# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_erk9164
_database_code_depnum_ccdc_archive 'CCDC 1862533'
_audit_update_record             
;
2018-08-17 deposited with the CCDC.
2019-01-14 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H21 B Cl F10 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         619.73

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   10.2284(12)
_cell_length_b                   11.0264(13)
_cell_length_c                   12.5397(13)
_cell_angle_alpha                88.589(8)
_cell_angle_beta                 80.364(7)
_cell_angle_gamma                79.511(8)
_cell_volume                     1371.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2983
_cell_measurement_theta_min      4.0775
_cell_measurement_theta_max      64.6307
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             628

_exptl_absorpt_coefficient_mu    2.050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            20385
_diffrn_reflns_av_R_equivalents  0.0958
_diffrn_reflns_av_unetI/netI     0.1026
_diffrn_reflns_theta_min         4.46
_diffrn_reflns_theta_max         66.76
_diffrn_reflns_theta_full        66.76
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_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.

A badly disordered half C3H4 (allene) molecule was found in the 
asymmetrical unit and could not be satisfactorily refined. The program 
SQUEEZE (Spek, A.L. (2015). Acta Cryst. C71, 9-18) was therefore used to
remove mathematically the effect of the solvent.
The quoted formula and derived parameters are not included the squeezed
alene molecule. 

The CH2-CCl=CH2 unit was found disordered over two positions in the
asymmetric unit. Several restraints (SADI, SAME, ISOR and SIMU) were used
in order to improve refinement stability. 
;

_reflns_number_total             4780
_reflns_number_gt                2842
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1670
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.977
_refine_ls_number_reflns         4780
_refine_ls_number_parameters     408
_refine_ls_number_restraints     64
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0709P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0046(6)

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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.3106(4) 0.2949(4) 0.6831(4) 0.0422(10) Uani d . . . 1.0 . .
N N1 0.3760(3) 0.2348(3) 0.5607(2) 0.0411(7) Uani d . . . 1.0 . .
C C1 0.2537(4) 0.1820(3) 0.7518(3) 0.0414(9) Uani d . . . 1.0 . .
H H1A 0.1758 0.167 0.7199 0.05 Uiso calc U . R 1.0 . .
H H1B 0.3246 0.1078 0.7355 0.05 Uiso calc U . R 1.0 . .
C C2 0.2080(3) 0.1843(3) 0.8767(3) 0.0407(8) Uani d . . . 1.0 . .
C C3 0.1341(4) 0.3131(3) 0.9204(3) 0.0434(9) Uani d . . . 1.0 . .
H H3A 0.193 0.3742 0.8976 0.052 Uiso calc U . R 1.0 . .
H H3B 0.0514 0.337 0.8878 0.052 Uiso calc U . R 1.0 . .
C C4 0.0959(4) 0.3173(3) 1.0417(3) 0.0422(9) Uani d . . . 1.0 . .
C C5 0.2112(4) 0.2732(4) 1.1019(3) 0.0491(10) Uani d . . . 1.0 . .
H H5A 0.1756 0.2636 1.1795 0.059 Uiso calc U . R 1.0 . .
H H5B 0.2709 0.3352 1.0959 0.059 Uiso calc U . R 1.0 . .
C C6 0.2913(4) 0.1507(4) 1.0562(3) 0.0472(9) Uani d . . . 1.0 . .
C C7 0.3314(4) 0.1473(4) 0.9357(3) 0.0436(9) Uani d . . . 1.0 . .
H H7A 0.3782 0.063 0.9128 0.052 Uiso calc U . R 1.0 . .
H H7B 0.3955 0.2044 0.9142 0.052 Uiso calc U . R 1.0 . .
C C8 0.1087(3) 0.0933(3) 0.9056(3) 0.0443(9) Uani d . . D 1.0 . .
H H8A 0.0865 0.0889 0.9854 0.053 Uiso calc U P R 0.600(6) A 1
H H8B 0.0241 0.1272 0.8783 0.053 Uiso calc U P R 0.600(6) A 1
H H8C 0.1064 0.0731 0.9832 0.053 Uiso calc U P R 0.400(6) A 2
H H8D 0.0178 0.1385 0.8981 0.053 Uiso calc U P R 0.400(6) A 2
C C9 0.1594(11) -0.0369(8) 0.8612(8) 0.044(2) Uani d U P D 0.600(6) A 1
Cl Cl1 0.1115(3) -0.0702(3) 0.7375(2) 0.0620(8) Uani d U P D 0.600(6) A 1
C C10 0.2576(13) -0.1350(9) 0.8848(10) 0.021(2) Uani d U P D 0.600(6) A 1
H H10A 0.3089 -0.1263 0.9398 0.025 Uiso calc U P R 0.600(6) A 1
H H10B 0.2731 -0.2105 0.8458 0.025 Uiso calc U P R 0.600(6) A 1
C C9A 0.1298(17) -0.0238(12) 0.8465(14) 0.055(5) Uani d U P D 0.400(6) A 2
Cl Cl1A 0.2476(10) -0.1319(8) 0.8969(8) 0.100(3) Uani d U P D 0.400(6) A 2
C C10A 0.0615(17) -0.0578(18) 0.7693(14) 0.064(5) Uani d U P D 0.400(6) A 2
H H10C -0.0109 -0.0011 0.7478 0.077 Uiso calc U P R 0.400(6) A 2
H H10D 0.087 -0.1378 0.7378 0.077 Uiso calc U P R 0.400(6) A 2
C C11 -0.0280(4) 0.3558(3) 1.0915(3) 0.0441(9) Uani d . . . 1.0 . .
H H11A -0.0982 0.3825 1.0507 0.053 Uiso calc U . R 1.0 . .
H H11B -0.0474 0.3568 1.1683 0.053 Uiso calc U . R 1.0 . .
C C12 0.3198(4) 0.0539(4) 1.1174(4) 0.0575(11) Uani d . . . 1.0 . .
H H12A 0.3677 -0.022 1.0853 0.069 Uiso calc U . R 1.0 . .
H H12B 0.2925 0.0599 1.1936 0.069 Uiso calc U . R 1.0 . .
C C21 0.3127(4) 0.1561(4) 0.5174(3) 0.0453(9) Uani d . . . 1.0 . .
H H21 0.2348 0.133 0.5591 0.054 Uiso calc U . R 1.0 . .
C C22 0.3569(4) 0.1081(4) 0.4151(3) 0.0509(10) Uani d . . . 1.0 . .
H H22 0.31 0.0525 0.3872 0.061 Uiso calc U . R 1.0 . .
C C23 0.4697(4) 0.1407(4) 0.3527(4) 0.0576(11) Uani d . . . 1.0 . .
H H23 0.5011 0.109 0.2814 0.069 Uiso calc U . R 1.0 . .
C C24 0.5355(4) 0.2211(4) 0.3972(3) 0.0557(11) Uani d . . . 1.0 . .
H H24 0.6141 0.2448 0.3569 0.067 Uiso calc U . R 1.0 . .
C C25 0.4859(4) 0.2666(4) 0.5007(3) 0.0503(10) Uani d . . . 1.0 . .
H H25 0.5312 0.3224 0.5303 0.06 Uiso calc U . R 1.0 . .
C C31 0.1952(4) 0.4111(3) 0.6525(3) 0.0404(8) Uani d . . . 1.0 . .
F F32 0.3668(2) 0.5189(2) 0.57215(19) 0.0509(6) Uani d . . . 1.0 . .
C C32 0.2334(4) 0.5139(4) 0.5995(3) 0.0448(9) Uani d . . . 1.0 . .
F F33 0.1935(2) 0.7119(2) 0.5208(2) 0.0616(7) Uani d . . . 1.0 . .
C C33 0.1462(4) 0.6158(4) 0.5714(3) 0.0477(10) Uani d . . . 1.0 . .
F F34 -0.0773(2) 0.7171(2) 0.5704(2) 0.0661(7) Uani d . . . 1.0 . .
C C34 0.0098(4) 0.6183(4) 0.5960(3) 0.0495(10) Uani d . . . 1.0 . .
F F35 -0.1688(2) 0.5175(2) 0.66489(19) 0.0591(7) Uani d . . . 1.0 . .
C C35 -0.0352(4) 0.5179(4) 0.6449(3) 0.0471(10) Uani d . . . 1.0 . .
F F36 -0.0008(2) 0.3218(2) 0.71268(19) 0.0523(6) Uani d . . . 1.0 . .
C C36 0.0563(4) 0.4167(4) 0.6694(3) 0.0439(9) Uani d . . . 1.0 . .
C C41 0.4325(3) 0.3381(3) 0.7339(3) 0.0390(8) Uani d . . . 1.0 . .
F F42 0.5750(2) 0.14489(19) 0.6889(2) 0.0507(6) Uani d . . . 1.0 . .
C C42 0.5540(4) 0.2568(3) 0.7377(3) 0.0421(9) Uani d . . . 1.0 . .
F F43 0.7708(2) 0.1961(2) 0.7848(2) 0.0599(7) Uani d . . . 1.0 . .
C C43 0.6571(4) 0.2802(4) 0.7880(3) 0.0470(10) Uani d . . . 1.0 . .
F F44 0.7393(2) 0.4143(2) 0.8939(2) 0.0626(7) Uani d . . . 1.0 . .
C C44 0.6421(4) 0.3894(4) 0.8420(4) 0.0509(10) Uani d . . . 1.0 . .
F F45 0.5072(2) 0.5823(2) 0.8955(2) 0.0578(6) Uani d . . . 1.0 . .
C C45 0.5252(4) 0.4744(4) 0.8433(3) 0.0459(9) Uani d . . . 1.0 . .
F F46 0.31441(19) 0.53683(19) 0.79651(18) 0.0466(5) Uani d . . . 1.0 . .
C C46 0.4253(3) 0.4469(3) 0.7899(3) 0.0398(8) Uani d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 C1 . 1.636(6) ?
B1 C41 . 1.639(6) ?
B1 C31 . 1.661(6) ?
B1 N1 . 1.669(5) ?
N1 C25 . 1.342(5) ?
N1 C21 . 1.346(5) ?
C1 C2 . 1.557(5) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 C3 . 1.548(5) ?
C2 C8 . 1.549(5) ?
C2 C7 . 1.555(5) ?
C3 C4 . 1.505(5) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C11 . 1.315(5) ?
C4 C5 . 1.507(5) ?
C5 C6 . 1.518(6) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C12 . 1.317(6) ?
C6 C7 . 1.497(6) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9A . 1.469(12) ?
C8 C9 . 1.521(8) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C8 H8C . 0.99 ?
C8 H8D . 0.99 ?
