#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:50:55 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178919 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/48/4114868.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_4114868
loop_
_publ_author_name
'Natalya V. Timosheva'
'A. Chandrasekaran'
'Roberta O. Day'
'Robert R. Holmes'
_publ_section_title
;
 Conversion of Tricoordinate to Hexacoordinate Phosphorus. Formation of a
 Phosphorane-Phosphatrane System1
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7035
_journal_page_last               7040
_journal_paper_doi               10.1021/ja012579m
_journal_volume                  124
_journal_year                    2002
_chemical_formula_sum            'C42 H64 N O4 P'
_chemical_formula_weight         677.91
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.1372(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4625(2)
_cell_length_b                   22.5793(4)
_cell_length_c                   13.7246(3)
_cell_measurement_reflns_used    7030
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      4.08
_cell_volume                     4007.54(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Nonius KappaCCD area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13167
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         4.08
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9480
_exptl_absorpt_correction_T_min  0.9331
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         7025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0553
_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)+(0.0586P)²+2.1327P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1450
_reflns_number_gt                5266
_reflns_number_total             7025
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja012579m_2.cif
_cod_data_source_block           ntp4(2)
_cod_database_code               4114868
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
P P 0.67971(4) 0.22147(3) 0.35997(4) 0.03704(17) Uani 1 1 d .
H1 H 0.6531(15) 0.1869(9) 0.4276(14) 0.033(5) Uiso 1 1 d .
O1 O 0.72938(11) 0.26753(7) 0.29022(10) 0.0391(4) Uani 1 1 d .
O2 O 0.62661(11) 0.28288(7) 0.40332(10) 0.0418(4) Uani 1 1 d .
O3 O 0.74654(12) 0.16333(7) 0.32210(11) 0.0437(4) Uani 1 1 d .
N N 0.80446(14) 0.23575(8) 0.48739(13) 0.0400(4) Uani 1 1 d .
C1 C 0.82361(16) 0.29452(10) 0.30350(16) 0.0389(5) Uani 1 1 d .
C2 C 0.85554(17) 0.30844(10) 0.21718(17) 0.0437(5) Uani 1 1 d .
C3 C 0.95150(19) 0.33657(12) 0.2350(2) 0.0555(7) Uani 1 1 d .
H3 H 0.9749 0.3462 0.1793 0.067 Uiso 1 1 calc R
C4 C 1.01392(19) 0.35101(12) 0.3309(2) 0.0592(7) Uani 1 1 d .
C5 C 0.97840(19) 0.33763(11) 0.4125(2) 0.0533(6) Uani 1 1 d .
H5 H 1.0186 0.3472 0.4774 0.064 Uiso 1 1 calc R
C6 C 0.88330(17) 0.30998(10) 0.40042(17) 0.0435(5) Uani 1 1 d .
C7 C 0.84520(18) 0.29746(11) 0.49032(17) 0.0453(6) Uani 1 1 d .
H7A H 0.7908 0.3253 0.4919 0.054 Uiso 1 1 calc R
H7B H 0.9013 0.3028 0.5517 0.054 Uiso 1 1 calc R
C8 C 0.76594(18) 0.22456(11) 0.57732(16) 0.0458(6) Uani 1 1 d .
H8A H 0.8222 0.2310 0.6382 0.055 Uiso 1 1 calc R
H8B H 0.7453 0.1834 0.5768 0.055 Uiso 1 1 calc R
C9 C 0.67581(17) 0.26308(10) 0.58201(16) 0.0417(5) Uani 1 1 d .
C10 C 0.65784(19) 0.27130(11) 0.67650(17) 0.0485(6) Uani 1 1 d .
H10 H 0.6983 0.2510 0.7325 0.058 Uiso 1 1 calc R
C11 C 0.58150(19) 0.30876(11) 0.68850(17) 0.0486(6) Uani 1 1 d .
C12 C 0.52644(18) 0.34043(11) 0.60414(17) 0.0462(6) Uani 1 1 d .
