#------------------------------------------------------------------------------
#$Date: 2016-03-23 16:33:29 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179383 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/80/4328061.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_4328061
loop_
_publ_author_name
'Diane A. Dickie'
'Kevin B. Gislason'
'Richard A. Kemp'
_publ_contact_author_address
;Advanced Materials Laboratory
Sandia National Laboratories
1001 University Blvd SE
Albuquerque, NM, 87106
USA
;
_publ_contact_author_email       rakemp@unm.edu
_publ_contact_author_name        'Kemp, Richard A.'
_publ_contact_author_phone       1-505-272-7609
_publ_section_title
;
 Formation of Phosphino-Substituted Isocyanate by Reaction of CO2 with
 Group 2 Complexes Based on the (Me3Si)(i-Pr2P)NH Ligand
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1162
_journal_page_last               1169
_journal_paper_doi               10.1021/ic202399z
_journal_volume                  51
_journal_year                    2012
_chemical_formula_sum            'C13 H28 N2 P2'
_chemical_formula_weight         274.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.085(2)
_cell_angle_beta                 89.399(2)
_cell_angle_gamma                89.489(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3294(3)
_cell_length_b                   8.4283(3)
_cell_length_c                   11.9681(4)
_cell_measurement_reflns_used    3573
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      26.55
_cell_measurement_theta_min      2.45
_cell_volume                     807.93(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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      223(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15621
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.9726
_exptl_absorpt_correction_T_min  0.9557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_description       chip
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3852
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0394
_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)+(0.0665P)²+0.1078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1259
_reflns_number_gt                2957
_reflns_number_total             3852
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic202399z_si_005.cif
_cod_data_source_block           rkdd98
_cod_database_code               4328061
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 -0.27460(6) 0.20712(6) 0.71201(4) 0.02649(15) Uani 1 1 d .
P2 P 0.14729(5) 0.02229(6) 0.90849(4) 0.02378(14) Uani 1 1 d .
N1 N -0.08123(18) 0.15499(19) 0.76171(12) 0.0261(3) Uani 1 1 d .
N2 N 0.16732(19) -0.0830(2) 1.04106(13) 0.0293(4) Uani 1 1 d .
C1 C -0.2407(3) 0.1949(3) 0.56119(17) 0.0358(5) Uani 1 1 d .
H1A H -0.1425 0.2571 0.5295 0.043 Uiso 1 1 calc R
C2 C -0.2163(4) 0.0147(3) 0.5642(2) 0.0583(7) Uani 1 1 d .
H2A H -0.1979 0.0062 0.4859 0.088 Uiso 1 1 calc R
H2B H -0.3113 -0.0474 0.5968 0.088 Uiso 1 1 calc R
H2C H -0.1242 -0.0295 0.6119 0.088 Uiso 1 1 calc R
C3 C -0.3831(3) 0.2707(4) 0.4854(2) 0.0594(7) Uani 1 1 d .
H3A H -0.3641 0.2646 0.4066 0.089 Uiso 1 1 calc R
H3B H -0.3960 0.3852 0.4854 0.089 Uiso 1 1 calc R
H3C H -0.4799 0.2105 0.5160 0.089 Uiso 1 1 calc R
C4 C -0.2797(2) 0.4339(2) 0.69182(17) 0.0324(4) Uani 1 1 d .
H4A H -0.3828 0.4743 0.6536 0.039 Uiso 1 1 calc R
C5 C -0.2849(3) 0.4695(3) 0.8102(2) 0.0491(6) Uani 1 1 d .
H5A H -0.2880 0.5878 0.7994 0.074 Uiso 1 1 calc R
H5B H -0.1899 0.4233 0.8538 0.074 Uiso 1 1 calc R
H5C H -0.3799 0.4199 0.8526 0.074 Uiso 1 1 calc R
C6 C -0.1478(3) 0.5335(3) 0.6153(2) 0.0475(6) Uani 1 1 d .
H6A H -0.1625 0.6496 0.6102 0.071 Uiso 1 1 calc R
H6B H -0.1531 0.5176 0.5382 0.071 Uiso 1 1 calc R
H6C H -0.0439 0.4968 0.6489 0.071 Uiso 1 1 calc R
C7 C 0.2808(2) 0.1997(2) 0.87886(17) 0.0336(4) Uani 1 1 d .
H7A H 0.3913 0.1562 0.8963 0.040 Uiso 1 1 calc R
C8 C 0.2806(3) 0.3023(3) 0.7528(2) 0.0507(6) Uani 1 1 d .
H8A H 0.3538 0.3941 0.7431 0.076 Uiso 1 1 calc R
H8B H 0.1731 0.3442 0.7316 0.076 Uiso 1 1 calc R
H8C H 0.3148 0.2343 0.7034 0.076 Uiso 1 1 calc R
C9 C 0.2420(3) 0.3033(3) 0.9622(2) 0.0543(7) Uani 1 1 d .
