# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_kby-ffa4ch3-y_auto
_database_code_depnum_ccdc_archive 'CCDC 2350732'
loop_
_audit_author_name
_audit_author_address
'Shiori Kobayashi'
;Shizuoka University
Japan
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2024-07-08 downloaded from the CCDC.
;
_audit_creation_date             2023-12-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 F3 N O2'
_chemical_formula_sum            'C15 H12 F3 N O2'
_chemical_formula_weight         295.26
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONF
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   12.3091(2)
_cell_length_b                   5.07340(10)
_cell_length_c                   41.7053(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2604.45(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    24943
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.9450
_cell_measurement_theta_min      2.0780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            45890
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.721
_diffrn_reflns_theta_min         2.119
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     37.00 106.00   0.50    0.16    --  107.12 -99.00  90.00  138
  2  ω     37.00 106.00   0.50    0.16    --  107.12 -99.00  60.00  138
  3  ω     38.00 112.00   0.50    0.16    --  107.12-125.00 -30.00  148
  4  ω     37.00 106.00   0.50    0.16    --  107.12 -99.00-120.00  138
  5  ω     19.00  93.00   0.50    0.05    --   47.44-125.00 -90.00  148
  6  ω     37.00 106.00   0.50    0.16    --  107.12 -99.00  90.00  138
  7  ω     35.00 109.00   0.50    0.16    --  107.12 -77.00 120.00  148
  8  ω     35.00  69.00   0.50    0.16    --  107.12 -57.00  90.00   68
  9  ω     35.00  69.00   0.50    0.16    --  107.12 -57.00  30.00   68
 10  ω     35.00  69.00   0.50    0.16    --  107.12 -57.00 -30.00   68
 11  ω    -27.00  30.00   0.50    0.05    --   47.44 -19.00   0.00  114
 12  ω     35.00  69.00   0.50    0.16    --  107.12 -57.00-120.00   68
 13  ω     35.00  69.00   0.50    0.16    --  107.12 -57.00 -90.00   68
 14  ω     94.00 178.00   0.50    0.16    --  107.12  38.00-150.00  168
 15  ω     92.00 178.00   0.50    0.16    --  107.12  57.00  90.00  172
 16  ω     85.00 178.00   0.50    0.16    --  107.12  77.00 150.00  186
 17  ω     85.00 178.00   0.50    0.16    --  107.12  77.00 150.00  186
 18  ω     25.00 120.00   0.50    0.05    --   47.44  77.00 -60.00  190
 19  ω     25.00 120.00   0.50    0.05    --   47.44  77.00-120.00  190
 20  ω     25.00 120.00   0.50    0.05    --   47.44  77.00-180.00  190
 21  ω    -23.00  28.00   0.50    0.05    --  -47.44  19.00 -90.00  102
 22  ω    -39.00  26.00   0.50    0.05    --  -47.44  38.00-120.00  130
 23  ω    -62.00  25.00   0.50    0.05    --  -47.44  57.00-150.00  174
 24  ω    -39.00  26.00   0.50    0.05    --  -47.44  38.00   0.00  130
 25  ω    -62.00 -32.00   0.50    0.16    -- -104.50  57.00-120.00   60
 26  ω    -62.00 -32.00   0.50    0.16    -- -104.50  57.00 -90.00   60
 27  ω   -107.00 -34.00   0.50    0.16    -- -104.50 104.00-155.00  146
 28  ω   -111.00 -35.00   0.50    0.16    -- -104.50 125.00 -60.00  152
 29  ω   -111.00 -35.00   0.50    0.16    -- -104.50 125.00 120.00  152
 30  ω   -174.00 -91.00   0.50    0.16    -- -104.50 -38.00 -30.00  166
 31  ω   -174.00 -91.00   0.50    0.16    -- -104.50 -38.00 -30.00  166
 32  ω   -174.00 -89.00   0.50    0.16    -- -104.50 -57.00 120.00  170
 33  ω   -174.00 -91.00   0.50    0.16    -- -104.50 -49.00  38.40  166
 34  ω   -174.00-106.00   0.50    0.16    -- -104.50 -51.00 -50.71  136
 35  ω   -174.00 -89.00   0.50    0.16    -- -104.50 -57.00-180.00  170
 36  ω   -120.00 -34.00   0.50    0.05    --  -47.44 -38.00-180.00  172
 37  ω   -119.00 -25.00   0.50    0.05    --  -47.44 -77.00  30.00  188
 38  ω   -119.00 -32.00   0.50    0.05    --  -47.44 -57.00  60.00  174
 39  ω   -120.00 -34.00   0.50    0.05    --  -47.44 -38.00  90.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0310431000
_diffrn_orient_matrix_UB_12      -0.0313673000
_diffrn_orient_matrix_UB_13      -0.1416575000
_diffrn_orient_matrix_UB_21      -0.1203999000
_diffrn_orient_matrix_UB_22      0.0058995000
_diffrn_orient_matrix_UB_23      0.0670075000
_diffrn_orient_matrix_UB_31      -0.0141180000
_diffrn_orient_matrix_UB_32      0.0185781000
_diffrn_orient_matrix_UB_33      -0.2602354000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.946
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                5152
_reflns_number_total             5415
_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 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 2351 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         5415
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.072
_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)+(0.0540P)²+1.1426P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1087
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N00A(H00A), N00C(H00C), C00D(H00D), C00G(H00G), C00M(H00M), C00P(H00P),
 C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00Y(H00Y),
 C00Z(H00Z), C011(H011), C012(H012), C013(H013)
2.b Idealised Me refined as rotating group:
 C014(H01D,H01E,H01F), C015(H01A,H01B,H01C)
2.c Idealised tetrahedral OH refined as rotating group:
 O007(H007)
;
_atom_sites_solution_hydrogens   mixed
_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 0.4065(3) 0.7413(5) 0.26722(7) 0.0530(7) Uani 1 1 d . . . . .
O8 O 0.4797(2) 0.7596(5) 0.49877(7) 0.0332(6) Uani 1 1 d . . . . .
O003 O 0.4106(2) 0.3615(5) 0.53405(6) 0.0333(5) Uani 1 1 d . . . . .
O004 O 0.3451(2) 0.6358(5) 0.46610(6) 0.0327(5) Uani 1 1 d . . . . .
F005 F 0.2423(2) 0.5935(5) 0.70962(7) 0.0569(6) Uani 1 1 d . . . . .
F006 F 0.5099(2) 0.4586(6) 0.28920(6) 0.0598(7) Uani 1 1 d . . . . .
O007 O 0.2771(3) 0.2377(5) 0.50151(7) 0.0340(6) Uani 1 1 d . . . . .
H007 H 0.300171 0.366999 0.490951 0.051 Uiso 1 1 calc R U . . .
F008 F 0.2192(3) 0.1857(6) 0.69841(7) 0.0678(9) Uani 1 1 d . . . . .
F009 F 0.3410(3) 0.3019(6) 0.73223(7) 0.0589(7) Uani 1 1 d . . . . .
N00A N 0.4137(2) 0.1572(6) 0.59320(6) 0.0293(6) Uani 1 1 d . . . . .
H00A H 0.463211 0.196414 0.578762 0.035 Uiso 1 1 calc R U . . .
