# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

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

data_exp_1593
_database_code_depnum_ccdc_archive 'CCDC 1882682'
loop_
_audit_author_name
_audit_author_address
'Feng Wu'
;SCUT
China
;
_audit_update_record             
;
2018-12-03 deposited with the CCDC.	2020-09-21 downloaded from the CCDC.
;
_audit_creation_date             2018-07-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H26 F2 O2'
_chemical_formula_sum            'C36 H26 F2 O2'
_chemical_formula_weight         528.57
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   23.2414(16)
_cell_length_b                   13.1722(9)
_cell_length_c                   17.5730(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.010(6)
_cell_angle_gamma                90
_cell_volume                     5280.8(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4948
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.0750
_cell_measurement_theta_min      2.7670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11712
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.945
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00 101.00   1.00    7.50    --   11.74 178.00 150.00   66
  2  ω    -20.00  86.00   1.00    7.50    --   11.74  77.00-180.00  106
  3  ω     61.00  87.00   1.00    7.50    --   11.74  77.00 -90.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0064076000
_diffrn_orient_matrix_UB_12      0.0214506000
_diffrn_orient_matrix_UB_13      0.0377017000
_diffrn_orient_matrix_UB_21      0.0039205000
_diffrn_orient_matrix_UB_22      -0.0493428000
_diffrn_orient_matrix_UB_23      0.0162923000
_diffrn_orient_matrix_UB_31      0.0301742000
_diffrn_orient_matrix_UB_32      0.0018614000
_diffrn_orient_matrix_UB_33      -0.0019886000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3772
_reflns_number_total             4670
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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         0.277
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4670
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.013
_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)+(0.0589P)²+3.4388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1202
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C9(H9), C2(H2), C20(H20), C30(H30), C17(H17), C34(H34), C5(H5),
 C25(H25), C21(H21), C3(H3), C31(H31), C19(H19), C4(H4), C33(H33), C28(H28),
 C26(H26), C27(H27)
2.c Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C36(H36A,H36B,H36C)
;
_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
O1 O 0.35781(5) 0.62409(9) 0.36427(7) 0.0272(3) Uani 1 1 d . . . . .
O2 O 0.50533(5) 0.43432(9) 0.39067(7) 0.0257(3) Uani 1 1 d . . . . .
F2 F 0.43521(6) 0.98849(8) 0.45044(8) 0.0483(4) Uani 1 1 d . . . . .
F1 F 0.29942(6) 0.17381(10) 0.45634(8) 0.0523(4) Uani 1 1 d . . . . .
C7 C 0.36827(8) 0.58114(12) 0.30694(10) 0.0208(4) Uani 1 1 d . . . . .
C1 C 0.33221(8) 0.51031(13) 0.17371(10) 0.0228(4) Uani 1 1 d . . . . .
C11 C 0.44928(8) 0.48156(13) 0.38795(10) 0.0217(4) Uani 1 1 d . . . . .
H11 H 0.453134 0.533158 0.428786 0.026 Uiso 1 1 calc R . . . .
C15 C 0.46489(8) 0.72005(13) 0.34370(10) 0.0232(4) Uani 1 1 d . . . . .
C29 C 0.40919(8) 0.39843(13) 0.40625(10) 0.0227(4) Uani 1 1 d . . . . .
C16 C 0.48549(8) 0.73384(13) 0.42280(11) 0.0263(4) Uani 1 1 d . . . . .
H16 H 0.506464 0.682030 0.451573 0.032 Uiso 1 1 calc R . . . .
C6 C 0.32381(8) 0.57464(12) 0.23432(10) 0.0217(4) Uani 1 1 d . . . . .
C9 C 0.42935(8) 0.46140(13) 0.24259(10) 0.0228(4) Uani 1 1 d . . . . .
H9 H 0.462214 0.420258 0.245458 0.027 Uiso 1 1 calc R . . . .
C10 C 0.38661(8) 0.45136(13) 0.18026(10) 0.0224(4) Uani 1 1 d . . . . .
C12 C 0.54735(8) 0.49095(13) 0.36489(10) 0.0228(4) Uani 1 1 d . . . . .
C2 C 0.28707(8) 0.50371(14) 0.10887(11) 0.0287(4) Uani 1 1 d . . . . .
H2 H 0.291112 0.460318 0.068471 0.034 Uiso 1 1 calc R . . . .
C24 C 0.60449(8) 0.44706(14) 0.37956(10) 0.0251(4) Uani 1 1 d . . . . .
C20 C 0.43508(8) 0.79999(13) 0.30125(11) 0.0276(4) Uani 1 1 d . . . . .
H20 H 0.421400 0.792258 0.248279 0.033 Uiso 1 1 calc R . . . .
C8 C 0.42845(8) 0.53399(13) 0.30838(10) 0.0214(4) Uani 1 1 d . . . . .
C13 C 0.53560(8) 0.57995(13) 0.32483(10) 0.0234(4) Uani 1 1 d . . . . .
C14 C 0.47390(8) 0.62207(13) 0.30182(10) 0.0223(4) Uani 1 1 d . . . . .