H12 H 0.4774 0.3675 0.6125 0.055 Uiso 1 1 calc R
C13 C 0.53998(16) 0.33421(10) 0.50806(16) 0.0401(5) Uani 1 1 d .
C14 C 0.61322(16) 0.29165(10) 0.49706(15) 0.0386(5) Uani 1 1 d .
C15 C 0.89188(17) 0.19402(11) 0.49279(18) 0.0464(6) Uani 1 1 d .
H15A H 0.9256 0.2049 0.4414 0.056 Uiso 1 1 calc R
H15B H 0.9422 0.1979 0.5585 0.056 Uiso 1 1 calc R
C16 C 0.85784(18) 0.13102(11) 0.47751(17) 0.0473(6) Uani 1 1 d .
C17 C 0.9012(2) 0.08719(13) 0.54779(19) 0.0584(7) Uani 1 1 d .
H17 H 0.9464 0.0977 0.6099 0.070 Uiso 1 1 calc R
C18 C 0.8779(2) 0.02866(13) 0.5261(2) 0.0654(8) Uani 1 1 d .
C19 C 0.8149(2) 0.01531(12) 0.4300(2) 0.0658(8) Uani 1 1 d .
H19 H 0.8014 -0.0245 0.4140 0.079 Uiso 1 1 calc R
C20 C 0.7701(2) 0.05700(11) 0.35518(19) 0.0525(6) Uani 1 1 d .
C21 C 0.78812(18) 0.11669(10) 0.38478(17) 0.0446(6) Uani 1 1 d .
C22 C 0.56103(17) 0.21213(11) 0.25551(16) 0.0428(5) Uani 1 1 d .
H22A H 0.5366 0.2506 0.2275 0.051 Uiso 1 1 calc R
H22B H 0.5762 0.1887 0.2022 0.051 Uiso 1 1 calc R
C23 C 0.47656(19) 0.18170(12) 0.2918(2) 0.0567(7) Uani 1 1 d .
H23A H 0.4157 0.1774 0.2358 0.085 Uiso 1 1 calc R
H23B H 0.4607 0.2052 0.3437 0.085 Uiso 1 1 calc R
H23C H 0.5002 0.1433 0.3186 0.085 Uiso 1 1 calc R
C24 C 0.78835(19) 0.29535(11) 0.10876(17) 0.0485(6) Uani 1 1 d .
C25 C 0.48050(18) 0.37376(11) 0.41940(18) 0.0481(6) Uani 1 1 d .
C26 C 0.7125(2) 0.03657(12) 0.2472(2) 0.0610(7) Uani 1 1 d .
C27 C 1.1177(2) 0.38067(18) 0.3438(3) 0.0939(12) Uani 1 1 d .
H27A H 1.1290 0.3866 0.2784 0.141 Uiso 0.50 1 calc PR
H27B H 1.1715 0.3560 0.3844 0.141 Uiso 0.50 1 calc PR
H27C H 1.1183 0.4182 0.3767 0.141 Uiso 0.50 1 calc PR
H27D H 1.1502 0.3873 0.4146 0.141 Uiso 0.50 1 calc PR
H27E H 1.1078 0.4179 0.3086 0.141 Uiso 0.50 1 calc PR
H27F H 1.1609 0.3556 0.3163 0.141 Uiso 0.50 1 calc PR
C28 C 0.5590(2) 0.31628(15) 0.78958(19) 0.0683(8) Uani 1 1 d .
H28A H 0.5035 0.3440 0.7827 0.102 Uiso 0.50 1 calc PR
H28B H 0.6197 0.3308 0.8385 0.102 Uiso 0.50 1 calc PR
H28C H 0.5397 0.2788 0.8117 0.102 Uiso 0.50 1 calc PR
H28D H 0.6051 0.2917 0.8393 0.102 Uiso 0.50 1 calc PR
H28E H 0.4889 0.3049 0.7835 0.102 Uiso 0.50 1 calc PR
H28F H 0.5689 0.3570 0.8103 0.102 Uiso 0.50 1 calc PR
C29 C 0.9222(3) -0.01984(15) 0.6025(3) 0.0917(11) Uani 1 1 d .
