# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_ch-ls-148-3
_database_code_depnum_ccdc_archive 'CCDC 2008226'
loop_
_audit_author_name
_audit_author_address
ShunLi
;SICHUAN UNIVERCITY
China
;
_audit_update_record             
;
2020-06-05 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;
_audit_creation_date             2019-05-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H10 F5 N O'
_chemical_formula_sum            'C18 H10 F5 N O'
_chemical_formula_weight         351.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.4580(5)
_cell_length_b                   18.7761(12)
_cell_length_c                   11.2910(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.946(7)
_cell_angle_gamma                90
_cell_volume                     1512.47(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2259
_cell_measurement_temperature    293.75(12)
_cell_measurement_theta_max      70.6980
_cell_measurement_theta_min      4.0730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7165
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.863
_diffrn_reflns_theta_min         4.710
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.75(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00  -9.00   1.00    1.00    --  -36.04 -77.00   0.00   95
  2  ω    -53.00  31.00   1.00    1.00    --  -36.04  57.00 120.00   84
  3  ω    -63.00  32.00   1.00    1.00    --  -36.04  77.00 120.00   95
  4  ω      1.00  75.00   1.00    1.00    --   36.04 -99.00 -90.00   74
  5  ω     37.00 109.00   1.00    1.41    --  106.21 -94.00-150.00   72
  6  ω     89.00 175.00   1.00    1.41    --  106.21  45.00  30.00   86
  7  ω     38.00 124.00   1.00    1.41    --  106.21 -45.00-120.00   86
  8  ω     36.00 113.00   1.00    1.41    --  106.21-111.00  60.00   77
  9  ω    100.00 176.00   1.00    1.41    --  106.21 111.00-120.00   76
 10  ω     35.00 145.00   1.00    1.41    --  106.21 -15.00 -60.00  110
 11  ω    100.00 176.00   1.00    1.41    --  106.21 111.00  30.00   76
 12  ω     37.00 106.00   1.00    1.41    --  106.21 -94.00 150.00   69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0151911000
_diffrn_orient_matrix_UB_12      -0.0815403000
_diffrn_orient_matrix_UB_13      0.0139682000
_diffrn_orient_matrix_UB_21      -0.1608668000
_diffrn_orient_matrix_UB_22      -0.0086972000
_diffrn_orient_matrix_UB_23      -0.1206445000
_diffrn_orient_matrix_UB_31      0.1428995000
_diffrn_orient_matrix_UB_32      -0.0010577000
_diffrn_orient_matrix_UB_33      -0.0746581000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2263
_reflns_number_total             2906
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.152
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2906
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0816
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1465P)²+0.0434P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2019
_refine_ls_wR_factor_ref         0.2212
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00H(H00H), C00J(H00J), C00L(H00L), C00M(H00M),
 C00N(H00N)
2.b Idealised Me refined as rotating group:
 C00P(H00A,H00B,H00C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.6550(2) 0.72366(9) 0.35440(13) 0.0800(5) Uani 1 1 d . . . . .
F002 F 0.4194(3) 0.95432(9) 0.37830(18) 0.0925(5) Uani 1 1 d . . . . .
F003 F 0.5854(3) 0.73820(11) 0.11218(16) 0.0989(6) Uani 1 1 d . . . . .
F004 F 0.3548(3) 0.96853(11) 0.1336(2) 0.1082(7) Uani 1 1 d . . . . .
F005 F 0.4446(3) 0.86131(13) -0.00053(15) 0.1128(8) Uani 1 1 d . . . . .
N006 N 0.5299(2) 0.76776(10) 0.55224(16) 0.0568(5) Uani 1 1 d . . . . .
O007 O 0.3754(4) 0.48963(13) 0.8306(2) 0.1018(7) Uani 1 1 d . . . . .
C008 C 0.5812(3) 0.82953(13) 0.5131(2) 0.0596(5) Uani 1 1 d . . . . .
C009 C 0.5383(3) 0.83794(13) 0.3765(2) 0.0596(5) Uani 1 1 d . . . . .
