# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_c1_4h_c1
_database_code_depnum_ccdc_archive 'CCDC 1982046'
loop_
_audit_author_name
_audit_author_address
'Morita Masato'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2020-02-05 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_audit_creation_date             2019-09-27
_audit_creation_method           
;
Olex2 1.3
(compiled Sep 10 2019 10:52:38 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 O2'
_chemical_formula_sum            'C16 H14 O2'
_chemical_formula_weight         238.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H14O2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.5051(5)
_cell_length_b                   5.7663(3)
_cell_length_c                   13.3375(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.705(5)
_cell_angle_gamma                90
_cell_volume                     654.06(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2491
_cell_measurement_temperature    293
_cell_measurement_theta_max      29.8360
_cell_measurement_theta_min      2.4110
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.954
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             252
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -3 16 0.1968
12 0 0 0.1413
-10 2 -9 0.2110
-12 0 0 0.1966
0 -2 18 0.2734
2 8 4 0.2381
1 7 -8 0.3734
-2 -8 -4 0.2326
0 2 -18 0.3004
-2 -7 -8 0.2603
2 6 11 0.3037
-1 7 7 0.2748
7 -6 -6 0.2928

_exptl_crystal_size_max          0.605
_exptl_crystal_size_mid          0.474
_exptl_crystal_size_min          0.34
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
5.0795 -2.6197 15.8276 -0.0008 -0.4040 0.9148
11.9707 -0.4492 0.2307 0.0009 -0.9980 0.0637
-10.2735 1.6949 -8.6770 -0.0001 0.8460 -0.5332
-11.9796 0.3795 0.2229 -0.0010 0.9993 -0.0381
0.3682 -2.3182 18.0145 0.0538 -0.0064 0.9985
1.7463 7.7991 4.4671 0.9902 -0.1030 -0.0938
1.0996 7.3676 -7.7708 0.7196 -0.0744 -0.6904
-1.7364 -7.8409 -4.0709 -0.9880 0.1027 0.1154
0.0008 1.9975 -17.9993 -0.0892 -0.0257 -0.9835
-2.0034 -7.0026 -8.0070 -0.9621 0.1211 -0.1170
2.0030 6.0028 11.0062 0.8997 -0.1197 0.3084
-0.9975 7.0029 7.0081 0.9321 0.1268 0.0586
6.9997 -6.0036 -6.0092 -0.7740 -0.6202 -0.0330

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4598
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         2.395
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  15.00   0.25    0.51    --    5.00  26.00 -90.00  100
  2  ω     -2.00  44.00   0.25    0.51    --  -11.80  26.00 -90.00  184
  3  ω     15.00  69.00   0.25    0.51    --    5.00  57.00  30.00  216
  4  ω     53.00  78.00   0.25    0.51    --  -11.80  57.00 -30.00  100
  5  ω    -47.00   9.00   0.25    0.51    --  -11.80  57.00-180.00  224
  6  ω    -46.00  11.00   0.25    0.51    --  -11.80  57.00 -30.00  228
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0040830000
_diffrn_orient_matrix_UB_12      0.1158531000
_diffrn_orient_matrix_UB_13      0.0178120000
_diffrn_orient_matrix_UB_21      -0.0832412000
_diffrn_orient_matrix_UB_22      0.0043428000
_diffrn_orient_matrix_UB_23      0.0019071000
_diffrn_orient_matrix_UB_31      0.0028059000
_diffrn_orient_matrix_UB_32      -0.0413282000
_diffrn_orient_matrix_UB_33      0.0500538000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1191
_reflns_number_total             1455
_reflns_odcompleteness_completeness 96.25
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1455
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.091
_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)+(0.0634P)²+0.0729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1229
_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:
 C004(H004), C005(H005), C006(H006), C007(H007)
2.b Idealised Me refined as rotating group:
 C009(H00A,H00B,H00C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O001 O 0.37409(10) 0.42980(17) 0.10668(6) 0.0569(3) Uani 1 1 d . . . . .
C002 C 0.29653(12) 0.4326(2) 0.19553(8) 0.0425(3) Uani 1 1 d . . . . .
C003 C 0.12822(12) 0.4730(2) 0.37306(8) 0.0441(3) Uani 1 1 d . . . . .
C004 C 0.30742(14) 0.2600(2) 0.26791(9) 0.0472(3) Uani 1 1 d . . . . .
H004 H 0.370757 0.130979 0.257551 0.057 Uiso 1 1 calc R U . . .
C005 C 0.22325(14) 0.2816(2) 0.35564(9) 0.0486(3) Uani 1 1 d . . . . .
H005 H 0.230478 0.165519 0.403891 0.058 Uiso 1 1 calc R U . . .
C006 C 0.20223(13) 0.6243(2) 0.21210(9) 0.0483(3) Uani 1 1 d . . . . .
H006 H 0.194743 0.740052 0.163699 0.058 Uiso 1 1 calc R U . . .
C007 C 0.11985(13) 0.6447(2) 0.29937(9) 0.0481(3) Uani 1 1 d . . . . .
H007 H 0.057461 0.774758 0.309645 0.058 Uiso 1 1 calc R U . . .
C008 C 0.03857(13) 0.4923(2) 0.46301(9) 0.0503(3) Uani 1 1 d . . . . .
C009 C 0.46475(18) 0.2316(3) 0.08362(10) 0.0664(4) Uani 1 1 d . . . . .
H00A H 0.512580 0.251898 0.019398 0.100 Uiso 1 1 calc R U . . .
H00B H 0.398022 0.097309 0.081845 0.100 Uiso 1 1 calc R U . . .
H00C H 0.545152 0.210974 0.133982 0.100 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C002 1.3635(13) . ?
O001 C009 1.4147(16) . ?
C002 C004 1.3887(17) . ?
C002 C006 1.3853(16) . ?
C003 C005 1.3893(17) . ?
C003 C007 1.3961(17) . ?
C003 C008 1.4338(15) . ?
C004 H004 0.9300 . ?
C004 C005 1.3847(16) . ?
C005 H005 0.9300 . ?
C006 H006 0.9300 . ?
C006 C007 1.3710(16) . ?
C007 H007 0.9300 . ?
C008 C008 1.195(2) 3_566 ?
C009 H00A 0.9600 . ?
C009 H00B 0.9600 . ?
C009 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
C002 O001 C009 117.99(10) . . ?
O001 C002 C004 124.54(11) . . ?
O001 C002 C006 115.81(10) . . ?
C006 C002 C004 119.66(11) . . ?
C005 C003 C007 118.06(10) . . ?
C005 C003 C008 121.21(11) . . ?
C007 C003 C008 120.72(11) . . ?
C002 C004 H004 120.3 . . ?
C005 C004 C002 119.49(11) . . ?
C005 C004 H004 120.3 . . ?
C003 C005 H005 119.3 . . ?
C004 C005 C003 121.36(11) . . ?
C004 C005 H005 119.3 . . ?
C002 C006 H006 119.8 . . ?
C007 C006 C002 120.43(11) . . ?
C007 C006 H006 119.8 . . ?
C003 C007 H007 119.5 . . ?
C006 C007 C003 120.99(11) . . ?
C006 C007 H007 119.5 . . ?
C008 C008 C003 178.81(15) 3_566 . ?
O001 C009 H00A 109.5 . . ?
O001 C009 H00B 109.5 . . ?
O001 C009 H00C 109.5 . . ?
H00A C009 H00B 109.5 . . ?
H00A C009 H00C 109.5 . . ?
H00B C009 H00C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C002 C004 C005 179.89(10) . . . . ?
O001 C002 C006 C007 -179.64(10) . . . . ?
C002 C004 C005 C003 -0.21(18) . . . . ?
C002 C006 C007 C003 -0.36(18) . . . . ?
C004 C002 C006 C007 0.03(18) . . . . ?
C005 C003 C007 C006 0.39(17) . . . . ?
C006 C002 C004 C005 0.25(18) . . . . ?
C007 C003 C005 C004 -0.10(17) . . . . ?
C008 C003 C005 C004 178.63(10) . . . . ?
C008 C003 C007 C006 -178.35(10) . . . . ?
C009 O001 C002 C004 3.92(18) . . . . ?
C009 O001 C002 C006 -176.42(11) . . . . ?

_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 1.550
_oxdiff_exptl_absorpt_empirical_full_min 0.656
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_c1-4h-cn
_database_code_depnum_ccdc_archive 'CCDC 1982048'
loop_
_audit_author_name
_audit_author_address
'Morita Masato'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2020-02-05 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_audit_creation_date             2019-09-27
_audit_creation_method           
;
Olex2 1.3
(compiled Sep 10 2019 10:52:38 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 N O'
_chemical_formula_sum            'C16 H11 N O'
_chemical_formula_weight         233.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H11NO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.0792(3)
_cell_length_b                   7.7395(3)
_cell_length_c                   28.2605(15)
_cell_angle_alpha                90
_cell_angle_beta                 106.747(5)
_cell_angle_gamma                90
_cell_volume                     1273.26(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6237
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.8440
_cell_measurement_theta_min      2.7010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 11 4 0.3051
6 7 -1 0.3523
-6 -7 1 0.2127
-5 8 5 0.3132
7 7 -2 0.3503
-7 -6 2 0.2091
6 -8 -9 0.3358
0 1 -38 0.0702
-6 -8 -1 0.2450
0 0 38 0.0497
3 -5 -36 0.2182
6 0 -34 0.3364
7 7 -11 0.3573
2 -2 -39 0.1255
4 7 17 0.3050
6 5 -31 0.3131
-1 0 39 0.0746
1 0 -39 0.0663

