#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:59:53 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178415 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/36/4023617.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4023617
loop_
_publ_author_name
'Isabelle Bonnaventure'
'André B. Charette'
_publ_contact_author_address
;
      Université de Montréal
      Département de Chimie
      C.P. 6128, Succ. Centre-ville
      Montréal, Québec
      Canada, H3C 3J7
;
_publ_contact_author_email       andre.charette@umontreal.ca
_publ_contact_author_fax         '+1 514 343 5900'
_publ_contact_author_name        'Dr André B. Charette'
_publ_contact_author_phone       '+1 514 343 6283'
_publ_section_title
;
 Probing the Importance of the Hemilabile Site of Bis(phosphine)
 Monoxide Ligands in the Copper-Catalyzed Addition of Diethylzinc to
 N-Phosphinoylimines: Discovery of New Effective Chiral Ligands
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6330
_journal_page_last               6340
_journal_paper_doi               10.1021/jo800969x
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration rm
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C19 H30 O P2'
_chemical_formula_sum            'C19 H30 O P2'
_chemical_formula_weight         336.37
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.983(3)
_cell_angle_beta                 93.624(3)
_cell_angle_gamma                107.887(3)
_cell_formula_units_Z            2
_cell_length_a                   9.2647(4)
_cell_length_b                   10.3599(4)
_cell_length_c                   10.5290(5)
_cell_measurement_reflns_used    4295
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.62
_cell_measurement_theta_min      4.30
_cell_volume                     939.84(7)
_computing_cell_refinement       'SMART (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker AXS Smart 2K/Platform'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_av_sigmaI/netI    0.0701
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10894
_diffrn_reflns_theta_full        70.61
_diffrn_reflns_theta_max         70.61
_diffrn_reflns_theta_min         4.30
_diffrn_standards_decay_%        0.00
_diffrn_standards_number         92
_exptl_absorpt_coefficient_mu    2.084
_exptl_absorpt_correction_T_max  0.9800
_exptl_absorpt_correction_T_min  0.4400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.818
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.170
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         3501
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0859
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1660P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2115
_refine_ls_wR_factor_ref         0.2156
_reflns_number_gt                3129
_reflns_number_total             3501
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo800969x-file004.cif
_cod_data_source_block           cha116
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (48
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (76 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023617
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P11 P 0.3964(2) 0.77699(17) 0.46917(16) 0.0200(4) Uani 1 1 d . . .
P12 P 0.4596(2) 0.60141(18) 0.20256(17) 0.0224(4) Uani 1 1 d . . .
O11 O 0.2593(6) 0.6487(5) 0.4257(5) 0.0252(11) Uani 1 1 d . . .
C11 C 0.5791(8) 0.7440(7) 0.4599(8) 0.0221(15) Uani 1 1 d . . .
C12 C 0.6110(9) 0.6674(7) 0.3429(7) 0.0226(15) Uani 1 1 d . . .
C13 C 0.7539(9) 0.6520(8) 0.3428(8) 0.0250(16) Uani 1 1 d . . .
H13 H 0.7775 0.6048 0.2652 0.030 Uiso 1 1 calc R . .
C14 C 0.8646(9) 0.7018(8) 0.4502(8) 0.0264(16) Uani 1 1 d . . .
H14 H 0.9611 0.6880 0.4463 0.032 Uiso 1 1 calc R . .
C15 C 0.8317(10) 0.7731(8) 0.5644(8) 0.0280(17) Uani 1 1 d . . .
H15 H 0.9053 0.8067 0.6396 0.034 Uiso 1 1 calc R . .
C16 C 0.6913(9) 0.7941(8) 0.5671(8) 0.0269(17) Uani 1 1 d . . .
H16 H 0.6708 0.8442 0.6445 0.032 Uiso 1 1 calc R . .
C111 C 0.3934(9) 0.9228(7) 0.3892(7) 0.0222(15) Uani 1 1 d . . .
C112 C 0.3884(10) 1.0360(8) 0.5065(8) 0.0276(17) Uani 1 1 d . . .
H11A H 0.4938 1.0955 0.5428 0.033 Uiso 1 1 calc R . .
H11B H 0.3328 1.0952 0.4768 0.033 Uiso 1 1 calc R . .
C113 C 0.3093(10) 0.9678(8) 0.6099(8) 0.0290(17) Uani 1 1 d . . .
H11C H 0.1995 0.9194 0.5794 0.035 Uiso 1 1 calc R . .