C00A C 0.5720(3) 0.75602(13) 0.67475(19) 0.0578(5) Uani 1 1 d . . . . .
C00B C 0.5762(3) 0.78388(13) 0.3034(2) 0.0618(5) Uani 1 1 d . . . . .
C00C C 0.5426(3) 0.79085(15) 0.1783(2) 0.0696(6) Uani 1 1 d . . . . .
C00D C 0.5199(3) 0.68555(13) 0.71327(19) 0.0580(5) Uani 1 1 d . . . . .
C00E C 0.6738(3) 0.88326(15) 0.5927(2) 0.0717(6) Uani 1 1 d . . . . .
H00E H 0.7078 0.9256 0.5623 0.086 Uiso 1 1 calc R . . . .
C00F C 0.5438(4) 0.66949(15) 0.8377(2) 0.0713(7) Uani 1 1 d . . . . .
H00F H 0.5930 0.7037 0.8980 0.086 Uiso 1 1 calc R . . . .
C00G C 0.4638(3) 0.89938(14) 0.3158(2) 0.0682(6) Uani 1 1 d . . . . .
C00H C 0.6641(4) 0.80762(16) 0.7598(2) 0.0742(7) Uani 1 1 d . . . . .
H00H H 0.6921 0.7990 0.8444 0.089 Uiso 1 1 calc R . . . .
C00I C 0.4214(3) 0.55228(16) 0.7850(2) 0.0723(6) Uani 1 1 d . . . . .
C00J C 0.3991(3) 0.56683(14) 0.6618(2) 0.0724(7) Uani 1 1 d . . . . .
H00J H 0.3504 0.5324 0.6019 0.087 Uiso 1 1 calc R . . . .
C00K C 0.4698(4) 0.85346(17) 0.1214(2) 0.0782(8) Uani 1 1 d . . . . .
C00L C 0.4498(3) 0.63307(14) 0.6277(2) 0.0652(6) Uani 1 1 d . . . . .
H00L H 0.4359 0.6422 0.5446 0.078 Uiso 1 1 calc R . . . .
C00M C 0.7130(4) 0.87131(17) 0.7176(3) 0.0812(8) Uani 1 1 d . . . . .
H00M H 0.7726 0.9063 0.7736 0.097 Uiso 1 1 calc R . . . .
C00N C 0.4951(4) 0.60359(18) 0.8721(2) 0.0790(7) Uani 1 1 d . . . . .
H00N H 0.5125 0.5937 0.9554 0.095 Uiso 1 1 calc R . . . .
C00O C 0.4286(3) 0.90723(15) 0.1894(3) 0.0770(7) Uani 1 1 d . . . . .
C00P C 0.2833(5) 0.43698(19) 0.7459(4) 0.1067(11) Uani 1 1 d . . . . .
H00A H 0.1745 0.4572 0.6879 0.160 Uiso 1 1 calc GR . . . .
H00B H 0.2458 0.3987 0.7898 0.160 Uiso 1 1 calc GR . . . .
H00C H 0.3667 0.4191 0.7023 0.160 Uiso 1 1 calc GR . . . .


_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
F001 C00B 1.326(3) . ?
F002 C00G 1.345(3) . ?
F003 C00C 1.332(3) . ?
F004 C00O 1.350(3) . ?
F005 C00K 1.342(3) . ?
N006 C008 1.336(3) . ?
N006 C00A 1.344(3) . ?
O007 C00I 1.367(4) . ?
O007 C00P 1.407(4) . ?
C008 C009 1.489(3) . ?
C008 C00E 1.393(3) . ?
C009 C00B 1.389(3) . ?
C009 C00G 1.374(4) . ?
C00A C00D 1.480(3) . ?
C00A C00H 1.396(3) . ?
C00B C00C 1.367(3) . ?
C00C C00K 1.373(4) . ?
C00D C00F 1.397(3) . ?
C00D C00L 1.372(3) . ?
C00E H00E 0.9300 . ?
C00E C00M 1.373(4) . ?
C00F H00F 0.9300 . ?
