# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_v100
_database_code_depnum_ccdc_archive 'CCDC 2212436'
loop_
_audit_author_name
_audit_author_address
'Joshua Barham'
;University of Regensburg
Germany
;
_audit_update_record             
;
2022-10-11 deposited with the CCDC.	2022-10-31 downloaded from the CCDC.
;
_audit_creation_date             2022-09-26
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
Shahboz.Yakubov@chemie.uni-regensburg.de
?
Sabine.Stempfhuber@chemie.uni-regensburg.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 F2 N O'
_chemical_formula_sum            'C17 H19 F2 N O'
_chemical_formula_weight         291.33
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H19 F2 N O'
_chemical_oxdiff_usercomment     Yabukov_Barham_SY220a
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'
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'
F F 0.0727 0.0534 '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           9
_space_group_name_H-M_alt        'I 1 a 1'
_space_group_name_Hall           'I -2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   9.67810(10)
_cell_length_b                   11.11540(10)
_cell_length_c                   14.2033(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.6270(10)
_cell_angle_gamma                90
_cell_volume                     1484.92(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9868
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      73.7330
_cell_measurement_theta_min      5.0880
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.844
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.646
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.108a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 5 -6 0.0108
0 -5 6 0.0108
0 -2 -9 0.0412
0 -1 9 0.0319
0 6 4 0.0383
0 6 5 0.0399
0 -6 -5 0.0475
-6 1 4 0.0984
6 0 -3 0.0985
5 -3 -5 0.0939
3 6 3 0.0710

_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.022
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0447 5.3846 -5.9831 0.0221 0.9669 0.2541
-0.0447 -5.3846 5.9831 -0.0221 -0.9669 -0.2541
0.1736 -2.2978 -8.5445 0.0186 0.6143 -0.7889
-0.1465 -0.8071 8.9477 -0.0236 -0.8899 0.4556
-0.1400 6.4956 3.9467 -0.0015 0.1334 0.9911
0.1231 6.0110 4.9101 0.0391 -0.0022 0.9992
0.0495 -6.0019 -4.9893 -0.0116 0.0045 -0.9999
-6.1364 0.8111 3.7530 -0.9737 -0.0798 0.2135
6.2319 -0.1643 -3.2660 0.9910 0.0807 -0.1070
4.9805 -3.3432 -5.2669 0.7815 0.0665 -0.6203
2.6066 5.6111 3.3320 0.4329 0.0301 0.9009

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14494
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.076
_diffrn_reflns_theta_min         5.109
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      7.00  34.00   0.50    0.50    --   14.00  93.00-132.02   54
  2  ω     13.00  43.00   0.50    0.50    --   18.00  90.00 -70.48   60
  3  ω     13.00  43.00   0.50    0.50    --   18.00  90.00  -9.18   60
  4  ω     17.00  43.00   0.50    0.50    --   18.00  84.00  81.51   52
  5  ω     12.00  43.00   0.50    0.50    --   14.00  86.00 158.98   62
  6  ω    -48.00 -22.00   0.50    0.50    --  -10.00 142.00  48.59   52
  7  ω   -123.00 -40.00   0.50    1.00    --  -78.25 151.00 -13.83  166
  8  ω   -110.00 -36.00   0.50    1.00    --  -78.25 132.00  55.12  148
  9  ω   -100.00 -32.00   0.50    0.50    --  -73.72 125.00  30.00  136
 10  ω   -118.00 -38.00   0.50    1.00    --  -78.25 144.00 115.14  160
 11  ω    -90.00 -22.00   0.50    0.50    --  -63.82 125.00 150.00  136
 12  ω   -100.00 -32.00   0.50    0.50    --  -73.72 125.00  90.00  136
 13  ω   -100.00 -32.00   0.50    0.50    --  -73.72 125.00 -90.00  136
 14  ω   -100.00 -32.00   0.50    0.50    --  -73.72 125.00-120.00  136
 15  ω   -103.00 -35.00   0.50    1.00    --  -76.77 125.00-150.00  136
 16  ω    -70.00 -38.00   0.50    1.00    --  -78.25  65.00  53.71   64
 17  ω   -101.00 -26.00   0.50    0.50    --  -63.82   0.00 150.00  150
 18  ω     56.00  88.00   0.50    0.50    --   46.00  60.00 119.89   64
 19  ω     44.00  75.00   0.50    0.50    --   38.00  72.00  88.67   62
 20  ω     43.00  75.00   0.50    0.50    --   38.00  74.00 170.25   64
 21  ω     45.00  77.00   0.50    0.50    --   42.00  77.00  22.54   64
 22  ω     43.00  75.00   0.50    0.50    --   38.00  74.00  -3.22   64
 23  ω     53.00  84.00   0.50    0.50    --   46.00  70.00 -79.69   62
 24  ω     43.00  75.00   0.50    0.50    --   38.00  74.00-132.00   64
 25  ω     39.00 113.00   0.50    1.00    --   75.87   0.00 -30.00  148
 26  ω     61.00  92.00   0.50    0.50    --   54.00  70.00  74.44   62
 27  ω     60.00  91.00   0.50    0.50    --   54.00  73.00 123.10   62
 28  ω     76.00 127.00   0.50    1.00    --   79.75  26.00  23.36  102
 29  ω     39.00 113.00   0.50    1.00    --   75.87   0.00 150.00  148
 30  ω     64.00  95.00   0.50    0.50    --   58.00  72.00-128.15   62
 31  ω     38.00  84.00   0.50    1.00    --   75.87 -95.00-120.00   92
