# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_compound3
_database_code_depnum_ccdc_archive 'CCDC 1450250'
_audit_update_record             
;
2016-01-27 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;
_audit_creation_date             2016-01-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H12 P, C O P'
_chemical_formula_sum            'C5 H12 O P2'
_chemical_formula_weight         150.09
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   18.159(5)
_cell_length_b                   7.4484(19)
_cell_length_c                   6.3101(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     853.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    468
_cell_measurement_temperature    115.05
_cell_measurement_theta_max      24.797
_cell_measurement_theta_min      3.418
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.897
_exptl_absorpt_coefficient_mu    0.430
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.0989 before and 0.0460 after correction.
The Ratio of minimum to maximum transmission is 0.7230.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.036
_exptl_crystal_size_min          0.022
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_unetI/netI     0.0746
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            2200
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.306
_diffrn_reflns_theta_min         2.243
_diffrn_ambient_temperature      115.05
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                573
_reflns_number_total             841
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2014)'
_computing_structure_solution    'ShelXS (Sheldrick, 2014)'
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     49
_refine_ls_number_reflns         841
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      0.995
_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)+(0.0230P)²+0.8167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0900
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: H2A(0.5) H2B(0.5) H2C(0.5) H3A(0.5) H3B(0.5) H3C(0.5)
4.a Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
P1 P 0.37393(6) 0.7500 0.4950(2) 0.0184(3) Uani 1 2 d S TU P . .
C2 C 0.4561(2) 0.7500 0.6492(7) 0.0270(11) Uani 1 2 d S TU P . .
H2A H 0.4611 0.6344 0.7219 0.040 Uiso 0.5 1 calc GR . . A -1
H2B H 0.4538 0.8468 0.7542 0.040 Uiso 0.5 1 calc GR . . A -1
H2C H 0.4986 0.7689 0.5562 0.040 Uiso 0.5 1 calc GR . . A -1
C3 C 0.2978(2) 0.7500 0.6730(7) 0.0261(12) Uani 1 2 d S TU P . .
H3A H 0.3021 0.8519 0.7705 0.039 Uiso 0.5 1 calc GR . . B -1
H3B H 0.2975 0.6378 0.7542 0.039 Uiso 0.5 1 calc GR . . B -1
H3C H 0.2518 0.7603 0.5924 0.039 Uiso 0.5 1 calc GR . . B -1
C1 C 0.37236(16) 0.5563(4) 0.3300(5) 0.0258(7) Uani 1 1 d . U . . .
H1A H 0.4154 0.5575 0.2363 0.039 Uiso 1 1 calc GR . . . .
H1B H 0.3273 0.5567 0.2446 0.039 Uiso 1 1 calc GR . . . .
H1C H 0.3735 0.4482 0.4184 0.039 Uiso 1 1 calc GR . . . .
O1 O 0.71617(17) 0.7500 0.3320(5) 0.0432(10) Uani 1 2 d S TU P . .
C4 C 0.6567(3) 0.7500 0.2443(7) 0.0268(11) Uani 1 2 d S TU P . .
P2 P 0.57930(7) 0.7500 0.1305(2) 0.0314(4) Uani 1 2 d S TU P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C2 1.781(4) . ?
P1 C3 1.782(4) . ?
P1 C1 1.779(3) . ?
P1 C1 1.779(3) 7_575 ?
O1 C4 1.213(5) . ?
C4 P2 1.579(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 P1 C3 107.8(2) . . ?
C1 P1 C2 109.45(13) . . ?
C1 P1 C2 109.45(13) 7_575 . ?
C1 P1 C3 110.88(13) 7_575 . ?
C1 P1 C3 110.88(13) . . ?
C1 P1 C1 108.3(2) 7_575 . ?
O1 C4 P2 179.9(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_compound5
_database_code_depnum_ccdc_archive 'CCDC 1450251'
_audit_update_record             
;
2016-01-27 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;
_audit_creation_date             2016-01-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C2 H3 N, 2(C O P), 2(C7 H18 N3)'
_chemical_formula_sum            'C18 H39 N7 O2 P2'
_chemical_formula_weight         447.50
_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                   11.8762(6)
_cell_length_b                   15.7545(8)
_cell_length_c                   13.6079(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.012(2)
_cell_angle_gamma                90
_cell_volume                     2539.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9866
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.168
_cell_measurement_theta_min      2.553
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1228 before and 0.0517 after correction.
The Ratio of minimum to maximum transmission is 0.9421.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.349
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.221
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            49655
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.198
_diffrn_reflns_theta_min         2.553
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4619
_reflns_number_total             5654
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2014)'
_computing_structure_solution    'ShelXS (Sheldrick, 2014)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         5654
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.052
_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)+(0.0278P)²+0.7915P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0741
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(N13)=Sof(N11)=Sof(N12)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C29)=
 Sof(H29A)=Sof(H29B)=Sof(H29C)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=Sof(C25)=
 Sof(H25A)=Sof(H25B)=Sof(H25C)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=Sof(C28)=
 Sof(H28A)=Sof(H28B)=Sof(H28C)=1-FVAR(1)
 Sof(N4)=Sof(N5)=Sof(N6)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H11C)=Sof(C12)=
 Sof(H12A)=Sof(H12B)=Sof(H12C)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(C14)=
 Sof(H14A)=Sof(H14B)=Sof(H14C)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(C16)=
 Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(1)
 Sof(N9)=Sof(N8)=Sof(N10)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=Sof(C19)=
 Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=Sof(C17)=
 Sof(H17A)=Sof(H17B)=Sof(H17C)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C21)=
 Sof(H21A)=Sof(H21B)=Sof(H21C)=1-FVAR(2)
 Sof(N1)=Sof(N3)=Sof(N2)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C7)=Sof(H7A)=
 Sof(H7B)=Sof(H7C)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(H5C)=Sof(C6)=Sof(H6A)=Sof(H6B)=
 Sof(H6C)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=Sof(C9)=Sof(H9A)=Sof(H9B)=
 Sof(H9C)=FVAR(2)
3.a Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C24(H24A,
 H24B,H24C), C29(H29A,H29B,H29C), C27(H27A,H27B,H27C), C25(H25A,H25B,H25C),
 C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C8(H8A,H8B,H8C), C7(H7A,H7B,H7C),
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C),
 C22(H22A,H22B,H22C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C17(H17A,H17B,
 H17C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C3 C 0.85413(10) 0.89833(8) 0.65008(9) 0.0246(3) Uani 1 1 d . . . . .
C4 C 0.91122(11) 0.82201(8) 0.68649(9) 0.0280(3) Uani 1 1 d . . . . .
H4A H 0.8840 0.7733 0.6469 0.042 Uiso 1 1 calc GR . . . .
H4B H 0.8954 0.8128 0.7554 0.042 Uiso 1 1 calc GR . . . .
H4C H 0.9928 0.8284 0.6818 0.042 Uiso 1 1 calc GR . . . .
C1 C 0.25354(10) 0.09872(8) 0.07514(9) 0.0237(3) Uani 1 1 d . . . . .
