# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_a230314b
_database_code_depnum_ccdc_archive 'CCDC 2253478'
loop_
_audit_author_name
_audit_author_address
JINGTI
;Tianjin Normal University
China
;
_audit_update_record             
;
2023-04-03 deposited with the CCDC.	2023-09-21 downloaded from the CCDC.
;
_audit_creation_date             2023-04-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 F3 N O'
_chemical_formula_sum            'C23 H20 F3 N O'
_chemical_formula_weight         383.40
_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                   11.6001(6)
_cell_length_b                   12.1058(5)
_cell_length_c                   14.3702(8)
_cell_angle_alpha                99.463(4)
_cell_angle_beta                 103.907(4)
_cell_angle_gamma                103.592(4)
_cell_volume                     1851.06(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5180
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      72.7330
_cell_measurement_theta_min      3.2300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.876
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (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    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12544
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.063
_diffrn_reflns_theta_max         67.063
_diffrn_reflns_theta_min         3.259
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00 -13.00   1.00    1.00    --  -41.42 125.00 120.00   27
  2  ω   -114.00 -25.00   1.00    1.00    --  -41.42 -38.00 -90.00   89
  3  ω    -76.00  39.00   1.00    1.00    --  -41.42  19.00  90.00  115
  4  ω      6.00  51.00   1.00    1.00    --   41.42 -99.00 120.00   45
  5  ω     29.00  66.00   1.00    1.00    --   41.42-125.00-120.00   37
  6  ω     53.00  97.00   1.00    1.00    --   41.42-125.00   0.00   44
  7  ω     28.00 106.00   1.00    2.24    --  105.20 -94.00 -30.00   78
  8  ω     32.00  68.00   1.00    2.24    --  105.20 -45.00  30.00   36
  9  ω     38.00  75.00   1.00    2.24    --  105.20 -61.00-120.00   37
 10  ω     32.00  93.00   1.00    2.24    --  105.20-125.00-120.00   61
 11  ω     86.00 169.00   1.00    2.24    --  105.20  30.00  30.00   83
 12  ω    128.00 178.00   1.00    2.24    --  105.20  77.00-120.00   50
 13  ω     88.00 131.00   1.00    2.24    --  105.20 -45.00  30.00   43
 14  ω     70.00 111.00   1.00    2.24    --  105.20-125.00-180.00   41
 15  ω    104.00 130.00   1.00    2.24    --  105.20  77.00 150.00   26
 16  ω    108.00 134.00   1.00    2.24    --  105.20 -61.00  60.00   26
 17  ω     54.00 153.00   1.00    2.24    --  105.20  15.00 -30.00   99
 18  ω     34.00 118.00   1.00    2.24    --  105.20 -45.00 -60.00   84
 19  ω     29.00  65.00   1.00    2.24    --  105.20-111.00 -96.00   36
 20  ω     68.00 109.00   1.00    2.24    --  105.20-111.00 -96.00   41
 21  ω     58.00 106.00   1.00    2.24    --  105.20 -94.00  60.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1315636000
_diffrn_orient_matrix_UB_12      -0.0520995000
_diffrn_orient_matrix_UB_13      -0.0721186000
_diffrn_orient_matrix_UB_21      -0.0492984000
_diffrn_orient_matrix_UB_22      -0.0347552000
_diffrn_orient_matrix_UB_23      0.0846491000
_diffrn_orient_matrix_UB_31      -0.0256126000
_diffrn_orient_matrix_UB_32      0.1192188000
_diffrn_orient_matrix_UB_33      0.0232042000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5433
_reflns_number_total             6601
_reflns_odcompleteness_completeness 99.94
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.672
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     515
_refine_ls_number_reflns         6601
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.046
_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)+(0.0618P)²+0.9114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1278
_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
 C44A-C43 = C44-C43 = C44A-C45A = C45-C44
 1.52 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C44) = Uanis(C44A)
Uanis(C45A) = Uanis(C45)
4. Others
 Sof(H43A)=Sof(C44A)=Sof(H44C)=Sof(H44D)=Sof(C45A)=Sof(H45D)=Sof(H45E)=
 Sof(H45F)=1-FVAR(1)
 Sof(H43)=Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(H45C)=
 FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C43(H43), C43(H43A), C20(H20)
5.b Secondary CH2 refined with riding coordinates:
 C42(H42A,H42B), C44(H44A,H44B), C44A(H44C,H44D), C19(H19A,H19B), C21(H21A,H21B)
5.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C33(H33),
 C36(H36), C37(H37), C38(H38), C39(H39), C40(H40), C3(H3), C4(H4), C6(H6),
 C7(H7), C8(H8), C9(H9), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
5.d Idealised Me refined as rotating group:
 C45(H45A,H45B,H45C), C45A(H45D,H45E,H45F), C22(H22A,H22B,H22C)
;
_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
F4 F 0.57986(12) 0.65973(12) 0.96733(10) 0.0470(3) Uani 1 1 d . . . . .
F5 F 0.68134(13) 0.55612(11) 1.04325(12) 0.0499(4) Uani 1 1 d . . . . .
F6 F 0.56104(11) 0.63413(11) 1.10716(11) 0.0452(3) Uani 1 1 d . . . . .
O2 O 0.69856(12) 0.85573(11) 1.12265(9) 0.0257(3) Uani 1 1 d . . . . .
N2 N 0.69826(17) 0.8403(2) 1.28496(13) 0.0419(5) Uani 1 1 d . . . . .
C23 C 0.75377(18) 0.76224(16) 1.10743(14) 0.0265(4) Uani 1 1 d . . . . .
C24 C 0.82903(17) 0.78586(16) 1.03539(13) 0.0249(4) Uani 1 1 d . . . . .
C25 C 0.91355(18) 0.72077(17) 1.02202(14) 0.0284(4) Uani 1 1 d . . . . .
H25 H 0.924788 0.665722 1.058851 0.034 Uiso 1 1 calc R . . . .
C26 C 0.97820(18) 0.73864(17) 0.95548(15) 0.0295(4) Uani 1 1 d . . . . .
H26 H 1.033038 0.695284 0.947639 0.035 Uiso 1 1 calc R . . . .
C27 C 0.96377(17) 0.82156(16) 0.89816(14) 0.0257(4) Uani 1 1 d . . . . .
C28 C 1.02899(18) 0.84035(18) 0.82725(15) 0.0310(4) Uani 1 1 d . . . . .
H28 H 1.086642 0.800124 0.820025 0.037 Uiso 1 1 calc R . . . .
C29 C 1.00764(19) 0.91675(18) 0.76992(16) 0.0343(5) Uani 1 1 d . . . . .
H29 H 1.050426 0.928067 0.723610 0.041 Uiso 1 1 calc R . . . .
C30 C 0.92070(19) 0.97895(18) 0.78051(16) 0.0342(5) Uani 1 1 d . . . . .
H30 H 0.904867 1.029217 0.739757 0.041 Uiso 1 1 calc R . . . .
C31 C 0.85965(18) 0.96566(16) 0.85040(15) 0.0287(4) Uani 1 1 d . . . . .
H31 H 0.804795 1.009026 0.858152 0.034 Uiso 1 1 calc R . . . .
C32 C 0.87915(16) 0.88671(15) 0.91085(14) 0.0242(4) Uani 1 1 d . . . . .
C33 C 0.81345(17) 0.86715(15) 0.98085(13) 0.0238(4) Uani 1 1 d . . . . .
H33 H 0.758753 0.910223 0.989985 0.029 Uiso 1 1 calc R . . . .
C34 C 0.64327(19) 0.65246(18) 1.05568(17) 0.0346(5) Uani 1 1 d . . . . .
C35 C 0.60846(17) 0.97642(16) 1.20959(14) 0.0265(4) Uani 1 1 d . . . . .
C36 C 0.56092(18) 1.00696(17) 1.28781(15) 0.0309(4) Uani 1 1 d . . . . .
H36 H 0.574681 0.972766 1.341325 0.037 Uiso 1 1 calc R . . . .
C37 C 0.4938(2) 1.08738(18) 1.28631(16) 0.0362(5) Uani 1 1 d . . . . .
H37 H 0.462246 1.106598 1.338511 0.043 Uiso 1 1 calc R . . . .
C38 C 0.47320(18) 1.13955(17) 1.20716(16) 0.0337(5) Uani 1 1 d . . . . .
H38 H 0.426888 1.192713 1.205730 0.040 Uiso 1 1 calc R . . . .
C39 C 0.52219(18) 1.11195(17) 1.12996(15) 0.0304(4) Uani 1 1 d . . . . .
H39 H 0.509934 1.147879 1.077419 0.036 Uiso 1 1 calc R . . . .
C40 C 0.58949(18) 1.03074(17) 1.13116(14) 0.0283(4) Uani 1 1 d . . . . .
H40 H 0.621999 1.012589 1.079354 0.034 Uiso 1 1 calc R . . . .
C41 C 0.67384(17) 0.88470(18) 1.21136(14) 0.0282(4) Uani 1 1 d . . . . .
C42 C 0.83188(19) 0.75095(19) 1.20524(15) 0.0320(4) Uani 1 1 d . . . . .
H42A H 0.855320 0.679120 1.194615 0.038 Uiso 1 1 calc R . . . .
H42B H 0.907266 0.815618 1.228982 0.038 Uiso 1 1 calc R . . . .
C43 C 0.7637(2) 0.7503(3) 1.28345(18) 0.0499(7) Uani 1 1 d D . . . .