_exptl_crystal_size_max          0.671
_exptl_crystal_size_mid          0.584
_exptl_crystal_size_min          0.139
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.9890 10.6090 3.9727 -0.6132 0.5501 0.5670
6.2114 7.2264 -0.8780 0.0746 -0.0686 0.9948
-6.3090 -7.0839 0.9649 -0.0875 0.0801 -0.9929
-5.4628 8.3727 4.9793 -0.7372 0.6622 0.1343
6.5051 6.8387 -1.7948 0.1217 -0.0879 0.9887
-6.7821 -6.3948 2.2612 -0.1632 0.1180 -0.9795
5.7354 -8.0891 -9.0699 0.8045 -0.5832 -0.1126
0.2800 0.6580 -38.4278 0.5827 0.8038 -0.1199
-5.5800 -7.9685 -0.6058 0.0153 0.0213 -0.9997
0.2513 0.1055 37.7883 -0.5736 -0.7912 0.2120
3.0000 -5.0000 -36.0009 0.9353 0.3033 -0.2629
6.0000 -0.0000 -34.0008 0.8717 0.2908 0.3308
7.0000 7.0000 -11.0001 0.2859 0.0756 0.9956
2.0000 -2.0000 -39.0009 0.8003 0.5738 -0.1588
4.0000 7.0000 17.0005 -0.3199 -0.2966 0.8838
6.0000 5.0000 -31.0006 0.6195 0.4627 0.6811
-1.0000 0.0000 39.0009 -0.6602 -0.7356 0.1073
1.0000 -0.0000 -39.0009 0.6602 0.7356 -0.1073

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            14685
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.737
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  24.00   0.25    3.84    --  -11.80  57.00  22.00  104
  2  ω    -47.00 -10.00   0.25    3.84    --  -11.80  57.00  22.00  148
  3  ω    -84.00  92.00   0.25    3.84    --    5.00  19.00 -60.00  704
  4  ω      8.00  33.00   0.25    3.84    --    5.00  57.00  22.00  100
  5  ω      0.00  26.00   0.25    3.84    --  -11.80  57.00 -60.00  104
  6  ω    -47.00  71.00   0.25    3.84    --  -11.80  57.00  90.00  472
  7  ω    -36.00 -10.00   0.25    3.84    --  -11.80  57.00 -60.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0577469000
_diffrn_orient_matrix_UB_12      -0.0411841000
_diffrn_orient_matrix_UB_13      -0.0154479000
_diffrn_orient_matrix_UB_21      -0.0683515000
_diffrn_orient_matrix_UB_22      0.0467532000
_diffrn_orient_matrix_UB_23      -0.0206144000
_diffrn_orient_matrix_UB_31      0.0827509000
_diffrn_orient_matrix_UB_32      0.0671333000
_diffrn_orient_matrix_UB_33      0.0048734000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2005
_reflns_number_total             2908
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2908
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.046
_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)+(0.0755P)²+0.0957P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1533
_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:
 C006(H006), C008(H008), C009(H009), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00F(H00F)
2.b Idealised Me refined as rotating group:
 C00I(H00A,H00G,H00H)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O -0.0291(2) 0.38591(15) 0.43486(4) 0.0955(4) Uani 1 1 d . . . . .
C002 C 0.3572(2) 0.38076(16) 0.18042(5) 0.0659(3) Uani 1 1 d . . . . .
C003 C 0.1441(2) 0.37838(16) 0.30340(5) 0.0674(4) Uani 1 1 d . . . . .
C004 C 0.5285(2) 0.36292(17) 0.09972(5) 0.0683(4) Uani 1 1 d . . . . .
C005 C 0.0378(2) 0.38086(17) 0.39293(5) 0.0706(4) Uani 1 1 d . . . . .
C006 C -0.0624(2) 0.44900(17) 0.30694(5) 0.0718(4) Uani 1 1 d . . . . .
H006 H -0.166233 0.495782 0.279024 0.086 Uiso 1 1 calc R U . . .
C10 C 0.2714(3) 0.38538(18) 0.22240(6) 0.0735(4) Uani 1 1 d . . . . .
C008 C -0.1130(2) 0.44992(18) 0.35089(6) 0.0742(4) Uani 1 1 d . . . . .
H008 H -0.250919 0.497658 0.352617 0.089 Uiso 1 1 calc R U . . .
C009 C 0.5646(2) 0.29705(18) 0.18378(5) 0.0718(4) Uani 1 1 d . . . . .
H009 H 0.646453 0.246480 0.213482 0.086 Uiso 1 1 calc R U . . .
C00A C 0.2076(3) 0.38211(17) 0.25865(5) 0.0734(4) Uani 1 1 d . . . . .
C00B C 0.2387(2) 0.45559(18) 0.13576(5) 0.0725(4) Uani 1 1 d . . . . .
H00B H 0.100670 0.512295 0.133009 0.087 Uiso 1 1 calc R U . . .
C00C C 0.6483(2) 0.28867(18) 0.14398(5) 0.0716(4) Uani 1 1 d . . . . .
H00C H 0.786708 0.232649 0.146700 0.086 Uiso 1 1 calc R U . . .
C00D C 0.2928(2) 0.30881(18) 0.34596(5) 0.0737(4) Uani 1 1 d . . . . .
H00D H 0.429907 0.259584 0.344294 0.088 Uiso 1 1 calc R U . . .
C00E C 0.2438(2) 0.31041(19) 0.39032(5) 0.0753(4) Uani 1 1 d . . . . .
H00E H 0.347675 0.264739 0.418410 0.090 Uiso 1 1 calc R U . . .
C00F C 0.3219(2) 0.4472(2) 0.09565(5) 0.0751(4) Uani 1 1 d . . . . .
H00F H 0.240688 0.497596 0.065867 0.090 Uiso 1 1 calc R U . . .
C00G C 0.6214(3) 0.3540(2) 0.05847(6) 0.0843(4) Uani 1 1 d . . . . .
N00H N 0.6984(3) 0.3466(3) 0.02614(6) 0.1165(6) Uani 1 1 d . . . . .
C00I C 0.1247(4) 0.3225(3) 0.47926(7) 0.1162(7) Uani 1 1 d . . . . .
H00A H 0.159102 0.203469 0.475039 0.174 Uiso 1 1 calc R U . . .
H00G H 0.055090 0.332406 0.505622 0.174 Uiso 1 1 calc R U . . .
H00H H 0.264024 0.388880 0.487177 0.174 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C005 1.3595(17) . ?
O1 C00I 1.419(2) . ?
C002 C10 1.427(2) . ?
C002 C009 1.3962(19) . ?
C002 C00B 1.3868(18) . ?
C003 C006 1.399(2) . ?
C003 C00A 1.4249(19) . ?
C003 C00D 1.3880(19) . ?
C004 C00C 1.3785(18) . ?
C004 C00F 1.3902(19) . ?
C004 C00G 1.436(2) . ?
C005 C008 1.382(2) . ?
C005 C00E 1.387(2) . ?
C006 H006 0.9300 . ?
C006 C008 1.3629(19) . ?
C10 C00A 1.1956(19) . ?
C008 H008 0.9300 . ?
C009 H009 0.9300 . ?
C009 C00C 1.3630(19) . ?
C00B H00B 0.9300 . ?
C00B C00F 1.3695(19) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00D C00E 1.3693(19) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00G N00H 1.142(2) . ?
C00I H00A 0.9600 . ?
C00I H00G 0.9600 . ?
C00I H00H 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
C005 O1 C00I 118.34(13) . . ?
C009 C002 C10 119.62(12) . . ?
C00B C002 C10 121.84(12) . . ?
C00B C002 C009 118.54(13) . . ?
C006 C003 C00A 122.25(12) . . ?
C00D C003 C006 117.60(13) . . ?
C00D C003 C00A 120.11(12) . . ?
C00C C004 C00F 119.94(13) . . ?
C00C C004 C00G 119.20(12) . . ?
C00F C004 C00G 120.86(12) . . ?
O1 C005 C008 116.55(12) . . ?
O1 C005 C00E 123.98(13) . . ?
C008 C005 C00E 119.46(13) . . ?
C003 C006 H006 119.7 . . ?
C008 C006 C003 120.67(12) . . ?
C008 C006 H006 119.7 . . ?
C00A C10 C002 176.43(15) . . ?
C005 C008 H008 119.6 . . ?
C006 C008 C005 120.87(12) . . ?
C006 C008 H008 119.6 . . ?
C002 C009 H009 119.7 . . ?
C00C C009 C002 120.70(12) . . ?
C00C C009 H009 119.7 . . ?
C10 C00A C003 176.94(14) . . ?
C002 C00B H00B 119.5 . . ?
C00F C00B C002 120.97(12) . . ?
C00F C00B H00B 119.5 . . ?
C004 C00C H00C 119.9 . . ?
C009 C00C C004 120.24(12) . . ?
C009 C00C H00C 119.9 . . ?
C003 C00D H00D 119.0 . . ?
C00E C00D C003 122.05(12) . . ?
C00E C00D H00D 119.0 . . ?
C005 C00E H00E 120.3 . . ?
C00D C00E C005 119.33(13) . . ?
C00D C00E H00E 120.3 . . ?
C004 C00F H00F 120.2 . . ?
C00B C00F C004 119.62(12) . . ?
C00B C00F H00F 120.2 . . ?
N00H C00G C004 179.02(16) . . ?
O1 C00I H00A 109.5 . . ?
O1 C00I H00G 109.5 . . ?
O1 C00I H00H 109.5 . . ?
H00A C00I H00G 109.5 . . ?
H00A C00I H00H 109.5 . . ?
H00G C00I H00H 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C005 C008 C006 -179.23(12) . . . . ?
O1 C005 C00E C00D 178.73(12) . . . . ?
C002 C009 C00C C004 -0.1(2) . . . . ?
C002 C00B C00F C004 -0.2(2) . . . . ?
C003 C006 C008 C005 -0.2(2) . . . . ?
C003 C00D C00E C005 1.1(2) . . . . ?
C006 C003 C00D C00E -1.0(2) . . . . ?
C10 C002 C009 C00C 179.01(12) . . . . ?
C10 C002 C00B C00F -178.86(13) . . . . ?
C008 C005 C00E C00D -0.8(2) . . . . ?
C009 C002 C00B C00F 0.32(19) . . . . ?
C00A C003 C006 C008 -177.10(12) . . . . ?
C00A C003 C00D C00E 176.66(12) . . . . ?
C00B C002 C009 C00C -0.19(19) . . . . ?
C00C C004 C00F C00B -0.1(2) . . . . ?
C00D C003 C006 C008 0.51(19) . . . . ?
C00E C005 C008 C006 0.3(2) . . . . ?
C00F C004 C00C C009 0.2(2) . . . . ?
C00G C004 C00C C009 179.34(13) . . . . ?
C00G C004 C00F C00B -179.20(13) . . . . ?
C00I O1 C005 C008 -177.56(15) . . . . ?
C00I O1 C005 C00E 2.9(2) . . . . ?