 32  ω     40.00  99.00   0.50    1.00    --   79.75-113.00  39.04  118
 33  ω     21.00  90.00   0.50    0.50    --   63.22-125.00  60.00  138
 34  ω   -109.00 -78.00   0.50    0.50    --  -74.00 -76.00 138.31   62
 35  ω   -113.00 -80.00   0.50    1.00    --  -78.25 -79.00 119.57   66
 36  ω   -106.00 -75.00   0.50    0.50    --  -70.00 -74.00  90.54   62
 37  ω   -114.00 -82.00   0.50    1.00    --  -78.25 -76.00  69.72   64
 38  ω   -114.00 -83.00   0.50    0.50    --  -74.00 -64.00  74.65   62
 39  ω   -115.00 -84.00   0.50    1.00    --  -78.25 -72.00  -9.49   62
 40  ω   -106.00 -74.00   0.50    0.50    --  -70.00 -75.00 -32.22   64
 41  ω   -113.00 -81.00   0.50    1.00    --  -78.25 -77.00-116.34   64
 42  ω   -114.00 -82.00   0.50    1.00    --  -78.25 -76.00 -83.37   64
 43  ω   -115.00 -83.00   0.50    0.50    --  -74.00 -62.00   2.49   64
 44  ω   -121.00 -89.00   0.50    1.00    --  -78.25 -55.00  11.46   64
 45  ω   -119.00 -87.00   0.50    1.00    --  -78.25 -62.00 175.03   64
 46  ω   -125.00 -91.00   0.50    1.00    --  -78.25 -39.00 123.67   68
 47  ω   -121.00 -89.00   0.50    1.00    --  -78.25 -55.00  44.87   64
 48  ω   -114.00 -81.00   0.50    0.50    --  -70.00 -51.00  18.45   66
 49  ω   -124.00 -90.00   0.50    1.00    --  -78.25 -43.00-177.10   68
 50  ω   -113.00 -79.00   0.50    1.00    --  -78.25 -86.00 -52.80   68
 51  ω   -118.00 -73.00   0.50    1.00    --  -76.77-125.00-180.00   90
 52  ω   -118.00 -73.00   0.50    1.00    --  -76.77-125.00-150.00   90
 53  ω   -118.00 -73.00   0.50    1.00    --  -76.77-125.00   0.00   90
 54  ω   -118.00 -73.00   0.50    1.00    --  -76.77-125.00 150.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1592237000
_diffrn_orient_matrix_UB_12      0.0030486000
_diffrn_orient_matrix_UB_13      0.0002415000
_diffrn_orient_matrix_UB_21      -0.0338456000
_diffrn_orient_matrix_UB_22      0.0763842000
_diffrn_orient_matrix_UB_23      -0.0931191000
_diffrn_orient_matrix_UB_31      0.0181745000
_diffrn_orient_matrix_UB_32      0.1155183000
_diffrn_orient_matrix_UB_33      0.0616311000
_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         0.953
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                2818
_reflns_number_total             2928
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1298 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2928
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.038
_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)+(0.0537P)²+0.7882P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0962
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C4(H4A,H4B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C13(H13), C16(H16), C14(H14)
;
_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
O1 O 0.27926(18) 0.53878(16) 0.56007(15) 0.0368(5) Uani 1 1 d . . . . .
F2 F 0.5064(3) 0.02964(17) 0.70726(17) 0.0659(7) Uani 1 1 d . . . . .
F1 F 0.7195(3) 0.83662(18) 0.35486(19) 0.0700(7) Uani 1 1 d . . . . .
N1 N 0.4955(2) 0.55386(17) 0.52491(15) 0.0253(4) Uani 1 1 d . . . . .
C11 C 0.3984(2) 0.4970(2) 0.56196(18) 0.0261(5) Uani 1 1 d . . . . .
C1 C 0.4685(2) 0.6643(2) 0.46584(16) 0.0233(5) Uani 1 1 d . . . . .
C2 C 0.4257(3) 0.7703(2) 0.52181(17) 0.0269(5) Uani 1 1 d . . . . .
H2A H 0.500881 0.785360 0.581198 0.032 Uiso 1 1 calc R U . . .
H2B H 0.336546 0.750867 0.541340 0.032 Uiso 1 1 calc R U . . .
C6 C 0.6088(3) 0.6972(2) 0.4387(2) 0.0326(6) Uani 1 1 d . . . . .
H6A H 0.683988 0.711498 0.498205 0.039 Uiso 1 1 calc R U . . .
H6B H 0.639393 0.629804 0.402740 0.039 Uiso 1 1 calc R U . . .
C12 C 0.4378(2) 0.3747(2) 0.60432(18) 0.0259(5) Uani 1 1 d . . . . .
C17 C 0.5183(2) 0.2945(2) 0.56355(18) 0.0275(5) Uani 1 1 d . . . . .
H17 H 0.557604 0.320186 0.511619 0.033 Uiso 1 1 calc R U . . .
C15 C 0.4830(3) 0.1438(3) 0.6733(2) 0.0419(7) Uani 1 1 d . . . . .
C13 C 0.3807(3) 0.3360(3) 0.6804(2) 0.0365(6) Uani 1 1 d . . . . .
H13 H 0.325004 0.389837 0.708130 0.044 Uiso 1 1 calc R U . . .
C4 C 0.5447(3) 0.9141(2) 0.4306(2) 0.0348(6) Uani 1 1 d . . . . .
H4A H 0.532591 0.987051 0.389449 0.042 Uiso 1 1 calc R U . . .
H4B H 0.619563 0.930303 0.489933 0.042 Uiso 1 1 calc R U . . .
C16 C 0.5412(3) 0.1783(2) 0.5980(2) 0.0345(6) Uani 1 1 d . . . . .
H16 H 0.595826 0.123515 0.570300 0.041 Uiso 1 1 calc R U . . .
C3 C 0.4039(3) 0.8832(2) 0.4576(2) 0.0344(6) Uani 1 1 d . . . . .
H3 H 0.374375 0.952006 0.493881 0.041 Uiso 1 1 calc R U . . .
C5 C 0.5873(3) 0.8092(3) 0.3765(2) 0.0403(7) Uani 1 1 d . . . . .
C14 C 0.4041(4) 0.2203(3) 0.7161(2) 0.0458(7) Uani 1 1 d . . . . .
H14 H 0.366738 0.194149 0.768754 0.055 Uiso 1 1 calc R U . . .
C7 C 0.3536(3) 0.6417(3) 0.3731(2) 0.0423(7) Uani 1 1 d . . . . .
H7A H 0.262449 0.621737 0.389652 0.051 Uiso 1 1 calc R U . . .
H7B H 0.381308 0.572950 0.337214 0.051 Uiso 1 1 calc R U . . .
C8 C 0.2896(4) 0.8595(3) 0.3660(3) 0.0541(9) Uani 1 1 d . . . . .
H8A H 0.274278 0.932589 0.325044 0.065 Uiso 1 1 calc R U . . .
