#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:41:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178529 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/34/4063421.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_4063421
loop_
_publ_author_name
'Panichakul, Duanghathai'
'Mathey, François'
_publ_section_title
;
 Serendipitous Discovery of a Phosphirene--Phosphindole Rearrangement
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              348
_journal_page_last               351
_journal_paper_doi               10.1021/om100990r
_journal_volume                  30
_journal_year                    2011
_chemical_formula_moiety         'C25 H24 N O5 P W'
_chemical_formula_sum            'C25 H24 N O5 P W'
_chemical_formula_weight         633.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 127.4470(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.1263(3)
_cell_length_b                   9.4786(2)
_cell_length_c                   20.0072(3)
_cell_measurement_reflns_used    9799
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      43.03
_cell_measurement_theta_min      3.36
_cell_volume                     2427.95(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            64898
_diffrn_reflns_theta_full        43.48
_diffrn_reflns_theta_max         43.48
_diffrn_reflns_theta_min         3.35
_exptl_absorpt_coefficient_mu    4.859
_exptl_absorpt_correction_T_max  0.3235
_exptl_absorpt_correction_T_min  0.2467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.30
_refine_diff_density_max         2.642
_refine_diff_density_min         -1.576
_refine_diff_density_rms         0.149
_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     302
_refine_ls_number_reflns         18315
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0252
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0212P)²+0.5263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0503
_refine_ls_wR_factor_ref         0.0556
_reflns_number_gt                14117
_reflns_number_total             18315
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100990r_si_002.cif
_cod_data_source_block           mat76s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1673 2011-04-08 12:14:43Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4063421
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
W1 W 0.338957(4) 0.299346(6) 0.929536(3) 0.01234(1) Uani 1 1 d . . .
C1 C 0.46357(11) 0.29342(16) 1.05433(8) 0.0169(2) Uani 1 1 d . . .
C2 C 0.32787(10) 0.51362(16) 0.93074(8) 0.0164(2) Uani 1 1 d . . .
C3 C 0.21659(12) 0.30229(16) 0.80394(9) 0.0184(2) Uani 1 1 d . . .
C4 C 0.35698(11) 0.08698(17) 0.92318(9) 0.0191(2) Uani 1 1 d . . .
C5 C 0.43623(11) 0.33402(16) 0.90107(8) 0.0167(2) Uani 1 1 d . . .
C6 C 0.07639(10) 0.31679(13) 0.86962(7) 0.01288(19) Uani 1 1 d . . .
C7 C 0.03894(11) 0.44086(15) 0.82362(8) 0.0156(2) Uani 1 1 d . . .
H7 H 0.0839 0.5194 0.8393 0.019 Uiso 1 1 calc R . .
C8 C -0.06609(11) 0.44827(16) 0.75380(8) 0.0173(2) Uani 1 1 d . . .
H8 H -0.0935 0.5329 0.7220 0.021 Uiso 1 1 calc R . .
C9 C -0.13076(11) 0.33160(17) 0.73079(8) 0.0180(2) Uani 1 1 d . . .
H9 H -0.2018 0.3369 0.6825 0.022 Uiso 1 1 calc R . .
C10 C -0.09293(10) 0.20760(15) 0.77735(8) 0.0160(2) Uani 1 1 d . . .
H10 H -0.1379 0.1289 0.7611 0.019 Uiso 1 1 calc R . .
C11 C 0.01180(10) 0.19933(14) 0.84822(7) 0.01274(18) Uani 1 1 d . . .
C12 C 0.06296(10) 0.08037(14) 0.90451(7) 0.01352(19) Uani 1 1 d . . .
H12 H 0.0272 -0.0049 0.8968 0.016 Uiso 1 1 calc R . .
C13 C 0.16642(9) 0.09920(14) 0.96962(7) 0.01237(18) Uani 1 1 d . . .
C14 C 0.33937(11) 0.05252(17) 1.10313(8) 0.0186(2) Uani 1 1 d . . .
H14 H 0.3525 0.1443 1.0864 0.022 Uiso 1 1 calc R . .
C15 C 0.42294(13) -0.0500(2) 1.11983(11) 0.0273(3) Uani 1 1 d . . .