H29A H 0.8978 -0.0577 0.5737 0.137 Uiso 0.50 1 calc PR
H29B H 0.9004 -0.0136 0.6627 0.137 Uiso 0.50 1 calc PR
H29C H 0.9963 -0.0189 0.6195 0.137 Uiso 0.50 1 calc PR
H29D H 0.9652 -0.0025 0.6635 0.137 Uiso 0.50 1 calc PR
H29E H 0.9626 -0.0465 0.5746 0.137 Uiso 0.50 1 calc PR
H29F H 0.8667 -0.0412 0.6177 0.137 Uiso 0.50 1 calc PR
C30 C 0.6842(2) 0.32792(13) 0.09018(19) 0.0598(7) Uani 1 1 d .
H30A H 0.6963 0.3697 0.0988 0.090 Uiso 1 1 calc R
H30B H 0.6489 0.3142 0.1378 0.090 Uiso 1 1 calc R
H30C H 0.6425 0.3201 0.0224 0.090 Uiso 1 1 calc R
C31 C 0.7684(2) 0.22892(12) 0.0941(2) 0.0612(7) Uani 1 1 d .
H31A H 0.8331 0.2085 0.1053 0.092 Uiso 1 1 calc R
H31B H 0.7265 0.2215 0.0263 0.092 Uiso 1 1 calc R
H31C H 0.7331 0.2150 0.1417 0.092 Uiso 1 1 calc R
C32 C 0.8403(3) 0.31575(18) 0.0284(2) 0.0840(10) Uani 1 1 d .
H32A H 0.8538 0.3575 0.0355 0.126 Uiso 1 1 calc R
H32B H 0.7954 0.3077 -0.0380 0.126 Uiso 1 1 calc R
H32C H 0.9043 0.2948 0.0373 0.126 Uiso 1 1 calc R
C33 C 0.4086(2) 0.33625(13) 0.3361(2) 0.0673(8) Uani 1 1 d .
H33A H 0.3612 0.3148 0.3639 0.101 Uiso 1 1 calc R
H33B H 0.4489 0.3088 0.3095 0.101 Uiso 1 1 calc R
H33C H 0.3705 0.3616 0.2825 0.101 Uiso 1 1 calc R
C34 C 0.5567(2) 0.40786(14) 0.3758(2) 0.0730(8) Uani 1 1 d .
H34A H 0.5190 0.4323 0.3207 0.109 Uiso 1 1 calc R
H34B H 0.5988 0.3803 0.3516 0.109 Uiso 1 1 calc R
H34C H 0.6000 0.4323 0.4277 0.109 Uiso 1 1 calc R
C35 C 0.4126(2) 0.41944(14) 0.4537(2) 0.0722(8) Uani 1 1 d .
H35A H 0.3637 0.3993 0.4813 0.108 Uiso 1 1 calc R
H35B H 0.3762 0.4429 0.3966 0.108 Uiso 1 1 calc R
H35C H 0.4554 0.4447 0.5046 0.108 Uiso 1 1 calc R
C36 C 0.6002(3) 0.0526(2) 0.2211(4) 0.1341(19) Uani 1 1 d .
H36A H 0.5934 0.0944 0.2293 0.201 Uiso 1 1 calc R
H36B H 0.5681 0.0318 0.2653 0.201 Uiso 1 1 calc R
H36C H 0.5673 0.0417 0.1521 0.201 Uiso 1 1 calc R
C37 C 0.7223(3) -0.03013(14) 0.2324(3) 0.0997(12) Uani 1 1 d .
H37A H 0.7941 -0.0409 0.2501 0.150 Uiso 1 1 calc R
H37B H 0.6903 -0.0402 0.1628 0.150 Uiso 1 1 calc R
H37C H 0.6887 -0.0512 0.2751 0.150 Uiso 1 1 calc R
C38 C 0.7633(4) 0.06579(17) 0.1730(2) 0.1098(15) Uani 1 1 d .
