# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_ai527-211209-tsr-112-fr10-19-1-ca
_database_code_depnum_ccdc_archive 'CCDC 2427406'
loop_
_audit_author_name
_audit_author_address
'Ai Ito'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2025-02-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        N-Difluoromethyl-acetanilide
_chemical_formula_moiety         'C9 H9 F2 N O'
_chemical_formula_sum            'C9 H9 F2 N O'
_chemical_formula_weight         185.17
_chemical_melting_point          349.8-351.5
_chemical_oxdiff_formula         C9H9F2NO
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                   7.2772(2)
_cell_length_b                   7.3942(3)
_cell_length_c                   16.1268(5)
_cell_angle_alpha                81.500(3)
_cell_angle_beta                 83.412(2)
_cell_angle_gamma                89.984(3)
_cell_volume                     852.45(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6723
_cell_measurement_temperature    93
_cell_measurement_theta_max      75.7590
_cell_measurement_theta_min      2.7710
_shelx_estimated_absorpt_T_max   0.873
_shelx_estimated_absorpt_T_min   0.839
_exptl_absorpt_coefficient_mu    1.074
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.711
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.63a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -10 0.0793
-1 0 10 0.0748
3 4 3 0.0334
0 2 -9 0.0795
4 -2 -4 0.0654
0 -2 9 0.0803
-4 2 4 0.0887
-4 3 0 0.0898
-2 -4 -5 0.0839
0 -4 -7 0.0757
0 -4 6 0.0791
3 -3 -5 0.0622
2 -2 8 0.0679
0 5 2 0.0473
-4 0 -4 0.0979
-5 -1 0 0.0961

_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
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
0.5033 -0.2558 -10.1645 -0.3070 -0.1262 0.9433
-1.0013 -0.4902 9.5821 0.1377 0.0560 -0.9889
2.6533 3.9496 2.8430 0.8909 0.3692 0.2646
-0.3304 2.0963 -8.6309 0.1576 -0.3786 0.9120
3.9360 -1.6168 -4.0277 -0.3129 0.7568 0.5739
0.0504 -1.9510 8.7787 -0.1333 0.3199 -0.9380
-3.8941 1.5276 4.3144 0.3048 -0.7372 -0.6031
-4.0248 2.5025 0.2339 0.3769 -0.9104 -0.1710
-2.4657 -3.8689 -4.7459 -0.9216 -0.3816 -0.0705
0.3474 -3.9956 -6.8464 -0.9299 0.1222 0.3470
0.0281 -3.6329 5.5562 -0.5381 0.3307 -0.7753
3.2043 -2.6412 -5.0409 -0.5525 0.6462 0.5266
1.8829 -2.0549 8.1561 -0.1228 0.6667 -0.7352
0.3908 4.7746 2.2565 0.9735 -0.1281 0.1896
-4.4686 0.0006 -4.4694 -0.2334 -0.9720 0.0284
-4.6252 -0.5274 0.4133 -0.2069 -0.8598 -0.4668

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9618
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.312
_diffrn_reflns_theta_min         2.789
_diffrn_ambient_temperature      93
_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 0.934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     68.00 122.00   0.50    0.05    --   48.70  28.00 121.00  108
  2  ω     94.00 170.00   0.50    0.05    --  107.74  28.00 121.00  152
  3  ω    140.00 170.00   0.50    0.05    --  107.74  37.00-150.00   60
  4  ω     95.00 134.00   0.50    0.05    --  107.74  37.00-150.00   78
  5  ω     80.00 105.00   0.50    0.05    --  107.74 -99.00-150.00   50
  6  ω     80.00 105.00   0.50    0.05    --  107.74 -99.00   0.00   50
  7  ω     63.00 111.00   0.50    0.05    --  107.74-125.00  60.00   96
  8  ω     -7.00  19.00   0.50    0.05    --   48.70 -99.00 150.00   52
  9  ω     35.00  70.00   0.50    0.05    --   48.70 -99.00 150.00   70
 10  ω     67.00  92.00   0.50    0.05    --  107.74 -77.00  60.00   50
 11  ω     65.00  90.00   0.50    0.05    --  107.74 -77.00 120.00   50
 12  ω    -26.00  18.00   0.50    0.05    --   48.70 -19.00   0.00   88
 13  ω    -13.00  13.00   0.50    0.05    --   48.70 -28.00 -39.00   52
 14  ω    -48.00  20.00   0.50    0.05    --  -48.70  37.00-120.00  136
 15  ω    -22.00  27.00   0.50    0.05    --  -48.70  19.00 -30.00   98
 16  ω    -36.00  11.00   0.50    0.05    --  -48.70  28.00 121.00   94
 17  ω   -111.00 -28.00   0.50    0.05    --  -97.00 125.00 120.00  166
 18  ω    -79.00 -42.00   0.50    0.05    --  -97.00 125.00  90.00   74
 19  ω   -108.00 -82.00   0.50    0.05    --  -97.00 125.00  90.00   52
 20  ω    -49.00 -24.00   0.50    0.05    --  -97.00 125.00 -60.00   50
 21  ω   -101.00 -58.00   0.50    0.05    --  -97.00 125.00-180.00   86
 22  ω    -86.00 -30.00   0.50    0.05    --  -97.00 125.00-150.00  112
 23  ω   -110.00 -79.00   0.50    0.05    --  -97.00 125.00 -60.00   62
 24  ω    -98.00 -72.00   0.50    0.05    --  -97.00  77.00 -30.00   52
 25  ω    -69.00 -31.00   0.50    0.05    --  -97.00  77.00 -30.00   76
 26  ω    -54.00 -24.00   0.50    0.05    --  -97.00  57.00 -60.00   60
 27  ω    -69.00 -24.00   0.50    0.05    --  -97.00  57.00-150.00   90
 28  ω    -66.00 -26.00   0.50    0.05    --  -97.00  57.00 -30.00   80
 29  ω    -62.00 -26.00   0.50    0.05    --  -97.00  57.00  90.00   72
 30  ω    -70.00 -24.00   0.50    0.05    --  -97.00  57.00 120.00   92
 31  ω   -109.00 -40.00   0.50    0.05    --  -48.70 -28.00 -39.00  138
 32  ω   -144.00-119.00   0.50    0.05    --  -97.00 -99.00-150.00   50
 33  ω   -163.00 -82.00   0.50    0.05    --  -97.00-125.00 -90.00  162
 34  ω   -167.00 -84.00   0.50    0.05    --  -97.00 -28.00 -39.00  166
 35  ω   -147.00 -82.00   0.50    0.05    --  -97.00-125.00 120.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0255406000
_diffrn_orient_matrix_UB_12      0.1891728000
_diffrn_orient_matrix_UB_13      0.0267119000
_diffrn_orient_matrix_UB_21      0.1941190000
_diffrn_orient_matrix_UB_22      -0.0537602000
_diffrn_orient_matrix_UB_23      0.0233808000
_diffrn_orient_matrix_UB_31      0.0842156000
_diffrn_orient_matrix_UB_32      0.0755958000
_diffrn_orient_matrix_UB_33      -0.0905342000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3008
_reflns_number_total             3339
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_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         0.188
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3339
_refine_ls_number_restraints     144
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.035
_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)+(0.0417P)²+0.2539P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0911
_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. Uiso/Uaniso restraints and constraints
C00N \\sim C00O \\sim C00K \\sim C00L \\sim C00I \\sim C00B: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
C00H \\sim C00J \\sim C00Q \\sim C00P \\sim C00D \\sim C00A: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
3. Rigid body (RIGU) restrains
 C00N, C00B, C00I, C00K, C00L, C00O
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00H, C00J, C00Q, C00P, C00D, C00A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Ternary CH refined with riding coordinates:
 C00F(H00J), C00G(H00G)
4.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00H(H00M), C00I(H00I), C00J(H00P), C00K(H00K), C00L(H00L),
 C00N(H00N), C00O(H00O), C00P(H00Q), C00Q(H00R)
4.c Idealised Me refined as rotating group:
 C00E(H00E,H00F,H00H), C00M(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 0.40505(12) 0.09625(12) 0.38829(5) 0.0374(2) Uani 1 1 d . . . . .
F002 F 0.50747(12) 0.11060(12) 0.10931(5) 0.0359(2) Uani 1 1 d . . . . .
F003 F 0.39983(13) 0.23207(13) 0.49814(6) 0.0422(2) Uani 1 1 d . . . . .
F3 F 0.71911(13) 0.08923(14) 0.00658(6) 0.0477(3) Uani 1 1 d . . . . .
O005 O 0.72022(12) 0.57117(12) 0.01235(5) 0.0247(2) Uani 1 1 d . . . . .
O006 O -0.06941(13) 0.22126(13) 0.49643(6) 0.0273(2) Uani 1 1 d . . . . .
N007 N 0.18682(14) 0.30942(14) 0.40559(6) 0.0205(2) Uani 1 1 d . . . . .
N008 N 0.75884(14) 0.29890(14) 0.09349(6) 0.0192(2) Uani 1 1 d . . . . .
C009 C 0.00188(17) 0.32335(17) 0.43462(8) 0.0211(3) Uani 1 1 d . . . . .
C00A C 0.84755(17) 0.18719(16) 0.15834(8) 0.0195(3) Uani 1 1 d . U . . .
C00B C 0.28482(16) 0.43816(17) 0.33903(8) 0.0194(3) Uani 1 1 d . U . . .
C00C C 0.79269(16) 0.48439(17) 0.07005(7) 0.0196(3) Uani 1 1 d . . . . .
C00D C 1.01053(18) 0.09990(17) 0.13623(8) 0.0236(3) Uani 1 1 d . U . . .
H00D H 1.065946 0.116472 0.079300 0.028 Uiso 1 1 calc R U . . .
C00E C 0.92262(18) 0.57128(18) 0.11868(8) 0.0239(3) Uani 1 1 d . . . . .
H00E H 0.939070 0.701339 0.095791 0.036 Uiso 1 1 calc R U . . .
H00F H 1.042515 0.510998 0.113880 0.036 Uiso 1 1 calc R U . . .
H00H H 0.871330 0.558379 0.178194 0.036 Uiso 1 1 calc R U . . .
C00F C 0.63121(18) 0.21112(18) 0.05165(8) 0.0233(3) Uani 1 1 d . . . . .
H00J H 0.566302 0.303430 0.014046 0.028 Uiso 1 1 calc R U . . .
C00G C 0.28854(18) 0.16628(18) 0.44661(8) 0.0239(3) Uani 1 1 d . . . . .
H00G H 0.202921 0.068740 0.479398 0.029 Uiso 1 1 calc R U . . .
C00H C 0.76482(18) 0.16398(18) 0.24119(8) 0.0234(3) Uani 1 1 d . U . . .
H00M H 0.652334 0.223310 0.255540 0.028 Uiso 1 1 calc R U . . .
C00I C 0.29102(17) 0.40731(17) 0.25591(8) 0.0216(3) Uani 1 1 d . U . . .
H00I H 0.229034 0.303832 0.242874 0.026 Uiso 1 1 calc R U . . .
C00J C 0.8482(2) 0.05312(19) 0.30290(8) 0.0281(3) Uani 1 1 d . U . . .
H00P H 0.793467 0.037548 0.359938 0.034 Uiso 1 1 calc R U . . .
C00K C 0.38817(18) 0.52835(18) 0.19199(8) 0.0251(3) Uani 1 1 d . U . . .
H00K H 0.392078 0.508539 0.134941 0.030 Uiso 1 1 calc R U . . .
C00L C 0.47955(18) 0.67826(18) 0.21149(9) 0.0269(3) Uani 1 1 d . U . . .
H00L H 0.547195 0.760508 0.167799 0.032 Uiso 1 1 calc R U . . .
C00M C -0.10391(18) 0.46987(19) 0.38703(8) 0.0255(3) Uani 1 1 d . . . . .
H00A H -0.236459 0.452018 0.405723 0.038 Uiso 1 1 calc R U . . .
H00B H -0.080722 0.463538 0.326461 0.038 Uiso 1 1 calc R U . . .
H00C H -0.063726 0.589903 0.397768 0.038 Uiso 1 1 calc R U . . .
C00N C 0.37413(17) 0.58846(18) 0.35901(8) 0.0241(3) Uani 1 1 d . U . . .
H00N H 0.368421 0.609490 0.415951 0.029 Uiso 1 1 calc R U . . .
C00O C 0.47243(18) 0.70836(18) 0.29448(9) 0.0281(3) Uani 1 1 d . U . . .
H00O H 0.535024 0.811499 0.307484 0.034 Uiso 1 1 calc R U . . .
C00P C 1.09175(19) -0.01196(18) 0.19823(9) 0.0283(3) Uani 1 1 d . U . . .
H00Q H 1.202996 -0.073108 0.183680 0.034 Uiso 1 1 calc R U . . .
C00Q C 1.0111(2) -0.03488(18) 0.28141(9) 0.0295(3) Uani 1 1 d . U . . .
H00R H 1.067691 -0.111010 0.323711 0.035 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 C00G 1.3536(15) . ?
F002 C00F 1.3534(15) . ?
F003 C00G 1.3628(16) . ?
F3 C00F 1.3552(15) . ?
O005 C00C 1.2213(15) . ?
O006 C009 1.2213(15) . ?
N007 C009 1.3823(16) . ?
N007 C00B 1.4455(15) . ?
N007 C00G 1.4180(17) . ?
N008 C00A 1.4463(15) . ?
N008 C00C 1.3821(16) . ?
N008 C00F 1.4187(16) . ?
C009 C00M 1.4982(18) . ?
C00A C00D 1.3860(18) . ?
C00A C00H 1.3874(17) . ?
C00B C00I 1.3885(18) . ?
C00B C00N 1.3840(18) . ?
C00C C00E 1.4971(18) . ?
C00D H00D 0.9500 . ?
C00D C00P 1.3871(19) . ?
C00E H00E 0.9800 . ?
C00E H00F 0.9800 . ?
C00E H00H 0.9800 . ?
C00F H00J 1.0000 . ?
C00G H00G 1.0000 . ?
C00H H00M 0.9500 . ?
C00H C00J 1.3883(19) . ?
C00I H00I 0.9500 . ?
C00I C00K 1.3870(18) . ?
C00J H00P 0.9500 . ?
C00J C00Q 1.386(2) . ?
