#------------------------------------------------------------------------------
#$Date: 2016-03-23 23:05:24 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179501 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/98/4339885.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_4339885
loop_
_publ_author_name
'Benson, Mark A.'
'Zacchini, Stefano'
'Boomishankar, Ramamoorthy'
'Chan, Yuri'
'Steiner, Alexander'
_publ_section_title
;
 Alkylation and acylation of cyclotriphosphazenes.
;
_journal_issue                   17
_journal_name_full               'Inorganic chemistry'
_journal_page_first              7097
_journal_page_last               7108
_journal_paper_doi               10.1021/ic7009463
_journal_volume                  46
_journal_year                    2007
_chemical_formula_sum            'C41 H79 Cl3 F6 N9 O6 P3 S2'
_chemical_formula_weight         1171.51
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 106.7540(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.7423(10)
_cell_length_b                   16.8937(8)
_cell_length_c                   17.5708(8)
_cell_measurement_temperature    100(2)
_cell_volume                     5611.5(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       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  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14492
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         4.25
_exptl_absorpt_coefficient_mu    0.394
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.811
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2472
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.036
_refine_diff_density_min         -1.108
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4951
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0444
_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)+(0.0495P)²+19.8005P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1134
_reflns_number_gt                4497
_reflns_number_total             4951
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic7009463-file003.cif
_cod_data_source_block           '[4Me2](CF3SO3)2.CHCl3'
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4339885
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
P1 P 1.0000 0.46260(5) 0.2500 0.01122(18) Uani 1 2 d S
P2 P 0.98253(3) 0.61884(3) 0.16425(3) 0.01229(15) Uani 1 1 d .
N1 N 0.98972(10) 0.51974(11) 0.17114(10) 0.0135(4) Uani 1 1 d .
N2 N 1.0000 0.65441(16) 0.2500 0.0154(6) Uani 1 2 d S
N3 N 1.06484(10) 0.40663(12) 0.24647(11) 0.0138(4) Uani 1 1 d D
H3 H 1.0891(13) 0.4274(15) 0.2263(15) 0.015(7) Uiso 1 1 d D
N4 N 1.03349(10) 0.64315(12) 0.11015(12) 0.0159(4) Uani 1 1 d D
H4 H 1.0664(12) 0.6177(15) 0.1160(16) 0.015(7) Uiso 1 1 d D
N5 N 0.90507(10) 0.64780(12) 0.11195(11) 0.0145(4) Uani 1 1 d D
H5 H 0.8958(15) 0.6397(17) 0.0671(13) 0.023(8) Uiso 1 1 d D
C1 C 0.97225(13) 0.47567(14) 0.09372(13) 0.0174(5) Uani 1 1 d .
H1A H 1.0130 0.4435 0.0916 0.026 Uiso 1 1 calc R
H1B H 0.9610 0.5136 0.0496 0.026 Uiso 1 1 calc R
H1C H 0.9314 0.4412 0.0894 0.026 Uiso 1 1 calc R
C31 C 1.09314(11) 0.33662(13) 0.29560(13) 0.0144(5) Uani 1 1 d .
H31 H 1.0619 0.3251 0.3301 0.017 Uiso 1 1 calc R
C32 C 1.16774(12) 0.35365(14) 0.34931(14) 0.0179(5) Uani 1 1 d .
H32A H 1.1988 0.3679 0.3161 0.022 Uiso 1 1 calc R
H32B H 1.1662 0.3992 0.3842 0.022 Uiso 1 1 calc R
C33 C 1.19824(12) 0.28195(15) 0.40027(14) 0.0211(5) Uani 1 1 d .
H33A H 1.1704 0.2718 0.4380 0.025 Uiso 1 1 calc R
H33B H 1.2476 0.2934 0.4316 0.025 Uiso 1 1 calc R
C34 C 1.19719(13) 0.20820(16) 0.34987(16) 0.0258(6) Uani 1 1 d .
H34A H 1.2136 0.1621 0.3851 0.031 Uiso 1 1 calc R
H34B H 1.2301 0.2155 0.3173 0.031 Uiso 1 1 calc R
C35 C 1.12275(13) 0.19204(15) 0.29539(15) 0.0234(5) Uani 1 1 d .
H35A H 1.0911 0.1785 0.3280 0.028 Uiso 1 1 calc R
H35B H 1.1241 0.1462 0.2607 0.028 Uiso 1 1 calc R
C36 C 1.09329(12) 0.26431(14) 0.24377(14) 0.0181(5) Uani 1 1 d .
H36A H 1.1226 0.2752 0.2078 0.022 Uiso 1 1 calc R
H36B H 1.0445 0.2531 0.2107 0.022 Uiso 1 1 calc R
C41 C 1.03803(12) 0.72708(14) 0.08734(13) 0.0159(5) Uani 1 1 d .