F00B F 0.5251(3) 0.8675(7) 0.30088(7) 0.0745(10) Uani 1 1 d . . . . .
N00C N 0.3404(2) 0.8456(5) 0.40729(6) 0.0299(6) Uani 1 1 d . . . . .
H00C H 0.291849 0.801390 0.421828 0.036 Uiso 1 1 calc R U . . .
C00D C 0.3929(3) 0.7732(6) 0.35069(9) 0.0286(8) Uani 1 1 d . . . . .
H00D H 0.454152 0.885954 0.352535 0.034 Uiso 1 1 calc R U . . .
C00E C 0.4242(3) 0.7784(6) 0.47164(9) 0.0266(7) Uani 1 1 d . . . . .
C00F C 0.3233(3) 0.7411(6) 0.37655(10) 0.0275(8) Uani 1 1 d . . . . .
C00G C 0.4652(3) 1.2127(6) 0.39854(9) 0.0295(7) Uani 1 1 d . . . . .
H00G H 0.436175 1.240108 0.377695 0.035 Uiso 1 1 calc R U . . .
C00H C 0.3315(3) 0.2191(6) 0.52861(9) 0.0282(7) Uani 1 1 d . . . . .
C00I C 0.3309(3) -0.0055(6) 0.58276(7) 0.0269(6) Uani 1 1 d . . . . .
C00J C 0.2897(2) 0.0184(6) 0.55093(8) 0.0264(6) Uani 1 1 d . . . . .
C00K C 0.4227(3) 1.0079(6) 0.41782(8) 0.0272(6) Uani 1 1 d . . . . .
C00L C 0.3763(3) 0.3921(6) 0.67750(8) 0.0304(6) Uani 1 1 d . . . . .
C00M C 0.2065(3) -0.1505(6) 0.54064(8) 0.0304(7) Uani 1 1 d . . . . .
H00M H 0.178990 -0.133587 0.519459 0.036 Uiso 1 1 calc R U . . .
C00N C 0.4648(2) 0.9823(6) 0.44926(7) 0.0276(6) Uani 1 1 d . . . . .
C00O C 0.4528(3) 0.6775(8) 0.29506(9) 0.0408(8) Uani 1 1 d . . . . .
C00P C 0.5470(3) 1.3719(6) 0.40923(8) 0.0327(7) Uani 1 1 d . . . . .
H00P H 0.574385 1.506247 0.395585 0.039 Uiso 1 1 calc R U . . .
C00Q C 0.4297(3) 0.2690(6) 0.62379(9) 0.0271(8) Uani 1 1 d . . . . .
C00R C 0.4639(3) 0.5631(7) 0.68076(8) 0.0323(7) Uani 1 1 d . . . . .
C00S C 0.5355(3) 0.5774(7) 0.65471(8) 0.0354(7) Uani 1 1 d . . . . .
H00S H 0.597163 0.689339 0.656154 0.042 Uiso 1 1 calc R U . . .
C00T C 0.1639(3) -0.3407(7) 0.56062(9) 0.0349(7) Uani 1 1 d . . . . .
H00T H 0.106326 -0.450910 0.553516 0.042 Uiso 1 1 calc R U . . .
C00U C 0.2340(3) 0.5741(7) 0.37277(8) 0.0334(7) Uani 1 1 d . . . . .
H00U H 0.184248 0.552698 0.389998 0.040 Uiso 1 1 calc R U . . .
C00V C 0.2063(3) -0.3688(6) 0.59133(8) 0.0323(7) Uani 1 1 d . . . . .
H00V H 0.178528 -0.502413 0.605023 0.039 Uiso 1 1 calc R U . . .
C00W C 0.2885(3) -0.2052(6) 0.60230(9) 0.0294(7) Uani 1 1 d . . . . .
H00W H 0.316477 -0.228813 0.623336 0.035 Uiso 1 1 calc R U . . .
C00X C 0.2858(3) 0.4680(7) 0.31793(8) 0.0346(7) Uani 1 1 d . . . . .
C00Y C 0.5912(3) 1.3408(7) 0.43994(9) 0.0348(7) Uani 1 1 d . . . . .
H00Y H 0.648953 1.450173 0.447076 0.042 Uiso 1 1 calc R U . . .
C00Z C 0.5192(3) 0.4338(7) 0.62702(8) 0.0323(7) Uani 1 1 d . . . . .
H00Z H 0.569928 0.447875 0.609932 0.039 Uiso 1 1 calc R U . . .
C010 C 0.3731(3) 0.6399(6) 0.32183(8) 0.0309(7) Uani 1 1 d . . . . .
C011 C 0.3578(3) 0.2466(6) 0.64974(10) 0.0297(8) Uani 1 1 d . . . . .
H011 H 0.296684 0.132739 0.648365 0.036 Uiso 1 1 calc R U . . .
C012 C 0.2166(3) 0.4395(7) 0.34442(9) 0.0363(7) Uani 1 1 d . . . . .
H012 H 0.155977 0.324260 0.342837 0.044 Uiso 1 1 calc R U . . .
C013 C 0.5488(3) 1.1473(6) 0.45961(9) 0.0319(7) Uani 1 1 d . . . . .
H013 H 0.577390 1.125829 0.480608 0.038 Uiso 1 1 calc R U . . .
C014 C 0.4864(4) 0.7298(8) 0.71003(11) 0.0416(9) Uani 1 1 d . . . . .
H01D H 0.418773 0.756300 0.722020 0.062 Uiso 1 1 calc R U . . .
H01E H 0.515424 0.901039 0.703347 0.062 Uiso 1 1 calc R U . . .
H01F H 0.539519 0.640187 0.723717 0.062 Uiso 1 1 calc R U . . .
C015 C 0.2623(4) 0.3136(9) 0.28768(11) 0.0446(9) Uani 1 1 d . . . . .
H01A H 0.230940 0.431360 0.271517 0.067 Uiso 1 1 calc R U . . .
H01B H 0.210851 0.171669 0.292476 0.067 Uiso 1 1 calc R U . . .
H01C H 0.330048 0.237871 0.279441 0.067 Uiso 1 1 calc R U . . .
C016 C 0.2950(3) 0.3667(8) 0.70425(9) 0.0402(8) Uani 1 1 d . . . . .
H8 H 0.456(4) 0.610(11) 0.5113(12) 0.065(15) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C00O 1.334(5) . ?
O8 C00E 1.325(5) . ?
O8 H8 0.97(5) . ?
O003 C00H 1.233(4) . ?
O004 C00E 1.234(4) . ?
F005 C016 1.339(5) . ?
F006 C00O 1.337(5) . ?
O007 H007 0.8400 . ?
O007 C00H 1.317(5) . ?
F008 C016 1.331(5) . ?
F009 C016 1.338(5) . ?
N00A H00A 0.8800 . ?
N00A C00I 1.382(4) . ?
N00A C00Q 1.410(5) . ?
F00B C00O 1.334(5) . ?
N00C H00C 0.8800 . ?
N00C C00F 1.403(5) . ?
N00C C00K 1.378(4) . ?
C00D H00D 0.9500 . ?
C00D C00F 1.387(6) . ?
C00D C010 1.401(5) . ?
C00E C00N 1.481(4) . ?
C00F C00U 1.397(5) . ?
C00G H00G 0.9500 . ?
