#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:50:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178408 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/29/4022931.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_4022931
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            'C42 H42 N2 O2 P2'
_chemical_formula_weight         668.72
_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                 100.319(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.5460(10)
_cell_length_b                   14.9535(16)
_cell_length_c                   12.3925(12)
_cell_measurement_reflns_used    452
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      37.307
_cell_measurement_theta_min      4.335
_cell_volume                     1740.4(3)
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.1105
_diffrn_reflns_av_sigmaI/netI    0.1865
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9305
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             708
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.804
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3067
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.804
_refine_ls_R_factor_all          0.1372
_refine_ls_R_factor_gt           0.0611
_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0928
_reflns_number_gt                1559
_reflns_number_total             3067
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070276qsi20070208_111405.cif
_cod_data_source_block           c:\sir97\fernando\r571_2w2\r571_2m
_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               4022931
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
P1 P 0.23844(11) 0.19986(8) 0.58613(9) 0.0222(3) Uani 1 1 d .
O2 O 0.2562(2) 0.17436(18) 0.70373(19) 0.0288(8) Uani 1 1 d .
N1 N 0.2266(3) 0.1171(2) 0.4953(2) 0.0225(9) Uani 1 1 d .
C1 C 0.0845(4) 0.0609(3) 0.3191(3) 0.0210(10) Uani 1 1 d .
C2 C -0.0154(4) -0.0036(3) 0.2824(3) 0.0283(11) Uani 1 1 d .
C3 C -0.0130(5) -0.0502(3) 0.1857(4) 0.0369(13) Uani 1 1 d .
C4 C 0.0932(5) -0.0321(3) 0.1273(4) 0.0353(13) Uani 1 1 d .
C5 C 0.1913(5) 0.0335(3) 0.1603(4) 0.0309(12) Uani 1 1 d .
C6 C 0.1864(5) 0.0808(3) 0.2555(3) 0.0267(11) Uani 1 1 d .
C7 C 0.3806(4) 0.2739(2) 0.5657(3) 0.0171(10) Uani 1 1 d .
C8 C 0.3937(4) 0.3065(3) 0.4627(3) 0.0274(11) Uani 1 1 d .
C9 C 0.4953(5) 0.3682(3) 0.4509(4) 0.0341(13) Uani 1 1 d .
C10 C 0.5874(5) 0.3994(3) 0.5424(4) 0.0377(13) Uani 1 1 d .
C11 C 0.5770(4) 0.3686(3) 0.6456(4) 0.0346(13) Uani 1 1 d .
C12 C 0.4750(4) 0.3057(3) 0.6568(4) 0.0290(11) Uani 1 1 d .
C13 C 0.0669(4) 0.2508(3) 0.5256(3) 0.0235(11) Uani 1 1 d .
C14 C -0.0415(5) 0.2323(3) 0.5957(4) 0.0345(13) Uani 1 1 d .
C15 C -0.1752(4) 0.2144(3) 0.5529(4) 0.0332(12) Uani 1 1 d .
C16 C -0.2220(4) 0.2108(3) 0.4344(4) 0.0315(12) Uani 1 1 d .
C17 C -0.1296(4) 0.2099(3) 0.3680(4) 0.0279(11) Uani 1 1 d .
C18 C 0.0286(4) 0.2069(3) 0.4121(3) 0.0218(10) Uani 1 1 d .
H18 H 0.0802 0.2385 0.3598 0.026 Uiso 1 1 calc R
C19 C 0.0824(4) 0.1104(3) 0.4266(3) 0.0199(10) Uani 1 1 d .
C20 C 0.3120(5) 0.0358(3) 0.5198(4) 0.0280(12) Uani 1 1 d .
C21 C 0.4598(5) 0.0437(3) 0.4905(4) 0.0320(13) Uani 1 1 d .
H19 H 0.020(3) 0.0737(19) 0.468(2) 0.003(9) Uiso 1 1 d .
H20B H 0.263(4) -0.012(2) 0.485(3) 0.038(14) Uiso 1 1 d .
H15 H -0.243(3) 0.200(2) 0.598(3) 0.031(11) Uiso 1 1 d .
H3 H -0.084(3) -0.090(2) 0.169(3) 0.020(12) Uiso 1 1 d .
H6 H 0.257(3) 0.126(2) 0.280(3) 0.022(11) Uiso 1 1 d .
H21A H 0.507(4) 0.096(3) 0.539(3) 0.048(14) Uiso 1 1 d .
H17 H -0.157(3) 0.209(2) 0.293(3) 0.029(12) Uiso 1 1 d .
H10 H 0.653(3) 0.444(2) 0.530(2) 0.003(9) Uiso 1 1 d .
H20A H 0.326(4) 0.023(3) 0.604(3) 0.053(14) Uiso 1 1 d .
