# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_18
_database_code_depnum_ccdc_archive 'CCDC 1850877'
_audit_update_record             
;
2018-06-25 deposited with the CCDC.
2018-07-12 downloaded from the CCDC.
;
_audit_creation_date             2018-06-25
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C4 H3 F3 O2'
_chemical_formula_moiety         'C4 H3 F3 O2'
_chemical_formula_weight         140.06
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/n
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.165(2)
_cell_length_b                   11.201(5)
_cell_length_c                   8.564(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.626(12)
_cell_angle_gamma                90.0000
_cell_volume                     485.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1520
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.40
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.917
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280.00
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.797
_exptl_absorpt_correction_T_max  0.989

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            5412
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_theta_max         25.387
_diffrn_reflns_theta_min         3.034
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             885
_reflns_number_gt                775
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.0912
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         885
_refine_ls_number_parameters     85
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0342P)²+0.4784P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.2399(3) 0.01249(13) 0.23277(18) 0.0333(4) Uani 1 1 d . . . . .
F2 F 0.2735(3) -0.10454(14) -0.03731(17) 0.0385(4) Uani 1 1 d . . . . .
F3 F 0.6743(3) -0.16834(14) 0.05936(17) 0.0359(4) Uani 1 1 d . . . . .
O4 O 0.8503(3) -0.11873(15) 0.4004(2) 0.0297(4) Uani 1 1 d . . . . .
O5 O 0.6961(3) 0.06829(15) 0.4059(2) 0.0303(4) Uani 1 1 d D . . . .
H5 H 0.868(3) 0.091(3) 0.464(3) 0.045 Uiso 1 1 d D U . . .
C1 C 0.4328(4) -0.0721(2) 0.2448(3) 0.0253(5) Uani 1 1 d . . . . .
C2 C 0.4409(4) -0.1398(2) 0.0959(3) 0.0275(5) Uani 1 1 d . . . . .
C3 C 0.3423(5) -0.2024(2) 0.2206(3) 0.0289(5) Uani 1 1 d . . . . .
H3A H 0.456379 -0.264653 0.281264 0.035 Uiso 1 1 calc R U . . .
H3B H 0.150261 -0.218819 0.202892 0.035 Uiso 1 1 calc R U . . .
C4 C 0.6799(4) -0.0412(2) 0.3600(3) 0.0232(5) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.364(3) . ?
F2 C2 1.344(3) . ?
F3 C2 1.344(3) . ?
O4 C4 1.235(3) . ?
O5 C4 1.285(3) . ?
O5 H5 0.960(10) . ?
C1 C4 1.488(3) . ?
C1 C2 1.491(3) . ?
C1 C3 1.534(3) . ?
C2 C3 1.453(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?

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
C4 O5 H5 114.4(19) . . ?
F1 C1 C4 113.83(19) . . ?
F1 C1 C2 115.76(19) . . ?
C4 C1 C2 121.14(19) . . ?
F1 C1 C3 116.92(18) . . ?
C4 C1 C3 120.56(19) . . ?
C2 C1 C3 57.40(15) . . ?
F3 C2 F2 109.04(19) . . ?
F3 C2 C3 121.3(2) . . ?
F2 C2 C3 120.3(2) . . ?
F3 C2 C1 120.09(19) . . ?
F2 C2 C1 116.9(2) . . ?
C3 C2 C1 62.78(16) . . ?
C2 C3 C1 59.82(16) . . ?
C2 C3 H3A 117.8 . . ?
C1 C3 H3A 117.8 . . ?
C2 C3 H3B 117.8 . . ?
C1 C3 H3B 117.8 . . ?
H3A C3 H3B 114.9 . . ?
O4 C4 O5 125.9(2) . . ?
O4 C4 C1 119.3(2) . . ?
O5 C4 C1 114.78(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 F3 141.1(2) . . . . ?
C4 C1 C2 F3 -3.6(3) . . . . ?
C3 C1 C2 F3 -112.2(2) . . . . ?
F1 C1 C2 F2 5.3(3) . . . . ?
C4 C1 C2 F2 -139.4(2) . . . . ?
C3 C1 C2 F2 112.0(2) . . . . ?
F1 C1 C2 C3 -106.7(2) . . . . ?
C4 C1 C2 C3 108.6(2) . . . . ?
F3 C2 C3 C1 110.3(2) . . . . ?
F2 C2 C3 C1 -106.8(2) . . . . ?
F1 C1 C3 C2 104.7(2) . . . . ?
C4 C1 C3 C2 -109.6(2) . . . . ?
F1 C1 C4 O4 168.00(19) . . . . ?
C2 C1 C4 O4 -46.7(3) . . . . ?
C3 C1 C4 O4 21.3(3) . . . . ?
F1 C1 C4 O5 -13.4(3) . . . . ?
C2 C1 C4 O5 131.9(2) . . . . ?
C3 C1 C4 O5 -160.1(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
_geom_hbond_publ_flag
O5 H5 O4 0.960(10) 1.697(12) 2.644(2) 168(3) 3_756 yes

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate'
####################################################################### 
# 
# 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_19a
_database_code_depnum_ccdc_archive 'CCDC 1850881'
_audit_update_record             
;
2018-06-25 deposited with the CCDC.
2018-07-12 downloaded from the CCDC.
;
_audit_creation_date             2018-06-25
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C10 H8 F3 N O'
_chemical_formula_moiety         'C10 H8 F3 N O'
_chemical_formula_weight         215.17
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/n
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.6878(14)
_cell_length_b                   20.542(5)
_cell_length_c                   8.921(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 107.525(6)
_cell_angle_gamma                90.0000
_cell_volume                     993.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1565
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      26.50
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440.00
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_T_max  0.999

