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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/7/01/58/7015860.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_7015860
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            'C7 H15 Cl3 N5 O P3'
_chemical_formula_weight         384.50
_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                 114.007(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.7916(4)
_cell_length_b                   17.6220(5)
_cell_length_c                   15.4171(4)
_cell_measurement_reflns_used    82060
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     3174.60(16)
_computing_cell_refinement       'DENZO, COLLECT'
_computing_data_reduction        'DENZO, COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            32010
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.94
_diffrn_standards_decay_%        negligible
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.878
_exptl_absorpt_correction_T_max  0.8440
_exptl_absorpt_correction_T_min  0.8440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.067
_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     176
_refine_ls_number_reflns         3643
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.056
_refine_ls_shift/su_mean         0.030
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0752P)²+4.8207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1452
_reflns_number_gt                2745
_reflns_number_total             3643
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt10176e.txt
_cod_data_source_block           2006src1518r
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      C2/c
_cod_database_code               7015860
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4863(4) -0.0936(2) 0.1030(3) 0.0848(13) Uani 1 1 d . . .
H1A H 0.4518 -0.0853 0.0335 0.102 Uiso 1 1 calc R . .
H1B H 0.4243 -0.1109 0.1212 0.102 Uiso 1 1 calc R . .
C2 C 0.5684(4) -0.1545(2) 0.1231(4) 0.0909(14) Uani 1 1 d . . .
H2A H 0.5403 -0.1972 0.1494 0.109 Uiso 1 1 calc R . .
H2B H 0.5675 -0.1718 0.0617 0.109 Uiso 1 1 calc R . .
C3 C 0.6827(4) -0.1415(2) 0.1846(5) 0.115(2) Uani 1 1 d . . .
H3A H 0.6934 -0.1620 0.2475 0.137 Uiso 1 1 calc R . .
H3B H 0.7305 -0.1727 0.1616 0.137 Uiso 1 1 calc R . .
C4 C 0.8385(4) 0.0259(2) 0.5162(2) 0.0684(10) Uani 1 1 d . . .
H4A H 0.8392 -0.0255 0.4904 0.082 Uiso 1 1 calc R . .
H4B H 0.7660 0.0330 0.5239 0.082 Uiso 1 1 calc R . .
C5 C 0.9403(4) 0.0373(2) 0.6092(3) 0.0730(10) Uani 1 1 d . . .
H5A H 0.9208 0.0242 0.6633 0.088 Uiso 1 1 calc R . .
H5B H 1.0054 0.0054 0.6124 0.088 Uiso 1 1 calc R . .
C6 C 0.9686(5) 0.1184(3) 0.6110(3) 0.109(2) Uani 1 1 d . . .
H6A H 1.0521 0.1260 0.6462 0.131 Uiso 1 1 calc R . .
H6B H 0.9287 0.1478 0.6432 0.131 Uiso 1 1 calc R . .
C7 C 0.9318(3) 0.1449(2) 0.5113(2) 0.0651(9) Uani 1 1 d . . .
H7A H 0.8922 0.1944 0.5019 0.078 Uiso 1 1 calc R . .
H7B H 0.9983 0.1500 0.4944 0.078 Uiso 1 1 calc R . .
N1 N 0.6828(2) 0.02965(15) 0.30466(19) 0.0566(7) Uani 1 1 d . . .
N2 N 0.7983(2) 0.15615(14) 0.29129(17) 0.0497(6) Uani 1 1 d . . .
N3 N 0.6933(2) 0.06424(16) 0.13973(18) 0.0575(7) Uani 1 1 d . . .
N4 N 0.5258(2) -0.02344(17) 0.1469(3) 0.0711(9) Uani 1 1 d D . .
N5 N 0.8526(2) 0.08510(14) 0.45341(17) 0.0495(6) Uani 1 1 d . . .
O1 O 0.7270(2) -0.07016(13) 0.1990(2) 0.0725(7) Uani 1 1 d . . .
P1 P 0.65760(7) 0.00325(4) 0.19947(6) 0.0484(2) Uani 1 1 d . . .
P2 P 0.75116(7) 0.10376(4) 0.35166(5) 0.0443(2) Uani 1 1 d . . .
P3 P 0.75262(7) 0.14107(4) 0.18169(5) 0.0449(2) Uani 1 1 d . . .
Cl1 Cl 0.63792(10) 0.17052(7) 0.38131(8) 0.0837(3) Uani 1 1 d . . .
Cl2 Cl 0.64757(11) 0.22638(6) 0.11138(8) 0.0931(4) Uani 1 1 d . . .
