# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1883638'
loop_
_audit_author_name
_audit_author_address
'Tu Jin'
;Wuhan University
China
;
_audit_update_record             
;
2018-12-07 deposited with the CCDC.	2019-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 N O'
_chemical_formula_weight         273.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   12.0916(17)
_cell_length_b                   11.4255(16)
_cell_length_c                   10.9413(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.999(3)
_cell_angle_gamma                90.00
_cell_volume                     1478.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    57
_cell_measurement_theta_min      7.5
_cell_measurement_theta_max      20

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9559
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         26.50
_reflns_number_total             3056
_reflns_number_gt                2273
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0378P)²+0.3419P] 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       0.029(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3056
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1052
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.78412(11) 0.14310(11) 0.00306(13) 0.0450(3) Uani 1 1 d . . .
C2 C 0.86034(13) 0.07894(13) -0.04716(14) 0.0538(4) Uani 1 1 d . . .
H2 H 0.9297 0.1114 -0.0528 0.065 Uiso 1 1 calc R . .
C3 C 0.83359(14) -0.03354(14) -0.08914(15) 0.0609(4) Uani 1 1 d . . .
H3 H 0.8854 -0.0768 -0.1225 0.073 Uiso 1 1 calc R . .
C4 C 0.73142(14) -0.08212(13) -0.08221(15) 0.0597(4) Uani 1 1 d . . .
H4 H 0.7136 -0.1576 -0.1115 0.072 Uiso 1 1 calc R . .
C5 C 0.65588(13) -0.01884(13) -0.03193(16) 0.0592(4) Uani 1 1 d . . .
H5 H 0.5866 -0.0517 -0.0268 0.071 Uiso 1 1 calc R . .
C6 C 0.68156(12) 0.09370(12) 0.01141(15) 0.0541(4) Uani 1 1 d . . .
H6 H 0.6300 0.1360 0.0461 0.065 Uiso 1 1 calc R . .
C7 C 0.74047(11) 0.35295(11) -0.00186(13) 0.0454(3) Uani 1 1 d . . .
C8 C 0.67122(12) 0.34612(12) -0.12000(14) 0.0531(4) Uani 1 1 d . . .
H8 H 0.6722 0.2793 -0.1683 0.064 Uiso 1 1 calc R . .
C9 C 0.60134(13) 0.43789(13) -0.16566(15) 0.0576(4) Uani 1 1 d . . .
H9 H 0.5545 0.4315 -0.2444 0.069 Uiso 1 1 calc R . .
C10 C 0.59884(12) 0.53921(12) -0.09773(15) 0.0528(4) Uani 1 1 d . . .
C11 C 0.66814(12) 0.54636(12) 0.02052(16) 0.0557(4) Uani 1 1 d . . .
H11 H 0.6674 0.6139 0.0678 0.067 Uiso 1 1 calc R . .
C12 C 0.73764(12) 0.45500(12) 0.06842(15) 0.0535(4) Uani 1 1 d . . .
H12 H 0.7831 0.4609 0.1480 0.064 Uiso 1 1 calc R . .
C13 C 0.52300(14) 0.63464(15) -0.1496(2) 0.0711(5) Uani 1 1 d . . .
H13 H 0.4761 0.6219 -0.2273 0.085 Uiso 1 1 calc R . .
C14 C 0.91775(11) 0.27947(12) 0.12798(13) 0.0460(3) Uani 1 1 d . . .
C15 C 0.98844(13) 0.36592(14) 0.10096(16) 0.0616(4) Uani 1 1 d . . .
H15 H 0.9647 0.4134 0.0314 0.074 Uiso 1 1 calc R . .
C16 C 1.09360(14) 0.38293(17) 0.1756(2) 0.0753(5) Uani 1 1 d . . .
H16 H 1.1402 0.4418 0.1560 0.090 Uiso 1 1 calc R . .
C17 C 1.13005(15) 0.31445(18) 0.27765(18) 0.0754(6) Uani 1 1 d . . .
H17 H 1.2014 0.3260 0.3277 0.090 Uiso 1 1 calc R . .
C18 C 1.06066(16) 0.22810(19) 0.30614(15) 0.0747(5) Uani 1 1 d . . .
H18 H 1.0852 0.1813 0.3760 0.090 Uiso 1 1 calc R . .
C19 C 0.95382(14) 0.20996(15) 0.23128(15) 0.0608(4) Uani 1 1 d . . .
H19 H 0.9072 0.1512 0.2510 0.073 Uiso 1 1 calc R . .
N1 N 0.81062(10) 0.25959(10) 0.04765(12) 0.0534(3) Uani 1 1 d . . .
O1 O 0.51541(11) 0.72782(10) -0.10160(15) 0.0867(4) Uani 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
C1 C2 1.378(2) . ?
C1 C6 1.3827(19) . ?
C1 N1 1.4308(17) . ?
C2 C3 1.380(2) . ?
C3 C4 1.371(2) . ?
C4 C5 1.367(2) . ?
C5 C6 1.383(2) . ?
C7 C8 1.3885(19) . ?
C7 N1 1.3999(17) . ?
C7 C12 1.4011(19) . ?
C8 C9 1.3739(19) . ?
C9 C10 1.379(2) . ?
C10 C11 1.390(2) . ?
C10 C13 1.461(2) . ?
C11 C12 1.374(2) . ?
C13 O1 1.199(2) . ?
C14 C19 1.376(2) . ?
C14 C15 1.378(2) . ?
C14 N1 1.4243(17) . ?
C15 C16 1.374(2) . ?
C16 C17 1.360(3) . ?
C17 C18 1.372(3) . ?
C18 C19 1.394(2) . ?

