# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

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

data_brf4
_database_code_depnum_ccdc_archive 'CCDC 2080843'
loop_
_audit_author_name
_audit_author_address
'Jean M. F. Custodio'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2021-04-28 deposited with the CCDC.	2021-07-09 downloaded from the CCDC.
;
_audit_creation_date             2021-03-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        
1E,4E-1-(4-fluorophenyl)-5-(2,6,6-trimethylcyclohexen-1-yl)penta-1,4-dien-3-one
_chemical_formula_moiety         '2(C10 H11.5 F0.5 O0.5)'
_chemical_formula_sum            'C20 H23 F O'
_chemical_formula_weight         298.38
_chemical_absolute_configuration .
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   21.691(3)
_cell_length_b                   14.305(3)
_cell_length_c                   10.6099(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3292.3(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7603
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.82
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6953
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0616 before and 0.0532 after correction.
The Ratio of minimum to maximum transmission is 0.9324.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plaque
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            70248
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         1.705
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5127
_reflns_number_total             7256
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         7256
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.023
_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)+(0.0473P)²+0.2336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.1010
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9(12)
 0.1(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
C1A \\sim C15B \\sim C14 \\sim C15 \\sim C14A \\sim C1B \\sim C14B \\sim C15A:
within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 1.7A
4. Others
 Sof(H16G)=Sof(H16H)=Sof(H16C)=Sof(H16D)=Sof(C14B)=Sof(H14A)=Sof(H14B)=
 Sof(C15B)=Sof(H15C)=Sof(H15D)=Sof(C15)=Sof(H15E)=Sof(H15F)=Sof(C1B)=Sof(H1BA)=
 Sof(H1BB)=1-FVAR(1)
 Sof(H16E)=Sof(H16F)=Sof(H16A)=Sof(H16B)=Sof(C15A)=Sof(H15A)=Sof(H15B)=
 Sof(C14)=Sof(H14E)=Sof(H14F)=Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(C1A)=Sof(H1AA)=
 Sof(H1AB)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C16*(H16G,H16H), C16*(H16E,H16F), C16(H16C,H16D), C16(H16A,H16B), C14B(H14A,
 H14B), C15A(H15A,H15B), C15B(H15C,H15D), C14(H14E,H14F), C15(H15E,H15F),
 C14A(H14C,H14D), C1A(H1AA,H1AB), C1B(H1BA,H1BB)
5.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C5*(H5*), C11(H11), C10(H10), C7*(H7*), C8*(H8*), C5(H5), C11*(H11*),
 C8(H8), C1(H1), C10*(H10*), C4*(H4*), C4(H4), C2(H2), C1*(H1*), C2*(H2*)
5.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C18*(H18D,H18E,H18F), C20*(H20D,H20E,H20F), C20(H20A,
 H20B,H20C), C19*(H19D,H19E,H19F), C19(H19A,H19B,H19C)
;
_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
F1 F 0.69784(8) 0.76821(11) 0.24896(19) 0.0442(5) Uani 1 1 d . . . . .
F1* F 0.70085(10) -0.19191(12) 0.7517(2) 0.0540(6) Uani 1 1 d . . . . .
O1 O 0.67178(10) 0.26476(14) -0.15063(18) 0.0318(5) Uani 1 1 d . . . . .
O1* O 0.67550(10) 0.31048(14) 0.34904(18) 0.0336(5) Uani 1 1 d . . . . .
C6* C 0.68441(13) 0.0568(2) 0.5613(3) 0.0219(7) Uani 1 1 d . . . . .
C7 C 0.67725(12) 0.4293(2) -0.0060(3) 0.0236(7) Uani 1 1 d . . . . .
H7 H 0.675532 0.433528 -0.093378 0.028 Uiso 1 1 calc R U . . .
C9* C 0.66102(13) 0.3125(2) 0.4608(3) 0.0233(6) Uani 1 1 d . . . . .
C17* C 0.59864(13) 0.57434(19) 0.6734(3) 0.0243(6) Uani 1 1 d . . . . .
C9 C 0.66004(13) 0.2625(2) -0.0370(3) 0.0225(7) Uani 1 1 d . . . . .
C5* C 0.69237(12) 0.0551(2) 0.6910(3) 0.0239(7) Uani 1 1 d . . . . .
