# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_7071-8899-ima065_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 1847444'
_audit_update_record             
;
2018-06-05 deposited with the CCDC.
2018-10-03 downloaded from the CCDC.
;
_audit_creation_date             2018-05-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 Cl O'
_chemical_formula_sum            'C23 H17 Cl O'
_chemical_formula_weight         344.82
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 O2 Cl1 H24'
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.23180(10)
_cell_length_b                   19.0611(3)
_cell_length_c                   30.5102(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.1740(10)
_cell_angle_gamma                90
_cell_volume                     3609.39(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12167
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.7930
_cell_measurement_theta_min      2.3530
_shelx_estimated_absorpt_T_max   0.701
_shelx_estimated_absorpt_T_min   0.607
_exptl_absorpt_coefficient_mu    1.911
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1440
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            7095
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.210
_diffrn_reflns_theta_min         2.737
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  15.00   0.50    4.56    --  -41.35 101.00 137.00   66
  2  ω    -69.00 -22.00   0.50    4.56    --  -41.35 101.00 137.00   94
  3  ω     72.00  98.00   0.50   18.24    --  101.00-101.00  32.00   52
  4  ω    120.00 146.00   0.50   18.24    --  101.00 101.00 137.00   52
  5  ω    -99.00 -21.00   0.50    4.56    --  -41.35 -65.00  30.00  156
  6  ω   -104.00 -75.00   0.50    4.56    --  -41.35 -32.00-180.00   58
  7  ω    -69.00 -42.00   0.50    4.56    --  -41.35 -32.00  60.00   54
  8  ω    -66.00 -37.00   0.50    4.56    --  -41.35 -32.00-180.00   58
  9  ω   -103.00 -73.00   0.50    4.56    --  -41.35 -32.00  60.00   60
 10  ω      2.00  37.00   0.50    4.56    --   41.35-101.00  32.00   70
 11  ω    -21.00  27.00   0.50    4.56    --   41.35 -32.00-120.00   96
 12  ω    -22.00  19.00   0.50    4.56    --   41.35 -77.00 -30.00   82
 13  ω     44.00 101.00   0.50    4.56    --   41.35  43.00 120.00  114
 14  ω     25.00 101.00   0.50    4.56    --   41.35  65.00 150.00  152
 15  ω     25.00  64.00   0.50    4.56    --   41.35 -77.00 -30.00   78
 16  ω      6.00  32.00   0.50    4.56    --   41.35 -54.00 -30.00   52
 17  ω     51.00  76.00   0.50    4.56    --   41.35-101.00  32.00   50
 18  ω     34.00  59.00   0.50    4.56    --   41.35 -54.00 -30.00   50
 19  ω    -20.00   6.00   0.50    4.56    --   41.35 -43.00  60.00   52
 20  ω     28.00  53.00   0.50    4.56    --   41.35 -43.00  60.00   50
 21  ω     88.00 114.00   0.50   18.24    --  101.00 -42.00 150.00   52
 22  ω     92.00 146.00   0.50   18.24    --  101.00  33.00 150.00  108
 23  ω     40.00  68.00   0.50   18.24    --  101.00 -42.00 150.00   56
 24  ω     39.00  64.00   0.50   18.24    --  101.00-133.00 150.00   50
 25  ω     41.00 132.00   0.50   18.24    --  101.00 -93.00-120.00  182
 26  ω     55.00  81.00   0.50   18.24    --  101.00 -17.00 -30.00   52
 27  ω    129.00 157.00   0.50   18.24    --  101.00  33.00-120.00   56
 28  ω    100.00 126.00   0.50   18.24    --  101.00  33.00-120.00   52
 29  ω     43.00 119.00   0.50   18.24    --  101.00 -77.00  60.00  152
 30  ω     99.00 143.00   0.50   18.24    --  101.00  25.00   0.00   88
 31  ω     41.00 110.00   0.50   18.24    --  101.00 -33.00 -30.00  138
 32  ω     42.00  98.00   0.50   18.24    --  101.00 -77.00  30.00  112
 33  ω     52.00  82.00   0.50   18.24    --  101.00-111.00-150.00   60
 34  ω     36.00 116.00   0.50   18.24    --  101.00 -93.00  30.00  160
 35  ω    106.00 150.00   0.50   18.24    --  101.00  33.00  90.00   88
 36  ω     83.00 148.00   0.50   18.24    --  101.00 111.00 -60.00  130
 37  ω    124.00 157.00   0.50   18.24    --  101.00  77.00 120.00   66
 38  ω     91.00 116.00   0.50   18.24    --  101.00 -50.00   0.00   50
 39  ω     42.00  67.00   0.50   18.24    --  101.00 -50.00   0.00   50
 40  ω     91.00 155.00   0.50   18.24    --  101.00  17.00  60.00  128
 41  ω     76.00 112.00   0.50   18.24    --  101.00  77.00 120.00   72
 42  ω     72.00 115.00   0.50   18.24    --  101.00 -59.00  60.00   86
 43  ω     89.00 114.00   0.50   18.24    --  101.00 -87.00  60.00   50
 44  ω     88.00 153.00   0.50   18.24    --  101.00  42.00 -60.00  130
 45  ω      5.00  30.00   0.50    4.56    --   41.35-101.00  32.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0720141000
_diffrn_orient_matrix_UB_12      -0.0066933000
_diffrn_orient_matrix_UB_13      -0.0494359000
_diffrn_orient_matrix_UB_21      -0.0656752000
_diffrn_orient_matrix_UB_22      -0.0768323000
_diffrn_orient_matrix_UB_23      0.0070611000
_diffrn_orient_matrix_UB_31      -0.2283342000
_diffrn_orient_matrix_UB_32      0.0243098000
_diffrn_orient_matrix_UB_33      0.0085649000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6209
_reflns_number_total             7095
_reflns_special_details          
;
 _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 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_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         0.374
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         7095
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0525
_refine_ls_restrained_S_all      1.080
_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)+(0.1195P)²+0.4248P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1576
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.37(5)
 0.63(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W),
 C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013),
 C014(H014), C015(H015), C016(H016), C018(H018), C019(H019), C01A(H01A),
 C01B(H01B), C01C(H01C), C01D(H01D), C01E(H01E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl01 Cl -0.56763(8) 0.56982(3) 0.14458(2) 0.04733(16) Uani 1 1 d . . . . .
Cl02 Cl 1.26057(9) 0.05021(3) 0.51784(2) 0.05059(17) Uani 1 1 d . . . . .
O003 O 0.56488(18) 0.32847(7) 0.32527(4) 0.0315(3) Uani 1 1 d . . . . .
O004 O 0.11346(17) 0.24923(7) 0.31059(4) 0.0291(3) Uani 1 1 d . . . . .
C005 C 0.4441(2) 0.21022(8) 0.22336(5) 0.0242(3) Uani 1 1 d . . . . .
C006 C 0.2373(2) 0.38760(8) 0.40841(5) 0.0246(3) Uani 1 1 d . . . . .
C007 C 0.0572(3) 0.43825(9) 0.40842(5) 0.0253(3) Uani 1 1 d . . . . .
C008 C 0.3268(2) 0.36122(8) 0.45237(5) 0.0248(3) Uani 1 1 d . . . . .
C009 C 0.4877(2) 0.32150(9) 0.36066(5) 0.0279(3) Uani 1 1 d . . . . .
C00A C 0.6248(2) 0.16072(9) 0.21818(5) 0.0255(3) Uani 1 1 d . . . . .
C00B C 0.7951(3) 0.17051(9) 0.46002(6) 0.0324(4) Uani 1 1 d . . . . .
H00B H 0.6595 0.1882 0.4668 0.039 Uiso 1 1 calc R . . . .
C00C C 0.3685(2) 0.21826(9) 0.26311(5) 0.0269(3) Uani 1 1 d . . . . .
H00C H 0.4383 0.1906 0.2861 0.032 Uiso 1 1 calc R . . . .
C00D C 0.3922(3) 0.33070(10) 0.12487(6) 0.0348(4) Uani 1 1 d . . . . .
H00D H 0.4785 0.3637 0.1111 0.042 Uiso 1 1 calc R . . . .
C00E C 1.1101(3) 0.10219(10) 0.47974(7) 0.0383(4) Uani 1 1 d . . . . .
C00F C 0.8743(3) 0.18869(9) 0.41993(6) 0.0305(4) Uani 1 1 d . . . . .
C00G C 0.1958(3) 0.31980(9) 0.47665(5) 0.0283(3) Uani 1 1 d . . . . .
H00G H 0.0513 0.3106 0.4655 0.034 Uiso 1 1 calc R . . . .
C00H C 0.5362(3) 0.37626(9) 0.46992(5) 0.0294(3) Uani 1 1 d . . . . .
H00H H 0.6266 0.4049 0.4539 0.035 Uiso 1 1 calc R . . . .
C00I C 0.1162(3) 0.32494(9) 0.24961(5) 0.0265(3) Uani 1 1 d . . . . .
H00I H 0.2050 0.3449 0.2292 0.032 Uiso 1 1 calc R . . . .
C00J C 0.9468(3) 0.10051(9) 0.24817(6) 0.0316(4) Uani 1 1 d . . . . .
H00J H 1.0545 0.0928 0.2717 0.038 Uiso 1 1 calc R . . . .
C00K C 0.1788(3) 0.31996(10) 0.10845(5) 0.0354(4) Uani 1 1 d . . . . .
H00K H 0.1191 0.3457 0.0836 0.042 Uiso 1 1 calc R . . . .
C00L C 0.7840(2) 0.14882(9) 0.25287(5) 0.0267(3) Uani 1 1 d . . . . .
H00L H 0.7803 0.1739 0.2797 0.032 Uiso 1 1 calc R . . . .
C00M C 0.1930(2) 0.26375(9) 0.27624(5) 0.0260(3) Uani 1 1 d . . . . .
C00N C -0.1858(2) 0.40867(9) 0.22805(5) 0.0269(3) Uani 1 1 d . . . . .
C00O C 0.3111(2) 0.36920(9) 0.36980(5) 0.0274(3) Uani 1 1 d . . . . .
H00O H 0.2375 0.3903 0.3445 0.033 Uiso 1 1 calc R . . . .
C00P C 0.2746(3) 0.29199(10) 0.51691(6) 0.0342(4) Uani 1 1 d . . . . .
H00P H 0.1855 0.2628 0.5328 0.041 Uiso 1 1 calc R . . . .
C00Q C -0.2767(3) 0.53667(10) 0.40716(6) 0.0336(4) Uani 1 1 d . . . . .
H00Q H -0.3900 0.5700 0.4069 0.040 Uiso 1 1 calc R . . . .
C00R C 0.6130(3) 0.34948(10) 0.51076(6) 0.0348(4) Uani 1 1 d . . . . .
H00R H 0.7549 0.3605 0.5228 0.042 Uiso 1 1 calc R . . . .
C00S C -0.3807(3) 0.43498(9) 0.24041(5) 0.0289(3) Uani 1 1 d . . . . .
H00S H -0.4351 0.4179 0.2665 0.035 Uiso 1 1 calc R . . . .
C00T C -0.1080(3) 0.43507(9) 0.18931(6) 0.0300(3) Uani 1 1 d . . . . .
H00T H 0.0253 0.4185 0.1805 0.036 Uiso 1 1 calc R . . . .
C00U C -0.0786(2) 0.35238(9) 0.25421(5) 0.0269(3) Uani 1 1 d . . . . .
H00U H -0.1552 0.3332 0.2769 0.032 Uiso 1 1 calc R . . . .
C00V C 0.0526(3) 0.48820(9) 0.44182(5) 0.0300(3) Uani 1 1 d . . . . .
H00V H 0.1634 0.4886 0.4654 0.036 Uiso 1 1 calc R . . . .
C00W C 1.0736(3) 0.16104(10) 0.41049(6) 0.0347(4) Uani 1 1 d . . . . .
H00W H 1.1283 0.1720 0.3832 0.042 Uiso 1 1 calc R . . . .
C00X C 0.3518(2) 0.24633(8) 0.18261(5) 0.0249(3) Uani 1 1 d . . . . .
C00Y C -0.1096(2) 0.43830(9) 0.37435(5) 0.0262(3) Uani 1 1 d . . . . .
H00Y H -0.1095 0.4046 0.3514 0.031 Uiso 1 1 calc R . . . .
C00Z C 0.0542(3) 0.27140(10) 0.12857(6) 0.0339(4) Uani 1 1 d . . . . .
H00Z H -0.0901 0.2630 0.1169 0.041 Uiso 1 1 calc R . . . .
C010 C -0.2749(3) 0.48714(9) 0.37378(5) 0.0300(3) Uani 1 1 d . . . . .
H010 H -0.3871 0.4867 0.3505 0.036 Uiso 1 1 calc R . . . .
C011 C -0.2233(3) 0.48486(10) 0.16395(6) 0.0335(4) Uani 1 1 d . . . . .
H011 H -0.1700 0.5023 0.1379 0.040 Uiso 1 1 calc R . . . .
C012 C 0.5715(3) 0.26784(9) 0.39261(5) 0.0288(3) Uani 1 1 d . . . . .
H012 H 0.4889 0.2544 0.4159 0.035 Uiso 1 1 calc R . . . .
C013 C 0.6368(3) 0.12444(9) 0.17886(5) 0.0301(3) Uani 1 1 d . . . . .
H013 H 0.5328 0.1332 0.1548 0.036 Uiso 1 1 calc R . . . .
C014 C 1.1915(3) 0.11820(10) 0.44014(7) 0.0383(4) Uani 1 1 d . . . . .
H014 H 1.3266 0.0999 0.4335 0.046 Uiso 1 1 calc R . . . .
C015 C 0.9531(3) 0.06333(9) 0.20915(6) 0.0342(4) Uani 1 1 d . . . . .
H015 H 1.0631 0.0295 0.2063 0.041 Uiso 1 1 calc R . . . .
C016 C 0.1387(2) 0.23492(9) 0.16564(5) 0.0283(3) Uani 1 1 d . . . . .
H016 H 0.0515 0.2022 0.1795 0.034 Uiso 1 1 calc R . . . .
C017 C -0.4181(3) 0.50904(10) 0.17714(6) 0.0333(4) Uani 1 1 d . . . . .
C018 C 0.4788(3) 0.29342(9) 0.16118(5) 0.0286(3) Uani 1 1 d . . . . .
H018 H 0.6257 0.2999 0.1716 0.034 Uiso 1 1 calc R . . . .
C019 C 0.4839(3) 0.30685(10) 0.53401(6) 0.0367(4) Uani 1 1 d . . . . .
H019 H 0.5381 0.2878 0.5616 0.044 Uiso 1 1 calc R . . . .
C01A C 0.9108(3) 0.12731(10) 0.48977(6) 0.0362(4) Uani 1 1 d . . . . .
H01A H 0.8551 0.1149 0.5167 0.043 Uiso 1 1 calc R . . . .
C01B C -0.4969(3) 0.48537(10) 0.21556(6) 0.0328(4) Uani 1 1 d . . . . .
H01B H -0.6280 0.5033 0.2247 0.039 Uiso 1 1 calc R . . . .
C01C C -0.1120(3) 0.53711(9) 0.44092(5) 0.0339(4) Uani 1 1 d . . . . .
H01C H -0.1121 0.5712 0.4636 0.041 Uiso 1 1 calc R . . . .
C01D C 0.7639(3) 0.23793(9) 0.38886(5) 0.0301(4) Uani 1 1 d . . . . .
H01D H 0.8351 0.2499 0.3636 0.036 Uiso 1 1 calc R . . . .
C01E C 0.7985(3) 0.07568(10) 0.17443(6) 0.0345(4) Uani 1 1 d . . . . .
H01E H 0.8033 0.0507 0.1476 0.041 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
Cl01 C017 1.7409(18) . ?
Cl02 C00E 1.737(2) . ?
O003 C009 1.228(2) . ?
O004 C00M 1.231(2) . ?
C005 C00A 1.488(2) . ?
C005 C00C 1.349(2) . ?
C005 C00X 1.491(2) . ?
C006 C007 1.481(2) . ?
C006 C008 1.493(2) . ?
C006 C00O 1.349(2) . ?
C007 C00V 1.397(2) . ?
C007 C00Y 1.402(2) . ?
C008 C00G 1.396(2) . ?
C008 C00H 1.395(2) . ?
C009 C00O 1.474(2) . ?
C009 C012 1.475(2) . ?
C00A C00L 1.402(2) . ?
C00A C013 1.393(2) . ?
C00B H00B 0.9500 . ?
C00B C00F 1.403(2) . ?
C00B C01A 1.380(3) . ?
C00C H00C 0.9500 . ?
C00C C00M 1.479(2) . ?
C00D H00D 0.9500 . ?
C00D C00K 1.393(3) . ?
C00D C018 1.384(3) . ?
C00E C014 1.386(3) . ?
C00E C01A 1.391(3) . ?
C00F C00W 1.402(2) . ?
C00F C01D 1.461(3) . ?
C00G H00G 0.9500 . ?
C00G C00P 1.386(2) . ?
C00H H00H 0.9500 . ?
C00H C00R 1.391(2) . ?
C00I H00I 0.9500 . ?
C00I C00M 1.476(2) . ?
C00I C00U 1.341(2) . ?
C00J H00J 0.9500 . ?
C00J C00L 1.387(2) . ?
C00J C015 1.389(3) . ?
C00K H00K 0.9500 . ?
C00K C00Z 1.387(3) . ?
C00L H00L 0.9500 . ?
C00N C00S 1.398(2) . ?
C00N C00T 1.410(2) . ?
C00N C00U 1.463(2) . ?
C00O H00O 0.9500 . ?
C00P H00P 0.9500 . ?
C00P C019 1.389(3) . ?
C00Q H00Q 0.9500 . ?
C00Q C010 1.390(3) . ?
C00Q C01C 1.387(2) . ?
C00R H00R 0.9500 . ?
C00R C019 1.383(3) . ?
C00S H00S 0.9500 . ?
C00S C01B 1.387(2) . ?
C00T H00T 0.9500 . ?
C00T C011 1.384(3) . ?
C00U H00U 0.9500 . ?
C00V H00V 0.9500 . ?
C00V C01C 1.385(2) . ?
C00W H00W 0.9500 . ?
C00W C014 1.380(3) . ?
C00X C016 1.398(2) . ?
C00X C018 1.397(2) . ?
C00Y H00Y 0.9500 . ?
C00Y C010 1.387(2) . ?
C00Z H00Z 0.9500 . ?
C00Z C016 1.390(2) . ?
C010 H010 0.9500 . ?
C011 H011 0.9500 . ?
C011 C017 1.391(2) . ?
C012 H012 0.9500 . ?
C012 C01D 1.342(2) . ?
C013 H013 0.9500 . ?
C013 C01E 1.386(2) . ?
C014 H014 0.9500 . ?
C015 H015 0.9500 . ?
C015 C01E 1.387(3) . ?
C016 H016 0.9500 . ?
C017 C01B 1.387(3) . ?
C018 H018 0.9500 . ?
C019 H019 0.9500 . ?
C01A H01A 0.9500 . ?
C01B H01B 0.9500 . ?
C01C H01C 0.9500 . ?
C01D H01D 0.9500 . ?
C01E H01E 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00A C005 C00X 116.30(13) . . ?
C00C C005 C00A 119.76(14) . . ?
C00C C005 C00X 123.90(14) . . ?
C007 C006 C008 116.18(13) . . ?
C00O C006 C007 119.20(14) . . ?
C00O C006 C008 124.61(15) . . ?
C00V C007 C006 120.67(14) . . ?
C00V C007 C00Y 118.55(15) . . ?
C00Y C007 C006 120.77(14) . . ?
C00G C008 C006 118.58(14) . . ?
C00H C008 C006 122.46(14) . . ?
C00H C008 C00G 118.97(15) . . ?
O003 C009 C00O 117.26(16) . . ?
O003 C009 C012 120.83(15) . . ?
C00O C009 C012 121.91(14) . . ?
C00L C00A C005 120.86(14) . . ?
C013 C00A C005 120.39(14) . . ?
C013 C00A C00L 118.74(15) . . ?
C00F C00B H00B 119.4 . . ?
C01A C00B H00B 119.4 . . ?
C01A C00B C00F 121.12(16) . . ?
C005 C00C H00C 115.2 . . ?
C005 C00C C00M 129.56(15) . . ?
C00M C00C H00C 115.2 . . ?
C00K C00D H00D 119.9 . . ?
C018 C00D H00D 119.9 . . ?
C018 C00D C00K 120.20(17) . . ?
C014 C00E Cl02 119.44(15) . . ?
C014 C00E C01A 121.35(18) . . ?
C01A C00E Cl02 119.21(16) . . ?
C00B C00F C01D 122.82(15) . . ?
C00W C00F C00B 118.29(17) . . ?
C00W C00F C01D 118.80(16) . . ?
C008 C00G H00G 119.7 . . ?
C00P C00G C008 120.59(16) . . ?
C00P C00G H00G 119.7 . . ?
C008 C00H H00H 119.9 . . ?
C00R C00H C008 120.19(16) . . ?
C00R C00H H00H 119.9 . . ?
C00M C00I H00I 119.9 . . ?
C00U C00I H00I 119.9 . . ?
C00U C00I C00M 120.13(15) . . ?
C00L C00J H00J 119.8 . . ?
C00L C00J C015 120.33(16) . . ?
C015 C00J H00J 119.8 . . ?
C00D C00K H00K 120.2 . . ?
C00Z C00K C00D 119.57(16) . . ?
C00Z C00K H00K 120.2 . . ?
C00A C00L H00L 119.9 . . ?
C00J C00L C00A 120.23(15) . . ?
C00J C00L H00L 119.9 . . ?
O004 C00M C00C 117.59(15) . . ?
O004 C00M C00I 120.74(14) . . ?
C00I C00M C00C 121.67(14) . . ?
C00S C00N C00T 118.11(16) . . ?
C00S C00N C00U 118.78(15) . . ?
C00T C00N C00U 123.01(15) . . ?
C006 C00O C009 130.15(15) . . ?
C006 C00O H00O 114.9 . . ?
C009 C00O H00O 114.9 . . ?
C00G C00P H00P 120.0 . . ?
C00G C00P C019 120.03(16) . . ?
C019 C00P H00P 120.0 . . ?
C010 C00Q H00Q 120.2 . . ?
C01C C00Q H00Q 120.2 . . ?
C01C C00Q C010 119.61(16) . . ?
C00H C00R H00R 119.8 . . ?
C019 C00R C00H 120.39(16) . . ?
C019 C00R H00R 119.8 . . ?
C00N C00S H00S 119.2 . . ?
C01B C00S C00N 121.65(16) . . ?
C01B C00S H00S 119.2 . . ?
C00N C00T H00T 119.6 . . ?
C011 C00T C00N 120.87(15) . . ?
C011 C00T H00T 119.6 . . ?
C00I C00U C00N 127.03(15) . . ?
C00I C00U H00U 116.5 . . ?
C00N C00U H00U 116.5 . . ?
C007 C00V H00V 119.7 . . ?
C01C C00V C007 120.54(15) . . ?
C01C C00V H00V 119.7 . . ?
C00F C00W H00W 119.5 . . ?
C014 C00W C00F 121.10(17) . . ?
C014 C00W H00W 119.5 . . ?
C016 C00X C005 121.28(14) . . ?
C018 C00X C005 119.65(14) . . ?
C018 C00X C016 119.06(15) . . ?
C007 C00Y H00Y 119.7 . . ?
C010 C00Y C007 120.64(15) . . ?
C010 C00Y H00Y 119.7 . . ?
C00K C00Z H00Z 119.7 . . ?
C00K C00Z C016 120.51(16) . . ?
C016 C00Z H00Z 119.7 . . ?
C00Q C010 H010 119.9 . . ?
C00Y C010 C00Q 120.11(15) . . ?
C00Y C010 H010 119.9 . . ?
C00T C011 H011 120.4 . . ?
C00T C011 C017 119.20(16) . . ?
C017 C011 H011 120.4 . . ?
C009 C012 H012 119.9 . . ?
C01D C012 C009 120.27(15) . . ?
C01D C012 H012 119.9 . . ?
C00A C013 H013 119.6 . . ?
C01E C013 C00A 120.83(16) . . ?
C01E C013 H013 119.6 . . ?
C00E C014 H014 120.4 . . ?
C00W C014 C00E 119.13(17) . . ?
C00W C014 H014 120.4 . . ?
C00J C015 H015 120.1 . . ?
C01E C015 C00J 119.77(16) . . ?
C01E C015 H015 120.1 . . ?
C00X C016 H016 120.0 . . ?
C00Z C016 C00X 120.06(16) . . ?
C00Z C016 H016 120.0 . . ?
C011 C017 Cl01 119.45(14) . . ?
C01B C017 Cl01 119.11(13) . . ?
C01B C017 C011 121.44(16) . . ?
C00D C018 C00X 120.53(15) . . ?
C00D C018 H018 119.7 . . ?
C00X C018 H018 119.7 . . ?
C00P C019 H019 120.1 . . ?
C00R C019 C00P 119.79(16) . . ?
C00R C019 H019 120.1 . . ?
C00B C01A C00E 118.99(18) . . ?
C00B C01A H01A 120.5 . . ?
C00E C01A H01A 120.5 . . ?
C00S C01B C017 118.70(16) . . ?
C00S C01B H01B 120.6 . . ?
C017 C01B H01B 120.6 . . ?
C00Q C01C H01C 119.7 . . ?
C00V C01C C00Q 120.55(16) . . ?
C00V C01C H01C 119.7 . . ?
C00F C01D H01D 116.9 . . ?
C012 C01D C00F 126.14(16) . . ?
C012 C01D H01D 116.9 . . ?
C013 C01E C015 120.06(16) . . ?
C013 C01E H01E 120.0 . . ?
C015 C01E H01E 120.0 . . ?