H43 H 0.698347 0.675652 1.261266 0.060 Uiso 0.689(3) 1 calc R . P A 1
H43A H 0.711518 0.672603 1.280546 0.060 Uiso 0.311(3) 1 calc R . P A 2
C44 C 0.8442(3) 0.7458(3) 1.3809(2) 0.0366(8) Uani 0.689(3) 1 d D . P A 1
H44A H 0.894953 0.694384 1.370540 0.044 Uiso 0.689(3) 1 calc R . P A 1
H44B H 0.792864 0.715486 1.420464 0.044 Uiso 0.689(3) 1 calc R . P A 1
C45 C 0.9257(4) 0.8672(3) 1.4337(3) 0.0450(8) Uani 0.689(3) 1 d D . P A 1
H45A H 0.977060 0.896261 1.394634 0.067 Uiso 0.689(3) 1 calc GR . P A 1
H45B H 0.977031 0.865123 1.496296 0.067 Uiso 0.689(3) 1 calc GR . P A 1
H45C H 0.874902 0.917609 1.443833 0.067 Uiso 0.689(3) 1 calc GR . P A 1
C44A C 0.8635(8) 0.8151(7) 1.3935(5) 0.0366(8) Uani 0.311(3) 1 d D . P A 2
H44C H 0.927980 0.879245 1.388361 0.044 Uiso 0.311(3) 1 calc R . P A 2
H44D H 0.821382 0.846129 1.437765 0.044 Uiso 0.311(3) 1 calc R . P A 2
C45A C 0.9198(8) 0.7249(7) 1.4331(5) 0.0450(8) Uani 0.311(3) 1 d D . P A 2
H45D H 0.959793 0.693496 1.388200 0.067 Uiso 0.311(3) 1 calc GR . P A 2
H45E H 0.855704 0.662962 1.439879 0.067 Uiso 0.311(3) 1 calc GR . P A 2
H45F H 0.979681 0.761149 1.496299 0.067 Uiso 0.311(3) 1 calc GR . P A 2
F1 F 0.24985(11) 0.82386(10) 0.50450(8) 0.0328(3) Uani 1 1 d . . . . .
F2 F 0.17514(11) 0.83800(11) 0.35653(9) 0.0373(3) Uani 1 1 d . . . . .
F3 F 0.36964(12) 0.91645(10) 0.43183(10) 0.0380(3) Uani 1 1 d . . . . .
O1 O 0.19303(12) 0.61783(11) 0.36934(9) 0.0254(3) Uani 1 1 d . . . . .
N1 N 0.10394(14) 0.59673(14) 0.19839(12) 0.0263(3) Uani 1 1 d . . . . .
C00M C -0.00313(18) 0.48343(17) 0.29127(14) 0.0272(4) Uani 1 1 d . . . . .
C1 C 0.30172(16) 0.70890(15) 0.37738(13) 0.0227(4) Uani 1 1 d . . . . .
C2 C 0.40874(17) 0.69250(15) 0.45477(13) 0.0228(4) Uani 1 1 d . . . . .
C3 C 0.53331(17) 0.75203(16) 0.46345(14) 0.0259(4) Uani 1 1 d . . . . .
H3 H 0.550203 0.797171 0.419211 0.031 Uiso 1 1 calc R . . . .
C4 C 0.62876(17) 0.74319(17) 0.53680(14) 0.0275(4) Uani 1 1 d . . . . .
H4 H 0.709814 0.783232 0.541964 0.033 Uiso 1 1 calc R . . . .
C5 C 0.60658(17) 0.67454(16) 0.60469(14) 0.0242(4) Uani 1 1 d . . . . .
C6 C 0.70297(18) 0.66694(17) 0.68375(15) 0.0295(4) Uani 1 1 d . . . . .
H6 H 0.785006 0.704864 0.689915 0.035 Uiso 1 1 calc R . . . .
C7 C 0.67637(19) 0.60459(17) 0.75069(15) 0.0321(4) Uani 1 1 d . . . . .
H7 H 0.740222 0.602009 0.802953 0.039 Uiso 1 1 calc R . . . .
C8 C 0.55278(19) 0.54399(16) 0.74126(14) 0.0295(4) Uani 1 1 d . . . . .
H8 H 0.535570 0.501792 0.787280 0.035 Uiso 1 1 calc R . . . .
C9 C 0.45804(18) 0.54717(16) 0.66442(14) 0.0269(4) Uani 1 1 d . . . . .
H9 H 0.376989 0.505545 0.657699 0.032 Uiso 1 1 calc R . . . .
C10 C 0.48269(17) 0.61336(15) 0.59524(13) 0.0233(4) Uani 1 1 d . . . . .
C11 C 0.38528(17) 0.62441(15) 0.51867(13) 0.0238(4) Uani 1 1 d . . . . .
H11 H 0.303770 0.584279 0.512077 0.029 Uiso 1 1 calc R . . . .
C12 C 0.27421(17) 0.82228(17) 0.41836(14) 0.0264(4) Uani 1 1 d . . . . .
C13 C 0.10300(17) 0.57155(16) 0.27986(13) 0.0244(4) Uani 1 1 d . . . . .
C14 C -0.11624(18) 0.44825(16) 0.21793(15) 0.0279(4) Uani 1 1 d . . . . .
H14 H -0.123887 0.477683 0.161616 0.033 Uiso 1 1 calc R . . . .
C15 C -0.21747(19) 0.36945(18) 0.22865(16) 0.0343(5) Uani 1 1 d . . . . .
H15 H -0.293357 0.347753 0.180228 0.041 Uiso 1 1 calc R . . . .
C16 C -0.2063(2) 0.3229(2) 0.31094(17) 0.0457(6) Uani 1 1 d . . . . .
H16 H -0.274243 0.269694 0.317692 0.055 Uiso 1 1 calc R . . . .
C17 C -0.0937(3) 0.3558(3) 0.38302(17) 0.0599(8) Uani 1 1 d . . . . .
H17 H -0.085669 0.323793 0.437964 0.072 Uiso 1 1 calc R . . . .
C18 C 0.0075(2) 0.4367(2) 0.37385(16) 0.0490(6) Uani 1 1 d . . . . .
H18 H 0.082698 0.459554 0.423220 0.059 Uiso 1 1 calc R . . . .
C19 C 0.32699(17) 0.70791(16) 0.27764(13) 0.0234(4) Uani 1 1 d . . . . .
H19A H 0.367709 0.648183 0.264326 0.028 Uiso 1 1 calc R . . . .
H19B H 0.383562 0.782729 0.281467 0.028 Uiso 1 1 calc R . . . .
C20 C 0.21006(17) 0.68484(16) 0.19147(13) 0.0238(4) Uani 1 1 d . . . . .
H20 H 0.188050 0.758183 0.191298 0.029 Uiso 1 1 calc R . . . .
C21 C 0.23451(18) 0.64461(17) 0.09326(14) 0.0279(4) Uani 1 1 d . . . . .
H21A H 0.273405 0.582219 0.097935 0.033 Uiso 1 1 calc R . . . .
H21B H 0.155912 0.613102 0.041983 0.033 Uiso 1 1 calc R . . . .
C22 C 0.3168(2) 0.7419(2) 0.06385(16) 0.0380(5) Uani 1 1 d . . . . .
H22A H 0.330526 0.711249 0.002758 0.057 Uiso 1 1 calc GR . . . .
H22B H 0.394875 0.773670 0.114265 0.057 Uiso 1 1 calc GR . . . .
H22C H 0.277141 0.802421 0.055961 0.057 Uiso 1 1 calc GR . . . .


_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
F4 C34 1.334(3) . ?
F5 C34 1.341(2) . ?
F6 C34 1.342(3) . ?
O2 C23 1.437(2) . ?
O2 C41 1.381(2) . ?
N2 C41 1.266(3) . ?
N2 C43 1.467(3) . ?
C23 C24 1.526(3) . ?
C23 C34 1.542(3) . ?
C23 C42 1.525(3) . ?
C24 C25 1.422(3) . ?
C24 C33 1.373(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.364(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.414(3) . ?
C27 C28 1.424(3) . ?
C27 C32 1.422(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.362(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.414(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.370(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.414(3) . ?
C32 C33 1.418(3) . ?
C33 H33 0.9300 . ?
C35 C36 1.400(3) . ?
C35 C40 1.394(3) . ?
C35 C41 1.485(3) . ?
C36 H36 0.9300 . ?
C36 C37 1.382(3) . ?
C37 H37 0.9300 . ?
C37 C38 1.388(3) . ?
C38 H38 0.9300 . ?
C38 C39 1.391(3) . ?
C39 H39 0.9300 . ?
C39 C40 1.391(3) . ?
C40 H40 0.9300 . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C42 C43 1.522(3) . ?
C43 H43 0.9800 . ?
C43 H43A 0.9800 . ?
C43 C44 1.502(4) . ?
C43 C44A 1.656(7) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C44 C45 1.504(5) . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C44A H44C 0.9700 . ?
C44A H44D 0.9700 . ?
C44A C45A 1.518(7) . ?
C45A H45D 0.9600 . ?
C45A H45E 0.9600 . ?
C45A H45F 0.9600 . ?
F1 C12 1.332(2) . ?
F2 C12 1.347(2) . ?
F3 C12 1.339(2) . ?
O1 C1 1.433(2) . ?
O1 C13 1.379(2) . ?
N1 C13 1.259(2) . ?
N1 C20 1.463(2) . ?
C00M C13 1.489(3) . ?
C00M C14 1.392(3) . ?
C00M C18 1.388(3) . ?
C1 C2 1.530(3) . ?
C1 C12 1.537(3) . ?
C1 C19 1.529(2) . ?
C2 C3 1.420(3) . ?
C2 C11 1.364(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.413(3) . ?
C5 C6 1.422(3) . ?
C5 C10 1.416(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.365(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.411(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.371(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.415(3) . ?
C10 C11 1.424(3) . ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.386(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.383(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.380(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.390(3) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.534(2) . ?
C20 H20 0.9800 . ?
C20 C21 1.530(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.519(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C41 O2 C23 118.60(15) . . ?
C41 N2 C43 120.48(18) . . ?
O2 C23 C24 107.89(15) . . ?
O2 C23 C34 104.79(15) . . ?
O2 C23 C42 110.77(16) . . ?
C24 C23 C34 107.92(16) . . ?
C42 C23 C24 112.61(16) . . ?
C42 C23 C34 112.45(17) . . ?
C25 C24 C23 119.97(17) . . ?
C33 C24 C23 120.68(17) . . ?
C33 C24 C25 119.32(18) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.36(18) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 119.2 . . ?
C25 C26 C27 121.52(18) . . ?
C27 C26 H26 119.2 . . ?
C26 C27 C28 122.42(18) . . ?
