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

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

data_cain84_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2095177'
loop_
_audit_author_name
_audit_author_address
'Arnold L. Rheingold'
;University of California, San Diego
United States of America
;
_audit_update_record             
;
2021-07-08 deposited with the CCDC.	2021-08-10 downloaded from the CCDC.
;
_audit_creation_date             2020-01-15
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 Br F12 O2'
_chemical_formula_sum            'C14 H9 Br F12 O2'
_chemical_formula_weight         517.12
_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'
Br Br -0.2901 2.4595 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.9324(10)
_cell_length_b                   12.4694(12)
_cell_length_c                   12.4948(10)
_cell_angle_alpha                90
_cell_angle_beta                 116.905(4)
_cell_angle_gamma                90
_cell_volume                     1657.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1072
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   0.561
_shelx_estimated_absorpt_T_min   0.479
_exptl_absorpt_coefficient_mu    2.618
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0575 before and 0.0436 after correction.
The Ratio of minimum to maximum transmission is 0.8586.
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    2.072
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8685
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.386
_diffrn_reflns_theta_min         1.959
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX CCD'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2816
_reflns_number_total             3370
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_refine_diff_density_max         1.690
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.075
_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)+(0.0717P)²+4.2154P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1341
_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 Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C3(H3)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Br1 Br 0.51705(4) 0.26326(3) 0.28712(4) 0.01708(16) Uani 1 1 d . . . . .
F12 F 0.8013(2) 0.3404(2) 0.4264(2) 0.0238(6) Uani 1 1 d . . . . .
F11 F 0.9253(2) 0.3791(2) 0.3493(2) 0.0251(6) Uani 1 1 d . . . . .
F8 F 0.8153(2) 0.5668(2) 0.1954(3) 0.0270(6) Uani 1 1 d . . . . .
F7 F 0.6437(2) 0.5126(2) 0.0449(2) 0.0218(6) Uani 1 1 d . . . . .
F10 F 0.8458(2) 0.5052(2) 0.4111(2) 0.0249(6) Uani 1 1 d . . . . .
F9 F 0.8120(2) 0.4180(2) 0.1070(2) 0.0258(6) Uani 1 1 d . . . . .
O2 O 0.6912(3) 0.3082(2) 0.1916(2) 0.0140(6) Uani 1 1 d . . . . .
F5 F 0.1598(3) 0.5632(2) 0.2774(3) 0.0364(8) Uani 1 1 d . . . . .
F1 F 0.4091(3) 0.3270(2) 0.4573(2) 0.0325(7) Uani 1 1 d . . . . .
O1 O 0.2554(3) 0.3103(3) 0.2224(3) 0.0213(7) Uani 1 1 d . . . . .
F3 F 0.3582(3) 0.4911(2) 0.4645(3) 0.0330(7) Uani 1 1 d . . . . .
F6 F 0.0636(3) 0.4208(3) 0.1895(3) 0.0389(8) Uani 1 1 d . . . . .
F4 F 0.1446(3) 0.5233(2) 0.1045(3) 0.0361(7) Uani 1 1 d . . . . .
F2 F 0.2202(3) 0.3658(3) 0.4177(3) 0.0371(8) Uani 1 1 d . . . . .
C1 C 0.5002(3) 0.4135(3) 0.2566(3) 0.0095(8) Uani 1 1 d . . . . .
C6 C 0.5938(3) 0.4689(3) 0.2399(3) 0.0086(7) Uani 1 1 d . . . . .
C4 C 0.4934(4) 0.6364(3) 0.2454(4) 0.0151(8) Uani 1 1 d . . . . .
H4 H 0.493422 0.712587 0.245620 0.018 Uiso 1 1 calc R . . . .
C10 C 0.2187(4) 0.2988(4) 0.0949(4) 0.0199(9) Uani 1 1 d . . . . .
H10A H 0.134884 0.329607 0.048243 0.030 Uiso 1 1 calc GR . . . .
H10B H 0.217189 0.222539 0.075171 0.030 Uiso 1 1 calc GR . . . .
H10C H 0.279286 0.336369 0.075489 0.030 Uiso 1 1 calc GR . . . .
C5 C 0.5899(4) 0.5808(3) 0.2377(4) 0.0134(8) Uani 1 1 d . . . . .
H5 H 0.654815 0.619638 0.230703 0.016 Uiso 1 1 calc R . . . .
C2 C 0.3971(4) 0.4685(3) 0.2578(3) 0.0106(8) Uani 1 1 d . . . . .
C12 C 0.8208(4) 0.4099(3) 0.3547(4) 0.0168(9) Uani 1 1 d . . . . .
C3 C 0.3967(4) 0.5803(3) 0.2528(4) 0.0130(8) Uani 1 1 d . . . . .
H3 H 0.328761 0.618816 0.254430 0.016 Uiso 1 1 calc R . . . .
C13 C 0.7449(4) 0.4792(3) 0.1437(4) 0.0178(9) Uani 1 1 d . . . . .
C11 C 0.7061(3) 0.4152(3) 0.2295(3) 0.0095(8) Uani 1 1 d . . . . .
C14 C 0.5956(4) 0.2851(4) 0.0723(4) 0.0205(9) Uani 1 1 d . . . . .
H14A H 0.626982 0.302238 0.014215 0.031 Uiso 1 1 calc GR . . . .
H14B H 0.520796 0.328365 0.055201 0.031 Uiso 1 1 calc GR . . . .
H14C H 0.573697 0.208800 0.066355 0.031 Uiso 1 1 calc GR . . . .
C7 C 0.2861(4) 0.4132(3) 0.2683(4) 0.0129(8) Uani 1 1 d . . . . .
C8 C 0.1632(4) 0.4819(4) 0.2112(5) 0.0271(11) Uani 1 1 d . . . . .
C9 C 0.3192(4) 0.3993(4) 0.4042(4) 0.0254(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.905(4) . ?
F12 C12 1.340(5) . ?
F11 C12 1.336(5) . ?
F8 C13 1.351(5) . ?
F7 C13 1.344(5) . ?
F10 C12 1.345(5) . ?
F9 C13 1.328(5) . ?
O2 C11 1.400(5) . ?
O2 C14 1.438(5) . ?
F5 C8 1.320(6) . ?
F1 C9 1.326(6) . ?
O1 C10 1.455(5) . ?
O1 C7 1.386(5) . ?
F3 C9 1.333(5) . ?
F6 C8 1.332(5) . ?
F4 C8 1.351(6) . ?
F2 C9 1.334(5) . ?
C1 C6 1.408(5) . ?
C1 C2 1.414(5) . ?
C6 C5 1.396(5) . ?
C6 C11 1.554(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(6) . ?
C4 C3 1.388(6) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C5 H5 0.9500 . ?
C2 C3 1.395(5) . ?
C2 C7 1.552(5) . ?
C12 C11 1.545(5) . ?
C3 H3 0.9500 . ?
C13 C11 1.566(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C7 C8 1.564(6) . ?
C7 C9 1.569(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 C14 117.5(3) . . ?
C7 O1 C10 115.9(3) . . ?
C6 C1 Br1 119.5(3) . . ?
C6 C1 C2 121.1(4) . . ?
C2 C1 Br1 119.3(3) . . ?
C1 C6 C11 124.9(3) . . ?
C5 C6 C1 118.1(3) . . ?
C5 C6 C11 116.8(3) . . ?
C5 C4 H4 120.1 . . ?
C5 C4 C3 119.7(4) . . ?
C3 C4 H4 120.1 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C5 H5 119.3 . . ?
C4 C5 C6 121.4(4) . . ?
C4 C5 H5 119.3 . . ?
C1 C2 C7 124.4(3) . . ?
C3 C2 C1 118.0(4) . . ?
C3 C2 C7 117.5(3) . . ?
F12 C12 F10 106.6(3) . . ?
F12 C12 C11 111.3(3) . . ?
F11 C12 F12 107.3(3) . . ?
F11 C12 F10 106.8(3) . . ?
F11 C12 C11 112.4(3) . . ?
F10 C12 C11 112.2(3) . . ?
C4 C3 C2 121.3(4) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
F8 C13 C11 113.4(3) . . ?
F7 C13 F8 107.1(3) . . ?
F7 C13 C11 111.4(3) . . ?
F9 C13 F8 106.7(3) . . ?
F9 C13 F7 107.0(3) . . ?
F9 C13 C11 110.8(3) . . ?
O2 C11 C6 117.2(3) . . ?
O2 C11 C12 102.7(3) . . ?
O2 C11 C13 106.5(3) . . ?
C6 C11 C13 111.8(3) . . ?
C12 C11 C6 109.7(3) . . ?
C12 C11 C13 108.3(3) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C7 C2 116.9(3) . . ?
O1 C7 C8 107.5(3) . . ?
O1 C7 C9 103.7(3) . . ?
C2 C7 C8 112.2(3) . . ?
C2 C7 C9 109.5(3) . . ?
C8 C7 C9 106.3(3) . . ?
F5 C8 F6 106.8(4) . . ?
F5 C8 F4 106.7(4) . . ?
F5 C8 C7 115.0(4) . . ?
F6 C8 F4 106.5(4) . . ?
F6 C8 C7 110.2(4) . . ?
F4 C8 C7 111.2(4) . . ?
F1 C9 F3 107.8(4) . . ?
F1 C9 F2 106.6(4) . . ?
F1 C9 C7 111.5(4) . . ?
F3 C9 F2 107.5(4) . . ?
F3 C9 C7 111.6(4) . . ?
F2 C9 C7 111.5(4) . . ?

_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_cain100_0m_b
_database_code_depnum_ccdc_archive 'CCDC 2095180'
loop_
_audit_author_name
_audit_author_address
'Arnold L. Rheingold'
;University of California, San Diego
United States of America
;
_audit_update_record             
;
2021-07-08 deposited with the CCDC.	2021-08-10 downloaded from the CCDC.
;
_audit_creation_date             2021-05-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H13 F12 O2 P'
_chemical_formula_sum            'C20 H13 F12 O2 P'
_chemical_formula_weight         544.27
_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 0.0181 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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.4519(4)
_cell_length_b                   14.3030(9)
_cell_length_c                   11.4008(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.203(4)
_cell_angle_gamma                90
_cell_volume                     1051.31(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3393
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      69.60
_cell_measurement_theta_min      3.88
_shelx_estimated_absorpt_T_max   0.616
_shelx_estimated_absorpt_T_min   0.551
_exptl_absorpt_coefficient_mu    2.334
_exptl_absorpt_correction_T_max  0.5220
_exptl_absorpt_correction_T_min  0.4062
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0950 before and 0.0453 after correction.
The Ratio of minimum to maximum transmission is 0.7782.
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    1.719
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6831
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.023
_diffrn_reflns_theta_min         3.880
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    0.906
_reflns_Friedel_fraction_max     0.891
_reflns_number_gt                3241
_reflns_number_total             3721
_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 (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 1291 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         3721
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0572P)²+1.0023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1345
_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. Uiso/Uaniso restraints and constraints
Uanis(P1) = Uanis(P1')
Uanis(C17) = Uanis(C1')
Uanis(C18) = Uanis(O1')
Uanis(O2) = Uanis(O2')
3. Others
 Sof(P1')=1-FVAR(1)
 Sof(P1)=FVAR(1)
 Sof(O1')=Sof(O2')=Sof(C1')=Sof(H1'A)=Sof(H1'B)=Sof(H1'C)=1-FVAR(2)
 Sof(O1)=Sof(O2)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C14(H14), C15(H15), C16(H16)
4.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C1(H1A,H1B,H1C), C1'(H1'A,H1'B,H1'C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.5175(18) 0.6976(4) 0.6142(6) 0.112(4) Uani 1 1 d . . . . .
F2 F 0.3119(14) 0.8130(4) 0.6482(6) 0.084(3) Uani 1 1 d . . . . .
F3 F 0.5550(11) 0.7759(4) 0.7724(6) 0.0622(17) Uani 1 1 d . . . . .
F4 F 0.0685(14) 0.7966(4) 0.8341(5) 0.080(3) Uani 1 1 d . . . . .
F5 F 0.3006(9) 0.7381(4) 0.9475(4) 0.0509(14) Uani 1 1 d . . . . .
F6 F 0.0311(9) 0.6609(5) 0.9080(6) 0.0613(18) Uani 1 1 d . . . . .
