#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/40/2204024.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_2204024
loop_
_publ_author_name
'Pinkus, A. G.'
'Klausmeyer, Kevin K.'
'Feazell, Rodney P.'
'Wang, Ching T.'
'Moseley, Charles G.'
_publ_section_title
;
2-[(4-tert-Butylphenoxy)dichloromethyl]phenyl dichlorophosphoonate
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o1313
_journal_page_last               o1314
_journal_paper_doi               10.1107/S1600536804016289
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C17 H17 Cl4 O3 P'
_chemical_formula_moiety         'C17 H17 Cl4 O3 P'
_chemical_formula_sum            'C17 H17 Cl4 O3 P'
_chemical_formula_weight         442.08
_chemical_name_systematic
;
 ?
;
_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                 90.944(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.166(2)
_cell_length_b                   5.9811(5)
_cell_length_c                   24.158(2)
_cell_measurement_reflns_used    8132
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      30.47
_cell_measurement_theta_min      2.24
_cell_volume                     3924.7(6)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker X8 APEX CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0150
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            60962
_diffrn_reflns_theta_full        30.50
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  0.8587
_exptl_absorpt_correction_T_min  0.8184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.422
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         5988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0251
_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)+(0.0327P)²+3.2995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0687
_reflns_number_gt                5358
_reflns_number_total             5988
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl6108.cif
_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 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               2204024
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_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
Cl4 0.200052(9) 0.71226(4) 0.373034(11) 0.01940(6) Uani d . 1 Cl
Cl3 0.205345(9) 0.38244(5) 0.461396(10) 0.01996(6) Uani d . 1 Cl
Cl2 0.175260(11) 0.88158(5) 0.543468(13) 0.02884(7) Uani d . 1 Cl
Cl1 0.072379(14) 1.07744(5) 0.511177(13) 0.03343(8) Uani d . 1 Cl
P1 0.109345(10) 0.79097(5) 0.515584(11) 0.01665(6) Uani d . 1 P
O3 0.19826(3) 0.27940(13) 0.35503(3) 0.01636(14) Uani d . 1 O
O2 0.08542(3) 0.61912(15) 0.54841(3) 0.02300(16) Uani d . 1 O
O1 0.11955(3) 0.73374(13) 0.45310(3) 0.01923(15) Uani d . 1 O
C1 0.18091(3) 0.43453(17) 0.39198(4) 0.01403(17) Uani d . 1 C
C2 0.12529(3) 0.41515(17) 0.39318(4) 0.01433(17) Uani d . 1 C
C3 0.09591(4) 0.56082(18) 0.42358(4) 0.01589(18) Uani d . 1 C
C4 0.04495(4) 0.5418(2) 0.42382(5) 0.0207(2) Uani d . 1 C
H4 0.0261 0.6430 0.4436 0.025 Uiso calc R 1 H
C5 0.02237(4) 0.3696(2) 0.39411(5) 0.0226(2) Uani d . 1 C
H5 -0.0117 0.3547 0.3941 0.027 Uiso calc R 1 H
C6 0.05076(4) 0.2204(2) 0.36445(5) 0.0225(2) Uani d . 1 C
H6 0.0357 0.1047 0.3448 0.027 Uiso calc R 1 H
C7 0.10187(4) 0.24317(19) 0.36397(4) 0.01824(19) Uani d . 1 C
H7 0.1206 0.1423 0.3439 0.022 Uiso calc R 1 H
C8 0.24898(4) 0.27338(17) 0.34249(4) 0.01523(18) Uani d . 1 C
C9 0.26444(4) 0.37789(19) 0.29469(4) 0.01792(19) Uani d . 1 C
H9 0.2426 0.4624 0.2733 0.022 Uiso calc R 1 H
C10 0.31358(4) 0.35424(18) 0.27905(4) 0.01725(19) Uani d . 1 C
H10 0.3243 0.4251 0.2471 0.021 Uiso calc R 1 H
C11 0.34693(4) 0.22652(17) 0.31033(4) 0.01445(17) Uani d . 1 C
C12 0.32975(4) 0.12488(18) 0.35869(4) 0.01695(18) Uani d . 1 C
H12 0.3515 0.0413 0.3805 0.020 Uiso calc R 1 H
C13 0.28095(4) 0.14617(18) 0.37484(4) 0.01712(18) Uani d . 1 C
H13 0.2700 0.0763 0.4068 0.021 Uiso calc R 1 H
C14 0.40068(4) 0.18858(17) 0.29389(4) 0.01578(18) Uani d . 1 C
C15 0.40976(4) -0.0649(2) 0.28827(5) 0.0240(2) Uani d . 1 C
H15A 0.4037 -0.1368 0.3230 0.036 Uiso calc R 1 H
H15B 0.4433 -0.0905 0.2779 0.036 Uiso calc R 1 H
H15C 0.3880 -0.1252 0.2603 0.036 Uiso calc R 1 H
C16 0.41304(4) 0.3005(2) 0.23875(5) 0.0226(2) Uani d . 1 C
H16A 0.3916 0.2438 0.2101 0.034 Uiso calc R 1 H
H16B 0.4466 0.2687 0.2297 0.034 Uiso calc R 1 H
H16C 0.4087 0.4593 0.2419 0.034 Uiso calc R 1 H
C17 0.43511(4) 0.2843(2) 0.33924(5) 0.0210(2) Uani d . 1 C
H17A 0.4295 0.4421 0.3428 0.032 Uiso calc R 1 H
H17B 0.4687 0.2586 0.3294 0.032 Uiso calc R 1 H
H17C 0.4286 0.2121 0.3738 0.032 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 117.05(5) ?
