# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_av_ms454
_database_code_depnum_ccdc_archive 'CCDC 1894108'
loop_
_audit_author_name
_audit_author_address
'Alexander Villinger'
;University Rostock
Germany
;
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2019-02-27 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H27 N2 +, B F4 -, C H2 Cl2'
_chemical_formula_sum            'C34 H29 B Cl2 F4 N2'
_chemical_formula_weight         623.30

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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   14.616(4)
_cell_length_b                   16.962(4)
_cell_length_c                   24.922(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6178(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5011
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      19.84

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             2576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.261
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6684
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Apex Kappa-II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            63096
_diffrn_reflns_av_unetI/netI     0.0986
_diffrn_reflns_av_R_equivalents  0.1127
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.452
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10865
_reflns_number_gt                7054
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine. 

 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 > 2σ(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.

 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0417P)²+1.6603P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.48(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         10865
_refine_ls_number_parameters     798
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1207
_refine_ls_wR_factor_gt          0.1017
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6246(3) 1.0558(3) 0.7188(2) 0.0205(13) Uani 1 1 d . . . . .
N2 N 0.5804(4) 1.1077(3) 0.7131(2) 0.0284(14) Uani 1 1 d . . . . .
C1 C 0.6798(4) 0.9893(4) 0.7242(2) 0.0176(15) Uani 1 1 d . . . . .
C2 C 0.6729(4) 0.9460(4) 0.7717(2) 0.0202(16) Uani 1 1 d . . . . .
C3 C 0.7270(4) 0.8793(4) 0.7746(3) 0.0186(15) Uani 1 1 d . . . . .
H3 H 0.7246 0.8472 0.8058 0.022 Uiso 1 1 calc R U . . .
C4 C 0.7852(4) 0.8583(4) 0.7324(3) 0.0198(15) Uani 1 1 d . . . . .
C5 C 0.7912(4) 0.9066(4) 0.6867(2) 0.0182(15) Uani 1 1 d . . . . .
H5 H 0.8323 0.8925 0.6588 0.022 Uiso 1 1 calc R U . . .
C6 C 0.7393(4) 0.9737(4) 0.6813(2) 0.0177(15) Uani 1 1 d . . . . .
C7 C 0.6108(4) 0.9747(4) 0.8168(2) 0.0176(15) Uani 1 1 d . . . . .
H7 H 0.5487 0.9826 0.8008 0.021 Uiso 1 1 calc R U . . .
C8 C 0.6002(4) 0.9140(4) 0.8615(2) 0.0222(16) Uani 1 1 d . . . . .
C9 C 0.5398(4) 0.8505(4) 0.8541(3) 0.0267(17) Uani 1 1 d . . . . .
H9 H 0.5063 0.8467 0.8215 0.032 Uiso 1 1 calc R U . . .
C10 C 0.5283(4) 0.7939(4) 0.8929(3) 0.0339(18) Uani 1 1 d . . . . .
H10 H 0.4878 0.7511 0.8868 0.041 Uiso 1 1 calc R U . . .
C11 C 0.5752(4) 0.7989(4) 0.9406(3) 0.0324(18) Uani 1 1 d . . . . .
H11 H 0.5665 0.7600 0.9676 0.039 Uiso 1 1 calc R U . . .
C12 C 0.6350(5) 0.8608(4) 0.9493(3) 0.0333(18) Uani 1 1 d . . . . .
H12 H 0.6678 0.8642 0.9821 0.040 Uiso 1 1 calc R U . . .
C13 C 0.6473(4) 0.9182(4) 0.9100(2) 0.0271(16) Uani 1 1 d . . . . .
H13 H 0.6883 0.9606 0.9163 0.032 Uiso 1 1 calc R U . . .
C14 C 0.6435(4) 1.0559(4) 0.8364(2) 0.0202(16) Uani 1 1 d . . . . .
C15 C 0.5814(4) 1.1160(4) 0.8454(2) 0.0218(16) Uani 1 1 d . . . . .
H15 H 0.5180 1.1062 0.8404 0.026 Uiso 1 1 calc R U . . .
C16 C 0.6098(5) 1.1903(4) 0.8614(2) 0.0307(18) Uani 1 1 d . . . . .
H16 H 0.5663 1.2309 0.8676 0.037 Uiso 1 1 calc R U . . .
C17 C 0.7024(5) 1.2048(4) 0.8684(2) 0.0302(17) Uani 1 1 d . . . . .
H17 H 0.7226 1.2557 0.8790 0.036 Uiso 1 1 calc R U . . .
C18 C 0.7652(4) 1.1452(4) 0.8598(2) 0.0294(18) Uani 1 1 d . . . . .
H18 H 0.8286 1.1550 0.8651 0.035 Uiso 1 1 calc R U . . .
C19 C 0.7360(4) 1.0711(4) 0.8436(3) 0.0242(16) Uani 1 1 d . . . . .
H19 H 0.7796 1.0305 0.8373 0.029 Uiso 1 1 calc R U . . .
C20 C 0.8427(4) 0.7856(4) 0.7368(2) 0.0218(16) Uani 1 1 d . . . . .
H20A H 0.8617 0.7688 0.7009 0.033 Uiso 1 1 calc R U . . .
H20B H 0.8070 0.7436 0.7538 0.033 Uiso 1 1 calc R U . . .
H20C H 0.8969 0.7969 0.7586 0.033 Uiso 1 1 calc R U . . .
C21 C 0.7464(4) 1.0313(4) 0.6344(2) 0.0214(16) Uani 1 1 d . . . . .
H21 H 0.6826 1.0482 0.6255 0.026 Uiso 1 1 calc R U . . .
C22 C 0.7992(4) 1.1059(4) 0.6510(3) 0.0240(16) Uani 1 1 d . . . . .
C23 C 0.8446(4) 1.1143(4) 0.6994(3) 0.0298(17) Uani 1 1 d . . . . .
H23 H 0.8455 1.0716 0.7240 0.036 Uiso 1 1 calc R U . . .
C24 C 0.8891(4) 1.1849(4) 0.7126(3) 0.0384(19) Uani 1 1 d . . . . .
H24 H 0.9187 1.1900 0.7463 0.046 Uiso 1 1 calc R U . . .
C25 C 0.8902(5) 1.2463(4) 0.6772(3) 0.0406(19) Uani 1 1 d . . . . .
H25 H 0.9211 1.2938 0.6862 0.049 Uiso 1 1 calc R U . . .
C26 C 0.8464(5) 1.2393(4) 0.6286(3) 0.045(2) Uani 1 1 d . . . . .
H26 H 0.8476 1.2820 0.6039 0.055 Uiso 1 1 calc R U . . .
C27 C 0.7999(5) 1.1697(4) 0.6150(3) 0.0377(19) Uani 1 1 d . . . . .
H27 H 0.7690 1.1658 0.5815 0.045 Uiso 1 1 calc R U . . .
C28 C 0.7844(4) 0.9902(4) 0.5847(2) 0.0210(15) Uani 1 1 d . . . . .
C29 C 0.7247(4) 0.9544(4) 0.5492(3) 0.0285(17) Uani 1 1 d . . . . .
H29 H 0.6607 0.9569 0.5554 0.034 Uiso 1 1 calc R U . . .
C30 C 0.7578(5) 0.9143(4) 0.5041(3) 0.0352(18) Uani 1 1 d . . . . .
H30 H 0.7163 0.8909 0.4795 0.042 Uiso 1 1 calc R U . . .
C31 C 0.8500(5) 0.9088(4) 0.4955(3) 0.0309(18) Uani 1 1 d . . . . .
H31 H 0.8726 0.8809 0.4653 0.037 Uiso 1 1 calc R U . . .
C32 C 0.9103(5) 0.9439(4) 0.5309(2) 0.0287(17) Uani 1 1 d . . . . .
H32 H 0.9743 0.9399 0.5249 0.034 Uiso 1 1 calc R U . . .
C33 C 0.8778(4) 0.9849(4) 0.5750(2) 0.0248(16) Uani 1 1 d . . . . .
H33 H 0.9197 1.0096 0.5989 0.030 Uiso 1 1 calc R U . . .
N3 N 0.8799(3) 0.5564(3) 0.7209(2) 0.0198(13) Uani 1 1 d . . . . .
N4 N 0.9241(4) 0.6089(3) 0.7180(2) 0.0295(15) Uani 1 1 d . . . . .
C34 C 0.8240(4) 0.4896(4) 0.7245(2) 0.0186(15) Uani 1 1 d . . . . .
C35 C 0.7723(4) 0.4715(4) 0.6787(3) 0.0176(15) Uani 1 1 d . . . . .
C36 C 0.7218(4) 0.4029(4) 0.6828(2) 0.0199(15) Uani 1 1 d . . . . .
H36 H 0.6856 0.3868 0.6531 0.024 Uiso 1 1 calc R U . . .
C37 C 0.7221(4) 0.3568(4) 0.7287(2) 0.0189(15) Uani 1 1 d . . . . .
C38 C 0.7739(4) 0.3792(4) 0.7730(3) 0.0194(16) Uani 1 1 d . . . . .
H38 H 0.7730 0.3472 0.8043 0.023 Uiso 1 1 calc R U . . .
C39 C 0.8268(4) 0.4471(4) 0.7727(2) 0.0163(15) Uani 1 1 d . . . . .
C40 C 0.7755(4) 0.5248(4) 0.6300(2) 0.0217(15) Uani 1 1 d . . . . .
H40 H 0.8416 0.5328 0.6212 0.026 Uiso 1 1 calc R U . . .
C41 C 0.7323(4) 0.4848(4) 0.5812(2) 0.0223(16) Uani 1 1 d . . . . .
C42 C 0.7873(5) 0.4435(4) 0.5458(3) 0.0303(17) Uani 1 1 d . . . . .
H42 H 0.8517 0.4423 0.5509 0.036 Uiso 1 1 calc R U . . .
C43 C 0.7484(5) 0.4039(4) 0.5032(3) 0.0360(19) Uani 1 1 d . . . . .
H43 H 0.7866 0.3765 0.4786 0.043 Uiso 1 1 calc R U . . .
C44 C 0.6553(5) 0.4037(4) 0.4959(3) 0.0358(19) Uani 1 1 d . . . . .
H44 H 0.6289 0.3751 0.4670 0.043 Uiso 1 1 calc R U . . .
C45 C 0.6004(5) 0.4452(4) 0.5309(3) 0.0328(18) Uani 1 1 d . . . . .
H45 H 0.5359 0.4452 0.5262 0.039 Uiso 1 1 calc R U . . .
C46 C 0.6388(4) 0.4870(4) 0.5729(2) 0.0249(16) Uani 1 1 d . . . . .
H46 H 0.6009 0.5172 0.5960 0.030 Uiso 1 1 calc R U . . .
C47 C 0.7349(4) 0.6066(4) 0.6398(3) 0.0276(17) Uani 1 1 d . . . . .
C48 C 0.7565(5) 0.6661(4) 0.6029(3) 0.041(2) Uani 1 1 d . . . . .
H48 H 0.7988 0.6557 0.5749 0.049 Uiso 1 1 calc R U . . .
C49 C 0.7172(6) 0.7391(4) 0.6069(3) 0.052(2) Uani 1 1 d . . . . .
H49 H 0.7322 0.7791 0.5817 0.062 Uiso 1 1 calc R U . . .
C50 C 0.6556(5) 0.7547(4) 0.6479(4) 0.053(3) Uani 1 1 d . . . . .
H50 H 0.6272 0.8050 0.6500 0.064 Uiso 1 1 calc R U . . .
C51 C 0.6347(4) 0.6974(5) 0.6860(3) 0.045(2) Uani 1 1 d . . . . .
H51 H 0.5937 0.7087 0.7146 0.053 Uiso 1 1 calc R U . . .
C52 C 0.6754(4) 0.6224(4) 0.6812(3) 0.0323(18) Uani 1 1 d . . . . .
H52 H 0.6618 0.5825 0.7067 0.039 Uiso 1 1 calc R U . . .
C53 C 0.6681(4) 0.2814(4) 0.7302(2) 0.0256(16) Uani 1 1 d . . . . .
H53A H 0.6129 0.2890 0.7519 0.038 Uiso 1 1 calc R U . . .
H53B H 0.7056 0.2395 0.7460 0.038 Uiso 1 1 calc R U . . .
H53C H 0.6506 0.2665 0.6936 0.038 Uiso 1 1 calc R U . . .
C54 C 0.8823(4) 0.4777(4) 0.8204(2) 0.0201(15) Uani 1 1 d . . . . .
H54 H 0.9457 0.4875 0.8069 0.024 Uiso 1 1 calc R U . . .
C55 C 0.8447(4) 0.5571(4) 0.8383(2) 0.0183(15) Uani 1 1 d . . . . .
C56 C 0.7516(4) 0.5720(4) 0.8416(3) 0.0251(16) Uani 1 1 d . . . . .
H56 H 0.7093 0.5317 0.8324 0.030 Uiso 1 1 calc R U . . .
C57 C 0.7197(5) 0.6451(4) 0.8580(3) 0.0309(18) Uani 1 1 d . . . . .
H57 H 0.6556 0.6542 0.8603 0.037 Uiso 1 1 calc R U . . .
C58 C 0.7793(5) 0.7044(4) 0.8710(2) 0.0281(17) Uani 1 1 d . . . . .
H58 H 0.7566 0.7538 0.8830 0.034 Uiso 1 1 calc R U . . .
C59 C 0.8721(5) 0.6920(4) 0.8667(3) 0.0292(17) Uani 1 1 d . . . . .
H59 H 0.9136 0.7336 0.8744 0.035 Uiso 1 1 calc R U . . .
C60 C 0.9050(4) 0.6185(4) 0.8510(2) 0.0249(16) Uani 1 1 d . . . . .
H60 H 0.9691 0.6099 0.8489 0.030 Uiso 1 1 calc R U . . .
C61 C 0.8903(4) 0.4157(4) 0.8647(2) 0.0201(15) Uani 1 1 d . . . . .
C62 C 0.8395(4) 0.4193(4) 0.9114(2) 0.0262(16) Uani 1 1 d . . . . .
H62 H 0.7985 0.4620 0.9169 0.031 Uiso 1 1 calc R U . . .
C63 C 0.8476(4) 0.3616(4) 0.9501(3) 0.0315(18) Uani 1 1 d . . . . .
H63 H 0.8127 0.3650 0.9822 0.038 Uiso 1 1 calc R U . . .
C64 C 0.9062(4) 0.2991(5) 0.9423(3) 0.0379(19) Uani 1 1 d . . . . .
H64 H 0.9116 0.2592 0.9689 0.045 Uiso 1 1 calc R U . . .
C65 C 0.9569(5) 0.2943(4) 0.8961(3) 0.0370(18) Uani 1 1 d . . . . .
H65 H 0.9974 0.2513 0.8906 0.044 Uiso 1 1 calc R U . . .
C66 C 0.9485(4) 0.3526(4) 0.8574(3) 0.0284(17) Uani 1 1 d . . . . .
H66 H 0.9834 0.3491 0.8253 0.034 Uiso 1 1 calc R U . . .
B1A B 0.4666(6) 0.9283(6) 0.6784(4) 0.031(2) Uani 0.920(5) 1 d D . P A 1
F1A F 0.5340(4) 0.9562(3) 0.64275(18) 0.0425(15) Uani 0.920(5) 1 d D . P A 1
F2A F 0.3922(5) 0.9024(5) 0.6490(3) 0.0406(15) Uani 0.920(5) 1 d D . P A 1
F3A F 0.4422(3) 0.9885(3) 0.71281(17) 0.0448(13) Uani 0.920(5) 1 d D . P A 1
F4A F 0.5036(3) 0.8662(3) 0.70783(17) 0.0491(14) Uani 0.920(5) 1 d D . P A 1
B1B B 0.465(3) 0.945(2) 0.6624(15) 0.031(2) Uani 0.080(5) 1 d D U P A 2
F1B F 0.480(3) 0.929(3) 0.7174(15) 0.026(8) Uiso 0.080(5) 1 d D U P A 2
F2B F 0.390(5) 0.902(4) 0.646(3) 0.031(9) Uiso 0.080(5) 1 d D U P A 2
F3B F 0.542(4) 0.925(3) 0.634(2) 0.029(8) Uiso 0.080(5) 1 d D U P A 2
F4B F 0.448(3) 1.026(2) 0.6566(16) 0.030(8) Uiso 0.080(5) 1 d D U P A 2
F5 F 0.9776(3) 0.9272(3) 0.78468(15) 0.0606(13) Uani 1 1 d . . . . .
F6 F 0.8848(2) 0.9047(2) 0.85585(15) 0.0406(11) Uani 1 1 d . . . . .
F7 F 0.9532(3) 1.0238(3) 0.8451(2) 0.0643(14) Uani 1 1 d . . . . .
F8 F 1.0367(2) 0.9189(3) 0.86795(16) 0.0508(12) Uani 1 1 d . . . . .
B2 B 0.9622(6) 0.9420(5) 0.8381(3) 0.034(2) Uani 1 1 d . . . . .
Cl1 Cl 0.86986(13) 0.79753(12) 0.99361(8) 0.0521(6) Uani 1 1 d . . . . .
Cl2 Cl 0.98620(13) 0.91243(11) 1.04622(7) 0.0465(5) Uani 1 1 d . . . . .
C133 C 0.9251(5) 0.8879(4) 0.9875(3) 0.043(2) Uani 1 1 d . . . . .
H13A H 0.8793 0.9295 0.9800 0.052 Uiso 1 1 calc R U . . .
H13B H 0.9680 0.8858 0.9567 0.052 Uiso 1 1 calc R U . . .
Cl3 Cl 0.50237(12) 0.41776(11) 1.03967(7) 0.0416(5) Uani 1 1 d . . . . .
Cl4 Cl 0.59973(13) 0.29619(12) 0.98064(8) 0.0504(5) Uani 1 1 d . . . . .
C134 C 0.5600(5) 0.3941(4) 0.9794(3) 0.047(2) Uani 1 1 d . . . . .
H13C H 0.5178 0.4012 0.9487 0.056 Uiso 1 1 calc R U . . .
H13D H 0.6124 0.4304 0.9744 0.056 Uiso 1 1 calc R U . . .


#==============================================================================

# MOLECULAR GEOMETRY

_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
N1 N2 1.101(6) . ?
N1 C1 1.393(8) . ?
C1 C2 1.395(8) . ?
C1 C6 1.403(8) . ?
C2 C3 1.383(8) . ?
C2 C7 1.524(8) . ?
C3 C4 1.398(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.406(8) . ?
C4 C20 1.495(8) . ?
C5 C6 1.375(8) . ?
C5 H5 0.9500 . ?
C6 C21 1.528(8) . ?
C7 C8 1.526(8) . ?
C7 C14 1.537(8) . ?
C7 H7 1.0000 . ?
C8 C13 1.391(8) . ?
C8 C9 1.404(9) . ?
C9 C10 1.374(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.375(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.392(9) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.383(8) . ?
C14 C19 1.389(8) . ?
C15 C16 1.386(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(9) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(9) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(9) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C28 1.525(8) . ?
C21 C22 1.538(9) . ?
C21 H21 1.0000 . ?
C22 C23 1.384(9) . ?
C22 C27 1.406(8) . ?
C23 C24 1.403(9) . ?
C23 H23 0.9500 . ?
C24 C25 1.364(9) . ?
C24 H24 0.9500 . ?
C25 C26 1.376(10) . ?
C25 H25 0.9500 . ?
C26 C27 1.403(9) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.384(9) . ?
C28 C33 1.390(8) . ?
C29 C30 1.399(9) . ?
C29 H29 0.9500 . ?
C30 C31 1.367(9) . ?
C30 H30 0.9500 . ?
C31 C32 1.381(9) . ?
C31 H31 0.9500 . ?
C32 C33 1.386(8) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
N3 N4 1.102(6) . ?
N3 C34 1.400(8) . ?
C34 C35 1.402(8) . ?
C34 C39 1.404(8) . ?
C35 C36 1.381(8) . ?
C35 C40 1.515(8) . ?
C36 C37 1.386(8) . ?
C36 H36 0.9500 . ?
C37 C38 1.393(9) . ?
C37 C53 1.503(8) . ?
C38 C39 1.386(8) . ?
C38 H38 0.9500 . ?
C39 C54 1.530(8) . ?
C40 C41 1.527(8) . ?
C40 C47 1.531(9) . ?
C40 H40 1.0000 . ?
C41 C46 1.383(8) . ?
C41 C42 1.385(9) . ?
C42 C43 1.377(9) . ?
C42 H42 0.9500 . ?
C43 C44 1.374(9) . ?
C43 H43 0.9500 . ?
C44 C45 1.379(9) . ?
C44 H44 0.9500 . ?
C45 C46 1.382(8) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 C52 1.374(9) . ?
C47 C48 1.402(9) . ?
C48 C49 1.369(9) . ?
C48 H48 0.9500 . ?
C49 C50 1.387(11) . ?
C49 H49 0.9500 . ?
C50 C51 1.391(11) . ?
C50 H50 0.9500 . ?
C51 C52 1.411(9) . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 C55 1.522(8) . ?
C54 C61 1.529(8) . ?
C54 H54 1.0000 . ?
C55 C56 1.386(8) . ?
C55 C60 1.400(8) . ?
C56 C57 1.386(9) . ?
C56 H56 0.9500 . ?
C57 C58 1.369(9) . ?
C57 H57 0.9500 . ?
C58 C59 1.377(9) . ?
C58 H58 0.9500 . ?
C59 C60 1.392(9) . ?
C59 H59 0.9500 . ?
C60 H60 0.9500 . ?
C61 C66 1.378(8) . ?
C61 C62 1.382(8) . ?
C62 C63 1.379(9) . ?
C62 H62 0.9500 . ?
C63 C64 1.378(9) . ?
C63 H63 0.9500 . ?
C64 C65 1.373(9) . ?
C64 H64 0.9500 . ?
C65 C66 1.386(9) . ?
C65 H65 0.9500 . ?
C66 H66 0.9500 . ?
B1A F3A 1.380(10) . ?
B1A F2A 1.383(9) . ?
B1A F4A 1.393(11) . ?
B1A F1A 1.409(9) . ?
B1B F3B 1.381(17) . ?
B1B F2B 1.384(16) . ?
B1B F4B 1.394(17) . ?
B1B F1B 1.412(16) . ?
F5 B2 1.374(9) . ?
F6 B2 1.369(9) . ?
F7 B2 1.405(9) . ?
F8 B2 1.374(9) . ?
Cl1 C133 1.739(7) . ?
Cl2 C133 1.765(7) . ?
C133 H13A 0.9900 . ?
C133 H13B 0.9900 . ?
Cl3 C134 1.768(7) . ?
Cl4 C134 1.760(7) . ?
C134 H13C 0.9900 . ?
C134 H13D 0.9900 . ?