H14 H 0.468627 0.639200 0.246651 0.027 Uiso 1 1 calc R . . . .
C30 C 0.36707(8) 0.41931(14) 0.45041(10) 0.0277(4) Uani 1 1 d . . . . .
H30 H 0.363394 0.484934 0.468403 0.033 Uiso 1 1 calc R . . . .
C17 C 0.47524(9) 0.82369(14) 0.45944(11) 0.0306(4) Uani 1 1 d . . . . .
H17 H 0.488328 0.832049 0.512474 0.037 Uiso 1 1 calc R . . . .
C34 C 0.41426(9) 0.29944(14) 0.38058(11) 0.0287(4) Uani 1 1 d . . . . .
H34 H 0.442675 0.284224 0.351558 0.034 Uiso 1 1 calc R . . . .
C5 C 0.27259(8) 0.63064(14) 0.22864(11) 0.0269(4) Uani 1 1 d . . . . .
H5 H 0.267381 0.672359 0.269479 0.032 Uiso 1 1 calc R . . . .
C35 C 0.39342(9) 0.38178(14) 0.11487(11) 0.0302(4) Uani 1 1 d . . . . .
H35A H 0.362703 0.331977 0.107678 0.045 Uiso 1 1 calc GR . . . .
H35B H 0.430749 0.348320 0.126995 0.045 Uiso 1 1 calc GR . . . .
H35C H 0.391175 0.420557 0.068142 0.045 Uiso 1 1 calc GR . . . .
C18 C 0.44517(9) 0.90011(14) 0.41514(12) 0.0323(5) Uani 1 1 d . . . . .
C23 C 0.65118(8) 0.50148(14) 0.35645(10) 0.0279(4) Uani 1 1 d . . . . .
C25 C 0.61566(8) 0.35158(14) 0.41609(11) 0.0298(4) Uani 1 1 d . . . . .
H25 H 0.585337 0.316553 0.432136 0.036 Uiso 1 1 calc R . . . .
C21 C 0.58332(8) 0.63275(14) 0.30311(10) 0.0265(4) Uani 1 1 d . . . . .
H21 H 0.575765 0.694361 0.277282 0.032 Uiso 1 1 calc R . . . .
C3 C 0.23638(9) 0.56071(15) 0.10370(12) 0.0349(5) Uani 1 1 d . . . . .
H3 H 0.206964 0.555413 0.059845 0.042 Uiso 1 1 calc R . . . .
C32 C 0.33635(9) 0.24783(15) 0.44031(11) 0.0348(5) Uani 1 1 d . . . . .
C31 C 0.33052(9) 0.34353(16) 0.46794(11) 0.0342(5) Uani 1 1 d . . . . .
H31 H 0.302535 0.357407 0.497925 0.041 Uiso 1 1 calc R . . . .
C19 C 0.42556(8) 0.89071(14) 0.33683(12) 0.0321(5) Uani 1 1 d . . . . .
H19 H 0.406249 0.944149 0.308122 0.039 Uiso 1 1 calc R . . . .
C4 C 0.22913(9) 0.62500(15) 0.16273(12) 0.0335(5) Uani 1 1 d . . . . .
H4 H 0.195426 0.664306 0.158488 0.040 Uiso 1 1 calc R . . . .
C33 C 0.37761(9) 0.22325(15) 0.39762(11) 0.0353(5) Uani 1 1 d . . . . .
H33 H 0.381036 0.157150 0.380425 0.042 Uiso 1 1 calc R . . . .
C28 C 0.70752(9) 0.45651(16) 0.37189(11) 0.0339(5) Uani 1 1 d . . . . .
H28 H 0.738890 0.491182 0.358208 0.041 Uiso 1 1 calc R . . . .
C22 C 0.63961(8) 0.59780(15) 0.31816(10) 0.0287(4) Uani 1 1 d . . . . .
C26 C 0.67068(9) 0.31017(16) 0.42808(12) 0.0365(5) Uani 1 1 d . . . . .
H26 H 0.677320 0.246375 0.450733 0.044 Uiso 1 1 calc R . . . .
C27 C 0.71696(9) 0.36380(17) 0.40626(12) 0.0386(5) Uani 1 1 d . . . . .
H27 H 0.754407 0.335901 0.415307 0.046 Uiso 1 1 calc R . . . .
C36 C 0.68888(9) 0.65839(17) 0.29590(13) 0.0413(5) Uani 1 1 d . . . . .
H36A H 0.717489 0.673625 0.341517 0.062 Uiso 1 1 calc GR . . . .
H36B H 0.673615 0.720514 0.271454 0.062 Uiso 1 1 calc GR . . . .
H36C H 0.706898 0.619634 0.260539 0.062 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.220(2) . ?
O2 C11 1.436(2) . ?
O2 C12 1.373(2) . ?
F2 C18 1.360(2) . ?
F1 C32 1.363(2) . ?
C7 C6 1.483(2) . ?
C7 C8 1.526(2) . ?
C1 C6 1.403(2) . ?
C1 C10 1.469(2) . ?