F7 F 0.0334(10) 0.3373(5) 0.9067(7) 0.070(2) Uani 1 1 d . . . . .
F8 F 0.2999(9) 0.2549(5) 0.9391(5) 0.0625(18) Uani 1 1 d . . . . .
F9 F 0.0504(13) 0.2040(5) 0.8289(5) 0.074(2) Uani 1 1 d . . . . .
F10 F 0.5556(12) 0.2277(5) 0.7593(6) 0.071(2) Uani 1 1 d . . . . .
F11 F 0.3089(14) 0.1853(4) 0.6444(6) 0.084(3) Uani 1 1 d . . . . .
F12 F 0.4781(15) 0.3052(5) 0.5983(5) 0.084(2) Uani 1 1 d . . . . .
O1 O 0.0921(18) 0.6450(7) 0.6835(9) 0.031(3) Uani 0.677(16) 1 d . . P A 1
O1' O 0.154(4) 0.6529(17) 0.655(2) 0.0322(17) Uani 0.323(16) 1 d . . P A 2
O2 O 0.077(2) 0.3587(10) 0.6825(10) 0.030(2) Uani 0.677(16) 1 d . . P A 1
O2' O 0.136(5) 0.349(2) 0.655(3) 0.030(2) Uani 0.323(16) 1 d . . P A 2
C2 C 0.1325(6) 0.5050(9) 0.5146(3) 0.0356(12) Uani 1 1 d . . . . .
C3 C 0.3350(6) 0.5035(9) 0.4785(3) 0.0386(12) Uani 1 1 d . . . . .
H3 H 0.446833 0.503127 0.535239 0.046 Uiso 1 1 calc R U . . .
C4 C 0.3750(6) 0.5024(9) 0.3599(3) 0.0336(10) Uani 1 1 d . . . . .
H4 H 0.514593 0.504045 0.336336 0.040 Uiso 1 1 calc R U . . .
C5 C 0.2150(6) 0.4991(7) 0.2747(3) 0.0278(8) Uani 1 1 d . . . . .
C6 C 0.0141(6) 0.5005(8) 0.3115(3) 0.0315(9) Uani 1 1 d . . . . .
H6 H -0.097654 0.500949 0.254794 0.038 Uiso 1 1 calc R U . . .
C7 C -0.0280(6) 0.5012(8) 0.4298(3) 0.0316(9) Uani 1 1 d . . . . .
H7 H -0.167647 0.498962 0.453135 0.038 Uiso 1 1 calc R U . . .
C8 C 0.2618(7) 0.5001(9) 0.1462(3) 0.0373(10) Uani 1 1 d . . . . .
H8A H 0.278943 0.564788 0.120057 0.056 Uiso 1 1 calc R U . . .
H8B H 0.147049 0.470905 0.100810 0.056 Uiso 1 1 calc R U . . .
H8C H 0.389941 0.465141 0.134116 0.056 Uiso 1 1 calc R U . . .
C9 C 0.2599(13) 0.3261(6) 0.7506(7) 0.0311(17) Uani 1 1 d . . . . .
C10 C 0.403(2) 0.2603(7) 0.6873(8) 0.053(2) Uani 1 1 d . . . . .
C11 C 0.1621(15) 0.2792(6) 0.8575(8) 0.0356(19) Uani 1 1 d . . . . .
C12 C 0.2871(5) 0.4995(7) 0.7548(3) 0.0198(7) Uani 1 1 d . . . . .
C13 C 0.3709(12) 0.4155(5) 0.7903(6) 0.0225(15) Uani 1 1 d . . . . .
C14 C 0.5524(12) 0.4142(5) 0.8651(6) 0.0238(15) Uani 1 1 d . . . . .
H14 H 0.611338 0.356563 0.890963 0.029 Uiso 1 1 calc R U . . .
C15 C 0.6415(6) 0.4979(8) 0.8995(3) 0.0297(9) Uani 1 1 d . . . . .
H15 H 0.765049 0.497473 0.947626 0.036 Uiso 1 1 calc R U . . .
C16 C 0.5554(13) 0.5817(6) 0.8658(7) 0.0295(17) Uani 1 1 d . . . . .
H16 H 0.618515 0.638667 0.890975 0.035 Uiso 1 1 calc R U . . .
C17 C 0.3790(12) 0.5833(5) 0.7960(6) 0.0228(14) Uani 1 1 d . . . . .
C18 C 0.2662(14) 0.6713(6) 0.7561(6) 0.0322(17) Uani 1 1 d . . . . .
C19 C 0.1655(14) 0.7187(6) 0.8613(7) 0.0328(18) Uani 1 1 d . . . . .
C20 C 0.413(2) 0.7403(7) 0.6970(7) 0.055(3) Uani 1 1 d . . . . .
P1' P 0.0505(9) 0.4798(5) 0.6673(5) 0.0215(5) Uani 0.416(7) 1 d . . P A 1
P1 P 0.0496(6) 0.5280(3) 0.6649(3) 0.0215(5) Uani 0.584(7) 1 d . . P A 2
C1 C -0.011(3) 0.2882(12) 0.5942(15) 0.065(4) Uani 0.677(16) 1 d . . P A 1
H1A H 0.066465 0.291430 0.522112 0.098 Uiso 0.677(16) 1 calc R U P A 1
H1B H -0.157530 0.302603 0.576080 0.098 Uiso 0.677(16) 1 calc R U P A 1
H1C H 0.000317 0.225142 0.627391 0.098 Uiso 0.677(16) 1 calc R U P A 1
C1' C -0.002(3) 0.7134(15) 0.6016(16) 0.0228(14) Uani 0.323(16) 1 d . . P A 2
H1'A H -0.059307 0.753777 0.661813 0.034 Uiso 0.323(16) 1 calc R U P A 2
H1'B H -0.113683 0.675427 0.565256 0.034 Uiso 0.323(16) 1 calc R U P A 2
H1'C H 0.060386 0.752103 0.541462 0.034 Uiso 0.323(16) 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 C20 1.328(12) . ?
F2 C20 1.337(12) . ?
F3 C20 1.334(13) . ?
F4 C19 1.309(10) . ?
F5 C19 1.318(9) . ?
F6 C19 1.325(12) . ?
F7 C11 1.316(12) . ?
F8 C11 1.308(9) . ?
F9 C11 1.329(10) . ?
F10 C10 1.341(13) . ?
F11 C10 1.317(11) . ?
F12 C10 1.310(12) . ?
O1 C18 1.421(13) . ?
O1' C18 1.37(2) . ?
O1' P1 1.91(2) . ?
O1' C1' 1.44(3) . ?
O2 C9 1.463(16) . ?
O2 P1' 1.749(16) . ?
O2 C1 1.520(19) . ?
O2' C9 1.36(3) . ?
C2 C3 1.385(6) . ?
C2 C7 1.390(5) . ?
C2 P1' 1.874(7) . ?
C2 P1 1.844(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(6) . ?
C5 C6 1.378(6) . ?
C5 C8 1.508(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(5) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.520(14) . ?
C9 C11 1.548(12) . ?
C9 C13 1.526(10) . ?
C12 C13 1.372(11) . ?
C12 C17 1.410(11) . ?
C12 P1' 1.814(7) . ?
C12 P1 1.856(6) . ?
C13 C14 1.422(11) . ?
C14 H14 0.9500 . ?
C14 C15 1.379(13) . ?
C15 H15 0.9500 . ?
C15 C16 1.370(13) . ?
C16 H16 0.9500 . ?
C16 C17 1.364(11) . ?
C17 C18 1.515(10) . ?
C18 C19 1.542(11) . ?
C18 C20 1.541(14) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1' H1'A 0.9800 . ?
C1' H1'B 0.9800 . ?
C1' H1'C 0.9800 . ?

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
C18 O1' P1 107.8(15) . . ?
C18 O1' C1' 125(2) . . ?
C1' O1' P1 110.2(16) . . ?
C9 O2 P1' 116.2(9) . . ?
C9 O2 C1 114.5(11) . . ?
C1 O2 P1' 124.0(11) . . ?
C3 C2 C7 118.6(4) . . ?
C3 C2 P1' 125.1(4) . . ?
C3 C2 P1 126.1(4) . . ?
C7 C2 P1' 114.1(4) . . ?
C7 C2 P1 114.7(4) . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.4(4) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C8 120.5(4) . . ?
C6 C5 C4 117.9(3) . . ?
C6 C5 C8 121.5(4) . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.2(4) . . ?
C7 C6 H6 119.4 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.6(4) . . ?
C6 C7 H7 119.7 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 C10 116.0(8) . . ?
O2 C9 C11 102.2(8) . . ?
O2 C9 C13 104.5(8) . . ?
O2' C9 C10 96.9(13) . . ?
O2' C9 C11 119.3(15) . . ?
O2' C9 C13 106.7(16) . . ?
C10 C9 C11 112.2(7) . . ?
C10 C9 C13 111.9(8) . . ?
C13 C9 C11 109.3(6) . . ?
F10 C10 C9 111.7(7) . . ?
F11 C10 F10 105.2(8) . . ?
F11 C10 C9 113.7(10) . . ?
F12 C10 F10 111.1(11) . . ?
F12 C10 F11 106.8(8) . . ?
F12 C10 C9 108.3(8) . . ?
F7 C11 F9 105.7(9) . . ?
F7 C11 C9 110.1(7) . . ?
F8 C11 F7 106.7(8) . . ?
F8 C11 F9 107.9(8) . . ?
F8 C11 C9 112.9(8) . . ?
F9 C11 C9 113.0(7) . . ?
C13 C12 C17 119.4(3) . . ?
C13 C12 P1' 109.9(6) . . ?
C13 C12 P1 131.5(6) . . ?
C17 C12 P1' 130.5(7) . . ?
C17 C12 P1 109.0(6) . . ?
C12 C13 C9 118.1(7) . . ?
C12 C13 C14 119.6(6) . . ?
C14 C13 C9 122.3(7) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.0(7) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.3(4) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.9(8) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C18 114.6(6) . . ?
C16 C17 C12 120.7(7) . . ?
C16 C17 C18 124.7(7) . . ?
O1 C18 C17 108.3(7) . . ?
O1 C18 C19 102.8(8) . . ?
O1 C18 C20 113.6(8) . . ?
O1' C18 C17 109.1(12) . . ?
O1' C18 C19 121.1(12) . . ?
O1' C18 C20 94.0(11) . . ?
C17 C18 C19 110.1(6) . . ?
C17 C18 C20 111.5(8) . . ?
C20 C18 C19 110.1(7) . . ?
F4 C19 F5 107.1(7) . . ?
F4 C19 F6 108.2(9) . . ?
F4 C19 C18 113.7(7) . . ?
F5 C19 F6 104.8(8) . . ?
F5 C19 C18 112.7(7) . . ?
F6 C19 C18 109.9(7) . . ?
F1 C20 F2 108.4(8) . . ?
F1 C20 F3 106.2(12) . . ?
F1 C20 C18 110.8(8) . . ?
F2 C20 C18 112.4(11) . . ?
F3 C20 F2 106.4(8) . . ?
F3 C20 C18 112.4(7) . . ?
O2 P1' C2 104.6(7) . . ?
O2 P1' C12 91.3(6) . . ?
C12 P1' C2 102.7(4) . . ?
C2 P1 O1' 89.7(8) . . ?
C2 P1 C12 102.2(3) . . ?
C12 P1 O1' 87.3(8) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1' C1' H1'A 109.5 . . ?
O1' C1' H1'B 109.5 . . ?
O1' C1' H1'C 109.5 . . ?
H1'A C1' H1'B 109.5 . . ?
H1'A C1' H1'C 109.5 . . ?
H1'B C1' H1'C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C18 C19 F4 -66.1(11) . . . . ?
O1 C18 C19 F5 171.8(8) . . . . ?
O1 C18 C19 F6 55.3(9) . . . . ?
O1 C18 C20 F1 -71.9(12) . . . . ?
O1 C18 C20 F2 49.4(11) . . . . ?
O1 C18 C20 F3 169.5(9) . . . . ?
O1' C18 C19 F4 -52.6(17) . . . . ?
O1' C18 C19 F5 -174.7(14) . . . . ?
O1' C18 C19 F6 68.8(15) . . . . ?
O1' C18 C20 F1 -61.5(15) . . . . ?