N4 N 0.94898(14) 0.89085(11) 0.31204(12) 0.0168(4) Uani 0.5410(16) 1 d . . P A
1
N5 N 1.13132(14) 0.84013(11) 0.30169(12) 0.0174(4) Uani 0.5410(16) 1 d . . P A
1
N6 N 1.04132(14) 0.91200(11) 0.16941(12) 0.0165(4) Uani 0.5410(16) 1 d . . P A
1
C11 C 0.8341(8) 0.8873(7) 0.2649(7) 0.0217(13) Uani 0.5410(16) 1 d . . P A 1
H11A H 0.8376 0.8758 0.1944 0.033 Uiso 0.5410(16) 1 calc GR . P A 1
H11B H 0.7963 0.9418 0.2738 0.033 Uiso 0.5410(16) 1 calc GR . P A 1
H11C H 0.7918 0.8420 0.2951 0.033 Uiso 0.5410(16) 1 calc GR . P A 1
C12 C 0.9553(4) 0.9066(4) 0.4181(4) 0.0217(9) Uani 0.5410(16) 1 d . . P A 1
H12A H 0.9279 0.8566 0.4520 0.033 Uiso 0.5410(16) 1 calc GR . P A 1
H12B H 0.9084 0.9558 0.4319 0.033 Uiso 0.5410(16) 1 calc GR . P A 1
H12C H 1.0338 0.9180 0.4415 0.033 Uiso 0.5410(16) 1 calc GR . P A 1
C13 C 1.1242(10) 0.7749(7) 0.3753(8) 0.0196(15) Uani 0.5410(16) 1 d . . P A 1
H13A H 1.0455 0.7566 0.3774 0.029 Uiso 0.5410(16) 1 calc GR . P A 1
H13B H 1.1511 0.7975 0.4398 0.029 Uiso 0.5410(16) 1 calc GR . P A 1
H13C H 1.1709 0.7265 0.3587 0.029 Uiso 0.5410(16) 1 calc GR . P A 1
C14 C 1.2467(5) 0.8634(4) 0.2796(3) 0.0209(9) Uani 0.5410(16) 1 d . . P A 1
H14A H 1.2789 0.8180 0.2410 0.031 Uiso 0.5410(16) 1 calc GR . P A 1
H14B H 1.2931 0.8713 0.3413 0.031 Uiso 0.5410(16) 1 calc GR . P A 1
H14C H 1.2449 0.9163 0.2417 0.031 Uiso 0.5410(16) 1 calc GR . P A 1
C15 C 1.1016(10) 0.8707(8) 0.0926(8) 0.0218(17) Uani 0.5410(16) 1 d . . P A 1
H15A H 1.1654 0.9062 0.0763 0.033 Uiso 0.5410(16) 1 calc GR . P A 1
H15B H 1.0503 0.8628 0.0338 0.033 Uiso 0.5410(16) 1 calc GR . P A 1
H15C H 1.1297 0.8153 0.1163 0.033 Uiso 0.5410(16) 1 calc GR . P A 1
C16 C 0.9836(6) 0.9916(6) 0.1393(7) 0.0180(11) Uani 0.5410(16) 1 d . . P A 1
H16A H 0.9537 1.0185 0.1970 0.027 Uiso 0.5410(16) 1 calc GR . P A 1
H16B H 0.9213 0.9791 0.0903 0.027 Uiso 0.5410(16) 1 calc GR . P A 1
H16C H 1.0373 1.0300 0.1106 0.027 Uiso 0.5410(16) 1 calc GR . P A 1
N13 N 0.95146(16) 0.92331(13) 0.21915(14) 0.0170(5) Uani 0.4590(16) 1 d . . P A
2
N11 N 1.04525(17) 0.85040(13) 0.34851(14) 0.0179(5) Uani 0.4590(16) 1 d . . P A
2
N12 N 1.13213(16) 0.87114(12) 0.20249(14) 0.0159(5) Uani 0.4590(16) 1 d . . P A
2
C24 C 0.8383(9) 0.9002(8) 0.2432(7) 0.0193(14) Uani 0.4590(16) 1 d . . P A 2
H24A H 0.8415 0.8485 0.2833 0.029 Uiso 0.4590(16) 1 calc GR . P A 2
H24B H 0.7912 0.8900 0.1823 0.029 Uiso 0.4590(16) 1 calc GR . P A 2
H24C H 0.8057 0.9465 0.2801 0.029 Uiso 0.4590(16) 1 calc GR . P A 2
C29 C 0.9913(4) 0.8940(5) 0.4277(5) 0.0228(11) Uani 0.4590(16) 1 d . . P A 2
H29A H 0.9646 0.9498 0.4045 0.034 Uiso 0.4590(16) 1 calc GR . P A 2
H29B H 1.0459 0.9010 0.4844 0.034 Uiso 0.4590(16) 1 calc GR . P A 2
H29C H 0.9271 0.8603 0.4470 0.034 Uiso 0.4590(16) 1 calc GR . P A 2
C27 C 1.2481(6) 0.8683(5) 0.2457(3) 0.0223(11) Uani 0.4590(16) 1 d . . P A 2
H27A H 1.2497 0.8854 0.3150 0.033 Uiso 0.4590(16) 1 calc GR . P A 2
H27B H 1.2949 0.9073 0.2099 0.033 Uiso 0.4590(16) 1 calc GR . P A 2
H27C H 1.2775 0.8105 0.2411 0.033 Uiso 0.4590(16) 1 calc GR . P A 2
C25 C 0.9567(8) 0.9936(7) 0.1513(8) 0.0209(15) Uani 0.4590(16) 1 d . . P A 2
H25A H 0.9122 1.0411 0.1743 0.031 Uiso 0.4590(16) 1 calc GR . P A 2
H25B H 0.9259 0.9759 0.0858 0.031 Uiso 0.4590(16) 1 calc GR . P A 2
H25C H 1.0354 1.0114 0.1479 0.031 Uiso 0.4590(16) 1 calc GR . P A 2
C26 C 1.1204(12) 0.8595(9) 0.0950(8) 0.0192(17) Uani 0.4590(16) 1 d . . P A 2
H26A H 1.0402 0.8561 0.0730 0.029 Uiso 0.4590(16) 1 calc GR . P A 2
H26B H 1.1583 0.8069 0.0776 0.029 Uiso 0.4590(16) 1 calc GR . P A 2
H26C H 1.1549 0.9076 0.0629 0.029 Uiso 0.4590(16) 1 calc GR . P A 2
C28 C 1.1038(11) 0.7703(9) 0.3781(11) 0.0214(19) Uani 0.4590(16) 1 d . . P A 2
H28A H 1.1300 0.7422 0.3196 0.032 Uiso 0.4590(16) 1 calc GR . P A 2
H28B H 1.0515 0.7328 0.4098 0.032 Uiso 0.4590(16) 1 calc GR . P A 2
H28C H 1.1686 0.7830 0.4243 0.032 Uiso 0.4590(16) 1 calc GR . P A 2
N1 N 0.54204(9) 0.91799(7) 0.33050(8) 0.0170(3) Uani 0.8131(16) 1 d . . P B 1
N3 N 0.52909(10) 0.90458(7) 0.16050(8) 0.0200(3) Uani 0.8131(16) 1 d . . P B 1
N2 N 0.54767(9) 0.78444(7) 0.25829(8) 0.0172(3) Uani 0.8131(16) 1 d . . P B 1
C8 C 0.6031(3) 0.7318(2) 0.18762(17) 0.0216(5) Uani 0.8131(16) 1 d . . P B 1
H8A H 0.5461 0.6992 0.1481 0.032 Uiso 0.8131(16) 1 calc GR . P B 1
H8B H 0.6558 0.6928 0.2231 0.032 Uiso 0.8131(16) 1 calc GR . P B 1
H8C H 0.6446 0.7682 0.1442 0.032 Uiso 0.8131(16) 1 calc GR . P B 1
C7 C 0.4989(2) 0.73739(17) 0.33693(19) 0.0201(5) Uani 0.8131(16) 1 d . . P B 1
H7A H 0.4579 0.7765 0.3775 0.030 Uiso 0.8131(16) 1 calc GR . P B 1
H7B H 0.5593 0.7096 0.3779 0.030 Uiso 0.8131(16) 1 calc GR . P B 1
H7C H 0.4468 0.6943 0.3084 0.030 Uiso 0.8131(16) 1 calc GR . P B 1
C5 C 0.47735(14) 0.99677(11) 0.33421(16) 0.0198(4) Uani 0.8131(16) 1 d . . P B
1
H5A H 0.4304 1.0037 0.2726 0.030 Uiso 0.8131(16) 1 calc GR . P B 1
H5B H 0.5293 1.0449 0.3429 0.030 Uiso 0.8131(16) 1 calc GR . P B 1
H5C H 0.4290 0.9945 0.3896 0.030 Uiso 0.8131(16) 1 calc GR . P B 1
C6 C 0.6083(2) 0.89678(19) 0.42115(18) 0.0211(5) Uani 0.8131(16) 1 d . . P B 1
