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#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/84/4128474.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_4128474
loop_
_publ_author_name
'Arz, Marius I.'
'Annibale, Vincent T.'
'Kelly, Nicole L.'
'Hanna, John V.'
'Manners, Ian'
_publ_section_title
;
 Ring-Opening Polymerization of Cyclic Phosphonates: Access to Inorganic
 Polymers with a PV-O Main Chain.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2894
_journal_page_last               2899
_journal_paper_doi               10.1021/jacs.8b13435
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C9 H11 Cl2 O P'
_chemical_formula_sum            'C9 H11 Cl2 O P'
_chemical_formula_weight         237.05
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.579(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0851(9)
_cell_length_b                   6.8766(7)
_cell_length_c                   10.0457(11)
_cell_measurement_reflns_used    2937
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      2.67
_cell_volume                     526.23(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8511
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.884
_diffrn_reflns_theta_min         2.152
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0673 before and 0.0395 after correction. The Ratio of minimum to maximum transmission is 0.7056. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       block
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.252
_exptl_crystal_size_min          0.193
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     79
_refine_ls_number_reflns         1353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0281
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0359P)²+0.1973P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0705
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1168
_reflns_number_total             1353
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b13435_si_002.cif
_cod_data_source_block           MesPOCl2
_cod_database_code               4128474
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.873
_shelx_estimated_absorpt_t_min   0.818
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H7A(0.5) H7B(0.5) H7C(0.5) H8A(0.5) H8B(0.5) H8C(0.5) H9A(0.5)
 H9B(0.5) H9C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.32724(5) 0.52197(6) 0.08036(4) 0.02143(13) Uani 1 1 d . . . . .
P1 P 0.43445(7) 0.750000 0.20732(6) 0.01513(14) Uani 1 2 d S T P . .
O1 O 0.6251(2) 0.750000 0.24372(17) 0.0242(4) Uani 1 2 d S T P . .
C1 C 0.3451(3) 0.750000 0.3483(2) 0.0136(4) Uani 1 2 d S T P . .
C2 C 0.4627(3) 0.750000 0.4898(2) 0.0135(4) Uani 1 2 d S T P . .
C3 C 0.3924(3) 0.750000 0.5984(2) 0.0144(4) Uani 1 2 d S T P . .
H3 H 0.470590 0.750000 0.693167 0.017 Uiso 1 2 calc RS T P . .
C4 C 0.2127(3) 0.750000 0.5748(2) 0.0158(4) Uani 1 2 d S T P . .
C5 C 0.0998(3) 0.750000 0.4353(2) 0.0165(4) Uani 1 2 d S T P . .
H5 H -0.023226 0.750000 0.417489 0.020 Uiso 1 2 calc RS T P . .
C6 C 0.1605(3) 0.750000 0.3212(2) 0.0158(4) Uani 1 2 d S T P . .
C7 C 0.6611(3) 0.750000 0.5338(2) 0.0162(4) Uani 1 2 d S T P . .
H7A H 0.699481 0.859157 0.488601 0.024 Uiso 0.5 1 calc GR . . A -1
H7B H 0.700785 0.627573 0.504655 0.024 Uiso 0.5 1 calc GR . . A -1
H7C H 0.711521 0.763270 0.636715 0.024 Uiso 0.5 1 calc GR . . A -1
C8 C 0.1457(3) 0.750000 0.6973(2) 0.0232(5) Uani 1 2 d S T P . .
H8A H 0.028298 0.691903 0.668049 0.035 Uiso 0.5 1 calc GR . . B -1
H8B H 0.139872 0.883969 0.728708 0.035 Uiso 0.5 1 calc GR . . B -1
H8C H 0.225304 0.674127 0.775155 0.035 Uiso 0.5 1 calc GR . . B -1
C9 C 0.0228(3) 0.750000 0.1753(3) 0.0283(6) Uani 1 2 d S T P . .
H9A H 0.052458 0.651306 0.116607 0.043 Uiso 0.5 1 calc GR . . C -1
H9B H 0.019052 0.878306 0.131907 0.043 Uiso 0.5 1 calc GR . . C -1
H9C H -0.092288 0.720388 0.182900 0.043 Uiso 0.5 1 calc GR . . C -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'
Cl Cl 0.1484 0.1585 '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'
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
Cl1 P1 Cl1 101.58(3) 4_575 .
O1 P1 Cl1 110.55(4) . 4_575
O1 P1 Cl1 110.55(4) . .
O1 P1 C1 118.25(10) . .
C1 P1 Cl1 107.28(4) . .
C1 P1 Cl1 107.28(4) . 4_575
C2 C1 P1 118.59(15) . .
C2 C1 C6 119.89(19) . .
C6 C1 P1 121.52(16) . .
C1 C2 C7 125.49(19) . .
C3 C2 C1 118.24(19) . .
C3 C2 C7 116.28(19) . .
C2 C3 H3 118.5 . .
C2 C3 C4 123.0(2) . .
C4 C3 H3 118.5 . .
C3 C4 C5 117.8(2) . .
C3 C4 C8 120.2(2) . .
C5 C4 C8 122.0(2) . .
C4 C5 H5 118.8 . .
C6 C5 C4 122.43(19) . .
C6 C5 H5 118.8 . .
C1 C6 C9 124.61(19) . .
C5 C6 C1 118.63(19) . .
C5 C6 C9 116.76(19) . .
C2 C7 H7A 109.5 . .
C2 C7 H7B 109.5 . .
C2 C7 H7C 109.5 . .
H7A C7 H7B 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C4 C8 H8A 109.5 . .
C4 C8 H8B 109.5 . .
C4 C8 H8C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C6 C9 H9A 109.5 . .
C6 C9 H9B 109.5 . .
C6 C9 H9C 109.5 . .
H9A C9 H9B 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 P1 2.0238(5)
P1 O1 1.4604(16)
P1 C1 1.793(2)
C1 C2 1.421(3)
C1 C6 1.425(3)
C2 C3 1.389(3)
C2 C7 1.515(3)
C3 H3 0.9500
C3 C4 1.391(3)
C4 C5 1.393(3)
C4 C8 1.502(3)
C5 H5 0.9500
C5 C6 1.389(3)
C6 C9 1.515(3)
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 13863629