_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 1.737
_oxdiff_exptl_absorpt_empirical_full_min 0.405
####################################################################### 
# 
# 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_c1_4f_cf3
_database_code_depnum_ccdc_archive 'CCDC 1982050'
loop_
_audit_author_name
_audit_author_address
'Morita Masato'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2020-02-05 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_audit_creation_date             2019-12-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.11.21 svn.r41b79517 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H7 F7 O'
_chemical_formula_sum            'C16 H7 F7 O'
_chemical_formula_weight         348.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H7F7O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   5.6304(5)
_cell_length_b                   8.4095(9)
_cell_length_c                   15.7707(14)
_cell_angle_alpha                95.118(8)
_cell_angle_beta                 96.805(7)
_cell_angle_gamma                92.702(8)
_cell_volume                     737.25(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2665
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.7690
_cell_measurement_theta_min      2.3970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
8 -1 -7 0.2672
0 12 -2 0.1695
-8 1 7 0.2622
1 -12 2 0.1666
0 12 -2 0.1680
-8 1 7 0.2674
1 -12 -1 0.1622
8 0 0 0.2723
1 -1 -22 0.0569
-1 1 22 0.0422
-7 -4 -2 0.2937

_exptl_crystal_size_max          0.578
_exptl_crystal_size_mid          0.346
_exptl_crystal_size_min          0.108
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
7.7597 -0.5539 -7.2057 -0.0055 0.0390 0.9992
-0.2313 11.8539 -1.8932 0.1055 -0.9944 0.0089
-7.7463 1.2405 7.0708 0.0116 -0.0966 -0.9953
0.5093 -11.8531 1.6314 -0.1056 0.9940 0.0269
-0.3691 11.8554 -1.7637 0.1056 -0.9944 -0.0089
-7.7585 0.7529 7.1691 0.0073 -0.0557 -0.9984
0.5539 -11.7645 -0.7727 -0.2087 0.9764 0.0553
7.8512 0.2861 0.0867 0.3353 0.0010 0.9421
0.9089 -1.0944 -21.8661 -0.9489 -0.0008 0.3156
-0.6432 1.1026 21.8412 0.9590 0.0008 -0.2834
-7.0000 -4.0000 -2.0001 -0.4470 0.3021 -0.8275

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10044
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.436
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     15.00  49.00   0.25    2.65    --    5.00   0.00-120.00  136
  2  ω     -5.00  35.00   0.25    2.65    --    5.00  76.00  60.00  160
  3  ω    -47.00 -20.00   0.25    2.65    --    5.00   0.00-120.00  108
  4  ω     39.00  70.00   0.25    2.65    --    5.00  57.00  30.00  124
  5  ω     52.00  78.00   0.25    2.65    --  -11.60  57.00-120.00  104
  6  ω    -53.00  31.00   0.25    2.65    --  -11.60  76.00 -30.00  336
  7  ω    -46.00  29.00   0.25    2.65    --  -11.60  57.00-120.00  300
  8  ω    -35.00  62.00   0.25    2.65    --  -11.60  57.00-180.00  388
  9  ω    -52.00  41.00   0.25    2.65    --  -11.60  76.00  90.00  372
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0416110000
_diffrn_orient_matrix_UB_12      0.0167880000
_diffrn_orient_matrix_UB_13      0.0442854000
_diffrn_orient_matrix_UB_21      0.0031083000
_diffrn_orient_matrix_UB_22      -0.0831349000
_diffrn_orient_matrix_UB_23      0.0043248000
_diffrn_orient_matrix_UB_31      0.1200423000
_diffrn_orient_matrix_UB_32      0.0015740000
_diffrn_orient_matrix_UB_33      -0.0095214000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1731
_reflns_number_total             3370
_reflns_odcompleteness_completeness 99.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.023
_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)+(0.0903P)²+0.0008P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1675
_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. Others
 Sof(F1)=Sof(F2)=Sof(F0)=1-FVAR(1)
 Sof(F3)=Sof(F5)=Sof(F6)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00I(H00I), C00J(H00J), C00K(H00K)
3.b Idealised Me refined as rotating group:
 C00O(H00A,H00B,H00C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.09987(19) 0.16072(14) 0.35324(7) 0.1055(4) Uani 1 1 d . . . . .
F002 F 0.83853(18) 0.45831(14) 0.39802(7) 0.1064(4) Uani 1 1 d . . . . .
F003 F 0.05271(19) 0.21313(14) 0.19037(7) 0.1077(4) Uani 1 1 d . . . . .
F4 F 0.7954(2) 0.51194(14) 0.23595(7) 0.1134(4) Uani 1 1 d . . . . .
O1 O 0.5855(3) 0.07514(19) 0.87447(9) 0.1137(5) Uani 1 1 d . . . . .
C006 C 0.4706(3) 0.30731(19) 0.38117(10) 0.0763(4) Uani 1 1 d . . . . .
C007 C 0.5390(3) 0.19689(19) 0.62594(10) 0.0762(5) Uani 1 1 d . . . . .
C008 C 0.2726(3) 0.2489(2) 0.32470(11) 0.0792(5) Uani 1 1 d . . . . .
C009 C 0.6419(3) 0.3969(2) 0.34737(11) 0.0797(5) Uani 1 1 d . . . . .
C00A C 0.5174(3) 0.2384(2) 0.53964(12) 0.0819(5) Uani 1 1 d . . . . .
C00B C 0.4215(3) 0.3651(2) 0.20698(10) 0.0815(5) Uani 1 1 d . . . . .
C00C C 0.2492(3) 0.2761(2) 0.24061(11) 0.0809(5) Uani 1 1 d . . . . .
C00D C 0.6178(3) 0.4245(2) 0.26311(12) 0.0826(5) Uani 1 1 d . . . . .
F1 F 0.472(3) 0.5296(8) 0.1029(5) 0.185(5) Uani 0.450(13) 1 d . . P A 2
C00F C 0.4960(3) 0.2727(2) 0.46793(12) 0.0842(5) Uani 1 1 d . . . . .
C00G C 0.7422(3) 0.2456(2) 0.68215(12) 0.0865(5) Uani 1 1 d . . . . .
H00G H 0.865557 0.305019 0.663173 0.104 Uiso 1 1 calc R U . . .
C00H C 0.5836(3) 0.1198(2) 0.79386(11) 0.0849(5) Uani 1 1 d . . . . .
C00I C 0.7647(3) 0.2078(2) 0.76545(12) 0.0898(5) Uani 1 1 d . . . . .
H00I H 0.902200 0.241604 0.802541 0.108 Uiso 1 1 calc R U . . .
C00J C 0.3581(3) 0.1080(2) 0.65571(12) 0.0854(5) Uani 1 1 d . . . . .
H00J H 0.220337 0.073718 0.618860 0.103 Uiso 1 1 calc R U . . .
C00K C 0.3801(3) 0.0704(2) 0.73825(12) 0.0886(5) Uani 1 1 d . . . . .
H00K H 0.257121 0.010868 0.757403 0.106 Uiso 1 1 calc R U . . .
F2 F 0.3577(17) 0.2649(5) 0.0618(3) 0.119(3) Uani 0.450(13) 1 d . . P A 1
C00M C 0.3956(6) 0.3919(3) 0.11424(15) 0.1093(7) Uani 1 1 d . . . . .
F0 F 0.206(2) 0.354(4) 0.0741(6) 0.243(8) Uani 0.450(13) 1 d . . P A 2
C00O C 0.7919(5) 0.1187(3) 0.93415(15) 0.1328(9) Uani 1 1 d . . . . .
H00A H 0.930517 0.078440 0.911448 0.199 Uiso 1 1 calc R U . . .
H00B H 0.773882 0.074019 0.987120 0.199 Uiso 1 1 calc R U . . .
H00C H 0.811034 0.233101 0.944307 0.199 Uiso 1 1 calc R U . . .
F3 F 0.1764(13) 0.4582(6) 0.0930(4) 0.1397(18) Uani 0.550(13) 1 d . . P A 1
F5 F 0.5469(15) 0.4931(13) 0.0907(4) 0.172(4) Uani 0.550(13) 1 d . . P A 1
F6 F 0.543(3) 0.2956(11) 0.0767(4) 0.200(4) Uani 0.550(13) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C008 1.339(2) . ?
F002 C009 1.3393(19) . ?
F003 C00C 1.3394(19) . ?
F4 C00D 1.346(2) . ?
O1 C00H 1.356(2) . ?
O1 C00O 1.418(3) . ?
C006 C008 1.383(2) . ?
C006 C009 1.381(2) . ?
C006 C00F 1.416(3) . ?
C007 C00A 1.428(3) . ?
C007 C00G 1.383(2) . ?
C007 C00J 1.386(2) . ?
C008 C00C 1.358(3) . ?
C009 C00D 1.362(3) . ?
C00A C00F 1.186(3) . ?
C00B C00C 1.381(3) . ?
C00B C00D 1.376(3) . ?
C00B C00M 1.491(3) . ?
F1 C00M 1.252(8) . ?
C00G H00G 0.9300 . ?
C00G C00I 1.372(3) . ?
C00H C00I 1.372(3) . ?
C00H C00K 1.381(3) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00J C00K 1.360(3) . ?
C00K H00K 0.9300 . ?
F2 C00M 1.284(5) . ?
C00M F0 1.188(6) . ?
C00M F3 1.395(7) . ?
C00M F5 1.285(6) . ?
C00M F6 1.338(6) . ?
C00O H00A 0.9600 . ?
C00O H00B 0.9600 . ?
C00O 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
C00H O1 C00O 118.08(19) . . ?
C008 C006 C00F 121.19(16) . . ?
C009 C006 C008 116.11(15) . . ?
C009 C006 C00F 122.68(16) . . ?
C00G C007 C00A 120.42(16) . . ?
C00G C007 C00J 118.34(16) . . ?
C00J C007 C00A 121.24(16) . . ?
F001 C008 C006 119.21(16) . . ?
F001 C008 C00C 118.75(16) . . ?
C00C C008 C006 122.03(16) . . ?
F002 C009 C006 119.75(15) . . ?
F002 C009 C00D 118.43(16) . . ?
C00D C009 C006 121.81(16) . . ?
C00F C00A C007 179.1(2) . . ?
C00C C00B C00M 121.1(2) . . ?
C00D C00B C00C 116.49(17) . . ?
C00D C00B C00M 122.4(2) . . ?
F003 C00C C008 117.91(16) . . ?
F003 C00C C00B 120.44(16) . . ?
C008 C00C C00B 121.65(17) . . ?
F4 C00D C009 117.46(17) . . ?
F4 C00D C00B 120.64(17) . . ?
C009 C00D C00B 121.90(16) . . ?
C00A C00F C006 177.80(19) . . ?
C007 C00G H00G 119.5 . . ?
C00I C00G C007 121.08(17) . . ?
C00I C00G H00G 119.5 . . ?
O1 C00H C00I 125.13(18) . . ?
O1 C00H C00K 115.25(18) . . ?
C00I C00H C00K 119.61(18) . . ?
C00G C00I C00H 119.79(18) . . ?
C00G C00I H00I 120.1 . . ?
C00H C00I H00I 120.1 . . ?
C007 C00J H00J 119.7 . . ?
C00K C00J C007 120.66(17) . . ?
C00K C00J H00J 119.7 . . ?
C00H C00K H00K 119.7 . . ?
C00J C00K C00H 120.51(18) . . ?
C00J C00K H00K 119.7 . . ?
F1 C00M C00B 111.7(4) . . ?
F1 C00M F6 104.1(10) . . ?
F2 C00M C00B 115.4(3) . . ?
F2 C00M F3 97.4(6) . . ?
F2 C00M F5 112.5(7) . . ?
F0 C00M C00B 116.7(4) . . ?
F0 C00M F1 112.9(11) . . ?
F0 C00M F6 103.0(19) . . ?
F3 C00M C00B 108.8(3) . . ?
F5 C00M C00B 116.9(4) . . ?
F5 C00M F3 103.0(5) . . ?
F6 C00M C00B 107.1(3) . . ?
O1 C00O H00A 109.5 . . ?
O1 C00O H00B 109.5 . . ?
O1 C00O H00C 109.5 . . ?
H00A C00O H00B 109.5 . . ?
H00A C00O H00C 109.5 . . ?
H00B C00O H00C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F001 C008 C00C F003 0.2(2) . . . . ?
F001 C008 C00C C00B -179.56(14) . . . . ?
F002 C009 C00D F4 0.3(2) . . . . ?
F002 C009 C00D C00B 179.79(14) . . . . ?
O1 C00H C00I C00G 179.97(16) . . . . ?
O1 C00H C00K C00J -179.96(15) . . . . ?
C006 C008 C00C F003 179.13(13) . . . . ?
C006 C008 C00C C00B -0.6(3) . . . . ?
C006 C009 C00D F4 -179.34(14) . . . . ?
C006 C009 C00D C00B 0.2(3) . . . . ?
C007 C00G C00I C00H 0.2(3) . . . . ?
C007 C00J C00K C00H -0.2(3) . . . . ?
C008 C006 C009 F002 179.70(14) . . . . ?
C008 C006 C009 C00D -0.7(2) . . . . ?
C009 C006 C008 F001 179.84(14) . . . . ?
C009 C006 C008 C00C 0.9(2) . . . . ?
C00A C007 C00G C00I 179.45(16) . . . . ?
C00A C007 C00J C00K -179.45(16) . . . . ?
C00C C00B C00D F4 179.64(14) . . . . ?
C00C C00B C00D C009 0.2(3) . . . . ?
C00C C00B C00M F1 142.8(8) . . . . ?
C00C C00B C00M F2 -53.3(6) . . . . ?
C00C C00B C00M F0 10.9(18) . . . . ?
C00C C00B C00M F3 54.9(4) . . . . ?
C00C C00B C00M F5 171.0(7) . . . . ?
C00C C00B C00M F6 -103.8(8) . . . . ?
C00D C00B C00C F003 -179.68(14) . . . . ?
C00D C00B C00C C008 0.1(3) . . . . ?
C00D C00B C00M F1 -38.3(8) . . . . ?
C00D C00B C00M F2 125.5(6) . . . . ?
C00D C00B C00M F0 -170.2(18) . . . . ?
C00D C00B C00M F3 -126.2(4) . . . . ?
C00D C00B C00M F5 -10.1(7) . . . . ?
C00D C00B C00M F6 75.0(8) . . . . ?
C00F C006 C008 F001 1.3(2) . . . . ?
C00F C006 C008 C00C -177.62(15) . . . . ?
C00F C006 C009 F002 -1.8(2) . . . . ?
C00F C006 C009 C00D 177.83(15) . . . . ?
C00G C007 C00J C00K 0.2(3) . . . . ?
C00I C00H C00K C00J 0.1(3) . . . . ?
C00J C007 C00G C00I -0.2(3) . . . . ?
C00K C00H C00I C00G -0.1(3) . . . . ?
C00M C00B C00C F003 -0.7(3) . . . . ?
C00M C00B C00C C008 178.99(17) . . . . ?
C00M C00B C00D F4 0.7(3) . . . . ?
C00M C00B C00D C009 -178.75(17) . . . . ?
C00O O1 C00H C00I -1.6(3) . . . . ?
C00O O1 C00H C00K 178.45(17) . . . . ?