C9 C10 . 1.398(11) ?
C9 Cl1 . 1.770(9) ?
C10 H10A . 0.95 ?
C10 H10B . 0.95 ?
C9A C10A . 1.379(13) ?
C9A Cl1A . 1.723(12) ?
C10A H10C . 0.95 ?
C10A H10D . 0.95 ?
C11 H11A . 0.95 ?
C11 H11B . 0.95 ?
C12 H12A . 0.95 ?
C12 H12B . 0.95 ?
C21 C22 . 1.372(6) ?
C21 H21 . 0.95 ?
C22 C23 . 1.381(6) ?
C22 H22 . 0.95 ?
C23 C24 . 1.385(6) ?
C23 H23 . 0.95 ?
C24 C25 . 1.383(6) ?
C24 H24 . 0.95 ?
C25 H25 . 0.95 ?
C31 C32 . 1.384(5) ?
C31 C36 . 1.391(5) ?
F32 C32 . 1.360(4) ?
C32 C33 . 1.380(5) ?
F33 C33 . 1.345(5) ?
C33 C34 . 1.372(6) ?
F34 C34 . 1.345(4) ?
C34 C35 . 1.368(6) ?
F35 C35 . 1.349(4) ?
C35 C36 . 1.384(5) ?
F36 C36 . 1.349(4) ?
C41 C46 . 1.389(5) ?
C41 C42 . 1.401(5) ?
F42 C42 . 1.356(4) ?
C42 C43 . 1.381(6) ?
F43 C43 . 1.344(4) ?
C43 C44 . 1.368(6) ?
F44 C44 . 1.346(5) ?
C44 C45 . 1.377(6) ?
F45 C45 . 1.341(4) ?
C45 C46 . 1.391(5) ?
F46 C46 . 1.356(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 B1 C41 . . 111.8(3) ?
C1 B1 C31 . . 116.2(3) ?
C41 B1 C31 . . 114.0(3) ?
C1 B1 N1 . . 104.6(3) ?
C41 B1 N1 . . 107.6(3) ?
C31 B1 N1 . . 101.1(3) ?
C25 N1 C21 . . 118.1(3) ?
C25 N1 B1 . . 122.6(3) ?
C21 N1 B1 . . 119.2(3) ?
C2 C1 B1 . . 124.1(3) ?
C2 C1 H1A . . 106.3 ?
B1 C1 H1A . . 106.3 ?
C2 C1 H1B . . 106.3 ?
B1 C1 H1B . . 106.3 ?
H1A C1 H1B . . 106.4 ?
C3 C2 C8 . . 107.5(3) ?
C3 C2 C7 . . 107.0(3) ?
C8 C2 C7 . . 110.2(3) ?
C3 C2 C1 . . 112.9(3) ?
C8 C2 C1 . . 108.5(3) ?
C7 C2 C1 . . 110.7(3) ?
C4 C3 C2 . . 113.1(3) ?
C4 C3 H3A . . 109.0 ?
C2 C3 H3A . . 109.0 ?
C4 C3 H3B . . 109.0 ?
C2 C3 H3B . . 109.0 ?
H3A C3 H3B . . 107.8 ?
C11 C4 C3 . . 123.0(4) ?
C11 C4 C5 . . 122.4(4) ?
C3 C4 C5 . . 114.6(3) ?
C4 C5 C6 . . 110.5(3) ?
C4 C5 H5A . . 109.6 ?
C6 C5 H5A . . 109.6 ?
C4 C5 H5B . . 109.6 ?
C6 C5 H5B . . 109.6 ?
H5A C5 H5B . . 108.1 ?
C12 C6 C7 . . 122.6(4) ?
C12 C6 C5 . . 122.6(4) ?
C7 C6 C5 . . 114.7(3) ?
C6 C7 C2 . . 112.1(3) ?
C6 C7 H7A . . 109.2 ?
C2 C7 H7A . . 109.2 ?
C6 C7 H7B . . 109.2 ?
C2 C7 H7B . . 109.2 ?
H7A C7 H7B . . 107.9 ?
C9A C8 C2 . . 120.4(9) ?
C9 C8 C2 . . 115.4(5) ?
C9 C8 H8A . . 108.4 ?
C2 C8 H8A . . 108.4 ?
C9 C8 H8B . . 108.4 ?
C2 C8 H8B . . 108.4 ?
H8A C8 H8B . . 107.5 ?
C9A C8 H8C . . 107.2 ?
C2 C8 H8C . . 107.2 ?
C9A C8 H8D . . 107.2 ?
C2 C8 H8D . . 107.2 ?
H8C C8 H8D . . 106.9 ?
C10 C9 C8 . . 134.2(8) ?
C10 C9 Cl1 . . 108.1(6) ?
C8 C9 Cl1 . . 116.5(6) ?
C9 C10 H10A . . 120.0 ?
C9 C10 H10B . . 120.0 ?
H10A C10 H10B . . 120.0 ?
C10A C9A C8 . . 129.5(13) ?
C10A C9A Cl1A . . 119.9(11) ?
C8 C9A Cl1A . . 110.2(9) ?
C9A C10A H10C . . 120.0 ?
C9A C10A H10D . . 120.0 ?
H10C C10A H10D . . 120.0 ?
C4 C11 H11A . . 120.0 ?
C4 C11 H11B . . 120.0 ?
H11A C11 H11B . . 120.0 ?
C6 C12 H12A . . 120.0 ?
C6 C12 H12B . . 120.0 ?
H12A C12 H12B . . 120.0 ?
N1 C21 C22 . . 122.3(4) ?
N1 C21 H21 . . 118.8 ?
C22 C21 H21 . . 118.8 ?
C21 C22 C23 . . 119.9(4) ?
C21 C22 H22 . . 120.0 ?
C23 C22 H22 . . 120.0 ?
C22 C23 C24 . . 118.0(4) ?
C22 C23 H23 . . 121.0 ?
C24 C23 H23 . . 121.0 ?
C25 C24 C23 . . 119.4(4) ?
C25 C24 H24 . . 120.3 ?
C23 C24 H24 . . 120.3 ?
N1 C25 C24 . . 122.3(4) ?
N1 C25 H25 . . 118.9 ?
C24 C25 H25 . . 118.9 ?
C32 C31 C36 . . 112.5(3) ?
C32 C31 B1 . . 120.6(3) ?
C36 C31 B1 . . 126.8(3) ?
F32 C32 C33 . . 115.4(3) ?
F32 C32 C31 . . 119.4(3) ?
C33 C32 C31 . . 125.3(3) ?
F33 C33 C34 . . 120.1(3) ?
F33 C33 C32 . . 120.7(3) ?
C34 C33 C32 . . 119.1(4) ?
F34 C34 C35 . . 120.9(3) ?
F34 C34 C33 . . 120.2(4) ?
C35 C34 C33 . . 118.8(3) ?
F35 C35 C34 . . 119.1(3) ?
F35 C35 C36 . . 120.9(4) ?
C34 C35 C36 . . 119.9(3) ?
F36 C36 C35 . . 114.0(3) ?
F36 C36 C31 . . 121.9(3) ?
C35 C36 C31 . . 124.1(4) ?
C46 C41 C42 . . 111.7(3) ?
C46 C41 B1 . . 126.7(3) ?
C42 C41 B1 . . 121.1(3) ?
F42 C42 C43 . . 115.7(3) ?
F42 C42 C41 . . 118.9(3) ?
C43 C42 C41 . . 125.4(4) ?
F43 C43 C44 . . 120.2(4) ?
F43 C43 C42 . . 120.4(4) ?
C44 C43 C42 . . 119.4(3) ?
F44 C44 C43 . . 121.1(3) ?
F44 C44 C45 . . 119.9(4) ?
C43 C44 C45 . . 119.0(4) ?
F45 C45 C44 . . 120.6(4) ?
F45 C45 C46 . . 120.2(3) ?
C44 C45 C46 . . 119.2(4) ?
F46 C46 C41 . . 120.5(3) ?
F46 C46 C45 . . 114.4(3) ?
C41 C46 C45 . . 125.2(3) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 B1 N1 C25 . . . . -145.1(3) ?
C41 B1 N1 C25 . . . . -26.1(5) ?
C31 B1 N1 C25 . . . . 93.7(4) ?
C1 B1 N1 C21 . . . . 38.5(4) ?
C41 B1 N1 C21 . . . . 157.6(3) ?
C31 B1 N1 C21 . . . . -82.6(4) ?
C41 B1 C1 C2 . . . . 51.6(5) ?
C31 B1 C1 C2 . . . . -81.6(4) ?
N1 B1 C1 C2 . . . . 167.8(3) ?
B1 C1 C2 C3 . . . . 37.4(5) ?
B1 C1 C2 C8 . . . . 156.5(3) ?
B1 C1 C2 C7 . . . . -82.5(4) ?
C8 C2 C3 C4 . . . . 63.3(4) ?
C7 C2 C3 C4 . . . . -55.1(4) ?
C1 C2 C3 C4 . . . . -177.1(3) ?
C2 C3 C4 C11 . . . . -125.6(4) ?
C2 C3 C4 C5 . . . . 54.1(4) ?
C11 C4 C5 C6 . . . . 131.3(4) ?
C3 C4 C5 C6 . . . . -48.5(4) ?
C4 C5 C6 C12 . . . . -128.4(4) ?
C4 C5 C6 C7 . . . . 49.6(4) ?
C12 C6 C7 C2 . . . . 122.5(4) ?
C5 C6 C7 C2 . . . . -55.5(4) ?
C3 C2 C7 C6 . . . . 55.6(4) ?
C8 C2 C7 C6 . . . . -61.0(4) ?
C1 C2 C7 C6 . . . . 179.0(3) ?
C3 C2 C8 C9A . . . . 159.7(7) ?
C7 C2 C8 C9A . . . . -84.1(8) ?
C1 C2 C8 C9A . . . . 37.3(8) ?
C3 C2 C8 C9 . . . . 175.3(5) ?
C7 C2 C8 C9 . . . . -68.5(6) ?
C1 C2 C8 C9 . . . . 52.9(6) ?
C2 C8 C9 C10 . . . . 70.7(15) ?
C2 C8 C9 Cl1 . . . . -95.3(7) ?
C2 C8 C9A C10A . . . . -106.(2) ?
C2 C8 C9A Cl1A . . . . 81.3(13) ?
C25 N1 C21 C22 . . . . 0.1(6) ?
B1 N1 C21 C22 . . . . 176.6(3) ?
N1 C21 C22 C23 . . . . -0.3(6) ?
C21 C22 C23 C24 . . . . 0.6(6) ?
C22 C23 C24 C25 . . . . -0.8(6) ?
C21 N1 C25 C24 . . . . -0.3(6) ?
B1 N1 C25 C24 . . . . -176.7(4) ?
C23 C24 C25 N1 . . . . 0.6(7) ?
C1 B1 C31 C32 . . . . 176.5(3) ?
C41 B1 C31 C32 . . . . 44.3(5) ?
N1 B1 C31 C32 . . . . -70.9(4) ?
C1 B1 C31 C36 . . . . -7.1(6) ?
C41 B1 C31 C36 . . . . -139.3(4) ?
N1 B1 C31 C36 . . . . 105.5(4) ?
C36 C31 C32 F32 . . . . -176.6(3) ?
B1 C31 C32 F32 . . . . 0.3(5) ?
C36 C31 C32 C33 . . . . 3.8(6) ?
B1 C31 C32 C33 . . . . -179.3(4) ?
F32 C32 C33 F33 . . . . -0.3(6) ?
C31 C32 C33 F33 . . . . 179.4(4) ?
F32 C32 C33 C34 . . . . 180.0(4) ?
C31 C32 C33 C34 . . . . -0.4(7) ?
F33 C33 C34 F34 . . . . -0.4(6) ?
C32 C33 C34 F34 . . . . 179.4(4) ?
F33 C33 C34 C35 . . . . 178.3(4) ?
C32 C33 C34 C35 . . . . -2.0(6) ?
F34 C34 C35 F35 . . . . 1.7(6) ?
C33 C34 C35 F35 . . . . -177.0(4) ?
F34 C34 C35 C36 . . . . 179.2(4) ?
C33 C34 C35 C36 . . . . 0.5(6) ?
F35 C35 C36 F36 . . . . 0.5(5) ?
C34 C35 C36 F36 . . . . -177.0(4) ?
F35 C35 C36 C31 . . . . -179.1(4) ?
C34 C35 C36 C31 . . . . 3.4(6) ?
C32 C31 C36 F36 . . . . 175.2(3) ?
B1 C31 C36 F36 . . . . -1.5(6) ?
C32 C31 C36 C35 . . . . -5.3(6) ?
B1 C31 C36 C35 . . . . 178.0(4) ?
C1 B1 C41 C46 . . . . -108.1(4) ?
C31 B1 C41 C46 . . . . 26.2(5) ?
N1 B1 C41 C46 . . . . 137.5(4) ?
C1 B1 C41 C42 . . . . 62.5(4) ?
C31 B1 C41 C42 . . . . -163.1(3) ?
N1 B1 C41 C42 . . . . -51.9(4) ?
C46 C41 C42 F42 . . . . 178.4(3) ?
B1 C41 C42 F42 . . . . 6.5(5) ?
C46 C41 C42 C43 . . . . -1.4(5) ?
B1 C41 C42 C43 . . . . -173.4(4) ?
F42 C42 C43 F43 . . . . 1.5(5) ?
C41 C42 C43 F43 . . . . -178.7(3) ?
F42 C42 C43 C44 . . . . -178.0(3) ?
C41 C42 C43 C44 . . . . 1.9(6) ?
F43 C43 C44 F44 . . . . -0.8(6) ?
C42 C43 C44 F44 . . . . 178.6(4) ?
F43 C43 C44 C45 . . . . 179.4(3) ?
C42 C43 C44 C45 . . . . -1.1(6) ?
F44 C44 C45 F45 . . . . 0.2(6) ?
C43 C44 C45 F45 . . . . 179.9(3) ?
F44 C44 C45 C46 . . . . -179.6(3) ?
C43 C44 C45 C46 . . . . 0.2(6) ?
C42 C41 C46 F46 . . . . -179.2(3) ?
B1 C41 C46 F46 . . . . -7.9(5) ?
C42 C41 C46 C45 . . . . 0.4(5) ?
B1 C41 C46 C45 . . . . 171.8(4) ?
F45 C45 C46 F46 . . . . 0.1(5) ?
C44 C45 C46 F46 . . . . 179.8(3) ?
F45 C45 C46 C41 . . . . -179.6(3) ?
C44 C45 C46 C41 . . . . 0.2(6) ?