H11D H 0.3190 1.0374 0.6901 0.035 Uiso 1 1 calc R . .
C114 C 0.3914(9) 0.8631(8) 0.6355(7) 0.0256(16) Uani 1 1 d . . .
H114 H 0.4985 0.9159 0.6762 0.031 Uiso 1 1 calc R . .
C115 C 0.5333(10) 0.9769(8) 0.3213(9) 0.0301(18) Uani 1 1 d . . .
H11E H 0.5343 0.9055 0.2473 0.045 Uiso 1 1 calc R . .
H11F H 0.6260 1.0000 0.3825 0.045 Uiso 1 1 calc R . .
H11G H 0.5296 1.0599 0.2905 0.045 Uiso 1 1 calc R . .
C116 C 0.2483(10) 0.8787(8) 0.2942(8) 0.0274(17) Uani 1 1 d . . .
H11H H 0.2421 0.9576 0.2573 0.041 Uiso 1 1 calc R . .
H11I H 0.1593 0.8465 0.3399 0.041 Uiso 1 1 calc R . .
H11J H 0.2501 0.8035 0.2243 0.041 Uiso 1 1 calc R . .
C117 C 0.3180(12) 0.7624(10) 0.7183(9) 0.038(2) Uani 1 1 d . . .
H11K H 0.3185 0.8132 0.8061 0.058 Uiso 1 1 calc R . .
H11L H 0.3755 0.6977 0.7228 0.058 Uiso 1 1 calc R . .
H11M H 0.2124 0.7106 0.6800 0.058 Uiso 1 1 calc R . .
C121 C 0.3924(9) 0.4106(8) 0.2037(8) 0.0261(16) Uani 1 1 d . . .
H121 H 0.2962 0.3685 0.1416 0.031 Uiso 1 1 calc R . .
C122 C 0.5129(10) 0.3549(8) 0.1431(9) 0.0332(19) Uani 1 1 d . . .
H12A H 0.6039 0.3775 0.2078 0.040 Uiso 1 1 calc R . .
H12B H 0.4709 0.2529 0.1144 0.040 Uiso 1 1 calc R . .
C123 C 0.5566(11) 0.4208(9) 0.0288(9) 0.035(2) Uani 1 1 d . . .
H12C H 0.4795 0.3716 -0.0477 0.042 Uiso 1 1 calc R . .
H12D H 0.6566 0.4135 0.0071 0.042 Uiso 1 1 calc R . .
C124 C 0.5668(10) 0.5755(8) 0.0607(8) 0.0287(17) Uani 1 1 d . . .
H124 H 0.6765 0.6339 0.0852 0.034 Uiso 1 1 calc R . .
C125 C 0.3539(11) 0.3705(8) 0.3332(9) 0.037(2) Uani 1 1 d . . .
H12E H 0.3079 0.2697 0.3200 0.055 Uiso 1 1 calc R . .
H12F H 0.2815 0.4151 0.3681 0.055 Uiso 1 1 calc R . .
H12G H 0.4475 0.4011 0.3946 0.055 Uiso 1 1 calc R . .
C126 C 0.4993(12) 0.6213(9) -0.0536(8) 0.037(2) Uani 1 1 d . . .
H12H H 0.5461 0.5972 -0.1314 0.055 Uiso 1 1 calc R . .
H12I H 0.5202 0.7218 -0.0326 0.055 Uiso 1 1 calc R . .
H12J H 0.3886 0.5743 -0.0700 0.055 Uiso 1 1 calc R . .
P21 P 0.8644(2) 0.28545(17) 0.69735(18) 0.0220(4) Uani 1 1 d . . .
P22 P 0.9343(2) 0.09880(17) 0.89558(17) 0.0215(4) Uani 1 1 d . . .
O21 O 0.7317(6) 0.1545(5) 0.6853(5) 0.0253(11) Uani 1 1 d . . .
C21 C 0.9378(9) 0.3632(8) 0.8678(8) 0.0256(16) Uani 1 1 d . . .
C22 C 0.9570(9) 0.2835(8) 0.9574(7) 0.0220(15) Uani 1 1 d . . .
C23 C 0.9991(9) 0.3472(8) 1.0886(8) 0.0250(16) Uani 1 1 d . . .
H23 H 1.0102 0.2927 1.1501 0.030 Uiso 1 1 calc R . .
C24 C 1.0256(10) 0.4893(8) 1.1321(8) 0.0280(17) Uani 1 1 d . . .
H24 H 1.0557 0.5309 1.2216 0.034 Uiso 1 1 calc R . .
