# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_exp_10074
_database_code_depnum_ccdc_archive 'CCDC 2108960'
loop_
_audit_author_name
_audit_author_address
'Li Xue'
;HuaQiao university
China
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2022-04-19 downloaded from the CCDC.
;
_audit_creation_date             2021-09-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r1)
;
_chemical_formula_moiety         '0.67(C12 H12 F2 N2 O3)'
_chemical_formula_sum            'C8 H8 F1.333 N1.333 O2'
_chemical_formula_weight         180.16
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.7214(13)
_cell_length_b                   9.3290(16)
_cell_length_c                   9.6652(12)
_cell_measurement_temperature    298
_cell_angle_alpha                112.760(14)
_cell_angle_beta                 100.215(12)
_cell_angle_gamma                90.229(14)
_cell_volume                     629.80(19)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    1237
_cell_measurement_theta_max      27.4260
_exptl_crystal_description       block
_cell_measurement_theta_min      4.3520
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.4249
_exptl_crystal_F_000             280.2023
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4569
_diffrn_ambient_temperature      298
_diffrn_reflns_theta_full        24.9990
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.73
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.9964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  27.00   1.00    1.31    --   15.65 -57.00  30.00   79
  2  ω     -4.00  21.00   1.00    1.31    --  -16.28 -99.00  30.00   25
  3  ω    -16.00  22.00   1.00    1.31    --  -16.28 -99.00 -60.00   38
  4  ω    -52.00  42.00   1.00    1.31    --   15.65 -77.00 150.00   94
  5  ω    -11.00  79.00   1.00    1.31    --   15.65  77.00 -90.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0821137000
_diffrn_orient_matrix_UB_12      0.0196481000
_diffrn_orient_matrix_UB_13      -0.0140830000
_diffrn_orient_matrix_UB_21      0.0356581000
_diffrn_orient_matrix_UB_22      0.0296603000
_diffrn_orient_matrix_UB_23      0.0795398000
_diffrn_orient_matrix_UB_31      0.0274693000
_diffrn_orient_matrix_UB_32      -0.0746750000
_diffrn_orient_matrix_UB_33      -0.0075021000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              10
_reflns_limit_k_min              -11
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                1542
_reflns_number_total             2212
_reflns_odcompleteness_completeness 99.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.2445
_refine_diff_density_min         -0.3082
_refine_diff_density_rms         0.0732
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             5.4642
_refine_ls_goodness_of_fit_ref   0.9742
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      0.9742
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1576
_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 Ternary CH refined with riding coordinates:
 C00D(H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00B(H00B), C00F(H00F), C00A(H00A), C00E(H00E)
2.c Idealised Me refined as rotating group:
 C00I(H00c,H00h,H00i), C00J(H00j,H00k,H00l)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
F001 F 0.14242(18) -0.01726(14) 0.28049(18) 0.0755(5) Uani 1.000000 .
F002 F 0.3125(2) 0.09388(18) 0.19373(16) 0.0806(5) Uani 1.000000 .
O003 O 0.3465(2) 0.16164(16) 0.44244(17) 0.0626(5) Uani 1.000000 .
O004 O 0.9129(2) 0.4906(2) 1.13787(19) 0.0704(5) Uani 1.000000 .
N005 N -0.0852(2) 0.22425(19) 0.3191(2) 0.0516(5) Uani 1.000000 .
N006 N 0.8315(2) 0.5795(2) 1.0898(2) 0.0576(6) Uani 1.000000 .
O007 O 0.8480(3) 0.7202(2) 1.1573(2) 0.0902(7) Uani 1.000000 .
C008 C 0.4634(2) 0.3852(2) 0.6729(2) 0.0441(5) Uani 1.000000 .
C009 C 0.7052(2) 0.5125(2) 0.9435(2) 0.0473(6) Uani 1.000000 .
C00A C 0.5743(3) 0.2903(2) 0.7238(3) 0.0521(6) Uani 1.000000 .
C00B C 0.5992(3) 0.6095(2) 0.8950(3) 0.0537(6) Uani 1.000000 .
C00C C 0.3310(3) 0.3186(2) 0.5319(2) 0.0461(6) Uani 1.000000 .
C00D C 0.1001(3) 0.2555(2) 0.3245(2) 0.0499(6) Uani 1.000000 .
C00E C 0.1973(3) 0.3758(2) 0.4718(3) 0.0546(6) Uani 1.000000 .
C00F C 0.6946(3) 0.3546(3) 0.8598(3) 0.0540(6) Uani 1.000000 .
C00G C 0.4793(3) 0.5460(2) 0.7602(3) 0.0530(6) Uani 1.000000 .
C00H C 0.2231(3) 0.1214(2) 0.3105(2) 0.0520(6) Uani 1.000000 .
C00I C -0.1804(3) 0.1224(3) 0.1674(3) 0.0685(8) Uani 1.000000 .
C00J C -0.1260(4) 0.1790(3) 0.4384(3) 0.0742(8) Uani 1.000000 .