####################################################################### 
# 
# 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_erk9169
_database_code_depnum_ccdc_archive 'CCDC 1862535'
_audit_update_record             
;
2018-08-17 deposited with the CCDC.
2019-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H42 B F10 P'
_chemical_formula_weight         706.48

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'
B B 0.0013 0.0007 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9507(3)
_cell_length_b                   11.7835(3)
_cell_length_c                   16.0070(5)
_cell_angle_alpha                71.517(1)
_cell_angle_beta                 86.117(1)
_cell_angle_gamma                70.299(1)
_cell_volume                     1674.26(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4144
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9790
_exptl_absorpt_correction_T_max  0.9951
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15352
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.13
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5781
_reflns_number_gt                4799
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP-SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0168P)²+3.1977P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5781
_refine_ls_number_parameters     442
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1266
_refine_ls_wR_factor_gt          0.1147
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.93907(8) 0.16513(6) 0.23749(5) 0.01974(17) Uani 1 1 d . . .
C1 C 0.8141(3) -0.1250(3) 0.13666(18) 0.0231(6) Uani 1 1 d . . .
H1A H 0.9093 -0.1493 0.1115 0.028 Uiso 1 1 calc R . .
H1B H 0.7598 -0.1743 0.1233 0.028 Uiso 1 1 calc R . .
C2 C 0.7354(3) 0.0174(2) 0.09167(18) 0.0205(6) Uani 1 1 d . . .
C3 C 0.5840(3) 0.0625(3) 0.12459(18) 0.0231(6) Uani 1 1 d . . .
H3A H 0.5320 0.0063 0.1198 0.028 Uiso 1 1 calc R . .
H3B H 0.5906 0.0552 0.1876 0.028 Uiso 1 1 calc R . .
C4 C 0.5000(3) 0.1982(3) 0.0732(2) 0.0276(7) Uani 1 1 d . . .
C5 C 0.4938(3) 0.2262(3) -0.0255(2) 0.0342(7) Uani 1 1 d . . .
H5A H 0.4305 0.1860 -0.0411 0.041 Uiso 1 1 calc R . .
H5B H 0.4527 0.3190 -0.0542 0.041 Uiso 1 1 calc R . .
C6 C 0.6389(3) 0.1778(3) -0.05903(19) 0.0282(7) Uani 1 1 d . . .
C7 C 0.7228(3) 0.0428(3) -0.00893(18) 0.0253(6) Uani 1 1 d . . .
H7A H 0.8200 0.0212 -0.0319 0.030 Uiso 1 1 calc R . .
H7B H 0.6765 -0.0139 -0.0197 0.030 Uiso 1 1 calc R . .
C8 C 0.8267(3) 0.0923(3) 0.10634(17) 0.0203(6) Uani 1 1 d . . .
H8A H 0.9131 0.0762 0.0714 0.024 Uiso 1 1 calc R . .
H8B H 0.7716 0.1841 0.0838 0.024 Uiso 1 1 calc R . .
C9 C 0.8727(3) 0.0592(2) 0.20227(18) 0.0193(6) Uani 1 1 d . . .
C10 C 0.8672(3) -0.0478(3) 0.26313(18) 0.0203(6) Uani 1 1 d . . .
H10 H 0.8838 -0.0568 0.3230 0.024 Uiso 1 1 calc R . .
C11 C 0.4358(3) 0.2867(3) 0.1112(2) 0.0375(8) Uani 1 1 d . . .
H11A H 0.3840 0.3705 0.0760 0.045 Uiso 1 1 calc R . .
H11B H 0.4416 0.2661 0.1735 0.045 Uiso 1 1 calc R . .
C12 C 0.6905(4) 0.2469(3) -0.1268(2) 0.0435(9) Uani 1 1 d . . .
H12A H 0.6345 0.3321 -0.1568 0.052 Uiso 1 1 calc R . .
H12B H 0.7836 0.2113 -0.1454 0.052 Uiso 1 1 calc R . .
C21 C 0.9371(3) 0.3097(3) 0.14032(19) 0.0284(7) Uani 1 1 d . . .
C22 C 1.0259(4) 0.3817(3) 0.1631(2) 0.0393(8) Uani 1 1 d . . .
H22A H 1.0087 0.4637 0.1170 0.059 Uiso 1 1 calc R . .
H22B H 1.1276 0.3315 0.1669 0.059 Uiso 1 1 calc R . .
H22C H 0.9977 0.3958 0.2198 0.059 Uiso 1 1 calc R . .
C23 C 1.0005(4) 0.2752(3) 0.0570(2) 0.0360(8) Uani 1 1 d . . .
H23A H 0.9240 0.2770 0.0206 0.054 Uiso 1 1 calc R . .
H23B H 1.0721 0.1901 0.0746 0.054 Uiso 1 1 calc R . .
H23C H 1.0456 0.3369 0.0229 0.054 Uiso 1 1 calc R . .
C24 C 0.7841(4) 0.4031(3) 0.1144(2) 0.0407(9) Uani 1 1 d . . .
H24A H 0.7850 0.4713 0.0601 0.061 Uiso 1 1 calc R . .
H24B H 0.7471 0.4396 0.1619 0.061 Uiso 1 1 calc R . .
H24C H 0.7229 0.3581 0.1047 0.061 Uiso 1 1 calc R . .
C25 C 1.1302(3) 0.0731(3) 0.28371(19) 0.0256(6) Uani 1 1 d . . .
C26 C 1.2313(3) 0.0571(3) 0.2085(2) 0.0358(8) Uani 1 1 d . . .
H26A H 1.3273 0.0020 0.2332 0.054 Uiso 1 1 calc R . .
H26B H 1.2347 0.1403 0.1721 0.054 Uiso 1 1 calc R . .
H26C H 1.1965 0.0187 0.1723 0.054 Uiso 1 1 calc R . .
C27 C 1.1831(3) 0.1373(3) 0.3386(2) 0.0338(7) Uani 1 1 d . . .
H27A H 1.2844 0.0912 0.3556 0.051 Uiso 1 1 calc R . .
H27B H 1.1277 0.1365 0.3916 0.051 Uiso 1 1 calc R . .
H27C H 1.1709 0.2253 0.3033 0.051 Uiso 1 1 calc R . .
C28 C 1.1469(3) -0.0631(3) 0.3422(2) 0.0280(7) Uani 1 1 d . . .
H28A H 1.1287 -0.1104 0.3062 0.042 Uiso 1 1 calc R . .
H28B H 1.0784 -0.0604 0.3890 0.042 Uiso 1 1 calc R . .
H28C H 1.2443 -0.1050 0.3684 0.042 Uiso 1 1 calc R . .
C29 C 0.8183(3) 0.2165(3) 0.32554(19) 0.0255(6) Uani 1 1 d . . .
C30 C 0.8348(4) 0.3330(3) 0.3423(2) 0.0360(8) Uani 1 1 d . . .
H30A H 0.8121 0.4045 0.2875 0.054 Uiso 1 1 calc R . .
H30B H 0.9333 0.3128 0.3625 0.054 Uiso 1 1 calc R . .
H30C H 0.7694 0.3559 0.3874 0.054 Uiso 1 1 calc R . .
C31 C 0.8489(3) 0.1106(3) 0.41501(19) 0.0294(7) Uani 1 1 d . . .
H31A H 0.7817 0.1392 0.4577 0.044 Uiso 1 1 calc R . .
H31B H 0.9468 0.0906 0.4362 0.044 Uiso 1 1 calc R . .
H31C H 0.8376 0.0346 0.4080 0.044 Uiso 1 1 calc R . .
C32 C 0.6626(3) 0.2466(3) 0.2973(2) 0.0333(7) Uani 1 1 d . . .
H32A H 0.5998 0.2691 0.3436 0.050 Uiso 1 1 calc R . .
H32B H 0.6516 0.1719 0.2879 0.050 Uiso 1 1 calc R . .
H32C H 0.6370 0.3179 0.2425 0.050 Uiso 1 1 calc R . .
B1 B 0.8347(3) -0.1632(3) 0.2433(2) 0.0217(7) Uani 1 1 d . . .
C41 C 0.6996(3) -0.2015(3) 0.29702(19) 0.0232(6) Uani 1 1 d . . .
F42 F 0.7243(2) -0.35478(16) 0.22514(12) 0.0357(4) Uani 1 1 d . . .
C42 C 0.6590(3) -0.2977(3) 0.2859(2) 0.0280(7) Uani 1 1 d . . .
F43 F 0.5265(2) -0.43940(18) 0.31890(15) 0.0467(5) Uani 1 1 d . . .
C43 C 0.5592(3) -0.3455(3) 0.3348(2) 0.0334(8) Uani 1 1 d . . .
F44 F 0.3990(2) -0.34439(19) 0.44996(14) 0.0509(6) Uani 1 1 d . . .
C44 C 0.4944(3) -0.2980(3) 0.4003(2) 0.0343(8) Uani 1 1 d . . .
F45 F 0.4644(2) -0.15239(19) 0.47811(12) 0.0437(5) Uani 1 1 d . . .
C45 C 0.5276(3) -0.2012(3) 0.4142(2) 0.0321(7) Uani 1 1 d . . .
F46 F 0.65049(19) -0.05837(17) 0.38114(12) 0.0359(4) Uani 1 1 d . . .
C46 C 0.6261(3) -0.1545(3) 0.3622(2) 0.0265(6) Uani 1 1 d . . .
C51 C 0.9761(3) -0.2931(2) 0.28835(18) 0.0214(6) Uani 1 1 d . . .
F52 F 1.04381(19) -0.35507(15) 0.15909(11) 0.0303(4) Uani 1 1 d . . .
C52 C 1.0660(3) -0.3743(3) 0.24565(18) 0.0239(6) Uani 1 1 d . . .
F53 F 1.2667(2) -0.55000(17) 0.23886(13) 0.0393(5) Uani 1 1 d . . .
C53 C 1.1828(3) -0.4789(3) 0.2860(2) 0.0271(7) Uani 1 1 d . . .
F54 F 1.3263(2) -0.61146(18) 0.41367(13) 0.0457(5) Uani 1 1 d . . .
C54 C 1.2142(3) -0.5099(3) 0.3742(2) 0.0291(7) Uani 1 1 d . . .
F55 F 1.1545(2) -0.46583(17) 0.50800(11) 0.0408(5) Uani 1 1 d . . .
C55 C 1.1269(3) -0.4357(3) 0.42118(19) 0.0281(7) Uani 1 1 d . . .
F56 F 0.93371(19) -0.26386(16) 0.42971(11) 0.0322(4) Uani 1 1 d . . .
C56 C 1.0136(3) -0.3316(3) 0.37792(19) 0.0253(6) 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
P1 C9 1.834(3) . ?
P1 C29 1.902(3) . ?
P1 C21 1.904(3) . ?
P1 C25 1.905(3) . ?
C1 C2 1.541(4) . ?
C1 B1 1.630(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C8 1.536(4) . ?
C2 C3 1.537(4) . ?
C2 C7 1.547(4) . ?
C3 C4 1.513(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C11 1.328(4) . ?
C4 C5 1.509(4) . ?
C5 C6 1.494(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C12 1.323(5) . ?
C6 C7 1.502(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.521(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.343(4) . ?
C10 B1 1.624(4) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9500 . ?
C11 H11B 0.9500 . ?
C12 H12A 0.9500 . ?
C12 H12B 0.9500 . ?
C21 C24 1.539(5) . ?
C21 C22 1.542(4) . ?
C21 C23 1.550(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.532(4) . ?
C25 C28 1.538(4) . ?
C25 C27 1.541(4) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C32 1.534(4) . ?
C29 C31 1.540(4) . ?
C29 C30 1.541(4) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
B1 C41 1.661(4) . ?
B1 C51 1.682(4) . ?
C41 C46 1.386(4) . ?
C41 C42 1.388(4) . ?
F42 C42 1.362(3) . ?
C42 C43 1.381(4) . ?
F43 C43 1.352(4) . ?
C43 C44 1.366(5) . ?
F44 C44 1.343(4) . ?
C44 C45 1.373(5) . ?
F45 C45 1.347(4) . ?
C45 C46 1.386(4) . ?
F46 C46 1.358(3) . ?
C51 C52 1.392(4) . ?
C51 C56 1.395(4) . ?
F52 C52 1.352(3) . ?
C52 C53 1.385(4) . ?
F53 C53 1.347(3) . ?
C53 C54 1.371(4) . ?
F54 C54 1.339(3) . ?
C54 C55 1.379(4) . ?
F55 C55 1.344(3) . ?
C55 C56 1.375(4) . ?
F56 C56 1.363(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 P1 C29 107.84(13) . . ?
C9 P1 C21 110.57(13) . . ?
C29 P1 C21 110.10(13) . . ?
C9 P1 C25 108.03(13) . . ?
C29 P1 C25 110.90(13) . . ?