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            11961
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         1.983
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1814
_reflns_number_gt                1474
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1170
_refine_ls_wR_factor_gt          0.1065
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1814
_refine_ls_number_parameters     140
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0420P)²+0.5670P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.1117(2) 0.19361(7) 0.20576(15) 0.0516(4) Uani 1 1 d . . . . .
F2 F 0.1751(3) 0.06469(7) 0.1896(2) 0.0703(5) Uani 1 1 d . . . . .
F3 F 0.5524(3) 0.06829(7) 0.3478(2) 0.0724(5) Uani 1 1 d . . . . .
O4 O 0.6881(3) 0.19434(7) 0.49917(18) 0.0484(4) Uani 1 1 d . . . . .
N5 N 0.5102(3) 0.26684(8) 0.3034(2) 0.0341(4) Uani 1 1 d D . . . .
H5 H 0.372(3) 0.2754(11) 0.2132(19) 0.050(7) Uiso 1 1 d D . . . .
C1 C 0.3038(4) 0.16704(11) 0.3214(2) 0.0384(5) Uani 1 1 d . . . . .
C2 C 0.3292(4) 0.09560(12) 0.3139(3) 0.0497(6) Uani 1 1 d . . . . .
C3 C 0.2326(5) 0.12094(12) 0.4352(3) 0.0546(7) Uani 1 1 d . . . . .
H3A H 0.340998 0.119497 0.545284 0.065 Uiso 1 1 calc R U . . .
H3B H 0.054983 0.114637 0.422066 0.065 Uiso 1 1 calc R U . . .
C4 C 0.5213(4) 0.21108(10) 0.3827(2) 0.0342(5) Uani 1 1 d . . . . .
C6 C 0.6830(4) 0.31890(9) 0.3405(2) 0.0320(5) Uani 1 1 d . . . . .
C7 C 0.9309(4) 0.30976(11) 0.4210(3) 0.0391(5) Uani 1 1 d . . . . .
H7 H 0.991584 0.267605 0.456235 0.047 Uiso 1 1 calc R U . . .
C8 C 1.0888(4) 0.36283(11) 0.4494(3) 0.0449(6) Uani 1 1 d . . . . .
H8 H 1.258181 0.356842 0.505262 0.054 Uiso 1 1 calc R U . . .
C9 C 1.0034(4) 0.42422(11) 0.3978(3) 0.0448(6) Uani 1 1 d . . . . .
H9 H 1.113529 0.460160 0.416780 0.054 Uiso 1 1 calc R U . . .
C10 C 0.7561(4) 0.43303(11) 0.3182(3) 0.0432(5) Uani 1 1 d . . . . .
H10 H 0.695883 0.475251 0.283167 0.052 Uiso 1 1 calc R U . . .
C11 C 0.5968(4) 0.38080(10) 0.2895(2) 0.0383(5) Uani 1 1 d . . . . .
H11 H 0.427218 0.387142 0.234624 0.046 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.370(2) . ?
F2 C2 1.347(3) . ?
F3 C2 1.336(3) . ?
O4 C4 1.227(2) . ?
N5 C4 1.338(3) . ?
N5 C6 1.422(3) . ?
N5 H5 0.957(10) . ?
C1 C2 1.478(3) . ?
C1 C4 1.497(3) . ?
C1 C3 1.530(3) . ?
C2 C3 1.450(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C6 C11 1.389(3) . ?
C6 C7 1.389(3) . ?
C7 C8 1.386(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.380(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N5 C6 126.99(17) . . ?
C4 N5 H5 119.8(14) . . ?
C6 N5 H5 113.1(14) . . ?
F1 C1 C2 115.34(18) . . ?
F1 C1 C4 114.74(18) . . ?
C2 C1 C4 122.36(19) . . ?
F1 C1 C3 115.84(18) . . ?
C2 C1 C3 57.63(16) . . ?
C4 C1 C3 119.09(18) . . ?
F3 C2 F2 109.1(2) . . ?
F3 C2 C3 121.9(2) . . ?
F2 C2 C3 119.0(2) . . ?
F3 C2 C1 120.38(19) . . ?
F2 C2 C1 117.2(2) . . ?
C3 C2 C1 62.97(16) . . ?
C2 C3 C1 59.40(16) . . ?
C2 C3 H3A 117.8 . . ?
C1 C3 H3A 117.8 . . ?
C2 C3 H3B 117.8 . . ?
C1 C3 H3B 117.8 . . ?
H3A C3 H3B 115.0 . . ?
O4 C4 N5 126.10(19) . . ?
O4 C4 C1 118.93(19) . . ?
N5 C4 C1 114.97(17) . . ?
C11 C6 C7 119.74(19) . . ?
C11 C6 N5 117.47(18) . . ?
C7 C6 N5 122.77(18) . . ?
C8 C7 C6 119.3(2) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C9 C8 C7 120.9(2) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 119.5(2) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C6 120.3(2) . . ?
C10 C11 H11 119.8 . . ?
C6 C11 H11 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 F3 141.4(2) . . . . ?
C4 C1 C2 F3 -6.6(3) . . . . ?
C3 C1 C2 F3 -112.9(3) . . . . ?
F1 C1 C2 F2 4.8(3) . . . . ?
C4 C1 C2 F2 -143.3(2) . . . . ?
C3 C1 C2 F2 110.5(2) . . . . ?
F1 C1 C2 C3 -105.7(2) . . . . ?
C4 C1 C2 C3 106.2(2) . . . . ?
F3 C2 C3 C1 110.5(2) . . . . ?
F2 C2 C3 C1 -107.7(2) . . . . ?
F1 C1 C3 C2 104.8(2) . . . . ?
C4 C1 C3 C2 -111.9(2) . . . . ?
C6 N5 C4 O4 -2.5(3) . . . . ?
C6 N5 C4 C1 176.26(18) . . . . ?
F1 C1 C4 O4 171.04(19) . . . . ?
C2 C1 C4 O4 -40.7(3) . . . . ?
C3 C1 C4 O4 27.4(3) . . . . ?
F1 C1 C4 N5 -7.8(3) . . . . ?
C2 C1 C4 N5 140.4(2) . . . . ?
C3 C1 C4 N5 -151.5(2) . . . . ?
C4 N5 C6 C11 -153.7(2) . . . . ?
C4 N5 C6 C7 27.8(3) . . . . ?
C11 C6 C7 C8 0.1(3) . . . . ?
N5 C6 C7 C8 178.51(19) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C7 C8 C9 C10 0.8(3) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C9 C10 C11 C6 0.1(3) . . . . ?
C7 C6 C11 C10 0.1(3) . . . . ?
N5 C6 C11 C10 -178.38(19) . . . . ?