H38A H 0.8353 0.0555 0.1908 0.165 Uiso 1 1 calc R
H38B H 0.7564 0.1080 0.1761 0.165 Uiso 1 1 calc R
H38C H 0.7302 0.0523 0.1055 0.165 Uiso 1 1 calc R
C1S C 0.2814(6) 0.0586(3) 0.1418(7) 0.206(4) Uani 1 1 d .
H1S1 H 0.2509 0.0960 0.1166 0.309 Uiso 1 1 calc R
H1S2 H 0.2407 0.0270 0.1037 0.309 Uiso 1 1 calc R
H1S3 H 0.3504 0.0566 0.1350 0.309 Uiso 1 1 calc R
C2S C 0.2846(8) 0.0528(3) 0.2459(8) 0.222(4) Uani 1 1 d .
H2S1 H 0.3277 0.0843 0.2835 0.266 Uiso 1 1 calc R
H2S2 H 0.2153 0.0588 0.2521 0.266 Uiso 1 1 calc R
O1S O 0.3200(5) 0.0010(2) 0.2896(5) 0.208(2) Uani 1 1 d .
C3S C 0.3591(8) -0.0039(5) 0.3879(8) 0.216(4) Uani 1 1 d .
H3S1 H 0.3106 0.0135 0.4204 0.259 Uiso 1 1 calc R
H3S2 H 0.4220 0.0195 0.4076 0.259 Uiso 1 1 calc R
C4S C 0.3834(7) -0.0638(4) 0.4280(6) 0.215(4) Uani 1 1 d .
H4S1 H 0.4117 -0.0620 0.5003 0.322 Uiso 1 1 calc R
H4S2 H 0.4330 -0.0815 0.3983 0.322 Uiso 1 1 calc R
H4S3 H 0.3215 -0.0873 0.4117 0.322 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 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
H1 P O1 171.0(8) y
H1 P O2 90.8(8) y
H1 P O3 91.6(8) y
H1 P C22 97.6(8) y
H1 P N 79.4(8) y
O1 P O2 88.15(8) y
O1 P O3 88.63(8) y
O1 P C22 91.38(9) y
O1 P N 91.54(7) y
O2 P O3 173.64(8) y
O2 P C22 90.43(9) y
O2 P N 84.36(7) y
O3 P C22 95.13(9) y
O3 P N 90.25(7) y
C22 P N 173.94(9) y
C1 O1 P 134.52(13) y
C14 O2 P 127.87(14) y
C21 O3 P 122.79(14) y
C8 N C15 107.66(17) ?
C8 N C7 110.25(17) ?
C15 N C7 107.99(18) ?
C8 N P 106.52(13) ?
C15 N P 112.58(13) ?
C7 N P 111.77(13) ?
O1 C1 C6 120.27(19) ?
O1 C1 C2 118.41(18) ?
C6 C1 C2 121.3(2) ?
C3 C2 C1 116.0(2) ?
C3 C2 C24 121.5(2) ?
C1 C2 C24 122.5(2) ?
C4 C3 C2 124.0(2) ?
C5 C4 C3 117.8(2) ?
C5 C4 C27 121.5(3) ?
C3 C4 C27 120.7(3) ?
C4 C5 C6 121.4(2) ?
C5 C6 C1 119.5(2) ?
C5 C6 C7 120.3(2) ?
C1 C6 C7 120.2(2) ?
C6 C7 N 111.30(18) ?
N C8 C9 114.05(18) ?
C14 C9 C10 119.7(2) ?
C14 C9 C8 122.55(19) ?
C10 C9 C8 117.7(2) ?
C11 C10 C9 121.4(2) ?
C10 C11 C12 117.4(2) ?
C10 C11 C28 121.8(2) ?
C12 C11 C28 120.8(2) ?