_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 1.800
_oxdiff_exptl_absorpt_empirical_full_min 0.529
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.37(5) 2 25381 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.63(5) 5 25381 nmt 0.9999 0.0004 0.0012 -0.0048 0.9994 -0.0015 -0.0368
0.0046 0.9994

_twin_special_details            
;
Component 2 rotated by 0.4687° 
 around [0.12 0.94 -0.31] (reciprocal) or [0.76 0.64 -0.07] (direct)
;
####################################################################### 
# 
# 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_9202_ima052
_database_code_depnum_ccdc_archive 'CCDC 1847456'
_audit_update_record             
;
2018-06-05 deposited with the CCDC.
2018-10-03 downloaded from the CCDC.
;
_audit_creation_date             2018-04-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 F O2'
_chemical_formula_sum            'C17 H13 F O2'
_chemical_formula_weight         268.27
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Cl2 F C25'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   30.335(6)
_cell_length_b                   5.7303(10)
_cell_length_c                   7.3960(18)
_cell_angle_alpha                90
_cell_angle_beta                 92.47(2)
_cell_angle_gamma                90
_cell_volume                     1284.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    886
_cell_measurement_temperature    100(3)
_cell_measurement_theta_max      75.5760
_cell_measurement_theta_min      5.7730
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.853
_exptl_absorpt_coefficient_mu    0.823
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1108
_diffrn_reflns_av_unetI/netI     0.0985
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3924
_diffrn_reflns_point_group_measured_fraction_full 0.823
_diffrn_reflns_point_group_measured_fraction_max 0.820
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.846
_diffrn_reflns_theta_min         2.916
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00 -39.00   1.00   35.00    --  -40.38 178.00  30.00   27
  2  ω   -100.00 -40.00   1.00   35.00    --  -40.38 178.00  90.00   60
  3  ω   -100.00 -14.00   1.00   35.00    --  -40.38 -38.00-120.00   86
  4  ω    -66.00  36.00   1.00   35.00    --  -40.38  38.00  60.00  102
  5  ω     98.00 129.00   1.00   35.00    --   40.38 178.00  30.00   31
  6  ω     67.00 129.00   1.00   35.00    --   40.38 178.00-150.00   62
  7  ω     53.00 139.00   1.00   52.50    --  113.00  15.00 -60.00   86
  8  ω     72.00 109.00   1.00   52.50    --  113.00 -95.00  90.00   37
  9  ω     38.00 123.00   1.00   52.50    --  113.00 -45.00   0.00   85
 10  ω    122.00 166.00   1.00   52.50    --  113.00  77.00 -30.00   44
 11  ω     88.00 176.00   1.00   52.50    --  113.00  30.00-180.00   88
 12  ω     30.00 109.00   1.00   52.50    --  113.00 -95.00  30.00   79
 13  ω     57.00 146.00   1.00   52.50    --  113.00 178.00  30.00   89
 14  ω    111.00 149.00   1.00   52.50    --  113.00  45.00  60.00   38
 15  ω     37.00  64.00   1.00   52.50    --  113.00-112.00-180.00   27
 16  ω     36.00 111.00   1.00   52.50    --  113.00-112.00   0.00   75
 17  ω     81.00 173.00   1.00   52.50    --  113.00  77.00 120.00   92
 18  ω     58.00 109.00   1.00   52.50    --  113.00 -95.00-180.00   51
 19  ω     41.00 116.00   1.00   52.50    --  113.00 -61.00 150.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0497019000
_diffrn_orient_matrix_UB_12      -0.0476656000
_diffrn_orient_matrix_UB_13      -0.0325615000
_diffrn_orient_matrix_UB_21      -0.0049513000
_diffrn_orient_matrix_UB_22      -0.0237505000
_diffrn_orient_matrix_UB_23      0.2056652000
_diffrn_orient_matrix_UB_31      -0.0095442000
_diffrn_orient_matrix_UB_32      0.2627622000
_diffrn_orient_matrix_UB_33      0.0130068000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.641
_reflns_Friedel_fraction_full    0.648
_reflns_Friedel_fraction_max     0.642
_reflns_number_gt                1473
_reflns_number_total             1996
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.55
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         0.484
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.121
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.2(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1996
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1187
_refine_ls_R_factor_gt           0.0982
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1906P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2545
_refine_ls_wR_factor_ref         0.2959
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C7(H7), C2(H2A), C5(H5), C11(H11), C9(H9), C4(H4), C13(H13),
 C10(H10), C16(H16), C8(H8), C17(H17)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.52217(17) 0.0591(8) -0.2104(8) 0.0419(13) Uani 1 1 d . . . . .
O1 O -0.2397(2) -1.0233(10) -0.2769(11) 0.0469(17) Uani 1 1 d . . . . .
O2 O -0.31581(19) -0.8803(10) -0.3414(9) 0.0432(16) Uani 1 1 d . . . . .
H2 H -0.3410 -0.9180 -0.3090 0.065 Uiso 1 1 calc GR . . . .
C1 C -0.2293(3) -0.8273(14) -0.2076(12) 0.0360(18) Uani 1 1 d . . . . .
C6 C -0.1824(3) -0.7899(14) -0.1381(13) 0.037(2) Uani 1 1 d . . . . .
C15 C -0.4874(3) -0.0870(13) -0.2312(11) 0.0320(17) Uani 1 1 d . . . . .
C3 C -0.3038(3) -0.6818(14) -0.2624(12) 0.0361(18) Uani 1 1 d . . . . .
C14 C -0.4950(3) -0.2985(14) -0.3146(12) 0.0335(17) Uani 1 1 d . . . . .
H14 H -0.5239 -0.3437 -0.3551 0.040 Uiso 1 1 calc R . . . .
C12 C -0.4161(3) -0.3784(13) -0.2778(12) 0.0313(17) Uani 1 1 d . . . . .
C7 C -0.1683(3) -0.5924(14) -0.0447(13) 0.0372(19) Uani 1 1 d . . . . .
H7 H -0.1889 -0.4719 -0.0221 0.045 Uiso 1 1 calc R . . . .
C2 C -0.2614(3) -0.6454(14) -0.1968(12) 0.0363(19) Uani 1 1 d . . . . .
H2A H -0.2534 -0.4995 -0.1442 0.044 Uiso 1 1 calc R . . . .
C5 C -0.3796(2) -0.5397(13) -0.2994(11) 0.0324(18) Uani 1 1 d . . . . .
H5 H -0.3865 -0.6834 -0.3583 0.039 Uiso 1 1 calc R . . . .
C11 C -0.1520(3) -0.9669(14) -0.1734(13) 0.0363(19) Uani 1 1 d . . . . .
H11 H -0.1613 -1.1033 -0.2374 0.044 Uiso 1 1 calc R . . . .
C9 C -0.0944(3) -0.7449(14) -0.0214(12) 0.0337(18) Uani 1 1 d . . . . .
H9 H -0.0643 -0.7292 0.0172 0.040 Uiso 1 1 calc R . . . .
C4 C -0.3375(3) -0.5068(15) -0.2450(13) 0.0377(19) Uani 1 1 d . . . . .
H4 H -0.3294 -0.3609 -0.1922 0.045 Uiso 1 1 calc R . . . .
C13 C -0.4589(3) -0.4443(12) -0.3375(11) 0.0308(17) Uani 1 1 d . . . . .
H13 H -0.4633 -0.5914 -0.3947 0.037 Uiso 1 1 calc R . . . .
C10 C -0.1082(3) -0.9409(13) -0.1137(12) 0.0351(19) Uani 1 1 d . . . . .
H10 H -0.0875 -1.0605 -0.1373 0.042 Uiso 1 1 calc R . . . .
C16 C -0.4461(3) -0.0154(14) -0.1722(11) 0.0340(18) Uani 1 1 d . . . . .
H16 H -0.4422 0.1323 -0.1154 0.041 Uiso 1 1 calc R . . . .
C8 C -0.1245(3) -0.5669(14) 0.0169(12) 0.0364(19) Uani 1 1 d . . . . .
H8 H -0.1152 -0.4323 0.0832 0.044 Uiso 1 1 calc R . . . .
C17 C -0.4104(3) -0.1583(13) -0.1955(11) 0.0325(17) Uani 1 1 d . . . . .
H17 H -0.3818 -0.1083 -0.1559 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 C15 1.361(9) . ?
O1 C1 1.269(10) . ?
O2 C3 1.323(10) . ?
C1 C6 1.505(11) . ?
C1 C2 1.432(11) . ?
C6 C7 1.384(12) . ?
C6 C11 1.404(11) . ?
C15 C14 1.375(11) . ?
C15 C16 1.371(12) . ?
C3 C2 1.368(12) . ?
C3 C4 1.444(11) . ?
C14 C13 1.394(11) . ?
C12 C5 1.456(10) . ?
C12 C13 1.404(11) . ?
C12 C17 1.408(11) . ?
C7 C8 1.393(12) . ?
C5 C4 1.335(11) . ?
C11 C10 1.390(12) . ?
C9 C10 1.370(12) . ?
C9 C8 1.406(11) . ?
C16 C17 1.374(11) . ?

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
O1 C1 C6 118.6(7) . . ?
O1 C1 C2 120.6(8) . . ?
C2 C1 C6 120.9(7) . . ?
C7 C6 C1 123.7(7) . . ?
C7 C6 C11 119.4(7) . . ?
C11 C6 C1 116.9(7) . . ?
F1 C15 C14 118.5(7) . . ?
F1 C15 C16 118.8(7) . . ?
C16 C15 C14 122.7(8) . . ?
O2 C3 C2 121.6(7) . . ?
O2 C3 C4 116.9(7) . . ?
C2 C3 C4 121.4(7) . . ?
C15 C14 C13 117.8(7) . . ?
C13 C12 C5 119.4(7) . . ?
C13 C12 C17 118.1(7) . . ?
C17 C12 C5 122.4(7) . . ?
C6 C7 C8 121.3(7) . . ?
C3 C2 C1 120.0(7) . . ?
C4 C5 C12 126.8(7) . . ?
C10 C11 C6 119.4(8) . . ?
C10 C9 C8 120.6(7) . . ?
C5 C4 C3 123.2(8) . . ?
C14 C13 C12 121.4(7) . . ?
C9 C10 C11 120.8(7) . . ?
C15 C16 C17 119.7(7) . . ?
C7 C8 C9 118.4(8) . . ?
C16 C17 C12 120.4(7) . . ?

