# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

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

data_exp_hjx20230524-4-cn-f_auto
_database_code_depnum_ccdc_archive 'CCDC 2293353'
loop_
_audit_author_name
_audit_author_address
'Jun Xu'
;Tianjin University
China
;
_audit_update_record             
;
2023-09-06 deposited with the CCDC.	2024-07-04 downloaded from the CCDC.
;
_audit_creation_date             2023-09-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 F N3 O'
_chemical_formula_sum            'C24 H20 F N3 O'
_chemical_formula_weight         385.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.3241(2)
_cell_length_b                   10.9750(2)
_cell_length_c                   11.7780(2)
_cell_angle_alpha                111.810(2)
_cell_angle_beta                 91.382(2)
_cell_angle_gamma                112.051(2)
_cell_volume                     1018.22(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    25538
_cell_measurement_temperature    301.57(10)
_cell_measurement_theta_max      74.8760
_cell_measurement_theta_min      4.1000
_shelx_estimated_absorpt_T_max   0.875
_shelx_estimated_absorpt_T_min   0.771
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.63a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0097
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            35065
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.136
_diffrn_reflns_theta_min         4.118
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.57(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     27.00 125.00   0.50    0.05    --   52.00  78.00 177.58  196
  2  ω     43.00  70.00   0.50    0.05    --   68.00  78.00 140.31   54
  3  ω     27.00 125.00   0.50    0.05    --   52.00  77.00 -32.82  196
  4  ω     39.00 137.00   0.50    0.05    --   64.00  77.00 -86.22  196
  5  ω     81.00 117.00   0.50    0.05    --  104.81  77.00-180.00   72
  6  ω    121.00 165.00   0.50    0.05    --  104.81  77.00-180.00   88
  7  ω     80.00 147.00   0.50    0.05    --  104.81  77.00 -90.00  134
  8  ω     28.00 125.00   0.50    0.05    --   52.00  75.00-135.64  194
  9  ω     32.00 129.00   0.50    0.05    --   56.00  76.00 -99.74  194
 10  ω     32.00 129.00   0.50    0.05    --   56.00  75.00   4.31  194
 11  ω     36.00 132.00   0.50    0.05    --   60.00  76.00  56.88  192
 12  ω     32.00 129.00   0.50    0.05    --   56.00  75.00  41.85  194
 13  ω     41.00 137.00   0.50    0.05    --   64.00  73.00   5.31  192
 14  ω     41.00 137.00   0.50    0.05    --   64.00  72.00 -23.50  192
 15  ω     44.00  80.00   0.50    0.05    --   68.00  76.00  83.45   72
 16  ω     36.00 132.00   0.50    0.05    --   60.00  76.00  89.78  192
 17  ω     32.00 129.00   0.50    0.05    --   56.00  75.00 133.27  194
 18  ω     41.00 137.00   0.50    0.05    --   64.00  73.00 129.27  192
 19  ω     86.00 157.00   0.50    0.05    --  104.81  61.00 150.00  142
 20  ω     86.00 112.00   0.50    0.05    --  104.81  61.00 -90.00   52
 21  ω     81.00 175.00   0.50    0.05    --  104.81  93.00 -30.00  188
 22  ω     29.00 120.00   0.50    0.05    --   45.63  37.00-150.00  182
 23  ω      6.00  36.00   0.50    0.05    --   36.00  89.00 -99.69   60