C26 C27 C32 118.46(18) . . ?
C32 C27 C28 119.12(18) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 C27 120.54(19) . . ?
C29 C28 H28 119.7 . . ?
C28 C29 H29 119.8 . . ?
C28 C29 C30 120.31(19) . . ?
C30 C29 H29 119.8 . . ?
C29 C30 H30 119.8 . . ?
C31 C30 C29 120.44(19) . . ?
C31 C30 H30 119.8 . . ?
C30 C31 H31 119.6 . . ?
C30 C31 C32 120.72(18) . . ?
C32 C31 H31 119.6 . . ?
C31 C32 C27 118.80(18) . . ?
C31 C32 C33 122.10(17) . . ?
C33 C32 C27 119.05(17) . . ?
C24 C33 C32 121.28(17) . . ?
C24 C33 H33 119.4 . . ?
C32 C33 H33 119.4 . . ?
F4 C34 F5 107.87(18) . . ?
F4 C34 F6 105.99(17) . . ?
F4 C34 C23 112.21(17) . . ?
F5 C34 F6 106.70(17) . . ?
F5 C34 C23 111.13(17) . . ?
F6 C34 C23 112.58(18) . . ?
C36 C35 C41 118.99(18) . . ?
C40 C35 C36 118.81(19) . . ?
C40 C35 C41 122.17(17) . . ?
C35 C36 H36 119.7 . . ?
C37 C36 C35 120.7(2) . . ?
C37 C36 H36 119.7 . . ?
C36 C37 H37 119.9 . . ?
C36 C37 C38 120.22(19) . . ?
C38 C37 H37 119.9 . . ?
C37 C38 H38 120.1 . . ?
C37 C38 C39 119.7(2) . . ?
C39 C38 H38 120.1 . . ?
C38 C39 H39 119.9 . . ?
C38 C39 C40 120.2(2) . . ?
C40 C39 H39 119.9 . . ?
C35 C40 H40 119.8 . . ?
C39 C40 C35 120.38(18) . . ?
C39 C40 H40 119.8 . . ?
O2 C41 C35 110.30(16) . . ?
N2 C41 O2 127.21(19) . . ?
N2 C41 C35 122.47(18) . . ?
C23 C42 H42A 109.1 . . ?
C23 C42 H42B 109.1 . . ?
H42A C42 H42B 107.8 . . ?
C43 C42 C23 112.57(17) . . ?
C43 C42 H42A 109.1 . . ?
C43 C42 H42B 109.1 . . ?
N2 C43 C42 111.68(18) . . ?
N2 C43 H43 105.2 . . ?
N2 C43 H43A 113.4 . . ?
N2 C43 C44 116.6(2) . . ?
N2 C43 C44A 93.5(3) . . ?
C42 C43 H43 105.2 . . ?
C42 C43 H43A 113.4 . . ?
C42 C43 C44A 109.7(3) . . ?
C44 C43 C42 112.0(2) . . ?
C44 C43 H43 105.2 . . ?
C44A C43 H43A 113.4 . . ?
C43 C44 H44A 109.9 . . ?
C43 C44 H44B 109.9 . . ?
C43 C44 C45 109.0(3) . . ?
H44A C44 H44B 108.3 . . ?
C45 C44 H44A 109.9 . . ?
C45 C44 H44B 109.9 . . ?
C44 C45 H45A 109.5 . . ?
C44 C45 H45B 109.5 . . ?
C44 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C43 C44A H44C 110.1 . . ?
C43 C44A H44D 110.1 . . ?
H44C C44A H44D 108.4 . . ?
C45A C44A C43 108.1(6) . . ?
C45A C44A H44C 110.1 . . ?
C45A C44A H44D 110.1 . . ?
C44A C45A H45D 109.5 . . ?
C44A C45A H45E 109.5 . . ?
C44A C45A H45F 109.5 . . ?
H45D C45A H45E 109.5 . . ?
H45D C45A H45F 109.5 . . ?
H45E C45A H45F 109.5 . . ?
C13 O1 C1 119.88(14) . . ?
C13 N1 C20 120.00(16) . . ?
C14 C00M C13 119.19(17) . . ?
C18 C00M C13 121.59(18) . . ?
C18 C00M C14 119.21(19) . . ?
O1 C1 C2 107.05(14) . . ?
O1 C1 C12 104.52(14) . . ?
O1 C1 C19 111.54(14) . . ?
C2 C1 C12 108.62(14) . . ?
C19 C1 C2 112.77(15) . . ?
C19 C1 C12 111.89(15) . . ?
C3 C2 C1 120.27(16) . . ?
C11 C2 C1 120.33(16) . . ?
C11 C2 C3 119.35(17) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.25(17) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.39(18) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 122.80(18) . . ?
C4 C5 C10 118.56(17) . . ?
C10 C5 C6 118.62(17) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.69(19) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.55(18) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.16(18) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.47(18) . . ?
C10 C9 H9 119.8 . . ?
C5 C10 C11 118.91(17) . . ?
C9 C10 C5 119.48(17) . . ?
C9 C10 C11 121.55(17) . . ?
C2 C11 C10 121.53(17) . . ?
C2 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
F1 C12 F2 106.45(15) . . ?
F1 C12 F3 107.26(15) . . ?
F1 C12 C1 112.74(15) . . ?
F2 C12 C1 111.73(15) . . ?
F3 C12 F2 106.70(15) . . ?
F3 C12 C1 111.60(15) . . ?
O1 C13 C00M 109.90(15) . . ?
N1 C13 O1 127.86(17) . . ?
N1 C13 C00M 122.23(17) . . ?
C00M C14 H14 119.9 . . ?
C15 C14 C00M 120.16(19) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.7(2) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.3(2) . . ?
C18 C17 H17 119.9 . . ?
C00M C18 C17 120.2(2) . . ?
C00M C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C1 C19 H19A 108.8 . . ?
C1 C19 H19B 108.8 . . ?
C1 C19 C20 113.83(15) . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
N1 C20 C19 113.02(15) . . ?
N1 C20 H20 108.3 . . ?
N1 C20 C21 108.33(15) . . ?
C19 C20 H20 108.3 . . ?
C21 C20 C19 110.52(15) . . ?
C21 C20 H20 108.3 . . ?
C20 C21 H21A 108.9 . . ?
C20 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C22 C21 C20 113.22(17) . . ?
C22 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
O2 C23 C24 C25 167.37(16) . . . . ?
O2 C23 C24 C33 -14.6(2) . . . . ?
O2 C23 C34 F4 63.6(2) . . . . ?
O2 C23 C34 F5 -175.53(16) . . . . ?
O2 C23 C34 F6 -55.9(2) . . . . ?
O2 C23 C42 C43 48.3(2) . . . . ?
N2 C43 C44 C45 -48.7(3) . . . . ?
N2 C43 C44A C45A 160.4(5) . . . . ?
C23 O2 C41 N2 2.6(3) . . . . ?
C23 O2 C41 C35 -175.63(15) . . . . ?
C23 C24 C25 C26 177.87(18) . . . . ?
C23 C24 C33 C32 -177.49(16) . . . . ?
C23 C42 C43 N2 -44.1(3) . . . . ?
C23 C42 C43 C44 -176.8(2) . . . . ?
C23 C42 C43 C44A -146.4(3) . . . . ?
C24 C23 C34 F4 -51.2(2) . . . . ?
C24 C23 C34 F5 69.7(2) . . . . ?
C24 C23 C34 F6 -170.69(16) . . . . ?
C24 C23 C42 C43 169.25(19) . . . . ?
C24 C25 C26 C27 0.0(3) . . . . ?
C25 C24 C33 C32 0.6(3) . . . . ?
C25 C26 C27 C28 -179.05(19) . . . . ?
C25 C26 C27 C32 -0.3(3) . . . . ?
C26 C27 C28 C29 176.58(19) . . . . ?
C26 C27 C32 C31 -176.93(17) . . . . ?
C26 C27 C32 C33 0.6(3) . . . . ?
C27 C28 C29 C30 0.3(3) . . . . ?
C27 C32 C33 C24 -0.8(3) . . . . ?
C28 C27 C32 C31 1.9(3) . . . . ?
C28 C27 C32 C33 179.44(17) . . . . ?
C28 C29 C30 C31 1.9(3) . . . . ?
C29 C30 C31 C32 -2.2(3) . . . . ?
C30 C31 C32 C27 0.3(3) . . . . ?
C30 C31 C32 C33 -177.19(18) . . . . ?
C31 C32 C33 C24 176.67(18) . . . . ?
C32 C27 C28 C29 -2.2(3) . . . . ?
C33 C24 C25 C26 -0.2(3) . . . . ?
C34 C23 C24 C25 -79.9(2) . . . . ?
C34 C23 C24 C33 98.1(2) . . . . ?
C34 C23 C42 C43 -68.6(2) . . . . ?
C35 C36 C37 C38 -0.4(3) . . . . ?
C36 C35 C40 C39 -1.4(3) . . . . ?
C36 C35 C41 O2 171.80(16) . . . . ?
C36 C35 C41 N2 -6.5(3) . . . . ?
C36 C37 C38 C39 -1.0(3) . . . . ?
C37 C38 C39 C40 1.2(3) . . . . ?
C38 C39 C40 C35 0.0(3) . . . . ?
C40 C35 C36 C37 1.6(3) . . . . ?
C40 C35 C41 O2 -6.2(2) . . . . ?
C40 C35 C41 N2 175.43(19) . . . . ?
C41 O2 C23 C24 -151.78(15) . . . . ?
C41 O2 C23 C34 93.41(19) . . . . ?
C41 O2 C23 C42 -28.1(2) . . . . ?
C41 N2 C43 C42 19.3(3) . . . . ?
C41 N2 C43 C44 149.7(2) . . . . ?
C41 N2 C43 C44A 132.1(4) . . . . ?
C41 C35 C36 C37 -176.52(17) . . . . ?
C41 C35 C40 C39 176.67(17) . . . . ?
C42 C23 C24 C25 44.8(2) . . . . ?
C42 C23 C24 C33 -137.13(18) . . . . ?
C42 C23 C34 F4 -176.01(17) . . . . ?