C25 C 1.0071(10) 0.5673(7) 1.0431(8) 0.0287(18) Uani 1 1 d . . .
H25 H 1.0239 0.6636 1.0713 0.034 Uiso 1 1 calc R . .
C26 C 0.9636(10) 0.5062(8) 0.9109(9) 0.0293(18) Uani 1 1 d . . .
H26 H 0.9515 0.5611 0.8501 0.035 Uiso 1 1 calc R . .
C211 C 1.0152(9) 0.2679(8) 0.5961(8) 0.0252(16) Uani 1 1 d . . .
C212 C 0.9921(11) 0.3445(9) 0.4847(8) 0.034(2) Uani 1 1 d . . .
H21A H 1.0692 0.4380 0.5017 0.041 Uiso 1 1 calc R . .
H21B H 1.0057 0.2923 0.4007 0.041 Uiso 1 1 calc R . .
C213 C 0.8321(11) 0.3563(9) 0.4779(8) 0.0334(19) Uani 1 1 d . . .
H21C H 0.7541 0.2649 0.4433 0.040 Uiso 1 1 calc R . .
H21D H 0.8223 0.4213 0.4218 0.040 Uiso 1 1 calc R . .
C214 C 0.8142(10) 0.4111(7) 0.6180(8) 0.0263(17) Uani 1 1 d . . .
H214 H 0.8944 0.5035 0.6494 0.032 Uiso 1 1 calc R . .
C215 C 1.1773(10) 0.3336(10) 0.6690(9) 0.0355(19) Uani 1 1 d . . .
H21E H 1.1895 0.2841 0.7382 0.053 Uiso 1 1 calc R . .
H21F H 1.1938 0.4310 0.7072 0.053 Uiso 1 1 calc R . .
H21G H 1.2520 0.3277 0.6083 0.053 Uiso 1 1 calc R . .
C216 C 0.9884(10) 0.1144(8) 0.5411(8) 0.0272(17) Uani 1 1 d . . .
H21H H 1.0693 0.1054 0.4880 0.041 Uiso 1 1 calc R . .
H21I H 0.8890 0.0740 0.4872 0.041 Uiso 1 1 calc R . .
H21J H 0.9898 0.0657 0.6128 0.041 Uiso 1 1 calc R . .
C217 C 0.6584(10) 0.4254(9) 0.6435(9) 0.0325(19) Uani 1 1 d . . .
H21K H 0.6449 0.5028 0.6078 0.049 Uiso 1 1 calc R . .
H21L H 0.6532 0.4429 0.7373 0.049 Uiso 1 1 calc R . .
H21M H 0.5773 0.3396 0.6016 0.049 Uiso 1 1 calc R . .
C221 C 0.7504(8) 0.0049(7) 0.9567(8) 0.0234(15) Uani 1 1 d . . .
H221 H 0.7028 -0.0852 0.8938 0.028 Uiso 1 1 calc R . .
C222 C 0.8005(10) -0.0295(9) 1.0855(9) 0.0299(17) Uani 1 1 d . . .
H22A H 0.8186 0.0508 1.1579 0.036 Uiso 1 1 calc R . .
H22B H 0.7203 -0.1095 1.1049 0.036 Uiso 1 1 calc R . .
C223 C 0.9468(10) -0.0640(9) 1.0689(9) 0.0319(18) Uani 1 1 d . . .
H22C H 0.9924 -0.0728 1.1533 0.038 Uiso 1 1 calc R . .
H22D H 0.9248 -0.1531 1.0067 0.038 Uiso 1 1 calc R . .
C224 C 1.0563(10) 0.0511(9) 1.0186(8) 0.0292(17) Uani 1 1 d . . .
H224 H 1.1009 0.1326 1.0920 0.035 Uiso 1 1 calc R . .
C225 C 0.6309(10) 0.0776(9) 0.9673(9) 0.0305(18) Uani 1 1 d . . .
H22E H 0.5389 0.0178 0.9946 0.046 Uiso 1 1 calc R . .
H22F H 0.6051 0.0973 0.8826 0.046 Uiso 1 1 calc R . .
H22G H 0.6716 0.1646 1.0316 0.046 Uiso 1 1 calc R . .
C226 C 1.1875(11) 0.0132(10) 0.9563(9) 0.0352(19) Uani 1 1 d . . .
H22H H 1.2481 -0.0133 1.0206 0.053 Uiso 1 1 calc R . .
H22I H 1.2529 0.0933 0.9265 0.053 Uiso 1 1 calc R . .