C00G C00K 1.414(5) . ?
C00G C00P 1.366(5) . ?
C00H C00J 1.472(5) . ?
C00I C00J 1.426(4) . ?
C00I C00W 1.401(5) . ?
C00J C00M 1.403(4) . ?
C00K C00N 1.416(4) . ?
C00L C00R 1.390(5) . ?
C00L C011 1.392(5) . ?
C00L C016 1.504(5) . ?
C00M H00M 0.9500 . ?
C00M C00T 1.379(5) . ?
C00N C013 1.398(5) . ?
C00O C010 1.498(5) . ?
C00P H00P 0.9500 . ?
C00P C00Y 1.400(5) . ?
C00Q C00Z 1.390(5) . ?
C00Q C011 1.403(6) . ?
C00R C00S 1.401(5) . ?
C00R C014 1.511(5) . ?
C00S H00S 0.9500 . ?
C00S C00Z 1.380(5) . ?
C00T H00T 0.9500 . ?
C00T C00V 1.390(5) . ?
C00U H00U 0.9500 . ?
C00U C012 1.382(5) . ?
C00V H00V 0.9500 . ?
C00V C00W 1.386(5) . ?
C00W H00W 0.9500 . ?
C00X C010 1.394(5) . ?
C00X C012 1.402(5) . ?
C00X C015 1.513(5) . ?
C00Y H00Y 0.9500 . ?
C00Y C013 1.381(5) . ?
C00Z H00Z 0.9500 . ?
C011 H011 0.9500 . ?
C012 H012 0.9500 . ?
C013 H013 0.9500 . ?
C014 H01D 0.9800 . ?
C014 H01E 0.9800 . ?
C014 H01F 0.9800 . ?
C015 H01A 0.9800 . ?
C015 H01B 0.9800 . ?
C015 H01C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00E O8 H8 111(3) . . ?
C00H O007 H007 109.5 . . ?
C00I N00A H00A 115.5 . . ?
C00I N00A C00Q 129.0(3) . . ?
C00Q N00A H00A 115.5 . . ?
C00F N00C H00C 115.6 . . ?
C00K N00C H00C 115.6 . . ?
C00K N00C C00F 128.8(3) . . ?
C00F C00D H00D 119.9 . . ?
C00F C00D C010 120.3(3) . . ?
C010 C00D H00D 119.9 . . ?
O8 C00E C00N 114.5(3) . . ?
O004 C00E O8 121.6(3) . . ?
O004 C00E C00N 123.9(3) . . ?
C00D C00F N00C 125.0(3) . . ?
C00D C00F C00U 118.0(3) . . ?
C00U C00F N00C 116.8(3) . . ?
C00K C00G H00G 119.3 . . ?
C00P C00G H00G 119.3 . . ?
C00P C00G C00K 121.4(3) . . ?
O003 C00H O007 121.2(3) . . ?
O003 C00H C00J 124.4(3) . . ?
O007 C00H C00J 114.4(3) . . ?
N00A C00I C00J 120.3(3) . . ?
N00A C00I C00W 121.5(3) . . ?
C00W C00I C00J 118.1(3) . . ?
C00I C00J C00H 121.6(3) . . ?
C00M C00J C00H 119.0(3) . . ?
C00M C00J C00I 119.5(3) . . ?
N00C C00K C00G 122.0(3) . . ?
N00C C00K C00N 120.7(3) . . ?
C00G C00K C00N 117.3(3) . . ?
C00R C00L C011 122.7(3) . . ?
C00R C00L C016 119.8(3) . . ?
C011 C00L C016 117.5(3) . . ?
C00J C00M H00M 119.3 . . ?
C00T C00M C00J 121.4(3) . . ?
C00T C00M H00M 119.3 . . ?
C00K C00N C00E 121.6(3) . . ?
C013 C00N C00E 118.3(3) . . ?
C013 C00N C00K 120.1(3) . . ?
F001 C00O F006 105.5(3) . . ?
F001 C00O F00B 105.6(3) . . ?
F001 C00O C010 113.5(3) . . ?
F006 C00O C010 112.0(3) . . ?
F00B C00O F006 106.4(4) . . ?
F00B C00O C010 113.2(3) . . ?
C00G C00P H00P 119.4 . . ?
C00G C00P C00Y 121.2(3) . . ?
C00Y C00P H00P 119.4 . . ?
C00Z C00Q N00A 116.2(3) . . ?
C00Z C00Q C011 118.3(3) . . ?
C011 C00Q N00A 125.2(3) . . ?
C00L C00R C00S 116.4(3) . . ?
C00L C00R C014 124.8(3) . . ?
C00S C00R C014 118.8(3) . . ?
C00R C00S H00S 119.0 . . ?
C00Z C00S C00R 122.0(3) . . ?
C00Z C00S H00S 119.0 . . ?
C00M C00T H00T 120.5 . . ?
C00M C00T C00V 119.1(3) . . ?
C00V C00T H00T 120.5 . . ?
C00F C00U H00U 119.4 . . ?
C012 C00U C00F 121.2(3) . . ?
C012 C00U H00U 119.4 . . ?
C00T C00V H00V 119.4 . . ?
C00W C00V C00T 121.1(3) . . ?
C00W C00V H00V 119.4 . . ?
C00I C00W H00W 119.6 . . ?
C00V C00W C00I 120.8(3) . . ?
C00V C00W H00W 119.6 . . ?
C010 C00X C012 116.2(3) . . ?
C010 C00X C015 124.6(3) . . ?
C012 C00X C015 119.2(3) . . ?
C00P C00Y H00Y 120.8 . . ?
C013 C00Y C00P 118.5(3) . . ?
C013 C00Y H00Y 120.8 . . ?
C00Q C00Z H00Z 119.5 . . ?
C00S C00Z C00Q 120.9(3) . . ?
C00S C00Z H00Z 119.5 . . ?
C00D C010 C00O 117.7(3) . . ?
C00X C010 C00D 122.4(3) . . ?
C00X C010 C00O 119.8(3) . . ?
C00L C011 C00Q 119.7(3) . . ?
C00L C011 H011 120.2 . . ?
C00Q C011 H011 120.2 . . ?
C00U C012 C00X 121.9(3) . . ?
C00U C012 H012 119.0 . . ?
C00X C012 H012 119.0 . . ?
C00N C013 H013 119.3 . . ?
C00Y C013 C00N 121.4(3) . . ?
C00Y C013 H013 119.3 . . ?
C00R C014 H01D 109.5 . . ?
C00R C014 H01E 109.5 . . ?
C00R C014 H01F 109.5 . . ?
H01D C014 H01E 109.5 . . ?
H01D C014 H01F 109.5 . . ?
H01E C014 H01F 109.5 . . ?
C00X C015 H01A 109.5 . . ?
C00X C015 H01B 109.5 . . ?
C00X C015 H01C 109.5 . . ?
H01A C015 H01B 109.5 . . ?
H01A C015 H01C 109.5 . . ?
H01B C015 H01C 109.5 . . ?
F005 C016 C00L 111.9(3) . . ?
F008 C016 F005 106.5(4) . . ?
F008 C016 F009 106.6(3) . . ?
F008 C016 C00L 112.9(3) . . ?
F009 C016 F005 105.7(3) . . ?