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
_geom_hbond_publ_flag
N5 H5 O4 0.957(10) 1.981(13) 2.892(2) 158(2) 4_565 yes

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/petroleum ether'
####################################################################### 
# 
# 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_19b
_database_code_depnum_ccdc_archive 'CCDC 1850880'
_audit_update_record             
;
2018-06-25 deposited with the CCDC.
2018-07-12 downloaded from the CCDC.
;
_audit_creation_date             2018-06-25
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C11 H10 F3 N O'
_chemical_formula_moiety         'C11 H10 F3 N O'
_chemical_formula_weight         229.20
_chemical_melting_point          ?
_chemical_absolute_configuration unk

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        Pca21
_space_group_name_Hall           'P 2c -2ac'
_space_group_IT_number           29
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,1/2+Z
3 1/2-X,+Y,1/2+Z
4 1/2+X,-Y,+Z
#------------------------------------------------------------------------------
_cell_length_a                   21.421(6)
_cell_length_b                   8.828(2)
_cell_length_c                   11.037(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     2087.1(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2270
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      24.30
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944.00
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_T_max  0.997

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            24311
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_min         1.901
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3681
_reflns_number_gt                2784
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_max     0.930
_reflns_Friedel_fraction_full    0.931

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0681
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3681
_refine_ls_number_parameters     297
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0305P)²+0.2203P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.15
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1020 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.02822(9) 0.3466(2) 0.19240(18) 0.0414(5) Uani 1 1 d . . . . .
F2 F -0.09919(11) 0.3570(3) -0.0097(2) 0.0644(7) Uani 1 1 d . . . . .
F3 F -0.03682(13) 0.5185(3) -0.0973(2) 0.0746(8) Uani 1 1 d . . . . .
F21 F -0.00897(10) -0.1654(3) 0.2719(2) 0.0494(6) Uani 1 1 d . . . . .
F22 F -0.01636(11) -0.1406(3) 0.5127(2) 0.0599(7) Uani 1 1 d . . . . .
F23 F 0.05863(11) 0.0260(3) 0.5225(2) 0.0575(7) Uani 1 1 d . . . . .
O4 O 0.05884(11) 0.6428(3) 0.0604(2) 0.0391(6) Uani 1 1 d . . . . .
O24 O 0.09867(11) 0.1375(3) 0.2824(2) 0.0379(6) Uani 1 1 d . . . . .
N5 N 0.09004(13) 0.4249(3) 0.1514(2) 0.0302(7) Uani 1 1 d D . . . .
H5 H 0.0760(17) 0.342(3) 0.194(3) 0.048(12) Uiso 1 1 d D . . . .
N25 N 0.10078(13) -0.0859(3) 0.1798(3) 0.0327(7) Uani 1 1 d D . . . .
H25 H 0.0786(15) -0.174(3) 0.156(3) 0.043(11) Uiso 1 1 d D . . . .
C1 C -0.01868(16) 0.4675(4) 0.1171(3) 0.0309(8) Uani 1 1 d . . . . .
C2 C -0.05967(19) 0.4733(5) 0.0095(4) 0.0454(10) Uani 1 1 d . . . . .
C3 C -0.07206(19) 0.5801(5) 0.1073(4) 0.0548(11) Uani 1 1 d . . . . .
H3A H -0.109441 0.562583 0.158151 0.066 Uiso 1 1 calc R U . . .
H3B H -0.061444 0.687846 0.093609 0.066 Uiso 1 1 calc R U . . .
C4 C 0.04733(16) 0.5197(4) 0.1081(3) 0.0292(8) Uani 1 1 d . . . . .
C6 C 0.15652(15) 0.4558(4) 0.1423(3) 0.0353(9) Uani 1 1 d . . . . .
H6A H 0.176625 0.430363 0.220466 0.042 Uiso 1 1 calc R U . . .
H6B H 0.162598 0.565535 0.127952 0.042 Uiso 1 1 calc R U . . .
C7 C 0.18844(16) 0.3684(4) 0.0423(3) 0.0298(8) Uani 1 1 d . . . . .
C8 C 0.15623(17) 0.3093(4) -0.0555(3) 0.0356(9) Uani 1 1 d . . . . .
H8 H 0.112427 0.324262 -0.061640 0.043 Uiso 1 1 calc R U . . .
C9 C 0.1873(2) 0.2287(5) -0.1446(3) 0.0448(10) Uani 1 1 d . . . . .
H9 H 0.164577 0.186899 -0.210575 0.054 Uiso 1 1 calc R U . . .
C10 C 0.2513(2) 0.2086(4) -0.1379(4) 0.0448(10) Uani 1 1 d . . . . .
H10 H 0.272667 0.153298 -0.198994 0.054 Uiso 1 1 calc R U . . .
C11 C 0.28363(19) 0.2696(5) -0.0419(4) 0.0478(11) Uani 1 1 d . . . . .
H11 H 0.327643 0.257619 -0.037324 0.057 Uiso 1 1 calc R U . . .
C12 C 0.25257(18) 0.3480(4) 0.0479(4) 0.0396(9) Uani 1 1 d . . . . .
H12 H 0.275364 0.388397 0.114287 0.047 Uiso 1 1 calc R U . . .
C21 C 0.01834(16) -0.0383(4) 0.3204(3) 0.0329(9) Uani 1 1 d . . . . .
C22 C 0.01141(19) -0.0251(5) 0.4538(3) 0.0430(10) Uani 1 1 d . . . . .
C23 C -0.02587(19) 0.0753(4) 0.3785(3) 0.0413(10) Uani 1 1 d . . . . .
H23A H -0.014100 0.183652 0.375868 0.050 Uiso 1 1 calc R U . . .
H23B H -0.071240 0.055143 0.372808 0.050 Uiso 1 1 calc R U . . .
C24 C 0.07626(15) 0.0133(4) 0.2576(3) 0.0297(8) Uani 1 1 d . . . . .
C26 C 0.16116(15) -0.0603(4) 0.1222(3) 0.0352(9) Uani 1 1 d . . . . .
H26A H 0.168483 0.050145 0.116232 0.042 Uiso 1 1 calc R U . . .
H26B H 0.159728 -0.101331 0.038743 0.042 Uiso 1 1 calc R U . . .
C27 C 0.21523(16) -0.1316(4) 0.1884(3) 0.0300(8) Uani 1 1 d . . . . .
C28 C 0.20821(17) -0.2150(4) 0.2939(3) 0.0359(9) Uani 1 1 d . . . . .
H28 H 0.167866 -0.227167 0.328315 0.043 Uiso 1 1 calc R U . . .
C29 C 0.2597(2) -0.2812(4) 0.3501(4) 0.0446(10) Uani 1 1 d . . . . .
H29 H 0.254086 -0.339314 0.421730 0.054 Uiso 1 1 calc R U . . .
C30 C 0.31836(19) -0.2629(5) 0.3026(4) 0.0459(11) Uani 1 1 d . . . . .
H30 H 0.353338 -0.308781 0.340739 0.055 Uiso 1 1 calc R U . . .
C31 C 0.32622(18) -0.1775(5) 0.1993(4) 0.0479(11) Uani 1 1 d . . . . .
H31 H 0.366891 -0.162956 0.166977 0.057 Uiso 1 1 calc R U . . .
