#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/42/2204240.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_2204240
loop_
_publ_author_name
'Pinkus, A. G.'
'Klausmeyer, Kevin K.'
'Feazell, Rodney P.'
'Meng, Liliy Y. C.'
_publ_section_title
;
 α,α,4-Trichloro-α-phenyl-o-tolyl dichlorophosphinate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1486
_journal_page_last               o1487
_journal_paper_doi               10.1107/S1600536804018719
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C13 H8 Cl5 O2 P'
_chemical_formula_moiety         'C13 H8 Cl5 O2 P'
_chemical_formula_sum            'C13 H8 Cl5 O2 P'
_chemical_formula_weight         404.41
_chemical_name_systematic        ?
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                73.238(4)
_cell_angle_beta                 75.348(4)
_cell_angle_gamma                87.593(4)
_cell_formula_units_Z            4
_cell_length_a                   9.5227(7)
_cell_length_b                   10.2195(7)
_cell_length_c                   17.5587(12)
_cell_measurement_reflns_used    7462
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      30.43
_cell_measurement_theta_min      2.25
_cell_volume                     1582.1(2)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2003)'
_computing_data_reduction        'SAINT-Plus (Bruker,2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX2 CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.039
_diffrn_reflns_av_sigmaI/netI    0.025
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            61218
_diffrn_reflns_theta_full        30.62
_diffrn_reflns_theta_max         30.6
_diffrn_reflns_theta_min         2.1
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.02
_exptl_absorpt_correction_T_max  0.879
_exptl_absorpt_correction_T_min  0.817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.58
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         9669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.031
_refine_ls_R_factor_gt           0.025
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0369P)²+0.3855P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.068
_refine_ls_wR_factor_ref         0.071
_reflns_number_gt                8283
_reflns_number_total             9669
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wk6025.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1582.07(19)
_cod_database_code               2204240
_cod_database_fobs_code          2204240
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_type_symbol
P1 -0.13974(3) 0.76283(3) 0.699523(18) 0.01543(6) Uani d . 1 P
P2 0.52687(3) 0.27191(3) 0.78272(2) 0.01898(7) Uani d . 1 P
Cl1 0.45493(3) 0.69691(3) 0.50420(2) 0.02724(7) Uani d . 1 Cl
Cl2 0.22158(4) 0.87340(3) 0.468955(18) 0.02478(7) Uani d . 1 Cl
Cl3 0.16681(3) 0.23039(3) 0.55572(2) 0.02343(7) Uani d . 1 Cl
Cl4 -0.07830(4) 0.94175(3) 0.70573(2) 0.02575(7) Uani d . 1 Cl
Cl5 -0.32895(3) 0.79918(3) 0.66931(2) 0.02687(7) Uani d . 1 Cl
Cl6 0.03597(3) 0.28948(3) 1.071648(17) 0.01839(6) Uani d . 1 Cl
Cl7 0.28474(3) 0.12613(3) 1.039248(18) 0.01940(6) Uani d . 1 Cl
Cl8 0.32268(3) 0.76368(3) 0.99378(2) 0.02212(6) Uani d . 1 Cl
Cl9 0.54032(4) 0.07053(3) 0.80646(2) 0.03011(8) Uani d . 1 Cl
Cl10 0.37796(4) 0.31984(4) 0.71823(2) 0.03195(8) Uani d . 1 Cl
O1 -0.02723(9) 0.75330(8) 0.61792(5) 0.01622(16) Uani d . 1 O
O2 -0.15010(10) 0.64852(9) 0.77330(5) 0.02134(18) Uani d . 1 O
