#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/60/2206097.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2206097
loop_
_publ_author_name
'Çaylak, Nagihan'
'Hökelek, Tuncer'
'Büyükgüngör, Orhan'
'Dal, Hakan'
'Süzen, Yasemin'
'Kılıç, Zeynel'
_publ_section_title
4',4',6',6'-Tetrachloro-3-(4,6-dimethylpyridin-2-yl)-3,4-dihydrospiro[1,3,2-benzoxazaphosphinine-2,2'-(2λ⁵,4λ⁵,6λ⁵-cyclotriphosphazene)]
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1557
_journal_page_last               o1560
_journal_paper_doi               10.1107/S1600536805013383
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C14 H14 Cl4 N5 O P3'
_chemical_formula_moiety         'C14 H14 Cl4 N5 O P3'
_chemical_formula_sum            'C14 H14 Cl4 N5 O P3'
_chemical_formula_weight         503.01
_chemical_name_systematic
;
4',4',6',6'-Tetrachloro-3-(4,6-dimethylpyridin-2-yl)-3,4-dihydrospiro[1,3,2-
benzoxazaphosphinine-2,2'-(2λ⁵,4λ⁵,6λ⁵-cyclotriphosphazene)]
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9310(5)
_cell_length_b                   11.9091(10)
_cell_length_c                   21.3948(15)
_cell_measurement_reflns_used    5847
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.24
_cell_measurement_theta_min      1.71
_cell_volume                     2020.8(3)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        X-RED
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Stoe IPDS-II'
_diffrn_measurement_method       φ
_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  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9087
_diffrn_reflns_theta_full        27.05
_diffrn_reflns_theta_max         27.05
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.840
_exptl_absorpt_correction_T_max  0.850
_exptl_absorpt_correction_T_min  0.758
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.452
_refine_ls_abs_structure_details 'Flack (1983), with 1667 Friedel pairs'
_refine_ls_abs_structure_Flack   0.06(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0298
_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)+(0.0536P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0744
_reflns_number_gt                3874
_reflns_number_total             4149
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6350.cif
_cod_data_source_block           I
_cod_database_code               2206097
_cod_database_fobs_code          2206097
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Cl1 0.86957(8) 0.99117(5) 0.88126(3) 0.02084(13) Uani d . 1 Cl
Cl2 0.77812(9) 0.76941(5) 0.94696(3) 0.02431(14) Uani d . 1 Cl
Cl3 0.26464(9) 1.00702(6) 0.80518(3) 0.02508(14) Uani d . 1 Cl
Cl4 0.20380(8) 0.79022(5) 0.87994(3) 0.02556(14) Uani d . 1 Cl
P1 0.67277(8) 0.91546(5) 0.92224(3) 0.01599(13) Uani d . 1 P
P2 0.34745(8) 0.92823(5) 0.88202(3) 0.01711(13) Uani d . 1 P
P3 0.43946(8) 1.03700(5) 0.99012(3) 0.01546(13) Uani d . 1 P
O1 0.3668(2) 1.00203(13) 1.05646(7) 0.0193(4) Uani d . 1 O
N1 0.5360(3) 0.89155(17) 0.86995(9) 0.0201(4) Uani d . 1 N
N2 0.2998(3) 0.99908(17) 0.94158(9) 0.0180(4) Uani d . 1 N
N3 0.6204(3) 0.98061(17) 0.98269(9) 0.0176(4) Uani d . 1 N
N4 0.4525(3) 1.17528(16) 0.99733(9) 0.0181(4) Uani d . 1 N
N5 0.5270(3) 1.18751(17) 0.89303(9) 0.0190(4) Uani d . 1 N
