# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_5366
_database_code_depnum_ccdc_archive 'CCDC 1919566'
loop_
_audit_author_name
_audit_author_address
'Gregor Schnakenburg'
;University of Bonn
Germany
;
_audit_update_record             
;
2019-05-29 deposited with the CCDC.	2020-01-13 downloaded from the CCDC.
;
_audit_creation_date             2017-09-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        NRN-142
_chemical_formula_moiety         'C30 H56 N6 P2 Se2'
_chemical_formula_sum            'C30 H56 N6 P2 Se2'
_chemical_formula_weight         720.66
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.2393(5)
_cell_length_b                   13.1195(7)
_cell_length_c                   16.0254(7)
_cell_angle_alpha                74.256(4)
_cell_angle_beta                 75.947(4)
_cell_angle_gamma                74.656(4)
_cell_volume                     1772.13(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10747
_cell_measurement_temperature    123
_cell_measurement_theta_max      29.42
_cell_measurement_theta_min      2.68
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.778
_exptl_absorpt_coefficient_mu    2.205
_exptl_absorpt_correction_T_max  0.8344
_exptl_absorpt_correction_T_min  0.5308
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13026
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         2.687
_diffrn_ambient_temperature      123
_diffrn_detector                 'Bruker Photon100 detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8-Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4985
_reflns_number_total             6846
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.996
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         6846
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0309P)²+5.1324P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1142
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,
 H10B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C19(H19A,H19B),
 C20(H20A,H20B), C21(H21A,H21B), C23(H23A,H23B), C25(H25A,H25B), C27(H27A,H27B),
  C29(H29A,H29B)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C), C18(H18A,H18B,H18C), C22(H22A,H22B,
 H22C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C30(H30A,
 H30B,H30C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.55262(6) 0.65419(4) 1.10827(3) 0.02562(14) Uani 1 1 d . . . . .
Se2 Se 1.37453(6) 0.77312(4) 0.52337(3) 0.02770(14) Uani 1 1 d . . . . .
P1 P 0.91800(14) 0.59005(9) 0.77974(7) 0.0178(3) Uani 1 1 d . . . . .
P2 P 0.90304(14) 0.87378(9) 0.80702(7) 0.0159(2) Uani 1 1 d . . . . .
N1 N 0.7325(4) 0.6122(3) 0.9430(2) 0.0170(8) Uani 1 1 d . . . . .
N2 N 0.7058(4) 0.7783(3) 0.9516(2) 0.0153(8) Uani 1 1 d . . . . .
N3 N 1.1391(5) 0.6767(3) 0.6464(2) 0.0189(8) Uani 1 1 d . . . . .
N4 N 1.1297(4) 0.8377(3) 0.6608(2) 0.0172(8) Uani 1 1 d . . . . .
N5 N 0.7844(5) 0.5916(3) 0.7244(3) 0.0217(9) Uani 1 1 d . . . . .
N6 N 0.7917(5) 0.9808(3) 0.7520(2) 0.0196(8) Uani 1 1 d . . . . .
C1 C 0.8145(5) 0.6642(4) 0.8644(3) 0.0164(9) Uani 1 1 d . . . . .
C2 C 0.6669(5) 0.6820(4) 0.9969(3) 0.0178(9) Uani 1 1 d . . . . .
C3 C 0.7953(5) 0.7693(4) 0.8701(3) 0.0166(9) Uani 1 1 d . . . . .
C4 C 0.7187(6) 0.4985(4) 0.9643(3) 0.0206(10) Uani 1 1 d . . . . .
H4A H 0.7145 0.4784 0.9098 0.025 Uiso 1 1 calc R . . . .
H4B H 0.6219 0.4906 1.0061 0.025 Uiso 1 1 calc R . . . .
C5 C 0.8513(6) 0.4213(4) 1.0047(3) 0.0264(11) Uani 1 1 d . . . . .
H5A H 0.8489 0.4358 1.0626 0.032 Uiso 1 1 calc R . . . .
H5B H 0.9489 0.4343 0.9659 0.032 Uiso 1 1 calc R . . . .
C6 C 0.8431(6) 0.3023(4) 1.0171(3) 0.0297(12) Uani 1 1 d . . . . .
H6A H 0.9220 0.2551 1.0509 0.036 Uiso 1 1 calc R . . . .
H6B H 0.7422 0.2914 1.0523 0.036 Uiso 1 1 calc R . . . .
C7 C 0.8665(7) 0.2681(4) 0.9306(4) 0.0365(13) Uani 1 1 d . . . . .
H7A H 0.9565 0.2911 0.8909 0.055 Uiso 1 1 calc GR . . . .
H7B H 0.7763 0.3020 0.9033 0.055 Uiso 1 1 calc GR . . . .
H7C H 0.8817 0.1891 0.9421 0.055 Uiso 1 1 calc GR . . . .
C8 C 0.6564(5) 0.8771(4) 0.9867(3) 0.0180(9) Uani 1 1 d . . . . .
H8A H 0.5548 0.8772 1.0253 0.022 Uiso 1 1 calc R . . . .
H8B H 0.6460 0.9413 0.9372 0.022 Uiso 1 1 calc R . . . .
C9 C 0.7681(5) 0.8854(4) 1.0390(3) 0.0203(10) Uani 1 1 d . . . . .
H9A H 0.8706 0.8830 1.0013 0.024 Uiso 1 1 calc R . . . .
H9B H 0.7756 0.8230 1.0901 0.024 Uiso 1 1 calc R . . . .
C10 C 0.7160(6) 0.9911(4) 1.0717(3) 0.0243(11) Uani 1 1 d . . . . .
H10A H 0.7106 1.0532 1.0203 0.029 Uiso 1 1 calc R . . . .
H10B H 0.6121 0.9940 1.1077 0.029 Uiso 1 1 calc R . . . .
C11 C 0.8221(6) 1.0019(4) 1.1264(4) 0.0311(12) Uani 1 1 d . . . . .
H11A H 0.9241 1.0025 1.0903 0.047 Uiso 1 1 calc GR . . . .
H11B H 0.8282 0.9405 1.1774 0.047 Uiso 1 1 calc GR . . . .
H11C H 0.7824 1.0697 1.1469 0.047 Uiso 1 1 calc GR . . . .
C12 C 1.0175(5) 0.6969(4) 0.7147(3) 0.0175(9) Uani 1 1 d . . . . .
C13 C 1.2064(5) 0.7626(4) 0.6127(3) 0.0186(10) Uani 1 1 d . . . . .
C14 C 1.0114(5) 0.7992(4) 0.7240(3) 0.0170(9) Uani 1 1 d . . . . .
C15 C 1.1975(6) 0.5725(4) 0.6194(3) 0.0246(11) Uani 1 1 d . . . . .
H15A H 1.2390 0.5856 0.5553 0.030 Uiso 1 1 calc R . . . .
H15B H 1.1130 0.5344 0.6311 0.030 Uiso 1 1 calc R . . . .
C16 C 1.3226(7) 0.5017(4) 0.6698(4) 0.0331(13) Uani 1 1 d . . . . .
H16A H 1.4051 0.5415 0.6588 0.040 Uiso 1 1 calc R . . . .
H16B H 1.2796 0.4892 0.7338 0.040 Uiso 1 1 calc R . . . .
C17 C 1.3905(8) 0.3934(5) 0.6453(5) 0.0492(17) Uani 1 1 d . . . . .