C00K H00K 0.9500 . ?
C00K C00L 1.386(2) . ?
C00L H00L 0.9500 . ?
C00L C00O 1.384(2) . ?
C00M H00A 0.9800 . ?
C00M H00B 0.9800 . ?
C00M H00C 0.9800 . ?
C00N H00N 0.9500 . ?
C00N C00O 1.3920(19) . ?
C00O H00O 0.9500 . ?
C00P H00Q 0.9500 . ?
C00P C00Q 1.387(2) . ?
C00Q H00R 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 N007 C00B 123.78(10) . . ?
C009 N007 C00G 118.02(10) . . ?
C00G N007 C00B 118.11(10) . . ?
C00C N008 C00A 123.71(10) . . ?
C00C N008 C00F 118.76(10) . . ?
C00F N008 C00A 117.53(10) . . ?
O006 C009 N007 120.96(12) . . ?
O006 C009 C00M 122.40(11) . . ?
N007 C009 C00M 116.63(11) . . ?
C00D C00A N008 119.44(11) . . ?
C00D C00A C00H 121.04(12) . . ?
C00H C00A N008 119.48(11) . . ?
C00I C00B N007 119.43(11) . . ?
C00N C00B N007 119.70(11) . . ?
C00N C00B C00I 120.86(12) . . ?
O005 C00C N008 121.18(11) . . ?
O005 C00C C00E 122.35(11) . . ?
N008 C00C C00E 116.47(11) . . ?
C00A C00D H00D 120.4 . . ?
C00A C00D C00P 119.21(12) . . ?
C00P C00D H00D 120.4 . . ?
C00C C00E H00E 109.5 . . ?
C00C C00E H00F 109.5 . . ?
C00C C00E H00H 109.5 . . ?
H00E C00E H00F 109.5 . . ?
H00E C00E H00H 109.5 . . ?
H00F C00E H00H 109.5 . . ?
F002 C00F F3 105.26(11) . . ?
F002 C00F N008 109.70(10) . . ?
F002 C00F H00J 110.5 . . ?
F3 C00F N008 110.36(10) . . ?
F3 C00F H00J 110.5 . . ?
N008 C00F H00J 110.5 . . ?
F001 C00G F003 105.23(11) . . ?
F001 C00G N007 109.30(10) . . ?
F001 C00G H00G 110.5 . . ?
F003 C00G N007 110.72(11) . . ?
F003 C00G H00G 110.5 . . ?
N007 C00G H00G 110.5 . . ?
C00A C00H H00M 120.4 . . ?
C00A C00H C00J 119.30(12) . . ?
C00J C00H H00M 120.4 . . ?
C00B C00I H00I 120.2 . . ?
C00K C00I C00B 119.66(12) . . ?
C00K C00I H00I 120.2 . . ?
C00H C00J H00P 120.0 . . ?
C00Q C00J C00H 120.09(12) . . ?
C00Q C00J H00P 120.0 . . ?
C00I C00K H00K 120.1 . . ?
C00L C00K C00I 119.89(12) . . ?
C00L C00K H00K 120.1 . . ?
C00K C00L H00L 119.9 . . ?
C00O C00L C00K 120.13(12) . . ?
C00O C00L H00L 119.9 . . ?
C009 C00M H00A 109.5 . . ?
C009 C00M H00B 109.5 . . ?
C009 C00M H00C 109.5 . . ?
H00A C00M H00B 109.5 . . ?
H00A C00M H00C 109.5 . . ?
H00B C00M H00C 109.5 . . ?
C00B C00N H00N 120.5 . . ?
C00B C00N C00O 119.05(12) . . ?
C00O C00N H00N 120.5 . . ?
C00L C00O C00N 120.42(13) . . ?
C00L C00O H00O 119.8 . . ?
C00N C00O H00O 119.8 . . ?
C00D C00P H00Q 119.9 . . ?
C00D C00P C00Q 120.25(12) . . ?
C00Q C00P H00Q 119.9 . . ?
C00J C00Q C00P 120.11(12) . . ?
C00J C00Q H00R 119.9 . . ?
C00P C00Q H00R 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N007 C00B C00I C00K -178.64(11) . . . . ?
N007 C00B C00N C00O 178.15(11) . . . . ?
N008 C00A C00D C00P -177.86(11) . . . . ?
N008 C00A C00H C00J 178.47(11) . . . . ?
C009 N007 C00B C00I -90.58(15) . . . . ?
C009 N007 C00B C00N 90.65(15) . . . . ?
C009 N007 C00G F001 140.53(11) . . . . ?
C009 N007 C00G F003 -104.00(13) . . . . ?
C00A N008 C00C O005 176.78(11) . . . . ?
C00A N008 C00C C00E -2.92(16) . . . . ?
C00A N008 C00F F002 50.37(14) . . . . ?
C00A N008 C00F F3 -65.16(14) . . . . ?
C00A C00D C00P C00Q -0.4(2) . . . . ?
C00A C00H C00J C00Q -0.8(2) . . . . ?
C00B N007 C009 O006 -172.76(11) . . . . ?
C00B N007 C009 C00M 6.71(17) . . . . ?
C00B N007 C00G F001 -42.84(15) . . . . ?
C00B N007 C00G F003 72.63(14) . . . . ?
C00B C00I C00K C00L 0.52(19) . . . . ?
C00B C00N C00O C00L 0.5(2) . . . . ?
C00C N008 C00A C00D -91.37(15) . . . . ?
C00C N008 C00A C00H 90.87(14) . . . . ?
C00C N008 C00F F002 -130.10(11) . . . . ?
C00C N008 C00F F3 114.37(12) . . . . ?
C00D C00A C00H C00J 0.75(19) . . . . ?
C00D C00P C00Q C00J 0.4(2) . . . . ?
C00F N008 C00A C00D 88.14(14) . . . . ?
C00F N008 C00A C00H -89.62(14) . . . . ?
C00F N008 C00C O005 -2.73(17) . . . . ?
C00F N008 C00C C00E 177.58(10) . . . . ?
C00G N007 C009 O006 3.66(18) . . . . ?
C00G N007 C009 C00M -176.87(11) . . . . ?
C00G N007 C00B C00I 93.01(14) . . . . ?
C00G N007 C00B C00N -85.77(15) . . . . ?
C00H C00A C00D C00P -0.14(19) . . . . ?
C00H C00J C00Q C00P 0.2(2) . . . . ?
C00I C00B C00N C00O -0.60(19) . . . . ?
C00I C00K C00L C00O -0.66(19) . . . . ?
C00K C00L C00O C00N 0.2(2) . . . . ?
C00N C00B C00I C00K 0.12(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 1.797
_oxdiff_exptl_absorpt_empirical_full_min 0.670
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2-nhex'
####################################################################### 
# 
# 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_ai627-220627-tsr236-fr23-29-ca
_database_code_depnum_ccdc_archive 'CCDC 2427407'
loop_
_audit_author_name
_audit_author_address
'Ai Ito'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2025-02-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        N-Difluoromethylbenzanilide
_chemical_formula_moiety         'C14 H11 F2 N O'
_chemical_formula_sum            'C14 H11 F2 N O'
_chemical_formula_weight         247.24
_chemical_absolute_configuration .
_chemical_melting_point          368.8-370
_chemical_oxdiff_formula         C14H11F2NO
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.0428(3)
_cell_length_b                   6.0775(3)
_cell_length_c                   12.1408(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.734(4)
_cell_angle_gamma                90
_cell_volume                     593.40(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2036
_cell_measurement_temperature    93
_cell_measurement_theta_max      72.8490
_cell_measurement_theta_min      3.6150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.63a (Rigaku Oxford Diffraction, 2020)
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    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.147
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.055
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3235
_diffrn_reflns_point_group_measured_fraction_full 0.797
_diffrn_reflns_point_group_measured_fraction_max 0.740
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.692
_diffrn_reflns_theta_min         3.641
_diffrn_ambient_temperature      93
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  22.00   0.50    0.40    --   46.70 -19.00   0.00   84
  2  ω    -10.00  32.00   0.50    0.40    --   46.70 -88.00  10.00   84
  3  ω     65.00  91.00   0.50    1.30    --  108.36 -88.00  10.00   52
  4  ω     66.00  91.00   0.50    1.30    --  108.36 -77.00-180.00   50
  5  ω     84.00 173.00   0.50    1.30    --  108.36  88.00 127.00  178
  6  ω    -60.00  26.00   0.50    0.40    --  -46.70  88.00 127.00  172
  7  ω    -93.00 -25.00   0.50    1.30    --  -97.00 125.00 150.00  136
  8  ω    -71.00 -25.00   0.50    1.30    --  -97.00  88.00 127.00   92
  9  ω   -115.00 -73.00   0.50    1.30    --  -97.00  88.00 127.00   84
 10  ω    -61.00 -24.00   0.50    1.30    --  -97.00  57.00 -90.00   74
 11  ω    -48.00  25.00   0.50    0.40    --  -46.70  37.00-120.00  146
 12  ω    -62.00 -26.00   0.50    1.30    --  -97.00  57.00 -30.00   72
 13  ω    -69.00 -39.00   0.50    1.30    --  -97.00  57.00  60.00   60
 14  ω    -69.00 -33.00   0.50    1.30    --  -97.00  57.00  90.00   72
 15  ω   -168.00-135.00   0.50    1.30    --  -97.00 -57.00  60.00   66
 16  ω   -168.00-111.00   0.50    1.30    --  -97.00 -99.00 -30.00  114
 17  ω   -161.00-136.00   0.50    1.30    --  -97.00 -88.00  10.00   50
 18  ω   -132.00 -84.00   0.50    1.30    --  -97.00 -57.00  60.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1599129000
_diffrn_orient_matrix_UB_12      -0.0828924000
_diffrn_orient_matrix_UB_13      0.0547704000
_diffrn_orient_matrix_UB_21      0.0900798000
_diffrn_orient_matrix_UB_22      -0.2136060000
_diffrn_orient_matrix_UB_23      0.0341341000
_diffrn_orient_matrix_UB_31      0.0550826000
_diffrn_orient_matrix_UB_32      0.1084867000
_diffrn_orient_matrix_UB_33      0.1092033000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.457
_reflns_Friedel_fraction_full    0.567
_reflns_Friedel_fraction_max     0.515
_reflns_number_gt                1688
_reflns_number_total             1801
_reflns_odcompleteness_completeness 98.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_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         0.304
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Flack x determined using 502 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1801
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.090
_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)+(0.0850P)²+0.2634P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1373
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C14(H14), C5(H5), C4(H4), C3(H3), C18(H18), C17(H17),
 C16(H16), C15(H15)
;
_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
F11 F 0.4989(3) 0.0139(4) 0.75200(18) 0.0302(6) Uani 1 1 d . . . . .
F10 F 0.3409(3) 0.3014(4) 0.75469(18) 0.0290(6) Uani 1 1 d . . . . .
O12 O 0.5761(3) 0.4934(6) 0.9556(2) 0.0281(7) Uani 1 1 d . . . . .
N1 N 0.6206(4) 0.3455(6) 0.7868(2) 0.0223(8) Uani 1 1 d . . . . .
C13 C 0.6729(5) 0.3792(7) 0.6736(3) 0.0215(8) Uani 1 1 d . . . . .
C7 C 0.6599(4) 0.4911(8) 0.8727(3) 0.0219(8) Uani 1 1 d . . . . .
C1 C 0.8067(5) 0.6391(8) 0.8615(3) 0.0219(8) Uani 1 1 d . . . . .
C9 C 0.4804(5) 0.2101(7) 0.8036(3) 0.0232(8) Uani 1 1 d . . . . .
H9 H 0.462297 0.187294 0.884146 0.028 Uiso 1 1 calc R U . . .
C6 C 0.7958(4) 0.8435(8) 0.9139(3) 0.0233(9) Uani 1 1 d . . . . .
H6 H 0.696419 0.883695 0.950229 0.028 Uiso 1 1 calc R U . . .
C2 C 0.9548(5) 0.5772(7) 0.8108(3) 0.0238(9) Uani 1 1 d . . . . .
H2 H 0.963452 0.437817 0.775862 0.029 Uiso 1 1 calc R U . . .
C14 C 0.7676(5) 0.2195(8) 0.6236(3) 0.0262(9) Uani 1 1 d . . . . .
H14 H 0.799537 0.090255 0.662475 0.031 Uiso 1 1 calc R U . . .
C5 C 0.9287(5) 0.9870(8) 0.9129(3) 0.0262(9) Uani 1 1 d . . . . .
H5 H 0.919958 1.127032 0.947115 0.031 Uiso 1 1 calc R U . . .
C4 C 1.0759(5) 0.9264(8) 0.8616(3) 0.0264(9) Uani 1 1 d . . . . .
H4 H 1.167432 1.025095 0.860632 0.032 Uiso 1 1 calc R U . . .
C3 C 1.0884(5) 0.7206(8) 0.8119(3) 0.0263(9) Uani 1 1 d . . . . .
H3 H 1.189635 0.678305 0.778408 0.032 Uiso 1 1 calc R U . . .
C18 C 0.6244(5) 0.5683(7) 0.6189(3) 0.0235(9) Uani 1 1 d . . . . .
H18 H 0.557525 0.675068 0.654460 0.028 Uiso 1 1 calc R U . . .
C17 C 0.6756(5) 0.6001(8) 0.5099(3) 0.0278(9) Uani 1 1 d . . . . .
H17 H 0.644258 0.729945 0.471346 0.033 Uiso 1 1 calc R U . . .
C16 C 0.7706(5) 0.4444(8) 0.4591(3) 0.0281(10) Uani 1 1 d . . . . .
H16 H 0.806042 0.467942 0.385659 0.034 Uiso 1 1 calc R U . . .
C15 C 0.8159(5) 0.2519(8) 0.5139(3) 0.0291(10) Uani 1 1 d . . . . .
H15 H 0.879272 0.142798 0.477285 0.035 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
F11 C9 1.356(5) . ?
F10 C9 1.380(4) . ?
O12 C7 1.219(4) . ?
N1 C13 1.457(4) . ?
N1 C7 1.401(5) . ?
N1 C9 1.413(5) . ?
C13 C14 1.380(6) . ?
C13 C18 1.380(6) . ?
C7 C1 1.492(6) . ?