H5* H 0.693869 0.111152 0.735370 0.029 Uiso 1 1 calc R U . . .
C12 C 0.57152(12) 0.09391(19) 0.1822(3) 0.0214(6) Uani 1 1 d . . . . .
C17 C 0.59140(12) 0.0050(2) 0.1751(3) 0.0232(6) Uani 1 1 d . . . . .
C6 C 0.68531(13) 0.5168(2) 0.0626(3) 0.0222(7) Uani 1 1 d . . . . .
C11 C 0.60682(12) 0.17312(19) 0.1302(3) 0.0227(6) Uani 1 1 d . . . . .
H11 H 0.612547 0.224289 0.183034 0.027 Uiso 1 1 calc R U . . .
C10 C 0.63120(13) 0.17880(19) 0.0161(3) 0.0235(6) Uani 1 1 d . . . . .
H10 H 0.629887 0.125581 -0.034217 0.028 Uiso 1 1 calc R U . . .
C7* C 0.67764(13) 0.1447(2) 0.4916(3) 0.0243(7) Uani 1 1 d . . . . .
H7* H 0.679513 0.141148 0.404123 0.029 Uiso 1 1 calc R U . . .
C8* C 0.66912(13) 0.2284(2) 0.5412(3) 0.0232(6) Uani 1 1 d . . . . .
H8* H 0.668176 0.234814 0.628369 0.028 Uiso 1 1 calc R U . . .
C5 C 0.69699(12) 0.5203(2) 0.1918(3) 0.0233(7) Uani 1 1 d . . . . .
H5 H 0.701516 0.464873 0.236743 0.028 Uiso 1 1 calc R U . . .
C3 C 0.69457(13) 0.6850(2) 0.1862(3) 0.0290(7) Uani 1 1 d . . . . .
C11* C 0.60984(12) 0.40545(19) 0.6285(3) 0.0230(6) Uani 1 1 d . . . . .
H11* H 0.614498 0.354520 0.682135 0.028 Uiso 1 1 calc R U . . .
C13* C 0.51417(13) 0.4624(2) 0.7399(3) 0.0284(7) Uani 1 1 d . . . . .
C12* C 0.57642(12) 0.4869(2) 0.6798(3) 0.0234(6) Uani 1 1 d . . . . .
C8 C 0.67208(13) 0.3440(2) 0.0433(3) 0.0226(7) Uani 1 1 d . . . . .
H8 H 0.676158 0.335984 0.129913 0.027 Uiso 1 1 calc R U . . .
C1 C 0.67970(13) 0.6010(2) -0.0023(3) 0.0299(7) Uani 1 1 d . . . . .
H1 H 0.673055 0.600043 -0.088927 0.036 Uiso 1 1 calc R U . . .
C10* C 0.63399(13) 0.39705(19) 0.5138(3) 0.0249(6) Uani 1 1 d . . . . .
H10* H 0.633595 0.449940 0.462817 0.030 Uiso 1 1 calc R U . . .
C13 C 0.51038(12) 0.1219(2) 0.2438(3) 0.0274(7) Uani 1 1 d . . . . .
C4* C 0.69812(12) -0.02848(19) 0.7554(3) 0.0271(7) Uani 1 1 d . . . . .
H4* H 0.703618 -0.029585 0.842321 0.033 Uiso 1 1 calc R U . . .
C4 C 0.70192(12) 0.6043(2) 0.2537(3) 0.0277(7) Uani 1 1 d . . . . .
H4 H 0.710088 0.606254 0.339700 0.033 Uiso 1 1 calc R U . . .
C18 C 0.65134(12) -0.0248(2) 0.1173(3) 0.0272(7) Uani 1 1 d . . . . .
H18A H 0.643679 -0.052757 0.036551 0.041 Uiso 1 1 calc R U . . .
H18B H 0.671192 -0.069398 0.171327 0.041 Uiso 1 1 calc R U . . .
H18C H 0.677524 0.028778 0.106967 0.041 Uiso 1 1 calc R U . . .
C2 C 0.68380(15) 0.6862(2) 0.0593(3) 0.0340(8) Uani 1 1 d . . . . .
H2 H 0.679372 0.742272 0.015868 0.041 Uiso 1 1 calc R U . . .
