#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/54/7035428.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_7035428
loop_
_publ_author_name
'Musina, Elvira I.'
'Fesenko, Tatiana I.'
'Strelnik, Igor D.'
'Polyancev, Fedor M.'
'Latypov, Shamil K.'
'Lönnecke, Peter'
'Hey-Hawkins, Evamarie'
'Karasik, Andrey A.'
'Sinyashin, Oleg G.'
_publ_section_title
;
 Synthesis and unique reversible splitting of 14-membered cyclic
 aminomethylphosphines on to 7-membered heterocycles.
;
_journal_issue                   30
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              13565
_journal_page_last               13572
_journal_paper_doi               10.1039/c5dt01910a
_journal_volume                  44
_journal_year                    2015
_chemical_formula_sum            'C38 H50 N2 P4'
_chemical_formula_weight         658.68
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2015-04-16T15:43:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-04-16 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.726(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.2485(4)
_cell_length_b                   8.13730(10)
_cell_length_c                   21.7857(4)
_cell_measurement_reflns_used    10019
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      32.2838
_cell_measurement_theta_min      2.9217
_cell_volume                     3607.50(11)
_computing_cell_refinement
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_data_collection
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_molecular_graphics
;
 ORTEP3 for Windows
 L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
;
_computing_publication_material
;
 WINGX
 L.J. Farrugia,
 J. Appl. Cryst., 1999, 32, 837-838.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
;
 SIR92
 A. Altomare, G. Cascarano, C. Giacovazzo and A. Guagliardi,
 J. Appl. Crystallogr. 1993, 26, 343-350.
;
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 16.356
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0018778865
_diffrn_orient_matrix_UB_12      0.0442393184
_diffrn_orient_matrix_UB_13      0.0285591319
_diffrn_orient_matrix_UB_21      0.0011144259
_diffrn_orient_matrix_UB_22      0.0749824482
_diffrn_orient_matrix_UB_23      -0.0163067328
_diffrn_orient_matrix_UB_31      -0.0348210457
_diffrn_orient_matrix_UB_32      0.0048147243
_diffrn_orient_matrix_UB_33      -0.0088629523
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.055
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            17896
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.503
_diffrn_reflns_theta_min         2.964
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.99257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       prism
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5502
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0578P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0923
_reflns_Friedel_coverage         0
_reflns_number_gt                4327
_reflns_number_total             5502
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5dt01910a2.cif
_cod_data_source_block           x0894fin
_cod_depositor_comments          'Adding full bibliography for 7035428.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7035428
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
P1 P 0.40114(2) 0.11343(4) 0.30225(2) 0.01877(8) Uani 1 1 d .
P2 P 0.37251(2) 0.03464(4) 0.09258(2) 0.01905(8) Uani 1 1 d .
N1 N 0.50048(4) -0.09599(11) 0.36725(4) 0.01826(18) Uani 1 1 d .
C1 C 0.54007(5) 0.03111(15) 0.40821(5) 0.0216(2) Uani 1 1 d .
C2 C 0.43036(5) -0.06384(14) 0.35710(5) 0.0205(2) Uani 1 1 d .
C3 C 0.40008(5) 0.01828(14) 0.22541(5) 0.0212(2) Uani 1 1 d .
C4 C 0.38001(6) 0.13966(15) 0.16921(5) 0.0232(2) Uani 1 1 d .
C5 C 0.52045(6) -0.26382(15) 0.39143(7) 0.0299(3) Uani 1 1 d D
C6 C 0.49207(9) -0.3893(2) 0.33978(14) 0.0705(7) Uani 1 1 d D
C7 C 0.50560(9) -0.3054(3) 0.45432(11) 0.0666(7) Uani 1 1 d D
C8 C 0.31486(5) 0.10354(13) 0.30220(5) 0.0182(2) Uani 1 1 d .
C9 C 0.26422(5) 0.02792(15) 0.25510(6) 0.0248(2) Uani 1 1 d .
C10 C 0.20038(6) 0.02602(16) 0.25955(7) 0.0296(3) Uani 1 1 d .
C11 C 0.18585(6) 0.09845(16) 0.31129(6) 0.0295(3) Uani 1 1 d .
C12 C 0.23555(6) 0.17318(16) 0.35880(6) 0.0291(3) Uani 1 1 d .
C13 C 0.29901(6) 0.17662(15) 0.35383(5) 0.0229(2) Uani 1 1 d .
C14 C 0.34642(5) 0.19717(14) 0.03264(5) 0.0188(2) Uani 1 1 d .
C15 C 0.32275(5) 0.14425(16) -0.03074(5) 0.0236(2) Uani 1 1 d .