C1 C6 1.399(6) . ?
C1 C2 1.399(5) . ?
C9 H9 1.0000 . ?
C6 H6 0.9500 . ?
C6 C5 1.380(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.406(5) . ?
C5 H5 0.9500 . ?
C5 C4 1.394(6) . ?
C4 H4 0.9500 . ?
C4 C3 1.393(7) . ?
C3 H3 0.9500 . ?
C18 H18 0.9500 . ?
C18 C17 1.405(5) . ?
C17 H17 0.9500 . ?
C17 C16 1.368(7) . ?
C16 H16 0.9500 . ?
C16 C15 1.392(7) . ?
C15 H15 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
C7 N1 C13 123.3(3) . . ?
C7 N1 C9 115.7(3) . . ?
C9 N1 C13 117.3(3) . . ?
C14 C13 N1 118.9(4) . . ?
C14 C13 C18 121.9(3) . . ?
C18 C13 N1 119.2(4) . . ?
O12 C7 N1 120.0(4) . . ?
O12 C7 C1 121.0(3) . . ?
N1 C7 C1 118.9(3) . . ?
C6 C1 C7 116.1(3) . . ?
C6 C1 C2 119.9(4) . . ?
C2 C1 C7 123.9(4) . . ?
F11 C9 F10 104.3(3) . . ?
F11 C9 N1 110.7(3) . . ?
F11 C9 H9 110.4 . . ?
F10 C9 N1 110.5(3) . . ?
F10 C9 H9 110.4 . . ?
N1 C9 H9 110.4 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.3(4) . . ?
C5 C6 H6 119.9 . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.4(4) . . ?
C3 C2 H2 120.3 . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.6(4) . . ?
C15 C14 H14 120.7 . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 119.9(4) . . ?
C4 C5 H5 120.0 . . ?
C5 C4 H4 120.1 . . ?
C3 C4 C5 119.8(4) . . ?
C3 C4 H4 120.1 . . ?
C2 C3 C4 120.6(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C13 C18 H18 120.6 . . ?
C13 C18 C17 118.9(4) . . ?
C17 C18 H18 120.6 . . ?
C18 C17 H17 119.9 . . ?
C16 C17 C18 120.1(4) . . ?
C16 C17 H17 119.9 . . ?
C17 C16 H16 119.7 . . ?
C17 C16 C15 120.7(3) . . ?
C15 C16 H16 119.7 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.8(4) . . ?
C16 C15 H15 120.1 . . ?

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
O12 C7 C1 C6 -32.3(5) . . . . ?
O12 C7 C1 C2 142.2(4) . . . . ?
N1 C13 C14 C15 179.3(3) . . . . ?
N1 C13 C18 C17 179.8(3) . . . . ?
N1 C7 C1 C6 148.7(3) . . . . ?
N1 C7 C1 C2 -36.7(5) . . . . ?
C13 N1 C7 O12 158.3(4) . . . . ?
C13 N1 C7 C1 -22.8(6) . . . . ?
C13 N1 C9 F11 52.2(5) . . . . ?
C13 N1 C9 F10 -62.8(4) . . . . ?
C13 C14 C15 C16 1.3(6) . . . . ?
C13 C18 C17 C16 0.6(6) . . . . ?
C7 N1 C13 C14 121.9(4) . . . . ?
C7 N1 C13 C18 -59.0(5) . . . . ?
C7 N1 C9 F11 -148.9(3) . . . . ?
C7 N1 C9 F10 96.1(4) . . . . ?
C7 C1 C6 C5 176.7(3) . . . . ?
C7 C1 C2 C3 -175.1(3) . . . . ?
C1 C6 C5 C4 -1.4(5) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C9 N1 C13 C14 -81.0(5) . . . . ?
C9 N1 C13 C18 98.2(4) . . . . ?
C9 N1 C7 O12 0.8(6) . . . . ?
C9 N1 C7 C1 179.7(4) . . . . ?
C6 C1 C2 C3 -0.8(5) . . . . ?
C6 C5 C4 C3 -0.2(5) . . . . ?
C2 C1 C6 C5 1.9(5) . . . . ?
C14 C13 C18 C17 -1.1(6) . . . . ?
C5 C4 C3 C2 1.4(5) . . . . ?
C18 C13 C14 C15 0.2(6) . . . . ?
C18 C17 C16 C15 0.8(6) . . . . ?
C17 C16 C15 C14 -1.8(6) . . . . ?

_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 1.990
_oxdiff_exptl_absorpt_empirical_full_min 0.531
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2-nhex'
####################################################################### 
# 
# 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_ai807-241120-4ry12c-ca_auto
_database_code_depnum_ccdc_archive 'CCDC 2427410'
loop_
_audit_author_name
_audit_author_address
'Ai Ito'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2024-12-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        
Methyl-p-((N-difluromethyl)benzamido)methyl)benzoate
_chemical_formula_moiety         'C17 H15 F2 N O3'
_chemical_formula_sum            'C17 H15 F2 N O3'
_chemical_formula_weight         319.30
_chemical_melting_point          342.5-344.5
_chemical_oxdiff_formula         C17H15F2NO3
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                   5.6213(3)
_cell_length_b                   8.9645(5)
_cell_length_c                   14.5753(7)
_cell_angle_alpha                84.447(4)
_cell_angle_beta                 87.484(5)
_cell_angle_gamma                81.834(5)
_cell_volume                     723.28(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4555
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      76.7560
_cell_measurement_theta_min      3.0440
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.893
_exptl_absorpt_coefficient_mu    1.001
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94914
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.130a (Rigaku Oxford Diffraction, 2024)
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    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.116
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7733
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.938
_diffrn_reflns_theta_min         3.048
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  38.00   0.50    0.07    --   46.95 -37.00   0.00  126
  2  ω    -25.00  37.00   0.50    0.07    --   46.95 -37.00 -60.00  124
  3  ω    -24.00  20.00   0.50    0.07    --   46.95 -19.00-120.00   88
  4  ω     57.00  82.00   0.50    0.28    --  108.36 -77.00 -90.00   50
  5  ω     85.00 111.00   0.50    0.28    --  108.36-125.00-150.00   52
  6  ω     50.00  81.00   0.50    0.28    --  108.36-125.00-150.00   62
  7  ω     52.00  83.00   0.50    0.28    --  108.36 -99.00-150.00   62
  8  ω     52.00  78.00   0.50    0.07    --   46.95 -96.00 -99.00   52
  9  ω     55.00 109.00   0.50    0.28    --  108.36-125.00  90.00  108
 10  ω     67.00 103.00   0.50    0.28    --  108.36 -99.00 120.00   72
 11  ω     38.00  64.00   0.50    0.28    --  108.36 -99.00 120.00   52
 12  ω     80.00 105.00   0.50    0.28    --  108.36 -99.00  60.00   50
 13  ω     67.00  92.00   0.50    0.28    --  108.36 -96.00 -99.00   50
 14  ω    -23.00  48.00   0.50    0.07    --   46.95 -96.00 -99.00  142
 15  ω    142.00 174.00   0.50    0.28    --  108.36  19.00-180.00   64
 16  ω     96.00 123.00   0.50    0.28    --  108.36  19.00-180.00   54
 17  ω    104.00 140.00   0.50    0.28    --  108.36  57.00 -60.00   72
 18  ω    149.00 174.00   0.50    0.28    --  108.36  57.00 -60.00   50
 19  ω     92.00 130.00   0.50    0.28    --  108.36  96.00   9.00   76
 20  ω     94.00 119.00   0.50    0.07    --   46.95 179.00 -60.00   50
 21  ω     59.00  85.00   0.50    0.07    --   46.95 179.00 -60.00   52
 22  ω    -21.00  19.00   0.50    0.07    --  -46.95  96.00   9.00   80
 23  ω    -66.00 -40.00   0.50    0.07    --  -46.95  96.00   9.00   52
 24  ω   -106.00 -72.00   0.50    0.28    --  -97.00 106.00-112.29   68
 25  ω   -105.00 -40.00   0.50    0.28    --  -97.00 125.00 -30.00  130
 26  ω   -106.00 -81.00   0.50    0.28    --  -97.00  96.00   9.00   50
 27  ω    -61.00 -36.00   0.50    0.28    --  -97.00  57.00 -30.00   50
 28  ω    -64.00 -34.00   0.50    0.28    --  -97.00  57.00 120.00   60
 29  ω    -62.00 -32.00   0.50    0.28    --  -97.00  57.00   0.00   60
 30  ω    -66.00 -40.00   0.50    0.28    --  -97.00  57.00-180.00   52
 31  ω   -169.00 -84.00   0.50    0.28    --  -97.00 -37.00-180.00  170
 32  ω   -154.00-115.00   0.50    0.28    --  -97.00-125.00-120.00   78
 33  ω   -168.00 -91.00   0.50    0.28    --  -97.00 -99.00 -60.00  154
 34  ω   -142.00 -91.00   0.50    0.28    --  -97.00 -96.00 -99.00  102
 35  ω   -152.00-121.00   0.50    0.28    --  -97.00 -99.00   0.00   62
 36  ω   -163.00 -84.00   0.50    0.28    --  -97.00-125.00 120.00  158
 37  ω   -166.00 -92.00   0.50    0.28    --  -97.00 -99.00 150.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-Custom'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0366090000
_diffrn_orient_matrix_UB_12      -0.1403736000
_diffrn_orient_matrix_UB_13      0.0703808000
_diffrn_orient_matrix_UB_21      -0.0870781000
_diffrn_orient_matrix_UB_22      -0.0961188000
_diffrn_orient_matrix_UB_23      -0.0705021000
_diffrn_orient_matrix_UB_31      0.2603917000
_diffrn_orient_matrix_UB_32      -0.0381079000
_diffrn_orient_matrix_UB_33      -0.0369310000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2435
_reflns_number_total             2850
_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 1.171.43.130a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.130a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.130a (Rigaku OD, 2024)'
_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         0.256
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0026(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2850
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.040
_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)+(0.0411P)²+0.2452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0931
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C2(H2), C19(H19), C5(H5), C3(H3), C6(H6), C21(H21), C22(H22),
 C20(H20)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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
F10 F 1.09448(14) 0.35187(9) 0.53785(6) 0.0225(2) Uani 1 1 d . . . . .
F11 F 0.82812(15) 0.32455(10) 0.43994(5) 0.0258(2) Uani 1 1 d . . . . .
O15 O 1.20870(17) 0.61926(11) 0.94476(7) 0.0235(2) Uani 1 1 d . . . . .
O17 O 0.87069(17) 0.78598(11) 0.95188(7) 0.0231(2) Uani 1 1 d . . . . .
O13 O 0.73960(17) 0.01088(11) 0.56191(7) 0.0237(2) Uani 1 1 d . . . . .
N8 N 0.76165(19) 0.25178(12) 0.59359(8) 0.0166(2) Uani 1 1 d . . . . .
C18 C 0.4967(2) 0.09222(14) 0.68790(9) 0.0170(3) Uani 1 1 d . . . . .
C1 C 0.7380(2) 0.46593(14) 0.69729(9) 0.0166(3) Uani 1 1 d . . . . .
C4 C 0.9082(2) 0.60515(15) 0.83997(9) 0.0175(3) Uani 1 1 d . . . . .
C12 C 0.6722(2) 0.11463(14) 0.60970(9) 0.0170(3) Uani 1 1 d . . . . .
C23 C 0.3157(2) 0.00579(15) 0.67360(10) 0.0188(3) Uani 1 1 d . . . . .
H23 H 0.303461 -0.030645 0.615153 0.023 Uiso 1 1 calc R U . . .
C2 C 0.9552(2) 0.40625(15) 0.73750(9) 0.0183(3) Uani 1 1 d . . . . .
H2 H 1.045538 0.317468 0.716592 0.022 Uiso 1 1 calc R U . . .
C19 C 0.5189(2) 0.14085(15) 0.77481(9) 0.0185(3) Uani 1 1 d . . . . .
H19 H 0.643250 0.198253 0.785116 0.022 Uiso 1 1 calc R U . . .
C5 C 0.6913(2) 0.66614(15) 0.79931(10) 0.0197(3) Uani 1 1 d . . . . .
H5 H 0.600787 0.754736 0.820356 0.024 Uiso 1 1 calc R U . . .
C9 C 0.9352(2) 0.25865(15) 0.51947(9) 0.0185(3) Uani 1 1 d . . . . .
H9 H 1.020404 0.155257 0.510081 0.022 Uiso 1 1 calc R U . . .
C3 C 1.0406(2) 0.47574(15) 0.80798(9) 0.0185(3) Uani 1 1 d . . . . .
H3 H 1.189967 0.435002 0.834570 0.022 Uiso 1 1 calc R U . . .
C14 C 0.9883(2) 0.68041(15) 0.91732(9) 0.0188(3) Uani 1 1 d . . . . .
C6 C 0.6081(2) 0.59748(15) 0.72829(9) 0.0194(3) Uani 1 1 d . . . . .
H6 H 0.461400 0.640114 0.700318 0.023 Uiso 1 1 calc R U . . .
C21 C 0.1747(2) 0.02338(15) 0.83120(10) 0.0213(3) Uani 1 1 d . . . . .
H21 H 0.063016 0.001600 0.879768 0.026 Uiso 1 1 calc R U . . .
C22 C 0.1538(2) -0.02675(15) 0.74487(10) 0.0210(3) Uani 1 1 d . . . . .
H22 H 0.028371 -0.083404 0.734698 0.025 Uiso 1 1 calc R U . . .
C20 C 0.3590(2) 0.10526(15) 0.84625(9) 0.0205(3) Uani 1 1 d . . . . .
H20 H 0.375860 0.137076 0.905650 0.025 Uiso 1 1 calc R U . . .
C7 C 0.6326(2) 0.39682(14) 0.62022(9) 0.0173(3) Uani 1 1 d . . . . .
H7A H 0.465606 0.381700 0.638826 0.021 Uiso 1 1 calc R U . . .
H7B H 0.624483 0.470787 0.565037 0.021 Uiso 1 1 calc R U . . .
C16 C 1.3090(3) 0.69483(17) 1.01412(10) 0.0251(3) Uani 1 1 d . . . . .
H16A H 1.344891 0.793989 0.987313 0.038 Uiso 1 1 calc R U . . .