H00G H 0.4076(3) 0.6103(2) 0.7263(3) 0.0637(7) Uiso 1.000000 R
H00B H 0.6092(3) 0.7163(2) 0.9529(3) 0.0645(7) Uiso 1.000000 R
H00F H 0.7678(3) 0.2916(3) 0.8944(3) 0.0648(7) Uiso 1.000000 R
H00A H 0.5670(3) 0.1836(2) 0.6659(3) 0.0626(7) Uiso 1.000000 R
H00D H 0.1094(3) 0.2910(2) 0.2428(2) 0.0599(7) Uiso 1.000000 R
H00E H 0.1669(3) 0.4779(2) 0.5153(3) 0.0656(8) Uiso 1.000000 R
H00c H -0.1563(19) 0.1610(13) 0.0935(4) 0.1027(12) Uiso 1.000000 GR
H00h H -0.1427(19) 0.0188(6) 0.1421(10) 0.1027(12) Uiso 1.000000 GR
H00i H -0.3048(4) 0.1201(17) 0.1668(6) 0.1027(12) Uiso 1.000000 GR
H00j H -0.101(2) 0.0726(7) 0.4163(11) 0.1113(12) Uiso 1.000000 GR
H00k H -0.0555(17) 0.2452(13) 0.5351(4) 0.1113(12) Uiso 1.000000 GR
H00l H -0.2488(6) 0.189(2) 0.4427(14) 0.1113(12) Uiso 1.000000 GR


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 C00H 1.336(3) . ?
F002 C00H 1.367(3) . ?
O003 C00C 1.402(2) . ?
O003 C00H 1.368(3) . ?
O004 N006 1.224(2) . ?
N005 C00D 1.447(3) . ?
N005 C00I 1.459(3) . ?
N005 C00J 1.454(3) . ?
N006 O007 1.213(2) . ?
N006 C009 1.471(3) . ?
C008 C00A 1.397(3) . ?
C008 C00C 1.461(3) . ?
C008 C00G 1.400(3) . ?
C009 C00B 1.381(3) . ?
C009 C00F 1.372(3) . ?
C00A C00F 1.379(3) . ?
C00A H00A 0.9300 . ?
C00B C00G 1.370(3) . ?
C00B H00B 0.9300 . ?
C00C C00E 1.312(3) . ?
C00D C00E 1.493(3) . ?
C00D C00H 1.553(3) . ?
C00D H00D 0.9800 . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00I H00c 0.9600 . ?
C00I H00h 0.9600 . ?
C00I H00i 0.9600 . ?
C00J H00j 0.9600 . ?
C00J H00k 0.9600 . ?
C00J H00l 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
C00H O003 C00C 107.19(15) . . ?
C00I N005 C00D 113.3(2) . . ?
C00J N005 C00D 116.02(17) . . ?
C00J N005 C00I 112.4(2) . . ?
O007 N006 O004 123.42(19) . . ?
C009 N006 O004 118.42(18) . . ?
C009 N006 O007 118.2(2) . . ?
C00C C008 C00A 120.97(18) . . ?
C00G C008 C00A 118.99(19) . . ?
C00G C008 C00C 120.04(17) . . ?
C00B C009 N006 119.23(19) . . ?
C00F C009 N006 118.96(19) . . ?
C00F C009 C00B 121.8(2) . . ?
C00F C00A C008 120.15(19) . . ?
H00A C00A C008 119.93(12) . . ?
H00A C00A C00F 119.93(12) . . ?
C00G C00B C009 118.97(19) . . ?
H00B C00B C009 120.52(12) . . ?
H00B C00B C00G 120.52(12) . . ?
C008 C00C O003 114.59(16) . . ?
C00E C00C O003 112.57(18) . . ?
C00E C00C C008 132.84(18) . . ?
C00E C00D N005 115.09(19) . . ?
C00H C00D N005 118.16(18) . . ?
C00H C00D C00E 98.92(15) . . ?
H00D C00D N005 108.00(12) . . ?
H00D C00D C00E 108.00(14) . . ?
H00D C00D C00H 108.00(13) . . ?
C00D C00E C00C 111.06(17) . . ?
H00E C00E C00C 124.47(12) . . ?
H00E C00E C00D 124.47(10) . . ?
C00A C00F C009 119.36(19) . . ?
H00F C00F C009 120.32(12) . . ?
H00F C00F C00A 120.32(12) . . ?
C00B C00G C008 120.72(19) . . ?
H00G C00G C008 119.64(12) . . ?
H00G C00G C00B 119.64(12) . . ?
F002 C00H F001 104.30(16) . . ?
O003 C00H F001 108.27(19) . . ?
O003 C00H F002 107.21(18) . . ?
C00D C00H F001 115.49(18) . . ?
C00D C00H F002 111.60(19) . . ?
C00D C00H O003 109.54(15) . . ?
H00c C00I N005 109.5 . . ?
H00h C00I N005 109.5 . . ?
H00h C00I H00c 109.5 . . ?
H00i C00I N005 109.5 . . ?
H00i C00I H00c 109.5 . . ?