F009 C016 C00L 112.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F001 C00O C010 C00D -129.7(3) . . . . ?
F001 C00O C010 C00X 53.0(5) . . . . ?
O8 C00E C00N C00K 172.7(3) . . . . ?
O8 C00E C00N C013 -5.6(5) . . . . ?
O003 C00H C00J C00I 7.5(5) . . . . ?
O003 C00H C00J C00M -173.2(3) . . . . ?
O004 C00E C00N C00K -7.5(5) . . . . ?
O004 C00E C00N C013 174.2(3) . . . . ?
F006 C00O C010 C00D 110.9(4) . . . . ?
F006 C00O C010 C00X -66.4(4) . . . . ?
O007 C00H C00J C00I -172.3(3) . . . . ?
O007 C00H C00J C00M 6.9(4) . . . . ?
N00A C00I C00J C00H -1.5(4) . . . . ?
N00A C00I C00J C00M 179.3(3) . . . . ?
N00A C00I C00W C00V -179.2(3) . . . . ?
N00A C00Q C00Z C00S 172.4(3) . . . . ?
N00A C00Q C011 C00L -172.3(3) . . . . ?
F00B C00O C010 C00D -9.4(5) . . . . ?
F00B C00O C010 C00X 173.3(4) . . . . ?
N00C C00F C00U C012 -173.1(3) . . . . ?
N00C C00K C00N C00E 1.3(5) . . . . ?
N00C C00K C00N C013 179.6(3) . . . . ?
C00D C00F C00U C012 1.6(5) . . . . ?
C00E C00N C013 C00Y 179.6(3) . . . . ?
C00F N00C C00K C00G 38.2(5) . . . . ?
C00F N00C C00K C00N -144.6(3) . . . . ?
C00F C00D C010 C00O -178.5(3) . . . . ?
C00F C00D C010 C00X -1.3(5) . . . . ?
C00F C00U C012 C00X -1.5(6) . . . . ?
C00G C00K C00N C00E 178.6(3) . . . . ?
C00G C00K C00N C013 -3.1(4) . . . . ?
C00G C00P C00Y C013 -1.1(5) . . . . ?
C00H C00J C00M C00T -179.6(3) . . . . ?
C00I N00A C00Q C00Z -177.8(3) . . . . ?
C00I N00A C00Q C011 -4.2(5) . . . . ?
C00I C00J C00M C00T -0.3(5) . . . . ?
C00J C00I C00W C00V -2.2(5) . . . . ?
C00J C00M C00T C00V -1.6(5) . . . . ?
C00K N00C C00F C00D 3.9(5) . . . . ?
C00K N00C C00F C00U 178.2(3) . . . . ?
C00K C00G C00P C00Y -0.8(5) . . . . ?
C00K C00N C013 C00Y 1.2(5) . . . . ?
C00L C00R C00S C00Z 1.2(5) . . . . ?
C00M C00T C00V C00W 1.6(5) . . . . ?
C00P C00G C00K N00C -179.9(3) . . . . ?
C00P C00G C00K C00N 2.9(5) . . . . ?
C00P C00Y C013 C00N 0.9(5) . . . . ?
C00Q N00A C00I C00J 143.6(3) . . . . ?
C00Q N00A C00I C00W -39.4(5) . . . . ?
C00R C00L C011 C00Q 0.5(5) . . . . ?
C00R C00L C016 F005 63.3(4) . . . . ?
C00R C00L C016 F008 -176.6(3) . . . . ?
C00R C00L C016 F009 -55.7(4) . . . . ?
C00R C00S C00Z C00Q 0.4(5) . . . . ?
C00T C00V C00W C00I 0.3(5) . . . . ?
C00W C00I C00J C00H -178.6(3) . . . . ?
C00W C00I C00J C00M 2.2(4) . . . . ?
C00Z C00Q C011 C00L 1.2(5) . . . . ?
C010 C00D C00F N00C 174.0(3) . . . . ?
C010 C00D C00F C00U -0.2(5) . . . . ?
C010 C00X C012 C00U 0.0(5) . . . . ?
C011 C00L C00R C00S -1.7(5) . . . . ?
C011 C00L C00R C014 178.6(4) . . . . ?
C011 C00L C016 F005 -114.6(4) . . . . ?
C011 C00L C016 F008 5.5(5) . . . . ?
C011 C00L C016 F009 126.5(3) . . . . ?
C011 C00Q C00Z C00S -1.7(5) . . . . ?
C012 C00X C010 C00D 1.4(5) . . . . ?
C012 C00X C010 C00O 178.5(3) . . . . ?
C014 C00R C00S C00Z -179.0(3) . . . . ?
C015 C00X C010 C00D -178.3(4) . . . . ?
C015 C00X C010 C00O -1.2(5) . . . . ?
C015 C00X C012 C00U 179.7(4) . . . . ?
C016 C00L C00R C00S -179.5(3) . . . . ?
C016 C00L C00R C014 0.8(5) . . . . ?
C016 C00L C011 C00Q 178.3(3) . . . . ?

_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 1.356
_oxdiff_exptl_absorpt_empirical_full_min 0.601
####################################################################### 
# 
# 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_ffa4ch3-2wb-231128_auto
_database_code_depnum_ccdc_archive 'CCDC 2350733'
loop_
_audit_author_name
_audit_author_address
'Shiori Kobayashi'
;Shizuoka University
Japan
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2024-07-08 downloaded from the CCDC.
