#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:02:01 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180056 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/02/7050219.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_7050219
loop_
_publ_author_name
'Virginie Vicente'
'Alain Fruchier'
'Marc Taillefer'
'Corinne Combes-Chamalet'
'Ian J. Scowen'
'Françoise Plénat'
'Henri-Jean Cristau'
_publ_section_title
;
 Synthesis and structural studies (1H, 13C, 31P NMR and X-ray) of new
 C-bonded cyclotriphosphazenes with heterocyclic substituents from
 novel phosphinic acid derivatives
;
_journal_issue                   3
_journal_name_full               'New J. Chem.'
_journal_page_first              418
_journal_page_last               424
_journal_paper_doi               10.1039/b311046j
_journal_volume                  28
_journal_year                    2004
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C12 H12 Cl1 N1 P1'
_chemical_formula_structural     'C12.5 H9.5 CL1.5 N1.5 P1.5 S3'
_chemical_formula_sum            'C25 H19 Cl3 N3 P3 S6'
_chemical_formula_weight         376.52
_chemical_name_systematic
;
Hexa(3-thienyl)cyclotriphosphazene
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      62
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m 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                   9.828(2)
_cell_length_b                   15.632(3)
_cell_length_c                   20.084(4)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      24.13
_cell_measurement_theta_min      2.03
_cell_volume                     3085.5(11)
_computing_cell_refinement       'IPDS software (Stoe, 1996)'
_computing_data_collection       'IPDS software (Stoe, 1996)'
_computing_data_reduction        'XRED (Stoe, 1.08, 1996)'
_computing_molecular_graphics    'ORTEP-III( Burnett and Johnson,1996)'
_computing_publication_material  'WINGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1998)'
_computing_structure_solution    'SIR97 (Altomare, et al.,1999)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'φ scan'
_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  0.0512
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14257
_diffrn_reflns_theta_full        24.13
_diffrn_reflns_theta_max         24.13
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        <0.1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.883
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       prism
_exptl_crystal_F_000             1524
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         2472
_refine_ls_number_restraints     375
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0485P)²+4.0609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                2108
_reflns_number_total             2472
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            b311046j.txt
_cod_data_source_block           taille31
_cod_database_code               7050219
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.83206(6) 0.16076(4) 0.55327(3) 0.0271(2) Uani 1 1 d U A .
P2 P 1.07391(9) 0.2500 0.53031(5) 0.0301(3) Uani 1 2 d SU . .
N1 N 0.9897(2) 0.16278(15) 0.53358(11) 0.0340(5) Uani 1 1 d U . .
N2 N 0.7542(3) 0.2500 0.56121(15) 0.0303(7) Uani 1 2 d SU . .
C11 C 0.8160(2) 0.09969(18) 0.62842(12) 0.0296(6) Uani 1 1 d DU . .
C12 C 0.6916(6) 0.0807(4) 0.6608(3) 0.0431(14) Uani 0.63 1 d PDU A 1
H12 H 0.6056 0.1006 0.6458 0.052 Uiso 0.63 1 calc PR A 1
C13 C 0.7088(7) 0.0288(5) 0.7178(3) 0.0458(18) Uani 0.63 1 d PDU A 1
H13 H 0.6375 0.0076 0.7452 0.055 Uiso 0.63 1 calc PR A 1
S14 S 0.8750(2) 0.01062(15) 0.72939(9) 0.0689(6) Uani 0.63 1 d PDU A 1
C15 C 0.9231(6) 0.0677(5) 0.6626(2) 0.0481(13) Uani 0.63 1 d PDU A 1
H15 H 1.0153 0.0765 0.6501 0.058 Uiso 0.63 1 calc PR A 1
C12A C 0.8829(10) 0.0196(7) 0.6416(5) 0.049(2) Uani 0.37 1 d PDU A 2
H12A H 0.9445 -0.0061 0.6112 0.058 Uiso 0.37 1 calc PR A 2
C13A C 0.8504(12) -0.0160(7) 0.7011(5) 0.053(3) Uani 0.37 1 d PDU A 2
H13A H 0.8835 -0.0692 0.7172 0.064 Uiso 0.37 1 calc PR A 2
S14A S 0.7416(4) 0.0494(3) 0.74225(16) 0.0729(13) Uani 0.37 1 d PDU A 2
C15A C 0.7359(12) 0.1207(8) 0.6781(5) 0.058(3) Uani 0.37 1 d PDU A 2
H15A H 0.6805 0.1705 0.6783 0.070 Uiso 0.37 1 calc PR A 2
C16 C 0.7429(2) 0.09816(17) 0.49296(12) 0.0292(6) Uani 1 1 d DU . .