H15A H 0.4201 -0.1365 1.1452 0.041 Uiso 1 1 calc R . .
H15B H 0.4920 -0.0064 1.1584 0.041 Uiso 1 1 calc R . .
H15C H 0.4105 -0.0729 1.0666 0.041 Uiso 1 1 calc R . .
C16 C 0.34871(15) 0.0807(2) 1.18255(9) 0.0291(3) Uani 1 1 d . . .
H16A H 0.2954 0.1491 1.1700 0.044 Uiso 1 1 calc R . .
H16B H 0.4182 0.1187 1.2265 0.044 Uiso 1 1 calc R . .
H16C H 0.3385 -0.0076 1.2022 0.044 Uiso 1 1 calc R . .
C17 C 0.19903(12) -0.13067(15) 1.04125(9) 0.0176(2) Uani 1 1 d . . .
H17 H 0.2620 -0.1745 1.0932 0.021 Uiso 1 1 calc R . .
C18 C 0.11799(14) -0.11816(19) 1.05718(10) 0.0240(3) Uani 1 1 d . . .
H18A H 0.1386 -0.0430 1.0982 0.036 Uiso 1 1 calc R . .
H18B H 0.1136 -0.2078 1.0793 0.036 Uiso 1 1 calc R . .
H18C H 0.0497 -0.0957 1.0043 0.036 Uiso 1 1 calc R . .
C19 C 0.16427(16) -0.23267(18) 0.96964(11) 0.0266(3) Uani 1 1 d . . .
H19A H 0.0998 -0.1978 0.9174 0.040 Uiso 1 1 calc R . .
H19B H 0.1516 -0.3259 0.9830 0.040 Uiso 1 1 calc R . .
H19C H 0.2190 -0.2399 0.9624 0.040 Uiso 1 1 calc R . .
C20 C 0.22484(10) 0.37716(14) 1.04427(7) 0.01405(19) Uani 1 1 d . . .
C21 C 0.14619(12) 0.37450(17) 1.05426(9) 0.0195(2) Uani 1 1 d . . .
H21 H 0.0855 0.3186 1.0178 0.023 Uiso 1 1 calc R . .
C22 C 0.15703(14) 0.45369(18) 1.11761(10) 0.0237(3) Uani 1 1 d . . .
H22 H 0.1036 0.4518 1.1243 0.028 Uiso 1 1 calc R . .
C23 C 0.24545(14) 0.53538(18) 1.17105(9) 0.0231(3) Uani 1 1 d . . .
H23 H 0.2528 0.5887 1.2146 0.028 Uiso 1 1 calc R . .
C24 C 0.32301(12) 0.53914(17) 1.16079(9) 0.0212(3) Uani 1 1 d . . .
H24 H 0.3834 0.5956 1.1972 0.025 Uiso 1 1 calc R . .
C25 C 0.31288(11) 0.46062(15) 1.09754(8) 0.0165(2) Uani 1 1 d . . .
H25 H 0.3662 0.4639 1.0906 0.020 Uiso 1 1 calc R . .
N1 N 0.23408(9) 0.00652(13) 1.03185(7) 0.01528(18) Uani 1 1 d . . .
O1 O 0.53448(10) 0.28808(14) 1.12387(7) 0.0257(2) Uani 1 1 d . . .
O2 O 0.32385(9) 0.63376(13) 0.92789(7) 0.0244(2) Uani 1 1 d . . .
O3 O 0.15044(11) 0.30712(14) 0.73317(7) 0.0287(3) Uani 1 1 d . . .
O4 O 0.37114(10) -0.02838(14) 0.91801(8) 0.0293(3) Uani 1 1 d . . .
O5 O 0.49146(9) 0.35787(14) 0.88443(7) 0.0229(2) Uani 1 1 d . . .
P1 P 0.20795(3) 0.27463(4) 0.95932(2) 0.01178(5) Uani 1 1 d . . .
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'
W W -0.8490 6.8722 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 W1 C2 85.94(6) . . ?
C5 W1 C1 89.63(6) . . ?
C2 W1 C1 92.36(6) . . ?
C5 W1 C3 89.18(6) . . ?