C32 C 0.27535(17) -0.1128(4) 0.1423(3) 0.0398(10) Uani 1 1 d . . . . .
H32 H 0.281407 -0.054716 0.070750 0.048 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.368(4) . ?
F2 C2 1.348(4) . ?
F3 C2 1.337(5) . ?
F21 C21 1.374(4) . ?
F22 C22 1.348(4) . ?
F23 C22 1.343(5) . ?
O4 C4 1.233(4) . ?
O24 C24 1.228(4) . ?
N5 C4 1.328(4) . ?
N5 C6 1.453(4) . ?
N5 H5 0.92(2) . ?
N25 C24 1.334(4) . ?
N25 C26 1.459(4) . ?
N25 H25 0.95(2) . ?
C1 C2 1.478(5) . ?
C1 C4 1.490(5) . ?
C1 C3 1.519(5) . ?
C2 C3 1.457(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C6 C7 1.510(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.384(5) . ?
C7 C12 1.387(5) . ?
C8 C9 1.384(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C21 C22 1.484(5) . ?
C21 C24 1.492(5) . ?
C21 C23 1.521(5) . ?
C22 C23 1.453(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C26 C27 1.507(5) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.386(5) . ?
C27 C32 1.395(5) . ?
C28 C29 1.393(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.371(6) . ?
C29 H29 0.9500 . ?
C30 C31 1.378(6) . ?
C30 H30 0.9500 . ?
C31 C32 1.382(5) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N5 C6 122.1(3) . . ?
C4 N5 H5 117(2) . . ?
C6 N5 H5 120(2) . . ?
C24 N25 C26 121.9(3) . . ?
C24 N25 H25 121(2) . . ?
C26 N25 H25 117(2) . . ?
F1 C1 C2 115.3(3) . . ?
F1 C1 C4 115.0(3) . . ?
C2 C1 C4 120.0(3) . . ?
F1 C1 C3 116.2(3) . . ?
C2 C1 C3 58.2(3) . . ?
C4 C1 C3 120.5(3) . . ?
F3 C2 F2 108.6(3) . . ?
F3 C2 C3 121.8(4) . . ?
F2 C2 C3 119.6(4) . . ?
F3 C2 C1 120.1(3) . . ?
F2 C2 C1 118.2(3) . . ?
C3 C2 C1 62.3(3) . . ?
C2 C3 C1 59.5(3) . . ?
C2 C3 H3A 117.8 . . ?
C1 C3 H3A 117.8 . . ?
C2 C3 H3B 117.8 . . ?
C1 C3 H3B 117.8 . . ?
H3A C3 H3B 115.0 . . ?
O4 C4 N5 124.8(3) . . ?
O4 C4 C1 119.4(3) . . ?
N5 C4 C1 115.8(3) . . ?
N5 C6 C7 113.4(3) . . ?
N5 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
N5 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C8 C7 C12 118.7(3) . . ?
C8 C7 C6 122.5(3) . . ?
C12 C7 C6 118.8(3) . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C10 120.2(4) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 119.3(4) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 120.4(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 120.7(4) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
F21 C21 C22 114.1(3) . . ?
F21 C21 C24 115.0(3) . . ?
C22 C21 C24 121.3(3) . . ?
F21 C21 C23 115.9(3) . . ?
C22 C21 C23 57.8(3) . . ?
C24 C21 C23 120.8(3) . . ?
F23 C22 F22 108.3(3) . . ?
F23 C22 C23 122.1(4) . . ?
F22 C22 C23 119.6(3) . . ?
F23 C22 C21 120.8(3) . . ?
F22 C22 C21 117.6(4) . . ?
C23 C22 C21 62.4(3) . . ?
C22 C23 C21 59.8(2) . . ?
C22 C23 H23A 117.8 . . ?
C21 C23 H23A 117.8 . . ?
C22 C23 H23B 117.8 . . ?
C21 C23 H23B 117.8 . . ?
H23A C23 H23B 114.9 . . ?
O24 C24 N25 125.1(3) . . ?
O24 C24 C21 119.6(3) . . ?
N25 C24 C21 115.2(3) . . ?
N25 C26 C27 113.9(3) . . ?
N25 C26 H26A 108.8 . . ?
C27 C26 H26A 108.8 . . ?
N25 C26 H26B 108.8 . . ?
C27 C26 H26B 108.8 . . ?
H26A C26 H26B 107.7 . . ?
C28 C27 C32 118.0(3) . . ?
C28 C27 C26 123.1(3) . . ?
C32 C27 C26 118.9(3) . . ?
C27 C28 C29 120.7(3) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 H28 119.6 . . ?
C30 C29 C28 120.4(4) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C31 119.5(4) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C30 C31 C32 120.5(4) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C31 C32 C27 120.8(4) . . ?
C31 C32 H32 119.6 . . ?
C27 C32 H32 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 F3 -141.1(3) . . . . ?
C4 C1 C2 F3 3.2(6) . . . . ?
C3 C1 C2 F3 112.6(4) . . . . ?
F1 C1 C2 F2 -4.3(5) . . . . ?
C4 C1 C2 F2 140.0(4) . . . . ?
C3 C1 C2 F2 -110.6(4) . . . . ?
F1 C1 C2 C3 106.3(4) . . . . ?
C4 C1 C2 C3 -109.4(4) . . . . ?
F3 C2 C3 C1 -109.9(4) . . . . ?
F2 C2 C3 C1 108.4(4) . . . . ?
F1 C1 C3 C2 -104.7(3) . . . . ?
C4 C1 C3 C2 108.5(4) . . . . ?
C6 N5 C4 O4 -2.3(5) . . . . ?
C6 N5 C4 C1 176.2(3) . . . . ?
F1 C1 C4 O4 -167.2(3) . . . . ?
C2 C1 C4 O4 48.4(5) . . . . ?
C3 C1 C4 O4 -20.0(5) . . . . ?
F1 C1 C4 N5 14.3(4) . . . . ?
C2 C1 C4 N5 -130.1(4) . . . . ?
C3 C1 C4 N5 161.4(3) . . . . ?
C4 N5 C6 C7 -101.9(4) . . . . ?
N5 C6 C7 C8 21.6(5) . . . . ?
N5 C6 C7 C12 -159.2(3) . . . . ?
C12 C7 C8 C9 1.4(5) . . . . ?
C6 C7 C8 C9 -179.4(3) . . . . ?
C7 C8 C9 C10 -1.2(6) . . . . ?
C8 C9 C10 C11 0.0(6) . . . . ?
C9 C10 C11 C12 1.0(6) . . . . ?
C10 C11 C12 C7 -0.8(6) . . . . ?
C8 C7 C12 C11 -0.4(5) . . . . ?
C6 C7 C12 C11 -179.6(3) . . . . ?
F21 C21 C22 F23 140.7(3) . . . . ?
C24 C21 C22 F23 -3.8(6) . . . . ?
C23 C21 C22 F23 -112.8(4) . . . . ?
F21 C21 C22 F22 4.3(5) . . . . ?
C24 C21 C22 F22 -140.2(4) . . . . ?
C23 C21 C22 F22 110.9(4) . . . . ?
F21 C21 C22 C23 -106.5(3) . . . . ?
C24 C21 C22 C23 109.0(4) . . . . ?
F23 C22 C23 C21 110.7(4) . . . . ?
F22 C22 C23 C21 -107.7(4) . . . . ?
F21 C21 C23 C22 103.3(4) . . . . ?
C24 C21 C23 C22 -109.9(4) . . . . ?
C26 N25 C24 O24 5.2(5) . . . . ?
C26 N25 C24 C21 -172.5(3) . . . . ?
F21 C21 C24 O24 169.1(3) . . . . ?
C22 C21 C24 O24 -46.7(5) . . . . ?
C23 C21 C24 O24 22.0(5) . . . . ?
F21 C21 C24 N25 -13.1(4) . . . . ?
C22 C21 C24 N25 131.1(4) . . . . ?
C23 C21 C24 N25 -160.2(3) . . . . ?
C24 N25 C26 C27 93.7(4) . . . . ?
N25 C26 C27 C28 0.5(5) . . . . ?
N25 C26 C27 C32 -179.1(3) . . . . ?
C32 C27 C28 C29 -1.7(5) . . . . ?
C26 C27 C28 C29 178.7(3) . . . . ?
C27 C28 C29 C30 1.0(5) . . . . ?
C28 C29 C30 C31 0.5(6) . . . . ?
C29 C30 C31 C32 -1.2(6) . . . . ?
C30 C31 C32 C27 0.4(6) . . . . ?
C28 C27 C32 C31 1.0(5) . . . . ?
C26 C27 C32 C31 -179.3(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
_geom_hbond_publ_flag
N5 H5 O24 0.92(2) 2.11(3) 2.926(4) 147(3) . yes
N25 H25 O4 0.95(2) 1.98(3) 2.878(4) 158(3) 1_545 yes

