# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_smghlb
_database_code_depnum_ccdc_archive 'CCDC 2040010'
loop_
_audit_author_name
_audit_author_address
'Stephen P. Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2020-10-22 deposited with the CCDC.	2021-03-15 downloaded from the CCDC.
;
_nottingham_internal_coll_name   SMGHLB
_nottingham_internal_coll_number 18405
_nottingham_internal_coll_client SMG/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '1.00, 4.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczspa
_nottingham_internal_coll_date   02/09/2019
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'SN, XDA 017-09'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 02/09/2019
_nottingham_internal_process_user pczspa
_nottingham_internal_solution_date 04/09/2019
_nottingham_internal_solution_user pczspa
_nottingham_internal_refinement_date 04/09/2019
_nottingham_internal_refinement_user pczspa
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 04/09/2019
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date ?
_refine_special_details          ?
_audit_creation_date             2019-09-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H21 F O'
_chemical_formula_sum            'C25 H21 F O'
_chemical_formula_weight         356.42
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C25H21F1O1
_chemical_oxdiff_usercomment     
'SMGHLB #SN-1524 FOMBLIM ON MICROMOUNT FOR SMG/HWL'
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'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.9239(4)
_cell_length_b                   5.6798(2)
_cell_length_c                   14.6714(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.215(4)
_cell_angle_gamma                90
_cell_volume                     932.42(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3624
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.8170
_cell_measurement_theta_min      3.9380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 0 5 0.0332
-3 0 -5 0.0332
0 -4 -1 0.1927
5 3 -1 0.1680
-5 2 2 0.1418
5 0 -1 0.0550
-5 0 1 0.0550
1 0 -5 0.0679
-1 0 5 0.0679

_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.066
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
3.0019 -0.0061 5.0014 -0.1088 -0.6519 0.4550
-3.0019 0.0061 -5.0014 0.1088 0.6519 -0.4550
-0.0084 -3.9955 -1.0172 1.0654 0.0911 0.2105
5.0070 2.9961 -0.9843 -0.9322 -0.0343 0.4747
-4.9966 1.9985 2.0059 -0.3983 -0.0518 -0.7410
5.0009 -0.0012 -0.9973 -0.1368 -0.0493 0.6420
-5.0009 0.0012 0.9973 0.1368 0.0493 -0.6420
0.9990 0.0043 -4.9992 -0.0045 0.5235 0.0686
-0.9990 -0.0043 4.9992 0.0045 -0.5235 -0.0686

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6375
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.140
_diffrn_reflns_theta_min         3.210
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -92.00 -54.00   1.00    1.00    --  -38.50-154.00-112.00   38
  2  ω      3.00  32.00   1.00    1.00    --  -38.50  38.00-150.00   29
  3  ω    -49.00  33.00   1.00    1.00    --  -38.50  38.00 -90.00   82
  4  ω    -44.00  31.00   1.00    1.00    --  -38.50  38.00-180.00   75
  5  ω     20.00  82.00   1.00    1.00    --   43.50 -99.00 -60.00   62
  6  ω    -22.00  63.00   1.00    1.00    --   43.50 -38.00   0.00   85
  7  ω     35.00  84.00   1.00    4.00    --  103.63 -95.00 -90.00   49
  8  ω     24.00 142.00   1.00    4.00    --  103.63 -15.00 120.00  118
  9  ω    131.00 177.00   1.00    4.00    --  103.63  30.00 -60.00   46
 10  ω     29.00  58.00   1.00    4.00    --  103.63 -30.00 -60.00   29
 11  ω     31.00  81.00   1.00    4.00    --  103.63 -30.00-120.00   50
 12  ω     61.00 116.00   1.00    4.00    --  103.63-125.00   0.00   55
 13  ω     34.00  91.00   1.00    4.00    --  103.63 -30.00  30.00   57
 14  ω     37.00  90.00   1.00    4.00    --  103.63 -30.00 -30.00   53
 15  ω     33.00 121.00   1.00    4.00    --  103.63 -61.00 120.00   88
 16  ω     80.00 117.00   1.00    4.00    --  103.63-125.00-180.00   37
 17  ω     38.00 127.00   1.00    4.00    --  103.63 -77.00   0.00   89
 18  ω     68.00  93.00   1.00    4.00    --  103.63 -95.00-150.00   25
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0284152000
_diffrn_orient_matrix_UB_12      -0.2653095000
_diffrn_orient_matrix_UB_13      -0.0050101000
_diffrn_orient_matrix_UB_21      -0.0320193000
_diffrn_orient_matrix_UB_22      0.0055488000
_diffrn_orient_matrix_UB_23      -0.1111138000
_diffrn_orient_matrix_UB_31      0.1308231000
_diffrn_orient_matrix_UB_32      -0.0561041000
_diffrn_orient_matrix_UB_33      0.0123817000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.941
_reflns_number_gt                3405
_reflns_number_total             3582
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_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         0.128
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1428 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3582
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.055
_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)+(0.0538P)²+0.2275P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0841
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
F1 F 0.18887(18) 0.5712(5) 0.94750(17) 0.0472(6) Uani 1 1 d . . . . .
C2 C 0.2798(3) 0.6339(7) 0.9170(2) 0.0317(7) Uani 1 1 d . . . . .
C3 C 0.3099(3) 0.4829(6) 0.8554(3) 0.0317(7) Uani 1 1 d . . . . .
H3 H 0.268592 0.342916 0.834361 0.038 Uiso 1 1 calc R . . . .
C4 C 0.4046(3) 0.5491(6) 0.8260(2) 0.0286(7) Uani 1 1 d . . . . .
H4 H 0.428669 0.449373 0.785919 0.034 Uiso 1 1 calc R . . . .
C5 C 0.4638(3) 0.7614(6) 0.8556(2) 0.0236(6) Uani 1 1 d . . . . .
C6 C 0.4280(3) 0.9097(6) 0.9167(2) 0.0269(7) Uani 1 1 d . . . . .
H6 H 0.466355 1.053227 0.936123 0.032 Uiso 1 1 calc R . . . .
C7 C 0.3359(3) 0.8442(7) 0.9485(2) 0.0315(7) Uani 1 1 d . . . . .
H7 H 0.312784 0.940452 0.990126 0.038 Uiso 1 1 calc R . . . .
C8 C 0.5661(3) 0.8405(6) 0.8258(2) 0.0257(6) Uani 1 1 d . . . . .
O9 O 0.5987(2) 1.0441(4) 0.8375(2) 0.0364(6) Uani 1 1 d . . . . .
C10 C 0.6253(3) 0.6635(6) 0.7796(2) 0.0252(6) Uani 1 1 d . . . . .
H10A H 0.576906 0.644747 0.711628 0.030 Uiso 1 1 calc R . . . .
H10B H 0.629483 0.512088 0.811144 0.030 Uiso 1 1 calc R . . . .
C11 C 0.7518(3) 0.7400(6) 0.7874(2) 0.0260(7) Uani 1 1 d . . . . .
H11 H 0.753102 0.909319 0.775051 0.031 Uiso 1 1 calc R . . . .
C12 C 0.7969(3) 0.6039(6) 0.7176(2) 0.0236(6) Uani 1 1 d . . . . .
C13 C 0.8842(3) 0.4518(6) 0.7639(2) 0.0254(6) Uani 1 1 d . . . . .
C14 C 0.9030(3) 0.4475(7) 0.8719(2) 0.0313(7) Uani 1 1 d . . . . .
H14A H 0.987346 0.442764 0.910702 0.038 Uiso 1 1 calc R . . . .
H14B H 0.863422 0.313163 0.888285 0.038 Uiso 1 1 calc R . . . .
C15 C 0.8460(3) 0.6790(7) 0.8871(2) 0.0310(7) Uani 1 1 d . . . . .
H15A H 0.905674 0.802342 0.908094 0.037 Uiso 1 1 calc R . . . .
H15B H 0.808462 0.659978 0.935737 0.037 Uiso 1 1 calc R . . . .
C16 C 0.7343(3) 0.6320(6) 0.6111(2) 0.0230(6) Uani 1 1 d . . . . .
C17 C 0.6566(3) 0.4558(6) 0.5607(2) 0.0290(7) Uani 1 1 d . . . . .
H17 H 0.648168 0.320112 0.593259 0.035 Uiso 1 1 calc R . . . .
C18 C 0.5915(3) 0.4800(7) 0.4623(2) 0.0353(8) Uani 1 1 d . . . . .
H18 H 0.538110 0.362931 0.429732 0.042 Uiso 1 1 calc R . . . .
C19 C 0.6060(3) 0.6781(7) 0.4128(2) 0.0353(8) Uani 1 1 d . . . . .
H19 H 0.563954 0.692770 0.346583 0.042 Uiso 1 1 calc R . . . .
C20 C 0.6832(3) 0.8545(7) 0.4620(2) 0.0331(7) Uani 1 1 d . . . . .
H20 H 0.693070 0.987738 0.428681 0.040 Uiso 1 1 calc R . . . .
C21 C 0.7462(3) 0.8339(6) 0.5611(2) 0.0277(7) Uani 1 1 d . . . . .
H21 H 0.796434 0.954930 0.593982 0.033 Uiso 1 1 calc R . . . .
C22 C 0.9553(3) 0.3038(6) 0.7217(2) 0.0263(7) Uani 1 1 d . . . . .
C23 C 0.9769(3) 0.3707(6) 0.6372(2) 0.0287(7) Uani 1 1 d . . . . .
H23 H 0.943922 0.509827 0.605939 0.034 Uiso 1 1 calc R . . . .
C24 C 1.0465(3) 0.2336(7) 0.5996(3) 0.0355(8) Uani 1 1 d . . . . .
H24 H 1.060258 0.282134 0.543844 0.043 Uiso 1 1 calc R . . . .
C25 C 1.0955(3) 0.0251(7) 0.6443(3) 0.0395(8) Uani 1 1 d . . . . .
H25 H 1.141893 -0.067370 0.618731 0.047 Uiso 1 1 calc R . . . .
C26 C 1.0748(3) -0.0446(7) 0.7275(3) 0.0393(8) Uani 1 1 d . . . . .
H26 H 1.106259 -0.186244 0.757287 0.047 Uiso 1 1 calc R . . . .
C27 C 1.0077(3) 0.0951(6) 0.7668(2) 0.0325(7) Uani 1 1 d . . . . .
H27 H 0.997332 0.048880 0.824228 0.039 Uiso 1 1 calc R . . . .


