?
C8 C9 H9 120.1 . . ?
C3 C9 H9 120.1 . . ?
N2 C10 C11 114.4(3) . . ?
N2 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
N2 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
F2 C11 F3 105.5(4) . . ?
F2 C11 F1 105.8(4) . . ?
F3 C11 F1 106.0(4) . . ?
F2 C11 C10 112.7(4) . . ?
F3 C11 C10 113.8(4) . . ?
F1 C11 C10 112.4(4) . . ?
C2 N1 C3 117.6(3) . . ?
C1 N2 C10 124.1(3) . . ?
C1 N2 H2A 118.0 . . ?
C10 N2 H2A 118.0 . . ?

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
C5 C1 C2 N1 -1.4(5) . . . . ?
N2 C1 C2 N1 177.1(4) . . . . ?
N1 C3 C4 C6 179.6(3) . . . . ?
C9 C3 C4 C6 -0.6(5) . . . . ?
N1 C3 C4 C5 -2.0(5) . . . . ?
C9 C3 C4 C5 177.8(3) . . . . ?
N2 C1 C5 C4 -176.9(3) . . . . ?
C2 C1 C5 C4 1.6(5) . . . . ?
C3 C4 C5 C1 0.1(5) . . . . ?
C6 C4 C5 C1 178.4(3) . . . . ?
C3 C4 C6 C7 -0.1(5) . . . . ?
C5 C4 C6 C7 -178.5(4) . . . . ?
C4 C6 C7 C8 0.9(6) . . . . ?
C6 C7 C8 C9 -1.0(6) . . . . ?
C7 C8 C9 C3 0.2(6) . . . . ?
N1 C3 C9 C8 -179.6(4) . . . . ?
C4 C3 C9 C8 0.6(6) . . . . ?
N2 C10 C11 F2 177.7(4) . . . . ?
N2 C10 C11 F3 57.7(5) . . . . ?
N2 C10 C11 F1 -62.9(5) . . . . ?
C1 C2 N1 C3 -0.5(5) . . . . ?
C4 C3 N1 C2 2.2(5) . . . . ?
C9 C3 N1 C2 -177.6(4) . . . . ?
C5 C1 N2 C10 -9.5(5) . . . . ?
C2 C1 N2 C10 172.1(3) . . . . ?
C11 C10 N2 C1 92.4(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
N2 H2A N1 0.86 2.29 3.129(5) 163.8 6_454
C9 H9 F3 0.93 2.64 3.156(6) 116.0 8
C5 H5 F1 0.93 2.64 3.123(5) 113.2 .
N2 H2A N1 0.86 2.29 3.129(5) 163.8 6_454
C9 H9 F3 0.93 2.64 3.156(6) 116.0 8
C5 H5 F1 0.93 2.64 3.123(5) 113.2 .

_refine_diff_density_max         0.216
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.061