_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 1.688
_oxdiff_exptl_absorpt_empirical_full_min 0.448
####################################################################### 
# 
# 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_c1_4h_cf3
_database_code_depnum_ccdc_archive 'CCDC 1982047'
loop_
_audit_author_name
_audit_author_address
'Morita Masato'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2020-02-05 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 F3 O'
_chemical_formula_weight         276.25

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   6.2167(3)
_cell_length_b                   7.5783(4)
_cell_length_c                   28.6871(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1351.51(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3573
_cell_measurement_theta_min      2.6660
_cell_measurement_theta_max      28.0650

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.503
_exptl_crystal_size_mid          0.460
_exptl_crystal_size_min          0.366
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85935
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7803
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.688
_diffrn_reflns_theta_max         30.561
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.813
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             3364
_reflns_number_gt                2281
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_max     0.722
_reflns_Friedel_fraction_full    0.939

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1148P)²+0.0929P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 859 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3364
_refine_ls_number_parameters     182
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1998
_refine_ls_wR_factor_gt          0.1824
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O15 O 0.8501(5) 0.2630(4) 0.29703(10) 0.0874(8) Uani 1 1 d . . . . .
C9 C 0.5685(7) 0.2530(4) 0.42696(14) 0.0678(9) Uani 1 1 d . . . . .
C8 C 0.4569(8) 0.2493(5) 0.47087(16) 0.0773(10) Uani 1 1 d . . . . .
C14 C 0.4723(6) 0.3363(5) 0.38896(14) 0.0721(9) Uani 1 1 d . . . . .
H14 H 0.3393 0.3910 0.3924 0.086 Uiso 1 1 calc R U . . .
C13 C 0.5727(6) 0.3375(5) 0.34681(14) 0.0726(9) Uani 1 1 d . . . . .
H13 H 0.5091 0.3966 0.3220 0.087 Uiso 1 1 calc R U . . .
F18 F -0.2743(7) 0.2314(7) 0.67974(19) 0.1610(19) Uani 1 1 d . . . . .
C1 C 0.2449(7) 0.2462(4) 0.55003(14) 0.0687(9) Uani 1 1 d . . . . .
C17 C -0.0726(7) 0.2775(5) 0.68170(17) 0.0786(10) Uani 1 1 d . . . . .
C11 C 0.8649(6) 0.1693(5) 0.37775(14) 0.0740(9) Uani 1 1 d . . . . .
H11 H 0.9955 0.1113 0.3739 0.089 Uiso 1 1 calc R U . . .
C12 C 0.7680(6) 0.2525(4) 0.34013(13) 0.0667(8) Uani 1 1 d . . . . .
C10 C 0.7669(8) 0.1730(5) 0.42087(13) 0.0770(10) Uani 1 1 d . . . . .
H10 H 0.8351 0.1209 0.4462 0.092 Uiso 1 1 calc R U . . .
C4 C 0.0361(6) 0.2653(4) 0.63516(14) 0.0674(8) Uani 1 1 d . . . . .
F19 F -0.0786(9) 0.4353(6) 0.69769(14) 0.178(2) Uani 1 1 d . . . . .
C2 C 0.3426(6) 0.1794(5) 0.58994(14) 0.0746(9) Uani 1 1 d . . . . .
H2 H 0.4783 0.1283 0.5880 0.090 Uiso 1 1 calc R U . . .
C7 C 0.3591(7) 0.2445(4) 0.50614(15) 0.0738(9) Uani 1 1 d . . . . .
F20 F 0.0071(10) 0.1823(10) 0.71274(16) 0.207(3) Uani 1 1 d . . . . .
C5 C -0.0603(6) 0.3301(5) 0.59624(15) 0.0733(9) Uani 1 1 d . . . . .
H5 H -0.1961 0.3809 0.5984 0.088 Uiso 1 1 calc R U . . .
C3 C 0.2397(6) 0.1887(5) 0.63189(15) 0.0754(9) Uani 1 1 d . . . . .
H3 H 0.3056 0.1437 0.6585 0.091 Uiso 1 1 calc R U . . .
C6 C 0.0421(6) 0.3211(5) 0.55315(15) 0.0749(10) Uani 1 1 d . . . . .
H6 H -0.0251 0.3651 0.5266 0.090 Uiso 1 1 calc R U . . .
C16 C 1.0440(9) 0.1709(9) 0.2878(2) 0.1064(16) Uani 1 1 d . . . . .
H16A H 1.1010 0.2082 0.2583 0.160 Uiso 1 1 calc R U . . .
H16B H 1.0157 0.0464 0.2869 0.160 Uiso 1 1 calc R U . . .
H16C H 1.1465 0.1956 0.3120 0.160 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O15 C12 1.340(5) . ?
O15 C16 1.418(6) . ?
C9 C10 1.386(6) . ?
C9 C14 1.394(6) . ?
C9 C8 1.438(6) . ?
C8 C7 1.181(6) . ?
C14 C13 1.361(6) . ?
C14 H14 0.9300 . ?
C13 C12 1.388(6) . ?
C13 H13 0.9300 . ?
F18 C17 1.302(6) . ?
C1 C6 1.385(6) . ?
C1 C2 1.391(6) . ?
C1 C7 1.445(6) . ?
C17 F20 1.249(6) . ?
C17 F19 1.281(6) . ?
C17 C4 1.499(6) . ?
C11 C10 1.379(6) . ?
C11 C12 1.387(5) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C4 C5 1.359(6) . ?
C4 C3 1.396(5) . ?
C2 C3 1.365(6) . ?
C2 H2 0.9300 . ?
C5 C6 1.392(6) . ?
C5 H5 0.9300 . ?
C3 H3 0.9300 . ?
C6 H6 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C12 O15 C16 117.8(4) . . ?
C10 C9 C14 118.8(4) . . ?
C10 C9 C8 122.1(4) . . ?
C14 C9 C8 119.1(4) . . ?
C7 C8 C9 177.7(5) . . ?
C13 C14 C9 120.1(4) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
C14 C13 C12 121.4(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C6 C1 C2 119.5(4) . . ?
C6 C1 C7 120.4(4) . . ?
C2 C1 C7 120.0(4) . . ?
F20 C17 F19 107.2(6) . . ?
F20 C17 F18 104.9(5) . . ?
F19 C17 F18 103.8(5) . . ?
F20 C17 C4 114.8(4) . . ?
F19 C17 C4 112.9(4) . . ?
F18 C17 C4 112.3(4) . . ?
C10 C11 C12 119.8(4) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
O15 C12 C11 125.4(3) . . ?
O15 C12 C13 115.7(3) . . ?
C11 C12 C13 118.9(4) . . ?
C11 C10 C9 121.0(4) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 C17 120.7(3) . . ?
C3 C4 C17 119.6(3) . . ?
C3 C2 C1 120.2(4) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C8 C7 C1 177.2(4) . . ?
C4 C5 C6 120.7(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C1 C6 C5 119.6(4) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
O15 C16 H16A 109.5 . . ?
O15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.036

