# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1870332'
_audit_update_record             
;
2018-09-28 deposited with the CCDC.
2019-01-17 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H40 N P'
_chemical_formula_iupac          ?
_chemical_formula_weight         541.68
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.3710(2)
_cell_length_b                   13.7203(3)
_cell_length_c                   11.5632(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.1780(10)
_cell_angle_gamma                90
_cell_volume                     1484.43(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9390
_cell_measurement_theta_min      3.8286
_cell_measurement_theta_max      68.3263
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580

_exptl_absorpt_coefficient_mu    1.010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.91

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'BRUKER APEXII CCD'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            10494
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_theta_min         3.83
_diffrn_reflns_theta_max         68.32
_diffrn_reflns_theta_full        68.32
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             4403
_reflns_number_gt                4366
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1233
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_refine_ls_number_reflns         4403
_refine_ls_number_parameters     490
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0344P)²+0.7502P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.378
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 1526 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.106(8)

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'
N N 0.0311 0.0180 '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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.7236(4) 0.5285(3) 0.4670(4) 0.0510(10) Uani d . . . 1.0 . .
C C2 0.6435(5) 0.4437(3) 0.4713(4) 0.0565(11) Uani d . . . 1.0 . .
H H2 0.6004 0.4268 0.541 0.068 Uiso calc U . R 1.0 . .
C C3 0.6253(5) 0.3833(4) 0.3760(5) 0.0656(13) Uani d . . . 1.0 . .
H H3 0.5683 0.3263 0.3802 0.079 Uiso calc U . R 1.0 . .
C C4 0.6894(6) 0.4055(4) 0.2749(5) 0.0706(14) Uani d . . . 1.0 . .
H H4 0.6776 0.3637 0.2096 0.085 Uiso calc U . R 1.0 . .
C C5 0.7699(6) 0.4882(4) 0.2694(5) 0.0715(14) Uani d . . . 1.0 . .
H H5 0.8147 0.5037 0.2 0.086 Uiso calc U . R 1.0 . .
C C6 0.7867(5) 0.5500(4) 0.3651(4) 0.0634(12) Uani d . . . 1.0 . .
H H6 0.8423 0.6076 0.36 0.076 Uiso calc U . R 1.0 . .
C C7 0.8026(4) 0.7203(3) 0.5370(4) 0.0545(11) Uani d . . . 1.0 . .
C C8 0.7042(5) 0.7757(4) 0.4714(5) 0.0679(14) Uani d . . . 1.0 . .
H H8 0.6091 0.7526 0.4583 0.082 Uiso calc U . R 1.0 . .
C C9 0.7429(5) 0.8643(4) 0.4245(6) 0.0755(15) Uani d . . . 1.0 . .
H H9 0.6739 0.9014 0.3803 0.091 Uiso calc U . R 1.0 . .
C C10 0.8790(6) 0.8986(4) 0.4415(5) 0.0777(17) Uani d . . . 1.0 . .
H H10 0.9054 0.9588 0.4082 0.093 Uiso calc U . R 1.0 . .
C C11 0.9769(6) 0.8454(5) 0.5068(5) 0.0775(17) Uani d . . . 1.0 . .
H H11 1.0713 0.8697 0.5202 0.093 Uiso calc U . R 1.0 . .
C C12 0.9404(5) 0.7573(4) 0.5534(4) 0.0659(14) Uani d . . . 1.0 . .
H H12 1.0105 0.721 0.5975 0.079 Uiso calc U . R 1.0 . .
C C13 0.5884(5) 0.6156(3) 0.6593(3) 0.0505(10) Uani d . . . 1.0 . .
C C14 0.5732(6) 0.6189(4) 0.7788(3) 0.0738(16) Uani d . . . 1.0 . .
C C15 0.4375(8) 0.6190(5) 0.8198(4) 0.106(3) Uani d . . . 1.0 . .
C C16 0.3190(7) 0.6219(5) 0.7435(4) 0.090(2) Uani d . . . 1.0 . .
H H16 0.2266 0.6234 0.7733 0.107 Uiso calc U . R 1.0 . .
C C17 0.3311(5) 0.6227(3) 0.6259(4) 0.0579(11) Uani d . . . 1.0 . .
H H17 0.2487 0.6262 0.5744 0.069 Uiso calc U . R 1.0 . .
C C18 0.4666(4) 0.6182(3) 0.5844(3) 0.0451(9) Uani d . . . 1.0 . .
H H18 0.4768 0.6169 0.5031 0.054 Uiso calc U . R 1.0 . .
C C20 0.8030(7) 0.6894(5) 0.8641(5) 0.0780(17) Uani d . . . 1.0 . .
H H20 0.8565 0.6746 0.7937 0.094 Uiso calc U . R 1.0 A 1
C C23 0.9625(9) 0.8628(8) 0.9468(6) 0.114(3) Uani d . . . 1.0 . .
H H23 1.0368 0.9142 0.9379 0.137 Uiso calc U . R 1.0 B 1
C C25 0.7465(6) 0.7918(4) 0.8428(4) 0.0650(13) Uani d . . . 1.0 . .
H H25 0.6836 0.7914 0.7701 0.078 Uiso calc U . R 1.0 C 1
C C27 0.6603(6) 0.8252(5) 0.9398(5) 0.0766(15) Uani d . . . 1.0 . .
H H27A 0.5778 0.781 0.9472 0.092 Uiso calc U . R 1.0 . .
H H27B 0.6231 0.8915 0.923 0.092 Uiso calc U . R 1.0 . .
C C28 0.7528(6) 0.8262(5) 1.0543(4) 0.0738(15) Uani d . . . 1.0 . .
H H28 0.6951 0.8419 1.122 0.089 Uiso calc U . R 1.0 D 1
C C29 0.8754(6) 0.8946(5) 1.0452(4) 0.0788(16) Uani d . . . 1.0 . .
H H29A 0.9354 0.8943 1.1184 0.095 Uiso calc U . R 1.0 . .
H H29B 0.8396 0.9617 1.0313 0.095 Uiso calc U . R 1.0 . .