C42 C23 C34 F5 -55.1(2) . . . . ?
C42 C23 C34 F6 64.5(2) . . . . ?
C42 C43 C44 C45 81.6(3) . . . . ?
C42 C43 C44A C45A -85.1(6) . . . . ?
C43 N2 C41 O2 2.3(3) . . . . ?
C43 N2 C41 C35 -179.6(2) . . . . ?
O1 C1 C2 C3 165.63(15) . . . . ?
O1 C1 C2 C11 -17.1(2) . . . . ?
O1 C1 C12 F1 58.07(18) . . . . ?
O1 C1 C12 F2 -61.77(18) . . . . ?
O1 C1 C12 F3 178.86(14) . . . . ?
O1 C1 C19 C20 41.0(2) . . . . ?
N1 C20 C21 C22 163.63(16) . . . . ?
C00M C14 C15 C16 -1.6(3) . . . . ?
C1 O1 C13 N1 2.4(3) . . . . ?
C1 O1 C13 C00M -176.98(15) . . . . ?
C1 C2 C3 C4 175.86(17) . . . . ?
C1 C2 C11 C10 -176.09(16) . . . . ?
C1 C19 C20 N1 -39.3(2) . . . . ?
C1 C19 C20 C21 -160.94(15) . . . . ?
C2 C1 C12 F1 -55.94(19) . . . . ?
C2 C1 C12 F2 -175.78(15) . . . . ?
C2 C1 C12 F3 64.85(19) . . . . ?
C2 C1 C19 C20 161.53(15) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C2 C11 C10 1.3(3) . . . . ?
C3 C4 C5 C6 -177.61(18) . . . . ?
C3 C4 C5 C10 0.5(3) . . . . ?
C4 C5 C6 C7 176.39(18) . . . . ?
C4 C5 C10 C9 -177.93(17) . . . . ?
C4 C5 C10 C11 -0.8(3) . . . . ?
C5 C6 C7 C8 1.6(3) . . . . ?
C5 C10 C11 C2 -0.1(3) . . . . ?
C6 C5 C10 C9 0.3(3) . . . . ?
C6 C5 C10 C11 177.46(16) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 C10 -1.5(3) . . . . ?
C8 C9 C10 C5 1.3(3) . . . . ?
C8 C9 C10 C11 -175.75(17) . . . . ?
C9 C10 C11 C2 176.97(17) . . . . ?
C10 C5 C6 C7 -1.8(3) . . . . ?
C11 C2 C3 C4 -1.5(3) . . . . ?
C12 C1 C2 C3 -82.0(2) . . . . ?
C12 C1 C2 C11 95.29(19) . . . . ?
C12 C1 C19 C20 -75.66(19) . . . . ?
C13 O1 C1 C2 -147.14(15) . . . . ?
C13 O1 C1 C12 97.74(17) . . . . ?
C13 O1 C1 C19 -23.3(2) . . . . ?
C13 N1 C20 C19 19.0(2) . . . . ?
C13 N1 C20 C21 141.85(18) . . . . ?
C13 C00M C14 C15 -177.71(17) . . . . ?
C13 C00M C18 C17 179.1(2) . . . . ?
C14 C00M C13 O1 163.52(16) . . . . ?
C14 C00M C13 N1 -15.9(3) . . . . ?
C14 C00M C18 C17 -0.1(4) . . . . ?
C14 C15 C16 C17 0.4(4) . . . . ?
C15 C16 C17 C18 1.0(4) . . . . ?
C16 C17 C18 C00M -1.1(5) . . . . ?
C18 C00M C13 O1 -15.6(3) . . . . ?
C18 C00M C13 N1 164.9(2) . . . . ?
C18 C00M C14 C15 1.4(3) . . . . ?
C19 C1 C2 C3 42.6(2) . . . . ?
C19 C1 C2 C11 -140.09(17) . . . . ?
C19 C1 C12 F1 178.92(15) . . . . ?
C19 C1 C12 F2 59.1(2) . . . . ?
C19 C1 C12 F3 -60.3(2) . . . . ?
C19 C20 C21 C22 -72.0(2) . . . . ?
C20 N1 C13 O1 0.1(3) . . . . ?
C20 N1 C13 C00M 179.39(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 1.625
_oxdiff_exptl_absorpt_empirical_full_min 0.706
####################################################################### 
# 
# 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_a230509c
_database_code_depnum_ccdc_archive 'CCDC 2265601'
loop_
_audit_author_name
_audit_author_address
aa
;a
China
;
_audit_update_record             
;
2023-05-26 deposited with the CCDC.	2023-09-21 downloaded from the CCDC.
;
_audit_creation_date             2023-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H23 F2 N O'
_chemical_formula_sum            'C23 H23 F2 N O'
_chemical_formula_weight         367.42
_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      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                   20.5335(14)
_cell_length_b                   9.8096(6)
_cell_length_c                   9.9263(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.145(6)
_cell_angle_gamma                90
_cell_volume                     1999.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4987
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3860
_cell_measurement_theta_min      4.4330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (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    1.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            15300
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.064
_diffrn_reflns_theta_max         67.064
_diffrn_reflns_theta_min         2.152
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  29.00   1.00    4.76    --  -41.49  38.00   0.00   94
  2  ω    -21.00  33.00   1.00    4.76    --   41.49 -77.00-150.00   54
  3  ω     30.00  58.00   1.00    4.76    --   41.49-125.00 -90.00   28
  4  ω    113.00 173.00   1.00   19.05    --  105.20 125.00-120.00   60
  5  ω    102.00 171.00   1.00   19.05    --  105.20 125.00  60.00   69
  6  ω     87.00 178.00   1.00   19.05    --  105.20  45.00 -90.00   91
  7  ω    135.00 161.00   1.00   19.05    --  105.20 114.00  99.00   26
  8  ω    127.00 153.00   1.00   19.05    --  105.20  77.00   0.00   26
  9  ω     86.00 112.00   1.00   19.05    --  105.20-125.00   0.00   26
 10  ω     30.00 124.00   1.00   19.05    --  105.20 -30.00 -60.00   94
 11  ω     30.00  56.00   1.00    4.76    --   41.49  38.00-180.00   26
 12  ω      7.00 108.00   1.00    4.76    --   41.49  19.00  30.00  101
 13  ω     49.00  77.00   1.00    4.76    --   41.49-125.00  30.00   28
 14  ω     30.00 114.00   1.00    4.76    --   41.49  38.00  90.00   84
 15  ω     64.00  94.00   1.00   19.05    --  105.20 -77.00-150.00   30
 16  ω     33.00  59.00   1.00   19.05    --  105.20-125.00-120.00   26
 17  ω    143.00 178.00   1.00   19.05    --  105.20  30.00 120.00   35
 18  ω     76.00 105.00   1.00   19.05    --  105.20 -94.00  90.00   29
 19  ω     46.00  88.00   1.00   19.05    --  105.20 -94.00  30.00   42
 20  ω     77.00 158.00   1.00   19.05    --  105.20  30.00-180.00   81
 21  ω     29.00  73.00   1.00   19.05    --  105.20 -94.00  90.00   44
 22  ω    108.00 134.00   1.00   19.05    --  105.20  77.00 -60.00   26
 23  ω     43.00 109.00   1.00   19.05    --  105.20-114.00   9.00   66
 24  ω    130.00 156.00   1.00   19.05    --  105.20  77.00  60.00   26
 25  ω     78.00 112.00   1.00   19.05    --  105.20-125.00-120.00   34
 26  ω    109.00 176.00   1.00   19.05    --  105.20  77.00  30.00   67
 27  ω     86.00 138.00   1.00   19.05    --  105.20  30.00 120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0419288000
_diffrn_orient_matrix_UB_12      -0.1100043000
_diffrn_orient_matrix_UB_13      0.0691600000
_diffrn_orient_matrix_UB_21      0.0608654000
_diffrn_orient_matrix_UB_22      0.0899403000
_diffrn_orient_matrix_UB_23      -0.0178626000
_diffrn_orient_matrix_UB_31      -0.0129770000
_diffrn_orient_matrix_UB_32      0.0668635000
_diffrn_orient_matrix_UB_33      0.1377661000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2748
_reflns_number_total             3559
_reflns_odcompleteness_completeness 99.89
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0016(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3559
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1325
_refine_ls_R_factor_gt           0.1165
_refine_ls_restrained_S_all      1.032
_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)+(0.1154P)²+5.4556P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3155
_refine_ls_wR_factor_ref         0.3255
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C005(H005), C00C(H00D), C00G(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C), C00F(H00E,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 N002(H002), C009(H009), C00A(H00A), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q)
2.d Idealised Me refined as rotating group:
 C00R(H00R,H00S,H00T)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.70350(19) 0.8117(5) 0.5771(3) 0.0776(12) Uani 1 1 d . . . . .
N002 N 0.68577(18) 0.7419(4) 0.3636(4) 0.0541(10) Uani 1 1 d . . . . .
H002 H 0.7030 0.7298 0.2857 0.065 Uiso 1 1 calc R . . . .
F003 F 0.5302(2) 0.3452(5) 0.4662(5) 0.1216(16) Uani 1 1 d . . . . .
C004 C 0.7233(2) 0.7886(5) 0.4621(5) 0.0566(12) Uani 1 1 d . . . . .
C005 C 0.6167(2) 0.7096(6) 0.3799(5) 0.0557(12) Uani 1 1 d . . . . .
H005 H 0.6060 0.7229 0.4752 0.067 Uiso 1 1 calc R . . . .
F006 F 0.6140(2) 0.2416(5) 0.5425(6) 0.1277(18) Uani 1 1 d . . . . .
C007 C 0.7935(2) 0.8144(6) 0.4290(5) 0.0588(13) Uani 1 1 d . . . . .
C008 C 0.8169(3) 0.4210(6) 0.5003(6) 0.0694(15) Uani 1 1 d . . . . .
C009 C 0.8279(3) 0.7360(6) 0.3391(6) 0.0696(15) Uani 1 1 d . . . . .
H009 H 0.8067 0.6675 0.2913 0.083 Uiso 1 1 calc R . . . .