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
N2 N1 C1 178.0(7) . . ?
N1 C1 C2 117.7(6) . . ?
N1 C1 C6 116.0(5) . . ?
C2 C1 C6 126.3(6) . . ?
C3 C2 C1 115.7(6) . . ?
C3 C2 C7 124.3(6) . . ?
C1 C2 C7 120.0(6) . . ?
C2 C3 C4 121.1(6) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 119.9(6) . . ?
C3 C4 C20 119.8(6) . . ?
C5 C4 C20 120.3(6) . . ?
C6 C5 C4 121.8(6) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 115.1(6) . . ?
C5 C6 C21 124.5(5) . . ?
C1 C6 C21 120.4(5) . . ?
C2 C7 C8 112.6(5) . . ?
C2 C7 C14 109.6(5) . . ?
C8 C7 C14 113.8(5) . . ?
C2 C7 H7 106.8 . . ?
C8 C7 H7 106.8 . . ?
C14 C7 H7 106.8 . . ?
C13 C8 C9 117.6(6) . . ?
C13 C8 C7 123.4(6) . . ?
C9 C8 C7 119.0(5) . . ?
C10 C9 C8 121.3(6) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 120.3(7) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 119.7(7) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 120.2(6) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C12 120.8(7) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C19 118.8(6) . . ?
C15 C14 C7 120.6(5) . . ?
C19 C14 C7 120.6(6) . . ?
C14 C15 C16 121.4(6) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C17 C16 C15 119.4(7) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C18 C17 C16 119.9(7) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.3(6) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 120.3(6) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C4 C20 H20A 109.5 . . ?
C4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C28 C21 C6 110.8(5) . . ?
C28 C21 C22 114.3(5) . . ?
C6 C21 C22 110.8(5) . . ?
C28 C21 H21 106.9 . . ?
C6 C21 H21 106.9 . . ?
C22 C21 H21 106.9 . . ?
C23 C22 C27 118.2(6) . . ?
C23 C22 C21 124.0(6) . . ?
C27 C22 C21 117.8(6) . . ?
C22 C23 C24 121.1(7) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C25 C24 C23 120.3(7) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 119.9(7) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C27 120.7(7) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C26 C27 C22 119.9(7) . . ?
C26 C27 H27 120.1 . . ?
C22 C27 H27 120.1 . . ?
C29 C28 C33 118.7(6) . . ?
C29 C28 C21 119.4(6) . . ?
C33 C28 C21 121.8(6) . . ?
C28 C29 C30 120.6(6) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C31 C30 C29 119.9(7) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C32 120.0(6) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C31 C32 C33 120.3(6) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C32 C33 C28 120.4(6) . . ?
C32 C33 H33 119.8 . . ?
C28 C33 H33 119.8 . . ?
N4 N3 C34 179.9(8) . . ?
N3 C34 C35 116.1(6) . . ?
N3 C34 C39 117.0(5) . . ?
C35 C34 C39 126.9(6) . . ?
C36 C35 C34 114.4(6) . . ?
C36 C35 C40 125.3(6) . . ?
C34 C35 C40 120.3(6) . . ?
C35 C36 C37 122.3(6) . . ?
C35 C36 H36 118.8 . . ?
C37 C36 H36 118.8 . . ?
C36 C37 C38 120.1(6) . . ?
C36 C37 C53 120.0(6) . . ?
C38 C37 C53 119.9(6) . . ?
C39 C38 C37 121.8(6) . . ?
C39 C38 H38 119.1 . . ?
C37 C38 H38 119.1 . . ?
C38 C39 C34 114.5(6) . . ?
C38 C39 C54 125.0(6) . . ?
C34 C39 C54 120.4(5) . . ?
C35 C40 C41 111.1(5) . . ?
C35 C40 C47 113.6(5) . . ?
C41 C40 C47 111.7(5) . . ?
C35 C40 H40 106.7 . . ?
C41 C40 H40 106.7 . . ?
C47 C40 H40 106.7 . . ?
C46 C41 C42 119.4(6) . . ?
C46 C41 C40 121.1(6) . . ?
C42 C41 C40 119.4(6) . . ?
C43 C42 C41 119.9(6) . . ?
C43 C42 H42 120.0 . . ?
C41 C42 H42 120.0 . . ?
C44 C43 C42 120.9(7) . . ?
C44 C43 H43 119.6 . . ?
C42 C43 H43 119.6 . . ?
C43 C44 C45 119.3(7) . . ?
C43 C44 H44 120.3 . . ?
C45 C44 H44 120.3 . . ?
C44 C45 C46 120.3(7) . . ?
C44 C45 H45 119.8 . . ?
C46 C45 H45 119.8 . . ?
C45 C46 C41 120.1(6) . . ?
C45 C46 H46 120.0 . . ?
C41 C46 H46 120.0 . . ?
C52 C47 C48 119.7(7) . . ?
C52 C47 C40 122.8(6) . . ?
C48 C47 C40 117.4(6) . . ?
C49 C48 C47 120.6(8) . . ?
C49 C48 H48 119.7 . . ?
C47 C48 H48 119.7 . . ?
C48 C49 C50 119.9(8) . . ?
C48 C49 H49 120.1 . . ?
C50 C49 H49 120.1 . . ?
C49 C50 C51 120.8(7) . . ?
C49 C50 H50 119.6 . . ?
C51 C50 H50 119.6 . . ?
C50 C51 C52 118.7(7) . . ?
C50 C51 H51 120.7 . . ?
C52 C51 H51 120.7 . . ?
C47 C52 C51 120.3(7) . . ?
C47 C52 H52 119.8 . . ?
C51 C52 H52 119.8 . . ?
C37 C53 H53A 109.5 . . ?
C37 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C37 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C55 C54 C61 115.1(5) . . ?
C55 C54 C39 109.7(5) . . ?
C61 C54 C39 111.6(5) . . ?
C55 C54 H54 106.6 . . ?
C61 C54 H54 106.6 . . ?
C39 C54 H54 106.6 . . ?
C56 C55 C60 117.9(6) . . ?
C56 C55 C54 122.2(6) . . ?
C60 C55 C54 119.9(5) . . ?
C55 C56 C57 120.8(7) . . ?
C55 C56 H56 119.6 . . ?
C57 C56 H56 119.6 . . ?
C58 C57 C56 120.8(6) . . ?
C58 C57 H57 119.6 . . ?
C56 C57 H57 119.6 . . ?
C57 C58 C59 119.8(7) . . ?
C57 C58 H58 120.1 . . ?
C59 C58 H58 120.1 . . ?
C58 C59 C60 119.9(7) . . ?
C58 C59 H59 120.1 . . ?
C60 C59 H59 120.1 . . ?
C59 C60 C55 120.9(6) . . ?
C59 C60 H60 119.6 . . ?
C55 C60 H60 119.6 . . ?
C66 C61 C62 118.5(6) . . ?
C66 C61 C54 119.1(6) . . ?
C62 C61 C54 122.4(6) . . ?
C63 C62 C61 120.8(7) . . ?
C63 C62 H62 119.6 . . ?
C61 C62 H62 119.6 . . ?
C64 C63 C62 120.1(7) . . ?
C64 C63 H63 120.0 . . ?
C62 C63 H63 120.0 . . ?
C65 C64 C63 120.0(7) . . ?
C65 C64 H64 120.0 . . ?
C63 C64 H64 120.0 . . ?
C64 C65 C66 119.6(7) . . ?
C64 C65 H65 120.2 . . ?
C66 C65 H65 120.2 . . ?
C61 C66 C65 121.1(6) . . ?
C61 C66 H66 119.5 . . ?
C65 C66 H66 119.5 . . ?
F3A B1A F2A 111.2(7) . . ?
F3A B1A F4A 109.5(7) . . ?
F2A B1A F4A 110.2(8) . . ?
F3A B1A F1A 108.9(7) . . ?
F2A B1A F1A 108.7(8) . . ?
F4A B1A F1A 108.3(7) . . ?
F3B B1B F2B 111(2) . . ?
F3B B1B F4B 110(2) . . ?
F2B B1B F4B 110(2) . . ?
F3B B1B F1B 109(2) . . ?
F2B B1B F1B 108(2) . . ?
F4B B1B F1B 108(2) . . ?
F6 B2 F8 110.4(6) . . ?
F6 B2 F5 111.3(6) . . ?
F8 B2 F5 110.0(6) . . ?
F6 B2 F7 109.8(6) . . ?
F8 B2 F7 106.8(6) . . ?
F5 B2 F7 108.4(7) . . ?
Cl1 C133 Cl2 111.7(4) . . ?
Cl1 C133 H13A 109.3 . . ?
Cl2 C133 H13A 109.3 . . ?
Cl1 C133 H13B 109.3 . . ?
Cl2 C133 H13B 109.3 . . ?
H13A C133 H13B 107.9 . . ?
Cl4 C134 Cl3 110.8(4) . . ?
Cl4 C134 H13C 109.5 . . ?
Cl3 C134 H13C 109.5 . . ?
Cl4 C134 H13D 109.5 . . ?
Cl3 C134 H13D 109.5 . . ?
H13C C134 H13D 108.1 . . ?

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
N1 C1 C2 C3 178.2(5) . . . . ?
C6 C1 C2 C3 -3.5(9) . . . . ?
N1 C1 C2 C7 -3.7(8) . . . . ?
C6 C1 C2 C7 174.6(6) . . . . ?
C1 C2 C3 C4 0.7(9) . . . . ?
C7 C2 C3 C4 -177.3(5) . . . . ?
C2 C3 C4 C5 1.8(9) . . . . ?
C2 C3 C4 C20 -179.8(5) . . . . ?
C3 C4 C5 C6 -1.8(9) . . . . ?
C20 C4 C5 C6 179.8(5) . . . . ?
C4 C5 C6 C1 -0.7(8) . . . . ?
C4 C5 C6 C21 176.3(6) . . . . ?
N1 C1 C6 C5 -178.2(5) . . . . ?
C2 C1 C6 C5 3.5(9) . . . . ?
N1 C1 C6 C21 4.7(8) . . . . ?
C2 C1 C6 C21 -173.6(6) . . . . ?
C3 C2 C7 C8 -11.1(8) . . . . ?
C1 C2 C7 C8 171.0(5) . . . . ?
C3 C2 C7 C14 116.7(6) . . . . ?
C1 C2 C7 C14 -61.2(7) . . . . ?
C2 C7 C8 C13 101.2(7) . . . . ?
C14 C7 C8 C13 -24.3(8) . . . . ?
C2 C7 C8 C9 -79.0(7) . . . . ?
C14 C7 C8 C9 155.5(5) . . . . ?
C13 C8 C9 C10 -0.7(9) . . . . ?
C7 C8 C9 C10 179.4(6) . . . . ?
C8 C9 C10 C11 0.9(10) . . . . ?
C9 C10 C11 C12 -0.8(10) . . . . ?
C10 C11 C12 C13 0.4(10) . . . . ?
C9 C8 C13 C12 0.4(9) . . . . ?
C7 C8 C13 C12 -179.8(6) . . . . ?
C11 C12 C13 C8 -0.3(10) . . . . ?
C2 C7 C14 C15 135.0(6) . . . . ?
C8 C7 C14 C15 -97.8(6) . . . . ?
C2 C7 C14 C19 -42.6(7) . . . . ?
C8 C7 C14 C19 84.5(7) . . . . ?
C19 C14 C15 C16 -0.2(9) . . . . ?
C7 C14 C15 C16 -177.9(6) . . . . ?
C14 C15 C16 C17 0.4(10) . . . . ?
C15 C16 C17 C18 -0.7(10) . . . . ?
C16 C17 C18 C19 0.9(10) . . . . ?
C17 C18 C19 C14 -0.8(10) . . . . ?
C15 C14 C19 C18 0.4(9) . . . . ?
C7 C14 C19 C18 178.1(5) . . . . ?
C5 C6 C21 C28 24.6(8) . . . . ?
C1 C6 C21 C28 -158.6(5) . . . . ?
C5 C6 C21 C22 -103.3(7) . . . . ?
C1 C6 C21 C22 73.5(7) . . . . ?
C28 C21 C22 C23 -117.7(6) . . . . ?
C6 C21 C22 C23 8.3(8) . . . . ?
C28 C21 C22 C27 63.4(7) . . . . ?
C6 C21 C22 C27 -170.6(5) . . . . ?
C27 C22 C23 C24 0.8(9) . . . . ?
C21 C22 C23 C24 -178.1(6) . . . . ?
C22 C23 C24 C25 -1.4(10) . . . . ?
C23 C24 C25 C26 0.8(10) . . . . ?
C24 C25 C26 C27 0.5(10) . . . . ?
C25 C26 C27 C22 -1.1(10) . . . . ?
C23 C22 C27 C26 0.4(10) . . . . ?
C21 C22 C27 C26 179.4(6) . . . . ?
C6 C21 C28 C29 89.4(7) . . . . ?
C22 C21 C28 C29 -144.6(6) . . . . ?
C6 C21 C28 C33 -87.9(8) . . . . ?
C22 C21 C28 C33 38.1(8) . . . . ?
C33 C28 C29 C30 -0.7(10) . . . . ?
C21 C28 C29 C30 -178.1(6) . . . . ?
C28 C29 C30 C31 1.5(11) . . . . ?
C29 C30 C31 C32 -1.0(11) . . . . ?
C30 C31 C32 C33 -0.2(10) . . . . ?
C31 C32 C33 C28 1.0(10) . . . . ?
C29 C28 C33 C32 -0.5(10) . . . . ?
C21 C28 C33 C32 176.8(6) . . . . ?
N3 C34 C35 C36 176.7(5) . . . . ?
C39 C34 C35 C36 -2.0(9) . . . . ?
N3 C34 C35 C40 -2.7(8) . . . . ?
C39 C34 C35 C40 178.7(6) . . . . ?
C34 C35 C36 C37 0.6(8) . . . . ?
C40 C35 C36 C37 180.0(6) . . . . ?
C35 C36 C37 C38 0.5(9) . . . . ?
C35 C36 C37 C53 -178.1(6) . . . . ?
C36 C37 C38 C39 -0.5(9) . . . . ?
C53 C37 C38 C39 178.1(5) . . . . ?
C37 C38 C39 C34 -0.6(8) . . . . ?
C37 C38 C39 C54 177.3(6) . . . . ?
N3 C34 C39 C38 -176.7(5) . . . . ?
C35 C34 C39 C38 2.0(9) . . . . ?
N3 C34 C39 C54 5.3(8) . . . . ?
C35 C34 C39 C54 -176.0(6) . . . . ?
C36 C35 C40 C41 -12.2(8) . . . . ?
C34 C35 C40 C41 167.1(5) . . . . ?
C36 C35 C40 C47 114.8(6) . . . . ?
C34 C35 C40 C47 -66.0(7) . . . . ?
C35 C40 C41 C46 84.2(7) . . . . ?
C47 C40 C41 C46 -43.8(8) . . . . ?
C35 C40 C41 C42 -93.5(7) . . . . ?
C47 C40 C41 C42 138.5(6) . . . . ?
C46 C41 C42 C43 -1.0(10) . . . . ?
C40 C41 C42 C43 176.7(6) . . . . ?
C41 C42 C43 C44 -1.3(11) . . . . ?
C42 C43 C44 C45 1.6(11) . . . . ?
C43 C44 C45 C46 0.3(10) . . . . ?
C44 C45 C46 C41 -2.5(10) . . . . ?
C42 C41 C46 C45 2.9(10) . . . . ?
C40 C41 C46 C45 -174.8(6) . . . . ?
C35 C40 C47 C52 -20.2(8) . . . . ?
C41 C40 C47 C52 106.4(7) . . . . ?
C35 C40 C47 C48 163.2(6) . . . . ?
C41 C40 C47 C48 -70.2(7) . . . . ?
C52 C47 C48 C49 -1.7(10) . . . . ?
C40 C47 C48 C49 175.1(6) . . . . ?
C47 C48 C49 C50 0.1(11) . . . . ?
C48 C49 C50 C51 1.7(11) . . . . ?
C49 C50 C51 C52 -1.8(10) . . . . ?
C48 C47 C52 C51 1.4(10) . . . . ?
C40 C47 C52 C51 -175.1(6) . . . . ?
C50 C51 C52 C47 0.3(9) . . . . ?
C38 C39 C54 C55 -116.1(6) . . . . ?
C34 C39 C54 C55 61.7(7) . . . . ?
C38 C39 C54 C61 12.8(8) . . . . ?
C34 C39 C54 C61 -169.5(5) . . . . ?
C61 C54 C55 C56 -84.9(7) . . . . ?
C39 C54 C55 C56 41.9(8) . . . . ?
C61 C54 C55 C60 96.5(6) . . . . ?
C39 C54 C55 C60 -136.7(6) . . . . ?
C60 C55 C56 C57 -1.3(9) . . . . ?
C54 C55 C56 C57 -179.9(6) . . . . ?
C55 C56 C57 C58 0.5(10) . . . . ?
C56 C57 C58 C59 1.4(10) . . . . ?
C57 C58 C59 C60 -2.4(10) . . . . ?
C58 C59 C60 C55 1.5(10) . . . . ?
C56 C55 C60 C59 0.4(9) . . . . ?
C54 C55 C60 C59 179.0(6) . . . . ?
C55 C54 C61 C66 -159.7(6) . . . . ?
C39 C54 C61 C66 74.4(7) . . . . ?
C55 C54 C61 C62 22.2(8) . . . . ?
C39 C54 C61 C62 -103.7(7) . . . . ?
C66 C61 C62 C63 0.8(9) . . . . ?
C54 C61 C62 C63 179.0(6) . . . . ?
C61 C62 C63 C64 -0.6(10) . . . . ?
C62 C63 C64 C65 0.2(10) . . . . ?
C63 C64 C65 C66 -0.1(10) . . . . ?
C62 C61 C66 C65 -0.7(9) . . . . ?
C54 C61 C66 C65 -178.9(6) . . . . ?
C64 C65 C66 C61 0.3(10) . . . . ?

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_jb_ms402
_database_code_depnum_ccdc_archive 'CCDC 1894112'
loop_
_audit_author_name
_audit_author_address
'Alexander Villinger'
;University Rostock
Germany
;
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2019-02-27 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H27 I'
_chemical_formula_sum            'C33 H27 I'
_chemical_formula_weight         550.44

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.5977(10)
_cell_length_b                   11.6939(11)
_cell_length_c                   22.470(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.856(4)
_cell_angle_gamma                90
_cell_volume                     2512.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9583
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      32.47

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.294
_shelx_estimated_absorpt_T_min   0.791
_shelx_estimated_absorpt_T_max   0.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6916
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Bruker D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            118940
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.386
_diffrn_reflns_theta_max         30.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7992
_reflns_number_gt                7091
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2013

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine.
 
 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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.0430P)²+5.0618P] 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         7992
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0960
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.51436(2) 0.79693(2) 0.70626(2) 0.02277(6) Uani 1 1 d . . . . .
C1 C 0.6086(2) 0.64788(18) 0.67484(9) 0.0129(4) Uani 1 1 d . . . . .
C2 C 0.5280(2) 0.57340(18) 0.63697(9) 0.0122(4) Uani 1 1 d . . . . .
C3 C 0.5926(2) 0.47427(19) 0.61779(9) 0.0133(4) Uani 1 1 d . . . . .
H3 H 0.5399 0.4224 0.5923 0.016 Uiso 1 1 calc R U . . .
C4 C 0.7326(2) 0.44959(18) 0.63520(9) 0.0133(4) Uani 1 1 d . . . . .
C5 C 0.8098(2) 0.52765(19) 0.67118(9) 0.0138(4) Uani 1 1 d . . . . .
H5 H 0.9056 0.5120 0.6824 0.017 Uiso 1 1 calc R U . . .
C6 C 0.7511(2) 0.62830(18) 0.69133(9) 0.0134(4) Uani 1 1 d . . . . .
C7 C 0.3778(2) 0.60312(18) 0.61404(9) 0.0128(4) Uani 1 1 d . . . . .
H7 H 0.3311 0.6316 0.6493 0.015 Uiso 1 1 calc R U . . .
C8 C 0.3757(2) 0.70212(19) 0.56976(9) 0.0141(4) Uani 1 1 d . . . . .
C9 C 0.4827(2) 0.7181(2) 0.53225(10) 0.0187(4) Uani 1 1 d . . . . .
H9 H 0.5586 0.6658 0.5337 0.022 Uiso 1 1 calc R U . . .
C10 C 0.4792(3) 0.8102(2) 0.49252(11) 0.0228(5) Uani 1 1 d . . . . .
H10 H 0.5529 0.8206 0.4674 0.027 Uiso 1 1 calc R U . . .
C11 C 0.3685(3) 0.8864(2) 0.48979(11) 0.0229(5) Uani 1 1 d . . . . .
H11 H 0.3662 0.9493 0.4629 0.028 Uiso 1 1 calc R U . . .
C12 C 0.2606(3) 0.8705(2) 0.52665(11) 0.0217(5) Uani 1 1 d . . . . .
H12 H 0.1842 0.9224 0.5247 0.026 Uiso 1 1 calc R U . . .
C13 C 0.2641(2) 0.7789(2) 0.56637(10) 0.0182(4) Uani 1 1 d . . . . .
H13 H 0.1900 0.7686 0.5913 0.022 Uiso 1 1 calc R U . . .
C14 C 0.2929(2) 0.50036(19) 0.58999(10) 0.0156(4) Uani 1 1 d . . . . .
C15 C 0.2397(3) 0.4927(2) 0.53059(11) 0.0233(5) Uani 1 1 d . . . . .
H15 H 0.2592 0.5519 0.5035 0.028 Uiso 1 1 calc R U . . .
C16 C 0.1581(3) 0.3997(3) 0.51008(14) 0.0334(6) Uani 1 1 d . . . . .
H16 H 0.1205 0.3967 0.4696 0.040 Uiso 1 1 calc R U . . .
C17 C 0.1320(3) 0.3117(3) 0.54890(17) 0.0358(7) Uani 1 1 d . . . . .
H17 H 0.0780 0.2475 0.5350 0.043 Uiso 1 1 calc R U . . .
C18 C 0.1851(3) 0.3177(2) 0.60834(17) 0.0341(7) Uani 1 1 d . . . . .
H18 H 0.1677 0.2574 0.6351 0.041 Uiso 1 1 calc R U . . .
C19 C 0.2637(3) 0.4118(2) 0.62866(13) 0.0260(5) Uani 1 1 d . . . . .
H19 H 0.2980 0.4159 0.6695 0.031 Uiso 1 1 calc R U . . .
C20 C 0.7995(2) 0.3416(2) 0.61478(10) 0.0189(4) Uani 1 1 d . . . . .
H20A H 0.8699 0.3610 0.5873 0.028 Uiso 1 1 calc R U . . .
H20B H 0.7278 0.2925 0.5943 0.028 Uiso 1 1 calc R U . . .
H20C H 0.8443 0.3011 0.6495 0.028 Uiso 1 1 calc R U . . .
C21 C 0.8407(2) 0.71728(19) 0.72661(9) 0.0148(4) Uani 1 1 d . . . . .
H21 H 0.7816 0.7488 0.7573 0.018 Uiso 1 1 calc R U . . .
C22 C 0.8746(2) 0.81778(19) 0.68682(9) 0.0153(4) Uani 1 1 d . . . . .
C23 C 0.9091(2) 0.9235(2) 0.71307(10) 0.0177(4) Uani 1 1 d . . . . .
H23 H 0.9162 0.9306 0.7553 0.021 Uiso 1 1 calc R U . . .
C24 C 0.9333(2) 1.0179(2) 0.67828(11) 0.0205(4) Uani 1 1 d . . . . .
H24 H 0.9556 1.0893 0.6969 0.025 Uiso 1 1 calc R U . . .
C25 C 0.9252(2) 1.0094(2) 0.61656(11) 0.0207(4) Uani 1 1 d . . . . .
H25 H 0.9418 1.0744 0.5928 0.025 Uiso 1 1 calc R U . . .
C26 C 0.8927(3) 0.9051(2) 0.58997(11) 0.0260(5) Uani 1 1 d . . . . .
H26 H 0.8876 0.8982 0.5477 0.031 Uiso 1 1 calc R U . . .
C27 C 0.8673(3) 0.8100(2) 0.62471(11) 0.0242(5) Uani 1 1 d . . . . .
H27 H 0.8447 0.7388 0.6059 0.029 Uiso 1 1 calc R U . . .
C28 C 0.9685(2) 0.6649(2) 0.76070(9) 0.0158(4) Uani 1 1 d . . . . .
C29 C 0.9545(3) 0.6177(2) 0.81682(10) 0.0202(4) Uani 1 1 d . . . . .
H29 H 0.8673 0.6228 0.8338 0.024 Uiso 1 1 calc R U . . .
C30 C 1.0667(3) 0.5632(2) 0.84837(11) 0.0227(5) Uani 1 1 d . . . . .
H30 H 1.0561 0.5328 0.8869 0.027 Uiso 1 1 calc R U . . .
C31 C 1.1937(3) 0.5532(2) 0.82389(11) 0.0243(5) Uani 1 1 d . . . . .
H31 H 1.2693 0.5139 0.8449 0.029 Uiso 1 1 calc R U . . .
C32 C 1.2092(3) 0.6011(3) 0.76857(12) 0.0275(5) Uani 1 1 d . . . . .
H32 H 1.2963 0.5952 0.7516 0.033 Uiso 1 1 calc R U . . .
C33 C 1.0979(3) 0.6578(3) 0.73752(11) 0.0235(5) Uani 1 1 d . . . . .
H33 H 1.1106 0.6921 0.7000 0.028 Uiso 1 1 calc R U . . .


#==============================================================================

# MOLECULAR GEOMETRY

_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
I1 C1 2.112(2) . ?
C1 C2 1.403(3) . ?
C1 C6 1.406(3) . ?
C2 C3 1.400(3) . ?
C2 C7 1.529(3) . ?
C3 C4 1.398(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(3) . ?
C4 C20 1.506(3) . ?
C5 C6 1.397(3) . ?
C5 H5 0.9500 . ?
C6 C21 1.528(3) . ?
C7 C14 1.525(3) . ?
C7 C8 1.525(3) . ?
C7 H7 1.0000 . ?
C8 C13 1.394(3) . ?
C8 C9 1.395(3) . ?
C9 C10 1.398(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.391(3) . ?
C14 C19 1.396(3) . ?
C15 C16 1.396(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C28 1.519(3) . ?
C21 C22 1.528(3) . ?
C21 H21 1.0000 . ?
C22 C27 1.394(3) . ?
C22 C23 1.398(3) . ?
C23 C24 1.384(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.392(4) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C33 1.389(3) . ?
C28 C29 1.393(3) . ?
C29 C30 1.393(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.383(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.383(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.394(3) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.20(19) . . ?
C2 C1 I1 119.03(15) . . ?
C6 C1 I1 118.75(15) . . ?
C3 C2 C1 117.72(19) . . ?
C3 C2 C7 120.92(18) . . ?
C1 C2 C7 121.24(19) . . ?
C4 C3 C2 121.68(19) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C5 C4 C3 118.7(2) . . ?
C5 C4 C20 120.48(19) . . ?
C3 C4 C20 120.84(19) . . ?
C4 C5 C6 122.11(19) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C1 117.52(19) . . ?
C5 C6 C21 121.17(19) . . ?
C1 C6 C21 121.20(19) . . ?
C14 C7 C8 112.94(17) . . ?
C14 C7 C2 113.60(18) . . ?
C8 C7 C2 110.64(17) . . ?
C14 C7 H7 106.4 . . ?
C8 C7 H7 106.4 . . ?
C2 C7 H7 106.4 . . ?
C13 C8 C9 118.8(2) . . ?
C13 C8 C7 119.5(2) . . ?
C9 C8 C7 121.72(19) . . ?
C8 C9 C10 120.7(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.6(2) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 120.5(2) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
C15 C14 C19 118.2(2) . . ?
C15 C14 C7 122.2(2) . . ?
C19 C14 C7 119.6(2) . . ?
C14 C15 C16 121.1(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 119.8(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 121.0(3) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
C4 C20 H20A 109.5 . . ?
C4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C28 C21 C6 112.44(18) . . ?
C28 C21 C22 113.72(19) . . ?
C6 C21 C22 111.00(17) . . ?
C28 C21 H21 106.4 . . ?
C6 C21 H21 106.4 . . ?
C22 C21 H21 106.4 . . ?
C27 C22 C23 118.1(2) . . ?
C27 C22 C21 122.7(2) . . ?
C23 C22 C21 119.21(19) . . ?
C24 C23 C22 120.8(2) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 120.7(2) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C26 C25 C24 119.2(2) . . ?
C26 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
C25 C26 C27 120.4(2) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C26 C27 C22 120.8(2) . . ?
C26 C27 H27 119.6 . . ?
C22 C27 H27 119.6 . . ?
C33 C28 C29 118.3(2) . . ?
C33 C28 C21 123.0(2) . . ?
C29 C28 C21 118.7(2) . . ?
C30 C29 C28 120.8(2) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C31 C30 C29 120.4(2) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C32 C31 C30 119.3(2) . . ?
C32 C31 H31 120.4 . . ?
C30 C31 H31 120.4 . . ?
C31 C32 C33 120.4(2) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C28 C33 C32 120.8(2) . . ?
C28 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?

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
C6 C1 C2 C3 3.0(3) . . . . ?
I1 C1 C2 C3 -178.83(15) . . . . ?
C6 C1 C2 C7 -173.06(19) . . . . ?
I1 C1 C2 C7 5.2(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C7 C2 C3 C4 175.74(19) . . . . ?
C2 C3 C4 C5 -1.8(3) . . . . ?
C2 C3 C4 C20 179.1(2) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C20 C4 C5 C6 -179.5(2) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C4 C5 C6 C21 -175.1(2) . . . . ?
C2 C1 C6 C5 -3.4(3) . . . . ?
I1 C1 C6 C5 178.41(15) . . . . ?
C2 C1 C6 C21 172.83(19) . . . . ?
I1 C1 C6 C21 -5.4(3) . . . . ?
C3 C2 C7 C14 21.7(3) . . . . ?
C1 C2 C7 C14 -162.40(19) . . . . ?
C3 C2 C7 C8 -106.5(2) . . . . ?
C1 C2 C7 C8 69.4(2) . . . . ?
C14 C7 C8 C13 83.6(2) . . . . ?
C2 C7 C8 C13 -147.7(2) . . . . ?
C14 C7 C8 C9 -96.2(2) . . . . ?
C2 C7 C8 C9 32.4(3) . . . . ?
C13 C8 C9 C10 0.9(3) . . . . ?
C7 C8 C9 C10 -179.3(2) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C11 C12 C13 C8 0.1(4) . . . . ?
C9 C8 C13 C12 -0.7(3) . . . . ?
C7 C8 C13 C12 179.4(2) . . . . ?
C8 C7 C14 C15 9.8(3) . . . . ?
C2 C7 C14 C15 -117.2(2) . . . . ?
C8 C7 C14 C19 -168.4(2) . . . . ?
C2 C7 C14 C19 64.5(3) . . . . ?
C19 C14 C15 C16 0.6(4) . . . . ?
C7 C14 C15 C16 -177.7(2) . . . . ?
C14 C15 C16 C17 -1.6(4) . . . . ?
C15 C16 C17 C18 1.2(4) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C17 C18 C19 C14 -1.2(4) . . . . ?
C15 C14 C19 C18 0.9(4) . . . . ?
C7 C14 C19 C18 179.2(2) . . . . ?
C5 C6 C21 C28 -27.0(3) . . . . ?
C1 C6 C21 C28 156.9(2) . . . . ?
C5 C6 C21 C22 101.6(2) . . . . ?
C1 C6 C21 C22 -74.4(3) . . . . ?
C28 C21 C22 C27 107.5(3) . . . . ?
C6 C21 C22 C27 -20.5(3) . . . . ?
C28 C21 C22 C23 -75.1(3) . . . . ?
C6 C21 C22 C23 156.9(2) . . . . ?
C27 C22 C23 C24 1.0(4) . . . . ?
C21 C22 C23 C24 -176.6(2) . . . . ?
C22 C23 C24 C25 -0.7(4) . . . . ?
C23 C24 C25 C26 0.0(4) . . . . ?
C24 C25 C26 C27 0.5(4) . . . . ?
C25 C26 C27 C22 -0.2(4) . . . . ?
C23 C22 C27 C26 -0.5(4) . . . . ?
C21 C22 C27 C26 177.0(2) . . . . ?
C6 C21 C28 C33 92.8(3) . . . . ?
C22 C21 C28 C33 -34.4(3) . . . . ?
C6 C21 C28 C29 -84.6(3) . . . . ?
C22 C21 C28 C29 148.2(2) . . . . ?
C33 C28 C29 C30 -1.0(4) . . . . ?
C21 C28 C29 C30 176.5(2) . . . . ?
C28 C29 C30 C31 -1.2(4) . . . . ?
C29 C30 C31 C32 2.0(4) . . . . ?
C30 C31 C32 C33 -0.6(4) . . . . ?
C29 C28 C33 C32 2.5(4) . . . . ?
C21 C28 C33 C32 -175.0(2) . . . . ?
C31 C32 C33 C28 -1.7(5) . . . . ?