H17A H 1.4267 0.4057 0.5807 0.059 Uiso 1 1 calc R . . . .
H17B H 1.4804 0.3578 0.6738 0.059 Uiso 1 1 calc R . . . .
C18 C 1.2828(11) 0.3195(6) 0.6712(6) 0.076(3) Uani 1 1 d . . . . .
H18A H 1.2043 0.3470 0.6344 0.115 Uiso 1 1 calc GR . . . .
H18B H 1.2344 0.3155 0.7333 0.115 Uiso 1 1 calc GR . . . .
H18C H 1.3386 0.2471 0.6631 0.115 Uiso 1 1 calc GR . . . .
C19 C 1.1763(6) 0.9403(4) 0.6489(3) 0.0201(10) Uani 1 1 d . . . . .
H19A H 1.2892 0.9273 0.6350 0.024 Uiso 1 1 calc R . . . .
H19B H 1.1420 0.9649 0.7050 0.024 Uiso 1 1 calc R . . . .
C20 C 1.1124(6) 1.0300(4) 0.5760(3) 0.0210(10) Uani 1 1 d . . . . .
H20A H 0.9995 1.0474 0.5911 0.025 Uiso 1 1 calc R . . . .
H20B H 1.1421 1.0052 0.5199 0.025 Uiso 1 1 calc R . . . .
C21 C 1.1734(6) 1.1311(4) 0.5645(3) 0.0263(11) Uani 1 1 d . . . . .
H21A H 1.1592 1.1481 0.6228 0.032 Uiso 1 1 calc R . . . .
H21B H 1.2843 1.1164 0.5403 0.032 Uiso 1 1 calc R . . . .
C22 C 1.0940(7) 1.2287(4) 0.5032(3) 0.0337(13) Uani 1 1 d . . . . .
H22A H 1.1151 1.2147 0.4440 0.051 Uiso 1 1 calc GR . . . .
H22B H 1.1321 1.2927 0.5008 0.051 Uiso 1 1 calc GR . . . .
H22C H 0.9836 1.2418 0.5255 0.051 Uiso 1 1 calc GR . . . .
C23 C 0.7741(6) 0.4862(4) 0.7109(3) 0.0247(11) Uani 1 1 d . . . . .
H23A H 0.6750 0.4689 0.7440 0.030 Uiso 1 1 calc R . . . .
H23B H 0.8562 0.4286 0.7354 0.030 Uiso 1 1 calc R . . . .
C24 C 0.7880(7) 0.4859(4) 0.6148(3) 0.0347(13) Uani 1 1 d . . . . .
H24A H 0.8868 0.5015 0.5817 0.052 Uiso 1 1 calc GR . . . .
H24B H 0.7055 0.5415 0.5904 0.052 Uiso 1 1 calc GR . . . .
H24C H 0.7807 0.4146 0.6100 0.052 Uiso 1 1 calc GR . . . .
C25 C 0.6575(6) 0.6828(4) 0.7051(3) 0.0225(10) Uani 1 1 d . . . . .
H25A H 0.6369 0.6858 0.6466 0.027 Uiso 1 1 calc R . . . .
H25B H 0.6888 0.7507 0.7013 0.027 Uiso 1 1 calc R . . . .
C26 C 0.5094(6) 0.6781(4) 0.7730(4) 0.0311(12) Uani 1 1 d . . . . .
H26A H 0.4277 0.7378 0.7523 0.047 Uiso 1 1 calc GR . . . .
H26B H 0.5247 0.6847 0.8296 0.047 Uiso 1 1 calc GR . . . .
H26C H 0.4810 0.6088 0.7805 0.047 Uiso 1 1 calc GR . . . .
C27 C 0.7445(6) 1.0809(4) 0.7862(3) 0.0243(11) Uani 1 1 d . . . . .
H27A H 0.7913 1.0683 0.8386 0.029 Uiso 1 1 calc R . . . .
H27B H 0.6323 1.0956 0.8060 0.029 Uiso 1 1 calc R . . . .
C28 C 0.7873(7) 1.1802(4) 0.7210(3) 0.0322(13) Uani 1 1 d . . . . .
H28A H 0.7421 1.1935 0.6687 0.048 Uiso 1 1 calc GR . . . .
H28B H 0.8987 1.1686 0.7038 0.048 Uiso 1 1 calc GR . . . .
H28C H 0.7488 1.2430 0.7482 0.048 Uiso 1 1 calc GR . . . .
C29 C 0.7152(5) 0.9781(4) 0.6823(3) 0.0200(10) Uani 1 1 d . . . . .
H29A H 0.7685 0.9135 0.6578 0.024 Uiso 1 1 calc R . . . .
H29B H 0.7249 1.0430 0.6340 0.024 Uiso 1 1 calc R . . . .
C30 C 0.5480(6) 0.9749(5) 0.7130(4) 0.0345(13) Uani 1 1 d . . . . .
H30A H 0.5075 0.9657 0.6650 0.052 Uiso 1 1 calc GR . . . .
H30B H 0.4916 1.0429 0.7302 0.052 Uiso 1 1 calc GR . . . .
H30C H 0.5363 0.9140 0.7637 0.052 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C2 1.835(5) . ?
Se2 C13 1.845(5) . ?
P1 N5 1.679(4) . ?
P1 C1 1.815(4) . ?
P1 C12 1.822(5) . ?
P2 N6 1.677(4) . ?
P2 C3 1.836(5) . ?
P2 C14 1.809(4) . ?
N1 C1 1.403(6) . ?
N1 C2 1.354(6) . ?
N1 C4 1.471(6) . ?
N2 C2 1.367(6) . ?
N2 C3 1.381(5) . ?
N2 C8 1.471(5) . ?
N3 C12 1.391(6) . ?
N3 C13 1.351(6) . ?
N3 C15 1.471(6) . ?
N4 C13 1.359(6) . ?
N4 C14 1.397(6) . ?
N4 C19 1.471(6) . ?
N5 C23 1.486(6) . ?
N5 C25 1.461(6) . ?
N6 C27 1.480(6) . ?
N6 C29 1.472(6) . ?
C1 C3 1.370(6) . ?
C4 C5 1.523(7) . ?
C5 C6 1.539(7) . ?
C6 C7 1.520(7) . ?
C8 C9 1.520(6) . ?
C9 C10 1.531(6) . ?
C10 C11 1.519(7) . ?
C12 C14 1.375(6) . ?
C15 C16 1.526(7) . ?
C16 C17 1.509(7) . ?
C17 C18 1.482(11) . ?
C19 C20 1.523(6) . ?
C20 C21 1.525(6) . ?
C21 C22 1.520(7) . ?
C23 C24 1.516(7) . ?
C25 C26 1.531(7) . ?
C27 C28 1.509(7) . ?
C29 C30 1.511(7) . ?

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
N5 P1 C1 104.3(2) . . ?
N5 P1 C12 106.4(2) . . ?
C1 P1 C12 94.5(2) . . ?
N6 P2 C3 111.2(2) . . ?
N6 P2 C14 104.23(19) . . ?
C14 P2 C3 95.4(2) . . ?
C1 N1 C4 125.2(4) . . ?
C2 N1 C1 110.3(4) . . ?
C2 N1 C4 124.5(4) . . ?
C2 N2 C3 111.1(4) . . ?
C2 N2 C8 123.2(4) . . ?
C3 N2 C8 125.7(4) . . ?
C12 N3 C15 125.0(4) . . ?