C16 C 0.30403(6) 0.25585(16) -0.08086(5) 0.0271(2) Uani 1 1 d .
C17 C 0.30736(6) 0.42160(17) -0.06827(6) 0.0276(3) Uani 1 1 d .
C18 C 0.32981(6) 0.47744(16) -0.00550(6) 0.0301(3) Uani 1 1 d .
C19 C 0.34964(6) 0.36581(15) 0.04454(6) 0.0266(2) Uani 1 1 d .
H1A H 0.5421(7) 0.0145(19) 0.4537(8) 0.039(4) Uiso 1 1 d .
H1B H 0.5231(6) 0.1426(17) 0.3948(6) 0.026(3) Uiso 1 1 d .
H2A H 0.4051(6) -0.1634(17) 0.3369(6) 0.026(3) Uiso 1 1 d .
H2B H 0.4166(7) -0.0358(17) 0.3975(7) 0.031(4) Uiso 1 1 d .
H3A H 0.4438(6) -0.0219(16) 0.2308(6) 0.021(3) Uiso 1 1 d .
H3B H 0.3686(7) -0.0810(18) 0.2159(7) 0.030(4) Uiso 1 1 d .
H4A H 0.4122(7) 0.2354(19) 0.1740(7) 0.037(4) Uiso 1 1 d .
H4B H 0.3364(7) 0.1846(17) 0.1664(6) 0.028(3) Uiso 1 1 d .
H5 H 0.5676(7) -0.2669(16) 0.3991(6) 0.023(3) Uiso 1 1 d .
H6A H 0.4463(5) -0.3983(19) 0.3342(7) 0.082(7) Uiso 1 1 d D
H6B H 0.5111(7) -0.4928(13) 0.3529(7) 0.086(7) Uiso 1 1 d D
H6C H 0.4993(8) -0.3579(19) 0.3013(5) 0.118(11) Uiso 1 1 d D
H7A H 0.4597(5) -0.311(2) 0.4462(7) 0.096(8) Uiso 1 1 d D
H7B H 0.5232(8) -0.4106(15) 0.4676(6) 0.080(6) Uiso 1 1 d D
H7C H 0.5235(9) -0.2278(18) 0.4854(6) 0.141(14) Uiso 1 1 d D
H9 H 0.2720(7) -0.0229(18) 0.2198(7) 0.030(4) Uiso 1 1 d .
H10 H 0.1651(8) -0.024(2) 0.2262(8) 0.043(4) Uiso 1 1 d .
H11 H 0.1445(7) 0.0944(17) 0.3153(7) 0.028(4) Uiso 1 1 d .
H12 H 0.2269(8) 0.230(2) 0.3971(8) 0.046(4) Uiso 1 1 d .
H13 H 0.3329(7) 0.2360(18) 0.3853(7) 0.034(4) Uiso 1 1 d .
H15 H 0.3189(7) 0.0299(19) -0.0397(7) 0.029(4) Uiso 1 1 d .
H16 H 0.2858(8) 0.217(2) -0.1254(8) 0.044(4) Uiso 1 1 d .
H17 H 0.2930(7) 0.494(2) -0.1002(8) 0.039(4) Uiso 1 1 d .
H18 H 0.3304(8) 0.598(2) 0.0014(8) 0.052(5) Uiso 1 1 d .
H19 H 0.3634(7) 0.407(2) 0.0853(7) 0.037(4) 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
P P 0.1023 0.0942 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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
C8 P1 C3 103.33(5) . .
C8 P1 C2 96.61(5) . .
C3 P1 C2 99.93(5) . .
C14 P2 C4 103.95(5) . .
C14 P2 C1 95.90(5) . 2_655
C4 P2 C1 100.91(5) . 2_655
C1 N1 C2 110.30(9) . .
C1 N1 C5 112.28(9) . .
C2 N1 C5 113.15(8) . .
N1 C1 P2 113.90(8) . 2_655
N1 C1 H1A 111.5(9) . .
P2 C1 H1A 104.8(9) 2_655 .
N1 C1 H1B 111.8(8) . .
P2 C1 H1B 105.3(8) 2_655 .
H1A C1 H1B 109.2(12) . .
N1 C2 P1 111.84(7) . .
N1 C2 H2A 108.4(8) . .
P1 C2 H2A 107.9(8) . .
N1 C2 H2B 115.9(8) . .
P1 C2 H2B 104.6(8) . .
H2A C2 H2B 107.8(11) . .
C4 C3 P1 112.52(8) . .
C4 C3 H3A 110.7(8) . .
P1 C3 H3A 106.0(8) . .
C4 C3 H3B 109.2(8) . .
P1 C3 H3B 110.4(8) . .