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 C1 C6 119.50(13) . . ?
C2 C1 N1 120.65(13) . . ?
C6 C1 N1 119.84(13) . . ?
C1 C2 C3 119.87(14) . . ?
C4 C3 C2 120.67(15) . . ?
C5 C4 C3 119.56(14) . . ?
C4 C5 C6 120.56(15) . . ?
C1 C6 C5 119.82(14) . . ?
C8 C7 N1 121.13(12) . . ?
C8 C7 C12 118.61(13) . . ?
N1 C7 C12 120.25(13) . . ?
C9 C8 C7 120.13(13) . . ?
C8 C9 C10 121.69(14) . . ?
C9 C10 C11 118.32(13) . . ?
C9 C10 C13 119.95(15) . . ?
C11 C10 C13 121.72(14) . . ?
C12 C11 C10 120.86(13) . . ?
C11 C12 C7 120.38(14) . . ?
O1 C13 C10 126.26(18) . . ?
C19 C14 C15 119.02(14) . . ?
C19 C14 N1 120.47(13) . . ?
C15 C14 N1 120.47(13) . . ?
C16 C15 C14 120.83(16) . . ?
C17 C16 C15 120.54(18) . . ?
C16 C17 C18 119.42(16) . . ?
C17 C18 C19 120.60(17) . . ?
C14 C19 C18 119.58(16) . . ?
C7 N1 C14 121.16(11) . . ?
C7 N1 C1 120.14(11) . . ?
C14 N1 C1 117.99(11) . . ?

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 C1 C2 C3 0.3(2) . . . . ?
N1 C1 C2 C3 179.67(13) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
N1 C1 C6 C5 179.88(13) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
N1 C7 C8 C9 178.65(14) . . . . ?
C12 C7 C8 C9 -0.3(2) . . . . ?
C7 C8 C9 C10 1.1(2) . . . . ?
C8 C9 C10 C11 -1.0(2) . . . . ?
C8 C9 C10 C13 -179.82(15) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C13 C10 C11 C12 179.02(15) . . . . ?
C10 C11 C12 C7 0.5(2) . . . . ?
C8 C7 C12 C11 -0.4(2) . . . . ?
N1 C7 C12 C11 -179.42(13) . . . . ?
C9 C10 C13 O1 -177.71(18) . . . . ?
C11 C10 C13 O1 3.5(3) . . . . ?
C19 C14 C15 C16 0.1(2) . . . . ?
N1 C14 C15 C16 -177.67(15) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C15 C14 C19 C18 -0.1(2) . . . . ?
N1 C14 C19 C18 177.66(14) . . . . ?
C17 C18 C19 C14 -0.1(3) . . . . ?
C8 C7 N1 C14 146.52(14) . . . . ?
C12 C7 N1 C14 -34.5(2) . . . . ?
C8 C7 N1 C1 -23.6(2) . . . . ?
C12 C7 N1 C1 155.37(14) . . . . ?
C19 C14 N1 C7 139.20(15) . . . . ?
C15 C14 N1 C7 -43.1(2) . . . . ?
C19 C14 N1 C1 -50.5(2) . . . . ?
C15 C14 N1 C1 127.25(15) . . . . ?
C2 C1 N1 C7 122.22(15) . . . . ?
C6 C1 N1 C7 -58.42(19) . . . . ?
C2 C1 N1 C14 -48.22(19) . . . . ?
C6 C1 N1 C14 131.14(15) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.029
####################################################################### 
# 
# 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_mo_180123F_0m
_database_code_depnum_ccdc_archive 'CCDC 1883639'
loop_
_audit_author_name
_audit_author_address
'Tu Jin'
;Wuhan University
China
;
_audit_update_record             
;
2018-12-07 deposited with the CCDC.	2019-08-31 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         ?
_chemical_formula_sum            'C19 H13 Cl2 N O'
_chemical_formula_weight         342.20

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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, z+1/2'

_cell_length_a                   9.117(4)
_cell_length_b                   8.400(3)
_cell_length_c                   11.068(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.736(7)
_cell_angle_gamma                90
_cell_volume                     807.2(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1633
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      24.82

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.405
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5621
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.345
_diffrn_reflns_theta_max         25.499
_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 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.915
_reflns_number_total             2737
_reflns_number_gt                2235
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_max     0.831
_reflns_Friedel_fraction_full    0.832