C1* C 0.68234(14) -0.0280(2) 0.4970(3) 0.0301(7) Uani 1 1 d . . . . .
H1* H 0.677020 -0.027975 0.409987 0.036 Uiso 1 1 calc R U . . .
C3* C 0.69545(15) -0.1101(2) 0.6866(3) 0.0341(8) Uani 1 1 d . . . . .
C18* C 0.65990(13) 0.6008(2) 0.6187(3) 0.0304(7) Uani 1 1 d . . . . .
H18D H 0.683850 0.545354 0.604240 0.046 Uiso 1 1 calc R U . . .
H18E H 0.681348 0.640888 0.676446 0.046 Uiso 1 1 calc R U . . .
H18F H 0.653755 0.632978 0.540300 0.046 Uiso 1 1 calc R U . . .
C16* C 0.56350(14) 0.6573(2) 0.7243(3) 0.0342(8) Uani 1 1 d . . . . .
H16G H 0.568040 0.709568 0.666798 0.041 Uiso 0.538(7) 1 calc R U P A 2
H16H H 0.580933 0.675500 0.804839 0.041 Uiso 0.538(7) 1 calc R U P A 2
H16E H 0.592294 0.701007 0.762002 0.041 Uiso 0.462(7) 1 calc R U P A 1
H16F H 0.542880 0.688933 0.655295 0.041 Uiso 0.462(7) 1 calc R U P A 1
C2* C 0.68803(16) -0.1122(2) 0.5599(3) 0.0380(9) Uani 1 1 d . . . . .
H2* H 0.686795 -0.168587 0.516468 0.046 Uiso 1 1 calc R U . . .
C20* C 0.52165(16) 0.3943(3) 0.8488(3) 0.0489(10) Uani 1 1 d . . . . .
H20D H 0.540802 0.337971 0.818895 0.073 Uiso 1 1 calc R U . . .
H20E H 0.481894 0.379747 0.883357 0.073 Uiso 1 1 calc R U . . .
H20F H 0.546988 0.422065 0.912787 0.073 Uiso 1 1 calc R U . . .
C20 C 0.52010(15) 0.1907(3) 0.3505(3) 0.0454(9) Uani 1 1 d . . . . .
H20A H 0.537172 0.247599 0.317660 0.068 Uiso 1 1 calc R U . . .
H20B H 0.547976 0.164354 0.411180 0.068 Uiso 1 1 calc R U . . .
H20C H 0.481304 0.203736 0.390380 0.068 Uiso 1 1 calc R U . . .
C19* C 0.47269(15) 0.4169(3) 0.6412(3) 0.0478(9) Uani 1 1 d . . . . .
H19D H 0.467132 0.459073 0.571700 0.072 Uiso 1 1 calc R U . . .
H19E H 0.433357 0.402822 0.678055 0.072 Uiso 1 1 calc R U . . .
H19F H 0.491490 0.360243 0.611643 0.072 Uiso 1 1 calc R U . . .
C19 C 0.46903(15) 0.1681(3) 0.1451(3) 0.0480(9) Uani 1 1 d . . . . .
H19A H 0.430987 0.186994 0.183747 0.072 Uiso 1 1 calc R U . . .
H19B H 0.460621 0.124490 0.078585 0.072 Uiso 1 1 calc R U . . .
H19C H 0.489531 0.221991 0.111088 0.072 Uiso 1 1 calc R U . . .
C16 C 0.55446(14) -0.0753(2) 0.2269(3) 0.0319(8) Uani 1 1 d . . . . .