H8B H 0.198940 0.839056 0.383034 0.065 Uiso 1 1 calc R U . . .
C9 C 0.4765(5) 0.7863(3) 0.2837(2) 0.0617(11) Uani 1 1 d . . . . .
H9A H 0.506687 0.718932 0.247638 0.074 Uiso 1 1 calc R U . . .
H9B H 0.464349 0.858889 0.242146 0.074 Uiso 1 1 calc R U . . .
C10 C 0.3361(5) 0.7552(3) 0.3101(2) 0.0623(10) Uani 1 1 d . . . . .
H10 H 0.261320 0.740620 0.249379 0.075 Uiso 1 1 calc R U . . .
H1 H 0.589(3) 0.524(3) 0.540(2) 0.031(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.238(3) . ?
F2 C15 1.357(3) . ?
F1 C5 1.418(4) . ?
N1 C11 1.339(3) . ?
N1 C1 1.475(3) . ?
N1 H1 0.94(3) . ?
C11 C12 1.500(3) . ?
C1 C2 1.532(3) . ?
C1 C6 1.540(3) . ?
C1 C7 1.531(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.536(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.512(4) . ?
C12 C17 1.395(3) . ?
C12 C13 1.393(3) . ?
C17 H17 0.9500 . ?
C17 C16 1.381(4) . ?
C15 C16 1.376(4) . ?
C15 C14 1.376(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.539(4) . ?
C4 C5 1.506(4) . ?
C16 H16 0.9500 . ?
C3 H3 1.0000 . ?
C3 C8 1.520(5) . ?
C5 C9 1.512(5) . ?
C14 H14 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C10 1.533(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C10 1.531(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.532(6) . ?
C10 H10 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C1 124.72(19) . . ?
C11 N1 H1 117.9(19) . . ?
C1 N1 H1 117.3(19) . . ?
O1 C11 N1 123.5(2) . . ?
O1 C11 C12 119.8(2) . . ?
N1 C11 C12 116.75(19) . . ?
N1 C1 C2 112.23(18) . . ?
N1 C1 C6 106.92(18) . . ?
N1 C1 C7 110.4(2) . . ?
C2 C1 C6 108.1(2) . . ?
C7 C1 C2 110.0(2) . . ?
C7 C1 C6 109.1(2) . . ?
C1 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
C1 C2 C3 109.67(19) . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
C1 C6 H6A 109.8 . . ?
C1 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
C5 C6 C1 109.5(2) . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
C17 C12 C11 121.8(2) . . ?
C13 C12 C11 118.7(2) . . ?
C13 C12 C17 119.2(2) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.6(2) . . ?
C16 C17 H17 119.7 . . ?
F2 C15 C16 118.2(3) . . ?
F2 C15 C14 119.0(3) . . ?
C14 C15 C16 122.8(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13 119.7 . . ?
H4A C4 H4B 108.3 . . ?
C3 C4 H4A 110.0 . . ?
C3 C4 H4B 110.0 . . ?
C5 C4 H4A 110.0 . . ?
C5 C4 H4B 110.0 . . ?
C5 C4 C3 108.6(2) . . ?
C17 C16 H16 120.8 . . ?
C15 C16 C17 118.4(2) . . ?
C15 C16 H16 120.8 . . ?
C2 C3 C4 108.9(2) . . ?
C2 C3 H3 109.6 . . ?
C4 C3 H3 109.6 . . ?
C8 C3 C2 109.7(2) . . ?
C8 C3 C4 109.5(2) . . ?
C8 C3 H3 109.6 . . ?
F1 C5 C6 107.3(2) . . ?
F1 C5 C4 108.3(2) . . ?
F1 C5 C9 109.8(3) . . ?
C4 C5 C6 110.9(2) . . ?
C4 C5 C9 110.6(3) . . ?
C9 C5 C6 110.0(3) . . ?
C15 C14 C13 118.3(3) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
C1 C7 H7A 109.9 . . ?
C1 C7 H7B 109.9 . . ?
C1 C7 C10 109.0(2) . . ?
H7A C7 H7B 108.3 . . ?
C10 C7 H7A 109.9 . . ?
C10 C7 H7B 109.9 . . ?
C3 C8 H8A 109.8 . . ?
C3 C8 H8B 109.8 . . ?
C3 C8 C10 109.4(2) . . ?
H8A C8 H8B 108.2 . . ?
C10 C8 H8A 109.8 . . ?
C10 C8 H8B 109.8 . . ?
C5 C9 H9A 110.1 . . ?
C5 C9 H9B 110.1 . . ?
C5 C9 C10 108.2(2) . . ?
H9A C9 H9B 108.4 . . ?
C10 C9 H9A 110.1 . . ?
C10 C9 H9B 110.1 . . ?
C7 C10 H10 109.2 . . ?
C8 C10 C7 109.0(3) . . ?
C8 C10 C9 110.0(3) . . ?
C8 C10 H10 109.2 . . ?
C9 C10 C7 110.3(3) . . ?
C9 C10 H10 109.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C11 C12 C17 141.4(2) . . . . ?
O1 C11 C12 C13 -32.1(3) . . . . ?
F2 C15 C16 C17 -179.7(2) . . . . ?
F2 C15 C14 C13 -179.7(3) . . . . ?
F1 C5 C9 C10 179.1(3) . . . . ?
N1 C11 C12 C17 -36.5(3) . . . . ?
N1 C11 C12 C13 150.0(2) . . . . ?
N1 C1 C2 C3 178.14(19) . . . . ?
N1 C1 C6 C5 179.2(2) . . . . ?
N1 C1 C7 C10 -175.9(3) . . . . ?
C11 N1 C1 C2 62.0(3) . . . . ?
C11 N1 C1 C6 -179.7(2) . . . . ?
C11 N1 C1 C7 -61.1(3) . . . . ?
C11 C12 C17 C16 -173.5(2) . . . . ?
C11 C12 C13 C14 174.4(3) . . . . ?
C1 N1 C11 O1 -8.7(4) . . . . ?
C1 N1 C11 C12 169.1(2) . . . . ?
C1 C2 C3 C4 -61.1(3) . . . . ?
C1 C2 C3 C8 58.7(3) . . . . ?
C1 C6 C5 F1 179.1(2) . . . . ?