C00F C00N 1.376(4) . ?
C00G C00O 1.381(4) . ?
C00H H00H 0.9300 . ?
C00H C00M 1.375(4) . ?
C00I C00J 1.379(4) . ?
C00I C00N 1.372(4) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.387(4) . ?
C00K C00O 1.357(4) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00P H00A 0.9600 . ?
C00P H00B 0.9600 . ?
C00P H00C 0.9600 . ?

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
C008 N006 C00A 118.63(19) . . ?
C00I O007 C00P 118.4(3) . . ?
N006 C008 C009 116.02(19) . . ?
N006 C008 C00E 123.5(2) . . ?
C00E C008 C009 120.5(2) . . ?
C00B C009 C008 121.3(2) . . ?
C00G C009 C008 122.7(2) . . ?
C00G C009 C00B 116.1(2) . . ?
N006 C00A C00D 116.52(19) . . ?
N006 C00A C00H 121.0(2) . . ?
C00H C00A C00D 122.5(2) . . ?
F001 C00B C009 120.4(2) . . ?
F001 C00B C00C 117.1(2) . . ?
C00C C00B C009 122.5(2) . . ?
F003 C00C C00B 120.4(2) . . ?
F003 C00C C00K 120.0(2) . . ?
C00B C00C C00K 119.6(2) . . ?
C00F C00D C00A 121.4(2) . . ?
C00L C00D C00A 120.9(2) . . ?
C00L C00D C00F 117.6(2) . . ?
C008 C00E H00E 121.3 . . ?
C00M C00E C008 117.5(3) . . ?
C00M C00E H00E 121.3 . . ?
C00D C00F H00F 119.6 . . ?
C00N C00F C00D 120.7(2) . . ?
C00N C00F H00F 119.6 . . ?
F002 C00G C009 120.5(2) . . ?
F002 C00G C00O 117.3(2) . . ?
C009 C00G C00O 122.2(2) . . ?
C00A C00H H00H 120.3 . . ?
C00M C00H C00A 119.5(2) . . ?
C00M C00H H00H 120.3 . . ?
O007 C00I C00J 125.5(3) . . ?
O007 C00I C00N 115.2(2) . . ?
C00N C00I C00J 119.3(3) . . ?
C00I C00J H00J 120.2 . . ?
C00L C00J C00I 119.7(2) . . ?
C00L C00J H00J 120.2 . . ?
F005 C00K C00C 119.5(3) . . ?
F005 C00K C00O 120.8(3) . . ?
C00O C00K C00C 119.7(2) . . ?
C00D C00L C00J 121.8(2) . . ?
C00D C00L H00L 119.1 . . ?
C00J C00L H00L 119.1 . . ?
C00E C00M H00M 120.0 . . ?
C00H C00M C00E 120.0(2) . . ?
C00H C00M H00M 120.0 . . ?
C00F C00N H00N 119.6 . . ?
C00I C00N C00F 120.8(2) . . ?
C00I C00N H00N 119.6 . . ?
F004 C00O C00G 120.2(3) . . ?
F004 C00O C00K 119.9(3) . . ?
C00K C00O C00G 119.9(2) . . ?
O007 C00P H00A 109.5 . . ?
O007 C00P H00B 109.5 . . ?
O007 C00P H00C 109.5 . . ?
H00A C00P H00B 109.5 . . ?
H00A C00P H00C 109.5 . . ?
