# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# 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 
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data_4149f
_database_code_depnum_ccdc_archive 'CCDC 1428161'
_audit_update_record             
;
2015-09-28 deposited with the CCDC.
2015-11-16 downloaded from the CCDC.
;
_audit_creation_date             2015-06-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        PKM-VAN-1
_chemical_formula_moiety         'C29 H33 N2 P'
_chemical_formula_sum            'C29 H33 N2 P'
_chemical_formula_weight         440.54
_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'

_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                   11.3578(19)
_cell_length_b                   9.9307(13)
_cell_length_c                   22.539(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.838(13)
_cell_angle_gamma                90
_cell_volume                     2478.6(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2682
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.31
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5954
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1214 before and 0.0790 after correction.
The Ratio of minimum to maximum transmission is 0.7982.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_unetI/netI     0.0864
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            21757
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.755
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker X8-KappaApexII'
_diffrn_measurement_method       'fine slicing ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3909
_reflns_number_total             5947
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         5947
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.006
_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)+(0.0512P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1218
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25),
 C26(H26), C27(H27), C28(H28), C29(H29)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C13(H13A,H13B,H13C),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_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
P1 P 0.37230(4) 0.94324(4) 0.30521(2) 0.01512(13) Uani 1 1 d . . . . .
N1 N 0.31828(12) 1.21760(14) 0.28320(7) 0.0158(3) Uani 1 1 d . . . . .
N2 N 0.34419(12) 1.17420(13) 0.37901(7) 0.0139(3) Uani 1 1 d . . . . .
C1 C 0.23670(15) 0.89430(16) 0.24792(9) 0.0150(4) Uani 1 1 d . . . . .
C2 C 0.26121(15) 0.81336(16) 0.20075(9) 0.0174(4) Uani 1 1 d . . . . .
C3 C 0.16870(16) 0.77713(17) 0.15203(9) 0.0206(4) Uani 1 1 d . . . . .
H3 H 0.1866 0.7214 0.1209 0.025 Uiso 1 1 calc R . . . .
C4 C 0.05099(16) 0.82008(18) 0.14756(9) 0.0206(4) Uani 1 1 d . . . . .
C5 C 0.02701(15) 0.89814(18) 0.19410(9) 0.0205(4) Uani 1 1 d . . . . .
H5 H -0.0536 0.9271 0.1918 0.025 Uiso 1 1 calc R . . . .
C6 C 0.11647(15) 0.93628(17) 0.24449(9) 0.0182(4) Uani 1 1 d . . . . .
C7 C 0.38764(16) 0.76673(19) 0.20017(10) 0.0240(5) Uani 1 1 d . . . . .
H7A H 0.4352 0.8432 0.1910 0.036 Uiso 1 1 calc GR . . . .
H7B H 0.3840 0.6971 0.1690 0.036 Uiso 1 1 calc GR . . . .
H7C H 0.4257 0.7296 0.2401 0.036 Uiso 1 1 calc GR . . . .
C8 C -0.04683(17) 0.7826(2) 0.09287(10) 0.0308(5) Uani 1 1 d . . . . .
H8A H -0.0744 0.8637 0.0690 0.046 Uiso 1 1 calc GR . . . .
H8B H -0.1148 0.7419 0.1065 0.046 Uiso 1 1 calc GR . . . .
H8C H -0.0147 0.7180 0.0676 0.046 Uiso 1 1 calc GR . . . .
C9 C 0.07822(16) 1.01902(19) 0.29335(10) 0.0254(5) Uani 1 1 d . . . . .
H9A H 0.1264 0.9928 0.3333 0.038 Uiso 1 1 calc GR . . . .
H9B H -0.0075 1.0030 0.2920 0.038 Uiso 1 1 calc GR . . . .
H9C H 0.0910 1.1148 0.2863 0.038 Uiso 1 1 calc GR . . . .
C10 C 0.33103(14) 1.11583(17) 0.32409(9) 0.0151(4) Uani 1 1 d . . . . .
C11 C 0.32386(15) 1.34167(16) 0.31279(9) 0.0168(4) Uani 1 1 d . . . . .
C12 C 0.34087(15) 1.31462(16) 0.37296(9) 0.0158(4) Uani 1 1 d . . . . .
C13 C 0.30473(17) 1.19930(18) 0.21794(9) 0.0223(4) Uani 1 1 d . . . . .
H13A H 0.2195 1.1839 0.1989 0.033 Uiso 1 1 calc GR . . . .
H13B H 0.3526 1.1215 0.2105 0.033 Uiso 1 1 calc GR . . . .
H13C H 0.3330 1.2802 0.2005 0.033 Uiso 1 1 calc GR . . . .
C14 C 0.31610(17) 1.47141(17) 0.27936(10) 0.0236(5) Uani 1 1 d . . . . .