_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
F1 C2 1.356(4) . ?
C2 C3 1.380(5) . ?
C2 C7 1.369(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(5) . ?
C5 C6 1.401(4) . ?
C5 C8 1.499(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(5) . ?
C7 H7 0.9300 . ?
C8 O9 1.213(4) . ?
C8 C10 1.517(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.534(4) . ?
C11 H11 0.9800 . ?
C11 C12 1.522(4) . ?
C11 C15 1.545(4) . ?
C12 C13 1.343(5) . ?
C12 C16 1.489(4) . ?
C13 C14 1.522(4) . ?
C13 C22 1.473(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.531(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.390(5) . ?
C16 C21 1.395(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.391(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.382(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.384(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.391(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.403(4) . ?
C22 C27 1.396(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.384(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.382(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.384(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.387(5) . ?
C27 H27 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C2 C3 118.1(3) . . ?
F1 C2 C7 118.1(3) . . ?
C7 C2 C3 123.8(3) . . ?
C2 C3 H3 121.4 . . ?
C2 C3 C4 117.2(3) . . ?
C4 C3 H3 121.4 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 C8 123.1(3) . . ?
C6 C5 C8 117.7(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.5(3) . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C6 118.2(3) . . ?
C2 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C5 C8 C10 118.9(3) . . ?
O9 C8 C5 119.9(3) . . ?
O9 C8 C10 121.3(3) . . ?
C8 C10 H10A 109.2 . . ?
C8 C10 H10B 109.2 . . ?
C8 C10 C11 112.1(3) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C10 C11 H11 110.0 . . ?
C10 C11 C15 112.4(2) . . ?
C12 C11 C10 111.9(3) . . ?
C12 C11 H11 110.0 . . ?
C12 C11 C15 102.3(3) . . ?
C15 C11 H11 110.0 . . ?
C13 C12 C11 112.2(3) . . ?
C13 C12 C16 128.3(3) . . ?
C16 C12 C11 119.1(3) . . ?
C12 C13 C14 110.3(3) . . ?
C12 C13 C22 127.7(3) . . ?
C22 C13 C14 122.0(3) . . ?
C13 C14 H14A 111.2 . . ?
C13 C14 H14B 111.2 . . ?
C13 C14 C15 103.0(3) . . ?
H14A C14 H14B 109.1 . . ?
C15 C14 H14A 111.2 . . ?
C15 C14 H14B 111.2 . . ?
C11 C15 H15A 110.6 . . ?
C11 C15 H15B 110.6 . . ?
C14 C15 C11 105.6(3) . . ?
C14 C15 H15A 110.6 . . ?
C14 C15 H15B 110.6 . . ?
H15A C15 H15B 108.8 . . ?
C17 C16 C12 118.8(3) . . ?
C17 C16 C21 118.8(3) . . ?
C21 C16 C12 122.4(3) . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.8(3) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.4(3) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 H21 119.9 . . ?
C20 C21 C16 120.2(3) . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C13 121.7(3) . . ?
C27 C22 C13 120.9(3) . . ?
C27 C22 C23 117.4(3) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.2(3) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.4(3) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 120.4 . . ?
C24 C25 C26 119.2(3) . . ?
C26 C25 H25 120.4 . . ?
C25 C26 H26 119.7 . . ?
C25 C26 C27 120.5(3) . . ?
C27 C26 H26 119.7 . . ?
C22 C27 H27 119.4 . . ?
C26 C27 C22 121.1(3) . . ?
C26 C27 H27 119.4 . . ?

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_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 1.300
_oxdiff_exptl_absorpt_empirical_full_min 0.797
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pentane, Et2O'
####################################################################### 
# 
# 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_smghlc
_database_code_depnum_ccdc_archive 'CCDC 2040011'
loop_
_audit_author_name
_audit_author_address
'Stephen P. Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2020-10-22 deposited with the CCDC.	2021-03-15 downloaded from the CCDC.
;
_nottingham_internal_coll_name   SMGHLC
_nottingham_internal_coll_number 18635
_nottingham_internal_coll_client SMG/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '20.00, 5.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczspa
_nottingham_internal_coll_date   18/02/2020
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 19/02/2020
_nottingham_internal_process_user pczspa
_nottingham_internal_solution_date 19/02/2020
_nottingham_internal_solution_user pczspa
_nottingham_internal_refinement_date 19/02/2020
_nottingham_internal_refinement_user pczspa
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 19/02/2020
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date ?
_refine_special_details          
'Conformational disorder is modelled in the fluorophenyl ring moiety. Occupancies of the two disorder components were refined and constrained to sum to unity. The geometries of the two disorder components were restrained to be similar (SAME). Rigid bond and similarity restraints were applied to the anisoptropic displacement parameters of the disordered atoms (RIGU, SIMU). Carbon atoms C20 and C20a were constrained to have identical anisotropic displacement parameters.'
_audit_creation_date             2020-02-19
_audit_creation_method           
;
Olex2 1.2
(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 H19 F O S'
_chemical_formula_sum            'C23 H19 F O S'
_chemical_formula_weight         362.44
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23H19FOS
_chemical_oxdiff_usercomment     
'MNSLGF #186xx GVB-1776 for SLG/NRC in Fomblin film on a micromount'
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.4023(2)
_cell_length_b                   11.0606(2)
_cell_length_c                   9.9012(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.589(2)
_cell_angle_gamma                90
_cell_volume                     907.31(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6551
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.6920
_cell_measurement_theta_min      5.3250
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.757
_exptl_absorpt_coefficient_mu    1.731
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.740
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             380
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 5 3 0.0135
-1 -5 -3 0.0135
0 -5 3 0.0278
0 5 -3 0.0278
5 1 -2 0.0602
-2 5 -2 0.0477
-4 -4 3 0.0661

_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.027
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
1.0005 4.9949 3.0037 -0.8439 -0.1979 0.1470
-1.0005 -4.9949 -3.0037 0.8439 0.1979 -0.1470
-0.0017 -5.0063 2.9972 0.0522 0.5523 -0.6341
0.0017 5.0063 -2.9972 -0.0522 -0.5523 0.6341
4.9997 0.9998 -1.9970 -0.1040 -0.8200 -0.4493
-1.9981 5.0061 -1.9982 -0.0689 -0.2337 0.8385
-4.0007 -4.0030 2.9958 0.1806 0.9684 -0.0156