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

data_c1_4f_cn
_database_code_depnum_ccdc_archive 'CCDC 1982051'
loop_
_audit_author_name
_audit_author_address
'Morita Masato'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2020-02-05 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_audit_creation_date             2020-01-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.11.21 svn.r41b79517 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H7 F4 N O'
_chemical_formula_sum            'C16 H7 F4 N O'
_chemical_formula_weight         305.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H7F4NO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.2399(3)
_cell_length_b                   7.7358(3)
_cell_length_c                   28.6607(8)
_cell_angle_alpha                95.911(2)
_cell_angle_beta                 90.746(3)
_cell_angle_gamma                98.579(3)
_cell_volume                     1360.15(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7674
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.5090
_cell_measurement_theta_min      2.6510
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 11 1 0.1461
9 0 -1 0.1650
2 -11 -1 0.1388
-8 -2 1 0.1459
0 0 -40 0.0588
1 -11 14 0.1599
0 1 40 0.0627
-2 9 -27 0.1273
2 0 39 0.0827
-5 1 -32 0.1200
-5 5 -29 0.1432
2 9 -22 0.1722
-1 9 -23 0.1320

_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.302
_exptl_crystal_size_min          0.135
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.0316 10.7950 0.5943 -0.0848 -0.0383 0.9957
8.6854 0.1078 -1.1395 0.9130 0.4076 0.0188
2.1662 -10.7793 -0.6115 0.0991 0.0447 -0.9941
-8.2380 -2.2512 1.0157 -0.8915 -0.3979 -0.2165
-0.0213 0.1384 -40.2245 -0.4055 0.9083 -0.1023
1.2013 -10.5946 13.5820 0.1415 -0.3171 -0.9378
-0.0904 0.8477 39.7290 0.4001 -0.8962 0.1918
-2.0313 8.9998 -26.9636 -0.3829 0.5734 0.7511
2.0793 0.0001 38.9412 0.6130 -0.7882 0.1143
-5.0644 1.0006 -31.9073 -0.8479 0.5043 -0.0059
-5.0477 5.0005 -28.9154 -0.7696 0.4613 0.3720
1.9811 8.9990 -22.0223 0.0933 0.6379 0.7707
-1.0227 8.9996 -22.9805 -0.2356 0.5277 0.7639

