#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/15/2201535.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_2201535
loop_
_publ_author_name
'Jones, Peter G.'
'Kunze, Christine'
'Thönnessen, Holger'
'Schmutzler, Reinhard'
_publ_section_title
;
 2-Chloro-1,3-dioxa-2σ³λ³-phosphaanthracen-4-one
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1432
_journal_page_last               o1433
_journal_paper_doi               10.1107/S1600536802021189
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C11 H6 Cl O3 P'
_chemical_formula_moiety         'C11 H6 Cl O3 P'
_chemical_formula_sum            'C11 H6 Cl O3 P'
_chemical_formula_weight         252.58
_chemical_name_systematic
;
2-Chloro-1,3-dioxa-2σ³λ³-phosphaanthracen-4-one
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0031(15)
_cell_length_b                   10.0697(15)
_cell_length_c                   17.028(3)
_cell_measurement_reflns_used    56
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      11.5
_cell_measurement_theta_min      10
_cell_volume                     1029.3(4)
_computing_cell_refinement       DIF4
_computing_data_collection       'DIF4 (Stoe & Cie, 1992)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1992)'
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Stoe Stadi-4'
_diffrn_measurement_method       ω/θ
_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  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3936
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         3.13
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.511
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.255
_refine_ls_abs_structure_details
'Flack (1983), 971 Friedel pairs [Please check]'
_refine_ls_abs_structure_Flack   -0.03(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2367
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0353
_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)+(0.0289P)²+0.1959P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0828
_reflns_number_gt                2114
_reflns_number_total             2367
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na6183.cif
_cod_data_source_block           I
_cod_database_code               2201535
_cod_database_fobs_code          2201535
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'
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
P 0.67867(10) 0.24783(6) 0.17797(4) 0.03157(15) Uani d . 1 . . P
Cl 0.85239(13) 0.26700(7) 0.07228(4) 0.04888(19) Uani d . 1 . . Cl
O1 0.4731(3) 0.34694(16) 0.16174(10) 0.0324(4) Uani d . 1 . . O
O2 0.8378(3) 0.34102(15) 0.23247(9) 0.0319(4) Uani d . 1 . . O
O3 1.0008(3) 0.52884(17) 0.26724(9) 0.0378(4) Uani d . 1 . . O
C1 0.7046(4) 0.6836(2) 0.17491(13) 0.0249(5) Uani d . 1 . . C
H1 0.8309 0.7280 0.1959 0.030 Uiso calc R 1 . . H
C2 0.6850(4) 0.5482(2) 0.18433(12) 0.0243(4) Uani d . 1 . . C
C3 0.4976(4) 0.4830(2) 0.15187(12) 0.0260(5) Uani d . 1 . . C
C4 0.3362(4) 0.5502(2) 0.11288(12) 0.0257(4) Uani d . 1 . . C
H4 0.2128 0.5036 0.0914 0.031 Uiso calc R 1 . . H
C5 0.1849(4) 0.7650(2) 0.06539(12) 0.0275(4) Uani d . 1 . . C
H5 0.0574 0.7216 0.0446 0.033 Uiso calc R 1 . . H
C6 0.2063(4) 0.8993(2) 0.05764(13) 0.0335(5) Uani d . 1 . . C
H6 0.0930 0.9486 0.0318 0.040 Uiso calc R 1 . . H
C7 0.3940(5) 0.9654(2) 0.08749(13) 0.0349(6) Uani d . 1 . . C
H7 0.4065 1.0589 0.0816 0.042 Uiso calc R 1 . . H
C8 0.5586(4) 0.8968(2) 0.12493(13) 0.0307(5) Uani d . 1 . . C
H8 0.6854 0.9425 0.1445 0.037 Uiso calc R 1 . . H
C9 0.5411(4) 0.7575(2) 0.13470(11) 0.0242(4) Uani d . 1 . . C
C10 0.3511(4) 0.6898(2) 0.10407(12) 0.0243(4) Uani d . 1 . . C
C11 0.8551(4) 0.4777(2) 0.23058(12) 0.0283(5) Uani d . 1 . . C
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'
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
O1 P O2 100.95(9) y
O1 P Cl 100.21(7) y
O2 P Cl 98.33(7) y
C3 O1 P 123.43(16) y
C11 O2 P 127.24(15) y
C2 C1 C9 121.3(2) ?