O1' C18 C20 F2 59.9(14) . . . . ?
O1' C18 C20 F3 179.9(14) . . . . ?
O2 C9 C10 F10 -174.5(9) . . . . ?
O2 C9 C10 F11 -55.7(12) . . . . ?
O2 C9 C10 F12 62.8(12) . . . . ?
O2 C9 C11 F7 -52.6(10) . . . . ?
O2 C9 C11 F8 -171.8(9) . . . . ?
O2 C9 C11 F9 65.4(11) . . . . ?
O2 C9 C13 C12 -1.5(9) . . . . ?
O2 C9 C13 C14 176.4(8) . . . . ?
O2' C9 C10 F10 176.9(17) . . . . ?
O2' C9 C10 F11 -64.3(17) . . . . ?
O2' C9 C10 F12 54.2(17) . . . . ?
O2' C9 C11 F7 -65.3(18) . . . . ?
O2' C9 C11 F8 175.5(17) . . . . ?
O2' C9 C11 F9 52.7(19) . . . . ?
O2' C9 C13 C12 19.9(15) . . . . ?
O2' C9 C13 C14 -162.2(13) . . . . ?
C2 C3 C4 C5 -3(2) . . . . ?
C3 C2 C7 C6 -3.2(19) . . . . ?
C3 C2 P1' O2 -73.7(12) . . . . ?
C3 C2 P1' C12 21.0(13) . . . . ?
C3 C2 P1 O1' 65.3(13) . . . . ?
C3 C2 P1 C12 -21.9(13) . . . . ?
C3 C4 C5 C6 2.5(18) . . . . ?
C3 C4 C5 C8 178.7(12) . . . . ?
C4 C5 C6 C7 -2.7(17) . . . . ?
C5 C6 C7 C2 3.1(18) . . . . ?
C7 C2 C3 C4 3(2) . . . . ?
C7 C2 P1' O2 89.6(10) . . . . ?
C7 C2 P1' C12 -175.7(9) . . . . ?
C7 C2 P1 O1' -106.1(12) . . . . ?
C7 C2 P1 C12 166.7(9) . . . . ?
C8 C5 C6 C7 -178.9(11) . . . . ?
C9 O2 P1' C2 102.8(8) . . . . ?
C9 O2 P1' C12 -0.7(8) . . . . ?
C9 C13 C14 C15 -178.5(7) . . . . ?
C10 C9 C11 F7 -177.5(7) . . . . ?
C10 C9 C11 F8 63.3(10) . . . . ?
C10 C9 C11 F9 -59.5(11) . . . . ?
C10 C9 C13 C12 124.8(7) . . . . ?
C10 C9 C13 C14 -57.3(9) . . . . ?
C11 C9 C10 F10 -57.6(11) . . . . ?
C11 C9 C10 F11 61.3(10) . . . . ?
C11 C9 C10 F12 179.8(8) . . . . ?
C11 C9 C13 C12 -110.3(7) . . . . ?
C11 C9 C13 C14 67.6(9) . . . . ?
C12 C13 C14 C15 -0.6(10) . . . . ?
C12 C17 C18 O1 -0.8(10) . . . . ?
C12 C17 C18 O1' -24.1(13) . . . . ?
C12 C17 C18 C19 110.9(7) . . . . ?
C12 C17 C18 C20 -126.5(6) . . . . ?
C13 C9 C10 F10 65.7(10) . . . . ?
C13 C9 C10 F11 -175.4(7) . . . . ?
C13 C9 C10 F12 -56.9(10) . . . . ?
C13 C9 C11 F7 57.8(9) . . . . ?
C13 C9 C11 F8 -61.4(10) . . . . ?
C13 C9 C11 F9 175.8(8) . . . . ?
C13 C12 C17 C16 3.2(7) . . . . ?
C13 C12 C17 C18 -176.9(7) . . . . ?
C13 C12 P1' O2 -0.2(6) . . . . ?
C13 C12 P1' C2 -105.5(6) . . . . ?
C13 C12 P1 O1' -167.5(8) . . . . ?
C13 C12 P1 C2 -78.4(7) . . . . ?
C13 C14 C15 C16 1.8(7) . . . . ?
C14 C15 C16 C17 -0.5(8) . . . . ?
C15 C16 C17 C12 -2.0(11) . . . . ?
C15 C16 C17 C18 178.1(7) . . . . ?
C16 C17 C18 O1 179.1(9) . . . . ?
C16 C17 C18 O1' 155.8(12) . . . . ?
C16 C17 C18 C19 -69.1(10) . . . . ?
C16 C17 C18 C20 53.4(10) . . . . ?
C17 C12 C13 C9 176.1(7) . . . . ?
C17 C12 C13 C14 -1.8(6) . . . . ?
C17 C12 P1' O2 -174.6(6) . . . . ?
C17 C12 P1' C2 80.1(7) . . . . ?
C17 C12 P1 O1' 17.1(8) . . . . ?
C17 C12 P1 C2 106.2(6) . . . . ?
C17 C18 C19 F4 178.6(8) . . . . ?
C17 C18 C19 F5 56.5(10) . . . . ?
C17 C18 C19 F6 -60.0(9) . . . . ?
C17 C18 C20 F1 50.8(11) . . . . ?
C17 C18 C20 F2 172.2(6) . . . . ?
C17 C18 C20 F3 -67.8(10) . . . . ?
C19 C18 C20 F1 173.4(8) . . . . ?
C19 C18 C20 F2 -65.3(9) . . . . ?
C19 C18 C20 F3 54.8(11) . . . . ?
C20 C18 C19 F4 55.3(11) . . . . ?
C20 C18 C19 F5 -66.8(10) . . . . ?
C20 C18 C19 F6 176.7(7) . . . . ?
P1' O2 C9 C10 -122.4(8) . . . . ?
P1' O2 C9 C11 115.2(8) . . . . ?
P1' O2 C9 C13 1.3(10) . . . . ?
P1' C2 C3 C4 165.5(10) . . . . ?
P1' C2 C7 C6 -167.6(10) . . . . ?
P1' C12 C13 C9 1.0(7) . . . . ?
P1' C12 C13 C14 -176.9(6) . . . . ?
P1' C12 C17 C16 177.1(6) . . . . ?
P1' C12 C17 C18 -3.0(9) . . . . ?
P1 O1' C18 C17 36.0(15) . . . . ?
P1 O1' C18 C19 -93.3(15) . . . . ?
P1 O1' C18 C20 150.4(11) . . . . ?
P1 C2 C3 C4 -168.2(10) . . . . ?
P1 C2 C7 C6 168.9(10) . . . . ?
P1 C12 C13 C9 1.2(9) . . . . ?
P1 C12 C13 C14 -176.8(5) . . . . ?
P1 C12 C17 C16 179.2(6) . . . . ?
P1 C12 C17 C18 -0.9(7) . . . . ?
C1 O2 C9 C10 32.9(14) . . . . ?
C1 O2 C9 C11 -89.6(12) . . . . ?
C1 O2 C9 C13 156.5(11) . . . . ?
C1 O2 P1' C2 -49.9(14) . . . . ?
C1 O2 P1' C12 -153.4(12) . . . . ?
C1' O1' C18 C17 168.2(18) . . . . ?
C1' O1' C18 C19 39(3) . . . . ?
C1' O1' C18 C20 -77(2) . . . . ?

_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_cain80_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2095181'
loop_
_audit_author_name
_audit_author_address
'Arnold L. Rheingold'
;University of California, San Diego
United States of America
;
_audit_update_record             
;
2021-07-08 deposited with the CCDC.	2021-08-10 downloaded from the CCDC.
;
_audit_creation_date             2019-05-23
_audit_creation_method           
;
Olex2 1.2-beta
(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         'C11 H7 Br F6 O3'
_chemical_formula_sum            'C11 H7 Br F6 O3'
_chemical_formula_weight         381.08
_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'
Br Br -0.2901 2.4595 '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           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                   13.9233(7)
_cell_length_b                   14.4415(9)
_cell_length_c                   12.9349(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.826(2)
_cell_angle_gamma                90
_cell_volume                     2554.6(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2736
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.77
_shelx_estimated_absorpt_T_max   0.458
_shelx_estimated_absorpt_T_min   0.418
_exptl_absorpt_coefficient_mu    3.300
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0833 before and 0.0669 after correction. The Ratio of minimum to maximum transmission is 0.7726. 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    1.982
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8847
_diffrn_reflns_point_group_measured_fraction_full 0.745
_diffrn_reflns_point_group_measured_fraction_max 0.726
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.287
_diffrn_reflns_theta_min         2.051
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 8.258
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.452
_reflns_Friedel_fraction_full    0.491
_reflns_Friedel_fraction_max     0.453
_reflns_number_gt                4370
_reflns_number_total             4616
_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 (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 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         0.414
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.007(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.833
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         4616
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0230
_refine_ls_restrained_S_all      0.833
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0533
_refine_ls_wR_factor_ref         0.0541
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C9'(H9'), C7'(H7'), C8'(H8'), C7(H7)
2.b Idealised Me refined as rotating group:
 C11'(H11A,H11B,H11C), C11(H11D,H11E,H11F)
2.c Idealised tetrahedral OH refined as rotating group:
 O1'(H1')
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Br1' Br 0.56688(2) 0.56276(2) 0.68114(2) 0.01416(8) Uani 1 1 d . . . . .
Br1 Br 0.52561(2) 0.12663(2) 0.66614(2) 0.01445(8) Uani 1 1 d . . . . .
F1 F 0.54751(15) -0.07546(15) 0.57671(16) 0.0191(4) Uani 1 1 d . . . . .
F4' F 0.26846(17) 0.61011(17) 0.45232(17) 0.0234(5) Uani 1 1 d . . . . .
F2' F 0.27356(15) 0.46697(17) 0.32178(16) 0.0227(5) Uani 1 1 d . . . . .
F4 F 0.33857(16) -0.07664(16) 0.30171(17) 0.0228(5) Uani 1 1 d . . . . .
F6' F 0.34172(16) 0.59434(17) 0.61390(16) 0.0234(5) Uani 1 1 d . . . . .
O1' O 0.41658(17) 0.42804(17) 0.57602(18) 0.0142(5) Uani 1 1 d . . . . .
H1' H 0.4705 0.4050 0.5694 0.021 Uiso 1 1 calc GR . . . .
F6 F 0.26006(15) 0.03646(16) 0.35898(17) 0.0213(5) Uani 1 1 d . . . . .
F3 F 0.43356(15) -0.17188(15) 0.51465(18) 0.0234(5) Uani 1 1 d . . . . .
O1 O 0.36866(17) -0.00249(19) 0.56786(18) 0.0136(5) Uani 1 1 d . . . . .
F1' F 0.40319(16) 0.38118(15) 0.35636(17) 0.0222(5) Uani 1 1 d . . . . .
O3 O 0.59237(18) 0.35246(18) 0.5804(2) 0.0198(5) Uani 1 1 d . . . . .
F2 F 0.51977(16) -0.10923(16) 0.41165(17) 0.0227(5) Uani 1 1 d . . . . .
O3' O 0.77502(17) 0.66093(19) 0.5833(2) 0.0177(5) Uani 1 1 d . . . . .
F3' F 0.28209(17) 0.35691(17) 0.43405(19) 0.0282(5) Uani 1 1 d . . . . .
F5 F 0.25843(16) -0.09959(17) 0.42569(17) 0.0240(5) Uani 1 1 d . . . . .
O2 O 0.70807(16) 0.24372(17) 0.60009(19) 0.0161(5) Uani 1 1 d . . . . .
O2' O 0.66827(16) 0.76122(16) 0.62966(18) 0.0151(5) Uani 1 1 d . . . . .
F5' F 0.22880(16) 0.49849(19) 0.5464(2) 0.0321(6) Uani 1 1 d . . . . .
C10 C 0.6211(2) 0.2765(2) 0.5604(2) 0.0119(6) Uani 1 1 d . . . . .
C11' C 0.7487(2) 0.8046(3) 0.7012(3) 0.0187(7) Uani 1 1 d . . . . .
H11A H 0.7985 0.8249 0.6617 0.028 Uiso 1 1 calc GR . . . .
H11B H 0.7775 0.7598 0.7552 0.028 Uiso 1 1 calc GR . . . .
H11C H 0.7243 0.8582 0.7348 0.028 Uiso 1 1 calc GR . . . .