H00B C00P H00C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2019-05-22
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.565
_oxdiff_exptl_absorpt_empirical_full_min 0.608
####################################################################### 
# 
# 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_ch-ls-319-2
_database_code_depnum_ccdc_archive 'CCDC 2008227'
loop_
_audit_author_name
_audit_author_address
ShunLi
;SICHUAN UNIVERCITY
China
;
_audit_update_record             
;
2020-06-05 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;
_audit_creation_date             2019-09-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H6 F5 N'
_chemical_formula_sum            'C15 H6 F5 N'
_chemical_formula_weight         295.21
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.3188(3)
_cell_length_b                   7.6606(5)
_cell_length_c                   12.6995(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.260(5)
_cell_angle_gamma                90
_cell_volume                     600.71(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1194
_cell_measurement_temperature    294.54(12)
_cell_measurement_theta_max      71.4770
_cell_measurement_theta_min      7.1570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.337
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2777
_diffrn_reflns_point_group_measured_fraction_full 0.793
_diffrn_reflns_point_group_measured_fraction_max 0.768
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.744
_diffrn_reflns_theta_min         3.562
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.54(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00 -19.00   1.00    1.00    --  -36.04 -57.00 150.00   84
  2  ω    -63.00  32.00   1.00    1.00    --  -36.04  77.00 -90.00   95
  3  ω     19.00 103.00   1.00    1.00    --   36.04  57.00  60.00   84
  4  ω     23.00  89.00   1.00    1.00    --   36.04-125.00   0.00   66
  5  ω     19.00 103.00   1.00    1.00    --   36.04  57.00-180.00   84
  6  ω     37.00 109.00   1.00    1.26    --  106.21 -94.00   0.00   72
  7  ω     79.00 174.00   1.00    1.26    --  106.21  77.00 -30.00   95
  8  ω     36.00 113.00   1.00    1.26    --  106.21-111.00 -60.00   77
  9  ω     89.00 175.00   1.00    1.26    --  106.21  45.00-120.00   86
 10  ω     36.00 128.00   1.00    1.26    --  106.21 -30.00-180.00   92
 11  ω     39.00 133.00   1.00    1.26    --  106.21 -77.00-150.00   94
 12  ω     85.00 135.00   1.00    1.26    --  106.21  30.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0052792000
_diffrn_orient_matrix_UB_12      -0.0248954000
_diffrn_orient_matrix_UB_13      0.1209581000
_diffrn_orient_matrix_UB_21      0.0587473000
_diffrn_orient_matrix_UB_22      0.1940787000
_diffrn_orient_matrix_UB_23      0.0202368000
_diffrn_orient_matrix_UB_31      -0.2422717000
_diffrn_orient_matrix_UB_32      0.0465300000
_diffrn_orient_matrix_UB_33      -0.0195261000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.456
_reflns_Friedel_fraction_full    0.551
_reflns_Friedel_fraction_max     0.522
_reflns_number_gt                1639
_reflns_number_total             1808
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.114
_refine_ls_abs_structure_details 
;
 Flack x determined using 411 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1808
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0694
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1304P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1740
_refine_ls_wR_factor_ref         0.1823
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.7592(4) 0.6523(4) 0.4040(2) 0.0606(7) Uani 1 1 d . . . . .
F002 F 0.0891(4) 0.3703(4) 0.3890(2) 0.0628(8) Uani 1 1 d . . . . .
F003 F 0.0349(5) 0.3456(5) 0.1749(2) 0.0735(9) Uani 1 1 d . . . . .
F004 F 0.7021(5) 0.6238(5) 0.1906(2) 0.0765(9) Uani 1 1 d . . . . .
F005 F 0.3388(6) 0.4724(6) 0.0741(2) 0.0823(10) Uani 1 1 d . . . . .
N006 N 0.6412(5) 0.4585(4) 0.5808(3) 0.0446(7) Uani 1 1 d . . . . .
C007 C 0.5814(6) 0.5723(6) 0.3509(3) 0.0466(9) Uani 1 1 d . . . . .
C008 C 0.4586(6) 0.5220(5) 0.5250(3) 0.0433(8) Uani 1 1 d . . . . .
C009 C 0.6735(6) 0.4622(5) 0.6905(3) 0.0456(9) Uani 1 1 d . . . . .
C00A C 0.5174(7) 0.5329(6) 0.7443(3) 0.0493(10) Uani 1 1 d . . . . .
C00B C 0.5520(7) 0.5604(7) 0.2404(4) 0.0539(10) Uani 1 1 d . . . . .
C00C C 0.2123(7) 0.4223(6) 0.2320(3) 0.0534(10) Uani 1 1 d . . . . .