C C19A 0.3725(13) 0.6469(11) 0.9477(8) 0.066(3) Uani d . P . 0.484(7) E 1
H H19A 0.4518 0.6571 1.0053 0.099 Uiso calc U P R 0.484(7) E 1
H H19B 0.3123 0.5933 0.9728 0.099 Uiso calc U P R 0.484(7) E 1
H H19C 0.3153 0.7066 0.9399 0.099 Uiso calc U P R 0.484(7) E 1
C C21A 0.918(2) 0.7013(14) 0.9586(16) 0.061(4) Uani d . P . 0.484(7) E 1
H H21A 0.9712 0.6383 0.9679 0.074 Uiso calc U P R 0.484(7) E 1
C C22A 1.026(2) 0.7824(19) 0.9462(16) 0.093(7) Uani d . P . 0.484(7) E 1
H H22A 1.0996 0.7797 1.0111 0.111 Uiso calc U P R 0.484(7) E 1
H H22B 1.0745 0.7746 0.8728 0.111 Uiso calc U P R 0.484(7) E 1
C C24A 0.856(4) 0.868(2) 0.833(2) 0.108(12) Uani d . P . 0.484(7) E 1
H H24C 0.8101 0.9334 0.8267 0.13 Uiso calc U P R 0.484(7) E 1
H H24B 0.9096 0.8576 0.7622 0.13 Uiso calc U P R 0.484(7) E 1
C C28A 0.830(3) 0.7174(16) 1.068(3) 0.080(9) Uani d . P . 0.484(7) E 1
H H28C 0.894 0.7152 1.1389 0.095 Uiso calc U P R 0.484(7) E 1
H H28B 0.7569 0.6658 1.0728 0.095 Uiso calc U P R 0.484(7) E 1
C C30A 0.6644(12) 0.5254(8) 0.9287(8) 0.064(3) Uani d . P . 0.484(7) E 1
H H30A 0.5616 0.5193 0.9429 0.077 Uiso calc U P R 0.484(7) E 1
H H30B 0.7201 0.5251 1.0041 0.077 Uiso calc U P R 0.484(7) E 1
C C31A 0.713(2) 0.441(2) 0.850(3) 0.075(9) Uani d . P . 0.484(7) E 1
H H31A 0.8034 0.4455 0.8162 0.09 Uiso calc U P R 0.484(7) E 1
C C32A 0.6314(9) 0.3649(8) 0.8289(7) 0.052(2) Uani d . P . 0.484(7) E 1
H H32A 0.5373 0.3685 0.8552 0.063 Uiso calc U P R 0.484(7) E 1
C C43A 0.618(2) 0.1083(17) 0.7224(18) 0.067(7) Uani d . P . 0.484(7) E 1
H H43A 0.556 0.0539 0.7276 0.081 Uiso calc U P R 0.484(7) E 1
C C44A 0.581(5) 0.203(4) 0.768(3) 0.090(12) Uani d . P . 0.484(7) E 1
H H44A 0.4898 0.2124 0.7985 0.107 Uiso calc U P R 0.484(7) E 1
C C45A 0.669(2) 0.2730(14) 0.7687(12) 0.046(3) Uani d . P . 0.484(7) E 1
C C46A 0.801(2) 0.2700(13) 0.7164(12) 0.059(3) Uani d . P . 0.484(7) E 1
H H46A 0.8567 0.3274 0.7106 0.071 Uiso calc U P R 0.484(7) E 1
C C47A 0.847(3) 0.183(3) 0.674(3) 0.084(11) Uani d . P . 0.484(7) E 1
H H47A 0.9412 0.1773 0.6477 0.101 Uiso calc U P R 0.484(7) E 1
C C48A 0.750(3) 0.101(3) 0.670(2) 0.066(7) Uani d . P . 0.484(7) E 1
H H48A 0.7755 0.042 0.6318 0.08 Uiso calc U P R 0.484(7) E 1
C C19B 0.4478(14) 0.5912(11) 0.9503(8) 0.076(3) Uani d . P . 0.516(7) E 2
H H19D 0.5403 0.6124 0.9853 0.114 Uiso calc U P R 0.516(7) E 2
H H19E 0.439 0.5204 0.9582 0.114 Uiso calc U P R 0.516(7) E 2
H H19F 0.3706 0.6232 0.9897 0.114 Uiso calc U P R 0.516(7) E 2
C C21B 0.8694(18) 0.6837(15) 0.9931(13) 0.066(4) Uani d . P . 0.516(7) E 2
H H21B 0.8908 0.6143 1.014 0.079 Uiso calc U P R 0.516(7) E 2
C C22B 1.008(2) 0.7403(15) 0.9867(13) 0.077(5) Uani d . P . 0.516(7) E 2
H H22C 1.0685 0.7108 0.9282 0.092 Uiso calc U P R 0.516(7) E 2
H H22D 1.0625 0.7392 1.0627 0.092 Uiso calc U P R 0.516(7) E 2
C C24B 0.890(3) 0.853(2) 0.835(2) 0.082(7) Uani d . P . 0.516(7) E 2
H H24A 0.9531 0.8201 0.7818 0.099 Uiso calc U P R 0.516(7) E 2
H H24D 0.8665 0.9184 0.8035 0.099 Uiso calc U P R 0.516(7) E 2
C C28B 0.787(3) 0.730(2) 1.085(3) 0.087(8) Uani d . P . 0.516(7) E 2
H H28A 0.6975 0.6925 1.0947 0.104 Uiso calc U P R 0.516(7) E 2
H H28D 0.8437 0.7288 1.1596 0.104 Uiso calc U P R 0.516(7) E 2
C C30B 0.8012(12) 0.5183(7) 0.8637(8) 0.062(3) Uani d . P . 0.516(7) E 2
H H30C 0.8752 0.5282 0.807 0.075 Uiso calc U P R 0.516(7) E 2
H H30D 0.85 0.5113 0.9414 0.075 Uiso calc U P R 0.516(7) E 2
C C31B 0.724(2) 0.4333(14) 0.836(2) 0.056(6) Uani d . P . 0.516(7) E 2
H H31B 0.633 0.424 0.866 0.067 Uiso calc U P R 0.516(7) E 2
C C32B 0.7789(8) 0.3623(6) 0.7654(7) 0.047(2) Uani d . P . 0.516(7) E 2
H H32B 0.8613 0.3811 0.7265 0.057 Uiso calc U P R 0.516(7) E 2
C C43B 0.659(2) 0.0657(11) 0.7098(13) 0.064(4) Uani d . P . 0.516(7) E 2
H H43B 0.6331 -0.001 0.7009 0.077 Uiso calc U P R 0.516(7) E 2
C C44B 0.560(2) 0.136(2) 0.7462(19) 0.078(8) Uani d . P . 0.516(7) E 2
H H44B 0.4657 0.1152 0.7597 0.094 Uiso calc U P R 0.516(7) E 2
C C45B 0.821(2) 0.195(2) 0.697(2) 0.059(7) Uani d . P . 0.516(7) E 2
H H45B 0.9089 0.2184 0.6714 0.071 Uiso calc U P R 0.516(7) E 2
C C46B 0.7293(19) 0.2634(10) 0.7417(10) 0.041(3) Uani d . P . 0.516(7) E 2
C C47B 0.795(3) 0.099(2) 0.687(2) 0.069(6) Uani d . P . 0.516(7) E 2
H H47B 0.8676 0.0552 0.666 0.083 Uiso calc U P R 0.516(7) E 2
C C48B 0.591(2) 0.222(3) 0.7613(18) 0.065(9) Uani d . P . 0.516(7) E 2
H H48B 0.5192 0.2646 0.7874 0.079 Uiso calc U P R 0.516(7) E 2
N N1 0.6923(7) 0.6160(4) 0.8628(4) 0.1026(19) Uani d . . . 1.0 . .
P P1 0.76576(12) 0.59975(10) 0.59921(10) 0.0604(3) Uani d . . . 1.0 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.379(7) ?
C1 C2 . 1.387(6) ?
C1 P1 . 1.839(4) ?
C2 C3 . 1.381(7) ?
C2 H2 . 0.95 ?
C3 C4 . 1.378(7) ?
C3 H3 . 0.95 ?
C4 C5 . 1.365(8) ?
C4 H4 . 0.95 ?
C5 C6 . 1.397(7) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C7 C8 . 1.388(7) ?
C7 C12 . 1.390(6) ?
C7 P1 . 1.844(5) ?
C8 C9 . 1.387(7) ?
C8 H8 . 0.95 ?
C9 C10 . 1.363(7) ?
C9 H9 . 0.95 ?
C10 C11 . 1.366(9) ?
C10 H10 . 0.95 ?
C11 C12 . 1.375(9) ?
C11 H11 . 0.95 ?
C12 H12 . 0.95 ?
C13 C18 . 1.395(5) ?
C13 C14 . 1.398(6) ?
C13 P1 . 1.849(4) ?
C14 C15 . 1.382(9) ?
C14 N1 . 1.438(7) ?
C15 C16 . 1.380(9) ?
C15 C19B . 1.554(11) ?
C15 C19A . 1.674(11) ?
C16 C17 . 1.370(6) ?
C16 H16 . 0.95 ?
C17 C18 . 1.384(6) ?
C17 H17 . 0.95 ?
C18 H18 . 0.95 ?
C20 N1 . 1.446(8) ?
C20 C21A . 1.50(2) ?
C20 C25 . 1.516(8) ?
C20 C21B . 1.586(16) ?
C20 H20 . 1.0 ?
C23 C22A . 1.25(3) ?
C23 C24B . 1.43(3) ?
C23 C29 . 1.501(8) ?
C23 C24A . 1.61(3) ?
C23 C22B . 1.79(2) ?
C23 H23 . 1.0 ?
C25 C24A . 1.48(3) ?
C25 C27 . 1.491(7) ?
C25 C24B . 1.59(3) ?
C25 H25 . 1.0 ?
C27 C28 . 1.542(7) ?
C27 H27A . 0.99 ?
C27 H27B . 0.99 ?
C28 C28B . 1.40(3) ?
C28 C29 . 1.492(8) ?
C28 C28A . 1.66(3) ?
C28 H28 . 1.0 ?
C29 H29A . 0.99 ?
C29 H29B . 0.99 ?
C19A H19A . 0.98 ?
C19A H19B . 0.98 ?
C19A H19C . 0.98 ?
C21A C22A . 1.52(2) ?
C21A C28A . 1.56(3) ?
C21A H21A . 1.0 ?
C22A H22A . 0.99 ?
C22A H22B . 0.99 ?
C24A H24C . 0.99 ?
C24A H24B . 0.99 ?
C28A H28C . 0.99 ?
C28A H28B . 0.99 ?
C30A N1 . 1.489(10) ?