C11 C 0.7693(2) 0.3018(3) 0.6772(3) 0.0194(7) Uani 1 1 d . . . . .
H11D H 0.7844 0.3594 0.6436 0.029 Uiso 1 1 calc GR . . . .
H11E H 0.8302 0.2690 0.7055 0.029 Uiso 1 1 calc GR . . . .
H11F H 0.7347 0.3161 0.7346 0.029 Uiso 1 1 calc GR . . . .
C10' C 0.6923(2) 0.6889(2) 0.5762(2) 0.0121(6) Uani 1 1 d . . . . .
C5' C 0.5403(2) 0.5886(2) 0.5345(2) 0.0108(6) Uani 1 1 d . . . . .
C9 C 0.4632(2) 0.0886(3) 0.3376(3) 0.0135(6) Uani 1 1 d . . . . .
H9 H 0.4301 0.0465 0.2865 0.016 Uiso 1 1 calc R . . . .
C8 C 0.5130(2) 0.1629(3) 0.3045(3) 0.0147(7) Uani 1 1 d . . . . .
H8 H 0.5132 0.1713 0.2317 0.018 Uiso 1 1 calc R . . . .
C3 C 0.4774(3) -0.0937(3) 0.4945(3) 0.0158(7) Uani 1 1 d . . . . .
C4' C 0.4622(2) 0.5516(2) 0.4612(3) 0.0102(6) Uani 1 1 d . . . . .
C5 C 0.5130(2) 0.1355(2) 0.5178(2) 0.0097(6) Uani 1 1 d . . . . .
C4 C 0.4602(2) 0.0738(2) 0.4441(2) 0.0105(6) Uani 1 1 d . . . . .
C6 C 0.5633(2) 0.2104(2) 0.4833(3) 0.0120(6) Uani 1 1 d . . . . .
C9' C 0.4529(2) 0.5805(2) 0.3567(3) 0.0139(6) Uani 1 1 d . . . . .
H9' H 0.4008 0.5563 0.3059 0.017 Uiso 1 1 calc R . . . .
C2' C 0.3835(2) 0.4872(2) 0.4916(3) 0.0122(6) Uani 1 1 d . . . . .
C7' C 0.5938(2) 0.6781(3) 0.3974(3) 0.0148(7) Uani 1 1 d . . . . .
H7' H 0.6381 0.7209 0.3761 0.018 Uiso 1 1 calc R . . . .
C6' C 0.6061(2) 0.6507(2) 0.5014(3) 0.0114(6) Uani 1 1 d . . . . .
C8' C 0.5169(3) 0.6434(3) 0.3242(3) 0.0161(7) Uani 1 1 d . . . . .
H8' H 0.5078 0.6622 0.2527 0.019 Uiso 1 1 calc R . . . .
C3' C 0.3339(3) 0.4235(3) 0.3989(3) 0.0175(7) Uani 1 1 d . . . . .
C1' C 0.3041(3) 0.5484(3) 0.5266(3) 0.0175(7) Uani 1 1 d . . . . .
C2 C 0.4052(2) -0.0115(2) 0.4749(2) 0.0116(6) Uani 1 1 d . . . . .
C1 C 0.3148(3) -0.0381(3) 0.3887(3) 0.0166(7) Uani 1 1 d . . . . .
C7 C 0.5624(2) 0.2247(2) 0.3776(3) 0.0140(7) Uani 1 1 d . . . . .
H7 H 0.5953 0.2764 0.3552 0.017 Uiso 1 1 calc R . . . .
H1 H 0.345(3) 0.046(3) 0.568(3) 0.012(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1' C5' 1.900(3) . ?
Br1 C5 1.898(3) . ?
F1 C3 1.327(4) . ?
F4' C1' 1.336(4) . ?
F2' C3' 1.334(4) . ?
F4 C1 1.352(4) . ?
F6' C1' 1.330(4) . ?
O1' H1' 0.8400 . ?
O1' C2' 1.395(4) . ?
F6 C1 1.333(4) . ?
F3 C3 1.332(4) . ?
O1 C2 1.396(4) . ?
O1 H1 0.78(4) . ?
F1' C3' 1.344(4) . ?
O3 C10 1.211(4) . ?
F2 C3 1.336(4) . ?
O3' C10' 1.208(4) . ?
F3' C3' 1.333(4) . ?
F5 C1 1.332(4) . ?
O2 C10 1.312(4) . ?
O2 C11 1.451(4) . ?
O2' C11' 1.453(4) . ?
O2' C10' 1.329(4) . ?
F5' C1' 1.336(4) . ?
C10 C6 1.502(5) . ?
C11' H11A 0.9800 . ?
C11' H11B 0.9800 . ?
C11' H11C 0.9800 . ?
C11 H11D 0.9800 . ?
C11 H11E 0.9800 . ?
C11 H11F 0.9800 . ?
C10' C6' 1.498(5) . ?
C5' C4' 1.407(5) . ?
C5' C6' 1.405(4) . ?
C9 H9 0.9500 . ?
C9 C8 1.388(5) . ?
C9 C4 1.403(4) . ?
C8 H8 0.9500 . ?
C8 C7 1.385(5) . ?
C3 C2 1.546(5) . ?
C4' C9' 1.396(4) . ?
C4' C2' 1.544(4) . ?
C5 C4 1.408(5) . ?
C5 C6 1.406(5) . ?
C4 C2 1.542(4) . ?
C6 C7 1.380(4) . ?
C9' H9' 0.9500 . ?
C9' C8' 1.392(5) . ?
C2' C3' 1.565(5) . ?
C2' C1' 1.547(5) . ?
C7' H7' 0.9500 . ?
C7' C6' 1.383(5) . ?
C7' C8' 1.383(5) . ?
C8' H8' 0.9500 . ?
C2 C1 1.565(5) . ?
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
C2' O1' H1' 109.5 . . ?
C2 O1 H1 108(3) . . ?
C10 O2 C11 116.1(3) . . ?
C10' O2' C11' 115.5(3) . . ?
O3 C10 O2 124.1(3) . . ?
O3 C10 C6 124.1(3) . . ?
O2 C10 C6 111.7(3) . . ?
O2' C11' H11A 109.5 . . ?
O2' C11' H11B 109.5 . . ?
O2' C11' H11C 109.5 . . ?
H11A C11' H11B 109.5 . . ?
H11A C11' H11C 109.5 . . ?
H11B C11' H11C 109.5 . . ?
O2 C11 H11D 109.5 . . ?
O2 C11 H11E 109.5 . . ?
O2 C11 H11F 109.5 . . ?
H11D C11 H11E 109.5 . . ?
H11D C11 H11F 109.5 . . ?
H11E C11 H11F 109.5 . . ?
O3' C10' O2' 123.6(3) . . ?
O3' C10' C6' 124.2(3) . . ?
O2' C10' C6' 112.1(3) . . ?
C4' C5' Br1' 125.4(2) . . ?
C6' C5' Br1' 114.4(2) . . ?
C6' C5' C4' 120.2(3) . . ?
C8 C9 H9 119.0 . . ?
C8 C9 C4 121.9(3) . . ?
C4 C9 H9 119.0 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 C9 120.1(3) . . ?
C7 C8 H8 120.0 . . ?
F1 C3 F3 107.9(3) . . ?
F1 C3 F2 107.9(3) . . ?
F1 C3 C2 109.7(3) . . ?
F3 C3 F2 107.6(3) . . ?
F3 C3 C2 112.0(3) . . ?
F2 C3 C2 111.6(3) . . ?
C5' C4' C2' 123.6(3) . . ?
C9' C4' C5' 117.3(3) . . ?
C9' C4' C2' 119.0(3) . . ?
C4 C5 Br1 125.4(2) . . ?
C6 C5 Br1 114.6(2) . . ?
C6 C5 C4 120.0(3) . . ?
C9 C4 C5 117.4(3) . . ?
C9 C4 C2 118.9(3) . . ?
C5 C4 C2 123.5(3) . . ?
C5 C6 C10 121.0(3) . . ?
C7 C6 C10 117.8(3) . . ?
C7 C6 C5 121.2(3) . . ?
C4' C9' H9' 118.7 . . ?
C8' C9' C4' 122.6(3) . . ?
C8' C9' H9' 118.7 . . ?
O1' C2' C4' 115.0(3) . . ?
O1' C2' C3' 105.8(3) . . ?
O1' C2' C1' 105.6(3) . . ?
C4' C2' C3' 113.0(3) . . ?
C4' C2' C1' 108.1(3) . . ?
C1' C2' C3' 108.9(3) . . ?
C6' C7' H7' 120.0 . . ?
C6' C7' C8' 120.0(3) . . ?
C8' C7' H7' 120.0 . . ?
C5' C6' C10' 121.9(3) . . ?
C7' C6' C10' 117.4(3) . . ?
C7' C6' C5' 120.7(3) . . ?
C9' C8' H8' 120.4 . . ?
C7' C8' C9' 119.2(3) . . ?
C7' C8' H8' 120.4 . . ?
F2' C3' F1' 107.9(3) . . ?
F2' C3' C2' 114.9(3) . . ?
F1' C3' C2' 109.5(3) . . ?
F3' C3' F2' 106.8(3) . . ?
F3' C3' F1' 106.7(3) . . ?
F3' C3' C2' 110.6(3) . . ?
F4' C1' F5' 107.4(3) . . ?
F4' C1' C2' 111.1(3) . . ?
F6' C1' F4' 108.1(3) . . ?
F6' C1' F5' 107.7(3) . . ?
F6' C1' C2' 110.2(3) . . ?
F5' C1' C2' 112.2(3) . . ?
O1 C2 C3 105.1(3) . . ?
O1 C2 C4 115.3(3) . . ?
O1 C2 C1 105.2(2) . . ?
C3 C2 C1 109.9(3) . . ?
C4 C2 C3 108.4(2) . . ?
C4 C2 C1 112.6(3) . . ?
F4 C1 C2 113.8(3) . . ?
F6 C1 F4 107.9(3) . . ?
F6 C1 C2 110.3(3) . . ?
F5 C1 F4 106.1(3) . . ?
F5 C1 F6 107.4(3) . . ?
F5 C1 C2 110.9(3) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 C8 119.4(3) . . ?
C6 C7 H7 120.3 . . ?

_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_cain57_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2095178'
loop_
_audit_author_name
_audit_author_address
'Arnold L. Rheingold'
;University of California, San Diego
United States of America
;
_audit_update_record             
;
2021-07-08 deposited with the CCDC.	2021-08-10 downloaded from the CCDC.
;
_audit_creation_date             2017-06-22
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H29 Br O2'
_chemical_formula_sum            'C26 H29 Br O2'
_chemical_formula_weight         453.40
_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'
Br Br -0.2901 2.4595 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4093(13)
_cell_length_b                   8.2707(14)
_cell_length_c                   18.706(3)
_cell_angle_alpha                101.293(4)
_cell_angle_beta                 100.471(5)
_cell_angle_gamma                94.032(6)
_cell_volume                     1098.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4237
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.285
_cell_measurement_theta_min      2.526
_shelx_estimated_absorpt_T_max   0.620
_shelx_estimated_absorpt_T_min   0.583
_exptl_absorpt_coefficient_mu    1.890
_exptl_absorpt_correction_T_max  0.2590
_exptl_absorpt_correction_T_min  0.2112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0637 before and 0.0404 after correction. The Ratio of minimum to maximum transmission is 0.8154. 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    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11445
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.372
_diffrn_reflns_theta_min         2.813
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX CCD'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3478
_reflns_number_total             3990
_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       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'XT (Sheldrick, 2008)'
_refine_diff_density_max         2.092
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3990
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0679P)²+1.2910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1231
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C5(H5), C20(H20), C11(H11), C3(H3), C4(H4), C22(H22)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C26(H26A,H26B,
 H26C), C25(H25A,H25B,H25C), C16(H16A,H16B,H16C)
;
_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
Br1 Br 0.20580(5) 0.14291(4) 0.50604(2) 0.02226(15) Uani 1 1 d . . . . .
O1 O 0.3198(3) 0.4135(3) 0.68291(13) 0.0170(5) Uani 1 1 d . . . . .
O2 O 0.1719(3) 0.2549(3) 0.32476(13) 0.0177(5) Uani 1 1 d . . . . .