_refine_diff_density_max         0.783
_refine_diff_density_min         -1.053
_refine_diff_density_rms         0.108

#==============================================================================

# SHELX FILES

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_av_ts047
_database_code_depnum_ccdc_archive 'CCDC 1894116'
loop_
_audit_author_name
_audit_author_address
'Alexander Villinger'
;University Rostock
Germany
;
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2019-02-27 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H33 Cl1.63 I0.37 P'
_chemical_formula_sum            'C36 H33 Cl1.63 I0.37 P'
_chemical_formula_weight         600.87

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'


#==============================================================================

# CRYSTAL DATA 

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.2059(5)
_cell_length_b                   19.1823(9)
_cell_length_c                   14.8511(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.670(2)
_cell_angle_gamma                90
_cell_volume                     3073.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9988
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      32.57

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             1245
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.621
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6889
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'

#==============================================================================

# EXPERIMENTAL DATA


_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            67030
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.166
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             8147
_reflns_number_gt                6650
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

#==============================================================================

# REFINEMENT DATA 

_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 > 2σ(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     
'w=1/[σ²(Fo²)+5.9550P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0115(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8147
_refine_ls_number_parameters     504
_refine_ls_number_restraints     260
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0712
_refine_ls_wR_factor_ref         0.1540
_refine_ls_wR_factor_gt          0.1481
_refine_ls_goodness_of_fit_ref   1.266
_refine_ls_restrained_S_all      1.250
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.04514(8) 0.59262(5) 0.60460(6) 0.0333(2) Uani 1 1 d . . . . .
Cl1 Cl -0.0079(3) 0.69439(17) 0.6318(2) 0.0402(5) Uani 0.709(2) 1 d . . P A 1
Cl2 Cl -0.0689(4) 0.5827(3) 0.4690(3) 0.0354(6) Uani 0.9262(19) 1 d . . P A 1
I1 I 0.0039(2) 0.70525(12) 0.66194(12) 0.0413(4) Uani 0.291(2) 1 d . . P A 2
I2 I -0.0899(12) 0.5919(8) 0.4506(9) 0.0300(19) Uani 0.0738(19) 1 d . . P A 2
C1 C 0.1998(3) 0.60755(15) 0.5888(2) 0.0244(6) Uani 1 1 d . . . . .
C2 C 0.2940(3) 0.56994(16) 0.6542(2) 0.0260(6) Uani 1 1 d . . . . .
C3 C 0.4157(3) 0.57467(17) 0.6492(2) 0.0297(6) Uani 1 1 d . . . . .
H3 H 0.4777 0.5485 0.6922 0.036 Uiso 1 1 calc R U . . .
C4 C 0.4503(3) 0.61618(17) 0.5837(2) 0.0275(6) Uani 1 1 d . . . . .
C5 C 0.3572(3) 0.65439(16) 0.5227(2) 0.0267(6) Uani 1 1 d . . . . .
H5 H 0.3794 0.6843 0.4788 0.032 Uiso 1 1 calc R U . . .
C6 C 0.2332(3) 0.65096(16) 0.5229(2) 0.0251(6) Uani 1 1 d . . . . .
C7A C 0.2661(7) 0.5288(4) 0.7318(4) 0.0255(13) Uani 0.765(17) 1 d D . P B 1
H7A H 0.1891 0.5017 0.7026 0.031 Uiso 0.765(17) 1 calc R U P B 1
C8A C 0.2347(6) 0.5751(3) 0.8054(4) 0.0286(12) Uani 0.765(17) 1 d D . P B 1
C9A C 0.2862(8) 0.6405(4) 0.8287(6) 0.0454(17) Uani 0.765(17) 1 d D . P B 1
H9A H 0.3414 0.6589 0.7961 0.055 Uiso 0.765(17) 1 calc R U P B 1
C10A C 0.2580(8) 0.6795(4) 0.8993(6) 0.0530(19) Uani 0.765(17) 1 d D . P B 1
H10A H 0.2948 0.7240 0.9154 0.064 Uiso 0.765(17) 1 calc R U P B 1
C11A C 0.1757(8) 0.6534(4) 0.9462(5) 0.048(2) Uani 0.765(17) 1 d D . P B 1
H11A H 0.1554 0.6799 0.9941 0.057 Uiso 0.765(17) 1 calc R U P B 1
C12A C 0.1241(7) 0.5886(4) 0.9226(5) 0.0422(16) Uani 0.765(17) 1 d D . P B 1
H12A H 0.0677 0.5706 0.9543 0.051 Uiso 0.765(17) 1 calc R U P B 1
C13A C 0.1530(7) 0.5493(4) 0.8535(5) 0.0351(13) Uani 0.765(17) 1 d D . P B 1
H13A H 0.1171 0.5045 0.8386 0.042 Uiso 0.765(17) 1 calc R U P B 1
C14A C 0.3649(5) 0.4749(3) 0.7760(4) 0.0284(12) Uani 0.765(17) 1 d D . P B 1
C15A C 0.3583(7) 0.4084(3) 0.7373(3) 0.0390(15) Uani 0.765(17) 1 d D . P B 1
H15A H 0.2888 0.3961 0.6872 0.047 Uiso 0.765(17) 1 calc R U P B 1
C16A C 0.4507(8) 0.3600(3) 0.7703(4) 0.0471(19) Uani 0.765(17) 1 d D . P B 1
H16A H 0.4453 0.3152 0.7422 0.057 Uiso 0.765(17) 1 calc R U P B 1
C17A C 0.5506(7) 0.3766(4) 0.8440(4) 0.0446(16) Uani 0.765(17) 1 d D . P B 1
H17A H 0.6148 0.3435 0.8662 0.054 Uiso 0.765(17) 1 calc R U P B 1
C18A C 0.5578(7) 0.4412(4) 0.8855(5) 0.0405(15) Uani 0.765(17) 1 d D . P B 1
H18A H 0.6261 0.4521 0.9372 0.049 Uiso 0.765(17) 1 calc R U P B 1
C19A C 0.4654(7) 0.4907(4) 0.8521(5) 0.0340(15) Uani 0.765(17) 1 d D . P B 1
H19A H 0.4709 0.5352 0.8810 0.041 Uiso 0.765(17) 1 calc R U P B 1
C7B C 0.268(3) 0.5238(15) 0.7442(15) 0.031(3) Uani 0.235(17) 1 d D U P B 2
H7B H 0.1936 0.4936 0.7221 0.037 Uiso 0.235(17) 1 calc R U P B 2
C8B C 0.250(2) 0.5762(11) 0.8167(17) 0.036(3) Uani 0.235(17) 1 d DG U P B 2
C9B C 0.3165(19) 0.6381(12) 0.8328(16) 0.035(3) Uani 0.235(17) 1 d DG U P B 2
H9B H 0.3773 0.6475 0.8005 0.042 Uiso 0.235(17) 1 calc R U P B 2
C10B C 0.2945(18) 0.6864(10) 0.8963(15) 0.037(3) Uani 0.235(17) 1 d DG U P B 2
H10B H 0.3402 0.7287 0.9073 0.045 Uiso 0.235(17) 1 calc R U P B 2
C11B C 0.2056(18) 0.6728(10) 0.9436(14) 0.037(3) Uani 0.235(17) 1 d DG U P B 2
H11B H 0.1905 0.7058 0.9869 0.044 Uiso 0.235(17) 1 calc R U P B 2
C12B C 0.1387(19) 0.6109(11) 0.9274(15) 0.037(3) Uani 0.235(17) 1 d DG U P B 2
H12B H 0.0780 0.6016 0.9597 0.044 Uiso 0.235(17) 1 calc R U P B 2
C13B C 0.161(2) 0.5626(9) 0.8639(18) 0.037(3) Uani 0.235(17) 1 d DG U P B 2
H13B H 0.1151 0.5203 0.8529 0.044 Uiso 0.235(17) 1 calc R U P B 2
C14B C 0.3852(19) 0.4791(9) 0.7801(13) 0.033(3) Uani 0.235(17) 1 d DG U P B 2
C15B C 0.4035(16) 0.4232(8) 0.7256(9) 0.033(3) Uani 0.235(17) 1 d DG U P B 2
H15B H 0.3476 0.4155 0.6658 0.040 Uiso 0.235(17) 1 calc R U P B 2
C16B C 0.5038(16) 0.3788(8) 0.7586(9) 0.033(3) Uani 0.235(17) 1 d DG U P B 2
H16B H 0.5163 0.3406 0.7214 0.040 Uiso 0.235(17) 1 calc R U P B 2
C17B C 0.5856(15) 0.3901(9) 0.8461(10) 0.034(3) Uani 0.235(17) 1 d DG U P B 2
H17B H 0.6541 0.3597 0.8687 0.040 Uiso 0.235(17) 1 calc R U P B 2
C18B C 0.567(2) 0.4459(12) 0.9005(11) 0.033(3) Uani 0.235(17) 1 d DG U P B 2
H18B H 0.6232 0.4537 0.9603 0.040 Uiso 0.235(17) 1 calc R U P B 2
C19B C 0.467(2) 0.4904(12) 0.8675(14) 0.032(3) Uani 0.235(17) 1 d DG U P B 2
H19B H 0.4545 0.5285 0.9047 0.038 Uiso 0.235(17) 1 calc R U P B 2
C20A C 0.5860(6) 0.6240(4) 0.5820(6) 0.0362(9) Uani 0.777(6) 1 d D . P C 1
C21A C 0.6698(4) 0.5692(3) 0.6390(4) 0.0521(15) Uani 0.777(6) 1 d D . P C 1
H21A H 0.6372 0.5228 0.6181 0.078 Uiso 0.777(6) 1 calc R U P C 1
H21B H 0.6733 0.5751 0.7053 0.078 Uiso 0.777(6) 1 calc R U P C 1
H21C H 0.7532 0.5740 0.6308 0.078 Uiso 0.777(6) 1 calc R U P C 1
C22A C 0.5963(5) 0.6250(4) 0.4821(4) 0.067(2) Uani 0.777(6) 1 d D . P C 1
H22A H 0.5593 0.5825 0.4498 0.100 Uiso 0.777(6) 1 calc R U P C 1
H22B H 0.6838 0.6275 0.4825 0.100 Uiso 0.777(6) 1 calc R U P C 1
H22C H 0.5523 0.6658 0.4494 0.100 Uiso 0.777(6) 1 calc R U P C 1
C23A C 0.6312(4) 0.6972(3) 0.6273(4) 0.0517(14) Uani 0.777(6) 1 d D . P C 1
H23A H 0.7173 0.7050 0.6265 0.078 Uiso 0.777(6) 1 calc R U P C 1
H23B H 0.6258 0.6979 0.6921 0.078 Uiso 0.777(6) 1 calc R U P C 1
H23C H 0.5786 0.7341 0.5916 0.078 Uiso 0.777(6) 1 calc R U P C 1
C20B C 0.5802(19) 0.6161(12) 0.5777(15) 0.0362(9) Uani 0.223(6) 1 d D U P C 2
C21B C 0.6057(15) 0.6723(8) 0.5141(11) 0.040(3) Uani 0.223(6) 1 d D U P C 2
H21D H 0.6934 0.6709 0.5148 0.060 Uiso 0.223(6) 1 calc R U P C 2
H21E H 0.5862 0.7180 0.5361 0.060 Uiso 0.223(6) 1 calc R U P C 2
H21F H 0.5541 0.6644 0.4502 0.060 Uiso 0.223(6) 1 calc R U P C 2
C22B C 0.6680(16) 0.6239(10) 0.6747(10) 0.049(4) Uani 0.223(6) 1 d D U P C 2
H22D H 0.6569 0.5845 0.7137 0.074 Uiso 0.223(6) 1 calc R U P C 2
H22E H 0.6501 0.6675 0.7028 0.074 Uiso 0.223(6) 1 calc R U P C 2
H22F H 0.7537 0.6246 0.6703 0.074 Uiso 0.223(6) 1 calc R U P C 2
C23B C 0.6077(15) 0.5437(7) 0.5368(12) 0.043(3) Uani 0.223(6) 1 d D U P C 2
H23D H 0.5501 0.5367 0.4749 0.064 Uiso 0.223(6) 1 calc R U P C 2
H23E H 0.5969 0.5061 0.5787 0.064 Uiso 0.223(6) 1 calc R U P C 2
H23F H 0.6930 0.5432 0.5316 0.064 Uiso 0.223(6) 1 calc R U P C 2
C24 C 0.1416(3) 0.69498(16) 0.4498(2) 0.0269(6) Uani 1 1 d . . . . .
H24 H 0.0643 0.6989 0.4708 0.032 Uiso 1 1 calc R U . . .
C25 C 0.1047(3) 0.66253(17) 0.3522(2) 0.0307(7) Uani 1 1 d . . . . .
C26 C 0.1696(3) 0.6099(2) 0.3238(3) 0.0425(9) Uani 1 1 d . . . . .
H26 H 0.2399 0.5901 0.3671 0.051 Uiso 1 1 calc R U . . .
C27 C 0.1332(4) 0.5852(3) 0.2323(3) 0.0549(11) Uani 1 1 d . . . . .
H27 H 0.1796 0.5493 0.2134 0.066 Uiso 1 1 calc R U . . .
C28 C 0.0316(4) 0.6121(2) 0.1695(3) 0.0517(10) Uani 1 1 d . . . . .
H28 H 0.0079 0.5952 0.1070 0.062 Uiso 1 1 calc R U . . .
C29 C -0.0362(4) 0.6633(3) 0.1966(3) 0.0628(13) Uani 1 1 d . . . . .
H29 H -0.1077 0.6817 0.1531 0.075 Uiso 1 1 calc R U . . .
C30 C -0.0005(4) 0.6885(2) 0.2873(3) 0.0504(10) Uani 1 1 d . . . . .
H30 H -0.0483 0.7239 0.3057 0.060 Uiso 1 1 calc R U . . .
C31 C 0.1901(3) 0.76939(16) 0.4453(2) 0.0278(6) Uani 1 1 d . . . . .
C32 C 0.2625(3) 0.78721(17) 0.3863(2) 0.0331(7) Uani 1 1 d . . . . .
H32 H 0.2810 0.7529 0.3459 0.040 Uiso 1 1 calc R U . . .
C33 C 0.3083(3) 0.85461(19) 0.3854(3) 0.0388(8) Uani 1 1 d . . . . .
H33 H 0.3598 0.8657 0.3460 0.047 Uiso 1 1 calc R U . . .
C34 C 0.2786(3) 0.90539(19) 0.4418(3) 0.0409(8) Uani 1 1 d . . . . .
H34 H 0.3088 0.9516 0.4407 0.049 Uiso 1 1 calc R U . . .
C35 C 0.2050(3) 0.88868(18) 0.4996(3) 0.0402(8) Uani 1 1 d . . . . .
H35 H 0.1844 0.9235 0.5384 0.048 Uiso 1 1 calc R U . . .
C36 C 0.1609(3) 0.82132(18) 0.5014(2) 0.0328(7) Uani 1 1 d . . . . .
H36 H 0.1101 0.8104 0.5414 0.039 Uiso 1 1 calc R U . . .


#==============================================================================

# MOLECULAR GEOMETRY

_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 C1 1.833(3) . ?
P1 Cl2 2.082(4) . ?
P1 Cl1 2.111(3) . ?
P1 I2 2.377(12) . ?
P1 I1 2.412(2) . ?
C1 C6 1.411(4) . ?
C1 C2 1.422(4) . ?
C2 C3 1.388(4) . ?
C2 C7A 1.498(9) . ?
C2 C7B 1.69(3) . ?
C3 C4 1.390(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(4) . ?
C4 C20B 1.48(2) . ?
C4 C20A 1.535(7) . ?
C5 C6 1.392(4) . ?
C5 H5 0.9500 . ?
C6 C24 1.531(4) . ?
C7A C8A 1.523(5) . ?
C7A C14A 1.528(5) . ?
C7A H7A 1.0000 . ?
C8A C9A 1.384(5) . ?
C8A C13A 1.395(5) . ?
C9A C10A 1.393(6) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.391(6) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.375(6) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.380(6) . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9500 . ?
C14A C15A 1.393(5) . ?
C14A C19A 1.397(5) . ?
C15A C16A 1.378(6) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.375(6) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.377(6) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.393(6) . ?
C18A H18A 0.9500 . ?
C19A H19A 0.9500 . ?
C7B C8B 1.528(8) . ?
C7B C14B 1.535(8) . ?
C7B H7B 1.0000 . ?
C8B C9B 1.3900 . ?
C8B C13B 1.3900 . ?
C9B C10B 1.3900 . ?
C9B H9B 0.9500 . ?
C10B C11B 1.3900 . ?
C10B H10B 0.9500 . ?
C11B C12B 1.3900 . ?
C11B H11B 0.9500 . ?
C12B C13B 1.3900 . ?
C12B H12B 0.9500 . ?
C13B H13B 0.9500 . ?
C14B C15B 1.3900 . ?
C14B C19B 1.3900 . ?
C15B C16B 1.3900 . ?
C15B H15B 0.9500 . ?
C16B C17B 1.3900 . ?
C16B H16B 0.9500 . ?
C17B C18B 1.3900 . ?
C17B H17B 0.9500 . ?
C18B C19B 1.3900 . ?
C18B H18B 0.9500 . ?
C19B H19B 0.9500 . ?
C20A C21A 1.509(9) . ?
C20A C22A 1.519(10) . ?
C20A C23A 1.580(11) . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
C22A H22A 0.9800 . ?
C22A H22B 0.9800 . ?
C22A H22C 0.9800 . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C23A H23C 0.9800 . ?
C20B C21B 1.510(15) . ?
C20B C22B 1.517(15) . ?
C20B C23B 1.579(16) . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?
C22B H22D 0.9800 . ?
C22B H22E 0.9800 . ?
C22B H22F 0.9800 . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?
C24 C25 1.529(4) . ?
C24 C31 1.535(4) . ?
C24 H24 1.0000 . ?
C25 C26 1.375(5) . ?
C25 C30 1.397(5) . ?
C26 C27 1.393(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.363(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.368(7) . ?
C28 H28 0.9500 . ?
C29 C30 1.385(6) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.387(4) . ?
C31 C36 1.394(4) . ?
C32 C33 1.392(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.382(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.380(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.386(5) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 Cl2 104.20(17) . . ?
C1 P1 Cl1 101.81(13) . . ?
Cl2 P1 Cl1 97.96(16) . . ?
C1 P1 I2 104.8(4) . . ?
C1 P1 I1 100.55(11) . . ?
I2 P1 I1 102.2(4) . . ?
C6 C1 C2 119.0(3) . . ?
C6 C1 P1 128.2(2) . . ?
C2 C1 P1 112.7(2) . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 C7A 119.2(4) . . ?
C1 C2 C7A 121.4(4) . . ?
C3 C2 C7B 117.0(8) . . ?
C1 C2 C7B 123.5(8) . . ?
C2 C3 C4 122.6(3) . . ?
C2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C3 C4 C5 117.1(3) . . ?
C3 C4 C20B 120.4(9) . . ?
C5 C4 C20B 122.4(9) . . ?
C3 C4 C20A 122.2(4) . . ?
C5 C4 C20A 120.6(4) . . ?
C4 C5 C6 123.1(3) . . ?
C4 C5 H5 118.4 . . ?
C6 C5 H5 118.4 . . ?
C5 C6 C1 118.8(3) . . ?
C5 C6 C24 116.8(3) . . ?
C1 C6 C24 124.4(3) . . ?
C2 C7A C8A 112.4(4) . . ?
C2 C7A C14A 114.2(6) . . ?
C8A C7A C14A 111.6(4) . . ?
C2 C7A H7A 106.0 . . ?
C8A C7A H7A 106.0 . . ?
C14A C7A H7A 106.0 . . ?
C9A C8A C13A 118.7(4) . . ?
C9A C8A C7A 123.1(4) . . ?
C13A C8A C7A 118.1(4) . . ?
C8A C9A C10A 120.7(5) . . ?
C8A C9A H9A 119.7 . . ?
C10A C9A H9A 119.7 . . ?
C11A C10A C9A 120.0(5) . . ?
C11A C10A H10A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C12A C11A C10A 119.2(4) . . ?
C12A C11A H11A 120.4 . . ?
C10A C11A H11A 120.4 . . ?
C11A C12A C13A 121.1(4) . . ?
C11A C12A H12A 119.4 . . ?
C13A C12A H12A 119.4 . . ?
C12A C13A C8A 120.3(4) . . ?
C12A C13A H13A 119.8 . . ?
C8A C13A H13A 119.8 . . ?
C15A C14A C19A 118.3(4) . . ?
C15A C14A C7A 119.4(4) . . ?
C19A C14A C7A 122.2(4) . . ?
C16A C15A C14A 121.3(4) . . ?
C16A C15A H15A 119.4 . . ?
C14A C15A H15A 119.4 . . ?
C17A C16A C15A 119.9(4) . . ?
C17A C16A H16A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C16A C17A C18A 120.1(5) . . ?
C16A C17A H17A 119.9 . . ?
C18A C17A H17A 119.9 . . ?
C17A C18A C19A 120.4(4) . . ?
C17A C18A H18A 119.8 . . ?
C19A C18A H18A 119.8 . . ?
C18A C19A C14A 120.0(4) . . ?
C18A C19A H19A 120.0 . . ?
C14A C19A H19A 120.0 . . ?
C8B C7B C14B 113.0(11) . . ?
C8B C7B C2 107.3(14) . . ?
C14B C7B C2 105(2) . . ?
C8B C7B H7B 110.5 . . ?
C14B C7B H7B 110.5 . . ?
C2 C7B H7B 110.5 . . ?
C9B C8B C13B 120.0 . . ?
C9B C8B C7B 120.9(9) . . ?
C13B C8B C7B 119.1(9) . . ?
C8B C9B C10B 120.0 . . ?
C8B C9B H9B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C11B C10B C9B 120.0 . . ?
C11B C10B H10B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
C10B C11B C12B 120.0 . . ?
C10B C11B H11B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C13B C12B C11B 120.0 . . ?
C13B C12B H12B 120.0 . . ?
C11B C12B H12B 120.0 . . ?
C12B C13B C8B 120.0 . . ?
C12B C13B H13B 120.0 . . ?
C8B C13B H13B 120.0 . . ?
C15B C14B C19B 120.0 . . ?
C15B C14B C7B 118.4(8) . . ?
C19B C14B C7B 121.5(8) . . ?
C16B C15B C14B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C14B C15B H15B 120.0 . . ?
C15B C16B C17B 120.0 . . ?
C15B C16B H16B 120.0 . . ?
C17B C16B H16B 120.0 . . ?
C16B C17B C18B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C18B C17B H17B 120.0 . . ?
C19B C18B C17B 120.0 . . ?
C19B C18B H18B 120.0 . . ?
C17B C18B H18B 120.0 . . ?
C18B C19B C14B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C14B C19B H19B 120.0 . . ?
C21A C20A C22A 110.9(6) . . ?
C21A C20A C4 113.0(5) . . ?
C22A C20A C4 110.8(5) . . ?
C21A C20A C23A 107.5(6) . . ?
C22A C20A C23A 107.8(6) . . ?
C4 C20A C23A 106.6(5) . . ?
C20A C21A H21A 109.5 . . ?
C20A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C20A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C20A C22A H22A 109.5 . . ?
C20A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C20A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
C20A C23A H23A 109.5 . . ?
C20A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
C20A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
C4 C20B C21B 113.1(15) . . ?
C4 C20B C22B 109.7(15) . . ?
C21B C20B C22B 109.9(13) . . ?
C4 C20B C23B 108.7(14) . . ?
C21B C20B C23B 107.4(13) . . ?
C22B C20B C23B 107.9(14) . . ?
C20B C21B H21D 109.5 . . ?
C20B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C20B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C20B C22B H22D 109.5 . . ?
C20B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C20B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
C20B C23B H23D 109.5 . . ?
C20B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
C20B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
C25 C24 C6 114.0(3) . . ?
C25 C24 C31 110.2(2) . . ?
C6 C24 C31 111.5(2) . . ?
C25 C24 H24 106.9 . . ?
C6 C24 H24 106.9 . . ?
C31 C24 H24 106.9 . . ?
C26 C25 C30 117.9(3) . . ?
C26 C25 C24 124.0(3) . . ?
C30 C25 C24 118.1(3) . . ?
C25 C26 C27 120.6(4) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C28 C27 C26 120.6(4) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C28 C29 119.9(4) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 H28 120.1 . . ?
C28 C29 C30 119.9(4) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C29 C30 C25 121.0(4) . . ?
C29 C30 H30 119.5 . . ?
C25 C30 H30 119.5 . . ?
C32 C31 C36 118.3(3) . . ?
C32 C31 C24 122.1(3) . . ?
C36 C31 C24 119.6(3) . . ?
C31 C32 C33 121.0(3) . . ?
C31 C32 H32 119.5 . . ?
C33 C32 H32 119.5 . . ?
C34 C33 C32 119.9(3) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C35 C34 C33 119.7(3) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C34 C35 C36 120.3(3) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C35 C36 C31 120.8(3) . . ?
C35 C36 H36 119.6 . . ?
C31 C36 H36 119.6 . . ?