C21 P1 C25 109.37(14) . . ?
C2 C1 B1 113.5(2) . . ?
C2 C1 H1A 108.9 . . ?
B1 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
B1 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C8 C2 C3 111.5(2) . . ?
C8 C2 C1 108.5(2) . . ?
C3 C2 C1 112.4(2) . . ?
C8 C2 C7 107.2(2) . . ?
C3 C2 C7 108.0(2) . . ?
C1 C2 C7 109.0(2) . . ?
C4 C3 C2 112.7(2) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C11 C4 C5 122.0(3) . . ?
C11 C4 C3 123.2(3) . . ?
C5 C4 C3 114.8(3) . . ?
C6 C5 C4 111.4(2) . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C12 C6 C5 123.5(3) . . ?
C12 C6 C7 122.3(3) . . ?
C5 C6 C7 114.2(3) . . ?
C6 C7 C2 113.6(2) . . ?
C6 C7 H7A 108.8 . . ?
C2 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C2 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C2 114.0(2) . . ?
C9 C8 H8A 108.7 . . ?
C2 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C2 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C8 121.4(2) . . ?
C10 C9 P1 118.2(2) . . ?
C8 C9 P1 120.39(19) . . ?
C9 C10 B1 125.7(3) . . ?
C9 C10 H10 117.1 . . ?
B1 C10 H10 117.1 . . ?
C4 C11 H11A 120.0 . . ?
C4 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
C6 C12 H12A 120.0 . . ?
C6 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
C24 C21 C22 107.6(3) . . ?
C24 C21 C23 107.2(3) . . ?
C22 C21 C23 106.7(3) . . ?
C24 C21 P1 111.3(2) . . ?
C22 C21 P1 110.9(2) . . ?
C23 C21 P1 113.0(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C28 104.9(2) . . ?
C26 C25 C27 109.0(3) . . ?
C28 C25 C27 107.9(2) . . ?
C26 C25 P1 110.1(2) . . ?
C28 C25 P1 111.9(2) . . ?
C27 C25 P1 112.8(2) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C32 C29 C31 107.0(3) . . ?
C32 C29 C30 109.4(2) . . ?
C31 C29 C30 106.4(2) . . ?
C32 C29 P1 108.8(2) . . ?
C31 C29 P1 111.96(19) . . ?
C30 C29 P1 113.0(2) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C10 B1 C1 107.0(2) . . ?
C10 B1 C41 114.7(2) . . ?
C1 B1 C41 113.0(2) . . ?
C10 B1 C51 105.2(2) . . ?
C1 B1 C51 114.3(2) . . ?
C41 B1 C51 102.5(2) . . ?
C46 C41 C42 112.7(3) . . ?
C46 C41 B1 126.0(3) . . ?
C42 C41 B1 121.0(3) . . ?
F42 C42 C43 115.8(3) . . ?
F42 C42 C41 119.2(3) . . ?
C43 C42 C41 124.9(3) . . ?
F43 C43 C44 120.0(3) . . ?
F43 C43 C42 120.5(3) . . ?
C44 C43 C42 119.5(3) . . ?
F44 C44 C43 120.7(3) . . ?
F44 C44 C45 120.4(3) . . ?
C43 C44 C45 118.9(3) . . ?
F45 C45 C44 119.9(3) . . ?
F45 C45 C46 120.6(3) . . ?
C44 C45 C46 119.5(3) . . ?
F46 C46 C45 114.7(3) . . ?
F46 C46 C41 120.8(3) . . ?
C45 C46 C41 124.5(3) . . ?
C52 C51 C56 112.3(2) . . ?
C52 C51 B1 126.9(2) . . ?
C56 C51 B1 120.8(2) . . ?
F52 C52 C53 114.6(2) . . ?
F52 C52 C51 121.0(2) . . ?
C53 C52 C51 124.3(3) . . ?
F53 C53 C54 119.6(3) . . ?
F53 C53 C52 120.3(3) . . ?
C54 C53 C52 120.0(3) . . ?
F54 C54 C53 120.3(3) . . ?
F54 C54 C55 121.0(3) . . ?
C53 C54 C55 118.7(3) . . ?
F55 C55 C56 121.3(3) . . ?
F55 C55 C54 119.6(3) . . ?
C56 C55 C54 119.1(3) . . ?
F56 C56 C55 114.9(3) . . ?
F56 C56 C51 119.6(2) . . ?
C55 C56 C51 125.5(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
B1 C1 C2 C8 63.2(3) . . . . ?
B1 C1 C2 C3 -60.6(3) . . . . ?
B1 C1 C2 C7 179.6(2) . . . . ?
C8 C2 C3 C4 64.7(3) . . . . ?
C1 C2 C3 C4 -173.2(2) . . . . ?
C7 C2 C3 C4 -52.9(3) . . . . ?
C2 C3 C4 C11 -127.2(3) . . . . ?
C2 C3 C4 C5 52.9(3) . . . . ?
C11 C4 C5 C6 131.3(3) . . . . ?
C3 C4 C5 C6 -48.9(4) . . . . ?
C4 C5 C6 C12 -131.0(3) . . . . ?
C4 C5 C6 C7 48.8(4) . . . . ?
C12 C6 C7 C2 126.3(3) . . . . ?
C5 C6 C7 C2 -53.5(4) . . . . ?
C8 C2 C7 C6 -66.7(3) . . . . ?
C3 C2 C7 C6 53.6(3) . . . . ?
C1 C2 C7 C6 176.1(2) . . . . ?
C3 C2 C8 C9 72.6(3) . . . . ?
C1 C2 C8 C9 -51.8(3) . . . . ?
C7 C2 C8 C9 -169.3(2) . . . . ?
C2 C8 C9 C10 17.1(4) . . . . ?
C2 C8 C9 P1 -163.44(18) . . . . ?
C29 P1 C9 C10 -59.6(2) . . . . ?
C21 P1 C9 C10 180.0(2) . . . . ?
C25 P1 C9 C10 60.3(2) . . . . ?
C29 P1 C9 C8 120.9(2) . . . . ?
C21 P1 C9 C8 0.5(3) . . . . ?
C25 P1 C9 C8 -119.2(2) . . . . ?
C8 C9 C10 B1 9.1(4) . . . . ?
P1 C9 C10 B1 -170.4(2) . . . . ?
C9 P1 C21 C24 74.3(2) . . . . ?
C29 P1 C21 C24 -44.7(2) . . . . ?
C25 P1 C21 C24 -166.8(2) . . . . ?
C9 P1 C21 C22 -165.9(2) . . . . ?
C29 P1 C21 C22 75.0(3) . . . . ?
C25 P1 C21 C22 -47.1(3) . . . . ?
C9 P1 C21 C23 -46.3(3) . . . . ?
C29 P1 C21 C23 -165.3(2) . . . . ?
C25 P1 C21 C23 72.6(3) . . . . ?
C9 P1 C25 C26 74.0(2) . . . . ?
C29 P1 C25 C26 -168.0(2) . . . . ?
C21 P1 C25 C26 -46.4(2) . . . . ?
C9 P1 C25 C28 -42.2(2) . . . . ?
C29 P1 C25 C28 75.8(2) . . . . ?
C21 P1 C25 C28 -162.6(2) . . . . ?
C9 P1 C25 C27 -164.0(2) . . . . ?
C29 P1 C25 C27 -46.0(3) . . . . ?
C21 P1 C25 C27 75.6(2) . . . . ?
C9 P1 C29 C32 -42.1(2) . . . . ?
C21 P1 C29 C32 78.6(2) . . . . ?
C25 P1 C29 C32 -160.2(2) . . . . ?
C9 P1 C29 C31 76.0(2) . . . . ?
C21 P1 C29 C31 -163.3(2) . . . . ?
C25 P1 C29 C31 -42.1(3) . . . . ?
C9 P1 C29 C30 -163.9(2) . . . . ?
C21 P1 C29 C30 -43.1(2) . . . . ?
C25 P1 C29 C30 78.1(2) . . . . ?
C9 C10 B1 C1 1.2(4) . . . . ?
C9 C10 B1 C41 -124.9(3) . . . . ?
C9 C10 B1 C51 123.2(3) . . . . ?
C2 C1 B1 C10 -37.5(3) . . . . ?
C2 C1 B1 C41 89.7(3) . . . . ?
C2 C1 B1 C51 -153.6(2) . . . . ?
C10 B1 C41 C46 -7.6(4) . . . . ?
C1 B1 C41 C46 -130.6(3) . . . . ?
C51 B1 C41 C46 105.8(3) . . . . ?
C10 B1 C41 C42 179.5(3) . . . . ?
C1 B1 C41 C42 56.5(3) . . . . ?
C51 B1 C41 C42 -67.1(3) . . . . ?
C46 C41 C42 F42 -178.7(2) . . . . ?
B1 C41 C42 F42 -4.9(4) . . . . ?
C46 C41 C42 C43 -1.5(4) . . . . ?
B1 C41 C42 C43 172.3(3) . . . . ?
F42 C42 C43 F43 -2.8(4) . . . . ?
C41 C42 C43 F43 179.9(3) . . . . ?
F42 C42 C43 C44 176.6(3) . . . . ?
C41 C42 C43 C44 -0.8(5) . . . . ?
F43 C43 C44 F44 0.6(4) . . . . ?
C42 C43 C44 F44 -178.7(3) . . . . ?
F43 C43 C44 C45 -179.0(3) . . . . ?
C42 C43 C44 C45 1.7(5) . . . . ?
F44 C44 C45 F45 0.0(4) . . . . ?
C43 C44 C45 F45 179.6(3) . . . . ?
F44 C44 C45 C46 -179.9(3) . . . . ?
C43 C44 C45 C46 -0.3(4) . . . . ?
F45 C45 C46 F46 -0.3(4) . . . . ?
C44 C45 C46 F46 179.6(3) . . . . ?
F45 C45 C46 C41 177.9(3) . . . . ?
C44 C45 C46 C41 -2.2(5) . . . . ?
C42 C41 C46 F46 -178.9(2) . . . . ?
B1 C41 C46 F46 7.6(4) . . . . ?
C42 C41 C46 C45 2.9(4) . . . . ?
B1 C41 C46 C45 -170.5(3) . . . . ?
C10 B1 C51 C52 -123.1(3) . . . . ?
C1 B1 C51 C52 -6.0(4) . . . . ?
C41 B1 C51 C52 116.6(3) . . . . ?
C10 B1 C51 C56 58.0(3) . . . . ?
C1 B1 C51 C56 175.1(3) . . . . ?
C41 B1 C51 C56 -62.3(3) . . . . ?
C56 C51 C52 F52 177.8(3) . . . . ?
B1 C51 C52 F52 -1.2(4) . . . . ?
C56 C51 C52 C53 -2.3(4) . . . . ?
B1 C51 C52 C53 178.7(3) . . . . ?
F52 C52 C53 F53 2.1(4) . . . . ?
C51 C52 C53 F53 -177.9(3) . . . . ?
F52 C52 C53 C54 -178.5(3) . . . . ?
C51 C52 C53 C54 1.6(5) . . . . ?
F53 C53 C54 F54 -1.1(5) . . . . ?
C52 C53 C54 F54 179.4(3) . . . . ?
F53 C53 C54 C55 180.0(3) . . . . ?
C52 C53 C54 C55 0.5(5) . . . . ?
F54 C54 C55 F55 -0.1(5) . . . . ?
C53 C54 C55 F55 178.8(3) . . . . ?
F54 C54 C55 C56 179.5(3) . . . . ?
C53 C54 C55 C56 -1.5(5) . . . . ?
F55 C55 C56 F56 -0.1(4) . . . . ?
C54 C55 C56 F56 -179.8(3) . . . . ?
F55 C55 C56 C51 -179.7(3) . . . . ?
C54 C55 C56 C51 0.7(5) . . . . ?
C52 C51 C56 F56 -178.4(3) . . . . ?
B1 C51 C56 F56 0.7(4) . . . . ?
C52 C51 C56 C55 1.2(4) . . . . ?
B1 C51 C56 C55 -179.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.060
#=============================================================================
#  end of cif data for "erk9169" (compound 12)
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================
####################################################################### 
# 
# 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_erk9371
_database_code_depnum_ccdc_archive 'CCDC 1881527'
_audit_update_record             
;
2018-11-27 deposited with the CCDC.
2019-01-14 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27.50 H43 Cl'
_chemical_formula_iupac          ?
_chemical_formula_weight         409.07

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   10.8108(3)
_cell_length_b                   12.1099(3)
_cell_length_c                   19.1989(5)
_cell_angle_alpha                76.7030(10)
_cell_angle_beta                 75.1760(10)
_cell_angle_gamma                87.9660(10)
_cell_volume                     2363.95(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9965
_cell_measurement_theta_min      2.4454
_cell_measurement_theta_max      66.8503
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             900

_exptl_absorpt_coefficient_mu    1.479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            25656
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         66.84
_diffrn_reflns_theta_full        66.84
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_refine_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.