H14A H 0.3818 1.4767 0.2577 0.035 Uiso 1 1 calc GR . . . .
H14B H 0.3230 1.5462 0.3083 0.035 Uiso 1 1 calc GR . . . .
H14C H 0.2383 1.4769 0.2500 0.035 Uiso 1 1 calc GR . . . .
C15 C 0.35716(16) 1.40706(17) 0.42574(9) 0.0207(4) Uani 1 1 d . . . . .
H15A H 0.2984 1.3849 0.4502 0.031 Uiso 1 1 calc GR . . . .
H15B H 0.3447 1.5001 0.4112 0.031 Uiso 1 1 calc GR . . . .
H15C H 0.4391 1.3973 0.4507 0.031 Uiso 1 1 calc GR . . . .
C16 C 0.35032(16) 1.10196(17) 0.43630(9) 0.0183(4) Uani 1 1 d . . . . .
H16A H 0.2818 1.0399 0.4317 0.027 Uiso 1 1 calc GR . . . .
H16B H 0.3473 1.1667 0.4687 0.027 Uiso 1 1 calc GR . . . .
H16C H 0.4260 1.0510 0.4468 0.027 Uiso 1 1 calc GR . . . .
C17 C 0.40358(15) 0.83746(16) 0.36843(9) 0.0160(4) Uani 1 1 d . . . . .
C18 C 0.53462(15) 0.82184(16) 0.39376(9) 0.0160(4) Uani 1 1 d . . . . .
C19 C 0.61628(15) 0.92944(17) 0.39830(9) 0.0189(4) Uani 1 1 d . . . . .
H19 H 0.5858 1.0175 0.3881 0.023 Uiso 1 1 calc R . . . .
C20 C 0.74055(16) 0.91130(19) 0.41729(9) 0.0227(4) Uani 1 1 d . . . . .
H20 H 0.7931 0.9863 0.4191 0.027 Uiso 1 1 calc R . . . .
C21 C 0.78803(16) 0.78530(19) 0.43358(9) 0.0248(5) Uani 1 1 d . . . . .
H21 H 0.8728 0.7728 0.4463 0.030 Uiso 1 1 calc R . . . .
C22 C 0.70954(17) 0.67703(19) 0.43098(9) 0.0225(4) Uani 1 1 d . . . . .
H22 H 0.7409 0.5898 0.4424 0.027 Uiso 1 1 calc R . . . .
C23 C 0.58634(16) 0.69515(17) 0.41195(9) 0.0199(4) Uani 1 1 d . . . . .
H23 H 0.5346 0.6196 0.4111 0.024 Uiso 1 1 calc R . . . .
C24 C 0.31927(15) 0.77627(16) 0.40094(9) 0.0170(4) Uani 1 1 d . . . . .
C25 C 0.35158(17) 0.75683(17) 0.46434(9) 0.0196(4) Uani 1 1 d . . . . .
H25 H 0.4304 0.7823 0.4854 0.024 Uiso 1 1 calc R . . . .
C26 C 0.27404(17) 0.70228(17) 0.49749(10) 0.0248(5) Uani 1 1 d . . . . .
H26 H 0.3004 0.6906 0.5402 0.030 Uiso 1 1 calc R . . . .
C27 C 0.15750(18) 0.66458(18) 0.46818(11) 0.0274(5) Uani 1 1 d . . . . .
H27 H 0.1035 0.6272 0.4905 0.033 Uiso 1 1 calc R . . . .
C28 C 0.12203(17) 0.68272(18) 0.40592(11) 0.0268(5) Uani 1 1 d . . . . .
H28 H 0.0425 0.6581 0.3854 0.032 Uiso 1 1 calc R . . . .
C29 C 0.20035(16) 0.73616(17) 0.37279(10) 0.0212(4) Uani 1 1 d . . . . .
H29 H 0.1734 0.7461 0.3300 0.025 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
P1 C1 1.8416(17) . ?
P1 C10 1.8512(18) . ?
P1 C17 1.7420(19) . ?
N1 C10 1.354(2) . ?
N1 C11 1.396(2) . ?
N1 C13 1.456(2) . ?
N2 C10 1.345(2) . ?
N2 C12 1.401(2) . ?
N2 C16 1.465(2) . ?
C1 C2 1.409(3) . ?
C1 C6 1.413(2) . ?
C2 C3 1.388(2) . ?
C2 C7 1.512(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C4 C5 1.379(3) . ?
C4 C8 1.511(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(2) . ?
C6 C9 1.513(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 C12 1.354(3) . ?
C11 C14 1.485(2) . ?
C12 C15 1.481(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.479(2) . ?
C17 C24 1.461(3) . ?
C18 C19 1.404(2) . ?
C18 C23 1.410(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.393(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.380(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.390(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.381(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.407(3) . ?
C24 C29 1.416(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.386(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.393(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.383(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.388(3) . ?
C29 H29 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 C10 100.98(7) . . ?
