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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_d8v19305_0m
_database_code_depnum_ccdc_archive 'CCDC 1961106'
loop_
_audit_author_name
_audit_author_address
mengyuandu
;Shanghai University
China
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2020-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Br F3 N2 O2'
_chemical_formula_weight         379.18

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.2263(4)
_cell_length_b                   15.7424(7)
_cell_length_c                   11.8768(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.325(2)
_cell_angle_gamma                90
_cell_volume                     1637.56(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    6954
_cell_measurement_theta_min      5.329
_cell_measurement_theta_max      55.016

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.547
_shelx_estimated_absorpt_T_min   0.671
_shelx_estimated_absorpt_T_max   0.750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4692
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(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            16250
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.588
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3207
_reflns_number_gt                2687
_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-2013 (Sheldrick, 2013)'
_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)+(0.0359P)²+0.6839P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0023(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3207
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0753
_refine_ls_wR_factor_gt          0.0706
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_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
Br1 Br 1.12257(3) 0.87770(2) 0.84319(2) 0.03849(11) Uani 1 1 d . . . . .
F1 F 0.83397(18) 0.39169(9) 0.69046(17) 0.0595(5) Uani 1 1 d . . . . .
F2 F 1.02597(16) 0.46193(10) 0.80139(16) 0.0594(5) Uani 1 1 d . . . . .
F3 F 0.93024(16) 0.49319(10) 0.61680(15) 0.0532(4) Uani 1 1 d . . . . .
O1 O 0.40497(16) 0.57494(9) 0.55628(14) 0.0302(4) Uani 1 1 d . . . . .
O2 O 0.54220(16) 0.61970(9) 0.74027(14) 0.0311(4) Uani 1 1 d . . . . .
N1 N 0.64996(19) 0.53456(12) 0.64124(17) 0.0264(4) Uani 1 1 d . . . . .
H1 H 0.640(3) 0.5006(16) 0.585(2) 0.032(7) Uiso 1 1 d . . . . .
N2 N 0.7320(3) 0.46462(18) 0.9273(2) 0.0632(7) Uani 1 1 d . . . . .
C1 C 0.7867(2) 0.53231(13) 0.7424(2) 0.0294(5) Uani 1 1 d . . . . .
C2 C 0.8958(3) 0.46906(16) 0.7115(3) 0.0433(6) Uani 1 1 d . . . . .
C3 C 0.7550(3) 0.49547(16) 0.8494(2) 0.0408(6) Uani 1 1 d . . . . .
C4 C 0.8654(2) 0.61939(13) 0.7707(2) 0.0265(5) Uani 1 1 d . . . . .
C5 C 0.9432(3) 0.64359(15) 0.8854(2) 0.0338(5) Uani 1 1 d . . . . .
H5 H 0.9451 0.6069 0.9494 0.041 Uiso 1 1 calc R U . . .
C6 C 1.0186(3) 0.72105(15) 0.9081(2) 0.0357(5) Uani 1 1 d . . . . .
H6 H 1.0726 0.7376 0.9871 0.043 Uiso 1 1 calc R U . . .
C7 C 1.0140(2) 0.77326(13) 0.8146(2) 0.0292(5) Uani 1 1 d . . . . .
C8 C 0.9347(3) 0.75111(14) 0.6996(2) 0.0335(5) Uani 1 1 d . . . . .
H8 H 0.9309 0.7885 0.6360 0.040 Uiso 1 1 calc R U . . .
C9 C 0.8608(2) 0.67361(15) 0.6781(2) 0.0322(5) Uani 1 1 d . . . . .
H9 H 0.8063 0.6575 0.5990 0.039 Uiso 1 1 calc R U . . .
C10 C 0.5216(2) 0.57699(13) 0.6405(2) 0.0251(5) Uani 1 1 d . . . . .
C11 C 0.4143(3) 0.66615(15) 0.7639(2) 0.0341(5) Uani 1 1 d . . . . .
C12 C 0.4901(3) 0.70113(19) 0.8865(2) 0.0537(7) Uani 1 1 d . . . . .
H12A H 0.5252 0.6541 0.9425 0.081 Uiso 1 1 calc R U . . .
H12B H 0.4167 0.7358 0.9107 0.081 Uiso 1 1 calc R U . . .
H12C H 0.5776 0.7363 0.8861 0.081 Uiso 1 1 calc R U . . .