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            18706
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.144
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  13.00   0.25    2.95    --    5.00  76.00 -30.00  104
  2  ω    -53.00  22.00   0.25    2.95    --  -11.60  76.00 120.00  300
  3  ω    -47.00  -2.00   0.25    2.95    --  -11.60  57.00  30.00  180
  4  ω    -48.00  58.00   0.25    2.95    --  -11.60  38.00-120.00  424
  5  ω    -53.00  78.00   0.25    2.95    --  -11.60  76.00 -90.00  524
  6  ω   -101.00   8.00   0.25    2.95    --  -11.60   0.00 -90.00  436
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1062914000
_diffrn_orient_matrix_UB_12      0.0115977000
_diffrn_orient_matrix_UB_13      0.0100657000
_diffrn_orient_matrix_UB_21      0.0438925000
_diffrn_orient_matrix_UB_22      0.0059569000
_diffrn_orient_matrix_UB_23      -0.0225843000
_diffrn_orient_matrix_UB_31      0.0013948000
_diffrn_orient_matrix_UB_32      0.0923387000
_diffrn_orient_matrix_UB_33      0.0028603000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4012
_reflns_number_total             6186
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         6186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.005
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1558
_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:
 C00K(H00K), C00N(H00N), C00P(H00P), C00Q(H00Q), C00W(H00W), C00X(H00X),
 C011(H011), C014(H014)
2.b Idealised Me refined as rotating group:
 C017(H01A,H01B,H01C), C018(H01D,H01E,H01F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.46876(13) 0.29342(12) 0.63644(3) 0.0761(2) Uani 1 1 d . . . . .
F002 F 1.26672(13) 0.49624(12) 0.57191(3) 0.0807(3) Uani 1 1 d . . . . .
F003 F 0.56205(14) 0.18189(11) 0.54883(3) 0.0787(3) Uani 1 1 d . . . . .
F004 F 1.16971(15) 0.61052(11) 0.65912(3) 0.0835(3) Uani 1 1 d . . . . .
F005 F -0.27630(14) 0.45954(12) 0.90462(3) 0.0824(3) Uani 1 1 d . . . . .
F006 F -0.20669(15) 0.32140(11) 0.81802(3) 0.0854(3) Uani 1 1 d . . . . .
F8 F 0.43570(15) 0.76469(11) 0.91502(3) 0.0888(3) Uani 1 1 d . . . . .
F7 F 0.50180(15) 0.63272(13) 0.82792(3) 0.0915(3) Uani 1 1 d . . . . .
O1 O 1.25757(18) -0.04206(15) 0.29752(3) 0.0809(3) Uani 1 1 d . . . . .
O2 O -0.1918(2) 1.00391(15) 1.17664(4) 0.0857(3) Uani 1 1 d . . . . .
C00B C 0.8170(2) 0.45432(16) 0.64972(4) 0.0573(3) Uani 1 1 d . . . . .
C00C C 0.9191(2) 0.33453(16) 0.55782(4) 0.0560(3) Uani 1 1 d . . . . .
C00D C 0.6656(2) 0.34441(17) 0.62038(5) 0.0570(3) Uani 1 1 d . . . . .
C00E C 0.7135(2) 0.28736(16) 0.57573(4) 0.0574(3) Uani 1 1 d . . . . .
C00F C 1.0896(2) 0.14803(16) 0.42977(5) 0.0568(3) Uani 1 1 d . . . . .
C00G C 1.2144(2) 0.02636(17) 0.34107(5) 0.0601(3) Uani 1 1 d . . . . .
C19 C 0.9723(2) 0.26971(17) 0.51246(5) 0.0629(3) Uani 1 1 d . . . . .
C00I C 1.0210(2) 0.50311(16) 0.63203(5) 0.0605(3) Uani 1 1 d . . . . .
C00J C 1.0685(2) 0.44510(17) 0.58754(5) 0.0590(3) Uani 1 1 d . . . . .
C00K C 0.9438(2) 0.03627(17) 0.39892(5) 0.0611(3) Uani 1 1 d . . . . .
H00K H 0.802925 0.001948 0.408200 0.073 Uiso 1 1 calc R U . . .
C00L C 1.0269(2) 0.21285(16) 0.47491(5) 0.0610(3) Uani 1 1 d . . . . .
C00M C -0.0826(2) 0.50234(17) 0.88560(5) 0.0639(4) Uani 1 1 d . . . . .
C00N C 1.0039(2) -0.02328(18) 0.35559(5) 0.0630(3) Uani 1 1 d . . . . .
H00N H 0.904188 -0.097553 0.335492 0.076 Uiso 1 1 calc R U . . .
C00O C 0.1500(3) 0.47383(18) 0.82055(5) 0.0653(3) Uani 1 1 d . . . . .
C00P C 1.3617(2) 0.13559(18) 0.37129(5) 0.0647(3) Uani 1 1 d . . . . .
H00P H 1.502684 0.168852 0.361942 0.078 Uiso 1 1 calc R U . . .
C00Q C 1.3003(2) 0.19500(17) 0.41503(5) 0.0649(3) Uani 1 1 d . . . . .
H00Q H 1.400879 0.267896 0.435234 0.078 Uiso 1 1 calc R U . . .
C00R C 0.0770(2) 0.61640(16) 0.91242(5) 0.0611(3) Uani 1 1 d . . . . .
C00S C -0.0488(2) 0.43231(17) 0.84158(5) 0.0638(3) Uani 1 1 d . . . . .
C00T C 0.2751(2) 0.65614(17) 0.89106(5) 0.0657(4) Uani 1 1 d . . . . .
C00U C -0.1304(2) 0.94687(17) 1.13340(5) 0.0633(3) Uani 1 1 d . . . . .
C00V C -0.0424(2) 0.81570(17) 1.04308(5) 0.0638(4) Uani 1 1 d . . . . .
C00W C 0.1179(2) 0.91824(17) 1.07175(5) 0.0672(4) Uani 1 1 d . . . . .
H00W H 0.256748 0.944079 1.060444 0.081 Uiso 1 1 calc R U . . .
C00X C 0.0759(2) 0.98254(18) 1.11654(5) 0.0672(4) Uani 1 1 d . . . . .
H00X H 0.186087 1.049974 1.135497 0.081 Uiso 1 1 calc R U . . .
C20 C 0.0393(3) 0.68618(18) 0.95817(6) 0.0692(4) Uani 1 1 d . . . . .
C00Z C 0.3104(2) 0.58825(18) 0.84658(5) 0.0657(4) Uani 1 1 d . . . . .
C010 C 0.7677(3) 0.51746(19) 0.69619(5) 0.0708(4) Uani 1 1 d . . . . .
C011 C -0.2506(2) 0.78105(18) 1.06055(5) 0.0699(4) Uani 1 1 d . . . . .
H011 H -0.360907 0.712999 1.041769 0.084 Uiso 1 1 calc R U . . .
C012 C 0.0025(3) 0.74594(17) 0.99673(5) 0.0681(4) Uani 1 1 d . . . . .
N013 N 0.7317(3) 0.5715(2) 0.73320(5) 0.1012(5) Uani 1 1 d . . . . .
C014 C -0.2931(2) 0.8458(2) 1.10465(6) 0.0715(4) Uani 1 1 d . . . . .
H014 H -0.432643 0.822237 1.115783 0.086 Uiso 1 1 calc R U . . .
N015 N 0.2136(3) 0.3401(2) 0.73718(6) 0.1031(5) Uani 1 1 d . . . . .
C016 C 0.1858(3) 0.3992(2) 0.77414(6) 0.0763(4) Uani 1 1 d . . . . .
C017 C 1.4660(3) 0.0084(3) 0.27972(6) 0.0938(5) Uani 1 1 d . . . . .
H01A H 1.474145 -0.050392 0.248757 0.141 Uiso 1 1 calc R U . . .
H01B H 1.574250 -0.023566 0.299912 0.141 Uiso 1 1 calc R U . . .
H01C H 1.490686 0.133280 0.278425 0.141 Uiso 1 1 calc R U . . .
C018 C -0.0293(3) 1.0963(2) 1.20922(6) 0.0935(5) Uani 1 1 d . . . . .
H01D H 0.042113 1.198651 1.196323 0.140 Uiso 1 1 calc R U . . .
H01E H 0.074811 1.021047 1.215246 0.140 Uiso 1 1 calc R U . . .
H01F H -0.095492 1.131377 1.238017 0.140 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C00D 1.3357(16) . ?
F002 C00J 1.3389(15) . ?
F003 C00E 1.3321(14) . ?
F004 C00I 1.3312(15) . ?
F005 C00M 1.3424(17) . ?
F006 C00S 1.3319(16) . ?
F8 C00T 1.3391(16) . ?
F7 C00Z 1.3277(18) . ?
O1 C00G 1.3512(16) . ?
O1 C017 1.418(2) . ?
O2 C00U 1.3521(17) . ?
O2 C018 1.426(2) . ?
C00B C00D 1.3836(18) . ?
C00B C00I 1.3905(19) . ?
C00B C010 1.4243(19) . ?
C00C C00E 1.3997(18) . ?
C00C C19 1.4066(19) . ?
C00C C00J 1.3843(18) . ?
C00D C00E 1.3619(18) . ?
C00F C00K 1.3942(19) . ?
C00F C00L 1.4198(18) . ?
C00F C00Q 1.3939(19) . ?
C00G C00N 1.394(2) . ?
C00G C00P 1.3807(19) . ?
C19 C00L 1.1936(18) . ?
C00I C00J 1.3589(19) . ?
C00K H00K 0.9300 . ?
C00K C00N 1.3568(19) . ?
C00M C00R 1.393(2) . ?
C00M C00S 1.353(2) . ?
C00N H00N 0.9300 . ?
C00O C00S 1.395(2) . ?
C00O C00Z 1.386(2) . ?
C00O C016 1.428(2) . ?
C00P H00P 0.9300 . ?
C00P C00Q 1.3697(19) . ?
C00Q H00Q 0.9300 . ?
C00R C00T 1.394(2) . ?
C00R C20 1.402(2) . ?
C00T C00Z 1.361(2) . ?
C00U C00X 1.380(2) . ?
C00U C014 1.389(2) . ?
C00V C00W 1.383(2) . ?
C00V C011 1.397(2) . ?
C00V C012 1.429(2) . ?
C00W H00W 0.9300 . ?
C00W C00X 1.371(2) . ?
C00X H00X 0.9300 . ?
C20 C012 1.192(2) . ?
C010 N013 1.1371(19) . ?
C011 H011 0.9300 . ?
C011 C014 1.355(2) . ?
C014 H014 0.9300 . ?
N015 C016 1.136(2) . ?
C017 H01A 0.9600 . ?
C017 H01B 0.9600 . ?
C017 H01C 0.9600 . ?
C018 H01D 0.9600 . ?
C018 H01E 0.9600 . ?
C018 H01F 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
C00G O1 C017 118.46(13) . . ?
C00U O2 C018 118.24(13) . . ?
C00D C00B C00I 117.43(12) . . ?
C00D C00B C010 121.94(12) . . ?
C00I C00B C010 120.62(12) . . ?
C00E C00C C19 121.67(12) . . ?
C00J C00C C00E 116.40(11) . . ?
C00J C00C C19 121.92(12) . . ?
F001 C00D C00B 118.99(12) . . ?
F001 C00D C00E 119.59(12) . . ?
C00E C00D C00B 121.42(12) . . ?
F003 C00E C00C 119.38(12) . . ?
F003 C00E C00D 119.13(12) . . ?
C00D C00E C00C 121.47(12) . . ?
C00K C00F C00L 121.44(12) . . ?
C00Q C00F C00K 117.99(12) . . ?
C00Q C00F C00L 120.57(12) . . ?
O1 C00G C00N 115.41(13) . . ?
O1 C00G C00P 125.16(12) . . ?
C00P C00G C00N 119.42(12) . . ?
C00L C19 C00C 176.66(15) . . ?
F004 C00I C00B 119.01(12) . . ?
F004 C00I C00J 120.04(12) . . ?
C00J C00I C00B 120.95(12) . . ?
F002 C00J C00C 118.81(12) . . ?
F002 C00J C00I 118.88(12) . . ?
C00I C00J C00C 122.32(11) . . ?
C00F C00K H00K 119.4 . . ?
C00N C00K C00F 121.14(12) . . ?
C00N C00K H00K 119.4 . . ?
C19 C00L C00F 178.70(14) . . ?
F005 C00M C00R 118.33(13) . . ?
F005 C00M C00S 119.15(13) . . ?
C00S C00M C00R 122.52(13) . . ?
C00G C00N H00N 119.8 . . ?
C00K C00N C00G 120.30(12) . . ?
C00K C00N H00N 119.8 . . ?
C00S C00O C016 120.82(14) . . ?
C00Z C00O C00S 117.42(13) . . ?
C00Z C00O C016 121.75(14) . . ?
C00G C00P H00P 120.0 . . ?
C00Q C00P C00G 120.04(12) . . ?
C00Q C00P H00P 120.0 . . ?
C00F C00Q H00Q 119.4 . . ?
C00P C00Q C00F 121.10(12) . . ?
C00P C00Q H00Q 119.4 . . ?
C00M C00R C00T 115.99(13) . . ?
C00M C00R C20 121.60(13) . . ?
C00T C00R C20 122.41(13) . . ?
F006 C00S C00M 119.70(13) . . ?
F006 C00S C00O 119.42(13) . . ?
C00M C00S C00O 120.88(13) . . ?
F8 C00T C00R 118.96(13) . . ?
F8 C00T C00Z 118.97(13) . . ?
C00Z C00T C00R 122.07(13) . . ?
O2 C00U C00X 125.23(13) . . ?
O2 C00U C014 115.38(13) . . ?
C00X C00U C014 119.39(13) . . ?
C00W C00V C011 118.34(13) . . ?
C00W C00V C012 121.22(14) . . ?
C011 C00V C012 120.43(13) . . ?
C00V C00W H00W 119.4 . . ?
C00X C00W C00V 121.25(14) . . ?
C00X C00W H00W 119.4 . . ?
C00U C00X H00X 120.1 . . ?
C00W C00X C00U 119.78(13) . . ?
C00W C00X H00X 120.1 . . ?
C012 C20 C00R 178.50(16) . . ?
F7 C00Z C00O 119.61(13) . . ?
F7 C00Z C00T 119.28(13) . . ?
C00T C00Z C00O 121.12(13) . . ?
N013 C010 C00B 178.34(17) . . ?
C00V C011 H011 119.7 . . ?
C014 C011 C00V 120.56(14) . . ?
C014 C011 H011 119.7 . . ?
C20 C012 C00V 179.38(15) . . ?
C00U C014 H014 119.7 . . ?
C011 C014 C00U 120.67(14) . . ?
C011 C014 H014 119.7 . . ?
N015 C016 C00O 179.7(2) . . ?
O1 C017 H01A 109.5 . . ?
O1 C017 H01B 109.5 . . ?
O1 C017 H01C 109.5 . . ?
H01A C017 H01B 109.5 . . ?
H01A C017 H01C 109.5 . . ?
H01B C017 H01C 109.5 . . ?
O2 C018 H01D 109.5 . . ?
O2 C018 H01E 109.5 . . ?
O2 C018 H01F 109.5 . . ?
H01D C018 H01E 109.5 . . ?
H01D C018 H01F 109.5 . . ?
H01E C018 H01F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F001 C00D C00E F003 0.23(19) . . . . ?
F001 C00D C00E C00C -178.62(11) . . . . ?
F004 C00I C00J F002 0.74(19) . . . . ?
F004 C00I C00J C00C -179.44(11) . . . . ?
F005 C00M C00R C00T 179.85(11) . . . . ?
F005 C00M C00R C20 -0.07(19) . . . . ?
F005 C00M C00S F006 -0.54(19) . . . . ?
F005 C00M C00S C00O 179.86(12) . . . . ?
F8 C00T C00Z F7 -0.7(2) . . . . ?
F8 C00T C00Z C00O 179.30(12) . . . . ?
O1 C00G C00N C00K 179.26(12) . . . . ?
O1 C00G C00P C00Q -178.98(12) . . . . ?
O2 C00U C00X C00W -179.43(12) . . . . ?
O2 C00U C014 C011 -179.90(13) . . . . ?
C00B C00D C00E F003 -179.89(11) . . . . ?
C00B C00D C00E C00C 1.3(2) . . . . ?
C00B C00I C00J F002 179.64(11) . . . . ?
C00B C00I C00J C00C -0.5(2) . . . . ?
C00D C00B C00I F004 179.17(11) . . . . ?
C00D C00B C00I C00J 0.3(2) . . . . ?
C00E C00C C00J F002 -179.08(11) . . . . ?
C00E C00C C00J C00I 1.11(19) . . . . ?
C00F C00K C00N C00G 0.1(2) . . . . ?
C00G C00P C00Q C00F -0.4(2) . . . . ?
C19 C00C C00E F003 -1.69(19) . . . . ?
C19 C00C C00E C00D 177.15(11) . . . . ?
C19 C00C C00J F002 2.31(19) . . . . ?
C19 C00C C00J C00I -177.50(12) . . . . ?
C00I C00B C00D F001 179.27(11) . . . . ?
C00I C00B C00D C00E -0.6(2) . . . . ?
C00J C00C C00E F003 179.70(11) . . . . ?
C00J C00C C00E C00D -1.46(19) . . . . ?
C00K C00F C00Q C00P 1.0(2) . . . . ?
C00L C00F C00K C00N 179.09(12) . . . . ?
C00L C00F C00Q C00P -178.94(12) . . . . ?
C00M C00R C00T F8 -179.82(11) . . . . ?
C00M C00R C00T C00Z 0.3(2) . . . . ?
C00N C00G C00P C00Q -0.3(2) . . . . ?
C00P C00G C00N C00K 0.5(2) . . . . ?
C00Q C00F C00K C00N -0.9(2) . . . . ?
C00R C00M C00S F006 178.74(12) . . . . ?
C00R C00M C00S C00O -0.9(2) . . . . ?
C00R C00T C00Z F7 179.18(12) . . . . ?
C00R C00T C00Z C00O -0.8(2) . . . . ?
C00S C00M C00R C00T 0.6(2) . . . . ?
C00S C00M C00R C20 -179.36(12) . . . . ?
C00S C00O C00Z F7 -179.49(12) . . . . ?
C00S C00O C00Z C00T 0.5(2) . . . . ?
C00V C00W C00X C00U -0.9(2) . . . . ?
C00V C011 C014 C00U -0.4(2) . . . . ?
C00W C00V C011 C014 -0.4(2) . . . . ?
C00X C00U C014 C011 0.5(2) . . . . ?
C20 C00R C00T F8 0.1(2) . . . . ?
C20 C00R C00T C00Z -179.82(12) . . . . ?
C00Z C00O C00S F006 -179.28(12) . . . . ?
C00Z C00O C00S C00M 0.3(2) . . . . ?
C010 C00B C00D F001 -1.3(2) . . . . ?
C010 C00B C00D C00E 178.83(12) . . . . ?
C010 C00B C00I F004 -0.3(2) . . . . ?
C010 C00B C00I C00J -179.20(12) . . . . ?
C011 C00V C00W C00X 1.0(2) . . . . ?
C012 C00V C00W C00X -178.78(12) . . . . ?
C012 C00V C011 C014 179.41(13) . . . . ?
C014 C00U C00X C00W 0.1(2) . . . . ?
C016 C00O C00S F006 0.1(2) . . . . ?
C016 C00O C00S C00M 179.74(12) . . . . ?
C016 C00O C00Z F7 1.1(2) . . . . ?
C016 C00O C00Z C00T -178.93(13) . . . . ?
C017 O1 C00G C00N 177.52(13) . . . . ?
C017 O1 C00G C00P -3.8(2) . . . . ?
C018 O2 C00U C00X -5.4(2) . . . . ?
C018 O2 C00U C014 175.04(14) . . . . ?