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/petroleum ether'
####################################################################### 
# 
# 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_22
_database_code_depnum_ccdc_archive 'CCDC 1850879'
_audit_update_record             
;
2018-06-25 deposited with the CCDC.
2018-07-12 downloaded from the CCDC.
;
_audit_creation_date             2018-06-25
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H12 Br F2 N O2'
_chemical_formula_moiety         'C16 H12 Br F2 N O2'
_chemical_formula_weight         368.18
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/n
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   4.7918(2)
_cell_length_b                   9.3365(6)
_cell_length_c                   33.8797(16)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.292(5)
_cell_angle_gamma                90.0000
_cell_volume                     1514.52(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6830
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      25.97
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736.00
_exptl_absorpt_coefficient_mu    2.749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.601
_exptl_absorpt_correction_T_max  0.947

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            19235
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_theta_max         29.015
_diffrn_reflns_theta_min         2.263
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.862
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.862
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       44
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3492
_reflns_number_gt                2269
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0758
_refine_ls_wR_factor_ref         0.2133
_refine_ls_wR_factor_gt          0.1993
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3492
_refine_ls_number_parameters     202
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0709P)²+6.0642P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         1.32
_refine_diff_density_min         -0.66
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Br16 Br 0.82486(18) 0.70105(11) 0.96809(2) 0.0722(4) Uani 1 1 d . . . . .
F2 F 1.2801(7) 0.9464(4) 0.78230(11) 0.0482(9) Uani 1 1 d . . . . .
F3 F 0.8738(7) 0.9723(4) 0.75078(11) 0.0490(9) Uani 1 1 d . . . . .
O4 O 0.7558(7) 0.7441(5) 0.69097(12) 0.0429(11) Uani 1 1 d . . . . .
O12 O 1.1622(7) 0.6579(4) 0.79913(11) 0.0314(8) Uani 1 1 d . . . . .
N5 N 1.1773(8) 0.7288(5) 0.66331(13) 0.0269(9) Uani 1 1 d D . . . .
H5 H 1.369(6) 0.700(7) 0.6686(18) 0.040 Uiso 1 1 d D U . . .
C1 C 1.1634(10) 0.7670(6) 0.73249(15) 0.0282(11) Uani 1 1 d . . . . .
H1 H 1.366806 0.742724 0.733327 0.034 Uiso 1 1 calc R U . . .
C2 C 1.0782(11) 0.8787(6) 0.76056(16) 0.0321(12) Uani 1 1 d . . . . .
C3 C 1.0074(10) 0.7309(6) 0.76965(15) 0.0277(11) Uani 1 1 d . . . . .
H3 H 0.806621 0.703220 0.765754 0.033 Uiso 1 1 calc R U . . .
C4 C 1.0115(10) 0.7456(6) 0.69362(16) 0.0283(11) Uani 1 1 d . . . . .
C6 C 1.0863(10) 0.6995(6) 0.62350(16) 0.0308(11) Uani 1 1 d . . . . .
C7 C 1.2189(13) 0.5953(8) 0.60281(18) 0.0468(15) Uani 1 1 d . . . . .
H7 H 1.363704 0.540400 0.615397 0.056 Uiso 1 1 calc R U . . .
C8 C 1.1428(15) 0.5699(9) 0.5638(2) 0.0573(19) Uani 1 1 d . . . . .
H8 H 1.234879 0.497303 0.549625 0.069 Uiso 1 1 calc R U . . .
C9 C 0.9349(16) 0.6488(9) 0.5455(2) 0.059(2) Uani 1 1 d . . . . .
H9 H 0.885748 0.632366 0.518393 0.071 Uiso 1 1 calc R U . . .
C10 C 0.7980(14) 0.7512(8) 0.5661(2) 0.0525(18) Uani 1 1 d . . . . .
H10 H 0.650670 0.804211 0.553412 0.063 Uiso 1 1 calc R U . . .
C11 C 0.8722(12) 0.7781(7) 0.60508(18) 0.0398(14) Uani 1 1 d . . . . .
H11 H 0.777718 0.849882 0.619271 0.048 Uiso 1 1 calc R U . . .
C13 C 1.0744(11) 0.6733(5) 0.83714(16) 0.0297(11) Uani 1 1 d . . . . .
C14 C 0.8646(12) 0.7698(7) 0.84776(18) 0.0418(14) Uani 1 1 d . . . . .
H14 H 0.773427 0.829143 0.828464 0.050 Uiso 1 1 calc R U . . .
C15 C 0.7939(13) 0.7762(8) 0.88693(19) 0.0493(16) Uani 1 1 d . . . . .