H16C H 0.571643 -0.093934 0.307528 0.038 Uiso 0.538(7) 1 calc R U P A 2
H16D H 0.557807 -0.128136 0.170015 0.038 Uiso 0.538(7) 1 calc R U P A 2
H16A H 0.533788 -0.107008 0.158038 0.038 Uiso 0.462(7) 1 calc R U P A 1
H16B H 0.582190 -0.119712 0.266455 0.038 Uiso 0.462(7) 1 calc R U P A 1
C14B C 0.4849(3) -0.0502(4) 0.2449(8) 0.0348(16) Uani 0.538(7) 1 d . U P A 2
H14A H 0.465188 -0.041181 0.163685 0.042 Uiso 0.538(7) 1 calc R U P A 2
H14B H 0.463670 -0.100082 0.289105 0.042 Uiso 0.538(7) 1 calc R U P A 2
C15A C 0.5076(4) -0.0445(5) 0.3209(9) 0.039(2) Uani 0.462(7) 1 d . U P A 1
H15A H 0.480510 -0.096135 0.341931 0.047 Uiso 0.462(7) 1 calc R U P A 1
H15B H 0.527871 -0.023749 0.397456 0.047 Uiso 0.462(7) 1 calc R U P A 1
C15B C 0.4934(3) 0.6351(5) 0.7417(8) 0.0436(18) Uani 0.538(7) 1 d . U P A 2
H15C H 0.473413 0.685292 0.787514 0.052 Uiso 0.538(7) 1 calc R U P A 2
H15D H 0.473627 0.628926 0.660135 0.052 Uiso 0.538(7) 1 calc R U P A 2
C14 C 0.5166(4) 0.6289(5) 0.8209(8) 0.0363(19) Uani 0.462(7) 1 d . U P A 1
H14E H 0.536789 0.604068 0.895295 0.044 Uiso 0.462(7) 1 calc R U P A 1
H14F H 0.491738 0.682225 0.845616 0.044 Uiso 0.462(7) 1 calc R U P A 1
C15 C 0.4880(5) 0.5443(7) 0.8147(8) 0.037(2) Uani 0.538(7) 1 d . U P A 2
H15E H 0.445028 0.532387 0.833821 0.045 Uiso 0.538(7) 1 calc R U P A 2
H15F H 0.510136 0.550027 0.893787 0.045 Uiso 0.538(7) 1 calc R U P A 2
C14A C 0.4716(5) 0.0329(8) 0.2657(10) 0.038(2) Uani 0.462(7) 1 d . U P A 1
H14C H 0.437594 0.047785 0.321455 0.046 Uiso 0.462(7) 1 calc R U P A 1
H14D H 0.454442 0.012595 0.185872 0.046 Uiso 0.462(7) 1 calc R U P A 1
C1A C 0.4776(5) 0.5563(8) 0.7612(10) 0.037(2) Uani 0.462(7) 1 d . U P A 1
H1AA H 0.462704 0.579246 0.680677 0.044 Uiso 0.462(7) 1 calc R U P A 1
H1AB H 0.442094 0.544200 0.814302 0.044 Uiso 0.462(7) 1 calc R U P A 1
C1B C 0.4827(4) 0.0401(7) 0.3219(8) 0.0347(19) Uani 0.538(7) 1 d . U P A 2
H1BA H 0.506031 0.032239 0.399180 0.042 Uiso 0.538(7) 1 calc R U P A 2
H1BB H 0.440382 0.054420 0.344165 0.042 Uiso 0.538(7) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.366(3) . ?
F1* C3* 1.364(3) . ?
O1 C9 1.233(3) . ?
O1* C9* 1.227(3) . ?
C6* C5* 1.387(4) . ?
C6* C7* 1.465(4) . ?
C6* C1* 1.393(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.458(4) . ?
C7 C8 1.333(4) . ?
C9* C8* 1.485(4) . ?
C9* C10* 1.457(4) . ?
C17* C12* 1.342(4) . ?
C17* C18* 1.498(4) . ?
C17* C16* 1.510(4) . ?
C9 C10 1.463(4) . ?
C9 C8 1.467(4) . ?
C5* H5* 0.9300 . ?
C5* C4* 1.383(4) . ?
C12 C17 1.346(4) . ?
C12 C11 1.474(4) . ?
C12 C13 1.532(4) . ?
C17 C18 1.499(4) . ?
C17 C16 1.505(4) . ?
C6 C5 1.395(4) . ?
C6 C1 1.393(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.324(4) . ?
C10 H10 0.9300 . ?
C7* H7* 0.9300 . ?
C7* C8* 1.321(4) . ?
C8* H8* 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.374(4) . ?
C3 C4 1.368(4) . ?
C3 C2 1.366(4) . ?
C11* H11* 0.9300 . ?
C11* C12* 1.477(4) . ?
C11* C10* 1.331(4) . ?
C13* C12* 1.534(4) . ?