H22J H 1.1451 -0.0645 0.8822 0.053 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0000 '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 0.0492 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O11 P11 C11 . . . 113.6(3) y
O11 P11 C114 . . . 110.9(3) y
C11 P11 C114 . . . 109.0(4) y
O11 P11 C111 . . . 114.3(3) y
C11 P11 C111 . . . 110.7(4) y
C114 P11 C111 . . . 97.2(3) y
C12 P12 C124 . . . 103.5(4) y
C12 P12 C121 . . . 101.0(3) y
C124 P12 C121 . . . 92.0(4) y
C16 C11 C12 . . . 118.6(7) y
C16 C11 P11 . . . 119.9(6) y
C12 C11 P11 . . . 121.5(6) y
C13 C12 C11 . . . 117.7(7) y
C13 C12 P12 . . . 124.7(6) y
C11 C12 P12 . . . 117.6(6) y
C12 C13 C14 . . . 123.3(7) y
C12 C13 H13 . . . 118.4 ?
C14 C13 H13 . . . 118.4 ?
C13 C14 C15 . . . 118.8(7) y
C13 C14 H14 . . . 120.6 ?
C15 C14 H14 . . . 120.6 ?
C16 C15 C14 . . . 119.6(7) y
C16 C15 H15 . . . 120.2 ?
C14 C15 H15 . . . 120.2 ?
C15 C16 C11 . . . 122.0(7) y
C15 C16 H16 . . . 119 ?
C11 C16 H16 . . . 119 ?
C116 C111 C115 . . . 110.5(7) y
C116 C111 C112 . . . 110.4(6) y
C115 C111 C112 . . . 110.3(6) y
C116 C111 P11 . . . 109.2(5) y
C115 C111 P11 . . . 114.0(5) y
C112 C111 P11 . . . 102.1(5) y
C113 C112 C111 . . . 109.8(6) y
C113 C112 H11A . . . 109.7 ?
C111 C112 H11A . . . 109.7 ?
C113 C112 H11B . . . 109.7 ?
C111 C112 H11B . . . 109.7 ?
H11A C112 H11B . . . 108.2 ?
C112 C113 C114 . . . 105.4(7) y
C112 C113 H11C . . . 110.7 ?
C114 C113 H11C . . . 110.7 ?
C112 C113 H11D . . . 110.7 ?
C114 C113 H11D . . . 110.7 ?
H11C C113 H11D . . . 108.8 ?
C117 C114 C113 . . . 116.7(7) y
C117 C114 P11 . . . 112.6(6) y
C113 C114 P11 . . . 101.2(5) y
C117 C114 H114 . . . 108.7 ?
C113 C114 H114 . . . 108.7 ?
P11 C114 H114 . . . 108.7 ?
C111 C115 H11E . . . 109.5 ?
C111 C115 H11F . . . 109.5 ?
H11E C115 H11F . . . 109.5 ?
C111 C115 H11G . . . 109.5 ?
H11E C115 H11G . . . 109.5 ?
H11F C115 H11G . . . 109.5 ?
C111 C116 H11H . . . 109.5 ?
C111 C116 H11I . . . 109.5 ?
H11H C116 H11I . . . 109.5 ?
C111 C116 H11J . . . 109.5 ?
H11H C116 H11J . . . 109.5 ?
H11I C116 H11J . . . 109.5 ?
C114 C117 H11K . . . 109.5 ?
C114 C117 H11L . . . 109.5 ?
H11K C117 H11L . . . 109.5 ?
C114 C117 H11M . . . 109.5 ?
H11K C117 H11M . . . 109.5 ?
H11L C117 H11M . . . 109.5 ?
C125 C121 C122 . . . 114.5(7) y
C125 C121 P12 . . . 116.6(5) y
C122 C121 P12 . . . 105.3(5) y
C125 C121 H121 . . . 106.6 ?
C122 C121 H121 . . . 106.6 ?
P12 C121 H121 . . . 106.6 ?
C123 C122 C121 . . . 108.2(7) y
C123 C122 H12A . . . 110.1 ?
C121 C122 H12A . . . 110.1 ?
C123 C122 H12B . . . 110.1 ?
C121 C122 H12B . . . 110.1 ?
H12A C122 H12B . . . 108.4 ?
C122 C123 C124 . . . 110.2(7) y
C122 C123 H12C . . . 109.6 ?
C124 C123 H12C . . . 109.6 ?
C122 C123 H12D . . . 109.6 ?