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0538P)²] 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 824 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2737
_refine_ls_number_parameters     208
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1121
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_restrained_S_all      1.188
_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 0.8864(5) 0.8058(5) 0.8010(4) 0.0442(10) Uani 1 1 d . . . . .
C2 C 0.9300(6) 0.7476(5) 0.9230(5) 0.0458(10) Uani 1 1 d . . . . .
H2 H 0.8742 0.6645 0.9431 0.055 Uiso 1 1 calc R U . . .
C3 C 1.0535(5) 0.8087(6) 1.0158(4) 0.0523(11) Uani 1 1 d . . . . .
H3 H 1.0802 0.7698 1.0983 0.063 Uiso 1 1 calc R U . . .
C4 C 1.1367(5) 0.9290(6) 0.9834(5) 0.0537(12) Uani 1 1 d . . . . .
C5 C 1.1003(6) 0.9849(6) 0.8645(5) 0.0579(13) Uani 1 1 d . . . . .
H5 H 1.1597 1.0647 0.8443 0.069 Uiso 1 1 calc R U . . .
C6 C 0.9745(5) 0.9240(5) 0.7715(4) 0.0498(10) Uani 1 1 d . . . . .
H6 H 0.9495 0.9629 0.6891 0.060 Uiso 1 1 calc R U . . .
C7 C 0.7546(5) 0.7461(5) 0.5791(4) 0.0447(10) Uani 1 1 d . . . . .
C8 C 0.8770(6) 0.6845(6) 0.5450(5) 0.0565(12) Uani 1 1 d . . . . .
H8 H 0.9603 0.6402 0.6067 0.068 Uiso 1 1 calc R U . . .
C9 C 0.8768(6) 0.6879(7) 0.4222(5) 0.0639(14) Uani 1 1 d . . . . .
H9 H 0.9612 0.6498 0.4004 0.077 Uiso 1 1 calc R U . . .
C10 C 0.7525(7) 0.7475(6) 0.3311(5) 0.0645(16) Uani 1 1 d . . . . .
C11 C 0.6295(7) 0.8077(7) 0.3614(5) 0.0655(14) Uani 1 1 d . . . . .
H11 H 0.5451 0.8477 0.2984 0.079 Uiso 1 1 calc R U . . .
C12 C 0.6314(6) 0.8088(6) 0.4853(5) 0.0580(12) Uani 1 1 d . . . . .
H12 H 0.5488 0.8523 0.5067 0.070 Uiso 1 1 calc R U . . .
C13 C 0.6241(5) 0.6959(5) 0.7364(4) 0.0453(10) Uani 1 1 d . . . . .
C14 C 0.5814(6) 0.7629(5) 0.8342(5) 0.0485(11) Uani 1 1 d . . . . .
H14 H 0.6393 0.8461 0.8805 0.058 Uiso 1 1 calc R U . . .
C15 C 0.4550(5) 0.7089(6) 0.8645(4) 0.0508(11) Uani 1 1 d . . . . .
H15 H 0.4286 0.7551 0.9314 0.061 Uiso 1 1 calc R U . . .
C16 C 0.3664(5) 0.5860(6) 0.7959(4) 0.0503(11) Uani 1 1 d . . . . .
C17 C 0.4065(6) 0.5222(6) 0.6955(5) 0.0538(12) Uani 1 1 d . . . . .
H17 H 0.3471 0.4410 0.6476 0.065 Uiso 1 1 calc R U . . .
C18 C 0.5317(6) 0.5763(5) 0.6652(4) 0.0524(11) Uani 1 1 d . . . . .
H18 H 0.5557 0.5328 0.5963 0.063 Uiso 1 1 calc R U . . .
C19 C 0.2317(6) 0.5233(7) 0.8346(5) 0.0557(12) Uani 1 1 d . . . . .
H19 H 0.2089 0.5717 0.9023 0.067 Uiso 1 1 calc R U . . .
Cl1 Cl 1.29118(19) 1.0126(2) 1.10037(17) 0.0903(6) Uani 1 1 d . . . . .
Cl2 Cl 0.7503(3) 0.7511(3) 0.17304(18) 0.1125(8) Uani 1 1 d . . . . .
N1 N 0.7557(4) 0.7461(5) 0.7061(3) 0.0485(9) Uani 1 1 d . . . . .
O1 O 0.1620(7) 0.4267(8) 0.7882(5) 0.1101(17) Uani 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
C1 C2 1.376(7) . ?
C1 C6 1.377(6) . ?
C1 N1 1.418(6) . ?
C2 C3 1.371(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.341(7) . ?
C4 Cl1 1.744(5) . ?
C5 C6 1.384(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.380(7) . ?
C7 C8 1.383(7) . ?
C7 N1 1.403(6) . ?
C8 C9 1.359(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.362(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.362(9) . ?
C10 Cl2 1.744(5) . ?
C11 C12 1.366(8) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.377(7) . ?
C13 C18 1.391(6) . ?
C13 N1 1.406(6) . ?
C14 C15 1.372(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(7) . ?
C16 C19 1.513(7) . ?
C17 C18 1.361(7) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O1 1.061(7) . ?
C19 H19 0.9300 . ?