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
Cl2 P1 C1 C6 42.7(3) . . . . ?
Cl1 P1 C1 C6 -58.8(3) . . . . ?
I2 P1 C1 C6 37.5(5) . . . . ?
I1 P1 C1 C6 -68.3(3) . . . . ?
Cl2 P1 C1 C2 -138.3(2) . . . . ?
Cl1 P1 C1 C2 120.2(2) . . . . ?
I2 P1 C1 C2 -143.5(4) . . . . ?
I1 P1 C1 C2 110.7(2) . . . . ?
C6 C1 C2 C3 -2.6(4) . . . . ?
P1 C1 C2 C3 178.3(2) . . . . ?
C6 C1 C2 C7A 173.7(4) . . . . ?
P1 C1 C2 C7A -5.4(4) . . . . ?
C6 C1 C2 C7B 172.6(9) . . . . ?
P1 C1 C2 C7B -6.5(10) . . . . ?
C1 C2 C3 C4 1.5(5) . . . . ?
C7A C2 C3 C4 -174.9(4) . . . . ?
C7B C2 C3 C4 -174.0(9) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C2 C3 C4 C20B -176.3(10) . . . . ?
C2 C3 C4 C20A 176.8(5) . . . . ?
C3 C4 C5 C6 -2.0(5) . . . . ?
C20B C4 C5 C6 175.0(11) . . . . ?
C20A C4 C5 C6 -178.1(4) . . . . ?
C4 C5 C6 C1 0.9(5) . . . . ?
C4 C5 C6 C24 -178.6(3) . . . . ?
C2 C1 C6 C5 1.4(4) . . . . ?
P1 C1 C6 C5 -179.6(2) . . . . ?
C2 C1 C6 C24 -179.1(3) . . . . ?
P1 C1 C6 C24 -0.1(4) . . . . ?
C3 C2 C7A C8A 106.9(4) . . . . ?
C1 C2 C7A C8A -69.4(5) . . . . ?
C3 C2 C7A C14A -21.5(6) . . . . ?
C1 C2 C7A C14A 162.2(4) . . . . ?
C2 C7A C8A C9A -32.4(7) . . . . ?
C14A C7A C8A C9A 97.4(8) . . . . ?
C2 C7A C8A C13A 149.6(5) . . . . ?
C14A C7A C8A C13A -80.6(8) . . . . ?
C13A C8A C9A C10A 0.5(8) . . . . ?
C7A C8A C9A C10A -177.4(6) . . . . ?
C8A C9A C10A C11A -1.0(9) . . . . ?
C9A C10A C11A C12A 0.6(9) . . . . ?
C10A C11A C12A C13A 0.2(8) . . . . ?
C11A C12A C13A C8A -0.7(7) . . . . ?
C9A C8A C13A C12A 0.3(7) . . . . ?
C7A C8A C13A C12A 178.3(5) . . . . ?
C2 C7A C14A C15A -87.3(9) . . . . ?
C8A C7A C14A C15A 143.9(7) . . . . ?
C2 C7A C14A C19A 89.9(6) . . . . ?
C8A C7A C14A C19A -39.0(9) . . . . ?
C19A C14A C15A C16A -2.6(8) . . . . ?
C7A C14A C15A C16A 174.7(6) . . . . ?
C14A C15A C16A C17A 1.2(9) . . . . ?
C15A C16A C17A C18A 0.7(10) . . . . ?
C16A C17A C18A C19A -1.3(9) . . . . ?
C17A C18A C19A C14A 0.0(8) . . . . ?
C15A C14A C19A C18A 1.9(8) . . . . ?
C7A C14A C19A C18A -175.3(7) . . . . ?
C3 C2 C7B C8B 102.5(11) . . . . ?
C1 C2 C7B C8B -72.8(15) . . . . ?
C3 C2 C7B C14B -18.0(15) . . . . ?
C1 C2 C7B C14B 166.8(8) . . . . ?
C14B C7B C8B C9B 79(3) . . . . ?
C2 C7B C8B C9B -36.2(18) . . . . ?
C14B C7B C8B C13B -104(3) . . . . ?
C2 C7B C8B C13B 141.2(14) . . . . ?
C13B C8B C9B C10B 0.0 . . . . ?
C7B C8B C9B C10B 177.4(18) . . . . ?
C8B C9B C10B C11B 0.0 . . . . ?
C9B C10B C11B C12B 0.0 . . . . ?
C10B C11B C12B C13B 0.0 . . . . ?
C11B C12B C13B C8B 0.0 . . . . ?
C9B C8B C13B C12B 0.0 . . . . ?
C7B C8B C13B C12B -177.4(18) . . . . ?
C8B C7B C14B C15B 171.4(15) . . . . ?
C2 C7B C14B C15B -72(2) . . . . ?
C8B C7B C14B C19B -4(3) . . . . ?
C2 C7B C14B C19B 112.4(13) . . . . ?
C19B C14B C15B C16B 0.0 . . . . ?
C7B C14B C15B C16B -176(2) . . . . ?
C14B C15B C16B C17B 0.0 . . . . ?
C15B C16B C17B C18B 0.0 . . . . ?
C16B C17B C18B C19B 0.0 . . . . ?
C17B C18B C19B C14B 0.0 . . . . ?
C15B C14B C19B C18B 0.0 . . . . ?
C7B C14B C19B C18B 176(2) . . . . ?
C3 C4 C20A C21A 15.3(8) . . . . ?
C5 C4 C20A C21A -168.9(5) . . . . ?
C3 C4 C20A C22A 140.4(6) . . . . ?
C5 C4 C20A C22A -43.7(8) . . . . ?
C3 C4 C20A C23A -102.6(5) . . . . ?
C5 C4 C20A C23A 73.3(6) . . . . ?
C3 C4 C20B C21B -170.7(10) . . . . ?
C5 C4 C20B C21B 12.3(19) . . . . ?
C3 C4 C20B C22B -47.6(17) . . . . ?
C5 C4 C20B C22B 135.4(11) . . . . ?
C3 C4 C20B C23B 70.1(15) . . . . ?
C5 C4 C20B C23B -106.8(12) . . . . ?
C5 C6 C24 C25 79.3(3) . . . . ?
C1 C6 C24 C25 -100.2(3) . . . . ?
C5 C6 C24 C31 -46.2(4) . . . . ?
C1 C6 C24 C31 134.3(3) . . . . ?
C6 C24 C25 C26 -17.2(5) . . . . ?
C31 C24 C25 C26 109.0(4) . . . . ?
C6 C24 C25 C30 163.6(3) . . . . ?
C31 C24 C25 C30 -70.2(4) . . . . ?
C30 C25 C26 C27 2.1(6) . . . . ?
C24 C25 C26 C27 -177.1(4) . . . . ?
C25 C26 C27 C28 -1.0(7) . . . . ?
C26 C27 C28 C29 -0.6(7) . . . . ?
C27 C28 C29 C30 0.9(7) . . . . ?
C28 C29 C30 C25 0.4(7) . . . . ?
C26 C25 C30 C29 -1.9(6) . . . . ?
C24 C25 C30 C29 177.4(4) . . . . ?
C25 C24 C31 C32 -37.9(4) . . . . ?
C6 C24 C31 C32 89.6(3) . . . . ?
C25 C24 C31 C36 141.8(3) . . . . ?
C6 C24 C31 C36 -90.7(3) . . . . ?
C36 C31 C32 C33 2.2(5) . . . . ?
C24 C31 C32 C33 -178.2(3) . . . . ?
C31 C32 C33 C34 -2.0(5) . . . . ?
C32 C33 C34 C35 0.8(5) . . . . ?
C33 C34 C35 C36 0.1(5) . . . . ?
C34 C35 C36 C31 0.1(5) . . . . ?
C32 C31 C36 C35 -1.2(5) . . . . ?
C24 C31 C36 C35 179.1(3) . . . . ?

_refine_diff_density_max         0.307
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_is_ms432
_database_code_depnum_ccdc_archive 'CCDC 1894113'
loop_
_audit_author_name
_audit_author_address
'Alexander Villinger'
;University Rostock
Germany
;
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2019-02-27 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '0.885(C33 H27 Cl2 Sb), 0.115(C33 H27 I2 Sb)'
_chemical_formula_sum            'C33 H27 Cl1.77 I0.23 Sb'
_chemical_formula_weight         636.85

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5535(9)
_cell_length_b                   12.4822(12)
_cell_length_c                   13.5312(13)
_cell_angle_alpha                104.561(4)
_cell_angle_beta                 106.008(4)
_cell_angle_gamma                109.385(4)
_cell_volume                     1354.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9982
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      26.10

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_F_000             636
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.471
_shelx_estimated_absorpt_T_min   0.820
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6893
_exptl_absorpt_correction_T_max  0.7472
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa Apex-II CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            82814
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.361
_diffrn_reflns_theta_max         32.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9811
_reflns_number_gt                8009
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex3 2017.3'
_computing_cell_refinement       'Bruker Apex3 2017.3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2013

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine.
 
 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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.0192P)²+1.5263P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_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         9811
_refine_ls_number_parameters     340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0765
_refine_ls_wR_factor_gt          0.0700
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.57621(2) 0.69281(2) 0.49153(2) 0.01800(4) Uani 1 1 d . . . . .
Cl1 Cl 0.5723(2) 0.51295(17) 0.37219(14) 0.0294(2) Uani 0.9666(11) 1 d . . P A
1
Cl2 Cl 0.74195(19) 0.83464(16) 0.43637(16) 0.0295(3) Uani 0.8076(13) 1 d . . P
A 1
I1 I 0.594(2) 0.5051(16) 0.3656(13) 0.0294(2) Uani 0.0334(11) 1 d . . P A 2
I2 I 0.7826(2) 0.87123(16) 0.44748(18) 0.0253(4) Uani 0.1924(13) 1 d . . P A 2
C1 C 0.3438(2) 0.67681(18) 0.38957(16) 0.0135(4) Uani 1 1 d . . . . .
C2 C 0.2504(2) 0.69993(18) 0.45050(16) 0.0137(4) Uani 1 1 d . . . . .
C3 C 0.0999(2) 0.69347(19) 0.39580(17) 0.0154(4) Uani 1 1 d . . . . .
H3 H 0.0375 0.7081 0.4370 0.018 Uiso 1 1 calc R U . . .
C4 C 0.0381(2) 0.6659(2) 0.28144(17) 0.0160(4) Uani 1 1 d . . . . .
C5 C 0.1307(2) 0.64455(19) 0.22324(16) 0.0149(4) Uani 1 1 d . . . . .
H5 H 0.0900 0.6266 0.1456 0.018 Uiso 1 1 calc R U . . .
C6 C 0.2822(2) 0.64838(18) 0.27427(16) 0.0132(4) Uani 1 1 d . . . . .
C7 C 0.3104(2) 0.72797(19) 0.57643(16) 0.0150(4) Uani 1 1 d . . . . .
H7 H 0.3258 0.6552 0.5860 0.018 Uiso 1 1 calc R U . . .
C8 C 0.4747(2) 0.83814(19) 0.64332(16) 0.0156(4) Uani 1 1 d . . . . .
C9 C 0.5274(3) 0.9337(2) 0.60836(17) 0.0189(4) Uani 1 1 d . . . . .
H9 H 0.4596 0.9321 0.5412 0.023 Uiso 1 1 calc R U . . .
C10 C 0.6790(3) 1.0325(2) 0.67064(19) 0.0244(5) Uani 1 1 d . . . . .
H10 H 0.7140 1.0973 0.6456 0.029 Uiso 1 1 calc R U . . .
C11 C 0.7778(3) 1.0360(2) 0.7683(2) 0.0282(5) Uani 1 1 d . . . . .
H11 H 0.8819 1.1024 0.8101 0.034 Uiso 1 1 calc R U . . .
C12 C 0.7246(3) 0.9422(2) 0.80541(19) 0.0275(5) Uani 1 1 d . . . . .
H12 H 0.7919 0.9453 0.8735 0.033 Uiso 1 1 calc R U . . .
C13 C 0.5745(3) 0.8442(2) 0.74419(18) 0.0217(4) Uani 1 1 d . . . . .
H13 H 0.5389 0.7808 0.7707 0.026 Uiso 1 1 calc R U . . .
C14 C 0.1872(3) 0.7395(2) 0.62407(16) 0.0172(4) Uani 1 1 d . . . . .
C15 C 0.1747(3) 0.8491(2) 0.65877(19) 0.0242(5) Uani 1 1 d . . . . .
H15 H 0.2468 0.9200 0.6547 0.029 Uiso 1 1 calc R U . . .
C16 C 0.0585(3) 0.8567(3) 0.6994(2) 0.0292(5) Uani 1 1 d . . . . .
H16 H 0.0516 0.9325 0.7231 0.035 Uiso 1 1 calc R U . . .
C17 C -0.0472(3) 0.7541(3) 0.70538(19) 0.0295(6) Uani 1 1 d . . . . .
H17 H -0.1261 0.7593 0.7339 0.035 Uiso 1 1 calc R U . . .
C18 C -0.0379(3) 0.6439(3) 0.66977(19) 0.0280(5) Uani 1 1 d . . . . .
H18 H -0.1120 0.5726 0.6722 0.034 Uiso 1 1 calc R U . . .
C19 C 0.0800(3) 0.6372(2) 0.63043(18) 0.0220(4) Uani 1 1 d . . . . .
H19 H 0.0873 0.5614 0.6076 0.026 Uiso 1 1 calc R U . . .
C20 C -0.1245(3) 0.6610(3) 0.22548(19) 0.0278(5) Uani 1 1 d . . . . .
H20A H -0.1476 0.6441 0.1465 0.042 Uiso 1 1 calc R U . . .
H20B H -0.1247 0.7399 0.2602 0.042 Uiso 1 1 calc R U . . .
H20C H -0.2074 0.5958 0.2332 0.042 Uiso 1 1 calc R U . . .
C21 C 0.3697(2) 0.61926(19) 0.19955(16) 0.0139(4) Uani 1 1 d . . . . .
H21 H 0.4849 0.6485 0.2495 0.017 Uiso 1 1 calc R U . . .
C22 C 0.3063(2) 0.48222(19) 0.13353(16) 0.0147(4) Uani 1 1 d . . . . .
C23 C 0.1529(3) 0.3958(2) 0.10951(17) 0.0181(4) Uani 1 1 d . . . . .
H23 H 0.0820 0.4213 0.1356 0.022 Uiso 1 1 calc R U . . .
C24 C 0.1015(3) 0.2724(2) 0.04775(19) 0.0221(4) Uani 1 1 d . . . . .
H24 H -0.0038 0.2144 0.0322 0.027 Uiso 1 1 calc R U . . .
C25 C 0.2028(3) 0.2340(2) 0.00912(18) 0.0223(4) Uani 1 1 d . . . . .
H25 H 0.1683 0.1496 -0.0324 0.027 Uiso 1 1 calc R U . . .
C26 C 0.3560(3) 0.3198(2) 0.03153(18) 0.0225(5) Uani 1 1 d . . . . .
H26 H 0.4263 0.2942 0.0047 0.027 Uiso 1 1 calc R U . . .
C27 C 0.4062(3) 0.4421(2) 0.09266(18) 0.0192(4) Uani 1 1 d . . . . .
H27 H 0.5109 0.5000 0.1071 0.023 Uiso 1 1 calc R U . . .
C28 C 0.3699(2) 0.6918(2) 0.12356(17) 0.0157(4) Uani 1 1 d . . . . .
C29 C 0.2667(3) 0.6387(2) 0.01216(19) 0.0231(5) Uani 1 1 d . . . . .
H29 H 0.1935 0.5542 -0.0193 0.028 Uiso 1 1 calc R U . . .
C30 C 0.2697(3) 0.7081(3) -0.0538(2) 0.0307(6) Uani 1 1 d . . . . .
H30 H 0.1986 0.6708 -0.1299 0.037 Uiso 1 1 calc R U . . .
C31 C 0.3747(3) 0.8304(3) -0.0095(2) 0.0315(6) Uani 1 1 d . . . . .
H31 H 0.3759 0.8776 -0.0548 0.038 Uiso 1 1 calc R U . . .
C32 C 0.4783(4) 0.8843(2) 0.1008(2) 0.0332(6) Uani 1 1 d . . . . .
H32 H 0.5514 0.9688 0.1318 0.040 Uiso 1 1 calc R U . . .
C33 C 0.4759(3) 0.8154(2) 0.1665(2) 0.0252(5) Uani 1 1 d . . . . .
H33 H 0.5480 0.8533 0.2424 0.030 Uiso 1 1 calc R U . . .


#==============================================================================

# MOLECULAR STRUCTURE

_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
Sb1 C1 2.180(2) . ?
Sb1 Cl2 2.3777(17) . ?
Sb1 Cl1 2.3955(14) . ?
Sb1 I1 2.617(13) . ?
Sb1 I2 2.7574(18) . ?
C1 C6 1.408(3) . ?
C1 C2 1.420(3) . ?
C2 C3 1.388(3) . ?
C2 C7 1.544(3) . ?
C3 C4 1.398(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C4 C20 1.502(3) . ?
C5 C6 1.400(3) . ?
C5 H5 0.9500 . ?
C6 C21 1.529(3) . ?
C7 C14 1.519(3) . ?
C7 C8 1.527(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.385(3) . ?
C8 C13 1.400(3) . ?
C9 C10 1.395(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C14 C19 1.387(3) . ?
C15 C16 1.388(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.529(3) . ?
C21 C28 1.531(3) . ?
C21 H21 1.0000 . ?
C22 C23 1.389(3) . ?
C22 C27 1.391(3) . ?
C23 C24 1.392(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.379(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.390(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.381(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.388(3) . ?
C28 C33 1.390(3) . ?
C29 C30 1.391(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.373(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.379(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.382(3) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Sb1 Cl2 97.85(7) . . ?
C1 Sb1 Cl1 98.39(7) . . ?
Cl2 Sb1 Cl1 96.36(7) . . ?
C1 Sb1 I1 101.7(4) . . ?
C1 Sb1 I2 100.55(7) . . ?
I1 Sb1 I2 97.2(4) . . ?
C6 C1 C2 119.18(18) . . ?
C6 C1 Sb1 127.05(14) . . ?
C2 C1 Sb1 113.76(14) . . ?
C3 C2 C1 119.76(18) . . ?
C3 C2 C7 119.02(17) . . ?
C1 C2 C7 121.19(17) . . ?
C2 C3 C4 121.46(18) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 118.22(18) . . ?
C5 C4 C20 121.91(19) . . ?
C3 C4 C20 119.87(18) . . ?
C4 C5 C6 122.51(18) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C5 C6 C1 118.86(18) . . ?
C5 C6 C21 117.12(17) . . ?
C1 C6 C21 124.01(17) . . ?
C14 C7 C8 111.35(17) . . ?
C14 C7 C2 112.99(16) . . ?
C8 C7 C2 113.25(16) . . ?
C14 C7 H7 106.2 . . ?
C8 C7 H7 106.2 . . ?
C2 C7 H7 106.2 . . ?
C9 C8 C13 118.7(2) . . ?
C9 C8 C7 122.08(18) . . ?
C13 C8 C7 119.23(19) . . ?
C8 C9 C10 120.7(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.7(2) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C8 120.3(2) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
C15 C14 C19 118.4(2) . . ?
C15 C14 C7 122.0(2) . . ?
C19 C14 C7 119.6(2) . . ?
C14 C15 C16 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 120.0(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 119.8(2) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 120.0(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C14 C19 C18 120.9(2) . . ?
C14 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C4 C20 H20A 109.5 . . ?
C4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C6 113.75(16) . . ?
C22 C21 C28 111.51(16) . . ?
C6 C21 C28 110.90(16) . . ?
C22 C21 H21 106.7 . . ?
C6 C21 H21 106.7 . . ?
C28 C21 H21 106.7 . . ?
C23 C22 C27 118.1(2) . . ?
C23 C22 C21 123.64(18) . . ?
C27 C22 C21 118.23(18) . . ?
C22 C23 C24 120.9(2) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C25 C24 C23 120.2(2) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 119.4(2) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C27 C26 C25 120.1(2) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C22 121.2(2) . . ?
C26 C27 H27 119.4 . . ?
C22 C27 H27 119.4 . . ?
C29 C28 C33 118.1(2) . . ?
C29 C28 C21 122.3(2) . . ?
C33 C28 C21 119.58(19) . . ?
C28 C29 C30 120.5(2) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C31 C30 C29 120.5(2) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C30 C31 C32 119.7(2) . . ?
C30 C31 H31 120.2 . . ?
C32 C31 H31 120.2 . . ?
C31 C32 C33 120.0(3) . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C32 C33 C28 121.3(2) . . ?
C32 C33 H33 119.4 . . ?
C28 C33 H33 119.4 . . ?

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
C6 C1 C2 C3 0.4(3) . . . . ?
Sb1 C1 C2 C3 179.66(15) . . . . ?
C6 C1 C2 C7 178.30(18) . . . . ?
Sb1 C1 C2 C7 -2.4(2) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C7 C2 C3 C4 -178.68(19) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C2 C3 C4 C20 -179.4(2) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C20 C4 C5 C6 -179.8(2) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C4 C5 C6 C21 178.24(19) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
Sb1 C1 C6 C5 -178.74(15) . . . . ?
C2 C1 C6 C21 -178.72(18) . . . . ?
Sb1 C1 C6 C21 2.1(3) . . . . ?
C3 C2 C7 C14 2.7(3) . . . . ?
C1 C2 C7 C14 -175.24(18) . . . . ?
C3 C2 C7 C8 -125.1(2) . . . . ?
C1 C2 C7 C8 57.0(3) . . . . ?
C14 C7 C8 C9 -100.3(2) . . . . ?
C2 C7 C8 C9 28.3(3) . . . . ?
C14 C7 C8 C13 78.6(2) . . . . ?
C2 C7 C8 C13 -152.79(19) . . . . ?
C13 C8 C9 C10 1.9(3) . . . . ?
C7 C8 C9 C10 -179.2(2) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 -1.2(4) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C11 C12 C13 C8 0.5(4) . . . . ?
C9 C8 C13 C12 -2.0(3) . . . . ?
C7 C8 C13 C12 179.1(2) . . . . ?
C8 C7 C14 C15 43.0(3) . . . . ?
C2 C7 C14 C15 -85.7(2) . . . . ?
C8 C7 C14 C19 -138.9(2) . . . . ?
C2 C7 C14 C19 92.3(2) . . . . ?
C19 C14 C15 C16 0.3(3) . . . . ?
C7 C14 C15 C16 178.3(2) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
C16 C17 C18 C19 1.5(4) . . . . ?
C15 C14 C19 C18 0.5(3) . . . . ?
C7 C14 C19 C18 -177.59(19) . . . . ?
C17 C18 C19 C14 -1.4(3) . . . . ?
C5 C6 C21 C22 -78.2(2) . . . . ?
C1 C6 C21 C22 101.0(2) . . . . ?
C5 C6 C21 C28 48.5(2) . . . . ?
C1 C6 C21 C28 -132.4(2) . . . . ?
C6 C21 C22 C23 22.5(3) . . . . ?
C28 C21 C22 C23 -103.8(2) . . . . ?
C6 C21 C22 C27 -159.24(18) . . . . ?
C28 C21 C22 C27 74.4(2) . . . . ?
C27 C22 C23 C24 1.0(3) . . . . ?
C21 C22 C23 C24 179.2(2) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C26 -0.6(3) . . . . ?
C24 C25 C26 C27 0.5(3) . . . . ?
C25 C26 C27 C22 0.4(3) . . . . ?
C23 C22 C27 C26 -1.1(3) . . . . ?
C21 C22 C27 C26 -179.41(19) . . . . ?
C22 C21 C28 C29 25.2(3) . . . . ?
C6 C21 C28 C29 -102.7(2) . . . . ?
C22 C21 C28 C33 -155.12(19) . . . . ?
C6 C21 C28 C33 77.0(2) . . . . ?
C33 C28 C29 C30 -0.3(3) . . . . ?
C21 C28 C29 C30 179.3(2) . . . . ?
C28 C29 C30 C31 -0.1(4) . . . . ?
C29 C30 C31 C32 0.3(4) . . . . ?
C30 C31 C32 C33 -0.2(4) . . . . ?
C31 C32 C33 C28 -0.2(4) . . . . ?
C29 C28 C33 C32 0.5(3) . . . . ?
C21 C28 C33 C32 -179.2(2) . . . . ?

_refine_diff_density_max         1.537
_refine_diff_density_min         -0.861
_refine_diff_density_rms         0.113

#==============================================================================

# SHELX FILES

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_jb_ms404
_database_code_depnum_ccdc_archive 'CCDC 1894109'
loop_
_audit_author_name
_audit_author_address
'Alexander Villinger'
;University Rostock
Germany
;
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2019-02-27 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H27 Br'
_chemical_formula_sum            'C33 H27 Br'
_chemical_formula_weight         503.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.5947(12)
_cell_length_b                   11.5473(14)
_cell_length_c                   22.342(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.331(4)
_cell_angle_gamma                90
_cell_volume                     2468.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9155
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      30.71

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.685
_shelx_estimated_absorpt_T_min   0.751
_shelx_estimated_absorpt_T_max   0.877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6945
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Bruker D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            76496
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.379
_diffrn_reflns_theta_max         30.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7533
_reflns_number_gt                5740
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2013

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine.
 