C17 P1 C1 113.65(8) . . ?
C17 P1 C10 112.73(9) . . ?
C10 N1 C11 110.31(16) . . ?
C10 N1 C13 124.47(15) . . ?
C11 N1 C13 125.19(15) . . ?
C10 N2 C12 110.15(15) . . ?
C10 N2 C16 125.03(14) . . ?
C12 N2 C16 124.62(15) . . ?
C2 C1 P1 113.89(12) . . ?
C2 C1 C6 118.52(16) . . ?
C6 C1 P1 127.43(14) . . ?
C1 C2 C7 121.91(16) . . ?
C3 C2 C1 120.20(16) . . ?
C3 C2 C7 117.86(18) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.76(19) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C8 120.42(19) . . ?
C5 C4 C3 117.91(17) . . ?
C5 C4 C8 121.67(17) . . ?
C4 C5 H5 118.7 . . ?
C4 C5 C6 122.66(17) . . ?
C6 C5 H5 118.7 . . ?
C1 C6 C9 123.41(17) . . ?
C5 C6 C1 118.93(18) . . ?
C5 C6 C9 117.66(16) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 P1 121.94(14) . . ?
N2 C10 P1 128.95(13) . . ?
N2 C10 N1 106.14(15) . . ?
N1 C11 C14 122.15(18) . . ?
C12 C11 N1 106.55(15) . . ?
C12 C11 C14 131.26(17) . . ?
N2 C12 C15 122.88(17) . . ?
C11 C12 N2 106.84(15) . . ?
C11 C12 C15 130.26(16) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 P1 112.57(13) . . ?
C24 C17 P1 128.58(13) . . ?
C24 C17 C18 118.57(16) . . ?
C19 C18 C17 122.70(15) . . ?
C19 C18 C23 115.60(16) . . ?
C23 C18 C17 121.61(15) . . ?
C18 C19 H19 118.9 . . ?
C20 C19 C18 122.15(16) . . ?
C20 C19 H19 118.9 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.58(17) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 120.6 . . ?
C20 C21 C22 118.77(17) . . ?
C22 C21 H21 120.6 . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.56(17) . . ?
C23 C22 H22 119.7 . . ?
C18 C23 H23 118.9 . . ?
C22 C23 C18 122.29(17) . . ?
C22 C23 H23 118.9 . . ?
C25 C24 C17 120.94(16) . . ?
C25 C24 C29 115.09(17) . . ?
C29 C24 C17 123.95(18) . . ?
C24 C25 H25 118.4 . . ?
C26 C25 C24 123.20(18) . . ?
C26 C25 H25 118.4 . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 120.0(2) . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 120.7 . . ?
C28 C27 C26 118.55(19) . . ?
C28 C27 H27 120.7 . . ?
C27 C28 H28 119.4 . . ?
C27 C28 C29 121.26(18) . . ?
C29 C28 H28 119.4 . . ?
C24 C29 H29 119.1 . . ?
C28 C29 C24 121.88(19) . . ?
C28 C29 H29 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C2 C3 -175.25(14) . . . . ?
P1 C1 C2 C7 2.9(2) . . . . ?
P1 C1 C6 C5 173.92(14) . . . . ?
P1 C1 C6 C9 -7.2(3) . . . . ?
P1 C17 C18 C19 40.0(2) . . . . ?
P1 C17 C18 C23 -136.53(17) . . . . ?
P1 C17 C24 C25 -145.46(15) . . . . ?
P1 C17 C24 C29 32.6(2) . . . . ?
N1 C11 C12 N2 -0.57(18) . . . . ?
N1 C11 C12 C15 177.87(17) . . . . ?
C1 P1 C10 N1 -66.85(15) . . . . ?
C1 P1 C10 N2 135.44(16) . . . . ?
C1 P1 C17 C18 146.09(12) . . . . ?
C1 P1 C17 C24 -40.14(19) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C2 C1 C6 C9 177.73(17) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
C2 C3 C4 C8 177.96(18) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C4 C5 C6 C9 -178.44(17) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C6 C1 C2 C7 178.60(16) . . . . ?
C7 C2 C3 C4 -177.29(17) . . . . ?
C8 C4 C5 C6 -178.67(18) . . . . ?
C10 P1 C1 C2 144.09(14) . . . . ?
C10 P1 C1 C6 -31.15(18) . . . . ?
C10 P1 C17 C18 -99.77(14) . . . . ?
C10 P1 C17 C24 74.00(17) . . . . ?
C10 N1 C11 C12 0.25(19) . . . . ?
C10 N1 C11 C14 178.18(16) . . . . ?
C10 N2 C12 C11 0.71(19) . . . . ?
C10 N2 C12 C15 -177.86(16) . . . . ?
C11 N1 C10 P1 -161.92(12) . . . . ?
C11 N1 C10 N2 0.19(19) . . . . ?