H5 H 0.270(3) 0.047(2) 0.125(3) 0.032(12) Uiso 1 1 d .
H2 H -0.084(3) -0.018(2) 0.329(3) 0.030(12) Uiso 1 1 d .
H16 H -0.323(3) 0.208(2) 0.407(3) 0.032(12) Uiso 1 1 d .
H12 H 0.463(3) 0.281(2) 0.719(2) 0.022(12) Uiso 1 1 d .
H21B H 0.456(3) 0.059(2) 0.422(3) 0.026(13) Uiso 1 1 d .
H8 H 0.329(3) 0.286(2) 0.400(3) 0.034(13) Uiso 1 1 d .
H9 H 0.514(3) 0.386(2) 0.388(3) 0.027(13) Uiso 1 1 d .
H14 H -0.011(3) 0.241(2) 0.675(3) 0.024(11) Uiso 1 1 d .
H4 H 0.104(3) -0.065(2) 0.067(3) 0.022(11) Uiso 1 1 d .
H13 H 0.089(3) 0.315(2) 0.525(3) 0.019(11) Uiso 1 1 d .
H11 H 0.640(4) 0.388(3) 0.709(3) 0.045(14) 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
O2 P1 N1 117.06(17) .
O2 P1 C7 109.79(16) .
N1 P1 C7 108.85(16) .
O2 P1 C13 116.28(17) .
N1 P1 C13 94.83(17) .
C7 P1 C13 109.02(19) .
C20 N1 C19 119.1(3) .
C20 N1 P1 120.6(3) .
C19 N1 P1 112.4(2) .
C2 C1 C6 118.4(4) .
C2 C1 C19 120.8(4) .
C6 C1 C19 120.7(4) .
C1 C2 C3 121.3(4) .
C1 C2 H2 117(2) .
C3 C2 H2 121(2) .
C4 C3 C2 118.9(4) .
C4 C3 H3 127(2) .
C2 C3 H3 114(2) .
C5 C4 C3 120.9(4) .
C5 C4 H4 117(2) .
C3 C4 H4 122(2) .
C4 C5 C6 119.7(4) .
C4 C5 H5 125(2) .
C6 C5 H5 115(2) .
C5 C6 C1 120.6(4) .
C5 C6 H6 120(2) .
C1 C6 H6 120(2) .
C8 C7 C12 118.1(4) .
C8 C7 P1 122.5(3) .
C12 C7 P1 119.2(3) .
C9 C8 C7 121.1(4) .
C9 C8 H8 120(2) .
C7 C8 H8 119(2) .
C8 C9 C10 120.0(5) .
C8 C9 H9 124(2) .
C10 C9 H9 116(2) .
C11 C10 C9 120.4(5) .
C11 C10 H10 123.2(19) .
C9 C10 H10 116.4(18) .
C12 C11 C10 119.4(4) .
C12 C11 H11 119(2) .
C10 C11 H11 122(2) .
C11 C12 C7 121.1(4) .
C11 C12 H12 125(2) .
C7 C12 H12 114(2) .
C14 C13 C18 112.2(3) .
C14 C13 P1 110.3(3) .
C18 C13 P1 104.2(3) .
C14 C13 H13 110.6(19) .
C18 C13 H13 115.5(19) .
P1 C13 H13 103.4(18) .
C15 C14 C13 121.7(4) .
C15 C14 H14 121.6(19) .
C13 C14 H14 116(2) .
C14 C15 C16 120.8(4) .
C14 C15 H15 121(2) .
C16 C15 H15 118(2) .
C17 C16 C15 120.9(4) .
C17 C16 H16 122(2) .
C15 C16 H16 117(2) .
C16 C17 C18 121.0(4) .
C16 C17 H17 122(2) .
C18 C17 H17 117(2) .
C17 C18 C19 111.3(3) .
C17 C18 C13 112.1(3) .
C19 C18 C13 106.0(3) .
C17 C18 H18 109.1 .
C19 C18 H18 109.1 .
C13 C18 H18 109.1 .
N1 C19 C1 112.1(3) .
N1 C19 C18 105.1(3) .
C1 C19 C18 114.2(3) .
N1 C19 H19 108.6(15) .
C1 C19 H19 106.1(16) .
C18 C19 H19 110.7(17) .
N1 C20 C21 113.0(4) .
N1 C20 H20B 110(2) .
C21 C20 H20B 111(2) .
N1 C20 H20A 109(2) .
C21 C20 H20A 107(2) .
H20B C20 H20A 107(3) .
C21 C21 C20 111.2(5) 3_656
C21 C21 H21A 114(2) 3_656
C20 C21 H21A 104(2) .
C21 C21 H21B 108(3) 3_656
C20 C21 H21B 112(2) .
H21A C21 H21B 108(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O2 1.486(2) .