O3 0.44815(9) 0.28127(8) 0.87097(5) 0.01741(16) Uani d . 1 O
O4 0.66453(11) 0.34640(12) 0.74122(7) 0.0378(3) Uani d . 1 O
C1 0.27050(12) 0.73667(12) 0.54840(7) 0.0159(2) Uani d . 1 C
C2 0.16518(12) 0.61616(11) 0.56818(7) 0.0142(2) Uani d . 1 C
C3 0.01698(12) 0.62775(11) 0.60313(7) 0.0145(2) Uani d . 1 C
C4 -0.08346(12) 0.52235(12) 0.62118(7) 0.0160(2) Uani d . 1 C
H4 -0.1812 0.5343 0.6429 0.019 Uiso calc R 1 H
C5 -0.03828(13) 0.39850(12) 0.60686(7) 0.0162(2) Uani d . 1 C
H5 -0.1046 0.3265 0.6194 0.019 Uiso calc R 1 H
C6 0.10834(13) 0.38494(12) 0.57338(7) 0.0162(2) Uani d . 1 C
C7 0.20937(12) 0.49165(12) 0.55359(7) 0.0161(2) Uani d . 1 C
H7 0.3067 0.4800 0.5306 0.019 Uiso calc R 1 H
C8 0.27608(12) 0.78307(11) 0.62247(7) 0.0147(2) Uani d . 1 C
C9 0.24355(12) 0.68792(12) 0.70028(7) 0.0170(2) Uani d . 1 C
H9 0.2140 0.5990 0.7065 0.020 Uiso calc R 1 H
C10 0.25530(13) 0.72601(13) 0.76821(8) 0.0198(2) Uani d . 1 C
H10 0.2343 0.6622 0.8198 0.024 Uiso calc R 1 H
C11 0.29820(14) 0.85889(14) 0.75966(8) 0.0226(2) Uani d . 1 C
H11 0.3041 0.8845 0.8055 0.027 Uiso calc R 1 H
C12 0.33218(14) 0.95336(13) 0.68218(9) 0.0242(3) Uani d . 1 C
H12 0.3619 1.0421 0.6762 0.029 Uiso calc R 1 H
C13 0.32203(13) 0.91584(12) 0.61355(8) 0.0196(2) Uani d . 1 C
H13 0.3458 0.9792 0.5618 0.024 Uiso calc R 1 H
C14 0.18971(12) 0.26992(11) 0.99076(7) 0.0142(2) Uani d . 1 C
C15 0.29254(12) 0.39614(11) 0.95896(7) 0.0143(2) Uani d . 1 C
C16 0.42031(12) 0.39987(11) 0.89709(7) 0.0152(2) Uani d . 1 C
C17 0.51970(13) 0.50929(12) 0.86723(7) 0.0174(2) Uani d . 1 C
H17 0.6050 0.5072 0.8277 0.021 Uiso calc R 1 H
C18 0.49027(13) 0.62247(12) 0.89719(7) 0.0177(2) Uani d . 1 C
H18 0.5551 0.6973 0.8774 0.021 Uiso calc R 1 H
C19 0.36323(13) 0.62196(12) 0.95676(7) 0.0165(2) Uani d . 1 C
C20 0.26536(12) 0.50973(12) 0.98883(7) 0.0160(2) Uani d . 1 C
H20 0.1822 0.5107 1.0300 0.019 Uiso calc R 1 H
C21 0.12703(11) 0.24326(11) 0.92468(7) 0.0136(2) Uani d . 1 C
C22 0.06552(12) 0.35417(11) 0.87725(7) 0.0157(2) Uani d . 1 C
H22 0.0716 0.4406 0.8840 0.019 Uiso calc R 1 H
C23 -0.00433(13) 0.33606(12) 0.82034(8) 0.0193(2) Uani d . 1 C
H23 -0.0457 0.4099 0.7895 0.023 Uiso calc R 1 H
C24 -0.01229(14) 0.20659(13) 0.80953(8) 0.0215(2) Uani d . 1 C
H24 -0.0594 0.1938 0.7717 0.026 Uiso calc R 1 H
C25 0.05059(14) 0.09686(12) 0.85563(8) 0.0206(2) Uani d . 1 C
H25 0.0467 0.0110 0.8478 0.025 Uiso calc R 1 H
C26 0.11945(13) 0.11459(12) 0.91347(7) 0.0173(2) Uani d . 1 C
H26 0.1602 0.0405 0.9445 0.021 Uiso calc R 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'
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
O2 P1 O1 117.54(5) ?
O2 P1 Cl4 115.69(4) ?
O1 P1 Cl4 100.43(3) ?
O2 P1 Cl5 112.58(4) ?
O1 P1 Cl5 104.90(4) ?
Cl4 P1 Cl5 104.02(2) ?
O4 P2 O3 118.43(6) ?
O4 P2 Cl9 114.03(5) ?
O3 P2 Cl9 99.59(4) ?
O4 P2 Cl10 113.31(6) ?
O3 P2 Cl10 105.19(4) ?
Cl9 P2 Cl10 104.54(2) ?
C3 O1 P1 122.67(7) y
C16 O3 P2 127.64(8) y
C21 C14 C15 113.26(9) y
C21 C14 Cl7 112.89(8) ?
C15 C14 Cl7 108.10(8) ?
C21 C14 Cl6 106.40(7) ?
C15 C14 Cl6 110.76(8) ?
Cl7 C14 Cl6 105.13(6) ?
C6 C5 C4 118.41(11) ?
C6 C5 H5 120.8 ?
C4 C5 H5 120.8 ?
C4 C3 C2 122.19(10) ?
C4 C3 O1 120.55(10) ?
C2 C3 O1 117.25(10) ?
C8 C1 C2 114.14(9) y
C8 C1 Cl2 111.82(8) ?
C2 C1 Cl2 107.41(8) ?
C8 C1 Cl1 106.14(8) ?
C2 C1 Cl1 111.62(8) ?
Cl2 C1 Cl1 105.41(6) ?
C21 C26 C25 119.92(11) ?
C21 C26 H26 120.0 ?
C25 C26 H26 120.0 ?
C3 C4 C5 120.00(10) ?
C3 C4 H4 120.0 ?
C5 C4 H4 120.0 ?