H6A H 0.6552 0.8470 0.4101 0.032 Uiso 0.8131(16) 1 calc GR . P B 1
H6B H 0.5575 0.8841 0.4730 0.032 Uiso 0.8131(16) 1 calc GR . P B 1
H6C H 0.6567 0.9449 0.4415 0.032 Uiso 0.8131(16) 1 calc GR . P B 1
C10 C 0.5778(2) 0.98748(16) 0.13880(19) 0.0233(5) Uani 0.8131(16) 1 d . . P B 1
H10A H 0.6233 1.0079 0.1969 0.035 Uiso 0.8131(16) 1 calc GR . P B 1
H10B H 0.5169 1.0280 0.1217 0.035 Uiso 0.8131(16) 1 calc GR . P B 1
H10C H 0.6256 0.9819 0.0833 0.035 Uiso 0.8131(16) 1 calc GR . P B 1
C9 C 0.4677(3) 0.8631(2) 0.0764(2) 0.0273(6) Uani 0.8131(16) 1 d . . P B 1
H9A H 0.4115 0.9023 0.0461 0.041 Uiso 0.8131(16) 1 calc GR . P B 1
H9B H 0.4297 0.8122 0.0991 0.041 Uiso 0.8131(16) 1 calc GR . P B 1
H9C H 0.5210 0.8469 0.0278 0.041 Uiso 0.8131(16) 1 calc GR . P B 1
N9 N 0.5313(4) 0.8229(3) 0.1637(3) 0.0110(10) Uani 0.1869(16) 1 d . . P B 2
N8 N 0.5454(4) 0.8358(3) 0.3344(3) 0.0128(11) Uani 0.1869(16) 1 d . . P B 2
N10 N 0.5287(4) 0.9569(3) 0.2367(3) 0.0124(11) Uani 0.1869(16) 1 d . . P B 2
C22 C 0.4719(8) 1.0108(6) 0.3032(6) 0.017(2) Uiso 0.1869(16) 1 d . . P B 2
H22A H 0.4389 0.9758 0.3533 0.026 Uiso 0.1869(16) 1 calc GR . P B 2
H22B H 0.4121 1.0426 0.2661 0.026 Uiso 0.1869(16) 1 calc GR . P B 2
H22C H 0.5263 1.0506 0.3352 0.026 Uiso 0.1869(16) 1 calc GR . P B 2
C19 C 0.5967(13) 0.7451(9) 0.1552(8) 0.020(2) Uani 0.1869(16) 1 d . . P B 2
H19A H 0.6465 0.7373 0.2150 0.030 Uiso 0.1869(16) 1 calc GR . P B 2
H19B H 0.6423 0.7493 0.0980 0.030 Uiso 0.1869(16) 1 calc GR . P B 2
H19C H 0.5453 0.6966 0.1468 0.030 Uiso 0.1869(16) 1 calc GR . P B 2
C18 C 0.4953(11) 0.7525(7) 0.3562(9) 0.016(3) Uiso 0.1869(16) 1 d . . P B 2
H18A H 0.4474 0.7333 0.2989 0.024 Uiso 0.1869(16) 1 calc GR . P B 2
H18B H 0.4496 0.7580 0.4131 0.024 Uiso 0.1869(16) 1 calc GR . P B 2
H18C H 0.5556 0.7111 0.3711 0.024 Uiso 0.1869(16) 1 calc GR . P B 2
C17 C 0.6078(12) 0.8737(7) 0.4225(10) 0.021(3) Uiso 0.1869(16) 1 d . . P B 2
H17A H 0.6496 0.9238 0.4026 0.032 Uiso 0.1869(16) 1 calc GR . P B 2
H17B H 0.6608 0.8319 0.4525 0.032 Uiso 0.1869(16) 1 calc GR . P B 2
H17C H 0.5541 0.8905 0.4705 0.032 Uiso 0.1869(16) 1 calc GR . P B 2
C20 C 0.4635(15) 0.8435(9) 0.0752(13) 0.024(3) Uiso 0.1869(16) 1 d . . P B 2
H20A H 0.4221 0.7929 0.0514 0.036 Uiso 0.1869(16) 1 calc GR . P B 2
H20B H 0.5124 0.8632 0.0248 0.036 Uiso 0.1869(16) 1 calc GR . P B 2
H20C H 0.4098 0.8884 0.0893 0.036 Uiso 0.1869(16) 1 calc GR . P B 2
C21 C 0.5716(11) 1.0044(7) 0.1580(8) 0.022(3) Uiso 0.1869(16) 1 d . . P B 2
H21A H 0.6179 0.9674 0.1193 0.032 Uiso 0.1869(16) 1 calc GR . P B 2
H21B H 0.6178 1.0515 0.1852 0.032 Uiso 0.1869(16) 1 calc GR . P B 2
H21C H 0.5085 1.0269 0.1156 0.032 Uiso 0.1869(16) 1 calc GR . P B 2
C23 C 0.53879(8) 0.86957(7) 0.24901(8) 0.0148(2) Uani 1 1 d . . . . .
N7 N 0.80959(11) 0.95817(8) 0.62080(9) 0.0417(3) Uani 1 1 d . . . . .
P1 P 0.19229(3) 0.18438(2) 0.03909(2) 0.02797(9) Uani 1 1 d . . . . .
C30 C 1.04202(9) 0.88140(7) 0.25920(8) 0.0154(2) Uani 1 1 d . . . . .
C2 C 0.69775(10) 0.14139(8) 0.41998(9) 0.0247(3) Uani 1 1 d . . . . .
P2 P 0.77504(3) 0.12766(2) 0.33093(3) 0.03195(9) Uani 1 1 d . . . . .
O1 O 0.63856(9) 0.15177(8) 0.48624(8) 0.0566(3) Uani 1 1 d . . . . .
O4 O 0.30030(10) 0.03547(7) 0.10249(10) 0.0569(3) 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
C3 C4 1.4505(18) . ?
C3 N7 1.1394(17) . ?
C1 P1 1.5942(13) . ?
C1 O4 1.1879(15) . ?
N4 C11 1.467(10) . ?
N4 C12 1.461(6) . ?
N4 C30 1.3679(19) . ?
N5 C13 1.441(10) . ?
N5 C14 1.469(6) . ?
N5 C30 1.340(2) . ?
N6 C15 1.461(10) . ?
N6 C16 1.473(8) . ?
N6 C30 1.3130(19) . ?
N13 C24 1.452(10) . ?
N13 C25 1.446(10) . ?
N13 C30 1.344(2) . ?
N11 C29 1.462(7) . ?
N11 C28 1.483(13) . ?
N11 C30 1.308(2) . ?
N12 C27 1.460(7) . ?
N12 C26 1.471(11) . ?
N12 C30 1.372(2) . ?
N1 C5 1.462(2) . ?
N1 C6 1.455(3) . ?
N1 C23 1.3442(15) . ?
N3 C10 1.467(3) . ?
N3 C9 1.467(3) . ?
N3 C23 1.3224(15) . ?
N2 C8 1.461(3) . ?
N2 C7 1.455(3) . ?
N2 C23 1.3507(15) . ?
N9 C19 1.460(14) . ?
N9 C20 1.438(18) . ?
N9 C23 1.371(4) . ?
N8 C18 1.479(14) . ?
N8 C17 1.491(14) . ?
N8 C23 1.275(4) . ?
N10 C22 1.441(10) . ?
N10 C21 1.430(13) . ?
N10 C23 1.390(4) . ?
C2 P2 1.5853(13) . ?
C2 O1 1.1927(16) . ?

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
N7 C3 C4 179.49(14) . . ?
O4 C1 P1 179.18(12) . . ?
C12 N4 C11 114.8(4) . . ?
C30 N4 C11 121.8(4) . . ?
C30 N4 C12 123.4(2) . . ?
C13 N5 C14 114.9(5) . . ?
C30 N5 C13 124.2(5) . . ?
C30 N5 C14 120.8(2) . . ?
C15 N6 C16 115.0(6) . . ?
C30 N6 C15 122.0(5) . . ?
C30 N6 C16 122.9(4) . . ?
C25 N13 C24 114.7(6) . . ?
C30 N13 C24 120.8(4) . . ?
C30 N13 C25 124.5(4) . . ?
C29 N11 C28 114.9(6) . . ?
C30 N11 C29 121.5(3) . . ?
C30 N11 C28 123.6(6) . . ?
C27 N12 C26 114.7(6) . . ?
C30 N12 C27 121.9(2) . . ?
C30 N12 C26 123.4(6) . . ?
C6 N1 C5 114.83(16) . . ?
C23 N1 C5 121.69(12) . . ?
C23 N1 C6 123.49(14) . . ?
C10 N3 C9 114.91(18) . . ?
C23 N3 C10 122.98(14) . . ?
C23 N3 C9 122.11(17) . . ?
C7 N2 C8 114.59(17) . . ?
C23 N2 C8 122.52(14) . . ?
C23 N2 C7 122.84(14) . . ?