 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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.0339P)²+2.6632P] 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         7533
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.0936
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.52660(2) 0.78493(2) 0.70225(2) 0.02109(6) Uani 1 1 d . . . . .
C1 C 0.6113(2) 0.64788(16) 0.67424(8) 0.0137(4) Uani 1 1 d . . . . .
C2 C 0.7528(2) 0.62778(16) 0.69118(8) 0.0135(4) Uani 1 1 d . . . . .
C3 C 0.8111(2) 0.52547(17) 0.67131(8) 0.0150(4) Uani 1 1 d . . . . .
H3 H 0.9066 0.5092 0.6826 0.018 Uiso 1 1 calc R U . . .
C4 C 0.7337(2) 0.44630(16) 0.63536(8) 0.0142(4) Uani 1 1 d . . . . .
C5 C 0.5945(2) 0.47200(16) 0.61794(8) 0.0140(4) Uani 1 1 d . . . . .
H5 H 0.5417 0.4192 0.5927 0.017 Uiso 1 1 calc R U . . .
C6 C 0.53053(19) 0.57302(16) 0.63652(8) 0.0132(3) Uani 1 1 d . . . . .
C7 C 0.8412(2) 0.71779(17) 0.72654(8) 0.0147(3) Uani 1 1 d . . . . .
H7 H 0.7817 0.7492 0.7576 0.018 Uiso 1 1 calc R U . . .
C8 C 0.8752(2) 0.82007(17) 0.68670(8) 0.0151(4) Uani 1 1 d . . . . .
C9 C 0.8683(3) 0.81267(18) 0.62430(9) 0.0238(5) Uani 1 1 d . . . . .
H9 H 0.8454 0.7409 0.6052 0.029 Uiso 1 1 calc R U . . .
C10 C 0.8945(3) 0.90905(19) 0.58955(10) 0.0255(5) Uani 1 1 d . . . . .
H10 H 0.8896 0.9024 0.5471 0.031 Uiso 1 1 calc R U . . .
C11 C 0.9277(2) 1.01449(18) 0.61628(10) 0.0206(4) Uani 1 1 d . . . . .
H11 H 0.9451 1.0803 0.5924 0.025 Uiso 1 1 calc R U . . .
C12 C 0.9352(2) 1.02283(18) 0.67850(9) 0.0200(4) Uani 1 1 d . . . . .
H12 H 0.9577 1.0949 0.6974 0.024 Uiso 1 1 calc R U . . .
C13 C 0.9102(2) 0.92643(17) 0.71320(9) 0.0176(4) Uani 1 1 d . . . . .
H13 H 0.9170 0.9331 0.7557 0.021 Uiso 1 1 calc R U . . .
C14 C 0.9690(2) 0.66393(17) 0.76042(8) 0.0155(4) Uani 1 1 d . . . . .
C15 C 1.1003(2) 0.6639(2) 0.73839(9) 0.0245(5) Uani 1 1 d . . . . .
H15 H 1.1148 0.7045 0.7024 0.029 Uiso 1 1 calc R U . . .
C16 C 1.2111(2) 0.6048(2) 0.76867(10) 0.0292(5) Uani 1 1 d . . . . .
H16 H 1.3002 0.6043 0.7528 0.035 Uiso 1 1 calc R U . . .
C17 C 1.1922(2) 0.54689(19) 0.82182(9) 0.0224(4) Uani 1 1 d . . . . .
H17 H 1.2675 0.5060 0.8422 0.027 Uiso 1 1 calc R U . . .
C18 C 1.0628(2) 0.54922(17) 0.84486(9) 0.0187(4) Uani 1 1 d . . . . .
H18 H 1.0496 0.5114 0.8818 0.022 Uiso 1 1 calc R U . . .
C19 C 0.9518(2) 0.60656(18) 0.81444(9) 0.0176(4) Uani 1 1 d . . . . .
H19 H 0.8630 0.6068 0.8305 0.021 Uiso 1 1 calc R U . . .
C20 C 0.7999(2) 0.33565(18) 0.61586(9) 0.0194(4) Uani 1 1 d . . . . .
H20A H 0.7270 0.2832 0.5987 0.029 Uiso 1 1 calc R U . . .
H20B H 0.8501 0.2987 0.6506 0.029 Uiso 1 1 calc R U . . .
H20C H 0.8655 0.3530 0.5855 0.029 Uiso 1 1 calc R U . . .
C21 C 0.38065(19) 0.60443(17) 0.61425(8) 0.0145(4) Uani 1 1 d . . . . .
H21 H 0.3341 0.6326 0.6501 0.017 Uiso 1 1 calc R U . . .
C22 C 0.3785(2) 0.70548(17) 0.57021(8) 0.0149(4) Uani 1 1 d . . . . .
C23 C 0.2671(2) 0.78296(18) 0.56757(9) 0.0186(4) Uani 1 1 d . . . . .
H23 H 0.1938 0.7729 0.5934 0.022 Uiso 1 1 calc R U . . .
C24 C 0.2622(2) 0.87514(18) 0.52729(9) 0.0219(4) Uani 1 1 d . . . . .
H24 H 0.1858 0.9277 0.5259 0.026 Uiso 1 1 calc R U . . .
C25 C 0.3683(2) 0.89065(18) 0.48917(9) 0.0220(4) Uani 1 1 d . . . . .
H25 H 0.3649 0.9537 0.4618 0.026 Uiso 1 1 calc R U . . .
C26 C 0.4790(2) 0.81372(19) 0.49132(10) 0.0224(4) Uani 1 1 d . . . . .
H26 H 0.5517 0.8238 0.4652 0.027 Uiso 1 1 calc R U . . .
C27 C 0.4844(2) 0.72148(18) 0.53162(9) 0.0189(4) Uani 1 1 d . . . . .
H27 H 0.5608 0.6691 0.5328 0.023 Uiso 1 1 calc R U . . .
C28 C 0.2949(2) 0.50135(17) 0.58959(9) 0.0169(4) Uani 1 1 d . . . . .
C29 C 0.2661(2) 0.4101(2) 0.62790(11) 0.0265(5) Uani 1 1 d . . . . .
H29 H 0.3015 0.4123 0.6688 0.032 Uiso 1 1 calc R U . . .
C30 C 0.1857(3) 0.3159(2) 0.60674(13) 0.0343(6) Uani 1 1 d . . . . .
H30 H 0.1675 0.2540 0.6331 0.041 Uiso 1 1 calc R U . . .
C31 C 0.1324(3) 0.3124(2) 0.54732(13) 0.0340(6) Uani 1 1 d . . . . .
H31 H 0.0779 0.2482 0.5329 0.041 Uiso 1 1 calc R U . . .
C32 C 0.1587(3) 0.4023(2) 0.50938(11) 0.0317(5) Uani 1 1 d . . . . .
H32 H 0.1213 0.4006 0.4688 0.038 Uiso 1 1 calc R U . . .
C33 C 0.2400(2) 0.4959(2) 0.53029(10) 0.0227(4) Uani 1 1 d . . . . .
H33 H 0.2583 0.5570 0.5035 0.027 Uiso 1 1 calc R U . . .


#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.9061(19) . ?
C1 C6 1.400(3) . ?
C1 C2 1.401(3) . ?
C2 C3 1.394(3) . ?
C2 C7 1.524(3) . ?
C3 C4 1.394(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(3) . ?
C4 C20 1.506(3) . ?
C5 C6 1.396(3) . ?
C5 H5 0.9500 . ?
C6 C21 1.529(3) . ?
C7 C14 1.524(3) . ?
C7 C8 1.529(3) . ?
C7 H7 1.0000 . ?
C8 C13 1.393(3) . ?
C8 C9 1.393(3) . ?
C9 C10 1.391(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.387(3) . ?
C14 C19 1.397(3) . ?
C15 C16 1.395(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.526(3) . ?
C21 C28 1.526(3) . ?
C21 H21 1.0000 . ?
C22 C23 1.392(3) . ?
C22 C27 1.393(3) . ?
C23 C24 1.393(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.387(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.393(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C33 1.390(3) . ?
C28 C29 1.398(3) . ?
C29 C30 1.395(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.387(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.375(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.393(3) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.78(17) . . ?
C6 C1 Br1 118.69(14) . . ?
C2 C1 Br1 118.51(14) . . ?
C3 C2 C1 117.28(17) . . ?
C3 C2 C7 121.47(17) . . ?
C1 C2 C7 121.14(17) . . ?
C4 C3 C2 122.02(17) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 118.60(17) . . ?
C3 C4 C20 120.37(17) . . ?
C5 C4 C20 121.03(17) . . ?
C4 C5 C6 121.88(17) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 117.35(17) . . ?
C5 C6 C21 121.67(17) . . ?
C1 C6 C21 120.90(17) . . ?
C2 C7 C14 111.99(16) . . ?
C2 C7 C8 111.10(15) . . ?
C14 C7 C8 113.93(16) . . ?
C2 C7 H7 106.4 . . ?
C14 C7 H7 106.4 . . ?
C8 C7 H7 106.4 . . ?
C13 C8 C9 118.09(18) . . ?
C13 C8 C7 119.27(17) . . ?
C9 C8 C7 122.61(17) . . ?
C10 C9 C8 120.83(19) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.06(19) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C13 C12 C11 120.33(19) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C8 121.07(18) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
C15 C14 C19 118.42(18) . . ?
C15 C14 C7 122.82(17) . . ?
C19 C14 C7 118.67(18) . . ?
C14 C15 C16 120.5(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 119.3(2) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 120.36(19) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 120.89(19) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C4 C20 H20A 109.5 . . ?
C4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C28 112.53(15) . . ?
C22 C21 C6 110.96(15) . . ?
C28 C21 C6 113.61(16) . . ?
C22 C21 H21 106.4 . . ?
C28 C21 H21 106.4 . . ?
C6 C21 H21 106.4 . . ?
C23 C22 C27 118.82(18) . . ?
C23 C22 C21 119.45(17) . . ?
C27 C22 C21 121.71(17) . . ?
C22 C23 C24 120.47(19) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C25 C24 C23 120.32(19) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C24 119.55(19) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C27 120.3(2) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C22 120.54(19) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?
C33 C28 C29 118.1(2) . . ?
C33 C28 C21 122.34(18) . . ?
C29 C28 C21 119.53(18) . . ?
C30 C29 C28 120.7(2) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C31 C30 C29 120.1(2) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C32 C31 C30 119.8(2) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C31 C32 C33 120.2(2) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C28 C33 C32 121.2(2) . . ?
C28 C33 H33 119.4 . . ?
C32 C33 H33 119.4 . . ?

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
C6 C1 C2 C3 -3.1(3) . . . . ?
Br1 C1 C2 C3 178.41(14) . . . . ?
C6 C1 C2 C7 173.12(17) . . . . ?
Br1 C1 C2 C7 -5.3(2) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C7 C2 C3 C4 -175.37(17) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C2 C3 C4 C20 -178.78(18) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C20 C4 C5 C6 178.72(18) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C4 C5 C6 C21 176.20(17) . . . . ?
C2 C1 C6 C5 3.1(3) . . . . ?
Br1 C1 C6 C5 -178.48(13) . . . . ?
C2 C1 C6 C21 -173.90(17) . . . . ?
Br1 C1 C6 C21 4.5(2) . . . . ?
C3 C2 C7 C14 -26.1(2) . . . . ?
C1 C2 C7 C14 157.81(17) . . . . ?
C3 C2 C7 C8 102.6(2) . . . . ?
C1 C2 C7 C8 -73.5(2) . . . . ?
C2 C7 C8 C13 157.56(18) . . . . ?
C14 C7 C8 C13 -74.8(2) . . . . ?
C2 C7 C8 C9 -20.3(3) . . . . ?
C14 C7 C8 C9 107.3(2) . . . . ?
C13 C8 C9 C10 -0.5(3) . . . . ?
C7 C8 C9 C10 177.4(2) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C8 -0.9(3) . . . . ?
C9 C8 C13 C12 1.0(3) . . . . ?
C7 C8 C13 C12 -176.91(18) . . . . ?
C2 C7 C14 C15 97.2(2) . . . . ?
C8 C7 C14 C15 -29.9(3) . . . . ?
C2 C7 C14 C19 -79.2(2) . . . . ?
C8 C7 C14 C19 153.65(18) . . . . ?
C19 C14 C15 C16 2.0(3) . . . . ?
C7 C14 C15 C16 -174.5(2) . . . . ?
C14 C15 C16 C17 -1.1(4) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
C16 C17 C18 C19 1.6(3) . . . . ?
C17 C18 C19 C14 -0.7(3) . . . . ?
C15 C14 C19 C18 -1.1(3) . . . . ?
C7 C14 C19 C18 175.50(18) . . . . ?
C5 C6 C21 C22 -107.9(2) . . . . ?
C1 C6 C21 C22 68.9(2) . . . . ?
C5 C6 C21 C28 20.1(3) . . . . ?
C1 C6 C21 C28 -163.10(17) . . . . ?
C28 C21 C22 C23 83.3(2) . . . . ?
C6 C21 C22 C23 -148.15(18) . . . . ?
C28 C21 C22 C27 -95.6(2) . . . . ?
C6 C21 C22 C27 32.9(2) . . . . ?
C27 C22 C23 C24 -0.4(3) . . . . ?
C21 C22 C23 C24 -179.33(18) . . . . ?
C22 C23 C24 C25 0.2(3) . . . . ?
C23 C24 C25 C26 0.1(3) . . . . ?
C24 C25 C26 C27 -0.2(3) . . . . ?
C25 C26 C27 C22 0.0(3) . . . . ?
C23 C22 C27 C26 0.3(3) . . . . ?
C21 C22 C27 C26 179.22(18) . . . . ?
C22 C21 C28 C33 9.1(3) . . . . ?
C6 C21 C28 C33 -118.1(2) . . . . ?
C22 C21 C28 C29 -168.93(18) . . . . ?
C6 C21 C28 C29 63.9(2) . . . . ?
C33 C28 C29 C30 0.7(3) . . . . ?
C21 C28 C29 C30 178.8(2) . . . . ?
C28 C29 C30 C31 -0.6(4) . . . . ?
C29 C30 C31 C32 -0.2(4) . . . . ?
C30 C31 C32 C33 0.8(4) . . . . ?
C29 C28 C33 C32 -0.1(3) . . . . ?
C21 C28 C33 C32 -178.1(2) . . . . ?
C31 C32 C33 C28 -0.7(4) . . . . ?

_refine_diff_density_max         0.451
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.080

#==============================================================================

# SHELX FILES

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_MS516_2
_database_code_depnum_ccdc_archive 'CCDC 1894117'
loop_
_audit_author_name
_audit_author_address
'Alexander Villinger'
;University Rostock
Germany
;
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2019-02-27 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H27 Cl1.52 I0.48 P'
_chemical_formula_sum            'C33 H27 Cl1.52 I0.48 P'
_chemical_formula_weight         569.31

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'
P P 0.2955 0.4335 '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'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.4208(5)
_cell_length_b                   14.0280(7)
_cell_length_c                   20.0898(10)
_cell_angle_alpha                71.795(5)
_cell_angle_beta                 81.683(4)
_cell_angle_gamma                77.745(4)
_cell_volume                     2716.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.01(10)
_cell_measurement_reflns_used    7075
_cell_measurement_theta_min      4.3110
_cell_measurement_theta_max      76.1110

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             1165
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    6.698
_shelx_estimated_absorpt_T_min   0.379
_shelx_estimated_absorpt_T_max   0.824
_exptl_absorpt_correction_T_min  0.60897
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan

_oxdiff_exptl_absorpt_empirical_full_min 0.823
_oxdiff_exptl_absorpt_empirical_full_max 1.579
_oxdiff_exptl_absorpt_empirical_details 
;
CrysAlisPro 1.171.38.43b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.5035
_diffrn_reflns_number            28346
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.492
_diffrn_reflns_theta_max         76.253
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             11218
_reflns_number_gt                8677
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    .
_computing_publication_material  .

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)²+0.9461P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11218
_refine_ls_number_parameters     690
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1280
_refine_ls_wR_factor_gt          0.1165
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.4860(6) 0.2174(5) 0.7874(3) 0.0405(2) Uani 0.499(2) 1 d . . P . .
C1 C 1.2884(3) 0.0935(2) 0.88976(15) 0.0251(6) Uani 1 1 d . . . . .
P1 P 1.46872(8) 0.08129(6) 0.87526(5) 0.03508(19) Uani 1 1 d . . . . .
I1 I 1.50335(12) 0.22031(11) 0.77393(6) 0.0405(2) Uani 0.501(2) 1 d . . P . .
Cl2 Cl 1.52324(8) 0.12537(7) 0.95472(5) 0.0416(2) Uani 1 1 d . . . . .
C2 C 1.2413(3) 0.0111(2) 0.88033(15) 0.0241(5) Uani 1 1 d . . . . .
C6 C 1.1963(3) 0.1752(2) 0.90602(15) 0.0267(6) Uani 1 1 d . . . . .
C5 C 1.0619(3) 0.1713(2) 0.91169(16) 0.0298(6) Uani 1 1 d . . . . .
H5 H 1.0000 0.2265 0.9216 0.036 Uiso 1 1 calc R U . . .
C4 C 1.0153(3) 0.0913(2) 0.90353(17) 0.0308(6) Uani 1 1 d . . . . .
C7 C 0.8691(3) 0.0910(3) 0.9103(2) 0.0380(7) Uani 1 1 d . . . . .
H7A H 0.8204 0.1601 0.9070 0.057 Uiso 1 1 calc R U . . .
H7B H 0.8445 0.0444 0.9558 0.057 Uiso 1 1 calc R U . . .
H7C H 0.8475 0.0685 0.8724 0.057 Uiso 1 1 calc R U . . .
C8 C 1.2357(3) 0.2664(2) 0.91886(15) 0.0267(6) Uani 1 1 d . . . . .
H8 H 1.3270 0.2721 0.8965 0.032 Uiso 0.66(5) 1 calc R U P A 1
H8B H 1.3241 0.2728 0.8927 0.032 Uiso 0.34(5) 1 calc R U P A 2
C15 C 1.2374(12) 0.2476(11) 0.9990(4) 0.025(2) Uani 0.66(5) 1 d G . P A 1
C16 C 1.1591(12) 0.1876(11) 1.0499(4) 0.0329(18) Uani 0.66(5) 1 d G . P A 1
H16 H 1.1050 0.1512 1.0365 0.040 Uiso 0.66(5) 1 calc R U P A 1
C17 C 1.1601(12) 0.1807(11) 1.1203(4) 0.042(2) Uani 0.66(5) 1 d G . P A 1
H17 H 1.1066 0.1397 1.1551 0.050 Uiso 0.66(5) 1 calc R U P A 1
C18 C 1.2392(14) 0.2340(12) 1.1399(5) 0.042(3) Uani 0.66(5) 1 d G . P A 1
H18 H 1.2399 0.2293 1.1881 0.050 Uiso 0.66(5) 1 calc R U P A 1
C19 C 1.3175(13) 0.2940(11) 1.0891(7) 0.049(3) Uani 0.66(5) 1 d G . P A 1
H19 H 1.3716 0.3304 1.1024 0.059 Uiso 0.66(5) 1 calc R U P A 1
C20 C 1.3166(12) 0.3009(10) 1.0186(6) 0.033(2) Uani 0.66(5) 1 d G . P A 1
H20 H 1.3700 0.3419 0.9838 0.040 Uiso 0.66(5) 1 calc R U P A 1
C15B C 1.250(2) 0.2656(18) 0.9934(7) 0.028(4) Uani 0.34(5) 1 d G . P A 2
C16B C 1.185(3) 0.2037(15) 1.0504(9) 0.033(4) Uani 0.34(5) 1 d G . P A 2
H16B H 1.1311 0.1619 1.0429 0.040 Uiso 0.34(5) 1 calc R U P A 2
C17B C 1.199(3) 0.2030(15) 1.1184(7) 0.040(5) Uani 0.34(5) 1 d G . P A 2
H17B H 1.1539 0.1607 1.1573 0.048 Uiso 0.34(5) 1 calc R U P A 2
C18B C 1.277(3) 0.264(2) 1.1293(10) 0.046(6) Uani 0.34(5) 1 d G . P A 2
H18B H 1.2867 0.2638 1.1758 0.055 Uiso 0.34(5) 1 calc R U P A 2
C19B C 1.3427(19) 0.326(3) 1.0724(15) 0.054(6) Uani 0.34(5) 1 d G . P A 2
H19B H 1.3966 0.3680 1.0799 0.064 Uiso 0.34(5) 1 calc R U P A 2
C20B C 1.329(2) 0.327(2) 1.0044(12) 0.042(4) Uani 0.34(5) 1 d G . P A 2
H20B H 1.3738 0.3691 0.9654 0.051 Uiso 0.34(5) 1 calc R U P A 2
C9 C 1.1434(3) 0.3654(2) 0.88518(16) 0.0274(6) Uani 1 1 d . . . . .
C10 C 1.1628(4) 0.4114(3) 0.81315(19) 0.0411(8) Uani 1 1 d . . . . .
H10 H 1.2346 0.3829 0.7863 0.049 Uiso 1 1 calc R U . . .
C11 C 1.0770(4) 0.4996(3) 0.7803(2) 0.0485(9) Uani 1 1 d . . . . .
H11 H 1.0909 0.5307 0.7312 0.058 Uiso 1 1 calc R U . . .
C12 C 0.9724(4) 0.5416(3) 0.8186(2) 0.0425(8) Uani 1 1 d . . . . .
H12 H 0.9137 0.6010 0.7959 0.051 Uiso 1 1 calc R U . . .
C13 C 0.9533(4) 0.4971(3) 0.8901(2) 0.0413(8) Uani 1 1 d . . . . .
H13 H 0.8815 0.5259 0.9169 0.050 Uiso 1 1 calc R U . . .
C14 C 1.0392(3) 0.4102(2) 0.92297(19) 0.0359(7) Uani 1 1 d . . . . .
H14 H 1.0263 0.3809 0.9724 0.043 Uiso 1 1 calc R U . . .
Cl3 Cl 1.0053(6) 0.2874(4) 0.7147(4) 0.0440(2) Uani 0.541(2) 1 d . . P . .
C3 C 1.1061(3) 0.0108(2) 0.88850(16) 0.0278(6) Uani 1 1 d . . . . .
H3 H 1.0753 -0.0456 0.8837 0.033 Uiso 1 1 calc R U . . .
I2 I 1.02039(16) 0.26902(10) 0.72334(9) 0.0440(2) Uani 0.459(2) 1 d . . P . .
P2 P 0.98447(8) 0.34505(8) 0.60238(5) 0.0392(2) Uani 1 1 d . . . . .
Cl40 Cl 1.04547(8) 0.48362(8) 0.58205(5) 0.0460(2) Uani 1 1 d . . . . .
C40 C 0.3819(3) 0.4102(3) 0.5995(2) 0.0424(8) Uani 1 1 d . . . . .
H40A H 0.3535 0.4632 0.5567 0.064 Uiso 1 1 calc R U . . .
H40B H 0.3370 0.4300 0.6409 0.064 Uiso 1 1 calc R U . . .
H40C H 0.3596 0.3455 0.6001 0.064 Uiso 1 1 calc R U . . .
C39 C 0.7174(3) 0.4424(2) 0.63647(15) 0.0272(6) Uani 1 1 d . . . . .
C38 C 0.5805(3) 0.4510(2) 0.63522(16) 0.0295(6) Uani 1 1 d . . . . .
H38 H 0.5221 0.4945 0.6586 0.035 Uiso 1 1 calc R U . . .
C37 C 0.5282(3) 0.3980(2) 0.60096(17) 0.0303(6) Uani 1 1 d . . . . .
C36 C 0.6153(3) 0.3348(2) 0.56693(16) 0.0299(6) Uani 1 1 d . . . . .
H36 H 0.5807 0.2995 0.5423 0.036 Uiso 1 1 calc R U . . .
C35 C 0.7513(3) 0.3215(2) 0.56772(15) 0.0269(6) Uani 1 1 d . . . . .
C34 C 0.8039(3) 0.3762(2) 0.60302(15) 0.0272(6) Uani 1 1 d . . . . .
C33 C 1.2166(3) -0.1954(3) 0.82589(18) 0.0337(7) Uani 1 1 d . . . . .
H33 H 1.2036 -0.1487 0.7805 0.040 Uiso 1 1 calc R U . . .
C32 C 1.1704(4) -0.2870(3) 0.8452(2) 0.0430(8) Uani 1 1 d . . . . .
H32 H 1.1260 -0.3024 0.8128 0.052 Uiso 1 1 calc R U . . .
C31 C 1.1883(4) -0.3559(3) 0.9107(2) 0.0436(8) Uani 1 1 d . . . . .
H31 H 1.1567 -0.4185 0.9233 0.052 Uiso 1 1 calc R U . . .
C30 C 1.2522(4) -0.3333(3) 0.9575(2) 0.0424(8) Uani 1 1 d . . . . .
H30 H 1.2647 -0.3804 1.0028 0.051 Uiso 1 1 calc R U . . .
C29 C 1.2986(3) -0.2417(3) 0.93914(18) 0.0353(7) Uani 1 1 d . . . . .
H29 H 1.3421 -0.2267 0.9721 0.042 Uiso 1 1 calc R U . . .
C28 C 1.2822(3) -0.1718(2) 0.87316(16) 0.0269(6) Uani 1 1 d . . . . .
C27 C 1.2904(4) 0.0375(3) 0.72992(19) 0.0411(8) Uani 1 1 d . . . . .
H27 H 1.2037 0.0617 0.7470 0.049 Uiso 1 1 calc R U . . .
C26 C 1.3298(4) 0.0720(3) 0.6593(2) 0.0485(9) Uani 1 1 d . . . . .
H26 H 1.2697 0.1191 0.6280 0.058 Uiso 1 1 calc R U . . .
C25 C 1.4557(4) 0.0386(3) 0.63382(19) 0.0463(9) Uani 1 1 d . . . . .
H25 H 1.4827 0.0631 0.5852 0.056 Uiso 1 1 calc R U . . .
C24 C 1.5417(4) -0.0298(4) 0.6788(2) 0.0552(10) Uani 1 1 d . . . . .
H24 H 1.6288 -0.0529 0.6616 0.066 Uiso 1 1 calc R U . . .
C23 C 1.5010(3) -0.0659(3) 0.7502(2) 0.0450(9) Uani 1 1 d . . . . .
H23 H 1.5605 -0.1144 0.7812 0.054 Uiso 1 1 calc R U . . .
C22 C 1.3763(3) -0.0320(2) 0.77610(16) 0.0277(6) Uani 1 1 d . . . . .
C21 C 1.3357(3) -0.0729(2) 0.85506(15) 0.0249(6) Uani 1 1 d . . . . .
H21 H 1.4173 -0.0889 0.8801 0.030 Uiso 1 1 calc R U . . .
C43 C 0.8140(4) 0.1185(3) 0.65968(19) 0.0435(8) Uani 1 1 d . . . . .
H43 H 0.7435 0.1671 0.6718 0.052 Uiso 1 1 calc R U . . .
C42 C 0.8779(3) 0.1409(2) 0.59325(16) 0.0275(6) Uani 1 1 d . . . . .
C41 C 0.8394(3) 0.2413(2) 0.53599(15) 0.0261(6) Uani 1 1 d . . . . .
H41 H 0.9225 0.2678 0.5148 0.031 Uiso 1 1 calc R U . . .
C61 C 0.6770(3) 0.5095(2) 0.74138(16) 0.0291(6) Uani 1 1 d . . . . .
C44 C 0.8516(5) 0.0249(3) 0.7096(2) 0.0509(10) Uani 1 1 d . . . . .
H44 H 0.8077 0.0109 0.7555 0.061 Uiso 1 1 calc R U . . .
C66 C 0.6863(4) 0.4197(3) 0.79598(19) 0.0414(8) Uani 1 1 d . . . . .
H66 H 0.7458 0.3609 0.7901 0.050 Uiso 1 1 calc R U . . .
C45 C 0.9525(4) -0.0474(3) 0.6924(2) 0.0453(9) Uani 1 1 d . . . . .
H45 H 0.9782 -0.1108 0.7264 0.054 Uiso 1 1 calc R U . . .
C65 C 0.6097(5) 0.4144(3) 0.8592(2) 0.0529(10) Uani 1 1 d . . . . .
H65 H 0.6176 0.3522 0.8962 0.063 Uiso 1 1 calc R U . . .
C46 C 1.0153(4) -0.0262(3) 0.6254(2) 0.0482(9) Uani 1 1 d . . . . .
H46 H 1.0839 -0.0757 0.6129 0.058 Uiso 1 1 calc R U . . .
C64 C 0.5231(4) 0.4981(3) 0.8687(2) 0.0509(10) Uani 1 1 d . . . . .
H64 H 0.4708 0.4942 0.9120 0.061 Uiso 1 1 calc R U . . .
C47 C 0.9789(3) 0.0665(3) 0.57656(19) 0.0407(8) Uani 1 1 d . . . . .
H47 H 1.0231 0.0802 0.5307 0.049 Uiso 1 1 calc R U . . .
C63 C 0.5122(4) 0.5885(3) 0.8147(2) 0.0443(8) Uani 1 1 d . . . . .
H63 H 0.4518 0.6468 0.8208 0.053 Uiso 1 1 calc R U . . .
C48 C 0.7769(3) 0.2253(2) 0.47690(16) 0.0291(6) Uani 1 1 d . . . . .
C62 C 0.5893(3) 0.5941(3) 0.75156(18) 0.0355(7) Uani 1 1 d . . . . .
H62 H 0.5819 0.6567 0.7149 0.043 Uiso 1 1 calc R U . . .
C49 C 0.7104(3) 0.1457(3) 0.48739(18) 0.0354(7) Uani 1 1 d . . . . .
H49 H 0.7059 0.0971 0.5324 0.042 Uiso 1 1 calc R U . . .
C50 C 0.6502(4) 0.1356(3) 0.4334(2) 0.0424(8) Uani 1 1 d . . . . .
H50 H 0.6041 0.0808 0.4416 0.051 Uiso 1 1 calc R U . . .
C60 C 0.8337(4) 0.6802(3) 0.6372(2) 0.0438(8) Uani 1 1 d . . . . .
H60 H 0.8866 0.6533 0.6759 0.053 Uiso 1 1 calc R U . . .
C51 C 0.6574(4) 0.2056(3) 0.3673(2) 0.0443(9) Uani 1 1 d . . . . .
H51 H 0.6168 0.1987 0.3301 0.053 Uiso 1 1 calc R U . . .
C59 C 0.8308(4) 0.7807(3) 0.5962(2) 0.0513(10) Uani 1 1 d . . . . .
H59 H 0.8817 0.8218 0.6070 0.062 Uiso 1 1 calc R U . . .
C52 C 0.7237(4) 0.2853(3) 0.35587(19) 0.0462(9) Uani 1 1 d . . . . .
H52 H 0.7286 0.3334 0.3106 0.055 Uiso 1 1 calc R U . . .
C58 C 0.7544(4) 0.8209(3) 0.5400(2) 0.0485(9) Uani 1 1 d . . . . .
H58 H 0.7513 0.8899 0.5122 0.058 Uiso 1 1 calc R U . . .
C53 C 0.7831(4) 0.2953(3) 0.40997(18) 0.0401(8) Uani 1 1 d . . . . .
H53 H 0.8286 0.3504 0.4016 0.048 Uiso 1 1 calc R U . . .
C57 C 0.6827(4) 0.7600(3) 0.5247(2) 0.0529(10) Uani 1 1 d . . . . .
H57 H 0.6308 0.7866 0.4856 0.064 Uiso 1 1 calc R U . . .
C54 C 0.7606(3) 0.5104(2) 0.67219(15) 0.0264(6) Uani 1 1 d . . . . .
H54 H 0.8535 0.4805 0.6839 0.032 Uiso 1 1 calc R U . . .
C56 C 0.6855(4) 0.6599(3) 0.56579(19) 0.0439(8) Uani 1 1 d . . . . .
H56 H 0.6348 0.6190 0.5547 0.053 Uiso 1 1 calc R U . . .
C55 C 0.7607(3) 0.6187(2) 0.62251(16) 0.0296(6) Uani 1 1 d . . . . .