C1 C6 C5 C4 61.1(3) . . . . ?
C1 C6 C5 C9 -61.6(3) . . . . ?
C1 C7 C10 C8 -61.0(4) . . . . ?
C1 C7 C10 C9 59.9(3) . . . . ?
C2 C1 C6 C5 -59.8(3) . . . . ?
C2 C1 C7 C10 59.8(3) . . . . ?
C2 C3 C8 C10 -60.4(3) . . . . ?
C6 C1 C2 C3 60.5(3) . . . . ?
C6 C1 C7 C10 -58.6(3) . . . . ?
C6 C5 C9 C10 61.3(3) . . . . ?
C12 C17 C16 C15 -0.1(4) . . . . ?
C12 C13 C14 C15 -1.2(5) . . . . ?
C17 C12 C13 C14 0.6(4) . . . . ?
C13 C12 C17 C16 0.0(4) . . . . ?
C4 C3 C8 C10 59.1(3) . . . . ?
C4 C5 C9 C10 -61.5(3) . . . . ?
C16 C15 C14 C13 1.1(5) . . . . ?
C3 C4 C5 F1 -178.0(2) . . . . ?
C3 C4 C5 C6 -60.6(3) . . . . ?
C3 C4 C5 C9 61.7(3) . . . . ?
C3 C8 C10 C7 61.6(4) . . . . ?
C3 C8 C10 C9 -59.4(3) . . . . ?
C5 C4 C3 C2 59.9(3) . . . . ?
C5 C4 C3 C8 -60.0(3) . . . . ?
C5 C9 C10 C7 -60.6(3) . . . . ?
C5 C9 C10 C8 59.6(3) . . . . ?
C14 C15 C16 C17 -0.5(5) . . . . ?
C7 C1 C2 C3 -58.6(3) . . . . ?
C7 C1 C6 C5 59.8(3) . . . . ?

_olex2_date_sample_data_collection 2022-09-20
_olex2_date_sample_submission    2022-09-14
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder inert oil'
_olex2_submission_original_sample_id SY220a
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.330
_oxdiff_exptl_absorpt_empirical_full_min 0.595
####################################################################### 
# 
# 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_V108
_database_code_depnum_ccdc_archive 'CCDC 2212438'
loop_
_audit_author_name
_audit_author_address
'Joshua Barham'
;University of Regensburg
Germany
;
_audit_update_record             
;
2022-10-11 deposited with the CCDC.	2022-10-31 downloaded from the CCDC.
;
_audit_creation_date             2022-09-28
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
loop_
_audit_author_email
Shahboz.Yakubov@chemie.uni-regensburg.de
?
xray@chemie.uni-regensburg.de
_chemical_name_systematic        'SY 635'
_chemical_formula_moiety         'C25 H35.086 F0.914 O5'
_chemical_formula_sum            'C25 H35.086 F0.914 O5'
_chemical_formula_weight         433.023
_chemical_absolute_configuration ad
_chemical_oxdiff_formula         'C25 H35 F O5'
_chemical_oxdiff_usercomment     Yabukov_Barham_SY635
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.07537 0.05506 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           ' P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_symmetry_Int_Tables_number      4
_cell_length_a                   10.4636(4)
_cell_length_b                   6.90652(18)
_cell_length_c                   16.1323(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.458(4)
_cell_angle_gamma                90
_cell_volume                     1105.87(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3924
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      73.2540
_cell_measurement_theta_min      2.8700
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.39a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       needle
_exptl_crystal_F_000             468.262
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.028
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.9895
_diffrn_reflns_Laue_measured_fraction_max 0.9686
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11859
_diffrn_reflns_point_group_measured_fraction_full 0.8780
_diffrn_reflns_point_group_measured_fraction_max 0.8444
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         75.16
_diffrn_reflns_theta_min         2.89
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.9895
_diffrn_measured_fraction_theta_max 0.9686
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     43.00  68.00   0.50    1.20    --   78.43-111.00-136.00   50
  2  ω     19.00  81.00   0.50    1.20    --   60.79-111.00-136.00  124
  3  ω     33.00  94.00   0.50    1.20    --   74.37-111.00-136.00  122
  4  ω     38.00  84.00   0.50    1.20    --   82.00-121.00  23.12   92
  5  ω     40.00 109.00   0.50    1.20    --   82.00  -3.00  79.79  138
  6  ω     43.00  81.00   0.50    1.20    --   82.00  -4.00  35.96   76
  7  ω     11.00  36.00   0.50    1.20    --   60.79 -30.00-180.00   50
  8  ω     48.00  75.00   0.50    1.20    --   82.00  -4.00  -8.27   54
  9  ω     89.00 122.00   0.50    1.20    --   82.00  93.00 -49.80   66
 10  ω     47.00  94.00   0.50    1.20    --   82.00   1.00 -52.18   94
 11  ω     64.00  99.00   0.50    1.20    --   56.00  61.00  44.78   70
 12  ω     55.00  81.00   0.50    1.20    --   44.00  68.00 114.88   52
 13  ω     87.00 130.00   0.50    1.20    --   82.00  18.00 178.23   86
 14  ω     96.00 128.00   0.50    1.20    --   82.00  50.00  90.46   64
 15  ω     90.00 127.00   0.50    1.20    --   82.00  57.00  58.98   74
 16  ω     55.00 100.00   0.50    1.20    --   82.00  20.00  35.66   90
 17  ω     98.00 124.00   0.50    1.20    --   82.00  61.00-177.94   52
 18  ω    -74.00 -49.00   0.50    1.20    --  -80.00  70.00  83.56   50
 19  ω    -87.00 -42.00   0.50    1.20    --  -80.00  97.00 124.13   90
 20  ω   -105.00 -61.00   0.50    1.20    --  -80.00 121.00  21.68   88
