#------------------------------------------------------------------------------
#$Date: 2016-03-23 16:20:08 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179372 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/69/4326903.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_4326903
loop_
_publ_author_name
'Diane A. Dickie'
'Eric N. Coker'
'Richard A. Kemp'
_publ_section_title
;
 Formation of a Reversible, Intramolecular Main-Group Metal-CO2 Adduct
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              11288
_journal_page_last               11290
_journal_paper_doi               10.1021/ic201697g
_journal_volume                  50
_journal_year                    2011
_chemical_formula_sum            'C12 H29 N P2'
_chemical_formula_weight         249.30
_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                 97.590(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   36.0394(14)
_cell_length_b                   8.7728(4)
_cell_length_c                   9.9798(4)
_cell_measurement_reflns_used    9210
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.60
_cell_measurement_theta_min      2.59
_cell_volume                     3127.6(2)
_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      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            58695
_diffrn_reflns_theta_full        29.14
_diffrn_reflns_theta_max         29.14
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.9725
_exptl_absorpt_correction_T_min  0.8962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.059
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.941
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.293
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         8400
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.293
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.1069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0331P)²+24.3554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2600
_refine_ls_wR_factor_ref         0.2627
_reflns_number_gt                7488
_reflns_number_total             8400
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic201697g_si_001.cif
_cod_data_source_block           rkdd112a
_cod_database_code               4326903
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
N1 N 0.37774(11) 0.7289(5) 1.0190(4) 0.0168(7) Uani 1 1 d .
N2 N 0.12234(11) 0.2663(5) 0.1368(4) 0.0169(7) Uani 1 1 d .
P1 P 0.42114(3) 0.68168(14) 0.98189(12) 0.0178(3) Uani 1 1 d .
P2 P 0.34394(3) 0.79511(14) 0.89728(12) 0.0176(2) Uani 1 1 d .
P3 P 0.07904(3) 0.31429(14) 0.05758(12) 0.0174(2) Uani 1 1 d .
P4 P 0.15585(3) 0.19487(14) 0.04876(12) 0.0171(2) Uani 1 1 d .
C1 C 0.42716(14) 0.4824(6) 1.0432(5) 0.0238(10) Uani 1 1 d .
H1A H 0.4545 0.4587 1.0508 0.029 Uiso 1 1 calc R
C2 C 0.41502(18) 0.4527(7) 1.1822(6) 0.0344(13) Uani 1 1 d .
H2A H 0.4193 0.3453 1.2065 0.052 Uiso 1 1 calc R
H2B H 0.3883 0.4763 1.1792 0.052 Uiso 1 1 calc R
H2C H 0.4296 0.5175 1.2498 0.052 Uiso 1 1 calc R
C3 C 0.4072(2) 0.3745(7) 0.9368(7) 0.0385(14) Uani 1 1 d .
H3A H 0.4104 0.2691 0.9688 0.058 Uiso 1 1 calc R
H3B H 0.4179 0.3859 0.8521 0.058 Uiso 1 1 calc R
H3C H 0.3804 0.3994 0.9216 0.058 Uiso 1 1 calc R
C4 C 0.45235(13) 0.7847(6) 1.1148(5) 0.0231(10) Uani 1 1 d .
H4A H 0.4453 0.7570 1.2052 0.028 Uiso 1 1 calc R
C5 C 0.49291(16) 0.7402(8) 1.1107(8) 0.0435(15) Uani 1 1 d .
H5A H 0.5090 0.7955 1.1814 0.065 Uiso 1 1 calc R
H5B H 0.5001 0.7662 1.0221 0.065 Uiso 1 1 calc R
H5C H 0.4959 0.6303 1.1260 0.065 Uiso 1 1 calc R
C6 C 0.44744(17) 0.9568(7) 1.0940(6) 0.0336(12) Uani 1 1 d .
H6A H 0.4639 1.0110 1.1643 0.050 Uiso 1 1 calc R
H6B H 0.4213 0.9847 1.0993 0.050 Uiso 1 1 calc R
H6C H 0.4540 0.9848 1.0049 0.050 Uiso 1 1 calc R
C7 C 0.30172(13) 0.7136(6) 0.9584(5) 0.0231(10) Uani 1 1 d .
H7A H 0.3018 0.7425 1.0553 0.028 Uiso 1 1 calc R
C8 C 0.26573(16) 0.7710(8) 0.8772(7) 0.0386(14) Uani 1 1 d .
H8A H 0.2442 0.7251 0.9123 0.058 Uiso 1 1 calc R
H8B H 0.2654 0.7429 0.7820 0.058 Uiso 1 1 calc R
H8C H 0.2645 0.8822 0.8850 0.058 Uiso 1 1 calc R
C9 C 0.30287(17) 0.5386(7) 0.9476(6) 0.0334(12) Uani 1 1 d .