Cl3 Cl 0.88050(10) 0.15964(7) 0.14171(8) 0.0860(4) Uani 1 1 d . . .
H4N H 0.470(3) 0.005(2) 0.158(3) 0.112(15) Uiso 1 1 d 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 C1 C2 117.6(3) . . ?
N4 C1 H1A 107.9 . . ?
C2 C1 H1A 107.9 . . ?
N4 C1 H1B 107.9 . . ?
C2 C1 H1B 107.9 . . ?
H1A C1 H1B 107.2 . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2A 107.4 . . ?
C1 C2 H2A 107.4 . . ?
C3 C2 H2B 107.5 . . ?
C1 C2 H2B 107.5 . . ?
H2A C2 H2B 107.0 . . ?
O1 C3 C2 120.8(4) . . ?
O1 C3 H3A 107.1 . . ?
C2 C3 H3A 107.1 . . ?
O1 C3 H3B 107.1 . . ?
C2 C3 H3B 107.1 . . ?
H3A C3 H3B 106.8 . . ?
N5 C4 C5 103.9(3) . . ?
N5 C4 H4A 111.0 . . ?
C5 C4 H4A 111.0 . . ?
N5 C4 H4B 111.0 . . ?
C5 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
C6 C5 C4 104.9(3) . . ?
C6 C5 H5A 110.8 . . ?
C4 C5 H5A 110.8 . . ?
C6 C5 H5B 110.8 . . ?
C4 C5 H5B 110.8 . . ?
H5A C5 H5B 108.8 . . ?
C5 C6 C7 108.2(3) . . ?
C5 C6 H6A 110.0 . . ?
C7 C6 H6A 110.1 . . ?
C5 C6 H6B 110.1 . . ?
C7 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
N5 C7 C6 104.6(3) . . ?
N5 C7 H7A 110.8 . . ?
C6 C7 H7A 110.8 . . ?
N5 C7 H7B 110.8 . . ?
C6 C7 H7B 110.8 . . ?
H7A C7 H7B 108.9 . . ?
P2 N1 P1 123.79(17) . . ?
P3 N2 P2 117.86(15) . . ?
P3 N3 P1 123.37(16) . . ?
C1 N4 P1 126.7(3) . . ?
C1 N4 H4N 114(3) . . ?
P1 N4 H4N 118(3) . . ?
C7 N5 C4 110.0(2) . . ?
C7 N5 P2 121.6(2) . . ?
C4 N5 P2 121.0(2) . . ?
C3 O1 P1 124.3(3) . . ?
O1 P1 N1 111.44(17) . . ?
O1 P1 N3 104.88(16) . . ?
N1 P1 N3 113.87(13) . . ?
O1 P1 N4 103.56(14) . . ?
N1 P1 N4 109.51(17) . . ?
N3 P1 N4 113.04(18) . . ?
O1 P1 H4N 123.8(10) . . ?
N1 P1 H4N 92.2(11) . . ?
N3 P1 H4N 110.7(13) . . ?
N4 P1 H4N 22.0(10) . . ?
N1 P2 N2 118.90(13) . . ?
N1 P2 N5 110.81(14) . . ?
N2 P2 N5 109.92(14) . . ?
N1 P2 Cl1 105.48(12) . . ?
N2 P2 Cl1 105.45(11) . . ?
N5 P2 Cl1 105.15(11) . . ?
N3 P3 N2 119.94(14) . . ?
N3 P3 Cl3 109.63(11) . . ?
N2 P3 Cl3 108.19(11) . . ?
N3 P3 Cl2 108.64(12) . . ?
N2 P3 Cl2 109.13(11) . . ?
Cl3 P3 Cl2 99.36(7) . . ?
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
C1 N4 1.402(4) . ?
C1 C2 1.443(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.400(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O1 1.360(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N5 1.483(4) . ?
C4 C5 1.508(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.473(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.487(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N5 1.482(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
N1 P2 1.575(3) . ?
N1 P1 1.589(3) . ?
N2 P3 1.570(2) . ?
N2 P2 1.593(3) . ?
N3 P3 1.558(3) . ?
N3 P1 1.598(3) . ?
N4 P1 1.615(3) . ?
N4 H4N 0.938(10) . ?
N5 P2 1.611(3) . ?
O1 P1 1.571(2) . ?
P1 H4N 2.21(3) . ?
P2 Cl1 2.0568(12) . ?
P3 Cl3 1.9958(12) . ?
P3 Cl2 2.0137(12) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139156582