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9932
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.796
_diffrn_reflns_theta_min         4.529
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  38.00   1.00    5.00    --  -41.70  19.00   0.00   43
  2  ω     -5.00  38.00   1.00    5.00    --  -41.70  19.00-120.00   43
  3  ω    -21.00  33.00   1.00    5.00    --  -41.70  38.00 -90.00   54
  4  ω     -5.00  38.00   1.00    5.00    --  -41.70  19.00  60.00   43
  5  ω     -5.00  38.00   1.00    5.00    --  -41.70  19.00 120.00   43
  6  ω     -5.00  38.00   1.00    5.00    --  -41.70  19.00 -30.00   43
  7  ω   -116.00 -17.00   1.00    5.00    --  -41.70 -38.00-180.00   99
  8  ω    -21.00  33.00   1.00    5.00    --  -41.70  38.00 -60.00   54
  9  ω     -5.00  38.00   1.00    5.00    --  -41.70  19.00  90.00   43
 10  ω     27.00  98.00   1.00    5.00    --   41.70-125.00  90.00   71
 11  ω     79.00 177.00   1.00   20.00    --  104.36  45.00-120.00   98
 12  ω     75.00 177.00   1.00   20.00    --  104.36  61.00-150.00  102
 13  ω     28.00  57.00   1.00   20.00    --  104.36 -30.00 -90.00   29
 14  ω     31.00  72.00   1.00   20.00    --  104.36 -45.00 150.00   41
 15  ω     75.00 177.00   1.00   20.00    --  104.36  61.00-180.00  102
 16  ω     22.00 106.00   1.00   20.00    --  104.36 -94.00 -30.00   84
 17  ω     22.00 106.00   1.00   20.00    --  104.36 -94.00  30.00   84
 18  ω     31.00  72.00   1.00   20.00    --  104.36 -45.00  30.00   41
 19  ω     76.00 178.00   1.00   20.00    --  104.36  30.00  90.00  102
 20  ω     28.00  57.00   1.00   20.00    --  104.36 -30.00 -60.00   29
 21  ω    103.00 178.00   1.00   20.00    --  104.36  77.00   0.00   75
 22  ω     76.00 178.00   1.00   20.00    --  104.36  30.00-180.00  102
 23  ω     31.00  72.00   1.00   20.00    --  104.36 -45.00 -60.00   41
 24  ω     79.00 177.00   1.00   20.00    --  104.36  45.00 -90.00   98
 25  ω     32.00  93.00   1.00   20.00    --  104.36 -61.00-120.00   61
 26  ω     32.00  93.00   1.00   20.00    --  104.36 -61.00  90.00   61
 27  ω   -114.00 -23.00   1.00    5.00    --  -41.70 -57.00 -30.00   91
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas S2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0531858000
_diffrn_orient_matrix_UB_12      -0.0841919000
_diffrn_orient_matrix_UB_13      -0.1232438000
_diffrn_orient_matrix_UB_21      -0.1198936000
_diffrn_orient_matrix_UB_22      -0.0630459000
_diffrn_orient_matrix_UB_23      0.0789057000
_diffrn_orient_matrix_UB_31      -0.1317328000
_diffrn_orient_matrix_UB_32      0.0913355000
_diffrn_orient_matrix_UB_33      -0.0590770000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                3479
_reflns_number_total             3539
_reflns_odcompleteness_completeness 100.00
_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 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_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         0.205
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1593 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3539
_refine_ls_number_restraints     323
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0252
_refine_ls_restrained_S_all      0.984
_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)+(0.0412P)²+0.1337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0672
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C20A-C11 \\sim C20-C11
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim F26 \\sim C20A
\\sim C21A \\sim C22A \\sim C23A \\sim C24A \\sim C25A \\sim F26A: within 2A
with sigma of 0.015 and sigma for terminal atoms of 0.03
Uanis(C20) = Uanis(C20A)
4. Rigid body (RIGU) restrains
 C20, C21, C22, C23, C24, C25, F26, C20A, C21A, C22A, C23A, C24A, C25A, F26A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{C20, C21, C22, C23, C24, C25, F26} sigma for 1-2: 0.02, 1-3: 0.04
as
{C20A, C21A, C22A, C23A, C24A, C25A, F26A}
6. Others
 Sof(C20A)=Sof(C21A)=Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=
 Sof(H24A)=Sof(C25A)=Sof(H25A)=Sof(F26A)=1-FVAR(1)
 Sof(C20)=Sof(C21)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=
 Sof(C25)=Sof(H25)=Sof(F26)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C9(H9)
7.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B)
7.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19),
 C22(H22), C23(H23), C24(H24), C25(H25), C22A(H22A), C23A(H23A), C24A(H24A),
 C25A(H25A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 1.22755(6) 0.29367(4) 1.07116(5) 0.02962(13) Uani 1 1 d . . . . .
C2 C 1.1029(2) 0.39992(17) 0.97900(19) 0.0220(4) Uani 1 1 d . . . . .
C3 C 1.1179(2) 0.5128(2) 1.0420(2) 0.0284(4) Uani 1 1 d . . . . .
H3 H 1.059050 0.582661 1.007551 0.034 Uiso 1 1 calc R . . . .
C4 C 1.2333(3) 0.5096(3) 1.1649(2) 0.0407(5) Uani 1 1 d . . . . .
H4 H 1.260223 0.577858 1.222460 0.049 Uiso 1 1 calc R . . . .
C5 C 1.3008(3) 0.3988(3) 1.1911(2) 0.0413(6) Uani 1 1 d . . . . .
H5 H 1.380740 0.381713 1.268434 0.050 Uiso 1 1 calc R . . . .
C6 C 1.0008(2) 0.36163(18) 0.8518(2) 0.0233(4) Uani 1 1 d . . . . .
O7 O 0.9978(2) 0.25563(14) 0.81699(17) 0.0346(4) Uani 1 1 d . . . . .
C8 C 0.8966(2) 0.45467(18) 0.7657(2) 0.0266(4) Uani 1 1 d . . . . .
H8A H 0.923729 0.456574 0.672186 0.032 Uiso 1 1 calc R . . . .
H8B H 0.917484 0.535905 0.806843 0.032 Uiso 1 1 calc R . . . .
C9 C 0.7190(2) 0.42204(19) 0.7587(2) 0.0246(4) Uani 1 1 d . . . . .
H9 H 0.699782 0.338657 0.720398 0.029 Uiso 1 1 calc R . . . .
C10 C 0.6000(2) 0.50931(18) 0.67612(19) 0.0212(4) Uani 1 1 d . . . . .
C11 C 0.4759(2) 0.53417(17) 0.7415(2) 0.0223(4) Uani 1 1 d D . . . .
C12 C 0.4963(3) 0.4731(2) 0.8799(2) 0.0300(4) Uani 1 1 d . . . . .
H12A H 0.418994 0.405515 0.879449 0.036 Uiso 1 1 calc R . . . .
H12B H 0.480266 0.531289 0.952409 0.036 Uiso 1 1 calc R . . . .
C13 C 0.6682(3) 0.4273(3) 0.9013(2) 0.0449(6) Uani 1 1 d . . . . .
H13A H 0.674743 0.345953 0.943576 0.054 Uiso 1 1 calc R . . . .
H13B H 0.739884 0.482633 0.962246 0.054 Uiso 1 1 calc R . . . .
C14 C 0.6232(2) 0.55335(17) 0.53918(19) 0.0200(4) Uani 1 1 d . . . . .
C15 C 0.5925(2) 0.67432(18) 0.5030(2) 0.0249(4) Uani 1 1 d . . . . .
H15 H 0.555503 0.727925 0.566097 0.030 Uiso 1 1 calc R . . . .
C16 C 0.6156(3) 0.7169(2) 0.3754(2) 0.0300(5) Uani 1 1 d . . . . .
H16 H 0.595684 0.799538 0.352254 0.036 Uiso 1 1 calc R . . . .
C17 C 0.6676(3) 0.6392(2) 0.2821(2) 0.0318(5) Uani 1 1 d . . . . .
H17 H 0.682264 0.668043 0.194621 0.038 Uiso 1 1 calc R . . . .
C18 C 0.6981(3) 0.5196(2) 0.3171(2) 0.0307(4) Uani 1 1 d . . . . .
H18 H 0.733185 0.466137 0.252982 0.037 Uiso 1 1 calc R . . . .
C19 C 0.6780(2) 0.47647(18) 0.4450(2) 0.0247(4) Uani 1 1 d . . . . .
H19 H 0.701584 0.394366 0.468453 0.030 Uiso 1 1 calc R . . . .
C20 C 0.323(2) 0.5911(18) 0.6740(17) 0.0180(16) Uani 0.461(5) 1 d D U P A 1
C21 C 0.2530(18) 0.6754(13) 0.7471(11) 0.026(2) Uani 0.461(5) 1 d D U P A 1
C22 C 0.1040(13) 0.7357(10) 0.6938(11) 0.033(2) Uani 0.461(5) 1 d D U P A 1
H22 H 0.057136 0.793026 0.746838 0.039 Uiso 0.461(5) 1 calc R . P A 1
C23 C 0.0328(12) 0.7068(9) 0.5633(9) 0.0308(19) Uani 0.461(5) 1 d D U P A 1
H23 H -0.064424 0.746025 0.523863 0.037 Uiso 0.461(5) 1 calc R . P A 1
C24 C 0.0998(14) 0.6219(10) 0.4886(10) 0.030(2) Uani 0.461(5) 1 d D U P A 1
H24 H 0.047885 0.602483 0.398572 0.036 Uiso 0.461(5) 1 calc R . P A 1
C25 C 0.2393(16) 0.5657(11) 0.5421(11) 0.019(2) Uani 0.461(5) 1 d D U P A 1
H25 H 0.282253 0.506784 0.488294 0.023 Uiso 0.461(5) 1 calc R . P A 1
F26 F 0.3277(4) 0.7116(3) 0.8749(4) 0.0424(10) Uani 0.461(5) 1 d D U P A 1
C20A C 0.3281(17) 0.6070(14) 0.6994(14) 0.0180(16) Uani 0.539(5) 1 d D U P A 2
C21A C 0.2355(16) 0.5877(11) 0.5732(10) 0.0232(18) Uani 0.539(5) 1 d D U P A 2
C22A C 0.0907(12) 0.6510(8) 0.5245(8) 0.0269(17) Uani 0.539(5) 1 d D U P A 2
H22A H 0.032198 0.637255 0.435124 0.032 Uiso 0.539(5) 1 calc R . P A 2
C23A C 0.0380(10) 0.7336(7) 0.6123(8) 0.0267(15) Uani 0.539(5) 1 d D U P A 2
H23A H -0.058558 0.778036 0.583702 0.032 Uiso 0.539(5) 1 calc R . P A 2
C24A C 0.1259(10) 0.7514(8) 0.7414(8) 0.0265(15) Uani 0.539(5) 1 d D U P A 2
H24A H 0.087919 0.807151 0.801729 0.032 Uiso 0.539(5) 1 calc R . P A 2
C25A C 0.2656(14) 0.6905(11) 0.7838(9) 0.0229(17) Uani 0.539(5) 1 d D U P A 2
H25A H 0.323022 0.704827 0.873470 0.027 Uiso 0.539(5) 1 calc R . P A 2
F26A F 0.2771(3) 0.4994(3) 0.4876(3) 0.0342(8) Uani 0.539(5) 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.7299(18) . ?
S1 C5 1.702(3) . ?
C2 C3 1.391(3) . ?
C2 C6 1.464(3) . ?
C3 C4 1.425(3) . ?
C4 C5 1.357(4) . ?
C6 O7 1.221(3) . ?
C6 C8 1.518(3) . ?
C8 C9 1.526(3) . ?
C9 C10 1.526(3) . ?
C9 C13 1.543(3) . ?
C10 C11 1.344(3) . ?
C10 C14 1.484(3) . ?
C11 C12 1.511(3) . ?
C11 C20 1.488(12) . ?
C11 C20A 1.481(10) . ?
C12 C13 1.512(3) . ?
C14 C15 1.398(3) . ?
C14 C19 1.395(3) . ?
C15 C16 1.393(3) . ?
C16 C17 1.384(3) . ?
C17 C18 1.381(3) . ?
C18 C19 1.390(3) . ?
C20 C21 1.371(13) . ?
C20 C25 1.404(12) . ?
C21 C22 1.439(16) . ?
C21 F26 1.375(9) . ?
C22 C23 1.368(11) . ?
C23 C24 1.372(9) . ?
C24 C25 1.354(14) . ?
C20A C21A 1.374(11) . ?
C20A C25A 1.405(10) . ?
C21A C22A 1.416(13) . ?
C21A F26A 1.376(8) . ?
C22A C23A 1.384(8) . ?
C23A C24A 1.380(8) . ?
C24A C25A 1.358(12) . ?