C12 N2 C10 P1 159.87(13) . . . . ?
C12 N2 C10 N1 -0.55(18) . . . . ?
C13 N1 C10 P1 16.2(2) . . . . ?
C13 N1 C10 N2 178.31(15) . . . . ?
C13 N1 C11 C12 -177.85(16) . . . . ?
C13 N1 C11 C14 0.1(3) . . . . ?
C14 C11 C12 N2 -178.24(17) . . . . ?
C14 C11 C12 C15 0.2(3) . . . . ?
C16 N2 C10 P1 -25.2(2) . . . . ?
C16 N2 C10 N1 174.42(14) . . . . ?
C16 N2 C12 C11 -174.29(15) . . . . ?
C16 N2 C12 C15 7.1(3) . . . . ?
C17 P1 C1 C2 -94.93(15) . . . . ?
C17 P1 C1 C6 89.83(18) . . . . ?
C17 P1 C10 N1 171.52(13) . . . . ?
C17 P1 C10 N2 13.81(19) . . . . ?
C17 C18 C19 C20 -174.33(19) . . . . ?
C17 C18 C23 C22 174.56(19) . . . . ?
C17 C24 C25 C26 178.42(16) . . . . ?
C17 C24 C29 C28 -177.71(16) . . . . ?
C18 C17 C24 C25 28.0(2) . . . . ?
C18 C17 C24 C29 -153.92(16) . . . . ?
C18 C19 C20 C21 -1.2(3) . . . . ?
C19 C18 C23 C22 -2.2(3) . . . . ?
C19 C20 C21 C22 -0.3(3) . . . . ?
C20 C21 C22 C23 0.5(3) . . . . ?
C21 C22 C23 C18 0.8(3) . . . . ?
C23 C18 C19 C20 2.4(3) . . . . ?
C24 C17 C18 C19 -134.46(19) . . . . ?
C24 C17 C18 C23 49.0(3) . . . . ?
C24 C25 C26 C27 -0.5(3) . . . . ?
C25 C24 C29 C28 0.5(2) . . . . ?
C25 C26 C27 C28 0.1(3) . . . . ?
C26 C27 C28 C29 0.5(3) . . . . ?
C27 C28 C29 C24 -0.8(3) . . . . ?
C29 C24 C25 C26 0.2(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_2547
_database_code_depnum_ccdc_archive 'CCDC 1428162'
_audit_update_record             
;
2015-09-28 deposited with the CCDC.
2015-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C27 H32 B N2 P), C4 H8 O'
_chemical_formula_sum            'C58 H72 B2 N4 O P2'
_chemical_formula_weight         924.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   25.984(2)
_cell_length_b                   9.734(1)
_cell_length_c                   21.550(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.32(1)
_cell_angle_gamma                90
_cell_volume                     5174.2(1)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2990
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      27.49

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_F_000             1984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.7027
_exptl_absorpt_correction_T_max  0.9124
_exptl_absorpt_process_details   'STOE XRed (TwinAbs, V1.44)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS2T'
_diffrn_measurement_method       'fine slicing φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33319
_diffrn_reflns_av_unetI/netI     0.3540
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.960
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             33319
_reflns_number_gt                10263
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0461P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         33319
_refine_ls_number_parameters     340
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.2228
_refine_ls_R_factor_gt           0.0776
_refine_ls_wR_factor_ref         0.1936
_refine_ls_wR_factor_gt          0.1453
_refine_ls_goodness_of_fit_ref   0.754
_refine_ls_restrained_S_all      0.755
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.3298(3) 0.1757(7) 0.4159(3) 0.0277(16) Uani 1 1 d . . . . .
C2 C 0.3027(3) 0.0967(7) 0.5002(3) 0.0315(18) Uani 1 1 d . . . . .
C3 C 0.2940(3) 0.0722(7) 0.3938(3) 0.0284(16) Uani 1 1 d . . . . .
H3A H 0.2816 0.0388 0.3501 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3671(3) 0.2937(8) 0.5255(3) 0.043(2) Uani 1 1 d . . . . .
H4A H 0.3583 0.3841 0.5049 0.052 Uiso 1 1 calc R U . . .
H4B H 0.4056 0.2739 0.5334 0.052 Uiso 1 1 calc R U . . .
H4C H 0.3594 0.2935 0.5672 0.052 Uiso 1 1 calc R U . . .
C5 C 0.2407(3) -0.0899(8) 0.4406(4) 0.041(2) Uani 1 1 d . . . . .
H5A H 0.2190 -0.0721 0.4697 0.049 Uiso 1 1 calc R U . . .
H5B H 0.2611 -0.1755 0.4537 0.049 Uiso 1 1 calc R U . . .
H5C H 0.2166 -0.0983 0.3955 0.049 Uiso 1 1 calc R U . . .