 24  ω     -7.00  36.00   0.50    0.05    --   24.00  91.00 -83.68   86
 25  ω     27.00 123.00   0.50    0.05    --   45.63  19.00-180.00  192
 26  ω     23.00 121.00   0.50    0.05    --   48.00  78.00 138.92  196
 27  ω     29.00 120.00   0.50    0.05    --   45.63  37.00  60.00  182
 28  ω     77.00 102.00   0.50    0.05    --  104.81 -77.00 120.00   50
 29  ω     32.00  58.00   0.50    0.05    --  104.81 -77.00 120.00   52
 30  ω     43.00  70.00   0.50    0.05    --  104.81-125.00 120.00   54
 31  ω     85.00 112.00   0.50    0.05    --  104.81-125.00 120.00   54
 32  ω     68.00 109.00   0.50    0.05    --  104.81-125.00  60.00   82
 33  ω     38.00  65.00   0.50    0.05    --  104.81-125.00  60.00   54
 34  ω     60.00 101.00   0.50    0.05    --  104.81 -94.00  30.00   82
 35  ω     70.00 112.00   0.50    0.05    --  104.81-125.00   0.00   84
 36  ω     32.00  66.00   0.50    0.05    --  104.81 -61.00-120.00   68
 37  ω     41.00  67.00   0.50    0.05    --  104.81 -93.00-142.00   52
 38  ω     72.00 101.00   0.50    0.05    --  104.81 -93.00-142.00   58
 39  ω     52.00 100.00   0.50    0.05    --  104.81-125.00-180.00   96
 40  ω    -26.00  78.00   0.50    0.05    --   45.63 -93.00-142.00  208
 41  ω    -41.00 -12.00   0.50    0.05    --  -40.00 -83.00  86.70   58
 42  ω    -41.00 -15.00   0.50    0.05    --  -44.00 -86.00 -75.95   52
 43  ω   -173.00 -87.00   0.50    0.05    -- -100.00 -93.00-142.00  172
 44  ω   -136.00-111.00   0.50    0.05    --  -88.00 -76.00 -10.66   50
 45  ω   -164.00 -75.00   0.50    0.05    -- -100.00 -77.00  26.98  178
 46  ω   -167.00 -72.00   0.50    0.05    --  -96.00 -76.00   2.85  190
 47  ω   -160.00-105.00   0.50    0.05    --  -88.00 -76.00 131.39  110
 48  ω    -92.00 -63.00   0.50    0.05    --  -88.00 -76.00 131.39   58
 49  ω    -97.00 -71.00   0.50    0.05    --  -96.00 -76.00 173.35   52
 50  ω   -163.00-128.00   0.50    0.05    --  -96.00 -76.00 173.35   70
 51  ω   -158.00 -72.00   0.50    0.05    --  -96.00 -75.00  40.72  172
 52  ω    -86.00 -60.00   0.50    0.05    --  -84.00 -75.00 176.40   52
 53  ω    -96.00 -63.00   0.50    0.05    --  -88.00 -76.00 -10.66   66
 54  ω    -87.00 -60.00   0.50    0.05    --  -84.00 -74.00  47.91   54
 55  ω    -88.00 -56.00   0.50    0.05    --  -80.00 -74.00 -78.00   64
 56  ω    -83.00 -52.00   0.50    0.05    --  -76.00 -74.00-137.11   62
 57  ω    -87.00 -60.00   0.50    0.05    --  -84.00 -75.00-110.40   54
 58  ω    -89.00 -57.00   0.50    0.05    --  -80.00 -72.00-179.73   64
 59  ω    -96.00 -65.00   0.50    0.05    --  -88.00 -72.00-151.72   62
 60  ω   -156.00-117.00   0.50    0.05    --  -84.00 -75.00-110.40   78
 61  ω   -161.00-135.00   0.50    0.05    --  -88.00 -72.00-151.72   52
 62  ω    -86.00 -54.00   0.50    0.05    --  -76.00 -72.00-106.15   64
 63  ω    -90.00 -64.00   0.50    0.05    --  -88.00 -74.00  35.48   52
 64  ω    -84.00 -57.00   0.50    0.05    --  -80.00 -72.00 -45.80   54
 65  ω    -92.00 -65.00   0.50    0.05    --  -88.00 -74.00 102.97   54
 66  ω    -83.00 -57.00   0.50    0.05    --  -80.00 -72.00 130.77   52
 67  ω    -71.00 -45.00   0.50    0.05    --  -68.00 -72.00 147.83   52