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
C5 S1 C2 91.17(11) . . ?
C3 C2 S1 111.79(15) . . ?
C3 C2 C6 129.92(18) . . ?
C6 C2 S1 118.29(15) . . ?
C2 C3 C4 111.0(2) . . ?
C5 C4 C3 112.9(2) . . ?
C4 C5 S1 113.14(17) . . ?
C2 C6 C8 119.18(17) . . ?
O7 C6 C2 120.14(19) . . ?
O7 C6 C8 120.67(19) . . ?
C6 C8 C9 109.48(16) . . ?
C8 C9 C13 111.53(18) . . ?
C10 C9 C8 115.05(16) . . ?
C10 C9 C13 102.13(17) . . ?
C11 C10 C9 111.27(17) . . ?
C11 C10 C14 127.13(18) . . ?
C14 C10 C9 121.55(16) . . ?
C10 C11 C12 111.44(17) . . ?
C10 C11 C20 123.5(8) . . ?
C10 C11 C20A 131.1(7) . . ?
C20 C11 C12 123.7(9) . . ?
C20A C11 C12 117.5(7) . . ?
C11 C12 C13 103.78(17) . . ?
C12 C13 C9 106.72(18) . . ?
C15 C14 C10 120.09(18) . . ?
C19 C14 C10 121.24(17) . . ?
C19 C14 C15 118.66(18) . . ?
C16 C15 C14 120.57(19) . . ?
C17 C16 C15 120.18(19) . . ?
C18 C17 C16 119.55(19) . . ?
C17 C18 C19 120.8(2) . . ?
C18 C19 C14 120.22(19) . . ?
C21 C20 C11 117.7(11) . . ?
C21 C20 C25 115.9(9) . . ?
C25 C20 C11 126.5(11) . . ?
C20 C21 C22 123.0(9) . . ?
C20 C21 F26 121.0(12) . . ?
F26 C21 C22 116.0(10) . . ?
C23 C22 C21 117.1(9) . . ?
C22 C23 C24 121.0(8) . . ?
C25 C24 C23 120.6(8) . . ?
C24 C25 C20 122.5(9) . . ?
C21A C20A C11 119.6(9) . . ?
C21A C20A C25A 115.6(8) . . ?
C25A C20A C11 124.6(9) . . ?
C20A C21A C22A 123.8(8) . . ?
C20A C21A F26A 120.4(10) . . ?
F26A C21A C22A 115.7(8) . . ?
C23A C22A C21A 117.3(7) . . ?
C24A C23A C22A 119.9(6) . . ?
C25A C24A C23A 121.2(7) . . ?
C24A C25A C20A 122.1(7) . . ?

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_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 1.503
_oxdiff_exptl_absorpt_empirical_full_min 0.773
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pentane'
####################################################################### 
# 
# 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_smghld
_database_code_depnum_ccdc_archive 'CCDC 2040013'
loop_
_audit_author_name
_audit_author_address
'Stephen P. Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2020-10-22 deposited with the CCDC.	2021-03-15 downloaded from the CCDC.
;
_nottingham_internal_coll_name   SMGHLD
_nottingham_internal_coll_number 18636
_nottingham_internal_coll_client SMG/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '8.00, 2.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczspa
_nottingham_internal_coll_date   19/02/2020
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 19/02/2020
_nottingham_internal_process_user pczspa
_nottingham_internal_solution_date 18/05/2020
_nottingham_internal_solution_user pczspa
_nottingham_internal_refinement_date 18/05/2020
_nottingham_internal_refinement_user pczspa
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 18/05/2020
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date 18/05/2020
_refine_special_details          
;
 Conformational disorder is observed for fluorophenyl moiety
 F1-C7. The occupancies of the coplanar disorder components 
 were refined and restrained to sum to unity, having values
 of 0.92(1) and 0.08(1) each. The geometries of the two
 components are restrained to be similar (SAME). The
 anisotropic displacement parameters of the coincident
 atoms are contrained to be identical (EADP). A rigid bond
 and similarity restraint was applied to all atoms in the
 disordered moieties. All hydrogen atoms were observed in
 the electron density map before being geometrically
 placed and refined with a riding model.
;
_audit_creation_date             2020-05-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H25 F O'
_chemical_formula_sum            'C23 H25 F O'
_chemical_formula_weight         336.43
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23H25FO
_chemical_oxdiff_usercomment     
'SMGHLD #18635 GVB-1778 for SMG/HWL in Fomblin film on a micromount'
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'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.21190(10)
_cell_length_b                   5.63310(10)
_cell_length_c                   14.27120(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.5980(10)
_cell_angle_gamma                90
_cell_volume                     940.82(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8202
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.7380
_cell_measurement_theta_min      3.7720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             360
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 0 4 0.0411
5 0 -4 0.0411
-1 0 -1 0.0476
1 0 1 0.0476
-1 -4 1 0.2595
1 4 -1 0.3348
1 0 -5 0.0363
-1 0 5 0.0363
1 0 0 0.0394
-1 0 0 0.0394

_exptl_crystal_size_max          0.611
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.073
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
-4.9969 0.0008 3.9934 -0.2993 0.6135 -0.0119
4.9969 -0.0008 -3.9934 0.2993 -0.6135 0.0119
-0.9988 0.0006 -1.0008 -0.1767 -0.0224 -0.0820
0.9988 -0.0006 1.0008 0.1767 0.0224 0.0820
-0.9993 -3.9978 1.0010 -0.4789 -0.0541 0.9926
0.9993 3.9978 -1.0010 0.4789 0.0541 -0.9926
1.0008 0.0007 -4.9975 -0.2127 -0.4612 -0.1835
-1.0008 -0.0007 4.9975 0.2127 0.4612 0.1835
0.9991 -0.0003 0.0011 0.1118 -0.0582 0.0378
-0.9991 0.0003 -0.0011 -0.1118 0.0582 -0.0378