H9A H 0.3136 0.3972 0.9466 0.081 Uiso 1 1 calc R
H9B H 0.2560 0.2366 1.0416 0.081 Uiso 1 1 calc R
H9C H 0.1318 0.3421 0.9513 0.081 Uiso 1 1 calc R
C10 C 0.2096(2) -0.1025(2) 0.81380(16) 0.0325(4) Uani 1 1 d .
H10A H 0.2064 -0.0321 0.7327 0.039 Uiso 1 1 calc R
C11 C 0.3813(3) -0.1643(3) 0.8397(2) 0.0462(6) Uani 1 1 d .
H11A H 0.4123 -0.2304 0.7881 0.069 Uiso 1 1 calc R
H11B H 0.3880 -0.2311 0.9197 0.069 Uiso 1 1 calc R
H11C H 0.4529 -0.0709 0.8278 0.069 Uiso 1 1 calc R
C12 C 0.0942(3) -0.2449(3) 0.8246(2) 0.0484(6) Uani 1 1 d .
H12A H 0.1290 -0.3100 0.7732 0.073 Uiso 1 1 calc R
H12B H -0.0128 -0.2016 0.8031 0.073 Uiso 1 1 calc R
H12C H 0.0928 -0.3137 0.9041 0.073 Uiso 1 1 calc R
C13 C -0.0594(2) 0.0951(2) 0.87201(15) 0.0233(4) 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'
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
N1 P1 C1 97.22(8) . .
N1 P1 C4 102.31(8) . .
C1 P1 C4 101.82(9) . .
N2 P2 C10 109.27(9) . .
N2 P2 C7 109.10(9) . .
C10 P2 C7 107.12(9) . .
N2 P2 C13 113.34(8) . .
C10 P2 C13 108.76(9) . .
C7 P2 C13 109.07(8) . .
C13 N1 P1 118.67(13) . .
C13 N2 P2 126.53(13) 2_557 .
C2 C1 C3 111.4(2) . .
C2 C1 P1 108.40(15) . .
C3 C1 P1 110.01(16) . .
C6 C4 C5 110.69(19) . .
C6 C4 P1 116.40(15) . .
C5 C4 P1 109.63(14) . .
C8 C7 C9 112.06(19) . .
C8 C7 P2 113.71(15) . .
C9 C7 P2 109.60(14) . .
C12 C10 C11 111.31(18) . .
C12 C10 P2 110.54(14) . .
C11 C10 P2 110.79(14) . .
N1 C13 N2 127.98(17) . 2_557
N1 C13 P2 113.12(13) . .
N2 C13 P2 118.89(13) 2_557 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 N1 1.7336(15) .
P1 C1 1.855(2) .
P1 C4 1.860(2) .
P2 N2 1.6012(15) .
P2 C10 1.8144(19) .
P2 C7 1.825(2) .
P2 C13 1.8386(18) .
N1 C13 1.292(2) .
N2 C13 1.351(2) 2_557
C1 C2 1.521(3) .
C1 C3 1.526(3) .
C4 C6 1.524(3) .
C4 C5 1.527(3) .
C7 C8 1.519(3) .
C7 C9 1.526(3) .
C10 C12 1.521(3) .
C10 C11 1.523(3) .
C13 N2 1.351(2) 2_557
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
C1 P1 N1 C13 -157.30(15) .
C4 P1 N1 C13 98.87(15) .
C10 P2 N2 C13 -134.41(17) 2_557
C7 P2 N2 C13 108.78(17) 2_557
C13 P2 N2 C13 -13.0(2) 2_557
N1 P1 C1 C2 70.02(17) .
C4 P1 C1 C2 174.28(16) .
N1 P1 C1 C3 -168.00(17) .
C4 P1 C1 C3 -63.75(18) .
N1 P1 C4 C6 54.21(17) .
C1 P1 C4 C6 -46.00(18) .
N1 P1 C4 C5 -72.36(16) .
C1 P1 C4 C5 -172.57(15) .
N2 P2 C7 C8 175.91(15) .
C10 P2 C7 C8 57.75(18) .
C13 P2 C7 C8 -59.80(17) .
N2 P2 C7 C9 -57.80(17) .
C10 P2 C7 C9 -175.96(15) .
C13 P2 C7 C9 66.49(17) .
N2 P2 C10 C12 67.40(17) .
C7 P2 C10 C12 -174.54(15) .
C13 P2 C10 C12 -56.79(16) .
N2 P2 C10 C11 -56.47(17) .
C7 P2 C10 C11 61.58(17) .
C13 P2 C10 C11 179.33(14) .
P1 N1 C13 N2 -8.0(3) 2_557
P1 N1 C13 P2 172.73(8) .
N2 P2 C13 N1 -168.82(13) .
C10 P2 C13 N1 -47.08(16) .
C7 P2 C13 N1 69.43(15) .
N2 P2 C13 N2 11.9(2) 2_557
C10 P2 C13 N2 133.61(15) 2_557
C7 P2 C13 N2 -109.88(15) 2_557