C20 N9 C19 113.1(8) . . ?
C23 N9 C19 120.9(6) . . ?
C23 N9 C20 126.0(7) . . ?
C18 N8 C17 112.2(7) . . ?
C23 N8 C18 123.6(6) . . ?
C23 N8 C17 124.1(6) . . ?
C21 N10 C22 111.6(6) . . ?
C23 N10 C22 123.2(5) . . ?
C23 N10 C21 125.2(5) . . ?
N1 C23 N2 119.27(10) . . ?
N3 C23 N1 120.68(10) . . ?
N3 C23 N2 120.04(10) . . ?
N9 C23 N10 115.4(3) . . ?
N8 C23 N9 122.9(3) . . ?
N8 C23 N10 121.5(3) . . ?
N5 C30 N4 118.03(13) . . ?
N6 C30 N4 119.76(13) . . ?
N6 C30 N5 122.20(13) . . ?
N13 C30 N12 117.58(14) . . ?
N11 C30 N13 122.06(14) . . ?
N11 C30 N12 120.35(14) . . ?
O1 C2 P2 179.26(12) . . ?

_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_compound6
_database_code_depnum_ccdc_archive 'CCDC 1450252'
_audit_update_record             
;
2016-01-27 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;
_audit_creation_date             2016-01-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C4 H12 N, C O P'
_chemical_formula_sum            'C5 H12 N O P'
_chemical_formula_weight         133.13
_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           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.9410(5)
_cell_length_b                   7.4092(6)
_cell_length_c                   8.8324(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.184(4)
_cell_angle_gamma                90
_cell_volume                     383.80(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2211
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.01
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/4
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             144
_exptl_crystal_size_max          0.415
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.126
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4874
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.135
_diffrn_reflns_theta_min         2.336
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_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'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                807
_reflns_number_total             921
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2014)'
_computing_structure_solution    'ShelXS (Sheldrick, 2014)'
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     47
_refine_ls_number_reflns         921
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      1.066
_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)+(0.0326P)²+0.1491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0735
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups
2.a Riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
N1 N 0.4564(2) 0.7500 0.75334(16) 0.0138(3) Uani 1 2 d S T P . .
C1 C 0.6044(2) 0.58546(16) 0.75924(15) 0.0180(3) Uani 1 1 d . . . . .
H1A H 0.7148 0.5863 0.8544 0.027 Uiso 1 1 calc GR . . . .
H1B H 0.6858 0.5855 0.6711 0.027 Uiso 1 1 calc GR . . . .
H1C H 0.5092 0.4770 0.7561 0.027 Uiso 1 1 calc GR . . . .
C2 C 0.3316(3) 0.7500 0.8880(2) 0.0206(4) Uani 1 2 d S T P . .
H2A H 0.4383 0.7500 0.9731 0.031 Uiso 1 2 d RS T P . .
H2B H 0.2385 0.8558 0.8821 0.031 Uiso 1 1 d R . . . .
C3 C 0.2876(3) 0.7500 0.6078(2) 0.0215(4) Uani 1 2 d S T P . .
H3A H 0.1877 0.8583 0.6088 0.032 Uiso 1 1 d R . . . .
H3B H 0.3695 0.7500 0.5238 0.032 Uiso 1 2 d RS T P . .
P1 P 0.95284(8) 0.7500 0.16655(6) 0.01863(16) Uani 1 2 d S T P . .
O1 O 0.7632(2) 0.7500 0.43762(15) 0.0287(3) Uani 1 2 d S T P . .
C4 C 0.8460(3) 0.7500 0.3219(2) 0.0168(4) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.4990(14) 4_575 ?
N1 C1 1.4990(14) . ?
N1 C2 1.499(2) . ?
N1 C3 1.499(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9023 . ?
C2 H2B 0.9557 . ?
C3 H3A 0.9991 . ?
C3 H3B 0.9502 . ?
P1 C4 1.6011(19) . ?
O1 C4 1.203(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C1 108.84(13) . 4_575 ?
C2 N1 C1 109.52(9) . . ?
C2 N1 C1 109.52(9) . 4_575 ?
C3 N1 C1 109.76(9) . . ?
C3 N1 C1 109.76(9) . 4_575 ?
C3 N1 C2 109.43(14) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 106.9 . . ?
N1 C2 H2B 108.2 . . ?
H2A C2 H2B 111.6 . . ?
N1 C3 H3A 108.1 . . ?
N1 C3 H3B 108.3 . . ?
H3A C3 H3B 112.7 . . ?
O1 C4 P1 179.22(16) . . ?

_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_mj47
_database_code_depnum_ccdc_archive 'CCDC 1454441'
_audit_update_record             
;
2016-02-18 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT360_mj47                
;
PROBLEM: Short  C(sp3)-C(sp3) Bond   C25    -   C26    ..       1.22 Ang.
RESPONSE: Due to the heavy disorder of the nButyl groups this issue cannot be solved. Since the dataset was measured on an outdated spectrometer a fully correct interpretation of the disorder is not possible.
;
_vrf_PLAT242_mj47                
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        C38 Check
RESPONSE: see above
;
_vrf_PLAT342_mj47                
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0612 Ang.
RESPONSE: see above
;
_vrf_PLAT360_mj47_2              
;
PROBLEM: Short  C(sp3)-C(sp3) Bond   C23    -   C24    ..       1.27 Ang.
RESPONSE: see above
;
_vrf_PLAT412_mj47                
;
PROBLEM: Short Intra XH3 .. XHn     H6B    ..  H9C     ..       1.79 Ang.
RESPONSE: see above
;

# Added during the CSD deposition process: Thursday 18th of February 2016 12:18:07 PM
# end Validation Reply Form

_audit_creation_date             2016-02-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '3(C13 H30 P), Sb11'
_chemical_formula_sum            'C39 H90 P3 Sb11'
_chemical_formula_weight         1991.26
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   31.443(2)
_cell_length_b                   11.2133(7)
_cell_length_c                   21.6617(11)
_cell_angle_alpha                90
_cell_angle_beta                 123.210(4)
_cell_angle_gamma                90
_cell_volume                     6390.1(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8794
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      24.65
_cell_measurement_theta_min      1.49
_shelx_estimated_absorpt_T_max   0.835
_shelx_estimated_absorpt_T_min   0.504
_exptl_absorpt_coefficient_mu    4.667
_exptl_absorpt_correction_T_max  0.8823
_exptl_absorpt_correction_T_min  0.5248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            black
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    2.070
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             3720
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1463
_diffrn_reflns_av_unetI/netI     0.1957
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            29052
_diffrn_reflns_point_group_measured_fraction_full 0.900
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.827
_diffrn_reflns_theta_min         1.907
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       rotational
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_full    0.800
_reflns_Friedel_fraction_max     0.775
_reflns_number_gt                5394
_reflns_number_total             12094
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.632
_refine_diff_density_min         -1.087
_refine_diff_density_rms         0.199
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.13(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.719
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     496
_refine_ls_number_reflns         12094
_refine_ls_number_restraints     386
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      0.713
_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)+(0.0503P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1339
_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
2. Restrained distances
 C12-C13
 1.55 with sigma of 0.02
 C4-C5
 1.55 with sigma of 0.02
 C4-C5A
 1.55 with sigma of 0.02
 C8-C9
 1.55 with sigma of 0.02
 C8-C9A
 1.55 with sigma of 0.02
 C19-C20
 1.55 with sigma of 0.02
 C21-C22
 1.55 with sigma of 0.02
 C20-C21
 1.55 with sigma of 0.02
 C38-C39
 1.55 with sigma of 0.02
 C7-C9A
 2.6 with sigma of 0.04
3. Rigid bond restraints
 P1, C1, C2, C3, C4, C5, C5A, C6, C7, C8, C9, C9A, C10, C11, C12, C13
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 P2, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 P3, C27, C28, C29, C30, C31, C32, C33, C34, C35, C36, C37, C38, C39
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C5A) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C9A) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
5. Rigid body (RIGU) restrains
 P1, C1, C2, C3, C4, C5, C5A, C6, C7, C8, C9, C9A, C10, C11, C12, C13
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 P2, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 P3, C27, C28, C29, C30, C31, C32, C33, C34, C35, C36, C37, C38, C39
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Same fragment restrains
{C6, C7, C8, C9} sigma for 1-2: 0.02, 1-3: 0.04
as
{C10, C11, C12, C13}
{C15, C16, C17, C18} sigma for 1-2: 0.02, 1-3: 0.04
as
{C19, C20, C21, C22}
7. Others
 Fixed Sof: H4AA(0.7) H4AB(0.7) H4BC(0.3) H4BD(0.3) C5(0.7) H5A(0.7) H5B(0.7)
 H5C(0.7) C5A(0.3) H5AA(0.3) H5AB(0.3) H5AC(0.3) H8AA(0.7) H8AB(0.7) H8BC(0.3)
 H8BD(0.3) C9(0.7) H9A(0.7) H9B(0.7) H9C(0.7) C9A(0.3) H9AA(0.3) H9AB(0.3)
 H9AC(0.3)
8.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4AA,H4AB), C4(H4BC,H4BD), C6(H6A,H6B), C7(H7A,
 H7B), C8(H8AA,H8AB), C8(H8BC,H8BD), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,
 H12B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C19(H19A,H19B),
 C20(H20A,H20B), C21(H21A,H21B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B),
  C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C32(H32A,H32B), C33(H33A,
 H33B), C34(H34A,H34B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B)
8.b Me refined with riding coordinates:
 C1(H1A,H1B,H1C), C5(H5A,H5B,H5C), C5A(H5AA,H5AB,H5AC), C9(H9A,H9B,H9C),
 C9A(H9AA,H9AB,H9AC), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C18(H18A,H18B,
 H18C), C22(H22A,H22B,H22C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C31(H31A,
 H31B,H31C), C35(H35A,H35B,H35C), C39(H39A,H39B,H39C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.7639(12) 0.913(2) 0.6977(16) 0.072(7) Uani 1 1 d . U . . .