C13 N3 C12 111.1(4) . . ?
C13 N3 C15 123.7(4) . . ?
C13 N4 C14 110.2(4) . . ?
C13 N4 C19 122.6(4) . . ?
C14 N4 C19 127.1(4) . . ?
C23 N5 P1 117.4(3) . . ?
C25 N5 P1 124.9(3) . . ?
C25 N5 C23 116.3(4) . . ?
C27 N6 P2 117.4(3) . . ?
C29 N6 P2 125.2(3) . . ?
C29 N6 C27 116.5(4) . . ?
N1 C1 P1 120.4(3) . . ?
C3 C1 P1 133.0(3) . . ?
C3 C1 N1 106.7(4) . . ?
N1 C2 Se1 127.8(3) . . ?
N1 C2 N2 105.4(4) . . ?
N2 C2 Se1 126.7(3) . . ?
N2 C3 P2 120.3(3) . . ?
C1 C3 P2 130.7(3) . . ?
C1 C3 N2 106.5(4) . . ?
N1 C4 C5 112.3(4) . . ?
C4 C5 C6 111.2(4) . . ?
C7 C6 C5 113.4(4) . . ?
N2 C8 C9 112.2(4) . . ?
C8 C9 C10 110.7(4) . . ?
C11 C10 C9 112.7(4) . . ?
N3 C12 P1 120.4(3) . . ?
C14 C12 P1 132.9(3) . . ?
C14 C12 N3 106.2(4) . . ?
N3 C13 Se2 127.1(3) . . ?
N3 C13 N4 105.9(4) . . ?
N4 C13 Se2 126.9(4) . . ?
N4 C14 P2 120.6(3) . . ?
C12 C14 P2 132.1(4) . . ?
C12 C14 N4 106.7(4) . . ?
N3 C15 C16 110.5(4) . . ?
C17 C16 C15 114.1(5) . . ?
C18 C17 C16 113.9(6) . . ?
N4 C19 C20 113.6(4) . . ?
C19 C20 C21 110.1(4) . . ?
C22 C21 C20 112.3(4) . . ?
N5 C23 C24 113.2(4) . . ?
N5 C25 C26 114.6(4) . . ?
N6 C27 C28 114.8(4) . . ?
N6 C29 C30 114.1(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_5537f
_database_code_depnum_ccdc_archive 'CCDC 1919567'
loop_
_audit_author_name
_audit_author_address
'Gregor Schnakenburg'
;University of Bonn
Germany
;
_audit_update_record             
;
2019-05-29 deposited with the CCDC.	2020-01-13 downloaded from the CCDC.
;
_audit_creation_date             2018-02-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        NRN-148
_chemical_formula_moiety         '2(Cl), C30 H58 N6 O2 P2, 2(H2 O), 2(C3 H8 O)'
_chemical_formula_sum            'C36 H78 Cl2 N6 O6 P2'
_chemical_formula_weight         823.88
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.0162(3)
_cell_length_b                   10.5594(4)
_cell_length_c                   12.6500(4)
_cell_angle_alpha                75.8224(11)
_cell_angle_beta                 80.3081(11)
_cell_angle_gamma                64.3590(10)
_cell_volume                     1166.45(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9527
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.57
_cell_measurement_theta_min      4.73
_shelx_estimated_absorpt_T_max   0.805
_shelx_estimated_absorpt_T_min   0.465
_exptl_absorpt_coefficient_mu    2.262
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.3325
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1628 before and 0.1066 after correction. The Ratio of minimum to maximum transmission is 0.4412. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29578
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.749
_diffrn_reflns_theta_min         4.735
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon100 detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8-Venture'
_diffrn_measurement_method       'fine slicing ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4043
_reflns_number_total             4192
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         4192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0800P)²+0.8763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1291
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B),
 C12(H12A,H12B), C14(H14A,H14B)
2.c Me refined with riding coordinates:
 C6(H6A,H6B,H6C), C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl 0.21851(5) 0.54069(5) 0.91030(4) 0.02077(16) Uani 1 1 d . . . . .
P P 0.06400(4) -0.09546(4) 0.13843(3) 0.00892(15) Uani 1 1 d . . . . .
O1 O -0.02374(14) -0.08043(13) 0.24377(9) 0.0138(3) Uani 1 1 d . . . . .
N1 N 0.13110(16) 0.14629(16) 0.09035(11) 0.0104(3) Uani 1 1 d . . . . .
N2 N 0.05929(15) 0.25485(15) -0.07258(11) 0.0103(3) Uani 1 1 d . . . . .
N3 N 0.23660(16) -0.21038(16) 0.14933(12) 0.0138(3) Uani 1 1 d . . . . .
C1 C 0.06933(18) 0.06827(18) 0.05736(13) 0.0104(3) Uani 1 1 d . . . . .
C2 C 0.12192(18) 0.25759(19) 0.01088(14) 0.0117(3) Uani 1 1 d . . . . .
H2 H 0.1551 0.3285 0.0133 0.014 Uiso 1 1 calc R . . . .
C3 C 0.1948(2) 0.1171(2) 0.19564(13) 0.0133(4) Uani 1 1 d . . . . .
H3A H 0.2611 0.1671 0.1862 0.016 Uiso 1 1 calc R . . . .
H3B H 0.2557 0.0131 0.2163 0.016 Uiso 1 1 calc R . . . .
C4 C 0.0768(2) 0.1651(2) 0.28770(14) 0.0160(4) Uani 1 1 d . . . . .
H4A H 0.0118 0.2680 0.2663 0.019 Uiso 1 1 calc R . . . .
H4B H 0.0145 0.1104 0.3016 0.019 Uiso 1 1 calc R . . . .
C5 C 0.1505(2) 0.1406(3) 0.39067(16) 0.0273(5) Uani 1 1 d . . . . .
H5A H 0.2066 0.2012 0.3770 0.033 Uiso 1 1 calc R . . . .
H5B H 0.2227 0.0394 0.4067 0.033 Uiso 1 1 calc R . . . .
C6 C 0.0427(3) 0.1735(2) 0.49027(15) 0.0252(5) Uani 1 1 d . . . . .
H6A H 0.0978 0.1553 0.5534 0.038 Uiso 1 1 calc R . . . .
H6B H -0.0277 0.2742 0.4760 0.038 Uiso 1 1 calc R . . . .
H6C H -0.0116 0.1121 0.5057 0.038 Uiso 1 1 calc R . . . .
C7 C 0.03646(19) 0.36077(19) -0.17641(14) 0.0123(4) Uani 1 1 d . . . . .
H7A H 0.0232 0.4536 -0.1619 0.015 Uiso 1 1 calc R . . . .
H7B H -0.0553 0.3751 -0.2063 0.015 Uiso 1 1 calc R . . . .
C8 C 0.1663(2) 0.3130(2) -0.26042(14) 0.0147(4) Uani 1 1 d . . . . .
H8A H 0.1828 0.2182 -0.2731 0.018 Uiso 1 1 calc R . . . .
H8B H 0.2575 0.3037 -0.2327 0.018 Uiso 1 1 calc R . . . .
C9 C 0.1343(2) 0.4217(2) -0.36730(16) 0.0241(4) Uani 1 1 d . . . . .
H9A H 0.0421 0.4312 -0.3935 0.029 Uiso 1 1 calc R . . . .
H9B H 0.1170 0.5161 -0.3534 0.029 Uiso 1 1 calc R . . . .