H41 H 1.0045 0.7583 0.1086 0.019 Uiso 1 1 calc R
C42 C 1.01616(13) 0.73741(15) -0.00237(14) 0.0220(5) Uani 1 1 d .
H42A H 0.9678 0.7164 -0.0255 0.026 Uiso 1 1 calc R
H42B H 1.0487 0.7072 -0.0251 0.026 Uiso 1 1 calc R
C43 C 1.01811(14) 0.82532(16) -0.02348(15) 0.0267(6) Uani 1 1 d .
H43A H 1.0054 0.8311 -0.0820 0.032 Uiso 1 1 calc R
H43B H 0.9826 0.8545 -0.0045 0.032 Uiso 1 1 calc R
C44 C 1.09119(13) 0.86121(15) 0.01384(15) 0.0229(5) Uani 1 1 d .
H44A H 1.1256 0.8371 -0.0106 0.028 Uiso 1 1 calc R
H44B H 1.0895 0.9188 0.0029 0.028 Uiso 1 1 calc R
C45 C 1.11568(13) 0.84763(15) 0.10342(15) 0.0230(5) Uani 1 1 d .
H45A H 1.0855 0.8787 0.1287 0.028 Uiso 1 1 calc R
H45B H 1.1649 0.8667 0.1250 0.028 Uiso 1 1 calc R
C46 C 1.11221(13) 0.76001(15) 0.12446(14) 0.0212(5) Uani 1 1 d .
H46A H 1.1467 0.7296 0.1049 0.025 Uiso 1 1 calc R
H46B H 1.1251 0.7540 0.1829 0.025 Uiso 1 1 calc R
C51 C 0.84247(11) 0.65123(14) 0.14162(13) 0.0151(5) Uani 1 1 d .
H51 H 0.8580 0.6687 0.1984 0.018 Uiso 1 1 calc R
C52 C 0.80664(12) 0.57090(14) 0.13721(15) 0.0207(5) Uani 1 1 d .
H52A H 0.8394 0.5334 0.1729 0.025 Uiso 1 1 calc R
H52B H 0.7961 0.5502 0.0823 0.025 Uiso 1 1 calc R
C53 C 0.73803(13) 0.57571(16) 0.16094(16) 0.0253(6) Uani 1 1 d .
H53A H 0.7147 0.5232 0.1536 0.030 Uiso 1 1 calc R
H53B H 0.7491 0.5900 0.2179 0.030 Uiso 1 1 calc R
C54 C 0.68781(13) 0.63703(17) 0.11114(16) 0.0275(6) Uani 1 1 d .
H54A H 0.6731 0.6203 0.0548 0.033 Uiso 1 1 calc R
H54B H 0.6449 0.6410 0.1294 0.033 Uiso 1 1 calc R
C55 C 0.72368(13) 0.71725(17) 0.11838(16) 0.0273(6) Uani 1 1 d .
H55A H 0.7350 0.7359 0.1741 0.033 Uiso 1 1 calc R
H55B H 0.6910 0.7560 0.0843 0.033 Uiso 1 1 calc R
C56 C 0.79174(13) 0.71265(15) 0.09346(15) 0.0230(5) Uani 1 1 d .
H56A H 0.7798 0.6989 0.0363 0.028 Uiso 1 1 calc R
H56B H 0.8151 0.7651 0.1009 0.028 Uiso 1 1 calc R
S1 S 1.17175(3) 0.48062(4) 0.09896(3) 0.01749(15) Uani 1 1 d .
O1 O 1.13915(9) 0.40985(11) 0.05899(10) 0.0243(4) Uani 1 1 d .
O2 O 1.17489(10) 0.54609(12) 0.04757(12) 0.0351(5) Uani 1 1 d .
O3 O 1.14932(10) 0.50277(12) 0.16718(11) 0.0309(4) Uani 1 1 d .
C10 C 1.26400(13) 0.45253(16) 0.14082(16) 0.0265(6) Uani 1 1 d .
F1 F 1.26995(9) 0.39512(10) 0.19528(11) 0.0425(4) Uani 1 1 d .
F2 F 1.29116(9) 0.42421(11) 0.08610(11) 0.0434(5) Uani 1 1 d .
F3 F 1.30370(7) 0.51345(9) 0.17661(9) 0.0297(4) Uani 1 1 d .
C11 C 0.9752(3) 0.9599(4) 0.2475(4) 0.0370(14) Uani 0.50 1 d P
H11 H 0.9230 0.9604 0.2400 0.044 Uiso 0.50 1 calc PR
Cl1 Cl 1.0000 0.85887(8) 0.2500 0.0795(6) Uani 1 2 d S
Cl2 Cl 0.98770(8) 1.00550(7) 0.16543(7) 0.0829(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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
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
N3 P1 N3 107.92(15) . 2_755
N3 P1 N1 118.00(9) . 2_755
N3 P1 N1 102.58(9) 2_755 2_755
N3 P1 N1 102.58(9) . .