_olex2_date_sample_data_collection 2018-03-24
_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 3.052
_oxdiff_exptl_absorpt_empirical_full_min 0.506
####################################################################### 
# 
# 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_9137_avv363
_database_code_depnum_ccdc_archive 'CCDC 1847453'
_audit_update_record             
;
2018-06-05 deposited with the CCDC.
2018-10-03 downloaded from the CCDC.
;
_audit_creation_date             2018-03-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 F O'
_chemical_formula_sum            'C23 H17 F O'
_chemical_formula_weight         328.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'F O C30'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.20717(15)
_cell_length_b                   38.6061(11)
_cell_length_c                   14.5881(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.406(2)
_cell_angle_gamma                90
_cell_volume                     3448.81(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14414
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.7140
_cell_measurement_theta_min      2.2280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1376
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27840
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.967
_diffrn_reflns_theta_min         2.289
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -78.00 -32.00   0.50    0.20    --  -41.35 136.00 -41.00   92
  2  ω    -71.00 -45.00   0.50    0.20    --  -41.35 133.00 140.00   52
  3  ω     11.00  36.00   0.50    0.20    --   41.35-133.00  71.00   50
  4  ω     30.00  55.00   0.50    0.20    --   41.35-136.00-106.00   50
  5  ω     88.00 113.00   0.50    0.43    --  101.00 136.00 -41.00   50
  6  ω     83.00 109.00   0.50    0.43    --  101.00-136.00-106.00   52
  7  ω     78.00 124.00   0.50    0.43    --  101.00-133.00  71.00   92
  8  ω    113.00 138.00   0.50    0.43    --  101.00 133.00 140.00   50
  9  ω   -104.00 -70.00   0.50    0.20    --  -41.35 -54.00  30.00   68
 10  ω    -64.00 -26.00   0.50    0.20    --  -41.35 -54.00  30.00   76
 11  ω    -49.00 -17.00   0.50    0.20    --  -41.35 -77.00-120.00   64
 12  ω   -104.00 -70.00   0.50    0.20    --  -41.35 -77.00-120.00   68
 13  ω    -19.00  53.00   0.50    0.20    --   41.35 -43.00  30.00  144
 14  ω     54.00  98.00   0.50    0.20    --   41.35  32.00 -30.00   88
 15  ω     17.00  92.00   0.50    0.20    --   41.35  77.00 120.00  150
 16  ω     27.00  53.00   0.50    0.20    --   41.35  54.00 120.00   52
 17  ω     24.00  62.00   0.50    0.20    --   41.35 -65.00 150.00   76
 18  ω     70.00  95.00   0.50    0.20    --   41.35-133.00  71.00   50
 19  ω    -15.00  41.00   0.50    0.20    --   41.35 -43.00-180.00  112
 20  ω     71.00  97.00   0.50    0.20    --   41.35  54.00 120.00   52
 21  ω     62.00  90.00   0.50    0.43    --  101.00-111.00-180.00   56
 22  ω     52.00 100.00   0.50    0.43    --  101.00 -50.00-150.00   96
 23  ω     43.00 132.00   0.50    0.43    --  101.00 -93.00-120.00  178
 24  ω     81.00 143.00   0.50    0.43    --  101.00  93.00   0.00  124
 25  ω     78.00 104.00   0.50    0.43    --  101.00 -25.00 -30.00   52
 26  ω     64.00 123.00   0.50    0.43    --  101.00 -68.00  30.00  118
 27  ω    125.00 151.00   0.50    0.43    --  101.00  17.00 -30.00   52
 28  ω     88.00 117.00   0.50    0.43    --  101.00  17.00 -30.00   58
 29  ω    132.00 157.00   0.50    0.43    --  101.00  33.00 -30.00   50
 30  ω     88.00 135.00   0.50    0.43    --  101.00  59.00 -30.00   94
 31  ω     32.00  80.00   0.50    0.43    --  101.00 -93.00   0.00   96
 32  ω     89.00 114.00   0.50    0.43    --  101.00 -93.00   0.00   50
 33  ω     37.00  67.00   0.50    0.43    --  101.00 -68.00 -60.00   60
 34  ω     99.00 156.00   0.50    0.43    --  101.00  33.00 -90.00  114
 35  ω     71.00 113.00   0.50    0.43    --  101.00 -59.00-150.00   84
 36  ω     80.00 136.00   0.50    0.43    --  101.00 111.00   0.00  112
 37  ω     36.00 100.00   0.50    0.43    --  101.00-111.00-120.00  128
 38  ω     76.00 109.00   0.50    0.43    --  101.00  77.00-180.00   66
 39  ω     84.00 154.00   0.50    0.43    --  101.00 133.00 150.00  140
 40  ω     95.00 121.00   0.50    0.43    --  101.00  33.00 -30.00   52
 41  ω    122.00 147.00   0.50    0.43    --  101.00  77.00-180.00   50
 42  ω     36.00 110.00   0.50    0.43    --  101.00 -33.00-180.00  148
 43  ω     88.00 113.00   0.50    0.43    --  101.00 136.00 -41.00   50
 44  ω    -66.00 -40.00   0.50    0.20    --  -41.35 -32.00  60.00   52
 45  ω    -34.00  -8.00   0.50    0.20    --  -41.35  32.00-180.00   52
 46  ω     -7.00  20.00   0.50    0.20    --  -41.35  32.00-180.00   54
 47  ω     61.00  87.00   0.50    0.20    --   41.35  32.00-180.00   52
 48  ω      2.00  38.00   0.50    0.20    --   41.35 -54.00  90.00   72
 49  ω     37.00  78.00   0.50    0.20    --   41.35  32.00-120.00   82
 50  ω     66.00 100.00   0.50    0.20    --   41.35  11.00-120.00   68
 51  ω     19.00  45.00   0.50    0.20    --   41.35  11.00-120.00   52
 52  ω     72.00  98.00   0.50    0.43    --  101.00 133.00 -60.00   52
 53  ω     81.00 110.00   0.50    0.43    --  101.00 -25.00  60.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0170356000
_diffrn_orient_matrix_UB_12      0.0109513000
_diffrn_orient_matrix_UB_13      0.1024785000
_diffrn_orient_matrix_UB_21      0.0070491000
_diffrn_orient_matrix_UB_22      -0.0383757000
_diffrn_orient_matrix_UB_23      0.0293267000
_diffrn_orient_matrix_UB_31      0.2508918000
_diffrn_orient_matrix_UB_32      0.0003340000
_diffrn_orient_matrix_UB_33      0.0098186000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5883
_reflns_number_total             6752
_reflns_odcompleteness_completeness 99.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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         0.216
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6752
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.073
_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)+(0.0561P)²+0.8845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1144
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C19A(H19A), C2A(H2A), C4(H4), C5(H5), C13A(H13A), C4A(H4A), C19(H19),
 C17(H17), C17A(H17A), C2(H2), C5A(H5A), C11(H11), C7(H7), C23(H23), C10(H10),
 C23A(H23A), C11A(H11A), C10A(H10A), C20A(H20A), C21A(H21A), C13(H13),
 C16A(H16A), C7A(H7A), C22(H22), C16(H16), C15(H15), C22A(H22A), C8(H8),
 C14(H14), C20(H20), C15A(H15A), C8A(H8A), C14A(H14A), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F25 F 0.10518(14) 0.17308(2) 0.35173(6) 0.0341(2) Uani 1 1 d . . . . .
F50 F 1.36179(14) 0.31812(2) 0.59095(6) 0.0329(2) Uani 1 1 d . . . . .
O37 O 0.74004(14) 0.51207(2) 0.54732(6) 0.0239(2) Uani 1 1 d . . . . .
O12 O 0.72232(15) 0.36756(3) 0.40152(6) 0.0262(2) Uani 1 1 d . . . . .
C12 C 0.29011(19) 0.50581(3) 0.77975(9) 0.0183(3) Uani 1 1 d . . . . .
C18 C 0.5489(2) 0.45530(3) 0.77534(8) 0.0173(2) Uani 1 1 d . . . . .
C12A C 1.18534(19) 0.36206(3) 0.17233(9) 0.0183(3) Uani 1 1 d . . . . .
C18A C 0.9322(2) 0.31106(3) 0.17527(8) 0.0174(2) Uani 1 1 d . . . . .
C19A C 1.0738(2) 0.28318(3) 0.17006(8) 0.0194(3) Uani 1 1 d . . . . .
H19A H 1.2221 0.2857 0.1923 0.023 Uiso 1 1 calc R . . . .
C2A C 0.9589(2) 0.35824(3) 0.29584(9) 0.0197(3) Uani 1 1 d . . . . .
H2A H 1.0286 0.3789 0.3157 0.024 Uiso 1 1 calc R . . . .
C1A C 1.02198(18) 0.34402(3) 0.21959(8) 0.0176(2) Uani 1 1 d . . . . .
C1 C 0.45211(19) 0.48801(3) 0.73167(8) 0.0172(2) Uani 1 1 d . . . . .
C4 C 0.7398(2) 0.45369(3) 0.59659(8) 0.0193(3) Uani 1 1 d . . . . .
H4 H 0.6571 0.4365 0.6190 0.023 Uiso 1 1 calc R . . . .
C6 C 1.0268(2) 0.41110(3) 0.56867(8) 0.0195(3) Uani 1 1 d . . . . .
C5 C 0.9235(2) 0.44527(3) 0.56479(8) 0.0203(3) Uani 1 1 d . . . . .
H5 H 0.9925 0.4630 0.5374 0.024 Uiso 1 1 calc R . . . .
C13A C 1.1715(2) 0.35958(3) 0.07575(9) 0.0215(3) Uani 1 1 d . . . . .
H13A H 1.0637 0.3459 0.0418 0.026 Uiso 1 1 calc R . . . .
C3A C 0.7967(2) 0.34612(3) 0.35256(8) 0.0204(3) Uani 1 1 d . . . . .
C4A C 0.7228(2) 0.30953(3) 0.35046(8) 0.0205(3) Uani 1 1 d . . . . .
H4A H 0.8080 0.2924 0.3295 0.025 Uiso 1 1 calc R . . . .
C19 C 0.7691(2) 0.45308(3) 0.81492(8) 0.0206(3) Uani 1 1 d . . . . .
H19 H 0.8590 0.4724 0.8150 0.025 Uiso 1 1 calc R . . . .
C3 C 0.66788(19) 0.49022(3) 0.59621(8) 0.0189(3) Uani 1 1 d . . . . .
C17 C 0.11900(19) 0.52537(3) 0.72983(9) 0.0204(3) Uani 1 1 d . . . . .
H17 H 0.1021 0.5263 0.6653 0.024 Uiso 1 1 calc R . . . .
C17A C 1.3530(2) 0.38236(3) 0.22195(9) 0.0209(3) Uani 1 1 d . . . . .
H17A H 1.3665 0.3840 0.2862 0.025 Uiso 1 1 calc R . . . .
C2 C 0.5080(2) 0.50225(3) 0.65433(9) 0.0198(3) Uani 1 1 d . . . . .
H2 H 0.4353 0.5227 0.6346 0.024 Uiso 1 1 calc R . . . .
C6A C 0.4314(2) 0.26670(3) 0.37370(8) 0.0203(3) Uani 1 1 d . . . . .
C5A C 0.5348(2) 0.30096(3) 0.37835(8) 0.0207(3) Uani 1 1 d . . . . .
