#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:50:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178408 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/29/4022930.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_4022930
loop_
_publ_author_name
'Gloria Ruiz-Gómez'
'María José Iglesias'
'Manuel Serrano-Ruiz'
'Santiago García-Granda'
'Andrés Francesch'
'Fernando López-Ortiz'
'Carmen Cuevas'
_publ_section_title
;
 Double Dearomatization of Bis(diphenylphosphinamides)
 through Anionic Cyclization. A Facile Route of Accessing
 Multifunctional Systems with Antitumor Properties
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3790
_journal_page_last               3799
_journal_paper_doi               10.1021/jo070276q
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C40 H38 N2 O2 P2'
_chemical_formula_weight         640.66
_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                 111.2240(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.1159(6)
_cell_length_b                   13.2673(7)
_cell_length_c                   11.7064(7)
_cell_measurement_reflns_used    701
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      35.417
_cell_measurement_theta_min      4.833
_cell_volume                     1609.34(15)
_computing_cell_refinement       'Bruker APEX'
_computing_data_collection       'Bruker APEX'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7411
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             676
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         2318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0417
_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)+(0.0572P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                1896
_reflns_number_total             2318
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070276qsi20070208_111333.cif
_cod_data_source_block           c:\sir97\fernando\g740p\g740pm
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022930
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
P1 P 0.71488(6) 0.84495(4) 0.04119(6) 0.0293(2) Uani 1 1 d
O1 O 0.64373(16) 0.75110(11) -0.00943(15) 0.0380(5) Uani 1 1 d
N1 N 0.64597(18) 0.92999(13) 0.10425(18) 0.0275(5) Uani 1 1 d
C1 C 0.6735(2) 1.02692(18) 0.2934(2) 0.0325(6) Uani 1 1 d
C2 C 0.6288(3) 1.0226(3) 0.3897(3) 0.0478(8) Uani 1 1 d
C3 C 0.6056(3) 1.1102(3) 0.4414(3) 0.0661(10) Uani 1 1 d
C4 C 0.6236(3) 1.2012(3) 0.3985(4) 0.0706(12) Uani 1 1 d
C5 C 0.6680(3) 1.2082(2) 0.3012(3) 0.0576(9) Uani 1 1 d
C6 C 0.6945(3) 1.1209(2) 0.2515(3) 0.0391(7) Uani 1 1 d
C7 C 0.7527(2) 0.91133(16) -0.0753(2) 0.0282(6) Uani 1 1 d
C8 C 0.8252(3) 0.99971(19) -0.0488(3) 0.0368(7) Uani 1 1 d
C9 C 0.8549(3) 1.0490(2) -0.1384(3) 0.0403(7) Uani 1 1 d
C10 C 0.8120(3) 1.0129(2) -0.2565(3) 0.0391(7) Uani 1 1 d
C11 C 0.7371(3) 0.9268(2) -0.2845(3) 0.0422(7) Uani 1 1 d
C12 C 0.7092(3) 0.87588(19) -0.1943(2) 0.0358(7) Uani 1 1 d
C13 C 0.8537(2) 0.83433(16) 0.1796(2) 0.0284(6) Uani 1 1 d
C14 C 0.9353(2) 0.7577(2) 0.2096(3) 0.0351(7) Uani 1 1 d
C15 C 1.0315(3) 0.7440(2) 0.3355(3) 0.0430(7) Uani 1 1 d
C16 C 1.0091(3) 0.8109(2) 0.4275(3) 0.0416(7) Uani 1 1 d
C17 C 0.9245(3) 0.8848(2) 0.3988(2) 0.0376(7) Uani 1 1 d
C18 C 0.8472(2) 0.91300(18) 0.2690(2) 0.0317(6) Uani 1 1 d
C19 C 0.7013(2) 0.93087(17) 0.2402(2) 0.0301(6) Uani 1 1 d
C20 C 0.5095(2) 0.95440(18) 0.0418(3) 0.0307(6) Uani 1 1 d
H18 H 0.883(2) 0.9809(17) 0.254(2) 0.032(6) Uiso 1 1 d
H20A H 0.466(2) 0.9021(17) -0.007(2) 0.034(7) Uiso 1 1 d
H19 H 0.667(2) 0.8783(16) 0.2742(19) 0.023(6) Uiso 1 1 d
H15B H 1.116(3) 0.7569(17) 0.336(2) 0.043(8) Uiso 1 1 d
H16 H 1.059(2) 0.8017(17) 0.506(2) 0.030(7) Uiso 1 1 d
H14 H 0.928(2) 0.7079(16) 0.154(2) 0.026(6) Uiso 1 1 d
H6 H 0.725(2) 1.1216(16) 0.190(2) 0.027(7) Uiso 1 1 d
H10 H 0.833(2) 1.0399(15) -0.314(2) 0.023(6) Uiso 1 1 d
H15A H 1.029(2) 0.6804(19) 0.355(2) 0.042(8) Uiso 1 1 d
H12 H 0.664(2) 0.8156(18) -0.210(2) 0.044(7) Uiso 1 1 d
H17 H 0.914(2) 0.9276(17) 0.456(2) 0.037(7) Uiso 1 1 d
H8 H 0.855(2) 1.0214(18) 0.027(2) 0.036(7) Uiso 1 1 d
H5 H 0.674(2) 1.270(2) 0.271(2) 0.044(8) Uiso 1 1 d
H20B H 0.471(2) 0.9659(16) 0.104(2) 0.035(7) Uiso 1 1 d
H11 H 0.707(2) 0.9017(17) -0.364(2) 0.039(7) Uiso 1 1 d
H4 H 0.607(3) 1.250(2) 0.433(3) 0.061(10) Uiso 1 1 d
H9 H 0.905(2) 1.1091(18) -0.117(2) 0.034(7) Uiso 1 1 d
H2 H 0.610(3) 0.953(2) 0.420(3) 0.088(11) Uiso 1 1 d
H3 H 0.576(3) 1.110(2) 0.507(3) 0.078(11) Uiso 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'
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
O1 P1 N1 118.64(10) . .
