#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/04/4310431.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_4310431
loop_
_publ_author_name
'Eric Rivard'
'Alan J. Lough'
'Tristram Chivers'
'Ian Manners'
_publ_section_title
;
 Synthesis of Linear and Cyclic Carbophosphazenes via an Oxidative
 Chlorination Strategy
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              802
_journal_page_last               811
_journal_paper_doi               10.1021/ic034954c
_journal_volume                  43
_journal_year                    2004
_chemical_formula_moiety         'C23 H25 Cl N2 P, Cl'
_chemical_formula_sum            'C23 H25 Cl2 N2 P'
_chemical_formula_weight         431.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.4710(1)
_cell_length_b                   8.7260(4)
_cell_length_c                   22.9941(5)
_cell_measurement_reflns_used    44349
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     4508.7(2)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'SHELXTL V6.12'
_computing_publication_material  'SHELXTL V6.12'
_computing_structure_refinement  'SHELXTL V6.12(Sheldrick, 2001)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.1330
_diffrn_reflns_av_sigmaI/netI    0.0728
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            36451
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.66
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.370
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995) 
;
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0023(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         5178
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0549
_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)+(0.0710P)²+1.4549P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1482
_reflns_number_gt                3556
_reflns_number_total             5178
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic034954csi20031103_051734_3.cif
_cod_data_source_block           compound(6)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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_database_code               4310431
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.21873(3) 0.68122(7) 0.36396(3) 0.0399(2) Uani 1 1 d . . .
Cl2 Cl 0.10910(3) 1.12999(8) 0.59814(3) 0.0470(2) Uani 1 1 d . . .
P1 P 0.15577(3) 0.83367(7) 0.33886(3) 0.03029(18) Uani 1 1 d . . .
N1 N 0.10262(9) 1.0927(2) 0.46329(9) 0.0316(5) Uani 1 1 d . . .
N2 N 0.13551(10) 0.9591(2) 0.38321(9) 0.0382(5) Uani 1 1 d . . .
C1 C 0.13164(10) 0.9769(3) 0.44017(10) 0.0291(5) Uani 1 1 d . . .
C2 C 0.16338(11) 0.8724(3) 0.48114(10) 0.0302(5) Uani 1 1 d . . .
C3 C 0.13287(14) 0.7688(4) 0.51535(14) 0.0552(8) Uani 1 1 d . . .
H3A H 0.0907 0.7636 0.5139 0.066 Uiso 1 1 calc R . .
C4 C 0.16511(19) 0.6710(4) 0.55246(15) 0.0695(10) Uani 1 1 d . . .
H4A H 0.1446 0.5986 0.5759 0.083 Uiso 1 1 calc R . .
C5 C 0.22558(16) 0.6796(3) 0.55499(13) 0.0524(8) Uani 1 1 d . . .
H5A H 0.2470 0.6130 0.5801 0.063 Uiso 1 1 calc R . .
C6 C 0.25564(14) 0.7831(3) 0.52164(12) 0.0481(7) Uani 1 1 d . . .
H6A H 0.2978 0.7892 0.5240 0.058 Uiso 1 1 calc R . .
C7 C 0.22502(12) 0.8789(3) 0.48451(12) 0.0388(6) Uani 1 1 d . . .
H7A H 0.2463 0.9499 0.4611 0.047 Uiso 1 1 calc R . .
C8 C 0.07131(11) 1.2177(3) 0.43118(12) 0.0383(6) Uani 1 1 d . . .
C9 C 0.04449(15) 1.3222(4) 0.47782(15) 0.0593(9) Uani 1 1 d . . .
H9A H 0.0764 1.3645 0.5020 0.089 Uiso 1 1 calc R . .
H9B H 0.0172 1.2628 0.5022 0.089 Uiso 1 1 calc R . .
H9C H 0.0227 1.4060 0.4591 0.089 Uiso 1 1 calc R . .
C10 C 0.11611(13) 1.3075(3) 0.39475(14) 0.0473(7) Uani 1 1 d . . .
H10A H 0.1474 1.3484 0.4201 0.071 Uiso 1 1 calc R . .
H10B H 0.0958 1.3923 0.3751 0.071 Uiso 1 1 calc R . .
H10C H 0.1339 1.2394 0.3657 0.071 Uiso 1 1 calc R . .
C11 C 0.02150(12) 1.1519(3) 0.39317(14) 0.0460(7) Uani 1 1 d . . .
H11A H 0.0388 1.0861 0.3630 0.069 Uiso 1 1 calc R . .
H11B H -0.0005 1.2359 0.3748 0.069 Uiso 1 1 calc R . .
H11C H -0.0057 1.0914 0.4174 0.069 Uiso 1 1 calc R . .
C12 C 0.09561(11) 0.7140(3) 0.31564(11) 0.0334(5) Uani 1 1 d . . .
C13 C 0.04284(12) 0.7060(3) 0.34711(12) 0.0400(6) Uani 1 1 d . . .
H13A H 0.0369 0.7690 0.3803 0.048 Uiso 1 1 calc R . .
C14 C -0.00096(12) 0.6048(3) 0.32930(14) 0.0490(7) Uani 1 1 d . . .
H14A H -0.0373 0.5986 0.3503 0.059 Uiso 1 1 calc R . .