H3A C3 H3B 107.9(11) . .
C3 C4 P2 110.87(8) . .
C3 C4 H4A 112.6(8) . .
P2 C4 H4A 109.1(9) . .
C3 C4 H4B 109.2(8) . .
P2 C4 H4B 106.5(8) . .
H4A C4 H4B 108.3(12) . .
N1 C5 C6 110.26(12) . .
N1 C5 C7 114.26(12) . .
C6 C5 C7 112.11(17) . .
N1 C5 H5 105.2(8) . .
C6 C5 H5 106.4(8) . .
C7 C5 H5 108.0(8) . .
C5 C6 H6A 108.8(8) . .
C5 C6 H6B 109.5(8) . .
H6A C6 H6B 107.8(9) . .
C5 C6 H6C 110.5(9) . .
H6A C6 H6C 109.6(10) . .
H6B C6 H6C 110.5(10) . .
C5 C7 H7A 108.2(8) . .
C5 C7 H7B 108.0(8) . .
H7A C7 H7B 108.3(10) . .
C5 C7 H7C 110.9(9) . .
H7A C7 H7C 110.7(10) . .
H7B C7 H7C 110.6(10) . .
C13 C8 C9 117.75(10) . .
C13 C8 P1 116.96(8) . .
C9 C8 P1 125.29(8) . .
C10 C9 C8 121.00(11) . .
C10 C9 H9 117.6(9) . .
C8 C9 H9 121.4(9) . .
C11 C10 C9 120.27(12) . .
C11 C10 H10 118.8(9) . .
C9 C10 H10 120.9(10) . .
C10 C11 C12 119.60(11) . .
C10 C11 H11 120.8(9) . .
C12 C11 H11 119.5(9) . .
C13 C12 C11 119.98(11) . .
C13 C12 H12 117.8(9) . .
C11 C12 H12 122.2(9) . .
C12 C13 C8 121.38(11) . .
C12 C13 H13 119.8(9) . .
C8 C13 H13 118.7(9) . .
C19 C14 C15 118.19(10) . .
C19 C14 P2 126.17(8) . .
C15 C14 P2 115.62(9) . .
C16 C15 C14 121.13(11) . .
C16 C15 H15 119.5(9) . .
C14 C15 H15 119.4(9) . .
C17 C16 C15 119.91(11) . .
C17 C16 H16 119.7(9) . .
C15 C16 H16 120.3(10) . .
C16 C17 C18 120.08(12) . .
C16 C17 H17 120.1(10) . .
C18 C17 H17 119.7(10) . .
C19 C18 C17 119.99(12) . .
C19 C18 H18 122.7(10) . .
C17 C18 H18 117.3(10) . .
C18 C19 C14 120.68(11) . .
C18 C19 H19 117.7(10) . .
C14 C19 H19 121.6(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C8 1.8348(11) .
P1 C3 1.8387(11) .
P1 C2 1.8620(11) .
P2 C14 1.8289(11) .
P2 C4 1.8411(12) .
P2 C1 1.8628(11) 2_655
N1 C1 1.4633(14) .
N1 C2 1.4654(13) .
N1 C5 1.4812(15) .
C1 P2 1.8627(11) 2_655
C1 H1A 0.988(16) .
C1 H1B 0.989(14) .
C2 H2A 1.002(14) .
C2 H2B 1.030(14) .
C3 C4 1.5349(15) .
C3 H3A 0.960(13) .
C3 H3B 1.031(15) .
C4 H4A 1.022(15) .
C4 H4B 0.981(14) .
C5 C6 1.511(2) .
C5 C7 1.530(2) .
C5 H5 0.968(13) .
C6 H6A 0.948(10) .
C6 H6B 0.942(10) .
C6 H6C 0.930(10) .
C7 H7A 0.941(10) .
C7 H7B 0.945(10) .
C7 H7C 0.924(10) .
C8 C13 1.3965(15) .
C8 C9 1.3978(15) .
C9 C10 1.3875(17) .
C9 H9 0.929(15) .
C10 C11 1.3834(19) .
C10 H10 0.970(16) .
C11 C12 1.3882(19) .
C11 H11 0.908(14) .
C12 C13 1.3839(17) .
C12 H12 1.017(16) .
C13 H13 0.969(15) .
C14 C19 1.3946(16) .
C14 C15 1.3948(15) .
C15 C16 1.3875(16) .
C15 H15 0.949(15) .
C16 C17 1.3741(18) .
C16 H16 0.988(16) .
C17 C18 1.3886(18) .
C17 H17 0.893(16) .
C18 C19 1.3882(17) .
C18 H18 0.993(18) .
C19 H19 0.913(16) .