#==============================================================================

# MOLECULAR GEOMETRY

_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
Cl1 P1 2.178(6) . ?
C1 C2 1.420(4) . ?
C1 C6 1.421(4) . ?
C1 P1 1.839(3) . ?
P1 Cl2 2.0693(12) . ?
P1 I1 2.3839(14) . ?
C2 C3 1.395(4) . ?
C2 C21 1.533(4) . ?
C6 C5 1.400(4) . ?
C6 C8 1.528(4) . ?
C5 C4 1.376(4) . ?
C5 H5 0.9500 . ?
C4 C3 1.392(4) . ?
C4 C7 1.510(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C15B 1.523(14) . ?
C8 C9 1.531(4) . ?
C8 C15 1.550(8) . ?
C8 H8 1.0000 . ?
C8 H8B 1.0000 . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C16 C17 1.3900 . ?
C16 H16 0.9500 . ?
C17 C18 1.3900 . ?
C17 H17 0.9500 . ?
C18 C19 1.3900 . ?
C18 H18 0.9500 . ?
C19 C20 1.3900 . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C15B C16B 1.3900 . ?
C15B C20B 1.3900 . ?
C16B C17B 1.3900 . ?
C16B H16B 0.9500 . ?
C17B C18B 1.3900 . ?
C17B H17B 0.9500 . ?
C18B C19B 1.3900 . ?
C18B H18B 0.9500 . ?
C19B C20B 1.3900 . ?
C19B H19B 0.9500 . ?
C20B H20B 0.9500 . ?
C9 C14 1.385(5) . ?
C9 C10 1.393(5) . ?
C10 C11 1.398(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
Cl3 P2 2.172(6) . ?
C3 H3 0.9500 . ?
I2 P2 2.3785(18) . ?
P2 C34 1.838(3) . ?
P2 Cl40 2.0744(13) . ?
C40 C37 1.501(4) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C39 C34 1.409(4) . ?
C39 C38 1.410(4) . ?
C39 C54 1.527(4) . ?
C38 C37 1.387(4) . ?
C38 H38 0.9500 . ?
C37 C36 1.391(5) . ?
C36 C35 1.391(4) . ?
C36 H36 0.9500 . ?
C35 C34 1.422(4) . ?
C35 C41 1.535(4) . ?
C33 C32 1.389(5) . ?
C33 C28 1.400(4) . ?
C33 H33 0.9500 . ?
C32 C31 1.379(6) . ?
C32 H32 0.9500 . ?
C31 C30 1.374(5) . ?
C31 H31 0.9500 . ?
C30 C29 1.392(5) . ?
C30 H30 0.9500 . ?
C29 C28 1.389(5) . ?
C29 H29 0.9500 . ?
C28 C21 1.523(4) . ?
C27 C26 1.379(5) . ?
C27 C22 1.385(5) . ?
C27 H27 0.9500 . ?
C26 C25 1.377(6) . ?
C26 H26 0.9500 . ?
C25 C24 1.367(6) . ?
C25 H25 0.9500 . ?
C24 C23 1.398(6) . ?
C24 H24 0.9500 . ?
C23 C22 1.371(5) . ?
C23 H23 0.9500 . ?
C22 C21 1.538(4) . ?
C21 H21 1.0000 . ?
C43 C42 1.376(5) . ?
C43 C44 1.398(5) . ?
C43 H43 0.9500 . ?
C42 C47 1.400(5) . ?
C42 C41 1.532(4) . ?
C41 C48 1.529(4) . ?
C41 H41 1.0000 . ?
C61 C66 1.384(5) . ?
C61 C62 1.387(5) . ?
C61 C54 1.528(4) . ?
C44 C45 1.382(6) . ?
C44 H44 0.9500 . ?
C66 C65 1.389(5) . ?
C66 H66 0.9500 . ?
C45 C46 1.382(6) . ?
C45 H45 0.9500 . ?
C65 C64 1.368(6) . ?
C65 H65 0.9500 . ?
C46 C47 1.378(5) . ?
C46 H46 0.9500 . ?
C64 C63 1.383(6) . ?
C64 H64 0.9500 . ?
C47 H47 0.9500 . ?
C63 C62 1.389(5) . ?
C63 H63 0.9500 . ?
C48 C49 1.381(5) . ?
C48 C53 1.398(5) . ?
C62 H62 0.9500 . ?
C49 C50 1.387(5) . ?
C49 H49 0.9500 . ?
C50 C51 1.385(6) . ?
C50 H50 0.9500 . ?
C60 C55 1.384(5) . ?
C60 C59 1.389(5) . ?
C60 H60 0.9500 . ?
C51 C52 1.379(6) . ?
C51 H51 0.9500 . ?
C59 C58 1.379(6) . ?
C59 H59 0.9500 . ?
C52 C53 1.382(5) . ?
C52 H52 0.9500 . ?
C58 C57 1.374(6) . ?
C58 H58 0.9500 . ?
C53 H53 0.9500 . ?
C57 C56 1.385(5) . ?
C57 H57 0.9500 . ?
C54 C55 1.535(4) . ?
C54 H54 1.0000 . ?
C56 C55 1.379(5) . ?
C56 H56 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.1(3) . . ?
C2 C1 P1 113.2(2) . . ?
C6 C1 P1 127.7(2) . . ?
C1 P1 Cl2 105.10(10) . . ?
C1 P1 Cl1 100.28(19) . . ?
Cl2 P1 Cl1 99.87(18) . . ?
C1 P1 I1 104.07(10) . . ?
Cl2 P1 I1 102.42(5) . . ?
Cl1 P1 I1 5.47(17) . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 C21 119.3(2) . . ?
C1 C2 C21 120.9(2) . . ?
C5 C6 C1 118.3(3) . . ?
C5 C6 C8 118.0(3) . . ?
C1 C6 C8 123.6(3) . . ?
C4 C5 C6 123.0(3) . . ?
C4 C5 H5 118.5 . . ?
C6 C5 H5 118.5 . . ?
C5 C4 C3 118.4(3) . . ?
C5 C4 C7 120.8(3) . . ?
C3 C4 C7 120.8(3) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C15B C8 C6 120.1(8) . . ?
C15B C8 C9 107.5(10) . . ?
C6 C8 C9 110.9(2) . . ?
C6 C8 C15 109.4(6) . . ?
C9 C8 C15 111.9(5) . . ?
C6 C8 H8 108.2 . . ?
C9 C8 H8 108.2 . . ?
C15 C8 H8 108.2 . . ?
C15B C8 H8B 105.8 . . ?
C6 C8 H8B 105.8 . . ?
C9 C8 H8B 105.8 . . ?
C16 C15 C20 120.0 . . ?
C16 C15 C8 123.9(6) . . ?
C20 C15 C8 116.0(6) . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C15 120.0 . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?
C16B C15B C20B 120.0 . . ?
C16B C15B C8 120.1(10) . . ?
C20B C15B C8 119.9(10) . . ?
C17B C16B C15B 120.0 . . ?
C17B C16B H16B 120.0 . . ?
C15B C16B H16B 120.0 . . ?
C16B C17B C18B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C18B C17B H17B 120.0 . . ?
C17B C18B C19B 120.0 . . ?
C17B C18B H18B 120.0 . . ?
C19B C18B H18B 120.0 . . ?
C18B C19B C20B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C20B C19B H19B 120.0 . . ?
C19B C20B C15B 120.0 . . ?
C19B C20B H20B 120.0 . . ?
C15B C20B H20B 120.0 . . ?
C14 C9 C10 118.4(3) . . ?
C14 C9 C8 122.9(3) . . ?
C10 C9 C8 118.8(3) . . ?
C9 C10 C11 120.2(4) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 119.7(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 119.9(4) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C9 C14 C13 121.4(3) . . ?
C9 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C34 P2 Cl40 105.29(11) . . ?
C34 P2 Cl3 100.1(2) . . ?
Cl40 P2 Cl3 99.01(18) . . ?
C34 P2 I2 103.38(11) . . ?
Cl40 P2 I2 101.74(6) . . ?
Cl3 P2 I2 5.15(18) . . ?
C37 C40 H40A 109.5 . . ?
C37 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C37 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C34 C39 C38 118.9(3) . . ?
C34 C39 C54 124.8(3) . . ?
C38 C39 C54 116.2(3) . . ?
C37 C38 C39 122.1(3) . . ?
C37 C38 H38 118.9 . . ?
C39 C38 H38 118.9 . . ?
C38 C37 C36 118.1(3) . . ?
C38 C37 C40 120.8(3) . . ?
C36 C37 C40 121.1(3) . . ?
C37 C36 C35 122.4(3) . . ?
C37 C36 H36 118.8 . . ?
C35 C36 H36 118.8 . . ?
C36 C35 C34 119.1(3) . . ?
C36 C35 C41 118.8(3) . . ?
C34 C35 C41 121.8(3) . . ?
C39 C34 C35 119.4(3) . . ?
C39 C34 P2 127.2(2) . . ?
C35 C34 P2 113.3(2) . . ?
C32 C33 C28 120.1(3) . . ?
C32 C33 H33 119.9 . . ?
C28 C33 H33 119.9 . . ?
C31 C32 C33 120.9(3) . . ?
C31 C32 H32 119.5 . . ?
C33 C32 H32 119.5 . . ?
C30 C31 C32 119.4(3) . . ?
C30 C31 H31 120.3 . . ?
C32 C31 H31 120.3 . . ?
C31 C30 C29 120.4(3) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C28 C29 C30 120.9(3) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C29 C28 C33 118.3(3) . . ?
C29 C28 C21 119.1(3) . . ?
C33 C28 C21 122.7(3) . . ?
C26 C27 C22 120.5(3) . . ?
C26 C27 H27 119.8 . . ?
C22 C27 H27 119.8 . . ?
C25 C26 C27 120.5(4) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C24 C25 C26 119.7(3) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C25 C24 C23 119.8(4) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C22 C23 C24 120.8(4) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C23 C22 C27 118.7(3) . . ?
C23 C22 C21 119.2(3) . . ?
C27 C22 C21 122.0(3) . . ?
C28 C21 C2 113.5(2) . . ?
C28 C21 C22 112.6(2) . . ?
C2 C21 C22 109.7(2) . . ?
C28 C21 H21 106.9 . . ?
C2 C21 H21 106.9 . . ?
C22 C21 H21 106.9 . . ?
C42 C43 C44 120.7(4) . . ?
C42 C43 H43 119.7 . . ?
C44 C43 H43 119.7 . . ?
C43 C42 C47 118.2(3) . . ?
C43 C42 C41 123.1(3) . . ?
C47 C42 C41 118.7(3) . . ?
C48 C41 C42 111.8(2) . . ?
C48 C41 C35 112.2(2) . . ?
C42 C41 C35 110.9(2) . . ?
C48 C41 H41 107.2 . . ?
C42 C41 H41 107.2 . . ?
C35 C41 H41 107.2 . . ?
C66 C61 C62 118.2(3) . . ?
C66 C61 C54 118.8(3) . . ?
C62 C61 C54 123.0(3) . . ?
C45 C44 C43 120.4(4) . . ?
C45 C44 H44 119.8 . . ?
C43 C44 H44 119.8 . . ?
C61 C66 C65 120.9(4) . . ?
C61 C66 H66 119.5 . . ?
C65 C66 H66 119.5 . . ?
C46 C45 C44 119.3(3) . . ?
C46 C45 H45 120.4 . . ?
C44 C45 H45 120.4 . . ?
C64 C65 C66 120.5(4) . . ?
C64 C65 H65 119.8 . . ?
C66 C65 H65 119.8 . . ?
C47 C46 C45 120.2(4) . . ?
C47 C46 H46 119.9 . . ?
C45 C46 H46 119.9 . . ?
C65 C64 C63 119.5(4) . . ?
C65 C64 H64 120.3 . . ?
C63 C64 H64 120.3 . . ?
C46 C47 C42 121.3(3) . . ?
C46 C47 H47 119.4 . . ?
C42 C47 H47 119.4 . . ?
C64 C63 C62 120.1(4) . . ?
C64 C63 H63 119.9 . . ?
C62 C63 H63 119.9 . . ?
C49 C48 C53 118.2(3) . . ?
C49 C48 C41 122.6(3) . . ?
C53 C48 C41 119.1(3) . . ?
C61 C62 C63 120.8(3) . . ?
C61 C62 H62 119.6 . . ?
C63 C62 H62 119.6 . . ?
C48 C49 C50 121.2(3) . . ?
C48 C49 H49 119.4 . . ?
C50 C49 H49 119.4 . . ?
C51 C50 C49 119.8(4) . . ?
C51 C50 H50 120.1 . . ?
C49 C50 H50 120.1 . . ?
C55 C60 C59 121.0(3) . . ?
C55 C60 H60 119.5 . . ?
C59 C60 H60 119.5 . . ?
C52 C51 C50 119.8(3) . . ?
C52 C51 H51 120.1 . . ?
C50 C51 H51 120.1 . . ?
C58 C59 C60 120.3(4) . . ?
C58 C59 H59 119.9 . . ?
C60 C59 H59 119.9 . . ?
C51 C52 C53 120.2(3) . . ?
C51 C52 H52 119.9 . . ?
C53 C52 H52 119.9 . . ?
C57 C58 C59 119.1(3) . . ?
C57 C58 H58 120.5 . . ?
C59 C58 H58 120.5 . . ?
C52 C53 C48 120.8(3) . . ?
C52 C53 H53 119.6 . . ?
C48 C53 H53 119.6 . . ?
C58 C57 C56 120.5(4) . . ?
C58 C57 H57 119.8 . . ?
C56 C57 H57 119.8 . . ?
C39 C54 C61 110.8(2) . . ?
C39 C54 C55 111.5(2) . . ?
C61 C54 C55 112.5(2) . . ?
C39 C54 H54 107.3 . . ?
C61 C54 H54 107.3 . . ?
C55 C54 H54 107.3 . . ?
C55 C56 C57 121.2(3) . . ?
C55 C56 H56 119.4 . . ?
C57 C56 H56 119.4 . . ?
C56 C55 C60 118.0(3) . . ?
C56 C55 C54 123.1(3) . . ?
C60 C55 C54 118.8(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
C2 C1 P1 Cl2 -138.06(19) . . . . ?
C6 C1 P1 Cl2 44.4(3) . . . . ?
C2 C1 P1 Cl1 118.7(3) . . . . ?
C6 C1 P1 Cl1 -58.8(3) . . . . ?
C2 C1 P1 I1 114.6(2) . . . . ?
C6 C1 P1 I1 -62.9(3) . . . . ?
C6 C1 C2 C3 -1.2(4) . . . . ?
P1 C1 C2 C3 -179.0(2) . . . . ?
C6 C1 C2 C21 173.4(3) . . . . ?
P1 C1 C2 C21 -4.3(3) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
P1 C1 C6 C5 177.0(2) . . . . ?
C2 C1 C6 C8 178.6(3) . . . . ?
P1 C1 C6 C8 -4.0(4) . . . . ?
C1 C6 C5 C4 1.2(5) . . . . ?
C8 C6 C5 C4 -177.8(3) . . . . ?
C6 C5 C4 C3 -0.4(5) . . . . ?
C6 C5 C4 C7 179.9(3) . . . . ?
C5 C6 C8 C15B 85.2(12) . . . . ?
C1 C6 C8 C15B -93.8(12) . . . . ?
C5 C6 C8 C9 -41.1(4) . . . . ?
C1 C6 C8 C9 140.0(3) . . . . ?
C5 C6 C8 C15 82.8(6) . . . . ?
C1 C6 C8 C15 -96.2(6) . . . . ?
C15B C8 C15 C16 163(8) . . . . ?
C6 C8 C15 C16 -28.2(8) . . . . ?
C9 C8 C15 C16 95.0(7) . . . . ?
C15B C8 C15 C20 -13(7) . . . . ?
C6 C8 C15 C20 156.3(5) . . . . ?
C9 C8 C15 C20 -80.5(6) . . . . ?
C20 C15 C16 C17 0.0 . . . . ?
C8 C15 C16 C17 -175.4(10) . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C15 0.0 . . . . ?
C16 C15 C20 C19 0.0 . . . . ?
C8 C15 C20 C19 175.7(9) . . . . ?
C6 C8 C15B C16B -23.3(18) . . . . ?
C9 C8 C15B C16B 104.5(14) . . . . ?
C15 C8 C15B C16B -11(7) . . . . ?
C6 C8 C15B C20B 156.6(9) . . . . ?
C9 C8 C15B C20B -75.5(14) . . . . ?
C15 C8 C15B C20B 169(9) . . . . ?
C20B C15B C16B C17B 0.0 . . . . ?
C8 C15B C16B C17B 180(2) . . . . ?
C15B C16B C17B C18B 0.0 . . . . ?
C16B C17B C18B C19B 0.0 . . . . ?
C17B C18B C19B C20B 0.0 . . . . ?
C18B C19B C20B C15B 0.0 . . . . ?
C16B C15B C20B C19B 0.0 . . . . ?
C8 C15B C20B C19B -180(2) . . . . ?
C15B C8 C9 C14 -33.9(9) . . . . ?
C6 C8 C9 C14 99.2(3) . . . . ?
C15 C8 C9 C14 -23.2(7) . . . . ?
C15B C8 C9 C10 147.6(9) . . . . ?
C6 C8 C9 C10 -79.4(3) . . . . ?
C15 C8 C9 C10 158.2(6) . . . . ?
C14 C9 C10 C11 -1.2(5) . . . . ?
C8 C9 C10 C11 177.4(3) . . . . ?
C9 C10 C11 C12 -0.1(6) . . . . ?
C10 C11 C12 C13 0.9(6) . . . . ?
C11 C12 C13 C14 -0.2(6) . . . . ?
C10 C9 C14 C13 1.9(5) . . . . ?
C8 C9 C14 C13 -176.6(3) . . . . ?
C12 C13 C14 C9 -1.2(5) . . . . ?
C5 C4 C3 C2 -1.3(5) . . . . ?
C7 C4 C3 C2 178.4(3) . . . . ?
C1 C2 C3 C4 2.1(4) . . . . ?
C21 C2 C3 C4 -172.6(3) . . . . ?
C34 C39 C38 C37 -1.3(5) . . . . ?
C54 C39 C38 C37 176.2(3) . . . . ?
C39 C38 C37 C36 -0.1(5) . . . . ?
C39 C38 C37 C40 -179.0(3) . . . . ?
C38 C37 C36 C35 1.6(5) . . . . ?
C40 C37 C36 C35 -179.6(3) . . . . ?
C37 C36 C35 C34 -1.6(5) . . . . ?
C37 C36 C35 C41 173.2(3) . . . . ?
C38 C39 C34 C35 1.3(4) . . . . ?
C54 C39 C34 C35 -176.0(3) . . . . ?
C38 C39 C34 P2 -175.5(2) . . . . ?
C54 C39 C34 P2 7.2(4) . . . . ?
C36 C35 C34 C39 0.1(4) . . . . ?
C41 C35 C34 C39 -174.5(3) . . . . ?
C36 C35 C34 P2 177.3(2) . . . . ?
C41 C35 C34 P2 2.7(4) . . . . ?
Cl40 P2 C34 C39 -45.2(3) . . . . ?
Cl3 P2 C34 C39 57.1(3) . . . . ?
I2 P2 C34 C39 61.2(3) . . . . ?
Cl40 P2 C34 C35 137.8(2) . . . . ?
Cl3 P2 C34 C35 -119.8(3) . . . . ?
I2 P2 C34 C35 -115.8(2) . . . . ?
C28 C33 C32 C31 -0.1(6) . . . . ?
C33 C32 C31 C30 0.3(6) . . . . ?
C32 C31 C30 C29 0.0(6) . . . . ?
C31 C30 C29 C28 -0.4(6) . . . . ?
C30 C29 C28 C33 0.6(5) . . . . ?
C30 C29 C28 C21 -179.5(3) . . . . ?
C32 C33 C28 C29 -0.4(5) . . . . ?
C32 C33 C28 C21 179.7(3) . . . . ?
C22 C27 C26 C25 -0.7(6) . . . . ?
C27 C26 C25 C24 0.6(7) . . . . ?
C26 C25 C24 C23 0.3(7) . . . . ?
C25 C24 C23 C22 -1.2(7) . . . . ?
C24 C23 C22 C27 1.0(6) . . . . ?
C24 C23 C22 C21 -179.6(4) . . . . ?
C26 C27 C22 C23 -0.1(6) . . . . ?
C26 C27 C22 C21 -179.4(3) . . . . ?
C29 C28 C21 C2 -84.4(3) . . . . ?
C33 C28 C21 C2 95.5(3) . . . . ?
C29 C28 C21 C22 150.2(3) . . . . ?
C33 C28 C21 C22 -29.9(4) . . . . ?
C3 C2 C21 C28 -26.6(4) . . . . ?
C1 C2 C21 C28 158.7(3) . . . . ?
C3 C2 C21 C22 100.2(3) . . . . ?
C1 C2 C21 C22 -74.4(3) . . . . ?
C23 C22 C21 C28 -86.8(4) . . . . ?
C27 C22 C21 C28 92.5(4) . . . . ?
C23 C22 C21 C2 145.8(3) . . . . ?
C27 C22 C21 C2 -34.9(4) . . . . ?
C44 C43 C42 C47 1.7(6) . . . . ?
C44 C43 C42 C41 178.9(3) . . . . ?
C43 C42 C41 C48 -110.3(3) . . . . ?
C47 C42 C41 C48 66.9(4) . . . . ?
C43 C42 C41 C35 15.8(4) . . . . ?
C47 C42 C41 C35 -167.0(3) . . . . ?
C36 C35 C41 C48 29.1(4) . . . . ?
C34 C35 C41 C48 -156.3(3) . . . . ?
C36 C35 C41 C42 -96.7(3) . . . . ?
C34 C35 C41 C42 77.9(3) . . . . ?
C42 C43 C44 C45 -1.1(7) . . . . ?
C62 C61 C66 C65 0.1(5) . . . . ?
C54 C61 C66 C65 -178.3(3) . . . . ?
C43 C44 C45 C46 -0.2(6) . . . . ?
C61 C66 C65 C64 0.2(7) . . . . ?
C44 C45 C46 C47 0.9(6) . . . . ?
C66 C65 C64 C63 0.0(7) . . . . ?
C45 C46 C47 C42 -0.2(6) . . . . ?
C43 C42 C47 C46 -1.1(5) . . . . ?
C41 C42 C47 C46 -178.3(3) . . . . ?
C65 C64 C63 C62 -0.4(6) . . . . ?
C42 C41 C48 C49 27.0(4) . . . . ?
C35 C41 C48 C49 -98.4(4) . . . . ?
C42 C41 C48 C53 -155.1(3) . . . . ?
C35 C41 C48 C53 79.5(4) . . . . ?
C66 C61 C62 C63 -0.5(5) . . . . ?
C54 C61 C62 C63 177.7(3) . . . . ?
C64 C63 C62 C61 0.7(6) . . . . ?
C53 C48 C49 C50 -0.6(5) . . . . ?
C41 C48 C49 C50 177.4(3) . . . . ?
C48 C49 C50 C51 0.6(6) . . . . ?
C49 C50 C51 C52 -0.4(6) . . . . ?
C55 C60 C59 C58 0.1(7) . . . . ?
C50 C51 C52 C53 0.1(6) . . . . ?
C60 C59 C58 C57 -0.8(7) . . . . ?
C51 C52 C53 C48 0.0(6) . . . . ?
C49 C48 C53 C52 0.3(5) . . . . ?
C41 C48 C53 C52 -177.7(3) . . . . ?
C59 C58 C57 C56 1.0(7) . . . . ?
C34 C39 C54 C61 -138.4(3) . . . . ?
C38 C39 C54 C61 44.2(4) . . . . ?
C34 C39 C54 C55 95.4(3) . . . . ?
C38 C39 C54 C55 -81.9(3) . . . . ?
C66 C61 C54 C39 65.9(4) . . . . ?
C62 C61 C54 C39 -112.4(3) . . . . ?
C66 C61 C54 C55 -168.6(3) . . . . ?
C62 C61 C54 C55 13.1(4) . . . . ?
C58 C57 C56 C55 -0.5(7) . . . . ?
C57 C56 C55 C60 -0.1(6) . . . . ?
C57 C56 C55 C54 176.2(4) . . . . ?
C59 C60 C55 C56 0.3(6) . . . . ?
C59 C60 C55 C54 -176.2(4) . . . . ?
C39 C54 C55 C56 23.4(4) . . . . ?
C61 C54 C55 C56 -101.8(4) . . . . ?
C39 C54 C55 C60 -160.3(3) . . . . ?
C61 C54 C55 C60 74.6(4) . . . . ?