C124 C123 H12D . . . 109.6 ?
H12C C123 H12D . . . 108.1 ?
C126 C124 C123 . . . 112.7(7) y
C126 C124 P12 . . . 109.1(6) y
C123 C124 P12 . . . 108.1(6) y
C126 C124 H124 . . . 109 ?
C123 C124 H124 . . . 109 ?
P12 C124 H124 . . . 109 ?
C121 C125 H12E . . . 109.5 ?
C121 C125 H12F . . . 109.5 ?
H12E C125 H12F . . . 109.5 ?
C121 C125 H12G . . . 109.5 ?
H12E C125 H12G . . . 109.5 ?
H12F C125 H12G . . . 109.5 ?
C124 C126 H12H . . . 109.5 ?
C124 C126 H12I . . . 109.5 ?
H12H C126 H12I . . . 109.5 ?
C124 C126 H12J . . . 109.5 ?
H12H C126 H12J . . . 109.5 ?
H12I C126 H12J . . . 109.5 ?
O21 P21 C214 . . . 112.1(3) y
O21 P21 C21 . . . 111.0(3) y
C214 P21 C21 . . . 109.8(4) y
O21 P21 C211 . . . 114.5(3) y
C214 P21 C211 . . . 95.5(4) y
C21 P21 C211 . . . 113.1(4) y
C22 P22 C224 . . . 105.5(4) y
C22 P22 C221 . . . 102.8(3) y
C224 P22 C221 . . . 92.6(4) y
C22 C21 C26 . . . 119.5(7) y
C22 C21 P21 . . . 121.8(6) y
C26 C21 P21 . . . 118.4(6) y
C21 C22 C23 . . . 118.9(7) y
C21 C22 P22 . . . 118.1(6) y
C23 C22 P22 . . . 122.9(6) y
C22 C23 C24 . . . 121.9(7) y
C22 C23 H23 . . . 119 ?
C24 C23 H23 . . . 119 ?
C25 C24 C23 . . . 118.8(7) y
C25 C24 H24 . . . 120.6 ?
C23 C24 H24 . . . 120.6 ?
C24 C25 C26 . . . 120.6(7) y
C24 C25 H25 . . . 119.7 ?
C26 C25 H25 . . . 119.7 ?
C25 C26 C21 . . . 120.2(7) y
C25 C26 H26 . . . 119.9 ?
C21 C26 H26 . . . 119.9 ?
C216 C211 C215 . . . 109.1(7) y
C216 C211 C212 . . . 110.6(6) y
C215 C211 C212 . . . 110.7(7) y
C216 C211 P21 . . . 109.7(5) y
C215 C211 P21 . . . 113.5(6) y
C212 C211 P21 . . . 103.1(5) y
C213 C212 C211 . . . 109.4(7) y
C213 C212 H21A . . . 109.8 ?
C211 C212 H21A . . . 109.8 ?
C213 C212 H21B . . . 109.8 ?
C211 C212 H21B . . . 109.8 ?
H21A C212 H21B . . . 108.2 ?
C212 C213 C214 . . . 104.6(7) y
C212 C213 H21C . . . 110.8 ?
C214 C213 H21C . . . 110.8 ?
C212 C213 H21D . . . 110.8 ?
C214 C213 H21D . . . 110.8 ?
H21C C213 H21D . . . 108.9 ?
C213 C214 C217 . . . 116.8(7) y
C213 C214 P21 . . . 100.1(5) y
C217 C214 P21 . . . 113.9(6) y
C213 C214 H214 . . . 108.5 ?
C217 C214 H214 . . . 108.5 ?
P21 C214 H214 . . . 108.5 ?
C211 C215 H21E . . . 109.5 ?
C211 C215 H21F . . . 109.5 ?
H21E C215 H21F . . . 109.5 ?
C211 C215 H21G . . . 109.5 ?
H21E C215 H21G . . . 109.5 ?
H21F C215 H21G . . . 109.5 ?
C211 C216 H21H . . . 109.5 ?
C211 C216 H21I . . . 109.5 ?
H21H C216 H21I . . . 109.5 ?
C211 C216 H21J . . . 109.5 ?
H21H C216 H21J . . . 109.5 ?
H21I C216 H21J . . . 109.5 ?
C214 C217 H21K . . . 109.5 ?
C214 C217 H21L . . . 109.5 ?
H21K C217 H21L . . . 109.5 ?
C214 C217 H21M . . . 109.5 ?
H21K C217 H21M . . . 109.5 ?