H15 H 0.653822 0.841099 0.894758 0.059 Uiso 1 1 calc R U . . .
C16 C 0.9255(14) 0.6892(8) 0.91453(17) 0.0454(15) Uani 1 1 d . . . . .
C17 C 1.1340(14) 0.5960(7) 0.90411(18) 0.0456(15) Uani 1 1 d . . . . .
H17 H 1.226610 0.537975 0.923584 0.055 Uiso 1 1 calc R U . . .
C18 C 1.2064(13) 0.5880(7) 0.86532(18) 0.0421(14) Uani 1 1 d . . . . .
H18 H 1.348007 0.523228 0.857911 0.050 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Br16 C16 1.899(6) . ?
F2 C2 1.349(6) . ?
F3 C2 1.344(6) . ?
O4 C4 1.225(6) . ?
O12 C13 1.378(6) . ?
O12 C3 1.398(6) . ?
N5 C4 1.333(7) . ?
N5 C6 1.427(7) . ?
N5 H5 0.97(2) . ?
C1 C2 1.480(7) . ?
C1 C4 1.492(8) . ?
C1 C3 1.527(7) . ?
C1 H1 1.0000 . ?
C2 C3 1.457(8) . ?
C3 H3 1.0000 . ?
C6 C7 1.370(9) . ?
C6 C11 1.389(8) . ?
C7 C8 1.376(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.368(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.367(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(9) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C13 C18 1.378(8) . ?
C13 C14 1.407(8) . ?
C14 C15 1.384(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.373(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(10) . ?
C17 C18 1.374(9) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O12 C3 116.3(4) . . ?
C4 N5 C6 125.6(4) . . ?
C4 N5 H5 119(4) . . ?
C6 N5 H5 112(4) . . ?
C2 C1 C4 121.6(5) . . ?
C2 C1 C3 57.9(3) . . ?
C4 C1 C3 117.4(4) . . ?
C2 C1 H1 115.8 . . ?
C4 C1 H1 115.8 . . ?
C3 C1 H1 115.8 . . ?
F3 C2 F2 109.2(4) . . ?
F3 C2 C3 119.6(4) . . ?
F2 C2 C3 119.8(5) . . ?
F3 C2 C1 121.1(5) . . ?
F2 C2 C1 118.1(4) . . ?
C3 C2 C1 62.7(4) . . ?
O12 C3 C2 119.5(4) . . ?
O12 C3 C1 115.7(4) . . ?
C2 C3 C1 59.4(3) . . ?
O12 C3 H3 116.6 . . ?
C2 C3 H3 116.6 . . ?
C1 C3 H3 116.6 . . ?
O4 C4 N5 124.6(5) . . ?
O4 C4 C1 121.1(5) . . ?
N5 C4 C1 114.3(4) . . ?
C7 C6 C11 119.6(5) . . ?
C7 C6 N5 119.3(5) . . ?
C11 C6 N5 121.0(5) . . ?
C6 C7 C8 120.2(6) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 120.2(7) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 120.0(6) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.4(7) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C6 119.5(6) . . ?
C10 C11 H11 120.3 . . ?
C6 C11 H11 120.3 . . ?
C18 C13 O12 116.0(5) . . ?
C18 C13 C14 120.4(5) . . ?
O12 C13 C14 123.6(5) . . ?
C15 C14 C13 118.5(6) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C16 C15 C14 120.3(6) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 121.1(6) . . ?
C15 C16 Br16 119.3(5) . . ?
C17 C16 Br16 119.7(5) . . ?
C18 C17 C16 119.5(6) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C13 120.3(6) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C1 C2 F3 -5.1(8) . . . . ?
C3 C1 C2 F3 -109.8(5) . . . . ?
C4 C1 C2 F2 -144.5(5) . . . . ?
C3 C1 C2 F2 110.9(5) . . . . ?
C4 C1 C2 C3 104.6(5) . . . . ?
C13 O12 C3 C2 87.3(5) . . . . ?
C13 O12 C3 C1 155.1(4) . . . . ?
F3 C2 C3 O12 -143.8(5) . . . . ?
F2 C2 C3 O12 -4.2(7) . . . . ?
C1 C2 C3 O12 104.1(5) . . . . ?
F3 C2 C3 C1 112.0(5) . . . . ?
F2 C2 C3 C1 -108.4(5) . . . . ?
C2 C1 C3 O12 -110.5(5) . . . . ?
C4 C1 C3 O12 137.7(5) . . . . ?
C4 C1 C3 C2 -111.8(5) . . . . ?
C6 N5 C4 O4 -3.3(9) . . . . ?
C6 N5 C4 C1 176.6(5) . . . . ?
C2 C1 C4 O4 -44.8(8) . . . . ?
C3 C1 C4 O4 22.6(8) . . . . ?
C2 C1 C4 N5 135.2(5) . . . . ?
C3 C1 C4 N5 -157.3(5) . . . . ?
C4 N5 C6 C7 -134.4(6) . . . . ?
C4 N5 C6 C11 47.8(8) . . . . ?
C11 C6 C7 C8 0.8(10) . . . . ?
N5 C6 C7 C8 -177.0(6) . . . . ?
C6 C7 C8 C9 0.2(11) . . . . ?
C7 C8 C9 C10 -1.4(11) . . . . ?
C8 C9 C10 C11 1.5(11) . . . . ?
C9 C10 C11 C6 -0.5(10) . . . . ?
C7 C6 C11 C10 -0.7(9) . . . . ?
N5 C6 C11 C10 177.1(5) . . . . ?
C3 O12 C13 C18 172.5(5) . . . . ?
C3 O12 C13 C14 -7.8(7) . . . . ?
C18 C13 C14 C15 -0.2(9) . . . . ?
O12 C13 C14 C15 -179.9(5) . . . . ?
C13 C14 C15 C16 -0.5(10) . . . . ?
C14 C15 C16 C17 1.4(11) . . . . ?
C14 C15 C16 Br16 179.8(5) . . . . ?
C15 C16 C17 C18 -1.5(10) . . . . ?
Br16 C16 C17 C18 -179.9(5) . . . . ?
C16 C17 C18 C13 0.8(9) . . . . ?
O12 C13 C18 C17 179.8(5) . . . . ?
C14 C13 C18 C17 0.1(9) . . . . ?