C30A C31A . 1.55(4) ?
C30A H30A . 0.99 ?
C30A H30B . 0.99 ?
C31A C32A . 1.32(3) ?
C31A H31A . 0.95 ?
C32A C45A . 1.49(2) ?
C32A H32A . 0.95 ?
C43A C48A . 1.42(4) ?
C43A C44A . 1.45(5) ?
C43A H43A . 0.95 ?
C44A C45A . 1.27(5) ?
C44A H44A . 0.95 ?
C45A C46A . 1.404(17) ?
C46A C47A . 1.37(5) ?
C46A H46A . 0.95 ?
C47A C48A . 1.45(5) ?
C47A H47A . 0.95 ?
C48A H48A . 0.95 ?
C19B H19D . 0.98 ?
C19B H19E . 0.98 ?
C19B H19F . 0.98 ?
C21B C28B . 1.49(3) ?
C21B C22B . 1.52(2) ?
C21B H21B . 1.0 ?
C22B H22C . 0.99 ?
C22B H22D . 0.99 ?
C24B H24A . 0.99 ?
C24B H24D . 0.99 ?
C28B H28A . 0.99 ?
C28B H28D . 0.99 ?
C30B C31B . 1.40(3) ?
C30B N1 . 1.684(11) ?
C30B H30C . 0.99 ?
C30B H30D . 0.99 ?
C31B C32B . 1.39(3) ?
C31B H31B . 0.95 ?
C32B C46B . 1.456(15) ?
C32B H32B . 0.95 ?
C43B C47B . 1.40(4) ?
C43B C44B . 1.41(3) ?
C43B H43B . 0.95 ?
C44B C48B . 1.23(5) ?
C44B H44B . 0.95 ?
C45B C47B . 1.34(4) ?
C45B C46B . 1.39(3) ?
C45B H45B . 0.95 ?
C46B C48B . 1.44(3) ?
C47B H47B . 0.95 ?
C48B H48B . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 118.0(4) ?
C6 C1 P1 . . 120.9(4) ?
C2 C1 P1 . . 120.5(4) ?
C3 C2 C1 . . 121.1(5) ?
C3 C2 H2 . . 119.4 ?
C1 C2 H2 . . 119.4 ?
C4 C3 C2 . . 120.3(5) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C5 C4 C3 . . 119.4(5) ?
C5 C4 H4 . . 120.3 ?
C3 C4 H4 . . 120.3 ?
C4 C5 C6 . . 120.4(5) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C1 C6 C5 . . 120.8(5) ?
C1 C6 H6 . . 119.6 ?
C5 C6 H6 . . 119.6 ?
C8 C7 C12 . . 117.3(5) ?
C8 C7 P1 . . 124.8(3) ?
C12 C7 P1 . . 117.8(4) ?
C9 C8 C7 . . 120.8(5) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C10 C9 C8 . . 120.6(6) ?
C10 C9 H9 . . 119.7 ?
C8 C9 H9 . . 119.7 ?
C9 C10 C11 . . 119.3(5) ?
C9 C10 H10 . . 120.4 ?
C11 C10 H10 . . 120.4 ?
C10 C11 C12 . . 120.8(5) ?
C10 C11 H11 . . 119.6 ?
C12 C11 H11 . . 119.6 ?
C11 C12 C7 . . 121.1(6) ?
C11 C12 H12 . . 119.4 ?
C7 C12 H12 . . 119.4 ?
C18 C13 C14 . . 119.2(4) ?
C18 C13 P1 . . 119.4(3) ?
C14 C13 P1 . . 121.2(4) ?
C15 C14 C13 . . 119.0(4) ?
C15 C14 N1 . . 117.6(4) ?
C13 C14 N1 . . 123.3(5) ?
C16 C15 C14 . . 120.3(4) ?
C16 C15 C19B . . 129.2(7) ?
C14 C15 C19B . . 108.9(7) ?
C16 C15 C19A . . 103.8(7) ?
C14 C15 C19A . . 133.6(6) ?
C17 C16 C15 . . 121.8(5) ?
C17 C16 H16 . . 119.1 ?
C15 C16 H16 . . 119.1 ?
C16 C17 C18 . . 118.1(5) ?
C16 C17 H17 . . 120.9 ?
C18 C17 H17 . . 120.9 ?
C17 C18 C13 . . 121.4(3) ?
C17 C18 H18 . . 119.3 ?
C13 C18 H18 . . 119.3 ?
N1 C20 C21A . . 124.8(8) ?
N1 C20 C25 . . 113.6(5) ?
C21A C20 C25 . . 104.3(8) ?
N1 C20 C21B . . 102.7(9) ?
C25 C20 C21B . . 108.3(8) ?
N1 C20 H20 . . 104.0 ?
C21A C20 H20 . . 104.0 ?
C25 C20 H20 . . 104.0 ?
C22A C23 C29 . . 122.5(11) ?
C24B C23 C29 . . 117.3(12) ?
C22A C23 C24A . . 108.1(17) ?
C29 C23 C24A . . 105.6(14) ?
C24B C23 C22B . . 103.8(15) ?
C29 C23 C22B . . 102.1(7) ?
C22A C23 H23 . . 106.5 ?
C29 C23 H23 . . 106.5 ?
C24A C23 H23 . . 106.5 ?
C24A C25 C27 . . 104.4(13) ?
C24A C25 C20 . . 115.8(15) ?
C27 C25 C20 . . 111.2(5) ?
C27 C25 C24B . . 111.9(11) ?
C20 C25 C24B . . 102.1(13) ?
C24A C25 H25 . . 108.4 ?
C27 C25 H25 . . 108.4 ?
C20 C25 H25 . . 108.4 ?
C25 C27 C28 . . 110.2(4) ?
C25 C27 H27A . . 109.6 ?
C28 C27 H27A . . 109.6 ?
C25 C27 H27B . . 109.6 ?
C28 C27 H27B . . 109.6 ?
H27A C27 H27B . . 108.1 ?
C28B C28 C29 . . 116.6(14) ?
C28B C28 C27 . . 108.5(13) ?
C29 C28 C27 . . 110.1(5) ?
C29 C28 C28A . . 103.7(10) ?
C27 C28 C28A . . 107.2(11) ?
C29 C28 H28 . . 111.8 ?
C27 C28 H28 . . 111.8 ?
C28A C28 H28 . . 111.8 ?
C28 C29 C23 . . 108.9(5) ?
C28 C29 H29A . . 109.9 ?
C23 C29 H29A . . 109.9 ?
C28 C29 H29B . . 109.9 ?
C23 C29 H29B . . 109.9 ?
H29A C29 H29B . . 108.3 ?
C15 C19A H19A . . 109.5 ?
C15 C19A H19B . . 109.5 ?
H19A C19A H19B . . 109.5 ?
C15 C19A H19C . . 109.5 ?
H19A C19A H19C . . 109.5 ?
H19B C19A H19C . . 109.5 ?
C20 C21A C22A . . 117.9(13) ?
C20 C21A C28A . . 102.3(15) ?
C22A C21A C28A . . 110.9(16) ?
C20 C21A H21A . . 108.4 ?
C22A C21A H21A . . 108.4 ?
C28A C21A H21A . . 108.4 ?
C23 C22A C21A . . 109.0(17) ?
C23 C22A H22A . . 109.9 ?
C21A C22A H22A . . 109.9 ?
C23 C22A H22B . . 109.9 ?
C21A C22A H22B . . 109.9 ?
H22A C22A H22B . . 108.3 ?
C25 C24A C23 . . 107.5(15) ?
C25 C24A H24C . . 110.2 ?
C23 C24A H24C . . 110.2 ?
C25 C24A H24B . . 110.2 ?
C23 C24A H24B . . 110.2 ?
H24C C24A H24B . . 108.5 ?
C21A C28A C28 . . 107.3(16) ?
C21A C28A H28C . . 110.2 ?
C28 C28A H28C . . 110.2 ?
C21A C28A H28B . . 110.2 ?
C28 C28A H28B . . 110.2 ?
H28C C28A H28B . . 108.5 ?
N1 C30A C31A . . 104.6(11) ?
N1 C30A H30A . . 110.8 ?
C31A C30A H30A . . 110.8 ?
N1 C30A H30B . . 110.8 ?
C31A C30A H30B . . 110.8 ?
H30A C30A H30B . . 108.9 ?
C32A C31A C30A . . 120.7(19) ?