H5A H 0.4615 0.3187 0.4035 0.025 Uiso 1 1 calc R . . . .
C11 C 1.2144(2) 0.40670(3) 0.52754(8) 0.0208(3) Uani 1 1 d . . . . .
H11 H 1.2641 0.4251 0.4954 0.025 Uiso 1 1 calc R . . . .
C7 C 0.9536(2) 0.38292(3) 0.61623(9) 0.0222(3) Uani 1 1 d . . . . .
H7 H 0.8290 0.3853 0.6435 0.027 Uiso 1 1 calc R . . . .
C23 C 0.4155(2) 0.42616(3) 0.77620(9) 0.0216(3) Uani 1 1 d . . . . .
H23 H 0.2675 0.4276 0.7522 0.026 Uiso 1 1 calc R . . . .
C10 C 1.3275(2) 0.37548(3) 0.53374(9) 0.0227(3) Uani 1 1 d . . . . .
H10 H 1.4515 0.3727 0.5063 0.027 Uiso 1 1 calc R . . . .
C23A C 0.7112(2) 0.30736(3) 0.13748(9) 0.0211(3) Uani 1 1 d . . . . .
H23A H 0.6158 0.3259 0.1391 0.025 Uiso 1 1 calc R . . . .
C11A C 0.2417(2) 0.26206(4) 0.41287(9) 0.0221(3) Uani 1 1 d . . . . .
H11A H 0.1881 0.2805 0.4436 0.027 Uiso 1 1 calc R . . . .
C10A C 0.1318(2) 0.23059(4) 0.40681(9) 0.0240(3) Uani 1 1 d . . . . .
H10A H 0.0066 0.2277 0.4333 0.029 Uiso 1 1 calc R . . . .
C20A C 0.9949(2) 0.25170(3) 0.13201(9) 0.0227(3) Uani 1 1 d . . . . .
H20A H 1.0895 0.2331 0.1308 0.027 Uiso 1 1 calc R . . . .
C21A C 0.7742(2) 0.24810(4) 0.09581(9) 0.0249(3) Uani 1 1 d . . . . .
H21A H 0.7208 0.2271 0.0705 0.030 Uiso 1 1 calc R . . . .
C9 C 1.2496(2) 0.34882(3) 0.58203(9) 0.0239(3) Uani 1 1 d . . . . .
C13 C 0.3077(2) 0.50425(3) 0.87673(9) 0.0221(3) Uani 1 1 d . . . . .
H13 H 0.4162 0.4907 0.9108 0.027 Uiso 1 1 calc R . . . .
C16A C 1.4989(2) 0.39998(3) 0.17586(10) 0.0256(3) Uani 1 1 d . . . . .
H16A H 1.6089 0.4134 0.2095 0.031 Uiso 1 1 calc R . . . .
C7A C 0.5096(2) 0.23851(4) 0.32778(9) 0.0230(3) Uani 1 1 d . . . . .
H7A H 0.6359 0.2410 0.3018 0.028 Uiso 1 1 calc R . . . .
C22 C 0.5031(2) 0.39504(4) 0.81282(9) 0.0273(3) Uani 1 1 d . . . . .
H22 H 0.4149 0.3755 0.8107 0.033 Uiso 1 1 calc R . . . .
C16 C -0.0249(2) 0.54337(3) 0.77570(10) 0.0252(3) Uani 1 1 d . . . . .
H16 H -0.1378 0.5561 0.7417 0.030 Uiso 1 1 calc R . . . .
C15 C -0.0016(2) 0.54249(4) 0.87211(10) 0.0274(3) Uani 1 1 d . . . . .
H15 H -0.0965 0.5550 0.9027 0.033 Uiso 1 1 calc R . . . .
C22A C 0.6338(2) 0.27613(4) 0.09760(9) 0.0250(3) Uani 1 1 d . . . . .
H22A H 0.4871 0.2739 0.0719 0.030 Uiso 1 1 calc R . . . .
C8 C 1.0645(2) 0.35166(4) 0.62304(9) 0.0249(3) Uani 1 1 d . . . . .
H8 H 1.0158 0.3330 0.6544 0.030 Uiso 1 1 calc R . . . .
C14 C 0.1647(2) 0.52276(4) 0.92265(10) 0.0269(3) Uani 1 1 d . . . . .
H14 H 0.1803 0.5219 0.9871 0.032 Uiso 1 1 calc R . . . .
C9A C 0.2140(2) 0.20383(4) 0.36028(9) 0.0251(3) Uani 1 1 d . . . . .
C20 C 0.8547(2) 0.42209(4) 0.85425(9) 0.0270(3) Uani 1 1 d . . . . .
H20 H 1.0008 0.4209 0.8816 0.032 Uiso 1 1 calc R . . . .
C15A C 1.4811(2) 0.39767(3) 0.07975(11) 0.0274(3) Uani 1 1 d . . . . .
H15A H 1.5781 0.4096 0.0490 0.033 Uiso 1 1 calc R . . . .
C8A C 0.4011(2) 0.20699(4) 0.32067(10) 0.0268(3) Uani 1 1 d . . . . .
H8A H 0.4528 0.1884 0.2900 0.032 Uiso 1 1 calc R . . . .
C14A C 1.3174(2) 0.37741(4) 0.03002(10) 0.0257(3) Uani 1 1 d . . . . .
H14A H 1.3052 0.3758 -0.0342 0.031 Uiso 1 1 calc R . . . .
C21 C 0.7223(3) 0.39299(4) 0.85271(10) 0.0305(3) Uani 1 1 d . . . . .
H21 H 0.7800 0.3722 0.8782 0.037 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
F25 C9A 1.3616(15) . ?
F50 C9 1.3701(15) . ?
O37 C3 1.2348(15) . ?
O12 C3A 1.2314(16) . ?
C12 C1 1.4853(17) . ?
C12 C17 1.4057(17) . ?
C12 C13 1.4022(18) . ?
C18 C1 1.4954(17) . ?
C18 C19 1.3966(17) . ?
C18 C23 1.3983(17) . ?
C12A C1A 1.4891(17) . ?
C12A C13A 1.4008(18) . ?
C12A C17A 1.4051(17) . ?
C18A C19A 1.3993(17) . ?
C18A C1A 1.4932(17) . ?
C18A C23A 1.3999(17) . ?
C19A H19A 0.9300 . ?
C19A C20A 1.3916(18) . ?
C2A H2A 0.9300 . ?
C2A C1A 1.3544(17) . ?
C2A C3A 1.4799(17) . ?
C1 C2 1.3504(17) . ?
C4 H4 0.9300 . ?
C4 C5 1.3395(18) . ?
C4 C3 1.4790(18) . ?
C6 C5 1.4640(18) . ?
C6 C11 1.4047(17) . ?
C6 C7 1.4052(18) . ?
C5 H5 0.9300 . ?
C13A H13A 0.9300 . ?
C13A C14A 1.3915(18) . ?
C3A C4A 1.4839(18) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.3386(18) . ?
C19 H19 0.9300 . ?
C19 C20 1.3940(18) . ?
C3 C2 1.4814(17) . ?
C17 H17 0.9300 . ?
C17 C16 1.3872(18) . ?
C17A H17A 0.9300 . ?
C17A C16A 1.3906(19) . ?
C2 H2 0.9300 . ?
C6A C5A 1.4669(18) . ?
C6A C11A 1.4018(18) . ?
C6A C7A 1.4054(18) . ?
C5A H5A 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.3905(18) . ?
C7 H7 0.9300 . ?
C7 C8 1.3850(19) . ?
C23 H23 0.9300 . ?
C23 C22 1.3893(19) . ?
C10 H10 0.9300 . ?
C10 C9 1.3786(19) . ?
C23A H23A 0.9300 . ?
C23A C22A 1.3898(19) . ?
C11A H11A 0.9300 . ?
C11A C10A 1.3889(19) . ?
C10A H10A 0.9300 . ?
C10A C9A 1.379(2) . ?
C20A H20A 0.9300 . ?
C20A C21A 1.3921(19) . ?
C21A H21A 0.9300 . ?
C21A C22A 1.393(2) . ?
C9 C8 1.3836(19) . ?
C13 H13 0.9300 . ?
C13 C14 1.3934(18) . ?
C16A H16A 0.9300 . ?
C16A C15A 1.391(2) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.3867(19) . ?
C22 H22 0.9300 . ?
C22 C21 1.392(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.390(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.393(2) . ?
C22A H22A 0.9300 . ?
C8 H8 0.9300 . ?
C14 H14 0.9300 . ?
C9A C8A 1.3845(19) . ?
C20 H20 0.9300 . ?
C20 C21 1.390(2) . ?
C15A H15A 0.9300 . ?
C15A C14A 1.389(2) . ?
C8A H8A 0.9300 . ?
C14A H14A 0.9300 . ?
C21 H21 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
C17 C12 C1 121.09(11) . . ?
C13 C12 C1 120.62(11) . . ?
C13 C12 C17 118.26(11) . . ?
C19 C18 C1 121.72(11) . . ?
C19 C18 C23 119.21(12) . . ?
C23 C18 C1 119.06(11) . . ?
C13A C12A C1A 119.95(11) . . ?
C13A C12A C17A 118.35(12) . . ?
C17A C12A C1A 121.69(11) . . ?
C19A C18A C1A 119.05(11) . . ?
C19A C18A C23A 118.95(11) . . ?
C23A C18A C1A 122.00(11) . . ?
C18A C19A H19A 119.7 . . ?
C20A C19A C18A 120.68(11) . . ?
C20A C19A H19A 119.7 . . ?
C1A C2A H2A 114.9 . . ?
C1A C2A C3A 130.19(12) . . ?
C3A C2A H2A 114.9 . . ?
C12A C1A C18A 115.62(10) . . ?
C2A C1A C12A 120.04(11) . . ?
C2A C1A C18A 124.31(11) . . ?
C12 C1 C18 116.45(10) . . ?
C2 C1 C12 119.49(11) . . ?
C2 C1 C18 124.02(11) . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C3 120.23(11) . . ?
C3 C4 H4 119.9 . . ?
C11 C6 C5 118.74(11) . . ?
C11 C6 C7 118.36(12) . . ?
C7 C6 C5 122.81(11) . . ?
C4 C5 C6 126.70(12) . . ?
C4 C5 H5 116.6 . . ?
C6 C5 H5 116.6 . . ?
C12A C13A H13A 119.6 . . ?
C14A C13A C12A 120.71(12) . . ?
C14A C13A H13A 119.6 . . ?
O12 C3A C2A 117.75(12) . . ?
O12 C3A C4A 120.51(11) . . ?
C2A C3A C4A 121.74(11) . . ?
C3A C4A H4A 119.6 . . ?
C5A C4A C3A 120.74(12) . . ?
C5A C4A H4A 119.6 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.29(12) . . ?
C20 C19 H19 119.9 . . ?
O37 C3 C4 121.05(11) . . ?
O37 C3 C2 117.17(11) . . ?
C4 C3 C2 121.79(11) . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.72(12) . . ?
C16 C17 H17 119.6 . . ?
C12A C17A H17A 119.7 . . ?
C16A C17A C12A 120.63(12) . . ?
C16A C17A H17A 119.7 . . ?
C1 C2 C3 129.65(12) . . ?
C1 C2 H2 115.2 . . ?
C3 C2 H2 115.2 . . ?
C11A C6A C5A 119.13(12) . . ?
C11A C6A C7A 118.30(12) . . ?
C7A C6A C5A 122.51(11) . . ?
C4A C5A C6A 127.27(12) . . ?
C4A C5A H5A 116.4 . . ?
C6A C5A H5A 116.4 . . ?
C6 C11 H11 119.3 . . ?
C10 C11 C6 121.47(12) . . ?
C10 C11 H11 119.3 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.86(12) . . ?
C8 C7 H7 119.6 . . ?
C18 C23 H23 119.9 . . ?
C22 C23 C18 120.26(12) . . ?
C22 C23 H23 119.9 . . ?
C11 C10 H10 121.2 . . ?
C9 C10 C11 117.69(12) . . ?
C9 C10 H10 121.2 . . ?
C18A C23A H23A 119.9 . . ?
C22A C23A C18A 120.19(12) . . ?
C22A C23A H23A 119.9 . . ?
C6A C11A H11A 119.3 . . ?
C10A C11A C6A 121.48(12) . . ?
C10A C11A H11A 119.3 . . ?
C11A C10A H10A 121.0 . . ?
C9A C10A C11A 118.00(12) . . ?
C9A C10A H10A 121.0 . . ?
C19A C20A H20A 120.0 . . ?
C19A C20A C21A 119.93(12) . . ?
C21A C20A H20A 120.0 . . ?
C20A C21A H21A 120.1 . . ?
C20A C21A C22A 119.70(12) . . ?
C22A C21A H21A 120.1 . . ?
F50 C9 C10 118.63(12) . . ?
F50 C9 C8 118.18(12) . . ?
C10 C9 C8 123.19(12) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.82(12) . . ?
C14 C13 H13 119.6 . . ?
C17A C16A H16A 119.8 . . ?
C17A C16A C15A 120.35(12) . . ?
C15A C16A H16A 119.8 . . ?
C6A C7A H7A 119.5 . . ?
C8A C7A C6A 120.92(12) . . ?
C8A C7A H7A 119.5 . . ?
C23 C22 H22 119.9 . . ?
C23 C22 C21 120.28(13) . . ?
C21 C22 H22 119.9 . . ?
C17 C16 H16 119.8 . . ?
C17 C16 C15 120.45(12) . . ?
C15 C16 H16 119.8 . . ?
C16 C15 H15 120.2 . . ?
C16 C15 C14 119.63(12) . . ?
C14 C15 H15 120.2 . . ?
C23A C22A C21A 120.48(12) . . ?
C23A C22A H22A 119.8 . . ?
C21A C22A H22A 119.8 . . ?
C7 C8 H8 120.8 . . ?
C9 C8 C7 118.43(12) . . ?
C9 C8 H8 120.8 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.08(13) . . ?
C15 C14 H14 120.0 . . ?
F25 C9A C10A 118.71(12) . . ?
F25 C9A C8A 118.42(12) . . ?
C10A C9A C8A 122.86(13) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.14(13) . . ?
C21 C20 H20 119.9 . . ?
C16A C15A H15A 120.2 . . ?
C14A C15A C16A 119.55(12) . . ?
C14A C15A H15A 120.2 . . ?
C7A C8A H8A 120.8 . . ?
C9A C8A C7A 118.44(13) . . ?
C9A C8A H8A 120.8 . . ?
C13A C14A H14A 119.8 . . ?
C15A C14A C13A 120.39(13) . . ?
C15A C14A H14A 119.8 . . ?
C22 C21 H21 120.1 . . ?
C20 C21 C22 119.74(13) . . ?
C20 C21 H21 120.1 . . ?