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10485
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.901
_diffrn_reflns_theta_min         3.777
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  38.00   1.00    2.00    --  -41.70  19.00-180.00   43
  2  ω    -21.00  33.00   1.00    2.00    --  -41.70  38.00-120.00   54
  3  ω     -5.00  38.00   1.00    2.00    --  -41.70  19.00 120.00   43
  4  ω     -5.00  38.00   1.00    2.00    --  -41.70  19.00  30.00   43
  5  ω    -21.00  33.00   1.00    2.00    --  -41.70  38.00  90.00   54
  6  ω    -21.00  33.00   1.00    2.00    --  -41.70  38.00-150.00   54
  7  ω   -116.00 -17.00   1.00    2.00    --  -41.70 -38.00-180.00   99
  8  ω     -5.00  38.00   1.00    2.00    --  -41.70  19.00 150.00   43
  9  ω     10.00  36.00   1.00    2.00    --   41.70  75.00-138.12   26
 10  ω      9.00  42.00   1.00    2.00    --   41.70  79.00 -49.24   33
 11  ω    103.00 178.00   1.00    8.00    --  104.36  77.00   0.00   75
 12  ω     31.00  72.00   1.00    8.00    --  104.36 -45.00 150.00   41
 13  ω     22.00 106.00   1.00    8.00    --  104.36 -94.00  90.00   84
 14  ω     75.00 177.00   1.00    8.00    --  104.36  61.00-150.00  102
 15  ω     32.00  93.00   1.00    8.00    --  104.36 -61.00 120.00   61
 16  ω     74.00 177.00   1.00    8.00    --  104.36  66.00 137.20  103
 17  ω     75.00 177.00   1.00    8.00    --  104.36  61.00-120.00  102
 18  ω     79.00 177.00   1.00    8.00    --  104.36  45.00 -90.00   98
 19  ω     28.00  57.00   1.00    8.00    --  104.36 -30.00  90.00   29
 20  ω     75.00 177.00   1.00    8.00    --  104.36  61.00-180.00  102
 21  ω     79.00 177.00   1.00    8.00    --  104.36  45.00-180.00   98
 22  ω     97.00 178.00   1.00    8.00    --  104.36 125.00  90.00   81
 23  ω     28.00  57.00   1.00    8.00    --  104.36 -30.00-150.00   29
 24  ω     79.00 174.00   1.00    8.00    --  104.36  45.00-150.00   95
 25  ω     83.00 115.00   1.00    8.00    --  104.36  45.00-120.00   32
 26  ω     79.00 117.00   1.00    8.00    --  104.36  45.00 150.00   38
 27  ω     75.00 103.00   1.00    8.00    --  104.36  61.00 150.00   28
 28  ω    153.00 178.00   1.00    8.00    --  104.36  36.00-157.87   25
 29  ω     81.00 108.00   1.00    8.00    --  104.36  36.00-157.87   27
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas S2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1118356000
_diffrn_orient_matrix_UB_12      0.1081011000
_diffrn_orient_matrix_UB_13      0.0649641000
_diffrn_orient_matrix_UB_21      -0.0583380000
_diffrn_orient_matrix_UB_22      0.0483031000
_diffrn_orient_matrix_UB_23      0.0806148000
_diffrn_orient_matrix_UB_31      0.0376843000
_diffrn_orient_matrix_UB_32      -0.2466393000
_diffrn_orient_matrix_UB_33      0.0442199000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                3543
_reflns_number_total             3588
_reflns_odcompleteness_completeness 99.95
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1498 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3588
_refine_ls_number_restraints     311
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0287
_refine_ls_restrained_S_all      1.006
_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)+(0.0387P)²+0.1594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0722
_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
 C8-C3B \\sim C8-C3A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A \\sim C6A \\sim C7A \\sim F1B \\sim
C2B \\sim C3B \\sim C4B \\sim C5B \\sim C6B \\sim C7B: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C4A) = Uanis(C2B)
Uanis(C5A) = Uanis(C7B)
Uanis(C7A) = Uanis(C5B)
Uanis(C6A) = Uanis(C6B)
Uanis(C3A) = Uanis(C3B)
Uanis(C2A) = Uanis(C4B)
4. Rigid body (RIGU) restrains
 F1A, C2A, C3A, C4A, C5A, C6A, C7A, F1B, C2B, C3B, C4B, C5B, C6B, C7B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{F1A, C2A, C3A, C4A, C5A, C6A, C7A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{F1B, C2B, C3B, C4B, C5B, C6B, C7B}
6. Others
 Sof(F1B)=Sof(C2B)=Sof(C3B)=Sof(C4B)=Sof(H4B)=Sof(C5B)=Sof(H5B)=Sof(C6B)=
 Sof(H6B)=Sof(C7B)=Sof(H7B)=1-FVAR(1)
 Sof(F1A)=Sof(C2A)=Sof(C3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=
 Sof(H6A)=Sof(C7A)=Sof(H7A)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C10(H10)
7.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C19(H19A,H19B)
7.c Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C4B(H4B), C5B(H5B), C6B(H6B), C7B(H7B)
7.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
F1A F 0.83056(10) 0.9407(3) 0.21308(8) 0.0380(4) Uani 0.923(4) 1 d D U P A 1
C2A C 0.8939(4) 0.7859(6) 0.2789(3) 0.0250(8) Uani 0.923(4) 1 d D U P A 1
C3A C 0.8409(2) 0.5835(7) 0.3014(3) 0.0202(8) Uani 0.923(4) 1 d D U P A 1
C4A C 0.9097(6) 0.4328(16) 0.3715(9) 0.0234(4) Uani 0.923(4) 1 d D U P A 1
H4A H 0.878741 0.292423 0.387066 0.028 Uiso 0.923(4) 1 calc R U P A 1
C5A C 1.0229(4) 0.4867(9) 0.4186(7) 0.0270(9) Uani 0.923(4) 1 d D U P A 1
H5A H 1.066435 0.384670 0.466042 0.032 Uiso 0.923(4) 1 calc R U P A 1
C6A C 1.0712(4) 0.6928(11) 0.3949(10) 0.0296(8) Uani 0.923(4) 1 d D U P A 1
H6A H 1.147038 0.729279 0.426554 0.035 Uiso 0.923(4) 1 calc R U P A 1
C7A C 1.0064(4) 0.8442(8) 0.3240(2) 0.0293(7) Uani 0.923(4) 1 d D U P A 1
H7A H 1.038079 0.982239 0.307184 0.035 Uiso 0.923(4) 1 calc R U P A 1
C8 C 0.72172(13) 0.5189(3) 0.24858(11) 0.0218(3) Uani 1 1 d D . . . .
C9 C 0.63988(12) 0.4549(3) 0.28928(10) 0.0202(3) Uani 1 1 d . . . . .
C10 C 0.53691(13) 0.3512(3) 0.21312(11) 0.0240(3) Uani 1 1 d . . . . .
H10 H 0.541965 0.177624 0.215941 0.029 Uiso 1 1 calc R U . . .
C11 C 0.55641(16) 0.4369(5) 0.11595(12) 0.0385(5) Uani 1 1 d . . . . .
H11A H 0.531350 0.317478 0.065393 0.046 Uiso 1 1 calc R U . . .
H11B H 0.514774 0.582784 0.093961 0.046 Uiso 1 1 calc R U . . .
C12 C 0.68502(15) 0.4781(4) 0.13919(11) 0.0297(4) Uani 1 1 d . . . . .
H12A H 0.722989 0.340492 0.122002 0.036 Uiso 1 1 calc R U . . .
H12B H 0.701440 0.615671 0.104617 0.036 Uiso 1 1 calc R U . . .
C13 C 0.64670(11) 0.4584(3) 0.39425(10) 0.0179(3) Uani 1 1 d . . . . .
C14 C 0.60169(12) 0.2718(3) 0.43614(11) 0.0203(3) Uani 1 1 d . . . . .
H14 H 0.568456 0.143227 0.397550 0.024 Uiso 1 1 calc R U . . .
C15 C 0.60570(13) 0.2749(3) 0.53456(12) 0.0222(3) Uani 1 1 d . . . . .
H15 H 0.574885 0.149515 0.561071 0.027 Uiso 1 1 calc R U . . .
C16 C 0.65569(12) 0.4651(3) 0.59325(10) 0.0229(3) Uani 1 1 d . . . . .
H16 H 0.659084 0.467007 0.659180 0.027 Uiso 1 1 calc R U . . .
C17 C 0.70056(13) 0.6523(3) 0.55267(11) 0.0222(3) Uani 1 1 d . . . . .
H17 H 0.734153 0.779951 0.591682 0.027 Uiso 1 1 calc R U . . .
C18 C 0.69560(12) 0.6502(3) 0.45427(11) 0.0196(3) Uani 1 1 d . . . . .
H18 H 0.725094 0.777613 0.427833 0.024 Uiso 1 1 calc R U . . .
C19 C 0.42004(13) 0.4267(3) 0.22169(11) 0.0221(3) Uani 1 1 d . . . . .
H19A H 0.420301 0.418118 0.289642 0.026 Uiso 1 1 calc R U . . .
H19B H 0.405577 0.590171 0.200444 0.026 Uiso 1 1 calc R U . . .
C20 C 0.32461(13) 0.2696(3) 0.16023(11) 0.0212(3) Uani 1 1 d . . . . .
O21 O 0.34062(11) 0.0588(2) 0.15533(10) 0.0340(3) Uani 1 1 d . . . . .
C22 C 0.20959(13) 0.3827(3) 0.10866(11) 0.0215(3) Uani 1 1 d . . . . .
C23 C 0.16570(15) 0.5236(4) 0.18260(12) 0.0303(4) Uani 1 1 d . . . . .
H23A H 0.155735 0.418318 0.232447 0.045 Uiso 1 1 calc R U . . .
H23B H 0.093837 0.595957 0.149687 0.045 Uiso 1 1 calc R U . . .
H23C H 0.220051 0.644536 0.211947 0.045 Uiso 1 1 calc R U . . .
C24 C 0.12342(15) 0.1904(4) 0.06082(14) 0.0317(4) Uani 1 1 d . . . . .
H24A H 0.151330 0.103857 0.014406 0.048 Uiso 1 1 calc R U . . .
H24B H 0.051592 0.262927 0.027907 0.048 Uiso 1 1 calc R U . . .
H24C H 0.113228 0.083685 0.110103 0.048 Uiso 1 1 calc R U . . .
C25 C 0.22781(14) 0.5503(3) 0.02932(11) 0.0250(3) Uani 1 1 d . . . . .
H25A H 0.275809 0.680171 0.059693 0.038 Uiso 1 1 calc R U . . .
H25B H 0.155324 0.610457 -0.009095 0.038 Uiso 1 1 calc R U . . .
H25C H 0.263649 0.464859 -0.012159 0.038 Uiso 1 1 calc R U . . .
F1B F 0.8577(12) 0.228(3) 0.3865(12) 0.037(4) Uani 0.077(4) 1 d D U P A 2
C2B C 0.906(7) 0.43(2) 0.368(11) 0.0234(4) Uani 0.077(4) 1 d D U P A 2
C3B C 0.845(3) 0.573(10) 0.290(5) 0.0202(8) Uani 0.077(4) 1 d D U P A 2
C4B C 0.891(5) 0.801(9) 0.293(5) 0.0250(8) Uani 0.077(4) 1 d D U P A 2
H4B H 0.844785 0.925576 0.262587 0.030 Uiso 0.077(4) 1 calc R U P A 2
C5B C 1.006(5) 0.843(11) 0.341(5) 0.0293(7) Uani 0.077(4) 1 d D U P A 2
H5B H 1.037512 0.990794 0.335996 0.035 Uiso 0.077(4) 1 calc R U P A 2
C6B C 1.073(5) 0.666(17) 0.396(13) 0.0296(8) Uani 0.077(4) 1 d D U P A 2
H6B H 1.151127 0.685725 0.420317 0.035 Uiso 0.077(4) 1 calc R U P A 2
C7B C 1.022(5) 0.459(15) 0.414(9) 0.0270(9) Uani 0.077(4) 1 d D U P A 2
H7B H 1.063186 0.342985 0.455367 0.032 Uiso 0.077(4) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1A C2A 1.352(4) . ?
C2A C3A 1.393(4) . ?
C2A C7A 1.380(3) . ?
C3A C4A 1.395(4) . ?
C3A C8 1.481(3) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.388(3) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.387(4) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.386(5) . ?
C7A H7A 0.9300 . ?
C8 C9 1.341(2) . ?
C8 C12 1.514(2) . ?
C8 C3B 1.49(2) . ?
C9 C10 1.524(2) . ?
C9 C13 1.4766(19) . ?
C10 H10 0.9800 . ?
C10 C11 1.550(2) . ?
C10 C19 1.527(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.527(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.397(2) . ?
C13 C18 1.402(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.391(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.389(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(2) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.525(2) . ?
C20 O21 1.209(2) . ?
C20 C22 1.526(2) . ?
C22 C23 1.534(2) . ?
C22 C24 1.528(2) . ?
C22 C25 1.539(2) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
F1B C2B 1.35(3) . ?
C2B C3B 1.40(3) . ?
C2B C7B 1.38(3) . ?
C3B C4B 1.40(3) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.39(3) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.38(3) . ?
C6B H6B 0.9300 . ?
C6B C7B 1.38(3) . ?
C7B H7B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1A C2A C3A 118.5(3) . . ?
F1A C2A C7A 117.8(3) . . ?
C7A C2A C3A 123.6(3) . . ?
C2A C3A C4A 116.1(2) . . ?
C2A C3A C8 122.5(3) . . ?
C4A C3A C8 121.2(3) . . ?
C3A C4A H4A 119.1 . . ?
C5A C4A C3A 121.8(3) . . ?
C5A C4A H4A 119.1 . . ?
C4A C5A H5A 120.0 . . ?
C6A C5A C4A 119.9(3) . . ?
C6A C5A H5A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C7A C6A C5A 120.0(3) . . ?
C7A C6A H6A 120.0 . . ?
C2A C7A C6A 118.6(3) . . ?
C2A C7A H7A 120.7 . . ?
C6A C7A H7A 120.7 . . ?
C3A C8 C12 121.4(2) . . ?
C9 C8 C3A 126.3(2) . . ?
C9 C8 C12 111.61(14) . . ?
C9 C8 C3B 133(3) . . ?
C3B C8 C12 114(3) . . ?
C8 C9 C10 111.05(13) . . ?
C8 C9 C13 127.09(14) . . ?
C13 C9 C10 121.64(13) . . ?
C9 C10 H10 108.9 . . ?
C9 C10 C11 102.27(14) . . ?
C9 C10 C19 115.84(13) . . ?
C11 C10 H10 108.9 . . ?
C19 C10 H10 108.9 . . ?
C19 C10 C11 111.78(14) . . ?
C10 C11 H11A 110.7 . . ?
C10 C11 H11B 110.7 . . ?
H11A C11 H11B 108.8 . . ?
C12 C11 C10 105.33(14) . . ?
C12 C11 H11A 110.7 . . ?
C12 C11 H11B 110.7 . . ?
C8 C12 C11 103.30(13) . . ?
C8 C12 H12A 111.1 . . ?
C8 C12 H12B 111.1 . . ?
C11 C12 H12A 111.1 . . ?
C11 C12 H12B 111.1 . . ?
H12A C12 H12B 109.1 . . ?
C14 C13 C9 120.59(15) . . ?
C14 C13 C18 118.00(13) . . ?
C18 C13 C9 121.39(14) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.18(15) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.06(15) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.47(14) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.45(15) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.83(14) . . ?
C17 C18 H18 119.6 . . ?
C10 C19 H19A 109.3 . . ?
C10 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 C10 111.76(14) . . ?
C20 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C19 C20 C22 118.83(14) . . ?
O21 C20 C19 119.56(15) . . ?
O21 C20 C22 121.58(14) . . ?
C20 C22 C23 109.78(13) . . ?
C20 C22 C24 109.95(14) . . ?
C20 C22 C25 107.72(13) . . ?
C23 C22 C25 109.95(14) . . ?
C24 C22 C23 110.03(14) . . ?
C24 C22 C25 109.39(14) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
F1B C2B C3B 118(4) . . ?
F1B C2B C7B 117(4) . . ?
C7B C2B C3B 123(4) . . ?
C2B C3B C8 117(4) . . ?
C4B C3B C8 124(4) . . ?
C4B C3B C2B 112(3) . . ?
C3B C4B H4B 119.6 . . ?
C5B C4B C3B 121(3) . . ?
C5B C4B H4B 119.6 . . ?
C4B C5B H5B 119.9 . . ?
C6B C5B C4B 120(3) . . ?
C6B C5B H5B 119.9 . . ?
C5B C6B H6B 120.3 . . ?
C7B C6B C5B 119(3) . . ?
C7B C6B H6B 120.3 . . ?
C2B C7B H7B 121.3 . . ?
C6B C7B C2B 117(3) . . ?
C6B C7B H7B 121.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1A C2A C3A C4A -178.5(9) . . . . ?
F1A C2A C3A C8 6.7(5) . . . . ?
F1A C2A C7A C6A 177.1(8) . . . . ?
C2A C3A C4A C5A 2.4(17) . . . . ?
C2A C3A C8 C9 -132.0(3) . . . . ?
C2A C3A C8 C12 58.8(5) . . . . ?
C3A C2A C7A C6A 0.7(9) . . . . ?
C3A C4A C5A C6A -1(2) . . . . ?
C3A C8 C9 C10 -167.8(3) . . . . ?
C3A C8 C9 C13 6.8(3) . . . . ?
C3A C8 C12 C11 -175.6(2) . . . . ?
C4A C3A C8 C9 53.5(9) . . . . ?
C4A C3A C8 C12 -115.8(9) . . . . ?
C4A C5A C6A C7A -0.2(19) . . . . ?
C5A C6A C7A C2A 0.5(16) . . . . ?
C7A C2A C3A C4A -2.1(9) . . . . ?
C7A C2A C3A C8 -176.9(4) . . . . ?
C8 C3A C4A C5A 177.3(10) . . . . ?
C8 C9 C10 C11 -17.1(2) . . . . ?
C8 C9 C10 C19 -138.87(16) . . . . ?
C8 C9 C13 C14 -138.42(17) . . . . ?
C8 C9 C13 C18 43.2(2) . . . . ?
C8 C3B C4B C5B 174(6) . . . . ?
C9 C8 C12 C11 13.7(2) . . . . ?
C9 C8 C3B C2B 39(12) . . . . ?
C9 C8 C3B C4B -109(6) . . . . ?
C9 C10 C11 C12 24.6(2) . . . . ?
C9 C10 C19 C20 -165.73(14) . . . . ?
C9 C13 C14 C15 -178.83(14) . . . . ?
C9 C13 C18 C17 179.42(14) . . . . ?
C10 C9 C13 C14 35.7(2) . . . . ?
C10 C9 C13 C18 -142.75(15) . . . . ?
C10 C11 C12 C8 -23.5(2) . . . . ?
C10 C19 C20 O21 38.6(2) . . . . ?
C10 C19 C20 C22 -143.15(15) . . . . ?
C11 C10 C19 C20 77.68(19) . . . . ?
C12 C8 C9 C10 2.3(2) . . . . ?
C12 C8 C9 C13 176.94(17) . . . . ?
C12 C8 C3B C2B -127(10) . . . . ?
C12 C8 C3B C4B 86(7) . . . . ?
C13 C9 C10 C11 167.99(16) . . . . ?
C13 C9 C10 C19 46.2(2) . . . . ?
C13 C14 C15 C16 -0.4(2) . . . . ?
C14 C13 C18 C17 1.0(2) . . . . ?
C14 C15 C16 C17 0.6(2) . . . . ?
C15 C16 C17 C18 0.0(2) . . . . ?
C16 C17 C18 C13 -0.8(2) . . . . ?
C18 C13 C14 C15 -0.4(2) . . . . ?
C19 C10 C11 C12 149.15(16) . . . . ?
C19 C20 C22 C23 -52.75(19) . . . . ?
C19 C20 C22 C24 -173.93(14) . . . . ?
C19 C20 C22 C25 66.95(17) . . . . ?
O21 C20 C22 C23 125.45(18) . . . . ?
O21 C20 C22 C24 4.3(2) . . . . ?
O21 C20 C22 C25 -114.85(18) . . . . ?
F1B C2B C3B C8 14(20) . . . . ?
F1B C2B C3B C4B 166(13) . . . . ?
F1B C2B C7B C6B 180(16) . . . . ?
C2B C3B C4B C5B 25(12) . . . . ?
C3B C8 C9 C10 -163(3) . . . . ?
C3B C8 C9 C13 11(3) . . . . ?
C3B C8 C12 C11 -178(2) . . . . ?
C3B C2B C7B C6B 14(25) . . . . ?
C3B C4B C5B C6B -7(14) . . . . ?
C4B C5B C6B C7B -9(22) . . . . ?
C5B C6B C7B C2B 6(25) . . . . ?
C7B C2B C3B C8 180(14) . . . . ?
C7B C2B C3B C4B -29(21) . . . . ?