C11 C12 C13 124.1(2) ?
C12 C13 C14 116.7(2) ?
C12 C13 C25 121.0(2) ?
C14 C13 C25 122.25(19) ?
O2 C14 C9 121.0(2) ?
O2 C14 C13 118.60(19) ?
C9 C14 C13 120.19(19) ?
C16 C15 N 112.81(19) ?
C17 C16 C21 120.9(2) ?
C17 C16 C15 121.8(2) ?
C21 C16 C15 116.9(2) ?
C18 C17 C16 120.5(2) ?
C17 C18 C19 117.2(2) ?
C17 C18 C29 121.5(3) ?
C19 C18 C29 121.2(3) ?
C18 C19 C20 125.1(3) ?
C19 C20 C21 115.3(2) ?
C19 C20 C26 120.2(2) ?
C21 C20 C26 124.4(2) ?
O3 C21 C16 116.5(2) ?
O3 C21 C20 123.0(2) ?
C16 C21 C20 120.3(2) ?
C23 C22 P 111.26(16) ?
C31 C24 C32 107.4(2) ?
C31 C24 C2 110.5(2) ?
C32 C24 C2 112.0(2) ?
C31 C24 C30 109.2(2) ?
C32 C24 C30 108.3(2) ?
C2 C24 C30 109.4(2) ?
C34 C25 C33 109.8(2) ?
C34 C25 C35 107.6(2) ?
C33 C25 C35 107.0(2) ?
C34 C25 C13 110.0(2) ?
C33 C25 C13 110.5(2) ?
C35 C25 C13 111.7(2) ?
C36 C26 C38 110.2(3) ?
C36 C26 C37 108.9(3) ?
C38 C26 C37 105.4(3) ?
C36 C26 C20 111.3(3) ?
C38 C26 C20 108.3(2) ?
C37 C26 C20 112.6(2) ?
O1S C2S C1S 115.9(7) ?
C3S O1S C2S 121.8(8) ?
O1S C3S C4S 116.7(8) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P H1 1.34(2) y
P O1 1.6736(16) y
P O2 1.7390(16) y
P O3 1.7501(16) y
P C22 1.838(2) y
P N 2.0857(18) y
O1 C1 1.373(3) ?
O2 C14 1.362(2) ?
O3 C21 1.376(3) ?
N C8 1.487(3) ?
N C15 1.493(3) ?
N C7 1.494(3) ?
C1 C6 1.394(3) ?
C1 C2 1.404(3) ?
C2 C3 1.399(3) ?
C2 C24 1.540(3) ?
C3 C4 1.389(4) ?
C4 C5 1.369(4) ?
C4 C27 1.514(4) ?
C5 C6 1.392(3) ?
C6 C7 1.489(3) ?
C8 C9 1.509(3) ?
C9 C14 1.393(3) ?
C9 C10 1.396(3) ?
C10 C11 1.376(3) ?
C11 C12 1.387(3) ?
C11 C28 1.509(3) ?
C12 C13 1.388(3) ?
C13 C14 1.415(3) ?
C13 C25 1.542(3) ?
C15 C16 1.491(3) ?
C16 C17 1.392(3) ?
C16 C21 1.393(3) ?
C17 C18 1.372(4) ?
C18 C19 1.389(4) ?
C18 C29 1.519(4) ?
C19 C20 1.400(4) ?
C20 C21 1.409(3) ?
C20 C26 1.539(4) ?
C22 C23 1.525(3) ?
C24 C31 1.527(4) ?
C24 C32 1.533(4) ?
C24 C30 1.540(4) ?
C25 C34 1.531(4) ?
C25 C33 1.532(4) ?
C25 C35 1.536(4) ?
C26 C36 1.498(5) ?
C26 C38 1.526(4) ?
C26 C37 1.530(4) ?
C1S C2S 1.423(9) ?
C2S O1S 1.340(8) ?
O1S C3S 1.309(8) ?
C3S C4S 1.463(10) ?