C6 C 0.3374(3) 0.2381(7) 0.2889(3) 0.0281(17) Uani 1 1 d . . . . .
H6A H 0.3495 0.1405 0.2892 0.034 Uiso 1 1 calc R U . . .
C7 C 0.2756(3) 0.2455(7) 0.2550(3) 0.0268(16) Uani 1 1 d . . . . .
C8 C 0.2559(3) 0.1760(7) 0.1944(3) 0.0283(17) Uani 1 1 d . . . . .
H8A H 0.2799 0.1246 0.1780 0.034 Uiso 1 1 calc R U . . .
C9 C 0.2010(3) 0.1839(8) 0.1592(3) 0.0328(18) Uani 1 1 d . . . . .
H9A H 0.1874 0.1369 0.1187 0.039 Uiso 1 1 calc R U . . .
C10 C 0.1664(3) 0.2584(7) 0.1823(3) 0.0329(18) Uani 1 1 d . . . . .
H10A H 0.1290 0.2634 0.1576 0.040 Uiso 1 1 calc R U . . .
C11 C 0.1854(3) 0.3272(7) 0.2420(3) 0.0328(18) Uani 1 1 d . . . . .
H11A H 0.1614 0.3792 0.2582 0.039 Uiso 1 1 calc R U . . .
C12 C 0.2404(3) 0.3182(7) 0.2774(3) 0.0299(17) Uani 1 1 d . . . . .
H12A H 0.2536 0.3641 0.3182 0.036 Uiso 1 1 calc R U . . .
C13 C 0.3661(3) 0.3240(8) 0.2518(3) 0.0339(18) Uani 1 1 d . . . . .
C14 C 0.4086(3) 0.2698(9) 0.2335(4) 0.047(2) Uani 1 1 d . . . . .
H14A H 0.4199 0.1779 0.2452 0.057 Uiso 1 1 calc R U . . .
C15 C 0.4346(4) 0.3471(11) 0.1987(4) 0.059(3) Uani 1 1 d . . . . .
H15A H 0.4634 0.3079 0.1865 0.070 Uiso 1 1 calc R U . . .
C16 C 0.4191(4) 0.4802(10) 0.1817(4) 0.054(2) Uani 1 1 d . . . . .
H16A H 0.4372 0.5333 0.1579 0.065 Uiso 1 1 calc R U . . .
C17 C 0.3770(3) 0.5360(9) 0.1996(4) 0.044(2) Uani 1 1 d . . . . .
H17A H 0.3660 0.6280 0.1880 0.053 Uiso 1 1 calc R U . . .
C18 C 0.3506(3) 0.4584(8) 0.2344(3) 0.0353(19) Uani 1 1 d . . . . .
H18A H 0.3217 0.4979 0.2464 0.042 Uiso 1 1 calc R U . . .
C19 C 0.4326(3) 0.2716(7) 0.4032(3) 0.0229(15) Uani 1 1 d . . . . .
C20 C 0.4581(3) 0.1420(7) 0.4149(3) 0.0276(17) Uani 1 1 d . . . . .
C21 C 0.5146(3) 0.1343(7) 0.4372(3) 0.0309(18) Uani 1 1 d . . . . .
H21A H 0.5314 0.0465 0.4436 0.037 Uiso 1 1 calc R U . . .
C22 C 0.5470(3) 0.2506(8) 0.4502(3) 0.0313(17) Uani 1 1 d . . . . .
C23 C 0.5219(3) 0.3770(7) 0.4383(3) 0.0281(17) Uani 1 1 d . . . . .
H23A H 0.5437 0.4575 0.4459 0.034 Uiso 1 1 calc R U . . .
C24 C 0.4655(3) 0.3906(7) 0.4152(3) 0.0267(16) Uani 1 1 d . . . . .
C25 C 0.4275(3) 0.0075(7) 0.4021(4) 0.039(2) Uani 1 1 d . . . . .
H25A H 0.4019 0.0076 0.3576 0.047 Uiso 1 1 calc R U . . .
H25B H 0.4075 -0.0038 0.4335 0.047 Uiso 1 1 calc R U . . .
H25C H 0.4532 -0.0685 0.4069 0.047 Uiso 1 1 calc R U . . .
C26 C 0.6083(3) 0.2394(8) 0.4737(4) 0.0392(19) Uani 1 1 d . . . . .
H26A H 0.6197 0.1726 0.4467 0.047 Uiso 1 1 calc R U . . .
H26B H 0.6205 0.2090 0.5194 0.047 Uiso 1 1 calc R U . . .
H26C H 0.6241 0.3293 0.4703 0.047 Uiso 1 1 calc R U . . .
C27 C 0.4424(3) 0.5332(7) 0.3998(3) 0.0344(19) Uani 1 1 d . . . . .
H27C H 0.4715 0.6010 0.4150 0.041 Uiso 1 1 calc R U . . .