;
_audit_creation_date             2023-11-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 F3 N O2'
_chemical_formula_sum            'C15 H12 F3 N O2'
_chemical_formula_weight         295.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONF
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   6.6355(5)
_cell_length_b                   7.3234(5)
_cell_length_c                   15.7183(10)
_cell_angle_alpha                82.822(5)
_cell_angle_beta                 80.835(6)
_cell_angle_gamma                65.136(7)
_cell_volume                     682.74(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4225
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      77.2210
_cell_measurement_theta_min      2.8600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.064
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.102a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6755
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.477
_diffrn_reflns_theta_min         2.854
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     95.00 121.00   0.50    0.09    --  108.21  57.00   0.00   52
  2  ω    142.00 170.00   0.50    0.09    --  108.21  57.00   0.00   56
  3  ω     93.00 167.00   0.50    0.09    --  108.21  19.00   0.00  148
  4  ω     98.00 137.00   0.50    0.09    --  108.21  38.00 -60.00   78
  5  ω    142.00 171.00   0.50    0.09    --  108.21  38.00 -60.00   58
  6  ω     89.00 118.00   0.50    0.05    --   47.23 125.00   0.00   58
  7  ω     64.00 115.00   0.50    0.05    --   47.23 145.00 100.00  102
  8  ω     91.00 116.00   0.50    0.09    --  108.21 145.00 100.00   50
  9  ω     94.00 119.00   0.50    0.05    --   47.23 127.00 -68.00   50
 10  ω     98.00 133.00   0.50    0.09    --  108.21 127.00 -68.00   70
 11  ω     47.00 103.00   0.50    0.09    --  108.21 -77.00  90.00  112
 12  ω     67.00 103.00   0.50    0.09    --  108.21 -77.00  30.00   72
 13  ω     37.00  63.00   0.50    0.09    --  108.21 -57.00   0.00   52
 14  ω     36.00  61.00   0.50    0.09    --  108.21 -57.00 -90.00   50
 15  ω     43.00  88.00   0.50    0.09    --  108.21 -77.00-150.00   90
 16  ω     37.00  93.00   0.50    0.09    --  108.21 -77.00-120.00  112
 17  ω    -20.00  24.00   0.50    0.05    --   47.23 -19.00-150.00   88
 18  ω    -28.00  25.00   0.50    0.05    --   47.23 -19.00  90.00  106
 19  ω     40.00  65.00   0.50    0.09    --  108.21 -57.00  90.00   50
 20  ω     40.00  65.00   0.50    0.09    --  108.21 -57.00 150.00   50
 21  ω     45.00  70.00   0.50    0.05    --   47.23-145.00  47.00   50
 22  ω     60.00 102.00   0.50    0.09    --  108.21-145.00  47.00   84
 23  ω     77.00 102.00   0.50    0.09    --  108.21-127.00-144.00   50
 24  ω     38.00  63.00   0.50    0.05    --   47.23-127.00-144.00   50
 25  ω    -25.00  27.00   0.50    0.05    --  -47.23  19.00  60.00  104
 26  ω     -1.00  27.00   0.50    0.05    --  -47.23  38.00 120.00   56
 27  ω    -42.00 -10.00   0.50    0.05    --  -47.23  38.00 120.00   64
 28  ω   -112.00 -39.00   0.50    0.09    -- -106.00 127.00 -68.00  146
 29  ω    -96.00 -45.00   0.50    0.05    --  -47.23 127.00 -68.00  102
 30  ω   -110.00 -33.00   0.50    0.09    -- -106.00 125.00   0.00  154
 31  ω   -104.00 -79.00   0.50    0.09    -- -106.00 145.00 100.00   50
 32  ω   -101.00 -62.00   0.50    0.05    --  -47.23 145.00 100.00   78
 33  ω    -60.00 -35.00   0.50    0.09    -- -106.00  57.00 -30.00   50
 34  ω    -65.00 -37.00   0.50    0.09    -- -106.00  57.00-120.00   56
 35  ω    -66.00 -41.00   0.50    0.09    -- -106.00  57.00  90.00   50
 36  ω    -64.00 -34.00   0.50    0.09    -- -106.00  57.00 120.00   60
 37  ω   -172.00 -93.00   0.50    0.09    -- -106.00 -38.00 120.00  158
 38  ω   -177.00-101.00   0.50    0.09    -- -106.00 -38.00  90.00  152
 39  ω   -177.00-149.00   0.50    0.09    -- -106.00 -38.00-120.00   56
 40  ω   -132.00-107.00   0.50    0.09    -- -106.00 -38.00-120.00   50
 41  ω   -120.00 -95.00   0.50    0.05    --  -47.23-127.00-144.00   50
 42  ω   -149.00-124.00   0.50    0.09    -- -106.00-127.00-144.00   50
 43  ω   -110.00 -60.00   0.50    0.05    --  -47.23-145.00  47.00  100
 44  ω   -127.00 -97.00   0.50    0.09    -- -106.00-145.00  47.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1288884000
_diffrn_orient_matrix_UB_12      -0.2242416000
_diffrn_orient_matrix_UB_13      0.0274036000
_diffrn_orient_matrix_UB_21      -0.0554677000
_diffrn_orient_matrix_UB_22      0.0507737000
_diffrn_orient_matrix_UB_23      0.0954553000
_diffrn_orient_matrix_UB_31      -0.2161579000
_diffrn_orient_matrix_UB_32      -0.0334579000
_diffrn_orient_matrix_UB_33      0.0059095000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2303
_reflns_number_total             2658
_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 1.171.41.102a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2658
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0614
_refine_ls_restrained_S_all      1.084
_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)+(0.1315P)²+0.0951P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1776
_refine_ls_wR_factor_ref         0.1873
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N006(H006), C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H),
 C00I(H00I), C00J(H00J)
2.b Idealised Me refined as rotating group:
 C00L(H00A,H00C,H00G)
2.c Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_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 0.13949(19) 0.08124(17) 0.92083(8) 0.0320(3) Uani 1 1 d . . . . .
O002 O 0.27601(19) -0.20232(17) 1.00458(8) 0.0342(3) Uani 1 1 d . . . . .
H002 H 0.141662 -0.159185 1.026476 0.051 Uiso 1 1 calc R U . . .
F003 F 0.0409(2) 0.87967(19) 0.58804(9) 0.0578(4) Uani 1 1 d . . . . .
F004 F 0.3104(2) 0.7211(2) 0.49384(8) 0.0661(5) Uani 1 1 d . . . . .
F005 F 0.0854(3) 0.5901(2) 0.55555(11) 0.0767(5) Uani 1 1 d . . . . .
N006 N 0.4241(2) 0.1806(2) 0.80666(10) 0.0340(4) Uani 1 1 d . . . . .
H006 H 0.285157 0.193092 0.819737 0.041 Uiso 1 1 calc R U . . .
C007 C 0.3016(3) -0.0716(2) 0.94284(10) 0.0262(4) Uani 1 1 d . . . . .
C008 C 0.5322(3) -0.1227(2) 0.90318(10) 0.0258(4) Uani 1 1 d . . . . .
C009 C 0.4573(3) 0.3410(2) 0.75524(11) 0.0288(4) Uani 1 1 d . . . . .
C00A C 0.5876(3) 0.0074(2) 0.83812(11) 0.0270(4) Uani 1 1 d . . . . .
C00B C 0.3307(3) 0.4301(2) 0.68733(12) 0.0311(4) Uani 1 1 d . . . . .
H00B H 0.234035 0.375742 0.673109 0.037 Uiso 1 1 calc R U . . .
C00C C 0.3446(3) 0.5990(2) 0.63992(11) 0.0326(4) Uani 1 1 d . . . . .
C00D C 0.7033(3) -0.3032(2) 0.93119(11) 0.0298(4) Uani 1 1 d . . . . .
H00D H 0.665933 -0.390336 0.974462 0.036 Uiso 1 1 calc R U . . .
C00E C 0.6004(3) 0.4195(2) 0.77406(12) 0.0318(4) Uani 1 1 d . . . . .
H00E H 0.688118 0.359904 0.820439 0.038 Uiso 1 1 calc R U . . .
C00F C 0.9773(3) -0.2272(2) 0.83429(12) 0.0322(4) Uani 1 1 d . . . . .
H00F H 1.129343 -0.261491 0.811616 0.039 Uiso 1 1 calc R U . . .
C00G C 0.4877(3) 0.6809(2) 0.65784(12) 0.0348(4) Uani 1 1 d . . . . .
C00H C 0.8142(3) -0.0510(2) 0.80438(12) 0.0305(4) Uani 1 1 d . . . . .
H00H H 0.854947 0.032603 0.760256 0.037 Uiso 1 1 calc R U . . .
C00I C 0.9227(3) -0.3561(2) 0.89742(12) 0.0321(4) Uani 1 1 d . . . . .
H00I H 1.036000 -0.478870 0.916785 0.038 Uiso 1 1 calc R U . . .
C00J C 0.6157(3) 0.5855(3) 0.72506(13) 0.0347(4) Uani 1 1 d . . . . .
H00J H 0.717369 0.635669 0.737971 0.042 Uiso 1 1 calc R U . . .
