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#$Date: 2025-08-21 14:21:36 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301847 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/58/7015865.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_7015865
loop_
_publ_author_name
'Beşli, Serap'
'Coles, Simon J.'
'Davies, David B.'
'Kılıç, Adem'
'Okutan, Elif'
'Shaw, Robert A.'
'Eçik, Esra Tanrıverdi'
'Çiftçi, Gönül Yenilmez'
_publ_section_title
;
 Competitive formation of cis and trans derivatives in the nucleophilic
 substitution reactions of cyclophosphazenes having a mono-spiro P-NHR
 group.
;
_journal_issue                   18
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4959
_journal_page_last               4969
_journal_paper_doi               10.1039/c1dt10176e
_journal_volume                  40
_journal_year                    2011
_chemical_formula_sum            'C9 H12 Cl3 N4 O2 P3'
_chemical_formula_weight         407.49
_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
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.6597(17)
_cell_length_b                   8.0541(10)
_cell_length_c                   35.094(5)
_cell_measurement_reflns_used    2479
_cell_measurement_temperature    296.0(2)
_cell_measurement_theta_max      26.1831
_cell_measurement_theta_min      2.9050
_cell_volume                     3295.6(8)
_computing_cell_refinement       'SAINT V7.66A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.66A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.0(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  Apex2
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            10456
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.16
_diffrn_source                   ImuS
_exptl_absorpt_coefficient_mu    0.854
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.285
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0371
_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)+(0.0367P)²+0.4545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0918
_reflns_number_gt                2020
_reflns_number_total             2907
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt10176e.txt
_cod_data_source_block           8a
_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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7015865
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_type_symbol
_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_disorder_assembly
_atom_site_disorder_group
P P1 0.58426(8) -0.06387(10) 0.36631(2) 0.0377(2) Uani d . 1 . .
P P2 0.56800(7) 0.17407(10) 0.30899(2) 0.0330(2) Uani d . 1 . .
P P3 0.45135(8) 0.21056(10) 0.37709(2) 0.0390(2) Uani d . 1 . .
N N1 0.6099(2) -0.0050(3) 0.32467(7) 0.0431(7) Uani d . 1 . .
N N2 0.4984(2) 0.2835(3) 0.33869(7) 0.0434(7) Uani d . 1 . .
N N3 0.4998(3) 0.0394(3) 0.39196(8) 0.0524(8) Uani d . 1 . .
N N4 0.6725(2) 0.2824(3) 0.29118(8) 0.0424(7) Uani d . 1 . .
H H4 0.716(3) 0.325(4) 0.3054(10) 0.064 Uiso d . 1 . .
O O1 0.48966(16) 0.1434(3) 0.27322(6) 0.0377(5) Uani d . 1 . .
O O2 0.4669(2) 0.3506(3) 0.40774(6) 0.0461(6) Uani d . 1 . .
Cl Cl1 0.53282(8) -0.29977(10) 0.36547(3) 0.0528(3) Uani d . 1 . .
Cl Cl2 0.73424(8) -0.08947(12) 0.39439(3) 0.0609(3) Uani d . 1 . .
Cl Cl3 0.28004(8) 0.18809(14) 0.37414(3) 0.0692(3) Uani d . 1 . .
C C1 0.5409(3) 0.0874(4) 0.23783(9) 0.0466(9) Uani d . 1 . .
H H1A 0.4827 0.0836 0.2181 0.056 Uiso calc R 1 . .
H H1B 0.5707 -0.0241 0.2412 0.056 Uiso calc R 1 . .
C C2 0.6359(3) 0.1999(5) 0.22552(10) 0.0535(10) Uani d . 1 . .
H H2A 0.6044 0.3081 0.2194 0.064 Uiso calc R 1 . .
H H2B 0.6711 0.1555 0.2027 0.064 Uiso calc R 1 . .
C C3 0.7257(3) 0.2193(4) 0.25584(10) 0.0499(9) Uani d . 1 . .
H H3A 0.7618 0.1129 0.2607 0.06 Uiso calc R 1 . .
H H3B 0.7843 0.2961 0.2472 0.06 Uiso calc R 1 . .