C10 C 0.2587(2) 0.3819(3) -0.45604(16) 0.0288(5) Uani 1 1 d . . . . .
H10A H 0.2316 0.4557 -0.5225 0.043 Uiso 1 1 calc R . . . .
H10B H 0.3499 0.3746 -0.4314 0.043 Uiso 1 1 calc R . . . .
H10C H 0.2749 0.2896 -0.4716 0.043 Uiso 1 1 calc R . . . .
C11 C -0.02312(18) -0.13780(18) 0.04550(13) 0.0096(3) Uani 1 1 d . . . . .
C12 C 0.3395(2) -0.2402(2) 0.05048(16) 0.0181(4) Uani 1 1 d . . . . .
H12A H 0.2806 -0.2162 -0.0126 0.022 Uiso 1 1 calc R . . . .
H12B H 0.4040 -0.3440 0.0615 0.022 Uiso 1 1 calc R . . . .
C13 C 0.4373(2) -0.1577(2) 0.02292(18) 0.0259(5) Uani 1 1 d . . . . .
H13A H 0.5019 -0.1826 -0.0429 0.039 Uiso 1 1 calc R . . . .
H13B H 0.3746 -0.0547 0.0098 0.039 Uiso 1 1 calc R . . . .
H13C H 0.4982 -0.1825 0.0841 0.039 Uiso 1 1 calc R . . . .
C14 C 0.2805(2) -0.3153(2) 0.25310(16) 0.0191(4) Uani 1 1 d . . . . .
H14A H 0.3005 -0.4115 0.2414 0.023 Uiso 1 1 calc R . . . .
H14B H 0.1966 -0.2895 0.3092 0.023 Uiso 1 1 calc R . . . .
C15 C 0.4167(3) -0.3218(2) 0.29544(19) 0.0300(5) Uani 1 1 d . . . . .
H15A H 0.4403 -0.3926 0.3638 0.045 Uiso 1 1 calc R . . . .
H15B H 0.5009 -0.3496 0.2410 0.045 Uiso 1 1 calc R . . . .
H15C H 0.3969 -0.2276 0.3089 0.045 Uiso 1 1 calc R . . . .
O2 O 0.28883(17) 0.38706(17) 0.15494(14) 0.0261(3) Uani 1 1 d . . . . .
H2A H 0.374(3) 0.368(3) 0.167(2) 0.031 Uiso 1 1 d R . . . .
H2B H 0.286(3) 0.431(3) 0.091(3) 0.031 Uiso 1 1 d R . . . .
O3 O 0.57178(19) 0.3161(2) 0.20735(13) 0.0388(4) Uani 1 1 d . . . . .
H3 H 0.6263 0.3557 0.1708 0.058 Uiso 1 1 calc GR . . . .
C16 C 0.5751(3) 0.1044(3) 0.3296(3) 0.0455(7) Uani 1 1 d . . . . .
H16A H 0.6279 0.0269 0.3883 0.068 Uiso 1 1 calc R . . . .
H16B H 0.4727 0.1573 0.3565 0.068 Uiso 1 1 calc R . . . .
H16C H 0.5747 0.0639 0.2678 0.068 Uiso 1 1 calc R . . . .
C17 C 0.6525(2) 0.2049(2) 0.29286(19) 0.0275(5) Uani 1 1 d . . . . .
H17 H 0.7557 0.1510 0.2631 0.033 Uiso 1 1 calc R . . . .
C18 C 0.6596(3) 0.2693(3) 0.3844(2) 0.0389(6) Uani 1 1 d . . . . .
H18A H 0.7149 0.1929 0.4426 0.058 Uiso 1 1 calc R . . . .
H18B H 0.7098 0.3339 0.3567 0.058 Uiso 1 1 calc R . . . .
H18C H 0.5587 0.3233 0.4135 0.058 Uiso 1 1 calc R . . . .


_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
P O1 1.4704(12) . ?
P N3 1.6318(15) . ?
P C1 1.7991(18) . ?
P C11 1.8121(17) . ?
N1 C1 1.390(2) . ?
N1 C2 1.326(2) . ?
N1 C3 1.480(2) . ?
N2 C2 1.328(2) . ?
N2 C7 1.479(2) . ?
N2 C11 1.384(2) 2 ?
N3 C12 1.484(2) . ?
N3 C14 1.485(2) . ?
C1 C11 1.374(2) 2 ?
C3 C4 1.522(2) . ?
C4 C5 1.517(3) . ?
C5 C6 1.519(3) . ?
C7 C8 1.518(2) . ?
C8 C9 1.522(3) . ?
C9 C10 1.515(3) . ?
C11 N2 1.384(2) 2 ?
C11 C1 1.374(2) 2 ?
C12 C13 1.521(3) . ?
C14 C15 1.517(3) . ?
O3 C17 1.432(3) . ?
C16 C17 1.514(3) . ?
C17 C18 1.504(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P N3 113.88(8) . . ?
O1 P C1 114.69(7) . . ?
O1 P C11 111.44(7) . . ?
N3 P C1 106.13(8) . . ?
N3 P C11 110.44(8) . . ?
C1 P C11 99.22(8) . . ?
C1 N1 C3 127.87(15) . . ?
C2 N1 C1 108.33(14) . . ?
C2 N1 C3 123.79(14) . . ?
C2 N2 C7 123.93(14) . . ?
C2 N2 C11 108.63(14) . 2 ?
C11 N2 C7 127.43(14) 2 . ?
C12 N3 P 120.69(12) . . ?
C12 N3 C14 117.57(15) . . ?
C14 N3 P 119.43(12) . . ?
N1 C1 P 123.43(13) . . ?
C11 C1 P 129.82(13) 2 . ?
C11 C1 N1 106.70(15) 2 . ?
N1 C2 N2 109.67(15) . . ?
N1 C3 C4 112.86(14) . . ?
C5 C4 C3 109.74(15) . . ?
C4 C5 C6 113.96(17) . . ?
N2 C7 C8 111.91(14) . . ?
C7 C8 C9 109.90(15) . . ?
C10 C9 C8 113.33(18) . . ?
N2 C11 P 122.38(13) 2 . ?
C1 C11 P 130.95(13) 2 . ?
C1 C11 N2 106.66(14) 2 2 ?
N3 C12 C13 114.03(15) . . ?
N3 C14 C15 113.14(16) . . ?
O3 C17 C16 107.48(19) . . ?
O3 C17 C18 109.9(2) . . ?
C18 C17 C16 112.4(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5631g
_database_code_depnum_ccdc_archive 'CCDC 1919569'
loop_
_audit_author_name
_audit_author_address
'Gregor Schnakenburg'
;University of Bonn
Germany
;
_audit_update_record             
;
2019-05-29 deposited with the CCDC.	2020-01-13 downloaded from the CCDC.