C17 C 0.7868(8) 0.0171(6) 0.4673(5) 0.0334(19) Uani 0.76 1 d PDU A 1
H17A H 0.8689 -0.0099 0.4808 0.040 Uiso 0.76 1 calc PR A 1
C18 C 0.7020(14) -0.0167(9) 0.4231(8) 0.051(3) Uani 0.76 1 d PDU A 1
H18A H 0.7170 -0.0698 0.4013 0.061 Uiso 0.76 1 calc PR A 1
S19 S 0.56295(19) 0.04634(12) 0.40999(8) 0.0577(5) Uani 0.76 1 d PDU A 1
C20 C 0.6225(7) 0.1224(5) 0.4649(3) 0.0397(15) Uani 0.76 1 d PDU A 1
H20A H 0.5771 0.1746 0.4745 0.048 Uiso 0.76 1 calc PR A 1
C20A C 0.5987(19) 0.1028(14) 0.4805(10) 0.050(6) Uani 0.24 1 d PDU A 2
H20B H 0.5410 0.1439 0.5008 0.060 Uiso 0.24 1 calc PR A 2
C19A C 0.5535(19) 0.0431(14) 0.4371(7) 0.049(4) Uani 0.24 1 d PDU A 2
H19A H 0.4620 0.0366 0.4227 0.059 Uiso 0.24 1 calc PR A 2
S18A S 0.6842(15) -0.0174(9) 0.4131(8) 0.067(3) Uani 0.24 1 d PDU A 2
C17A C 0.802(2) 0.0322(17) 0.4608(16) 0.033(5) Uani 0.24 1 d PDU A 2
H17B H 0.8954 0.0162 0.4643 0.039 Uiso 0.24 1 calc PR A 2
C21 C 1.1973(4) 0.2500 0.5968(2) 0.0402(10) Uani 1 2 d SU . .
C22 C 1.1610(7) 0.2247(4) 0.6639(3) 0.052(3) Uani 0.50 1 d PU . .
C23 C 1.2705(8) 0.2242(5) 0.7056(3) 0.066(3) Uani 0.50 1 d PU . .
S24 S 1.41477(14) 0.2500 0.66501(8) 0.0702(4) Uani 1 2 d SU . .
C25 C 1.3330(4) 0.2500 0.5900(2) 0.0433(10) Uani 1 2 d SU . .
H25 H 1.3784 0.2500 0.5482 0.052 Uiso 1 2 calc SR . .
C26 C 1.1750(4) 0.2500 0.45663(19) 0.0325(9) Uani 1 2 d SU . .
C27 C 1.2195(4) 0.1782(3) 0.42424(18) 0.0618(11) Uani 1 1 d U . .
C28 C 1.310(2) 0.2006(15) 0.3730(7) 0.055(4) Uani 0.50 1 d PU . .
S29 S 1.3009(6) 0.1925(4) 0.35433(19) 0.0517(9) Uani 0.50 1 d PU . .
C1 C 0.8178(5) 0.2500 0.3472(2) 0.0584(14) Uani 1 2 d SU . .
Cl12 Cl 0.90350(14) 0.15921(8) 0.32363(6) 0.0909(4) Uani 1 1 d U . .
Cl1A Cl 0.65702(17) 0.2342(4) 0.31178(11) 0.097(2) Uani 0.50 1 d PU . .