 21  ω    -81.00 -19.00   0.50    1.20    --  -61.39 111.00 -43.00  124
 22  ω    -86.00 -38.00   0.50    1.20    --  -75.76 111.00 -43.00   96
 23  ω    -90.00 -44.00   0.50    1.20    --  -80.00  95.00 -52.24   92
 24  ω   -123.00 -98.00   0.50    1.20    --  -80.00 -44.00-147.75   50
 25  ω   -122.00 -91.00   0.50    1.20    --  -80.00 -57.00-157.24   62
 26  ω   -106.00 -81.00   0.50    1.20    --  -80.00 -79.00 -94.18   50
 27  ω   -109.00 -84.00   0.50    1.20    --  -72.00 -74.00-107.08   50
 28  ω   -115.00 -89.00   0.50    1.20    --  -80.00 -76.00 -43.69   52
 29  ω   -124.00 -97.00   0.50    1.20    --  -80.00 -57.00   8.47   54
 30  ω   -113.00 -86.00   0.50    1.20    --  -68.00 -51.00  70.95   54
 31  ω   -111.00 -77.00   0.50    1.20    --  -68.00 -50.00 -60.77   68
 32  ω   -111.00 -85.00   0.50    1.20    --  -80.00 -81.00 -62.75   52
 33  ω   -113.00 -74.00   0.50    1.20    --  -75.28-125.00 -90.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1314916000
_diffrn_orient_matrix_UB_12      0.0990931000
_diffrn_orient_matrix_UB_13      -0.0006567000
_diffrn_orient_matrix_UB_21      -0.0361829000
_diffrn_orient_matrix_UB_22      -0.0398116000
_diffrn_orient_matrix_UB_23      -0.0987179000
_diffrn_orient_matrix_UB_31      -0.0740229000
_diffrn_orient_matrix_UB_32      0.1958175000
_diffrn_orient_matrix_UB_33      -0.0197038000
_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         0.697
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              20
_reflns_limit_l_min              -19
_reflns_number_gt                2981
_reflns_number_total             3857
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.43.39a (Rigaku OD, 2022)'
_computing_data_collection       
'CrysAlisPro system (CCD 42.68a 64-bit (release 08-09-2022))'
_computing_data_reduction        'CrysAlisPro 1.171.43.39a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.2077
_refine_diff_density_min         -0.2155
_refine_diff_density_rms         0.0549
_refine_ls_abs_structure_details 
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.12(12)
_refine_ls_d_res_high            0.7975
_refine_ls_d_res_low             15.3024
_refine_ls_goodness_of_fit_ref   1.0399
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    17
_refine_ls_number_parameters     413
_refine_ls_number_reflns         3857
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.0381
_refine_ls_shift/su_max          -0.0010
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0485P)²+0.1782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1052
_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. Uiso/Uaniso restraints and constraints
F1 \\sim C00E: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.01 within 2A
Uanis(F4) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
3. Others
 Sof(H00w)=1-FVAR(1)
 Sof(F002)=FVAR(1)
 Sof(H00y)=1-FVAR(2)
 Sof(F4)=FVAR(2)
 Sof(H00E)=1-FVAR(3)
 Sof(F1)=FVAR(3)
4.a Ternary CH refined with riding coordinates:
 C00E(H00E)
4.b Secondary CH2 refined with riding coordinates:
 C00Q(H00v,H00w), C00R(H00y,H00x)
4.c Idealised Me refined as rotating group with stretchable bonds:
 C00V(H2,Hd,He)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_group
O001 O 0.57370(18) 0.0619(3) 0.54352(12) 0.0286(5) Uani 1.000000 . . .
F002 F 0.83035(18) 0.2380(3) 0.62292(12) 0.0299(7) Uani 0.808(6) . . 1
O003 O 0.60258(19) 0.7502(3) 0.74798(14) 0.0327(5) Uani 1.000000 . . .
O004 O 0.0255(2) 0.3564(3) 0.38426(14) 0.0356(5) Uani 1.000000 . . .
O005 O 1.2631(2) 0.9942(4) 0.91387(15) 0.0516(7) Uani 1.000000 . . .
C006 C 0.5029(3) 0.0689(4) 0.59024(17) 0.0209(6) Uani 1.000000 . . .
C007 C 0.6906(3) 0.4253(4) 0.77963(18) 0.0206(6) Uani 1.000000 . . .
O008 O 1.3300(2) 0.7021(5) 0.88229(18) 0.0668(9) Uani 1.000000 . . .
C009 C 0.4128(3) 0.3428(4) 0.65410(18) 0.0206(6) Uani 1.000000 . . .
H009 H 0.409(3) 0.404(5) 0.6026(19) 0.024(8) Uiso 1.000000 . . .
C00A C 0.5805(3) 0.5773(4) 0.75374(17) 0.0236(6) Uani 1.000000 . . .
C00B C 0.6643(2) 0.3089(4) 0.69235(17) 0.0208(6) Uani 1.000000 . . .
H00B H 0.657(2) 0.415(4) 0.6443(17) 0.015(7) Uiso 1.000000 . . .
C00C C 0.1198(3) 0.3501(4) 0.45169(18) 0.0253(6) Uani 1.000000 . . .
C00D C 0.1393(3) 0.4916(5) 0.5253(2) 0.0272(6) Uani 1.000000 . . .
H00a H 0.217(3) 0.573(5) 0.5278(18) 0.028(8) Uiso 1.000000 . . .
H00c H 0.061(2) 0.587(4) 0.5130(16) 0.013(6) Uiso 1.000000 . . .
C00E C 0.8379(2) 0.4943(4) 0.79758(18) 0.0227(6) Uani 1.000000 . U .
H00E H 0.8386(2) 0.5983(4) 0.75460(18) 0.0272(7) Uiso 0.973(4) R . 2
C00F C 0.2753(2) 0.2368(5) 0.63546(17) 0.0220(6) Uani 1.000000 . . .
C00G C 0.2543(3) 0.0956(4) 0.55808(18) 0.0225(6) Uani 1.000000 . . .
H00G H 0.171(3) 0.023(5) 0.5557(19) 0.031(8) Uiso 1.000000 . . .
C00H C 0.5327(3) 0.1960(4) 0.66957(17) 0.0204(6) Uani 1.000000 . . .
H00H H 0.530(3) 0.112(5) 0.7174(19) 0.025(8) Uiso 1.000000 . . .
C00I C 0.6778(3) 0.2984(5) 0.85489(19) 0.0269(7) Uani 1.000000 . . .
H00d H 0.695(3) 0.371(6) 0.908(2) 0.047(10) Uiso 1.000000 . . .
H00f H 0.588(3) 0.244(5) 0.8430(19) 0.032(8) Uiso 1.000000 . . .