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
_geom_hbond_publ_flag
N5 H5 O4 0.97(2) 2.02(4) 2.894(5) 150(5) 1_655 yes

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol/dichloromethane/chloroform'
####################################################################### 
# 
# 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_23b
_database_code_depnum_ccdc_archive 'CCDC 1850878'
_audit_update_record             
;
2018-06-25 deposited with the CCDC.
2018-07-12 downloaded from the CCDC.
;
_audit_creation_date             2018-06-25
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H12 Br F2 N O S'
_chemical_formula_moiety         'C16 H12 Br F2 N O S'
_chemical_formula_weight         384.24
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/n
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   4.81051(8)
_cell_length_b                   9.39477(13)
_cell_length_c                   34.2042(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.9598(14)
_cell_angle_gamma                90.0000
_cell_volume                     1543.75(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10479
_cell_measurement_theta_min      4.68
_cell_measurement_theta_max      67.82
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768.00
_exptl_absorpt_coefficient_mu    5.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43i (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.554
_exptl_absorpt_correction_T_max  0.858

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            16124
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_theta_max         68.275
_diffrn_reflns_theta_min         2.587
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       40
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2816
_reflns_number_gt                2707
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.0702
_refine_ls_wR_factor_gt          0.0695
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2816
_refine_ls_number_parameters     203
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0313P)²+0.9384P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.43
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.6763 1.2805
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Br16 Br 0.68747(6) 0.72152(3) 0.51908(2) 0.06340(11) Uani 1 1 d . . . . .
S12 S 0.30727(11) 0.49635(5) 0.68572(2) 0.04051(13) Uani 1 1 d . . . . .
F2 F 0.2087(3) 0.80937(13) 0.70848(4) 0.0516(3) Uani 1 1 d . . . . .
F3 F 0.6137(3) 0.84209(13) 0.73895(4) 0.0525(3) Uani 1 1 d . . . . .
O4 O 0.7561(2) 0.62640(16) 0.80010(4) 0.0380(3) Uani 1 1 d . . . . .
N5 N 0.3363(3) 0.62161(15) 0.82799(4) 0.0276(3) Uani 1 1 d D . . . .
H5 H 0.140(2) 0.611(2) 0.8229(6) 0.042(6) Uiso 1 1 d D . . . .
C1 C 0.3416(3) 0.63681(19) 0.75882(5) 0.0285(3) Uani 1 1 d . . . . .
H1 H 0.140679 0.609476 0.758711 0.034 Uiso 1 1 calc R U . . .
C2 C 0.4149(4) 0.74546(19) 0.72998(6) 0.0337(4) Uani 1 1 d . . . . .
C3 C 0.4954(3) 0.59878(18) 0.72145(5) 0.0284(3) Uani 1 1 d . . . . .
H3 H 0.697948 0.576078 0.725453 0.034 Uiso 1 1 calc R U . . .
C4 C 0.5011(3) 0.62750(17) 0.79751(5) 0.0270(3) Uani 1 1 d . . . . .
C6 C 0.4303(3) 0.61649(19) 0.86809(5) 0.0310(4) Uani 1 1 d . . . . .
C7 C 0.2897(4) 0.5289(2) 0.89290(6) 0.0434(5) Uani 1 1 d . . . . .
H7 H 0.140996 0.470861 0.882826 0.052 Uiso 1 1 calc R U . . .
C8 C 0.3668(5) 0.5263(3) 0.93263(7) 0.0580(6) Uani 1 1 d . . . . .
H8 H 0.270127 0.466278 0.949695 0.070 Uiso 1 1 calc R U . . .
C9 C 0.5822(5) 0.6099(3) 0.94737(6) 0.0586(7) Uani 1 1 d . . . . .
H9 H 0.634960 0.607341 0.974509 0.070 Uiso 1 1 calc R U . . .
C10 C 0.7213(5) 0.6976(3) 0.92262(7) 0.0534(6) Uani 1 1 d . . . . .
H10 H 0.868822 0.755953 0.932903 0.064 Uiso 1 1 calc R U . . .
C11 C 0.6478(4) 0.7016(2) 0.88269(6) 0.0401(4) Uani 1 1 d . . . . .
H11 H 0.745113 0.761567 0.865702 0.048 Uiso 1 1 calc R U . . .
C13 C 0.4243(4) 0.56576(19) 0.64125(5) 0.0333(4) Uani 1 1 d . . . . .
C14 C 0.6279(4) 0.6683(2) 0.63868(6) 0.0421(4) Uani 1 1 d . . . . .
H14 H 0.715199 0.707160 0.661844 0.051 Uiso 1 1 calc R U . . .
C15 C 0.7053(5) 0.7148(3) 0.60232(6) 0.0517(5) Uani 1 1 d . . . . .
H15 H 0.845748 0.785227 0.600526 0.062 Uiso 1 1 calc R U . . .