H16B H 1.457254 0.633485 1.036269 0.038 Uiso 1 1 calc R U . . .
H16C H 1.192783 0.708241 1.065791 0.038 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
F10 C9 1.3598(15) . ?
F11 C9 1.3721(15) . ?
O15 C14 1.3429(17) . ?
O15 C16 1.4456(16) . ?
O17 C14 1.2132(16) . ?
O13 C12 1.2230(16) . ?
N8 C12 1.3889(17) . ?
N8 C9 1.4262(17) . ?
N8 C7 1.4739(16) . ?
C18 C12 1.4919(19) . ?
C18 C23 1.3975(19) . ?
C18 C19 1.3952(19) . ?
C1 C2 1.3918(19) . ?
C1 C6 1.3991(18) . ?
C1 C7 1.5146(17) . ?
C4 C5 1.396(2) . ?
C4 C3 1.3951(19) . ?
C4 C14 1.4858(18) . ?
C23 H23 0.9500 . ?
C23 C22 1.388(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.3876(19) . ?
C19 H19 0.9500 . ?
C19 C20 1.3886(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.3843(19) . ?
C9 H9 1.0000 . ?
C3 H3 0.9500 . ?
C6 H6 0.9500 . ?
C21 H21 0.9500 . ?
C21 C22 1.391(2) . ?
C21 C20 1.388(2) . ?
C22 H22 0.9500 . ?
C20 H20 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C14 O15 C16 115.77(10) . . ?
C12 N8 C9 114.80(10) . . ?
C12 N8 C7 123.90(11) . . ?
C9 N8 C7 117.04(11) . . ?
C23 C18 C12 116.68(12) . . ?
C19 C18 C12 123.32(12) . . ?
C19 C18 C23 119.73(12) . . ?
C2 C1 C6 119.16(12) . . ?
C2 C1 C7 123.56(11) . . ?
C6 C1 C7 117.29(11) . . ?
C5 C4 C14 118.25(12) . . ?
C3 C4 C5 119.52(12) . . ?
C3 C4 C14 122.22(12) . . ?
O13 C12 N8 120.84(12) . . ?
O13 C12 C18 119.60(12) . . ?
N8 C12 C18 119.54(11) . . ?
C18 C23 H23 120.0 . . ?
C22 C23 C18 119.93(13) . . ?
C22 C23 H23 120.0 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.35(12) . . ?
C3 C2 H2 119.8 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 119.95(12) . . ?
C20 C19 H19 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 119.97(12) . . ?
C6 C5 H5 120.0 . . ?
F10 C9 F11 105.01(10) . . ?
F10 C9 N8 109.35(10) . . ?
F10 C9 H9 110.6 . . ?
F11 C9 N8 110.60(10) . . ?
F11 C9 H9 110.6 . . ?
N8 C9 H9 110.6 . . ?
C4 C3 H3 119.8 . . ?
C2 C3 C4 120.32(12) . . ?
C2 C3 H3 119.8 . . ?
O15 C14 C4 112.34(11) . . ?
O17 C14 O15 123.23(12) . . ?
O17 C14 C4 124.43(12) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.66(12) . . ?
C5 C6 H6 119.7 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 119.91(13) . . ?
C23 C22 C21 120.18(13) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.26(13) . . ?
C21 C20 H20 119.9 . . ?
N8 C7 C1 116.51(10) . . ?
N8 C7 H7A 108.2 . . ?
N8 C7 H7B 108.2 . . ?
C1 C7 H7A 108.2 . . ?
C1 C7 H7B 108.2 . . ?
H7A C7 H7B 107.3 . . ?
O15 C16 H16A 109.5 . . ?
O15 C16 H16B 109.5 . . ?
O15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C18 C23 C22 C21 -1.5(2) . . . . ?
C18 C19 C20 C21 -1.0(2) . . . . ?
C1 C2 C3 C4 0.7(2) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
C12 N8 C9 F10 -148.42(11) . . . . ?
C12 N8 C9 F11 96.42(13) . . . . ?
C12 N8 C7 C1 110.93(14) . . . . ?
C12 C18 C23 C22 176.52(11) . . . . ?
C12 C18 C19 C20 -174.86(12) . . . . ?
C23 C18 C12 O13 -37.70(18) . . . . ?
C23 C18 C12 N8 143.95(12) . . . . ?
C23 C18 C19 C20 -1.00(19) . . . . ?
C2 C1 C6 C5 -1.3(2) . . . . ?
C2 C1 C7 N8 5.27(18) . . . . ?
C19 C18 C12 O13 136.32(14) . . . . ?
C19 C18 C12 N8 -42.02(18) . . . . ?
C19 C18 C23 C22 2.26(19) . . . . ?
C5 C4 C3 C2 -1.3(2) . . . . ?
C5 C4 C14 O15 -174.41(11) . . . . ?
C5 C4 C14 O17 5.0(2) . . . . ?
C9 N8 C12 O13 -0.71(18) . . . . ?
C9 N8 C12 C18 177.61(11) . . . . ?
C9 N8 C7 C1 -93.54(14) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C3 C4 C14 O15 6.37(18) . . . . ?
C3 C4 C14 O17 -174.20(13) . . . . ?
C14 C4 C5 C6 -178.70(12) . . . . ?
C14 C4 C3 C2 177.92(12) . . . . ?
C6 C1 C2 C3 0.55(19) . . . . ?
C6 C1 C7 N8 -175.23(11) . . . . ?
C22 C21 C20 C19 1.7(2) . . . . ?
C20 C21 C22 C23 -0.5(2) . . . . ?
C7 N8 C12 O13 155.31(12) . . . . ?
C7 N8 C12 C18 -26.36(18) . . . . ?
C7 N8 C9 F10 53.83(14) . . . . ?
C7 N8 C9 F11 -61.33(14) . . . . ?
C7 C1 C2 C3 -179.95(12) . . . . ?
C7 C1 C6 C5 179.16(12) . . . . ?
C16 O15 C14 O17 -4.85(19) . . . . ?
C16 O15 C14 C4 174.59(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 1.352
_oxdiff_exptl_absorpt_empirical_full_min 0.742
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: AcOEt-nhex'
####################################################################### 
# 
# 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_ai768-240515-sat-275-recry-hex-ca_auto
_database_code_depnum_ccdc_archive 'CCDC 2427409'
loop_
_audit_author_name
_audit_author_address
'Ai Ito'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2024-05-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        
N-Difluoromethyl-N-pentafluorophenyl-benzanilide
_chemical_formula_moiety         'C14 H6 F7 N O'
_chemical_formula_sum            'C14 H6 F7 N O'
_chemical_formula_weight         337.20
_chemical_melting_point          330.0-330.5
_chemical_oxdiff_formula         C14H6F7NO
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/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                   11.5847(4)
_cell_length_b                   7.5874(2)
_cell_length_c                   15.3165(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.138(4)
_cell_angle_gamma                90
_cell_volume                     1279.39(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5271
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      75.8830
_cell_measurement_theta_min      3.9810
_shelx_estimated_absorpt_T_max   0.860
_shelx_estimated_absorpt_T_min   0.734
_exptl_absorpt_coefficient_mu    1.634
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78695
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
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    1.751
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: AcOEt-nhex'
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.095
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7633
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.097
_diffrn_reflns_theta_min         4.015
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  26.00   0.50    0.05    --   46.26 -92.00  27.00   98
  2  ω    -11.00  18.00   0.50    0.05    --   46.26 -19.00   0.00   58
  3  ω     37.00 102.00   0.50    0.12    --  108.36 -92.00  27.00  130
  4  ω     67.00 124.00   0.50    0.12    --  108.36 -77.00  30.00  114
  5  ω     81.00 151.00   0.50    0.12    --  108.36  92.00 139.00  140
  6  ω    115.00 172.00   0.50    0.12    --  108.36  19.00-150.00  114
  7  ω    -24.00  16.00   0.50    0.05    --   46.26 -19.00 -90.00   80
  8  ω    -76.00  24.00   0.50    0.05    --  -46.26  92.00 139.00  200
  9  ω    -94.00 -51.00   0.50    0.12    --  -97.00  92.00 139.00   86
 10  ω   -118.00 -31.00   0.50    0.05    --  -46.26 -57.00  30.00  174
 11  ω   -162.00-130.00   0.50    0.12    --  -97.00 -92.00  27.00   64
 12  ω   -162.00-109.00   0.50    0.12    --  -97.00 -19.00 -90.00  106
 13  ω    -71.00 -46.00   0.50    0.12    --  -97.00  57.00 -30.00   50
 14  ω    -71.00 -25.00   0.50    0.12    --  -97.00  57.00 -90.00   92
 15  ω   -119.00 -24.00   0.50    0.12    --  -97.00  77.00 -30.00  190
 16  ω    -69.00 -42.00   0.50    0.12    --  -97.00  57.00-120.00   54
 17  ω    -71.00 -31.00   0.50    0.12    --  -97.00  57.00  90.00   80
 18  ω    -71.00 -25.00   0.50    0.12    --  -97.00  57.00 120.00   92
 19  ω    -64.00 -24.00   0.50    0.12    --  -97.00  57.00 150.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1178986000
_diffrn_orient_matrix_UB_12      -0.0206453000
_diffrn_orient_matrix_UB_13      -0.0254908000
_diffrn_orient_matrix_UB_21      -0.0402829000
_diffrn_orient_matrix_UB_22      -0.1860175000
_diffrn_orient_matrix_UB_23      -0.0377495000
_diffrn_orient_matrix_UB_31      -0.0636130000
_diffrn_orient_matrix_UB_32      0.0790019000
_diffrn_orient_matrix_UB_33      -0.0954636000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2055
_reflns_number_total             2464
_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 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (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         0.244
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2464
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.043
_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)+(0.0516P)²+0.7941P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1036
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C00L(H00L)
2.b Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N)
;
_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 0.92903(9) 0.71134(14) 0.31154(7) 0.0290(3) Uani 1 1 d . . . . .
F002 F 0.64683(11) 1.04063(14) 0.08237(7) 0.0326(3) Uani 1 1 d . . . . .
F003 F 0.88062(10) 0.97812(14) 0.18829(8) 0.0325(3) Uani 1 1 d . . . . .
F004 F 0.46419(10) 0.83848(16) 0.10165(7) 0.0331(3) Uani 1 1 d . . . . .
F005 F 0.51171(9) 0.57580(15) 0.22722(7) 0.0308(3) Uani 1 1 d . . . . .
F006 F 0.66544(12) 0.29099(15) 0.22854(8) 0.0377(3) Uani 1 1 d . . . . .
F007 F 0.86091(12) 0.30497(16) 0.28171(9) 0.0431(3) Uani 1 1 d . . . . .
O008 O 0.85813(12) 0.41316(17) 0.48156(8) 0.0284(3) Uani 1 1 d . . . . .
N009 N 0.74759(13) 0.49713(19) 0.33723(10) 0.0230(3) Uani 1 1 d . . . . .
C00A C 0.72206(16) 0.6359(2) 0.27149(11) 0.0219(4) Uani 1 1 d . . . . .
C00B C 0.80260(16) 0.5290(2) 0.43164(12) 0.0225(4) Uani 1 1 d . . . . .
C00C C 0.78512(16) 0.7085(2) 0.46507(11) 0.0227(4) Uani 1 1 d . . . . .
C00D C 0.60403(16) 0.6720(2) 0.21706(12) 0.0236(4) Uani 1 1 d . . . . .
C00E C 0.81413(16) 0.7414(2) 0.25997(11) 0.0227(4) Uani 1 1 d . . . . .
C00F C 0.67216(18) 0.9106(2) 0.14381(12) 0.0255(4) Uani 1 1 d . . . . .
C00G C 0.79024(17) 0.8786(2) 0.19726(12) 0.0252(4) Uani 1 1 d . . . . .
C00H C 0.57882(16) 0.8065(2) 0.15378(12) 0.0249(4) Uani 1 1 d . . . . .
C00I C 0.67112(18) 0.7882(2) 0.44221(12) 0.0269(4) Uani 1 1 d . . . . .
H00I H 0.602385 0.731468 0.401197 0.032 Uiso 1 1 calc R U . . .
C00J C 0.88573(18) 0.7924(3) 0.52519(13) 0.0292(4) Uani 1 1 d . . . . .
H00J H 0.963268 0.737550 0.541549 0.035 Uiso 1 1 calc R U . . .
C00K C 0.6587(2) 0.9506(3) 0.47962(13) 0.0336(5) Uani 1 1 d . . . . .
H00K H 0.580924 1.004506 0.464751 0.040 Uiso 1 1 calc R U . . .
C00L C 0.75839(19) 0.3230(3) 0.30622(13) 0.0314(4) Uani 1 1 d . . . . .
H00L H 0.757855 0.235302 0.354848 0.038 Uiso 1 1 calc R U . . .
C00M C 0.7588(2) 1.0347(3) 0.53853(14) 0.0368(5) Uani 1 1 d . . . . .
H00M H 0.749700 1.146460 0.563580 0.044 Uiso 1 1 calc R U . . .
C00N C 0.8722(2) 0.9561(3) 0.56103(14) 0.0364(5) Uani 1 1 d . . . . .
H00N H 0.940892 1.014495 0.601112 0.044 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 C00E 1.339(2) . ?
F002 C00F 1.331(2) . ?
F003 C00G 1.332(2) . ?
F004 C00H 1.341(2) . ?
F005 C00D 1.343(2) . ?
F006 C00L 1.355(2) . ?
F007 C00L 1.359(2) . ?
O008 C00B 1.210(2) . ?
N009 C00A 1.423(2) . ?
N009 C00B 1.408(2) . ?
N009 C00L 1.423(2) . ?
C00A C00D 1.389(3) . ?
C00A C00E 1.388(3) . ?
C00B C00C 1.491(2) . ?
C00C C00I 1.395(3) . ?
C00C C00J 1.394(3) . ?
C00D C00H 1.375(3) . ?
C00E C00G 1.385(3) . ?
C00F C00G 1.380(3) . ?
C00F C00H 1.386(3) . ?
C00I H00I 0.9500 . ?
C00I C00K 1.385(3) . ?
C00J H00J 0.9500 . ?
C00J C00N 1.387(3) . ?
C00K H00K 0.9500 . ?
C00K C00M 1.384(3) . ?
C00L H00L 1.0000 . ?