 68  ω   -104.00 -69.00   0.50    0.05    --  -92.00 -72.00 146.30   70
 69  ω    -99.00 -65.00   0.50    0.05    --  -88.00 -71.00  85.46   68
 70  ω   -127.00 -78.00   0.50    0.05    -- -100.00 -70.00 122.94   98
 71  ω    -86.00 -58.00   0.50    0.05    --  -80.00 -71.00 -64.58   56
 72  ω    -82.00 -49.00   0.50    0.05    --  -72.00 -71.00-174.74   66
 73  ω   -134.00 -79.00   0.50    0.05    -- -100.00 -71.00-178.78  110
 74  ω   -144.00-118.00   0.50    0.05    --  -72.00 -71.00-174.74   52
 75  ω   -106.00 -71.00   0.50    0.05    --  -92.00 -68.00-136.69   70
 76  ω   -107.00 -79.00   0.50    0.05    -- -100.00 -68.00-123.17   56
 77  ω   -165.00-120.00   0.50    0.05    --  -92.00 -68.00-136.69   90
 78  ω   -140.00 -79.00   0.50    0.05    -- -100.00 -67.00 -50.96  122
 79  ω   -112.00 -70.00   0.50    0.05    --  -92.00 -69.00  63.27   84
 80  ω   -163.00-131.00   0.50    0.05    -- -100.00 -70.00 122.94   64
 81  ω   -168.00-120.00   0.50    0.05    -- -100.00 -67.00 159.83   96
 82  ω   -114.00 -79.00   0.50    0.05    -- -100.00 -67.00 159.83   70
 83  ω    -87.00 -60.00   0.50    0.05    --  -80.00 -64.00 -17.94   54
 84  ω    -79.00 -49.00   0.50    0.05    --  -68.00 -63.00 -15.87   60
 85  ω    -96.00 -64.00   0.50    0.05    --  -84.00 -64.00 -42.93   64
 86  ω   -127.00 -94.00   0.50    0.05    -- -100.00 -61.00 -90.00   66
 87  ω   -173.00-130.00   0.50    0.05    -- -100.00 -61.00 -90.00   86
 88  ω   -155.00-122.00   0.50    0.05    --  -96.00 -53.00 -80.60   66
 89  ω   -157.00-119.00   0.50    0.05    --  -84.00 -64.00 -42.93   76
 90  ω   -115.00 -85.00   0.50    0.05    --  -96.00 -53.00 -80.60   60
 91  ω   -151.00-124.00   0.50    0.05    -- -100.00 -61.00  90.00   54
 92  ω   -117.00 -82.00   0.50    0.05    -- -100.00 -61.00  90.00   70
 93  ω   -172.00 -82.00   0.50    0.05    -- -100.00 -58.00  76.48  180
 94  ω   -119.00 -28.00   0.50    0.05    --  -45.63 -45.00  86.02  182
 95  ω    -71.00 -31.00   0.50    0.05    -- -100.00  77.00 -30.00   80
 96  ω    -73.00 -29.00   0.50    0.05    -- -100.00  61.00-180.00   88
 97  ω   -107.00 -76.00   0.50    0.05    -- -100.00  77.00 -30.00   62
 98  ω    -54.00 -28.00   0.50    0.05    -- -100.00  45.00 -90.00   52
 99  ω    -53.00 -28.00   0.50    0.05    -- -100.00  45.00 -30.00   50
100  ω    -74.00 -28.00   0.50    0.05    -- -100.00  61.00  30.00   92
101  ω    -73.00 -28.00   0.50    0.05    -- -100.00  61.00 120.00   90
102  ω    -84.00 -23.00   0.50    0.05    --  -36.00 125.00 159.72  122
103  ω    -93.00 -23.00   0.50    0.05    --  -45.63 125.00 120.00  140
104  ω    -78.00  27.00   0.50    0.05    --  -45.63  93.00 -30.00  210
105  ω   -105.00 -27.00   0.50    0.05    -- -100.00  93.00 -30.00  156
106  ω   -107.00 -33.00   0.50    0.05    -- -100.00 106.00-173.06  148
;
_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      0.1642755000
_diffrn_orient_matrix_UB_12      -0.0009845000
_diffrn_orient_matrix_UB_13      -0.0078366000
_diffrn_orient_matrix_UB_21      0.0647671000
_diffrn_orient_matrix_UB_22      0.1211976000
_diffrn_orient_matrix_UB_23      0.1322970000
_diffrn_orient_matrix_UB_31      -0.0422880000