H22 H 1.067(7) 0.2500 0.686(3) 0.11(2) Uiso 1 2 d S . .
H27 H 1.212(4) 0.129(3) 0.436(2) 0.077(15) Uiso 1 1 d . . .
H1 H 0.811(7) 0.2500 0.394(3) 0.10(2) Uiso 1 2 d S . .
H28 H 1.359(8) 0.166(5) 0.333(4) 0.06(2) Uiso 0.50 1 d P . .
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'
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
_geom_angle_publ_flag
N1 P1 N2 118.11(13) . . ?
N1 P1 C16 108.55(12) . . ?
N2 P1 C16 108.10(14) . . ?
N1 P1 C11 107.71(12) . . ?
N2 P1 C11 109.77(14) . . ?
C16 P1 C11 103.64(12) . . ?
N1 P2 N1 117.32(16) . 7_565 ?
N1 P2 C26 108.86(10) . . ?
N1 P2 C26 108.86(10) 7_565 . ?
N1 P2 C21 108.55(11) . . ?
N1 P2 C21 108.55(11) 7_565 . ?
C26 P2 C21 103.88(18) . . ?
P2 N1 P1 121.96(14) . . ?
P1 N2 P1 121.46(18) . 7_565 ?
C15A C11 C15 100.0(5) . . ?
C15A C11 C12 35.5(6) . . ?
C15 C11 C12 111.2(4) . . ?
C15A C11 C12A 110.6(5) . . ?
C15 C11 C12A 39.6(4) . . ?
C12 C11 C12A 97.3(5) . . ?
C15A C11 P1 124.1(5) . . ?
C15 C11 P1 123.7(3) . . ?
C12 C11 P1 125.1(3) . . ?
C12A C11 P1 125.3(4) . . ?
C13 C12 C11 112.9(5) . . ?
C12 C13 S14 109.1(5) . . ?
C13 S14 C15 94.2(3) . . ?
C11 C15 S14 112.5(4) . . ?
C13A C12A C11 114.3(8) . . ?
C12A C13A S14A 109.3(8) . . ?
C13A S14A C15A 92.6(5) . . ?
C11 C15A S14A 113.1(6) . . ?
C17A C16 C20 113.0(12) . . ?
C17A C16 C17 12.3(19) . . ?
C20 C16 C17 111.0(4) . . ?
C17A C16 C20A 112.4(11) . . ?
C20 C16 C20A 20.1(8) . . ?
C17 C16 C20A 106.1(11) . . ?
C17A C16 P1 122.0(9) . . ?
C20 C16 P1 123.6(3) . . ?
C17 C16 P1 125.4(4) . . ?
C20A C16 P1 124.9(9) . . ?
C18 C17 C16 113.8(7) . . ?
C17 C18 S19 112.1(8) . . ?
C18 S19 C20 91.6(5) . . ?
C16 C20 S19 111.5(5) . . ?
C19A C20A C16 113.7(17) . . ?
C20A C19A S18A 109.0(14) . . ?
C19A S18A C17A 96.0(11) . . ?
C16 C17A S18A 108.8(14) . . ?
C25 C21 C22 109.9(4) . 7_565 ?
C25 C21 C22 109.9(4) . . ?
C22 C21 C22 31.6(6) 7_565 . ?
C25 C21 P2 126.4(3) . . ?
C22 C21 P2 121.5(3) 7_565 . ?
C22 C21 P2 121.5(3) . . ?
C22 C22 C23 90.3(4) 7_565 . ?
C22 C22 C21 74.2(3) 7_565 . ?
C23 C22 C21 112.2(6) . . ?
C22 C22 C23 59.7(4) 7_565 7_565 ?
C23 C22 C23 30.6(6) . 7_565 ?
C21 C22 C23 100.8(5) . 7_565 ?
C23 C23 C22 89.7(4) 7_565 . ?
C23 C23 C22 59.7(4) 7_565 7_565 ?
C22 C23 C22 30.0(5) . 7_565 ?