C1 C2 1.396(3) . ?
C11 C29 1.512(2) . ?
C11 C8 1.552(2) . ?
C15 C16 1.393(3) . ?
C15 C20 1.396(3) . ?
C15 C14 1.520(2) . ?
C29 C30 1.388(3) . ?
C29 C34 1.392(3) . ?
C16 C17 1.390(3) . ?
C6 C5 1.388(2) . ?
C9 C10 1.337(2) . ?
C9 C8 1.504(2) . ?
C10 C35 1.502(2) . ?
C12 C24 1.426(2) . ?
C12 C13 1.368(2) . ?
C2 C3 1.385(3) . ?
C24 C23 1.423(3) . ?
C24 C25 1.413(3) . ?
C20 C19 1.386(3) . ?
C8 C14 1.588(2) . ?
C13 C14 1.519(2) . ?
C13 C21 1.422(3) . ?
C30 C31 1.383(3) . ?
C17 C18 1.378(3) . ?
C34 C33 1.386(3) . ?
C5 C4 1.386(3) . ?
C18 C19 1.370(3) . ?
C23 C28 1.415(3) . ?
C23 C22 1.437(3) . ?
C25 C26 1.369(3) . ?
C21 C22 1.364(3) . ?
C3 C4 1.374(3) . ?
C32 C31 1.367(3) . ?
C32 C33 1.364(3) . ?
C28 C27 1.362(3) . ?
C22 C36 1.507(3) . ?
C26 C27 1.400(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O2 C11 116.83(13) . . ?
O1 C7 C6 121.43(16) . . ?
O1 C7 C8 120.10(15) . . ?
C6 C7 C8 118.46(14) . . ?
C6 C1 C10 120.13(16) . . ?
C2 C1 C6 117.72(16) . . ?
C2 C1 C10 122.14(16) . . ?
O2 C11 C29 105.73(13) . . ?
O2 C11 C8 110.35(13) . . ?
C29 C11 C8 114.54(14) . . ?
C16 C15 C20 118.42(17) . . ?
C16 C15 C14 122.76(16) . . ?
C20 C15 C14 118.82(16) . . ?
C30 C29 C11 120.31(16) . . ?
C30 C29 C34 118.64(17) . . ?
C34 C29 C11 121.05(16) . . ?
C17 C16 C15 121.12(17) . . ?
C1 C6 C7 120.85(15) . . ?
C5 C6 C7 118.57(15) . . ?
C5 C6 C1 120.54(16) . . ?
C10 C9 C8 125.13(16) . . ?
C1 C10 C35 118.53(15) . . ?
C9 C10 C1 120.35(16) . . ?
C9 C10 C35 121.11(16) . . ?
O2 C12 C24 114.63(15) . . ?
C13 C12 O2 123.44(16) . . ?
C13 C12 C24 121.86(16) . . ?
C3 C2 C1 121.11(17) . . ?
C23 C24 C12 118.61(16) . . ?
C25 C24 C12 121.78(17) . . ?
C25 C24 C23 119.61(17) . . ?
C19 C20 C15 121.00(18) . . ?
C7 C8 C11 108.86(14) . . ?
C7 C8 C14 108.77(13) . . ?
C11 C8 C14 107.05(14) . . ?
C9 C8 C7 113.16(14) . . ?
C9 C8 C11 111.23(14) . . ?
C9 C8 C14 107.55(14) . . ?
C12 C13 C14 122.39(16) . . ?
C12 C13 C21 117.92(16) . . ?
C21 C13 C14 119.68(16) . . ?
C15 C14 C8 115.48(14) . . ?
C13 C14 C15 113.06(14) . . ?
C13 C14 C8 108.73(14) . . ?
C31 C30 C29 120.69(18) . . ?
C18 C17 C16 118.27(18) . . ?
C33 C34 C29 120.98(18) . . ?
C4 C5 C6 120.66(17) . . ?
F2 C18 C17 118.67(18) . . ?
F2 C18 C19 118.86(17) . . ?
C19 C18 C17 122.46(17) . . ?
C24 C23 C22 119.58(17) . . ?
C28 C23 C24 117.55(17) . . ?
C28 C23 C22 122.87(17) . . ?
C26 C25 C24 120.63(18) . . ?
C22 C21 C13 123.45(17) . . ?
C4 C3 C2 120.65(18) . . ?
F1 C32 C31 118.49(19) . . ?
F1 C32 C33 118.70(19) . . ?
C33 C32 C31 122.82(18) . . ?
C32 C31 C30 118.66(19) . . ?
C18 C19 C20 118.68(17) . . ?
C3 C4 C5 119.28(18) . . ?
C32 C33 C34 118.20(19) . . ?
C27 C28 C23 121.68(19) . . ?
C23 C22 C36 120.36(17) . . ?
C21 C22 C23 118.39(17) . . ?
C21 C22 C36 121.26(18) . . ?
C25 C26 C27 120.04(19) . . ?
C28 C27 C26 120.45(18) . . ?


_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.385
_oxdiff_exptl_absorpt_empirical_full_min 0.640