H00i C00I H00h 109.5 . . ?
H00j C00J N005 109.5 . . ?
H00k C00J N005 109.5 . . ?
H00k C00J H00j 109.5 . . ?
H00l C00J N005 109.5 . . ?
H00l C00J H00j 109.5 . . ?
H00l C00J H00k 109.5 . . ?

_olex2_date_sample_data_collection 2021-09-10
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.888
_oxdiff_exptl_absorpt_empirical_full_min 0.610
####################################################################### 
# 
# 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_exp_10450
_database_code_depnum_ccdc_archive 'CCDC 2124886'
loop_
_audit_author_name
_audit_author_address
'Li Xue'
;HuaQiao university
China
;
_audit_update_record             
;
2021-11-29 deposited with the CCDC.	2022-04-19 downloaded from the CCDC.
;
_audit_creation_date             2021-11-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r1)
;
_chemical_formula_moiety         'C18 H17 F2 N O'
_chemical_formula_sum            'C18 H17 F2 N O'
_chemical_formula_weight         301.34
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   9.4835(17)
_cell_length_b                   9.8772(13)
_cell_length_c                   9.941(2)
_cell_measurement_temperature    298
_cell_angle_alpha                107.076(15)
_cell_angle_beta                 117.98(2)
_cell_angle_gamma                93.602(12)
_cell_volume                     763.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1110
_cell_measurement_theta_max      23.2280
_cell_measurement_theta_min      4.2940
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81688
_exptl_crystal_description       block
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.3105
_exptl_crystal_F_000             316.1876
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_ambient_temperature      298
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5930
_diffrn_reflns_theta_full        24.9996
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.72
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.9970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  35.00   1.00    1.50    --   15.65 -38.00   0.00   88
  2  ω     -6.00  19.00   1.00    1.50    --  -16.28 -99.00 -30.00   25
  3  ω      7.00  74.00   1.00    1.50    --   15.65-134.00 -22.00   67
  4  ω     -9.00  18.00   1.00    1.50    --  -16.28 -99.00 150.00   27
  5  ω     -1.00  30.00   1.00    1.50    --   15.65  57.00 150.00   31
  6  ω    -19.00  13.00   1.00    1.50    --   15.65 -99.00 -90.00   32
  7  ω      4.00  84.00   1.00    1.50    --   15.65  38.00-180.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0038011000
_diffrn_orient_matrix_UB_12      -0.0757319000
_diffrn_orient_matrix_UB_13      -0.0197519000
_diffrn_orient_matrix_UB_21      -0.0821267000
_diffrn_orient_matrix_UB_22      -0.0156453000
_diffrn_orient_matrix_UB_23      -0.0652243000
_diffrn_orient_matrix_UB_31      0.0290276000
_diffrn_orient_matrix_UB_32      0.0010105000
_diffrn_orient_matrix_UB_33      -0.0538167000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -11
_reflns_limit_k_max              10
_reflns_limit_k_min              -11
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                1669
_reflns_number_total             2677
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.2202
_refine_diff_density_min         -0.3049
_refine_diff_density_rms         0.0659
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             5.4745
_refine_ls_goodness_of_fit_ref   0.9366
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2677
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0541
_refine_ls_restrained_S_all      0.9366
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1767
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C006(H006)
2.b Secondary CH2 refined with riding coordinates:
 C00C(H00b,H00c)
2.c Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00M(H00o), C00I(H00I), C00L(H00n), C00E(H00E), C00D(H00D),
 C00H(H00H), C00G(H00G), C00F(H00F), C00A(H00A), C009(H009)
2.d Idealised Me refined as rotating group:
 C00K(H00k,H00l,H00m)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
F001 F 0.4217(2) 0.50547(15) 0.3036(2) 0.0747(5) Uani 1.000000 .
O002 O 0.2957(2) 0.58995(17) 0.4366(2) 0.0594(5) Uani 1.000000 .
F003 F 0.19865(19) 0.57045(19) 0.1796(2) 0.0885(6) Uani 1.000000 .
N004 N 0.6083(2) 0.7871(2) 0.4511(2) 0.0511(5) Uani 1.000000 .
C005 C 0.6669(3) 0.7689(2) 0.3423(3) 0.0480(6) Uani 1.000000 .
C006 C 0.4337(3) 0.7648(3) 0.3888(3) 0.0531(6) Uani 1.000000 .
C007 C 0.3180(3) 0.7307(2) 0.5405(3) 0.0503(6) Uani 1.000000 .
C008 C 0.2627(3) 0.7369(3) 0.6567(3) 0.0518(6) Uani 1.000000 .
C009 C 0.3911(3) 0.8324(3) 0.5168(3) 0.0568(7) Uani 1.000000 .
C00A C 0.8353(3) 0.8063(3) 0.4022(3) 0.0578(7) Uani 1.000000 .
C00B C 0.3388(3) 0.6055(3) 0.3259(3) 0.0573(7) Uani 1.000000 .
C00C C 0.7135(3) 0.7805(3) 0.6128(3) 0.0565(7) Uani 1.000000 .