;
_audit_creation_date             2018-06-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        NRN-198
_chemical_formula_moiety         'C30 H57 Au2 Cl2 N6 O2 P2, 2(Cl)'
_chemical_formula_sum            'C30 H57 Au2 Cl4 N6 O2 P2'
_chemical_formula_weight         1131.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.102(13)
_cell_length_b                   10.857(14)
_cell_length_c                   11.856(13)
_cell_angle_alpha                103.05(6)
_cell_angle_beta                 97.19(7)
_cell_angle_gamma                116.10(6)
_cell_volume                     1099(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1958
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.10
_cell_measurement_theta_min      2.21
_shelx_estimated_absorpt_T_max   0.513
_shelx_estimated_absorpt_T_min   0.321
_exptl_absorpt_coefficient_mu    7.012
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.2655
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1498 before and 0.0808 after correction. The Ratio of minimum to maximum transmission is 0.3966. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             551
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1058
_diffrn_reflns_av_unetI/netI     0.1060
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23427
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         1.824
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker X8-KappaApexII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3674
_reflns_number_total             5302
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         6.077
_refine_diff_density_min         -2.424
_refine_diff_density_rms         0.340
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         5302
_refine_ls_number_restraints     264
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0773
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0976P)²+29.4002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1799
_refine_ls_wR_factor_ref         0.2138
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C13S-C12S
 1.5 with sigma of 0.001
 C7S-C6S
 1.5 with sigma of 0.01
 C5-C4
 1.5 with sigma of 0.01
 C12S-N3S
 1.47 with sigma of 0.001
 N3S-C13S
 2.7 with sigma of 0.01
 C7-C6 = C6-C5 = C5-C4 = C5S-C4 = C6S-C5S = C7S-C6S = C9-C8 = C9-C10 = C11-C10
 = C13S-C12S = C13-C12 = C15-C14 = C15S-C14S
 1.5 with sigma of 0.01
 N3-C12 = N3S-C12S = N3-C14 = N3S-C14S
 1.46 with sigma of 0.01
3. Rigid bond restraints
 C10, C11
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 P, O1S
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
C4 \\sim C5 \\sim C5S \\sim C6 \\sim C6S \\sim C7 \\sim C7S: within 2A with
sigma of 0.002 and sigma for terminal atoms of 0.004
C15S \\sim C14S \\sim N3S \\sim C14 \\sim C15 \\sim C12S \\sim N3 \\sim C12
\\sim C13 \\sim C13S: within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.002
Uanis(C14S) \\sim Ueq, Uanis(C13S) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma
of 0.001 and sigma for terminal atoms of 0.002
Uanis(C2) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Rigid body (RIGU) restrains
 C15S, C14S, N3S, N3, C12, C13, C13S, C12S, C14, C15
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(N3S)=Sof(C12S)=Sof(H12C)=Sof(H12D)=Sof(C13S)=Sof(H13D)=Sof(H13E)=
 Sof(H13F)=Sof(C14S)=Sof(H14C)=Sof(H14D)=Sof(C15S)=Sof(H15D)=Sof(H15E)=
 Sof(H15F)=1-FVAR(1)
 Sof(N3)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1)
 Sof(H4BC)=Sof(H4BD)=Sof(C5S)=Sof(H5SA)=Sof(H5SB)=Sof(C6S)=Sof(H6SA)=Sof(H6SB)=
 Sof(C7S)=Sof(H7SA)=Sof(H7SB)=Sof(H7SC)=1-FVAR(2)
 Sof(H4AA)=Sof(H4AB)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(C6)=Sof(H6A)=Sof(H6B)=
 Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=FVAR(2)
 Fixed Sof: O(0.5) O1S(0.5) H1S(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C4(H4AA,H4AB), C4(H4BC,H4BD), C5(H5A,H5B), C5S(H5SA,H5SB), C6(H6A,H6B),
 C6S(H6SA,H6SB), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B),
 C12S(H12C,H12D), C14(H14A,H14B), C14S(H14C,H14D)
7.b Me refined with riding coordinates:
 C7(H7A,H7B,H7C), C7S(H7SA,H7SB,H7SC), C11(H11A,H11B,H11C), C13(H13A,H13B,
 H13C), C13S(H13D,H13E,H13F), C15(H15A,H15B,H15C), C15S(H15D,H15E,H15F)
7.c Idealised tetrahedral OH refined as rotating group:
 O1S(H1S)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au Au -0.07691(6) 0.59981(6) 0.48632(5) 0.0282(2) Uani 1 1 d . . . . .
Cl1 Cl -0.3222(4) 0.4555(4) 0.4844(4) 0.0341(8) Uani 1 1 d . . . . .
P P 0.4780(5) 0.9114(5) 0.3451(4) 0.0397(10) Uani 1 1 d . U . . .
O O 0.431(2) 0.902(2) 0.230(2) 0.028(5) Uani 0.5 1 d . . P A 1
O1S O 0.399(3) 0.967(3) 0.255(2) 0.055(7) Uani 0.5 1 d . U P A 2
H1S H 0.3551 0.9025 0.1879 0.082 Uiso 0.5 1 calc GR . P A 2
N1 N 0.2045(11) 0.7443(11) 0.4002(10) 0.021(2) Uani 1 1 d . . . . .
N2 N 0.2343(12) 0.8506(11) 0.5831(10) 0.023(2) Uani 1 1 d . . . . .
N3 N 0.558(2) 0.789(2) 0.3446(15) 0.042(2) Uani 0.629(13) 1 d D U P A 1
N3S N 0.532(3) 0.801(3) 0.292(2) 0.042(2) Uani 0.371(13) 1 d D U P A 2
C1 C 0.3505(14) 0.8617(15) 0.4403(14) 0.028(3) Uani 1 1 d . . . . .
C2 C 0.1383(11) 0.7385(11) 0.4894(9) 0.0089(19) Uani 1 1 d . U . . .
C3 C 0.3670(13) 0.9268(12) 0.5532(12) 0.018(2) Uani 1 1 d . . . . .
C4 C 0.138(2) 0.637(2) 0.2824(15) 0.059(3) Uani 1 1 d D U . . .
H4AA H 0.0901 0.5388 0.2896 0.071 Uiso 0.46(2) 1 calc R . P B 1
H4AB H 0.2174 0.6471 0.2388 0.071 Uiso 0.46(2) 1 calc R . P B 1
H4BC H 0.0500 0.5518 0.2891 0.071 Uiso 0.54(2) 1 calc R . P B 2
H4BD H 0.2140 0.6073 0.2639 0.071 Uiso 0.54(2) 1 calc R . P B 2
C5 C 0.020(4) 0.662(5) 0.216(3) 0.061(3) Uani 0.46(2) 1 d D U P B 1
H5A H -0.0688 0.6248 0.2508 0.073 Uiso 0.46(2) 1 calc R . P B 1
H5B H 0.0618 0.7679 0.2394 0.073 Uiso 0.46(2) 1 calc R . P B 1
C5S C 0.083(4) 0.670(4) 0.175(2) 0.061(3) Uani 0.54(2) 1 d D U P B 2
H5SA H 0.1709 0.7361 0.1516 0.073 Uiso 0.54(2) 1 calc R . P B 2
H5SB H 0.0224 0.5793 0.1071 0.073 Uiso 0.54(2) 1 calc R . P B 2
C6 C -0.044(5) 0.607(5) 0.083(3) 0.061(3) Uani 0.46(2) 1 d D U P B 1
H6A H -0.1164 0.5016 0.0594 0.073 Uiso 0.46(2) 1 calc R . P B 1
H6B H 0.0398 0.6193 0.0443 0.073 Uiso 0.46(2) 1 calc R . P B 1
C6S C -0.014(4) 0.738(4) 0.206(3) 0.061(3) Uani 0.54(2) 1 d D U P B 2
H6SA H 0.0472 0.8302 0.2720 0.074 Uiso 0.54(2) 1 calc R . P B 2
H6SB H -0.1007 0.6730 0.2312 0.074 Uiso 0.54(2) 1 calc R . P B 2
C7 C -0.126(5) 0.679(5) 0.038(4) 0.062(4) Uani 0.46(2) 1 d D U P B 1
H7A H -0.1643 0.6376 -0.0495 0.093 Uiso 0.46(2) 1 calc R . P B 1
H7B H -0.2111 0.6651 0.0741 0.093 Uiso 0.46(2) 1 calc R . P B 1
H7C H -0.0547 0.7830 0.0590 0.093 Uiso 0.46(2) 1 calc R . P B 1
C7S C -0.070(4) 0.765(5) 0.095(3) 0.062(4) Uani 0.54(2) 1 d D U P B 2
H7SA H -0.1343 0.8098 0.1127 0.093 Uiso 0.54(2) 1 calc R . P B 2
H7SB H 0.0166 0.8295 0.0711 0.093 Uiso 0.54(2) 1 calc R . P B 2
H7SC H -0.1307 0.6729 0.0305 0.093 Uiso 0.54(2) 1 calc R . P B 2
C8 C 0.2024(17) 0.8740(16) 0.7036(13) 0.038(4) Uani 1 1 d D . . . .