N3 P1 N1 118.00(9) 2_755 .
N1 P1 N1 108.52(13) 2_755 .
N2 P2 N5 109.94(9) . .
N2 P2 N4 117.69(9) . .
N5 P2 N4 103.59(10) . .
N2 P2 N1 108.80(11) . .
N5 P2 N1 112.87(10) . .
N4 P2 N1 103.90(10) . .
C1 N1 P1 114.26(15) . .
C1 N1 P2 115.85(14) . .
P1 N1 P2 128.99(11) . .
P2 N2 P2 134.86(18) . 2_755
C31 N3 P1 128.34(16) . .
C41 N4 P2 119.73(16) . .
C51 N5 P2 124.26(15) . .
N3 C31 C36 111.00(18) . .
N3 C31 C32 110.17(18) . .
C36 C31 C32 110.60(18) . .
C33 C32 C31 111.11(19) . .
C32 C33 C34 111.8(2) . .
C33 C34 C35 111.0(2) . .
C34 C35 C36 111.1(2) . .
C31 C36 C35 110.53(19) . .
N4 C41 C42 111.64(19) . .
N4 C41 C46 110.99(19) . .
C42 C41 C46 110.62(19) . .
C41 C42 C43 110.0(2) . .
C44 C43 C42 111.5(2) . .
C45 C44 C43 111.3(2) . .
C44 C45 C46 111.8(2) . .
C41 C46 C45 110.7(2) . .
N5 C51 C56 108.37(18) . .
N5 C51 C52 111.81(19) . .
C56 C51 C52 111.01(19) . .
C51 C52 C53 111.9(2) . .
C54 C53 C52 111.1(2) . .
C55 C54 C53 110.4(2) . .
C54 C55 C56 111.0(2) . .
C51 C56 C55 111.6(2) . .
O2 S1 O1 115.18(11) . .
O2 S1 O3 113.63(13) . .
O1 S1 O3 114.80(11) . .
O2 S1 C10 103.58(12) . .
O1 S1 C10 103.59(11) . .
O3 S1 C10 104.07(12) . .
F2 C10 F3 108.4(2) . .
F2 C10 F1 106.7(2) . .
F3 C10 F1 107.6(2) . .
F2 C10 S1 111.72(18) . .
F3 C10 S1 111.86(18) . .
F1 C10 S1 110.36(18) . .
Cl2 C11 Cl2 115.4(4) 2_755 .
Cl2 C11 Cl1 112.0(4) 2_755 .
Cl2 C11 Cl1 110.3(3) . .
C11 Cl1 C11 31.4(4) 2_755 .
C11 Cl2 C11 32.8(4) 2_755 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 N3 1.6070(19) .
P1 N3 1.6070(19) 2_755
P1 N1 1.6526(18) 2_755
P1 N1 1.6526(18) .
P2 N2 1.5654(11) .
P2 N5 1.6161(19) .
P2 N4 1.623(2) .
P2 N1 1.6817(19) .
N1 C1 1.501(3) .
N2 P2 1.5654(11) 2_755
N3 C31 1.476(3) .
N4 C41 1.483(3) .
N5 C51 1.474(3) .
C31 C36 1.524(3) .
C31 C32 1.530(3) .
C32 C33 1.523(3) .
C33 C34 1.525(4) .
C34 C35 1.530(3) .
C35 C36 1.532(3) .
C41 C42 1.519(3) .
C41 C46 1.526(3) .
C42 C43 1.534(3) .
C43 C44 1.528(4) .
C44 C45 1.525(3) .
C45 C46 1.532(3) .
C51 C56 1.519(3) .
C51 C52 1.522(3) .
C52 C53 1.530(3) .
C53 C54 1.524(4) .
C54 C55 1.517(4) .
C55 C56 1.530(3) .
S1 O2 1.440(2) .
S1 O1 1.4410(18) .
S1 O3 1.4419(19) .
S1 C10 1.820(3) .
C10 F2 1.318(3) .
C10 F3 1.336(3) .
C10 F1 1.344(3) .
C11 Cl2 1.681(7) 2_755
C11 Cl2 1.715(6) .
C11 Cl1 1.773(6) .
Cl1 C11 1.773(6) 2_755
Cl2 C11 1.681(7) 2_755
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
N3 H3 O3 0.76(2) 2.20(2) 2.950(3) 171(3) .
N4 H4 O3 0.76(2) 2.53(2) 3.246(3) 157(3) .
N5 H5 O1 0.77(2) 2.28(2) 3.036(3) 168(3) 5_765