H1A H 0.7966 0.9150 0.7021 0.108 Uiso 1 1 calc R . . . .
H1B H 0.7363 0.9060 0.6456 0.108 Uiso 1 1 calc R . . . .
H1C H 0.7597 0.9872 0.7179 0.108 Uiso 1 1 calc R . . . .
C2 C 0.7021(13) 0.782(3) 0.741(2) 0.085(6) Uani 1 1 d . U . . .
H2A H 0.7031 0.7155 0.7718 0.103 Uiso 1 1 calc R . . . .
H2B H 0.6976 0.8571 0.7613 0.103 Uiso 1 1 calc R . . . .
C3 C 0.6603(13) 0.767(3) 0.669(2) 0.088(8) Uani 1 1 d . U . . .
H3A H 0.6615 0.6870 0.6503 0.106 Uiso 1 1 calc R . . . .
H3B H 0.6610 0.8276 0.6360 0.106 Uiso 1 1 calc R . . . .
C4 C 0.6082(14) 0.781(3) 0.668(2) 0.108(10) Uani 1 1 d D U . . .
H4AA H 0.6098 0.7346 0.7079 0.130 Uiso 0.7 1 calc R . P A 1
H4AB H 0.6011 0.8659 0.6722 0.130 Uiso 0.7 1 calc R . P A 1
H4BC H 0.5972 0.7043 0.6771 0.130 Uiso 0.3 1 calc R . P B 2
H4BD H 0.6121 0.8410 0.7044 0.130 Uiso 0.3 1 calc R . P B 2
C5 C 0.569(2) 0.731(7) 0.592(3) 0.16(3) Uani 0.7 1 d D U P C 1
H5A H 0.5351 0.7339 0.5844 0.239 Uiso 0.7 1 calc R . P C 1
H5B H 0.5687 0.7776 0.5539 0.239 Uiso 0.7 1 calc R . P C 1
H5C H 0.5773 0.6475 0.5893 0.239 Uiso 0.7 1 calc R . P C 1
C5A C 0.571(4) 0.825(11) 0.588(4) 0.11(3) Uani 0.3 1 d D U P C 2
H5AA H 0.5375 0.8376 0.5793 0.167 Uiso 0.3 1 calc R . P C 2
H5AB H 0.5837 0.9000 0.5805 0.167 Uiso 0.3 1 calc R . P C 2
H5AC H 0.5689 0.7647 0.5534 0.167 Uiso 0.3 1 calc R . P C 2
C6 C 0.8197(12) 0.812(3) 0.8506(15) 0.086(7) Uani 1 1 d D U . . .
H6A H 0.8083 0.8633 0.8759 0.103 Uiso 1 1 calc R . . . .
H6B H 0.8289 0.7333 0.8757 0.103 Uiso 1 1 calc R . . . .
C7 C 0.8668(15) 0.866(4) 0.860(2) 0.138(12) Uani 1 1 d D U . . .
H7A H 0.8586 0.9466 0.8374 0.165 Uiso 1 1 calc R . . . .
H7B H 0.8782 0.8165 0.8338 0.165 Uiso 1 1 calc R . . . .
C8 C 0.9096(16) 0.875(5) 0.942(2) 0.169(17) Uani 1 1 d D U . . .
H8AA H 0.9423 0.8475 0.9499 0.203 Uiso 0.7 1 calc R . P D 1
H8AB H 0.9138 0.9587 0.9592 0.203 Uiso 0.7 1 calc R . P D 1
H8BC H 0.9303 0.9465 0.9475 0.203 Uiso 0.3 1 calc R . P E 2
H8BD H 0.9318 0.8049 0.9540 0.203 Uiso 0.3 1 calc R . P E 2
C9 C 0.892(3) 0.795(6) 0.980(3) 0.16(2) Uani 0.7 1 d D U P F 1
H9A H 0.9179 0.7953 1.0337 0.240 Uiso 0.7 1 calc R . P F 1
H9B H 0.8599 0.8234 0.9710 0.240 Uiso 0.7 1 calc R . P F 1
H9C H 0.8882 0.7130 0.9617 0.240 Uiso 0.7 1 calc R . P F 1
C9A C 0.895(4) 0.884(17) 0.999(4) 0.16(3) Uani 0.3 1 d D U P F 2
H9AA H 0.9264 0.8895 1.0482 0.238 Uiso 0.3 1 calc R . P F 2
H9AB H 0.8745 0.9554 0.9889 0.238 Uiso 0.3 1 calc R . P F 2
H9AC H 0.8761 0.8131 0.9955 0.238 Uiso 0.3 1 calc R . P F 2
C10 C 0.7719(11) 0.649(2) 0.7136(15) 0.066(6) Uani 1 1 d D U . . .
H10A H 0.7685 0.5827 0.7409 0.079 Uiso 1 1 calc R . . . .
H10B H 0.7439 0.6406 0.6612 0.079 Uiso 1 1 calc R . . . .
C11 C 0.8216(11) 0.632(2) 0.7188(16) 0.071(7) Uani 1 1 d D U . . .
H11A H 0.8503 0.6340 0.7712 0.085 Uiso 1 1 calc R . . . .
H11B H 0.8263 0.6981 0.6927 0.085 Uiso 1 1 calc R . . . .
C12 C 0.8208(11) 0.514(2) 0.6844(16) 0.074(7) Uani 1 1 d D U . . .
H12A H 0.8150 0.4485 0.7098 0.089 Uiso 1 1 calc R . . . .
H12B H 0.7923 0.5131 0.6319 0.089 Uiso 1 1 calc R . . . .
C13 C 0.8704(11) 0.492(3) 0.6900(18) 0.088(9) Uani 1 1 d D U . . .
H13A H 0.8689 0.4152 0.6675 0.132 Uiso 1 1 calc R . . . .
H13B H 0.8759 0.5560 0.6642 0.132 Uiso 1 1 calc R . . . .
H13C H 0.8985 0.4915 0.7421 0.132 Uiso 1 1 calc R . . . .
C14 C 0.6431(17) 0.232(3) 0.378(2) 0.106(9) Uani 1 1 d . U . . .
H14A H 0.6063 0.2429 0.3454 0.159 Uiso 1 1 calc R . . . .
H14B H 0.6605 0.3012 0.3741 0.159 Uiso 1 1 calc R . . . .
H14C H 0.6531 0.1598 0.3633 0.159 Uiso 1 1 calc R . . . .
C15 C 0.6475(16) 0.345(3) 0.498(2) 0.127(10) Uani 1 1 d D U . . .
H15A H 0.6531 0.3258 0.5469 0.152 Uiso 1 1 calc R . . . .
H15B H 0.6734 0.4054 0.5074 0.152 Uiso 1 1 calc R . . . .