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 C1 C6 118.2(4) . . ?
C2 C1 N1 121.8(4) . . ?
C6 C1 N1 119.9(4) . . ?
C3 C2 C1 121.9(4) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 118.2(4) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 121.4(5) . . ?
C5 C4 Cl1 119.4(4) . . ?
C3 C4 Cl1 119.2(4) . . ?
C4 C5 C6 120.1(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 120.1(4) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C12 C7 C8 118.5(5) . . ?
C12 C7 N1 120.6(4) . . ?
C8 C7 N1 120.9(4) . . ?
C9 C8 C7 120.6(5) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 119.7(5) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 121.1(5) . . ?
C9 C10 Cl2 120.1(5) . . ?
C11 C10 Cl2 118.8(5) . . ?
C10 C11 C12 119.4(5) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C7 120.7(5) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
C14 C13 C18 118.3(4) . . ?
C14 C13 N1 122.0(4) . . ?
C18 C13 N1 119.7(4) . . ?
C15 C14 C13 121.1(4) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 120.3(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 118.5(4) . . ?
C17 C16 C19 122.0(5) . . ?
C15 C16 C19 119.5(4) . . ?
C18 C17 C16 121.1(4) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C13 120.6(4) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
O1 C19 C16 123.2(5) . . ?
O1 C19 H19 118.4 . . ?
C16 C19 H19 118.4 . . ?
C7 N1 C13 119.5(4) . . ?
C7 N1 C1 119.3(4) . . ?
C13 N1 C1 121.0(4) . . ?

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 C1 C2 C3 2.9(7) . . . . ?
N1 C1 C2 C3 -177.9(4) . . . . ?
C1 C2 C3 C4 -1.5(7) . . . . ?
C2 C3 C4 C5 -0.7(7) . . . . ?
C2 C3 C4 Cl1 178.3(4) . . . . ?
C3 C4 C5 C6 1.5(8) . . . . ?
Cl1 C4 C5 C6 -177.6(4) . . . . ?
C2 C1 C6 C5 -2.1(7) . . . . ?
N1 C1 C6 C5 178.6(4) . . . . ?
C4 C5 C6 C1 0.0(8) . . . . ?
C12 C7 C8 C9 1.0(7) . . . . ?
N1 C7 C8 C9 -178.5(4) . . . . ?
C7 C8 C9 C10 -2.4(8) . . . . ?
C8 C9 C10 C11 1.8(8) . . . . ?
C8 C9 C10 Cl2 -179.5(4) . . . . ?
C9 C10 C11 C12 0.2(8) . . . . ?
Cl2 C10 C11 C12 -178.5(4) . . . . ?
C10 C11 C12 C7 -1.6(8) . . . . ?
C8 C7 C12 C11 1.0(7) . . . . ?
N1 C7 C12 C11 -179.4(5) . . . . ?
C18 C13 C14 C15 2.8(7) . . . . ?
N1 C13 C14 C15 -178.1(4) . . . . ?
C13 C14 C15 C16 -0.6(7) . . . . ?
C14 C15 C16 C17 -1.4(7) . . . . ?
C14 C15 C16 C19 177.2(5) . . . . ?
C15 C16 C17 C18 1.2(7) . . . . ?
C19 C16 C17 C18 -177.4(5) . . . . ?
C16 C17 C18 C13 1.0(7) . . . . ?
C14 C13 C18 C17 -3.0(7) . . . . ?
N1 C13 C18 C17 177.9(4) . . . . ?
C17 C16 C19 O1 0.9(9) . . . . ?
C15 C16 C19 O1 -177.7(6) . . . . ?
C12 C7 N1 C13 46.5(6) . . . . ?
C8 C7 N1 C13 -133.9(4) . . . . ?
C12 C7 N1 C1 -129.8(5) . . . . ?
C8 C7 N1 C1 49.8(6) . . . . ?
C14 C13 N1 C7 -145.6(4) . . . . ?
C18 C13 N1 C7 33.5(6) . . . . ?
C14 C13 N1 C1 30.6(7) . . . . ?
C18 C13 N1 C1 -150.3(4) . . . . ?
C2 C1 N1 C7 -149.3(4) . . . . ?
C6 C1 N1 C7 29.9(6) . . . . ?
C2 C1 N1 C13 34.5(7) . . . . ?
C6 C1 N1 C13 -146.3(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
C18 H18 Cl2 0.93 2.94 3.382(5) 110.7 2_565
C9 H9 O1 0.93 2.59 3.497(7) 166.4 2_664
C3 H3 O1 0.93 2.60 3.488(8) 160.6 2_665
C18 H18 Cl2 0.93 2.94 3.382(5) 110.7 2_565
C9 H9 O1 0.93 2.59 3.497(7) 166.4 2_664
C3 H3 O1 0.93 2.60 3.488(8) 160.6 2_665

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_T
_database_code_depnum_ccdc_archive 'CCDC 1883640'
loop_
_audit_author_name
_audit_author_address
'Tu Jin'
;Wuhan University
China
;
_audit_update_record             
;
2018-12-07 deposited with the CCDC.	2019-08-31 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         'C19 H13 Br2 N O'
_chemical_formula_sum            'C19 H13 Br2 N O'
_chemical_formula_weight         431.12

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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, z+1/2'

_cell_length_a                   9.244(4)
_cell_length_b                   8.389(4)
_cell_length_c                   11.306(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.570(8)
_cell_angle_gamma                90
_cell_volume                     835.9(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    996
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      22.30

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.852
_shelx_estimated_absorpt_T_min   0.530
_shelx_estimated_absorpt_T_max   0.643
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5366
_diffrn_reflns_av_unetI/netI     0.1146
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.311
_diffrn_reflns_theta_max         24.403
_diffrn_reflns_theta_full        24.403
_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 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.921
_reflns_number_total             2547
_reflns_number_gt                1637
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_max     0.844
_reflns_Friedel_fraction_full    0.844