Two Chx groups and one methyl group are disordered over 
two positions. Several restraints (SADI, SAME, ISOR and
SIMU) were used in order to improve refinement stability.
;

_reflns_number_total             8246
_reflns_number_gt                5834
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_gt          0.1555
_refine_ls_wR_factor_ref         0.1720
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.021
_refine_ls_number_reflns         8246
_refine_ls_number_parameters     639
_refine_ls_number_restraints     321
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0638P)²+3.0825P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.720
_refine_diff_density_min         -0.554
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;

APEX3 v2016.1-0 (Bruker AXS Inc., 2016)
;
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1A 0.8270(3) 0.0354(2) 0.12183(16) 0.0219(6) Uani d . . . 1.0 . .
C C2A 0.8447(3) 0.1449(2) 0.13056(16) 0.0203(6) Uani d . . . 1.0 . .
C C3A 0.8353(3) 0.2398(2) 0.07361(16) 0.0192(6) Uani d . . . 1.0 . .
C C4A 0.8057(3) 0.2249(2) 0.00898(15) 0.0185(6) Uani d . . . 1.0 . .
C C5A 0.7877(3) 0.1133(2) 0.00150(16) 0.0201(6) Uani d . . . 1.0 . .
C C6A 0.7909(3) 0.0195(2) 0.05941(16) 0.0203(6) Uani d . . . 1.0 . .
C C7A 0.8530(3) -0.0692(3) 0.17730(18) 0.0312(7) Uani d . . . 1.0 . .
H H731 0.9094 -0.0478 0.205 0.047 Uiso calc U . R 1.0 . .
H H732 0.8943 -0.1263 0.1509 0.047 Uiso calc U . R 1.0 . .
H H733 0.772 -0.1005 0.2117 0.047 Uiso calc U . R 1.0 . .
C C8A 0.8643(3) 0.3580(3) 0.08105(17) 0.0249(7) Uani d . . . 1.0 . .
H H831 0.8843 0.41 0.0321 0.037 Uiso calc U . R 1.0 . .
H H832 0.9377 0.3552 0.1025 0.037 Uiso calc U . R 1.0 . .
H H833 0.7895 0.3848 0.1133 0.037 Uiso calc U . R 1.0 . .
C C9A 0.7750(3) 0.0966(3) -0.07273(17) 0.0275(7) Uani d . . . 1.0 . .
H H931 0.7928 0.0177 -0.0756 0.041 Uiso calc U . R 1.0 . .
H H932 0.8362 0.1473 -0.113 0.041 Uiso calc U . R 1.0 . .
H H933 0.6878 0.1142 -0.0773 0.041 Uiso calc U . R 1.0 . .
C C11A 0.8685(3) 0.1677(3) 0.20192(16) 0.0239(6) Uani d . . . 1.0 . .
H H11A 0.8505 0.25 0.1986 0.029 Uiso calc U . R 1.0 . .
C C12A 1.0093(3) 0.1574(3) 0.20551(16) 0.0236(6) Uani d . . . 1.0 . .
H H12A 1.0349 0.0774 0.2089 0.028 Uiso calc U . R 1.0 . .
H H12B 1.0645 0.2041 0.1595 0.028 Uiso calc U . R 1.0 . .
C C13A 1.0295(3) 0.1963(3) 0.27203(18) 0.0327(8) Uani d . . . 1.0 . .
H H13A 1.1183 0.1808 0.2758 0.039 Uiso calc U . R 1.0 . .
H H13B 1.0177 0.2793 0.2645 0.039 Uiso calc U . R 1.0 . .
C C14A 0.9370(3) 0.1368(3) 0.34379(17) 0.0310(7) Uani d . . . 1.0 . .
H H14A 0.9492 0.1681 0.3849 0.037 Uiso calc U . R 1.0 . .
H H14B 0.9555 0.0548 0.3546 0.037 Uiso calc U . R 1.0 . .
C C15A 0.7988(3) 0.1520(3) 0.33882(17) 0.0302(7) Uani d . . . 1.0 . .
H H15A 0.7784 0.2335 0.3317 0.036 Uiso calc U . R 1.0 . .
H H15B 0.7407 0.1108 0.3857 0.036 Uiso calc U . R 1.0 . .
C C16A 0.7774(3) 0.1074(3) 0.27468(17) 0.0314(7) Uani d . . . 1.0 . .
H H16A 0.6878 0.12 0.2716 0.038 Uiso calc U . R 1.0 . .
H H16B 0.792 0.0247 0.2835 0.038 Uiso calc U . R 1.0 . .
C C21A 0.7849(3) 0.3236(2) -0.05256(16) 0.0212(6) Uani d . . . 1.0 . .
H H21A 0.7483 0.2868 -0.0847 0.025 Uiso calc U . R 1.0 . .
C C22A 0.9077(3) 0.3845(3) -0.10466(17) 0.0252(7) Uani d . . . 1.0 . .
H H22A 0.9504 0.4235 -0.0768 0.03 Uiso calc U . R 1.0 . .
H H22B 0.9671 0.3279 -0.1238 0.03 Uiso calc U . R 1.0 . .
C C23A 0.8781(3) 0.4711(3) -0.16953(17) 0.0304(7) Uani d . . . 1.0 . .
H H23A 0.9575 0.5141 -0.1994 0.036 Uiso calc U . R 1.0 . .
H H23B 0.8477 0.4307 -0.2016 0.036 Uiso calc U . R 1.0 . .
C C24A 0.7767(3) 0.5539(3) -0.14362(18) 0.0286(7) Uani d . . . 1.0 . .
H H24A 0.8106 0.6006 -0.1162 0.034 Uiso calc U . R 1.0 . .
H H24B 0.7565 0.6055 -0.1872 0.034 Uiso calc U . R 1.0 . .
C C25A 0.6558(3) 0.4912(3) -0.09403(17) 0.0255(7) Uani d . . . 1.0 . .
H H25A 0.618 0.4497 -0.1228 0.031 Uiso calc U . R 1.0 . .
H H25B 0.5928 0.5467 -0.0767 0.031 Uiso calc U . R 1.0 . .
C C26A 0.6825(3) 0.4073(3) -0.02718(17) 0.0244(7) Uani d . . . 1.0 . .
H H26A 0.6027 0.3649 0.0027 0.029 Uiso calc U . R 1.0 . .
H H26B 0.7123 0.4492 0.0043 0.029 Uiso calc U . R 1.0 . .
C C31A 0.7469(3) -0.0995(3) 0.05947(18) 0.0256(7) Uani d . . . 1.0 . .
H H31A 0.737 -0.1424 0.1118 0.031 Uiso calc U . R 1.0 . .
C C32A 0.6151(3) -0.1063(3) 0.0480(2) 0.0398(9) Uani d . . . 1.0 . .
H H32A 0.6164 -0.069 -0.0038 0.048 Uiso calc U . R 1.0 . .
H H32B 0.5548 -0.0653 0.0809 0.048 Uiso calc U . R 1.0 . .
C C33A 0.5689(3) -0.2301(3) 0.0646(2) 0.0383(9) Uani d . . . 1.0 . .
H H33A 0.5587 -0.2651 0.1178 0.046 Uiso calc U . R 1.0 . .
H H33B 0.4844 -0.2326 0.0538 0.046 Uiso calc U . R 1.0 . .
C C34A 0.6643(3) -0.2973(3) 0.0179(2) 0.0429(9) Uani d . . . 1.0 . .
H H34A 0.6356 -0.3779 0.0322 0.051 Uiso calc U . R 1.0 . .
H H34B 0.6657 -0.2682 -0.0349 0.051 Uiso calc U . R 1.0 . .
C C35A 0.7967(3) -0.2896(3) 0.0271(2) 0.0359(8) Uani d . . . 1.0 . .
H H35A 0.8558 -0.3277 -0.0082 0.043 Uiso calc U . R 1.0 . .
H H35B 0.7981 -0.3309 0.0777 0.043 Uiso calc U . R 1.0 . .
C C36A 0.8449(3) -0.1683(3) 0.01433(18) 0.0261(7) Uani d . . . 1.0 . .
H H36A 0.8614 -0.1314 -0.039 0.031 Uiso calc U . R 1.0 . .
H H36B 0.9266 -0.1691 0.0287 0.031 Uiso calc U . R 1.0 . .
C C1B 0.7013(3) 0.6637(3) 0.46407(17) 0.0281(7) Uani d . . . 1.0 . .
C C2B 0.7304(3) 0.6783(3) 0.52902(17) 0.0254(7) Uani d . . . 1.0 . .
C C3B 0.7753(3) 0.5850(3) 0.57397(17) 0.0265(7) Uani d . . . 1.0 . .
C C5B 0.7593(3) 0.4662(3) 0.49083(19) 0.0328(8) Uani d U . D 1.0 . .
C C9B 0.778(2) 0.3532(8) 0.4677(7) 0.052(3) Uani d U P D 0.78(5) A 1
H H901 0.808 0.2972 0.505 0.078 Uiso calc U P R 0.78(5) A 1
H H902 0.6964 0.3265 0.4633 0.078 Uiso calc U P R 0.78(5) A 1
H H903 0.8414 0.3632 0.4199 0.078 Uiso calc U P R 0.78(5) A 1
C C9D 0.817(3) 0.3580(16) 0.4687(18) 0.030(7) Uani d U P D 0.22(5) A 2
H H911 0.8394 0.3073 0.5113 0.045 Uiso calc U P R 0.22(5) A 2
H H912 0.7551 0.3196 0.4526 0.045 Uiso calc U P R 0.22(5) A 2
H H913 0.8948 0.378 0.4281 0.045 Uiso calc U P R 0.22(5) A 2
C C7B 0.6586(4) 0.7654(3) 0.4132(2) 0.0440(10) Uani d . . . 1.0 . .
H H741 0.5659 0.7596 0.4198 0.066 Uiso calc U . R 1.0 . .
H H742 0.7027 0.7664 0.3616 0.066 Uiso calc U . R 1.0 . .
H H743 0.6796 0.8355 0.4254 0.066 Uiso calc U . R 1.0 . .
C C8B 0.8225(4) 0.6023(3) 0.6392(2) 0.0407(9) Uani d . . . 1.0 . .
H H841 0.8691 0.6753 0.6253 0.061 Uiso calc U . R 1.0 . .
H H842 0.8795 0.5408 0.6525 0.061 Uiso calc U . R 1.0 . .
H H843 0.7491 0.602 0.6816 0.061 Uiso calc U . R 1.0 . .
C C11B 0.7111(3) 0.7899(3) 0.5546(2) 0.0346(8) Uani d . . . 1.0 . .
H H11B 0.7201 0.7658 0.6065 0.042 Uiso calc U . R 1.0 . .
C C12B 0.5777(3) 0.8385(3) 0.5662(2) 0.0449(10) Uani d . . . 1.0 . .
H H12C 0.557 0.8636 0.5177 0.054 Uiso calc U . R 1.0 . .
H H12D 0.5146 0.7783 0.5973 0.054 Uiso calc U . R 1.0 . .
C C13B 0.5663(3) 0.9378(3) 0.6028(2) 0.0395(9) Uani d . . . 1.0 . .
H H13C 0.4821 0.9727 0.6028 0.047 Uiso calc U . R 1.0 . .
H H13D 0.5688 0.9091 0.6551 0.047 Uiso calc U . R 1.0 . .
C C14B 0.6686(4) 1.0266(3) 0.5663(2) 0.0494(10) Uani d . . . 1.0 . .
H H14C 0.6617 1.083 0.5971 0.059 Uiso calc U . R 1.0 . .
H H14D 0.6551 1.0665 0.5178 0.059 Uiso calc U . R 1.0 . .
C C15B 0.8026(3) 0.9790(3) 0.5545(2) 0.0411(9) Uani d . . . 1.0 . .
H H15C 0.8645 1.0397 0.5228 0.049 Uiso calc U . R 1.0 . .
H H15D 0.8239 0.9561 0.6029 0.049 Uiso calc U . R 1.0 . .
C C16B 0.8176(3) 0.8788(3) 0.5194(2) 0.0423(9) Uani d . . . 1.0 . .
H H16C 0.9003 0.8431 0.5229 0.051 Uiso calc U . R 1.0 . .
H H16D 0.8205 0.9059 0.4663 0.051 Uiso calc U . R 1.0 . .
C C4B 0.7831(3) 0.4772(3) 0.55793(17) 0.0279(7) Uani d . . D 1.0 . .
C C21B 0.8098(10) 0.3624(8) 0.6048(5) 0.027(3) Uani d U P D 0.500(8) B 1
H H21B 0.7823 0.3061 0.5805 0.032 Uiso calc U P R 0.500(8) B 1
C C22B 0.7232(6) 0.3334(6) 0.6828(4) 0.0321(19) Uani d U P D 0.500(8) B 1
H H22C 0.7352 0.3924 0.7087 0.039 Uiso calc U P R 0.500(8) B 1
H H22D 0.633 0.335 0.6799 0.039 Uiso calc U P R 0.500(8) B 1
C C23B 0.7480(8) 0.2182(7) 0.7279(5) 0.030(2) Uani d U P D 0.500(8) B 1
H H23C 0.7039 0.213 0.7806 0.036 Uiso calc U P R 0.500(8) B 1
H H23D 0.7104 0.1584 0.7114 0.036 Uiso calc U P R 0.500(8) B 1
C C24B 0.8875(7) 0.1955(8) 0.7216(4) 0.039(2) Uani d U P D 0.500(8) B 1
H H24C 0.8964 0.1145 0.7443 0.047 Uiso calc U P R 0.500(8) B 1
H H24D 0.919 0.2411 0.7505 0.047 Uiso calc U P R 0.500(8) B 1
C C25B 0.9709(7) 0.2218(6) 0.6438(4) 0.0338(19) Uani d U P D 0.500(8) B 1
H H25C 0.954 0.1637 0.6183 0.041 Uiso calc U P R 0.500(8) B 1
H H25D 1.0617 0.2165 0.6455 0.041 Uiso calc U P R 0.500(8) B 1
C C26B 0.9503(11) 0.3376(14) 0.5990(10) 0.036(4) Uani d U P D 0.500(8) B 1
H H26C 0.9953 0.343 0.5465 0.043 Uiso calc U P R 0.500(8) B 1
H H26D 0.9885 0.396 0.6163 0.043 Uiso calc U P R 0.500(8) B 1
C C21D 0.8089(9) 0.3833(7) 0.6224(5) 0.024(2) Uani d U P D 0.500(8) B 2
H H21D 0.795 0.4189 0.6658 0.029 Uiso calc U P R 0.500(8) B 2
C C22D 0.7062(7) 0.2871(6) 0.6447(5) 0.041(2) Uani d U P D 0.500(8) B 2
H H22E 0.6199 0.3198 0.6537 0.049 Uiso calc U P R 0.500(8) B 2
H H22F 0.716 0.2479 0.6037 0.049 Uiso calc U P R 0.500(8) B 2
C C23D 0.7189(9) 0.2026(8) 0.7136(6) 0.039(3) Uani d U P D 0.500(8) B 2
H H23E 0.6536 0.141 0.7261 0.047 Uiso calc U P R 0.500(8) B 2
H H23F 0.7025 0.2408 0.7553 0.047 Uiso calc U P R 0.500(8) B 2
C C24D 0.8503(7) 0.1518(6) 0.7038(4) 0.0316(17) Uani d U P D 0.500(8) B 2
H H24E 0.8629 0.1058 0.6662 0.038 Uiso calc U P R 0.500(8) B 2
H H24F 0.8566 0.101 0.7511 0.038 Uiso calc U P R 0.500(8) B 2
C C25D 0.9548(8) 0.2441(7) 0.6796(6) 0.042(2) Uani d U P D 0.500(8) B 2
H H25E 0.9515 0.2804 0.7212 0.051 Uiso calc U P R 0.500(8) B 2
H H25F 1.0392 0.2085 0.668 0.051 Uiso calc U P R 0.500(8) B 2
C C26D 0.9430(11) 0.3350(13) 0.6124(9) 0.034(4) Uani d U P D 0.500(8) B 2
H H26E 0.9635 0.3022 0.5682 0.041 Uiso calc U P R 0.500(8) B 2
H H26F 1.006 0.3973 0.6038 0.041 Uiso calc U P R 0.500(8) B 2
C C6B 0.7162(3) 0.5586(3) 0.44438(17) 0.0305(7) Uani d . . D 1.0 . .
C C31B 0.6764(6) 0.5590(6) 0.3724(3) 0.0268(15) Uani d U P D 0.674(9) C 1
H H31B 0.6297 0.631 0.3609 0.032 Uiso calc U P R 0.674(9) C 1
C C32B 0.7938(9) 0.5642(12) 0.3064(4) 0.039(3) Uani d U P D 0.674(9) C 1
H H32C 0.8412 0.4928 0.3137 0.047 Uiso calc U P R 0.674(9) C 1
H H32D 0.8518 0.6278 0.3029 0.047 Uiso calc U P R 0.674(9) C 1
C C33B 0.7487(6) 0.5814(6) 0.2342(3) 0.0368(16) Uani d U P D 0.674(9) C 1
H H33C 0.7028 0.6536 0.2264 0.044 Uiso calc U P R 0.674(9) C 1
H H33D 0.8237 0.5854 0.1913 0.044 Uiso calc U P R 0.674(9) C 1
C C34B 0.6592(6) 0.4817(6) 0.2401(3) 0.0366(15) Uani d U P D 0.674(9) C 1
H H34C 0.6325 0.4905 0.1935 0.044 Uiso calc U P R 0.674(9) C 1
H H34D 0.7044 0.4092 0.2486 0.044 Uiso calc U P R 0.674(9) C 1
C C35B 0.5426(10) 0.4809(11) 0.3044(4) 0.040(3) Uani d U P D 0.674(9) C 1
H H35C 0.4819 0.4195 0.3076 0.048 Uiso calc U P R 0.674(9) C 1
H H35D 0.4987 0.5541 0.296 0.048 Uiso calc U P R 0.674(9) C 1