H8A H 0.0923 0.8416 0.6941 0.045 Uiso 1 1 calc R . . . .
H8B H 0.2599 0.9783 0.7496 0.045 Uiso 1 1 calc R . . . .
C9 C 0.248(2) 0.7908(19) 0.7704(14) 0.056(5) Uani 1 1 d D . . . .
H9A H 0.2007 0.6889 0.7189 0.067 Uiso 1 1 calc R . . . .
H9B H 0.3604 0.8311 0.7869 0.067 Uiso 1 1 calc R . . . .
C10 C 0.203(3) 0.795(2) 0.8859(15) 0.080(7) Uani 1 1 d D U . . .
H10A H 0.2455 0.7465 0.9290 0.096 Uiso 1 1 calc R . . . .
H10B H 0.0909 0.7403 0.8687 0.096 Uiso 1 1 calc R . . . .
C11 C 0.259(5) 0.947(3) 0.965(3) 0.142(14) Uani 1 1 d D U . . .
H11A H 0.2271 0.9437 1.0394 0.213 Uiso 1 1 calc R . . . .
H11B H 0.3708 1.0005 0.9836 0.213 Uiso 1 1 calc R . . . .
H11C H 0.2162 0.9942 0.9234 0.213 Uiso 1 1 calc R . . . .
C12 C 0.642(2) 0.795(3) 0.456(2) 0.042(2) Uani 0.629(13) 1 d D U P A 1
H12A H 0.6220 0.6956 0.4527 0.050 Uiso 0.629(13) 1 calc R . P A 1
H12B H 0.6062 0.8306 0.5236 0.050 Uiso 0.629(13) 1 calc R . P A 1
C12S C 0.599(2) 0.742(2) 0.367(3) 0.042(2) Uani 0.371(13) 1 d D U P A 2
H12C H 0.5786 0.6490 0.3122 0.051 Uiso 0.371(13) 1 calc R . P A 2
H12D H 0.5321 0.7173 0.4218 0.051 Uiso 0.371(13) 1 calc R . P A 2
C13 C 0.812(2) 0.891(3) 0.480(2) 0.042(2) Uani 0.629(13) 1 d D U P A 1
H13A H 0.8645 0.8918 0.5553 0.063 Uiso 0.629(13) 1 calc R . P A 1
H13B H 0.8484 0.8546 0.4141 0.063 Uiso 0.629(13) 1 calc R . P A 1
H13C H 0.8326 0.9896 0.4849 0.063 Uiso 0.629(13) 1 calc R . P A 1
C13S C 0.756(3) 0.802(4) 0.445(3) 0.042(2) Uani 0.371(13) 1 d D U P A 2
H13D H 0.7588 0.7306 0.4827 0.063 Uiso 0.371(13) 1 calc R . P A 2
H13E H 0.8301 0.8218 0.3964 0.063 Uiso 0.371(13) 1 calc R . P A 2
H13F H 0.7829 0.8912 0.5077 0.063 Uiso 0.371(13) 1 calc R . P A 2
C14 C 0.575(3) 0.715(2) 0.2330(19) 0.043(2) Uani 0.629(13) 1 d D U P A 1
H14A H 0.6848 0.7562 0.2359 0.051 Uiso 0.629(13) 1 calc R . P A 1
H14B H 0.5257 0.7332 0.1657 0.051 Uiso 0.629(13) 1 calc R . P A 1
C14S C 0.487(5) 0.765(4) 0.161(2) 0.042(2) Uani 0.371(13) 1 d D U P A 2
H14C H 0.5820 0.7966 0.1337 0.051 Uiso 0.371(13) 1 calc R . P A 2
H14D H 0.4423 0.8256 0.1442 0.051 Uiso 0.371(13) 1 calc R . P A 2
C15 C 0.507(3) 0.555(2) 0.209(3) 0.044(2) Uani 0.629(13) 1 d D U P A 1
H15A H 0.5217 0.5115 0.1335 0.065 Uiso 0.629(13) 1 calc R . P A 1
H15B H 0.5567 0.5363 0.2746 0.065 Uiso 0.629(13) 1 calc R . P A 1
H15C H 0.3975 0.5133 0.2044 0.065 Uiso 0.629(13) 1 calc R . P A 1
C15S C 0.379(5) 0.613(4) 0.080(4) 0.043(3) Uani 0.371(13) 1 d D U P A 2
H15D H 0.3636 0.6121 -0.0035 0.064 Uiso 0.371(13) 1 calc R . P A 2
H15E H 0.4211 0.5495 0.0902 0.064 Uiso 0.371(13) 1 calc R . P A 2
H15F H 0.2804 0.5787 0.1008 0.064 Uiso 0.371(13) 1 calc R . P A 2
Cl2 Cl 0.8217(9) 0.8112(10) 0.7975(6) 0.101(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au Au 3.221(3) 2_566 ?
Au Cl1 2.269(4) . ?
Au C2 2.017(10) . ?
P O 1.35(2) . ?
P O1S 1.63(3) . ?
P N3 1.83(2) . ?
P N3S 1.57(3) . ?
P C1 1.803(14) . ?
P C3 1.772(13) 2_676 ?
O1S H1S 0.8400 . ?
N1 C1 1.387(16) . ?
N1 C2 1.319(14) . ?
N1 C4 1.45(2) . ?
N2 C2 1.318(15) . ?
N2 C3 1.372(14) . ?
N2 C8 1.494(17) . ?
N3 C12 1.458(10) . ?
N3 C14 1.459(10) . ?
N3S C12S 1.4699(16) . ?
N3S C14S 1.469(10) . ?
C1 C3 1.32(2) . ?
C3 P 1.772(13) 2_676 ?
C4 H4AA 0.9900 . ?
C4 H4AB 0.9900 . ?
C4 H4BC 0.9900 . ?
C4 H4BD 0.9900 . ?
C4 C5 1.499(7) . ?
C4 C5S 1.498(10) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.495(10) . ?
C5S H5SA 0.9900 . ?
C5S H5SB 0.9900 . ?
C5S C6S 1.493(10) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.497(10) . ?
C6S H6SA 0.9900 . ?
C6S H6SB 0.9900 . ?
C6S C7S 1.501(7) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7S H7SA 0.9800 . ?
C7S H7SB 0.9800 . ?