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0611P)²+0.7115P] 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 507 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.04(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2547
_refine_ls_number_parameters     182
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1605
_refine_ls_wR_factor_gt          0.1391
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.961
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.002

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
Br1 Br 0.5372(4) 0.7527(5) 1.4832(3) 0.1011(15) Uani 0.712(8) 1 d . . P A 1
O1 O 1.138(2) 1.074(2) 0.869(2) 0.095(6) Uani 0.712(8) 1 d D . P A 1
C19 C 1.044(3) 0.972(4) 0.825(3) 0.065(3) Uani 0.712(8) 1 d D . P A 1
H19 H 1.0556 0.9234 0.7543 0.078 Uiso 0.712(8) 1 calc R U P A 1
Br2 Br -0.0018(2) 0.4895(3) 0.54903(19) 0.0878(8) Uani 1 1 d . . . . .
C1 C 0.5355(9) 0.7550(10) 1.0709(5) 0.038(3) Uani 1 1 d G . . . .
C2 C 0.4098(8) 0.8142(10) 1.0998(7) 0.056(4) Uani 1 1 d G . . . .
H2 H 0.3272 0.8532 1.0372 0.067 Uiso 1 1 calc R U . . .
C3 C 0.4075(9) 0.8149(11) 1.2221(7) 0.056(4) Uani 1 1 d DG . . . .
H3 H 0.3233 0.8545 1.2414 0.067 Uiso 1 1 calc R U . . .
C4 C 0.5309(10) 0.7566(11) 1.3157(6) 0.055(4) Uani 1 1 d DG . . . .
C5 C 0.6567(9) 0.6974(10) 1.2869(6) 0.060(4) Uani 1 1 d DG . . . .
H5 H 0.7393 0.6584 1.3494 0.072 Uiso 1 1 calc R U . . .
C6 C 0.6590(8) 0.6966(10) 1.1645(7) 0.052(3) Uani 1 1 d G . . . .
H6 H 0.7431 0.6571 1.1452 0.062 Uiso 1 1 calc R U . . .
N1 N 0.5383(13) 0.7573(14) 0.9486(9) 0.048(3) Uani 1 1 d . . . . .
C7 C 0.6713(8) 0.8022(10) 0.9211(7) 0.045(3) Uani 1 1 d G . . . .
C8 C 0.7586(9) 0.9250(10) 0.9894(6) 0.053(4) Uani 1 1 d G . . . .
H8 H 0.7328 0.9698 1.0556 0.063 Uiso 1 1 calc R U . . .
C9 C 0.8844(9) 0.9808(9) 0.9589(8) 0.060(4) Uani 1 1 d DG . . . .
H9 H 0.9428 1.0629 1.0046 0.072 Uiso 1 1 calc R U . . .
C10 C 0.9229(8) 0.9138(10) 0.8600(8) 0.051(3) Uani 1 1 d DG . . . .
C11 C 0.8356(9) 0.7911(10) 0.7917(6) 0.049(3) Uani 1 1 d DG . . . .
H11 H 0.8613 0.7463 0.7255 0.059 Uiso 1 1 calc R U . . .
C12 C 0.7098(8) 0.7353(9) 0.8222(7) 0.048(3) Uani 1 1 d G . . . .
H12 H 0.6514 0.6531 0.7765 0.058 Uiso 1 1 calc R U . . .
Br1' Br 1.0819(7) 1.0102(10) 0.8249(7) 0.065(3) Uani 0.288(8) 1 d . . P A 2
C13 C 0.4101(8) 0.6982(9) 0.8546(6) 0.042(3) Uani 1 1 d G . . . .
C14 C 0.3222(9) 0.5786(10) 0.8833(6) 0.053(3) Uani 1 1 d G . . . .
H14 H 0.3470 0.5385 0.9636 0.063 Uiso 1 1 calc R U . . .
C15 C 0.1971(9) 0.5189(9) 0.7919(8) 0.053(4) Uani 1 1 d G . . . .
H15 H 0.1383 0.4389 0.8112 0.063 Uiso 1 1 calc R U . . .
C16 C 0.1600(8) 0.5789(10) 0.6719(7) 0.056(4) Uani 1 1 d G . . . .
C17 C 0.2479(9) 0.6985(10) 0.6432(6) 0.047(3) Uani 1 1 d G . . . .
H17 H 0.2231 0.7386 0.5629 0.057 Uiso 1 1 calc R U . . .
C18 C 0.3729(8) 0.7582(8) 0.7345(7) 0.042(3) Uani 1 1 d G . . . .
H18 H 0.4318 0.8382 0.7153 0.050 Uiso 1 1 calc R U . . .
O1' O 0.635(4) 0.721(6) 1.527(4) 0.095(6) Uani 0.288(8) 1 d D . P A 2
C19' C 0.527(2) 0.758(2) 1.4374(14) 0.1011(15) Uani 0.288(8) 1 d D . P A 2
H19' H 0.4372 0.7896 1.4521 0.121 Uiso 0.288(8) 1 calc R 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
Br1 C4 1.878(6) . ?
O1 C19 1.215(13) . ?
C19 C10 1.384(13) . ?
C19 H19 0.9300 . ?
Br2 C16 1.864(6) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 N1 1.392(12) . ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C19' 1.389(14) . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N1 C7 1.408(13) . ?
N1 C13 1.421(12) . ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C8 C9 1.3900 . ?
C8 H8 0.9300 . ?
C9 C10 1.3900 . ?
C9 H9 0.9300 . ?
C10 C11 1.3900 . ?
C10 Br1' 1.824(8) . ?
C11 C12 1.3900 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.3900 . ?
C13 C18 1.3900 . ?
C14 C15 1.3900 . ?
C14 H14 0.9300 . ?
C15 C16 1.3900 . ?
C15 H15 0.9300 . ?
C16 C17 1.3900 . ?
C17 C18 1.3900 . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
O1' C19' 1.233(14) . ?
C19' H19' 0.9300 . ?