C9 C 0.4142(5) 0.3949(5) 0.75211(19) 0.0172(7) Uani 1 1 d . . . . .
C18 C 0.0838(5) 0.1614(4) 0.25527(19) 0.0172(7) Uani 1 1 d . . . . .
C13 C 0.5742(5) 0.5178(5) 0.8762(2) 0.0239(8) Uani 1 1 d . . . . .
H13 H 0.620182 0.613324 0.914302 0.029 Uiso 1 1 calc R . . . .
C24 C 0.0386(5) 0.4310(5) 0.2127(2) 0.0234(8) Uani 1 1 d . . . . .
H24A H -0.058209 0.473080 0.238346 0.035 Uiso 1 1 calc GR . . . .
H24B H 0.026436 0.466055 0.165086 0.035 Uiso 1 1 calc GR . . . .
H24C H 0.160003 0.475318 0.243638 0.035 Uiso 1 1 calc GR . . . .
C14 C 0.4820(5) 0.5373(5) 0.8068(2) 0.0189(8) Uani 1 1 d . . . . .
C10 C 0.4363(5) 0.2357(5) 0.7652(2) 0.0204(8) Uani 1 1 d . . . . .
C17 C 0.4616(5) 0.7078(5) 0.7915(2) 0.0243(8) Uani 1 1 d . . . . .
H17A H 0.557331 0.737887 0.765056 0.036 Uiso 1 1 calc GR . . . .
H17B H 0.474584 0.788327 0.838615 0.036 Uiso 1 1 calc GR . . . .
H17C H 0.339500 0.708181 0.760756 0.036 Uiso 1 1 calc GR . . . .
C19 C 0.0193(5) 0.2451(5) 0.1989(2) 0.0187(8) Uani 1 1 d . . . . .
C2 C 0.3472(5) 0.4811(4) 0.56610(19) 0.0143(7) Uani 1 1 d . . . . .
C12 C 0.6002(5) 0.3620(5) 0.8905(2) 0.0263(9) Uani 1 1 d . . . . .
C21 C -0.0882(5) -0.0224(5) 0.1154(2) 0.0245(9) Uani 1 1 d . . . . .
C6 C 0.1519(5) 0.4236(4) 0.44098(19) 0.0152(7) Uani 1 1 d . . . . .
C5 C 0.1739(5) 0.5923(4) 0.44172(19) 0.0181(8) Uani 1 1 d . . . . .
H5 H 0.113927 0.632033 0.400246 0.022 Uiso 1 1 calc R . . . .
C20 C -0.0663(5) 0.1495(5) 0.1296(2) 0.0227(8) Uani 1 1 d . . . . .
H20 H -0.111193 0.203838 0.090686 0.027 Uiso 1 1 calc R . . . .
C23 C 0.0678(5) -0.0109(5) 0.2425(2) 0.0203(8) Uani 1 1 d . . . . .
C8 C 0.0438(5) 0.3069(4) 0.37228(19) 0.0175(7) Uani 1 1 d . . . . .
H8A H -0.016395 0.209506 0.385699 0.021 Uiso 1 1 calc R . . . .
H8B H -0.053042 0.363416 0.346262 0.021 Uiso 1 1 calc R . . . .
C11 C 0.5307(5) 0.2227(5) 0.8346(2) 0.0250(9) Uani 1 1 d . . . . .
H11 H 0.548286 0.115773 0.844254 0.030 Uiso 1 1 calc R . . . .
C7 C 0.2378(5) 0.3714(4) 0.50380(19) 0.0135(7) Uani 1 1 d . . . . .
C3 C 0.3678(5) 0.6474(4) 0.5627(2) 0.0174(7) Uani 1 1 d . . . . .
H3 H 0.443084 0.724621 0.603349 0.021 Uiso 1 1 calc R . . . .
C15 C 0.3635(6) 0.0824(5) 0.7058(2) 0.0266(9) Uani 1 1 d . . . . .
H15A H 0.268403 0.109780 0.667602 0.040 Uiso 1 1 calc GR . . . .
H15B H 0.309981 -0.002564 0.728031 0.040 Uiso 1 1 calc GR . . . .
H15C H 0.464803 0.040290 0.683023 0.040 Uiso 1 1 calc GR . . . .
C1 C 0.4457(5) 0.4257(4) 0.63328(19) 0.0159(7) Uani 1 1 d . . . . .
H1A H 0.489953 0.316557 0.617837 0.019 Uiso 1 1 calc R . . . .
H1B H 0.553954 0.506571 0.658974 0.019 Uiso 1 1 calc R . . . .
C4 C 0.2820(5) 0.7032(4) 0.5021(2) 0.0199(8) Uani 1 1 d . . . . .
H4 H 0.296736 0.817979 0.501530 0.024 Uiso 1 1 calc R . . . .
C22 C -0.0183(6) -0.1003(5) 0.1723(2) 0.0257(9) Uani 1 1 d . . . . .
H22 H -0.029831 -0.218062 0.162863 0.031 Uiso 1 1 calc R . . . .
C26 C 0.1386(6) -0.1006(5) 0.3031(2) 0.0282(9) Uani 1 1 d . . . . .
H26A H 0.223074 -0.023312 0.343805 0.042 Uiso 1 1 calc GR . . . .
H26B H 0.204166 -0.192364 0.282963 0.042 Uiso 1 1 calc GR . . . .
H26C H 0.034337 -0.144444 0.321898 0.042 Uiso 1 1 calc GR . . . .
C25 C -0.1889(6) -0.1229(6) 0.0403(2) 0.0370(11) Uani 1 1 d . . . . .
H25A H -0.289975 -0.063955 0.020163 0.055 Uiso 1 1 calc GR . . . .
H25B H -0.239133 -0.231421 0.045914 0.055 Uiso 1 1 calc GR . . . .
H25C H -0.102648 -0.138134 0.006115 0.055 Uiso 1 1 calc GR . . . .
C16 C 0.7060(6) 0.3434(6) 0.9649(2) 0.0371(11) Uani 1 1 d . . . . .
H16A H 0.836783 0.381760 0.969996 0.056 Uiso 1 1 calc GR . . . .
H16B H 0.693210 0.226447 0.968221 0.056 Uiso 1 1 calc GR . . . .
H16C H 0.656647 0.409807 1.004857 0.056 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
Br1 C7 1.897(3) . ?
O1 C9 1.397(4) . ?
O1 C1 1.443(4) . ?
O2 C18 1.393(4) . ?
O2 C8 1.445(4) . ?
C9 C14 1.395(5) . ?
C9 C10 1.401(5) . ?
C18 C19 1.403(5) . ?
C18 C23 1.391(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.396(5) . ?
C13 C12 1.386(6) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C24 C19 1.501(5) . ?
C14 C17 1.506(5) . ?
C10 C11 1.387(5) . ?
C10 C15 1.506(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 C20 1.391(5) . ?
C2 C7 1.406(5) . ?
C2 C3 1.389(5) . ?
C2 C1 1.503(5) . ?
C12 C11 1.391(6) . ?
C12 C16 1.510(5) . ?
C21 C20 1.387(5) . ?
C21 C22 1.389(6) . ?
C21 C25 1.516(5) . ?
C6 C5 1.390(5) . ?
C6 C8 1.502(5) . ?
C6 C7 1.392(5) . ?
C5 H5 0.9500 . ?
C5 C4 1.386(5) . ?
C20 H20 0.9500 . ?
C23 C22 1.388(5) . ?
C23 C26 1.510(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C11 H11 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.374(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C4 H4 0.9500 . ?
C22 H22 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 O1 C1 110.7(2) . . ?
C18 O2 C8 112.6(3) . . ?
O1 C9 C10 119.7(3) . . ?
C14 C9 O1 118.4(3) . . ?
C14 C9 C10 121.8(3) . . ?
O2 C18 C19 118.5(3) . . ?
C23 C18 O2 119.8(3) . . ?
C23 C18 C19 121.7(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.4(4) . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
C9 C14 C13 118.1(3) . . ?
C9 C14 C17 121.3(3) . . ?
C13 C14 C17 120.6(3) . . ?
C9 C10 C15 121.6(3) . . ?
C11 C10 C9 117.9(3) . . ?
C11 C10 C15 120.4(3) . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 C19 C24 121.5(3) . . ?
C20 C19 C18 117.7(3) . . ?
C20 C19 C24 120.8(3) . . ?
C7 C2 C1 123.3(3) . . ?
C3 C2 C7 116.9(3) . . ?
C3 C2 C1 119.7(3) . . ?
C13 C12 C11 118.9(4) . . ?
C13 C12 C16 120.7(4) . . ?
C11 C12 C16 120.4(4) . . ?
C20 C21 C22 118.4(3) . . ?
C20 C21 C25 120.8(4) . . ?
C22 C21 C25 120.8(4) . . ?
C5 C6 C8 119.0(3) . . ?
C5 C6 C7 117.6(3) . . ?
C7 C6 C8 123.4(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C19 C20 H20 118.9 . . ?
C21 C20 C19 122.1(4) . . ?
C21 C20 H20 118.9 . . ?
C18 C23 C26 121.6(3) . . ?
C22 C23 C18 118.3(3) . . ?
C22 C23 C26 120.1(3) . . ?
O2 C8 C6 107.5(3) . . ?
O2 C8 H8A 110.2 . . ?
O2 C8 H8B 110.2 . . ?
C6 C8 H8A 110.2 . . ?
C6 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
C10 C11 C12 121.8(4) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C2 C7 Br1 118.3(3) . . ?
C6 C7 Br1 118.9(3) . . ?
C6 C7 C2 122.8(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C1 C2 109.0(3) . . ?
O1 C1 H1A 109.9 . . ?
O1 C1 H1B 109.9 . . ?
C2 C1 H1A 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C21 C22 H22 119.1 . . ?
C23 C22 C21 121.8(4) . . ?
C23 C22 H22 119.1 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C21 C25 H25A 109.5 . . ?
C21 C25 H25B 109.5 . . ?
C21 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_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_cain58
_database_code_depnum_ccdc_archive 'CCDC 2095179'
loop_
_audit_author_name
_audit_author_address
'Arnold L. Rheingold'
;University of California, San Diego
United States of America
;
_audit_update_record             
;
2021-07-08 deposited with the CCDC.	2021-08-10 downloaded from the CCDC.
;
_audit_creation_date             2017-06-30
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.06.29 svn.r3433 for OlexSys, GUI svn.r5356)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C78 H87 O6 P3'
_chemical_formula_sum            'C78 H87 O6 P3'
_chemical_formula_weight         1213.38
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.515(5)
_cell_length_b                   15.037(8)
_cell_length_c                   22.719(11)
_cell_angle_alpha                100.80(3)
_cell_angle_beta                 94.78(2)
_cell_angle_gamma                103.351(19)
_cell_volume                     3403(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.714
_cell_measurement_theta_min      2.305
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.2571
_exptl_absorpt_correction_T_min  0.2038
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1176 before and 0.0648 after correction. The Ratio of minimum to maximum transmission is 0.7927. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_unetI/netI     0.0804
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.670
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            45744
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.670
_diffrn_reflns_theta_full        23.409
_diffrn_reflns_theta_max         23.409
_diffrn_reflns_theta_min         1.425
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.670
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6904
_reflns_number_total             9821
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX2 v2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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         0.408
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     803
_refine_ls_number_reflns         9821
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0788
_refine_ls_restrained_S_all      1.096
_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)+(0.0134P)²+15.2377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1660
_refine_ls_wR_factor_ref         0.1799
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9938(5)
 0.0062(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C7(H7A,H7B), C59(H59A,H59B), C69(H69A,H69B), C33(H33A,H33B),
 C43(H43A,H43B)
3.b Aromatic/amide H refined with riding coordinates:
 C57(H57), C3(H3), C55(H55), C20(H20), C22(H22), C74(H74), C72(H72), C38(H38),
 C5(H5), C56(H56), C64(H64), C4(H4), C31(H31), C62(H62), C36(H36), C29(H29),
 C48(H48), C10(H10), C30(H30), C12(H12), C46(H46)
3.c Idealised Me refined as rotating group:
 C76(H76A,H76B,H76C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C50(H50A,H50B,
 H50C), C40(H40A,H40B,H40C), C25(H25A,H25B,H25C), C66(H66A,H66B,H66C), C78(H78A,
 H78B,H78C), C16(H16A,H16B,H16C), C77(H77A,H77B,H77C), C68(H68A,H68B,H68C),
 C41(H41A,H41B,H41C), C67(H67A,H67B,H67C), C14(H14A,H14B,H14C), C42(H42A,H42B,
 H42C), C52(H52A,H52B,H52C), C15(H15A,H15B,H15C), C51(H51A,H51B,H51C)
;
_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
P2 P 0.27531(12) 0.73306(10) 0.70456(6) 0.0227(3) Uani 1 1 d . . . . .