C00D C 0.5624(3) 0.7166(3) 0.1731(3) 0.0601(7) Uani 1.000000 .
C00E C 0.1966(3) 0.6111(3) 0.6626(3) 0.0615(7) Uani 1.000000 .
C00F C 0.8940(3) 0.7912(3) 0.2965(4) 0.0689(8) Uani 1.000000 .
C00G C 0.7895(4) 0.7401(3) 0.1306(4) 0.0709(8) Uani 1.000000 .
C00H C 0.6240(4) 0.7028(3) 0.0697(4) 0.0703(8) Uani 1.000000 .
C00I C 0.1599(4) 0.7532(4) 0.8784(4) 0.0727(8) Uani 1.000000 .
C00J C 0.2765(4) 0.8704(3) 0.7635(4) 0.0661(7) Uani 1.000000 .
C00K C 0.8013(4) 0.9282(3) 0.7486(4) 0.0757(8) Uani 1.000000 .
C00L C 0.1454(3) 0.6201(3) 0.7737(4) 0.0712(8) Uani 1.000000 .
C00M C 0.2256(4) 0.8784(3) 0.8737(4) 0.0774(9) Uani 1.000000 .
H00J H 0.3206(4) 0.9556(3) 0.7608(4) 0.0794(9) Uiso 1.000000 R
H00o H 0.2358(4) 0.9688(3) 0.9453(4) 0.0929(10) Uiso 1.000000 R
H00I H 0.1252(4) 0.7588(4) 0.9528(4) 0.0873(10) Uiso 1.000000 R
H00n H 0.1010(3) 0.5354(3) 0.7771(4) 0.0855(10) Uiso 1.000000 R
H00E H 0.1866(3) 0.5204(3) 0.5916(3) 0.0738(9) Uiso 1.000000 R
H00D H 0.4495(3) 0.6905(3) 0.1290(3) 0.0721(8) Uiso 1.000000 R
H00H H 0.5519(4) 0.6677(3) -0.0430(4) 0.0844(9) Uiso 1.000000 R
H00G H 0.8303(4) 0.7310(3) 0.0604(4) 0.0850(10) Uiso 1.000000 R
H00F H 1.0067(3) 0.8163(3) 0.3388(4) 0.0827(9) Uiso 1.000000 R
H00A H 0.9087(3) 0.8418(3) 0.5146(3) 0.0694(8) Uiso 1.000000 R
H006 H 0.3842(3) 0.8039(3) 0.3015(3) 0.0638(8) Uiso 1.000000 R
H009 H 0.4129(3) 0.9322(3) 0.5719(3) 0.0682(8) Uiso 1.000000 R
H00b H 0.6466(3) 0.7265(3) 0.6385(3) 0.0678(8) Uiso 1.000000 R
H00c H 0.7947(3) 0.7271(3) 0.6086(3) 0.0678(8) Uiso 1.000000 R
H00k H 0.8707(19) 0.9814(8) 0.7262(12) 0.1136(13) Uiso 1.000000 GR
H00l H 0.7219(4) 0.9813(9) 0.7553(15) 0.1136(13) Uiso 1.000000 GR
H00m H 0.8671(18) 0.9160(3) 0.8507(5) 0.1136(13) Uiso 1.000000 GR


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 1.333(3) . ?
O002 C007 1.399(3) . ?
O002 C00B 1.384(3) . ?
F003 C00B 1.354(3) . ?
N004 C005 1.404(3) . ?
N004 C006 1.444(3) . ?
N004 C00C 1.466(3) . ?
C005 C00A 1.395(3) . ?
C005 C00D 1.393(3) . ?
C006 C009 1.499(3) . ?
C006 C00B 1.547(3) . ?
C006 H006 0.9800 . ?
C007 C008 1.464(3) . ?
C007 C009 1.324(3) . ?
C008 C00E 1.385(3) . ?
C008 C00J 1.381(4) . ?
C009 H009 0.9300 . ?
C00A C00F 1.380(3) . ?
C00A H00A 0.9300 . ?
C00C C00K 1.510(4) . ?
C00C H00b 0.9700 . ?
C00C H00c 0.9700 . ?
C00D C00H 1.381(3) . ?
C00D H00D 0.9300 . ?
C00E C00L 1.384(3) . ?
C00E H00E 0.9300 . ?
C00F C00G 1.368(4) . ?
C00F H00F 0.9300 . ?
C00G C00H 1.368(4) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00I C00L 1.367(4) . ?
C00I C00M 1.373(4) . ?
C00I H00I 0.9300 . ?
C00J C00M 1.374(4) . ?
C00J H00J 0.9300 . ?
C00K H00k 0.9600 . ?
C00K H00l 0.9600 . ?
C00K H00m 0.9600 . ?
C00L H00n 0.9300 . ?
C00M H00o 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
C00B O002 C007 106.83(17) . . ?
C006 N004 C005 119.6(2) . . ?
C00C N004 C005 119.34(18) . . ?
C00C N004 C006 118.03(17) . . ?
