#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/41/4324125.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_4324125
loop_
_publ_author_name
'Dheeraj Kumar'
'Nem Singh'
'Karunesh Keshav'
'Anil J. Elias'
_publ_contact_author_address
;DEPARTMENT OF CHEMISTRY
INDIAN INSTITUTE OF TECHNOLOGY DELHI
HAUZ KHAS, NEW DELHI 110016
INDIA
;
_publ_contact_author_email       elias@chemistry.iitd.ac.in
_publ_contact_author_fax         +91-11-26581504
_publ_contact_author_name        'Prof.Anil J. Elias'
_publ_contact_author_phone       +91-11-26591504
_publ_section_title
;
 Ring-Closing Metathesis Reactions of Terminal Alkene-Derived Cyclic
 Phosphazenes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              250
_journal_page_last               260
_journal_paper_doi               10.1021/ic101884s
_journal_volume                  50
_journal_year                    2011
_chemical_formula_moiety         'C18 H25 N3 O5 P2 S'
_chemical_formula_sum            'C18 H25 N3 O5 P2 S'
_chemical_formula_weight         457.42
_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                 114.430(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.880(6)
_cell_length_b                   8.602(3)
_cell_length_c                   16.825(7)
_cell_measurement_temperature    293(2)
_cell_volume                     2092.5(14)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0697
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19382
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    0.343
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960.0
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.126
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.229
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3682
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.229
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0750
_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)+(0.0577P)²+2.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.1624
_reflns_number_gt                3209
_reflns_number_total             3682
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic101884s_si_001_7.cif
_cod_data_source_block           13
_cod_original_sg_symbol_Hall     -P2yn
_cod_database_code               4324125
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
S1 S 0.81520(7) 0.16110(11) 1.08948(6) 0.0310(3) Uani 1 1 d . . .
P1 P 0.81707(7) 0.38929(12) 0.97340(7) 0.0320(3) Uani 1 1 d . . .
P2 P 0.71675(7) 0.12236(12) 0.91090(7) 0.0321(3) Uani 1 1 d . . .
O1 O 0.8899(2) 0.0810(4) 1.15698(19) 0.0457(8) Uani 1 1 d . . .
O2 O 0.6104(2) 0.1048(3) 0.8817(2) 0.0489(8) Uani 1 1 d . . .
O3 O 0.7848(2) 0.5620(3) 0.9705(2) 0.0464(8) Uani 1 1 d . . .
O4 O 0.90846(18) 0.4068(3) 0.95989(18) 0.0385(7) Uani 1 1 d . . .
O5 O 0.7358(2) 0.0010(3) 0.85096(18) 0.0439(8) Uani 1 1 d . . .
N1 N 0.8474(2) 0.3223(4) 1.0694(2) 0.0385(8) Uani 1 1 d . . .
N2 N 0.7428(2) 0.2928(4) 0.8968(2) 0.0357(8) Uani 1 1 d . . .
N3 N 0.7660(2) 0.0572(4) 1.0086(2) 0.0380(8) Uani 1 1 d . . .
C1 C 0.5385(3) 0.2042(6) 0.8209(3) 0.0461(11) Uani 1 1 d . . .
H1A H 0.4876 0.1403 0.7825 0.055 Uiso 1 1 calc R . .
H1B H 0.5630 0.2607 0.7852 0.055 Uiso 1 1 calc R . .
C2 C 0.5038(3) 0.3175(6) 0.8681(3) 0.0479(12) Uani 1 1 d . . .
H2A H 0.5037 0.2673 0.9197 0.058 Uiso 1 1 calc R . .
H2B H 0.4403 0.3445 0.8307 0.058 Uiso 1 1 calc R . .
C3 C 0.5597(3) 0.4643(6) 0.8953(3) 0.0520(13) Uani 1 1 d . . .
H3 H 0.5663 0.5203 0.8510 0.062 Uiso 1 1 calc R . .
C4 C 0.5998(3) 0.5221(6) 0.9730(4) 0.0549(13) Uani 1 1 d . . .
H4 H 0.5932 0.4696 1.0184 0.066 Uiso 1 1 calc R . .
C5 C 0.6561(3) 0.6681(6) 0.9944(4) 0.0618(15) Uani 1 1 d . . .
H5A H 0.6408 0.7292 1.0351 0.074 Uiso 1 1 calc R . .
H5B H 0.6398 0.7289 0.9415 0.074 Uiso 1 1 calc R . .
C6 C 0.7582(3) 0.6378(5) 1.0335(4) 0.0524(13) Uani 1 1 d . . .
H6A H 0.7913 0.7354 1.0516 0.063 Uiso 1 1 calc R . .
H6B H 0.7747 0.5724 1.0846 0.063 Uiso 1 1 calc R . .
C7 C 0.9074(3) 0.4743(5) 0.8802(3) 0.0454(11) Uani 1 1 d . . .
H7A H 0.9343 0.5776 0.8918 0.054 Uiso 1 1 calc R . .