C1 0.4524(3) 1.0409(2) 1.10965(10) 0.0198(5) Uani d . 1 C
C2 0.4860(4) 0.9669(2) 1.15773(12) 0.0248(6) Uani d . 1 C
C3 0.5686(4) 1.0064(3) 1.20972(12) 0.0299(6) Uani d . 1 C
C4 0.6180(4) 1.1168(3) 1.21357(13) 0.0318(7) Uani d . 1 C
C5 0.5837(4) 1.1911(3) 1.16475(12) 0.0275(6) Uani d . 1 C
C6 0.4974(3) 1.1528(2) 1.11187(11) 0.0207(5) Uani d . 1 C
C7 0.4513(4) 1.2308(2) 1.05925(11) 0.0202(5) Uani d . 1 C
C8 0.4779(3) 1.2430(2) 0.94425(11) 0.0184(5) Uani d . 1 C
C9 0.4534(3) 1.3584(2) 0.94720(12) 0.0200(5) Uani d . 1 C
C10 0.4846(3) 1.4211(2) 0.89364(12) 0.0217(5) Uani d . 1 C
C11 0.5380(4) 1.3649(2) 0.84073(12) 0.0232(5) Uani d . 1 C
C12 0.5561(3) 1.2492(2) 0.84108(11) 0.0220(5) Uani d . 1 C
C13 0.6144(4) 1.1877(2) 0.78389(12) 0.0298(6) Uani d . 1 C
C14 0.4592(4) 1.5466(2) 0.89427(14) 0.0310(6) Uani d . 1 C
H13A 0.6194 1.1087 0.7926 0.045 Uiso calc R 1 H
H13B 0.7243 1.2141 0.7722 0.045 Uiso calc R 1 H
H13C 0.5367 1.2010 0.7503 0.045 Uiso calc R 1 H
H14A 0.4220 1.5697 0.9350 0.046 Uiso calc R 1 H
H14B 0.3757 1.5667 0.8638 0.046 Uiso calc R 1 H
H14C 0.5636 1.5833 0.8845 0.046 Uiso calc R 1 H
H21 0.450(4) 0.896(2) 1.1557(12) 0.013(7) Uiso d . 1 H
H31 0.595(4) 0.957(2) 1.2419(14) 0.023(8) Uiso d . 1 H
H41 0.670(5) 1.144(3) 1.2455(16) 0.031(9) Uiso d . 1 H
H51 0.620(5) 1.262(3) 1.1681(16) 0.032(9) Uiso d . 1 H
H71 0.345(5) 1.258(2) 1.0663(13) 0.021(7) Uiso d . 1 H
H72 0.533(4) 1.292(2) 1.0605(13) 0.019(7) Uiso d . 1 H
H91 0.410(4) 1.393(2) 0.9848(12) 0.014(7) Uiso d . 1 H
H111 0.552(6) 1.400(3) 0.8056(17) 0.046(11) Uiso d . 1 H
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'
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_publ_flag
N1 P1 Cl1 107.76(9) ?
N1 P1 Cl2 108.44(8) ?
N3 P1 N1 119.42(12) yes
N3 P1 Cl2 108.88(8) ?
N3 P1 Cl1 110.21(9) ?
Cl2 P1 Cl1 100.45(4) ?
N1 P2 Cl3 107.81(9) ?
N1 P2 Cl4 107.96(8) ?
N2 P2 N1 120.52(11) yes
N2 P2 Cl4 108.77(9) ?
N2 P2 Cl3 109.54(8) ?
Cl4 P2 Cl3 100.36(4) ?
O1 P3 N3 107.80(10) yes
O1 P3 N4 101.54(9) yes
N2 P3 O1 104.94(11) yes
N2 P3 N3 116.38(11) yes
N2 P3 N4 112.83(11) yes
N3 P3 N4 111.85(12) yes
C1 O1 P3 117.58(16) ?
P2 N1 P1 118.89(13) yes
P2 N2 P3 121.04(14) yes
P1 N3 P3 122.09(13) yes
C7 N4 P3 121.79(16) ?
C8 N4 C7 117.82(19) ?
C8 N4 P3 120.22(16) ?
C8 N5 C12 117.0(2) ?
C6 C1 C2 122.7(3) ?
C6 C1 O1 118.1(2) ?
C2 C1 O1 119.1(2) ?
C3 C2 C1 118.5(3) ?
C3 C2 H21 121.0(18) ?
C1 C2 H21 120.5(18) ?
C2 C3 C4 120.8(3) ?
C2 C3 H31 119.2(19) ?
C4 C3 H31 120.0(19) ?
C3 C4 C5 120.4(3) ?
C3 C4 H41 123(2) ?
C5 C4 H41 117(2) ?
C4 C5 C6 119.6(3) ?
C4 C5 H51 118(2) ?
C6 C5 H51 122(2) ?
C1 C6 C5 118.0(3) ?
C1 C6 C7 120.5(2) ?
C5 C6 C7 121.5(2) ?
N4 C7 C6 113.1(2) ?
N4 C7 H71 108.1(19) ?
C6 C7 H71 108.6(18) ?
N4 C7 H72 110.7(17) ?
C6 C7 H72 106.2(17) ?
H71 C7 H72 110(3) ?
N5 C8 C9 124.5(2) ?
N5 C8 N4 114.8(2) ?
C9 C8 N4 120.7(2) ?
C8 C9 C10 118.0(2) ?
C8 C9 H91 120.9(16) ?
C10 C9 H91 121.0(16) ?
C11 C10 C9 118.0(2) ?
C11 C10 C14 121.9(2) ?
C9 C10 C14 120.1(2) ?
C10 C11 C12 120.6(2) ?
C10 C11 H111 121(3) ?
C12 C11 H111 118(3) ?
N5 C12 C11 121.8(2) ?
N5 C12 C13 117.3(2) ?
C11 C12 C13 120.9(2) ?
C12 C13 H13A 109.5 ?
C12 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C12 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
C10 C14 H14A 109.5 ?