C00A C005 N004 120.2(2) . . ?
C00D C005 N004 122.5(2) . . ?
C00D C005 C00A 117.3(2) . . ?
C009 C006 N004 113.8(2) . . ?
C00B C006 N004 115.9(2) . . ?
C00B C006 C009 98.82(17) . . ?
H006 C006 N004 109.28(12) . . ?
H006 C006 C009 109.28(14) . . ?
H006 C006 C00B 109.28(14) . . ?
C008 C007 O002 114.92(18) . . ?
C009 C007 O002 112.4(2) . . ?
C009 C007 C008 132.7(2) . . ?
C00E C008 C007 121.3(2) . . ?
C00J C008 C007 119.9(2) . . ?
C00J C008 C00E 118.8(2) . . ?
C007 C009 C006 110.7(2) . . ?
H009 C009 C006 124.67(12) . . ?
H009 C009 C007 124.67(15) . . ?
C00F C00A C005 120.7(2) . . ?
H00A C00A C005 119.66(14) . . ?
H00A C00A C00F 119.66(16) . . ?
O002 C00B F001 108.0(2) . . ?
F003 C00B F001 105.8(2) . . ?
F003 C00B O002 107.81(17) . . ?
C006 C00B F001 114.66(18) . . ?
C006 C00B O002 109.03(19) . . ?
C006 C00B F003 111.3(2) . . ?
C00K C00C N004 113.8(2) . . ?
H00b C00C N004 108.79(11) . . ?
H00b C00C C00K 108.79(14) . . ?
H00c C00C N004 108.79(12) . . ?
H00c C00C C00K 108.79(14) . . ?
H00c C00C H00b 107.7 . . ?
C00H C00D C005 121.0(2) . . ?
H00D C00D C005 119.48(13) . . ?
H00D C00D C00H 119.48(16) . . ?
C00L C00E C008 120.2(2) . . ?
H00E C00E C008 119.92(15) . . ?
H00E C00E C00L 119.92(16) . . ?
C00G C00F C00A 121.3(2) . . ?
H00F C00F C00A 119.37(16) . . ?
H00F C00F C00G 119.37(15) . . ?
C00H C00G C00F 118.9(2) . . ?
H00G C00G C00F 120.57(15) . . ?
H00G C00G C00H 120.57(17) . . ?
C00G C00H C00D 120.9(3) . . ?
H00H C00H C00D 119.55(16) . . ?
H00H C00H C00G 119.55(17) . . ?
C00M C00I C00L 120.0(3) . . ?
H00I C00I C00L 120.00(15) . . ?
H00I C00I C00M 120.00(17) . . ?
C00M C00J C008 120.7(2) . . ?
H00J C00J C008 119.66(14) . . ?
H00J C00J C00M 119.66(16) . . ?
H00k C00K C00C 109.5 . . ?
H00l C00K C00C 109.5 . . ?
H00l C00K H00k 109.5 . . ?
H00m C00K C00C 109.5 . . ?
H00m C00K H00k 109.5 . . ?
H00m C00K H00l 109.5 . . ?
C00I C00L C00E 120.2(2) . . ?
H00n C00L C00E 119.89(16) . . ?
H00n C00L C00I 119.89(15) . . ?
C00J C00M C00I 120.1(3) . . ?
H00o C00M C00I 119.94(17) . . ?
H00o C00M C00J 119.94(16) . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.691
####################################################################### 
# 
# 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_exp_10563
_database_code_depnum_ccdc_archive 'CCDC 2131035'
loop_
_audit_author_name
_audit_author_address
'Li Xue'
;HuaQiao university
China
;
_audit_update_record             
;
2021-12-27 deposited with the CCDC.	2022-04-19 downloaded from the CCDC.