C13* C20* 1.519(5) . ?
C13* C19* 1.527(5) . ?
C13* C15 1.524(10) . ?
C13* C1A 1.577(12) . ?
C8 H8 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.386(4) . ?
C10* H10* 0.9300 . ?
C13 C20 1.515(4) . ?
C13 C19 1.530(4) . ?
C13 C14A 1.542(12) . ?
C13 C1B 1.553(9) . ?
C4* H4* 0.9300 . ?
C4* C3* 1.378(4) . ?
C4 H4 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C2 H2 0.9300 . ?
C1* H1* 0.9300 . ?
C1* C2* 1.383(4) . ?
C3* C2* 1.354(5) . ?
C18* H18D 0.9600 . ?
C18* H18E 0.9600 . ?
C18* H18F 0.9600 . ?
C16* H16G 0.9700 . ?
C16* H16H 0.9700 . ?
C16* H16E 0.9700 . ?
C16* H16F 0.9700 . ?
C16* C15B 1.564(7) . ?
C16* C14 1.500(8) . ?
C2* H2* 0.9300 . ?
C20* H20D 0.9600 . ?
C20* H20E 0.9600 . ?
C20* H20F 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19* H19D 0.9600 . ?
C19* H19E 0.9600 . ?
C19* H19F 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C16 H16C 0.9700 . ?
C16 H16D 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C14B 1.563(7) . ?
C16 C15A 1.490(8) . ?
C14B H14A 0.9700 . ?
C14B H14B 0.9700 . ?
C14B C1B 1.530(12) . ?
C15A H15A 0.9700 . ?
C15A H15B 0.9700 . ?
C15A C14A 1.476(16) . ?
C15B H15C 0.9700 . ?
C15B H15D 0.9700 . ?
C15B C15 1.517(12) . ?
C14 H14E 0.9700 . ?
C14 H14F 0.9700 . ?
C14 C1A 1.482(15) . ?
C15 H15E 0.9700 . ?
C15 H15F 0.9700 . ?
C14A H14C 0.9700 . ?
C14A H14D 0.9700 . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C1B H1BA 0.9700 . ?
C1B H1BB 0.9700 . ?

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* C6* C7* 121.9(3) . . ?
C5* C6* C1* 118.3(3) . . ?
C1* C6* C7* 119.8(3) . . ?
C6 C7 H7 116.6 . . ?
C8 C7 H7 116.6 . . ?
C8 C7 C6 126.9(3) . . ?
O1* C9* C8* 120.4(3) . . ?
O1* C9* C10* 119.7(3) . . ?
C10* C9* C8* 119.9(2) . . ?
C12* C17* C18* 125.0(3) . . ?
C12* C17* C16* 122.2(3) . . ?
C18* C17* C16* 112.8(2) . . ?
O1 C9 C10 119.1(3) . . ?
O1 C9 C8 120.7(3) . . ?
C10 C9 C8 120.2(2) . . ?
C6* C5* H5* 119.4 . . ?
C4* C5* C6* 121.1(3) . . ?
C4* C5* H5* 119.4 . . ?
C17 C12 C11 122.7(2) . . ?
C17 C12 C13 123.2(2) . . ?
C11 C12 C13 114.1(2) . . ?
C12 C17 C18 124.7(3) . . ?
C12 C17 C16 122.1(3) . . ?
C18 C17 C16 113.3(2) . . ?
C5 C6 C7 122.9(3) . . ?
C1 C6 C7 119.0(3) . . ?
C1 C6 C5 118.1(3) . . ?
C12 C11 H11 116.7 . . ?
C10 C11 C12 126.6(3) . . ?
C10 C11 H11 116.7 . . ?
C9 C10 H10 117.5 . . ?
C11 C10 C9 124.9(3) . . ?
C11 C10 H10 117.5 . . ?
C6* C7* H7* 116.9 . . ?
C8* C7* C6* 126.2(3) . . ?
C8* C7* H7* 116.9 . . ?
C9* C8* H8* 119.3 . . ?
C7* C8* C9* 121.5(3) . . ?
C7* C8* H8* 119.3 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
F1 C3 C4 118.3(3) . . ?
F1 C3 C2 118.6(3) . . ?