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_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 1.439
_oxdiff_exptl_absorpt_empirical_full_min 0.867
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pentane'
####################################################################### 
# 
# 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_smghle
_database_code_depnum_ccdc_archive 'CCDC 2040012'
loop_
_audit_author_name
_audit_author_address
'Stephen P. Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2020-10-22 deposited with the CCDC.	2021-03-15 downloaded from the CCDC.
;
_nottingham_internal_coll_name   SMGHLE
_nottingham_internal_coll_number 18637
_nottingham_internal_coll_client SMG/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '1.00, 2.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczspa
_nottingham_internal_coll_date   19/02/2020
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 19/02/2020
_nottingham_internal_process_user pczspa
_nottingham_internal_solution_date 18/05/2020
_nottingham_internal_solution_user pczspa
_nottingham_internal_refinement_date 18/05/2020
_nottingham_internal_refinement_user pczspa
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 18/05/2020
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date ?
_refine_special_details          
;
 Conformational disorder is modelled for thiophene moiety S1-C5. The
 occupancies of the two disorder components were refined and
 constrained to sum unity, resulting in values of 0.66(1) and 0.34(1)
 respectively. The geometries of the two disorder components were
 restrained to be similar (SADI), planar (FLAT) and have 1,2 and
 1,3 bond distances set a target values generated by the FragmentDB
 function in the Software Olex2 v1.3 (DFIX, DANG). Rigid bond and
 similarity restraints (RIGU, SIMU) were applied to the anisotropic
 displacement parameters of all atoms in the disordered moieties. The
 three pairs of overlapping atoms in the disordered moieties were
 constrained to have identical anisotropic displacement parameters
 (EADP). All hydrogen atoms in the structure were observed in the
 electron density map before being geometrically placed and
 refined using a riding model. 
;
_audit_creation_date             2020-05-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 O S2'
_chemical_formula_sum            'C21 H18 O S2'
_chemical_formula_weight         350.47
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H18OS2
_chemical_oxdiff_usercomment     
'SMGHLE #18637 GVA-1783 for SMG/HWL fomblin micromount'
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.42830(10)
_cell_length_b                   6.96610(10)
_cell_length_c                   16.5307(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.4000(10)
_cell_angle_gamma                90
_cell_volume                     853.90(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14030
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.4740
_cell_measurement_theta_min      5.3500
_shelx_estimated_absorpt_T_max   0.834
_shelx_estimated_absorpt_T_min   0.438
_exptl_absorpt_coefficient_mu    2.844
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.302
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 2 5 0.0331
2 -2 -5 0.0331
3 4 1 0.1033
-1 -3 5 0.0965
1 0 5 0.1333
0 0 -1 0.0938
-2 -1 -2 0.1726
0 1 -5 0.1086
1 -1 -1 0.0531

_exptl_crystal_size_max          0.348
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.066
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
-1.9991 2.0003 4.9980 -0.0124 0.7388 0.1294
1.9991 -2.0003 -4.9980 0.0124 -0.7388 -0.1294
3.0001 3.9974 0.9977 1.0525 0.2779 -0.0144
-1.0009 -2.9975 4.9990 -0.5836 -0.1193 0.5781
0.9993 0.0005 4.9977 0.1653 0.0878 0.4873
0.0001 -0.0002 -0.9996 -0.0018 -0.0412 -0.0837
-1.9995 -0.9993 -1.9984 -0.4616 0.0063 -0.2287
0.0007 0.9988 -4.9982 0.1364 -0.0583 -0.4947
0.9994 -0.9999 -0.9996 0.0089 -0.3075 0.0609