C32A C31A H31A . . 119.6 ?
C30A C31A H31A . . 119.6 ?
C31A C32A C45A . . 127.5(17) ?
C31A C32A H32A . . 116.2 ?
C45A C32A H32A . . 116.2 ?
C48A C43A C44A . . 117.(3) ?
C48A C43A H43A . . 121.4 ?
C44A C43A H43A . . 121.4 ?
C45A C44A C43A . . 121.(3) ?
C45A C44A H44A . . 119.6 ?
C43A C44A H44A . . 119.6 ?
C44A C45A C46A . . 124.(3) ?
C44A C45A C32A . . 118.(2) ?
C46A C45A C32A . . 118.(2) ?
C47A C46A C45A . . 119.0(18) ?
C47A C46A H46A . . 120.5 ?
C45A C46A H46A . . 120.5 ?
C46A C47A C48A . . 119.(2) ?
C46A C47A H47A . . 120.6 ?
C48A C47A H47A . . 120.6 ?
C43A C48A C47A . . 119.(2) ?
C43A C48A H48A . . 120.5 ?
C47A C48A H48A . . 120.5 ?
C15 C19B H19D . . 109.5 ?
C15 C19B H19E . . 109.5 ?
H19D C19B H19E . . 109.5 ?
C15 C19B H19F . . 109.5 ?
H19D C19B H19F . . 109.5 ?
H19E C19B H19F . . 109.5 ?
C28B C21B C22B . . 107.5(18) ?
C28B C21B C20 . . 117.2(16) ?
C22B C21B C20 . . 102.7(12) ?
C28B C21B H21B . . 109.7 ?
C22B C21B H21B . . 109.7 ?
C20 C21B H21B . . 109.7 ?
C21B C22B C23 . . 107.3(12) ?
C21B C22B H22C . . 110.3 ?
C23 C22B H22C . . 110.3 ?
C21B C22B H22D . . 110.3 ?
C23 C22B H22D . . 110.3 ?
H22C C22B H22D . . 108.5 ?
C23 C24B C25 . . 111.2(17) ?
C23 C24B H24A . . 109.4 ?
C25 C24B H24A . . 109.4 ?
C23 C24B H24D . . 109.4 ?
C25 C24B H24D . . 109.4 ?
H24A C24B H24D . . 108.0 ?
C28 C28B C21B . . 110.(2) ?
C28 C28B H28A . . 109.7 ?
C21B C28B H28A . . 109.7 ?
C28 C28B H28D . . 109.7 ?
C21B C28B H28D . . 109.7 ?
H28A C28B H28D . . 108.2 ?
C31B C30B N1 . . 111.0(10) ?
C31B C30B H30C . . 109.4 ?
N1 C30B H30C . . 109.4 ?
C31B C30B H30D . . 109.4 ?
N1 C30B H30D . . 109.4 ?
H30C C30B H30D . . 108.0 ?
C32B C31B C30B . . 121.3(18) ?
C32B C31B H31B . . 119.4 ?
C30B C31B H31B . . 119.4 ?
C31B C32B C46B . . 129.9(13) ?
C31B C32B H32B . . 115.1 ?
C46B C32B H32B . . 115.1 ?
C47B C43B C44B . . 116.9(19) ?
C47B C43B H43B . . 121.6 ?
C44B C43B H43B . . 121.6 ?
C48B C44B C43B . . 123.(2) ?
C48B C44B H44B . . 118.5 ?
C43B C44B H44B . . 118.5 ?
C47B C45B C46B . . 126.(2) ?
C47B C45B H45B . . 117.2 ?
C46B C45B H45B . . 117.2 ?
C45B C46B C48B . . 111.9(19) ?
C45B C46B C32B . . 120.1(16) ?
C48B C46B C32B . . 128.(2) ?
C45B C47B C43B . . 118.(3) ?
C45B C47B H47B . . 121.1 ?
C43B C47B H47B . . 121.1 ?
C44B C48B C46B . . 124.(2) ?
C44B C48B H48B . . 118.0 ?
C46B C48B H48B . . 118.0 ?
C14 N1 C20 . . 121.2(4) ?
C14 N1 C30A . . 102.6(6) ?
C20 N1 C30A . . 136.2(6) ?
C14 N1 C30B . . 118.3(5) ?
C20 N1 C30B . . 96.9(5) ?
C1 P1 C7 . . 100.9(2) ?
C1 P1 C13 . . 102.63(19) ?
C7 P1 C13 . . 103.47(19) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -1.1(6) ?
P1 C1 C2 C3 . . . . -172.2(4) ?
C1 C2 C3 C4 . . . . 1.3(7) ?
C2 C3 C4 C5 . . . . -0.6(8) ?
C3 C4 C5 C6 . . . . -0.3(8) ?
C2 C1 C6 C5 . . . . 0.1(7) ?
P1 C1 C6 C5 . . . . 171.2(4) ?
C4 C5 C6 C1 . . . . 0.6(8) ?
C12 C7 C8 C9 . . . . -0.1(7) ?
P1 C7 C8 C9 . . . . -177.7(4) ?
C7 C8 C9 C10 . . . . 0.4(8) ?
C8 C9 C10 C11 . . . . -1.0(8) ?
C9 C10 C11 C12 . . . . 1.3(8) ?
C10 C11 C12 C7 . . . . -1.0(7) ?
C8 C7 C12 C11 . . . . 0.4(7) ?
P1 C7 C12 C11 . . . . 178.2(4) ?
C18 C13 C14 C15 . . . . 3.6(7) ?
P1 C13 C14 C15 . . . . -172.3(5) ?
C18 C13 C14 N1 . . . . 179.6(4) ?
P1 C13 C14 N1 . . . . 3.7(6) ?
C13 C14 C15 C16 . . . . -3.9(9) ?
N1 C14 C15 C16 . . . . 179.9(6) ?
C13 C14 C15 C19B . . . . 162.9(7) ?
N1 C14 C15 C19B . . . . -13.4(9) ?
C13 C14 C15 C19A . . . . -163.8(9) ?
N1 C14 C15 C19A . . . . 20.0(12) ?
C14 C15 C16 C17 . . . . 1.3(10) ?
C19B C15 C16 C17 . . . . -162.4(9) ?
C19A C15 C16 C17 . . . . 166.5(7) ?
C15 C16 C17 C18 . . . . 1.5(8) ?
C16 C17 C18 C13 . . . . -1.7(7) ?
C14 C13 C18 C17 . . . . -0.9(6) ?
P1 C13 C18 C17 . . . . 175.2(3) ?
N1 C20 C25 C24A . . . . -174.6(13) ?
C21A C20 C25 C24A . . . . 46.5(15) ?
N1 C20 C25 C27 . . . . 66.5(6) ?
C21A C20 C25 C27 . . . . -72.4(9) ?
C21B C20 C25 C27 . . . . -46.8(9) ?
N1 C20 C25 C24B . . . . -174.0(10) ?
C21B C20 C25 C24B . . . . 72.7(13) ?
C24A C25 C27 C28 . . . . -65.1(15) ?
C20 C25 C27 C28 . . . . 60.4(7) ?
C24B C25 C27 C28 . . . . -53.1(14) ?
C25 C27 C28 C28B . . . . -68.0(15) ?
C25 C27 C28 C29 . . . . 60.8(7) ?
C25 C27 C28 C28A . . . . -51.4(12) ?
C28B C28 C29 C23 . . . . 65.5(15) ?
C27 C28 C29 C23 . . . . -58.7(8) ?
C28A C28 C29 C23 . . . . 55.7(12) ?
C22A C23 C29 C28 . . . . -63.3(15) ?
C24B C23 C29 C28 . . . . 55.6(17) ?
C24A C23 C29 C28 . . . . 60.9(13) ?
C22B C23 C29 C28 . . . . -57.1(9) ?
N1 C20 C21A C22A . . . . -179.9(14) ?
C25 C20 C21A C22A . . . . -47.1(18) ?
N1 C20 C21A C28A . . . . -58.0(15) ?
C25 C20 C21A C28A . . . . 74.8(13) ?
C29 C23 C22A C21A . . . . 57.6(18) ?
C24A C23 C22A C21A . . . . -65.4(17) ?
C20 C21A C22A C23 . . . . 63.3(19) ?
C28A C21A C22A C23 . . . . -54.(2) ?
C27 C25 C24A C23 . . . . 68.(2) ?
C20 C25 C24A C23 . . . . -54.(2) ?