H21L C217 H21M . . . 109.5 ?
C225 C221 C222 . . . 113.7(7) y
C225 C221 P22 . . . 116.4(5) y
C222 C221 P22 . . . 105.4(5) y
C225 C221 H221 . . . 107 ?
C222 C221 H221 . . . 107 ?
P22 C221 H221 . . . 107 ?
C223 C222 C221 . . . 107.0(7) y
C223 C222 H22A . . . 110.3 ?
C221 C222 H22A . . . 110.3 ?
C223 C222 H22B . . . 110.3 ?
C221 C222 H22B . . . 110.3 ?
H22A C222 H22B . . . 108.6 ?
C224 C223 C222 . . . 108.2(6) y
C224 C223 H22C . . . 110.1 ?
C222 C223 H22C . . . 110.1 ?
C224 C223 H22D . . . 110.1 ?
C222 C223 H22D . . . 110.1 ?
H22C C223 H22D . . . 108.4 ?
C223 C224 C226 . . . 114.8(7) y
C223 C224 P22 . . . 105.2(6) y
C226 C224 P22 . . . 110.5(6) y
C223 C224 H224 . . . 108.7 ?
C226 C224 H224 . . . 108.7 ?
P22 C224 H224 . . . 108.7 ?
C221 C225 H22E . . . 109.5 ?
C221 C225 H22F . . . 109.5 ?
H22E C225 H22F . . . 109.5 ?
C221 C225 H22G . . . 109.5 ?
H22E C225 H22G . . . 109.5 ?
H22F C225 H22G . . . 109.5 ?
C224 C226 H22H . . . 109.5 ?
C224 C226 H22I . . . 109.5 ?
H22H C226 H22I . . . 109.5 ?
C224 C226 H22J . . . 109.5 ?
H22H C226 H22J . . . 109.5 ?
H22I C226 H22J . . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P11 O11 . . 1.506(5) y
P11 C11 . . 1.831(7) y
P11 C114 . . 1.833(8) y
P11 C111 . . 1.859(7) y
P12 C12 . . 1.848(8) y
P12 C124 . . 1.871(9) y
P12 C121 . . 1.884(8) y
C11 C16 . . 1.393(11) y
C11 C12 . . 1.444(10) y
C12 C13 . . 1.382(11) y
C13 C14 . . 1.387(11) y
C13 H13 . . 0.95 ?
C14 C15 . . 1.400(12) y
C14 H14 . . 0.95 ?
C15 C16 . . 1.385(12) y
C15 H15 . . 0.95 ?
C16 H16 . . 0.95 ?
C111 C116 . . 1.52(1) y
C111 C115 . . 1.521(12) y
C111 C112 . . 1.562(10) y
C112 C113 . . 1.507(12) y
C112 H11a . . 0.99 ?
C112 H11b . . 0.99 ?
C113 C114 . . 1.552(11) y
C113 H11c . . 0.99 ?
C113 H11d . . 0.99 ?
C114 C117 . . 1.505(12) y
C114 H114 . . 1 ?
C115 H11e . . 0.98 ?
C115 H11f . . 0.98 ?
C115 H11g . . 0.98 ?
C116 H11h . . 0.98 ?
C116 H11i . . 0.98 ?
C116 H11j . . 0.98 ?
C117 H11k . . 0.98 ?
C117 H11l . . 0.98 ?
C117 H11m . . 0.98 ?
C121 C125 . . 1.525(12) y
C121 C122 . . 1.532(11) y
C121 H121 . . 1 ?
C122 C123 . . 1.502(13) y
C122 H12a . . 0.99 ?
C122 H12b . . 0.99 ?
C123 C124 . . 1.551(11) y
C123 H12c . . 0.99 ?
C123 H12d . . 0.99 ?
C124 C126 . . 1.533(12) y
C124 H124 . . 1 ?
C125 H12e . . 0.98 ?
C125 H12f . . 0.98 ?
C125 H12g . . 0.98 ?
C126 H12h . . 0.98 ?
C126 H12i . . 0.98 ?
C126 H12j . . 0.98 ?
P21 O21 . . 1.504(5) y
P21 C214 . . 1.819(7) y
P21 C21 . . 1.828(8) y
P21 C211 . . 1.844(8) y
P22 C22 . . 1.853(8) y
P22 C224 . . 1.892(8) y
P22 C221 . . 1.898(8) y
C21 C22 . . 1.393(11) y
C21 C26 . . 1.412(10) y
C22 C23 . . 1.397(11) y
C23 C24 . . 1.403(10) y
C23 H23 . . 0.95 ?