C C4 0.4302(3) 0.3370(4) 0.44636(9) 0.0446(9) Uani d . 1 . .
C C5 0.4950(4) 0.2503(5) 0.47134(11) 0.0700(12) Uani d . 1 . .
H H5 0.5602 0.194 0.4633 0.084 Uiso calc R 1 . .
C C6 0.4615(5) 0.2474(6) 0.50949(13) 0.0905(16) Uani d . 1 . .
H H6 0.5038 0.1866 0.5271 0.109 Uiso calc R 1 . .
C C7 0.3678(6) 0.3329(6) 0.52087(13) 0.0876(17) Uani d . 1 . .
H H7 0.3468 0.3328 0.5464 0.105 Uiso calc R 1 . .
C C8 0.3045(5) 0.4184(6) 0.49528(14) 0.0904(16) Uani d . 1 . .
H H8 0.2397 0.4759 0.5033 0.109 Uiso calc R 1 . .
C C9 0.3352(4) 0.4211(5) 0.45709(11) 0.0715(12) Uani d . 1 . .
H H9 0.2917 0.4793 0.4393 0.086 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 P1 N3 . . 119.61(14) ?
N1 P1 Cl1 . . 109.43(11) ?
N3 P1 Cl1 . . 108.92(12) ?
N1 P1 Cl2 . . 108.75(11) ?
N3 P1 Cl2 . . 108.50(13) ?
Cl1 P1 Cl2 . . 99.82(5) ?
O1 P2 N2 . . 108.33(14) ?
O1 P2 N1 . . 107.86(13) ?
N2 P2 N1 . . 115.20(14) ?
O1 P2 N4 . . 102.30(13) ?
N2 P2 N4 . . 109.75(15) ?
N1 P2 N4 . . 112.51(15) ?
O2 P3 N2 . . 106.20(13) ?
O2 P3 N3 . . 111.10(14) ?
N2 P3 N3 . . 119.08(14) ?
O2 P3 Cl3 . . 102.41(10) ?
N2 P3 Cl3 . . 109.71(12) ?
N3 P3 Cl3 . . 107.10(12) ?
P1 N1 P2 . . 121.96(16) ?
P3 N2 P2 . . 122.29(16) ?
P1 N3 P3 . . 119.78(17) ?
C3 N4 P2 . . 117.0(2) ?
C3 N4 H4 . . 114.(3) ?
P2 N4 H4 . . 118.(3) ?
C1 O1 P2 . . 119.55(19) ?
C4 O2 P3 . . 124.17(19) ?
O1 C1 C2 . . 111.3(3) ?
O1 C1 H1A . . 109.4 ?
C2 C1 H1A . . 109.4 ?
O1 C1 H1B . . 109.4 ?
C2 C1 H1B . . 109.4 ?
H1A C1 H1B . . 108.0 ?
C1 C2 C3 . . 112.0(3) ?
C1 C2 H2A . . 109.2 ?
C3 C2 H2A . . 109.2 ?
C1 C2 H2B . . 109.2 ?
C3 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
N4 C3 C2 . . 109.8(3) ?
N4 C3 H3A . . 109.7 ?
C2 C3 H3A . . 109.7 ?
N4 C3 H3B . . 109.7 ?
C2 C3 H3B . . 109.7 ?
H3A C3 H3B . . 108.2 ?
C9 C4 C5 . . 122.4(4) ?
C9 C4 O2 . . 118.2(3) ?
C5 C4 O2 . . 119.3(3) ?
C4 C5 C6 . . 118.4(4) ?
C4 C5 H5 . . 120.8 ?
C6 C5 H5 . . 120.8 ?
C7 C6 C5 . . 120.1(5) ?
C7 C6 H6 . . 120.0 ?
C5 C6 H6 . . 120.0 ?
C8 C7 C6 . . 120.3(5) ?
C8 C7 H7 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
C7 C8 C9 . . 120.6(5) ?
C7 C8 H8 . . 119.7 ?
C9 C8 H8 . . 119.7 ?
C4 C9 C8 . . 118.2(4) ?