P3 P 0.11065(12) 0.60595(10) 0.69161(6) 0.0233(3) Uani 1 1 d . . . . .
P1 P 0.20464(12) 0.68538(10) 0.78430(6) 0.0229(3) Uani 1 1 d . . . . .
O6 O -0.0511(3) 0.3706(2) 0.70373(15) 0.0245(8) Uani 1 1 d . . . . .
O2 O 0.5561(3) 0.7449(2) 0.78244(15) 0.0246(8) Uani 1 1 d . . . . .
O1 O 0.0898(3) 0.5570(2) 0.93357(15) 0.0270(8) Uani 1 1 d . . . . .
O4 O 0.1390(3) 0.7449(3) 0.56882(16) 0.0333(9) Uani 1 1 d . . . . .
O3 O 0.4426(3) 1.0065(2) 0.81269(17) 0.0335(9) Uani 1 1 d . . . . .
O5 O 0.3542(3) 0.5448(3) 0.53672(15) 0.0321(9) Uani 1 1 d . . . . .
C6 C 0.2497(5) 0.5803(4) 0.8649(2) 0.0239(12) Uani 1 1 d . . . . .
C75 C -0.2555(5) 0.3940(4) 0.7362(2) 0.0239(12) Uani 1 1 d . . . . .
C58 C 0.1750(5) 0.4409(4) 0.7056(2) 0.0229(12) Uani 1 1 d . . . . .
C57 C 0.2456(5) 0.3728(4) 0.6975(2) 0.0252(12) Uani 1 1 d . . . . .
H57 H 0.2301 0.3245 0.7196 0.030 Uiso 1 1 calc R . . . .
C17 C 0.5027(5) 0.6476(4) 0.7585(2) 0.0245(12) Uani 1 1 d . . . . .
H17A H 0.5753 0.6176 0.7490 0.029 Uiso 1 1 calc R . . . .
H17B H 0.4438 0.6387 0.7204 0.029 Uiso 1 1 calc R . . . .
C3 C 0.4848(5) 0.5459(4) 0.8333(2) 0.0263(12) Uani 1 1 d . . . . .
H3 H 0.5661 0.5343 0.8231 0.032 Uiso 1 1 calc R . . . .
C28 C 0.0942(5) 0.8331(4) 0.6632(2) 0.0289(13) Uani 1 1 d . . . . .
C1 C 0.3045(4) 0.6163(3) 0.8166(2) 0.0187(11) Uani 1 1 d . . . . .
C2 C 0.4265(5) 0.6012(3) 0.8025(2) 0.0223(12) Uani 1 1 d . . . . .
C53 C 0.2001(4) 0.5136(3) 0.6746(2) 0.0202(11) Uani 1 1 d . . . . .
C18 C 0.6811(4) 0.7648(3) 0.8159(2) 0.0209(11) Uani 1 1 d . . . . .
C27 C 0.1925(4) 0.8299(4) 0.7089(2) 0.0224(12) Uani 1 1 d . . . . .
C7 C 0.1280(5) 0.6038(4) 0.8869(2) 0.0273(13) Uani 1 1 d . . . . .
H7A H 0.1456 0.6722 0.9021 0.033 Uiso 1 1 calc R . . . .
H7B H 0.0553 0.5850 0.8529 0.033 Uiso 1 1 calc R . . . .
C60 C 0.3811(5) 0.6111(4) 0.5010(2) 0.0261(12) Uani 1 1 d . . . . .
C23 C 0.7901(5) 0.7646(3) 0.7849(2) 0.0223(12) Uani 1 1 d . . . . .
C55 C 0.3564(5) 0.4428(4) 0.6238(2) 0.0275(13) Uani 1 1 d . . . . .
H55 H 0.4174 0.4424 0.5953 0.033 Uiso 1 1 calc R . . . .
C59 C 0.3093(5) 0.5827(4) 0.5915(2) 0.0303(13) Uani 1 1 d . . . . .
H59A H 0.2257 0.5998 0.5818 0.036 Uiso 1 1 calc R . . . .
H59B H 0.3755 0.6400 0.6134 0.036 Uiso 1 1 calc R . . . .
C39 C 0.6619(5) 0.9907(4) 0.8017(2) 0.0277(13) Uani 1 1 d . . . . .
C20 C 0.8191(5) 0.8114(3) 0.9097(2) 0.0260(12) Uani 1 1 d . . . . .
H20 H 0.8292 0.8268 0.9527 0.031 Uiso 1 1 calc R . . . .
C19 C 0.6942(5) 0.7892(3) 0.8783(2) 0.0256(12) Uani 1 1 d . . . . .
C70 C -0.1604(5) 0.3427(4) 0.7332(2) 0.0246(12) Uani 1 1 d . . . . .
C65 C 0.5060(5) 0.6697(4) 0.5086(2) 0.0288(13) Uani 1 1 d . . . . .
C22 C 0.9142(5) 0.7891(4) 0.8187(3) 0.0303(13) Uani 1 1 d . . . . .
H22 H 0.9896 0.7902 0.7983 0.036 Uiso 1 1 calc R . . . .
C32 C 0.2440(5) 0.9083(4) 0.7557(2) 0.0285(13) Uani 1 1 d . . . . .
C54 C 0.2880(5) 0.5118(4) 0.6306(2) 0.0251(12) Uani 1 1 d . . . . .
C35 C 0.6034(5) 1.0509(4) 0.8999(2) 0.0321(13) Uani 1 1 d . . . . .
C74 C -0.3683(5) 0.3586(4) 0.7614(2) 0.0289(13) Uani 1 1 d . . . . .
H74 H -0.4351 0.3918 0.7634 0.035 Uiso 1 1 calc R . . . .
C72 C -0.2897(5) 0.2291(4) 0.7796(2) 0.0315(13) Uani 1 1 d . . . . .
H72 H -0.3005 0.1736 0.7949 0.038 Uiso 1 1 calc R . . . .
C76 C -0.2388(5) 0.4816(4) 0.7134(2) 0.0304(13) Uani 1 1 d . . . . .
H76A H -0.2081 0.5355 0.7474 0.046 Uiso 1 1 calc GR . . . .
H76B H -0.3234 0.4838 0.6929 0.046 Uiso 1 1 calc GR . . . .
H76C H -0.1738 0.4835 0.6849 0.046 Uiso 1 1 calc GR . . . .
C44 C 0.1583(5) 0.8097(4) 0.5317(2) 0.0312(13) Uani 1 1 d . . . . .
C71 C -0.1767(5) 0.2599(4) 0.7538(2) 0.0286(13) Uani 1 1 d . . . . .
C34 C 0.5710(5) 1.0146(3) 0.8389(2) 0.0272(13) Uani 1 1 d . . . . .
C38 C 0.7912(5) 1.0052(3) 0.8288(3) 0.0311(14) Uani 1 1 d . . . . .
H38 H 0.8558 0.9899 0.8047 0.037 Uiso 1 1 calc R . . . .
C69 C 0.0643(5) 0.4260(4) 0.7437(2) 0.0247(12) Uani 1 1 d . . . . .
H69A H 0.0858 0.3931 0.7756 0.030 Uiso 1 1 calc R . . . .
H69B H 0.0498 0.4868 0.7632 0.030 Uiso 1 1 calc R . . . .
C33 C 0.3593(5) 0.9139(4) 0.8021(2) 0.0291(13) Uani 1 1 d . . . . .
H33A H 0.3275 0.9006 0.8402 0.035 Uiso 1 1 calc R . . . .
H33B H 0.4085 0.8676 0.7868 0.035 Uiso 1 1 calc R . . . .
C8 C 0.0154(5) 0.6008(4) 0.9724(2) 0.0287(13) Uani 1 1 d . . . . .
C21 C 0.9309(5) 0.8120(4) 0.8811(2) 0.0297(13) Uani 1 1 d . . . . .
C5 C 0.3102(5) 0.5243(4) 0.8938(2) 0.0307(13) Uani 1 1 d . . . . .
H5 H 0.2706 0.4972 0.9245 0.037 Uiso 1 1 calc R . . . .
C73 C -0.3870(5) 0.2778(4) 0.7835(2) 0.0284(13) Uani 1 1 d . . . . .
C56 C 0.3381(5) 0.3748(4) 0.6576(2) 0.0307(13) Uani 1 1 d . . . . .
H56 H 0.3886 0.3296 0.6534 0.037 Uiso 1 1 calc R . . . .
C61 C 0.2816(5) 0.6148(4) 0.4585(2) 0.0335(14) Uani 1 1 d . . . . .
C9 C -0.1204(5) 0.5853(4) 0.9544(3) 0.0343(14) Uani 1 1 d . . . . .
C49 C 0.2738(5) 0.8801(4) 0.5427(2) 0.0318(14) Uani 1 1 d . . . . .
C24 C 0.5755(5) 0.7929(4) 0.9116(2) 0.0335(14) Uani 1 1 d . . . . .
H24A H 0.5172 0.8225 0.8906 0.050 Uiso 1 1 calc GR . . . .
H24B H 0.6053 0.8294 0.9530 0.050 Uiso 1 1 calc GR . . . .
H24C H 0.5276 0.7292 0.9128 0.050 Uiso 1 1 calc GR . . . .
C64 C 0.5312(5) 0.7364(4) 0.4730(2) 0.0330(14) Uani 1 1 d . . . . .
H64 H 0.6165 0.7777 0.4778 0.040 Uiso 1 1 calc R . . . .
C4 C 0.4280(5) 0.5081(4) 0.8778(3) 0.0329(14) Uani 1 1 d . . . . .
H4 H 0.4698 0.4704 0.8980 0.039 Uiso 1 1 calc R . . . .
C31 C 0.1936(5) 0.9864(4) 0.7601(3) 0.0375(15) Uani 1 1 d . . . . .
H31 H 0.2269 1.0386 0.7929 0.045 Uiso 1 1 calc R . . . .
C37 C 0.8271(5) 1.0414(4) 0.8905(3) 0.0345(14) Uani 1 1 d . . . . .
C45 C 0.0634(5) 0.7981(5) 0.4822(3) 0.0409(16) Uani 1 1 d . . . . .
C26 C 0.7757(5) 0.7437(4) 0.7167(2) 0.0335(14) Uani 1 1 d . . . . .
H26A H 0.7839 0.6800 0.7018 0.050 Uiso 1 1 calc GR . . . .
H26B H 0.8448 0.7884 0.7033 0.050 Uiso 1 1 calc GR . . . .
H26C H 0.6889 0.7491 0.7007 0.050 Uiso 1 1 calc GR . . . .
C63 C 0.4327(6) 0.7431(4) 0.4305(2) 0.0350(14) Uani 1 1 d . . . . .
C13 C 0.0788(6) 0.6547(4) 1.0271(2) 0.0331(14) Uani 1 1 d . . . . .
C62 C 0.3089(6) 0.6820(4) 0.4239(2) 0.0381(15) Uani 1 1 d . . . . .
H62 H 0.2411 0.6864 0.3950 0.046 Uiso 1 1 calc R . . . .
C36 C 0.7336(6) 1.0647(4) 0.9252(3) 0.0351(14) Uani 1 1 d . . . . .
H36 H 0.7584 1.0906 0.9671 0.042 Uiso 1 1 calc R . . . .
C43 C 0.0410(5) 0.7563(4) 0.6086(2) 0.0335(14) Uani 1 1 d . . . . .
H43A H 0.0079 0.6969 0.6217 0.040 Uiso 1 1 calc R . . . .
H43B H -0.0343 0.7702 0.5861 0.040 Uiso 1 1 calc R . . . .
C29 C 0.0479(5) 0.9137(4) 0.6693(3) 0.0432(16) Uani 1 1 d . . . . .
H29 H -0.0187 0.9168 0.6394 0.052 Uiso 1 1 calc R . . . .