H7B H 0.8443 0.4826 0.8364 0.054 Uiso 1 1 calc R . .
C8 C 0.9628(4) 0.3703(6) 0.8476(4) 0.0577(14) Uani 1 1 d . . .
H8A H 1.0231 0.3514 0.8944 0.069 Uiso 1 1 calc R . .
H8B H 0.9718 0.4216 0.8004 0.069 Uiso 1 1 calc R . .
C9 C 0.9139(5) 0.2173(8) 0.8156(4) 0.0753(18) Uani 1 1 d . . .
H9 H 0.8689 0.2159 0.7585 0.090 Uiso 1 1 calc R . .
C10 C 0.9266(4) 0.0948(7) 0.8560(4) 0.0705(16) Uani 1 1 d . . .
H10 H 0.9747 0.0947 0.9115 0.085 Uiso 1 1 calc R . .
C11 C 0.8744(4) -0.0556(6) 0.8273(3) 0.0561(13) Uani 1 1 d . . .
H11A H 0.8339 -0.0488 0.7656 0.067 Uiso 1 1 calc R . .
H11B H 0.9181 -0.1391 0.8347 0.067 Uiso 1 1 calc R . .
C12 C 0.8177(3) -0.0944(5) 0.8770(3) 0.0488(12) Uani 1 1 d . . .
H12A H 0.7997 -0.2029 0.8676 0.059 Uiso 1 1 calc R . .
H12B H 0.8552 -0.0800 0.9389 0.059 Uiso 1 1 calc R . .
C13 C 0.7324(3) 0.1995(4) 1.1330(3) 0.0318(9) Uani 1 1 d . . .
C14 C 0.6492(3) 0.1207(5) 1.1021(3) 0.0426(11) Uani 1 1 d . . .
H14 H 0.6342 0.0508 1.0561 0.051 Uiso 1 1 calc R . .
C15 C 0.5882(3) 0.1470(6) 1.1405(4) 0.0569(14) Uani 1 1 d . . .
H15 H 0.5321 0.0944 1.1203 0.068 Uiso 1 1 calc R . .
C16 C 0.6107(4) 0.2506(7) 1.2083(4) 0.0605(15) Uani 1 1 d . . .
H16 H 0.5697 0.2675 1.2341 0.073 Uiso 1 1 calc R . .
C17 C 0.6925(4) 0.3285(6) 1.2380(3) 0.0597(14) Uani 1 1 d . . .
H17 H 0.7069 0.3992 1.2836 0.072 Uiso 1 1 calc R . .
C18 C 0.7540(3) 0.3034(5) 1.2009(3) 0.0440(11) Uani 1 1 d . . .
H18 H 0.8100 0.3564 1.2217 0.053 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 0.0033 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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 '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
O1 S1 N3 111.82(19) . . ?
O1 S1 N1 111.11(19) . . ?
N3 S1 N1 114.51(18) . . ?
O1 S1 C13 105.83(18) . . ?
N3 S1 C13 106.2(2) . . ?
N1 S1 C13 106.70(19) . . ?
O3 P1 O4 102.40(16) . . ?
O3 P1 N2 110.48(18) . . ?
O4 P1 N2 110.91(17) . . ?
O3 P1 N1 109.46(18) . . ?
O4 P1 N1 105.84(17) . . ?
N2 P1 N1 116.71(19) . . ?
O2 P2 O5 101.86(17) . . ?
O2 P2 N2 111.24(17) . . ?
O5 P2 N2 113.13(18) . . ?
O2 P2 N3 107.16(18) . . ?
O5 P2 N3 106.57(17) . . ?
N2 P2 N3 115.78(18) . . ?
C1 O2 P2 126.7(3) . . ?
C6 O3 P1 126.5(3) . . ?
C7 O4 P1 120.9(3) . . ?
C12 O5 P2 125.0(3) . . ?
S1 N1 P1 123.5(2) . . ?
P2 N2 P1 121.6(2) . . ?
S1 N3 P2 123.8(2) . . ?
O2 C1 C2 111.2(4) . . ?
O2 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
O2 C1 H1B 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C1 C2 C3 114.0(4) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.6 . . ?
C4 C3 C2 127.8(5) . . ?
C4 C3 H3 116.1 . . ?
C2 C3 H3 116.1 . . ?
C3 C4 C5 124.1(5) . . ?
C3 C4 H4 117.9 . . ?
C5 C4 H4 117.9 . . ?
C4 C5 C6 113.0(4) . . ?
C4 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
O3 C6 C5 110.3(4) . . ?
O3 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
O3 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
O4 C7 C8 108.2(4) . . ?
O4 C7 H7A 110.1 . . ?
C8 C7 H7A 110.1 . . ?
O4 C7 H7B 110.1 . . ?
C8 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
C7 C8 C9 110.9(4) . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C8 127.6(6) . . ?
C10 C9 H9 116.2 . . ?
C8 C9 H9 116.2 . . ?
C9 C10 C11 128.2(7) . . ?
C9 C10 H10 115.9 . . ?