C23 C23 S24 76.2(3) 7_565 . ?
C22 C23 S24 111.4(5) . . ?
C22 C23 S24 101.3(4) 7_565 . ?
C23 S24 C23 27.7(5) . 7_565 ?
C23 S24 C25 91.8(3) . . ?
C23 S24 C25 91.8(3) 7_565 . ?
C21 C25 S24 112.2(4) . . ?
C27 C26 C27 110.2(4) . 7_565 ?
C27 C26 P2 124.9(2) . . ?
C27 C26 P2 124.9(2) 7_565 . ?
C26 C27 C28 110.2(10) . . ?
C26 C27 S29 116.9(4) . . ?
C28 C27 S29 12.9(9) . . ?
C27 C28 C28 104.5(10) . 7_565 ?
C27 C28 S29 111.7(14) . 7_565 ?
C28 C28 S29 13.0(6) 7_565 7_565 ?
C27 S29 C28 88.4(7) . 7_565 ?
C27 S29 S29 97.9(3) . 7_565 ?
C28 S29 S29 13.0(6) 7_565 7_565 ?
Cl12 C1 Cl12 111.5(3) 7_565 . ?
Cl12 C1 Cl1A 116.5(3) 7_565 . ?
Cl12 C1 Cl1A 102.4(3) . . ?
Cl12 C1 Cl1A 102.4(3) 7_565 7_565 ?
Cl12 C1 Cl1A 116.5(3) . 7_565 ?
Cl1A C1 Cl1A 16.2(4) . 7_565 ?
Cl1A Cl1A C1 81.9(2) 7_565 . ?
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
P1 N1 1.599(2) . ?
P1 N2 1.5991(15) . ?
P1 C16 1.787(3) . ?
P1 C11 1.793(3) . ?
P2 N1 1.596(2) . ?
P2 N1 1.596(2) 7_565 ?
P2 C26 1.782(4) . ?
P2 C21 1.804(4) . ?
N2 P1 1.5991(15) 7_565 ?
C11 C15A 1.313(9) . ?
C11 C15 1.353(6) . ?
C11 C12 1.416(6) . ?
C11 C12A 1.438(9) . ?
C12 C13 1.413(9) . ?
C13 S14 1.674(8) . ?
S14 C15 1.680(6) . ?
C12A C13A 1.357(13) . ?
C13A S14A 1.694(10) . ?
S14A C15A 1.704(9) . ?
C16 C17A 1.35(2) . ?
C16 C20 1.365(7) . ?
C16 C17 1.434(8) . ?
C16 C20A 1.441(18) . ?
C17 C18 1.328(14) . ?
C18 S19 1.705(11) . ?
S19 C20 1.724(7) . ?
C20A C19A 1.35(2) . ?
C19A S18A 1.667(16) . ?
S18A C17A 1.69(2) . ?
C21 C25 1.341(6) . ?
C21 C22 1.450(7) 7_565 ?
C21 C22 1.450(7) . ?
C22 C22 0.790(13) 7_565 ?
C22 C23 1.364(9) . ?
C22 C23 1.580(9) 7_565 ?
C23 C23 0.805(14) 7_565 ?
C23 C22 1.580(9) 7_565 ?
C23 S24 1.684(8) . ?
S24 C23 1.684(8) 7_565 ?
S24 C25 1.708(5) . ?
C26 C27 1.370(4) . ?
C26 C27 1.370(4) 7_565 ?
C27 C28 1.41(2) . ?
C27 S29 1.631(5) . ?
C28 C28 1.54(5) 7_565 ?
C28 S29 1.71(2) 7_565 ?
S29 C28 1.71(2) 7_565 ?
S29 S29 1.798(12) 7_565 ?
C1 Cl12 1.717(3) 7_565 ?
C1 Cl12 1.717(3) . ?
C1 Cl1A 1.751(5) . ?
C1 Cl1A 1.751(5) 7_565 ?
Cl1A Cl1A 0.493(13) 7_565 ?