;
_audit_creation_date             2021-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r1)
;
_chemical_formula_moiety         'C20 H23 F5 N2 O3'
_chemical_formula_sum            'C20 H23 F5 N2 O3'
_chemical_formula_weight         434.41
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   12.2619(15)
_cell_length_b                   10.4477(16)
_cell_length_c                   16.5000(17)
_cell_angle_alpha                90
_cell_angle_beta                 99.896(12)
_cell_angle_gamma                90
_cell_volume                     2082.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2780
_cell_measurement_theta_max      28.2430
_cell_measurement_temperature    298
_cell_measurement_theta_min      4.0930
_exptl_absorpt_coefficient_mu    0.123
_exptl_crystal_description       block
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.3855
_exptl_crystal_F_000             904.6947
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_ambient_temperature      298
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10248
_diffrn_reflns_theta_full        24.9994
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.79
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9965
_diffrn_measured_fraction_theta_max 0.9965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  19.00   1.00    5.00    --  -16.43 -99.00 -30.00   43
  2  ω    -50.00  25.00   1.00    5.00    --   15.65 -57.00 150.00   75
  3  ω      6.00  68.00   1.00    5.00    --   15.65  19.00 150.00   62
  4  ω     -9.00  18.00   1.00    5.00    --  -16.43 -99.00 150.00   27
  5  ω     40.00  71.00   1.00    5.00    --   15.65 178.00 150.00   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0547447000
_diffrn_orient_matrix_UB_12      -0.0187959000
_diffrn_orient_matrix_UB_13      0.0029634000
_diffrn_orient_matrix_UB_21      -0.0169913000
_diffrn_orient_matrix_UB_22      0.0649204000
_diffrn_orient_matrix_UB_23      -0.0037687000
_diffrn_orient_matrix_UB_31      -0.0124576000
_diffrn_orient_matrix_UB_32      -0.0069062000
_diffrn_orient_matrix_UB_33      -0.0433943000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                2547
_reflns_number_total             3668
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.1056
_refine_diff_density_min         -0.8487
_refine_diff_density_rms         0.0922
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             5.3717
_refine_ls_goodness_of_fit_ref   1.6056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3668
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1232
_refine_ls_R_factor_gt           0.0922
_refine_ls_restrained_S_all      1.6056
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2491
_refine_ls_wR_factor_ref         0.2709
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C00D(H00a,H00d), C00I(H00e,H00f), C00M(H00h,H00i), C00Q(H00o,H00p)
2.c Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00L(H00L), C00K(H00K), C00C(H00C), C00B(H00B)
2.d Idealised Me refined as rotating group:
 C00O(H00j,H00m,H00n), C00R(H00q,H00r,H00s), C00S(H00t,H00u,H00v)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
O001 O 0.8482(2) 0.5260(3) 0.60275(13) 0.0496(8) Uani 1.000000 .
O002 O 0.4857(2) 0.4342(3) 0.18026(16) 0.0588(9) Uani 1.000000 .
F003 F 0.53411(19) 0.3875(3) 0.31085(14) 0.0835(10) Uani 1.000000 .
F004 F 0.5763(2) 0.2584(3) 0.2216(2) 0.0876(9) Uani 1.000000 .
N005 N 0.7357(2) 0.5153(3) 0.31033(16) 0.0423(8) Uani 1.000000 .
O006 O 0.7550(3) 0.7134(3) 0.57574(17) 0.0667(9) Uani 1.000000 .
N007 N 0.8040(3) 0.5955(3) 0.47373(18) 0.0579(10) Uani 1.000000 .
C008 C 0.4535(3) 0.5977(4) 0.07623(19) 0.0420(9) Uani 1.000000 .
C009 C 0.6769(3) 0.4572(4) 0.2355(2) 0.0444(10) Uani 1.000000 .
C00A C 0.5325(3) 0.5333(4) 0.1400(2) 0.0421(9) Uani 1.000000 .
C00B C 0.6375(3) 0.5496(4) 0.1679(2) 0.0436(10) Uani 1.000000 .
C00C C 0.3432(3) 0.5620(4) 0.0593(2) 0.0464(10) Uani 1.000000 .
C00D C 0.7792(3) 0.4221(4) 0.3743(2) 0.0445(10) Uani 1.000000 .
C00E C 0.2692(3) 0.6281(4) 0.0016(2) 0.0507(10) Uani 1.000000 .
C00F C 0.7993(3) 0.6196(4) 0.5529(2) 0.0469(10) Uani 1.000000 .
C00G C 0.4876(3) 0.7004(4) 0.0338(2) 0.0521(11) Uani 1.000000 .
C00H C 0.8543(3) 0.5379(5) 0.6930(2) 0.0522(11) Uani 1.000000 .
C00I C 0.8578(3) 0.4870(4) 0.4419(2) 0.0508(11) Uani 1.000000 .
C00J C 0.5679(3) 0.3843(5) 0.2380(2) 0.0516(11) Uani 1.000000 .
C00K C 0.3050(4) 0.7295(5) -0.0403(2) 0.0581(12) Uani 1.000000 .
C00L C 0.4145(4) 0.7642(5) -0.0238(2) 0.0592(12) Uani 1.000000 .
C00M C 0.6799(4) 0.6201(4) 0.3439(2) 0.0578(12) Uani 1.000000 .
C00N C 0.1539(4) 0.5876(7) -0.0162(3) 0.0775(16) Uani 1.000000 .
C00O C 0.9188(5) 0.4189(5) 0.7235(3) 0.0817(16) Uani 1.000000 .
F00P F 0.1253(3) 0.5027(7) 0.0270(4) 0.219(4) Uani 1.000000 .
C00Q C 0.7590(5) 0.6877(4) 0.4105(2) 0.0680(14) Uani 1.000000 .
C00R C 0.9181(4) 0.6552(5) 0.7240(3) 0.0824(16) Uani 1.000000 .
C00S C 0.7409(4) 0.5349(6) 0.7137(3) 0.0841(17) Uani 1.000000 .
F00T F 0.0856(3) 0.6742(5) -0.0142(6) 0.254(5) Uani 1.000000 .
F00U F 0.1213(4) 0.5456(9) -0.0880(3) 0.227(4) Uani 1.000000 .