_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 1.731
_oxdiff_exptl_absorpt_empirical_full_min 0.493
####################################################################### 
# 
# 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_7072-8496_vasilev073
_database_code_depnum_ccdc_archive 'CCDC 1847451'
_audit_update_record             
;
2018-06-05 deposited with the CCDC.
2018-10-03 downloaded from the CCDC.
;
_audit_creation_date             2018-01-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 F O'
_chemical_formula_sum            'C23 H17 F O'
_chemical_formula_weight         328.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H17 F O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.47709(19)
_cell_length_b                   19.3161(4)
_cell_length_c                   10.6412(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.210(2)
_cell_angle_gamma                90
_cell_volume                     1732.22(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8068
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.5430
_cell_measurement_theta_min      3.1730
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            30881
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.637
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -93.00   -4.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -77.0000  120.0000 89

#__ type_ start__ end____ width___ exp.time_
  2 omega  -78.00  -50.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -      -22.4241 -178.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -87.00  -55.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -57.0000 -150.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega  -45.00   39.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -57.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega   63.00   89.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -       23.3616   57.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   38.00   64.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -       23.3616  178.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega  -18.00    8.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -57.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   10.00   89.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -       23.3616   57.0000  -30.0000 79

#__ type_ start__ end____ width___ exp.time_
  9 omega   -5.00   39.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000   90.0000 44

#__ type_ start__ end____ width___ exp.time_
 10 omega  -52.00    7.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -77.0000 -150.0000 59

#__ type_ start__ end____ width___ exp.time_
 11 omega  -52.00  -27.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   77.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega   18.00   44.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega  -14.00   25.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -       23.3616   19.0000    0.0000 39

#__ type_ start__ end____ width___ exp.time_
 14 omega  -46.00   46.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   38.0000  150.0000 92

#__ type_ start__ end____ width___ exp.time_
 15 omega   65.00   92.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -       23.3616   57.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 16 omega  -25.00   65.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000  -90.0000 90