_diffrn_orient_matrix_UB_32      -0.1135858000
_diffrn_orient_matrix_UB_33      0.0550352000
_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                3772
_reflns_number_total             4022
_reflns_odcompleteness_completeness 99.75
_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 1.171.42.63a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4022
_refine_ls_number_restraints     284
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      0.998
_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)+(0.0541P)²+0.1611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1029
_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. Restrained distances
 C31-C36 \\sim C31-C36A
 with sigma of 0.02
 C31-C10 \\sim C31-C10A
 with sigma of 0.02
 C36-C39 \\sim C36A-C39A
 with sigma of 0.02
 C10-C21 \\sim C10A-C21A
 with sigma of 0.02
 C39-C11 \\sim C39A-C11A
 with sigma of 0.02
 C11-C21 \\sim C11A-C21A
 with sigma of 0.02
 C31-C39 \\sim C31-C39A
 with sigma of 0.04
 C31-C21 \\sim C31-C21A
 with sigma of 0.04
 C36-C11 \\sim C36A-C11A
 with sigma of 0.04
 C10-C11 \\sim C10A-C11A
 with sigma of 0.04
 C39-C21 \\sim C39A-C21A
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 C36, C10, C39, C11, C21
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C36A, C10A, C39A, C11A, C21A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Others
 Sof(C36A)=Sof(H36A)=Sof(C10A)=Sof(H10A)=Sof(C21A)=Sof(H21A)=Sof(C11A)=
 Sof(H11A)=Sof(C39A)=Sof(H39A)=1-FVAR(1)
 Sof(C36)=Sof(H36)=Sof(C10)=Sof(H10)=Sof(C39)=Sof(H39)=Sof(C11)=Sof(H11)=
 Sof(C21)=Sof(H21)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C40(H40A,H40B)
5.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C36(H36), C42(H42), C34(H34), C16(H16), C4(H4), C10(H10), C32(H32),
 C8(H8), C39(H39), C11(H11), C47(H47), C21(H21), C36A(H36A), C10A(H10A),
 C21A(H21A), C11A(H11A), C39A(H39A)
5.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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
O13 O 0.27325(9) 0.35921(7) 0.36897(7) 0.04340(18) Uani 1 1 d . . . . .
F25 F 0.05894(10) 0.40369(10) 0.41036(8) 0.0747(3) Uani 1 1 d . . . . .
N27 N 0.24545(11) 0.12579(9) 0.26024(8) 0.0451(2) Uani 1 1 d . . . . .
N2 N 0.21310(12) 0.19751(10) 0.46402(8) 0.0487(2) Uani 1 1 d . . . . .
C7 C 0.23897(12) 0.22612(11) 0.36946(10) 0.0415(2) Uani 1 1 d . . . . .
C31 C 0.41706(14) 0.01692(12) 0.31001(9) 0.0447(3) Uani 1 1 d D . . . .
C33 C 0.24238(13) 0.14174(11) 0.14589(10) 0.0449(2) Uani 1 1 d . . . . .
C29 C 0.25490(13) -0.00296(11) 0.26316(11) 0.0461(3) Uani 1 1 d . . . . .
H29A H 0.217099 -0.078971 0.179616 0.055 Uiso 1 1 calc R U . . .
H29B H 0.184748 -0.034847 0.315648 0.055 Uiso 1 1 calc R U . . .
C35 C 0.21696(13) 0.30034(11) 0.58015(10) 0.0433(2) Uani 1 1 d . . . . .
C9 C 0.09428(14) 0.25883(13) 0.64141(10) 0.0507(3) Uani 1 1 d . . . . .
H9 H 0.013353 0.166835 0.603429 0.061 Uiso 1 1 calc R U . . .
C49 C 0.14568(14) 0.20053(13) 0.11556(11) 0.0510(3) Uani 1 1 d . . . . .
C36 C 0.5561(8) 0.1425(7) 0.3493(11) 0.0513(14) Uani 0.61(2) 1 d D . P A 1
H36 H 0.554631 0.226555 0.348783 0.062 Uiso 0.61(2) 1 calc R U P A 1
C42 C 0.09018(14) 0.35125(13) 0.75727(10) 0.0523(3) Uani 1 1 d . . . . .