C13 C8 C9 119.56(11) ?
C13 C8 C1 121.33(10) ?
C9 C8 C1 118.98(10) ?
C15 C20 C19 119.94(11) ?
C15 C20 H20 120.0 ?
C19 C20 H20 120.0 ?
C6 C7 C2 120.23(10) ?
C6 C7 H7 119.9 ?
C2 C7 H7 119.9 ?
C7 C2 C3 117.37(10) ?
C7 C2 C1 122.80(10) ?
C3 C2 C1 119.83(10) ?
C17 C16 C15 122.46(11) ?
C17 C16 O3 121.15(10) ?
C15 C16 O3 116.22(10) ?
C20 C15 C16 117.56(10) ?
C20 C15 C14 122.84(10) ?
C16 C15 C14 119.60(10) ?
C18 C19 C20 121.67(11) ?
C18 C19 Cl8 119.86(9) ?
C20 C19 Cl8 118.47(9) ?
C12 C13 C8 119.94(12) ?
C12 C13 H13 120.0 ?
C8 C13 H13 120.0 ?
C23 C22 C21 120.57(10) ?
C23 C22 H22 119.7 ?
C21 C22 H22 119.7 ?
C22 C23 C24 119.82(11) ?
C22 C23 H23 120.1 ?
C24 C23 H23 120.1 ?
C25 C24 C23 119.69(11) ?
C25 C24 H24 120.2 ?
C23 C24 H24 120.2 ?
C5 C6 C7 121.78(11) ?
C5 C6 Cl3 118.99(9) ?
C7 C6 Cl3 119.22(9) ?
C26 C21 C22 119.43(10) ?
C26 C21 C14 123.46(10) ?
C22 C21 C14 116.95(10) ?
C19 C18 C17 119.08(11) ?
C19 C18 H18 120.5 ?
C17 C18 H18 120.5 ?
C16 C17 C18 119.22(11) ?
C16 C17 H17 120.4 ?
C18 C17 H17 120.4 ?
C10 C9 C8 120.04(11) ?
C10 C9 H9 120.0 ?
C8 C9 H9 120.0 ?
C11 C12 C13 120.37(12) ?
C11 C12 H12 119.8 ?
C13 C12 H12 119.8 ?
C10 C11 C12 119.62(12) ?
C10 C11 H11 120.2 ?
C12 C11 H11 120.2 ?
C9 C10 C11 120.46(12) ?
C9 C10 H10 119.8 ?
C11 C10 H10 119.8 ?
C24 C25 C26 120.56(11) ?
C24 C25 H25 119.7 ?
C26 C25 H25 119.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl6 C14 1.8132(11) y
P1 O2 1.4576(9) y
P1 O1 1.5830(9) y
P1 Cl4 1.9836(4) y
P1 Cl5 1.9948(4) y
Cl7 C14 1.8055(12) ?
Cl8 C19 1.7431(12) ?
Cl3 C6 1.7384(12) ?
Cl1 C1 1.8123(12) y
Cl2 C1 1.8070(12) y
P2 O4 1.4524(10) y
P2 O3 1.5699(9) y
P2 Cl9 1.9838(5) y
P2 Cl10 1.9917(5) y
O1 C3 1.4080(13) ?
O3 C16 1.4078(14) ?
C14 C21 1.5241(16) ?
C14 C15 1.5325(15) ?
C5 C6 1.3892(16) ?
C5 C4 1.3904(16) ?
C5 H5 0.9300 ?
C3 C4 1.3826(16) ?
C3 C2 1.4042(15) ?
C1 C8 1.5206(16) ?
C1 C2 1.5245(15) ?
C26 C21 1.3919(15) ?
C26 C25 1.3955(17) ?
C26 H26 0.9300 ?
C4 H4 0.9300 ?
C8 C13 1.3963(16) ?
C8 C9 1.3975(16) ?
C20 C15 1.3953(16) ?
C20 C19 1.3974(16) ?
C20 H20 0.9300 ?
C7 C6 1.3914(16) ?
C7 C2 1.3965(16) ?
C7 H7 0.9300 ?
C16 C17 1.3859(16) ?
C16 C15 1.4047(15) ?
C19 C18 1.3838(17) ?
C13 C12 1.3918(18) ?
C13 H13 0.9300 ?
C22 C23 1.3888(16) ?
C22 C21 1.4028(16) ?
C22 H22 0.9300 ?
C23 C24 1.3976(17) ?
C23 H23 0.9300 ?
C24 C25 1.3916(18) ?
C24 H24 0.9300 ?
C18 C17 1.3936(17) ?
C18 H18 0.9300 ?
C17 H17 0.9300 ?
C9 C10 1.3877(17) ?
C9 H9 0.9300 ?
C12 C11 1.390(2) ?
C12 H12 0.9300 ?
C11 C10 1.3897(18) ?
C11 H11 0.9300 ?
C10 H10 0.9300 ?
C25 H25 0.9300 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 226191