#__ type_ start__ end____ width___ exp.time_
 17 omega    3.00   28.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -       23.3616   57.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega   -5.00   21.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   55.00   81.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   47.00   83.00   1.0000   14.7100
omega____ theta____ kappa____ phi______ frames
    -       23.3616 -129.0000  162.2029 36
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0149797000
_diffrn_orient_matrix_UB_12      0.0162310000
_diffrn_orient_matrix_UB_13      0.0598922000
_diffrn_orient_matrix_UB_21      0.0664001000
_diffrn_orient_matrix_UB_22      -0.0219569000
_diffrn_orient_matrix_UB_23      0.0150997000
_diffrn_orient_matrix_UB_31      0.0494642000
_diffrn_orient_matrix_UB_32      0.0245686000
_diffrn_orient_matrix_UB_33      -0.0260833000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3446
_reflns_number_total             3969
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3969
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.032
_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)+(0.0457P)²+0.6189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1018
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22),
  C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.10616(11) 0.59106(4) 0.50474(8) 0.0412(2) Uani 1 1 d . . . . .
O2 O 0.10749(10) 0.47071(4) 0.16102(8) 0.0253(2) Uani 1 1 d . . . . .
C1 C 0.41174(13) 0.62626(6) 0.05419(10) 0.0171(2) Uani 1 1 d . . . . .
C2 C 0.37535(13) 0.57386(5) -0.16590(10) 0.0180(2) Uani 1 1 d . . . . .
C3 C 0.33248(12) 0.57436(5) -0.03431(10) 0.0166(2) Uani 1 1 d . . . . .
C4 C 0.15292(13) 0.52619(6) 0.12100(11) 0.0195(2) Uani 1 1 d . . . . .
C5 C 0.48653(13) 0.60610(6) 0.17187(11) 0.0205(2) Uani 1 1 d . . . . .
H5 H 0.4899 0.5585 0.1948 0.025 Uiso 1 1 calc R . . . .
C6 C 0.22768(13) 0.52768(6) 0.00155(11) 0.0187(2) Uani 1 1 d . . . . .
H6 H 0.1984 0.4915 -0.0568 0.022 Uiso 1 1 calc R . . . .
C7 C 0.53132(14) 0.58696(6) -0.19070(11) 0.0207(2) Uani 1 1 d . . . . .
H7 H 0.6094 0.5989 -0.1233 0.025 Uiso 1 1 calc R . . . .
C8 C 0.11939(13) 0.59297(6) 0.18225(11) 0.0204(2) Uani 1 1 d . . . . .
H8 H 0.1446 0.6350 0.1427 0.024 Uiso 1 1 calc R . . . .
C9 C 0.00958(13) 0.65882(6) 0.35420(11) 0.0228(2) Uani 1 1 d . . . . .
C10 C 0.05485(13) 0.59553(6) 0.29123(11) 0.0218(2) Uani 1 1 d . . . . .
H10 H 0.0368 0.5527 0.3313 0.026 Uiso 1 1 calc R . . . .
C11 C 0.57263(16) 0.58261(6) -0.31314(12) 0.0267(3) Uani 1 1 d . . . . .
H11 H 0.6796 0.5899 -0.3289 0.032 Uiso 1 1 calc R . . . .
C12 C 0.40956(14) 0.69635(6) 0.02118(11) 0.0224(2) Uani 1 1 d . . . . .
H12 H 0.3625 0.7105 -0.0598 0.027 Uiso 1 1 calc R . . . .
C13 C 0.26083(15) 0.55867(6) -0.26678(11) 0.0232(3) Uani 1 1 d . . . . .
H13 H 0.1542 0.5503 -0.2514 0.028 Uiso 1 1 calc R . . . .
C14 C 0.55622(15) 0.65537(7) 0.25581(12) 0.0255(3) Uani 1 1 d . . . . .
H14 H 0.6083 0.6413 0.3352 0.031 Uiso 1 1 calc R . . . .
C15 C 0.45819(18) 0.56764(6) -0.41240(12) 0.0302(3) Uani 1 1 d . . . . .
H15 H 0.4864 0.5655 -0.4963 0.036 Uiso 1 1 calc R . . . .
C16 C 0.47608(16) 0.74528(6) 0.10676(13) 0.0296(3) Uani 1 1 d . . . . .
H16 H 0.4711 0.7930 0.0851 0.036 Uiso 1 1 calc R . . . .
C17 C -0.07380(15) 0.65490(7) 0.45987(12) 0.0291(3) Uani 1 1 d . . . . .
C18 C 0.54970(16) 0.72498(7) 0.22359(13) 0.0288(3) Uani 1 1 d . . . . .
H18 H 0.5956 0.7587 0.2815 0.035 Uiso 1 1 calc R . . . .
C19 C 0.04131(15) 0.72597(7) 0.31286(12) 0.0280(3) Uani 1 1 d . . . . .
H19 H 0.1012 0.7317 0.2431 0.034 Uiso 1 1 calc R . . . .
C20 C 0.30258(17) 0.55584(6) -0.38938(12) 0.0293(3) Uani 1 1 d . . . . .
H20 H 0.2242 0.5458 -0.4577 0.035 Uiso 1 1 calc R . . . .
C21 C -0.12872(16) 0.71170(8) 0.52002(13) 0.0357(3) Uani 1 1 d . . . . .
H21 H -0.1860 0.7062 0.5913 0.043 Uiso 1 1 calc R . . . .
C22 C -0.09884(16) 0.77688(8) 0.47448(14) 0.0362(3) Uani 1 1 d . . . . .
H22 H -0.1373 0.8167 0.5137 0.043 Uiso 1 1 calc R . . . .
C23 C -0.01277(17) 0.78418(7) 0.37163(13) 0.0342(3) Uani 1 1 d . . . . .
H23 H 0.0092 0.8290 0.3414 0.041 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 C17 1.3609(16) . ?
O2 C4 1.2304(14) . ?
C1 C3 1.4854(15) . ?
C1 C5 1.3965(16) . ?
C1 C12 1.3984(15) . ?
C2 C3 1.4842(15) . ?
C2 C7 1.3990(16) . ?
C2 C13 1.3984(16) . ?
C3 C6 1.3496(15) . ?
C4 C6 1.4807(15) . ?
C4 C8 1.4865(16) . ?
C5 C14 1.3923(16) . ?
C7 C11 1.3878(17) . ?
C8 C10 1.3357(16) . ?
C9 C10 1.4650(17) . ?
C9 C17 1.3934(17) . ?
C9 C19 1.4051(18) . ?
C11 C15 1.385(2) . ?
C12 C16 1.3891(17) . ?
C13 C20 1.3893(17) . ?
C14 C18 1.3872(18) . ?
C15 C20 1.386(2) . ?
C16 C18 1.386(2) . ?
C17 C21 1.3764(19) . ?
C19 C23 1.3883(19) . ?
C21 C22 1.382(2) . ?
C22 C23 1.387(2) . ?