C2 C3 C4 123.1(3) . . ?
C12* C11* H11* 116.5 . . ?
C10* C11* H11* 116.5 . . ?
C10* C11* C12* 127.0(3) . . ?
C12* C13* C1A 107.9(5) . . ?
C20* C13* C12* 111.6(2) . . ?
C20* C13* C19* 108.1(3) . . ?
C20* C13* C15 97.9(4) . . ?
C20* C13* C1A 119.5(5) . . ?
C19* C13* C12* 109.3(3) . . ?
C19* C13* C1A 99.5(5) . . ?
C15 C13* C12* 111.5(4) . . ?
C15 C13* C19* 117.7(4) . . ?
C17* C12* C11* 122.7(3) . . ?
C17* C12* C13* 123.4(3) . . ?
C11* C12* C13* 113.9(2) . . ?
C7 C8 C9 121.0(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C6 C1 H1 119.3 . . ?
C2 C1 C6 121.4(3) . . ?
C2 C1 H1 119.3 . . ?
C9* C10* H10* 117.0 . . ?
C11* C10* C9* 125.9(3) . . ?
C11* C10* H10* 117.0 . . ?
C12 C13 C14A 108.7(5) . . ?
C12 C13 C1B 111.5(4) . . ?
C20 C13 C12 111.6(2) . . ?
C20 C13 C19 108.2(3) . . ?
C20 C13 C14A 120.0(5) . . ?
C20 C13 C1B 98.3(4) . . ?
C19 C13 C12 109.2(3) . . ?
C19 C13 C14A 98.1(5) . . ?
C19 C13 C1B 117.7(4) . . ?
C5* C4* H4* 121.1 . . ?
C3* C4* C5* 117.8(3) . . ?
C3* C4* H4* 121.1 . . ?
C5 C4 H4 120.7 . . ?
C3 C4 C5 118.6(3) . . ?
C3 C4 H4 120.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C3 C2 C1 117.7(3) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C6* C1* H1* 119.4 . . ?
C2* C1* C6* 121.3(3) . . ?
C2* C1* H1* 119.4 . . ?
F1* C3* C4* 117.1(3) . . ?
C2* C3* F1* 119.6(3) . . ?
C2* C3* C4* 123.3(3) . . ?
C17* C18* H18D 109.5 . . ?
C17* C18* H18E 109.5 . . ?
C17* C18* H18F 109.5 . . ?
H18D C18* H18E 109.5 . . ?
H18D C18* H18F 109.5 . . ?
H18E C18* H18F 109.5 . . ?
C17* C16* H16G 109.2 . . ?
C17* C16* H16H 109.2 . . ?
C17* C16* H16E 109.2 . . ?
C17* C16* H16F 109.2 . . ?
C17* C16* C15B 111.9(3) . . ?
H16G C16* H16H 107.9 . . ?
H16E C16* H16F 107.9 . . ?
C15B C16* H16G 109.2 . . ?
C15B C16* H16H 109.2 . . ?
C14 C16* C17* 112.0(4) . . ?
C14 C16* H16E 109.2 . . ?
C14 C16* H16F 109.2 . . ?
C1* C2* H2* 120.9 . . ?
C3* C2* C1* 118.1(3) . . ?
C3* C2* H2* 120.9 . . ?
C13* C20* H20D 109.5 . . ?
C13* C20* H20E 109.5 . . ?
C13* C20* H20F 109.5 . . ?
H20D C20* H20E 109.5 . . ?
H20D C20* H20F 109.5 . . ?
H20E C20* H20F 109.5 . . ?
C13 C20 H20A 109.5 . . ?
C13 C20 H20B 109.5 . . ?
C13 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C13* C19* H19D 109.5 . . ?
C13* C19* H19E 109.5 . . ?
C13* C19* H19F 109.5 . . ?
H19D C19* H19E 109.5 . . ?
H19D C19* H19F 109.5 . . ?
H19E C19* H19F 109.5 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C16 H16C 109.1 . . ?
C17 C16 H16D 109.1 . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C17 C16 C14B 112.5(3) . . ?
H16C C16 H16D 107.8 . . ?
H16A C16 H16B 107.8 . . ?
C14B C16 H16C 109.1 . . ?
C14B C16 H16D 109.1 . . ?