C00K C 0.1975(3) 0.6953(3) 0.56944(13) 0.0445(5) Uani 1 1 d . . . . .
C00L C 0.5088(4) 0.8646(3) 0.60909(16) 0.0515(6) Uani 1 1 d . . . . .
H00A H 0.587352 0.829620 0.551182 0.077 Uiso 1 1 calc R U . . .
H00C H 0.593400 0.911234 0.640143 0.077 Uiso 1 1 calc R U . . .
H00G H 0.359408 0.971974 0.604308 0.077 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 C007 1.2405(19) . ?
O002 H002 0.8400 . ?
O002 C007 1.319(2) . ?
F003 C00K 1.345(2) . ?
F004 C00K 1.337(3) . ?
F005 C00K 1.331(3) . ?
N006 H006 0.8800 . ?
N006 C009 1.416(2) . ?
N006 C00A 1.374(2) . ?
C007 C008 1.464(2) . ?
C008 C00A 1.421(2) . ?
C008 C00D 1.408(2) . ?
C009 C00B 1.386(2) . ?
C009 C00E 1.382(3) . ?
C00A C00H 1.409(2) . ?
C00B H00B 0.9500 . ?
C00B C00C 1.392(2) . ?
C00C C00G 1.395(3) . ?
C00C C00K 1.499(3) . ?
C00D H00D 0.9500 . ?
C00D C00I 1.372(2) . ?
C00E H00E 0.9500 . ?
C00E C00J 1.388(2) . ?
C00F H00F 0.9500 . ?
C00F C00H 1.376(2) . ?
C00F C00I 1.395(3) . ?
C00G C00J 1.389(3) . ?
C00G C00L 1.511(2) . ?
C00H H00H 0.9500 . ?
C00I H00I 0.9500 . ?
C00J H00J 0.9500 . ?
C00L H00A 0.9800 . ?
C00L H00C 0.9800 . ?
C00L H00G 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C007 O002 H002 109.5 . . ?
C009 N006 H006 116.8 . . ?
C00A N006 H006 116.8 . . ?
C00A N006 C009 126.39(14) . . ?
O001 C007 O002 121.36(14) . . ?
O001 C007 C008 123.72(14) . . ?
O002 C007 C008 114.92(13) . . ?
C00A C008 C007 121.50(14) . . ?
C00D C008 C007 119.18(14) . . ?
C00D C008 C00A 119.31(15) . . ?
C00B C009 N006 118.53(15) . . ?
C00E C009 N006 122.12(16) . . ?
C00E C009 C00B 119.21(15) . . ?
N006 C00A C008 120.93(14) . . ?
N006 C00A C00H 121.04(15) . . ?
C00H C00A C008 117.97(14) . . ?
C009 C00B H00B 119.9 . . ?
C009 C00B C00C 120.22(16) . . ?
C00C C00B H00B 119.9 . . ?
C00B C00C C00G 121.55(16) . . ?
C00B C00C C00K 118.32(17) . . ?
C00G C00C C00K 120.11(16) . . ?
C008 C00D H00D 119.2 . . ?
C00I C00D C008 121.52(16) . . ?
C00I C00D H00D 119.2 . . ?
C009 C00E H00E 120.1 . . ?
C009 C00E C00J 119.84(16) . . ?
C00J C00E H00E 120.1 . . ?
C00H C00F H00F 119.5 . . ?
C00H C00F C00I 120.97(16) . . ?
C00I C00F H00F 119.5 . . ?
C00C C00G C00L 123.94(17) . . ?
C00J C00G C00C 116.75(15) . . ?
C00J C00G C00L 119.31(18) . . ?
C00A C00H H00H 119.5 . . ?
C00F C00H C00A 121.08(16) . . ?
C00F C00H H00H 119.5 . . ?
C00D C00I C00F 119.13(15) . . ?
C00D C00I H00I 120.4 . . ?
C00F C00I H00I 120.4 . . ?
C00E C00J C00G 122.39(16) . . ?
C00E C00J H00J 118.8 . . ?
C00G C00J H00J 118.8 . . ?
F003 C00K C00C 112.05(17) . . ?
F004 C00K F003 105.81(16) . . ?
F004 C00K C00C 113.04(17) . . ?
F005 C00K F003 105.56(18) . . ?
F005 C00K F004 107.02(18) . . ?
F005 C00K C00C 112.79(17) . . ?
C00G C00L H00A 109.5 . . ?
C00G C00L H00C 109.5 . . ?
C00G C00L H00G 109.5 . . ?
H00A C00L H00C 109.5 . . ?
H00A C00L H00G 109.5 . . ?
H00C C00L H00G 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 C007 C008 C00A 3.0(3) . . . . ?
O001 C007 C008 C00D -178.07(15) . . . . ?
O002 C007 C008 C00A -177.49(14) . . . . ?
O002 C007 C008 C00D 1.5(2) . . . . ?
N006 C009 C00B C00C 174.55(14) . . . . ?
N006 C009 C00E C00J -175.67(15) . . . . ?
N006 C00A C00H C00F -178.28(16) . . . . ?
C007 C008 C00A N006 -3.8(3) . . . . ?
C007 C008 C00A C00H 178.84(14) . . . . ?
C007 C008 C00D C00I -178.64(15) . . . . ?
C008 C00A C00H C00F -0.9(3) . . . . ?
C008 C00D C00I C00F 0.4(3) . . . . ?
C009 N006 C00A C008 166.83(16) . . . . ?
C009 N006 C00A C00H -15.9(3) . . . . ?
C009 C00B C00C C00G 1.2(3) . . . . ?
C009 C00B C00C C00K -177.51(15) . . . . ?
C009 C00E C00J C00G 1.5(3) . . . . ?
C00A N006 C009 C00B 139.41(18) . . . . ?
C00A N006 C009 C00E -44.9(2) . . . . ?
C00A C008 C00D C00I 0.3(3) . . . . ?
C00B C009 C00E C00J 0.0(3) . . . . ?
C00B C00C C00G C00J 0.2(3) . . . . ?
C00B C00C C00G C00L -179.56(17) . . . . ?
C00B C00C C00K F003 112.37(19) . . . . ?
C00B C00C C00K F004 -128.17(19) . . . . ?
C00B C00C C00K F005 -6.6(3) . . . . ?
C00C C00G C00J C00E -1.5(3) . . . . ?
C00D C008 C00A N006 177.29(15) . . . . ?
C00D C008 C00A C00H -0.1(2) . . . . ?
C00E C009 C00B C00C -1.3(2) . . . . ?
C00G C00C C00K F003 -66.4(2) . . . . ?
C00G C00C C00K F004 53.1(2) . . . . ?
C00G C00C C00K F005 174.69(18) . . . . ?
C00H C00F C00I C00D -1.4(3) . . . . ?
C00I C00F C00H C00A 1.7(3) . . . . ?
C00K C00C C00G C00J 178.85(16) . . . . ?
C00K C00C C00G C00L -0.9(3) . . . . ?
C00L C00G C00J C00E 178.24(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 2.057
_oxdiff_exptl_absorpt_empirical_full_min 0.445
####################################################################### 
# 
# 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_ffa4ch3-8_auto
_database_code_depnum_ccdc_archive 'CCDC 2350734'
loop_
_audit_author_name
_audit_author_address
'Shiori Kobayashi'
;Shizuoka University
Japan
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2024-07-08 downloaded from the CCDC.