C C36B 0.5841(6) 0.4620(6) 0.3784(3) 0.0334(15) Uani d U P D 0.674(9) C 1
H H36C 0.5079 0.4609 0.4202 0.04 Uiso calc U P R 0.674(9) C 1
H H36D 0.6267 0.3883 0.3875 0.04 Uiso calc U P R 0.674(9) C 1
C C31D 0.7023(10) 0.5179(12) 0.3759(6) 0.023(3) Uani d U P D 0.326(9) C 2
H H31D 0.731 0.4376 0.3817 0.027 Uiso calc U P R 0.326(9) C 2
C C32D 0.786(2) 0.586(2) 0.3022(8) 0.035(5) Uani d U P D 0.326(9) C 2
H H32E 0.8766 0.5862 0.3041 0.043 Uiso calc U P R 0.326(9) C 2
H H32F 0.7581 0.666 0.2928 0.043 Uiso calc U P R 0.326(9) C 2
C C33D 0.7709(10) 0.5295(13) 0.2391(7) 0.034(3) Uani d U P D 0.326(9) C 2
H H33E 0.8256 0.5704 0.1909 0.041 Uiso calc U P R 0.326(9) C 2
H H33F 0.798 0.4497 0.2488 0.041 Uiso calc U P R 0.326(9) C 2
C C34D 0.6302(10) 0.5338(12) 0.2365(6) 0.029(3) Uani d U P D 0.326(9) C 2
H H34E 0.6195 0.5043 0.1944 0.035 Uiso calc U P R 0.326(9) C 2
H H34F 0.6006 0.613 0.2306 0.035 Uiso calc U P R 0.326(9) C 2
C C35D 0.5523(19) 0.4592(19) 0.3105(8) 0.027(4) Uani d U P D 0.326(9) C 2
H H35E 0.5875 0.3821 0.3187 0.032 Uiso calc U P R 0.326(9) C 2
H H35F 0.4618 0.4529 0.3096 0.032 Uiso calc U P R 0.326(9) C 2
C C36D 0.5621(10) 0.5172(13) 0.3738(7) 0.034(3) Uani d U P D 0.326(9) C 2
H H36E 0.5313 0.5959 0.3642 0.041 Uiso calc U P R 0.326(9) C 2
H H36F 0.5088 0.4746 0.4219 0.041 Uiso calc U P R 0.326(9) C 2
C C41 0.5090(4) 0.1562(4) 0.1524(2) 0.0499(11) Uani d . . . 1.0 . .
H H41A 0.5342 0.1838 0.0979 0.06 Uiso calc U . R 1.0 . .
H H41B 0.5741 0.1021 0.1664 0.06 Uiso calc U . R 1.0 . .
Cl Cl1 0.36170(9) 0.08547(9) 0.17809(6) 0.0542(3) Uani d . . . 1.0 . .
Cl Cl2 0.50842(9) 0.27147(8) 0.19336(5) 0.0410(2) Uani d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1A C2A . 1.401(4) ?
C1A C6A . 1.406(4) ?
C1A C7A . 1.524(4) ?
C2A C3A . 1.413(4) ?
C2A C11A . 1.542(4) ?
C3A C4A . 1.409(4) ?
C3A C8A . 1.521(4) ?
C4A C5A . 1.416(4) ?
C4A C21A . 1.530(4) ?
C5A C6A . 1.402(4) ?
C5A C9A . 1.525(4) ?
C6A C31A . 1.532(4) ?
C7A H731 . 0.98 ?
C7A H732 . 0.98 ?
C7A H733 . 0.98 ?
C8A H831 . 0.98 ?
C8A H832 . 0.98 ?
C8A H833 . 0.98 ?
C9A H931 . 0.98 ?
C9A H932 . 0.98 ?
C9A H933 . 0.98 ?
C11A C16A . 1.527(4) ?
C11A C12A . 1.541(4) ?
C11A H11A . 1.0 ?
C12A C13A . 1.526(4) ?
C12A H12A . 0.99 ?
C12A H12B . 0.99 ?
C13A C14A . 1.519(4) ?
C13A H13A . 0.99 ?
C13A H13B . 0.99 ?
C14A C15A . 1.523(4) ?
C14A H14A . 0.99 ?
C14A H14B . 0.99 ?
C15A C16A . 1.524(4) ?
C15A H15A . 0.99 ?
C15A H15B . 0.99 ?
C16A H16A . 0.99 ?
C16A H16B . 0.99 ?
C21A C22A . 1.535(4) ?
C21A C26A . 1.537(4) ?
C21A H21A . 1.0 ?
C22A C23A . 1.527(4) ?
C22A H22A . 0.99 ?
C22A H22B . 0.99 ?
C23A C24A . 1.525(4) ?
C23A H23A . 0.99 ?
C23A H23B . 0.99 ?
C24A C25A . 1.514(4) ?
C24A H24A . 0.99 ?
C24A H24B . 0.99 ?
C25A C26A . 1.527(4) ?
C25A H25A . 0.99 ?
C25A H25B . 0.99 ?
C26A H26A . 0.99 ?
C26A H26B . 0.99 ?
C31A C32A . 1.504(4) ?
C31A C36A . 1.538(4) ?
C31A H31A . 1.0 ?
C32A C33A . 1.533(5) ?
C32A H32A . 0.99 ?
C32A H32B . 0.99 ?
C33A C34A . 1.528(5) ?
C33A H33A . 0.99 ?
C33A H33B . 0.99 ?
C34A C35A . 1.495(5) ?
C34A H34A . 0.99 ?
C34A H34B . 0.99 ?
C35A C36A . 1.521(4) ?
C35A H35A . 0.99 ?
C35A H35B . 0.99 ?
C36A H36A . 0.99 ?
C36A H36B . 0.99 ?
C1B C6B . 1.401(5) ?
C1B C2B . 1.411(4) ?
C1B C7B . 1.523(5) ?
C2B C3B . 1.408(4) ?
C2B C11B . 1.531(5) ?
C3B C4B . 1.403(5) ?
C3B C8B . 1.525(4) ?
C5B C6B . 1.408(5) ?
C5B C4B . 1.412(5) ?
C5B C9B . 1.525(7) ?
C5B C9D . 1.533(16) ?
C9B H901 . 0.98 ?
C9B H902 . 0.98 ?
C9B H903 . 0.98 ?
C9D H911 . 0.98 ?
C9D H912 . 0.98 ?
C9D H913 . 0.98 ?
C7B H741 . 0.98 ?
C7B H742 . 0.98 ?
C7B H743 . 0.98 ?
C8B H841 . 0.98 ?
C8B H842 . 0.98 ?
C8B H843 . 0.98 ?
C11B C16B . 1.515(5) ?
C11B C12B . 1.521(5) ?
C11B H11B . 1.0 ?
C12B C13B . 1.513(5) ?
C12B H12C . 0.99 ?
C12B H12D . 0.99 ?
C13B C14B . 1.488(5) ?
C13B H13C . 0.99 ?
C13B H13D . 0.99 ?
C14B C15B . 1.521(5) ?
C14B H14C . 0.99 ?
C14B H14D . 0.99 ?
C15B C16B . 1.504(5) ?
C15B H15C . 0.99 ?
C15B H15D . 0.99 ?
C16B H16C . 0.99 ?
C16B H16D . 0.99 ?
C4B C21B . 1.535(9) ?
C4B C21D . 1.553(8) ?
C21B C26B . 1.519(11) ?
C21B C22B . 1.519(9) ?
C21B H21B . 1.0 ?
C22B C23B . 1.519(9) ?
C22B H22C . 0.99 ?
C22B H22D . 0.99 ?
C23B C24B . 1.502(9) ?
C23B H23C . 0.99 ?
C23B H23D . 0.99 ?
C24B C25B . 1.503(9) ?
C24B H24C . 0.99 ?
C24B H24D . 0.99 ?
C25B C26B . 1.509(11) ?
C25B H25C . 0.99 ?
C25B H25D . 0.99 ?
C26B H26C . 0.99 ?
C26B H26D . 0.99 ?
C21D C26D . 1.526(11) ?
C21D C22D . 1.547(10) ?
C21D H21D . 1.0 ?
C22D C23D . 1.509(10) ?
C22D H22E . 0.99 ?
C22D H22F . 0.99 ?
C23D C24D . 1.512(10) ?
C23D H23E . 0.99 ?
C23D H23F . 0.99 ?
C24D C25D . 1.524(9) ?
C24D H24E . 0.99 ?
C24D H24F . 0.99 ?
C25D C26D . 1.521(11) ?
C25D H25E . 0.99 ?
C25D H25F . 0.99 ?
C26D H26E . 0.99 ?
C26D H26F . 0.99 ?
C6B C31B . 1.548(6) ?
C6B C31D . 1.549(11) ?
C31B C36B . 1.533(7) ?
C31B C32B . 1.538(9) ?
C31B H31B . 1.0 ?
C32B C33B . 1.553(9) ?
C32B H32C . 0.99 ?
C32B H32D . 0.99 ?
C33B C34B . 1.539(8) ?
C33B H33C . 0.99 ?
C33B H33D . 0.99 ?
C34B C35B . 1.521(9) ?
C34B H34C . 0.99 ?
C34B H34D . 0.99 ?
C35B C36B . 1.562(9) ?
C35B H35C . 0.99 ?
C35B H35D . 0.99 ?
C36B H36C . 0.99 ?
C36B H36D . 0.99 ?
C31D C36D . 1.527(12) ?
C31D C32D . 1.537(13) ?
C31D H31D . 1.0 ?
C32D C33D . 1.570(13) ?
C32D H32E . 0.99 ?
C32D H32F . 0.99 ?
C33D C34D . 1.533(12) ?
C33D H33E . 0.99 ?
C33D H33F . 0.99 ?
C34D C35D . 1.547(13) ?
C34D H34E . 0.99 ?
C34D H34F . 0.99 ?
C35D C36D . 1.563(13) ?
C35D H35E . 0.99 ?
C35D H35F . 0.99 ?
C36D H36E . 0.99 ?
C36D H36F . 0.99 ?
C41 Cl1 . 1.736(4) ?
C41 Cl2 . 1.752(4) ?
C41 H41A . 0.99 ?
C41 H41B . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2A C1A C6A . . 120.5(3) ?
C2A C1A C7A . . 121.1(3) ?
C6A C1A C7A . . 118.3(3) ?
C1A C2A C3A . . 119.6(3) ?
C1A C2A C11A . . 122.7(3) ?
C3A C2A C11A . . 117.7(3) ?
C4A C3A C2A . . 120.4(3) ?
C4A C3A C8A . . 120.3(3) ?
C2A C3A C8A . . 119.2(3) ?
C3A C4A C5A . . 118.9(3) ?
C3A C4A C21A . . 123.4(3) ?
C5A C4A C21A . . 117.6(3) ?
C6A C5A C4A . . 120.6(3) ?
C6A C5A C9A . . 120.5(3) ?
C4A C5A C9A . . 118.7(3) ?
C5A C6A C1A . . 119.4(3) ?
C5A C6A C31A . . 121.9(3) ?
C1A C6A C31A . . 118.5(3) ?
C1A C7A H731 . . 109.5 ?
C1A C7A H732 . . 109.5 ?
H731 C7A H732 . . 109.5 ?
C1A C7A H733 . . 109.5 ?
H731 C7A H733 . . 109.5 ?
H732 C7A H733 . . 109.5 ?
C3A C8A H831 . . 109.5 ?
C3A C8A H832 . . 109.5 ?
H831 C8A H832 . . 109.5 ?
C3A C8A H833 . . 109.5 ?
H831 C8A H833 . . 109.5 ?
H832 C8A H833 . . 109.5 ?
C5A C9A H931 . . 109.5 ?
C5A C9A H932 . . 109.5 ?
H931 C9A H932 . . 109.5 ?
C5A C9A H933 . . 109.5 ?
H931 C9A H933 . . 109.5 ?
H932 C9A H933 . . 109.5 ?
C16A C11A C12A . . 111.7(3) ?
C16A C11A C2A . . 116.4(3) ?
C12A C11A C2A . . 114.1(2) ?
C16A C11A H11A . . 104.3 ?
C12A C11A H11A . . 104.3 ?
C2A C11A H11A . . 104.3 ?
C13A C12A C11A . . 111.4(3) ?
C13A C12A H12A . . 109.3 ?
C11A C12A H12A . . 109.3 ?
C13A C12A H12B . . 109.3 ?
C11A C12A H12B . . 109.3 ?
H12A C12A H12B . . 108.0 ?
C14A C13A C12A . . 112.0(3) ?
C14A C13A H13A . . 109.2 ?
C12A C13A H13A . . 109.2 ?
C14A C13A H13B . . 109.2 ?
C12A C13A H13B . . 109.2 ?
H13A C13A H13B . . 107.9 ?
C13A C14A C15A . . 111.1(3) ?
C13A C14A H14A . . 109.4 ?
C15A C14A H14A . . 109.4 ?
C13A C14A H14B . . 109.4 ?
C15A C14A H14B . . 109.4 ?
H14A C14A H14B . . 108.0 ?
C14A C15A C16A . . 110.9(3) ?
C14A C15A H15A . . 109.5 ?
C16A C15A H15A . . 109.5 ?
C14A C15A H15B . . 109.5 ?
C16A C15A H15B . . 109.5 ?
H15A C15A H15B . . 108.1 ?
C15A C16A C11A . . 110.4(3) ?
C15A C16A H16A . . 109.6 ?
C11A C16A H16A . . 109.6 ?
C15A C16A H16B . . 109.6 ?
C11A C16A H16B . . 109.6 ?
H16A C16A H16B . . 108.1 ?
C4A C21A C22A . . 115.1(2) ?
C4A C21A C26A . . 115.0(2) ?
C22A C21A C26A . . 112.2(2) ?
C4A C21A H21A . . 104.3 ?
C22A C21A H21A . . 104.3 ?
C26A C21A H21A . . 104.3 ?
C23A C22A C21A . . 111.1(3) ?
C23A C22A H22A . . 109.4 ?
C21A C22A H22A . . 109.4 ?
C23A C22A H22B . . 109.4 ?
C21A C22A H22B . . 109.4 ?
H22A C22A H22B . . 108.0 ?
C24A C23A C22A . . 112.0(3) ?
C24A C23A H23A . . 109.2 ?
C22A C23A H23A . . 109.2 ?
C24A C23A H23B . . 109.2 ?
C22A C23A H23B . . 109.2 ?
H23A C23A H23B . . 107.9 ?
C25A C24A C23A . . 111.0(3) ?
C25A C24A H24A . . 109.4 ?
C23A C24A H24A . . 109.4 ?
C25A C24A H24B . . 109.4 ?
C23A C24A H24B . . 109.4 ?
H24A C24A H24B . . 108.0 ?
C24A C25A C26A . . 111.6(3) ?
C24A C25A H25A . . 109.3 ?
C26A C25A H25A . . 109.3 ?
C24A C25A H25B . . 109.3 ?
C26A C25A H25B . . 109.3 ?
H25A C25A H25B . . 108.0 ?
C25A C26A C21A . . 110.3(2) ?
C25A C26A H26A . . 109.6 ?
C21A C26A H26A . . 109.6 ?
C25A C26A H26B . . 109.6 ?
C21A C26A H26B . . 109.6 ?
H26A C26A H26B . . 108.1 ?
C32A C31A C6A . . 114.9(3) ?
C32A C31A C36A . . 112.8(3) ?
C6A C31A C36A . . 116.4(2) ?
C32A C31A H31A . . 103.5 ?
C6A C31A H31A . . 103.5 ?
C36A C31A H31A . . 103.5 ?
C31A C32A C33A . . 111.0(3) ?
C31A C32A H32A . . 109.4 ?
C33A C32A H32A . . 109.4 ?
C31A C32A H32B . . 109.4 ?
C33A C32A H32B . . 109.4 ?
H32A C32A H32B . . 108.0 ?
C34A C33A C32A . . 110.7(3) ?
C34A C33A H33A . . 109.5 ?
C32A C33A H33A . . 109.5 ?
C34A C33A H33B . . 109.5 ?
C32A C33A H33B . . 109.5 ?
H33A C33A H33B . . 108.1 ?
C35A C34A C33A . . 112.4(3) ?
C35A C34A H34A . . 109.1 ?
C33A C34A H34A . . 109.1 ?
C35A C34A H34B . . 109.1 ?
C33A C34A H34B . . 109.1 ?
H34A C34A H34B . . 107.9 ?
C34A C35A C36A . . 113.4(3) ?
C34A C35A H35A . . 108.9 ?
C36A C35A H35A . . 108.9 ?
C34A C35A H35B . . 108.9 ?
C36A C35A H35B . . 108.9 ?
H35A C35A H35B . . 107.7 ?
C35A C36A C31A . . 111.3(3) ?
C35A C36A H36A . . 109.4 ?
C31A C36A H36A . . 109.4 ?
C35A C36A H36B . . 109.4 ?
C31A C36A H36B . . 109.4 ?
H36A C36A H36B . . 108.0 ?
C6B C1B C2B . . 121.0(3) ?
C6B C1B C7B . . 119.8(3) ?
C2B C1B C7B . . 119.2(3) ?
C3B C2B C1B . . 118.8(3) ?
C3B C2B C11B . . 118.1(3) ?
C1B C2B C11B . . 123.1(3) ?
C4B C3B C2B . . 121.2(3) ?
C4B C3B C8B . . 119.2(3) ?
C2B C3B C8B . . 119.5(3) ?
C6B C5B C4B . . 120.8(3) ?
C6B C5B C9B . . 118.5(5) ?
C4B C5B C9B . . 120.6(5) ?
C6B C5B C9D . . 125.9(15) ?
C4B C5B C9D . . 111.5(17) ?
C5B C9B H901 . . 109.5 ?
C5B C9B H902 . . 109.5 ?
H901 C9B H902 . . 109.5 ?
C5B C9B H903 . . 109.5 ?
H901 C9B H903 . . 109.5 ?
H902 C9B H903 . . 109.5 ?
C5B C9D H911 . . 109.5 ?
C5B C9D H912 . . 109.5 ?
H911 C9D H912 . . 109.5 ?
C5B C9D H913 . . 109.5 ?
H911 C9D H913 . . 109.5 ?
H912 C9D H913 . . 109.5 ?
C1B C7B H741 . . 109.5 ?
C1B C7B H742 . . 109.5 ?
H741 C7B H742 . . 109.5 ?
C1B C7B H743 . . 109.5 ?
H741 C7B H743 . . 109.5 ?
H742 C7B H743 . . 109.5 ?
C3B C8B H841 . . 109.5 ?
C3B C8B H842 . . 109.5 ?
H841 C8B H842 . . 109.5 ?
C3B C8B H843 . . 109.5 ?
H841 C8B H843 . . 109.5 ?
H842 C8B H843 . . 109.5 ?
C16B C11B C12B . . 113.8(3) ?
C16B C11B C2B . . 116.2(3) ?
C12B C11B C2B . . 117.5(3) ?
C16B C11B H11B . . 102.0 ?
C12B C11B H11B . . 102.0 ?
C2B C11B H11B . . 102.0 ?
C13B C12B C11B . . 112.2(3) ?
C13B C12B H12C . . 109.2 ?
C11B C12B H12C . . 109.2 ?
C13B C12B H12D . . 109.2 ?
C11B C12B H12D . . 109.2 ?
H12C C12B H12D . . 107.9 ?
C14B C13B C12B . . 113.8(3) ?