_refine_diff_density_max         1.349
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.073

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_jb_ms401_1
_database_code_depnum_ccdc_archive 'CCDC 1894110'
loop_
_audit_author_name
_audit_author_address
'Alexander Villinger'
;University Rostock
Germany
;
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2019-02-27 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H27 Cl'
_chemical_formula_sum            'C33 H27 Cl'
_chemical_formula_weight         458.99

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   17.0701(18)
_cell_length_b                   24.879(2)
_cell_length_c                   5.8722(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2493.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9917
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      32.11

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.172
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7105
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Bruker D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            67901
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.523
_diffrn_reflns_theta_max         32.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4399
_reflns_number_gt                3691
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2013

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine.
 
 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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.0436P)²+1.4711P] 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         4399
_refine_ls_number_parameters     161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1072
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.65932(3) 0.7500 0.69481(7) 0.02146(10) Uani 1 2 d S T P . .
C1 C 0.73917(9) 0.7500 0.5079(3) 0.0147(3) Uani 1 2 d S T P . .
C2 C 0.76872(6) 0.70051(4) 0.43331(18) 0.01450(19) Uani 1 1 d . . . . .
C3 C 0.83035(6) 0.70170(4) 0.2774(2) 0.0181(2) Uani 1 1 d . . . . .
H3 H 0.8516 0.6687 0.2244 0.022 Uiso 1 1 calc R U . . .
C4 C 0.86192(9) 0.7500 0.1967(3) 0.0201(3) Uani 1 2 d S T P . .
C5 C 0.72980(6) 0.64836(4) 0.50965(18) 0.0155(2) Uani 1 1 d . . . . .
H5 H 0.7181 0.6526 0.6755 0.019 Uiso 1 1 calc R U . . .
C6 C 0.65102(6) 0.64004(4) 0.3906(2) 0.0163(2) Uani 1 1 d . . . . .
C7 C 0.63344(7) 0.66344(5) 0.1819(2) 0.0218(2) Uani 1 1 d . . . . .
H7 H 0.6705 0.6865 0.1114 0.026 Uiso 1 1 calc R U . . .
C8 C 0.56166(8) 0.65338(5) 0.0742(2) 0.0284(3) Uani 1 1 d . . . . .
H8 H 0.5502 0.6698 -0.0680 0.034 Uiso 1 1 calc R U . . .
C9 C 0.50745(7) 0.61957(5) 0.1744(3) 0.0319(3) Uani 1 1 d . . . . .
H9 H 0.4590 0.6124 0.1010 0.038 Uiso 1 1 calc R U . . .
C10 C 0.52439(8) 0.59622(6) 0.3821(3) 0.0341(3) Uani 1 1 d . . . . .
H10 H 0.4873 0.5730 0.4515 0.041 Uiso 1 1 calc R U . . .
C11 C 0.59535(8) 0.60645(5) 0.4908(2) 0.0255(3) Uani 1 1 d . . . . .
H11 H 0.6059 0.5904 0.6343 0.031 Uiso 1 1 calc R U . . .
C12 C 0.78170(7) 0.59863(4) 0.48781(18) 0.0150(2) Uani 1 1 d . . . . .
C13 C 0.78080(7) 0.56657(4) 0.29260(19) 0.0177(2) Uani 1 1 d . . . . .
H13 H 0.7488 0.5765 0.1671 0.021 Uiso 1 1 calc R U . . .
C14 C 0.82636(7) 0.51999(4) 0.2795(2) 0.0203(2) Uani 1 1 d . . . . .
H14 H 0.8253 0.4986 0.1455 0.024 Uiso 1 1 calc R U . . .
C15 C 0.87307(7) 0.50493(4) 0.4620(2) 0.0217(2) Uani 1 1 d . . . . .
H15 H 0.9041 0.4733 0.4534 0.026 Uiso 1 1 calc R U . . .
C16 C 0.87423(8) 0.53640(5) 0.6571(2) 0.0238(2) Uani 1 1 d . . . . .
H16 H 0.9059 0.5261 0.7828 0.029 Uiso 1 1 calc R U . . .
C17 C 0.82907(7) 0.58310(4) 0.6697(2) 0.0206(2) Uani 1 1 d . . . . .
H17 H 0.8306 0.6045 0.8036 0.025 Uiso 1 1 calc R U . . .
C18 C 0.92738(12) 0.7500 0.0236(4) 0.0342(5) Uani 1 2 d S T P . .
H18A H 0.9085 0.7656 -0.1194 0.051 Uiso 0.5 1 calc R U P . .
H18B H 0.9448 0.7130 -0.0033 0.051 Uiso 0.5 1 calc R U P . .
H18C H 0.9713 0.7714 0.0813 0.051 Uiso 0.5 1 calc R U P . .


#==============================================================================

# MOLECULAR GEOMETRY

_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
Cl1 C1 1.7499(16) . ?
C1 C2 1.4009(12) . ?
C1 C2 1.4009(12) 7_575 ?
C2 C3 1.3948(16) . ?
C2 C5 1.5250(14) . ?
C3 C4 1.3997(13) . ?
C3 H3 0.9500 . ?
C4 C3 1.3997(13) 7_575 ?
C4 C18 1.511(2) . ?
C5 C12 1.5271(14) . ?
C5 C6 1.5297(16) . ?
C5 H5 1.0000 . ?
C6 C7 1.3896(16) . ?
C6 C11 1.3956(15) . ?
C7 C8 1.4016(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C17 1.3944(16) . ?
C12 C13 1.3965(15) . ?
C13 C14 1.3976(15) . ?
C13 H13 0.9500 . ?
C14 C15 1.3870(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3881(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.3962(16) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C2 123.02(14) . 7_575 ?
C2 C1 Cl1 118.47(7) . . ?
C2 C1 Cl1 118.47(7) 7_575 . ?
C3 C2 C1 117.27(10) . . ?
C3 C2 C5 122.65(9) . . ?
C1 C2 C5 119.93(10) . . ?
C2 C3 C4 122.06(11) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C3 118.31(15) 7_575 . ?
C3 C4 C18 120.84(7) 7_575 . ?
C3 C4 C18 120.84(7) . . ?
C2 C5 C12 114.32(9) . . ?
C2 C5 C6 111.33(9) . . ?
C12 C5 C6 111.22(8) . . ?
C2 C5 H5 106.5 . . ?
C12 C5 H5 106.5 . . ?
C6 C5 H5 106.5 . . ?
C7 C6 C11 118.40(11) . . ?
C7 C6 C5 122.42(10) . . ?
C11 C6 C5 119.15(11) . . ?
C6 C7 C8 120.79(11) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 120.13(13) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 119.45(13) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 120.64(12) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C6 120.57(13) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
C17 C12 C13 118.48(10) . . ?
C17 C12 C5 119.77(10) . . ?
C13 C12 C5 121.69(10) . . ?
C12 C13 C14 120.83(10) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 120.09(11) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 119.58(10) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 120.34(11) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C16 120.68(11) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_refine_diff_density_max         0.407
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.055

#==============================================================================

# SHELX FILES

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_av_ms455
_database_code_depnum_ccdc_archive 'CCDC 1894111'
loop_
_audit_author_name
_audit_author_address
'Alexander Villinger'
;University Rostock
Germany
;
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2019-02-27 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H27 F'
_chemical_formula_sum            'C33 H27 F'
_chemical_formula_weight         442.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   17.1693(12)
_cell_length_b                   24.7652(15)
_cell_length_c                   5.5609(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2364.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2583
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      31.26

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6736
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Apex Kappa-II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21181
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.887
_diffrn_reflns_theta_max         30.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3831
_reflns_number_gt                2695
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine. 

 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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.0443P)²+0.8786P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3831
_refine_ls_number_parameters     161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.31053(6) 0.7500 0.6545(2) 0.0239(2) Uani 1 2 d S T P . .
C1 C 0.24776(10) 0.7500 0.5029(3) 0.0173(3) Uani 1 2 d S T P . .
C2 C 0.21979(7) 0.70044(4) 0.4266(2) 0.0173(2) Uani 1 1 d . . . . .
C3 C 0.15738(7) 0.70151(5) 0.2672(2) 0.0195(2) Uani 1 1 d . . . . .
H3 H 0.1363 0.6683 0.2113 0.023 Uiso 1 1 calc R U . . .
C4 C 0.12477(10) 0.7500 0.1868(3) 0.0209(4) Uani 1 2 d S T P . .
C5 C 0.26394(7) 0.64935(4) 0.4947(2) 0.0186(2) Uani 1 1 d . . . . .
H5 H 0.2784 0.6529 0.6681 0.022 Uiso 1 1 calc R U . . .
C6 C 0.34013(7) 0.64551(5) 0.3533(2) 0.0202(3) Uani 1 1 d . . . . .
C7 C 0.35182(8) 0.67347(5) 0.1400(3) 0.0248(3) Uani 1 1 d . . . . .
H7 H 0.3118 0.6964 0.0804 0.030 Uiso 1 1 calc R U . . .
C8 C 0.42109(8) 0.66854(6) 0.0120(3) 0.0318(3) Uani 1 1 d . . . . .
H8 H 0.4282 0.6881 -0.1333 0.038 Uiso 1 1 calc R U . . .
C9 C 0.47947(8) 0.63526(6) 0.0960(3) 0.0359(4) Uani 1 1 d . . . . .
H9 H 0.5267 0.6316 0.0085 0.043 Uiso 1 1 calc R U . . .
C10 C 0.46883(8) 0.60717(6) 0.3086(3) 0.0362(4) Uani 1 1 d . . . . .
H10 H 0.5089 0.5842 0.3669 0.043 Uiso 1 1 calc R U . . .
C11 C 0.39981(8) 0.61234(5) 0.4374(3) 0.0269(3) Uani 1 1 d . . . . .
H11 H 0.3933 0.5931 0.5839 0.032 Uiso 1 1 calc R U . . .
C12 C 0.21442(7) 0.59847(4) 0.4727(2) 0.0185(2) Uani 1 1 d . . . . .
C13 C 0.21929(8) 0.56457(5) 0.2743(2) 0.0216(3) Uani 1 1 d . . . . .
H13 H 0.2539 0.5732 0.1467 0.026 Uiso 1 1 calc R U . . .
C14 C 0.17378(8) 0.51803(5) 0.2605(3) 0.0247(3) Uani 1 1 d . . . . .
H14 H 0.1776 0.4952 0.1239 0.030 Uiso 1 1 calc R U . . .
C15 C 0.12307(8) 0.50497(5) 0.4448(3) 0.0257(3) Uani 1 1 d . . . . .
H15 H 0.0921 0.4733 0.4353 0.031 Uiso 1 1 calc R U . . .
C16 C 0.11792(8) 0.53856(5) 0.6434(3) 0.0267(3) Uani 1 1 d . . . . .
H16 H 0.0832 0.5298 0.7707 0.032 Uiso 1 1 calc R U . . .
C17 C 0.16323(8) 0.58491(5) 0.6571(2) 0.0231(3) Uani 1 1 d . . . . .
H17 H 0.1592 0.6077 0.7941 0.028 Uiso 1 1 calc R U . . .
C18 C 0.05798(12) 0.7500 0.0097(4) 0.0313(5) Uani 1 2 d S T P . .
H18A H 0.0434 0.7873 -0.0279 0.047 Uiso 0.5 1 calc R U P . .
H18B H 0.0133 0.7312 0.0803 0.047 Uiso 0.5 1 calc R U P . .
H18C H 0.0740 0.7315 -0.1380 0.047 Uiso 0.5 1 calc R U P . .


#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.3682(19) . ?
C1 C2 1.3846(14) 7_575 ?
C1 C2 1.3846(14) . ?
C2 C3 1.3912(17) . ?
C2 C5 1.5227(16) . ?
C3 C4 1.3983(15) . ?
C3 H3 0.9500 . ?
C4 C3 1.3982(15) 7_575 ?
C4 C18 1.511(3) . ?
C5 C12 1.5249(16) . ?
C5 C6 1.5291(17) . ?
C5 H5 1.0000 . ?
C6 C7 1.3879(19) . ?
C6 C11 1.3941(17) . ?
C7 C8 1.3914(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.3892(17) . ?
C12 C17 1.3915(18) . ?
C13 C14 1.3945(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.3889(18) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C1 C2 117.51(8) . 7_575 ?
F1 C1 C2 117.51(8) . . ?
C2 C1 C2 124.86(16) 7_575 . ?
C1 C2 C3 116.46(11) . . ?
C1 C2 C5 119.20(11) . . ?
C3 C2 C5 123.90(10) . . ?
C2 C3 C4 121.91(12) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C3 118.35(16) 7_575 . ?
C3 C4 C18 120.80(8) 7_575 . ?
C3 C4 C18 120.80(8) . . ?
C2 C5 C12 112.89(10) . . ?
C2 C5 C6 110.48(10) . . ?
C12 C5 C6 112.62(10) . . ?
C2 C5 H5 106.8 . . ?
C12 C5 H5 106.8 . . ?
C6 C5 H5 106.8 . . ?
C7 C6 C11 118.32(13) . . ?
C7 C6 C5 122.15(11) . . ?
C11 C6 C5 119.53(12) . . ?
C6 C7 C8 121.13(13) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 120.03(15) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 119.59(14) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 120.43(14) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C6 120.51(14) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
C13 C12 C17 118.52(11) . . ?
C13 C12 C5 121.97(11) . . ?
C17 C12 C5 119.51(11) . . ?
C12 C13 C14 120.62(12) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 120.36(12) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.37(12) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C17 120.27(13) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 120.86(12) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C3 -178.19(12) . . . . ?
C2 C1 C2 C3 -2.1(3) 7_575 . . . ?
F1 C1 C2 C5 -5.6(2) . . . . ?
C2 C1 C2 C5 170.54(12) 7_575 . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C5 C2 C3 C4 -171.87(14) . . . . ?
C2 C3 C4 C3 1.2(3) . . . 7_575 ?
C2 C3 C4 C18 178.81(16) . . . . ?
C1 C2 C5 C12 161.04(13) . . . . ?
C3 C2 C5 C12 -26.94(17) . . . . ?
C1 C2 C5 C6 -71.85(16) . . . . ?
C3 C2 C5 C6 100.17(14) . . . . ?
C2 C5 C6 C7 -20.93(16) . . . . ?
C12 C5 C6 C7 106.33(13) . . . . ?
C2 C5 C6 C11 160.10(11) . . . . ?
C12 C5 C6 C11 -72.64(14) . . . . ?
C11 C6 C7 C8 0.24(19) . . . . ?
C5 C6 C7 C8 -178.74(12) . . . . ?
C6 C7 C8 C9 0.3(2) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
C8 C9 C10 C11 0.0(2) . . . . ?
C9 C10 C11 C6 0.6(2) . . . . ?
C7 C6 C11 C10 -0.65(19) . . . . ?
C5 C6 C11 C10 178.36(12) . . . . ?
C2 C5 C12 C13 99.50(14) . . . . ?
C6 C5 C12 C13 -26.47(16) . . . . ?
C2 C5 C12 C17 -81.21(14) . . . . ?
C6 C5 C12 C17 152.82(11) . . . . ?
C17 C12 C13 C14 0.05(18) . . . . ?
C5 C12 C13 C14 179.34(11) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
C15 C16 C17 C12 0.0(2) . . . . ?
C13 C12 C17 C16 -0.05(19) . . . . ?
C5 C12 C17 C16 -179.36(12) . . . . ?

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_is_ts037
_database_code_depnum_ccdc_archive 'CCDC 1894115'
loop_
_audit_author_name
_audit_author_address
'Alexander Villinger'
;University Rostock
Germany
;
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2019-02-27 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H35 P'
_chemical_formula_sum            'C36 H35 P'
_chemical_formula_weight         498.61

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   18.868(4)
_cell_length_b                   24.821(5)
_cell_length_c                   5.9471(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2785.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9940
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      34.94

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.790
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   0.910
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6458
_exptl_absorpt_correction_T_max  0.7470
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Apex Kappa-II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38890
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.310
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3777
_reflns_number_gt                3273
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine. 

 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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.0640P)²+1.7774P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3777
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1424
_refine_ls_wR_factor_gt          0.1368
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.70255(10) 0.2500 0.5017(3) 0.0153(4) Uani 1 2 d S T P . .
C2 C 0.73356(7) 0.29895(5) 0.5703(2) 0.0153(3) Uani 1 1 d . . . . .
C3 C 0.79336(7) 0.29803(5) 0.7082(2) 0.0168(3) Uani 1 1 d . . . . .
H3 H 0.8136 0.3312 0.7550 0.020 Uiso 1 1 calc R U . . .
C4 C 0.82453(10) 0.2500 0.7797(3) 0.0158(4) Uani 1 2 d S T P . .
C5 C 0.70258(7) 0.35284(5) 0.4905(2) 0.0162(3) Uani 1 1 d . . . . .
H5 H 0.6887 0.3476 0.3297 0.019 Uiso 1 1 calc R U . . .
C6 C 0.63520(7) 0.36928(5) 0.6152(3) 0.0182(3) Uani 1 1 d . . . . .
C7 C 0.61766(8) 0.34923(6) 0.8257(3) 0.0227(3) Uani 1 1 d . . . . .
H7 H 0.6478 0.3237 0.8963 0.027 Uiso 1 1 calc R U . . .
C8 C 0.55607(9) 0.36631(7) 0.9348(3) 0.0303(4) Uani 1 1 d . . . . .
H8 H 0.5447 0.3524 1.0792 0.036 Uiso 1 1 calc R U . . .
C9 C 0.51149(9) 0.40341(7) 0.8336(4) 0.0351(4) Uani 1 1 d . . . . .
H9 H 0.4695 0.4149 0.9077 0.042 Uiso 1 1 calc R U . . .
C10 C 0.52862(9) 0.42363(6) 0.6235(4) 0.0340(4) Uani 1 1 d . . . . .
H10 H 0.4982 0.4491 0.5533 0.041 Uiso 1 1 calc R U . . .
C11 C 0.58986(8) 0.40700(6) 0.5148(3) 0.0255(3) Uani 1 1 d . . . . .
H11 H 0.6012 0.4213 0.3710 0.031 Uiso 1 1 calc R U . . .
C12 C 0.75644(7) 0.39875(5) 0.4932(2) 0.0168(3) Uani 1 1 d . . . . .
C13 C 0.76383(8) 0.43260(6) 0.6778(3) 0.0205(3) Uani 1 1 d . . . . .
H13 H 0.7352 0.4270 0.8072 0.025 Uiso 1 1 calc R U . . .
C14 C 0.81286(8) 0.47469(6) 0.6752(3) 0.0253(3) Uani 1 1 d . . . . .
H14 H 0.8175 0.4975 0.8025 0.030 Uiso 1 1 calc R U . . .
C15 C 0.85479(8) 0.48320(6) 0.4871(3) 0.0291(4) Uani 1 1 d . . . . .
H15 H 0.8882 0.5118 0.4853 0.035 Uiso 1 1 calc R U . . .
C16 C 0.84772(9) 0.44983(7) 0.3019(3) 0.0299(4) Uani 1 1 d . . . . .
H16 H 0.8765 0.4555 0.1730 0.036 Uiso 1 1 calc R U . . .
C17 C 0.79850(8) 0.40793(6) 0.3040(3) 0.0232(3) Uani 1 1 d . . . . .
H17 H 0.7936 0.3855 0.1756 0.028 Uiso 1 1 calc R U . . .
C18 C 0.89516(11) 0.2500 0.9077(4) 0.0189(4) Uani 1 2 d S T P . .
C19 C 0.90357(10) 0.29969(7) 1.0579(3) 0.0339(4) Uani 1 1 d . . . . .
H19A H 0.9027 0.3323 0.9648 0.051 Uiso 1 1 calc R U . . .
H19B H 0.9488 0.2976 1.1383 0.051 Uiso 1 1 calc R U . . .
H19C H 0.8646 0.3010 1.1666 0.051 Uiso 1 1 calc R U . . .
C20 C 0.95361(13) 0.2500 0.7272(5) 0.0347(6) Uani 1 2 d S T P . .
H20A H 0.9481 0.2183 0.6306 0.052 Uiso 0.5 1 calc R U P . .
H20B H 1.0002 0.2490 0.8001 0.052 Uiso 1 2 calc R U P . .
H20C H 0.9497 0.2827 0.6358 0.052 Uiso 0.5 1 calc R U P . .
P1 P 0.62852(3) 0.2500 0.30086(10) 0.02399(16) Uani 1 2 d S T P . .
H1A H 0.588(3) 0.283(2) 0.426(9) 0.023(13) Uiso 0.5 1 d . . P . .
H2A H 0.590(3) 0.209(2) 0.362(9) 0.026(14) Uiso 0.5 1 d . . P . .


#==============================================================================

# MOLECULAR GEOMETRY

_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
C1 C2 1.4088(16) . ?
C1 C2 1.4089(16) 7_565 ?
C1 P1 1.838(2) . ?
C2 C3 1.3950(19) . ?
C2 C5 1.5350(18) . ?
C3 C4 1.3957(17) . ?
C3 H3 0.9500 . ?
C4 C3 1.3957(17) 7_565 ?
C4 C18 1.535(3) . ?
C5 C12 1.5268(19) . ?
C5 C6 1.5274(19) . ?
C5 H5 1.0000 . ?
C6 C7 1.387(2) . ?
C6 C11 1.402(2) . ?
C7 C8 1.397(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.390(2) . ?
C12 C17 1.396(2) . ?
C13 C14 1.395(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.394(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.531(2) . ?
C18 C19 1.531(2) 7_565 ?
C18 C20 1.539(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
P1 H1A 1.35(5) . ?
P1 H2A 1.31(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C2 119.17(17) . 7_565 ?
C2 C1 P1 120.25(9) . . ?
C2 C1 P1 120.25(9) 7_565 . ?
C3 C2 C1 119.47(13) . . ?
C3 C2 C5 120.26(12) . . ?
C1 C2 C5 120.26(13) . . ?
C2 C3 C4 122.28(13) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C3 117.32(18) 7_565 . ?
C3 C4 C18 121.14(9) 7_565 . ?
C3 C4 C18 121.14(9) . . ?
C12 C5 C6 110.46(11) . . ?
C12 C5 C2 113.18(11) . . ?
C6 C5 C2 113.56(11) . . ?
C12 C5 H5 106.3 . . ?
C6 C5 H5 106.3 . . ?
C2 C5 H5 106.3 . . ?
C7 C6 C11 118.59(14) . . ?
C7 C6 C5 122.75(13) . . ?
C11 C6 C5 118.64(14) . . ?
C6 C7 C8 120.58(15) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 120.35(18) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 119.43(16) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 120.47(16) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C6 120.57(17) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
C13 C12 C17 118.77(13) . . ?
C13 C12 C5 121.75(13) . . ?
C17 C12 C5 119.47(13) . . ?
C12 C13 C14 120.70(14) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 120.08(15) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 119.72(15) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.23(15) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 120.50(15) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C19 C18 C19 107.3(2) . 7_565 ?
C19 C18 C4 112.29(11) . . ?
C19 C18 C4 112.29(11) 7_565 . ?
C19 C18 C20 109.43(13) . . ?
C19 C18 C20 109.43(13) 7_565 . ?
C4 C18 C20 106.05(18) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 P1 H1A 94(2) . . ?
C1 P1 H2A 104(2) . . ?
H1A P1 H2A 90(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
C2 C1 C2 C3 -1.3(3) 7_565 . . . ?
P1 C1 C2 C3 -174.76(12) . . . . ?
C2 C1 C2 C5 177.62(11) 7_565 . . . ?
P1 C1 C2 C5 4.2(2) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C5 C2 C3 C4 -178.19(14) . . . . ?
C2 C3 C4 C3 -0.2(3) . . . 7_565 ?
C2 C3 C4 C18 172.64(16) . . . . ?
C3 C2 C5 C12 23.06(18) . . . . ?
C1 C2 C5 C12 -155.88(14) . . . . ?
C3 C2 C5 C6 -103.92(15) . . . . ?
C1 C2 C5 C6 77.13(17) . . . . ?
C12 C5 C6 C7 -106.81(15) . . . . ?
C2 C5 C6 C7 21.58(19) . . . . ?
C12 C5 C6 C11 71.90(16) . . . . ?
C2 C5 C6 C11 -159.70(13) . . . . ?
C11 C6 C7 C8 0.1(2) . . . . ?
C5 C6 C7 C8 178.77(14) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C10 C11 C6 0.3(2) . . . . ?
C7 C6 C11 C10 -0.3(2) . . . . ?
C5 C6 C11 C10 -179.09(14) . . . . ?
C6 C5 C12 C13 35.86(18) . . . . ?
C2 C5 C12 C13 -92.74(15) . . . . ?
C6 C5 C12 C17 -142.74(13) . . . . ?
C2 C5 C12 C17 88.66(16) . . . . ?
C17 C12 C13 C14 -0.6(2) . . . . ?
C5 C12 C13 C14 -179.23(13) . . . . ?
C12 C13 C14 C15 0.1(2) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C14 C15 C16 C17 0.2(2) . . . . ?
C15 C16 C17 C12 -0.7(2) . . . . ?
C13 C12 C17 C16 0.9(2) . . . . ?
C5 C12 C17 C16 179.58(13) . . . . ?
C3 C4 C18 C19 -154.27(17) 7_565 . . . ?
C3 C4 C18 C19 33.2(3) . . . . ?
C3 C4 C18 C19 -33.2(3) 7_565 . . 7_565 ?
C3 C4 C18 C19 154.27(17) . . . 7_565 ?
C3 C4 C18 C20 86.26(16) 7_565 . . . ?
C3 C4 C18 C20 -86.26(16) . . . . ?