C00A C 0.7473(3) 0.4518(6) 0.5190(6) 0.0730(15) Uani 1 1 d . . . . .
H00A H 0.7337 0.4889 0.6005 0.088 Uiso 1 1 calc R . . . .
C00B C 0.6029(2) 0.5606(6) 0.3459(5) 0.0646(14) Uani 1 1 d . . . . .
H00B H 0.5561 0.5478 0.3414 0.078 Uiso 1 1 calc R . . . .
H00C H 0.6204 0.5415 0.2571 0.078 Uiso 1 1 calc R . . . .
C00C C 0.6307(3) 0.4586(6) 0.4437(6) 0.0665(14) Uani 1 1 d . . . . .
H00D H 0.6260 0.4974 0.5341 0.080 Uiso 1 1 calc R . . . .
C00D C 0.7032(3) 0.4283(6) 0.4233(6) 0.0712(15) Uani 1 1 d . . . . .
C00E C 0.8326(3) 0.3638(6) 0.3752(7) 0.0810(17) Uani 1 1 d . . . . .
C00F C 0.5749(3) 0.8085(7) 0.2987(6) 0.0778(17) Uani 1 1 d . . . . .
H00E H 0.5867 0.8020 0.2044 0.093 Uiso 1 1 calc R . . . .
H00F H 0.5295 0.7821 0.3069 0.093 Uiso 1 1 calc R . . . .
C00G C 0.5934(3) 0.3259(7) 0.4418(8) 0.0860(19) Uani 1 1 d . . . . .
H00G H 0.5989 0.2809 0.3544 0.103 Uiso 1 1 calc R . . . .
C00H C 0.8633(3) 0.4462(8) 0.5951(8) 0.094(2) Uani 1 1 d . . . . .
H00H H 0.8515 0.4856 0.6766 0.112 Uiso 1 1 calc R . . . .
C00I C 0.9030(4) 0.3317(8) 0.3517(9) 0.100(2) Uani 1 1 d . . . . .
H00I H 0.9171 0.2952 0.2704 0.120 Uiso 1 1 calc R . . . .
C00J C 0.7874(4) 0.3405(7) 0.2766(7) 0.093(2) Uani 1 1 d . . . . .
H00J H 0.8003 0.3034 0.1947 0.112 Uiso 1 1 calc R . . . .
C00K C 0.9451(3) 0.3577(8) 0.4531(10) 0.097(2) Uani 1 1 d . . . . .
H00K H 0.9889 0.3363 0.4421 0.116 Uiso 1 1 calc R . . . .
C00L C 0.7236(3) 0.3712(7) 0.2975(7) 0.0837(18) Uani 1 1 d . . . . .
H00L H 0.6931 0.3551 0.2300 0.100 Uiso 1 1 calc R . . . .
C00M C 0.8938(3) 0.7585(8) 0.3192(8) 0.090(2) Uani 1 1 d . . . . .
H00M H 0.9172 0.7022 0.2615 0.108 Uiso 1 1 calc R . . . .
C00N C 0.9248(3) 0.8644(11) 0.3850(9) 0.107(3) Uani 1 1 d . . . . .
H00N H 0.9689 0.8798 0.3705 0.129 Uiso 1 1 calc R . . . .
C00O C 0.8249(3) 0.9189(8) 0.4957(6) 0.087(2) Uani 1 1 d . . . . .
H00O H 0.8025 0.9721 0.5576 0.105 Uiso 1 1 calc R . . . .
C00P C 0.9247(4) 0.4155(9) 0.5730(10) 0.104(2) Uani 1 1 d . . . . .
H00P H 0.9553 0.4331 0.6400 0.125 Uiso 1 1 calc R . . . .
C00Q C 0.8917(4) 0.9450(10) 0.4694(8) 0.108(3) Uani 1 1 d . . . . .
H00Q H 0.9124 1.0181 0.5109 0.129 Uiso 1 1 calc R . . . .
C00R C 0.5826(4) 0.9554(8) 0.3448(9) 0.110(3) Uani 1 1 d . . . . .
H00R H 0.5534 1.0127 0.2945 0.165 Uiso 1 1 calc GR . . . .
H00S H 0.6266 0.9845 0.3301 0.165 Uiso 1 1 calc GR . . . .
H00T H 0.5726 0.9619 0.4390 0.165 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C004 1.234(6) . ?
N002 H002 0.8600 . ?
N002 C004 1.325(6) . ?
N002 C005 1.462(6) . ?
F003 C00G 1.335(8) . ?
C004 C007 1.500(7) . ?
C005 H005 0.9800 . ?
C005 C00B 1.527(8) . ?
C005 C00F 1.525(7) . ?
F006 C00G 1.364(8) . ?
C007 C009 1.374(8) . ?
C007 C00O 1.380(8) . ?
C008 C00A 1.474(8) . ?
C008 C00E 1.400(9) . ?
C008 C00H 1.360(8) . ?
C009 H009 0.9300 . ?
C009 C00M 1.387(8) . ?
C00A H00A 0.9300 . ?
C00A C00D 1.330(8) . ?
C00B H00B 0.9700 . ?
C00B H00C 0.9700 . ?
C00B C00C 1.505(8) . ?
C00C H00D 0.9800 . ?
C00C C00D 1.533(8) . ?
C00C C00G 1.511(8) . ?
C00D C00L 1.431(9) . ?
C00E C00I 1.498(10) . ?
C00E C00J 1.367(9) . ?
C00F H00E 0.9700 . ?
C00F H00F 0.9700 . ?
C00F C00R 1.521(10) . ?
C00G H00G 0.9800 . ?
C00H H00H 0.9300 . ?
C00H C00P 1.314(10) . ?
C00I H00I 0.9300 . ?
C00I C00K 1.350(10) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.360(9) . ?
C00K H00K 0.9300 . ?
C00K C00P 1.384(11) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00N 1.381(12) . ?
C00N H00N 0.9300 . ?
C00N C00Q 1.339(12) . ?
C00O H00O 0.9300 . ?
C00O C00Q 1.419(10) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9600 . ?
C00R H00S 0.9600 . ?
C00R H00T 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C004 N002 H002 118.1 . . ?
C004 N002 C005 123.7(4) . . ?
C005 N002 H002 118.1 . . ?
O001 C004 N002 123.6(5) . . ?
O001 C004 C007 119.4(4) . . ?
N002 C004 C007 117.0(4) . . ?
N002 C005 H005 107.4 . . ?
N002 C005 C00B 111.2(4) . . ?
N002 C005 C00F 110.5(4) . . ?
C00B C005 H005 107.4 . . ?
C00F C005 H005 107.4 . . ?
C00F C005 C00B 112.8(4) . . ?
C009 C007 C004 122.9(5) . . ?
C009 C007 C00O 119.1(5) . . ?
C00O C007 C004 118.0(5) . . ?
C00E C008 C00A 114.8(5) . . ?
C00H C008 C00A 123.6(6) . . ?
C00H C008 C00E 121.6(6) . . ?
C007 C009 H009 119.8 . . ?
C007 C009 C00M 120.5(6) . . ?
C00M C009 H009 119.8 . . ?
C008 C00A H00A 118.9 . . ?
C00D C00A C008 122.2(6) . . ?
C00D C00A H00A 118.9 . . ?
C005 C00B H00B 108.5 . . ?
C005 C00B H00C 108.5 . . ?
H00B C00B H00C 107.5 . . ?
C00C C00B C005 115.1(4) . . ?
C00C C00B H00B 108.5 . . ?
C00C C00B H00C 108.5 . . ?
C00B C00C H00D 107.1 . . ?
C00B C00C C00D 114.2(5) . . ?
C00B C00C C00G 111.9(5) . . ?
C00D C00C H00D 107.1 . . ?
C00G C00C H00D 107.1 . . ?
C00G C00C C00D 108.9(5) . . ?
C00A C00D C00C 122.1(6) . . ?
C00A C00D C00L 119.4(6) . . ?
C00L C00D C00C 118.5(5) . . ?
C008 C00E C00I 116.5(6) . . ?
C00J C00E C008 123.0(7) . . ?
C00J C00E C00I 120.5(7) . . ?
C005 C00F H00E 109.1 . . ?
C005 C00F H00F 109.1 . . ?
H00E C00F H00F 107.8 . . ?
C00R C00F C005 112.7(5) . . ?
C00R C00F H00E 109.1 . . ?
C00R C00F H00F 109.1 . . ?
F003 C00G F006 104.6(6) . . ?
F003 C00G C00C 111.7(6) . . ?
F003 C00G H00G 109.8 . . ?
F006 C00G C00C 110.9(5) . . ?
F006 C00G H00G 109.8 . . ?
C00C C00G H00G 109.8 . . ?
C008 C00H H00H 119.6 . . ?
C00P C00H C008 120.9(8) . . ?
C00P C00H H00H 119.6 . . ?
C00E C00I H00I 121.3 . . ?
C00K C00I C00E 117.5(8) . . ?
C00K C00I H00I 121.3 . . ?
C00E C00J H00J 119.8 . . ?
C00L C00J C00E 120.4(7) . . ?
C00L C00J H00J 119.8 . . ?
C00I C00K H00K 119.2 . . ?
C00I C00K C00P 121.6(7) . . ?
C00P C00K H00K 119.2 . . ?
C00D C00L H00L 119.9 . . ?
C00J C00L C00D 120.2(6) . . ?
C00J C00L H00L 119.9 . . ?
C009 C00M H00M 120.0 . . ?
C00N C00M C009 120.0(7) . . ?
C00N C00M H00M 120.0 . . ?
C00M C00N H00N 119.8 . . ?
C00Q C00N C00M 120.4(7) . . ?
C00Q C00N H00N 119.8 . . ?
C007 C00O H00O 120.1 . . ?
C007 C00O C00Q 119.8(7) . . ?
C00Q C00O H00O 120.1 . . ?
C00H C00P C00K 122.0(8) . . ?
C00H C00P H00P 119.0 . . ?
C00K C00P H00P 119.0 . . ?
C00N C00Q C00O 120.0(7) . . ?
C00N C00Q H00Q 120.0 . . ?
C00O C00Q H00Q 120.0 . . ?