H00G H 0.5612(3) 0.7262(4) 0.0447(2) 0.0626(13) Uiso 1.000000 R
H00L H 0.4391(4) 0.8322(5) -0.0523(2) 0.0710(14) Uiso 1.000000 R
H00K H 0.2555(4) 0.7739(5) -0.0793(2) 0.0697(14) Uiso 1.000000 R
H00C H 0.3187(3) 0.4930(4) 0.0870(2) 0.0556(12) Uiso 1.000000 R
H009 H 0.7279(3) 0.3976(4) 0.2154(2) 0.0533(12) Uiso 1.000000 R
H00B H 0.6818(3) 0.6105(4) 0.1483(2) 0.0523(12) Uiso 1.000000 R
H00a H 0.7185(3) 0.3843(4) 0.3967(2) 0.0533(12) Uiso 1.000000 R
H00d H 0.8174(3) 0.3541(4) 0.3506(2) 0.0533(12) Uiso 1.000000 R
H00e H 0.9227(3) 0.5161(4) 0.4209(2) 0.0609(13) Uiso 1.000000 R
H00f H 0.8818(3) 0.4265(4) 0.4860(2) 0.0609(13) Uiso 1.000000 R
H00h H 0.6519(4) 0.6802(4) 0.3005(2) 0.0693(14) Uiso 1.000000 R
H00i H 0.6174(4) 0.5873(4) 0.3665(2) 0.0693(14) Uiso 1.000000 R
H00j H 0.8851(17) 0.3455(6) 0.6944(15) 0.123(2) Uiso 1.000000 GR
H00m H 0.9937(9) 0.4271(15) 0.7143(19) 0.123(2) Uiso 1.000000 GR
H00n H 0.919(3) 0.4085(19) 0.7813(5) 0.123(2) Uiso 1.000000 GR
H00o H 0.7205(5) 0.7551(4) 0.4345(2) 0.0816(17) Uiso 1.000000 R
H00p H 0.8187(5) 0.7261(4) 0.3872(2) 0.0816(17) Uiso 1.000000 R
H00q H 0.9836(16) 0.6609(19) 0.6996(17) 0.124(2) Uiso 1.000000 GR
H00r H 0.8730(11) 0.7296(6) 0.7095(19) 0.124(2) Uiso 1.000000 GR
H00s H 0.939(3) 0.6504(17) 0.7827(4) 0.124(2) Uiso 1.000000 GR
H00t H 0.6992(11) 0.607(2) 0.689(2) 0.126(3) Uiso 1.000000 GR
H00u H 0.7047(12) 0.4569(17) 0.694(2) 0.126(3) Uiso 1.000000 GR
H00v H 0.7456(4) 0.539(4) 0.7724(3) 0.126(3) Uiso 1.000000 GR


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
O001 C00F 1.351(4) . ?
O001 C00H 1.483(4) . ?
O002 C00A 1.405(4) . ?
O002 C00J 1.366(4) . ?
F003 C00J 1.337(4) . ?
F004 C00J 1.351(5) . ?
N005 C009 1.451(5) . ?
N005 C00D 1.468(4) . ?
N005 C00M 1.451(5) . ?
O006 C00F 1.211(4) . ?
N007 C00F 1.341(5) . ?
N007 C00I 1.454(5) . ?
N007 C00Q 1.457(5) . ?
C008 C00A 1.466(5) . ?
C008 C00C 1.384(5) . ?
C008 C00G 1.385(5) . ?
C009 C00B 1.492(5) . ?
C009 C00J 1.546(5) . ?
C009 H009 0.9800 . ?
C00A C00B 1.301(5) . ?
C00B H00B 0.9300 . ?
C00C C00E 1.382(5) . ?
C00C H00C 0.9300 . ?
C00D C00I 1.506(5) . ?
C00D H00a 0.9700 . ?
C00D H00d 0.9700 . ?
C00E C00K 1.377(6) . ?
C00E C00N 1.456(6) . ?
C00G C00L 1.363(5) . ?
C00G H00G 0.9300 . ?
C00H C00O 1.513(6) . ?
C00H C00R 1.496(6) . ?
C00H C00S 1.489(6) . ?
C00I H00e 0.9700 . ?
C00I H00f 0.9700 . ?
C00K C00L 1.372(6) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00M C00Q 1.510(6) . ?
C00M H00h 0.9700 . ?
C00M H00i 0.9700 . ?
C00N F00P 1.226(6) . ?
C00N F00T 1.237(7) . ?
C00N F00U 1.262(7) . ?
C00O H00j 0.9600 . ?
C00O H00m 0.9600 . ?
C00O H00n 0.9600 . ?
C00Q H00o 0.9700 . ?
C00Q H00p 0.9700 . ?
C00R H00q 0.9600 . ?
C00R H00r 0.9600 . ?
C00R H00s 0.9600 . ?
C00S H00t 0.9600 . ?
C00S H00u 0.9600 . ?
C00S H00v 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
C00H O001 C00F 119.4(3) . . ?
C00J O002 C00A 107.4(3) . . ?
C00D N005 C009 113.6(3) . . ?
C00M N005 C009 116.2(3) . . ?