H9A H 0.2806 0.4952 0.9800 0.050 Uiso 1 1 calc R
H9B H 0.3254 0.5000 1.0029 0.050 Uiso 1 1 calc R
H9C H 0.3033 0.5092 0.8531 0.050 Uiso 1 1 calc R
C10 C 0.34236(14) 1.0012(5) 0.9420(5) 0.0212(9) Uani 1 1 d .
H10A H 0.3684 1.0394 0.9385 0.025 Uiso 1 1 calc R
C11 C 0.33419(17) 1.0379(6) 1.0853(6) 0.0315(12) Uani 1 1 d .
H11A H 0.3341 1.1486 1.0979 0.047 Uiso 1 1 calc R
H11B H 0.3536 0.9923 1.1512 0.047 Uiso 1 1 calc R
H11C H 0.3097 0.9962 1.0984 0.047 Uiso 1 1 calc R
C12 C 0.31761(16) 1.0960(6) 0.8375(6) 0.0298(11) Uani 1 1 d .
H12A H 0.3179 1.2027 0.8668 0.045 Uiso 1 1 calc R
H12B H 0.2919 1.0572 0.8285 0.045 Uiso 1 1 calc R
H12C H 0.3271 1.0890 0.7501 0.045 Uiso 1 1 calc R
C13 C 0.04725(13) 0.2127(6) 0.1594(5) 0.0217(9) Uani 1 1 d .
H13A H 0.0540 0.2405 0.2567 0.026 Uiso 1 1 calc R
C14 C 0.00682(16) 0.2583(8) 0.1141(8) 0.0421(15) Uani 1 1 d .
H14A H -0.0097 0.2035 0.1682 0.063 Uiso 1 1 calc R
H14B H 0.0001 0.2324 0.0184 0.063 Uiso 1 1 calc R
H14C H 0.0040 0.3683 0.1263 0.063 Uiso 1 1 calc R
C15 C 0.05168(17) 0.0395(6) 0.1435(6) 0.0330(12) Uani 1 1 d .
H15A H 0.0349 -0.0137 0.1975 0.049 Uiso 1 1 calc R
H15B H 0.0776 0.0103 0.1748 0.049 Uiso 1 1 calc R
H15C H 0.0454 0.0115 0.0482 0.049 Uiso 1 1 calc R
C16 C 0.07328(14) 0.5144(5) 0.1128(5) 0.0225(9) Uani 1 1 d .
H16A H 0.0460 0.5388 0.0933 0.027 Uiso 1 1 calc R
C17 C 0.08488(18) 0.5446(7) 0.2628(6) 0.0334(12) Uani 1 1 d .
H17A H 0.0808 0.6523 0.2822 0.050 Uiso 1 1 calc R
H17B H 0.1114 0.5198 0.2867 0.050 Uiso 1 1 calc R
H17C H 0.0699 0.4810 0.3159 0.050 Uiso 1 1 calc R
C18 C 0.09344(19) 0.6205(7) 0.0260(6) 0.0363(13) Uani 1 1 d .
H18A H 0.0905 0.7261 0.0546 0.054 Uiso 1 1 calc R
H18B H 0.0828 0.6092 -0.0690 0.054 Uiso 1 1 calc R
H18C H 0.1201 0.5944 0.0363 0.054 Uiso 1 1 calc R
C19 C 0.19836(13) 0.2720(6) 0.1520(5) 0.0228(9) Uani 1 1 d .
H19A H 0.1972 0.2476 0.2492 0.027 Uiso 1 1 calc R
C20 C 0.19929(16) 0.4453(7) 0.1353(6) 0.0333(12) Uani 1 1 d .
H20A H 0.2217 0.4864 0.1899 0.050 Uiso 1 1 calc R
H20B H 0.1769 0.4900 0.1654 0.050 Uiso 1 1 calc R
H20C H 0.1999 0.4705 0.0400 0.050 Uiso 1 1 calc R
C21 C 0.23388(15) 0.2025(7) 0.1109(7) 0.0379(14) Uani 1 1 d .
H21A H 0.2557 0.2452 0.1672 0.057 Uiso 1 1 calc R
H21B H 0.2354 0.2258 0.0157 0.057 Uiso 1 1 calc R
H21C H 0.2334 0.0917 0.1233 0.057 Uiso 1 1 calc R
C22 C 0.15566(14) -0.0118(6) 0.0938(5) 0.0222(9) Uani 1 1 d .
H22A H 0.1294 -0.0468 0.0649 0.027 Uiso 1 1 calc R
C23 C 0.17988(16) -0.1089(6) 0.0127(6) 0.0297(11) Uani 1 1 d .
H23A H 0.1787 -0.2157 0.0406 0.045 Uiso 1 1 calc R
H23B H 0.2058 -0.0732 0.0291 0.045 Uiso 1 1 calc R
H23C H 0.1706 -0.1001 -0.0839 0.045 Uiso 1 1 calc R
C24 C 0.16334(18) -0.0484(7) 0.2454(6) 0.0330(12) Uani 1 1 d .