H27B H 0.4151 0.5488 0.4218 0.041 Uiso 1 1 calc R U . . .
H27A H 0.4254 0.5426 0.3524 0.041 Uiso 1 1 calc R U . . .
B B 0.2950(5) 0.0741(11) 0.5707(5) 0.043(2) Uani 1 1 d . . . . .
H28 H 0.308(3) 0.160(7) 0.601(4) 0.051 Uiso 1 1 d . U . . .
H29 H 0.252(3) 0.054(7) 0.567(4) 0.051 Uiso 1 1 d . U . . .
H30 H 0.319(3) -0.012(7) 0.595(4) 0.051 Uiso 1 1 d . U . . .
N1 N 0.3341(2) 0.1883(6) 0.4823(2) 0.0295(14) Uani 1 1 d . . . . .
N2 N 0.2784(2) 0.0238(6) 0.4450(3) 0.0300(14) Uani 1 1 d . . . . .
P P 0.35849(8) 0.3043(2) 0.37521(8) 0.0252(4) Uani 1 1 d . . . . .
O O 0.4792(5) 0.1807(12) 0.6686(5) 0.055(3) Uani 0.5 1 d . U P A -1
C28 C 0.5240(8) 0.222(2) 0.7208(8) 0.060(5) Uani 0.5 1 d D U P A -1
H28A H 0.5293 0.3226 0.7177 0.072 Uiso 0.5 1 calc R U P A -1
H28B H 0.5570 0.1756 0.7177 0.072 Uiso 0.5 1 calc R U P A -1
C29 C 0.5170(10) 0.191(3) 0.7834(10) 0.080(6) Uani 0.5 1 d D U P A -1
H29A H 0.5073 0.2743 0.8037 0.096 Uiso 0.5 1 calc R U P A -1
H29B H 0.5502 0.1501 0.8139 0.096 Uiso 0.5 1 calc R U P A -1
C30 C 0.4710(8) 0.0893(19) 0.7649(8) 0.064(5) Uani 0.5 1 d D U P A -1
H30A H 0.4816 0.0031 0.7901 0.077 Uiso 0.5 1 calc R U P A -1
H30B H 0.4387 0.1276 0.7737 0.077 Uiso 0.5 1 calc R U P A -1
C31 C 0.4595(8) 0.0632(18) 0.6942(8) 0.059(5) Uani 0.5 1 d D U P A -1
H31A H 0.4782 -0.0212 0.6872 0.071 Uiso 0.5 1 calc R U P A -1
H31B H 0.4200 0.0518 0.6725 0.071 Uiso 0.5 1 calc R U P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.352(9) . ?
C1 N1 1.407(8) . ?
C1 P 1.817(7) . ?
C2 N1 1.343(9) . ?
C2 N2 1.357(8) . ?
C2 B 1.609(11) . ?
C3 N2 1.374(9) . ?
C3 H3A 0.9500 . ?
C4 N1 1.467(8) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 N2 1.462(9) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C13 1.505(10) . ?
C6 C7 1.542(9) . ?
C6 P 1.881(6) . ?
C6 H6A 1.0000 . ?
C7 C12 1.358(10) . ?
C7 C8 1.416(8) . ?
C8 C9 1.393(9) . ?
C8 H8A 0.9500 . ?
C9 C10 1.365(11) . ?
C9 H9A 0.9500 . ?
C10 C11 1.395(9) . ?
C10 H10A 0.9500 . ?
C11 C12 1.395(9) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C18 1.385(10) . ?
C13 C14 1.388(11) . ?
C14 C15 1.380(12) . ?
C14 H14A 0.9500 . ?
C15 C16 1.371(12) . ?
C15 H15A 0.9500 . ?
C16 C17 1.380(12) . ?
C16 H16A 0.9500 . ?
C17 C18 1.388(11) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 C20 1.409(9) . ?
C19 C24 1.414(9) . ?
C19 P 1.857(7) . ?
C20 C21 1.396(10) . ?
C20 C25 1.511(9) . ?
C21 C22 1.386(9) . ?
C21 H21A 0.9500 . ?
C22 C23 1.378(9) . ?
C22 C26 1.516(10) . ?
C23 C24 1.399(10) . ?
C23 H23A 0.9500 . ?
C24 C27 1.508(9) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27C 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27A 0.9800 . ?
B H28 1.05(7) . ?
B H29 1.10(8) . ?
B H30 1.07(7) . ?
O C28 1.402(19) . ?
O C31 1.43(2) . ?
C28 C29 1.45(2) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.507(19) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.480(18) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C1 N1 104.4(6) . . ?
C3 C1 P 133.2(5) . . ?
N1 C1 P 121.2(5) . . ?
N1 C2 N2 104.7(6) . . ?
N1 C2 B 128.9(7) . . ?
N2 C2 B 126.4(7) . . ?
C1 C3 N2 108.4(6) . . ?