C00D C 0.3680(8) 0.4845(6) 0.1809(3) 0.0551(10) Uani 1 1 d . . . . .
C00E C 0.4267(6) 0.5110(5) 0.4050(3) 0.0441(9) Uani 1 1 d . . . . .
C00F C 0.2430(6) 0.4358(5) 0.3427(3) 0.0485(9) Uani 1 1 d . . . . .
C00G C 0.3262(7) 0.6017(6) 0.6801(4) 0.0535(11) Uani 1 1 d . . . . .
H00G H 0.2211 0.6503 0.7125 0.064 Uiso 1 1 calc R . . . .
C00H C 0.2951(6) 0.5974(6) 0.5716(3) 0.0508(10) Uani 1 1 d . . . . .
H00H H 0.1696 0.6427 0.5285 0.061 Uiso 1 1 calc R . . . .
C00I C 0.8668(7) 0.3918(7) 0.7516(3) 0.0551(10) Uani 1 1 d . . . . .
H00I H 0.9703 0.3460 0.7171 0.066 Uiso 1 1 calc R . . . .
C00J C 0.5614(8) 0.5291(7) 0.8578(4) 0.0647(13) Uani 1 1 d . . . . .
H00J H 0.4606 0.5743 0.8943 0.078 Uiso 1 1 calc R . . . .
C00K C 0.7501(9) 0.4598(9) 0.9147(4) 0.0755(15) Uani 1 1 d . . . . .
H00K H 0.7770 0.4585 0.9896 0.091 Uiso 1 1 calc R . . . .
C00L C 0.9029(9) 0.3908(8) 0.8615(4) 0.0694(13) Uani 1 1 d . . . . .
H00L H 1.0307 0.3436 0.9013 0.083 Uiso 1 1 calc R . . . .


_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
F001 C007 1.331(5) . ?
F002 C00F 1.336(5) . ?
F003 C00C 1.335(5) . ?
F004 C00B 1.337(5) . ?
F005 C00D 1.333(5) . ?
N006 C008 1.313(5) . ?
N006 C009 1.365(5) . ?
C007 C00B 1.380(6) . ?
C007 C00E 1.390(5) . ?
C008 C00E 1.497(5) . ?
C008 C00H 1.417(5) . ?
C009 C00A 1.421(5) . ?
C009 C00I 1.408(6) . ?
C00A C00G 1.409(6) . ?
C00A C00J 1.409(6) . ?
C00B C00D 1.374(6) . ?
C00C C00D 1.374(7) . ?
C00C C00F 1.382(6) . ?
C00E C00F 1.383(6) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.350(6) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00L 1.366(6) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.364(7) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.394(8) . ?
C00L H00L 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
C008 N006 C009 117.8(3) . . ?
F001 C007 C00B 117.6(4) . . ?
F001 C007 C00E 120.8(4) . . ?
C00B C007 C00E 121.5(4) . . ?
N006 C008 C00E 116.2(3) . . ?
N006 C008 C00H 124.1(4) . . ?
C00H C008 C00E 119.7(3) . . ?
N006 C009 C00A 122.0(3) . . ?
N006 C009 C00I 118.6(3) . . ?
C00I C009 C00A 119.4(3) . . ?
C00G C00A C009 117.5(3) . . ?
C00G C00A C00J 123.9(4) . . ?
C00J C00A C009 118.5(4) . . ?
F004 C00B C007 120.1(4) . . ?
F004 C00B C00D 119.8(4) . . ?
C00D C00B C007 120.2(4) . . ?
F003 C00C C00D 120.0(4) . . ?
F003 C00C C00F 120.4(4) . . ?
C00D C00C C00F 119.6(4) . . ?
F005 C00D C00B 120.5(4) . . ?
F005 C00D C00C 119.9(4) . . ?
C00B C00D C00C 119.7(4) . . ?
C007 C00E C008 121.8(4) . . ?
C00F C00E C007 116.8(4) . . ?
C00F C00E C008 121.4(3) . . ?
F002 C00F C00C 117.5(4) . . ?