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 C1 C3 120.71(10) . . ?
C5 C1 C12 119.19(10) . . ?
C12 C1 C3 120.08(10) . . ?
C7 C2 C3 120.64(10) . . ?
C13 C2 C3 120.34(10) . . ?
C13 C2 C7 119.00(11) . . ?
C2 C3 C1 117.54(9) . . ?
C6 C3 C1 122.56(10) . . ?
C6 C3 C2 119.88(10) . . ?
O2 C4 C6 119.54(10) . . ?
O2 C4 C8 121.48(10) . . ?
C6 C4 C8 118.65(10) . . ?
C14 C5 C1 120.30(11) . . ?
C3 C6 C4 127.71(10) . . ?
C11 C7 C2 120.39(12) . . ?
C10 C8 C4 121.91(11) . . ?
C17 C9 C10 120.31(11) . . ?
C17 C9 C19 115.71(11) . . ?
C19 C9 C10 123.96(11) . . ?
C8 C10 C9 125.47(11) . . ?
C15 C11 C7 120.10(12) . . ?
C16 C12 C1 120.04(11) . . ?
C20 C13 C2 120.19(12) . . ?
C18 C14 C5 120.08(12) . . ?
C11 C15 C20 120.06(11) . . ?
C18 C16 C12 120.47(12) . . ?
F1 C17 C9 118.12(11) . . ?
F1 C17 C21 117.90(12) . . ?
C21 C17 C9 123.96(13) . . ?
C16 C18 C14 119.86(11) . . ?
C23 C19 C9 121.53(12) . . ?
C15 C20 C13 120.22(12) . . ?
C17 C21 C22 118.62(13) . . ?
C21 C22 C23 120.09(13) . . ?
C22 C23 C19 120.05(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_9176_z-6
_database_code_depnum_ccdc_archive 'CCDC 1847454'
_audit_update_record             
;
2018-06-05 deposited with the CCDC.
2018-10-03 downloaded from the CCDC.
;
_audit_creation_date             2018-04-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 O S'
_chemical_formula_sum            'C21 H16 O S'
_chemical_formula_weight         316.40
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 O S'
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   7.6982(5)
_cell_length_b                   12.0382(7)
_cell_length_c                   17.5134(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1623.01(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5137
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.6020
_cell_measurement_theta_min      4.3850
_shelx_estimated_absorpt_T_max   0.777
_shelx_estimated_absorpt_T_min   0.708
_exptl_absorpt_coefficient_mu    1.768
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11405
_diffrn_reflns_point_group_measured_fraction_full 0.928
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.940
_diffrn_reflns_theta_min         4.457
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -95.00 -49.00   0.50    2.01    --  -41.35 -50.00 -34.00   92
  2  ω     -7.00  18.00   0.50    2.01    --  -41.35  95.00 -26.00   50
  3  ω    -61.00 -36.00   0.50    2.01    --  -41.35  95.00 -26.00   50
  4  ω    -23.00  19.00   0.50    2.01    --  -41.35  50.00 111.00   84
  5  ω     21.00  46.00   0.50    2.01    --   41.35 -82.00 114.00   50
  6  ω     53.00  78.00   0.50    2.01    --   41.35  50.00 111.00   50
  7  ω      4.00  33.00   0.50    2.01    --   41.35 -95.00-137.00   58
  8  ω    -16.00   9.00   0.50    2.01    --   41.35 -50.00 -34.00   50
  9  ω     99.00 125.00   0.50    8.05    --  101.00  50.00 111.00   52
 10  ω    118.00 151.00   0.50    8.05    --  101.00  82.00-123.00   66
 11  ω    111.00 155.00   0.50    8.05    --  101.00  95.00 -26.00   88
 12  ω     46.00  72.00   0.50    8.05    --  101.00 -95.00-137.00   52
 13  ω     74.00  99.00   0.50    8.05    --  101.00 -82.00 114.00   50
 14  ω     40.00 115.00   0.50    8.05    --  101.00 -50.00 -34.00  150
 15  ω    -93.00 -35.00   0.50    2.01    --  -41.35 -32.00-180.00  116
 16  ω    -58.00  22.00   0.50    2.01    --  -41.35  65.00 150.00  160
 17  ω    -23.00   2.00   0.50    2.01    --  -41.35  82.00-123.00   50
 18  ω     46.00 105.00   0.50    2.01    --   41.35  32.00-180.00  118
 19  ω    107.00 157.00   0.50    8.05    --  101.00  33.00-120.00  100
 20  ω     88.00 153.00   0.50    8.05    --  101.00  42.00 150.00  130
 21  ω     84.00 120.00   0.50    8.05    --  101.00 -59.00-120.00   72
 22  ω     37.00 115.00   0.50    8.05    --  101.00 -68.00-150.00  156
 23  ω     39.00  69.00   0.50    8.05    --  101.00 -87.00  30.00   60
 24  ω     83.00 126.00   0.50    8.05    --  101.00 -87.00  30.00   86
 25  ω     43.00  78.00   0.50    8.05    --  101.00 -59.00-120.00   70
 26  ω    107.00 132.00   0.50    8.05    --  101.00  17.00  60.00   50
 27  ω     70.00  95.00   0.50    8.05    --  101.00 -95.00-137.00   50
 28  ω     39.00  65.00   0.50    2.01    --   41.35  32.00-150.00   52
 29  ω     99.00 152.00   0.50    8.05    --  101.00  33.00  30.00  106
 30  ω    118.00 147.00   0.50    8.05    --  101.00 178.00-120.00   58
 31  ω     87.00 113.00   0.50    8.05    --  101.00-111.00 -30.00   52
 32  ω     64.00 113.00   0.50    8.05    --  101.00-133.00 150.00   98
 33  ω     38.00  91.00   0.50    8.05    --  101.00 178.00-120.00  106
 34  ω     35.00  60.00   0.50    8.05    --  101.00-111.00 -30.00   50
 35  ω    128.00 157.00   0.50    8.05    --  101.00  93.00 -30.00   58
 36  ω     48.00  83.00   0.50    8.05    --  101.00 -25.00 150.00   70
 37  ω     85.00 111.00   0.50    8.05    --  101.00  59.00-120.00   52
 38  ω     49.00 108.00   0.50    8.05    --  101.00 -25.00 -30.00  118
 39  ω    -67.00 -37.00   0.50    2.01    --  -41.35  82.00-123.00   60
 40  ω    -74.00 -31.00   0.50    2.01    --  -41.35 104.00 120.00   86
 41  ω    -46.00 -20.00   0.50    2.01    --  -41.35  21.00 150.00   52
 42  ω    -12.00  14.00   0.50    2.01    --  -41.35 104.00 120.00   52
 43  ω    -57.00 -15.00   0.50    2.01    --  -41.35  54.00  90.00   84
 44  ω     -1.00  24.00   0.50    2.01    --  -41.35  82.00-123.00   50
 45  ω     -5.00  27.00   0.50    2.01    --  -41.35  21.00 150.00   64
 46  ω      8.00  54.00   0.50    2.01    --   41.35 -43.00 -30.00   92
 47  ω     54.00  91.00   0.50    2.01    --   41.35-138.00  30.00   74
 48  ω     25.00  75.00   0.50    2.01    --   41.35  54.00 -60.00  100
 49  ω     25.00  70.00   0.50    2.01    --   41.35-104.00 -60.00   90
 50  ω     87.00 113.00   0.50    8.05    --  101.00  17.00 -60.00   52
 51  ω     86.00 111.00   0.50    8.05    --  101.00 -42.00 150.00   50
 52  ω     53.00  87.00   0.50    8.05    --  101.00 -68.00  60.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0959826000
_diffrn_orient_matrix_UB_12      0.0175744000
_diffrn_orient_matrix_UB_13      0.0762494000
_diffrn_orient_matrix_UB_21      -0.0766195000
_diffrn_orient_matrix_UB_22      -0.1179171000
_diffrn_orient_matrix_UB_23      -0.0057144000
_diffrn_orient_matrix_UB_31      0.1582046000
_diffrn_orient_matrix_UB_32      -0.0463580000
_diffrn_orient_matrix_UB_33      0.0434245000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.850
_reflns_Friedel_fraction_max     0.829
_reflns_number_gt                2681
_reflns_number_total             2925
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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         0.494
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 1027 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.30(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2925
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.041
_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)+(0.0405P)²+1.4819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1205
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Shared sites
{S1A, C10}
{S1, C7}
3. Restrained distances
 C6-S1A
 1.65 with sigma of 0.00002
4. Others
 Sof(S1)=Sof(H8A)=Sof(H8B)=Sof(C10)=Sof(H7)=1-FVAR(1)
 Sof(S1A)=Sof(H9A)=Sof(H9B)=Sof(H10)=Sof(C7)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C16(H16), C13(H13), C15(H15), C14(H14), C2(H2), C18(H18),
 C12(H12), C22(H22), C19(H19), C21(H21), C20(H20), C8(H8A), C8(H8B), C9(H9A),
 C9(H9B), C10(H10), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.76978(16) 0.55652(7) 0.71253(11) 0.0377(18) Uiso 0.596(5) 1 d D . P A 3
S1 S 0.6299(3) 0.72540(17) 0.79075(17) 0.035(2) Uiso 0.404(5) 1 d . . P A 5
O1 O 0.6259(4) 0.8806(2) 0.5092(2) 0.0406(8) Uani 1 1 d . . . . .
C3 C 0.6793(5) 0.7841(3) 0.5014(3) 0.0303(9) Uani 1 1 d . . . . .
C5 C 0.6496(5) 0.7416(4) 0.6377(3) 0.0298(9) Uani 1 1 d . . . . .
H5 H 0.5796 0.8064 0.6406 0.036 Uiso 1 1 calc R . . . .
C4 C 0.7147(5) 0.7144(3) 0.5691(3) 0.0280(9) Uani 1 1 d . . . . .
H4 H 0.7842 0.6497 0.5640 0.034 Uiso 1 1 calc R . . . .
C16 C 0.7072(5) 0.5359(4) 0.2719(3) 0.0283(9) Uani 1 1 d . . . . .
H16 H 0.6304 0.4857 0.2966 0.034 Uiso 1 1 calc R . . . .
C17 C 0.7102(5) 0.5370(3) 0.4414(3) 0.0258(8) Uani 1 1 d . . . . .
C1 C 0.7324(5) 0.6406(3) 0.3950(3) 0.0267(9) Uani 1 1 d . . . . .
C13 C 0.9359(5) 0.6791(4) 0.1992(3) 0.0365(11) Uani 1 1 d . . . . .
H13 H 1.0150 0.7279 0.1745 0.044 Uiso 1 1 calc R . . . .
C15 C 0.7478(5) 0.5208(4) 0.1951(3) 0.0314(10) Uani 1 1 d . . . . .
H15 H 0.6954 0.4619 0.1672 0.038 Uiso 1 1 calc R . . . .
C6 C 0.6775(2) 0.68005(8) 0.70780(19) 0.0321(9) Uani 1 1 d D . . . .
C14 C 0.8638(6) 0.5910(4) 0.1592(3) 0.0355(10) Uani 1 1 d . . . . .
H14 H 0.8941 0.5790 0.1073 0.043 Uiso 1 1 calc R . . . .
C2 C 0.7137(6) 0.7442(4) 0.4238(3) 0.0312(9) Uani 1 1 d . . . . .
H2 H 0.7249 0.8017 0.3870 0.037 Uiso 1 1 calc R . . . .
C11 C 0.7786(5) 0.6245(3) 0.3127(3) 0.0277(9) Uani 1 1 d . . . . .
C18 C 0.8425(6) 0.4580(3) 0.4408(3) 0.0292(9) Uani 1 1 d . . . . .
H18 H 0.9414 0.4693 0.4093 0.035 Uiso 1 1 calc R . . . .
C12 C 0.8925(6) 0.6961(4) 0.2753(3) 0.0340(11) Uani 1 1 d . . . . .
H12 H 0.9410 0.7573 0.3021 0.041 Uiso 1 1 calc R . . . .
C22 C 0.5630(6) 0.5163(4) 0.4849(3) 0.0356(10) Uani 1 1 d . . . . .
H22 H 0.4690 0.5674 0.4846 0.043 Uiso 1 1 calc R . . . .
C19 C 0.8320(7) 0.3630(4) 0.4855(3) 0.0386(11) Uani 1 1 d . . . . .
H19 H 0.9243 0.3106 0.4853 0.046 Uiso 1 1 calc R . . . .
C21 C 0.5538(8) 0.4194(4) 0.5291(3) 0.0485(14) Uani 1 1 d . . . . .
H21 H 0.4532 0.4052 0.5590 0.058 Uiso 1 1 calc R . . . .
C20 C 0.6884(8) 0.3451(4) 0.5297(3) 0.0447(13) Uani 1 1 d . . . . .
H20 H 0.6820 0.2808 0.5610 0.054 Uiso 1 1 calc R . . . .
C8 C 0.6904(8) 0.6321(5) 0.8390(4) 0.0602(17) Uani 1 1 d . . . . .
H8A H 0.6780 0.6327 0.8929 0.072 Uiso 0.404(5) 1 calc R . P A 5
H8B H 0.6780 0.6327 0.8929 0.072 Uiso 0.404(5) 1 calc R . P A 6
C9 C 0.7644(7) 0.5456(5) 0.8015(4) 0.0583(18) Uani 1 1 d . . . . .
H9A H 0.8100 0.4828 0.8275 0.070 Uiso 0.596(5) 1 calc R . P A 3
H9B H 0.8100 0.4828 0.8275 0.070 Uiso 0.596(5) 1 calc R . P A 4
C10 C 0.76978(16) 0.55652(7) 0.71253(11) 0.035(10) Uiso 0.404(5) 1 d . . P A 4
H10 H 0.8121 0.5081 0.6740 0.042 Uiso 0.596(5) 1 calc R . P A 4
C7 C 0.6299(3) 0.72540(17) 0.79075(17) 0.041(7) Uiso 0.596(5) 1 d . . P A 6
H7 H 0.5773 0.7936 0.8052 0.049 Uiso 0.404(5) 1 calc R . P A 6


_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
S1A C6 1.65000(8) . ?
S1A C9 1.565(7) . ?
S1 C6 1.595(5) . ?
S1 C8 1.481(7) . ?
O1 C3 1.240(5) . ?
C3 C4 1.477(6) . ?
C3 C2 1.465(7) . ?
C5 H5 0.9500 . ?
C5 C4 1.343(6) . ?
C5 C6 1.450(6) . ?
C4 H4 0.9500 . ?
C16 H16 0.9500 . ?
C16 C15 1.393(7) . ?
C16 C11 1.397(6) . ?
C17 C1 1.498(6) . ?
C17 C18 1.393(6) . ?
C17 C22 1.388(6) . ?
C1 C2 1.353(6) . ?
C1 C11 1.497(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(7) . ?
C13 C12 1.389(7) . ?
C15 H15 0.9500 . ?
C15 C14 1.381(6) . ?
C6 C10 1.65000(8) . ?
C6 C7 1.595(5) . ?
C14 H14 0.9500 . ?
C2 H2 0.9500 . ?
C11 C12 1.394(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.388(6) . ?
C12 H12 0.9500 . ?
C22 H22 0.9500 . ?
C22 C21 1.402(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.366(8) . ?
C21 H21 0.9500 . ?
C21 C20 1.369(8) . ?
C20 H20 0.9500 . ?
C8 H8A 0.9500 . ?
C8 H8B 0.9500 . ?
C8 C9 1.355(9) . ?
C8 C7 1.481(7) . ?
C9 H9A 0.9500 . ?
C9 H9B 0.9500 . ?
C9 C10 1.565(7) . ?
C10 H10 0.9500 . ?
C7 H7 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
C9 S1A C6 96.6(3) . . ?
C8 S1 C6 100.8(3) . . ?
O1 C3 C4 120.3(4) . . ?
O1 C3 C2 118.0(4) . . ?
C2 C3 C4 121.7(4) . . ?
C4 C5 H5 117.3 . . ?
C4 C5 C6 125.3(4) . . ?
C6 C5 H5 117.3 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C11 120.4(4) . . ?
C11 C16 H16 119.8 . . ?
C18 C17 C1 118.8(4) . . ?
C22 C17 C1 122.7(4) . . ?
C22 C17 C18 118.5(4) . . ?
C2 C1 C17 123.6(4) . . ?
C2 C1 C11 120.2(4) . . ?
C11 C1 C17 116.2(4) . . ?
C14 C13 H13 120.0 . . ?
C14 C13 C12 120.0(4) . . ?
C12 C13 H13 120.0 . . ?
C16 C15 H15 119.9 . . ?
C14 C15 C16 120.3(4) . . ?
C14 C15 H15 119.9 . . ?
C5 C6 S1A 124.5(3) . . ?
C5 C6 S1 124.22(19) . . ?
C5 C6 C10 124.5(3) . . ?
C5 C6 C7 124.22(19) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.9(5) . . ?
C15 C14 H14 120.1 . . ?
C3 C2 H2 114.1 . . ?
C1 C2 C3 131.8(4) . . ?
C1 C2 H2 114.1 . . ?
C16 C11 C1 119.9(4) . . ?
C12 C11 C16 118.6(4) . . ?
C12 C11 C1 121.5(4) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.0(4) . . ?
C19 C18 H18 119.5 . . ?
C13 C12 C11 120.8(4) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C17 C22 H22 120.2 . . ?
C17 C22 C21 119.6(5) . . ?
C21 C22 H22 120.2 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.8(5) . . ?
C20 C19 H19 120.1 . . ?
C22 C21 H21 119.7 . . ?
C20 C21 C22 120.6(5) . . ?
C20 C21 H21 119.7 . . ?
C19 C20 C21 120.3(5) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
S1 C8 H8A 122.0 . . ?
C9 C8 S1 116.0(5) . . ?
C9 C8 H8A 122.0 . . ?
C9 C8 H8B 122.0 . . ?
C9 C8 C7 116.0(5) . . ?
C7 C8 H8B 122.0 . . ?
S1A C9 H9A 122.3 . . ?
C8 C9 S1A 115.4(5) . . ?
C8 C9 H9A 122.3 . . ?
C8 C9 H9B 122.3 . . ?
C8 C9 C10 115.4(5) . . ?
C10 C9 H9B 122.3 . . ?
C6 C10 H10 131.7 . . ?
C9 C10 C6 96.6(3) . . ?
C9 C10 H10 131.7 . . ?
C6 C7 H7 129.6 . . ?
C8 C7 C6 100.8(3) . . ?
C8 C7 H7 129.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.330
_oxdiff_exptl_absorpt_empirical_full_min 0.545
####################################################################### 
# 
# 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_7071-8325_ima063
_database_code_depnum_ccdc_archive 'CCDC 1847452'
_audit_update_record             
;
2018-06-05 deposited with the CCDC.
2018-10-03 downloaded from the CCDC.
;
_audit_creation_date             2017-12-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 O'
_chemical_formula_sum            'C23 H18 O'
_chemical_formula_weight         310.37
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20
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'