C22A C23 C24A C25 . . . . 65.(2) ?
C29 C23 C24A C25 . . . . -68.(2) ?
C20 C21A C28A C28 . . . . -69.5(16) ?
C22A C21A C28A C28 . . . . 57.(2) ?
C29 C28 C28A C21A . . . . -58.7(17) ?
C27 C28 C28A C21A . . . . 57.8(17) ?
N1 C30A C31A C32A . . . . -132.4(17) ?
C30A C31A C32A C45A . . . . -171.3(12) ?
C48A C43A C44A C45A . . . . -5.(4) ?
C43A C44A C45A C46A . . . . 7.(4) ?
C43A C44A C45A C32A . . . . -173.(2) ?
C31A C32A C45A C44A . . . . 172.(2) ?
C31A C32A C45A C46A . . . . -8.(2) ?
C44A C45A C46A C47A . . . . -8.(3) ?
C32A C45A C46A C47A . . . . 171.5(17) ?
C45A C46A C47A C48A . . . . 9.(3) ?
C44A C43A C48A C47A . . . . 6.(4) ?
C46A C47A C48A C43A . . . . -8.(4) ?
N1 C20 C21B C28B . . . . -77.(2) ?
C25 C20 C21B C28B . . . . 44.(2) ?
N1 C20 C21B C22B . . . . 165.8(10) ?
C25 C20 C21B C22B . . . . -73.9(12) ?
C28B C21B C22B C23 . . . . -61.7(17) ?
C20 C21B C22B C23 . . . . 62.5(12) ?
C24B C23 C22B C21B . . . . -61.5(14) ?
C29 C23 C22B C21B . . . . 60.8(10) ?
C29 C23 C24B C25 . . . . -48.(2) ?
C22B C23 C24B C25 . . . . 63.(2) ?
C27 C25 C24B C23 . . . . 47.(2) ?
C20 C25 C24B C23 . . . . -72.(2) ?
C29 C28 C28B C21B . . . . -64.(2) ?
C27 C28 C28B C21B . . . . 61.(2) ?
C22B C21B C28B C28 . . . . 63.(2) ?
C20 C21B C28B C28 . . . . -52.(3) ?
N1 C30B C31B C32B . . . . 140.1(11) ?
C30B C31B C32B C46B . . . . 168.5(11) ?
C47B C43B C44B C48B . . . . -2.(4) ?
C47B C45B C46B C48B . . . . -9.(3) ?
C47B C45B C46B C32B . . . . 169.8(18) ?
C31B C32B C46B C45B . . . . -160.7(17) ?
C31B C32B C46B C48B . . . . 18.(2) ?
C46B C45B C47B C43B . . . . 9.(3) ?
C44B C43B C47B C45B . . . . -3.(3) ?
C43B C44B C48B C46B . . . . 1.(4) ?
C45B C46B C48B C44B . . . . 4.(3) ?
C32B C46B C48B C44B . . . . -174.9(18) ?
C15 C14 N1 C20 . . . . -124.5(6) ?
C13 C14 N1 C20 . . . . 59.5(8) ?
C15 C14 N1 C30A . . . . 57.4(7) ?
C13 C14 N1 C30A . . . . -118.6(6) ?
C15 C14 N1 C30B . . . . 116.6(7) ?
C13 C14 N1 C30B . . . . -59.5(7) ?
C21A C20 N1 C14 . . . . 170.1(10) ?
C25 C20 N1 C14 . . . . 40.9(8) ?
C21B C20 N1 C14 . . . . 157.6(8) ?
C21A C20 N1 C30A . . . . -12.6(15) ?
C25 C20 N1 C30A . . . . -141.8(9) ?
C25 C20 N1 C30B . . . . 170.0(6) ?
C21B C20 N1 C30B . . . . -73.4(8) ?
C31A C30A N1 C14 . . . . 78.5(10) ?
C31A C30A N1 C20 . . . . -99.1(11) ?
C31B C30B N1 C14 . . . . -35.2(13) ?
C31B C30B N1 C20 . . . . -166.3(12) ?
C6 C1 P1 C7 . . . . 31.2(4) ?
C2 C1 P1 C7 . . . . -157.9(3) ?
C6 C1 P1 C13 . . . . 137.8(4) ?
C2 C1 P1 C13 . . . . -51.3(4) ?
C8 C7 P1 C1 . . . . 62.1(4) ?
C12 C7 P1 C1 . . . . -115.5(3) ?
C8 C7 P1 C13 . . . . -43.9(5) ?
C12 C7 P1 C13 . . . . 138.5(3) ?
C18 C13 P1 C1 . . . . -29.4(4) ?
C14 C13 P1 C1 . . . . 146.6(4) ?
C18 C13 P1 C7 . . . . 75.3(4) ?
C14 C13 P1 C7 . . . . -108.8(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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1870333'
_audit_update_record             
;
2018-09-28 deposited with the CCDC.
2019-01-17 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H41 Cl3 N P'
_chemical_formula_iupac          ?
_chemical_formula_weight         697.08
_chemical_absolute_configuration unk

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.14120(10)
_cell_length_b                   17.5089(2)
_cell_length_c                   19.7319(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3503.62(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9926
_cell_measurement_theta_min      2.2391
_cell_measurement_theta_max      68.2675
_cell_measurement_temperature    173

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1464

_exptl_absorpt_coefficient_mu    3.034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.58
_exptl_absorpt_correction_T_max  0.75

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  goniometer
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            16906
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_theta_min         3.38
_diffrn_reflns_theta_max         68.26
_diffrn_reflns_theta_full        68.26
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             6126
_reflns_number_gt                6056
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1009
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_number_reflns         6126
_refine_ls_number_parameters     424
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0538P)²+1.4686P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.512
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 2490 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.036(3)

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'
N N 0.0311 0.0180 '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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.7485(3) 0.54933(15) 0.04756(14) 0.0232(5) Uani d . . . 1 . .
C C2 0.6224(3) 0.53193(14) 0.07023(12) 0.0201(5) Uani d . . . 1 . .
C C3 0.5301(3) 0.59329(15) 0.08190(12) 0.0209(5) Uani d . . . 1 . .
C C4 0.4006(3) 0.58034(16) 0.10743(13) 0.0247(5) Uani d . . . 1 . .
H H4 0.3723 0.5295 0.1159 0.03 Uiso calc U . R 1 . .
C C5 0.3161(3) 0.63983(18) 0.12000(15) 0.0302(6) Uani d . . . 1 . .
H H5 0.2314 0.6298 0.1385 0.036 Uiso calc U . R 1 . .
C C6 0.3536(3) 0.71592(17) 0.10582(16) 0.0332(7) Uani d . . . 1 . .
H H6 0.2941 0.7567 0.1141 0.04 Uiso calc U . R 1 . .
C C7 0.4761(3) 0.73026(17) 0.08010(15) 0.0311(6) Uani d . . . 1 . .
H H7 0.5008 0.7814 0.0703 0.037 Uiso calc U . R 1 . .
C C8 0.5673(3) 0.67037(15) 0.06767(13) 0.0246(5) Uani d . . . 1 . .
C C9 0.6940(3) 0.68434(15) 0.04123(15) 0.0291(6) Uani d . . . 1 . .
H H9 0.719 0.7351 0.0299 0.035 Uiso calc U . R 1 . .
C C10 0.7808(3) 0.62659(16) 0.03171(16) 0.0301(6) Uani d . . . 1 . .
H H10 0.8656 0.6378 0.0139 0.036 Uiso calc U . R 1 . .
C C11 0.9925(3) 0.51656(17) -0.01955(14) 0.0292(6) Uani d . . . 1 . .
C C12 0.9715(3) 0.5008(2) -0.08769(18) 0.0473(9) Uani d . . . 1 . .
H H12 0.899 0.4698 -0.1008 0.057 Uiso calc U . R 1 . .
C C13 1.0552(4) 0.5299(3) -0.13647(18) 0.0569(11) Uani d . . . 1 . .
H H13 1.0385 0.5197 -0.183 0.068 Uiso calc U . R 1 . .
C C14 1.1630(3) 0.5738(2) -0.11845(17) 0.0417(8) Uani d . . . 1 . .
H H14 1.2201 0.5937 -0.1523 0.05 Uiso calc U . R 1 . .
C C15 1.1868(3) 0.58822(17) -0.05086(16) 0.0325(6) Uani d . . . 1 . .