H00i H 0.748(3) 0.184(6) 0.867(2) 0.040(9) Uiso 1.000000 . . .
C00J C 0.1578(3) 0.3834(5) 0.6110(2) 0.0262(7) Uani 1.000000 . . .
H00j H 0.170(3) 0.470(6) 0.660(2) 0.042(10) Uiso 1.000000 . . .
H00k H 0.073(3) 0.311(5) 0.604(2) 0.039(9) Uiso 1.000000 . . .
C00K C 0.9122(3) 0.5699(5) 0.88992(19) 0.0266(6) Uani 1.000000 . . .
H00l H 0.914(3) 0.460(5) 0.931(2) 0.033(8) Uiso 1.000000 . . .
C00L C 0.3741(3) -0.0446(4) 0.5711(2) 0.0250(6) Uani 1.000000 . . .
H00m H 0.356(3) -0.123(6) 0.514(2) 0.044(10) Uiso 1.000000 . . .
H00n H 0.384(3) -0.125(5) 0.6207(19) 0.022(8) Uiso 1.000000 . . .
C00M C 0.4389(3) 0.4964(5) 0.72676(19) 0.0238(6) Uani 1.000000 . . .
H00o H 0.374(3) 0.604(5) 0.7074(18) 0.022(7) Uiso 1.000000 . . .
H00p H 0.430(3) 0.448(5) 0.782(2) 0.036(9) Uiso 1.000000 . . .
C00N C 0.2678(3) 0.1257(5) 0.7162(2) 0.0294(7) Uani 1.000000 . . .
H00q H 0.344(3) 0.039(5) 0.743(2) 0.037(9) Uiso 1.000000 . . .
H00r H 0.260(3) 0.219(5) 0.766(2) 0.035(8) Uiso 1.000000 . . .
H00s H 0.183(3) 0.063(5) 0.6989(19) 0.030(8) Uiso 1.000000 . . .
C00O C 1.2406(3) 0.8146(6) 0.8810(2) 0.0432(9) Uani 1.000000 . . .
C00P C 0.2262(3) 0.1949(5) 0.46858(18) 0.0253(6) Uani 1.000000 . . .
H00t H 0.191(3) 0.095(5) 0.4168(19) 0.024(7) Uiso 1.000000 . . .
H00u H 0.306(3) 0.258(5) 0.4607(18) 0.028(8) Uiso 1.000000 . . .
C00Q C 0.7983(3) 0.2059(5) 0.70215(18) 0.0290(7) Uani 1.000000 . . .
H00v H 0.7933(3) 0.0683(5) 0.71797(18) 0.0348(8) Uiso 1.000000 R . 2
H00w H 0.8200(3) 0.2121(5) 0.64675(18) 0.0348(8) Uiso 0.192(6) R . 2
C00R C 0.9051(3) 0.3120(5) 0.7746(2) 0.0284(7) Uani 1.000000 . . .
H00y H 0.9818(3) 0.3491(5) 0.7544(2) 0.0341(8) Uiso 0.922(6) R . 2
H00x H 0.9392(3) 0.2276(5) 0.8265(2) 0.0341(8) Uiso 1.000000 R . 1
C00S C 1.0622(3) 0.6089(5) 0.90474(19) 0.0289(7) Uani 1.000000 . . .
H00z H 1.105(3) 0.647(5) 0.970(2) 0.0346(8) Uiso 1.000000 R . .
H H 1.117(3) 0.481(5) 0.8960(19) 0.0346(8) Uiso 1.000000 R . .
C00T C 1.0932(3) 0.7692(5) 0.8482(2) 0.0383(8) Uani 1.000000 . . .
H00 H 1.038(3) 0.901(6) 0.847(2) 0.056(11) Uiso 1.000000 . . .
Ha H 1.066(3) 0.717(5) 0.784(2) 0.033(8) Uiso 1.000000 . . .
C00U C 0.8448(3) 0.7451(6) 0.9164(2) 0.0372(8) Uani 1.000000 . . .
H1 H 0.852(4) 0.853(7) 0.880(3) 0.062(13) Uiso 1.000000 . . .
Hb H 0.740(3) 0.720(6) 0.916(2) 0.041(9) Uiso 1.000000 . . .
Hc H 0.902(3) 0.778(6) 0.981(2) 0.051(10) Uiso 1.000000 . . .
C00V C 1.4037(4) 1.0514(7) 0.9487(3) 0.0763(16) Uani 1.000000 . . .
H2 H 1.4602(16) 0.988(4) 0.9088(16) 0.114(2) Uiso 1.000000 GR . .
Hd H 1.4111(5) 1.209(4) 0.9475(17) 0.114(2) Uiso 1.000000 GR . .
He H 1.4455(15) 1.000(4) 1.0160(18) 0.114(2) Uiso 1.000000 GR . .
F4 F 0.9904(19) 0.3696(8) 0.7299(14) 0.032(7) Uani 0.078(6) . U 1
F1 F 0.836(5) 0.6555(8) 0.736(3) 0.023(6) Uani 0.027(4) . U 1


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 C006 1.213(3) . ?
F002 C00Q 1.437(3) . ?
O003 C00A 1.225(4) . ?
O004 C00C 1.216(3) . ?
O005 C00O 1.340(4) . ?
O005 C00V 1.453(4) . ?
C006 C00H 1.501(4) . ?
C006 C00L 1.505(4) . ?
C007 C00A 1.516(4) . ?
C007 C00B 1.568(4) . ?
C007 C00E 1.551(4) . ?
C007 C00I 1.537(4) . ?
O008 C00O 1.211(4) . ?
C009 H009 0.92(3) . ?
C009 C00F 1.557(4) . ?
C009 C00H 1.570(4) . ?
C009 C00M 1.540(4) . ?
C00A C00M 1.513(4) . ?
C00B H00B 1.05(3) . ?
C00B C00H 1.523(4) . ?
C00B C00Q 1.535(4) . ?
C00C C00D 1.501(4) . ?
C00C C00P 1.507(4) . ?
C00D H00a 0.98(3) . ?
C00D H00c 1.02(3) . ?
C00D C00J 1.529(4) . ?
C00E H00E 1.0000 . ?
C00E C00K 1.537(4) . ?
C00E C00R 1.544(4) . ?
C00E F1 1.49(3) . ?