;
_audit_creation_date             2023-11-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 F3 N O2'
_chemical_formula_sum            'C15 H12 F3 N O2'
_chemical_formula_weight         295.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONF
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.9586(2)
_cell_length_b                   11.2709(4)
_cell_length_c                   24.1190(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.674(3)
_cell_angle_gamma                90
_cell_volume                     1341.36(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4251
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.0810
_cell_measurement_theta_min      3.6870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.102a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            8206
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.294
_diffrn_reflns_theta_min         3.683
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  -6.00   0.50    1.07    --  -47.48 103.00 -73.00  120
  2  ω     16.00  67.00   0.50    1.07    --   47.48-103.00-174.00  102
  3  ω   -176.00-114.00   0.50    4.30    -- -106.00-103.00-174.00  124
  4  ω    -98.00 -72.00   0.50    4.30    -- -106.00 103.00 -73.00   52
  5  ω     51.00 107.00   0.50    4.30    --  108.21-103.00-174.00  112
  6  ω     90.00 155.00   0.50    4.30    --  108.21 103.00 -73.00  130
  7  ω   -113.00 -74.00   0.50    1.07    --  -47.48-125.00  60.00   78
  8  ω   -104.00 -73.00   0.50    1.07    --  -47.48-125.00-120.00   62
  9  ω   -117.00 -78.00   0.50    1.07    --  -47.48-125.00 -90.00   78
 10  ω     82.00 116.00   0.50    1.07    --   47.48 125.00-150.00   68
 11  ω     82.00 107.00   0.50    1.07    --   47.48 125.00 120.00   50
 12  ω    -60.00 -34.00   0.50    4.30    -- -106.00  57.00 150.00   52
 13  ω   -164.00-138.00   0.50    4.30    -- -106.00 -99.00 120.00   52
 14  ω    -67.00 -42.00   0.50    4.30    -- -106.00  57.00  60.00   50
 15  ω    -67.00 -42.00   0.50    4.30    -- -106.00  57.00  30.00   50
 16  ω    -61.00 -35.00   0.50    4.30    -- -106.00  57.00-120.00   52
 17  ω    -67.00 -41.00   0.50    4.30    -- -106.00  57.00 120.00   52
 18  ω   -125.00 -97.00   0.50    4.30    -- -106.00 -38.00  90.00   56
 19  ω   -133.00 -91.00   0.50    4.30    -- -106.00 -99.00 120.00   84
 20  ω   -168.00-142.00   0.50    4.30    -- -106.00 -38.00  90.00   52
 21  ω    -63.00 -38.00   0.50    4.30    -- -106.00  57.00  90.00   50
 22  ω     35.00  60.00   0.50    4.30    --  108.21 -57.00-180.00   50
 23  ω     56.00  81.00   0.50    4.30    --  108.21 -77.00-150.00   50
 24  ω     72.00  98.00   0.50    4.30    --  108.21 -77.00-180.00   52
 25  ω     37.00  62.00   0.50    4.30    --  108.21 -77.00-180.00   50
 26  ω     37.00  64.00   0.50    4.30    --  108.21 -57.00-120.00   54
 27  ω     35.00  60.00   0.50    4.30    --  108.21 -57.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2388669000
_diffrn_orient_matrix_UB_12      0.0725405000
_diffrn_orient_matrix_UB_13      0.0183552000
_diffrn_orient_matrix_UB_21      0.1860072000
_diffrn_orient_matrix_UB_22      0.1091910000
_diffrn_orient_matrix_UB_23      0.0094477000
_diffrn_orient_matrix_UB_31      -0.0760454000
_diffrn_orient_matrix_UB_32      0.0388272000
_diffrn_orient_matrix_UB_33      -0.0607787000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2343
_reflns_number_total             2708
_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 1.171.41.102a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2708
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.067
_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)+(0.0715P)²+0.4718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1359
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N006(H006), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00L(H00L)
2.b Idealised Me refined as rotating group:
 C00K(H00A,H00B,H00C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
O2 O -0.2727(2) 0.51346(11) 0.45508(5) 0.0320(3) Uani 1 1 d . . . . .
O1 O -0.3801(2) 0.34806(11) 0.49874(5) 0.0343(3) Uani 1 1 d . . . . .
H1 H -0.492183 0.394166 0.511405 0.051 Uiso 1 1 calc R U . . .
F003 F 0.5486(3) 0.94078(11) 0.32220(5) 0.0572(4) Uani 1 1 d . . . . .
F004 F 0.5623(4) 0.87327(13) 0.40450(5) 0.0681(4) Uani 1 1 d . . . . .
F005 F 0.9044(3) 0.85442(13) 0.35716(8) 0.0779(5) Uani 1 1 d . . . . .
N006 N 0.0849(3) 0.49724(14) 0.37933(6) 0.0358(4) Uani 1 1 d . . . . .
H006 H -0.044649 0.538284 0.392845 0.043 Uiso 1 1 calc R U . . .
C007 C -0.0571(3) 0.33158(15) 0.43414(6) 0.0285(4) Uani 1 1 d . . . . .
C008 C 0.1036(3) 0.37960(16) 0.39401(6) 0.0288(4) Uani 1 1 d . . . . .
C009 C -0.2439(3) 0.40575(15) 0.46284(6) 0.0279(4) Uani 1 1 d . . . . .
C00A C 0.2508(3) 0.55954(16) 0.34493(7) 0.0307(4) Uani 1 1 d . . . . .
C00B C 0.5255(3) 0.73237(16) 0.33133(7) 0.0315(4) Uani 1 1 d . . . . .
C00C C 0.5856(3) 0.69137(16) 0.27902(7) 0.0323(4) Uani 1 1 d . . . . .
C00D C 0.2860(3) 0.30174(17) 0.37082(7) 0.0344(4) Uani 1 1 d . . . . .
H00D H 0.400441 0.331545 0.344695 0.041 Uiso 1 1 calc R U . . .
C00E C 0.3604(3) 0.66695(16) 0.36340(7) 0.0321(4) Uani 1 1 d . . . . .
H00E H 0.322305 0.696670 0.398651 0.039 Uiso 1 1 calc R U . . .
C00F C 0.2999(3) 0.52007(17) 0.29195(7) 0.0338(4) Uani 1 1 d . . . . .
H00F H 0.218856 0.448734 0.277456 0.041 Uiso 1 1 calc R U . . .
C00G C 0.4673(3) 0.58517(17) 0.26050(7) 0.0347(4) Uani 1 1 d . . . . .
H00G H 0.502044 0.555904 0.224964 0.042 Uiso 1 1 calc R U . . .
C00H C -0.0367(4) 0.21051(17) 0.44765(8) 0.0379(4) Uani 1 1 d . . . . .
H00H H -0.146230 0.179041 0.474286 0.045 Uiso 1 1 calc R U . . .
C00I C 0.3009(4) 0.18405(18) 0.38530(8) 0.0392(4) Uani 1 1 d . . . . .
H00I H 0.425497 0.134086 0.368953 0.047 Uiso 1 1 calc R U . . .