F002 C00F C00E 120.4(3) . . ?
C00C C00F C00E 122.2(4) . . ?
C00A C00G H00G 119.9 . . ?
C00H C00G C00A 120.1(3) . . ?
C00H C00G H00G 119.9 . . ?
C008 C00H H00H 120.8 . . ?
C00G C00H C008 118.4(4) . . ?
C00G C00H H00H 120.8 . . ?
C009 C00I H00I 119.9 . . ?
C00L C00I C009 120.1(4) . . ?
C00L C00I H00I 119.9 . . ?
C00A C00J H00J 119.7 . . ?
C00K C00J C00A 120.7(4) . . ?
C00K C00J H00J 119.7 . . ?
C00J C00K H00K 119.7 . . ?
C00J C00K C00L 120.6(4) . . ?
C00L C00K H00K 119.7 . . ?
C00I C00L C00K 120.7(5) . . ?
C00I C00L H00L 119.7 . . ?
C00K C00L H00L 119.7 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2019-09-24
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.962
_oxdiff_exptl_absorpt_empirical_full_min 0.709
####################################################################### 
# 
# 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_191024_s3_unk
_database_code_depnum_ccdc_archive 'CCDC 2008278'
loop_
_audit_author_name
_audit_author_address
ShunLi
;SICHUAN UNIVERCITY
China
;
_audit_update_record             
;
2020-06-05 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;
_audit_creation_date             2019-10-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H5 Br F5 N'
_chemical_formula_sum            'C15 H5 Br F5 N'
_chemical_formula_weight         374.11
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3br
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5060(9)
_cell_length_b                   7.9033(10)
_cell_length_c                   11.6955(12)
_cell_angle_alpha                71.161(10)
_cell_angle_beta                 84.470(9)
_cell_angle_gamma                85.894(10)
_cell_volume                     652.98(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1791
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9420
_cell_measurement_theta_min      3.6810
_shelx_estimated_absorpt_T_max   0.502
_shelx_estimated_absorpt_T_min   0.400
_exptl_absorpt_coefficient_mu    3.202
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.903
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5258
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         3.174
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106 -178.0000   90.0000 52

#__ type_ start__ end____ width___ exp.time_
  2 omega  -42.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106   77.0000   60.0000 95

#__ type_ start__ end____ width___ exp.time_
  3 omega  -25.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000 -180.0000 49

#__ type_ start__ end____ width___ exp.time_
  4 omega  -81.00   -1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -38.0000  120.0000 80

#__ type_ start__ end____ width___ exp.time_
  5 omega  -82.00   12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -77.0000  -60.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0514689000
_diffrn_orient_matrix_UB_12      0.0539243000
_diffrn_orient_matrix_UB_13      0.0212475000
_diffrn_orient_matrix_UB_21      0.0002328000
_diffrn_orient_matrix_UB_22      -0.0674434000
_diffrn_orient_matrix_UB_23      0.0573416000
_diffrn_orient_matrix_UB_31      0.0798820000
_diffrn_orient_matrix_UB_32      -0.0393994000
_diffrn_orient_matrix_UB_33      -0.0197896000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2152
_reflns_number_total             2669
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2669
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0298P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0734
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.92072(4) 0.75810(4) 0.30315(3) 0.05302(13) Uani 1 1 d . . . . .
F1 F 0.9498(2) 0.8159(2) 0.86715(16) 0.0607(5) Uani 1 1 d . . . . .
F2 F 0.9266(3) 0.5837(2) 1.09235(15) 0.0633(5) Uani 1 1 d . . . . .
F3 F 0.6030(3) 0.4938(2) 1.21113(14) 0.0625(5) Uani 1 1 d . . . . .
F4 F 0.3016(3) 0.6451(2) 1.10474(16) 0.0658(5) Uani 1 1 d . . . . .
F5 F 0.3225(2) 0.8790(2) 0.88080(16) 0.0628(5) Uani 1 1 d . . . . .
N1 N 0.5852(3) 1.1491(3) 0.7300(2) 0.0428(6) Uani 1 1 d . . . . .