C00M H00M 0.9500 . ?
C00M C00N 1.385(3) . ?
C00N H00N 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
C00A N009 C00L 118.14(14) . . ?
C00B N009 C00A 121.85(14) . . ?
C00B N009 C00L 116.33(14) . . ?
C00D C00A N009 121.30(16) . . ?
C00E C00A N009 121.21(16) . . ?
C00E C00A C00D 117.48(16) . . ?
O008 C00B N009 120.39(16) . . ?
O008 C00B C00C 123.28(16) . . ?
N009 C00B C00C 116.31(15) . . ?
C00I C00C C00B 121.96(16) . . ?
C00J C00C C00B 117.97(16) . . ?
C00J C00C C00I 119.97(17) . . ?
F005 C00D C00A 119.57(16) . . ?
F005 C00D C00H 118.88(16) . . ?
C00H C00D C00A 121.54(17) . . ?
F001 C00E C00A 119.25(16) . . ?
F001 C00E C00G 118.99(16) . . ?
C00G C00E C00A 121.76(16) . . ?
F002 C00F C00G 120.64(17) . . ?
F002 C00F C00H 119.51(16) . . ?
C00G C00F C00H 119.86(16) . . ?
F003 C00G C00E 120.26(17) . . ?
F003 C00G C00F 120.33(16) . . ?
C00F C00G C00E 119.42(17) . . ?
F004 C00H C00D 120.50(17) . . ?
F004 C00H C00F 119.55(16) . . ?
C00D C00H C00F 119.95(17) . . ?
C00C C00I H00I 120.2 . . ?
C00K C00I C00C 119.63(19) . . ?
C00K C00I H00I 120.2 . . ?
C00C C00J H00J 120.1 . . ?
C00N C00J C00C 119.75(19) . . ?
C00N C00J H00J 120.1 . . ?
C00I C00K H00K 119.8 . . ?
C00M C00K C00I 120.39(19) . . ?
C00M C00K H00K 119.8 . . ?
F006 C00L F007 105.27(15) . . ?
F006 C00L N009 109.32(16) . . ?
F006 C00L H00L 110.3 . . ?
F007 C00L N009 111.14(16) . . ?
F007 C00L H00L 110.3 . . ?
N009 C00L H00L 110.3 . . ?
C00K C00M H00M 120.0 . . ?
C00K C00M C00N 120.07(18) . . ?
C00N C00M H00M 120.0 . . ?
C00J C00N H00N 119.9 . . ?
C00M C00N C00J 120.17(19) . . ?
C00M C00N H00N 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F001 C00E C00G F003 0.4(2) . . . . ?
F001 C00E C00G C00F 179.99(15) . . . . ?
F002 C00F C00G F003 0.3(2) . . . . ?
F002 C00F C00G C00E -179.35(15) . . . . ?
F002 C00F C00H F004 -0.2(2) . . . . ?
F002 C00F C00H C00D -179.97(15) . . . . ?
F005 C00D C00H F004 -1.5(2) . . . . ?
F005 C00D C00H C00F 178.26(15) . . . . ?
O008 C00B C00C C00I -130.31(19) . . . . ?
O008 C00B C00C C00J 45.9(2) . . . . ?
N009 C00A C00D F005 0.8(2) . . . . ?
N009 C00A C00D C00H 179.66(15) . . . . ?
N009 C00A C00E F001 0.3(2) . . . . ?
N009 C00A C00E C00G -178.97(15) . . . . ?
N009 C00B C00C C00I 48.0(2) . . . . ?
N009 C00B C00C C00J -135.75(17) . . . . ?
C00A N009 C00B O008 -156.12(16) . . . . ?
C00A N009 C00B C00C 25.5(2) . . . . ?
C00A N009 C00L F006 -46.0(2) . . . . ?
C00A N009 C00L F007 69.8(2) . . . . ?
C00A C00D C00H F004 179.68(15) . . . . ?
C00A C00D C00H C00F -0.6(3) . . . . ?
C00A C00E C00G F003 179.60(15) . . . . ?
C00A C00E C00G C00F -0.8(3) . . . . ?
C00B N009 C00A C00D -119.24(19) . . . . ?
C00B N009 C00A C00E 60.1(2) . . . . ?
C00B N009 C00L F006 155.19(15) . . . . ?
C00B N009 C00L F007 -89.03(19) . . . . ?
C00B C00C C00I C00K 176.06(16) . . . . ?
C00B C00C C00J C00N -177.18(17) . . . . ?
C00C C00I C00K C00M 0.8(3) . . . . ?
C00C C00J C00N C00M 1.2(3) . . . . ?
C00D C00A C00E F001 179.63(14) . . . . ?
C00D C00A C00E C00G 0.4(3) . . . . ?
C00E C00A C00D F005 -178.56(15) . . . . ?
C00E C00A C00D C00H 0.3(3) . . . . ?
C00G C00F C00H F004 179.93(15) . . . . ?
C00G C00F C00H C00D 0.2(3) . . . . ?
C00H C00F C00G F003 -179.91(15) . . . . ?
C00H C00F C00G C00E 0.5(3) . . . . ?
C00I C00C C00J C00N -0.9(3) . . . . ?
C00I C00K C00M C00N -0.5(3) . . . . ?
C00J C00C C00I C00K -0.1(3) . . . . ?
C00K C00M C00N C00J -0.5(3) . . . . ?
C00L N009 C00A C00D 83.2(2) . . . . ?
C00L N009 C00A C00E -97.5(2) . . . . ?
C00L N009 C00B O008 1.8(2) . . . . ?
C00L N009 C00B C00C -176.56(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.437
_oxdiff_exptl_absorpt_empirical_full_min 0.777
####################################################################### 
# 
# 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_ai808-241120-4ry15a-ca_auto
_database_code_depnum_ccdc_archive 'CCDC 2427411'
loop_
_audit_author_name
_audit_author_address
'Ai Ito'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2024-12-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        
N-Difluoromethyl-(1-naphthalenylmethyl)benzamide
_chemical_formula_moiety         'C19 H15 F2 N O'
_chemical_formula_sum            'C19 H15 F2 N O'
_chemical_formula_weight         311.32
_chemical_melting_point          361.5-362.5
_chemical_oxdiff_formula         C19H15F2NO
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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.22942(11)
_cell_length_b                   10.17453(12)
_cell_length_c                   31.5753(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2965.08(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7784
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      76.5090
_cell_measurement_theta_min      2.7900
_shelx_estimated_absorpt_T_max   0.902
_shelx_estimated_absorpt_T_min   0.831
_exptl_absorpt_coefficient_mu    0.861
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77063
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.130a (Rigaku Oxford Diffraction, 2024)
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    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.122
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            10968
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.714
_diffrn_reflns_theta_min         2.799
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_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     42.00 102.00   0.50    0.05    --   46.70 179.00 120.00  120
  2  ω     95.00 163.00   0.50    0.19    --  108.36  57.00 120.00  136
  3  ω     -5.00  21.00   0.50    0.05    --   46.70 -19.00  60.00   52
  4  ω     39.00  91.00   0.50    0.19    --  108.36 -77.00-120.00  104
  5  ω     37.00 102.00   0.50    0.19    --  108.36 -78.00-163.00  130
  6  ω    -71.00   8.00   0.50    0.05    --  -46.70  80.00-151.00  158
  7  ω    -71.00 -24.00   0.50    0.19    --  -97.00  57.00-180.00   94
  8  ω   -168.00 -85.00   0.50    0.19    --  -97.00 -64.00 -44.00  166
  9  ω   -157.00-109.00   0.50    0.19    --  -97.00 -80.00  85.00   96
 10  ω    -50.00 -25.00   0.50    0.19    --  -97.00  57.00  90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-Custom'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1201297000
_diffrn_orient_matrix_UB_12      0.0236576000
_diffrn_orient_matrix_UB_13      0.0330096000
_diffrn_orient_matrix_UB_21      0.0777988000
_diffrn_orient_matrix_UB_22      0.1258025000
_diffrn_orient_matrix_UB_23      0.0148211000
_diffrn_orient_matrix_UB_31      -0.0860374000
_diffrn_orient_matrix_UB_32      0.0808223000
_diffrn_orient_matrix_UB_33      -0.0327095000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2692
_reflns_number_total             2978
_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 1.171.43.130a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.130a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.130a (Rigaku OD, 2024)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.00116(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2978
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.050
_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)+(0.0454P)²+1.0097P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0914
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C19(H19), C5(H5), C9(H9), C10(H10), C22(H22), C8(H8), C20(H20),
 C4(H4), C21(H21), C3(H3), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F14 F 0.05214(8) 0.69485(7) 0.08354(2) 0.02723(19) Uani 1 1 d . . . . .
F15 F -0.03931(8) 0.52062(8) 0.05548(2) 0.02845(19) Uani 1 1 d . . . . .
O17 O 0.18399(9) 0.37048(9) 0.16808(3) 0.0256(2) Uani 1 1 d . . . . .
N12 N 0.11317(10) 0.49281(9) 0.11146(3) 0.0188(2) Uani 1 1 d . . . . .
C6 C 0.64823(12) 0.73613(13) 0.09267(4) 0.0266(3) Uani 1 1 d . . . . .
H6 H 0.711899 0.797143 0.079545 0.032 Uiso 1 1 calc R U . . .
C16 C 0.10807(12) 0.45808(11) 0.15379(4) 0.0193(2) Uani 1 1 d . . . . .
C19 C 0.02877(13) 0.67335(12) 0.18535(4) 0.0222(3) Uani 1 1 d . . . . .
H19 H 0.092042 0.718245 0.166537 0.027 Uiso 1 1 calc R U . . .
C5 C 0.66550(13) 0.70713(14) 0.13461(4) 0.0301(3) Uani 1 1 d . . . . .
H5 H 0.739981 0.748617 0.150497 0.036 Uiso 1 1 calc R U . . .
C2 C 0.44075(12) 0.58606(12) 0.08843(3) 0.0198(2) Uani 1 1 d . . . . .
C9 C 0.40986(13) 0.64900(12) 0.00207(4) 0.0239(3) Uani 1 1 d . . . . .
H9 H 0.398910 0.668931 -0.027153 0.029 Uiso 1 1 calc R U . . .
C10 C 0.31366(12) 0.56042(12) 0.02179(4) 0.0217(3) Uani 1 1 d . . . . .
H10 H 0.238217 0.521671 0.005574 0.026 Uiso 1 1 calc R U . . .
C22 C -0.15829(13) 0.54165(13) 0.24028(4) 0.0248(3) Uani 1 1 d . . . . .
H22 H -0.222564 0.496987 0.258858 0.030 Uiso 1 1 calc R U . . .
C7 C 0.53677(12) 0.67662(12) 0.06840(4) 0.0215(3) Uani 1 1 d . . . . .
C18 C 0.01293(12) 0.53722(11) 0.18267(3) 0.0192(2) Uani 1 1 d . . . . .
C13 C 0.00281(12) 0.57149(11) 0.09322(3) 0.0201(2) Uani 1 1 d . . . . .
H13 H -0.081927 0.577360 0.112866 0.024 Uiso 1 1 calc R U . . .
C8 C 0.51837(13) 0.70605(12) 0.02476(4) 0.0237(3) Uani 1 1 d . . . . .
H8 H 0.582341 0.766066 0.011286 0.028 Uiso 1 1 calc R U . . .
C1 C 0.32658(12) 0.52886(11) 0.06398(3) 0.0192(2) Uani 1 1 d . . . . .
C11 C 0.22202(12) 0.43129(12) 0.08322(4) 0.0211(2) Uani 1 1 d . . . . .
H11A H 0.170993 0.384452 0.060140 0.025 Uiso 1 1 calc R U . . .
H11B H 0.277622 0.365354 0.099579 0.025 Uiso 1 1 calc R U . . .
C20 C -0.04868(13) 0.74273(13) 0.21573(4) 0.0257(3) Uani 1 1 d . . . . .
H20 H -0.037630 0.835336 0.217800 0.031 Uiso 1 1 calc R U . . .
C4 C 0.57276(14) 0.61564(14) 0.15428(4) 0.0289(3) Uani 1 1 d . . . . .
H4 H 0.586241 0.594546 0.183325 0.035 Uiso 1 1 calc R U . . .
C21 C -0.14225(14) 0.67768(13) 0.24314(4) 0.0262(3) Uani 1 1 d . . . . .
H21 H -0.195149 0.725772 0.263778 0.031 Uiso 1 1 calc R U . . .
C3 C 0.46348(13) 0.55688(13) 0.13195(4) 0.0243(3) Uani 1 1 d . . . . .
H3 H 0.401811 0.495607 0.145754 0.029 Uiso 1 1 calc R U . . .
C23 C -0.08024(13) 0.47169(12) 0.21026(3) 0.0214(2) Uani 1 1 d . . . . .
H23 H -0.090307 0.378929 0.208495 0.026 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
F14 C13 1.3698(14) . ?
F15 C13 1.3562(13) . ?
O17 C16 1.2202(14) . ?
N12 C16 1.3833(14) . ?
N12 C13 1.4177(15) . ?
N12 C11 1.4819(14) . ?
C6 H6 0.9500 . ?
C6 C5 1.3660(19) . ?
C6 C7 1.4184(17) . ?
C16 C18 1.5003(16) . ?
C19 H19 0.9500 . ?
C19 C18 1.3954(17) . ?
C19 C20 1.3892(17) . ?
C5 H5 0.9500 . ?
C5 C4 1.409(2) . ?
C2 C7 1.4263(17) . ?
C2 C1 1.4301(16) . ?
C2 C3 1.4215(16) . ?
C9 H9 0.9500 . ?
C9 C10 1.4101(17) . ?
C9 C8 1.3613(18) . ?
C10 H10 0.9500 . ?
C10 C1 1.3754(15) . ?
C22 H22 0.9500 . ?
C22 C21 1.3949(19) . ?
C22 C23 1.3872(17) . ?
C7 C8 1.4204(17) . ?
C18 C23 1.3938(16) . ?
C13 H13 1.0000 . ?
C8 H8 0.9500 . ?
C1 C11 1.5120(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C20 H20 0.9500 . ?
C20 C21 1.3902(18) . ?
C4 H4 0.9500 . ?
C4 C3 1.3681(18) . ?
C21 H21 0.9500 . ?