C7S H7SC 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.504(10) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.493(10) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.504(10) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.509(10) . ?
C12S H12C 0.9900 . ?
C12S H12D 0.9900 . ?
C12S C13S 1.500(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13S H13D 0.9800 . ?
C13S H13E 0.9800 . ?
C13S H13F 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.499(10) . ?
C14S H14C 0.9900 . ?
C14S H14D 0.9900 . ?
C14S C15S 1.504(10) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15S H15D 0.9800 . ?
C15S H15E 0.9800 . ?
C15S H15F 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
Cl1 Au Au 102.20(14) . 2_566 ?
C2 Au Au 81.3(3) . 2_566 ?
C2 Au Cl1 176.4(3) . . ?
O P N3 107.5(11) . . ?
O P C1 123.2(10) . . ?
O P C3 120.8(11) . 2_676 ?
O1S P C1 103.7(11) . . ?
O1S P C3 103.8(11) . 2_676 ?
N3S P O1S 119.1(15) . . ?
N3S P C1 116.9(11) . . ?
N3S P C3 110.8(10) . 2_676 ?
C1 P N3 101.7(8) . . ?
C3 P N3 99.5(8) 2_676 . ?
C3 P C1 100.2(6) 2_676 . ?
P O1S H1S 109.5 . . ?
C1 N1 C4 126.1(13) . . ?
C2 N1 C1 109.2(11) . . ?
C2 N1 C4 124.6(12) . . ?
C2 N2 C3 109.0(10) . . ?
C2 N2 C8 122.7(10) . . ?
C3 N2 C8 128.0(11) . . ?
C12 N3 P 120.3(16) . . ?
C12 N3 C14 118(2) . . ?
C14 N3 P 120.1(15) . . ?
C12S N3S P 122(2) . . ?
C14S N3S P 107(2) . . ?
C14S N3S C12S 131(3) . . ?
N1 C1 P 123.4(11) . . ?
C3 C1 P 130.2(10) . . ?
C3 C1 N1 106.3(11) . . ?
N1 C2 Au 128.3(8) . . ?
N2 C2 Au 123.8(8) . . ?
N2 C2 N1 107.6(9) . . ?
N2 C3 P 122.4(10) . 2_676 ?
C1 C3 P 129.7(9) . 2_676 ?
C1 C3 N2 107.9(11) . . ?
N1 C4 H4AA 110.1 . . ?
N1 C4 H4AB 110.1 . . ?
N1 C4 H4BC 106.9 . . ?
N1 C4 H4BD 106.9 . . ?
N1 C4 C5 107.9(19) . . ?
N1 C4 C5S 122(2) . . ?
H4AA C4 H4AB 108.4 . . ?
H4BC C4 H4BD 106.7 . . ?
C5 C4 H4AA 110.1 . . ?
C5 C4 H4AB 110.1 . . ?
C5S C4 H4BC 106.9 . . ?
C5S C4 H4BD 106.9 . . ?
C4 C5 H5A 105.9 . . ?
C4 C5 H5B 105.9 . . ?
H5A C5 H5B 106.3 . . ?
C6 C5 C4 126(3) . . ?
C6 C5 H5A 105.9 . . ?
C6 C5 H5B 105.9 . . ?
C4 C5S H5SA 109.9 . . ?
C4 C5S H5SB 109.9 . . ?
H5SA C5S H5SB 108.3 . . ?
C6S C5S C4 109(2) . . ?
C6S C5S H5SA 109.9 . . ?
C6S C5S H5SB 109.9 . . ?
C5 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C5 C6 C7 114(3) . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
C5S C6S H6SA 110.2 . . ?
C5S C6S H6SB 110.2 . . ?
C5S C6S C7S 108(3) . . ?
H6SA C6S H6SB 108.5 . . ?
C7S C6S H6SA 110.2 . . ?
C7S C6S H6SB 110.2 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6S C7S H7SA 109.5 . . ?
C6S C7S H7SB 109.5 . . ?
C6S C7S H7SC 109.5 . . ?
H7SA C7S H7SB 109.5 . . ?
H7SA C7S H7SC 109.5 . . ?
H7SB C7S H7SC 109.5 . . ?
N2 C8 H8A 109.7 . . ?
N2 C8 H8B 109.7 . . ?
N2 C8 C9 109.9(12) . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C8 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 C8 113.1(16) . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C9 C10 C11 112(2) . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 H12A 109.2 . . ?
N3 C12 H12B 109.2 . . ?
N3 C12 C13 112(2) . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
N3S C12S H12C 104.1 . . ?
N3S C12S H12D 104.1 . . ?
N3S C12S C13S 132.7(9) . . ?
H12C C12S H12D 105.5 . . ?
C13S C12S H12C 104.1 . . ?
C13S C12S H12D 104.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12S C13S H13D 109.5 . . ?
C12S C13S H13E 109.5 . . ?
C12S C13S H13F 109.5 . . ?
H13D C13S H13E 109.5 . . ?
H13D C13S H13F 109.5 . . ?
H13E C13S H13F 109.5 . . ?
N3 C14 H14A 108.9 . . ?
N3 C14 H14B 108.9 . . ?
N3 C14 C15 113(2) . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
N3S C14S H14C 106.7 . . ?
N3S C14S H14D 106.7 . . ?
N3S C14S C15S 123(3) . . ?
H14C C14S H14D 106.6 . . ?
C15S C14S H14C 106.7 . . ?
C15S C14S H14D 106.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14S C15S H15D 109.5 . . ?
C14S C15S H15E 109.5 . . ?
C14S C15S H15F 109.5 . . ?
H15D C15S H15E 109.5 . . ?
H15D C15S H15F 109.5 . . ?
H15E C15S H15F 109.5 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.491 0.267 0.139 16.0 10.2 ?
2 0.509 0.733 0.861 16.0 9.1 ?

_olex2_submission_special_instructions 'No special instructions were received'
#END---------------------------------------------------------------------------

####################################################################### 
# 
# 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_5630f
_database_code_depnum_ccdc_archive 'CCDC 1919568'
loop_
_audit_author_name
_audit_author_address
'Gregor Schnakenburg'
;University of Bonn
Germany
;
_audit_update_record             
;
2019-05-29 deposited with the CCDC.	2020-01-13 downloaded from the CCDC.
;
_audit_creation_date             2018-05-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        NRN-202
_chemical_formula_moiety         'C30 H56 N6 O2 P2'
_chemical_formula_sum            'C30 H56 N6 O2 P2'
_chemical_formula_weight         594.74
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.6880(5)
_cell_length_b                   20.2501(11)
_cell_length_c                   9.9593(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.166(2)
_cell_angle_gamma                90
_cell_volume                     1698.89(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.98
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6810
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0871 before and 0.0513 after correction. The Ratio of minimum to maximum transmission is 0.9126. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            52094
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         2.619
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8-KappaApexII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3876
_reflns_number_total             4102
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         4102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0368P)²+1.0232P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0966
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,
 H10B), C12(H12A,H12B), C14(H14A,H14B)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P 0.09765(4) 0.57360(2) 0.58698(3) 0.01378(9) Uani 1 1 d . . . . .
O O 0.07323(11) 0.64409(4) 0.54979(9) 0.0182(2) Uani 1 1 d . . . . .
N1 N 0.17299(13) 0.44615(5) 0.30741(11) 0.0164(2) Uani 1 1 d . . . . .