P1 N1 1.663(3) .
P1 C7 1.804(4) .
P1 C13 1.839(4) .
N1 C20 1.466(5) .
N1 C19 1.486(4) .
C1 C2 1.375(5) .
C1 C6 1.389(5) .
C1 C19 1.528(5) .
C2 C3 1.389(5) .
C2 H2 0.97(3) .
C3 C4 1.374(6) .
C3 H3 0.89(3) .
C4 C5 1.368(6) .
C4 H4 0.91(3) .
C5 C6 1.383(5) .
C5 H5 0.96(3) .
C6 H6 0.97(3) .
C7 C8 1.393(5) .
C7 C12 1.396(5) .
C8 C9 1.365(6) .
C8 H8 0.95(3) .
C9 C10 1.385(6) .
C9 H9 0.87(3) .
C10 C11 1.380(6) .
C10 H10 0.94(3) .
C11 C12 1.379(6) .
C11 H11 0.95(3) .
C12 H12 0.88(3) .
C13 C14 1.492(5) .
C13 C18 1.536(5) .
C13 H13 0.99(3) .
C14 C15 1.318(5) .
C14 H14 0.98(3) .
C15 C16 1.458(5) .
C15 H15 0.95(3) .
C16 C17 1.309(5) .
C16 H16 0.96(3) .
C17 C18 1.512(5) .
C17 H17 0.91(3) .
C18 C19 1.531(5) .
C18 H18 1.0000 .
C19 H19 1.01(3) .
C20 C21 1.523(6) .
C20 H20B 0.92(3) .
C20 H20A 1.04(4) .
C21 C21 1.511(9) 3_656
C21 H21A 1.03(4) .
C21 H21B 0.87(3) .
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
O2 P1 N1 C20 -37.4(4) .
C7 P1 N1 C20 87.8(3) .
C13 P1 N1 C20 -160.2(3) .
O2 P1 N1 C19 111.5(3) .
C7 P1 N1 C19 -123.3(3) .
C13 P1 N1 C19 -11.3(3) .
C6 C1 C2 C3 1.8(7) .
C19 C1 C2 C3 -178.8(4) .
C1 C2 C3 C4 1.3(8) .
C2 C3 C4 C5 -3.2(8) .
C3 C4 C5 C6 1.9(7) .
C4 C5 C6 C1 1.3(7) .
C2 C1 C6 C5 -3.1(6) .
C19 C1 C6 C5 177.6(4) .
O2 P1 C7 C8 178.0(3) .
N1 P1 C7 C8 48.7(4) .
C13 P1 C7 C8 -53.5(4) .
O2 P1 C7 C12 -7.2(4) .
N1 P1 C7 C12 -136.5(3) .
C13 P1 C7 C12 121.3(3) .
C12 C7 C8 C9 -0.3(6) .
P1 C7 C8 C9 174.5(3) .
C7 C8 C9 C10 -0.1(7) .
C8 C9 C10 C11 0.0(7) .
C9 C10 C11 C12 0.6(7) .
C10 C11 C12 C7 -1.1(7) .
C8 C7 C12 C11 1.0(6) .
P1 C7 C12 C11 -174.1(3) .
O2 P1 C13 C14 -17.4(4) .
N1 P1 C13 C14 106.0(3) .
C7 P1 C13 C14 -142.2(3) .
O2 P1 C13 C18 -138.0(3) .
N1 P1 C13 C18 -14.6(3) .
C7 P1 C13 C18 97.2(3) .
C18 C13 C14 C15 -25.8(6) .
P1 C13 C14 C15 -141.5(4) .
C13 C14 C15 C16 0.7(7) .
C14 C15 C16 C17 11.8(7) .
C15 C16 C17 C18 3.8(7) .
C16 C17 C18 C19 89.8(5) .
C16 C17 C18 C13 -28.7(6) .
C14 C13 C18 C17 37.6(5) .
P1 C13 C18 C17 156.9(3) .
C14 C13 C18 C19 -84.0(4) .
P1 C13 C18 C19 35.3(3) .
C20 N1 C19 C1 -52.0(5) .
P1 N1 C19 C1 158.6(3) .
C20 N1 C19 C18 -176.6(3) .
P1 N1 C19 C18 34.0(3) .
C2 C1 C19 N1 134.7(4) .
C6 C1 C19 N1 -46.0(5) .
C2 C1 C19 C18 -105.9(4) .
C6 C1 C19 C18 73.5(5) .
C17 C18 C19 N1 -166.0(3) .
C13 C18 C19 N1 -43.9(4) .
C17 C18 C19 C1 70.6(4) .
C13 C18 C19 C1 -167.2(3) .
C19 N1 C20 C21 126.7(4) .
P1 N1 C20 C21 -86.4(4) .
N1 C20 C21 C21 -176.0(5) 3_656