C2 C1 H1 119.4 ?
C9 C1 H1 119.4 ?
C1 C2 C3 118.8(2) ?
C1 C2 C11 118.7(2) ?
C3 C2 C11 122.49(19) ?
C4 C3 O1 118.4(2) ?
C4 C3 C2 121.9(2) ?
O1 C3 C2 119.7(2) ?
C3 C4 C10 120.1(2) ?
C3 C4 H4 119.9 ?
C10 C4 H4 119.9 ?
C6 C5 C10 120.6(2) ?
C6 C5 H5 119.7 ?
C10 C5 H5 119.7 ?
C5 C6 C7 120.7(2) ?
C5 C6 H6 119.7 ?
C7 C6 H6 119.7 ?
C8 C7 C6 120.7(2) ?
C8 C7 H7 119.6 ?
C6 C7 H7 119.6 ?
C7 C8 C9 120.2(2) ?
C7 C8 H8 119.9 ?
C9 C8 H8 119.9 ?
C1 C9 C8 121.9(2) ?
C1 C9 C10 118.8(2) ?
C8 C9 C10 119.30(19) ?
C5 C10 C4 122.4(2) ?
C5 C10 C9 118.57(19) ?
C4 C10 C9 119.0(2) ?
O3 C11 O2 118.3(2) ?
O3 C11 C2 125.5(2) ?
O2 C11 C2 116.1(2) ?
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
P O1 . 1.6110(18) y
P O2 . 1.6290(18) y
P Cl . 2.0890(9) y
O1 C3 . 1.388(3) ?
O2 C11 . 1.381(3) ?
O3 C11 . 1.191(3) ?
C1 C2 . 1.379(3) ?
C1 C9 . 1.410(3) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.414(3) ?
C2 C11 . 1.472(3) ?
C3 C4 . 1.356(3) ?
C4 C10 . 1.417(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.365(3) ?
C5 C10 . 1.415(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.404(4) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.364(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.416(3) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.428(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C1 H1 O2 3_755 0.95 2.60 3.542(3) 174
C8 H8 O3 3_755 0.95 2.56 3.484(3) 164
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
O2 P O1 C3 35.57(18)
Cl P O1 C3 -65.07(17)
O1 P O2 C11 -29.7(2)
Cl P O2 C11 72.5(2)
C9 C1 C2 C3 0.8(3)
C9 C1 C2 C11 -176.72(19)
P O1 C3 C4 157.61(16)
P O1 C3 C2 -24.2(3)
C1 C2 C3 C4 -0.9(3)
C11 C2 C3 C4 176.5(2)
C1 C2 C3 O1 -179.0(2)
C11 C2 C3 O1 -1.6(3)
O1 C3 C4 C10 177.7(2)
C2 C3 C4 C10 -0.4(3)
C10 C5 C6 C7 0.4(4)
C5 C6 C7 C8 -0.1(4)
C6 C7 C8 C9 -0.5(3)
C2 C1 C9 C8 179.7(2)
C2 C1 C9 C10 0.6(3)
C7 C8 C9 C1 -178.2(2)
C7 C8 C9 C10 0.8(3)
C6 C5 C10 C4 -179.5(2)
C6 C5 C10 C9 0.0(3)
C3 C4 C10 C5 -178.6(2)
C3 C4 C10 C9 1.9(3)
C1 C9 C10 C5 178.53(19)
C8 C9 C10 C5 -0.5(3)
C1 C9 C10 C4 -2.0(3)
C8 C9 C10 C4 179.0(2)
P O2 C11 O3 -170.25(17)
P O2 C11 C2 11.4(3)
C1 C2 C11 O3 7.1(4)
C3 C2 C11 O3 -170.3(2)
C1 C2 C11 O2 -174.6(2)
C3 C2 C11 O2 7.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13273493