H42 H 0.005447 0.322727 0.795779 0.063 Uiso 1 1 calc R U . . .
C40 C 0.04686(15) 0.24981(14) 0.20518(12) 0.0560(3) Uani 1 1 d . . . . .
H40A H -0.013884 0.173153 0.229587 0.067 Uiso 1 1 calc R U . . .
H40B H -0.026325 0.271698 0.164877 0.067 Uiso 1 1 calc R U . . .
C34 C 0.33133(16) 0.09300(14) 0.06170(11) 0.0560(3) Uani 1 1 d . . . . .
H34 H 0.394046 0.051951 0.081106 0.067 Uiso 1 1 calc R U . . .
C18 C 0.21250(15) 0.48668(13) 0.81624(10) 0.0514(3) Uani 1 1 d . . . . .
C20 C 0.15000(14) 0.38232(13) 0.31951(11) 0.0511(3) Uani 1 1 d . . . . .
C16 C 0.33943(16) 0.52666(14) 0.75836(12) 0.0630(3) Uani 1 1 d . . . . .
H16 H 0.423686 0.616250 0.798835 0.076 Uiso 1 1 calc R U . . .
C4 C 0.34153(15) 0.43455(14) 0.64133(12) 0.0584(3) Uani 1 1 d . . . . .
H4 H 0.426885 0.462569 0.603263 0.070 Uiso 1 1 calc R U . . .
C10 C 0.4224(9) -0.1084(7) 0.3144(10) 0.0483(11) Uani 0.61(2) 1 d D . P A 1
H10 H 0.330545 -0.192411 0.290176 0.058 Uiso 0.61(2) 1 calc R U P A 1
C30 C 0.20416(19) 0.58396(16) 0.93546(13) 0.0674(4) Uani 1 1 d . . . . .
N24 N 0.1924(2) 0.66011(17) 1.02845(13) 0.0988(5) Uani 1 1 d . . . . .
C32 C 0.1450(2) 0.21334(17) 0.00290(12) 0.0693(4) Uani 1 1 d . . . . .
H32 H 0.082923 0.254454 -0.017361 0.083 Uiso 1 1 calc R U . . .
C8 C 0.3267(2) 0.10546(17) -0.05063(12) 0.0710(4) Uani 1 1 d . . . . .
H8 H 0.386058 0.072565 -0.106783 0.085 Uiso 1 1 calc R U . . .
C14 C 0.2265(2) 0.51841(15) 0.30119(16) 0.0743(4) Uani 1 1 d . . . . .
H14A H 0.296438 0.593573 0.376837 0.111 Uiso 1 1 calc R U . . .
H14B H 0.146981 0.545954 0.279625 0.111 Uiso 1 1 calc R U . . .
H14C H 0.285149 0.503125 0.235342 0.111 Uiso 1 1 calc R U . . .
C39 C 0.6971(9) 0.1411(9) 0.3894(9) 0.0613(15) Uani 0.61(2) 1 d D . P A 1
H39 H 0.789899 0.224421 0.414696 0.074 Uiso 0.61(2) 1 calc R U P A 1
C11 C 0.7004(9) 0.0185(9) 0.3918(7) 0.0606(14) Uani 0.61(2) 1 d D . P A 1
H11 H 0.795386 0.019048 0.418690 0.073 Uiso 0.61(2) 1 calc R U P A 1
C47 C 0.2345(2) 0.16634(19) -0.07968(13) 0.0796(5) Uani 1 1 d . . . . .
H47 H 0.232491 0.175773 -0.154909 0.096 Uiso 1 1 calc R U . . .