O1 P1 C13 117.15(10) . .
N1 P1 C13 92.05(10) . .
O1 P1 C7 110.28(11) . .
N1 P1 C7 105.90(10) . .
C13 P1 C7 111.31(11) . .
C20 N1 C19 119.12(19) . .
C20 N1 P1 119.04(17) . .
C19 N1 P1 113.53(15) . .
C2 C1 C6 118.6(3) . .
C2 C1 C19 119.4(2) . .
C6 C1 C19 121.9(2) . .
C3 C2 C1 120.1(3) . .
C3 C2 H2 120.8(18) . .
C1 C2 H2 119.1(18) . .
C4 C3 C2 120.9(3) . .
C4 C3 H3 117(2) . .
C2 C3 H3 122(2) . .
C3 C4 C5 120.4(3) . .
C3 C4 H4 116(2) . .
C5 C4 H4 124(2) . .
C6 C5 C4 118.8(3) . .
C6 C5 H5 122.8(17) . .
C4 C5 H5 118.4(17) . .
C5 C6 C1 121.1(3) . .
C5 C6 H6 122.0(15) . .
C1 C6 H6 116.9(15) . .
C12 C7 C8 118.3(2) . .
C12 C7 P1 120.42(18) . .
C8 C7 P1 121.27(19) . .
C9 C8 C7 120.7(3) . .
C9 C8 H8 120.9(16) . .
C7 C8 H8 118.4(16) . .
C8 C9 C10 120.6(3) . .
C8 C9 H9 118.5(14) . .
C10 C9 H9 120.9(14) . .
C9 C10 C11 119.1(3) . .
C9 C10 H10 122.9(15) . .
C11 C10 H10 117.9(15) . .
C12 C11 C10 120.4(3) . .
C12 C11 H11 119.4(15) . .
C10 C11 H11 120.1(15) . .
C11 C12 C7 120.8(3) . .
C11 C12 H12 122.0(16) . .
C7 C12 H12 117.2(16) . .
C14 C13 C18 123.5(2) . .
C14 C13 P1 125.7(2) . .
C18 C13 P1 109.46(16) . .
C13 C14 C15 122.4(3) . .
C13 C14 H14 119.5(14) . .
C15 C14 H14 117.8(14) . .
C16 C15 C14 113.4(2) . .
C16 C15 H15B 108.0(15) . .
C14 C15 H15B 109.9(16) . .
C16 C15 H15A 110.8(17) . .
C14 C15 H15A 107.3(18) . .
H15B C15 H15A 107(2) . .
C17 C16 C15 123.6(3) . .
C17 C16 H16 118.7(15) . .
C15 C16 H16 117.7(15) . .
C16 C17 C18 122.7(3) . .
C16 C17 H17 122.7(15) . .
C18 C17 H17 114.3(15) . .
C17 C18 C13 112.3(2) . .
C17 C18 C19 115.4(2) . .
C13 C18 C19 105.4(2) . .
C17 C18 H18 106.2(13) . .
C13 C18 H18 112.0(12) . .
C19 C18 H18 105.4(12) . .
N1 C19 C1 112.62(19) . .
N1 C19 C18 103.09(19) . .
C1 C19 C18 113.4(2) . .
N1 C19 H19 111.8(13) . .
C1 C19 H19 106.2(12) . .
C18 C19 H19 109.9(13) . .
N1 C20 C20 112.0(2) . 3_675
N1 C20 H20A 111.0(15) . .
C20 C20 H20A 106.6(15) 3_675 .
N1 C20 H20B 108.2(14) . .