_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 1.770
_oxdiff_exptl_absorpt_empirical_full_min 0.591
####################################################################### 
# 
# 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_c1_4f_c1
_database_code_depnum_ccdc_archive 'CCDC 1982049'
loop_
_audit_author_name
_audit_author_address
'Morita Masato'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2020-02-05 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_audit_creation_date             2019-09-27
_audit_creation_method           
;
Olex2 1.3
(compiled Sep 10 2019 10:52:38 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10 F4 O2'
_chemical_formula_sum            'C16 H10 F4 O2'
_chemical_formula_weight         310.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10F4O2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   7.3516(4)
_cell_length_b                   8.5060(5)
_cell_length_c                   12.5385(7)
_cell_angle_alpha                100.778(5)
_cell_angle_beta                 96.710(4)
_cell_angle_gamma                113.627(5)
_cell_volume                     689.46(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3930
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.6390
_cell_measurement_theta_min      2.6660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             316
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 10 -8 0.1192
5 6 -11 0.1319
9 -1 -11 0.1380
8 -11 -3 0.1062
-8 -1 12 0.1174
-3 10 6 0.1697
-2 8 -15 0.1018
0 2 -17 0.0856
2 -10 -7 0.1003
3 -12 7 0.1097
1 -4 17 0.1134
0 10 2 0.1423
6 -6 13 0.1201
-6 1 -12 0.1367
-2 -5 -10 0.1154
-4 2 -15 0.1201
4 -1 14 0.1144
10 -6 1 0.1477
10 0 -2 0.1660
10 -2 -1 0.1590
3 8 -13 0.1156
2 6 -16 0.1074
-4 12 -6 0.1676
6 -3 13 0.1168
3 6 7 0.1465

_exptl_crystal_size_max          0.353
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.207
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.5083 10.4876 -8.1036 0.1820 0.3159 0.9312
4.7907 6.4987 -11.2454 0.3801 0.6598 0.6482
8.7072 -1.4468 -11.0876 0.4991 0.8665 0.0112
7.5015 -10.5005 -3.0256 0.2961 0.5143 -0.8049
-8.0830 -0.5748 11.6455 -0.4910 -0.8525 -0.1792
-2.5214 10.1267 5.7397 0.2788 -0.4816 0.8309
-1.9096 8.2545 -14.8354 -0.3468 0.5994 0.7214
-0.3198 1.8367 -17.3864 -0.4915 0.8493 0.1924
2.3868 -9.5331 -7.1781 -0.3147 0.5436 -0.7782
2.7870 -11.6099 7.3133 0.0891 -0.1541 -0.9840
0.7644 -3.6516 17.3377 0.4704 -0.8128 -0.3435
0.0010 9.9948 2.0063 0.4179 -0.2072 0.8601
6.0013 -6.0032 13.0014 0.7880 -0.3940 -0.4700
-6.0014 1.0050 -12.0038 -0.9365 0.3964 0.0355
-2.0019 -4.9935 -10.0066 -0.6840 0.4923 -0.4360
-4.0021 2.0056 -15.0045 -0.7880 0.6043 0.1544
4.0020 -1.0057 14.0047 0.7936 -0.5643 -0.0657
9.9986 -5.9986 0.9966 0.8323 0.3465 -0.3920
9.9984 0.0000 -2.0012 0.9563 0.4346 0.1333
9.9985 -1.9995 -1.0020 0.9150 0.4052 -0.0418
2.9978 8.0016 -13.0007 0.1985 0.6729 0.7589
1.9972 6.0038 -16.0030 -0.0652 0.8125 0.5797
-3.9999 11.9976 -5.9955 -0.1588 0.0429 0.9991
6.0014 -3.0045 13.0031 0.8952 -0.4258 -0.2106
3.0013 5.9943 7.0059 0.7308 -0.3177 0.5420