C1 C 0.8383(4) 0.8320(3) 0.4383(2) 0.0393(7) Uani 1 1 d . . . . .
C2 C 0.8328(4) 0.7032(3) 0.5529(3) 0.0433(7) Uani 1 1 d . . . . .
H2 H 0.8706 0.5856 0.5610 0.052 Uiso 1 1 calc R . . . .
C3 C 0.7726(4) 0.7491(3) 0.6526(2) 0.0411(7) Uani 1 1 d . . . . .
H3 H 0.7694 0.6628 0.7288 0.049 Uiso 1 1 calc R . . . .
C4 C 0.7146(3) 0.9279(3) 0.6409(2) 0.0336(6) Uani 1 1 d . . . . .
C5 C 0.6463(3) 0.9851(3) 0.7403(2) 0.0355(6) Uani 1 1 d . . . . .
C6 C 0.5938(4) 1.2699(4) 0.6173(3) 0.0466(8) Uani 1 1 d . . . . .
H6 H 0.5518 1.3865 0.6092 0.056 Uiso 1 1 calc R . . . .
C7 C 0.6591(4) 1.2331(3) 0.5157(3) 0.0434(7) Uani 1 1 d . . . . .
H7 H 0.6632 1.3228 0.4410 0.052 Uiso 1 1 calc R . . . .
C8 C 0.7211(4) 1.0567(3) 0.5245(2) 0.0344(6) Uani 1 1 d . . . . .
C9 C 0.7849(4) 1.0063(3) 0.4221(2) 0.0381(7) Uani 1 1 d . . . . .
H9 H 0.7903 1.0903 0.3450 0.046 Uiso 1 1 calc R . . . .
C10 C 0.6366(4) 0.8565(3) 0.8660(2) 0.0354(6) Uani 1 1 d . . . . .
C11 C 0.7872(4) 0.7782(4) 0.9238(2) 0.0401(7) Uani 1 1 d . . . . .
C12 C 0.7771(4) 0.6586(4) 1.0395(2) 0.0412(7) Uani 1 1 d . . . . .
C13 C 0.6141(4) 0.6149(3) 1.1000(2) 0.0434(7) Uani 1 1 d . . . . .
C14 C 0.4618(4) 0.6911(4) 1.0467(2) 0.0404(7) Uani 1 1 d . . . . .
C15 C 0.4749(4) 0.8104(3) 0.9311(2) 0.0395(7) 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
Br1 C1 1.892(2) . ?
F1 C11 1.336(3) . ?
F2 C12 1.339(3) . ?
F3 C13 1.341(3) . ?
F4 C14 1.336(3) . ?
F5 C15 1.336(3) . ?
N1 C5 1.315(3) . ?
N1 C6 1.354(3) . ?
C1 C2 1.396(4) . ?
C1 C9 1.364(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.357(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.416(3) . ?
C4 C5 1.417(3) . ?
C4 C8 1.411(4) . ?
C5 C10 1.492(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.352(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.413(3) . ?
C8 C9 1.412(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(4) . ?
C10 C15 1.375(4) . ?
C11 C12 1.377(4) . ?
C12 C13 1.361(4) . ?
C13 C14 1.362(4) . ?
C14 C15 1.375(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C6 117.1(2) . . ?
C2 C1 Br1 118.00(18) . . ?
C9 C1 Br1 120.0(2) . . ?
C9 C1 C2 122.0(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 123.4(2) . . ?
C8 C4 C3 118.9(2) . . ?
C8 C4 C5 117.6(2) . . ?
N1 C5 C4 124.0(2) . . ?
N1 C5 C10 115.4(2) . . ?
C4 C5 C10 120.6(2) . . ?
N1 C6 H6 117.7 . . ?
C7 C6 N1 124.6(2) . . ?
C7 C6 H6 117.7 . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.1(3) . . ?
C8 C7 H7 120.4 . . ?
C4 C8 C7 117.6(2) . . ?
C4 C8 C9 120.0(2) . . ?