C00F C00G 1.544(4) . ?
C00F C00J 1.545(4) . ?
C00F C00N 1.535(4) . ?
C00G H00G 0.99(3) . ?
C00G C00L 1.545(4) . ?
C00G C00P 1.540(4) . ?
C00H H00H 0.97(3) . ?
C00I H00d 0.96(4) . ?
C00I H00f 0.98(3) . ?
C00I H00i 1.05(4) . ?
C00J H00j 0.97(4) . ?
C00J H00k 0.99(3) . ?
C00K H00l 1.01(3) . ?
C00K C00S 1.535(4) . ?
C00K C00U 1.528(5) . ?
C00L H00m 1.03(4) . ?
C00L H00n 0.95(3) . ?
C00M H00o 0.99(3) . ?
C00M H00p 0.98(3) . ?
C00N H00q 0.98(3) . ?
C00N H00r 1.05(3) . ?
C00N H00s 0.95(3) . ?
C00O C00T 1.497(4) . ?
C00P H00t 1.06(3) . ?
C00P H00u 0.98(3) . ?
C00Q H00v 0.9900 . ?
C00Q H00w 0.9900 . ?
C00Q C00R 1.524(4) . ?
C00R H00y 0.9900 . ?
C00R H00x 0.9900 . ?
C00R F4 1.372(16) . ?
C00S H00z 1.04(3) . ?
C00S H 1.08(3) . ?
C00S C00T 1.533(4) . ?
C00T H00 1.08(4) . ?
C00T Ha 1.04(3) . ?
C00U H1 0.96(5) . ?
C00U Hb 1.11(3) . ?
C00U Hc 1.05(4) . ?
C00V H2 1.09(3) . ?
C00V Hd 1.09(3) . ?
C00V He 1.09(3) . ?

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
C00V O005 C00O 115.8(3) . . ?
C00H C006 O001 123.4(3) . . ?
C00L C006 O001 122.4(3) . . ?
C00L C006 C00H 114.2(2) . . ?
C00B C007 C00A 101.9(2) . . ?
C00E C007 C00A 117.5(2) . . ?
C00E C007 C00B 101.9(2) . . ?
C00I C007 C00A 111.4(2) . . ?
C00I C007 C00B 112.5(2) . . ?
C00I C007 C00E 110.9(2) . . ?
C00F C009 H009 105.8(17) . . ?
C00H C009 H009 104.0(17) . . ?
C00H C009 C00F 111.7(2) . . ?
C00M C009 H009 108.3(19) . . ?
C00M C009 C00F 113.7(2) . . ?
C00M C009 C00H 112.6(2) . . ?
C007 C00A O003 123.4(2) . . ?
C00M C00A O003 121.9(3) . . ?
C00M C00A C007 114.4(3) . . ?
H00B C00B C007 104.8(14) . . ?
C00H C00B C007 111.6(2) . . ?
C00H C00B H00B 109.1(14) . . ?
C00Q C00B C007 104.5(2) . . ?
C00Q C00B H00B 104.6(13) . . ?
C00Q C00B C00H 121.0(2) . . ?
C00D C00C O004 123.6(3) . . ?
C00P C00C O004 122.0(3) . . ?
C00P C00C C00D 114.4(2) . . ?
H00a C00D C00C 108.2(17) . . ?
H00c C00D C00C 111.5(15) . . ?
H00c C00D H00a 104(2) . . ?
C00J C00D C00C 110.1(3) . . ?
C00J C00D H00a 112.3(17) . . ?
C00J C00D H00c 110.7(14) . . ?
H00E C00E C007 108.41(14) . . ?
C00K C00E C007 116.9(2) . . ?
C00K C00E H00E 108.41(16) . . ?
C00R C00E C007 101.9(2) . . ?
C00R C00E H00E 108.41(16) . . ?
C00R C00E C00K 112.4(2) . . ?
F1 C00E C007 107.6(19) . . ?
F1 C00E H00E 2.7(15) . . ?
F1 C00E C00K 106.9(17) . . ?
F1 C00E C00R 111.1(16) . . ?
C00G C00F C009 109.8(2) . . ?
C00J C00F C009 110.7(2) . . ?
C00J C00F C00G 108.0(2) . . ?
C00N C00F C009 111.3(2) . . ?
C00N C00F C00G 109.8(3) . . ?
C00N C00F C00J 107.1(2) . . ?
H00G C00G C00F 104.4(17) . . ?
C00L C00G C00F 112.6(2) . . ?
C00L C00G H00G 110.5(19) . . ?
C00P C00G C00F 114.4(2) . . ?
C00P C00G H00G 106.4(18) . . ?
C00P C00G C00L 108.2(2) . . ?
C009 C00H C006 107.6(2) . . ?
C00B C00H C006 115.6(2) . . ?
C00B C00H C009 108.9(2) . . ?
H00H C00H C006 106.0(18) . . ?
H00H C00H C009 106.7(16) . . ?
H00H C00H C00B 111.6(17) . . ?
H00d C00I C007 112(2) . . ?
H00f C00I C007 112.6(18) . . ?
H00f C00I H00d 106(3) . . ?
H00i C00I C007 109.9(17) . . ?
H00i C00I H00d 108(3) . . ?
H00i C00I H00f 109(3) . . ?
C00F C00J C00D 114.4(2) . . ?
H00j C00J C00D 113(2) . . ?
H00j C00J C00F 108(2) . . ?
H00k C00J C00D 107.2(18) . . ?
H00k C00J C00F 107.9(19) . . ?
H00k C00J H00j 106(2) . . ?
H00l C00K C00E 106.4(18) . . ?
C00S C00K C00E 112.9(2) . . ?
C00S C00K H00l 103.2(17) . . ?
C00U C00K C00E 113.8(3) . . ?
C00U C00K H00l 108.9(17) . . ?
C00U C00K C00S 110.9(3) . . ?
C00G C00L C006 109.7(2) . . ?
H00m C00L C006 111.1(18) . . ?
H00m C00L C00G 107.0(19) . . ?
H00n C00L C006 106.3(16) . . ?
H00n C00L C00G 110.4(16) . . ?
H00n C00L H00m 112(3) . . ?
C00A C00M C009 113.3(2) . . ?
H00o C00M C009 109.9(17) . . ?