H24A H 0.1627 -0.1590 0.2584 0.049 Uiso 1 1 calc R
H24B H 0.1441 -0.0003 0.2922 0.049 Uiso 1 1 calc R
H24C H 0.1880 -0.0092 0.2823 0.049 Uiso 1 1 calc R
H1 H 0.3740(13) 0.724(5) 1.095(5) 0.001(10) Uiso 1 1 d .
H2 H 0.1256(15) 0.269(7) 0.212(6) 0.012(13) 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'
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
P2 N1 P1 121.2(2)
P4 N2 P3 121.3(2)
N1 P1 C1 103.2(2)
N1 P1 C4 102.3(2)
C1 P1 C4 100.9(2)
N1 P2 C7 100.0(2)
N1 P2 C10 101.6(2)
C7 P2 C10 104.1(2)
N2 P3 C13 102.8(2)
N2 P3 C16 103.1(2)
C13 P3 C16 100.9(2)
N2 P4 C19 99.7(2)
N2 P4 C22 102.0(2)
C19 P4 C22 104.4(2)
C3 C1 C2 111.0(5)
C3 C1 P1 109.3(4)
C2 C1 P1 115.1(4)
C5 C4 C6 110.1(5)
C5 C4 P1 110.5(4)
C6 C4 P1 109.6(4)
C8 C7 C9 108.8(5)
C8 C7 P2 112.1(4)
C9 C7 P2 109.3(4)
C12 C10 C11 110.9(4)
C12 C10 P2 113.5(4)
C11 C10 P2 116.3(4)
C14 C13 C15 109.7(5)
C14 C13 P3 110.3(4)
C15 C13 P3 109.7(4)
C18 C16 C17 111.4(5)
C18 C16 P3 109.1(4)
C17 C16 P3 115.4(4)
C21 C19 C20 109.7(5)
C21 C19 P4 111.5(4)
C20 C19 P4 109.3(4)
C23 C22 C24 111.4(4)
C23 C22 P4 113.2(4)
C24 C22 P4 115.7(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 P2 1.705(4)
N1 P1 1.706(4)
N2 P4 1.704(4)
N2 P3 1.706(4)
P1 C1 1.855(5)
P1 C4 1.856(5)
P2 C7 1.856(5)
P2 C10 1.865(5)
P3 C13 1.857(5)
P3 C16 1.860(5)
P4 C19 1.857(5)
P4 C22 1.869(5)
C1 C3 1.530(8)
C1 C2 1.531(7)
C4 C5 1.519(7)
C4 C6 1.531(8)
C7 C8 1.521(7)
C7 C9 1.540(8)
C10 C12 1.526(7)
C10 C11 1.532(7)
C13 C14 1.521(7)
C13 C15 1.538(7)
C16 C18 1.520(8)
C16 C17 1.522(7)
C19 C21 1.522(7)
C19 C20 1.530(8)
C22 C23 1.526(7)
C22 C24 1.535(7)
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
P2 N1 P1 C1 -125.1(3)
P2 N1 P1 C4 130.4(3)
P1 N1 P2 C7 146.5(3)
P1 N1 P2 C10 -106.8(3)
P4 N2 P3 C13 128.7(3)
P4 N2 P3 C16 -126.6(3)
P3 N2 P4 C19 148.3(3)
P3 N2 P4 C22 -104.6(3)
N1 P1 C1 C3 81.5(4)
C4 P1 C1 C3 -172.9(4)
N1 P1 C1 C2 -44.2(5)
C4 P1 C1 C2 61.4(4)
N1 P1 C4 C5 172.5(4)
C1 P1 C4 C5 66.2(5)
N1 P1 C4 C6 -66.0(4)
C1 P1 C4 C6 -172.3(4)
N1 P2 C7 C8 172.8(4)
C10 P2 C7 C8 68.1(4)
N1 P2 C7 C9 -66.5(4)
C10 P2 C7 C9 -171.2(4)
N1 P2 C10 C12 172.4(4)
C7 P2 C10 C12 -84.0(4)
N1 P2 C10 C11 -57.2(4)
C7 P2 C10 C11 46.4(4)
N2 P3 C13 C14 172.9(4)
C16 P3 C13 C14 66.6(4)
N2 P3 C13 C15 -66.1(4)
C16 P3 C13 C15 -172.4(4)
N2 P3 C16 C18 81.5(4)
C13 P3 C16 C18 -172.5(4)
N2 P3 C16 C17 -44.8(4)
C13 P3 C16 C17 61.3(4)
N2 P4 C19 C21 169.9(4)
C22 P4 C19 C21 64.7(4)
N2 P4 C19 C20 -68.7(4)
C22 P4 C19 C20 -173.9(4)
N2 P4 C22 C23 172.2(4)
C19 P4 C22 C23 -84.3(4)
N2 P4 C22 C24 -57.5(4)
C19 P4 C22 C24 46.0(4)