C15A C16 C17 112.5(4) . . ?
C15A C16 H16A 109.1 . . ?
C15A C16 H16B 109.1 . . ?
C16 C14B H14A 110.4 . . ?
C16 C14B H14B 110.4 . . ?
H14A C14B H14B 108.6 . . ?
C1B C14B C16 106.8(6) . . ?
C1B C14B H14A 110.4 . . ?
C1B C14B H14B 110.4 . . ?
C16 C15A H15A 110.0 . . ?
C16 C15A H15B 110.0 . . ?
H15A C15A H15B 108.4 . . ?
C14A C15A C16 108.5(7) . . ?
C14A C15A H15A 110.0 . . ?
C14A C15A H15B 110.0 . . ?
C16* C15B H15C 110.1 . . ?
C16* C15B H15D 110.1 . . ?
H15C C15B H15D 108.4 . . ?
C15 C15B C16* 108.0(6) . . ?
C15 C15B H15C 110.1 . . ?
C15 C15B H15D 110.1 . . ?
C16* C14 H14E 110.4 . . ?
C16* C14 H14F 110.4 . . ?
H14E C14 H14F 108.6 . . ?
C1A C14 C16* 106.5(7) . . ?
C1A C14 H14E 110.4 . . ?
C1A C14 H14F 110.4 . . ?
C13* C15 H15E 109.4 . . ?
C13* C15 H15F 109.4 . . ?
C15B C15 C13* 111.4(7) . . ?
C15B C15 H15E 109.4 . . ?
C15B C15 H15F 109.4 . . ?
H15E C15 H15F 108.0 . . ?
C13 C14A H14C 109.0 . . ?
C13 C14A H14D 109.0 . . ?
C15A C14A C13 113.0(8) . . ?
C15A C14A H14C 109.0 . . ?
C15A C14A H14D 109.0 . . ?
H14C C14A H14D 107.8 . . ?
C13* C1A H1AA 109.3 . . ?
C13* C1A H1AB 109.3 . . ?
C14 C1A C13* 111.8(8) . . ?
C14 C1A H1AA 109.3 . . ?
C14 C1A H1AB 109.3 . . ?
H1AA C1A H1AB 107.9 . . ?
C13 C1B H1BA 109.7 . . ?
C13 C1B H1BB 109.7 . . ?
C14B C1B C13 109.8(6) . . ?
C14B C1B H1BA 109.7 . . ?
C14B C1B H1BB 109.7 . . ?
H1BA C1B H1BB 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C3 C4 C5 178.2(2) . . . . ?
F1 C3 C2 C1 -179.0(3) . . . . ?
F1* C3* C2* C1* 179.6(3) . . . . ?
O1 C9 C10 C11 -167.9(3) . . . . ?
O1 C9 C8 C7 21.1(4) . . . . ?
O1* C9* C8* C7* -16.4(4) . . . . ?
O1* C9* C10* C11* 171.8(3) . . . . ?
C6* C5* C4* C3* -0.2(4) . . . . ?
C6* C7* C8* C9* -178.2(3) . . . . ?
C6* C1* C2* C3* 0.3(5) . . . . ?
C7 C6 C5 C4 -177.5(3) . . . . ?
C7 C6 C1 C2 176.7(3) . . . . ?
C17* C16* C15B C15 50.1(7) . . . . ?
C17* C16* C14 C1A -54.0(7) . . . . ?
C5* C6* C7* C8* -10.6(5) . . . . ?
C5* C6* C1* C2* 0.0(5) . . . . ?
C5* C4* C3* F1* -179.6(2) . . . . ?
C5* C4* C3* C2* 0.6(5) . . . . ?
C12 C17 C16 C14B 19.7(5) . . . . ?
C12 C17 C16 C15A -19.5(6) . . . . ?
C12 C11 C10 C9 172.9(3) . . . . ?
C12 C13 C14A C15A 45.7(9) . . . . ?
C12 C13 C1B C14B -46.8(8) . . . . ?
C17 C12 C11 C10 49.1(4) . . . . ?
C17 C12 C13 C20 121.8(3) . . . . ?
C17 C12 C13 C19 -118.7(3) . . . . ?
C17 C12 C13 C14A -12.7(6) . . . . ?