_refine_diff_density_max         0.620
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_MS520B
_database_code_depnum_ccdc_archive 'CCDC 1894118'
loop_
_audit_author_name
_audit_author_address
'Alexander Villinger'
;University Rostock
Germany
;
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2019-02-27 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/5
_shelx_SHELXL_version_number     2014/5

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 PH2[2,6-{CH(C6H4tBu)2}-4-Me-C6H2
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H29 P'
_chemical_formula_sum            'C33 H29 P'
_chemical_formula_weight         456.53

#==============================================================================

# CRYSTAL DATA

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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   34.4941(10)
_cell_length_b                   8.2825(2)
_cell_length_c                   17.2074(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4916.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4776
_cell_measurement_theta_min      5.0720
_cell_measurement_theta_max      76.2230

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_F_000             1936
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.117
_shelx_estimated_absorpt_T_min   0.841
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94784
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4102
_diffrn_reflns_number            16224
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.129
_diffrn_reflns_theta_max         76.384
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5118
_reflns_number_gt                4099
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    .
_computing_publication_material  .

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0351P)²+0.9037P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_atom_sites_solution_secondary   .
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5118
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0829
_refine_ls_wR_factor_gt          0.0759
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.43753(2) 0.19047(4) 0.52654(2) 0.02178(8) Uani 1 1 d . . . . .
H1 H 0.4493(5) 0.334(2) 0.5354(10) 0.034(5) Uiso 1 1 d . . . . .
H2 H 0.4227(6) 0.217(2) 0.4578(12) 0.046(6) Uiso 1 1 d . . . . .
C1 C 0.39174(4) 0.20800(14) 0.58231(7) 0.0187(2) Uani 1 1 d . . . . .
C2 C 0.39183(4) 0.27997(14) 0.65677(7) 0.0188(2) Uani 1 1 d . . . . .
C3 C 0.35705(4) 0.29329(15) 0.69732(7) 0.0211(2) Uani 1 1 d . . . . .
H3 H 0.3571 0.3425 0.7472 0.025 Uiso 1 1 calc R U . . .
C4 C 0.32222(4) 0.23649(15) 0.66690(8) 0.0219(3) Uani 1 1 d . . . . .
C5 C 0.32317(4) 0.15685(16) 0.59591(8) 0.0219(3) Uani 1 1 d . . . . .
H5 H 0.2998 0.1132 0.5756 0.026 Uiso 1 1 calc R U . . .
C6 C 0.35734(4) 0.13907(15) 0.55364(7) 0.0198(2) Uani 1 1 d . . . . .
C7 C 0.28462(4) 0.2536(2) 0.71095(9) 0.0333(3) Uani 1 1 d . . . . .
H7A H 0.2649 0.3012 0.6769 0.050 Uiso 0.41(2) 1 calc R U P A 1
H7B H 0.2886 0.3237 0.7561 0.050 Uiso 0.41(2) 1 calc R U P A 1
H7C H 0.2759 0.1470 0.7284 0.050 Uiso 0.41(2) 1 calc R U P A 1
H7D H 0.2882 0.2161 0.7645 0.050 Uiso 0.59(2) 1 calc R U P A 2
H7E H 0.2645 0.1886 0.6856 0.050 Uiso 0.59(2) 1 calc R U P A 2
H7F H 0.2767 0.3672 0.7113 0.050 Uiso 0.59(2) 1 calc R U P A 2
C8 C 0.43019(4) 0.33480(15) 0.69307(7) 0.0199(2) Uani 1 1 d . . . . .
H8 H 0.4507 0.2634 0.6704 0.024 Uiso 1 1 calc R U . . .
C9 C 0.44219(4) 0.50739(15) 0.67337(7) 0.0199(2) Uani 1 1 d . . . . .
C10 C 0.48121(4) 0.53867(17) 0.65712(8) 0.0243(3) Uani 1 1 d . . . . .
H10 H 0.4990 0.4514 0.6529 0.029 Uiso 1 1 calc R U . . .
C11 C 0.49424(4) 0.69568(18) 0.64710(8) 0.0290(3) Uani 1 1 d . . . . .
H11 H 0.5208 0.7154 0.6360 0.035 Uiso 1 1 calc R U . . .
C12 C 0.46873(4) 0.82346(17) 0.65323(8) 0.0292(3) Uani 1 1 d . . . . .
H12 H 0.4778 0.9311 0.6472 0.035 Uiso 1 1 calc R U . . .
C13 C 0.42991(4) 0.79433(17) 0.66814(9) 0.0283(3) Uani 1 1 d . . . . .
H13 H 0.4123 0.8821 0.6720 0.034 Uiso 1 1 calc R U . . .
C14 C 0.41661(4) 0.63628(16) 0.67754(8) 0.0245(3) Uani 1 1 d . . . . .
H14 H 0.3899 0.6169 0.6869 0.029 Uiso 1 1 calc R U . . .
C15 C 0.43181(3) 0.30851(15) 0.78102(7) 0.0206(2) Uani 1 1 d . . . . .
C16 C 0.41624(4) 0.41750(16) 0.83406(8) 0.0249(3) Uani 1 1 d . . . . .
H16 H 0.4033 0.5114 0.8158 0.030 Uiso 1 1 calc R U . . .
C17 C 0.41939(4) 0.39037(18) 0.91368(8) 0.0299(3) Uani 1 1 d . . . . .
H17 H 0.4081 0.4644 0.9493 0.036 Uiso 1 1 calc R U . . .
C18 C 0.43890(4) 0.2558(2) 0.94117(8) 0.0323(3) Uani 1 1 d . . . . .
H18 H 0.4417 0.2389 0.9955 0.039 Uiso 1 1 calc R U . . .
C19 C 0.45429(4) 0.14671(19) 0.88914(9) 0.0312(3) Uani 1 1 d . . . . .
H19 H 0.4675 0.0539 0.9077 0.037 Uiso 1 1 calc R U . . .
C20 C 0.45051(4) 0.17188(16) 0.80949(8) 0.0247(3) Uani 1 1 d . . . . .
H20 H 0.4608 0.0949 0.7742 0.030 Uiso 1 1 calc R U . . .
C21 C 0.35670(4) 0.04046(15) 0.47829(7) 0.0206(2) Uani 1 1 d . . . . .
H21 H 0.3838 0.0017 0.4694 0.025 Uiso 1 1 calc R U . . .
C22 C 0.33157(4) -0.11017(15) 0.48924(7) 0.0203(2) Uani 1 1 d . . . . .
C23 C 0.34549(4) -0.23187(17) 0.53786(8) 0.0255(3) Uani 1 1 d . . . . .
H23 H 0.3704 -0.2208 0.5608 0.031 Uiso 1 1 calc R U . . .
C24 C 0.32368(5) -0.36866(17) 0.55328(8) 0.0287(3) Uani 1 1 d . . . . .
H24 H 0.3336 -0.4502 0.5866 0.034 Uiso 1 1 calc R U . . .
C25 C 0.28728(4) -0.38632(17) 0.52009(9) 0.0300(3) Uani 1 1 d . . . . .
H25 H 0.2721 -0.4792 0.5311 0.036 Uiso 1 1 calc R U . . .
C26 C 0.27331(4) -0.26792(17) 0.47094(9) 0.0306(3) Uani 1 1 d . . . . .
H26 H 0.2485 -0.2801 0.4477 0.037 Uiso 1 1 calc R U . . .
C27 C 0.29541(4) -0.13054(16) 0.45521(8) 0.0253(3) Uani 1 1 d . . . . .
H27 H 0.2856 -0.0504 0.4209 0.030 Uiso 1 1 calc R U . . .
C28 C 0.34535(4) 0.13747(16) 0.40674(8) 0.0219(3) Uani 1 1 d . . . . .
C29 C 0.34883(5) 0.06615(18) 0.33337(8) 0.0305(3) Uani 1 1 d . . . . .
H29 H 0.3600 -0.0383 0.3288 0.037 Uiso 1 1 calc R U . . .
C30 C 0.33622(5) 0.1462(2) 0.26733(8) 0.0346(3) Uani 1 1 d . . . . .
H30 H 0.3383 0.0956 0.2180 0.042 Uiso 1 1 calc R U . . .
C31 C 0.32053(4) 0.3002(2) 0.27309(9) 0.0332(3) Uani 1 1 d . . . . .
H31 H 0.3115 0.3543 0.2279 0.040 Uiso 1 1 calc R U . . .
C32 C 0.31815(5) 0.37414(18) 0.34483(9) 0.0328(3) Uani 1 1 d . . . . .
H32 H 0.3080 0.4804 0.3489 0.039 Uiso 1 1 calc R U . . .
C33 C 0.33059(4) 0.29304(17) 0.41119(8) 0.0259(3) Uani 1 1 d . . . . .
H33 H 0.3289 0.3451 0.4603 0.031 Uiso 1 1 calc R U . . .



#==============================================================================

# MOLECULAR GEOMETRY

_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 C1 1.8538(13) . ?
P1 H1 1.266(18) . ?
P1 H2 1.31(2) . ?
C1 C6 1.4063(17) . ?
C1 C2 1.4131(17) . ?
C2 C3 1.3923(18) . ?
C2 C8 1.5320(17) . ?
C3 C4 1.3925(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3886(18) . ?
C4 C7 1.5087(18) . ?
C5 C6 1.3928(18) . ?
C5 H5 0.9500 . ?
C6 C21 1.5325(17) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 H7D 0.9800 . ?
C7 H7E 0.9800 . ?
C7 H7F 0.9800 . ?
C8 C9 1.5263(17) . ?
C8 C15 1.5301(17) . ?
C8 H8 1.0000 . ?
C9 C14 1.3869(18) . ?
C9 C10 1.3987(18) . ?
C10 C11 1.3867(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3965(19) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.3915(19) . ?
C15 C20 1.3916(18) . ?
C16 C17 1.393(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.378(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.392(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C28 1.5214(18) . ?
C21 C22 1.5308(17) . ?
C21 H21 1.0000 . ?
C22 C27 1.3882(18) . ?
C22 C23 1.3953(19) . ?
C23 C24 1.386(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.387(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.396(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C33 1.3875(19) . ?
C28 C29 1.3991(19) . ?
C29 C30 1.385(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.389(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.381(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.393(2) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 H1 97.9(8) . . ?
C1 P1 H2 97.0(9) . . ?
H1 P1 H2 94.4(12) . . ?
C6 C1 C2 119.42(11) . . ?
C6 C1 P1 120.37(9) . . ?
C2 C1 P1 120.04(9) . . ?
C3 C2 C1 119.08(11) . . ?
C3 C2 C8 121.09(11) . . ?
C1 C2 C8 119.77(11) . . ?
C2 C3 C4 121.89(12) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 118.08(12) . . ?
C5 C4 C7 120.46(12) . . ?
C3 C4 C7 121.40(12) . . ?
C4 C5 C6 121.99(12) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 119.20(11) . . ?
C5 C6 C21 119.07(11) . . ?
C1 C6 C21 121.70(11) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C7 H7D 109.5 . . ?
C4 C7 H7E 109.5 . . ?
H7D C7 H7E 109.5 . . ?
C4 C7 H7F 109.5 . . ?
H7D C7 H7F 109.5 . . ?
H7E C7 H7F 109.5 . . ?
C9 C8 C15 110.06(10) . . ?
C9 C8 C2 114.92(10) . . ?
C15 C8 C2 113.12(10) . . ?
C9 C8 H8 106.0 . . ?
C15 C8 H8 106.0 . . ?
C2 C8 H8 106.0 . . ?
C14 C9 C10 118.68(12) . . ?
C14 C9 C8 122.47(12) . . ?
C10 C9 C8 118.61(11) . . ?
C11 C10 C9 120.70(13) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 120.18(13) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 119.81(13) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 120.17(13) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 120.43(13) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C20 118.40(12) . . ?
C16 C15 C8 122.85(12) . . ?
C20 C15 C8 118.74(12) . . ?
C15 C16 C17 120.70(13) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 120.24(14) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 119.52(13) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.34(14) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C15 C20 C19 120.77(13) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C28 C21 C22 112.60(10) . . ?
C28 C21 C6 114.01(10) . . ?
C22 C21 C6 109.78(10) . . ?
C28 C21 H21 106.7 . . ?
C22 C21 H21 106.7 . . ?
C6 C21 H21 106.7 . . ?
C27 C22 C23 118.33(12) . . ?
C27 C22 C21 123.77(12) . . ?
C23 C22 C21 117.88(11) . . ?
C24 C23 C22 121.23(13) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 119.93(13) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 C24 119.54(13) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C27 120.43(13) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C22 C27 C26 120.52(13) . . ?
C22 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C33 C28 C29 118.25(13) . . ?
C33 C28 C21 122.70(12) . . ?
C29 C28 C21 119.03(12) . . ?
C30 C29 C28 120.75(14) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C29 C30 C31 120.19(14) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C32 C31 C30 119.65(14) . . ?
C32 C31 H31 120.2 . . ?
C30 C31 H31 120.2 . . ?
C31 C32 C33 120.04(14) . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C28 C33 C32 121.05(13) . . ?
C28 C33 H33 119.5 . . ?
C32 C33 H33 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -5.45(18) . . . . ?
P1 C1 C2 C3 179.39(9) . . . . ?
C6 C1 C2 C8 171.76(11) . . . . ?
P1 C1 C2 C8 -3.40(16) . . . . ?
C1 C2 C3 C4 0.56(19) . . . . ?
C8 C2 C3 C4 -176.62(11) . . . . ?
C2 C3 C4 C5 3.55(19) . . . . ?
C2 C3 C4 C7 -179.18(13) . . . . ?
C3 C4 C5 C6 -2.8(2) . . . . ?
C7 C4 C5 C6 179.89(13) . . . . ?
C4 C5 C6 C1 -2.03(19) . . . . ?
C4 C5 C6 C21 176.14(12) . . . . ?
C2 C1 C6 C5 6.17(18) . . . . ?
P1 C1 C6 C5 -178.69(9) . . . . ?
C2 C1 C6 C21 -171.95(11) . . . . ?
P1 C1 C6 C21 3.19(17) . . . . ?
C3 C2 C8 C9 -93.93(14) . . . . ?
C1 C2 C8 C9 88.91(14) . . . . ?
C3 C2 C8 C15 33.63(16) . . . . ?
C1 C2 C8 C15 -143.53(11) . . . . ?
C15 C8 C9 C14 -82.56(15) . . . . ?
C2 C8 C9 C14 46.53(17) . . . . ?
C15 C8 C9 C10 91.72(14) . . . . ?
C2 C8 C9 C10 -139.19(12) . . . . ?
C14 C9 C10 C11 1.4(2) . . . . ?
C8 C9 C10 C11 -173.07(12) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C10 C11 C12 C13 -1.1(2) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
C10 C9 C14 C13 -2.0(2) . . . . ?
C8 C9 C14 C13 172.24(12) . . . . ?
C12 C13 C14 C9 1.1(2) . . . . ?
C9 C8 C15 C16 46.49(16) . . . . ?
C2 C8 C15 C16 -83.57(15) . . . . ?
C9 C8 C15 C20 -131.81(12) . . . . ?
C2 C8 C15 C20 98.12(13) . . . . ?
C20 C15 C16 C17 0.1(2) . . . . ?
C8 C15 C16 C17 -178.22(13) . . . . ?
C15 C16 C17 C18 1.5(2) . . . . ?
C16 C17 C18 C19 -1.8(2) . . . . ?
C17 C18 C19 C20 0.5(2) . . . . ?
C16 C15 C20 C19 -1.4(2) . . . . ?
C8 C15 C20 C19 176.99(13) . . . . ?
C18 C19 C20 C15 1.1(2) . . . . ?
C5 C6 C21 C28 86.50(14) . . . . ?
C1 C6 C21 C28 -95.37(14) . . . . ?
C5 C6 C21 C22 -40.89(16) . . . . ?
C1 C6 C21 C22 137.23(12) . . . . ?
C28 C21 C22 C27 -19.81(18) . . . . ?
C6 C21 C22 C27 108.37(14) . . . . ?
C28 C21 C22 C23 161.90(12) . . . . ?
C6 C21 C22 C23 -69.92(14) . . . . ?
C27 C22 C23 C24 -1.2(2) . . . . ?
C21 C22 C23 C24 177.20(12) . . . . ?
C22 C23 C24 C25 0.0(2) . . . . ?
C23 C24 C25 C26 0.9(2) . . . . ?
C24 C25 C26 C27 -0.6(2) . . . . ?
C23 C22 C27 C26 1.5(2) . . . . ?
C21 C22 C27 C26 -176.82(13) . . . . ?
C25 C26 C27 C22 -0.6(2) . . . . ?
C22 C21 C28 C33 115.52(13) . . . . ?
C6 C21 C28 C33 -10.41(18) . . . . ?
C22 C21 C28 C29 -62.64(16) . . . . ?
C6 C21 C28 C29 171.43(12) . . . . ?
C33 C28 C29 C30 -2.9(2) . . . . ?
C21 C28 C29 C30 175.38(13) . . . . ?
C28 C29 C30 C31 1.2(2) . . . . ?
C29 C30 C31 C32 1.1(2) . . . . ?
C30 C31 C32 C33 -1.5(2) . . . . ?
C29 C28 C33 C32 2.4(2) . . . . ?
C21 C28 C33 C32 -175.74(13) . . . . ?
C31 C32 C33 C28 -0.3(2) . . . . ?

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.039

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_is_ts033_0506
_database_code_depnum_ccdc_archive 'CCDC 1894114'
loop_
_audit_author_name
_audit_author_address
'Alexander Villinger'
;University Rostock
Germany
;
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2019-02-27 downloaded from the CCDC.
;

_vrf_PLAT972_is_ts033_0506       
;
PROBLEM: Check Calcd Resid. Dens.  1.22A   From I1             -3.73 eA-3  
RESPONSE: Most probably due to absorption effects.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H33 I'
_chemical_formula_sum            'C36 H33 I'
_chemical_formula_weight         592.52

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   19.0070(19)
_cell_length_b                   24.840(2)
_cell_length_c                   5.9476(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2808.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9865
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      34.40

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.163
_shelx_estimated_absorpt_T_min   0.714
_shelx_estimated_absorpt_T_max   0.873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6540
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Apex Kappa-II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            62311
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.699
_diffrn_reflns_theta_max         32.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5162
_reflns_number_gt                4899
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine. 

 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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.0255P)²+6.5144P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5162
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.0982
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.303
_refine_ls_restrained_S_all      1.303
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.10985(2) 0.2500 1.21851(4) 0.01795(6) Uani 1 2 d S T P . .
C1 C 0.20185(16) 0.2500 1.0206(5) 0.0131(5) Uani 1 2 d S T P . .
C2 C 0.23168(11) 0.20064(8) 0.9576(4) 0.0127(4) Uani 1 1 d . . . . .
C3 C 0.29207(11) 0.20202(8) 0.8239(4) 0.0140(4) Uani 1 1 d . . . . .
H3 H 0.3129 0.1689 0.7797 0.017 Uiso 1 1 calc R U . . .
C4 C 0.32315(17) 0.2500 0.7523(5) 0.0138(5) Uani 1 2 d S T P . .
C7 C 0.20184(12) 0.14677(8) 1.0388(4) 0.0142(4) Uani 1 1 d . . . . .
H7 H 0.1891 0.1521 1.2005 0.017 Uiso 1 1 calc R U . . .
C8 C 0.13439(12) 0.12973(8) 0.9202(4) 0.0158(4) Uani 1 1 d . . . . .
C9 C 0.11609(13) 0.14792(10) 0.7077(5) 0.0210(4) Uani 1 1 d . . . . .
H9 H 0.1455 0.1731 0.6326 0.025 Uiso 1 1 calc R U . . .
C10 C 0.05501(15) 0.12970(11) 0.6033(6) 0.0287(6) Uani 1 1 d . . . . .
H10 H 0.0430 0.1425 0.4578 0.034 Uiso 1 1 calc R U . . .
C11 C 0.01155(14) 0.09292(11) 0.7108(7) 0.0354(7) Uani 1 1 d . . . . .
H11 H -0.0301 0.0804 0.6395 0.043 Uiso 1 1 calc R U . . .
C12 C 0.02948(14) 0.07481(11) 0.9226(7) 0.0345(7) Uani 1 1 d . . . . .
H12 H -0.0003 0.0500 0.9980 0.041 Uiso 1 1 calc R U . . .
C13 C 0.09061(13) 0.09251(10) 1.0267(5) 0.0247(5) Uani 1 1 d . . . . .
H13 H 0.1027 0.0792 1.1714 0.030 Uiso 1 1 calc R U . . .
C14 C 0.25589(12) 0.10137(8) 1.0340(4) 0.0139(4) Uani 1 1 d . . . . .
C15 C 0.26325(13) 0.06767(9) 0.8485(4) 0.0181(4) Uani 1 1 d . . . . .
H15 H 0.2343 0.0731 0.7203 0.022 Uiso 1 1 calc R U . . .
C16 C 0.31247(13) 0.02603(9) 0.8482(5) 0.0229(5) Uani 1 1 d . . . . .
H16 H 0.3171 0.0034 0.7203 0.027 Uiso 1 1 calc R U . . .
C17 C 0.35457(13) 0.01788(10) 1.0357(6) 0.0272(6) Uani 1 1 d . . . . .
H17 H 0.3881 -0.0105 1.0366 0.033 Uiso 1 1 calc R U . . .
C18 C 0.34775(14) 0.05091(12) 1.2209(5) 0.0285(6) Uani 1 1 d . . . . .
H18 H 0.3767 0.0453 1.3489 0.034 Uiso 1 1 calc R U . . .
C19 C 0.29848(13) 0.09246(10) 1.2205(4) 0.0212(4) Uani 1 1 d . . . . .
H19 H 0.2939 0.1149 1.3490 0.025 Uiso 1 1 calc R U . . .
C20 C 0.39375(17) 0.2500 0.6283(6) 0.0167(6) Uani 1 2 d S T P . .
C21 C 0.40227(15) 0.20038(11) 0.4782(5) 0.0274(6) Uani 1 1 d . . . . .
H21A H 0.3644 0.1996 0.3665 0.041 Uiso 1 1 calc R U . . .
H21B H 0.4001 0.1678 0.5707 0.041 Uiso 1 1 calc R U . . .
H21C H 0.4478 0.2020 0.4012 0.041 Uiso 1 1 calc R U . . .
C22 C 0.4516(2) 0.2500 0.8098(7) 0.0279(8) Uani 1 2 d S T P . .
H22A H 0.4462 0.2818 0.9060 0.042 Uiso 0.5 1 calc R U P . .
H22B H 0.4475 0.2174 0.9015 0.042 Uiso 0.5 1 calc R U P . .
H22C H 0.4979 0.2509 0.7375 0.042 Uiso 1 2 calc R U P . .


#==============================================================================

# MOLECULAR GEOMETRY

_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
I1 C1 2.108(3) . ?
C1 C2 1.402(3) . ?
C1 C2 1.402(3) 8_565 ?
C2 C3 1.397(3) . ?
C2 C7 1.531(3) . ?
C3 C4 1.397(3) . ?
C3 H3 0.9500 . ?
C4 C3 1.397(3) 8_565 ?
C4 C20 1.531(5) . ?
C7 C8 1.523(3) . ?
C7 C14 1.526(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.387(4) . ?
C8 C13 1.396(3) . ?
C9 C10 1.392(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.391(3) . ?
C14 C15 1.392(3) . ?
C15 C16 1.395(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.393(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.531(3) . ?
C20 C21 1.531(3) 8_565 ?
C20 C22 1.541(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C2 122.0(3) . 8_565 ?
C2 C1 I1 119.00(14) . . ?
C2 C1 I1 119.00(14) 8_565 . ?
C3 C2 C1 117.6(2) . . ?
C3 C2 C7 120.35(18) . . ?
C1 C2 C7 122.0(2) . . ?
C4 C3 C2 122.8(2) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C3 C4 C3 117.1(3) . 8_565 ?
C3 C4 C20 121.17(14) . . ?
C3 C4 C20 121.16(14) 8_565 . ?
C8 C7 C14 110.65(17) . . ?
C8 C7 C2 114.10(18) . . ?
C14 C7 C2 112.99(18) . . ?
C8 C7 H7 106.1 . . ?
C14 C7 H7 106.1 . . ?
C2 C7 H7 106.1 . . ?
C9 C8 C13 118.7(2) . . ?
C9 C8 C7 122.9(2) . . ?
C13 C8 C7 118.4(2) . . ?
C8 C9 C10 120.6(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 119.2(3) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
C19 C14 C15 118.5(2) . . ?
C19 C14 C7 119.6(2) . . ?
C15 C14 C7 121.8(2) . . ?
C14 C15 C16 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C18 C17 C16 120.0(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.2(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 120.7(3) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C21 107.3(3) . 8_565 ?
C21 C20 C4 111.94(18) . . ?
C21 C20 C4 111.94(18) 8_565 . ?
C21 C20 C22 109.5(2) . . ?
C21 C20 C22 109.5(2) 8_565 . ?
C4 C20 C22 106.7(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C2 C3 -1.4(4) 8_565 . . . ?
I1 C1 C2 C3 179.13(17) . . . . ?
C2 C1 C2 C7 176.03(18) 8_565 . . . ?
I1 C1 C2 C7 -3.5(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C7 C2 C3 C4 -177.4(2) . . . . ?
C2 C3 C4 C3 1.3(4) . . . 8_565 ?
C2 C3 C4 C20 173.1(3) . . . . ?
C3 C2 C7 C8 -106.9(2) . . . . ?
C1 C2 C7 C8 75.8(3) . . . . ?
C3 C2 C7 C14 20.7(3) . . . . ?
C1 C2 C7 C14 -156.7(2) . . . . ?
C14 C7 C8 C9 -104.8(2) . . . . ?
C2 C7 C8 C9 23.9(3) . . . . ?
C14 C7 C8 C13 72.5(3) . . . . ?
C2 C7 C8 C13 -158.7(2) . . . . ?
C13 C8 C9 C10 0.4(4) . . . . ?
C7 C8 C9 C10 177.8(2) . . . . ?
C8 C9 C10 C11 -0.1(4) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
C11 C12 C13 C8 1.1(4) . . . . ?
C9 C8 C13 C12 -1.0(4) . . . . ?
C7 C8 C13 C12 -178.4(2) . . . . ?
C8 C7 C14 C19 -141.9(2) . . . . ?
C2 C7 C14 C19 88.7(3) . . . . ?
C8 C7 C14 C15 37.0(3) . . . . ?
C2 C7 C14 C15 -92.4(3) . . . . ?
C19 C14 C15 C16 -0.4(3) . . . . ?
C7 C14 C15 C16 -179.3(2) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C15 C14 C19 C18 0.4(3) . . . . ?
C7 C14 C19 C18 179.4(2) . . . . ?
C17 C18 C19 C14 -0.3(4) . . . . ?
C3 C4 C20 C21 34.0(4) . . . . ?
C3 C4 C20 C21 -154.5(3) 8_565 . . . ?
C3 C4 C20 C21 154.5(3) . . . 8_565 ?
C3 C4 C20 C21 -34.0(4) 8_565 . . 8_565 ?
C3 C4 C20 C22 -85.7(3) . . . . ?
C3 C4 C20 C22 85.7(3) 8_565 . . . ?

_refine_diff_density_max         2.038
_refine_diff_density_min         -3.510
_refine_diff_density_rms         0.118