C14B C13B H13C . . 108.8 ?
C12B C13B H13C . . 108.8 ?
C14B C13B H13D . . 108.8 ?
C12B C13B H13D . . 108.8 ?
H13C C13B H13D . . 107.7 ?
C13B C14B C15B . . 113.1(3) ?
C13B C14B H14C . . 109.0 ?
C15B C14B H14C . . 109.0 ?
C13B C14B H14D . . 109.0 ?
C15B C14B H14D . . 109.0 ?
H14C C14B H14D . . 107.8 ?
C16B C15B C14B . . 113.6(3) ?
C16B C15B H15C . . 108.9 ?
C14B C15B H15C . . 108.9 ?
C16B C15B H15D . . 108.8 ?
C14B C15B H15D . . 108.9 ?
H15C C15B H15D . . 107.7 ?
C15B C16B C11B . . 113.6(3) ?
C15B C16B H16C . . 108.8 ?
C11B C16B H16C . . 108.8 ?
C15B C16B H16D . . 108.8 ?
C11B C16B H16D . . 108.8 ?
H16C C16B H16D . . 107.7 ?
C3B C4B C5B . . 118.6(3) ?
C3B C4B C21B . . 129.6(5) ?
C5B C4B C21B . . 111.8(5) ?
C3B C4B C21D . . 112.2(4) ?
C5B C4B C21D . . 129.0(5) ?
C26B C21B C22B . . 115.0(9) ?
C26B C21B C4B . . 115.2(7) ?
C22B C21B C4B . . 114.1(6) ?
C26B C21B H21B . . 103.4 ?
C22B C21B H21B . . 103.4 ?
C4B C21B H21B . . 103.4 ?
C23B C22B C21B . . 113.6(6) ?
C23B C22B H22C . . 108.8 ?
C21B C22B H22C . . 108.8 ?
C23B C22B H22D . . 108.8 ?
C21B C22B H22D . . 108.8 ?
H22C C22B H22D . . 107.7 ?
C24B C23B C22B . . 113.7(6) ?
C24B C23B H23C . . 108.8 ?
C22B C23B H23C . . 108.8 ?
C24B C23B H23D . . 108.8 ?
C22B C23B H23D . . 108.8 ?
H23C C23B H23D . . 107.7 ?
C23B C24B C25B . . 114.7(7) ?
C23B C24B H24C . . 108.6 ?
C25B C24B H24C . . 108.6 ?
C23B C24B H24D . . 108.6 ?
C25B C24B H24D . . 108.6 ?
H24C C24B H24D . . 107.6 ?
C24B C25B C26B . . 113.8(9) ?
C24B C25B H25C . . 108.8 ?
C26B C25B H25C . . 108.8 ?
C24B C25B H25D . . 108.8 ?
C26B C25B H25D . . 108.8 ?
H25C C25B H25D . . 107.7 ?
C25B C26B C21B . . 112.8(9) ?
C25B C26B H26C . . 109.0 ?
C21B C26B H26C . . 109.0 ?
C25B C26B H26D . . 109.0 ?
C21B C26B H26D . . 109.0 ?
H26C C26B H26D . . 107.8 ?
C26D C21D C22D . . 110.9(9) ?
C26D C21D C4B . . 117.6(7) ?
C22D C21D C4B . . 109.8(6) ?
C26D C21D H21D . . 105.9 ?
C22D C21D H21D . . 105.9 ?
C4B C21D H21D . . 105.9 ?
C23D C22D C21D . . 110.7(7) ?
C23D C22D H22E . . 109.5 ?
C21D C22D H22E . . 109.5 ?
C23D C22D H22F . . 109.5 ?
C21D C22D H22F . . 109.5 ?
H22E C22D H22F . . 108.1 ?
C22D C23D C24D . . 111.9(7) ?
C22D C23D H23E . . 109.2 ?
C24D C23D H23E . . 109.2 ?
C22D C23D H23F . . 109.2 ?
C24D C23D H23F . . 109.2 ?
H23E C23D H23F . . 107.9 ?
C23D C24D C25D . . 111.2(7) ?
C23D C24D H24E . . 109.4 ?
C25D C24D H24E . . 109.4 ?
C23D C24D H24F . . 109.4 ?
C25D C24D H24F . . 109.4 ?
H24E C24D H24F . . 108.0 ?
C26D C25D C24D . . 113.4(9) ?
C26D C25D H25E . . 108.9 ?
C24D C25D H25E . . 108.9 ?
C26D C25D H25F . . 108.9 ?
C24D C25D H25F . . 108.9 ?
H25E C25D H25F . . 107.7 ?
C25D C26D C21D . . 112.0(9) ?
C25D C26D H26E . . 109.2 ?
C21D C26D H26E . . 109.2 ?
C25D C26D H26F . . 109.2 ?
C21D C26D H26F . . 109.2 ?
H26E C26D H26F . . 107.9 ?
C1B C6B C5B . . 119.2(3) ?
C1B C6B C31B . . 113.2(4) ?
C5B C6B C31B . . 127.5(4) ?
C1B C6B C31D . . 133.4(6) ?
C5B C6B C31D . . 107.2(6) ?
C36B C31B C32B . . 110.8(6) ?
C36B C31B C6B . . 114.8(5) ?
C32B C31B C6B . . 111.5(5) ?
C36B C31B H31B . . 106.4 ?
C32B C31B H31B . . 106.4 ?
C6B C31B H31B . . 106.4 ?
C31B C32B C33B . . 109.2(7) ?
C31B C32B H32C . . 109.8 ?
C33B C32B H32C . . 109.8 ?
C31B C32B H32D . . 109.8 ?
C33B C32B H32D . . 109.8 ?
H32C C32B H32D . . 108.3 ?
C34B C33B C32B . . 109.4(6) ?
C34B C33B H33C . . 109.8 ?
C32B C33B H33C . . 109.8 ?
C34B C33B H33D . . 109.8 ?
C32B C33B H33D . . 109.8 ?
H33C C33B H33D . . 108.2 ?
C35B C34B C33B . . 108.4(6) ?
C35B C34B H34C . . 110.0 ?
C33B C34B H34C . . 110.0 ?
C35B C34B H34D . . 110.0 ?
C33B C34B H34D . . 110.0 ?
H34C C34B H34D . . 108.4 ?
C34B C35B C36B . . 110.1(8) ?
C34B C35B H35C . . 109.6 ?
C36B C35B H35C . . 109.6 ?
C34B C35B H35D . . 109.6 ?
C36B C35B H35D . . 109.6 ?
H35C C35B H35D . . 108.2 ?
C31B C36B C35B . . 108.6(6) ?
C31B C36B H36C . . 110.0 ?
C35B C36B H36C . . 110.0 ?
C31B C36B H36D . . 110.0 ?
C35B C36B H36D . . 110.0 ?
H36C C36B H36D . . 108.3 ?
C36D C31D C32D . . 110.7(13) ?
C36D C31D C6B . . 110.5(9) ?
C32D C31D C6B . . 113.6(9) ?
C36D C31D H31D . . 107.2 ?
C32D C31D H31D . . 107.2 ?
C6B C31D H31D . . 107.2 ?
C31D C32D C33D . . 107.9(12) ?
C31D C32D H32E . . 110.1 ?
C33D C32D H32E . . 110.1 ?
C31D C32D H32F . . 110.1 ?
C33D C32D H32F . . 110.1 ?
H32E C32D H32F . . 108.4 ?
C34D C33D C32D . . 108.8(13) ?
C34D C33D H33E . . 109.9 ?
C32D C33D H33E . . 109.9 ?
C34D C33D H33F . . 109.9 ?
C32D C33D H33F . . 109.9 ?
H33E C33D H33F . . 108.3 ?
C33D C34D C35D . . 107.1(12) ?
C33D C34D H34E . . 110.3 ?
C35D C34D H34E . . 110.3 ?
C33D C34D H34F . . 110.3 ?
C35D C34D H34F . . 110.3 ?
H34E C34D H34F . . 108.6 ?
C34D C35D C36D . . 107.6(12) ?
C34D C35D H35E . . 110.2 ?
C36D C35D H35E . . 110.2 ?
C34D C35D H35F . . 110.2 ?
C36D C35D H35F . . 110.2 ?
H35E C35D H35F . . 108.5 ?
C31D C36D C35D . . 107.9(12) ?
C31D C36D H36E . . 110.1 ?
C35D C36D H36E . . 110.1 ?
C31D C36D H36F . . 110.1 ?
C35D C36D H36F . . 110.1 ?
H36E C36D H36F . . 108.4 ?
Cl1 C41 Cl2 . . 113.1(2) ?
Cl1 C41 H41A . . 109.0 ?
Cl2 C41 H41A . . 109.0 ?
Cl1 C41 H41B . . 109.0 ?
Cl2 C41 H41B . . 109.0 ?
H41A C41 H41B . . 107.8 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6A C1A C2A C3A . . . . -4.6(4) ?
C7A C1A C2A C3A . . . . 172.1(3) ?
C6A C1A C2A C11A . . . . 172.6(3) ?
C7A C1A C2A C11A . . . . -10.7(4) ?
C1A C2A C3A C4A . . . . 1.3(4) ?
C11A C2A C3A C4A . . . . -176.0(2) ?
C1A C2A C3A C8A . . . . -175.5(3) ?
C11A C2A C3A C8A . . . . 7.1(4) ?
C2A C3A C4A C5A . . . . -1.1(4) ?
C8A C3A C4A C5A . . . . 175.7(3) ?
C2A C3A C4A C21A . . . . 175.7(3) ?
C8A C3A C4A C21A . . . . -7.5(4) ?
C3A C4A C5A C6A . . . . 4.2(4) ?
C21A C4A C5A C6A . . . . -172.8(3) ?
C3A C4A C5A C9A . . . . -171.2(3) ?
C21A C4A C5A C9A . . . . 11.8(4) ?
C4A C5A C6A C1A . . . . -7.5(4) ?
C9A C5A C6A C1A . . . . 167.9(3) ?
C4A C5A C6A C31A . . . . 168.0(3) ?
C9A C5A C6A C31A . . . . -16.6(4) ?
C2A C1A C6A C5A . . . . 7.7(4) ?
C7A C1A C6A C5A . . . . -169.2(3) ?
C2A C1A C6A C31A . . . . -168.0(3) ?
C7A C1A C6A C31A . . . . 15.2(4) ?
C1A C2A C11A C16A . . . . -48.7(4) ?
C3A C2A C11A C16A . . . . 128.5(3) ?
C1A C2A C11A C12A . . . . 83.7(3) ?
C3A C2A C11A C12A . . . . -99.0(3) ?
C16A C11A C12A C13A . . . . -53.1(4) ?
C2A C11A C12A C13A . . . . 172.3(3) ?
C11A C12A C13A C14A . . . . 52.8(4) ?
C12A C13A C14A C15A . . . . -55.3(4) ?
C13A C14A C15A C16A . . . . 57.7(4) ?
C14A C15A C16A C11A . . . . -57.7(4) ?
C12A C11A C16A C15A . . . . 55.5(4) ?
C2A C11A C16A C15A . . . . -171.0(3) ?
C3A C4A C21A C22A . . . . 77.7(3) ?
C5A C4A C21A C22A . . . . -105.4(3) ?
C3A C4A C21A C26A . . . . -55.1(4) ?
C5A C4A C21A C26A . . . . 121.8(3) ?
C4A C21A C22A C23A . . . . 172.8(3) ?
C26A C21A C22A C23A . . . . -53.1(3) ?
C21A C22A C23A C24A . . . . 53.4(4) ?
C22A C23A C24A C25A . . . . -55.7(4) ?
C23A C24A C25A C26A . . . . 57.1(4) ?
C24A C25A C26A C21A . . . . -56.3(3) ?
C4A C21A C26A C25A . . . . -171.5(2) ?
C22A C21A C26A C25A . . . . 54.4(3) ?
C5A C6A C31A C32A . . . . -52.8(4) ?
C1A C6A C31A C32A . . . . 122.8(3) ?
C5A C6A C31A C36A . . . . 82.2(4) ?
C1A C6A C31A C36A . . . . -102.3(3) ?
C6A C31A C32A C33A . . . . -168.4(3) ?
C36A C31A C32A C33A . . . . 55.0(4) ?
C31A C32A C33A C34A . . . . -55.7(4) ?
C32A C33A C34A C35A . . . . 54.7(5) ?
C33A C34A C35A C36A . . . . -52.7(5) ?
C34A C35A C36A C31A . . . . 50.3(4) ?
C32A C31A C36A C35A . . . . -51.8(4) ?
C6A C31A C36A C35A . . . . 172.3(3) ?
C6B C1B C2B C3B . . . . 0.1(5) ?
C7B C1B C2B C3B . . . . -177.2(3) ?
C6B C1B C2B C11B . . . . -177.6(3) ?
C7B C1B C2B C11B . . . . 5.0(5) ?
C1B C2B C3B C4B . . . . -4.3(5) ?
C11B C2B C3B C4B . . . . 173.6(3) ?
C1B C2B C3B C8B . . . . 172.7(3) ?
C11B C2B C3B C8B . . . . -9.4(4) ?
C3B C2B C11B C16B . . . . 99.0(4) ?
C1B C2B C11B C16B . . . . -83.2(4) ?
C3B C2B C11B C12B . . . . -121.3(4) ?
C1B C2B C11B C12B . . . . 56.5(5) ?
C16B C11B C12B C13B . . . . -48.6(5) ?
C2B C11B C12B C13B . . . . 170.9(3) ?
C11B C12B C13B C14B . . . . 50.8(5) ?
C12B C13B C14B C15B . . . . -51.1(5) ?
C13B C14B C15B C16B . . . . 49.0(5) ?
C14B C15B C16B C11B . . . . -47.1(5) ?
C12B C11B C16B C15B . . . . 47.4(5) ?
C2B C11B C16B C15B . . . . -171.5(3) ?
C2B C3B C4B C5B . . . . 7.3(5) ?
C8B C3B C4B C5B . . . . -169.7(3) ?
C2B C3B C4B C21B . . . . -170.0(5) ?
C8B C3B C4B C21B . . . . 13.0(7) ?
C2B C3B C4B C21D . . . . -168.7(5) ?
C8B C3B C4B C21D . . . . 14.4(6) ?
C6B C5B C4B C3B . . . . -6.3(5) ?
C9B C5B C4B C3B . . . . 174.6(10) ?
C9D C5B C4B C3B . . . . 159.4(12) ?
C6B C5B C4B C21B . . . . 171.5(5) ?
C9B C5B C4B C21B . . . . -7.6(11) ?
C6B C5B C4B C21D . . . . 168.9(5) ?
C9D C5B C4B C21D . . . . -25.4(14) ?
C3B C4B C21B C26B . . . . -83.7(13) ?
C5B C4B C21B C26B . . . . 98.8(12) ?
C3B C4B C21B C22B . . . . 52.5(11) ?
C5B C4B C21B C22B . . . . -124.9(7) ?
C26B C21B C22B C23B . . . . -45.2(14) ?
C4B C21B C22B C23B . . . . 178.4(7) ?
C21B C22B C23B C24B . . . . 45.1(11) ?
C22B C23B C24B C25B . . . . -47.6(11) ?
C23B C24B C25B C26B . . . . 49.3(14) ?
C24B C25B C26B C21B . . . . -47.8(19) ?
C22B C21B C26B C25B . . . . 46.(2) ?
C4B C21B C26B C25B . . . . -177.7(11) ?
C3B C4B C21D C26D . . . . -105.9(11) ?
C5B C4B C21D C26D . . . . 78.6(12) ?
C3B C4B C21D C22D . . . . 126.2(6) ?
C5B C4B C21D C22D . . . . -49.3(9) ?
C26D C21D C22D C23D . . . . 55.9(12) ?
C4B C21D C22D C23D . . . . -172.5(7) ?
C21D C22D C23D C24D . . . . -57.7(10) ?
C22D C23D C24D C25D . . . . 55.3(10) ?
C23D C24D C25D C26D . . . . -51.9(12) ?
C24D C25D C26D C21D . . . . 51.3(17) ?
C22D C21D C26D C25D . . . . -52.6(17) ?
C4B C21D C26D C25D . . . . 180.0(10) ?
C2B C1B C6B C5B . . . . 0.8(5) ?
C7B C1B C6B C5B . . . . 178.1(3) ?
C2B C1B C6B C31B . . . . 178.7(3) ?
C7B C1B C6B C31B . . . . -4.0(5) ?
C2B C1B C6B C31D . . . . -174.9(6) ?
C7B C1B C6B C31D . . . . 2.4(8) ?
C4B C5B C6B C1B . . . . 2.3(5) ?
C9B C5B C6B C1B . . . . -178.6(9) ?
C9D C5B C6B C1B . . . . -161.2(17) ?
C4B C5B C6B C31B . . . . -175.2(4) ?
C9B C5B C6B C31B . . . . 3.9(10) ?
C4B C5B C6B C31D . . . . 179.1(5) ?
C9D C5B C6B C31D . . . . 15.6(17) ?
C1B C6B C31B C36B . . . . -129.6(6) ?
C5B C6B C31B C36B . . . . 48.0(8) ?
C1B C6B C31B C32B . . . . 103.3(8) ?
C5B C6B C31B C32B . . . . -79.0(8) ?
C36B C31B C32B C33B . . . . 58.7(12) ?
C6B C31B C32B C33B . . . . -172.1(6) ?
C31B C32B C33B C34B . . . . -59.9(12) ?
C32B C33B C34B C35B . . . . 61.7(11) ?
C33B C34B C35B C36B . . . . -62.0(11) ?
C32B C31B C36B C35B . . . . -58.2(11) ?
C6B C31B C36B C35B . . . . 174.4(6) ?
C34B C35B C36B C31B . . . . 60.1(12) ?
C1B C6B C31D C36D . . . . -69.5(12) ?
C5B C6B C31D C36D . . . . 114.3(10) ?
C1B C6B C31D C32D . . . . 55.7(16) ?
C5B C6B C31D C32D . . . . -120.5(14) ?
C36D C31D C32D C33D . . . . -60.(2) ?
C6B C31D C32D C33D . . . . 175.3(12) ?
C31D C32D C33D C34D . . . . 61.(2) ?
C32D C33D C34D C35D . . . . -64.8(18) ?
C33D C34D C35D C36D . . . . 66.(2) ?
C32D C31D C36D C35D . . . . 61.2(19) ?
C6B C31D C36D C35D . . . . -172.0(11) ?
C34D C35D C36D C31D . . . . -63.(2) ?