C17 C12 C13 C1B 13.0(5) . . . . ?
C17 C16 C14B C1B -52.0(7) . . . . ?
C17 C16 C15A C14A 50.5(9) . . . . ?
C6 C7 C8 C9 175.9(3) . . . . ?
C6 C5 C4 C3 0.6(4) . . . . ?
C6 C1 C2 C3 1.0(5) . . . . ?
C11 C12 C17 C18 1.3(4) . . . . ?
C11 C12 C17 C16 -179.1(3) . . . . ?
C11 C12 C13 C20 -58.5(3) . . . . ?
C11 C12 C13 C19 61.0(3) . . . . ?
C11 C12 C13 C14A 166.9(5) . . . . ?
C11 C12 C13 C1B -167.3(4) . . . . ?
C10 C9 C8 C7 -156.1(3) . . . . ?
C7* C6* C5* C4* 179.4(3) . . . . ?
C7* C6* C1* C2* -179.4(3) . . . . ?
C8* C9* C10* C11* -6.4(4) . . . . ?
C5 C6 C1 C2 -1.8(5) . . . . ?
C12* C17* C16* C15B -18.8(5) . . . . ?
C12* C17* C16* C14 21.6(5) . . . . ?
C12* C11* C10* C9* -173.1(3) . . . . ?
C12* C13* C15 C15B 45.2(8) . . . . ?
C12* C13* C1A C14 -47.3(8) . . . . ?
C8 C7 C6 C5 8.9(5) . . . . ?
C8 C7 C6 C1 -169.5(3) . . . . ?
C8 C9 C10 C11 9.3(4) . . . . ?
C1 C6 C5 C4 1.0(4) . . . . ?
C10* C9* C8* C7* 161.8(3) . . . . ?
C10* C11* C12* C17* -50.3(4) . . . . ?
C10* C11* C12* C13* 129.3(3) . . . . ?
C13 C12 C17 C18 -179.0(3) . . . . ?
C13 C12 C17 C16 0.5(4) . . . . ?
C13 C12 C11 C10 -130.6(3) . . . . ?
C4* C3* C2* C1* -0.6(6) . . . . ?
C4 C3 C2 C1 0.6(5) . . . . ?
C18 C17 C16 C14B -160.7(4) . . . . ?
C18 C17 C16 C15A 160.1(5) . . . . ?
C2 C3 C4 C5 -1.4(5) . . . . ?
C1* C6* C5* C4* 0.0(5) . . . . ?
C1* C6* C7* C8* 168.8(3) . . . . ?
C18* C17* C12* C11* -2.2(4) . . . . ?
C18* C17* C12* C13* 178.2(3) . . . . ?
C18* C17* C16* C15B 162.2(4) . . . . ?
C18* C17* C16* C14 -157.4(4) . . . . ?
C16* C17* C12* C11* 178.9(3) . . . . ?
C16* C17* C12* C13* -0.6(4) . . . . ?
C16* C15B C15 C13* -64.7(9) . . . . ?
C16* C14 C1A C13* 69.4(9) . . . . ?
C20* C13* C12* C17* -120.6(3) . . . . ?
C20* C13* C12* C11* 59.8(3) . . . . ?
C20* C13* C15 C15B 162.3(7) . . . . ?
C20* C13* C1A C14 81.5(8) . . . . ?
C20 C13 C14A C15A -84.4(9) . . . . ?
C20 C13 C1B C14B -164.0(6) . . . . ?
C19* C13* C12* C17* 119.8(3) . . . . ?
C19* C13* C12* C11* -59.8(3) . . . . ?
C19* C13* C15 C15B -82.3(8) . . . . ?
C19* C13* C1A C14 -161.3(7) . . . . ?
C19 C13 C14A C15A 159.1(7) . . . . ?
C19 C13 C1B C14B 80.4(7) . . . . ?
C16 C14B C1B C13 66.2(8) . . . . ?
C16 C15A C14A C13 -66.2(10) . . . . ?
C15 C13* C12* C17* -12.2(5) . . . . ?
C15 C13* C12* C11* 168.2(4) . . . . ?
C1A C13* C12* C17* 12.5(5) . . . . ?
C1A C13* C12* C11* -167.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9(12)
2 0.1(12)

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