C24 C25 . . 1.375(12) y
C24 H24 . . 0.95 ?
C25 C26 . . 1.403(12) y
C25 H25 . . 0.95 ?
C26 H26 . . 0.95 ?
C211 C216 . . 1.531(10) y
C211 C215 . . 1.534(11) y
C211 C212 . . 1.564(12) y
C212 C213 . . 1.523(13) y
C212 H21a . . 0.99 ?
C212 H21b . . 0.99 ?
C213 C214 . . 1.524(12) y
C213 H21c . . 0.99 ?
C213 H21d . . 0.99 ?
C214 C217 . . 1.532(12) y
C214 H214 . . 1 ?
C215 H21e . . 0.98 ?
C215 H21f . . 0.98 ?
C215 H21g . . 0.98 ?
C216 H21h . . 0.98 ?
C216 H21i . . 0.98 ?
C216 H21j . . 0.98 ?
C217 H21k . . 0.98 ?
C217 H21l . . 0.98 ?
C217 H21m . . 0.98 ?
C221 C225 . . 1.518(11) y
C221 C222 . . 1.540(11) y
C221 H221 . . 1 ?
C222 C223 . . 1.517(12) y
C222 H22a . . 0.99 ?
C222 H22b . . 0.99 ?
C223 C224 . . 1.508(12) y
C223 H22c . . 0.99 ?
C223 H22d . . 0.99 ?
C224 C226 . . 1.538(11) y
C224 H224 . . 1 ?
C225 H22e . . 0.98 ?
C225 H22f . . 0.98 ?
C225 H22g . . 0.98 ?
C226 H22h . . 0.98 ?
C226 H22i . . 0.98 ?
C226 H22j . . 0.98 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O11 P11 C11 C16 . . . . -129.4(6) ?
C114 P11 C11 C16 . . . . -5.3(7) ?
C111 P11 C11 C16 . . . . 100.4(7) ?
O11 P11 C11 C12 . . . . 50.9(7) ?
C114 P11 C11 C12 . . . . 175.1(6) ?
C111 P11 C11 C12 . . . . -79.2(7) ?
C16 C11 C12 C13 . . . . -2.00(11) ?
P11 C11 C12 C13 . . . . 177.6(5) ?
C16 C11 C12 P12 . . . . 179.6(6) ?
P11 C11 C12 P12 . . . . -0.8(9) ?
C124 P12 C12 C13 . . . . -19.9(7) ?
C121 P12 C12 C13 . . . . 74.9(7) ?
C124 P12 C12 C11 . . . . 158.3(6) ?
C121 P12 C12 C11 . . . . -106.9(6) ?
C11 C12 C13 C14 . . . . 2.30(11) ?
P12 C12 C13 C14 . . . . -179.5(6) ?
C12 C13 C14 C15 . . . . -0.80(11) ?
C13 C14 C15 C16 . . . . -1.10(11) ?
C14 C15 C16 C11 . . . . 1.30(12) ?
C12 C11 C16 C15 . . . . 0.30(12) ?
P11 C11 C16 C15 . . . . -179.3(6) ?
O11 P11 C111 C116 . . . . -0.1(6) ?
C11 P11 C111 C116 . . . . 129.6(5) ?
C114 P11 C111 C116 . . . . -116.9(6) ?
O11 P11 C111 C115 . . . . -124.2(6) ?
C11 P11 C111 C115 . . . . 5.5(7) ?
C114 P11 C111 C115 . . . . 119.0(6) ?
O11 P11 C111 C112 . . . . 116.9(5) ?
C11 P11 C111 C112 . . . . -113.4(5) ?
C114 P11 C111 C112 . . . . 0.0(6) ?
C116 C111 C112 C113 . . . . 87.0(8) ?
C115 C111 C112 C113 . . . . -150.6(7) ?
P11 C111 C112 C113 . . . . -29.0(7) ?
C111 C112 C113 C114 . . . . 51.8(8) ?
C112 C113 C114 C117 . . . . -169.7(7) ?
C112 C113 C114 P11 . . . . -47.2(7) ?
O11 P11 C114 C117 . . . . 32.7(7) ?
C11 P11 C114 C117 . . . . -93.0(7) ?
C111 P11 C114 C117 . . . . 152.2(6) ?
O11 P11 C114 C113 . . . . -92.6(6) ?
C11 P11 C114 C113 . . . . 141.7(5) ?