C1 C3 H3A 125.8 . . ?
N2 C3 H3A 125.8 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C13 C6 C7 109.8(5) . . ?
C13 C6 P 107.2(5) . . ?
C7 C6 P 112.8(5) . . ?
C13 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
P C6 H6A 109.0 . . ?
C12 C7 C8 119.1(6) . . ?
C12 C7 C6 125.0(6) . . ?
C8 C7 C6 115.7(6) . . ?
C9 C8 C7 119.2(7) . . ?
C9 C8 H8A 120.4 . . ?
C7 C8 H8A 120.4 . . ?
C10 C9 C8 120.7(7) . . ?
C10 C9 H9A 119.7 . . ?
C8 C9 H9A 119.7 . . ?
C9 C10 C11 120.5(7) . . ?
C9 C10 H10A 119.7 . . ?
C11 C10 H10A 119.7 . . ?
C10 C11 C12 118.6(7) . . ?
C10 C11 H11A 120.7 . . ?
C12 C11 H11A 120.7 . . ?
C7 C12 C11 121.8(7) . . ?
C7 C12 H12A 119.1 . . ?
C11 C12 H12A 119.1 . . ?
C18 C13 C14 118.1(8) . . ?
C18 C13 C6 121.3(7) . . ?
C14 C13 C6 120.6(7) . . ?
C15 C14 C13 121.0(8) . . ?
C15 C14 H14A 119.5 . . ?
C13 C14 H14A 119.5 . . ?
C16 C15 C14 120.6(9) . . ?
C16 C15 H15A 119.7 . . ?
C14 C15 H15A 119.7 . . ?
C15 C16 C17 119.2(9) . . ?
C15 C16 H16A 120.4 . . ?
C17 C16 H16A 120.4 . . ?
C16 C17 C18 120.4(9) . . ?
C16 C17 H17A 119.8 . . ?
C18 C17 H17A 119.8 . . ?
C13 C18 C17 120.7(8) . . ?
C13 C18 H18A 119.7 . . ?
C17 C18 H18A 119.7 . . ?
C20 C19 C24 118.6(6) . . ?
C20 C19 P 126.3(5) . . ?
C24 C19 P 115.1(5) . . ?
C21 C20 C19 119.5(6) . . ?
C21 C20 C25 116.9(7) . . ?
C19 C20 C25 123.6(6) . . ?
C22 C21 C20 122.1(7) . . ?
C22 C21 H21A 118.9 . . ?
C20 C21 H21A 118.9 . . ?
C23 C22 C21 118.1(6) . . ?
C23 C22 C26 120.8(7) . . ?
C21 C22 C26 121.1(7) . . ?
C22 C23 C24 122.1(7) . . ?
C22 C23 H23A 118.9 . . ?
C24 C23 H23A 118.9 . . ?
C23 C24 C19 119.5(6) . . ?
C23 C24 C27 117.8(7) . . ?
C19 C24 C27 122.6(6) . . ?
C20 C25 H25A 109.5 . . ?
C20 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C20 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C26 H26A 109.5 . . ?
C22 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C22 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27C 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27C C27 H27B 109.5 . . ?
C24 C27 H27A 109.5 . . ?
H27C C27 H27A 109.5 . . ?
H27B C27 H27A 109.5 . . ?
C2 B H28 112(4) . . ?
C2 B H29 112(4) . . ?
H28 B H29 107(6) . . ?
C2 B H30 111(4) . . ?
H28 B H30 107(5) . . ?
H29 B H30 107(6) . . ?
C2 N1 C1 111.9(6) . . ?
C2 N1 C4 124.7(6) . . ?
C1 N1 C4 123.4(6) . . ?
C2 N2 C3 110.6(6) . . ?
C2 N2 C5 124.8(6) . . ?
C3 N2 C5 124.7(6) . . ?
C1 P C19 105.4(3) . . ?
C1 P C6 101.8(3) . . ?
C19 P C6 102.3(3) . . ?
C28 O C31 103.3(12) . . ?
O C28 C29 111.7(16) . . ?
O C28 H28A 109.3 . . ?
C29 C28 H28A 109.3 . . ?
O C28 H28B 109.3 . . ?
C29 C28 H28B 109.3 . . ?
H28A C28 H28B 107.9 . . ?
C28 C29 C30 102.3(14) . . ?
C28 C29 H29A 111.3 . . ?
C30 C29 H29A 111.3 . . ?
C28 C29 H29B 111.3 . . ?
C30 C29 H29B 111.3 . . ?
H29A C29 H29B 109.2 . . ?
C31 C30 C29 105.8(14) . . ?
C31 C30 H30A 110.6 . . ?
C29 C30 H30A 110.6 . . ?
C31 C30 H30B 110.6 . . ?
C29 C30 H30B 110.6 . . ?
H30A C30 H30B 108.7 . . ?