C00F C00R H00R 109.5 . . ?
C00F C00R H00S 109.5 . . ?
C00F C00R H00T 109.5 . . ?
H00R C00R H00S 109.5 . . ?
H00R C00R H00T 109.5 . . ?
H00S C00R H00T 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C004 C007 C009 146.2(5) . . . . ?
O001 C004 C007 C00O -31.6(8) . . . . ?
N002 C004 C007 C009 -34.0(7) . . . . ?
N002 C004 C007 C00O 148.2(5) . . . . ?
N002 C005 C00B C00C 68.9(5) . . . . ?
N002 C005 C00F C00R -61.9(7) . . . . ?
C004 N002 C005 C00B -121.1(5) . . . . ?
C004 N002 C005 C00F 112.8(5) . . . . ?
C004 C007 C009 C00M -175.5(5) . . . . ?
C004 C007 C00O C00Q 178.7(6) . . . . ?
C005 N002 C004 O001 -1.2(8) . . . . ?
C005 N002 C004 C007 179.0(4) . . . . ?
C005 C00B C00C C00D -80.3(6) . . . . ?
C005 C00B C00C C00G 155.3(5) . . . . ?
C007 C009 C00M C00N -3.1(10) . . . . ?
C007 C00O C00Q C00N -3.1(12) . . . . ?
C008 C00A C00D C00C 179.1(5) . . . . ?
C008 C00A C00D C00L 0.0(9) . . . . ?
C008 C00E C00I C00K 1.3(9) . . . . ?
C008 C00E C00J C00L -0.9(11) . . . . ?
C008 C00H C00P C00K 0.6(12) . . . . ?
C009 C007 C00O C00Q 0.8(9) . . . . ?
C009 C00M C00N C00Q 0.8(12) . . . . ?
C00A C008 C00E C00I 179.7(5) . . . . ?
C00A C008 C00E C00J 1.2(9) . . . . ?
C00A C008 C00H C00P 179.5(6) . . . . ?
C00A C00D C00L C00J 0.4(10) . . . . ?
C00B C005 C00F C00R 172.9(5) . . . . ?
C00B C00C C00D C00A 119.8(6) . . . . ?
C00B C00C C00D C00L -61.1(7) . . . . ?
C00B C00C C00G F003 -56.0(7) . . . . ?
C00B C00C C00G F006 -172.3(5) . . . . ?
C00C C00D C00L C00J -178.7(6) . . . . ?
C00D C00C C00G F003 176.7(5) . . . . ?
C00D C00C C00G F006 60.4(7) . . . . ?
C00E C008 C00A C00D -0.8(8) . . . . ?
C00E C008 C00H C00P -1.1(10) . . . . ?
C00E C00I C00K C00P -1.8(11) . . . . ?
C00E C00J C00L C00D 0.0(11) . . . . ?
C00F C005 C00B C00C -166.3(4) . . . . ?
C00G C00C C00D C00A -114.3(6) . . . . ?
C00G C00C C00D C00L 64.8(7) . . . . ?
C00H C008 C00A C00D 178.7(6) . . . . ?
C00H C008 C00E C00I 0.2(9) . . . . ?
C00H C008 C00E C00J -178.3(7) . . . . ?
C00I C00E C00J C00L -179.2(7) . . . . ?
C00I C00K C00P C00H 1.0(12) . . . . ?
C00J C00E C00I C00K 179.7(7) . . . . ?
C00M C00N C00Q C00O 2.3(12) . . . . ?
C00O C007 C009 C00M 2.3(9) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2023-05-09
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.160
_oxdiff_exptl_absorpt_empirical_full_min 0.434
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2265605'
loop_
_audit_author_name
_audit_author_address
bb
;bbbb
China
;
_audit_update_record             
;
2023-05-26 deposited with the CCDC.	2023-09-21 downloaded from the CCDC.
;
_audit_creation_date             2023-05-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H35 F2 N O S'
_chemical_formula_sum            'C33 H35 F2 N O S'
_chemical_formula_weight         531.68
_chemical_absolute_configuration ad
_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 0.0137 0.0067 '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 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.0610(5)
_cell_length_b                   19.1206(9)
_cell_length_c                   14.7518(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2837.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6856
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      55.23
_cell_measurement_theta_min      3.29
_shelx_estimated_absorpt_T_max   0.918
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.865
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.6551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0865 before and 0.0629 after correction.
The Ratio of minimum to maximum transmission is 0.8714.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0868
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            41287
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.575
_diffrn_reflns_theta_min         3.292
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON II'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   MetalJet
_diffrn_source_current           2.85
_diffrn_source_power             0.1986165
_diffrn_source_type              'Liquid Metal source'
_diffrn_source_voltage           69.69
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.913
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                3942
_reflns_number_total             6391
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX4 V2022.10-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.45(4)
_refine_ls_extinction_coef       0.0019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         6391
_refine_ls_number_restraints     112
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.017
_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)+(0.0428P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.1118
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.55(4)
 0.45(4)
2. 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
3. Restrained distances
 C31A-C30 \\sim C31B-C30 \\sim C33B-C30 \\sim C33A-C30 \\sim C32B-C30 \\sim
C32A-C30
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
C30 \\sim C31B \\sim C32B \\sim C33B \\sim C32A \\sim C31A \\sim C33A: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(C32A) \\sim Ueq, Uanis(C31A) \\sim Ueq, Uanis(C31B) \\sim Ueq,
Uanis(C33B) \\sim Ueq, Uanis(C33A) \\sim Ueq, Uanis(C32B) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(C32B)=Sof(H32A)=Sof(H32B)=Sof(H32C)=Sof(C33B)=Sof(H33A)=Sof(H33B)=
 Sof(H33C)=Sof(C31A)=Sof(H31D)=Sof(H31E)=Sof(H31F)=1-FVAR(1)
 Sof(C31B)=Sof(H31A)=Sof(H31B)=Sof(H31C)=Sof(C32A)=Sof(H32D)=Sof(H32E)=
 Sof(H32F)=Sof(C33A)=Sof(H33D)=Sof(H33E)=Sof(H33F)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C12(H12), C8(H8)
6.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C9(H9A,H9B)
6.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C22(H22), C14(H14), C1(H1A), C4(H4), C3(H3), C28(H28), C2(H2),
 C15(H15), C29(H29), C17(H17), C20(H20), C26(H26), C25(H25), C19(H19), C18(H18)
6.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C31B(H31A,H31B,H31C), C32B(H32A,H32B,H32C), C33B(H33A,
 H33B,H33C), C32A(H32D,H32E,H32F), C31A(H31D,H31E,H31F), C33A(H33D,H33E,H33F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.64119(12) 0.46216(7) 0.48370(10) 0.0627(4) Uani 1 1 d . . . . .
F1 F 0.4875(2) 0.56691(13) 0.52433(17) 0.0534(6) Uani 1 1 d . . . . .
F2 F 0.5588(2) 0.50982(13) 0.64024(16) 0.0525(7) Uani 1 1 d . . . . .
O1 O 0.9551(3) 0.75835(15) 0.50510(17) 0.0449(7) Uani 1 1 d . . . . .
N1 N 0.7355(3) 0.74100(17) 0.5303(2) 0.0361(8) Uani 1 1 d . . . . .
C6 C 0.8061(4) 0.7867(2) 0.3857(2) 0.0355(9) Uani 1 1 d . . . . .
C7 C 0.8380(4) 0.76105(19) 0.4790(3) 0.0356(8) Uani 1 1 d . . . . .
C13 C 0.8437(4) 0.5566(2) 0.5941(3) 0.0415(10) Uani 1 1 d . . . . .
C21 C 0.9846(4) 0.4876(2) 0.6940(3) 0.0461(11) Uani 1 1 d . . . . .
C5 C 0.8873(4) 0.8371(2) 0.3468(3) 0.0430(10) Uani 1 1 d . . . . .
H5 H 0.959086 0.856162 0.380577 0.052 Uiso 1 1 calc R U . . .
C12 C 0.7098(4) 0.5879(2) 0.5667(3) 0.0407(10) Uani 1 1 d . . . . .
H12 H 0.722535 0.609706 0.505778 0.049 Uiso 1 1 calc R U . . .
C8 C 0.7470(4) 0.7131(2) 0.6224(2) 0.0368(9) Uani 1 1 d . . . . .
H8 H 0.842348 0.701864 0.634873 0.044 Uiso 1 1 calc R U . . .
C23 C 0.5993(4) 0.5341(2) 0.5566(3) 0.0451(11) Uani 1 1 d . . . . .
C22 C 0.8590(4) 0.5140(2) 0.6671(3) 0.0431(10) Uani 1 1 d . . . . .
H22 H 0.782634 0.501350 0.701302 0.052 Uiso 1 1 calc R U . . .
C14 C 0.9579(4) 0.5755(3) 0.5446(3) 0.0530(11) Uani 1 1 d . . . . .
H14 H 0.949446 0.605494 0.493540 0.064 Uiso 1 1 calc R U . . .
C11 C 0.6650(4) 0.6463(2) 0.6307(3) 0.0413(10) Uani 1 1 d . . . . .
H11A H 0.570773 0.657489 0.617987 0.050 Uiso 1 1 calc R U . . .
H11B H 0.670546 0.629176 0.693918 0.050 Uiso 1 1 calc R U . . .
C9 C 0.6997(4) 0.7680(2) 0.6908(3) 0.0441(10) Uani 1 1 d . . . . .
H9A H 0.610838 0.784877 0.672101 0.053 Uiso 1 1 calc R U . . .
H9B H 0.690101 0.745420 0.750833 0.053 Uiso 1 1 calc R U . . .
C1 C 0.7020(4) 0.7590(2) 0.3346(3) 0.0479(11) Uani 1 1 d . . . . .
H1A H 0.644762 0.724952 0.360607 0.058 Uiso 1 1 calc R U . . .
C4 C 0.8643(5) 0.8597(2) 0.2589(3) 0.0525(12) Uani 1 1 d . . . . .
H4 H 0.919166 0.894925 0.233084 0.063 Uiso 1 1 calc R U . . .