C00J C 0.6351(4) 0.84792(18) 0.35405(8) 0.0403(4) Uani 1 1 d . . . . .
C00K C 0.7725(4) 0.75539(19) 0.24287(8) 0.0419(5) Uani 1 1 d . . . . .
H00A H 0.720621 0.839191 0.239664 0.063 Uiso 1 1 calc R U . . .
H00B H 0.757834 0.719251 0.205733 0.063 Uiso 1 1 calc R U . . .
H00C H 0.959859 0.749095 0.259838 0.063 Uiso 1 1 calc R U . . .
C00L C 0.1380(4) 0.13621(18) 0.42332(9) 0.0444(5) Uani 1 1 d . . . . .
H00L H 0.146867 0.054157 0.432312 0.053 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
O2 C009 1.234(2) . ?
O1 H1 0.8400 . ?
O1 C009 1.3208(19) . ?
F003 C00J 1.343(2) . ?
F004 C00J 1.334(2) . ?
F005 C00J 1.332(2) . ?
N006 H006 0.8800 . ?
N006 C008 1.373(2) . ?
N006 C00A 1.412(2) . ?
C007 C008 1.420(2) . ?
C007 C009 1.471(2) . ?
C007 C00H 1.404(3) . ?
C008 C00D 1.415(2) . ?
C00A C00E 1.383(3) . ?
C00A C00F 1.397(2) . ?
C00B C00C 1.403(2) . ?
C00B C00E 1.392(2) . ?
C00B C00J 1.494(3) . ?
C00C C00G 1.387(3) . ?
C00C C00K 1.516(2) . ?
C00D H00D 0.9500 . ?
C00D C00I 1.372(3) . ?
C00E H00E 0.9500 . ?
C00F H00F 0.9500 . ?
C00F C00G 1.388(2) . ?
C00G H00G 0.9500 . ?
C00H H00H 0.9500 . ?
C00H C00L 1.377(3) . ?
C00I H00I 0.9500 . ?
C00I C00L 1.389(3) . ?
C00K H00A 0.9800 . ?
C00K H00B 0.9800 . ?
C00K H00C 0.9800 . ?
C00L H00L 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C009 O1 H1 109.5 . . ?
C008 N006 H006 116.4 . . ?
C008 N006 C00A 127.12(13) . . ?
C00A N006 H006 116.4 . . ?
C008 C007 C009 121.74(15) . . ?
C00H C007 C008 119.74(15) . . ?
C00H C007 C009 118.51(14) . . ?
N006 C008 C007 121.03(14) . . ?
N006 C008 C00D 121.77(15) . . ?
C00D C008 C007 117.18(16) . . ?
O2 C009 O1 121.63(14) . . ?
O2 C009 C007 123.81(14) . . ?
O1 C009 C007 114.55(15) . . ?
C00E C00A N006 118.66(14) . . ?
C00E C00A C00F 118.35(15) . . ?
C00F C00A N006 122.94(17) . . ?
C00C C00B C00J 120.99(16) . . ?
C00E C00B C00C 120.94(17) . . ?
C00E C00B C00J 118.07(15) . . ?
C00B C00C C00K 123.82(17) . . ?
C00G C00C C00B 116.92(15) . . ?
C00G C00C C00K 119.25(15) . . ?
C008 C00D H00D 119.3 . . ?
C00I C00D C008 121.30(16) . . ?
C00I C00D H00D 119.3 . . ?
C00A C00E C00B 121.27(15) . . ?
C00A C00E H00E 119.4 . . ?
C00B C00E H00E 119.4 . . ?
C00A C00F H00F 120.0 . . ?
C00G C00F C00A 119.96(17) . . ?
C00G C00F H00F 120.0 . . ?
C00C C00G C00F 122.47(15) . . ?
C00C C00G H00G 118.8 . . ?
C00F C00G H00G 118.8 . . ?
C007 C00H H00H 119.1 . . ?
C00L C00H C007 121.73(16) . . ?
C00L C00H H00H 119.1 . . ?
C00D C00I H00I 119.2 . . ?
C00D C00I C00L 121.54(16) . . ?
C00L C00I H00I 119.2 . . ?
F003 C00J C00B 112.67(16) . . ?
F004 C00J F003 104.77(16) . . ?
F004 C00J C00B 113.57(16) . . ?
F005 C00J F003 104.53(17) . . ?
F005 C00J F004 107.27(18) . . ?
F005 C00J C00B 113.25(16) . . ?
C00C C00K H00A 109.5 . . ?
C00C C00K H00B 109.5 . . ?
C00C C00K H00C 109.5 . . ?
H00A C00K H00B 109.5 . . ?
H00A C00K H00C 109.5 . . ?
H00B C00K H00C 109.5 . . ?
C00H C00L C00I 118.46(18) . . ?
C00H C00L H00L 120.8 . . ?
C00I C00L H00L 120.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N006 C008 C00D C00I -179.25(17) . . . . ?
N006 C00A C00E C00B 179.98(15) . . . . ?
N006 C00A C00F C00G -179.40(16) . . . . ?
C007 C008 C00D C00I 1.9(3) . . . . ?
C007 C00H C00L C00I 1.3(3) . . . . ?
C008 N006 C00A C00E -130.95(18) . . . . ?
C008 N006 C00A C00F 51.9(3) . . . . ?
C008 C007 C009 O2 -1.0(2) . . . . ?
C008 C007 C009 O1 179.66(14) . . . . ?
C008 C007 C00H C00L 0.6(3) . . . . ?
C008 C00D C00I C00L 0.0(3) . . . . ?
C009 C007 C008 N006 -1.8(2) . . . . ?
C009 C007 C008 C00D 177.07(15) . . . . ?
C009 C007 C00H C00L -178.66(17) . . . . ?
C00A N006 C008 C007 172.68(16) . . . . ?
C00A N006 C008 C00D -6.1(3) . . . . ?
C00A C00F C00G C00C -1.6(3) . . . . ?
C00B C00C C00G C00F -1.0(3) . . . . ?
C00C C00B C00E C00A 0.1(3) . . . . ?
C00C C00B C00J F003 62.0(2) . . . . ?
C00C C00B C00J F004 -179.11(16) . . . . ?
C00C C00B C00J F005 -56.4(2) . . . . ?
C00D C00I C00L C00H -1.6(3) . . . . ?
C00E C00A C00F C00G 3.4(2) . . . . ?
C00E C00B C00C C00G 1.7(2) . . . . ?
C00E C00B C00C C00K -177.49(16) . . . . ?
C00E C00B C00J F003 -117.60(18) . . . . ?
C00E C00B C00J F004 1.3(2) . . . . ?
C00E C00B C00J F005 124.01(19) . . . . ?
C00F C00A C00E C00B -2.7(2) . . . . ?
C00H C007 C008 N006 178.99(16) . . . . ?
C00H C007 C008 C00D -2.2(2) . . . . ?
C00H C007 C009 O2 178.25(16) . . . . ?
C00H C007 C009 O1 -1.1(2) . . . . ?
C00J C00B C00C C00G -177.81(16) . . . . ?
C00J C00B C00C C00K 3.0(3) . . . . ?
C00J C00B C00E C00A 179.69(15) . . . . ?
C00K C00C C00G C00F 178.26(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.263
_oxdiff_exptl_absorpt_empirical_full_min 0.393