C16 C 0.5960(17) 0.403(4) 0.452(2) 0.136(14) Uani 1 1 d D U . . .
H16A H 0.5697 0.3404 0.4336 0.163 Uiso 1 1 calc R . . . .
H16B H 0.5933 0.4407 0.4086 0.163 Uiso 1 1 calc R . . . .
C17 C 0.5842(16) 0.500(3) 0.492(2) 0.122(12) Uani 1 1 d D U . . .
H17A H 0.5770 0.4612 0.5269 0.146 Uiso 1 1 calc R . . . .
H17B H 0.6137 0.5536 0.5209 0.146 Uiso 1 1 calc R . . . .
C18 C 0.5394(18) 0.568(4) 0.435(3) 0.157(18) Uani 1 1 d D U . . .
H18A H 0.5309 0.6291 0.4592 0.236 Uiso 1 1 calc R . . . .
H18B H 0.5469 0.6052 0.4017 0.236 Uiso 1 1 calc R . . . .
H18C H 0.5104 0.5132 0.4076 0.236 Uiso 1 1 calc R . . . .
C19 C 0.6336(12) 0.090(3) 0.4823(18) 0.102(8) Uani 1 1 d D U . . .
H19A H 0.6582 0.0235 0.4968 0.122 Uiso 1 1 calc R . . . .
H19B H 0.6318 0.1076 0.5256 0.122 Uiso 1 1 calc R . . . .
C20 C 0.5817(11) 0.044(3) 0.4209(18) 0.093(9) Uani 1 1 d D U . . .
H20A H 0.5840 0.0166 0.3795 0.111 Uiso 1 1 calc R . . . .
H20B H 0.5573 0.1114 0.4027 0.111 Uiso 1 1 calc R . . . .
C21 C 0.5608(12) -0.058(2) 0.4441(17) 0.086(8) Uani 1 1 d D U . . .
H21A H 0.5875 -0.1195 0.4702 0.104 Uiso 1 1 calc R . . . .
H21B H 0.5524 -0.0267 0.4790 0.104 Uiso 1 1 calc R . . . .
C22 C 0.5144(16) -0.114(4) 0.380(2) 0.152(18) Uani 1 1 d D U . . .
H22A H 0.5024 -0.1781 0.3969 0.229 Uiso 1 1 calc R . . . .
H22B H 0.4877 -0.0533 0.3542 0.229 Uiso 1 1 calc R . . . .
H22C H 0.5227 -0.1460 0.3454 0.229 Uiso 1 1 calc R . . . .
C23 C 0.7223(17) 0.200(4) 0.507(3) 0.128(9) Uani 1 1 d . U . . .
H23A H 0.7258 0.1343 0.4795 0.154 Uiso 1 1 calc R . . . .
H23B H 0.7334 0.2730 0.4933 0.154 Uiso 1 1 calc R . . . .
C24 C 0.7572(19) 0.182(5) 0.574(3) 0.159(14) Uani 1 1 d . U . . .
H24A H 0.7414 0.1320 0.5936 0.191 Uiso 1 1 calc R . . . .
H24B H 0.7639 0.2602 0.5983 0.191 Uiso 1 1 calc R . . . .
C25 C 0.815(2) 0.121(4) 0.607(3) 0.165(17) Uani 1 1 d . U . . .
H25A H 0.8383 0.1370 0.6609 0.198 Uiso 1 1 calc R . . . .
H25B H 0.8126 0.0333 0.5996 0.198 Uiso 1 1 calc R . . . .
C26 C 0.831(2) 0.168(4) 0.573(4) 0.18(2) Uani 1 1 d . U . . .
H26A H 0.8652 0.1363 0.5901 0.267 Uiso 1 1 calc R . . . .
H26B H 0.8082 0.1514 0.5202 0.267 Uiso 1 1 calc R . . . .
H26C H 0.8338 0.2545 0.5811 0.267 Uiso 1 1 calc R . . . .
C27 C 0.5295(11) 0.626(3) 0.1321(17) 0.084(7) Uani 1 1 d . U . . .
H27A H 0.5321 0.5945 0.1763 0.125 Uiso 1 1 calc R . . . .
H27B H 0.5174 0.5623 0.0949 0.125 Uiso 1 1 calc R . . . .
H27C H 0.5630 0.6531 0.1450 0.125 Uiso 1 1 calc R . . . .
C28 C 0.5100(10) 0.865(3) 0.1628(17) 0.074(6) Uani 1 1 d . U . . .
H28A H 0.5124 0.8329 0.2073 0.088 Uiso 1 1 calc R . . . .
H28B H 0.5451 0.8814 0.1767 0.088 Uiso 1 1 calc R . . . .
C29 C 0.4817(13) 0.984(3) 0.1436(19) 0.089(8) Uani 1 1 d . U . . .
H29A H 0.4464 0.9686 0.1295 0.106 Uiso 1 1 calc R . . . .
H29B H 0.4800 1.0182 0.1002 0.106 Uiso 1 1 calc R . . . .
C30 C 0.5061(16) 1.075(3) 0.206(2) 0.112(11) Uani 1 1 d . U . . .
H30A H 0.5409 1.0934 0.2196 0.135 Uiso 1 1 calc R . . . .
H30B H 0.5085 1.0412 0.2503 0.135 Uiso 1 1 calc R . . . .
C31 C 0.473(2) 1.194(4) 0.182(3) 0.149(17) Uani 1 1 d . U . . .
H31A H 0.4896 1.2518 0.2229 0.223 Uiso 1 1 calc R . . . .
H31B H 0.4715 1.2285 0.1390 0.223 Uiso 1 1 calc R . . . .
H31C H 0.4390 1.1764 0.1696 0.223 Uiso 1 1 calc R . . . .
C32 C 0.4800(11) 0.806(3) 0.0154(16) 0.073(6) Uani 1 1 d . U . . .
H32A H 0.4573 0.8765 -0.0011 0.088 Uiso 1 1 calc R . . . .
H32B H 0.5141 0.8350 0.0301 0.088 Uiso 1 1 calc R . . . .
C33 C 0.4610(11) 0.726(3) -0.0499(16) 0.075(7) Uani 1 1 d . U . . .
H33A H 0.4856 0.6598 -0.0356 0.090 Uiso 1 1 calc R . . . .
H33B H 0.4285 0.6901 -0.0621 0.090 Uiso 1 1 calc R . . . .
C34 C 0.4529(16) 0.782(3) -0.1165(19) 0.102(10) Uani 1 1 d . U . . .
H34A H 0.4858 0.8151 -0.1044 0.123 Uiso 1 1 calc R . . . .
H34B H 0.4296 0.8506 -0.1291 0.123 Uiso 1 1 calc R . . . .
C35 C 0.431(3) 0.704(4) -0.186(2) 0.17(2) Uani 1 1 d . U . . .
H35A H 0.4276 0.7513 -0.2263 0.258 Uiso 1 1 calc R . . . .
H35B H 0.4545 0.6370 -0.1751 0.258 Uiso 1 1 calc R . . . .
H35C H 0.3979 0.6726 -0.1999 0.258 Uiso 1 1 calc R . . . .
C36 C 0.4230(11) 0.700(3) 0.0690(17) 0.082(7) Uani 1 1 d . U . . .
H36A H 0.4029 0.7704 0.0652 0.098 Uiso 1 1 calc R . . . .
H36B H 0.4061 0.6636 0.0193 0.098 Uiso 1 1 calc R . . . .
C37 C 0.4212(17) 0.607(4) 0.122(2) 0.129(12) Uani 1 1 d . U . . .
H37A H 0.4437 0.5387 0.1305 0.155 Uiso 1 1 calc R . . . .
H37B H 0.3862 0.5767 0.0993 0.155 Uiso 1 1 calc R . . . .
C38 C 0.4398(16) 0.672(4) 0.1999(19) 0.128(14) Uani 1 1 d D U . . .
H38A H 0.4771 0.6817 0.2280 0.154 Uiso 1 1 calc R . . . .
H38B H 0.4244 0.7521 0.1896 0.154 Uiso 1 1 calc R . . . .
C39 C 0.426(3) 0.604(6) 0.248(3) 0.23(4) Uani 1 1 d D U . . .
H39A H 0.4385 0.6486 0.2936 0.348 Uiso 1 1 calc R . . . .