C24 C 0.4793(4) 0.4249(2) 0.4716(3) 0.0505(11) Uani 1 1 d . . . . .
C27 C 0.2219(4) 0.3677(2) 0.4551(3) 0.0462(11) Uani 1 1 d . . . . .
C16 C 1.0974(4) 0.5070(2) 0.6435(3) 0.0522(12) Uani 1 1 d . . . . .
C3 C 0.7625(5) 0.8314(3) 0.2091(3) 0.0579(13) Uani 1 1 d . . . . .
H3 H 0.747655 0.846745 0.148633 0.070 Uiso 1 1 calc R U . . .
C30 C 0.0833(5) 0.3360(2) 0.4471(3) 0.0551(12) Uani 1 1 d D U . . .
C28 C 0.3091(5) 0.3468(2) 0.5230(3) 0.0536(11) Uani 1 1 d . . . . .
H28 H 0.281138 0.312248 0.565151 0.064 Uiso 1 1 calc R U . . .
C2 C 0.6816(5) 0.7808(3) 0.2464(3) 0.0596(13) Uani 1 1 d . . . . .
H2 H 0.611862 0.760970 0.211429 0.071 Uiso 1 1 calc R U . . .
C15 C 1.0809(5) 0.5514(3) 0.5688(4) 0.0580(13) Uani 1 1 d . . . . .
H15 H 1.156391 0.564929 0.534373 0.070 Uiso 1 1 calc R U . . .
C29 C 0.4356(5) 0.3750(2) 0.5312(3) 0.0555(12) Uani 1 1 d . . . . .
H29 H 0.492482 0.359475 0.578572 0.067 Uiso 1 1 calc R U . . .
C17 C 1.2244(5) 0.4810(3) 0.6700(4) 0.0679(15) Uani 1 1 d . . . . .
H17 H 1.301638 0.494665 0.637467 0.081 Uiso 1 1 calc R U . . .
C20 C 0.9997(5) 0.4423(3) 0.7690(3) 0.0620(14) Uani 1 1 d . . . . .
H20 H 0.924627 0.428580 0.803754 0.074 Uiso 1 1 calc R U . . .
C10 C 0.7918(5) 0.8303(2) 0.7001(3) 0.0527(12) Uani 1 1 d . . . . .
H10A H 0.805383 0.851753 0.640492 0.079 Uiso 1 1 calc R U . . .
H10B H 0.877530 0.814745 0.724437 0.079 Uiso 1 1 calc R U . . .
H10C H 0.752158 0.864572 0.741364 0.079 Uiso 1 1 calc R U . . .
C26 C 0.2698(5) 0.4167(3) 0.3948(3) 0.0652(14) Uani 1 1 d . . . . .
H26 H 0.214300 0.431657 0.346497 0.078 Uiso 1 1 calc R U . . .
C25 C 0.3975(5) 0.4450(3) 0.4025(3) 0.0680(15) Uani 1 1 d . . . . .
H25 H 0.427468 0.478350 0.359394 0.082 Uiso 1 1 calc R U . . .
C19 C 1.1251(6) 0.4181(3) 0.7911(4) 0.0770(17) Uani 1 1 d . . . . .
H19 H 1.135313 0.387845 0.841740 0.092 Uiso 1 1 calc R U . . .
C18 C 1.2352(6) 0.4368(3) 0.7416(4) 0.0768(17) Uani 1 1 d . . . . .
H18 H 1.319858 0.418570 0.757659 0.092 Uiso 1 1 calc R U . . .
C31B C 0.000(2) 0.3440(13) 0.5304(14) 0.072(6) Uani 0.45(2) 1 d D U P A 1
H31A H 0.049015 0.325590 0.582792 0.108 Uiso 0.45(2) 1 calc R U P A 1
H31B H -0.082911 0.318088 0.522971 0.108 Uiso 0.45(2) 1 calc R U P A 1
H31C H -0.019307 0.393646 0.540172 0.108 Uiso 0.45(2) 1 calc R U P A 1
C32B C 0.0816(18) 0.2704(9) 0.3921(12) 0.070(4) Uani 0.55(2) 1 d D U P A 2
H32A H 0.106684 0.281116 0.329421 0.105 Uiso 0.55(2) 1 calc R U P A 2
H32B H -0.007956 0.250200 0.393059 0.105 Uiso 0.55(2) 1 calc R U P A 2
H32C H 0.144844 0.236799 0.417693 0.105 Uiso 0.55(2) 1 calc R U P A 2
C33B C -0.0184(12) 0.3892(8) 0.4089(15) 0.085(5) Uani 0.55(2) 1 d D U P A 2
H33A H -0.017206 0.431713 0.445984 0.128 Uiso 0.55(2) 1 calc R U P A 2
H33B H -0.107613 0.368600 0.410278 0.128 Uiso 0.55(2) 1 calc R U P A 2
H33C H 0.005134 0.400940 0.346257 0.128 Uiso 0.55(2) 1 calc R U P A 2
H1 H 0.660(4) 0.7471(19) 0.510(3) 0.038(11) Uiso 1 1 d . . . . .
C32A C 0.111(2) 0.2564(8) 0.4270(16) 0.073(5) Uani 0.45(2) 1 d D U P A 1
H32D H 0.173508 0.252417 0.376135 0.110 Uiso 0.45(2) 1 calc R U P A 1
H32E H 0.027829 0.232880 0.411573 0.110 Uiso 0.45(2) 1 calc R U P A 1
H32F H 0.150164 0.234428 0.480880 0.110 Uiso 0.45(2) 1 calc R U P A 1
C31A C 0.0316(18) 0.3174(10) 0.5433(9) 0.065(4) Uani 0.55(2) 1 d D U P A 2
H31D H 0.085646 0.279572 0.568756 0.097 Uiso 0.55(2) 1 calc R U P A 2
H31E H -0.061289 0.302241 0.539380 0.097 Uiso 0.55(2) 1 calc R U P A 2
H31F H 0.037743 0.358680 0.582453 0.097 Uiso 0.55(2) 1 calc R U P A 2
C33A C 0.012(2) 0.3625(12) 0.3617(14) 0.084(5) Uani 0.45(2) 1 d D U P A 1
H33D H 0.008250 0.413675 0.362962 0.126 Uiso 0.45(2) 1 calc R U P A 1
H33E H -0.077964 0.343386 0.359636 0.126 Uiso 0.45(2) 1 calc R U P A 1
H33F H 0.061566 0.347292 0.307796 0.126 Uiso 0.45(2) 1 calc R U P A 1


_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
S1 C23 1.796(5) . ?
S1 C24 1.787(5) . ?
F1 C23 1.372(5) . ?
F2 C23 1.380(5) . ?
O1 C7 1.241(4) . ?
N1 C7 1.335(5) . ?
N1 C8 1.465(5) . ?
N1 H1 0.82(4) . ?
C6 C7 1.495(5) . ?
C6 C5 1.388(5) . ?
C6 C1 1.395(6) . ?
C13 C12 1.528(6) . ?
C13 C22 1.360(6) . ?
C13 C14 1.409(6) . ?
C21 C22 1.417(6) . ?
C21 C16 1.408(6) . ?
C21 C20 1.413(6) . ?
C5 H5 0.9500 . ?
C5 C4 1.387(6) . ?
C12 H12 1.0000 . ?
C12 C23 1.521(6) . ?
C12 C11 1.530(6) . ?
C8 H8 1.0000 . ?
C8 C11 1.525(5) . ?
C8 C9 1.531(5) . ?
C22 H22 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.368(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.515(6) . ?
C1 H1A 0.9500 . ?
C1 C2 1.382(6) . ?
C4 H4 0.9500 . ?
C4 C3 1.372(6) . ?
C24 C29 1.372(6) . ?
C24 C25 1.364(7) . ?
C27 C30 1.525(6) . ?
C27 C28 1.390(6) . ?
C27 C26 1.379(6) . ?
C16 C15 1.401(7) . ?
C16 C17 1.425(6) . ?
C3 H3 0.9500 . ?
C3 C2 1.379(7) . ?
C30 C31B 1.494(15) . ?
C30 C32B 1.494(12) . ?
C30 C33B 1.549(11) . ?
C30 C32A 1.576(15) . ?
C30 C31A 1.553(13) . ?
C30 C33A 1.534(13) . ?
C28 H28 0.9500 . ?
C28 C29 1.387(6) . ?
C2 H2 0.9500 . ?
C15 H15 0.9500 . ?
C29 H29 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.357(8) . ?
C20 H20 0.9500 . ?
C20 C19 1.382(7) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C26 H26 0.9500 . ?
C26 C25 1.399(7) . ?
C25 H25 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.375(8) . ?
C18 H18 0.9500 . ?
C31B H31A 0.9800 . ?
C31B H31B 0.9800 . ?
C31B H31C 0.9800 . ?
C32B H32A 0.9800 . ?
C32B H32B 0.9800 . ?
C32B H32C 0.9800 . ?
C33B H33A 0.9800 . ?
C33B H33B 0.9800 . ?
C33B H33C 0.9800 . ?
C32A H32D 0.9800 . ?
C32A H32E 0.9800 . ?
C32A H32F 0.9800 . ?
C31A H31D 0.9800 . ?
C31A H31E 0.9800 . ?
C31A H31F 0.9800 . ?
C33A H33D 0.9800 . ?
C33A H33E 0.9800 . ?
C33A H33F 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
C24 S1 C23 98.7(2) . . ?
C7 N1 C8 124.7(3) . . ?
C7 N1 H1 117(3) . . ?
C8 N1 H1 118(3) . . ?
C5 C6 C7 118.8(3) . . ?
C5 C6 C1 118.9(4) . . ?
C1 C6 C7 122.3(4) . . ?
O1 C7 N1 123.0(4) . . ?
O1 C7 C6 120.2(3) . . ?
N1 C7 C6 116.8(3) . . ?
C22 C13 C12 122.9(4) . . ?
C22 C13 C14 118.2(4) . . ?
C14 C13 C12 118.8(4) . . ?
C16 C21 C22 118.5(4) . . ?
C16 C21 C20 119.3(4) . . ?
C20 C21 C22 122.3(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.3(4) . . ?
