#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/55/4315545.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_4315545
loop_
_publ_author_name
'Jamie S. Ritch'
'Stuart D. Robertson'
'Maarit Risto'
'Tristram Chivers'
_publ_section_title
;
 Synthesis, Multinuclear NMR Spectra, and X-ray Structures of
 tBu2PNP(I)tBu2 and EPR2NP(I)R2 (E = Se, Te; R =iPr,tBu)
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4681
_journal_page_last               4686
_journal_paper_doi               10.1021/ic1005055
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C16 H36 I N P2'
_chemical_formula_weight         431.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.7590(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8624(3)
_cell_length_b                   9.3548(2)
_cell_length_c                   15.9801(4)
_cell_measurement_reflns_used    8044
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      67.57
_cell_measurement_theta_min      4.16
_cell_volume                     2071.32(8)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker ApexII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12722
_diffrn_reflns_theta_full        66.52
_diffrn_reflns_theta_max         66.52
_diffrn_reflns_theta_min         5.54
_exptl_absorpt_coefficient_mu    13.536
_exptl_absorpt_correction_T_max  0.4106
_exptl_absorpt_correction_T_min  0.0743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Blessing, R. H. (1995) Acta Cryst. A51, 33-38'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.839
_refine_diff_density_min         -0.784
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3533
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0449
_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)+(0.0697P)²+5.8748P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1308
_reflns_number_gt                3339
_reflns_number_total             3533
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic1005055_si_001_5.cif
_cod_data_source_block           compound6'-I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4315545
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.89916(2) 0.80754(4) 0.86254(2) 0.03625(16) Uani 1 1 d . . .
P1 P 0.74475(8) 0.85003(12) 0.94013(7) 0.0206(3) Uani 1 1 d . . .
C1 C 0.7577(4) 1.0422(5) 0.9724(3) 0.0290(10) Uani 1 1 d . . .
C2 C 0.6736(5) 1.0766(6) 1.0289(4) 0.0436(14) Uani 1 1 d . . .
H2A H 0.6784 1.1762 1.0475 0.065 Uiso 1 1 calc R . .
H2B H 0.6761 1.0131 1.0777 0.065 Uiso 1 1 calc R . .
H2C H 0.6125 1.0625 0.9975 0.065 Uiso 1 1 calc R . .
C3 C 0.8516(4) 1.0566(6) 1.0244(3) 0.0379(12) Uani 1 1 d . . .
H3A H 0.8587 1.1554 1.0440 0.057 Uiso 1 1 calc R . .
H3B H 0.9063 1.0316 0.9898 0.057 Uiso 1 1 calc R . .
H3C H 0.8500 0.9921 1.0726 0.057 Uiso 1 1 calc R . .
C4 C 0.7595(5) 1.1468(6) 0.8985(4) 0.0456(14) Uani 1 1 d . . .
H4A H 0.7754 1.2428 0.9191 0.068 Uiso 1 1 calc R . .
H4B H 0.6959 1.1483 0.8699 0.068 Uiso 1 1 calc R . .
H4C H 0.8082 1.1159 0.8592 0.068 Uiso 1 1 calc R . .
C5 C 0.6533(4) 0.8140(5) 0.8539(3) 0.0289(11) Uani 1 1 d . . .
C6 C 0.5545(4) 0.8581(7) 0.8847(4) 0.0411(13) Uani 1 1 d . . .
H6A H 0.5040 0.8238 0.8453 0.062 Uiso 1 1 calc R . .
H6B H 0.5512 0.9626 0.8885 0.062 Uiso 1 1 calc R . .
H6C H 0.5447 0.8164 0.9400 0.062 Uiso 1 1 calc R . .
C7 C 0.6712(4) 0.8874(7) 0.7717(3) 0.0384(13) Uani 1 1 d . . .
H7A H 0.6243 0.8534 0.7291 0.058 Uiso 1 1 calc R . .
H7B H 0.7366 0.8654 0.7541 0.058 Uiso 1 1 calc R . .
H7C H 0.6643 0.9910 0.7786 0.058 Uiso 1 1 calc R . .