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16193
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.454
_diffrn_reflns_theta_min         5.361
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 4.2207
_diffrn_detector_type            'Agilent Diffraction Titan S2 detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  36.00   1.00    1.00    --  -41.87  19.00 -30.00   41
  2  ω    -21.00  30.00   1.00    1.00    --  -41.87  38.00  90.00   51
  3  ω     -5.00  36.00   1.00    1.00    --  -41.87  19.00 -60.00   41
  4  ω     17.00 113.00   1.00    1.00    --   41.87  38.00 -60.00   96
  5  ω     17.00 113.00   1.00    1.00    --   41.87  38.00  60.00   96
  6  ω     27.00  95.00   1.00    1.00    --   41.87-125.00 120.00   68
  7  ω     31.00  93.00   1.00    2.00    --  101.44 -61.00  60.00   62
  8  ω     31.00  72.00   1.00    2.00    --  101.44 -45.00 -60.00   41
  9  ω     75.00 171.00   1.00    2.00    --  101.44  61.00  60.00   96
 10  ω     28.00 113.00   1.00    2.00    --  101.44-125.00-180.00   85
 11  ω     31.00  72.00   1.00    2.00    --  101.44 -45.00 120.00   41
 12  ω     75.00 171.00   1.00    2.00    --  101.44  61.00-120.00   96
 13  ω     18.00 107.00   1.00    2.00    --  101.44 -94.00  30.00   89
 14  ω     28.00  57.00   1.00    2.00    --  101.44 -30.00  90.00   29
 15  ω     31.00  72.00   1.00    2.00    --  101.44 -45.00  30.00   41
 16  ω     31.00  93.00   1.00    2.00    --  101.44 -61.00-150.00   62
 17  ω     31.00  72.00   1.00    2.00    --  101.44 -45.00 -90.00   41
 18  ω     28.00  57.00   1.00    2.00    --  101.44 -30.00-120.00   29
 19  ω     28.00 113.00   1.00    2.00    --  101.44-125.00   0.00   85
 20  ω    103.00 176.00   1.00    2.00    --  101.44  77.00-180.00   73
 21  ω    103.00 176.00   1.00    2.00    --  101.44  77.00   0.00   73
 22  ω     77.00 172.00   1.00    2.00    --  101.44  45.00 150.00   95
 23  ω    -21.00  30.00   1.00    1.00    --  -41.87  38.00-150.00   51
 24  ω     27.00  95.00   1.00    1.00    --   41.87-125.00-120.00   68
 25  ω     16.00 112.00   1.00    1.00    --   41.87  57.00 -30.00   96
 26  ω     16.00 112.00   1.00    1.00    --   41.87  57.00-120.00   96
 27  ω     16.00 112.00   1.00    1.00    --   41.87  57.00  90.00   96
 28  ω     16.00 112.00   1.00    1.00    --   41.87  57.00-180.00   96
 29  ω     75.00 175.00   1.00    2.00    --  101.44  30.00 -30.00  100
 30  ω     75.00 171.00   1.00    2.00    --  101.44  61.00 -30.00   96
 31  ω     31.00  93.00   1.00    2.00    --  101.44 -61.00 150.00   62
 32  ω     75.00 171.00   1.00    2.00    --  101.44  61.00 -90.00   96
 33  ω     75.00 171.00   1.00    2.00    --  101.44  61.00  90.00   96
 34  ω     75.00 171.00   1.00    2.00    --  101.44  61.00-180.00   96
 35  ω     75.00 171.00   1.00    2.00    --  101.44  61.00-150.00   96
 36  ω     75.00 171.00   1.00    2.00    --  101.44  61.00  30.00   96
 37  ω     75.00 134.00   1.00    2.00    --  101.44  61.00 120.00   59
 38  ω     75.00 171.00   1.00    2.00    --  101.44  61.00   0.00   96
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Titan S2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1563248000
_diffrn_orient_matrix_UB_12      0.1455131000
_diffrn_orient_matrix_UB_13      0.0018093000
_diffrn_orient_matrix_UB_21      -0.1183373000
_diffrn_orient_matrix_UB_22      0.1480537000
_diffrn_orient_matrix_UB_23      0.0412240000
_diffrn_orient_matrix_UB_31      0.0686549000
_diffrn_orient_matrix_UB_32      -0.0760399000
_diffrn_orient_matrix_UB_33      0.0837898000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                3332
_reflns_number_total             3350
_reflns_odcompleteness_completeness 99.88
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1494 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3350
_refine_ls_number_restraints     314
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0233
_refine_ls_restrained_S_all      1.007
_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)+(0.0367P)²+0.2682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0635
_refine_ls_wR_factor_ref         0.0636
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C2A-C3A = C4A-C5A
 1.36 with sigma of 0.02
 C3A-C4A
 1.42 with sigma of 0.02
 C5B-C4B = C3B-C2B
 1.36 with sigma of 0.02
 C4B-C3B
 1.42 with sigma of 0.02
 S1A-C2A = S1A-C5A
 1.71 with sigma of 0.02
 S1B-C5B = S1B-C2B
 1.71 with sigma of 0.02
 S1B-C4B = S1B-C3B
 2.54 with sigma of 0.04
 S1A-C3A = S1A-C4A
 2.54 with sigma of 0.04
 C2A-C4A = C3A-C5A
 2.31 with sigma of 0.04
 C5B-C3B = C4B-C2B
 2.31 with sigma of 0.04
 S1B-C4B \\sim S1B-C3B
 with sigma of 0.04
 C2A-C3A \\sim C3A-C4A \\sim C4A-C5A
 with sigma of 0.03
 C2A-C4A \\sim C3A-C5A
 with sigma of 0.04
 S1A-C3A \\sim S1A-C4A
 with sigma of 0.04
 C5B-C4B \\sim C4B-C3B \\sim C3B-C2B
 with sigma of 0.03
 C5B-C3B \\sim C4B-C2B
 with sigma of 0.04
 S1B-C5B \\sim S1B-C2B
 with sigma of 0.02
 S1A-C2A \\sim S1A-C5A
 with sigma of 0.02
 S1B-C2B \\sim S1B-C5B \\sim S1A-C5A \\sim S1A-C2A
 with sigma of 0.02
 C6-C3A \\sim C6-C3B
 with sigma of 0.02
3. Restrained planarity
 S1A, C2A, C3A, C4A, C5A
 with sigma of 0.1
 S1B, C2B, C3B, C4B, C5B
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
S1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
S1B \\sim C2B \\sim C3B \\sim C4B \\sim C5B: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
S1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A \\sim S1B \\sim C2B \\sim C3B \\sim
C4B \\sim C5B: within 2.5A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2.5A
Uanis(C2A) = Uanis(C4B)
Uanis(C3A) = Uanis(C3B)
Uanis(C4A) = Uanis(C2B)
5. Rigid body (RIGU) restrains
 S1B, C2B, C3B, C4B, C5B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S1A, C2A, C3A, C4A, C5A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S1A, C2A, C3A, C4A, C5A, S1B, C2B, C3B, C4B, C5B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
6. Others
 Sof(S1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(C4B)=Sof(H4B)=Sof(C5B)=Sof(H5B)=1-
 FVAR(1)
 Sof(S1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C8(H8)
7.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C17(H17A,H17B)
7.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C22(H22), C23(H23),
 C24(H24), C2A(H2A), C4A(H4A), C5A(H5A), C2B(H2B), C4B(H4B), C5B(H5B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
C6 C 0.5321(3) 0.5519(3) 0.37613(13) 0.0166(4) Uani 1 1 d D . . . .
C7 C 0.5327(2) 0.6421(3) 0.30405(12) 0.0155(4) Uani 1 1 d . . . . .
C8 C 0.3696(3) 0.5851(3) 0.24881(12) 0.0180(4) Uani 1 1 d . . . . .
H8 H 0.314261 0.700306 0.221144 0.022 Uiso 1 1 calc R U . . .
C9 C 0.2408(3) 0.4982(3) 0.30888(13) 0.0227(5) Uani 1 1 d . . . . .
H9A H 0.152449 0.595134 0.325115 0.027 Uiso 1 1 calc R U . . .
H9B H 0.174538 0.387393 0.284214 0.027 Uiso 1 1 calc R U . . .
C10 C 0.3621(3) 0.4341(3) 0.38204(13) 0.0230(5) Uani 1 1 d . . . . .
H10A H 0.304440 0.461118 0.433319 0.028 Uiso 1 1 calc R U . . .
H10B H 0.388692 0.295113 0.379176 0.028 Uiso 1 1 calc R U . . .
C11 C 0.6684(3) 0.7805(3) 0.27625(12) 0.0153(4) Uani 1 1 d . . . . .
C12 C 0.7950(3) 0.7310(3) 0.22075(13) 0.0189(4) Uani 1 1 d . . . . .
H12 H 0.799006 0.603034 0.201105 0.023 Uiso 1 1 calc R U . . .
C13 C 0.9153(3) 0.8662(4) 0.19382(13) 0.0230(4) Uani 1 1 d . . . . .
H13 H 1.000273 0.830468 0.155817 0.028 Uiso 1 1 calc R U . . .
C14 C 0.9113(3) 1.0536(3) 0.22241(13) 0.0233(5) Uani 1 1 d . . . . .
H14 H 0.992254 1.146569 0.203365 0.028 Uiso 1 1 calc R U . . .
C15 C 0.7887(3) 1.1047(3) 0.27891(12) 0.0202(4) Uani 1 1 d . . . . .
H15 H 0.787753 1.231926 0.299623 0.024 Uiso 1 1 calc R U . . .
C16 C 0.6675(3) 0.9697(3) 0.30510(12) 0.0174(4) Uani 1 1 d . . . . .
H16 H 0.582770 1.006070 0.343121 0.021 Uiso 1 1 calc R U . . .
C17 C 0.4253(3) 0.4361(3) 0.18647(12) 0.0182(4) Uani 1 1 d . . . . .
H17A H 0.518590 0.493340 0.153554 0.022 Uiso 1 1 calc R U . . .
H17B H 0.480251 0.324638 0.215760 0.022 Uiso 1 1 calc R U . . .
C18 C 0.2712(3) 0.3656(3) 0.13018(12) 0.0171(4) Uani 1 1 d . . . . .
O19 O 0.1310(2) 0.4567(2) 0.11875(9) 0.0249(3) Uani 1 1 d . . . . .
S20 S 0.14221(6) 0.11235(9) 0.01312(3) 0.02281(13) Uani 1 1 d . . . . .
C21 C 0.2974(3) 0.1820(3) 0.08890(12) 0.0170(4) Uani 1 1 d . . . . .
C22 C 0.4379(3) 0.0473(3) 0.10113(12) 0.0168(4) Uani 1 1 d . . . . .
H22 H 0.536326 0.059304 0.140207 0.020 Uiso 1 1 calc R U . . .
C23 C 0.4110(3) -0.1100(3) 0.04621(13) 0.0233(4) Uani 1 1 d . . . . .
H23 H 0.490758 -0.216348 0.044811 0.028 Uiso 1 1 calc R U . . .
C24 C 0.2595(3) -0.0922(3) -0.00396(13) 0.0232(5) Uani 1 1 d . . . . .
H24 H 0.223237 -0.184184 -0.044131 0.028 Uiso 1 1 calc R U . . .
S1A S 0.8141(3) 0.4672(3) 0.58373(9) 0.0208(3) Uani 0.658(3) 1 d D U P A 1
C2A C 0.6372(8) 0.4468(16) 0.5131(5) 0.0196(6) Uani 0.658(3) 1 d D U P A 1
H2A H 0.531495 0.373811 0.520822 0.023 Uiso 0.658(3) 1 calc R U P A 1
C3A C 0.6666(17) 0.549(3) 0.4433(7) 0.0177(4) Uani 0.658(3) 1 d D U P A 1
C4A C 0.8374(18) 0.642(2) 0.4483(7) 0.0193(6) Uani 0.658(3) 1 d D U P A 1
H4A H 0.881770 0.716807 0.405744 0.023 Uiso 0.658(3) 1 calc R U P A 1
C5A C 0.9293(9) 0.6127(13) 0.5198(4) 0.0230(10) Uani 0.658(3) 1 d D U P A 1
H5A H 1.044820 0.665953 0.533591 0.028 Uiso 0.658(3) 1 calc R U P A 1
S1B S 0.9669(4) 0.6262(5) 0.53333(16) 0.0206(6) Uani 0.342(3) 1 d D U P A 2
C2B C 0.835(3) 0.656(4) 0.4463(13) 0.0193(6) Uani 0.342(3) 1 d D U P A 2
H2B H 0.867892 0.735554 0.403093 0.023 Uiso 0.342(3) 1 calc R U P A 2
C3B C 0.674(3) 0.553(5) 0.4440(14) 0.0177(4) Uani 0.342(3) 1 d D U P A 2
C4B C 0.6651(18) 0.446(3) 0.5174(11) 0.0196(6) Uani 0.342(3) 1 d D U P A 2
H4B H 0.568809 0.361708 0.527746 0.023 Uiso 0.342(3) 1 calc R U P A 2
C5B C 0.806(2) 0.477(3) 0.5705(9) 0.0213(13) Uani 0.342(3) 1 d D U P A 2
H5B H 0.815654 0.422652 0.623226 0.026 Uiso 0.342(3) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C6 C7 1.347(3) . ?
C6 C10 1.514(3) . ?
C6 C3A 1.449(8) . ?
C6 C3B 1.493(14) . ?
C7 C8 1.525(3) . ?
C7 C11 1.487(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.543(3) . ?
C8 C17 1.537(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.531(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.396(3) . ?
C11 C16 1.402(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(3) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.514(3) . ?
C18 O19 1.224(3) . ?
C18 C21 1.469(3) . ?
S20 C21 1.721(2) . ?
S20 C24 1.703(2) . ?
C21 C22 1.409(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.429(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.363(3) . ?
C24 H24 0.9500 . ?
S1A C2A 1.711(6) . ?
S1A C5A 1.727(8) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.386(10) . ?
C3A C4A 1.421(9) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.345(10) . ?
C5A H5A 0.9500 . ?
S1B C2B 1.706(16) . ?
S1B C5B 1.724(14) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.392(17) . ?
C3B C4B 1.426(17) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.341(17) . ?
C5B H5B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C6 C10 110.86(19) . . ?
C7 C6 C3A 130.2(6) . . ?
C7 C6 C3B 128.6(10) . . ?
C3A C6 C10 119.0(6) . . ?
C3B C6 C10 120.5(10) . . ?
C6 C7 C8 111.35(17) . . ?
C6 C7 C11 127.83(18) . . ?
C11 C7 C8 120.82(16) . . ?
C7 C8 H8 110.8 . . ?
C7 C8 C9 102.56(16) . . ?
C7 C8 C17 109.97(16) . . ?
C9 C8 H8 110.8 . . ?
C17 C8 H8 110.8 . . ?
C17 C8 C9 111.61(16) . . ?
C8 C9 H9A 110.7 . . ?
C8 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
C10 C9 C8 105.34(17) . . ?
C10 C9 H9A 110.7 . . ?
C10 C9 H9B 110.7 . . ?
C6 C10 C9 104.19(17) . . ?
C6 C10 H10A 110.9 . . ?
C6 C10 H10B 110.9 . . ?
C9 C10 H10A 110.9 . . ?
C9 C10 H10B 110.9 . . ?
H10A C10 H10B 108.9 . . ?
C12 C11 C7 122.58(18) . . ?
C12 C11 C16 118.21(19) . . ?
C16 C11 C7 119.19(18) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 120.97(19) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.06(19) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 120.98(19) . . ?
C15 C16 H16 119.5 . . ?
C8 C17 H17A 108.7 . . ?
C8 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C18 C17 C8 114.04(16) . . ?
C18 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
O19 C18 C17 122.16(19) . . ?
O19 C18 C21 121.01(18) . . ?
C21 C18 C17 116.83(17) . . ?
C24 S20 C21 91.67(11) . . ?
C18 C21 S20 118.80(15) . . ?
C22 C21 C18 129.14(18) . . ?
C22 C21 S20 112.05(16) . . ?
C21 C22 H22 124.9 . . ?
C21 C22 C23 110.15(19) . . ?
C23 C22 H22 124.9 . . ?
C22 C23 H23 123.3 . . ?
C24 C23 C22 113.4(2) . . ?
C24 C23 H23 123.3 . . ?
S20 C24 H24 123.6 . . ?
C23 C24 S20 112.76(17) . . ?
C23 C24 H24 123.6 . . ?
C2A S1A C5A 91.1(4) . . ?
S1A C2A H2A 124.1 . . ?
C3A C2A S1A 111.9(5) . . ?
C3A C2A H2A 124.1 . . ?
C2A C3A C6 120.6(9) . . ?
C2A C3A C4A 111.7(6) . . ?
C4A C3A C6 127.7(9) . . ?
C3A C4A H4A 123.6 . . ?
C5A C4A C3A 112.8(8) . . ?
C5A C4A H4A 123.6 . . ?
S1A C5A H5A 123.8 . . ?
C4A C5A S1A 112.5(7) . . ?
C4A C5A H5A 123.8 . . ?
C2B S1B C5B 89.7(10) . . ?
S1B C2B H2B 122.9 . . ?
C3B C2B S1B 114.3(13) . . ?
C3B C2B H2B 122.9 . . ?
C2B C3B C6 126.0(17) . . ?
C2B C3B C4B 109.1(12) . . ?
C4B C3B C6 124.9(16) . . ?
C3B C4B H4B 123.2 . . ?
C5B C4B C3B 113.5(12) . . ?
C5B C4B H4B 123.2 . . ?
S1B C5B H5B 123.4 . . ?
C4B C5B S1B 113.2(12) . . ?
C4B C5B H5B 123.4 . . ?