C3 H3 0.9500 . ?
C23 H23 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
C16 N12 C13 120.82(9) . . ?
C16 N12 C11 119.77(9) . . ?
C13 N12 C11 118.76(9) . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.07(12) . . ?
C7 C6 H6 119.5 . . ?
O17 C16 N12 121.62(10) . . ?
O17 C16 C18 120.23(10) . . ?
N12 C16 C18 118.04(10) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C20 C19 C18 119.49(11) . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 119.95(11) . . ?
C4 C5 H5 120.0 . . ?
C7 C2 C1 118.77(10) . . ?
C3 C2 C7 118.16(11) . . ?
C3 C2 C1 123.07(11) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.21(11) . . ?
C9 C10 H10 119.3 . . ?
C1 C10 C9 121.49(11) . . ?
C1 C10 H10 119.3 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C23 C22 C21 119.88(11) . . ?
C6 C7 C2 119.13(11) . . ?
C6 C7 C8 121.39(11) . . ?
C8 C7 C2 119.48(11) . . ?
C19 C18 C16 120.54(10) . . ?
C23 C18 C16 118.96(10) . . ?
C23 C18 C19 120.11(11) . . ?
F14 C13 N12 111.67(9) . . ?
F14 C13 H13 110.1 . . ?
F15 C13 F14 104.41(9) . . ?
F15 C13 N12 110.33(9) . . ?
F15 C13 H13 110.1 . . ?
N12 C13 H13 110.1 . . ?
C9 C8 C7 120.58(11) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C2 C1 C11 121.36(10) . . ?
C10 C1 C2 119.46(11) . . ?
C10 C1 C11 119.16(10) . . ?
N12 C11 C1 113.40(9) . . ?
N12 C11 H11A 108.9 . . ?
N12 C11 H11B 108.9 . . ?
C1 C11 H11A 108.9 . . ?
C1 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.51(12) . . ?
C21 C20 H20 119.7 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.62(11) . . ?
C3 C4 H4 119.7 . . ?
C22 C21 H21 120.1 . . ?
C20 C21 C22 119.87(11) . . ?
C20 C21 H21 120.1 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.05(12) . . ?
C4 C3 H3 119.5 . . ?
C22 C23 C18 120.13(11) . . ?
C22 C23 H23 119.9 . . ?
C18 C23 H23 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O17 C16 C18 C19 121.31(12) . . . . ?
O17 C16 C18 C23 -51.56(15) . . . . ?
N12 C16 C18 C19 -54.87(15) . . . . ?
N12 C16 C18 C23 132.27(11) . . . . ?
C6 C5 C4 C3 -1.14(19) . . . . ?
C6 C7 C8 C9 -179.32(11) . . . . ?
C16 N12 C13 F14 109.92(11) . . . . ?
C16 N12 C13 F15 -134.44(10) . . . . ?
C16 N12 C11 C1 -118.54(11) . . . . ?
C16 C18 C23 C22 173.34(10) . . . . ?
C19 C18 C23 C22 0.44(17) . . . . ?
C19 C20 C21 C22 0.23(18) . . . . ?
C5 C6 C7 C2 0.59(18) . . . . ?
C5 C6 C7 C8 -179.85(12) . . . . ?
C5 C4 C3 C2 0.18(19) . . . . ?
C2 C7 C8 C9 0.24(17) . . . . ?
C2 C1 C11 N12 74.92(13) . . . . ?
C9 C10 C1 C2 -0.55(17) . . . . ?
C9 C10 C1 C11 -178.85(10) . . . . ?
C10 C9 C8 C7 0.42(18) . . . . ?
C10 C1 C11 N12 -106.81(12) . . . . ?
C7 C6 C5 C4 0.74(19) . . . . ?
C7 C2 C1 C10 1.18(16) . . . . ?
C7 C2 C1 C11 179.44(10) . . . . ?
C7 C2 C3 C4 1.13(17) . . . . ?
C18 C19 C20 C21 -0.48(17) . . . . ?
C13 N12 C16 O17 165.06(11) . . . . ?
C13 N12 C16 C18 -18.83(15) . . . . ?
C13 N12 C11 C1 70.65(13) . . . . ?
C8 C9 C10 C1 -0.26(18) . . . . ?
C1 C2 C7 C6 178.55(10) . . . . ?
C1 C2 C7 C8 -1.02(16) . . . . ?
C1 C2 C3 C4 -178.92(11) . . . . ?
C11 N12 C16 O17 -5.55(16) . . . . ?
C11 N12 C16 C18 170.56(9) . . . . ?
C11 N12 C13 F14 -79.37(12) . . . . ?
C11 N12 C13 F15 36.27(13) . . . . ?
C20 C19 C18 C16 -172.64(10) . . . . ?
C20 C19 C18 C23 0.14(17) . . . . ?
C21 C22 C23 C18 -0.69(17) . . . . ?
C3 C2 C7 C6 -1.50(16) . . . . ?
C3 C2 C7 C8 178.93(11) . . . . ?
C3 C2 C1 C10 -178.77(11) . . . . ?
C3 C2 C1 C11 -0.51(17) . . . . ?
C23 C22 C21 C20 0.36(18) . . . . ?

_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 1.378
_oxdiff_exptl_absorpt_empirical_full_min 0.669
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2-nhex'
####################################################################### 
# 
# 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_ai812-241121-4ry16c-ca3_auto
_database_code_depnum_ccdc_archive 'CCDC 2427412'
loop_
_audit_author_name
_audit_author_address
'Ai Ito'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2024-12-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        
'N-Acetyl-N-difluoromethyl-L-phenylalanine methyl ester'
_chemical_formula_moiety         'C13 H15 F2 N O3'
_chemical_formula_sum            'C13 H15 F2 N O3'
_chemical_formula_weight         271.26
_chemical_melting_point          330.5-331.5
_chemical_oxdiff_formula         C13H15F2NO3
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                   10.0791(3)
_cell_length_b                   12.0372(3)
_cell_length_c                   10.7937(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.258(3)
_cell_angle_gamma                90
_cell_volume                     1309.53(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9060
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      75.6940
_cell_measurement_theta_min      5.4980
_shelx_estimated_absorpt_T_max   0.925
_shelx_estimated_absorpt_T_min   0.861
_exptl_absorpt_coefficient_mu    0.996
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76758
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.130a (Rigaku Oxford Diffraction, 2024)
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    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14509
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.598
_diffrn_reflns_theta_min         5.505
_diffrn_ambient_temperature      93.15
_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 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     67.00 111.00   0.50    0.21    --  108.36-125.00-180.00   88
  2  ω     81.00 106.00   0.50    0.21    --  108.36 -99.00-120.00   50
  3  ω     69.00 102.00   0.50    0.21    --  108.36-125.00 -30.00   66
  4  ω     42.00 111.00   0.50    0.21    --  108.36-125.00   0.00  138
  5  ω     64.00 103.00   0.50    0.21    --  108.36 -99.00  60.00   78
  6  ω     81.00 106.00   0.50    0.21    --  108.36 -99.00  90.00   50
  7  ω     64.00  91.00   0.50    0.21    --  108.36 -99.00  30.00   54
  8  ω     45.00 101.00   0.50    0.21    --  108.36 -99.00   0.00  112
  9  ω     47.00  72.00   0.50    0.21    --  108.36 -99.00-120.00   50
 10  ω      6.00  41.00   0.50    0.05    --   46.70 -99.00-180.00   70
 11  ω    -25.00  52.00   0.50    0.05    --   46.70 -50.00 143.00  154
 12  ω    -24.00  20.00   0.50    0.05    --   46.70 -19.00   0.00   88
 13  ω     49.00  79.00   0.50    0.05    --   46.70 -99.00-180.00   60
 14  ω    109.00 171.00   0.50    0.21    --  108.36  37.00  60.00  124
 15  ω     96.00 164.00   0.50    0.21    --  108.36  50.00 -69.00  136
 16  ω     70.00 112.00   0.50    0.05    --   46.70  57.00 -30.00   84
 17  ω     39.00  65.00   0.50    0.05    --   46.70  57.00 -30.00   52
 18  ω     37.00 119.00   0.50    0.05    --   46.70  50.00 -69.00  164
 19  ω    -18.00  25.00   0.50    0.05    --  -46.70  50.00 -69.00   86
 20  ω    -59.00 -24.00   0.50    0.21    --  -97.00  57.00  30.00   70
 21  ω    -70.00 -26.00   0.50    0.21    --  -97.00  57.00 120.00   88
 22  ω    -70.00 -43.00   0.50    0.21    --  -97.00  57.00 150.00   54
 23  ω    -70.00 -44.00   0.50    0.21    --  -97.00  77.00 150.00   52
 24  ω   -105.00 -79.00   0.50    0.21    --  -97.00  77.00 150.00   52
 25  ω    -57.00 -32.00   0.50    0.05    --  -46.70  50.00 -69.00   50
 26  ω    -59.00 -28.00   0.50    0.21    --  -97.00  50.00 -69.00   62
 27  ω   -108.00 -79.00   0.50    0.21    --  -97.00 109.00-104.77   58
 28  ω    -56.00 -27.00   0.50    0.21    --  -97.00 125.00-150.00   58
 29  ω    -67.00 -40.00   0.50    0.21    --  -97.00 109.00-104.77   54
 30  ω   -105.00 -74.00   0.50    0.21    --  -97.00 125.00 150.00   62
 31  ω    -71.00 -28.00   0.50    0.21    --  -97.00 125.00 150.00   86
 32  ω   -169.00 -89.00   0.50    0.21    --  -97.00 -50.00 143.00  160
 33  ω   -115.00 -89.00   0.50    0.05    --  -46.70 -50.00 143.00   52
 34  ω   -159.00-124.00   0.50    0.21    --  -97.00 -57.00-120.00   70
 35  ω   -120.00 -94.00   0.50    0.21    --  -97.00 -57.00-120.00   52
 36  ω   -153.00 -91.00   0.50    0.21    --  -97.00 -99.00-150.00  124
 37  ω   -167.00 -94.00   0.50    0.21    --  -97.00 -99.00 -90.00  146
 38  ω   -165.00 -87.00   0.50    0.21    --  -97.00-125.00  60.00  156
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0473608000
_diffrn_orient_matrix_UB_12      0.0627444000
_diffrn_orient_matrix_UB_13      0.1164900000
_diffrn_orient_matrix_UB_21      0.1190099000
_diffrn_orient_matrix_UB_22      0.0466244000
_diffrn_orient_matrix_UB_23      -0.0728001000
_diffrn_orient_matrix_UB_31      -0.0833997000
_diffrn_orient_matrix_UB_32      0.1012864000
_diffrn_orient_matrix_UB_33      -0.0389288000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2359
_reflns_number_total             2672
_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 1.171.43.130a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.130a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.130a (Rigaku OD, 2024)'
_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         0.174
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2672
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.054
_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)+(0.0400P)²+0.3687P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0878
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C5(H5), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C15(H15A,H15B,H15C)
;
_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
F12 F 0.56565(7) 0.40315(6) 0.56511(7) 0.03305(19) Uani 1 1 d . . . . .
F11 F 0.76166(8) 0.33986(6) 0.52765(7) 0.0360(2) Uani 1 1 d . . . . .
O17 O 0.88711(8) 0.37949(7) 0.92861(8) 0.0281(2) Uani 1 1 d . . . . .
O19 O 0.97726(9) 0.40358(7) 0.74061(8) 0.0295(2) Uani 1 1 d . . . . .
O14 O 0.85574(10) 0.63622(7) 0.73465(8) 0.0326(2) Uani 1 1 d . . . . .
N9 N 0.74240(10) 0.49342(8) 0.65069(8) 0.0231(2) Uani 1 1 d . . . . .
C13 C 0.80726(12) 0.59402(10) 0.64225(11) 0.0262(3) Uani 1 1 d . . . . .
C8 C 0.74111(12) 0.43336(10) 0.76948(10) 0.0231(2) Uani 1 1 d . . . . .
H8 H 0.695749 0.360815 0.753666 0.028 Uiso 1 1 calc R U . . .
C10 C 0.69320(12) 0.43607(10) 0.54576(11) 0.0264(3) Uani 1 1 d . . . . .
H10 H 0.698533 0.484279 0.470495 0.032 Uiso 1 1 calc R U . . .
C16 C 0.88323(12) 0.40596(9) 0.80848(10) 0.0235(2) Uani 1 1 d . . . . .
C6 C 0.42793(12) 0.42836(10) 0.82430(11) 0.0265(3) Uani 1 1 d . . . . .
H6 H 0.455959 0.353894 0.837296 0.032 Uiso 1 1 calc R U . . .
C1 C 0.51939(12) 0.51467(10) 0.83524(10) 0.0229(2) Uani 1 1 d . . . . .
C7 C 0.66150(12) 0.49241(10) 0.87133(10) 0.0259(3) Uani 1 1 d . . . . .
H7A H 0.662932 0.446038 0.947080 0.031 Uiso 1 1 calc R U . . .
H7B H 0.705273 0.563852 0.891355 0.031 Uiso 1 1 calc R U . . .
C2 C 0.47588(13) 0.62266(10) 0.81482(11) 0.0270(3) Uani 1 1 d . . . . .
H2 H 0.536893 0.682546 0.821407 0.032 Uiso 1 1 calc R U . . .
C5 C 0.29633(13) 0.45004(11) 0.79461(11) 0.0292(3) Uani 1 1 d . . . . .
H5 H 0.235075 0.390357 0.787659 0.035 Uiso 1 1 calc R U . . .
C18 C 1.01586(13) 0.34778(12) 0.97707(12) 0.0326(3) Uani 1 1 d . . . . .
H18A H 1.048731 0.282980 0.931615 0.049 Uiso 1 1 calc R U . . .
H18B H 1.007910 0.329214 1.065127 0.049 Uiso 1 1 calc R U . . .
H18C H 1.078078 0.409695 0.967269 0.049 Uiso 1 1 calc R U . . .
C3 C 0.34410(14) 0.64409(11) 0.78487(11) 0.0308(3) Uani 1 1 d . . . . .
H3 H 0.315861 0.718373 0.771033 0.037 Uiso 1 1 calc R U . . .
C4 C 0.25367(13) 0.55790(11) 0.77506(11) 0.0300(3) Uani 1 1 d . . . . .