C48 C 0.2907(5) 0.9418(5) 0.5046(3) 0.0418(16) Uani 1 1 d . . . . .
H48 H 0.3697 0.9904 0.5118 0.050 Uiso 1 1 calc R . . . .
C50 C 0.3800(5) 0.8880(4) 0.5938(2) 0.0360(14) Uani 1 1 d . . . . .
H50A H 0.3526 0.9131 0.6323 0.054 Uiso 1 1 calc GR . . . .
H50B H 0.4621 0.9300 0.5879 0.054 Uiso 1 1 calc GR . . . .
H50C H 0.3944 0.8260 0.5943 0.054 Uiso 1 1 calc GR . . . .
C10 C -0.1902(6) 0.6281(5) 0.9961(3) 0.0476(18) Uani 1 1 d . . . . .
H10 H -0.2821 0.6199 0.9855 0.057 Uiso 1 1 calc R . . . .
C40 C 0.6242(6) 0.9554(4) 0.7349(2) 0.0386(15) Uani 1 1 d . . . . .
H40A H 0.5729 0.8900 0.7268 0.058 Uiso 1 1 calc GR . . . .
H40B H 0.7040 0.9595 0.7152 0.058 Uiso 1 1 calc GR . . . .
H40C H 0.5709 0.9934 0.7192 0.058 Uiso 1 1 calc GR . . . .
C25 C 1.0672(5) 0.8394(4) 0.9172(3) 0.0378(15) Uani 1 1 d . . . . .
H25A H 1.0940 0.9073 0.9323 0.057 Uiso 1 1 calc GR . . . .
H25B H 1.1303 0.8203 0.8913 0.057 Uiso 1 1 calc GR . . . .
H25C H 1.0654 0.8082 0.9515 0.057 Uiso 1 1 calc GR . . . .
C66 C 0.6150(5) 0.6626(5) 0.5536(3) 0.0422(16) Uani 1 1 d . . . . .
H66A H 0.5768 0.6308 0.5843 0.063 Uiso 1 1 calc GR . . . .
H66B H 0.6681 0.7255 0.5730 0.063 Uiso 1 1 calc GR . . . .
H66C H 0.6711 0.6269 0.5326 0.063 Uiso 1 1 calc GR . . . .
C78 C -0.0760(5) 0.2026(4) 0.7466(3) 0.0386(15) Uani 1 1 d . . . . .
H78A H -0.0566 0.1933 0.7048 0.058 Uiso 1 1 calc GR . . . .
H78B H -0.1113 0.1416 0.7565 0.058 Uiso 1 1 calc GR . . . .
H78C H 0.0051 0.2356 0.7740 0.058 Uiso 1 1 calc GR . . . .
C16 C 0.2250(6) 0.6728(4) 1.0431(3) 0.0432(16) Uani 1 1 d . . . . .
H16A H 0.2494 0.6130 1.0390 0.065 Uiso 1 1 calc GR . . . .
H16B H 0.2509 0.7081 1.0850 0.065 Uiso 1 1 calc GR . . . .
H16C H 0.2702 0.7089 1.0159 0.065 Uiso 1 1 calc GR . . . .
C77 C -0.5102(5) 0.2428(4) 0.8110(3) 0.0427(16) Uani 1 1 d . . . . .
H77A H -0.4928 0.2645 0.8550 0.064 Uiso 1 1 calc GR . . . .
H77B H -0.5359 0.1742 0.8008 0.064 Uiso 1 1 calc GR . . . .
H77C H -0.5818 0.2669 0.7949 0.064 Uiso 1 1 calc GR . . . .
C11 C -0.1315(7) 0.6814(4) 1.0516(3) 0.0438(17) Uani 1 1 d . . . . .
C68 C 0.1465(6) 0.5471(5) 0.4502(3) 0.0511(18) Uani 1 1 d . . . . .
H68A H 0.1563 0.4830 0.4455 0.077 Uiso 1 1 calc GR . . . .
H68B H 0.0938 0.5526 0.4140 0.077 Uiso 1 1 calc GR . . . .
H68C H 0.1021 0.5620 0.4856 0.077 Uiso 1 1 calc GR . . . .
C41 C 0.9665(6) 1.0547(4) 0.9186(3) 0.0468(17) Uani 1 1 d . . . . .
H41A H 1.0190 1.0348 0.8874 0.070 Uiso 1 1 calc GR . . . .
H41B H 0.9671 1.0172 0.9495 0.070 Uiso 1 1 calc GR . . . .
H41C H 1.0043 1.1209 0.9373 0.070 Uiso 1 1 calc GR . . . .
C67 C 0.4589(7) 0.8155(4) 0.3920(3) 0.0480(17) Uani 1 1 d . . . . .
H67A H 0.4138 0.8645 0.4054 0.072 Uiso 1 1 calc GR . . . .
H67B H 0.4258 0.7857 0.3496 0.072 Uiso 1 1 calc GR . . . .
H67C H 0.5539 0.8434 0.3960 0.072 Uiso 1 1 calc GR . . . .
C30 C 0.0944(6) 0.9881(5) 0.7166(3) 0.0470(17) Uani 1 1 d . . . . .
H30 H 0.0588 1.0411 0.7197 0.056 Uiso 1 1 calc R . . . .
C12 C 0.0039(7) 0.6950(4) 1.0670(3) 0.0472(17) Uani 1 1 d . . . . .
H12 H 0.0457 0.7323 1.1053 0.057 Uiso 1 1 calc R . . . .
C47 C 0.1982(6) 0.9362(5) 0.4566(3) 0.055(2) Uani 1 1 d . . . . .
C14 C -0.1846(5) 0.5290(5) 0.8933(3) 0.0492(18) Uani 1 1 d . . . . .
H14A H -0.1779 0.5697 0.8641 0.074 Uiso 1 1 calc GR . . . .
H14B H -0.2776 0.5009 0.8951 0.074 Uiso 1 1 calc GR . . . .
H14C H -0.1401 0.4794 0.8806 0.074 Uiso 1 1 calc GR . . . .
C42 C 0.5015(6) 1.0786(5) 0.9380(3) 0.0519(18) Uani 1 1 d . . . . .
H42A H 0.4591 1.1201 0.9194 0.078 Uiso 1 1 calc GR . . . .
H42B H 0.5447 1.1112 0.9787 0.078 Uiso 1 1 calc GR . . . .
H42C H 0.4347 1.0224 0.9404 0.078 Uiso 1 1 calc GR . . . .
C46 C 0.0867(6) 0.8643(5) 0.4462(3) 0.054(2) Uani 1 1 d . . . . .
H46 H 0.0223 0.8593 0.4130 0.065 Uiso 1 1 calc R . . . .
C52 C -0.0590(6) 0.7177(5) 0.4662(3) 0.0538(18) Uani 1 1 d . . . . .
H52A H -0.0475 0.6684 0.4874 0.081 Uiso 1 1 calc GR . . . .
H52B H -0.0734 0.6927 0.4225 0.081 Uiso 1 1 calc GR . . . .
H52C H -0.1353 0.7400 0.4785 0.081 Uiso 1 1 calc GR . . . .
C15 C -0.2133(8) 0.7242(5) 1.0962(4) 0.074(2) Uani 1 1 d . . . . .
H15A H -0.2986 0.7231 1.0746 0.111 Uiso 1 1 calc GR . . . .
H15B H -0.1662 0.7889 1.1147 0.111 Uiso 1 1 calc GR . . . .
H15C H -0.2277 0.6879 1.1277 0.111 Uiso 1 1 calc GR . . . .
C51 C 0.2196(7) 1.0080(7) 0.4175(4) 0.107(4) Uani 1 1 d . . . . .
H51A H 0.1694 1.0542 0.4298 0.160 Uiso 1 1 calc GR . . . .
H51B H 0.1896 0.9768 0.3751 0.160 Uiso 1 1 calc GR . . . .
H51C H 0.3136 1.0395 0.4223 0.160 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
P2 P3 2.217(2) . ?
P2 P1 2.194(2) . ?
P2 C27 1.853(5) . ?
P3 P1 2.237(2) . ?
P3 C53 1.850(5) . ?
P1 C1 1.839(5) . ?
O6 C70 1.399(6) . ?
O6 C69 1.434(6) . ?
O2 C17 1.422(6) . ?
O2 C18 1.400(6) . ?
O1 C7 1.415(6) . ?
O1 C8 1.400(6) . ?
O4 C44 1.395(6) . ?
O4 C43 1.445(6) . ?
O3 C34 1.398(6) . ?
O3 C33 1.428(6) . ?
O5 C60 1.393(6) . ?
O5 C59 1.432(6) . ?
C6 C1 1.420(7) . ?
C6 C7 1.504(7) . ?
C6 C5 1.388(7) . ?
C75 C70 1.395(7) . ?
C75 C74 1.398(7) . ?
C75 C76 1.483(7) . ?
C58 C57 1.392(7) . ?
C58 C53 1.396(7) . ?
C58 C69 1.508(7) . ?
C57 H57 0.9500 . ?
C57 C56 1.384(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C2 1.505(7) . ?
C3 H3 0.9500 . ?
C3 C2 1.391(7) . ?
C3 C4 1.365(7) . ?
C28 C27 1.418(7) . ?
C28 C43 1.494(8) . ?
C28 C29 1.395(8) . ?
C1 C2 1.406(7) . ?
C53 C54 1.417(7) . ?
C18 C23 1.395(7) . ?
C18 C19 1.385(7) . ?
C27 C32 1.398(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C60 C65 1.379(7) . ?
C60 C61 1.382(7) . ?
C23 C22 1.391(7) . ?
C23 C26 1.509(7) . ?
C55 H55 0.9500 . ?
C55 C54 1.386(7) . ?
C55 C56 1.377(7) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
C59 C54 1.502(7) . ?
C39 C34 1.391(7) . ?
C39 C38 1.397(7) . ?
C39 C40 1.496(7) . ?
C20 H20 0.9500 . ?
C20 C19 1.378(7) . ?
C20 C21 1.389(7) . ?
C19 C24 1.518(7) . ?
C70 C71 1.390(7) . ?
C65 C64 1.397(7) . ?
C65 C66 1.507(7) . ?
C22 H22 0.9500 . ?
C22 C21 1.380(7) . ?
C32 C33 1.515(7) . ?
C32 C31 1.387(7) . ?
C35 C34 1.374(7) . ?
C35 C36 1.394(7) . ?
C35 C42 1.515(8) . ?
C74 H74 0.9500 . ?
C74 C73 1.379(7) . ?
C72 H72 0.9500 . ?
C72 C71 1.390(7) . ?
C72 C73 1.389(7) . ?
C76 H76A 0.9800 . ?
C76 H76B 0.9800 . ?
C76 H76C 0.9800 . ?
C44 C49 1.384(7) . ?
C44 C45 1.397(7) . ?
C71 C78 1.513(7) . ?
C38 H38 0.9500 . ?
C38 C37 1.389(8) . ?
C69 H69A 0.9900 . ?
C69 H69B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C8 C9 1.404(7) . ?
C8 C13 1.372(8) . ?
C21 C25 1.517(7) . ?
C5 H5 0.9500 . ?
C5 C4 1.380(7) . ?
C73 C77 1.513(7) . ?
C56 H56 0.9500 . ?
C61 C62 1.388(8) . ?
C61 C68 1.519(8) . ?
C9 C10 1.399(8) . ?
C9 C14 1.496(8) . ?
C49 C48 1.375(8) . ?
C49 C50 1.509(7) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C64 H64 0.9500 . ?
C64 C63 1.390(8) . ?
C4 H4 0.9500 . ?
C31 H31 0.9500 . ?
C31 C30 1.384(8) . ?
C37 C36 1.376(8) . ?
C37 C41 1.503(8) . ?
C45 C46 1.395(8) . ?
C45 C52 1.512(8) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C63 C62 1.387(8) . ?
C63 C67 1.511(8) . ?
C13 C16 1.499(8) . ?
C13 C12 1.394(8) . ?
C62 H62 0.9500 . ?
C36 H36 0.9500 . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C29 H29 0.9500 . ?
C29 C30 1.361(9) . ?
C48 H48 0.9500 . ?
C48 C47 1.376(8) . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C10 H10 0.9500 . ?
C10 C11 1.371(9) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C66 H66A 0.9800 . ?