C2 W1 C3 88.56(6) . . ?
C1 W1 C3 178.44(5) . . ?
C5 W1 C4 88.76(6) . . ?
C2 W1 C4 174.58(5) . . ?
C1 W1 C4 88.72(6) . . ?
C3 W1 C4 90.26(6) . . ?
C5 W1 P1 175.17(4) . . ?
C2 W1 P1 89.87(4) . . ?
C1 W1 P1 92.94(4) . . ?
C3 W1 P1 88.32(4) . . ?
C4 W1 P1 95.39(4) . . ?
O1 C1 W1 178.51(13) . . ?
O2 C2 W1 175.17(12) . . ?
O3 C3 W1 177.32(14) . . ?
O4 C4 W1 175.27(14) . . ?
O5 C5 W1 178.09(14) . . ?
C7 C6 C11 121.91(12) . . ?
C7 C6 P1 128.55(10) . . ?
C11 C6 P1 109.52(9) . . ?
C6 C7 C8 118.76(13) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C9 C8 C7 120.01(12) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 120.99(13) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 119.63(13) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C6 118.68(12) . . ?
C10 C11 C12 126.78(12) . . ?
C6 C11 C12 114.54(11) . . ?
C13 C12 C11 115.35(12) . . ?
C13 C12 H12 122.3 . . ?
C11 C12 H12 122.3 . . ?
N1 C13 C12 128.39(12) . . ?
N1 C13 P1 122.52(10) . . ?
C12 C13 P1 109.02(9) . . ?
N1 C14 C15 111.67(13) . . ?
N1 C14 C16 112.74(12) . . ?
C15 C14 C16 111.66(12) . . ?
N1 C14 H14 106.8 . . ?
C15 C14 H14 106.8 . . ?
C16 C14 H14 106.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 C19 112.93(11) . . ?
N1 C17 C18 113.66(12) . . ?
C19 C17 C18 111.91(14) . . ?
N1 C17 H17 105.9 . . ?
C19 C17 H17 105.9 . . ?
C18 C17 H17 105.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 119.48(12) . . ?
C25 C20 P1 121.32(9) . . ?
C21 C20 P1 119.18(10) . . ?
C22 C21 C20 119.89(14) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C23 C22 C21 120.34(14) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C23 C22 119.86(13) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 120.28(14) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C20 120.14(13) . . ?
C24 C25 H25 119.9 . . ?
C20 C25 H25 119.9 . . ?
C13 N1 C14 120.36(12) . . ?
C13 N1 C17 121.90(11) . . ?
C14 N1 C17 116.35(11) . . ?
C6 P1 C20 103.15(6) . . ?
C6 P1 C13 91.34(6) . . ?
C20 P1 C13 103.51(6) . . ?
C6 P1 W1 112.99(4) . . ?
C20 P1 W1 119.72(4) . . ?
C13 P1 W1 121.32(4) . . ?
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
W1 C5 1.9949(14) . ?
W1 C2 2.0403(16) . ?
W1 C1 2.0430(14) . ?
W1 C3 2.0443(14) . ?
W1 C4 2.0488(16) . ?
W1 P1 2.5307(3) . ?
C1 O1 1.1451(18) . ?
C2 O2 1.140(2) . ?
C3 O3 1.1437(18) . ?
C4 O4 1.135(2) . ?
C5 O5 1.1472(17) . ?
C6 C7 1.3853(18) . ?
C6 C11 1.4019(18) . ?
C6 P1 1.8032(13) . ?
C7 C8 1.396(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.3989(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.4459(18) . ?
C12 C13 1.3672(17) . ?
C12 H12 0.9500 . ?
C13 N1 1.3640(16) . ?
C13 P1 1.8503(13) . ?
C14 N1 1.4704(18) . ?
C14 C15 1.525(2) . ?
C14 C16 1.526(2) . ?
C14 H14 1.0000 . ?
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 N1 1.4749(19) . ?
C17 C19 1.525(2) . ?
C17 C18 1.526(2) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C25 1.3919(19) . ?
C20 C21 1.3991(18) . ?
C20 P1 1.8287(12) . ?
C21 C22 1.390(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.386(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.3895(19) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