H H15 1.2613 0.6177 -0.0378 0.039 Uiso calc U . R 1 . .
C C16 1.1019(3) 0.55972(16) -0.00186(15) 0.0290(6) Uani d . . . 1 . .
H H16 1.119 0.5699 0.0446 0.035 Uiso calc U . R 1 . .
C C17 0.9688(3) 0.49105(16) 0.12139(15) 0.0275(6) Uani d . . . 1 . .
C C18 0.9455(3) 0.5496(2) 0.16709(16) 0.0374(7) Uani d . . . 1 . .
H H18 0.8777 0.5856 0.1581 0.045 Uiso calc U . R 1 . .
C C19 1.0197(4) 0.5561(2) 0.22575(18) 0.0490(9) Uani d . . . 1 . .
H H19 1.0011 0.596 0.257 0.059 Uiso calc U . R 1 . .
C C20 1.1198(4) 0.5055(2) 0.23921(18) 0.0481(8) Uani d . . . 1 . .
H H20 1.172 0.5111 0.2789 0.058 Uiso calc U . R 1 . .
C C21 1.1437(4) 0.4467(2) 0.1945(2) 0.0493(9) Uani d . . . 1 . .
H H21 1.2121 0.4111 0.2037 0.059 Uiso calc U . R 1 . .
C C22 1.0685(3) 0.43907(19) 0.13631(18) 0.0391(7) Uani d . . . 1 . .
H H22 1.0852 0.3978 0.1062 0.047 Uiso calc U . R 1 . .
C C23 0.5631(3) 0.43725(16) 0.15623(13) 0.0257(5) Uani d . . . 1 . .
H H23A 0.4821 0.4065 0.1625 0.031 Uiso calc U . R 1 . .
H H23B 0.5519 0.4851 0.1824 0.031 Uiso calc U . R 1 . .
C C24 0.6773(3) 0.39380(16) 0.18555(14) 0.0269(6) Uani d . . . 1 . .
H H24 0.7138 0.3533 0.1595 0.032 Uiso calc U . R 1 . .
C C25 0.7297(3) 0.40842(17) 0.24502(14) 0.0301(6) Uani d . . . 1 . .
H H25 0.6944 0.4511 0.2686 0.036 Uiso calc U . R 1 . .
C C26 0.8362(3) 0.36699(17) 0.27973(14) 0.0297(6) Uani d . . . 1 . .
C C27 0.8717(4) 0.3882(2) 0.34536(16) 0.0392(7) Uani d . . . 1 . .
H H27 0.8268 0.4293 0.3667 0.047 Uiso calc U . R 1 . .
C C28 0.9701(4) 0.3510(3) 0.37965(18) 0.0507(10) Uani d . . . 1 . .
H H28 0.9919 0.3661 0.4245 0.061 Uiso calc U . R 1 . .
C C29 1.0375(5) 0.2917(3) 0.3493(2) 0.0611(12) Uani d . . . 1 . .
H H29 1.1053 0.2655 0.3731 0.073 Uiso calc U . R 1 . .
C C30 1.0048(5) 0.2709(2) 0.2838(3) 0.0634(12) Uani d . . . 1 . .
H H30 1.0524 0.2311 0.262 0.076 Uiso calc U . R 1 . .
C C31 0.9044(4) 0.30700(19) 0.24974(18) 0.0444(8) Uani d . . . 1 . .
H H31 0.8814 0.2908 0.2053 0.053 Uiso calc U . R 1 . .
C C32 0.5919(2) 0.39299(14) 0.03622(13) 0.0213(5) Uani d . . . 1 . .
H H32 0.681 0.37 0.0437 0.026 Uiso calc U . R 1 . .
C C33 0.4864(3) 0.33076(15) 0.04817(14) 0.0254(5) Uani d . . . 1 . .
H H33 0.4899 0.3137 0.0965 0.03 Uiso calc U . R 1 . .
C C34 0.5160(3) 0.26277(16) 0.00170(16) 0.0315(6) Uani d . . . 1 . .
H H34A 0.4507 0.2218 0.0098 0.038 Uiso calc U . R 1 . .
H H34B 0.6047 0.2423 0.0121 0.038 Uiso calc U . R 1 . .
C C35 0.5104(3) 0.28782(17) -0.07278(16) 0.0323(6) Uani d . . . 1 . .
H H35 0.5303 0.2434 -0.1029 0.039 Uiso calc U . R 1 . .
C C36 0.3723(3) 0.31872(19) -0.08848(16) 0.0355(7) Uani d . . . 1 . .
H H36A 0.3679 0.3351 -0.1364 0.043 Uiso calc U . R 1 . .
H H36B 0.3061 0.2779 -0.0815 0.043 Uiso calc U . R 1 . .
C C37 0.3411(3) 0.38653(17) -0.04210(16) 0.0326(6) Uani d . . . 1 . .
H H37 0.2508 0.4064 -0.0524 0.039 Uiso calc U . R 1 . .
C C38 0.4433(3) 0.44968(16) -0.05352(14) 0.0294(6) Uani d . . . 1 . .
H H38A 0.4235 0.4936 -0.0237 0.035 Uiso calc U . R 1 . .
H H38B 0.439 0.4674 -0.1011 0.035 Uiso calc U . R 1 . .
C C39 0.5821(3) 0.41949(15) -0.03814(13) 0.0248(5) Uani d . . . 1 . .
H H39 0.6483 0.4608 -0.0466 0.03 Uiso calc U . R 1 . .
C C40 0.6126(3) 0.35069(16) -0.08378(15) 0.0309(6) Uani d . . . 1 . .
H H40A 0.6117 0.3669 -0.1319 0.037 Uiso calc U . R 1 . .
H H40B 0.7017 0.3308 -0.0732 0.037 Uiso calc U . R 1 . .
C C41 0.3485(3) 0.36161(17) 0.03241(15) 0.0302(6) Uani d . . . 1 . .
H H41A 0.329 0.4057 0.0622 0.036 Uiso calc U . R 1 . .
H H41B 0.2819 0.3215 0.0413 0.036 Uiso calc U . R 1 . .
C C42 0.5491(4) 0.68911(19) 0.25288(17) 0.0403(7) Uani d . . . 1 . .
H H42 0.5075 0.6849 0.2071 0.048 Uiso calc U . R 1 . .
Cl Cl1 0.66746(10) 0.61703(6) 0.25943(6) 0.0586(3) Uani d . . . 1 . .
Cl Cl2 0.42490(12) 0.67858(7) 0.31319(7) 0.0729(4) Uani d . . . 1 . .
Cl Cl3 0.62164(18) 0.77843(6) 0.25851(10) 0.1061(7) Uani d . . . 1 . .
N N1 0.5748(2) 0.45700(12) 0.08402(10) 0.0214(4) Uani d . . . 1 . .
P P1 0.87691(7) 0.47471(4) 0.04256(4) 0.02771(17) Uani d . . . 1 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.389(4) ?
C1 C10 . 1.426(4) ?
C1 P1 . 1.848(3) ?
C2 N1 . 1.424(3) ?
C2 C3 . 1.443(4) ?
C3 C4 . 1.424(4) ?
C3 C8 . 1.429(4) ?
C4 C5 . 1.372(4) ?
C4 H4 . 0.95 ?
C5 C6 . 1.413(5) ?
C5 H5 . 0.95 ?
C6 C7 . 1.365(5) ?
C6 H6 . 0.95 ?
C7 C8 . 1.420(4) ?
C7 H7 . 0.95 ?
C8 C9 . 1.408(4) ?
C9 C10 . 1.353(4) ?
C9 H9 . 0.95 ?
C10 H10 . 0.95 ?
C11 C16 . 1.387(4) ?
C11 C12 . 1.389(4) ?
C11 P1 . 1.847(3) ?
C12 C13 . 1.381(6) ?
C12 H12 . 0.95 ?
C13 C14 . 1.382(6) ?
C13 H13 . 0.95 ?
C14 C15 . 1.379(5) ?
C14 H14 . 0.95 ?
C15 C16 . 1.387(4) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C17 C18 . 1.385(5) ?
C17 C22 . 1.392(4) ?
C17 P1 . 1.836(3) ?
C18 C19 . 1.386(5) ?
C18 H18 . 0.95 ?
C19 C20 . 1.373(5) ?
C19 H19 . 0.95 ?
C20 C21 . 1.377(6) ?
C20 H20 . 0.95 ?
C21 C22 . 1.385(6) ?