O2 P1 Cl2 114.65(4) ?
O1 P1 Cl2 102.30(3) ?
O2 P1 Cl1 114.04(4) ?
O1 P1 Cl1 103.44(3) ?
Cl2 P1 Cl1 103.63(2) ?
C1 O3 C8 120.05(8) y
C3 O1 P1 124.01(7) ?
O3 C1 C2 108.24(8) ?
O3 C1 Cl4 110.71(7) ?
C2 C1 Cl4 111.54(7) ?
O3 C1 Cl3 111.01(7) ?
C2 C1 Cl3 108.52(7) ?
Cl4 C1 Cl3 106.82(5) ?
C7 C2 C3 117.75(9) ?
C7 C2 C1 119.54(9) ?
C3 C2 C1 122.69(9) ?
C4 C3 C2 121.91(10) ?
C4 C3 O1 120.36(9) ?
C2 C3 O1 117.71(9) ?
C3 C4 C5 119.29(10) ?
C3 C4 H4 120.4 ?
C5 C4 H4 120.4 ?
C6 C5 C4 119.90(10) ?
C6 C5 H5 120.1 ?
C4 C5 H5 120.1 ?
C5 C6 C7 120.23(11) ?
C5 C6 H6 119.9 ?
C7 C6 H6 119.9 ?
C2 C7 C6 120.89(10) ?
C2 C7 H7 119.6 ?
C6 C7 H7 119.6 ?
C9 C8 C13 121.49(9) ?
C9 C8 O3 118.46(9) ?
C13 C8 O3 119.74(9) ?
C8 C9 C10 118.88(9) ?
C8 C9 H9 120.6 ?
C10 C9 H9 120.6 ?
C11 C10 C9 121.44(9) ?
C11 C10 H10 119.3 ?
C9 C10 H10 119.3 ?
C10 C11 C12 117.74(9) ?
C10 C11 C14 123.46(9) ?
C12 C11 C14 118.79(9) ?
C13 C12 C11 121.62(9) ?
C13 C12 H12 119.2 ?
C11 C12 H12 119.2 ?
C8 C13 C12 118.83(9) ?
C8 C13 H13 120.6 ?
C12 C13 H13 120.6 ?
C16 C14 C11 112.50(8) ?
C16 C14 C17 108.47(9) ?
C11 C14 C17 109.27(8) ?
C16 C14 C15 108.38(9) ?
C11 C14 C15 108.78(8) ?
C17 C14 C15 109.41(9) ?
C14 C15 H15A 109.5 ?
C14 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C14 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
C14 C16 H16A 109.5 ?
C14 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C14 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
C14 C17 H17A 109.5 ?
C14 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C14 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl4 C1 1.8020(10) ?
Cl3 C1 1.8200(10) ?
Cl2 P1 1.9784(4) y
Cl1 P1 1.9880(4) y
P1 O2 1.4577(9) y
P1 O1 1.5768(8) y
O3 C1 1.3760(10) y
O3 C8 1.4160(10) y
O1 C3 1.4055(13) ?
C1 C2 1.5162(13) ?
C2 C7 1.3950(14) ?
C2 C3 1.3982(14) ?
C3 C4 1.3892(14) ?
C4 C5 1.3919(17) ?
C4 H4 0.9300 ?
C5 C6 1.3868(16) ?
C5 H5 0.9300 ?
C6 C7 1.3952(14) ?
C6 H6 0.9300 ?
C7 H7 0.9300 ?
C8 C9 1.3845(14) ?
C8 C13 1.3862(14) ?
C9 C10 1.4006(14) ?
C9 H9 0.9300 ?
C10 C11 1.3973(14) ?
C10 H10 0.9300 ?
C11 C12 1.4036(14) ?
C11 C14 1.5366(13) ?
C12 C13 1.3940(14) ?
C12 H12 0.9300 ?
C13 H13 0.9300 ?
C14 C16 1.5329(15) ?
C14 C17 1.5393(15) ?
C14 C15 1.5423(15) ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C16 H16A 0.9600 ?
C16 H16B 0.9600 ?
C16 H16C 0.9600 ?
C17 H17A 0.9600 ?
C17 H17B 0.9600 ?
C17 H17C 0.9600 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21130612