C4 C5 H5 119.8 . . ?
C13 C12 H12 106.7 . . ?
C13 C12 C11 112.5(3) . . ?
C23 C12 C13 114.0(3) . . ?
C23 C12 H12 106.7 . . ?
C23 C12 C11 109.8(3) . . ?
C11 C12 H12 106.7 . . ?
N1 C8 H8 108.9 . . ?
N1 C8 C11 109.7(3) . . ?
N1 C8 C9 109.7(3) . . ?
C11 C8 H8 108.9 . . ?
C11 C8 C9 110.7(3) . . ?
C9 C8 H8 108.9 . . ?
F1 C23 S1 109.6(3) . . ?
F1 C23 F2 102.8(3) . . ?
F1 C23 C12 108.9(3) . . ?
F2 C23 S1 110.3(3) . . ?
F2 C23 C12 110.8(3) . . ?
C12 C23 S1 113.9(3) . . ?
C13 C22 C21 122.4(4) . . ?
C13 C22 H22 118.8 . . ?
C21 C22 H22 118.8 . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.1(5) . . ?
C15 C14 H14 119.5 . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C8 C11 C12 113.8(3) . . ?
C8 C11 H11A 108.8 . . ?
C8 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C8 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 C8 114.1(3) . . ?
C10 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C6 C1 H1A 119.8 . . ?
C2 C1 C6 120.4(4) . . ?
C2 C1 H1A 119.8 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 H4 119.9 . . ?
C29 C24 S1 120.4(4) . . ?
C25 C24 S1 120.8(4) . . ?
C25 C24 C29 118.8(4) . . ?
C28 C27 C30 121.3(4) . . ?
C26 C27 C30 122.6(4) . . ?
C26 C27 C28 116.0(4) . . ?
C21 C16 C17 119.1(5) . . ?
C15 C16 C21 118.7(4) . . ?
C15 C16 C17 122.2(5) . . ?
C4 C3 H3 119.9 . . ?
C4 C3 C2 120.2(4) . . ?
C2 C3 H3 119.9 . . ?
C27 C30 C33B 111.8(6) . . ?
C27 C30 C32A 103.5(9) . . ?
C27 C30 C31A 109.0(8) . . ?
C27 C30 C33A 111.0(7) . . ?
C31B C30 C27 113.9(11) . . ?
C31B C30 C32A 110.7(12) . . ?
C31B C30 C33A 112.5(11) . . ?
C32B C30 C27 112.7(8) . . ?
C32B C30 C33B 110.3(9) . . ?
C32B C30 C31A 107.5(10) . . ?
C33B C30 C31A 105.1(8) . . ?
C33A C30 C32A 104.4(10) . . ?
C27 C28 H28 119.0 . . ?
C29 C28 C27 122.1(4) . . ?
C29 C28 H28 119.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2 120.0 . . ?
C14 C15 C16 121.2(5) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C24 C29 C28 120.5(4) . . ?
C24 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(5) . . ?
C18 C17 H17 119.9 . . ?
C21 C20 H20 120.4 . . ?
C19 C20 C21 119.2(5) . . ?
C19 C20 H20 120.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C27 C26 H26 118.9 . . ?
C27 C26 C25 122.1(5) . . ?
C25 C26 H26 118.9 . . ?
C24 C25 C26 120.4(5) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C20 C19 H19 119.2 . . ?
C18 C19 C20 121.5(6) . . ?
C18 C19 H19 119.2 . . ?
C17 C18 C19 120.7(5) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C30 C31B H31A 109.5 . . ?
C30 C31B H31B 109.5 . . ?
C30 C31B H31C 109.5 . . ?
H31A C31B H31B 109.5 . . ?
H31A C31B H31C 109.5 . . ?
H31B C31B H31C 109.5 . . ?
C30 C32B H32A 109.5 . . ?
C30 C32B H32B 109.5 . . ?
C30 C32B H32C 109.5 . . ?
H32A C32B H32B 109.5 . . ?
H32A C32B H32C 109.5 . . ?
H32B C32B H32C 109.5 . . ?
C30 C33B H33A 109.5 . . ?
C30 C33B H33B 109.5 . . ?
C30 C33B H33C 109.5 . . ?
H33A C33B H33B 109.5 . . ?
H33A C33B H33C 109.5 . . ?
H33B C33B H33C 109.5 . . ?
C30 C32A H32D 109.5 . . ?
C30 C32A H32E 109.5 . . ?
C30 C32A H32F 109.5 . . ?
H32D C32A H32E 109.5 . . ?
H32D C32A H32F 109.5 . . ?
H32E C32A H32F 109.5 . . ?
C30 C31A H31D 109.5 . . ?
C30 C31A H31E 109.5 . . ?
C30 C31A H31F 109.5 . . ?
H31D C31A H31E 109.5 . . ?
H31D C31A H31F 109.5 . . ?
H31E C31A H31F 109.5 . . ?
C30 C33A H33D 109.5 . . ?
C30 C33A H33E 109.5 . . ?
C30 C33A H33F 109.5 . . ?
H33D C33A H33E 109.5 . . ?
H33D C33A H33F 109.5 . . ?
H33E C33A H33F 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
S1 C24 C29 C28 178.8(4) . . . . ?
S1 C24 C25 C26 -178.6(4) . . . . ?
N1 C8 C11 C12 60.9(4) . . . . ?
N1 C8 C9 C10 -70.2(4) . . . . ?
C6 C5 C4 C3 -1.3(7) . . . . ?
C6 C1 C2 C3 -1.5(7) . . . . ?
C7 N1 C8 C11 -131.4(4) . . . . ?
C7 N1 C8 C9 106.9(4) . . . . ?
C7 C6 C5 C4 177.1(4) . . . . ?
C7 C6 C1 C2 -175.6(4) . . . . ?
C13 C12 C23 S1 -52.1(4) . . . . ?
C13 C12 C23 F1 -174.7(3) . . . . ?
C13 C12 C23 F2 72.9(4) . . . . ?
C13 C12 C11 C8 70.5(4) . . . . ?
C13 C14 C15 C16 0.1(7) . . . . ?
C21 C16 C15 C14 -0.2(7) . . . . ?
C21 C16 C17 C18 1.6(7) . . . . ?
C21 C20 C19 C18 -0.4(8) . . . . ?
C5 C6 C7 O1 -31.8(6) . . . . ?
C5 C6 C7 N1 149.1(4) . . . . ?
C5 C6 C1 C2 0.9(6) . . . . ?
C5 C4 C3 C2 0.7(8) . . . . ?
C12 C13 C22 C21 -177.3(4) . . . . ?
C12 C13 C14 C15 177.1(4) . . . . ?
C8 N1 C7 O1 -0.5(6) . . . . ?
C8 N1 C7 C6 178.6(3) . . . . ?
C23 S1 C24 C29 -89.9(4) . . . . ?
C23 S1 C24 C25 90.9(4) . . . . ?
C23 C12 C11 C8 -161.4(3) . . . . ?
C22 C13 C12 C23 -52.7(5) . . . . ?
C22 C13 C12 C11 73.2(5) . . . . ?
C22 C13 C14 C15 0.4(7) . . . . ?
C22 C21 C16 C15 -0.1(6) . . . . ?
C22 C21 C16 C17 179.8(4) . . . . ?
C22 C21 C20 C19 179.5(5) . . . . ?
C14 C13 C12 C23 130.7(4) . . . . ?
C14 C13 C12 C11 -103.4(4) . . . . ?
C14 C13 C22 C21 -0.7(6) . . . . ?
C11 C12 C23 S1 -179.3(3) . . . . ?
C11 C12 C23 F1 58.0(4) . . . . ?
C11 C12 C23 F2 -54.4(4) . . . . ?
C11 C8 C9 C10 168.7(3) . . . . ?
C9 C8 C11 C12 -177.9(3) . . . . ?
C1 C6 C7 O1 144.8(4) . . . . ?
C1 C6 C7 N1 -34.4(6) . . . . ?
C1 C6 C5 C4 0.4(6) . . . . ?
C4 C3 C2 C1 0.7(8) . . . . ?
C24 S1 C23 F1 -45.7(3) . . . . ?
C24 S1 C23 F2 66.8(3) . . . . ?
C24 S1 C23 C12 -168.0(3) . . . . ?
C27 C28 C29 C24 -0.1(7) . . . . ?
C27 C26 C25 C24 -0.5(8) . . . . ?
C16 C21 C22 C13 0.6(6) . . . . ?
C16 C21 C20 C19 0.1(7) . . . . ?
C16 C17 C18 C19 -1.9(8) . . . . ?
C30 C27 C28 C29 179.8(4) . . . . ?
C30 C27 C26 C25 -179.5(5) . . . . ?
C28 C27 C30 C31B 57.3(12) . . . . ?
C28 C27 C30 C32B -86.9(10) . . . . ?
C28 C27 C30 C33B 148.2(10) . . . . ?
C28 C27 C30 C32A -63.1(11) . . . . ?
C28 C27 C30 C31A 32.4(10) . . . . ?
C28 C27 C30 C33A -174.5(13) . . . . ?
C28 C27 C26 C25 -1.4(7) . . . . ?
C15 C16 C17 C18 -178.4(5) . . . . ?
C29 C24 C25 C26 2.2(8) . . . . ?
C17 C16 C15 C14 179.8(5) . . . . ?
C20 C21 C22 C13 -178.9(4) . . . . ?
C20 C21 C16 C15 179.4(4) . . . . ?
C20 C21 C16 C17 -0.7(6) . . . . ?
C20 C19 C18 C17 1.3(9) . . . . ?
C26 C27 C30 C31B -124.7(12) . . . . ?
C26 C27 C30 C32B 91.2(10) . . . . ?
C26 C27 C30 C33B -33.7(11) . . . . ?
C26 C27 C30 C32A 115.0(10) . . . . ?
C26 C27 C30 C31A -149.6(9) . . . . ?
C26 C27 C30 C33A 3.6(13) . . . . ?
C26 C27 C28 C29 1.7(7) . . . . ?
C25 C24 C29 C28 -1.9(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.55(4)
2 0.45(4)