C15 C 0.00776(13) 0.5126(3) 0.28107(14) 0.0492(7) Uani 1 1 d . . .
H15A H -0.0221 0.4412 0.2701 0.059 Uiso 1 1 calc R . .
C16 C 0.05939(13) 0.5231(3) 0.24864(13) 0.0482(7) Uani 1 1 d . . .
H16A H 0.0646 0.4617 0.2149 0.058 Uiso 1 1 calc R . .
C17 C 0.10351(12) 0.6243(3) 0.26600(12) 0.0395(6) Uani 1 1 d . . .
H17A H 0.1392 0.6326 0.2441 0.047 Uiso 1 1 calc R . .
C18 C 0.18592(11) 0.9286(3) 0.27686(10) 0.0335(5) Uani 1 1 d . . .
C19 C 0.14918(13) 1.0395(3) 0.25100(12) 0.0422(6) Uani 1 1 d . . .
H19A H 0.1120 1.0644 0.2682 0.051 Uiso 1 1 calc R . .
C20 C 0.16696(16) 1.1118(3) 0.20098(13) 0.0533(8) Uani 1 1 d . . .
H20A H 0.1421 1.1864 0.1832 0.064 Uiso 1 1 calc R . .
C21 C 0.22131(17) 1.0751(3) 0.17662(13) 0.0584(9) Uani 1 1 d . . .
H21A H 0.2334 1.1244 0.1417 0.070 Uiso 1 1 calc R . .
C22 C 0.25829(15) 0.9686(3) 0.20181(13) 0.0524(8) Uani 1 1 d . . .
H22A H 0.2958 0.9463 0.1848 0.063 Uiso 1 1 calc R . .
C23 C 0.24067(13) 0.8936(3) 0.25229(12) 0.0412(6) Uani 1 1 d . . .
H23A H 0.2658 0.8193 0.2698 0.049 Uiso 1 1 calc R . .
H1N H 0.1036(18) 1.103(4) 0.5101(18) 0.087(12) 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'
Cl Cl 0.1484 0.1585 '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
N2 P1 C18 107.87(12) . . ?
N2 P1 C12 112.53(12) . . ?
C18 P1 C12 108.64(11) . . ?
N2 P1 Cl1 118.50(9) . . ?
C18 P1 Cl1 105.53(9) . . ?
C12 P1 Cl1 103.25(8) . . ?
C1 N1 C8 126.5(2) . . ?
C1 N2 P1 138.38(18) . . ?
N1 C1 N2 121.6(2) . . ?
N1 C1 C2 116.8(2) . . ?
N2 C1 C2 121.5(2) . . ?
C3 C2 C7 119.4(2) . . ?
C3 C2 C1 121.5(2) . . ?
C7 C2 C1 119.1(2) . . ?
C2 C3 C4 119.1(3) . . ?
C5 C4 C3 120.4(3) . . ?
C4 C5 C6 120.4(3) . . ?
C5 C6 C7 120.2(3) . . ?
C6 C7 C2 120.5(3) . . ?
N1 C8 C10 109.6(2) . . ?
N1 C8 C9 105.9(2) . . ?
C10 C8 C9 109.8(2) . . ?
N1 C8 C11 110.6(2) . . ?
C10 C8 C11 111.2(2) . . ?
C9 C8 C11 109.6(2) . . ?
C13 C12 C17 120.4(2) . . ?
C13 C12 P1 121.2(2) . . ?
C17 C12 P1 118.37(19) . . ?
C14 C13 C12 118.9(3) . . ?
C15 C14 C13 120.5(3) . . ?
C16 C15 C14 120.8(3) . . ?
C15 C16 C17 119.2(3) . . ?
C16 C17 C12 120.1(3) . . ?
C23 C18 C19 120.0(2) . . ?
C23 C18 P1 124.1(2) . . ?
C19 C18 P1 115.8(2) . . ?
C20 C19 C18 120.1(3) . . ?
C19 C20 C21 119.4(3) . . ?
C22 C21 C20 121.4(3) . . ?
C21 C22 C23 119.9(3) . . ?
C18 C23 C22 119.3(3) . . ?
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
Cl1 P1 2.0259(8) . ?
P1 N2 1.564(2) . ?
P1 C18 1.783(3) . ?
P1 C12 1.790(3) . ?
N1 C1 1.315(3) . ?
N1 C8 1.494(3) . ?
N2 C1 1.322(3) . ?
C1 C2 1.493(3) . ?
C2 C3 1.380(4) . ?
C2 C7 1.388(4) . ?
C3 C4 1.407(5) . ?
C4 C5 1.362(5) . ?
C5 C6 1.364(4) . ?
C6 C7 1.379(4) . ?
C8 C10 1.526(4) . ?
C8 C9 1.531(4) . ?
C8 C11 1.532(4) . ?
C12 C13 1.391(4) . ?
C12 C17 1.395(3) . ?
C13 C14 1.384(4) . ?
C14 C15 1.384(4) . ?
C15 C16 1.382(4) . ?
C16 C17 1.386(4) . ?
C18 C23 1.388(4) . ?
C18 C19 1.404(4) . ?
C19 C20 1.371(4) . ?
C20 C21 1.381(5) . ?
C21 C22 1.374(5) . ?
C22 C23 1.390(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N Cl2 1.08(4) 2.04(4) 3.121(2) 177(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660875