O C31 C30 106.2(12) . . ?
O C31 H31A 110.5 . . ?
C30 C31 H31A 110.5 . . ?
O C31 H31B 110.5 . . ?
C30 C31 H31B 110.5 . . ?
H31A C31 H31B 108.7 . . ?

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
N1 C1 C3 N2 -1.1(8) . . . . ?
P C1 C3 N2 -168.2(6) . . . . ?
C13 C6 C7 C12 -105.4(8) . . . . ?
P C6 C7 C12 14.1(10) . . . . ?
C13 C6 C7 C8 71.1(8) . . . . ?
P C6 C7 C8 -169.4(5) . . . . ?
C12 C7 C8 C9 0.0(10) . . . . ?
C6 C7 C8 C9 -176.7(6) . . . . ?
C7 C8 C9 C10 0.5(11) . . . . ?
C8 C9 C10 C11 -0.5(12) . . . . ?
C9 C10 C11 C12 0.0(11) . . . . ?
C8 C7 C12 C11 -0.5(11) . . . . ?
C6 C7 C12 C11 175.9(7) . . . . ?
C10 C11 C12 C7 0.5(11) . . . . ?
C7 C6 C13 C18 49.9(9) . . . . ?
P C6 C13 C18 -72.9(7) . . . . ?
C7 C6 C13 C14 -129.4(7) . . . . ?
P C6 C13 C14 107.7(7) . . . . ?
C18 C13 C14 C15 -0.3(11) . . . . ?
C6 C13 C14 C15 179.1(7) . . . . ?
C13 C14 C15 C16 0.3(13) . . . . ?
C14 C15 C16 C17 -0.2(13) . . . . ?
C15 C16 C17 C18 0.0(12) . . . . ?
C14 C13 C18 C17 0.1(10) . . . . ?
C6 C13 C18 C17 -179.3(7) . . . . ?
C16 C17 C18 C13 0.0(11) . . . . ?
C24 C19 C20 C21 -0.7(10) . . . . ?
P C19 C20 C21 -178.7(6) . . . . ?
C24 C19 C20 C25 -178.1(6) . . . . ?
P C19 C20 C25 3.9(10) . . . . ?
C19 C20 C21 C22 2.0(11) . . . . ?
C25 C20 C21 C22 179.5(7) . . . . ?
C20 C21 C22 C23 -2.4(11) . . . . ?
C20 C21 C22 C26 -179.4(7) . . . . ?
C21 C22 C23 C24 1.6(11) . . . . ?
C26 C22 C23 C24 178.6(7) . . . . ?
C22 C23 C24 C19 -0.4(10) . . . . ?
C22 C23 C24 C27 -176.2(7) . . . . ?
C20 C19 C24 C23 0.0(9) . . . . ?
P C19 C24 C23 178.2(5) . . . . ?
C20 C19 C24 C27 175.6(6) . . . . ?
P C19 C24 C27 -6.2(8) . . . . ?
N2 C2 N1 C1 0.5(8) . . . . ?
B C2 N1 C1 179.9(8) . . . . ?
N2 C2 N1 C4 177.8(6) . . . . ?
B C2 N1 C4 -2.8(12) . . . . ?
C3 C1 N1 C2 0.4(8) . . . . ?
P C1 N1 C2 169.4(5) . . . . ?
C3 C1 N1 C4 -177.0(6) . . . . ?
P C1 N1 C4 -8.0(9) . . . . ?
N1 C2 N2 C3 -1.2(8) . . . . ?
B C2 N2 C3 179.4(8) . . . . ?
N1 C2 N2 C5 179.2(6) . . . . ?
B C2 N2 C5 -0.2(12) . . . . ?
C1 C3 N2 C2 1.5(8) . . . . ?
C1 C3 N2 C5 -178.9(7) . . . . ?
C3 C1 P C19 -118.4(7) . . . . ?
N1 C1 P C19 76.3(6) . . . . ?
C3 C1 P C6 -11.9(8) . . . . ?
N1 C1 P C6 -177.2(5) . . . . ?
C20 C19 P C1 37.0(6) . . . . ?
C24 C19 P C1 -141.1(5) . . . . ?
C20 C19 P C6 -69.1(6) . . . . ?
C24 C19 P C6 112.8(5) . . . . ?
C13 C6 P C1 -171.4(5) . . . . ?
C7 C6 P C1 67.7(6) . . . . ?
C13 C6 P C19 -62.5(5) . . . . ?
C7 C6 P C19 176.6(5) . . . . ?
C31 O C28 C29 -31(2) . . . . ?
O C28 C29 C30 16(3) . . . . ?
C28 C29 C30 C31 5(3) . . . . ?
C28 O C31 C30 32.4(19) . . . . ?
C29 C30 C31 O -23(2) . . . . ?

_refine_diff_density_max         0.468
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.061

_shelxl_version_number           2013-2