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

_cell_length_a                   7.75140(10)
_cell_length_b                   12.0257(2)
_cell_length_c                   17.7094(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1650.80(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8400
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.4440
_cell_measurement_theta_min      4.3960
_shelx_estimated_absorpt_T_max   0.893
_shelx_estimated_absorpt_T_min   0.893
_exptl_absorpt_coefficient_mu    0.578
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14542
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.960
_diffrn_reflns_theta_min         4.444
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 -23.00   1.00    1.00    --  -40.38 -38.00 -30.00   46
  2  ω   -116.00 -28.00   1.00    1.00    --  -40.38 -38.00 120.00   88
  3  ω     94.00 128.00   1.00    1.00    --   40.38 178.00-120.00   34
  4  ω     94.00 119.00   1.00    1.00    --   40.38 178.00   0.00   25
  5  ω     38.00 173.00   1.00    1.00    --  113.00   0.00-180.00  135
  6  ω     76.00 103.00   1.00    1.00    --  113.00 -95.00 -60.00   27
  7  ω     68.00 107.00   1.00    1.00    --  113.00 -95.00  30.00   39
  8  ω     36.00  63.00   1.00    1.00    --  113.00 -95.00 -60.00   27
  9  ω     30.00  82.00   1.00    1.00    --  113.00 -95.00   0.00   52
 10  ω     35.00  62.00   1.00    1.00    --  113.00 -95.00  30.00   27
 11  ω     63.00 113.00   1.00    1.00    --   40.38 178.00  30.00   50
 12  ω     63.00 105.00   1.00    1.00    --  113.00 -95.00 120.00   42
 13  ω     41.00  68.00   1.00    1.00    --  113.00 -95.00-150.00   27
 14  ω     81.00 107.00   1.00    1.00    --  113.00 -95.00-150.00   26
 15  ω     75.00 101.00   1.00    1.00    --  113.00 -95.00  60.00   26
 16  ω     49.00 115.00   1.00    1.00    --  113.00 -45.00 -30.00   66
 17  ω     99.00 139.00   1.00    1.00    --  113.00 -15.00  90.00   40
 18  ω    -97.00 -45.00   1.00    1.00    --  -40.38 178.00-120.00   52
 19  ω    -74.00  31.00   1.00    1.00    --  -40.38  19.00 -60.00  105
 20  ω     65.00 125.00   1.00    1.00    --   40.38 178.00-180.00   60
 21  ω     45.00 143.00   1.00    1.00    --  113.00 -61.00 120.00   98
 22  ω    141.00 177.00   1.00    1.00    --  113.00  61.00-180.00   36
 23  ω     60.00 112.00   1.00    1.00    --  113.00 -45.00  30.00   52
 24  ω     92.00 136.00   1.00    1.00    --  113.00  61.00-180.00   44
 25  ω     98.00 125.00   1.00    1.00    --  113.00  45.00 150.00   27
 26  ω     66.00 115.00   1.00    1.00    --  113.00-112.00 -90.00   49
 27  ω     93.00 142.00   1.00    1.00    --  113.00 -30.00 150.00   49
 28  ω    105.00 134.00   1.00    1.00    --  113.00 112.00-150.00   29
 29  ω    148.00 174.00   1.00    1.00    --  113.00 112.00-150.00   26
 30  ω     43.00  69.00   1.00    1.00    --  113.00-112.00  30.00   26
 31  ω     79.00 115.00   1.00    1.00    --  113.00-112.00  30.00   36
 32  ω     53.00  79.00   1.00    1.00    --  113.00 -30.00 150.00   26
 33  ω     30.00  69.00   1.00    1.00    --  113.00 -95.00 -30.00   39
 34  ω     41.00  91.00   1.00    1.00    --  113.00 -61.00-120.00   50
 35  ω    144.00 176.00   1.00    1.00    --  113.00  45.00 150.00   32
 36  ω     91.00 117.00   1.00    1.00    --  113.00-114.00 152.12   26
 37  ω     -3.00  22.00   1.00    1.00    --   36.00  91.00  95.45   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0373991000
_diffrn_orient_matrix_UB_12      0.1237927000
_diffrn_orient_matrix_UB_13      0.0148332000
_diffrn_orient_matrix_UB_21      0.0406522000
_diffrn_orient_matrix_UB_22      0.0266922000
_diffrn_orient_matrix_UB_23      -0.0831969000
_diffrn_orient_matrix_UB_31      -0.1911351000
_diffrn_orient_matrix_UB_32      -0.0187943000
_diffrn_orient_matrix_UB_33      -0.0204797000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.934
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2977
_reflns_number_total             3045
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         0.153
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3045
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0305
_refine_ls_restrained_S_all      1.060
_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)+(0.0436P)²+0.2371P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0756
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.8(4)
 0.2(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C8(H8), C6(H6), C24(H24), C14(H14), C4(H4), C5(H5),
 C18(H18), C2(H2), C20(H20), C3(H3), C17(H17), C16(H16), C15(H15), C23(H23),
 C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O12 O 0.37738(18) 0.88443(12) 0.49116(9) 0.0274(3) Uani 1 1 d . . . . .
C7 C 0.2730(2) 0.64686(16) 0.60647(11) 0.0190(4) Uani 1 1 d . . . . .
C10 C 0.2863(2) 0.71690(16) 0.43454(12) 0.0198(4) Uani 1 1 d . . . . .
H10 H 0.2127 0.6564 0.4402 0.024 Uiso 1 1 calc R . . . .
C19 C 0.2935(2) 0.54378(16) 0.56126(11) 0.0192(4) Uani 1 1 d . . . . .
C11 C 0.3555(2) 0.73848(16) 0.36728(11) 0.0201(4) Uani 1 1 d . . . . .
H11 H 0.4281 0.7999 0.3643 0.024 Uiso 1 1 calc R . . . .
C8 C 0.2950(2) 0.75028(17) 0.57873(11) 0.0216(4) Uani 1 1 d . . . . .
H8 H 0.2900 0.8067 0.6146 0.026 Uiso 1 1 calc R . . . .
C9 C 0.3260(2) 0.78851(16) 0.50032(11) 0.0197(4) Uani 1 1 d . . . . .
C6 C 0.2861(2) 0.53917(16) 0.72796(12) 0.0215(4) Uani 1 1 d . . . . .
H6 H 0.3552 0.4868 0.7039 0.026 Uiso 1 1 calc R . . . .
C1 C 0.2269(2) 0.63205(17) 0.68781(11) 0.0195(4) Uani 1 1 d . . . . .
C13 C 0.3288(2) 0.67533(16) 0.29725(11) 0.0195(4) Uani 1 1 d . . . . .
C24 C 0.1606(2) 0.46545(17) 0.55994(11) 0.0226(4) Uani 1 1 d . . . . .
H24 H 0.0640 0.4756 0.5903 0.027 Uiso 1 1 calc R . . . .
C14 C 0.3931(2) 0.71805(17) 0.22963(12) 0.0240(4) Uani 1 1 d . . . . .
H14 H 0.4547 0.7844 0.2301 0.029 Uiso 1 1 calc R . . . .
C4 C 0.1363(2) 0.60066(19) 0.83949(11) 0.0261(4) Uani 1 1 d . . . . .
H4 H 0.1051 0.5899 0.8897 0.031 Uiso 1 1 calc R . . . .
C5 C 0.2426(2) 0.52456(17) 0.80338(12) 0.0242(4) Uani 1 1 d . . . . .
H5 H 0.2848 0.4635 0.8298 0.029 Uiso 1 1 calc R . . . .
C18 C 0.2399(2) 0.57377(16) 0.29538(11) 0.0221(4) Uani 1 1 d . . . . .
H18 H 0.1995 0.5426 0.3401 0.027 Uiso 1 1 calc R . . . .
C2 C 0.1227(2) 0.70914(17) 0.72536(12) 0.0221(4) Uani 1 1 d . . . . .
H2 H 0.0838 0.7719 0.6998 0.026 Uiso 1 1 calc R . . . .
C20 C 0.4409(2) 0.52420(18) 0.51772(11) 0.0255(4) Uani 1 1 d . . . . .
H20 H 0.5318 0.5747 0.5187 0.031 Uiso 1 1 calc R . . . .
C3 C 0.0768(2) 0.69320(18) 0.80025(12) 0.0265(4) Uani 1 1 d . . . . .
H3 H 0.0060 0.7446 0.8243 0.032 Uiso 1 1 calc R . . . .
C17 C 0.2119(2) 0.51945(18) 0.22737(13) 0.0249(4) Uani 1 1 d . . . . .
H17 H 0.1508 0.4529 0.2266 0.030 Uiso 1 1 calc R . . . .
C16 C 0.2748(2) 0.56404(17) 0.16028(11) 0.0243(4) Uani 1 1 d . . . . .
H16 H 0.2554 0.5276 0.1147 0.029 Uiso 1 1 calc R . . . .
C15 C 0.3665(3) 0.66316(18) 0.16170(12) 0.0268(4) Uani 1 1 d . . . . .
H15 H 0.4102 0.6928 0.1171 0.032 Uiso 1 1 calc R . . . .
C23 C 0.1713(3) 0.37313(18) 0.51391(13) 0.0302(5) Uani 1 1 d . . . . .
H23 H 0.0805 0.3227 0.5122 0.036 Uiso 1 1 calc R . . . .
C21 C 0.4519(3) 0.4301(2) 0.47324(12) 0.0357(5) Uani 1 1 d . . . . .
H21 H 0.5511 0.4171 0.4451 0.043 Uiso 1 1 calc R . . . .
C22 C 0.3171(3) 0.35523(19) 0.47020(13) 0.0361(5) Uani 1 1 d . . . . .
H22 H 0.3240 0.2932 0.4390 0.043 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
O12 C9 1.231(2) . ?
C7 C19 1.484(3) . ?
C7 C8 1.348(3) . ?
C7 C1 1.495(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.332(3) . ?
C10 C9 1.481(3) . ?
C19 C24 1.396(3) . ?
C19 C20 1.398(3) . ?
C11 H11 0.9300 . ?
C11 C13 1.469(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.482(3) . ?
C6 H6 0.9300 . ?
C6 C1 1.401(3) . ?
C6 C5 1.389(3) . ?
C1 C2 1.398(3) . ?
C13 C14 1.395(3) . ?
C13 C18 1.403(3) . ?
C24 H24 0.9300 . ?
C24 C23 1.380(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.387(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(3) . ?
C4 C3 1.391(3) . ?
C5 H5 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.387(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.381(3) . ?
C3 H3 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.392(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.388(3) . ?
C15 H15 0.9300 . ?
C23 H23 0.9300 . ?
C23 C22 1.386(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.381(4) . ?
C22 H22 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
C19 C7 C1 116.48(17) . . ?
C8 C7 C19 124.09(18) . . ?
C8 C7 C1 119.43(18) . . ?
C11 C10 H10 119.8 . . ?
C11 C10 C9 120.45(17) . . ?
C9 C10 H10 119.8 . . ?
C24 C19 C7 119.57(16) . . ?
C24 C19 C20 118.68(18) . . ?
C20 C19 C7 121.72(17) . . ?
C10 C11 H11 116.6 . . ?
C10 C11 C13 126.72(17) . . ?
C13 C11 H11 116.6 . . ?
C7 C8 H8 114.8 . . ?
C7 C8 C9 130.39(18) . . ?
C9 C8 H8 114.8 . . ?
O12 C9 C10 120.56(18) . . ?
O12 C9 C8 117.80(18) . . ?
C10 C9 C8 121.54(16) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C1 120.62(18) . . ?
C6 C1 C7 120.37(18) . . ?
C2 C1 C7 121.17(18) . . ?
C2 C1 C6 118.45(19) . . ?
C14 C13 C11 118.96(17) . . ?
C14 C13 C18 118.41(18) . . ?
C18 C13 C11 122.62(17) . . ?
C19 C24 H24 119.7 . . ?
C23 C24 C19 120.54(19) . . ?
C23 C24 H24 119.7 . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.07(18) . . ?
C15 C14 H14 119.5 . . ?
C5 C4 H4 120.2 . . ?
C5 C4 C3 119.64(19) . . ?
C3 C4 H4 120.2 . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.9 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.49(18) . . ?
C17 C18 H18 119.8 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.78(19) . . ?
C3 C2 H2 119.6 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C4 C3 H3 119.9 . . ?
C2 C3 C4 120.22(18) . . ?
C2 C3 H3 119.9 . . ?
C18 C17 H17 119.8 . . ?
C18 C17 C16 120.33(19) . . ?
C16 C17 H17 119.8 . . ?
C17 C16 H16 120.2 . . ?
C15 C16 C17 119.65(19) . . ?
C15 C16 H16 120.2 . . ?
C14 C15 C16 120.02(19) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C24 C23 H23 119.9 . . ?
C24 C23 C22 120.3(2) . . ?
C22 C23 H23 119.9 . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.6(2) . . ?
C22 C21 H21 119.7 . . ?
C23 C22 H22 120.2 . . ?
C21 C22 C23 119.6(2) . . ?
C21 C22 H22 120.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.082
_oxdiff_exptl_absorpt_empirical_full_min 0.404
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8(4)
2 0.2(4)