H39B H 0.3891 0.5956 0.2211 0.348 Uiso 1 1 calc R . . . .
H39C H 0.4420 0.5251 0.2595 0.348 Uiso 1 1 calc R . . . .
P1 P 0.7624(4) 0.7888(6) 0.7479(4) 0.069(2) Uani 1 1 d . U . . .
P2 P 0.6593(4) 0.2174(7) 0.4651(5) 0.089(3) Uani 1 1 d . U . . .
P3 P 0.4850(3) 0.7492(8) 0.0952(4) 0.073(2) Uani 1 1 d . U . . .
Sb1 Sb 0.64538(7) 0.85866(16) 0.17295(9) 0.0566(5) Uani 1 1 d . . . . .
Sb2 Sb 0.66648(7) 0.91828(14) 0.31080(9) 0.0548(5) Uani 1 1 d . . . . .
Sb3 Sb 0.63036(7) 0.71743(17) 0.34617(9) 0.0609(5) Uani 1 1 d . . . . .
Sb4 Sb 0.68956(8) 0.7394(2) 0.49735(10) 0.0836(7) Uani 1 1 d . . . . .
Sb5 Sb 0.78265(7) 0.73181(16) 0.51365(8) 0.0589(5) Uani 1 1 d . . . . .
Sb6 Sb 0.77327(8) 0.50998(15) 0.44642(10) 0.0650(5) Uani 1 1 d . . . . .
Sb7 Sb 0.84222(7) 0.54367(16) 0.40646(10) 0.0647(5) Uani 1 1 d . . . . .
Sb8 Sb 0.79669(7) 0.74405(17) 0.32053(9) 0.0580(5) Uani 1 1 d . . . . .
Sb9 Sb 0.70021(7) 0.64877(16) 0.21735(9) 0.0578(5) Uani 1 1 d . . . . .
Sb10 Sb 0.67701(7) 0.53483(15) 0.31225(10) 0.0623(5) Uani 1 1 d . . . . .
Sb11 Sb 0.77319(7) 0.88950(14) 0.40529(9) 0.0537(5) 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
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 P1 1.79(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.40(5) . ?
C2 P1 1.82(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.64(5) . ?
C4 H4AA 0.9900 . ?
C4 H4AB 0.9900 . ?
C4 H4BC 0.9900 . ?
C4 H4BD 0.9900 . ?
C4 C5 1.53(3) . ?
C4 C5A 1.54(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C5A H5AA 0.9800 . ?
C5A H5AB 0.9800 . ?
C5A H5AC 0.9800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.51(4) . ?
C6 P1 1.97(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.53(4) . ?
C8 H8AA 0.9900 . ?
C8 H8AB 0.9900 . ?
C8 H8BC 0.9900 . ?
C8 H8BD 0.9900 . ?
C8 C9 1.53(2) . ?
C8 C9A 1.53(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.51(3) . ?
C10 P1 1.83(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.52(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.52(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14 P2 1.67(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.51(3) . ?
C15 P2 1.73(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.56(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.48(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.52(2) . ?
C19 P2 1.78(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.53(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.50(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.27(6) . ?
C23 P2 1.68(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.70(7) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.23(7) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C27 P3 1.81(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.53(4) . ?
C28 P3 1.78(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.53(5) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.59(5) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.50(4) . ?
C32 P3 1.77(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.47(5) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 C35 1.54(5) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C36 C37 1.57(5) . ?
C36 P3 1.79(3) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C37 C38 1.62(6) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C38 C39 1.52(2) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
Sb1 Sb2 2.763(3) . ?
Sb1 Sb9 2.760(2) . ?
Sb2 Sb3 2.811(3) . ?
Sb2 Sb11 2.833(3) . ?
Sb3 Sb4 2.752(3) . ?
Sb3 Sb10 2.840(3) . ?
Sb4 Sb5 2.751(3) . ?
Sb5 Sb6 2.815(3) . ?
Sb5 Sb11 2.821(2) . ?
Sb6 Sb7 2.765(3) . ?
Sb6 Sb10 2.837(3) . ?
Sb7 Sb8 2.765(3) . ?
Sb8 Sb9 2.813(3) . ?
Sb8 Sb11 2.839(3) . ?
Sb9 Sb10 2.834(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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
P1 C1 H1A 109.5 . . ?
P1 C1 H1B 109.5 . . ?
P1 C1 H1C 109.5 . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C3 C2 P1 113(3) . . ?
P1 C2 H2A 109.0 . . ?
P1 C2 H2B 109.0 . . ?
C2 C3 H3A 110.0 . . ?
C2 C3 H3B 110.0 . . ?
C2 C3 C4 109(3) . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 H3A 110.0 . . ?
C4 C3 H3B 110.0 . . ?
C3 C4 H4AA 111.6 . . ?
C3 C4 H4AB 111.6 . . ?
C3 C4 H4BC 111.7 . . ?
C3 C4 H4BD 111.7 . . ?
H4AA C4 H4AB 109.4 . . ?
H4BC C4 H4BD 109.5 . . ?
C5 C4 C3 101(4) . . ?
C5 C4 H4AA 111.6 . . ?
C5 C4 H4AB 111.6 . . ?
C5A C4 C3 100(6) . . ?
C5A C4 H4BC 111.7 . . ?
C5A C4 H4BD 111.7 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C5A H5AA 109.5 . . ?
C4 C5A H5AB 109.5 . . ?
C4 C5A H5AC 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
H6A C6 H6B 107.5 . . ?
C7 C6 H6A 108.4 . . ?
C7 C6 H6B 108.4 . . ?
C7 C6 P1 115(2) . . ?
P1 C6 H6A 108.4 . . ?
P1 C6 H6B 108.4 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C6 C7 C8 111(3) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C7 C8 H8AA 110.9 . . ?
C7 C8 H8AB 110.9 . . ?
C7 C8 H8BC 107.7 . . ?
C7 C8 H8BD 107.7 . . ?
C7 C8 C9A 118(4) . . ?
H8AA C8 H8AB 109.0 . . ?
H8BC C8 H8BD 107.1 . . ?
C9 C8 C7 104(3) . . ?
C9 C8 H8AA 110.9 . . ?
C9 C8 H8AB 110.9 . . ?
C9A C8 H8BC 107.7 . . ?
C9A C8 H8BD 107.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C9A H9AA 109.5 . . ?
C8 C9A H9AB 109.5 . . ?
C8 C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
H10A C10 H10B 107.2 . . ?
C11 C10 H10A 107.9 . . ?
C11 C10 H10B 107.9 . . ?
C11 C10 P1 118(2) . . ?
P1 C10 H10A 107.9 . . ?
P1 C10 H10B 107.9 . . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
C10 C11 C12 109(2) . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 C11 111(2) . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
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 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
P2 C14 H14A 109.5 . . ?
P2 C14 H14B 109.5 . . ?
P2 C14 H14C 109.5 . . ?
H15A C15 H15B 107.1 . . ?
C16 C15 H15A 107.7 . . ?
C16 C15 H15B 107.7 . . ?
C16 C15 P2 118(3) . . ?
P2 C15 H15A 107.7 . . ?
P2 C15 H15B 107.7 . . ?
C15 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
C15 C16 C17 115(3) . . ?
H16A C16 H16B 107.5 . . ?
C17 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
C16 C17 H17A 110.2 . . ?
C16 C17 H17B 110.2 . . ?
H17A C17 H17B 108.5 . . ?
C18 C17 C16 107(3) . . ?
C18 C17 H17A 110.2 . . ?
C18 C17 H17B 110.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
H19A C19 H19B 107.1 . . ?
C20 C19 H19A 107.7 . . ?
C20 C19 H19B 107.7 . . ?
C20 C19 P2 119(2) . . ?
P2 C19 H19A 107.7 . . ?
P2 C19 H19B 107.7 . . ?
C19 C20 H20A 108.7 . . ?
C19 C20 H20B 108.7 . . ?
C19 C20 C21 114(2) . . ?
H20A C20 H20B 107.6 . . ?
C21 C20 H20A 108.7 . . ?
C21 C20 H20B 108.7 . . ?
C20 C21 H21A 109.1 . . ?
C20 C21 H21B 109.1 . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 C20 112(3) . . ?
C22 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H23A C23 H23B 105.6 . . ?
C24 C23 H23A 104.4 . . ?
C24 C23 H23B 104.4 . . ?