C16 C 0.5779(4) 0.6585(2) 0.56885(6) 0.0412(4) Uani 1 1 d . . . . .
C17 C 0.3755(5) 0.5571(3) 0.57084(6) 0.0517(5) Uani 1 1 d . . . . .
H17 H 0.288398 0.519012 0.547570 0.062 Uiso 1 1 calc R U . . .
C18 C 0.2986(5) 0.5105(2) 0.60707(6) 0.0509(5) Uani 1 1 d . . . . .
H18 H 0.158269 0.439903 0.608600 0.061 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43i (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43i (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43i (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Br16 C16 1.9025(19) . ?
S12 C3 1.7676(17) . ?
S12 C13 1.7732(19) . ?
F2 C2 1.345(2) . ?
F3 C2 1.342(2) . ?
O4 C4 1.225(2) . ?
N5 C4 1.343(2) . ?
N5 C6 1.422(2) . ?
N5 H5 0.957(10) . ?
C1 C2 1.475(2) . ?
C1 C4 1.498(2) . ?
C1 C3 1.551(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.465(2) . ?
C3 H3 1.0000 . ?
C6 C7 1.383(3) . ?
C6 C11 1.389(3) . ?
C7 C8 1.390(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.376(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C13 C14 1.380(3) . ?
C13 C18 1.389(3) . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.366(3) . ?
C17 C18 1.382(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 S12 C13 102.65(8) . . ?
C4 N5 C6 125.36(14) . . ?
C4 N5 H5 118.6(14) . . ?
C6 N5 H5 115.7(14) . . ?
C2 C1 C4 120.15(15) . . ?
C2 C1 C3 57.83(11) . . ?
C4 C1 C3 118.05(13) . . ?
C2 C1 H1 116.1 . . ?
C4 C1 H1 116.1 . . ?
C3 C1 H1 116.1 . . ?
F3 C2 F2 108.63(15) . . ?
F3 C2 C3 119.30(16) . . ?
F2 C2 C3 120.40(16) . . ?
F3 C2 C1 120.47(16) . . ?
F2 C2 C1 118.65(16) . . ?
C3 C2 C1 63.70(12) . . ?
C2 C3 C1 58.47(11) . . ?
C2 C3 S12 121.25(13) . . ?
C1 C3 S12 116.51(12) . . ?
C2 C3 H3 116.0 . . ?
C1 C3 H3 116.0 . . ?
S12 C3 H3 116.0 . . ?
O4 C4 N5 124.92(16) . . ?
O4 C4 C1 121.99(15) . . ?
N5 C4 C1 113.09(13) . . ?
C7 C6 C11 120.31(18) . . ?
C7 C6 N5 118.06(17) . . ?
C11 C6 N5 121.56(17) . . ?
C6 C7 C8 119.8(2) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 120.4(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.8(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C11 120.8(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C6 C11 C10 119.0(2) . . ?
C6 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C14 C13 C18 119.13(18) . . ?
C14 C13 S12 124.70(14) . . ?
C18 C13 S12 116.17(15) . . ?
C13 C14 C15 120.07(18) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 120.97(19) . . ?
C17 C16 Br16 119.51(15) . . ?
C15 C16 Br16 119.52(16) . . ?
C16 C17 C18 119.30(19) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C13 120.8(2) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C1 C2 F3 -3.9(3) . . . . ?
C3 C1 C2 F3 -110.03(19) . . . . ?
C4 C1 C2 F2 -142.00(16) . . . . ?
C3 C1 C2 F2 111.91(19) . . . . ?
C4 C1 C2 C3 106.09(17) . . . . ?
F3 C2 C3 C1 111.79(19) . . . . ?
F2 C2 C3 C1 -109.28(19) . . . . ?
F3 C2 C3 S12 -144.31(14) . . . . ?
F2 C2 C3 S12 -5.4(2) . . . . ?
C1 C2 C3 S12 103.90(15) . . . . ?
C4 C1 C3 C2 -109.70(18) . . . . ?
C2 C1 C3 S12 -111.97(15) . . . . ?
C4 C1 C3 S12 138.33(13) . . . . ?
C13 S12 C3 C2 76.83(16) . . . . ?
C13 S12 C3 C1 144.45(13) . . . . ?
C6 N5 C4 O4 1.5(3) . . . . ?
C6 N5 C4 C1 -178.06(15) . . . . ?
C2 C1 C4 O4 -48.6(2) . . . . ?
C3 C1 C4 O4 18.5(2) . . . . ?
C2 C1 C4 N5 131.00(17) . . . . ?
C3 C1 C4 N5 -161.84(15) . . . . ?
C4 N5 C6 C7 -140.51(18) . . . . ?
C4 N5 C6 C11 42.6(3) . . . . ?
C11 C6 C7 C8 0.0(3) . . . . ?
N5 C6 C7 C8 -176.90(18) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C7 C6 C11 C10 -0.2(3) . . . . ?
N5 C6 C11 C10 176.61(17) . . . . ?
C9 C10 C11 C6 0.5(3) . . . . ?
C3 S12 C13 C14 3.79(19) . . . . ?
C3 S12 C13 C18 -176.42(17) . . . . ?
C18 C13 C14 C15 -0.2(3) . . . . ?
S12 C13 C14 C15 179.63(18) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C14 C15 C16 Br16 -179.45(18) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
Br16 C16 C17 C18 179.32(19) . . . . ?
C16 C17 C18 C13 0.1(4) . . . . ?
C14 C13 C18 C17 0.0(3) . . . . ?
S12 C13 C18 C17 -179.79(19) . . . . ?

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
_geom_hbond_publ_flag
N5 H5 O4 0.957(10) 1.972(11) 2.9029(18) 164(2) 1_455 yes

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