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
O1 C19 C10 132.0(16) . . ?
O1 C19 H19 114.0 . . ?
C10 C19 H19 114.0 . . ?
C2 C1 C6 120.0 . . ?
C2 C1 N1 119.7(7) . . ?
C6 C1 N1 120.3(7) . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C19' C4 C3 119.2(6) . . ?
C19' C4 C5 120.8(6) . . ?
C3 C4 C5 120.0 . . ?
C3 C4 Br1 122.8(5) . . ?
C5 C4 Br1 117.2(5) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C1 N1 C7 120.2(9) . . ?
C1 N1 C13 118.5(9) . . ?
C7 N1 C13 121.0(8) . . ?
C8 C7 C12 120.0 . . ?
C8 C7 N1 118.3(6) . . ?
C12 C7 N1 121.5(6) . . ?
C9 C8 C7 120.0 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C19 C10 C9 121.0(6) . . ?
C19 C10 C11 119.0(6) . . ?
C9 C10 C11 120.0 . . ?
C9 C10 Br1' 114.5(5) . . ?
C11 C10 Br1' 125.3(5) . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 120.0 . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
C14 C13 C18 120.0 . . ?
C14 C13 N1 119.5(6) . . ?
C18 C13 N1 120.5(6) . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 120.0 . . ?
C17 C16 Br2 120.7(4) . . ?
C15 C16 Br2 119.2(5) . . ?
C16 C17 C18 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 120.0 . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
O1' C19' C4 124(3) . . ?
O1' C19' H19' 118.1 . . ?
C4 C19' H19' 118.2 . . ?

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
C6 C1 C2 C3 0.0 . . . . ?
N1 C1 C2 C3 -178.8(9) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C19' 180.0(4) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C2 C3 C4 Br1 -179.9(7) . . . . ?
C19' C4 C5 C6 -180.0(4) . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
Br1 C4 C5 C6 179.9(6) . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
N1 C1 C6 C5 178.8(9) . . . . ?
C2 C1 N1 C7 137.7(8) . . . . ?
C6 C1 N1 C7 -41.1(13) . . . . ?
C2 C1 N1 C13 -48.6(12) . . . . ?
C6 C1 N1 C13 132.6(8) . . . . ?
C1 N1 C7 C8 -38.0(12) . . . . ?
C13 N1 C7 C8 148.4(8) . . . . ?
C1 N1 C7 C12 146.9(8) . . . . ?
C13 N1 C7 C12 -26.6(13) . . . . ?
C12 C7 C8 C9 0.0 . . . . ?
N1 C7 C8 C9 -175.2(8) . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
O1 C19 C10 C9 4(6) . . . . ?
O1 C19 C10 C11 -178(4) . . . . ?
C8 C9 C10 C19 177(2) . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C8 C9 C10 Br1' 175.6(7) . . . . ?
C19 C10 C11 C12 -177(2) . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
Br1' C10 C11 C12 -175.1(8) . . . . ?
C10 C11 C12 C7 0.0 . . . . ?
C8 C7 C12 C11 0.0 . . . . ?
N1 C7 C12 C11 175.0(9) . . . . ?
C1 N1 C13 C14 -29.8(12) . . . . ?
C7 N1 C13 C14 143.9(8) . . . . ?
C1 N1 C13 C18 150.7(8) . . . . ?
C7 N1 C13 C18 -35.6(13) . . . . ?
C18 C13 C14 C15 0.0 . . . . ?
N1 C13 C14 C15 -179.5(8) . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C14 C15 C16 Br2 176.7(6) . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
Br2 C16 C17 C18 -176.7(6) . . . . ?
C16 C17 C18 C13 0.0 . . . . ?
C14 C13 C18 C17 0.0 . . . . ?
N1 C13 C18 C17 179.5(8) . . . . ?
C3 C4 C19' O1' -174(3) . . . . ?
C5 C4 C19' O1' 6(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
C17 H17 O1 0.93 2.62 3.52(2) 163.3 2_474
C11 H11 O1' 0.93 2.57 3.06(4) 113.4 1_554
C8 H8 Br1 0.93 2.91 3.379(8) 112.7 2_574
C6 H6 Br2 0.93 3.13 4.056(7) 172.9 2_665
C5 H5 Br2 0.93 3.09 4.019(7) 173.3 1_656
C3 H3 Br1' 0.93 2.90 3.830(9) 174.2 2_475
C3 H3 O1 0.93 2.62 3.51(2) 160.5 2_475
C2 H2 Br1' 0.93 3.06 3.983(11) 173.2 1_455