C9 C8 C7 122.4(2) . . ?
C1 C9 C8 118.7(2) . . ?
C1 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C11 C10 C5 122.4(3) . . ?
C15 C10 C5 121.4(2) . . ?
C15 C10 C11 116.2(3) . . ?
F1 C11 C10 120.1(3) . . ?
F1 C11 C12 117.8(3) . . ?
C12 C11 C10 122.1(3) . . ?
F2 C12 C11 120.4(3) . . ?
F2 C12 C13 119.9(3) . . ?
C13 C12 C11 119.7(3) . . ?
F3 C13 C12 120.1(3) . . ?
F3 C13 C14 119.8(3) . . ?
C12 C13 C14 120.1(3) . . ?
F4 C14 C13 120.1(3) . . ?
F4 C14 C15 120.6(3) . . ?
C13 C14 C15 119.3(3) . . ?
F5 C15 C10 119.8(2) . . ?
F5 C15 C14 117.5(3) . . ?
C10 C15 C14 122.7(3) . . ?

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
Br1 C1 C2 C3 -179.1(2) . . . . ?
Br1 C1 C9 C8 178.9(2) . . . . ?
F1 C11 C12 F2 0.1(3) . . . . ?
F1 C11 C12 C13 -179.3(2) . . . . ?
F2 C12 C13 F3 -1.6(4) . . . . ?
F2 C12 C13 C14 179.8(2) . . . . ?
F3 C13 C14 F4 -0.2(4) . . . . ?
F3 C13 C14 C15 -177.8(2) . . . . ?
F4 C14 C15 F5 0.9(3) . . . . ?
F4 C14 C15 C10 -177.4(2) . . . . ?
N1 C5 C10 C11 -115.6(3) . . . . ?
N1 C5 C10 C15 64.1(3) . . . . ?
N1 C6 C7 C8 1.1(5) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C1 C9 C8 -0.4(4) . . . . ?
C2 C3 C4 C5 178.6(3) . . . . ?
C2 C3 C4 C8 -0.2(4) . . . . ?
C3 C4 C5 N1 -177.1(3) . . . . ?
C3 C4 C5 C10 1.6(4) . . . . ?
C3 C4 C8 C7 178.8(3) . . . . ?
C3 C4 C8 C9 0.0(4) . . . . ?
C4 C5 C10 C11 65.6(3) . . . . ?
C4 C5 C10 C15 -114.7(3) . . . . ?
C4 C8 C9 C1 0.3(4) . . . . ?
C5 N1 C6 C7 0.5(5) . . . . ?
C5 C4 C8 C7 0.0(4) . . . . ?
C5 C4 C8 C9 -178.9(2) . . . . ?
C5 C10 C11 F1 -0.2(4) . . . . ?
C5 C10 C11 C12 -179.4(2) . . . . ?
C5 C10 C15 F5 1.1(3) . . . . ?
C5 C10 C15 C14 179.4(2) . . . . ?
C6 N1 C5 C4 -1.9(4) . . . . ?
C6 N1 C5 C10 179.3(2) . . . . ?
C6 C7 C8 C4 -1.2(4) . . . . ?
C6 C7 C8 C9 177.6(3) . . . . ?
C7 C8 C9 C1 -178.5(3) . . . . ?
C8 C4 C5 N1 1.7(4) . . . . ?
C8 C4 C5 C10 -179.6(2) . . . . ?
C9 C1 C2 C3 0.2(4) . . . . ?
C10 C11 C12 F2 179.3(2) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C11 C10 C15 F5 -179.2(2) . . . . ?
C11 C10 C15 C14 -0.9(4) . . . . ?
C11 C12 C13 F3 177.7(2) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C12 C13 C14 F4 178.3(2) . . . . ?
C12 C13 C14 C15 0.8(4) . . . . ?
C13 C14 C15 F5 178.4(2) . . . . ?
C13 C14 C15 C10 0.1(4) . . . . ?
C15 C10 C11 F1 -179.9(2) . . . . ?
C15 C10 C11 C12 0.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