####################################################################### 
# 
# 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_erk9170
_database_code_depnum_ccdc_archive 'CCDC 1862534'
_audit_update_record             
;
2018-08-17 deposited with the CCDC.
2019-01-14 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H21 B Br F10 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         664.19

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   10.2011(4)
_cell_length_b                   11.0143(4)
_cell_length_c                   12.5252(5)
_cell_angle_alpha                88.7430(10)
_cell_angle_beta                 80.8650(10)
_cell_angle_gamma                79.6490(10)
_cell_volume                     1366.81(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      3.5742
_cell_measurement_theta_max      70.1059
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.158
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664

_exptl_absorpt_coefficient_mu    2.870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_T_max  0.66

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            27371
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_theta_min         3.57
_diffrn_reflns_theta_max         70.23
_diffrn_reflns_theta_full        70.23
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_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_number_total             5152
_reflns_number_gt                4888
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0734
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.056
_refine_ls_number_reflns         5152
_refine_ls_number_parameters     407
_refine_ls_number_restraints     70
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0305P)²+0.9763P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.416
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;

APEX3 v2016.1-0 (Bruker AXS Inc., 2016)
;
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.69157(16) 0.70450(15) 0.31843(13) 0.0148(3) Uani d . . . 1.0 . .
C C1 0.74888(15) 0.81655(13) 0.24910(11) 0.0159(3) Uani d . . . 1.0 . .
H H1A 0.6785 0.8911 0.2654 0.019 Uiso calc U . R 1.0 . .
H H1B 0.8276 0.8312 0.2809 0.019 Uiso calc U . R 1.0 . .
C C11 1.02701(16) 0.64279(14) -0.09089(12) 0.0203(3) Uani d . . . 1.0 . .
H H11A 1.0972 0.6147 -0.0498 0.024 Uiso calc U . R 1.0 . .
H H11B 1.0461 0.6422 -0.1676 0.024 Uiso calc U . R 1.0 . .
C C2 0.79320(14) 0.81414(13) 0.12451(12) 0.0147(3) Uani d . . . 1.0 . .
C C12 0.67828(17) 0.94898(17) -0.11684(14) 0.0259(4) Uani d . . . 1.0 . .
H H12A 0.6307 1.0247 -0.0845 0.031 Uiso calc U . R 1.0 . .
H H12B 0.7045 0.9432 -0.1931 0.031 Uiso calc U . R 1.0 . .
C C3 0.86631(15) 0.68573(13) 0.08046(12) 0.0173(3) Uani d . . . 1.0 . .
H H3A 0.9497 0.6616 0.1127 0.021 Uiso calc U . R 1.0 . .
H H3B 0.8074 0.6244 0.103 0.021 Uiso calc U . R 1.0 . .
C C4 0.90270(15) 0.68269(13) -0.04117(12) 0.0174(3) Uani d . . . 1.0 . .
C C5 0.78657(16) 0.72941(15) -0.10115(13) 0.0225(3) Uani d . . . 1.0 . .
H H5A 0.8218 0.7394 -0.1786 0.027 Uiso calc U . R 1.0 . .
H H5B 0.7258 0.6681 -0.0958 0.027 Uiso calc U . R 1.0 . .
C C6 0.70803(15) 0.85125(15) -0.05550(12) 0.0196(3) Uani d . . . 1.0 . .
C C7 0.66977(15) 0.85341(14) 0.06578(12) 0.0178(3) Uani d . . . 1.0 . .
H H7A 0.6046 0.7971 0.0868 0.021 Uiso calc U . R 1.0 . .
H H7B 0.6245 0.9378 0.0895 0.021 Uiso calc U . R 1.0 . .
C C8 0.89454(15) 0.90521(14) 0.09546(12) 0.0177(3) Uani d U . D 1.0 . .
H H8A 0.9807 0.8684 0.1197 0.021 Uiso calc U P R 0.7392(10) A 1
H H8B 0.9128 0.9122 0.0158 0.021 Uiso calc U P R 0.7392(10) A 1
H H8C 0.9838 0.8634 0.1111 0.021 Uiso calc U P R 0.2608(10) A 2
H H8D 0.904 0.9196 0.0165 0.021 Uiso calc U P R 0.2608(10) A 2
C C9 0.8504(7) 1.0342(4) 0.1430(6) 0.0196(12) Uani d U P D 0.7392(10) A 1
Br Br1 0.90865(3) 1.06918(2) 0.27474(3) 0.02956(11) Uani d U P D 0.7392(10) A 1
C C10 0.7733(6) 1.1277(7) 0.0977(7) 0.043(2) Uani d U P D 0.7392(10) A 1
H H10A 0.7432 1.1148 0.0316 0.052 Uiso calc U P R 0.7392(10) A 1
H H10B 0.7494 1.2064 0.132 0.052 Uiso calc U P R 0.7392(10) A 1
C C9A 0.863(3) 1.0252(16) 0.149(2) 0.042(6) Uani d U P D 0.2608(10) A 2
Br Br1A 0.7344(2) 1.14654(19) 0.11026(16) 0.0265(3) Uani d U P D 0.2608(10) A 2
C C10A 0.9459(9) 1.0468(8) 0.2169(9) 0.0391(19) Uani d U P D 0.2608(10) A 2
H H10C 1.0209 0.9854 0.2274 0.047 Uiso calc U P R 0.2608(10) A 2
H H10D 0.9298 1.1236 0.2542 0.047 Uiso calc U P R 0.2608(10) A 2
N N21 0.62553(12) 0.76520(11) 0.43953(10) 0.0158(3) Uani d . . . 1.0 . .
C C22 0.68840(16) 0.84506(14) 0.48280(12) 0.0193(3) Uani d . . . 1.0 . .
H H22 0.7664 0.8681 0.4413 0.023 Uiso calc U . R 1.0 . .
C C23 0.64379(17) 0.89468(15) 0.58511(13) 0.0243(3) Uani d . . . 1.0 . .
H H23 0.6903 0.9511 0.6131 0.029 Uiso calc U . R 1.0 . .
C C24 0.53103(18) 0.86153(17) 0.64636(13) 0.0278(4) Uani d . . . 1.0 . .
H H24 0.4988 0.8943 0.7171 0.033 Uiso calc U . R 1.0 . .
C C25 0.46597(18) 0.77959(17) 0.60246(14) 0.0284(4) Uani d . . . 1.0 . .
H H25 0.388 0.7553 0.6428 0.034 Uiso calc U . R 1.0 . .
C C26 0.51528(16) 0.73323(15) 0.49942(13) 0.0222(3) Uani d . . . 1.0 . .
H H26 0.4699 0.677 0.4699 0.027 Uiso calc U . R 1.0 . .
C C31 0.80608(15) 0.58787(13) 0.34953(11) 0.0154(3) Uani d . . . 1.0 . .
C C32 0.94580(15) 0.58004(14) 0.33129(12) 0.0182(3) Uani d . . . 1.0 . .
F F32 1.00376(9) 0.67446(9) 0.28792(8) 0.0242(2) Uani d . . . 1.0 . .
C C33 1.03664(15) 0.47805(16) 0.35660(12) 0.0220(3) Uani d . . . 1.0 . .
F F33 1.17033(9) 0.47715(10) 0.33471(8) 0.0313(2) Uani d . . . 1.0 . .
C C34 0.99026(17) 0.37823(15) 0.40588(13) 0.0243(3) Uani d . . . 1.0 . .
F F34 1.07636(11) 0.27874(10) 0.43094(9) 0.0354(3) Uani d . . . 1.0 . .
C C35 0.85294(17) 0.38259(15) 0.43156(13) 0.0224(3) Uani d . . . 1.0 . .
F F35 0.80484(11) 0.28793(9) 0.48377(9) 0.0334(2) Uani d . . . 1.0 . .
C C36 0.76674(15) 0.48488(14) 0.40328(12) 0.0183(3) Uani d . . . 1.0 . .
F F36 0.63344(9) 0.48148(8) 0.43103(8) 0.0233(2) Uani d . . . 1.0 . .
C C41 0.56839(14) 0.66091(13) 0.26574(11) 0.0148(3) Uani d . . . 1.0 . .
C C42 0.57586(15) 0.55069(14) 0.21103(12) 0.0163(3) Uani d . . . 1.0 . .
F F42 0.68666(9) 0.46139(8) 0.20523(7) 0.02038(19) Uani d . . . 1.0 . .
C C43 0.47612(16) 0.52386(15) 0.15706(13) 0.0208(3) Uani d . . . 1.0 . .
F F43 0.49363(10) 0.41544(9) 0.10442(8) 0.0306(2) Uani d . . . 1.0 . .
C C44 0.35856(16) 0.60803(16) 0.15722(13) 0.0231(3) Uani d . . . 1.0 . .
F F44 0.26135(10) 0.58325(10) 0.10526(9) 0.0337(2) Uani d . . . 1.0 . .
C C45 0.34355(15) 0.71826(15) 0.21157(13) 0.0218(3) Uani d . . . 1.0 . .
F F45 0.23046(9) 0.80191(9) 0.21328(9) 0.0308(2) Uani d . . . 1.0 . .
C C46 0.44736(15) 0.74161(13) 0.26236(12) 0.0175(3) Uani d . . . 1.0 . .
F F46 0.42684(9) 0.85433(8) 0.31022(8) 0.0236(2) Uani d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 C1 . 1.634(2) ?
B1 C41 . 1.655(2) ?
B1 C31 . 1.658(2) ?
B1 N21 . 1.6612(19) ?
C1 C2 . 1.5536(19) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C11 C4 . 1.323(2) ?
C11 H11A . 0.95 ?
C11 H11B . 0.95 ?
C2 C3 . 1.545(2) ?
C2 C7 . 1.549(2) ?
C2 C8 . 1.5635(19) ?
C12 C6 . 1.327(2) ?
C12 H12A . 0.95 ?
C12 H12B . 0.95 ?
C3 C4 . 1.509(2) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.510(2) ?
C5 C6 . 1.507(2) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C7 . 1.507(2) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9A . 1.457(14) ?
C8 C9 . 1.515(4) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C8 H8C . 0.99 ?
C8 H8D . 0.99 ?
C9 C10 . 1.351(9) ?
C9 Br1 . 1.910(5) ?
C10 H10A . 0.95 ?
C10 H10B . 0.95 ?
C9A C10A . 1.342(18) ?
C9A Br1A . 1.813(17) ?
C10A H10C . 0.95 ?
C10A H10D . 0.95 ?
N21 C22 . 1.346(2) ?
N21 C26 . 1.347(2) ?
C22 C23 . 1.380(2) ?
C22 H22 . 0.95 ?
C23 C24 . 1.380(3) ?
C23 H23 . 0.95 ?
C24 C25 . 1.382(3) ?
C24 H24 . 0.95 ?
C25 C26 . 1.382(2) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?
C31 C32 . 1.394(2) ?
C31 C36 . 1.395(2) ?
C32 F32 . 1.3493(18) ?
C32 C33 . 1.387(2) ?
C33 F33 . 1.3460(18) ?
C33 C34 . 1.370(2) ?
C34 F34 . 1.3407(18) ?
C34 C35 . 1.379(2) ?
C35 F35 . 1.3444(19) ?
C35 C36 . 1.376(2) ?
C36 F36 . 1.3561(18) ?
C41 C42 . 1.391(2) ?
C41 C46 . 1.392(2) ?
C42 F42 . 1.3520(17) ?
C42 C43 . 1.384(2) ?
C43 F43 . 1.3466(18) ?
C43 C44 . 1.377(2) ?
C44 F44 . 1.3385(18) ?
C44 C45 . 1.377(2) ?
C45 F45 . 1.3384(18) ?
C45 C46 . 1.382(2) ?
C46 F46 . 1.3580(17) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 B1 C41 . . 111.25(12) ?
C1 B1 C31 . . 116.44(12) ?
C41 B1 C31 . . 113.73(12) ?
C1 B1 N21 . . 105.01(11) ?
C41 B1 N21 . . 107.48(11) ?
C31 B1 N21 . . 101.65(11) ?
C2 C1 B1 . . 124.43(12) ?
C2 C1 H1A . . 106.2 ?
B1 C1 H1A . . 106.2 ?
C2 C1 H1B . . 106.2 ?
B1 C1 H1B . . 106.2 ?
H1A C1 H1B . . 106.4 ?
C4 C11 H11A . . 120.0 ?
C4 C11 H11B . . 120.0 ?
H11A C11 H11B . . 120.0 ?
C3 C2 C7 . . 107.67(12) ?
C3 C2 C1 . . 113.10(12) ?
C7 C2 C1 . . 110.77(11) ?
C3 C2 C8 . . 107.09(11) ?
C7 C2 C8 . . 109.66(12) ?
C1 C2 C8 . . 108.45(12) ?
C6 C12 H12A . . 120.0 ?
C6 C12 H12B . . 120.0 ?
H12A C12 H12B . . 120.0 ?
C4 C3 C2 . . 112.73(12) ?
C4 C3 H3A . . 109.0 ?
C2 C3 H3A . . 109.0 ?
C4 C3 H3B . . 109.0 ?
C2 C3 H3B . . 109.0 ?
H3A C3 H3B . . 107.8 ?
C11 C4 C3 . . 122.37(14) ?
C11 C4 C5 . . 122.86(14) ?
C3 C4 C5 . . 114.77(13) ?
C6 C5 C4 . . 111.20(13) ?
C6 C5 H5A . . 109.4 ?
C4 C5 H5A . . 109.4 ?
C6 C5 H5B . . 109.4 ?
C4 C5 H5B . . 109.4 ?
H5A C5 H5B . . 108.0 ?
C12 C6 C7 . . 123.03(15) ?
C12 C6 C5 . . 122.72(15) ?
C7 C6 C5 . . 114.23(13) ?
C6 C7 C2 . . 112.57(12) ?
C6 C7 H7A . . 109.1 ?
C2 C7 H7A . . 109.1 ?
C6 C7 H7B . . 109.1 ?
C2 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.8 ?
C9A C8 C2 . . 117.9(13) ?
C9 C8 C2 . . 116.3(3) ?
C9 C8 H8A . . 108.2 ?
C2 C8 H8A . . 108.2 ?
C9 C8 H8B . . 108.2 ?
C2 C8 H8B . . 108.2 ?
H8A C8 H8B . . 107.4 ?
C9A C8 H8C . . 107.8 ?
C2 C8 H8C . . 107.8 ?
C9A C8 H8D . . 107.8 ?
C2 C8 H8D . . 107.8 ?
H8C C8 H8D . . 107.2 ?
C10 C9 C8 . . 124.5(6) ?
C10 C9 Br1 . . 117.1(4) ?
C8 C9 Br1 . . 118.4(4) ?
C9 C10 H10A . . 120.0 ?
C9 C10 H10B . . 120.0 ?
H10A C10 H10B . . 120.0 ?
C10A C9A C8 . . 116.6(13) ?
C10A C9A Br1A . . 121.7(10) ?
C8 C9A Br1A . . 121.0(12) ?
C9A C10A H10C . . 120.0 ?
C9A C10A H10D . . 120.0 ?
H10C C10A H10D . . 120.0 ?
C22 N21 C26 . . 118.05(13) ?
C22 N21 B1 . . 118.94(12) ?
C26 N21 B1 . . 122.91(12) ?
N21 C22 C23 . . 122.45(15) ?
N21 C22 H22 . . 118.8 ?
C23 C22 H22 . . 118.8 ?
C24 C23 C22 . . 119.36(16) ?
C24 C23 H23 . . 120.3 ?
C22 C23 H23 . . 120.3 ?
C23 C24 C25 . . 118.51(15) ?
C23 C24 H24 . . 120.7 ?
C25 C24 H24 . . 120.7 ?
C26 C25 C24 . . 119.47(16) ?
C26 C25 H25 . . 120.3 ?
C24 C25 H25 . . 120.3 ?
N21 C26 C25 . . 122.16(15) ?
N21 C26 H26 . . 118.9 ?
C25 C26 H26 . . 118.9 ?
C32 C31 C36 . . 112.39(13) ?
C32 C31 B1 . . 126.99(13) ?
C36 C31 B1 . . 120.58(13) ?
F32 C32 C33 . . 114.24(13) ?
F32 C32 C31 . . 121.59(13) ?
C33 C32 C31 . . 124.16(15) ?
F33 C33 C34 . . 119.61(14) ?
F33 C33 C32 . . 120.44(15) ?
C34 C33 C32 . . 119.94(14) ?
F34 C34 C33 . . 120.87(15) ?
F34 C34 C35 . . 120.24(16) ?
C33 C34 C35 . . 118.88(14) ?
F35 C35 C36 . . 120.86(15) ?
F35 C35 C34 . . 120.06(14) ?
C36 C35 C34 . . 119.08(15) ?
F36 C36 C35 . . 115.31(14) ?
F36 C36 C31 . . 119.29(13) ?
C35 C36 C31 . . 125.40(15) ?
C42 C41 C46 . . 112.50(13) ?
C42 C41 B1 . . 126.21(13) ?
C46 C41 B1 . . 120.93(13) ?
F42 C42 C43 . . 114.80(13) ?
F42 C42 C41 . . 120.79(13) ?
C43 C42 C41 . . 124.39(14) ?
F43 C43 C44 . . 119.86(14) ?
F43 C43 C42 . . 120.12(14) ?
C44 C43 C42 . . 120.02(15) ?
F44 C44 C45 . . 120.81(15) ?
F44 C44 C43 . . 120.61(15) ?
C45 C44 C43 . . 118.58(14) ?
F45 C45 C44 . . 120.00(14) ?
F45 C45 C46 . . 120.86(15) ?
C44 C45 C46 . . 119.13(14) ?
F46 C46 C45 . . 115.42(13) ?
F46 C46 C41 . . 119.21(13) ?
C45 C46 C41 . . 125.36(14) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C41 B1 C1 C2 . . . . -50.82(18) ?
C31 B1 C1 C2 . . . . 81.68(17) ?
N21 B1 C1 C2 . . . . -166.79(12) ?
B1 C1 C2 C3 . . . . -37.68(19) ?
B1 C1 C2 C7 . . . . 83.31(16) ?
B1 C1 C2 C8 . . . . -156.31(13) ?
C7 C2 C3 C4 . . . . 54.36(16) ?
C1 C2 C3 C4 . . . . 177.08(12) ?
C8 C2 C3 C4 . . . . -63.50(16) ?
C2 C3 C4 C11 . . . . 126.51(15) ?
C2 C3 C4 C5 . . . . -53.10(17) ?
C11 C4 C5 C6 . . . . -131.33(16) ?
C3 C4 C5 C6 . . . . 48.28(18) ?
C4 C5 C6 C12 . . . . 129.33(16) ?
C4 C5 C6 C7 . . . . -49.04(18) ?
C12 C6 C7 C2 . . . . -123.58(16) ?
C5 C6 C7 C2 . . . . 54.79(17) ?
C3 C2 C7 C6 . . . . -55.32(16) ?
C1 C2 C7 C6 . . . . -179.47(12) ?
C8 C2 C7 C6 . . . . 60.87(16) ?
C3 C2 C8 C9A . . . . -165.8(10) ?
C7 C2 C8 C9A . . . . 77.7(10) ?
C1 C2 C8 C9A . . . . -43.4(10) ?
C3 C2 C8 C9 . . . . -172.7(3) ?
C7 C2 C8 C9 . . . . 70.7(3) ?
C1 C2 C8 C9 . . . . -50.3(3) ?
C2 C8 C9 C10 . . . . -85.6(8) ?
C2 C8 C9 Br1 . . . . 95.4(4) ?
C2 C8 C9A C10A . . . . 114.(2) ?
C2 C8 C9A Br1A . . . . -76.(2) ?
C1 B1 N21 C22 . . . . -38.26(16) ?
C41 B1 N21 C22 . . . . -156.81(12) ?
C31 B1 N21 C22 . . . . 83.47(15) ?
C1 B1 N21 C26 . . . . 145.36(14) ?
C41 B1 N21 C26 . . . . 26.82(18) ?
C31 B1 N21 C26 . . . . -92.90(15) ?
C26 N21 C22 C23 . . . . -0.1(2) ?
B1 N21 C22 C23 . . . . -176.69(14) ?
N21 C22 C23 C24 . . . . 0.3(2) ?
C22 C23 C24 C25 . . . . -0.3(3) ?
C23 C24 C25 C26 . . . . 0.1(3) ?
C22 N21 C26 C25 . . . . 0.0(2) ?
B1 N21 C26 C25 . . . . 176.38(15) ?
C24 C25 C26 N21 . . . . 0.0(3) ?
C1 B1 C31 C32 . . . . 6.1(2) ?
C41 B1 C31 C32 . . . . 137.47(14) ?
N21 B1 C31 C32 . . . . -107.33(15) ?
C1 B1 C31 C36 . . . . -176.42(13) ?
C41 B1 C31 C36 . . . . -45.06(18) ?
N21 B1 C31 C36 . . . . 70.14(16) ?
C36 C31 C32 F32 . . . . -174.79(13) ?
B1 C31 C32 F32 . . . . 2.8(2) ?
C36 C31 C32 C33 . . . . 4.2(2) ?
B1 C31 C32 C33 . . . . -178.11(14) ?
F32 C32 C33 F33 . . . . -2.0(2) ?
C31 C32 C33 F33 . . . . 178.91(13) ?
F32 C32 C33 C34 . . . . 176.91(13) ?
C31 C32 C33 C34 . . . . -2.2(2) ?
F33 C33 C34 F34 . . . . -1.1(2) ?
C32 C33 C34 F34 . . . . 179.95(14) ?
F33 C33 C34 C35 . . . . 177.50(14) ?
C32 C33 C34 C35 . . . . -1.4(2) ?
F34 C34 C35 F35 . . . . 1.3(2) ?
C33 C34 C35 F35 . . . . -177.37(14) ?
F34 C34 C35 C36 . . . . -178.89(14) ?
C33 C34 C35 C36 . . . . 2.5(2) ?
F35 C35 C36 F36 . . . . -0.5(2) ?
C34 C35 C36 F36 . . . . 179.69(14) ?
F35 C35 C36 C31 . . . . 179.77(14) ?
C34 C35 C36 C31 . . . . -0.1(2) ?
C32 C31 C36 F36 . . . . 177.12(13) ?
B1 C31 C36 F36 . . . . -0.7(2) ?
C32 C31 C36 C35 . . . . -3.1(2) ?
B1 C31 C36 C35 . . . . 179.04(14) ?
C1 B1 C41 C42 . . . . 108.84(16) ?
C31 B1 C41 C42 . . . . -25.0(2) ?
N21 B1 C41 C42 . . . . -136.72(14) ?
C1 B1 C41 C46 . . . . -63.78(17) ?
C31 B1 C41 C46 . . . . 162.37(13) ?
N21 B1 C41 C46 . . . . 50.66(17) ?
C46 C41 C42 F42 . . . . 179.59(12) ?
B1 C41 C42 F42 . . . . 6.4(2) ?
C46 C41 C42 C43 . . . . 1.2(2) ?
B1 C41 C42 C43 . . . . -171.94(14) ?
F42 C42 C43 F43 . . . . 0.2(2) ?
C41 C42 C43 F43 . . . . 178.63(14) ?
F42 C42 C43 C44 . . . . -179.93(14) ?
C41 C42 C43 C44 . . . . -1.5(2) ?
F43 C43 C44 F44 . . . . -0.1(2) ?
C42 C43 C44 F44 . . . . 179.94(14) ?
F43 C43 C44 C45 . . . . -179.88(14) ?
C42 C43 C44 C45 . . . . 0.2(2) ?
F44 C44 C45 F45 . . . . 0.3(2) ?
C43 C44 C45 F45 . . . . -179.96(14) ?
F44 C44 C45 C46 . . . . -178.64(14) ?
C43 C44 C45 C46 . . . . 1.1(2) ?
F45 C45 C46 F46 . . . . -1.6(2) ?
C44 C45 C46 F46 . . . . 177.36(14) ?
F45 C45 C46 C41 . . . . 179.71(14) ?
C44 C45 C46 C41 . . . . -1.4(2) ?
C42 C41 C46 F46 . . . . -178.47(12) ?
B1 C41 C46 F46 . . . . -4.9(2) ?
C42 C41 C46 C45 . . . . 0.2(2) ?
B1 C41 C46 C45 . . . . 173.76(14) ?