_refine_diff_density_max         0.488
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_mo_180123D_0m
_database_code_depnum_ccdc_archive 'CCDC 1883641'
loop_
_audit_author_name
_audit_author_address
'Tu Jin'
;Wuhan University
China
;
_audit_update_record             
;
2018-12-07 deposited with the CCDC.	2019-08-31 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         ?
_chemical_formula_sum            'C19 H13 F2 N O'
_chemical_formula_weight         309.30

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   13.173(4)
_cell_length_b                   13.212(4)
_cell_length_c                   17.216(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2996.2(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1145
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      18.03

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19399
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_av_R_equivalents  0.0930
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.366
_diffrn_reflns_theta_max         24.776
_diffrn_reflns_theta_full        24.776
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2564
_reflns_number_gt                1447
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0462P)²+0.0716P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0031(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2564
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1206
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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 -0.02077(17) 0.55392(19) 0.32981(13) 0.0501(6) Uani 1 1 d . . . A 1
C2 C -0.03784(19) 0.4635(2) 0.36613(14) 0.0629(7) Uani 1 1 d . . . A 1
H2 H -0.0075 0.4048 0.3474 0.075 Uiso 1 1 calc R U . A 1
C3 C -0.0997(2) 0.4593(2) 0.43016(14) 0.0696(8) Uani 1 1 d . . . A 1
H3 H -0.1121 0.3981 0.4549 0.084 Uiso 1 1 calc R U . A 1
C4 C -0.14198(19) 0.5456(2) 0.45652(14) 0.0641(7) Uani 1 1 d . . . A 1
C5 C -0.1254(2) 0.6360(2) 0.42291(15) 0.0709(8) Uani 1 1 d . . . A 1
H5 H -0.1548 0.6946 0.4428 0.085 Uiso 1 1 calc R U . A 1
C6 C -0.06445(18) 0.6397(2) 0.35884(14) 0.0621(7) Uani 1 1 d . . . A 1
H6 H -0.0525 0.7015 0.3346 0.074 Uiso 1 1 calc R U . A 1
C7 C 0.12655(17) 0.62832(18) 0.26823(13) 0.0513(6) Uani 1 1 d . . . B 1
C8 C 0.19409(19) 0.62039(19) 0.32795(14) 0.0665(7) Uani 1 1 d . . . B 1
H8 H 0.1867 0.5692 0.3646 0.080 Uiso 1 1 calc R U . B 1
C9 C 0.2731(2) 0.6880(2) 0.33402(17) 0.0792(8) Uani 1 1 d . . . B 1
H9 H 0.3196 0.6834 0.3745 0.095 Uiso 1 1 calc R U . B 1
C10 C 0.2815(2) 0.7606(2) 0.28015(18) 0.0740(8) Uani 1 1 d . . . B 1
C11 C 0.2171(2) 0.7706(2) 0.21998(15) 0.0700(8) Uani 1 1 d . . . B 1
H11 H 0.2260 0.8214 0.1832 0.084 Uiso 1 1 calc R U . B 1
C12 C 0.13801(19) 0.70373(19) 0.21449(13) 0.0587(7) Uani 1 1 d . . . B 1
H12 H 0.0918 0.7096 0.1739 0.070 Uiso 1 1 calc R U . B 1
C13 C 0.02453(18) 0.50350(17) 0.19762(13) 0.0506(6) Uani 1 1 d . . . C 1
C14 C -0.07063(18) 0.46304(18) 0.18387(14) 0.0604(7) Uani 1 1 d . . . C 1
H14 H -0.1227 0.4740 0.2194 0.072 Uiso 1 1 calc R U . C 1
C15 C -0.08871(19) 0.40753(19) 0.11897(13) 0.0621(7) Uani 1 1 d . . . C 1
H15 H -0.1534 0.3816 0.1106 0.075 Uiso 1 1 calc R U . C 1
C16 C -0.0139(2) 0.38872(18) 0.06547(14) 0.0562(6) Uani 1 1 d . . . C 1
C17 C 0.0813(2) 0.42956(18) 0.07871(13) 0.0593(7) Uani 1 1 d . . . C 1
H17 H 0.1330 0.4184 0.0429 0.071 Uiso 1 1 calc R U . C 1
C18 C 0.10045(19) 0.48582(17) 0.14336(13) 0.0560(6) Uani 1 1 d . . . C 1
H18 H 0.1649 0.5126 0.1512 0.067 Uiso 1 1 calc R U . C 1
C19 C -0.0358(4) 0.3285(2) -0.00298(17) 0.0740(8) Uani 1 1 d . . . C 1
H19 H -0.1031 0.3094 -0.0099 0.089 Uiso 0.773(7) 1 d R U P D 1
H19' H 0.0174 0.3268 -0.0385 0.089 Uiso 0.227(7) 1 d R U P D 2
F1 F -0.20304(12) 0.54078(13) 0.51940(8) 0.0998(6) Uani 1 1 d . . . . .
F2 F 0.35921(14) 0.82669(16) 0.28635(11) 0.1260(8) Uani 1 1 d . . . . .
N1 N 0.04363(14) 0.55998(15) 0.26357(10) 0.0575(6) Uani 1 1 d . . . . .
O1 O 0.0219(2) 0.3013(2) -0.05061(16) 0.0866(12) Uani 0.773(7) 1 d . . P C 1
O1' O -0.1074(9) 0.2821(8) -0.0205(5) 0.101(5) Uani 0.227(7) 1 d . . P D 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
C1 C6 1.366(3) . ?
C1 C2 1.367(3) . ?
C1 N1 1.424(3) . ?
C2 C3 1.372(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.347(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.346(3) . ?
C4 F1 1.350(3) . ?
C5 C6 1.365(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.364(3) . ?
C7 C12 1.368(3) . ?
C7 N1 1.419(3) . ?
C8 C9 1.375(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.339(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.345(4) . ?
C10 F2 1.350(3) . ?
C11 C12 1.369(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 N1 1.382(3) . ?
C13 C14 1.383(3) . ?
C13 C18 1.388(3) . ?
C14 C15 1.358(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(3) . ?
C16 C19 1.451(4) . ?
C17 C18 1.362(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O1 1.174(3) . ?
C19 H19 0.9300 . ?