C00M N005 C00D 111.3(3) . . ?
C00I N007 C00F 126.6(3) . . ?
C00Q N007 C00F 119.9(3) . . ?
C00Q N007 C00I 113.4(3) . . ?
C00C C008 C00A 121.5(3) . . ?
C00G C008 C00A 119.9(3) . . ?
C00G C008 C00C 118.5(3) . . ?
C00B C009 N005 114.5(3) . . ?
C00J C009 N005 119.3(3) . . ?
C00J C009 C00B 99.7(3) . . ?
H009 C009 N005 107.53(19) . . ?
H009 C009 C00B 107.5(2) . . ?
H009 C009 C00J 107.5(2) . . ?
C008 C00A O002 113.8(3) . . ?
C00B C00A O002 112.9(3) . . ?
C00B C00A C008 133.2(4) . . ?
C00A C00B C009 110.7(3) . . ?
H00B C00B C009 124.7(2) . . ?
H00B C00B C00A 124.7(2) . . ?
C00E C00C C008 120.5(4) . . ?
H00C C00C C008 119.8(2) . . ?
H00C C00C C00E 119.8(2) . . ?
C00I C00D N005 109.9(3) . . ?
H00a C00D N005 109.68(18) . . ?
H00a C00D C00I 109.7(2) . . ?
H00d C00D N005 109.68(18) . . ?
H00d C00D C00I 109.7(2) . . ?
H00d C00D H00a 108.2 . . ?
C00K C00E C00C 120.1(4) . . ?
C00N C00E C00C 119.6(4) . . ?
C00N C00E C00K 120.3(4) . . ?
O006 C00F O001 124.9(3) . . ?
N007 C00F O001 111.6(3) . . ?
N007 C00F O006 123.5(4) . . ?
C00L C00G C008 120.8(4) . . ?
H00G C00G C008 119.6(2) . . ?
H00G C00G C00L 119.6(3) . . ?
C00O C00H O001 101.4(3) . . ?
C00R C00H O001 110.2(3) . . ?
C00R C00H C00O 110.3(4) . . ?
C00S C00H O001 110.0(3) . . ?
C00S C00H C00O 111.2(4) . . ?
C00S C00H C00R 113.1(4) . . ?
C00D C00I N007 110.3(3) . . ?
H00e C00I N007 109.6(2) . . ?
H00e C00I C00D 109.6(2) . . ?
H00f C00I N007 109.60(19) . . ?
H00f C00I C00D 109.6(2) . . ?
H00f C00I H00e 108.1 . . ?
F003 C00J O002 108.2(3) . . ?
F004 C00J O002 107.7(3) . . ?
F004 C00J F003 104.5(3) . . ?
C009 C00J O002 109.3(3) . . ?
C009 C00J F003 114.5(3) . . ?
C009 C00J F004 112.2(3) . . ?
C00L C00K C00E 119.3(4) . . ?
H00K C00K C00E 120.3(2) . . ?
H00K C00K C00L 120.3(3) . . ?
C00K C00L C00G 120.8(4) . . ?
H00L C00L C00G 119.6(3) . . ?
H00L C00L C00K 119.6(3) . . ?
C00Q C00M N005 110.1(3) . . ?
H00h C00M N005 109.64(18) . . ?
H00h C00M C00Q 109.6(2) . . ?
H00i C00M N005 109.6(2) . . ?
H00i C00M C00Q 109.6(3) . . ?
H00i C00M H00h 108.2 . . ?
F00P C00N C00E 117.2(4) . . ?
F00T C00N C00E 114.8(6) . . ?
F00T C00N F00P 104.5(6) . . ?
F00U C00N C00E 115.5(5) . . ?
F00U C00N F00P 102.6(7) . . ?
F00U C00N F00T 99.9(6) . . ?
H00j C00O C00H 109.5 . . ?
H00m C00O C00H 109.5 . . ?
H00m C00O H00j 109.5 . . ?
H00n C00O C00H 109.5 . . ?
H00n C00O H00j 109.5 . . ?
H00n C00O H00m 109.5 . . ?
C00M C00Q N007 109.2(4) . . ?
H00o C00Q N007 109.8(2) . . ?
H00o C00Q C00M 109.8(2) . . ?
H00p C00Q N007 109.8(3) . . ?
H00p C00Q C00M 109.8(3) . . ?
H00p C00Q H00o 108.3 . . ?
H00q C00R C00H 109.5 . . ?
H00r C00R C00H 109.5 . . ?
H00r C00R H00q 109.5 . . ?
H00s C00R C00H 109.5 . . ?
H00s C00R H00q 109.5 . . ?
H00s C00R H00r 109.5 . . ?
H00t C00S C00H 109.5 . . ?
H00u C00S C00H 109.5 . . ?
H00u C00S H00t 109.5 . . ?
H00v C00S C00H 109.5 . . ?
H00v C00S H00t 109.5 . . ?
H00v C00S H00u 109.5 . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.541
_oxdiff_exptl_absorpt_empirical_full_min 0.592