C24 C23 P2 131(5) . . ?
P2 C23 H23A 104.4 . . ?
P2 C23 H23B 104.4 . . ?
C23 C24 H24A 105.4 . . ?
C23 C24 H24B 105.4 . . ?
C23 C24 C25 128(6) . . ?
H24A C24 H24B 106.0 . . ?
C25 C24 H24A 105.4 . . ?
C25 C24 H24B 105.4 . . ?
C24 C25 H25A 110.6 . . ?
C24 C25 H25B 110.6 . . ?
H25A C25 H25B 108.8 . . ?
C26 C25 C24 106(4) . . ?
C26 C25 H25A 110.6 . . ?
C26 C25 H25B 110.6 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
P3 C27 H27A 109.5 . . ?
P3 C27 H27B 109.5 . . ?
P3 C27 H27C 109.5 . . ?
H28A C28 H28B 107.0 . . ?
C29 C28 H28A 107.6 . . ?
C29 C28 H28B 107.6 . . ?
C29 C28 P3 119(2) . . ?
P3 C28 H28A 107.6 . . ?
P3 C28 H28B 107.6 . . ?
C28 C29 H29A 108.7 . . ?
C28 C29 H29B 108.7 . . ?
C28 C29 C30 114(3) . . ?
H29A C29 H29B 107.6 . . ?
C30 C29 H29A 108.7 . . ?
C30 C29 H29B 108.7 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 C31 111(3) . . ?
H30A C30 H30B 108.1 . . ?
C31 C30 H30A 109.5 . . ?
C31 C30 H30B 109.5 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
H32A C32 H32B 107.0 . . ?
C33 C32 H32A 107.6 . . ?
C33 C32 H32B 107.6 . . ?
C33 C32 P3 119(2) . . ?
P3 C32 H32A 107.6 . . ?
P3 C32 H32B 107.6 . . ?
C32 C33 H33A 108.4 . . ?
C32 C33 H33B 108.4 . . ?
H33A C33 H33B 107.4 . . ?
C34 C33 C32 116(3) . . ?
C34 C33 H33A 108.4 . . ?
C34 C33 H33B 108.4 . . ?
C33 C34 H34A 108.0 . . ?
C33 C34 H34B 108.0 . . ?
C33 C34 C35 117(3) . . ?
H34A C34 H34B 107.3 . . ?
C35 C34 H34A 108.0 . . ?
C35 C34 H34B 108.0 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
H36A C36 H36B 107.4 . . ?
C37 C36 H36A 108.3 . . ?
C37 C36 H36B 108.3 . . ?
C37 C36 P3 116(2) . . ?
P3 C36 H36A 108.3 . . ?
P3 C36 H36B 108.3 . . ?
C36 C37 H37A 109.8 . . ?
C36 C37 H37B 109.8 . . ?
C36 C37 C38 109(3) . . ?
H37A C37 H37B 108.3 . . ?
C38 C37 H37A 109.8 . . ?
C38 C37 H37B 109.8 . . ?
C37 C38 H38A 108.7 . . ?
C37 C38 H38B 108.7 . . ?
H38A C38 H38B 107.6 . . ?
C39 C38 C37 114(3) . . ?
C39 C38 H38A 108.7 . . ?
C39 C38 H38B 108.7 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C1 P1 C2 110.8(15) . . ?
C1 P1 C6 105.8(15) . . ?
C1 P1 C10 111.0(14) . . ?
C2 P1 C6 111.4(16) . . ?
C2 P1 C10 109.2(14) . . ?
C10 P1 C6 108.6(13) . . ?
C14 P2 C15 112.8(19) . . ?
C14 P2 C19 114.9(17) . . ?
C14 P2 C23 99(2) . . ?
C15 P2 C19 111(2) . . ?
C23 P2 C15 109(2) . . ?
C23 P2 C19 109.4(18) . . ?
C28 P3 C27 107.9(14) . . ?
C28 P3 C36 113.4(16) . . ?
C32 P3 C27 110.0(16) . . ?
C32 P3 C28 107.7(15) . . ?
C32 P3 C36 107.6(14) . . ?
C36 P3 C27 110.2(16) . . ?
Sb9 Sb1 Sb2 95.47(7) . . ?
Sb1 Sb2 Sb3 101.94(8) . . ?
Sb1 Sb2 Sb11 103.98(8) . . ?
Sb3 Sb2 Sb11 101.96(7) . . ?
Sb2 Sb3 Sb10 99.45(8) . . ?
Sb4 Sb3 Sb2 98.14(9) . . ?
Sb4 Sb3 Sb10 105.31(9) . . ?
Sb5 Sb4 Sb3 97.39(8) . . ?
Sb4 Sb5 Sb6 99.12(9) . . ?
Sb4 Sb5 Sb11 104.70(8) . . ?
Sb6 Sb5 Sb11 100.94(7) . . ?
Sb5 Sb6 Sb10 101.18(8) . . ?
Sb7 Sb6 Sb5 99.40(8) . . ?
Sb7 Sb6 Sb10 104.21(8) . . ?
Sb8 Sb7 Sb6 96.67(8) . . ?
Sb7 Sb8 Sb9 99.30(8) . . ?
Sb7 Sb8 Sb11 104.69(8) . . ?
Sb9 Sb8 Sb11 100.52(8) . . ?
Sb1 Sb9 Sb8 98.57(8) . . ?
Sb1 Sb9 Sb10 106.10(8) . . ?
Sb8 Sb9 Sb10 100.89(7) . . ?
Sb6 Sb10 Sb3 102.60(8) . . ?
Sb9 Sb10 Sb3 103.72(7) . . ?
Sb9 Sb10 Sb6 103.49(8) . . ?
Sb2 Sb11 Sb8 102.88(7) . . ?
Sb5 Sb11 Sb2 102.47(8) . . ?
Sb5 Sb11 Sb8 103.40(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 C4 C5 -166(4) . . . . ?
C2 C3 C4 C5A 153(6) . . . . ?
C3 C2 P1 C1 62(3) . . . . ?
C3 C2 P1 C6 180(2) . . . . ?
C3 C2 P1 C10 -61(3) . . . . ?
C6 C7 C8 C9 15(6) . . . . ?
C6 C7 C8 C9A -26(10) . . . . ?
C10 C11 C12 C13 -179(2) . . . . ?
C11 C10 P1 C1 61(2) . . . . ?
C11 C10 P1 C2 -176(2) . . . . ?
C11 C10 P1 C6 -55(3) . . . . ?
C15 C16 C17 C18 166(4) . . . . ?
C16 C15 P2 C14 49(5) . . . . ?
C16 C15 P2 C19 -81(4) . . . . ?
C16 C15 P2 C23 158(4) . . . . ?
C19 C20 C21 C22 -170(4) . . . . ?
C20 C19 P2 C14 -32(4) . . . . ?
C20 C19 P2 C15 97(3) . . . . ?
C20 C19 P2 C23 -143(3) . . . . ?
C23 C24 C25 C26 44(8) . . . . ?
C24 C23 P2 C14 -178(5) . . . . ?
C24 C23 P2 C15 64(6) . . . . ?
C24 C23 P2 C19 -57(6) . . . . ?
C28 C29 C30 C31 -178(3) . . . . ?
C29 C28 P3 C27 176(2) . . . . ?
C29 C28 P3 C32 57(3) . . . . ?
C29 C28 P3 C36 -62(3) . . . . ?
C32 C33 C34 C35 -178(4) . . . . ?
C33 C32 P3 C27 61(3) . . . . ?
C33 C32 P3 C28 179(2) . . . . ?
C33 C32 P3 C36 -59(3) . . . . ?
C36 C37 C38 C39 164(5) . . . . ?
C37 C36 P3 C27 39(3) . . . . ?
C37 C36 P3 C28 -82(3) . . . . ?
C37 C36 P3 C32 159(3) . . . . ?
P1 C2 C3 C4 -172(2) . . . . ?
P1 C6 C7 C8 -178(3) . . . . ?
P1 C10 C11 C12 -177.4(19) . . . . ?
P2 C15 C16 C17 167(3) . . . . ?
P2 C19 C20 C21 -174(3) . . . . ?
P2 C23 C24 C25 158(4) . . . . ?
P3 C28 C29 C30 179(3) . . . . ?
P3 C32 C33 C34 174(2) . . . . ?
P3 C36 C37 C38 68(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