C10 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
C10 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P1 Cl1 2.0045(9) ?
P1 Cl2 2.0008(9) ?
P1 N1 1.584(2) yes
P1 N3 1.5643(19) yes
P2 Cl3 2.0036(9) ?
P2 Cl4 2.0003(9) ?
P2 N1 1.579(2) yes
P2 N2 1.5743(19) yes
P3 O1 1.5875(17) yes
P3 N2 1.584(2) yes
P3 N3 1.592(2) yes
P3 N4 1.657(2) yes
O1 C1 1.403(3) ?
N4 C7 1.481(3) ?
N5 C12 1.352(3) ?
C1 C6 1.380(4) ?
C1 C2 1.380(4) ?
C2 H21 0.89(3) ?
C3 C2 1.374(4) ?
C3 C4 1.375(5) ?
C3 H31 0.93(3) ?
C4 H41 0.86(4) ?
C5 C4 1.395(4) ?
C5 H51 0.90(4) ?
C6 C5 1.399(4) ?
C7 C6 1.505(3) ?
C7 H71 0.91(4) ?
C7 H72 0.97(3) ?
C8 N5 1.338(3) ?
C8 C9 1.389(3) ?
C8 N4 1.408(3) ?
C9 H91 0.97(3) ?
C9 C10 1.390(4) ?
C10 C11 1.382(4) ?
C10 C14 1.508(4) ?
C11 C12 1.385(4) ?
C11 H111 0.87(4) ?
C13 C12 1.499(3) ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
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_publ_flag
N3 P1 N1 P2 -3.4(2) yes
Cl2 P1 N1 P2 121.98(12) ?
Cl1 P1 N1 P2 -130.10(12) ?
N1 P1 N3 P3 -7.6(2) yes
Cl2 P1 N3 P3 -132.81(12) ?
Cl1 P1 N3 P3 117.91(13) ?
N2 P2 N1 P1 6.7(2) yes
Cl4 P2 N1 P1 -119.05(13) ?
Cl3 P2 N1 P1 133.33(12) ?
N1 P2 N2 P3 1.0(2) yes
Cl4 P2 N2 P3 126.38(13) ?
Cl3 P2 N2 P3 -124.83(12) ?
O1 P3 N2 P2 -130.47(14) yes
N3 P3 N2 P2 -11.4(2) yes
N4 P3 N2 P2 119.84(15) yes
N2 P3 O1 C1 -170.39(17) ?
N3 P3 O1 C1 64.95(18) ?
N4 P3 O1 C1 -52.72(19) ?
N2 P3 N4 C8 -54.7(2) ?
O1 P3 N4 C8 -166.5(2) ?
N3 P3 N4 C8 78.8(2) ?
N2 P3 N4 C7 130.1(2) ?
O1 P3 N4 C7 18.3(2) ?
N3 P3 N4 C7 -96.4(2) ?
N2 P3 N3 P1 14.8(2) yes
O1 P3 N3 P1 132.32(14) ?
N4 P3 N3 P1 -116.88(15) ?
P3 O1 C1 C6 46.9(3) ?
P3 O1 C1 C2 -134.1(2) ?
C8 N4 C7 C6 -155.4(2) ?
P3 N4 C7 C6 19.9(3) ?
C8 N5 C12 C11 0.7(4) ?
C8 N5 C12 C13 178.9(3) ?
C2 C1 C6 C5 1.4(4) ?
O1 C1 C6 C5 -179.6(2) ?
C2 C1 C6 C7 -177.4(2) ?
O1 C1 C6 C7 1.6(4) ?
C6 C1 C2 C3 -0.5(4) ?
O1 C1 C2 C3 -179.5(2) ?
C2 C3 C4 C5 0.5(5) ?
C6 C5 C4 C3 0.5(5) ?
C1 C6 C5 C4 -1.4(4) ?
C7 C6 C5 C4 177.4(3) ?
N4 C7 C6 C1 -33.7(4) ?
N4 C7 C6 C5 147.5(3) ?
N5 C8 C9 C10 -1.2(4) ?
N4 C8 C9 C10 178.4(2) ?
N5 C8 N4 C7 161.2(2) ?
C9 C8 N4 C7 -18.5(4) ?
N5 C8 N4 P3 -14.3(3) ?
C9 C8 N4 P3 166.1(2) ?
C9 C8 N5 C12 0.8(4) ?
N4 C8 N5 C12 -178.8(2) ?
C4 C3 C2 C1 -0.5(4) ?
C9 C10 C11 C12 1.3(4) ?
C14 C10 C11 C12 -178.3(3) ?
C11 C10 C9 C8 0.1(4) ?
C14 C10 C9 C8 179.7(3) ?
C10 C11 C12 N5 -1.8(4) ?
C10 C11 C12 C13 -179.9(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21129360