C66 H66B 0.9800 . ?
C66 H66C 0.9800 . ?
C78 H78A 0.9800 . ?
C78 H78B 0.9800 . ?
C78 H78C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C77 H77A 0.9800 . ?
C77 H77B 0.9800 . ?
C77 H77C 0.9800 . ?
C11 C12 1.396(9) . ?
C11 C15 1.527(8) . ?
C68 H68A 0.9800 . ?
C68 H68B 0.9800 . ?
C68 H68C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C67 H67A 0.9800 . ?
C67 H67B 0.9800 . ?
C67 H67C 0.9800 . ?
C30 H30 0.9500 . ?
C12 H12 0.9500 . ?
C47 C46 1.368(9) . ?
C47 C51 1.513(9) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C46 H46 0.9500 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?

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
P1 P2 P3 60.95(7) . . ?
C27 P2 P3 104.08(16) . . ?
C27 P2 P1 96.46(16) . . ?
P2 P3 P1 59.02(7) . . ?
C53 P3 P2 100.54(17) . . ?
C53 P3 P1 103.76(16) . . ?
P2 P1 P3 60.03(7) . . ?
C1 P1 P2 113.78(16) . . ?
C1 P1 P3 108.26(17) . . ?
C70 O6 C69 113.9(4) . . ?
C18 O2 C17 112.8(4) . . ?
C8 O1 C7 113.9(4) . . ?
C44 O4 C43 113.6(4) . . ?
C34 O3 C33 113.8(4) . . ?
C60 O5 C59 110.9(4) . . ?
C1 C6 C7 121.0(4) . . ?
C5 C6 C1 120.1(5) . . ?
C5 C6 C7 118.9(5) . . ?
C70 C75 C74 116.9(5) . . ?
C70 C75 C76 121.9(4) . . ?
C74 C75 C76 121.2(5) . . ?
C57 C58 C53 120.0(5) . . ?
C57 C58 C69 116.7(5) . . ?
C53 C58 C69 123.1(5) . . ?
C58 C57 H57 119.7 . . ?
C56 C57 C58 120.6(5) . . ?
C56 C57 H57 119.7 . . ?
O2 C17 H17A 109.4 . . ?
O2 C17 H17B 109.4 . . ?
O2 C17 C2 111.3(4) . . ?
H17A C17 H17B 108.0 . . ?
C2 C17 H17A 109.4 . . ?
C2 C17 H17B 109.4 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C4 C3 C2 121.6(5) . . ?
C27 C28 C43 123.6(5) . . ?
C29 C28 C27 117.6(5) . . ?
C29 C28 C43 118.8(5) . . ?
C6 C1 P1 112.1(3) . . ?
C2 C1 P1 129.1(4) . . ?
C2 C1 C6 118.6(4) . . ?
C3 C2 C17 117.8(4) . . ?
C3 C2 C1 119.1(5) . . ?
C1 C2 C17 123.0(4) . . ?
C58 C53 P3 117.4(4) . . ?
C58 C53 C54 119.1(5) . . ?
C54 C53 P3 123.4(4) . . ?
C23 C18 O2 118.7(4) . . ?
C19 C18 O2 119.4(4) . . ?
C19 C18 C23 121.8(4) . . ?
C28 C27 P2 123.2(4) . . ?
C32 C27 P2 116.8(4) . . ?
C32 C27 C28 119.4(5) . . ?
O1 C7 C6 110.4(4) . . ?
O1 C7 H7A 109.6 . . ?
O1 C7 H7B 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C65 C60 O5 119.2(5) . . ?
C65 C60 C61 122.3(5) . . ?
C61 C60 O5 118.5(5) . . ?
C18 C23 C26 121.4(4) . . ?
C22 C23 C18 117.9(5) . . ?
C22 C23 C26 120.6(4) . . ?
C54 C55 H55 119.2 . . ?
C56 C55 H55 119.2 . . ?
C56 C55 C54 121.6(5) . . ?
O5 C59 H59A 109.7 . . ?
O5 C59 H59B 109.7 . . ?
O5 C59 C54 109.8(4) . . ?
H59A C59 H59B 108.2 . . ?
C54 C59 H59A 109.7 . . ?
C54 C59 H59B 109.7 . . ?
C34 C39 C38 117.2(5) . . ?
C34 C39 C40 121.4(5) . . ?
C38 C39 C40 121.4(5) . . ?
C19 C20 H20 118.7 . . ?
C19 C20 C21 122.6(5) . . ?
C21 C20 H20 118.7 . . ?
C18 C19 C24 121.5(5) . . ?
C20 C19 C18 117.9(5) . . ?
C20 C19 C24 120.6(5) . . ?
C75 C70 O6 119.1(4) . . ?
C71 C70 O6 118.7(4) . . ?
C71 C70 C75 121.9(5) . . ?
C60 C65 C64 118.5(5) . . ?
C60 C65 C66 121.7(5) . . ?
C64 C65 C66 119.7(5) . . ?
C23 C22 H22 119.0 . . ?
C21 C22 C23 122.0(5) . . ?
C21 C22 H22 119.0 . . ?
C27 C32 C33 122.3(5) . . ?
C31 C32 C27 120.6(5) . . ?
C31 C32 C33 117.0(5) . . ?
C53 C54 C59 121.8(5) . . ?
C55 C54 C53 119.0(5) . . ?
C55 C54 C59 119.3(4) . . ?
C34 C35 C36 118.0(5) . . ?
C34 C35 C42 120.8(5) . . ?
C36 C35 C42 121.1(5) . . ?
C75 C74 H74 118.5 . . ?
C73 C74 C75 123.0(5) . . ?
C73 C74 H74 118.5 . . ?
C71 C72 H72 119.3 . . ?
C73 C72 H72 119.3 . . ?
C73 C72 C71 121.4(5) . . ?
C75 C76 H76A 109.5 . . ?
C75 C76 H76B 109.5 . . ?
C75 C76 H76C 109.5 . . ?
H76A C76 H76B 109.5 . . ?
H76A C76 H76C 109.5 . . ?
H76B C76 H76C 109.5 . . ?
O4 C44 C45 118.7(5) . . ?
C49 C44 O4 119.3(4) . . ?
C49 C44 C45 121.9(5) . . ?
C70 C71 C78 120.9(5) . . ?
C72 C71 C70 118.7(5) . . ?
C72 C71 C78 120.4(5) . . ?
C39 C34 O3 118.8(5) . . ?
C35 C34 O3 118.1(5) . . ?
C35 C34 C39 123.0(5) . . ?
C39 C38 H38 119.4 . . ?
C37 C38 C39 121.3(5) . . ?
C37 C38 H38 119.4 . . ?
O6 C69 C58 106.8(4) . . ?
O6 C69 H69A 110.4 . . ?
O6 C69 H69B 110.4 . . ?
C58 C69 H69A 110.4 . . ?
C58 C69 H69B 110.4 . . ?
H69A C69 H69B 108.6 . . ?
O3 C33 C32 107.3(4) . . ?
O3 C33 H33A 110.2 . . ?
O3 C33 H33B 110.2 . . ?
C32 C33 H33A 110.2 . . ?
C32 C33 H33B 110.2 . . ?
H33A C33 H33B 108.5 . . ?
O1 C8 C9 118.7(5) . . ?
C13 C8 O1 117.9(5) . . ?
C13 C8 C9 123.4(5) . . ?
C20 C21 C25 121.0(5) . . ?
C22 C21 C20 117.8(5) . . ?
C22 C21 C25 121.1(5) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.0(5) . . ?
C4 C5 H5 120.0 . . ?
C74 C73 C72 118.2(5) . . ?
C74 C73 C77 121.1(5) . . ?
C72 C73 C77 120.8(5) . . ?
C57 C56 H56 120.3 . . ?
C55 C56 C57 119.5(5) . . ?
C55 C56 H56 120.3 . . ?
C60 C61 C62 118.1(5) . . ?
C60 C61 C68 120.8(5) . . ?
C62 C61 C68 121.2(5) . . ?
C8 C9 C14 121.5(5) . . ?
C10 C9 C8 116.0(6) . . ?
C10 C9 C14 122.4(5) . . ?
C44 C49 C50 121.5(5) . . ?
C48 C49 C44 117.9(5) . . ?
C48 C49 C50 120.7(5) . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C65 C64 H64 119.7 . . ?
C63 C64 C65 120.7(5) . . ?
C63 C64 H64 119.7 . . ?
C3 C4 C5 120.4(5) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C32 C31 H31 120.1 . . ?
C30 C31 C32 119.7(6) . . ?
C30 C31 H31 120.1 . . ?
C38 C37 C41 120.1(5) . . ?
C36 C37 C38 119.2(5) . . ?
C36 C37 C41 120.6(5) . . ?
C44 C45 C52 123.2(6) . . ?
C46 C45 C44 116.8(6) . . ?
C46 C45 C52 120.0(5) . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C64 C63 C67 121.0(5) . . ?
C62 C63 C64 118.8(5) . . ?
C62 C63 C67 120.1(5) . . ?
C8 C13 C16 121.4(5) . . ?
C8 C13 C12 118.1(6) . . ?
C12 C13 C16 120.5(5) . . ?
C61 C62 H62 119.2 . . ?
C63 C62 C61 121.6(5) . . ?
C63 C62 H62 119.2 . . ?
C35 C36 H36 119.4 . . ?
C37 C36 C35 121.3(5) . . ?
C37 C36 H36 119.4 . . ?
O4 C43 C28 112.5(4) . . ?
O4 C43 H43A 109.1 . . ?
O4 C43 H43B 109.1 . . ?
C28 C43 H43A 109.1 . . ?
C28 C43 H43B 109.1 . . ?
H43A C43 H43B 107.8 . . ?
C28 C29 H29 118.7 . . ?
C30 C29 C28 122.5(6) . . ?
C30 C29 H29 118.7 . . ?
C49 C48 H48 118.6 . . ?
C49 C48 C47 122.8(6) . . ?
C47 C48 H48 118.6 . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C9 C10 H10 118.6 . . ?
C11 C10 C9 122.7(6) . . ?
C11 C10 H10 118.6 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C21 C25 H25A 109.5 . . ?
C21 C25 H25B 109.5 . . ?
C21 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C65 C66 H66A 109.5 . . ?
C65 C66 H66B 109.5 . . ?
C65 C66 H66C 109.5 . . ?
H66A C66 H66B 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?
C71 C78 H78A 109.5 . . ?
C71 C78 H78B 109.5 . . ?
C71 C78 H78C 109.5 . . ?
H78A C78 H78B 109.5 . . ?
H78A C78 H78C 109.5 . . ?
H78B C78 H78C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C73 C77 H77A 109.5 . . ?
C73 C77 H77B 109.5 . . ?
C73 C77 H77C 109.5 . . ?
H77A C77 H77B 109.5 . . ?
H77A C77 H77C 109.5 . . ?
H77B C77 H77C 109.5 . . ?
C10 C11 C12 118.9(6) . . ?
C10 C11 C15 120.5(7) . . ?
C12 C11 C15 120.6(7) . . ?
C61 C68 H68A 109.5 . . ?
C61 C68 H68B 109.5 . . ?
C61 C68 H68C 109.5 . . ?
H68A C68 H68B 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 109.5 . . ?
C37 C41 H41A 109.5 . . ?
C37 C41 H41B 109.5 . . ?
C37 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C63 C67 H67A 109.5 . . ?
C63 C67 H67B 109.5 . . ?
C63 C67 H67C 109.5 . . ?
H67A C67 H67B 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 109.5 . . ?
C31 C30 H30 120.0 . . ?
C29 C30 C31 120.0(6) . . ?
C29 C30 H30 120.0 . . ?
C13 C12 C11 121.0(6) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C48 C47 C51 120.7(6) . . ?
C46 C47 C48 117.7(6) . . ?
C46 C47 C51 121.6(6) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C35 C42 H42A 109.5 . . ?
C35 C42 H42B 109.5 . . ?
C35 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C45 C46 H46 118.6 . . ?
C47 C46 C45 122.8(5) . . ?
C47 C46 H46 118.6 . . ?
C45 C52 H52A 109.5 . . ?
C45 C52 H52B 109.5 . . ?
C45 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C47 C51 H51A 109.5 . . ?
C47 C51 H51B 109.5 . . ?
C47 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9938(5)
2 0.0062(5)