C8 C 0.6542(4) 0.6515(6) 0.8410(3) 0.0376(12) Uani 1 1 d . . .
H8A H 0.6073 0.6257 0.7963 0.056 Uiso 1 1 calc R . .
H8B H 0.6370 0.6038 0.8931 0.056 Uiso 1 1 calc R . .
H8C H 0.7188 0.6211 0.8252 0.056 Uiso 1 1 calc R . .
N1 N 0.7283(3) 0.7415(4) 1.0116(2) 0.0237(8) Uani 1 1 d . . .
P2 P 0.75179(9) 0.72466(13) 1.11533(7) 0.0261(3) Uani 1 1 d . . .
C9 C 0.8598(4) 0.6008(6) 1.1170(3) 0.0319(11) Uani 1 1 d . . .
C10 C 0.8726(4) 0.5289(7) 1.2023(4) 0.0498(16) Uani 1 1 d . . .
H10A H 0.9395 0.4962 1.2100 0.075 Uiso 1 1 calc R . .
H10B H 0.8289 0.4470 1.2053 0.075 Uiso 1 1 calc R . .
H10C H 0.8578 0.5975 1.2465 0.075 Uiso 1 1 calc R . .
C11 C 0.8600(5) 0.4897(6) 1.0465(4) 0.0471(14) Uani 1 1 d . . .
H11A H 0.9221 0.4394 1.0478 0.071 Uiso 1 1 calc R . .
H11B H 0.8505 0.5379 0.9924 0.071 Uiso 1 1 calc R . .
H11C H 0.8078 0.4209 1.0543 0.071 Uiso 1 1 calc R . .
C12 C 0.9469(4) 0.6996(6) 1.1058(4) 0.0431(14) Uani 1 1 d . . .
H12A H 1.0060 0.6423 1.1051 0.065 Uiso 1 1 calc R . .
H12B H 0.9512 0.7679 1.1522 0.065 Uiso 1 1 calc R . .
H12C H 0.9391 0.7516 1.0527 0.065 Uiso 1 1 calc R . .
C13 C 0.6411(4) 0.6201(6) 1.1449(3) 0.0354(12) Uani 1 1 d . . .
C14 C 0.6254(5) 0.4784(7) 1.1002(5) 0.0541(17) Uani 1 1 d . . .
H14A H 0.5616 0.4408 1.1130 0.081 Uiso 1 1 calc R . .
H14B H 0.6751 0.4103 1.1192 0.081 Uiso 1 1 calc R . .
H14C H 0.6295 0.4927 1.0397 0.081 Uiso 1 1 calc R . .
C15 C 0.6433(5) 0.5959(7) 1.2402(4) 0.0506(15) Uani 1 1 d . . .
H15A H 0.5794 0.5648 1.2576 0.076 Uiso 1 1 calc R . .
H15B H 0.6608 0.6852 1.2688 0.076 Uiso 1 1 calc R . .
H15C H 0.6911 0.5221 1.2549 0.076 Uiso 1 1 calc R . .
C16 C 0.5566(5) 0.7200(7) 1.1250(4) 0.0475(15) Uani 1 1 d . . .
H16A H 0.4970 0.6775 1.1452 0.071 Uiso 1 1 calc R . .
H16B H 0.5505 0.7346 1.0644 0.071 Uiso 1 1 calc R . .
H16C H 0.5680 0.8121 1.1528 0.071 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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
_geom_angle_publ_flag
N1 P1 C5 108.2(2) . . ?
N1 P1 C1 116.1(2) . . ?
C5 P1 C1 115.5(2) . . ?
N1 P1 I1 113.77(15) . . ?
C5 P1 I1 100.04(17) . . ?
C1 P1 I1 102.07(17) . . ?
C3 C1 C2 108.3(5) . . ?
C3 C1 C4 109.2(4) . . ?
C2 C1 C4 110.5(5) . . ?
C3 C1 P1 107.9(3) . . ?
C2 C1 P1 107.1(3) . . ?
C4 C1 P1 113.7(4) . . ?