C21 C 0.5639(10) -0.1059(8) 0.3547(10) 0.0615(12) Uani 0.61(2) 1 d D . P A 1
H21 H 0.567248 -0.188630 0.356799 0.074 Uiso 0.61(2) 1 calc R U P A 1
C36A C 0.5372(15) 0.1487(14) 0.3369(19) 0.063(3) Uani 0.39(2) 1 d D . P A 2
H36A H 0.514712 0.220084 0.326646 0.076 Uiso 0.39(2) 1 calc R U P A 2
C10A C 0.4586(19) -0.0822(16) 0.3255(18) 0.065(3) Uani 0.39(2) 1 d D . P A 2
H10A H 0.379225 -0.172962 0.307075 0.078 Uiso 0.39(2) 1 calc R U P A 2
C21A C 0.607(2) -0.059(2) 0.3657(15) 0.073(3) Uani 0.39(2) 1 d D . P A 2
H21A H 0.628173 -0.131433 0.375069 0.087 Uiso 0.39(2) 1 calc R U P A 2
C11A C 0.7269(18) 0.073(2) 0.3925(11) 0.076(3) Uani 0.39(2) 1 d D . P A 2
H11A H 0.830075 0.089915 0.419179 0.091 Uiso 0.39(2) 1 calc R U P A 2
C39A C 0.6939(15) 0.179(2) 0.3798(16) 0.072(3) Uani 0.39(2) 1 d D . P A 2
H39A H 0.773920 0.269414 0.399160 0.086 Uiso 0.39(2) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O13 C7 1.3753(12) . ?
O13 C20 1.4215(14) . ?
F25 C20 1.3884(14) . ?
N27 C7 1.3683(13) . ?
N27 C33 1.4221(14) . ?
N27 C29 1.4611(13) . ?
N2 C7 1.2700(14) . ?
N2 C35 1.4021(13) . ?
C31 C29 1.5036(16) . ?
C31 C36 1.397(5) . ?
C31 C10 1.415(6) . ?
C31 C36A 1.369(11) . ?
C31 C10A 1.352(11) . ?
C33 C49 1.3962(16) . ?
C33 C34 1.3914(16) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C35 C9 1.3890(16) . ?
C35 C4 1.3872(16) . ?
C9 H9 0.9300 . ?
C9 C42 1.3768(16) . ?
C49 C40 1.5009(17) . ?
C49 C32 1.3854(18) . ?
C36 H36 0.9300 . ?
C36 C39 1.393(7) . ?
C42 H42 0.9300 . ?
C42 C18 1.3836(17) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C40 C20 1.5118(17) . ?
C34 H34 0.9300 . ?
C34 C8 1.3810(19) . ?
C18 C16 1.3889(19) . ?
C18 C30 1.4392(17) . ?
C20 C14 1.4943(19) . ?
C16 H16 0.9300 . ?
C16 C4 1.3795(17) . ?
C4 H4 0.9300 . ?
C10 H10 0.9300 . ?
C10 C21 1.377(7) . ?
C30 N24 1.1420(18) . ?
C32 H32 0.9300 . ?
C32 C47 1.378(2) . ?
C8 H8 0.9300 . ?
C8 C47 1.375(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C39 H39 0.9300 . ?
C39 C11 1.369(6) . ?
C11 H11 0.9300 . ?
C11 C21 1.378(5) . ?
C47 H47 0.9300 . ?
C21 H21 0.9300 . ?
C36A H36A 0.9300 . ?
C36A C39A 1.406(11) . ?
C10A H10A 0.9300 . ?
C10A C21A 1.351(10) . ?
C21A H21A 0.9300 . ?
C21A C11A 1.363(10) . ?
C11A H11A 0.9300 . ?
C11A C39A 1.368(9) . ?
C39A H39A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O13 C20 118.31(8) . . ?
C7 N27 C33 122.87(9) . . ?
C7 N27 C29 117.62(9) . . ?
C33 N27 C29 119.51(8) . . ?
C7 N2 C35 122.86(9) . . ?
N27 C7 O13 114.38(9) . . ?
N2 C7 O13 124.37(9) . . ?
N2 C7 N27 121.10(10) . . ?
C36 C31 C29 127.3(4) . . ?
C36 C31 C10 118.9(4) . . ?
C10 C31 C29 113.7(3) . . ?
C36A C31 C29 116.6(7) . . ?
C10A C31 C29 127.3(7) . . ?
C10A C31 C36A 116.0(8) . . ?
C49 C33 N27 120.33(10) . . ?
C34 C33 N27 119.72(10) . . ?
C34 C33 C49 119.90(11) . . ?