C21 H21 . 0.95 ?
C22 H22 . 0.95 ?
C23 N1 . 1.471(3) ?
C23 C24 . 1.501(4) ?
C23 H23A . 0.99 ?
C23 H23B . 0.99 ?
C24 C25 . 1.314(4) ?
C24 H24 . 0.95 ?
C25 C26 . 1.470(4) ?
C25 H25 . 0.95 ?
C26 C31 . 1.390(5) ?
C26 C27 . 1.394(4) ?
C27 C28 . 1.370(5) ?
C27 H27 . 0.95 ?
C28 C29 . 1.379(7) ?
C28 H28 . 0.95 ?
C29 C30 . 1.384(7) ?
C29 H29 . 0.95 ?
C30 C31 . 1.373(6) ?
C30 H30 . 0.95 ?
C31 H31 . 0.95 ?
C32 N1 . 1.475(3) ?
C32 C39 . 1.542(4) ?
C32 C33 . 1.545(4) ?
C32 H32 . 1.0 ?
C33 C41 . 1.531(4) ?
C33 C34 . 1.532(4) ?
C33 H33 . 1.0 ?
C34 C35 . 1.535(4) ?
C34 H34A . 0.99 ?
C34 H34B . 0.99 ?
C35 C40 . 1.528(4) ?
C35 C36 . 1.533(4) ?
C35 H35 . 1.0 ?
C36 C37 . 1.532(4) ?
C36 H36A . 0.99 ?
C36 H36B . 0.99 ?
C37 C38 . 1.532(4) ?
C37 C41 . 1.535(4) ?
C37 H37 . 1.0 ?
C38 C39 . 1.534(4) ?
C38 H38A . 0.99 ?
C38 H38B . 0.99 ?
C39 C40 . 1.536(4) ?
C39 H39 . 1.0 ?
C40 H40A . 0.99 ?
C40 H40B . 0.99 ?
C41 H41A . 0.99 ?
C41 H41B . 0.99 ?
C42 Cl3 . 1.732(3) ?
C42 Cl2 . 1.743(3) ?
C42 Cl1 . 1.746(4) ?
C42 H42 . 1.0 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C10 . . 119.4(2) ?
C2 C1 P1 . . 120.8(2) ?
C10 C1 P1 . . 119.8(2) ?
C1 C2 N1 . . 125.2(2) ?
C1 C2 C3 . . 119.0(2) ?
N1 C2 C3 . . 115.8(2) ?
C4 C3 C8 . . 117.6(2) ?
C4 C3 C2 . . 122.4(2) ?
C8 C3 C2 . . 120.0(2) ?
C5 C4 C3 . . 121.3(3) ?
C5 C4 H4 . . 119.4 ?
C3 C4 H4 . . 119.4 ?
C4 C5 C6 . . 120.8(3) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C7 C6 C5 . . 119.5(3) ?
C7 C6 H6 . . 120.3 ?
C5 C6 H6 . . 120.3 ?
C6 C7 C8 . . 121.4(3) ?
C6 C7 H7 . . 119.3 ?
C8 C7 H7 . . 119.3 ?
C9 C8 C7 . . 122.0(3) ?
C9 C8 C3 . . 118.6(2) ?
C7 C8 C3 . . 119.4(3) ?
C10 C9 C8 . . 121.0(3) ?
C10 C9 H9 . . 119.5 ?
C8 C9 H9 . . 119.5 ?
C9 C10 C1 . . 121.9(3) ?
C9 C10 H10 . . 119.0 ?
C1 C10 H10 . . 119.0 ?
C16 C11 C12 . . 118.3(3) ?
C16 C11 P1 . . 123.8(2) ?
C12 C11 P1 . . 117.8(2) ?
C13 C12 C11 . . 120.5(3) ?
C13 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
C12 C13 C14 . . 120.8(3) ?
C12 C13 H13 . . 119.6 ?
C14 C13 H13 . . 119.6 ?
C15 C14 C13 . . 119.3(3) ?
C15 C14 H14 . . 120.4 ?
C13 C14 H14 . . 120.4 ?
C14 C15 C16 . . 120.0(3) ?
C14 C15 H15 . . 120.0 ?
C16 C15 H15 . . 120.0 ?
C11 C16 C15 . . 121.1(3) ?
C11 C16 H16 . . 119.4 ?
C15 C16 H16 . . 119.4 ?
C18 C17 C22 . . 118.0(3) ?
C18 C17 P1 . . 125.5(2) ?
C22 C17 P1 . . 116.5(2) ?
C17 C18 C19 . . 120.8(3) ?
C17 C18 H18 . . 119.6 ?
C19 C18 H18 . . 119.6 ?
C20 C19 C18 . . 120.7(3) ?
C20 C19 H19 . . 119.7 ?
C18 C19 H19 . . 119.7 ?
C19 C20 C21 . . 119.2(3) ?
C19 C20 H20 . . 120.4 ?
C21 C20 H20 . . 120.4 ?
C20 C21 C22 . . 120.4(3) ?
C20 C21 H21 . . 119.8 ?
C22 C21 H21 . . 119.8 ?
C21 C22 C17 . . 120.8(3) ?
C21 C22 H22 . . 119.6 ?
C17 C22 H22 . . 119.6 ?
N1 C23 C24 . . 115.5(2) ?
N1 C23 H23A . . 108.4 ?
C24 C23 H23A . . 108.4 ?
N1 C23 H23B . . 108.4 ?
C24 C23 H23B . . 108.4 ?
H23A C23 H23B . . 107.5 ?
C25 C24 C23 . . 123.9(3) ?
C25 C24 H24 . . 118.1 ?
C23 C24 H24 . . 118.1 ?
C24 C25 C26 . . 128.1(3) ?
C24 C25 H25 . . 115.9 ?
C26 C25 H25 . . 115.9 ?
C31 C26 C27 . . 117.9(3) ?
C31 C26 C25 . . 122.7(3) ?
C27 C26 C25 . . 119.4(3) ?
C28 C27 C26 . . 121.3(3) ?
C28 C27 H27 . . 119.3 ?
C26 C27 H27 . . 119.3 ?
C27 C28 C29 . . 120.3(3) ?
C27 C28 H28 . . 119.8 ?
C29 C28 H28 . . 119.8 ?
C28 C29 C30 . . 118.9(4) ?
C28 C29 H29 . . 120.5 ?
C30 C29 H29 . . 120.5 ?
C31 C30 C29 . . 120.9(4) ?
C31 C30 H30 . . 119.5 ?
C29 C30 H30 . . 119.5 ?
C30 C31 C26 . . 120.5(3) ?
C30 C31 H31 . . 119.7 ?
C26 C31 H31 . . 119.7 ?
N1 C32 C39 . . 111.8(2) ?
N1 C32 C33 . . 110.9(2) ?
C39 C32 C33 . . 108.2(2) ?
N1 C32 H32 . . 108.6 ?
C39 C32 H32 . . 108.6 ?
C33 C32 H32 . . 108.6 ?
C41 C33 C34 . . 109.4(2) ?
C41 C33 C32 . . 110.7(2) ?
C34 C33 C32 . . 108.7(2) ?
C41 C33 H33 . . 109.4 ?
C34 C33 H33 . . 109.4 ?
C32 C33 H33 . . 109.4 ?
C33 C34 C35 . . 110.1(2) ?
C33 C34 H34A . . 109.6 ?
C35 C34 H34A . . 109.6 ?
C33 C34 H34B . . 109.6 ?
C35 C34 H34B . . 109.6 ?
H34A C34 H34B . . 108.2 ?
C40 C35 C36 . . 109.7(3) ?
C40 C35 C34 . . 108.4(2) ?
C36 C35 C34 . . 109.2(3) ?
C40 C35 H35 . . 109.8 ?
C36 C35 H35 . . 109.8 ?
C34 C35 H35 . . 109.8 ?
C37 C36 C35 . . 110.0(2) ?
C37 C36 H36A . . 109.7 ?
C35 C36 H36A . . 109.7 ?
C37 C36 H36B . . 109.7 ?
C35 C36 H36B . . 109.7 ?
H36A C36 H36B . . 108.2 ?
C36 C37 C38 . . 109.4(3) ?
C36 C37 C41 . . 110.0(3) ?
C38 C37 C41 . . 108.2(2) ?
C36 C37 H37 . . 109.7 ?
C38 C37 H37 . . 109.7 ?