C7 C5 C6 109.3(4) . . ?
C7 C5 C8 109.4(5) . . ?
C6 C5 C8 108.8(5) . . ?
C7 C5 P1 115.6(4) . . ?
C6 C5 P1 107.9(4) . . ?
C8 C5 P1 105.6(3) . . ?
P1 N1 P2 139.2(3) . . ?
N1 P2 C13 99.2(2) . . ?
N1 P2 C9 101.6(2) . . ?
C13 P2 C9 109.1(2) . . ?
C10 C9 C11 110.8(5) . . ?
C10 C9 C12 107.4(4) . . ?
C11 C9 C12 107.6(5) . . ?
C10 C9 P2 110.7(4) . . ?
C11 C9 P2 115.1(4) . . ?
C12 C9 P2 104.7(4) . . ?
C14 C13 C16 109.9(6) . . ?
C14 C13 C15 109.5(5) . . ?
C16 C13 C15 106.7(5) . . ?
C14 C13 P2 116.1(4) . . ?
C16 C13 P2 104.8(4) . . ?
C15 C13 P2 109.3(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 P1 2.5377(12) . ?
P1 N1 1.550(4) . ?
P1 C5 1.875(5) . ?
P1 C1 1.878(5) . ?
C1 C3 1.527(7) . ?
C1 C2 1.530(8) . ?
C1 C4 1.535(7) . ?
C5 C7 1.508(7) . ?
C5 C6 1.527(8) . ?
C5 C8 1.535(7) . ?
N1 P2 1.686(4) . ?
P2 C13 1.892(6) . ?
P2 C9 1.892(5) . ?
C9 C10 1.525(7) . ?
C9 C11 1.532(8) . ?
C9 C12 1.536(8) . ?
C13 C14 1.517(8) . ?
C13 C16 1.524(9) . ?
C13 C15 1.540(8) . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 P1 C1 C3 66.9(4) . . . . ?
C5 P1 C1 C3 -164.8(4) . . . . ?
I1 P1 C1 C3 -57.4(4) . . . . ?
N1 P1 C1 C2 -49.4(4) . . . . ?
C5 P1 C1 C2 78.9(4) . . . . ?
I1 P1 C1 C2 -173.7(3) . . . . ?
N1 P1 C1 C4 -171.8(4) . . . . ?
C5 P1 C1 C4 -43.5(5) . . . . ?
I1 P1 C1 C4 63.9(4) . . . . ?
N1 P1 C5 C7 -167.4(4) . . . . ?
C1 P1 C5 C7 60.6(5) . . . . ?
I1 P1 C5 C7 -48.1(4) . . . . ?
N1 P1 C5 C6 69.9(4) . . . . ?
C1 P1 C5 C6 -62.2(4) . . . . ?
I1 P1 C5 C6 -170.8(3) . . . . ?
N1 P1 C5 C8 -46.4(4) . . . . ?
C1 P1 C5 C8 -178.4(3) . . . . ?
I1 P1 C5 C8 72.9(4) . . . . ?
C5 P1 N1 P2 -157.9(4) . . . . ?
C1 P1 N1 P2 -26.1(5) . . . . ?
I1 P1 N1 P2 91.9(4) . . . . ?
P1 N1 P2 C13 146.9(4) . . . . ?
P1 N1 P2 C9 -101.3(4) . . . . ?
N1 P2 C9 C10 -160.2(4) . . . . ?
C13 P2 C9 C10 -56.1(5) . . . . ?
N1 P2 C9 C11 -33.6(5) . . . . ?
C13 P2 C9 C11 70.5(5) . . . . ?
N1 P2 C9 C12 84.3(4) . . . . ?
C13 P2 C9 C12 -171.6(4) . . . . ?
N1 P2 C13 C14 57.9(5) . . . . ?
C9 P2 C13 C14 -47.8(5) . . . . ?
N1 P2 C13 C16 -63.5(4) . . . . ?
C9 P2 C13 C16 -169.2(4) . . . . ?
N1 P2 C13 C15 -177.5(4) . . . . ?
C9 P2 C13 C15 76.8(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660982