N27 C29 C31 114.85(9) . . ?
N27 C29 H29A 108.6 . . ?
N27 C29 H29B 108.6 . . ?
C31 C29 H29A 108.6 . . ?
C31 C29 H29B 108.6 . . ?
H29A C29 H29B 107.5 . . ?
C9 C35 N2 117.14(10) . . ?
C4 C35 N2 124.02(10) . . ?
C4 C35 C9 118.58(10) . . ?
C35 C9 H9 119.4 . . ?
C42 C9 C35 121.27(11) . . ?
C42 C9 H9 119.4 . . ?
C33 C49 C40 119.84(10) . . ?
C32 C49 C33 118.65(11) . . ?
C32 C49 C40 121.50(12) . . ?
C31 C36 H36 120.2 . . ?
C39 C36 C31 119.6(6) . . ?
C39 C36 H36 120.2 . . ?
C9 C42 H42 120.1 . . ?
C9 C42 C18 119.80(11) . . ?
C18 C42 H42 120.1 . . ?
C49 C40 H40A 109.6 . . ?
C49 C40 H40B 109.6 . . ?
C49 C40 C20 110.48(10) . . ?
H40A C40 H40B 108.1 . . ?
C20 C40 H40A 109.6 . . ?
C20 C40 H40B 109.6 . . ?
C33 C34 H34 119.9 . . ?
C8 C34 C33 120.11(12) . . ?
C8 C34 H34 119.9 . . ?
C42 C18 C16 119.36(11) . . ?
C42 C18 C30 119.20(12) . . ?
C16 C18 C30 121.43(12) . . ?
O13 C20 C40 110.32(9) . . ?
O13 C20 C14 106.66(11) . . ?
F25 C20 O13 106.54(9) . . ?
F25 C20 C40 108.08(10) . . ?
F25 C20 C14 108.86(10) . . ?
C14 C20 C40 115.99(12) . . ?
C18 C16 H16 119.7 . . ?
C4 C16 C18 120.54(11) . . ?
C4 C16 H16 119.7 . . ?
C35 C4 H4 119.8 . . ?
C16 C4 C35 120.33(11) . . ?
C16 C4 H4 119.8 . . ?
C31 C10 H10 120.0 . . ?
C21 C10 C31 119.9(5) . . ?
C21 C10 H10 120.0 . . ?
N24 C30 C18 177.67(18) . . ?
C49 C32 H32 119.4 . . ?
C47 C32 C49 121.27(13) . . ?
C47 C32 H32 119.4 . . ?
C34 C8 H8 119.9 . . ?
C47 C8 C34 120.19(13) . . ?
C47 C8 H8 119.9 . . ?
C20 C14 H14A 109.5 . . ?
C20 C14 H14B 109.5 . . ?
C20 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C36 C39 H39 119.6 . . ?
C11 C39 C36 120.7(6) . . ?
C11 C39 H39 119.6 . . ?
C39 C11 H11 119.8 . . ?
C39 C11 C21 120.4(6) . . ?
C21 C11 H11 119.8 . . ?
C32 C47 H47 120.1 . . ?
C8 C47 C32 119.84(13) . . ?
C8 C47 H47 120.1 . . ?
C10 C21 C11 120.5(6) . . ?
C10 C21 H21 119.8 . . ?
C11 C21 H21 119.8 . . ?
C31 C36A H36A 119.2 . . ?
C31 C36A C39A 121.5(11) . . ?
C39A C36A H36A 119.2 . . ?
C31 C10A H10A 117.7 . . ?
C21A C10A C31 124.6(9) . . ?
C21A C10A H10A 117.7 . . ?
C10A C21A H21A 120.4 . . ?
C10A C21A C11A 119.2(9) . . ?
C11A C21A H21A 120.4 . . ?
C21A C11A H11A 120.2 . . ?
C21A C11A C39A 119.6(10) . . ?
C39A C11A H11A 120.2 . . ?
C36A C39A H39A 120.5 . . ?
C11A C39A C36A 119.0(11) . . ?
C11A C39A H39A 120.5 . . ?

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
N27 C33 C49 C40 1.20(17) . . . . ?