C111 P11 C114 C113 . . . . 26.8(6) ?
C12 P12 C121 C125 . . . . 50.3(7) ?
C124 P12 C121 C125 . . . . 154.4(7) ?
C12 P12 C121 C122 . . . . -77.9(6) ?
C124 P12 C121 C122 . . . . 26.2(6) ?
C125 C121 C122 C123 . . . . -171.1(7) ?
P12 C121 C122 C123 . . . . -41.7(8) ?
C121 C122 C123 C124 . . . . 39.6(1) ?
C122 C123 C124 C126 . . . . -139.3(8) ?
C122 C123 C124 P12 . . . . -18.6(9) ?
C12 P12 C124 C126 . . . . -140.2(6) ?
C121 P12 C124 C126 . . . . 118.0(6) ?
C12 P12 C124 C123 . . . . 96.9(6) ?
C121 P12 C124 C123 . . . . -4.9(7) ?
O21 P21 C21 C22 . . . . 42.9(7) ?
C214 P21 C21 C22 . . . . 167.3(6) ?
C211 P21 C21 C22 . . . . -87.3(7) ?
O21 P21 C21 C26 . . . . -131.8(7) ?
C214 P21 C21 C26 . . . . -7.4(8) ?
C211 P21 C21 C26 . . . . 97.9(7) ?
C26 C21 C22 C23 . . . . 1.00(12) ?
P21 C21 C22 C23 . . . . -173.7(6) ?
C26 C21 C22 P22 . . . . -176.1(6) ?
P21 C21 C22 P22 . . . . 9.2(9) ?
C224 P22 C22 C21 . . . . 153.1(6) ?
C221 P22 C22 C21 . . . . -110.5(6) ?
C224 P22 C22 C23 . . . . -23.9(8) ?
C221 P22 C22 C23 . . . . 72.5(7) ?
C21 C22 C23 C24 . . . . -1.30(12) ?
P22 C22 C23 C24 . . . . 175.7(6) ?
C22 C23 C24 C25 . . . . 1.00(13) ?
C23 C24 C25 C26 . . . . -0.40(13) ?
C24 C25 C26 C21 . . . . 0.20(13) ?
C22 C21 C26 C25 . . . . -0.50(13) ?
P21 C21 C26 C25 . . . . 174.4(7) ?
O21 P21 C211 C216 . . . . -11.6(7) ?
C214 P21 C211 C216 . . . . -128.9(6) ?
C21 P21 C211 C216 . . . . 116.9(6) ?
O21 P21 C211 C215 . . . . -133.9(6) ?
C214 P21 C211 C215 . . . . 108.8(6) ?
C21 P21 C211 C215 . . . . -5.5(7) ?
O21 P21 C211 C212 . . . . 106.3(5) ?
C214 P21 C211 C212 . . . . -11.0(6) ?
C21 P21 C211 C212 . . . . -125.3(5) ?
C216 C211 C212 C213 . . . . 98.1(8) ?
C215 C211 C212 C213 . . . . -140.9(7) ?
P21 C211 C212 C213 . . . . -19.1(7) ?
C211 C212 C213 C214 . . . . 48.3(8) ?
C212 C213 C214 C217 . . . . -176.3(6) ?
C212 C213 C214 P21 . . . . -52.8(7) ?
O21 P21 C214 C213 . . . . -82.2(6) ?
C21 P21 C214 C213 . . . . 154.1(5) ?
C211 P21 C214 C213 . . . . 37.1(6) ?
O21 P21 C214 C217 . . . . 43.3(7) ?
C21 P21 C214 C217 . . . . -80.5(6) ?
C211 P21 C214 C217 . . . . 162.5(6) ?
C22 P22 C221 C225 . . . . 32.1(7) ?
C224 P22 C221 C225 . . . . 138.6(6) ?
C22 P22 C221 C222 . . . . -94.9(5) ?
C224 P22 C221 C222 . . . . 11.6(6) ?
C225 C221 C222 C223 . . . . -164.8(7) ?
P22 C221 C222 C223 . . . . -36.2(7) ?
C221 C222 C223 C224 . . . . 51.0(9) ?
C222 C223 C224 C226 . . . . -161.6(7) ?
C222 C223 C224 P22 . . . . -40.0(8) ?
C22 P22 C224 C223 . . . . 119.7(6) ?
C221 P22 C224 C223 . . . . 15.6(6) ?
C22 P22 C224 C226 . . . . -115.9(6) ?
C221 P22 C224 C226 . . . . 140.0(6) ?