H4 H 0.163466 0.572643 0.755149 0.036 Uiso 1 1 calc R U . . .
C15 C 0.81550(15) 0.64933(11) 0.51716(12) 0.0346(3) Uani 1 1 d . . . . .
H15A H 0.857720 0.722249 0.526056 0.052 Uiso 1 1 calc R U . . .
H15B H 0.725955 0.658628 0.482963 0.052 Uiso 1 1 calc R U . . .
H15C H 0.868185 0.603046 0.461174 0.052 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
F12 C10 1.3623(15) . ?
F11 C10 1.3627(14) . ?
O17 C16 1.3356(14) . ?
O17 C18 1.4482(15) . ?
O19 C16 1.2009(15) . ?
O14 C13 1.2194(15) . ?
N9 C13 1.3794(16) . ?
N9 C8 1.4721(14) . ?
N9 C10 1.4142(15) . ?
C13 C15 1.5080(17) . ?
C8 H8 1.0000 . ?
C8 C16 1.5273(16) . ?
C8 C7 1.5380(16) . ?
C10 H10 1.0000 . ?
C6 H6 0.9500 . ?
C6 C1 1.3936(17) . ?
C6 C5 1.3879(18) . ?
C1 C7 1.5067(16) . ?
C1 C2 1.3892(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C2 H2 0.9500 . ?
C2 C3 1.3897(19) . ?
C5 H5 0.9500 . ?
C5 C4 1.3836(19) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C3 H3 0.9500 . ?
C3 C4 1.385(2) . ?
C4 H4 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C16 O17 C18 115.84(10) . . ?
C13 N9 C8 119.65(9) . . ?
C13 N9 C10 122.70(10) . . ?
C10 N9 C8 116.96(9) . . ?
O14 C13 N9 120.00(11) . . ?
O14 C13 C15 121.66(11) . . ?
N9 C13 C15 118.34(10) . . ?
N9 C8 H8 106.6 . . ?
N9 C8 C16 109.52(9) . . ?
N9 C8 C7 113.72(9) . . ?
C16 C8 H8 106.6 . . ?
C16 C8 C7 113.23(9) . . ?
C7 C8 H8 106.6 . . ?
F12 C10 F11 104.69(9) . . ?
F12 C10 N9 110.30(9) . . ?
F12 C10 H10 110.3 . . ?
F11 C10 N9 110.72(10) . . ?
F11 C10 H10 110.3 . . ?
N9 C10 H10 110.3 . . ?
O17 C16 C8 110.02(10) . . ?
O19 C16 O17 124.53(11) . . ?
O19 C16 C8 125.37(10) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C1 120.69(11) . . ?
C6 C1 C7 121.13(11) . . ?
C2 C1 C6 118.42(11) . . ?
C2 C1 C7 120.44(11) . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C1 C7 C8 113.31(9) . . ?
C1 C7 H7A 108.9 . . ?
C1 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.75(11) . . ?
C3 C2 H2 119.6 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.51(12) . . ?
C4 C5 H5 119.7 . . ?
O17 C18 H18A 109.5 . . ?
O17 C18 H18B 109.5 . . ?
O17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.45(12) . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.17(12) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
N9 C8 C16 O17 163.26(9) . . . . ?
N9 C8 C16 O19 -19.79(16) . . . . ?
N9 C8 C7 C1 56.86(13) . . . . ?
C13 N9 C8 C16 -60.62(13) . . . . ?
C13 N9 C8 C7 67.18(14) . . . . ?
C13 N9 C10 F12 -131.79(11) . . . . ?
C13 N9 C10 F11 112.80(12) . . . . ?
C8 N9 C13 O14 -4.75(17) . . . . ?
C8 N9 C13 C15 175.52(11) . . . . ?
C8 N9 C10 F12 57.78(13) . . . . ?
C8 N9 C10 F11 -57.63(13) . . . . ?
C10 N9 C13 O14 -174.94(11) . . . . ?
C10 N9 C13 C15 5.33(17) . . . . ?
C10 N9 C8 C16 110.11(11) . . . . ?
C10 N9 C8 C7 -122.09(11) . . . . ?
C16 C8 C7 C1 -177.28(10) . . . . ?
C6 C1 C7 C8 70.48(14) . . . . ?
C6 C1 C2 C3 0.35(17) . . . . ?
C6 C5 C4 C3 0.32(18) . . . . ?
C1 C6 C5 C4 0.15(18) . . . . ?
C1 C2 C3 C4 0.11(18) . . . . ?
C7 C8 C16 O17 35.18(13) . . . . ?
C7 C8 C16 O19 -147.86(11) . . . . ?
C7 C1 C2 C3 -178.20(11) . . . . ?
C2 C1 C7 C8 -111.01(12) . . . . ?
C2 C3 C4 C5 -0.44(18) . . . . ?
C5 C6 C1 C7 178.07(11) . . . . ?
C5 C6 C1 C2 -0.47(17) . . . . ?
C18 O17 C16 O19 0.95(17) . . . . ?
C18 O17 C16 C8 177.94(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.471
_oxdiff_exptl_absorpt_empirical_full_min 0.747
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2-nhex'
####################################################################### 
# 
# 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_ai659-230425-sat-137-1-acoet-hex-ca_auto
_database_code_depnum_ccdc_archive 'CCDC 2427408'
loop_
_audit_author_name
_audit_author_address
'Ai Ito'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2023-05-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        N-Difluoromethyl-p-nitro-benzanilide
_chemical_formula_moiety         'C14 H10 F2 N2 O3'
_chemical_formula_sum            'C14 H10 F2 N2 O3'
_chemical_formula_weight         292.24
_chemical_melting_point          364-365
_chemical_oxdiff_formula         C14H10F2N2O3
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                   10.36230(10)
_cell_length_b                   24.6801(3)
_cell_length_c                   10.66670(10)
_cell_angle_alpha                90
_cell_angle_beta                 110.6000(10)
_cell_angle_gamma                90
_cell_volume                     2553.50(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12216
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      76.6620
_cell_measurement_theta_min      3.5740
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.853
_exptl_absorpt_coefficient_mu    1.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
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    1.520
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.064
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19618
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.149
_diffrn_reflns_theta_min         3.582
_diffrn_ambient_temperature      93.15
_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 0.946
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     42.00 103.00   0.50    0.42    --  108.36-121.00  82.00  122
  2  ω     46.00  71.00   0.50    0.10    --   46.95-151.00 -78.00   50
  3  ω     83.00 108.00   0.50    0.42    --  108.36-151.00 -78.00   50
  4  ω     40.00  93.00   0.50    0.42    --  108.36 -99.00  90.00  106
  5  ω     36.00  95.00   0.50    0.42    --  108.36 -77.00  90.00  118
  6  ω    -25.00   0.00   0.50    0.10    --   46.95 -19.00  60.00   50
  7  ω    -26.00  26.00   0.50    0.10    --   46.95 -19.00-120.00  104
  8  ω    -25.00  21.00   0.50    0.10    --   46.95 -19.00-180.00   92
  9  ω     66.00  91.00   0.50    0.10    --   46.95 151.00 -34.00   50
 10  ω     96.00 174.00   0.50    0.42    --  108.36  37.00-150.00  156
 11  ω     88.00 113.00   0.50    0.42    --  108.36 151.00 -34.00   50
 12  ω     96.00 165.00   0.50    0.42    --  108.36  37.00 150.00  138
 13  ω     86.00 128.00   0.50    0.42    --  108.36 121.00 164.00   84
 14  ω    -48.00  25.00   0.50    0.10    --  -46.95  37.00 -60.00  146
 15  ω    -75.00 -24.00   0.50    0.42    --  -97.00  77.00-180.00  102
 16  ω    -57.00 -32.00   0.50    0.42    --  -97.00  57.00-180.00   50
 17  ω    -70.00 -24.00   0.50    0.42    --  -97.00  57.00   0.00   92
 18  ω    -67.00 -24.00   0.50    0.42    --  -97.00  57.00  30.00   86
 19  ω    -97.00 -72.00   0.50    0.10    --  -46.95 151.00 -34.00   50
 20  ω    -89.00 -55.00   0.50    0.10    --  -46.95 121.00 164.00   68
 21  ω    -92.00 -67.00   0.50    0.42    --  -97.00 121.00 164.00   50
 22  ω   -123.00 -82.00   0.50    0.42    --  -97.00 141.00  78.89   82
 23  ω   -107.00 -82.00   0.50    0.42    --  -97.00 151.00 -34.00   50
 24  ω   -168.00-101.00   0.50    0.42    --  -97.00 -37.00 -30.00  134
 25  ω   -152.00-122.00   0.50    0.42    --  -97.00-121.00  82.00   60
 26  ω   -116.00 -65.00   0.50    0.10    --  -46.95-151.00 -78.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1094273000
_diffrn_orient_matrix_UB_12      -0.0342265000
_diffrn_orient_matrix_UB_13      -0.0313329000
_diffrn_orient_matrix_UB_21      0.0825188000
_diffrn_orient_matrix_UB_22      0.0517576000
_diffrn_orient_matrix_UB_23      -0.0012721000
_diffrn_orient_matrix_UB_31      0.0803662000
_diffrn_orient_matrix_UB_32      -0.0066400000
_diffrn_orient_matrix_UB_33      0.1510114000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4580
_reflns_number_total             5110
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.00073(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0300
_refine_ls_restrained_S_all      1.048
_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)+(0.0359P)²+0.7764P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0775
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C29(H29), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C26(H26), C27(H27), C21(H21), C3(H3), C2(H2), C24(H24), C23(H23),
 C6(H6), C38(H38), C41(H41), C17(H17), C42(H42), C20(H20), C39(H39), C40(H40),
 C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F9 F 0.39417(8) 0.47722(3) 0.19272(7) 0.02785(17) Uani 1 1 d . . . . .
F10 F 0.61399(8) 0.46684(3) 0.29171(8) 0.03262(19) Uani 1 1 d . . . . .
F30 F 0.99977(8) 0.59051(4) 0.11144(7) 0.0359(2) Uani 1 1 d . . . . .
F31 F 1.03800(8) 0.66908(3) 0.20739(8) 0.0358(2) Uani 1 1 d . . . . .
O33 O 1.16416(8) 0.61946(4) 0.49267(8) 0.02349(19) Uani 1 1 d . . . . .
O12 O 0.56447(9) 0.42585(3) 0.56337(8) 0.02387(19) Uani 1 1 d . . . . .
O15 O 0.30171(9) 0.23940(4) -0.13695(8) 0.0277(2) Uani 1 1 d . . . . .
O14 O 0.51662(9) 0.21886(4) -0.03878(9) 0.0263(2) Uani 1 1 d . . . . .
O36 O 0.33891(9) 0.56731(4) -0.00849(9) 0.0298(2) Uani 1 1 d . . . . .
O35 O 0.33170(9) 0.64095(4) 0.09897(10) 0.0322(2) Uani 1 1 d . . . . .
N7 N 0.46767(10) 0.40773(4) 0.34016(9) 0.0181(2) Uani 1 1 d . . . . .
N28 N 0.97484(9) 0.59870(4) 0.31453(9) 0.0181(2) Uani 1 1 d . . . . .
N13 N 0.41396(10) 0.24580(4) -0.04823(9) 0.0192(2) Uani 1 1 d . . . . .
N34 N 0.39441(10) 0.60335(4) 0.07106(10) 0.0207(2) Uani 1 1 d . . . . .
C4 C 0.42658(12) 0.28859(4) 0.05119(10) 0.0165(2) Uani 1 1 d . . . . .
C22 C 0.82648(11) 0.59954(5) 0.25398(11) 0.0165(2) Uani 1 1 d . . . . .
C5 C 0.55592(11) 0.29869(5) 0.14491(11) 0.0184(2) Uani 1 1 d . . . . .
H5 H 0.633998 0.278612 0.144513 0.022 Uiso 1 1 calc R U . . .
C16 C 0.48653(12) 0.33559(5) 0.50361(11) 0.0170(2) Uani 1 1 d . . . . .
C26 C 0.60969(12) 0.64172(5) 0.22870(11) 0.0174(2) Uani 1 1 d . . . . .
H26 H 0.557398 0.669141 0.251403 0.021 Uiso 1 1 calc R U . . .
C27 C 0.75232(12) 0.64056(5) 0.28717(11) 0.0177(2) Uani 1 1 d . . . . .
H27 H 0.799168 0.667723 0.349729 0.021 Uiso 1 1 calc R U . . .
C1 C 0.45269(12) 0.36744(4) 0.23737(11) 0.0164(2) Uani 1 1 d . . . . .
C37 C 0.98235(11) 0.58019(5) 0.54770(11) 0.0176(2) Uani 1 1 d . . . . .
C21 C 0.35528(12) 0.31271(5) 0.44993(11) 0.0187(2) Uani 1 1 d . . . . .
H21 H 0.281649 0.332820 0.388919 0.022 Uiso 1 1 calc R U . . .
C32 C 1.04725(11) 0.60161(5) 0.45242(11) 0.0178(2) Uani 1 1 d . . . . .
C11 C 0.51192(11) 0.39313(5) 0.47450(11) 0.0180(2) Uani 1 1 d . . . . .
C3 C 0.31005(12) 0.31749(5) 0.04575(11) 0.0180(2) Uani 1 1 d . . . . .
H3 H 0.223052 0.309971 -0.021016 0.022 Uiso 1 1 calc R U . . .
C2 C 0.32393(12) 0.35766(5) 0.14037(11) 0.0182(2) Uani 1 1 d . . . . .
H2 H 0.246176 0.378366 0.139049 0.022 Uiso 1 1 calc R U . . .
C25 C 0.54546(11) 0.60180(5) 0.13623(11) 0.0169(2) Uani 1 1 d . . . . .
C24 C 0.61795(12) 0.56104(5) 0.10092(11) 0.0182(2) Uani 1 1 d . . . . .
H24 H 0.571083 0.534544 0.036351 0.022 Uiso 1 1 calc R U . . .
C23 C 0.76019(12) 0.55962(5) 0.16155(11) 0.0180(2) Uani 1 1 d . . . . .
H23 H 0.811999 0.531652 0.140223 0.022 Uiso 1 1 calc R U . . .
C6 C 0.56865(12) 0.33884(5) 0.23940(11) 0.0183(2) Uani 1 1 d . . . . .