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9710
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         2.705
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  22.00   0.25    1.35    --    5.00  76.00 150.00  104
  2  ω     27.00  53.00   0.25    1.35    --    5.00  76.00 150.00  104
  3  ω     40.00  77.00   0.25    1.35    --  -11.60  57.00  30.00  148
  4  ω    -51.00  -9.00   0.25    1.35    --  -11.60  76.00 120.00  168
  5  ω    -33.00  -6.00   0.25    1.35    --  -11.60  57.00 -30.00  108
  6  ω      1.00  70.00   0.25    1.35    --  -11.60  57.00 -30.00  276
  7  ω    -53.00  28.00   0.25    1.35    --  -11.60  76.00-120.00  324
  8  ω    -47.00  15.00   0.25    1.35    --  -11.60  57.00  30.00  248
  9  ω    -66.00  76.00   0.25    1.35    --  -11.60  19.00 150.00  568
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1016826000
_diffrn_orient_matrix_UB_12      0.0357441000
_diffrn_orient_matrix_UB_13      0.0301758000
_diffrn_orient_matrix_UB_21      0.0333447000
_diffrn_orient_matrix_UB_22      -0.0105833000
_diffrn_orient_matrix_UB_23      -0.0505825000
_diffrn_orient_matrix_UB_31      0.0128994000
_diffrn_orient_matrix_UB_32      0.0864889000
_diffrn_orient_matrix_UB_33      -0.0021674000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1980
_reflns_number_total             3147
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.081
_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)+(0.0703P)²+0.0451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1455
_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:
 C00D(H00D), C00G(H00G), C00I(H00I), C00J(H00J)
2.b Idealised Me refined as rotating group:
 C00L(H00A,H00B,H00C), C00M(H00E,H00F,H00H)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.58720(16) 0.82813(13) 0.44327(8) 0.0867(4) Uani 1 1 d . . . . .
F002 F 0.78065(16) 1.17340(13) 0.46791(8) 0.0865(3) Uani 1 1 d . . . . .
F3 F 0.24794(16) 0.75560(14) 0.08341(9) 0.0890(4) Uani 1 1 d . . . . .
F4 F 0.44036(19) 1.10478(14) 0.10723(9) 0.0923(4) Uani 1 1 d . . . . .
O005 O -0.1496(2) -0.28552(14) 0.21546(11) 0.0857(4) Uani 1 1 d . . . . .
O006 O 0.7017(2) 1.32467(15) 0.29148(12) 0.0937(4) Uani 1 1 d . . . . .
C007 C 0.1147(2) 0.25346(19) 0.23729(13) 0.0608(4) Uani 1 1 d . . . . .
C008 C 0.5449(2) 0.8946(2) 0.35960(13) 0.0633(4) Uani 1 1 d . . . . .
C009 C -0.0700(2) -0.10984(19) 0.21692(14) 0.0621(4) Uani 1 1 d . . . . .
C00A C 0.4062(2) 0.78014(19) 0.26401(13) 0.0610(4) Uani 1 1 d . . . . .
C00B C 0.6448(2) 1.0741(2) 0.37228(13) 0.0644(4) Uani 1 1 d . . . . .
C00C C 0.4756(2) 1.0373(2) 0.19175(14) 0.0644(4) Uani 1 1 d . . . . .
C00D C 0.1500(2) 0.1845(2) 0.32559(14) 0.0648(4) Uani 1 1 d . . . . .
H00D H 0.236512 0.260765 0.392173 0.078 Uiso 1 1 calc R U . . .
C00E C 0.6101(2) 1.15107(19) 0.28905(14) 0.0639(4) Uani 1 1 d . . . . .
C00F C 0.3772(2) 0.8583(2) 0.17958(13) 0.0646(4) Uani 1 1 d . . . . .
C00G C 0.0589(2) 0.0053(2) 0.31550(14) 0.0662(4) Uani 1 1 d . . . . .
H00G H 0.083698 -0.039121 0.375164 0.079 Uiso 1 1 calc R U . . .
C00H C 0.3011(2) 0.5945(2) 0.25335(14) 0.0667(4) Uani 1 1 d . . . . .
C00I C -0.0181(2) 0.1369(2) 0.13998(13) 0.0673(4) Uani 1 1 d . . . . .
H00I H -0.045738 0.181007 0.080678 0.081 Uiso 1 1 calc R U . . .
C00J C -0.1100(2) -0.0437(2) 0.12960(13) 0.0664(4) Uani 1 1 d . . . . .
H00J H -0.198656 -0.120431 0.063710 0.080 Uiso 1 1 calc R U . . .
C00K C 0.2153(2) 0.4400(2) 0.24631(14) 0.0678(4) Uani 1 1 d . . . . .
C00L C -0.2705(4) -0.4111(2) 0.11416(18) 0.1015(7) Uani 1 1 d . . . . .
H00A H -0.191742 -0.399062 0.057755 0.152 Uiso 1 1 calc R U . . .
H00B H -0.386683 -0.390410 0.091824 0.152 Uiso 1 1 calc R U . . .
H00C H -0.315032 -0.528866 0.124360 0.152 Uiso 1 1 calc R U . . .
C00M C 0.7461(4) 1.4561(2) 0.38762(19) 0.1116(8) Uani 1 1 d . . . . .
H00E H 0.737178 1.557302 0.368522 0.167 Uiso 1 1 calc R U . . .
H00F H 0.881184 1.490242 0.427815 0.167 Uiso 1 1 calc R U . . .
H00H H 0.650687 1.411735 0.433112 0.167 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C008 1.3431(18) . ?
F002 C00B 1.3469(18) . ?
F3 C00F 1.3390(18) . ?
F4 C00C 1.3425(18) . ?
O005 C009 1.3646(18) . ?
O005 C00L 1.418(2) . ?
O006 C00E 1.3477(19) . ?
O006 C00M 1.386(2) . ?
C007 C00D 1.392(2) . ?
C007 C00I 1.385(2) . ?
C007 C00K 1.432(2) . ?
C008 C00A 1.381(2) . ?
C008 C00B 1.370(2) . ?
C009 C00G 1.384(2) . ?
C009 C00J 1.374(2) . ?
C00A C00F 1.390(2) . ?
C00A C00H 1.424(2) . ?
C00B C00E 1.382(2) . ?
C00C C00E 1.383(2) . ?
C00C C00F 1.367(2) . ?
C00D H00D 0.9300 . ?
C00D C00G 1.370(2) . ?
C00G H00G 0.9300 . ?
C00H C00K 1.188(2) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.381(2) . ?
C00J H00J 0.9300 . ?
C00L H00A 0.9600 . ?
C00L H00B 0.9600 . ?
C00L H00C 0.9600 . ?
C00M H00E 0.9600 . ?
C00M H00F 0.9600 . ?
C00M H00H 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
C009 O005 C00L 118.03(14) . . ?
C00E O006 C00M 121.54(15) . . ?
C00D C007 C00K 120.81(15) . . ?
C00I C007 C00D 118.33(14) . . ?
C00I C007 C00K 120.85(14) . . ?
F001 C008 C00A 119.06(14) . . ?
F001 C008 C00B 118.23(14) . . ?
C00B C008 C00A 122.70(15) . . ?
O005 C009 C00G 115.35(15) . . ?
O005 C009 C00J 124.86(15) . . ?
C00J C009 C00G 119.79(15) . . ?
C008 C00A C00F 115.55(14) . . ?
C008 C00A C00H 121.82(14) . . ?
C00F C00A C00H 122.63(15) . . ?
F002 C00B C008 117.95(15) . . ?
F002 C00B C00E 120.80(14) . . ?
C008 C00B C00E 121.24(15) . . ?
F4 C00C C00E 118.99(14) . . ?
F4 C00C C00F 119.23(15) . . ?
C00F C00C C00E 121.77(15) . . ?
C007 C00D H00D 119.6 . . ?
C00G C00D C007 120.70(15) . . ?
C00G C00D H00D 119.6 . . ?
O006 C00E C00B 126.39(16) . . ?
O006 C00E C00C 116.93(15) . . ?
C00B C00E C00C 116.60(14) . . ?
F3 C00F C00A 119.14(14) . . ?
F3 C00F C00C 118.78(15) . . ?
C00C C00F C00A 122.08(15) . . ?
C009 C00G H00G 119.9 . . ?
C00D C00G C009 120.29(16) . . ?
C00D C00G H00G 119.9 . . ?
C00K C00H C00A 178.8(2) . . ?
C007 C00I H00I 119.5 . . ?
C00J C00I C007 121.04(15) . . ?
C00J C00I H00I 119.5 . . ?
C009 C00J C00I 119.82(15) . . ?
C009 C00J H00J 120.1 . . ?
C00I C00J H00J 120.1 . . ?
C00H C00K C007 179.08(18) . . ?
O005 C00L H00A 109.5 . . ?
O005 C00L H00B 109.5 . . ?
O005 C00L H00C 109.5 . . ?
H00A C00L H00B 109.5 . . ?
H00A C00L H00C 109.5 . . ?
H00B C00L H00C 109.5 . . ?
O006 C00M H00E 109.5 . . ?
O006 C00M H00F 109.5 . . ?
O006 C00M H00H 109.5 . . ?
H00E C00M H00F 109.5 . . ?
H00E C00M H00H 109.5 . . ?
H00F C00M H00H 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F001 C008 C00A C00F -177.42(14) . . . . ?
F001 C008 C00A C00H 2.4(2) . . . . ?
F001 C008 C00B F002 0.4(2) . . . . ?
F001 C008 C00B C00E 179.35(14) . . . . ?
F002 C00B C00E O006 0.3(3) . . . . ?
F002 C00B C00E C00C 176.81(13) . . . . ?
F4 C00C C00E O006 -1.5(2) . . . . ?
F4 C00C C00E C00B -178.35(14) . . . . ?
F4 C00C C00F F3 -0.1(2) . . . . ?
F4 C00C C00F C00A -179.73(14) . . . . ?
O005 C009 C00G C00D 178.92(13) . . . . ?
O005 C009 C00J C00I -179.02(15) . . . . ?
C007 C00D C00G C009 0.1(3) . . . . ?
C007 C00I C00J C009 0.1(3) . . . . ?
C008 C00A C00F F3 178.71(13) . . . . ?
C008 C00A C00F C00C -1.7(2) . . . . ?
C008 C00B C00E O006 -178.69(15) . . . . ?
C008 C00B C00E C00C -2.1(2) . . . . ?
C00A C008 C00B F002 -178.49(14) . . . . ?
C00A C008 C00B C00E 0.5(3) . . . . ?
C00B C008 C00A C00F 1.4(2) . . . . ?
C00B C008 C00A C00H -178.72(15) . . . . ?
C00D C007 C00I C00J -1.4(2) . . . . ?
C00E C00C C00F F3 179.64(14) . . . . ?
C00E C00C C00F C00A 0.0(3) . . . . ?
C00F C00C C00E O006 178.78(14) . . . . ?
C00F C00C C00E C00B 1.9(2) . . . . ?
C00G C009 C00J C00I 1.3(3) . . . . ?
C00H C00A C00F F3 -1.1(2) . . . . ?
C00H C00A C00F C00C 178.47(15) . . . . ?
C00I C007 C00D C00G 1.3(2) . . . . ?
C00J C009 C00G C00D -1.4(3) . . . . ?
C00K C007 C00D C00G -177.79(14) . . . . ?
C00K C007 C00I C00J 177.72(14) . . . . ?
C00L O005 C009 C00G -175.32(16) . . . . ?
C00L O005 C009 C00J 5.0(3) . . . . ?
C00M O006 C00E C00B -38.5(3) . . . . ?
C00M O006 C00E C00C 144.97(19) . . . . ?

_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 1.350
_oxdiff_exptl_absorpt_empirical_full_min 0.773