C13 C 0.3612(3) 0.73685(17) 0.6743(2) 0.0456(7) Uani 1 1 d . . . . .
H13A H 0.4492 0.7709 0.6721 0.068 Uiso 1 1 calc R U . . .
H13B H 0.2885 0.7730 0.6970 0.068 Uiso 1 1 calc R U . . .
H13C H 0.3113 0.7125 0.5957 0.068 Uiso 1 1 calc R U . . .
C14 C 0.2889(3) 0.60330(18) 0.7628(3) 0.0517(7) Uani 1 1 d . . . . .
H14A H 0.2408 0.5827 0.6817 0.078 Uiso 1 1 calc R U . . .
H14B H 0.2122 0.6314 0.7911 0.078 Uiso 1 1 calc R U . . .
H14C H 0.3329 0.5553 0.8148 0.078 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
Br1 C7 1.899(2) . ?
F1 C2 1.335(3) . ?
F2 C2 1.338(3) . ?
F3 C2 1.317(3) . ?
O1 C10 1.218(2) . ?
O2 C10 1.324(3) . ?
O2 C11 1.488(3) . ?
N1 C10 1.357(3) . ?
N1 C1 1.444(3) . ?
N1 H1 0.84(2) . ?
N2 C3 1.123(3) . ?
C1 C3 1.507(3) . ?
C1 C4 1.538(3) . ?
C1 C2 1.539(3) . ?
C4 C5 1.379(3) . ?
C4 C9 1.382(3) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.371(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.376(3) . ?
C8 C9 1.382(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C11 C12 1.508(4) . ?
C11 C13 1.511(4) . ?
C11 C14 1.519(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C10 O2 C11 121.31(17) . . ?
C10 N1 C1 123.38(19) . . ?
C10 N1 H1 115.5(17) . . ?
C1 N1 H1 119.8(17) . . ?
N1 C1 C3 111.12(18) . . ?
N1 C1 C4 112.88(18) . . ?
C3 C1 C4 111.26(19) . . ?
N1 C1 C2 106.44(19) . . ?
C3 C1 C2 105.5(2) . . ?
C4 C1 C2 109.24(17) . . ?
F3 C2 F1 107.9(2) . . ?
F3 C2 F2 107.9(2) . . ?
F1 C2 F2 107.2(2) . . ?
F3 C2 C1 111.6(2) . . ?
F1 C2 C1 111.2(2) . . ?
F2 C2 C1 110.7(2) . . ?
N2 C3 C1 177.0(3) . . ?
C5 C4 C9 119.5(2) . . ?
C5 C4 C1 121.7(2) . . ?
C9 C4 C1 118.8(2) . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 118.9(2) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C8 121.6(2) . . ?
C6 C7 Br1 119.58(17) . . ?
C8 C7 Br1 118.84(17) . . ?
C7 C8 C9 119.0(2) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C8 C9 C4 120.5(2) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
O1 C10 O2 126.13(19) . . ?
O1 C10 N1 122.5(2) . . ?
O2 C10 N1 111.40(18) . . ?
O2 C11 C12 101.98(18) . . ?
O2 C11 C13 109.32(18) . . ?
C12 C11 C13 111.1(2) . . ?
O2 C11 C14 108.98(18) . . ?
C12 C11 C14 111.5(2) . . ?
C13 C11 C14 113.3(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C10 N1 C1 C3 58.8(3) . . . . ?
C10 N1 C1 C4 -67.0(3) . . . . ?
C10 N1 C1 C2 173.1(2) . . . . ?
N1 C1 C2 F3 60.5(2) . . . . ?
C3 C1 C2 F3 178.61(19) . . . . ?
C4 C1 C2 F3 -61.7(3) . . . . ?
N1 C1 C2 F1 -60.1(3) . . . . ?
C3 C1 C2 F1 58.1(3) . . . . ?
C4 C1 C2 F1 177.8(2) . . . . ?
N1 C1 C2 F2 -179.23(19) . . . . ?
C3 C1 C2 F2 -61.1(2) . . . . ?
C4 C1 C2 F2 58.6(3) . . . . ?
N1 C1 C4 C5 147.1(2) . . . . ?
C3 C1 C4 C5 21.4(3) . . . . ?
C2 C1 C4 C5 -94.7(3) . . . . ?
N1 C1 C4 C9 -34.5(3) . . . . ?
C3 C1 C4 C9 -160.19(19) . . . . ?
C2 C1 C4 C9 83.7(2) . . . . ?
C9 C4 C5 C6 -1.1(3) . . . . ?
C1 C4 C5 C6 177.3(2) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
C5 C6 C7 C8 1.0(3) . . . . ?
C5 C6 C7 Br1 -177.73(17) . . . . ?
C6 C7 C8 C9 -1.3(3) . . . . ?
Br1 C7 C8 C9 177.40(17) . . . . ?
C7 C8 C9 C4 0.4(3) . . . . ?
C5 C4 C9 C8 0.8(3) . . . . ?
C1 C4 C9 C8 -177.7(2) . . . . ?
C11 O2 C10 O1 5.1(3) . . . . ?
C11 O2 C10 N1 -175.52(17) . . . . ?
C1 N1 C10 O1 -176.48(19) . . . . ?
C1 N1 C10 O2 4.1(3) . . . . ?
C10 O2 C11 C12 178.2(2) . . . . ?
C10 O2 C11 C13 -64.1(3) . . . . ?
C10 O2 C11 C14 60.2(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
C14 H14A O1 0.98 2.44 3.002(3) 116.1 .
C13 H13C O1 0.98 2.43 2.997(3) 116.3 .
C13 H13B Br1 0.98 3.12 4.070(3) 163.2 1_455
N1 H1 O1 0.84(2) 1.99(3) 2.826(2) 174(2) 3_666

_refine_diff_density_max         0.521
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4