C20 C20 H20B 111.0(13) 3_675 .
H20A C20 H20B 108(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O1 1.4791(16) .
P1 N1 1.6775(19) .
P1 C13 1.793(3) .
P1 C7 1.797(2) .
N1 C20 1.462(3) .
N1 C19 1.484(3) .
C1 C2 1.388(4) .
C1 C6 1.390(4) .
C1 C19 1.499(3) .
C2 C3 1.378(4) .
C2 H2 1.03(3) .
C3 C4 1.351(5) .
C3 H3 0.94(3) .
C4 C5 1.398(5) .
C4 H4 0.82(3) .
C5 C6 1.375(4) .
C5 H5 0.90(2) .
C6 H6 0.90(2) .
C7 C12 1.381(3) .
C7 C8 1.393(3) .
C8 C9 1.374(4) .
C8 H8 0.88(3) .
C9 C10 1.375(4) .
C9 H9 0.95(2) .
C10 C11 1.382(4) .
C10 H10 0.87(2) .
C11 C12 1.379(4) .
C11 H11 0.93(2) .
C12 H12 0.93(2) .
C13 C14 1.322(3) .
C13 C18 1.498(3) .
C14 C15 1.487(4) .
C14 H14 0.91(2) .
C15 C16 1.485(4) .
C15 H15B 0.95(3) .
C15 H15A 0.88(2) .
C16 C17 1.316(4) .
C16 H16 0.90(2) .
C17 C18 1.498(3) .
C17 H17 0.92(2) .
C18 C19 1.551(3) .
C18 H18 1.02(2) .
C19 H19 0.95(2) .
C20 C20 1.522(5) 3_675
C20 H20A 0.91(2) .
C20 H20B 0.98(2) .
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_4
O1 P1 N1 C20 -43.8(2) .
C13 P1 N1 C20 -166.44(17) .
C7 P1 N1 C20 80.71(18) .
O1 P1 N1 C19 104.31(17) .
C13 P1 N1 C19 -18.36(17) .
C7 P1 N1 C19 -131.21(16) .
C6 C1 C2 C3 0.3(4) .
C19 C1 C2 C3 178.5(3) .
C1 C2 C3 C4 1.1(5) .
C2 C3 C4 C5 -0.8(5) .
C3 C4 C5 C6 -0.9(5) .
C4 C5 C6 C1 2.3(4) .
C2 C1 C6 C5 -2.0(4) .
C19 C1 C6 C5 179.8(3) .
O1 P1 C7 C12 3.7(2) .
N1 P1 C7 C12 -125.8(2) .
C13 P1 C7 C12 135.5(2) .
O1 P1 C7 C8 -176.78(19) .
N1 P1 C7 C8 53.7(2) .
C13 P1 C7 C8 -45.0(2) .
C12 C7 C8 C9 -1.3(4) .
P1 C7 C8 C9 179.1(2) .
C7 C8 C9 C10 1.0(4) .
C8 C9 C10 C11 0.7(4) .
C9 C10 C11 C12 -2.1(4) .
C10 C11 C12 C7 1.7(4) .
C8 C7 C12 C11 0.0(4) .
P1 C7 C12 C11 179.5(2) .
O1 P1 C13 C14 35.2(3) .
N1 P1 C13 C14 159.1(2) .
C7 P1 C13 C14 -93.0(2) .
O1 P1 C13 C18 -131.91(15) .
N1 P1 C13 C18 -8.04(16) .
C7 P1 C13 C18 99.92(17) .
C18 C13 C14 C15 -1.6(4) .
P1 C13 C14 C15 -167.0(2) .
C13 C14 C15 C16 11.8(4) .
C14 C15 C16 C17 -9.1(4) .
C15 C16 C17 C18 -3.8(4) .
C16 C17 C18 C13 13.6(4) .
C16 C17 C18 C19 134.5(3) .
C14 C13 C18 C17 -10.9(3) .
P1 C13 C18 C17 156.49(18) .
C14 C13 C18 C19 -137.4(2) .
P1 C13 C18 C19 30.0(2) .
C20 N1 C19 C1 -51.6(3) .
P1 N1 C19 C1 160.31(16) .
C20 N1 C19 C18 -174.19(19) .
P1 N1 C19 C18 37.8(2) .
C2 C1 C19 N1 133.2(2) .
C6 C1 C19 N1 -48.6(3) .
C2 C1 C19 C18 -110.2(3) .
C6 C1 C19 C18 68.0(3) .
C17 C18 C19 N1 -165.6(2) .
C13 C18 C19 N1 -41.0(2) .
C17 C18 C19 C1 72.4(3) .
C13 C18 C19 C1 -163.05(19) .
C19 N1 C20 C20 120.2(3) 3_675
P1 N1 C20 C20 -93.5(3) 3_675