N27 C33 C49 C32 -179.51(12) . . . . ?
N27 C33 C34 C8 178.72(12) . . . . ?
N2 C35 C9 C42 178.32(11) . . . . ?
N2 C35 C4 C16 -176.72(12) . . . . ?
C7 O13 C20 F25 77.68(11) . . . . ?
C7 O13 C20 C40 -39.40(13) . . . . ?
C7 O13 C20 C14 -166.17(10) . . . . ?
C7 N27 C33 C49 -38.66(16) . . . . ?
C7 N27 C33 C34 144.00(12) . . . . ?
C7 N27 C29 C31 -80.84(12) . . . . ?
C7 N2 C35 C9 134.07(12) . . . . ?
C7 N2 C35 C4 -51.88(17) . . . . ?
C31 C36 C39 C11 -0.7(15) . . . . ?
C31 C10 C21 C11 0.6(16) . . . . ?
C31 C36A C39A C11A 1(3) . . . . ?
C31 C10A C21A C11A -1(3) . . . . ?
C33 N27 C7 O13 -17.25(15) . . . . ?
C33 N27 C7 N2 167.03(11) . . . . ?
C33 N27 C29 C31 99.54(12) . . . . ?
C33 C49 C40 C20 69.16(15) . . . . ?
C33 C49 C32 C47 1.5(2) . . . . ?
C33 C34 C8 C47 0.2(2) . . . . ?
C29 N27 C7 O13 163.14(9) . . . . ?
C29 N27 C7 N2 -12.58(16) . . . . ?
C29 N27 C33 C49 140.94(11) . . . . ?
C29 N27 C33 C34 -36.40(15) . . . . ?
C29 C31 C36 C39 -179.6(7) . . . . ?
C29 C31 C10 C21 179.5(8) . . . . ?
C29 C31 C36A C39A -179.1(14) . . . . ?
C29 C31 C10A C21A 178.6(12) . . . . ?
C35 N2 C7 O13 -0.08(17) . . . . ?
C35 N2 C7 N27 175.20(10) . . . . ?
C35 C9 C42 C18 -2.03(19) . . . . ?
C9 C35 C4 C16 -2.8(2) . . . . ?
C9 C42 C18 C16 -1.09(19) . . . . ?
C9 C42 C18 C30 177.93(12) . . . . ?
C49 C33 C34 C8 1.4(2) . . . . ?
C49 C40 C20 O13 -50.37(14) . . . . ?
C49 C40 C20 F25 -166.48(10) . . . . ?
C49 C40 C20 C14 71.01(14) . . . . ?
C49 C32 C47 C8 0.0(3) . . . . ?
C36 C31 C29 N27 -0.4(6) . . . . ?
C36 C31 C10 C21 -1.3(13) . . . . ?
C36 C39 C11 C21 -0.1(15) . . . . ?
C42 C18 C16 C4 2.2(2) . . . . ?
C40 C49 C32 C47 -179.20(14) . . . . ?
C34 C33 C49 C40 178.54(11) . . . . ?
C34 C33 C49 C32 -2.17(18) . . . . ?
C34 C8 C47 C32 -0.8(3) . . . . ?
C18 C16 C4 C35 -0.3(2) . . . . ?
C20 O13 C7 N27 84.53(11) . . . . ?
C20 O13 C7 N2 -99.91(13) . . . . ?
C4 C35 C9 C42 3.94(18) . . . . ?
C10 C31 C29 N27 178.7(5) . . . . ?
C10 C31 C36 C39 1.3(13) . . . . ?
C30 C18 C16 C4 -176.75(13) . . . . ?
C32 C49 C40 C20 -110.11(14) . . . . ?
C39 C11 C21 C10 0.1(16) . . . . ?
C36A C31 C29 N27 -3.8(10) . . . . ?
C36A C31 C10A C21A 1(2) . . . . ?
C10A C31 C29 N27 178.1(10) . . . . ?
C10A C31 C36A C39A -1(2) . . . . ?
C10A C21A C11A C39A 1(2) . . . . ?
C21A C11A C39A C36A -1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.597
_oxdiff_exptl_absorpt_empirical_full_min 0.670