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 C1 C2 119.2(2) . . ?
C6 C1 N1 119.8(2) . . ?
C2 C1 N1 120.9(2) . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 122.6(2) . . ?
C5 C4 F1 118.9(3) . . ?
C3 C4 F1 118.5(3) . . ?
C4 C5 C6 118.3(3) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 120.9(2) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C8 C7 C12 119.6(2) . . ?
C8 C7 N1 119.7(2) . . ?
C12 C7 N1 120.7(2) . . ?
C7 C8 C9 120.1(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 118.4(3) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C9 C10 C11 123.5(3) . . ?
C9 C10 F2 118.1(3) . . ?
C11 C10 F2 118.4(3) . . ?
C10 C11 C12 118.0(3) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
C7 C12 C11 120.5(2) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
N1 C13 C14 120.9(2) . . ?
N1 C13 C18 120.8(2) . . ?
C14 C13 C18 118.2(2) . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 121.6(2) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C17 118.0(2) . . ?
C15 C16 C19 120.1(3) . . ?
C17 C16 C19 121.9(3) . . ?
C18 C17 C16 121.0(2) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C13 120.5(2) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
O1 C19 C16 127.3(4) . . ?
O1 C19 H19 116.3 . . ?
C16 C19 H19 116.3 . . ?
C13 N1 C7 122.01(19) . . ?
C13 N1 C1 121.3(2) . . ?
C7 N1 C1 116.68(18) . . ?

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 C1 C2 C3 1.1(4) . . . . ?
N1 C1 C2 C3 179.6(2) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C2 C3 C4 F1 179.8(2) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
F1 C4 C5 C6 -179.3(2) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
N1 C1 C6 C5 -179.1(2) . . . . ?
C12 C7 C8 C9 0.1(4) . . . . ?
N1 C7 C8 C9 -178.3(2) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C8 C9 C10 C11 -0.5(5) . . . . ?
C8 C9 C10 F2 -179.9(2) . . . . ?
C9 C10 C11 C12 1.1(4) . . . . ?
F2 C10 C11 C12 -179.5(2) . . . . ?
C8 C7 C12 C11 0.5(4) . . . . ?
N1 C7 C12 C11 178.8(2) . . . . ?
C10 C11 C12 C7 -1.1(4) . . . . ?
N1 C13 C14 C15 -179.9(2) . . . . ?
C18 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C16 0.7(4) . . . . ?
C14 C15 C16 C17 -1.1(4) . . . . ?
C14 C15 C16 C19 179.6(2) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C19 C16 C17 C18 -180.0(2) . . . . ?
C16 C17 C18 C13 0.0(4) . . . . ?
N1 C13 C18 C17 179.6(2) . . . . ?
C14 C13 C18 C17 -0.4(3) . . . . ?
C15 C16 C19 O1 -174.8(3) . . . . ?
C17 C16 C19 O1 5.9(5) . . . . ?
C14 C13 N1 C7 -159.3(2) . . . . ?
C18 C13 N1 C7 20.7(3) . . . . ?
C14 C13 N1 C1 19.3(3) . . . . ?
C18 C13 N1 C1 -160.7(2) . . . . ?
C8 C7 N1 C13 -126.1(2) . . . . ?
C12 C7 N1 C13 55.5(3) . . . . ?
C8 C7 N1 C1 55.3(3) . . . . ?
C12 C7 N1 C1 -123.1(2) . . . . ?
C6 C1 N1 C13 -123.9(2) . . . . ?
C2 C1 N1 C13 57.6(3) . . . . ?
C6 C1 N1 C7 54.7(3) . . . . ?
C2 C1 N1 C7 -123.7(2) . . . . ?

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
C12 H12 O1 0.93 2.60 3.521(4) 170.1 5_565
C9 H9 O1 0.93 2.46 3.356(4) 160.9 2_565
C8 H8 F1 0.93 2.48 3.384(3) 164.5 5_566
C2 H2 F2 0.93 2.45 3.270(3) 147.5 8_655

_refine_diff_density_max         0.151
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.032