C41 C37 H37 . . 109.7 ?
C37 C38 C39 . . 110.1(2) ?
C37 C38 H38A . . 109.6 ?
C39 C38 H38A . . 109.6 ?
C37 C38 H38B . . 109.6 ?
C39 C38 H38B . . 109.6 ?
H38A C38 H38B . . 108.2 ?
C38 C39 C40 . . 109.8(2) ?
C38 C39 C32 . . 110.6(2) ?
C40 C39 C32 . . 108.0(2) ?
C38 C39 H39 . . 109.5 ?
C40 C39 H39 . . 109.5 ?
C32 C39 H39 . . 109.5 ?
C35 C40 C39 . . 110.2(2) ?
C35 C40 H40A . . 109.6 ?
C39 C40 H40A . . 109.6 ?
C35 C40 H40B . . 109.6 ?
C39 C40 H40B . . 109.6 ?
H40A C40 H40B . . 108.1 ?
C33 C41 C37 . . 109.8(2) ?
C33 C41 H41A . . 109.7 ?
C37 C41 H41A . . 109.7 ?
C33 C41 H41B . . 109.7 ?
C37 C41 H41B . . 109.7 ?
H41A C41 H41B . . 108.2 ?
Cl3 C42 Cl2 . . 111.02(18) ?
Cl3 C42 Cl1 . . 110.9(2) ?
Cl2 C42 Cl1 . . 111.70(19) ?
Cl3 C42 H42 . . 107.7 ?
Cl2 C42 H42 . . 107.7 ?
Cl1 C42 H42 . . 107.7 ?
C2 N1 C23 . . 115.4(2) ?
C2 N1 C32 . . 122.5(2) ?
C23 N1 C32 . . 116.8(2) ?
C17 P1 C11 . . 100.27(13) ?
C17 P1 C1 . . 101.68(13) ?
C11 P1 C1 . . 101.68(13) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 C1 C2 N1 . . . . 176.1(2) ?
P1 C1 C2 N1 . . . . -7.5(3) ?
C10 C1 C2 C3 . . . . -4.5(4) ?
P1 C1 C2 C3 . . . . 171.91(18) ?
C1 C2 C3 C4 . . . . -177.7(2) ?
N1 C2 C3 C4 . . . . 1.7(3) ?
C1 C2 C3 C8 . . . . 2.4(3) ?
N1 C2 C3 C8 . . . . -178.2(2) ?
C8 C3 C4 C5 . . . . -2.0(4) ?
C2 C3 C4 C5 . . . . 178.0(2) ?
C3 C4 C5 C6 . . . . 2.1(4) ?
C4 C5 C6 C7 . . . . -0.8(4) ?
C5 C6 C7 C8 . . . . -0.5(4) ?
C6 C7 C8 C9 . . . . -179.9(3) ?
C6 C7 C8 C3 . . . . 0.5(4) ?
C4 C3 C8 C9 . . . . -178.9(2) ?
C2 C3 C8 C9 . . . . 1.1(4) ?
C4 C3 C8 C7 . . . . 0.8(4) ?
C2 C3 C8 C7 . . . . -179.3(2) ?
C7 C8 C9 C10 . . . . 178.0(3) ?
C3 C8 C9 C10 . . . . -2.4(4) ?
C8 C9 C10 C1 . . . . 0.2(5) ?
C2 C1 C10 C9 . . . . 3.3(4) ?
P1 C1 C10 C9 . . . . -173.1(2) ?
C16 C11 C12 C13 . . . . -2.3(6) ?
P1 C11 C12 C13 . . . . -179.4(3) ?
C11 C12 C13 C14 . . . . 1.5(7) ?
C12 C13 C14 C15 . . . . 0.2(6) ?
C13 C14 C15 C16 . . . . -0.9(5) ?
C12 C11 C16 C15 . . . . 1.6(5) ?
P1 C11 C16 C15 . . . . 178.5(2) ?
C14 C15 C16 C11 . . . . 0.0(5) ?
C22 C17 C18 C19 . . . . 0.2(5) ?
P1 C17 C18 C19 . . . . 179.1(3) ?
C17 C18 C19 C20 . . . . 1.3(6) ?
C18 C19 C20 C21 . . . . -1.7(6) ?
C19 C20 C21 C22 . . . . 0.7(6) ?
C20 C21 C22 C17 . . . . 0.8(5) ?
C18 C17 C22 C21 . . . . -1.3(5) ?
P1 C17 C22 C21 . . . . 179.8(3) ?
N1 C23 C24 C25 . . . . 136.9(3) ?
C23 C24 C25 C26 . . . . 176.4(3) ?
C24 C25 C26 C31 . . . . 5.0(5) ?
C24 C25 C26 C27 . . . . -175.3(3) ?
C31 C26 C27 C28 . . . . -0.4(5) ?
C25 C26 C27 C28 . . . . 179.8(3) ?
C26 C27 C28 C29 . . . . 0.7(6) ?
C27 C28 C29 C30 . . . . 0.4(6) ?
C28 C29 C30 C31 . . . . -1.8(7) ?
C29 C30 C31 C26 . . . . 2.1(7) ?
C27 C26 C31 C30 . . . . -0.9(6) ?
C25 C26 C31 C30 . . . . 178.8(4) ?
N1 C32 C33 C41 . . . . 64.8(3) ?
C39 C32 C33 C41 . . . . -58.2(3) ?
N1 C32 C33 C34 . . . . -175.0(2) ?
C39 C32 C33 C34 . . . . 61.9(3) ?
C41 C33 C34 C35 . . . . 60.0(3) ?
C32 C33 C34 C35 . . . . -61.0(3) ?
C33 C34 C35 C40 . . . . 59.6(3) ?
C33 C34 C35 C36 . . . . -59.9(3) ?
C40 C35 C36 C37 . . . . -59.6(3) ?
C34 C35 C36 C37 . . . . 59.2(3) ?
C35 C36 C37 C38 . . . . 59.7(3) ?
C35 C36 C37 C41 . . . . -59.0(3) ?
C36 C37 C38 C39 . . . . -59.3(3) ?
C41 C37 C38 C39 . . . . 60.5(3) ?
C37 C38 C39 C40 . . . . 58.6(3) ?
C37 C38 C39 C32 . . . . -60.4(3) ?
N1 C32 C39 C38 . . . . -64.5(3) ?
C33 C32 C39 C38 . . . . 57.9(3) ?
N1 C32 C39 C40 . . . . 175.3(2) ?
C33 C32 C39 C40 . . . . -62.2(3) ?
C36 C35 C40 C39 . . . . 58.7(3) ?
C34 C35 C40 C39 . . . . -60.5(3) ?
C38 C39 C40 C35 . . . . -58.3(3) ?
C32 C39 C40 C35 . . . . 62.3(3) ?
C34 C33 C41 C37 . . . . -59.1(3) ?
C32 C33 C41 C37 . . . . 60.6(3) ?
C36 C37 C41 C33 . . . . 58.9(3) ?
C38 C37 C41 C33 . . . . -60.5(3) ?
C1 C2 N1 C23 . . . . 105.0(3) ?
C3 C2 N1 C23 . . . . -74.4(3) ?
C1 C2 N1 C32 . . . . -48.4(4) ?
C3 C2 N1 C32 . . . . 132.2(2) ?
C24 C23 N1 C2 . . . . -96.7(3) ?
C24 C23 N1 C32 . . . . 58.3(3) ?
C39 C32 N1 C2 . . . . -35.5(3) ?
C33 C32 N1 C2 . . . . -156.4(2) ?
C39 C32 N1 C23 . . . . 171.5(2) ?
C33 C32 N1 C23 . . . . 50.6(3) ?
C18 C17 P1 C11 . . . . 100.3(3) ?
C22 C17 P1 C11 . . . . -80.8(2) ?
C18 C17 P1 C1 . . . . -4.0(3) ?
C22 C17 P1 C1 . . . . 174.9(2) ?
C16 C11 P1 C17 . . . . -10.6(3) ?
C12 C11 P1 C17 . . . . 166.4(3) ?
C16 C11 P1 C1 . . . . 93.7(3) ?
C12 C11 P1 C1 . . . . -89.3(3) ?
C2 C1 P1 C17 . . . . -98.6(2) ?
C10 C1 P1 C17 . . . . 77.8(2) ?
C2 C1 P1 C11 . . . . 158.2(2) ?
C10 C1 P1 C11 . . . . -25.4(3) ?