C4 C9 H9 . . 120.9 ?
C8 C9 H9 . . 120.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 N1 . 1.565(3) ?
P1 N3 . 1.573(3) ?
P1 Cl1 . 1.9926(12) ?
P1 Cl2 . 2.0179(12) ?
P2 O1 . 1.572(2) ?
P2 N2 . 1.588(3) ?
P2 N1 . 1.619(3) ?
P2 N4 . 1.624(3) ?
P3 O2 . 1.569(2) ?
P3 N2 . 1.569(3) ?
P3 N3 . 1.578(3) ?
P3 Cl3 . 2.0082(14) ?
N4 C3 . 1.477(4) ?
N4 H4 . 0.79(3) ?
O1 C1 . 1.451(3) ?
O2 C4 . 1.426(4) ?
C1 C2 . 1.495(5) ?
C1 H1A . 0.97 ?
C1 H1B . 0.97 ?
C2 C3 . 1.501(5) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
C4 C9 . 1.352(5) ?
C4 C5 . 1.352(5) ?
C5 C6 . 1.394(6) ?
C5 H5 . 0.93 ?
C6 C7 . 1.352(7) ?
C6 H6 . 0.93 ?
C7 C8 . 1.351(7) ?
C7 H7 . 0.93 ?
C8 C9 . 1.388(5) ?
C8 H8 . 0.93 ?
C9 H9 . 0.93 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N3 P1 N1 P2 . . . . 9.6(3) ?
Cl1 P1 N1 P2 . . . . 136.21(17) ?
Cl2 P1 N1 P2 . . . . -115.69(18) ?
O1 P2 N1 P1 . . . . -121.73(19) ?
N2 P2 N1 P1 . . . . -0.6(3) ?
N4 P2 N1 P1 . . . . 126.2(2) ?
O2 P3 N2 P2 . . . . 142.2(2) ?
N3 P3 N2 P2 . . . . 16.0(3) ?
Cl3 P3 N2 P2 . . . . -107.86(19) ?
O1 P2 N2 P3 . . . . 108.6(2) ?
N1 P2 N2 P3 . . . . -12.3(3) ?
N4 P2 N2 P3 . . . . -140.5(2) ?
N1 P1 N3 P3 . . . . -6.1(3) ?
Cl1 P1 N3 P3 . . . . -132.93(18) ?
Cl2 P1 N3 P3 . . . . 119.33(19) ?
O2 P3 N3 P1 . . . . -130.1(2) ?
N2 P3 N3 P1 . . . . -6.3(3) ?
Cl3 P3 N3 P1 . . . . 118.81(19) ?
O1 P2 N4 C3 . . . . -48.5(3) ?
N2 P2 N4 C3 . . . . -163.3(2) ?
N1 P2 N4 C3 . . . . 67.0(3) ?
N2 P2 O1 C1 . . . . 163.1(2) ?
N1 P2 O1 C1 . . . . -71.6(2) ?
N4 P2 O1 C1 . . . . 47.3(3) ?
N2 P3 O2 C4 . . . . 177.2(3) ?
N3 P3 O2 C4 . . . . -51.9(3) ?
Cl3 P3 O2 C4 . . . . 62.2(3) ?
P2 O1 C1 C2 . . . . -54.2(3) ?
O1 C1 C2 C3 . . . . 55.6(4) ?
P2 N4 C3 C2 . . . . 56.7(3) ?
C1 C2 C3 N4 . . . . -57.3(4) ?
P3 O2 C4 C9 . . . . -105.2(3) ?
P3 O2 C4 C5 . . . . 79.1(4) ?
C9 C4 C5 C6 . . . . 0.4(6) ?
O2 C4 C5 C6 . . . . 175.9(3) ?
C4 C5 C6 C7 . . . . -1.4(7) ?
C5 C6 C7 C8 . . . . 1.5(8) ?
C6 C7 C8 C9 . . . . -0.6(8) ?
C5 C4 C9 C8 . . . . 0.4(6) ?
O2 C4 C9 C8 . . . . -175.1(4) ?
C7 C8 C9 C4 . . . . -0.3(7) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139156588