N2 N 0.28631(13) 0.53289(5) 0.40602(11) 0.0164(2) Uani 1 1 d . . . . .
N3 N 0.23556(13) 0.56234(5) 0.73107(11) 0.0171(2) Uani 1 1 d . . . . .
C1 C 0.15406(15) 0.52265(6) 0.45983(12) 0.0149(2) Uani 1 1 d . . . . .
C2 C 0.08159(15) 0.46680(6) 0.39710(12) 0.0154(2) Uani 1 1 d . . . . .
C3 C 0.30051(16) 0.48629(6) 0.31042(13) 0.0183(3) Uani 1 1 d . . . . .
C4 C 0.14241(16) 0.38730(6) 0.21851(13) 0.0182(3) Uani 1 1 d . . . . .
H4A H 0.1928 0.3936 0.1404 0.022 Uiso 1 1 calc R . . . .
H4B H 0.0265 0.3833 0.1793 0.022 Uiso 1 1 calc R . . . .
C5 C 0.20318(17) 0.32301(6) 0.29204(14) 0.0203(3) Uani 1 1 d . . . . .
H5A H 0.1491 0.3147 0.3671 0.024 Uiso 1 1 calc R . . . .
H5B H 0.3186 0.3267 0.3341 0.024 Uiso 1 1 calc R . . . .
C6 C 0.17200(19) 0.26556(7) 0.18977(16) 0.0280(3) Uani 1 1 d . . . . .
H6A H 0.0568 0.2633 0.1459 0.034 Uiso 1 1 calc R . . . .
H6B H 0.2277 0.2740 0.1158 0.034 Uiso 1 1 calc R . . . .
C7 C 0.2264(3) 0.19949(8) 0.2571(2) 0.0444(5) Uani 1 1 d . . . . .
H7A H 0.1728 0.1910 0.3313 0.067 Uiso 1 1 calc GR . . . .
H7B H 0.3415 0.2005 0.2960 0.067 Uiso 1 1 calc GR . . . .
H7C H 0.2000 0.1644 0.1876 0.067 Uiso 1 1 calc GR . . . .
C8 C 0.39835(16) 0.58838(7) 0.44097(14) 0.0197(3) Uani 1 1 d . . . . .
H8A H 0.4995 0.5758 0.4189 0.024 Uiso 1 1 calc R . . . .
H8B H 0.4208 0.5966 0.5419 0.024 Uiso 1 1 calc R . . . .
C9 C 0.33778(17) 0.65207(7) 0.36454(14) 0.0225(3) Uani 1 1 d . . . . .
H9A H 0.2411 0.6664 0.3924 0.027 Uiso 1 1 calc R . . . .
H9B H 0.4191 0.6869 0.3940 0.027 Uiso 1 1 calc R . . . .
C10 C 0.2989(2) 0.64652(7) 0.20743(15) 0.0266(3) Uani 1 1 d . . . . .
H10A H 0.2117 0.6143 0.1764 0.032 Uiso 1 1 calc R . . . .
H10B H 0.3931 0.6299 0.1787 0.032 Uiso 1 1 calc R . . . .
C11 C 0.2494(2) 0.71292(8) 0.13800(17) 0.0372(4) Uani 1 1 d . . . . .
H11A H 0.2228 0.7074 0.0372 0.056 Uiso 1 1 calc GR . . . .
H11B H 0.3372 0.7444 0.1655 0.056 Uiso 1 1 calc GR . . . .
H11C H 0.1566 0.7297 0.1667 0.056 Uiso 1 1 calc GR . . . .
C12 C 0.28242(16) 0.61697(7) 0.83039(14) 0.0208(3) Uani 1 1 d . . . . .
H12A H 0.2492 0.6064 0.9162 0.025 Uiso 1 1 calc R . . . .
H12B H 0.2260 0.6576 0.7905 0.025 Uiso 1 1 calc R . . . .
C13 C 0.45908(19) 0.62991(10) 0.8664(2) 0.0438(5) Uani 1 1 d . . . . .
H13A H 0.4914 0.6437 0.7831 0.066 Uiso 1 1 calc GR . . . .
H13B H 0.5159 0.5895 0.9033 0.066 Uiso 1 1 calc GR . . . .
H13C H 0.4845 0.6649 0.9363 0.066 Uiso 1 1 calc GR . . . .
C14 C 0.28026(18) 0.49515(7) 0.78205(14) 0.0239(3) Uani 1 1 d . . . . .
H14A H 0.3970 0.4932 0.8179 0.029 Uiso 1 1 calc R . . . .
H14B H 0.2508 0.4639 0.7034 0.029 Uiso 1 1 calc R . . . .
C15 C 0.2024(2) 0.47276(8) 0.89572(16) 0.0348(4) Uani 1 1 d . . . . .
H15A H 0.0869 0.4775 0.8636 0.052 Uiso 1 1 calc GR . . . .
H15B H 0.2411 0.5000 0.9784 0.052 Uiso 1 1 calc GR . . . .
H15C H 0.2290 0.4264 0.9183 0.052 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P O 1.4769(9) . ?
P N3 1.6448(11) . ?
P C1 1.7921(13) . ?
P C2 1.8000(13) 3_566 ?
N1 C2 1.3966(16) . ?
N1 C3 1.3686(17) . ?
N1 C4 1.4695(16) . ?
N2 C1 1.3971(16) . ?
N2 C3 1.3674(17) . ?
N2 C8 1.4715(16) . ?
N3 C12 1.4734(16) . ?
N3 C14 1.4709(16) . ?
C1 C2 1.3688(17) . ?
C2 P 1.8000(13) 3_566 ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5234(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5262(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.519(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5245(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5220(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.525(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.511(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.523(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
O P N3 112.46(5) . . ?
O P C1 115.25(6) . . ?
O P C2 112.77(6) . 3_566 ?
N3 P C1 105.66(6) . . ?
N3 P C2 108.74(6) . 3_566 ?
C1 P C2 101.11(6) . 3_566 ?
C2 N1 C4 125.52(11) . . ?
C3 N1 C2 113.08(10) . . ?
C3 N1 C4 121.39(11) . . ?
C1 N2 C8 125.53(11) . . ?
C3 N2 C1 112.80(11) . . ?
C3 N2 C8 121.63(11) . . ?
C12 N3 P 120.28(9) . . ?
C14 N3 P 120.25(9) . . ?
C14 N3 C12 117.17(10) . . ?
N2 C1 P 125.34(9) . . ?
C2 C1 P 128.57(10) . . ?
C2 C1 N2 106.09(11) . . ?
N1 C2 P 124.04(9) . 3_566 ?
C1 C2 P 130.28(10) . 3_566 ?
C1 C2 N1 105.62(11) . . ?
N2 C3 N1 102.40(11) . . ?
N1 C4 H4A 108.7 . . ?
N1 C4 H4B 108.7 . . ?
N1 C4 C5 114.40(11) . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C4 C5 C6 110.28(11) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 C5 113.04(13) . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 H8A 108.8 . . ?
N2 C8 H8B 108.8 . . ?
N2 C8 C9 113.60(11) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C8 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 C8 114.42(11) . . ?
C10 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C9 C10 C11 111.59(12) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 H12A 109.0 . . ?
N3 C12 H12B 109.0 . . ?
N3 C12 C13 112.80(12) . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 H14A 108.8 . . ?
N3 C14 H14B 108.8 . . ?
N3 C14 C15 113.84(12) . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