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
C6 C7 C8 C9 17.7(2) . . . . ?
C6 C7 C8 C17 -101.12(19) . . . . ?
C6 C7 C11 C12 105.1(2) . . . . ?
C6 C7 C11 C16 -76.4(3) . . . . ?
C6 C3A C4A C5A 179.3(17) . . . . ?
C6 C3B C4B C5B -177(3) . . . . ?
C7 C6 C10 C9 -11.0(2) . . . . ?
C7 C6 C3A C2A 179.4(8) . . . . ?
C7 C6 C3A C4A -1.2(18) . . . . ?
C7 C6 C3B C2B 3(3) . . . . ?
C7 C6 C3B C4B -177.4(17) . . . . ?
C7 C8 C9 C10 -23.4(2) . . . . ?
C7 C8 C17 C18 178.27(17) . . . . ?
C7 C11 C12 C13 177.51(19) . . . . ?
C7 C11 C16 C15 -178.20(18) . . . . ?
C8 C7 C11 C12 -74.7(3) . . . . ?
C8 C7 C11 C16 103.8(2) . . . . ?
C8 C9 C10 C6 21.4(2) . . . . ?
C8 C17 C18 O19 20.6(3) . . . . ?
C8 C17 C18 C21 -159.81(17) . . . . ?
C9 C8 C17 C18 65.1(2) . . . . ?
C10 C6 C7 C8 -4.4(2) . . . . ?
C10 C6 C7 C11 175.79(19) . . . . ?
C10 C6 C3A C2A -2.4(18) . . . . ?
C10 C6 C3A C4A 177.0(9) . . . . ?
C10 C6 C3B C2B -179.4(16) . . . . ?
C10 C6 C3B C4B 1(4) . . . . ?
C11 C7 C8 C9 -162.48(17) . . . . ?
C11 C7 C8 C17 78.7(2) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C11 C16 C15 0.3(3) . . . . ?
C12 C13 C14 C15 1.0(3) . . . . ?
C13 C14 C15 C16 -1.6(3) . . . . ?
C14 C15 C16 C11 1.0(3) . . . . ?
C16 C11 C12 C13 -1.0(3) . . . . ?
C17 C8 C9 C10 94.2(2) . . . . ?
C17 C18 C21 S20 -170.37(15) . . . . ?
C17 C18 C21 C22 8.6(3) . . . . ?
C18 C21 C22 C23 -178.87(19) . . . . ?
O19 C18 C21 S20 9.2(3) . . . . ?
O19 C18 C21 C22 -171.8(2) . . . . ?
S20 C21 C22 C23 0.2(2) . . . . ?
C21 S20 C24 C23 0.51(18) . . . . ?
C21 C22 C23 C24 0.2(3) . . . . ?
C22 C23 C24 S20 -0.5(2) . . . . ?
C24 S20 C21 C18 178.77(16) . . . . ?
C24 S20 C21 C22 -0.39(16) . . . . ?
S1A C2A C3A C6 -179.6(12) . . . . ?
S1A C2A C3A C4A 1.0(11) . . . . ?
C2A S1A C5A C4A -0.4(10) . . . . ?
C2A C3A C4A C5A -1.3(12) . . . . ?
C3A C6 C7 C8 173.8(10) . . . . ?
C3A C6 C7 C11 -5.9(11) . . . . ?
C3A C6 C10 C9 170.5(9) . . . . ?
C3A C4A C5A S1A 1.1(11) . . . . ?
C5A S1A C2A C3A -0.3(10) . . . . ?
S1B C2B C3B C6 180(3) . . . . ?
S1B C2B C3B C4B -0.5(19) . . . . ?
C2B S1B C5B C4B 2.9(19) . . . . ?
C2B C3B C4B C5B 3(2) . . . . ?
C3B C6 C7 C8 173.8(19) . . . . ?
C3B C6 C7 C11 -6.0(19) . . . . ?
C3B C6 C10 C9 170.6(17) . . . . ?
C3B C4B C5B S1B -4(3) . . . . ?
C5B S1B C2B C3B -1.3(15) . . . . ?

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_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 1.458
_oxdiff_exptl_absorpt_empirical_full_min 0.796
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pentane'