C11 C10 H10 115.9 . . ?
C12 C11 C10 113.0(4) . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
O5 C12 C11 112.2(4) . . ?
O5 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
O5 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C18 C13 C14 120.1(4) . . ?
C18 C13 S1 119.3(3) . . ?
C14 C13 S1 120.6(3) . . ?
C13 C14 C15 119.2(4) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 120.1(5) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.3(5) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.3(5) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 119.9(5) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
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
S1 O1 1.434(3) . ?
S1 N3 1.544(4) . ?
S1 N1 1.562(4) . ?
S1 C13 1.780(4) . ?
P1 O3 1.566(3) . ?
P1 O4 1.566(3) . ?
P1 N2 1.575(4) . ?
P1 N1 1.591(4) . ?
P2 O2 1.559(3) . ?
P2 O5 1.566(3) . ?
P2 N2 1.568(4) . ?
P2 N3 1.601(4) . ?
O2 C1 1.454(5) . ?
O3 C6 1.448(5) . ?
O4 C7 1.456(5) . ?
O5 C12 1.444(5) . ?
C1 C2 1.501(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.502(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.292(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.497(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.499(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.507(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.509(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.225(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.504(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.498(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.377(6) . ?
C13 C14 1.382(6) . ?
C14 C15 1.386(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.360(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
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
O5 P2 O2 C1 -98.8(4) . . . . ?
N2 P2 O2 C1 22.0(4) . . . . ?
N3 P2 O2 C1 149.5(3) . . . . ?
O4 P1 O3 C6 -129.9(4) . . . . ?
N2 P1 O3 C6 111.9(4) . . . . ?
N1 P1 O3 C6 -17.9(4) . . . . ?
O3 P1 O4 C7 -61.7(3) . . . . ?
N2 P1 O4 C7 56.1(3) . . . . ?
N1 P1 O4 C7 -176.4(3) . . . . ?
O2 P2 O5 C12 -143.6(3) . . . . ?
N2 P2 O5 C12 96.9(4) . . . . ?
N3 P2 O5 C12 -31.5(4) . . . . ?
O1 S1 N1 P1 138.5(2) . . . . ?
N3 S1 N1 P1 10.7(3) . . . . ?
C13 S1 N1 P1 -106.6(3) . . . . ?
O3 P1 N1 S1 132.7(2) . . . . ?
O4 P1 N1 S1 -117.6(3) . . . . ?
N2 P1 N1 S1 6.3(3) . . . . ?
O2 P2 N2 P1 125.9(2) . . . . ?
O5 P2 N2 P1 -120.2(2) . . . . ?
N3 P2 N2 P1 3.3(3) . . . . ?
O3 P1 N2 P2 -139.4(2) . . . . ?
O4 P1 N2 P2 107.8(2) . . . . ?
N1 P1 N2 P2 -13.5(3) . . . . ?
O1 S1 N3 P2 -149.8(2) . . . . ?
N1 S1 N3 P2 -22.3(3) . . . . ?
C13 S1 N3 P2 95.2(3) . . . . ?
O2 P2 N3 S1 -108.9(3) . . . . ?
O5 P2 N3 S1 142.7(2) . . . . ?
N2 P2 N3 S1 15.9(3) . . . . ?
P2 O2 C1 C2 -100.9(4) . . . . ?
O2 C1 C2 C3 85.9(5) . . . . ?
C1 C2 C3 C4 -123.8(5) . . . . ?
C2 C3 C4 C5 178.6(4) . . . . ?
C3 C4 C5 C6 -101.2(6) . . . . ?
P1 O3 C6 C5 -109.5(4) . . . . ?
C4 C5 C6 O3 65.1(6) . . . . ?
P1 O4 C7 C8 -132.4(3) . . . . ?
O4 C7 C8 C9 68.7(5) . . . . ?
C7 C8 C9 C10 -96.1(7) . . . . ?
C8 C9 C10 C11 175.6(5) . . . . ?
C9 C10 C11 C12 -111.1(7) . . . . ?
P2 O5 C12 C11 -114.6(4) . . . . ?
C10 C11 C12 O5 74.3(6) . . . . ?
O1 S1 C13 C18 67.7(4) . . . . ?
N3 S1 C13 C18 -173.3(3) . . . . ?
N1 S1 C13 C18 -50.7(4) . . . . ?
O1 S1 C13 C14 -109.3(3) . . . . ?
N3 S1 C13 C14 9.7(4) . . . . ?
N1 S1 C13 C14 132.3(3) . . . . ?
C18 C13 C14 C15 -0.3(6) . . . . ?
S1 C13 C14 C15 176.6(3) . . . . ?
C13 C14 C15 C16 0.2(7) . . . . ?
C14 C15 C16 C17 0.3(8) . . . . ?
C15 C16 C17 C18 -0.6(8) . . . . ?
C16 C17 C18 C13 0.4(8) . . . . ?
C14 C13 C18 C17 0.1(7) . . . . ?
S1 C13 C18 C17 -176.9(4) . . . . ?