H00o C00M C00A 108.7(16) . . ?
H00p C00M C009 114(2) . . ?
H00p C00M C00A 103.2(18) . . ?
H00p C00M H00o 107(2) . . ?
H00q C00N C00F 115.0(17) . . ?
H00r C00N C00F 111.9(18) . . ?
H00r C00N H00q 107(2) . . ?
H00s C00N C00F 106.0(18) . . ?
H00s C00N H00q 114(3) . . ?
H00s C00N H00r 103(2) . . ?
O008 C00O O005 123.3(3) . . ?
C00T C00O O005 111.5(3) . . ?
C00T C00O O008 125.1(4) . . ?
C00G C00P C00C 113.4(2) . . ?
H00t C00P C00C 105.8(16) . . ?
H00t C00P C00G 111.4(16) . . ?
H00u C00P C00C 105.5(19) . . ?
H00u C00P C00G 113.6(17) . . ?
H00u C00P H00t 107(2) . . ?
C00B C00Q F002 107.4(2) . . ?
H00v C00Q F002 115.05(15) . . ?
H00v C00Q C00B 110.47(16) . . ?
H00w C00Q F002 6.41(15) . . ?
H00w C00Q C00B 110.47(15) . . ?
H00w C00Q H00v 108.7 . . ?
C00R C00Q F002 106.7(2) . . ?
C00R C00Q C00B 106.3(2) . . ?
C00R C00Q H00v 110.47(17) . . ?
C00R C00Q H00w 110.47(15) . . ?
C00Q C00R C00E 107.3(2) . . ?
H00y C00R C00E 110.26(14) . . ?
H00y C00R C00Q 110.26(15) . . ?
H00x C00R C00E 110.26(16) . . ?
H00x C00R C00Q 110.26(17) . . ?
H00x C00R H00y 108.5 . . ?
F4 C00R C00E 108.1(4) . . ?
F4 C00R C00Q 100.2(9) . . ?
F4 C00R H00y 12.2(9) . . ?
F4 C00R H00x 119.7(8) . . ?
H00z C00S C00K 107.0(16) . . ?
H C00S C00K 112.9(16) . . ?
H C00S H00z 105(2) . . ?
C00T C00S C00K 115.6(3) . . ?
C00T C00S H00z 108.5(18) . . ?
C00T C00S H 107.0(16) . . ?
C00S C00T C00O 109.2(3) . . ?
H00 C00T C00O 108.4(19) . . ?
H00 C00T C00S 114(2) . . ?
Ha C00T C00O 110.5(16) . . ?
Ha C00T C00S 107.3(19) . . ?
Ha C00T H00 107(3) . . ?
H1 C00U C00K 108(2) . . ?
Hb C00U C00K 115(2) . . ?
Hb C00U H1 113(3) . . ?
Hc C00U C00K 106(2) . . ?
Hc C00U H1 108(3) . . ?
Hc C00U Hb 107(2) . . ?
H2 C00V O005 109.5 . . ?
Hd C00V O005 109.5 . . ?
Hd C00V H2 109.5 . . ?
He C00V O005 109.5 . . ?
He C00V H2 109.5 . . ?
He C00V Hd 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 C006 C00H C009 118.0(3) . . . . ?
O001 C006 C00H C00B -3.9(3) . . . . ?
O001 C006 C00L C00G -119.3(3) . . . . ?
F002 C00Q C00B C007 -132.2(2) . . . . ?
F002 C00Q C00B C00H 101.1(2) . . . . ?
F002 C00Q C00R C00E 106.2(2) . . . . ?
F002 C00Q C00R F4 -6.6(5) . . . . ?
O003 C00A C007 C00B -111.7(3) . . . . ?
O003 C00A C007 C00E -1.4(3) . . . . ?
O003 C00A C007 C00I 128.2(3) . . . . ?
O003 C00A C00M C009 120.6(3) . . . . ?
O004 C00C C00D C00J 127.0(3) . . . . ?
O004 C00C C00P C00G -130.4(3) . . . . ?
O005 C00O C00T C00S -114.0(3) . . . . ?
C006 C00H C009 C00F 57.1(2) . . . . ?
C006 C00H C009 C00M -173.6(2) . . . . ?
C006 C00H C00B C007 -176.0(2) . . . . ?
C006 C00H C00B C00Q -52.6(3) . . . . ?
C006 C00L C00G C00F -53.8(3) . . . . ?
C006 C00L C00G C00P 73.6(3) . . . . ?
C007 C00A C00M C009 -53.8(2) . . . . ?
C007 C00B C00H C009 62.7(2) . . . . ?
C007 C00B C00Q C00R -18.3(2) . . . . ?
C007 C00E C00K C00S 172.3(3) . . . . ?
C007 C00E C00K C00U -60.1(3) . . . . ?
C007 C00E C00R C00Q 31.6(2) . . . . ?
C007 C00E C00R F4 138.9(10) . . . . ?
O008 C00O C00T C00S 62.7(4) . . . . ?
C009 C00F C00G C00L 53.0(3) . . . . ?
C009 C00F C00G C00P -71.1(2) . . . . ?
C009 C00F C00J C00D 65.2(2) . . . . ?
C009 C00H C00B C00Q -173.8(2) . . . . ?
C00B C00Q C00R C00E -8.2(2) . . . . ?
C00B C00Q C00R F4 -121.0(5) . . . . ?
C00C C00D C00J C00F 56.7(3) . . . . ?
C00C C00P C00G C00F -48.0(3) . . . . ?
C00C C00P C00G C00L -174.4(2) . . . . ?
C00D C00J C00F C00G -55.0(3) . . . . ?
C00D C00J C00F C00N -173.2(3) . . . . ?
C00E C00K C00S C00T 64.1(3) . . . . ?
C00K C00S C00T C00O 169.8(3) . . . . ?


_olex2_date_sample_data_collection 2022-09-27
_olex2_date_sample_submission    2022-08-26
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with mineral oil'
_olex2_submission_original_sample_id 'SY 635'
_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 1.738
_oxdiff_exptl_absorpt_empirical_full_min 0.517
loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
F4 0.0100

loop_
_restr_U_similar_atom_site_label_1
_restr_U_similar_atom_site_label_2
_restr_U_similar_weight_param
C00E F1 0.0100