H6 H 0.656098 0.346718 0.305015 0.022 Uiso 1 1 calc R U . . .
C38 C 1.04134(12) 0.59760(5) 0.68041(12) 0.0208(2) Uani 1 1 d . . . . .
H38 H 1.112527 0.624030 0.703594 0.025 Uiso 1 1 calc R U . . .
C41 C 0.83283(12) 0.52048(5) 0.61320(12) 0.0224(2) Uani 1 1 d . . . . .
H41 H 0.761219 0.494232 0.590413 0.027 Uiso 1 1 calc R U . . .
C17 C 0.59421(12) 0.30619(5) 0.59338(11) 0.0206(2) Uani 1 1 d . . . . .
H17 H 0.683537 0.321741 0.630177 0.025 Uiso 1 1 calc R U . . .
C42 C 0.87788(12) 0.54121(5) 0.51485(11) 0.0195(2) Uani 1 1 d . . . . .
H42 H 0.837668 0.528898 0.425055 0.023 Uiso 1 1 calc R U . . .
C20 C 0.33265(13) 0.26054(5) 0.48591(12) 0.0229(2) Uani 1 1 d . . . . .
H20 H 0.243470 0.244850 0.449355 0.028 Uiso 1 1 calc R U . . .
C39 C 0.99649(13) 0.57648(5) 0.77840(12) 0.0234(3) Uani 1 1 d . . . . .
H39 H 1.037169 0.588345 0.868525 0.028 Uiso 1 1 calc R U . . .
C40 C 0.89206(13) 0.53797(5) 0.74482(12) 0.0235(3) Uani 1 1 d . . . . .
H40 H 0.861164 0.523592 0.811954 0.028 Uiso 1 1 calc R U . . .
C29 C 1.05186(12) 0.61482(5) 0.23277(12) 0.0234(3) Uani 1 1 d . . . . .
H29 H 1.151324 0.605189 0.277363 0.028 Uiso 1 1 calc R U . . .
C18 C 0.57047(13) 0.25403(5) 0.62888(12) 0.0236(3) Uani 1 1 d . . . . .
H18 H 0.643762 0.233863 0.690166 0.028 Uiso 1 1 calc R U . . .
C19 C 0.44018(14) 0.23125(5) 0.57525(12) 0.0248(3) Uani 1 1 d . . . . .
H19 H 0.424506 0.195505 0.599723 0.030 Uiso 1 1 calc R U . . .
C8 C 0.49103(13) 0.46240(5) 0.31071(12) 0.0227(3) Uani 1 1 d . . . . .
H8 H 0.488673 0.487044 0.384279 0.027 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
F9 C8 1.3552(14) . ?
F10 C8 1.3631(15) . ?
F30 C29 1.3545(14) . ?
F31 C29 1.3637(15) . ?
O33 C32 1.2166(14) . ?
O12 C11 1.2183(14) . ?
O15 N13 1.2243(13) . ?
O14 N13 1.2282(13) . ?
O36 N34 1.2242(13) . ?
O35 N34 1.2280(14) . ?
N7 C1 1.4475(14) . ?
N7 C11 1.3897(15) . ?
N7 C8 1.4251(15) . ?
N28 C22 1.4430(14) . ?
N28 C32 1.3982(15) . ?
N28 C29 1.4302(15) . ?
N13 C4 1.4695(14) . ?
N34 C25 1.4728(14) . ?
C4 C5 1.3838(15) . ?
C4 C3 1.3861(16) . ?
C22 C27 1.3899(16) . ?
C22 C23 1.3921(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3864(16) . ?
C16 C21 1.3959(16) . ?
C16 C11 1.4964(16) . ?
C16 C17 1.3917(16) . ?
C26 H26 0.9500 . ?
C26 C27 1.3877(16) . ?
C26 C25 1.3873(16) . ?
C27 H27 0.9500 . ?
C1 C2 1.3920(16) . ?
C1 C6 1.3871(16) . ?
C37 C32 1.4985(16) . ?
C37 C38 1.3976(16) . ?
C37 C42 1.3975(16) . ?
C21 H21 0.9500 . ?
C21 C20 1.3868(17) . ?
C3 H3 0.9500 . ?
C3 C2 1.3856(16) . ?
C2 H2 0.9500 . ?
C25 C24 1.3846(16) . ?
C24 H24 0.9500 . ?
C24 C23 1.3861(16) . ?
C23 H23 0.9500 . ?
C6 H6 0.9500 . ?
C38 H38 0.9500 . ?
C38 C39 1.3863(17) . ?
C41 H41 0.9500 . ?
C41 C42 1.3875(17) . ?
C41 C40 1.3884(18) . ?
C17 H17 0.9500 . ?
C17 C18 1.3881(18) . ?
C42 H42 0.9500 . ?
C20 H20 0.9500 . ?
C20 C19 1.3875(18) . ?
C39 H39 0.9500 . ?
C39 C40 1.3891(18) . ?
C40 H40 0.9500 . ?
C29 H29 1.0000 . ?
C18 H18 0.9500 . ?
C18 C19 1.3866(19) . ?
C19 H19 0.9500 . ?
C8 H8 1.0000 . ?

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
C11 N7 C1 120.75(9) . . ?
C11 N7 C8 116.93(9) . . ?
C8 N7 C1 117.69(9) . . ?
C32 N28 C22 124.26(9) . . ?
C32 N28 C29 114.78(9) . . ?
C29 N28 C22 117.28(9) . . ?
O15 N13 O14 123.61(10) . . ?
O15 N13 C4 118.01(10) . . ?
O14 N13 C4 118.37(9) . . ?
O36 N34 O35 123.88(10) . . ?
O36 N34 C25 118.05(10) . . ?
O35 N34 C25 118.06(10) . . ?
C5 C4 N13 117.93(10) . . ?
C5 C4 C3 123.07(10) . . ?
C3 C4 N13 118.99(10) . . ?
C27 C22 N28 119.60(10) . . ?
C27 C22 C23 121.10(10) . . ?
C23 C22 N28 119.29(10) . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.31(11) . . ?
C6 C5 H5 120.8 . . ?
C21 C16 C11 121.05(10) . . ?
C17 C16 C21 120.06(11) . . ?
C17 C16 C11 118.73(10) . . ?
C27 C26 H26 120.9 . . ?
C25 C26 H26 120.9 . . ?
C25 C26 C27 118.26(10) . . ?
C22 C27 H27 120.1 . . ?
C26 C27 C22 119.84(10) . . ?
C26 C27 H27 120.1 . . ?
C2 C1 N7 120.10(10) . . ?
C6 C1 N7 118.44(10) . . ?
C6 C1 C2 121.46(10) . . ?
C38 C37 C32 115.97(10) . . ?
C38 C37 C42 119.32(11) . . ?
C42 C37 C32 124.44(10) . . ?
C16 C21 H21 120.1 . . ?
C20 C21 C16 119.82(11) . . ?
C20 C21 H21 120.1 . . ?
O33 C32 N28 119.27(10) . . ?
O33 C32 C37 121.14(10) . . ?
N28 C32 C37 119.51(9) . . ?
O12 C11 N7 121.69(11) . . ?
O12 C11 C16 122.05(10) . . ?
N7 C11 C16 116.22(9) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 C4 118.17(10) . . ?
C2 C3 H3 120.9 . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.49(10) . . ?
C3 C2 H2 120.3 . . ?
C26 C25 N34 118.78(10) . . ?
C24 C25 N34 118.60(10) . . ?
C24 C25 C26 122.61(10) . . ?
C25 C24 H24 120.6 . . ?
C25 C24 C23 118.75(10) . . ?
C23 C24 H24 120.6 . . ?
C22 C23 H23 120.3 . . ?
C24 C23 C22 119.43(10) . . ?
C24 C23 H23 120.3 . . ?
C5 C6 C1 119.48(10) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C37 C38 H38 119.8 . . ?
C39 C38 C37 120.32(11) . . ?
C39 C38 H38 119.8 . . ?
C42 C41 H41 119.9 . . ?
C42 C41 C40 120.22(11) . . ?
C40 C41 H41 119.9 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.68(11) . . ?
C18 C17 H17 120.2 . . ?
C37 C42 H42 120.0 . . ?
C41 C42 C37 120.08(11) . . ?
C41 C42 H42 120.0 . . ?
C21 C20 H20 120.0 . . ?
C21 C20 C19 120.05(11) . . ?
C19 C20 H20 120.0 . . ?
C38 C39 H39 120.0 . . ?
C38 C39 C40 120.01(11) . . ?
C40 C39 H39 120.0 . . ?
C41 C40 C39 120.03(11) . . ?
C41 C40 H40 120.0 . . ?
C39 C40 H40 120.0 . . ?
F30 C29 F31 105.45(10) . . ?
F30 C29 N28 109.82(10) . . ?
F30 C29 H29 110.3 . . ?
F31 C29 N28 110.60(10) . . ?
F31 C29 H29 110.3 . . ?
N28 C29 H29 110.3 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.25(11) . . ?
C19 C18 H18 119.9 . . ?
C20 C19 H19 119.9 . . ?
C18 C19 C20 120.14(11) . . ?
C18 C19 H19 119.9 . . ?
F9 C8 F10 105.42(9) . . ?
F9 C8 N7 109.43(10) . . ?
F9 C8 H8 110.5 . . ?
F10 C8 N7 110.44(10) . . ?
F10 C8 H8 110.5 . . ?
N7 C8 H8 110.5 . . ?

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
O15 N13 C4 C5 -174.90(10) . . . . ?
O15 N13 C4 C3 3.98(15) . . . . ?
O14 N13 C4 C5 4.30(15) . . . . ?
O14 N13 C4 C3 -176.81(10) . . . . ?
O36 N34 C25 C26 -178.69(10) . . . . ?
O36 N34 C25 C24 2.43(15) . . . . ?
O35 N34 C25 C26 1.85(15) . . . . ?
O35 N34 C25 C24 -177.02(10) . . . . ?
N7 C1 C2 C3 -177.46(10) . . . . ?
N7 C1 C6 C5 177.67(10) . . . . ?
N28 C22 C27 C26 179.66(10) . . . . ?
N28 C22 C23 C24 -178.52(10) . . . . ?
N13 C4 C5 C6 -179.75(10) . . . . ?
N13 C4 C3 C2 179.96(10) . . . . ?
N34 C25 C24 C23 179.67(10) . . . . ?
C4 C5 C6 C1 0.01(16) . . . . ?
C4 C3 C2 C1 -0.40(16) . . . . ?
C22 N28 C32 O33 -154.24(11) . . . . ?
C22 N28 C32 C37 28.79(16) . . . . ?
C22 N28 C29 F30 -46.04(14) . . . . ?
C22 N28 C29 F31 69.93(13) . . . . ?
C5 C4 C3 C2 -1.22(17) . . . . ?
C16 C21 C20 C19 0.14(17) . . . . ?
C16 C17 C18 C19 0.02(17) . . . . ?
C26 C25 C24 C23 0.84(17) . . . . ?
C27 C22 C23 C24 0.47(16) . . . . ?
C27 C26 C25 N34 -178.54(10) . . . . ?
C27 C26 C25 C24 0.28(16) . . . . ?
C1 N7 C11 O12 157.51(11) . . . . ?
C1 N7 C11 C16 -24.69(15) . . . . ?
C1 N7 C8 F9 51.53(13) . . . . ?
C1 N7 C8 F10 -64.08(13) . . . . ?
C37 C38 C39 C40 -0.24(18) . . . . ?
C21 C16 C11 O12 125.14(12) . . . . ?
C21 C16 C11 N7 -52.65(14) . . . . ?
C21 C16 C17 C18 0.17(16) . . . . ?
C21 C20 C19 C18 0.05(18) . . . . ?
C32 N28 C22 C27 51.92(15) . . . . ?
C32 N28 C22 C23 -129.07(12) . . . . ?
C32 N28 C29 F30 154.62(10) . . . . ?
C32 N28 C29 F31 -89.40(12) . . . . ?
C32 C37 C38 C39 -174.43(10) . . . . ?
C32 C37 C42 C41 174.33(11) . . . . ?
C11 N7 C1 C2 117.85(12) . . . . ?
C11 N7 C1 C6 -61.44(14) . . . . ?
C11 N7 C8 F9 -152.37(10) . . . . ?
C11 N7 C8 F10 92.02(12) . . . . ?
C11 C16 C21 C20 -175.56(10) . . . . ?
C11 C16 C17 C18 175.58(10) . . . . ?
C3 C4 C5 C6 1.41(17) . . . . ?
C2 C1 C6 C5 -1.60(17) . . . . ?
C25 C26 C27 C22 -1.03(16) . . . . ?
C25 C24 C23 C22 -1.20(16) . . . . ?
C23 C22 C27 C26 0.67(16) . . . . ?
C6 C1 C2 C3 1.80(17) . . . . ?
C38 C37 C32 O33 20.33(16) . . . . ?
C38 C37 C32 N28 -162.75(10) . . . . ?
C38 C37 C42 C41 0.53(17) . . . . ?
C38 C39 C40 C41 0.20(18) . . . . ?
C17 C16 C21 C20 -0.25(16) . . . . ?
C17 C16 C11 O12 -50.23(15) . . . . ?
C17 C16 C11 N7 131.98(11) . . . . ?
C17 C18 C19 C20 -0.13(18) . . . . ?
C42 C37 C32 O33 -153.66(11) . . . . ?
C42 C37 C32 N28 23.26(17) . . . . ?
C42 C37 C38 C39 -0.12(17) . . . . ?
C42 C41 C40 C39 0.21(18) . . . . ?
C40 C41 C42 C37 -0.57(18) . . . . ?
C29 N28 C22 C27 -105.27(12) . . . . ?
C29 N28 C22 C23 73.74(14) . . . . ?
C29 N28 C32 O33 3.46(16) . . . . ?
C29 N28 C32 C37 -173.52(10) . . . . ?
C8 N7 C1 C2 -87.01(13) . . . . ?
C8 N7 C1 C6 93.71(13) . . . . ?
C8 N7 C11 O12 2.18(16) . . . . ?
C8 N7 C11 C16 179.98(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.073
_oxdiff_exptl_absorpt_empirical_full_min 0.898
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: AcOEt-nhex'
