##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(Z)-(1,2-Dichlorovinyl)diphenylphosphine oxide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H11 Cl2 O P'
_chemical_formula_sum     'C14 H11 Cl2 O P'
_chemical_formula_iupac     'C14 H11 Cl2 O P'
_chemical_formula_weight     297.10
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     12.0621(11)
_cell_length_b     7.9521(8)
_cell_length_c     14.9913(15)
_cell_angle_alpha     90.00
_cell_angle_beta     102.8580(10)
_cell_angle_gamma     90.00
_cell_volume     1401.9(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3636
_cell_measurement_theta_min     2.453
_cell_measurement_theta_max     27.993
_cell_measurement_temperature     298(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.32
_exptl_crystal_density_diffrn     1.408
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     608
_exptl_absorpt_coefficient_mu     0.561
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2008)'
_exptl_absorpt_correction_T_min     0.7864
_exptl_absorpt_correction_T_max     0.8409
_exptl_special_details     ?
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6788
_diffrn_reflns_av_R_equivalents     0.0221
_diffrn_reflns_av_sigmaI/netI     0.0251
_diffrn_reflns_theta_min     2.45
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2475
_reflns_number_gt     2009
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0470
_refine_ls_R_factor_gt     0.0347
_refine_ls_wR_factor_gt     0.0831
_refine_ls_wR_factor_ref     0.0936
_refine_ls_goodness_of_fit_ref     1.077
_refine_ls_restrained_S_all     1.077
_refine_ls_number_reflns     2475
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0395P)²+0.7290P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.278
_refine_diff_density_min     -0.365
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2002)'
_computing_cell_refinement     'SAINT (Bruker, 2002)'
_computing_data_reduction     'SAINT (Bruker, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.64091(5) 0.30633(8) 0.48897(6) 0.0610(2) Uani d . 1 1 . .
    Cl Cl2 0.87750(6) 0.09961(8) 0.52709(5) 0.0558(2) Uani d . 1 1 . .
    O O1 0.90014(13) 0.6840(2) 0.53670(11) 0.0441(4) Uani d . 1 1 . .
    P P1 0.77986(4) 0.62950(7) 0.51027(4) 0.03243(16) Uani d . 1 1 . .
    C C1 0.77287(18) 0.4017(3) 0.51179(15) 0.0340(5) Uani d . 1 1 . .
    C C2 0.8685(2) 0.3151(3) 0.52622(15) 0.0386(5) Uani d . 1 1 . .
    H H2 0.9363 0.3754 0.5367 0.046 Uiso calc R 1 1 . .
    C C5 0.71157(19) 0.6946(3) 0.39607(15) 0.0358(5) Uani d . 1 1 . .
    C C6 0.7790(2) 0.7721(3) 0.34425(18) 0.0528(7) Uani d . 1 1 . .
    H H6 0.8557 0.7909 0.3694 0.063 Uiso calc R 1 1 . .
    C C7 0.7327(3) 0.8213(4) 0.2555(2) 0.0726(9) Uani d . 1 1 . .
    H H7 0.7782 0.8733 0.2211 0.087 Uiso calc R 1 1 . .
    C C8 0.6190(3) 0.7938(4) 0.2178(2) 0.0693(9) Uani d . 1 1 . .
    H H8 0.5883 0.8266 0.1579 0.083 Uiso calc R 1 1 . .
    C C9 0.5516(2) 0.7187(4) 0.26807(19) 0.0580(7) Uani d . 1 1 . .
    H H9 0.4749 0.7011 0.2422 0.070 Uiso calc R 1 1 . .
    C C10 0.5964(2) 0.6681(3) 0.35770(17) 0.0462(6) Uani d . 1 1 . .
    H H10 0.5500 0.6171 0.3918 0.055 Uiso calc R 1 1 . .
    C C11 0.69328(18) 0.7001(3) 0.58622(15) 0.0357(5) Uani d . 1 1 . .
    C C12 0.6898(3) 0.6104(3) 0.66513(18) 0.0570(7) Uani d . 1 1 . .
    H H12 0.7270 0.5076 0.6761 0.068 Uiso calc R 1 1 . .
    C C13 0.6313(3) 0.6733(4) 0.7274(2) 0.0720(9) Uani d . 1 1 . .
    H H13 0.6287 0.6122 0.7798 0.086 Uiso calc R 1 1 . .
    C C14 0.5770(3) 0.8255(4) 0.7119(2) 0.0646(8) Uani d . 1 1 . .
    H H14 0.5375 0.8672 0.7538 0.078 Uiso calc R 1 1 . .
    C C15 0.5807(2) 0.9163(4) 0.6352(2) 0.0574(7) Uani d . 1 1 . .
    H H15 0.5446 1.0202 0.6255 0.069 Uiso calc R 1 1 . .
    C C16 0.6382(2) 0.8539(3) 0.57215(17) 0.0450(6) Uani d . 1 1 . .
    H H16 0.6399 0.9157 0.5198 0.054 Uiso calc R 1 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Cl1 0.0402(4) 0.0432(4) 0.0962(6) -0.0081(3) 0.0078(3) 0.0024(3)
    Cl2 0.0635(4) 0.0370(3) 0.0740(5) 0.0102(3) 0.0305(4) 0.0031(3)
    O1 0.0339(8) 0.0455(9) 0.0512(10) -0.0043(7) 0.0057(7) -0.0002(8)
    P1 0.0304(3) 0.0327(3) 0.0339(3) -0.0002(2) 0.0064(2) 0.0015(2)
    C1 0.0356(12) 0.0325(11) 0.0348(12) -0.0024(9) 0.0100(9) -0.0005(9)
    C2 0.0436(13) 0.0330(12) 0.0430(14) 0.0015(10) 0.0181(11) 0.0019(10)
    C5 0.0396(12) 0.0333(11) 0.0351(12) 0.0037(9) 0.0095(10) 0.0002(9)
    C6 0.0531(15) 0.0594(16) 0.0476(15) -0.0026(13) 0.0152(12) 0.0103(13)
    C7 0.088(2) 0.086(2) 0.0489(18) 0.0013(18) 0.0252(16) 0.0236(16)
    C8 0.088(2) 0.078(2) 0.0381(16) 0.0183(18) 0.0070(16) 0.0105(15)
    C9 0.0536(16) 0.0668(18) 0.0458(16) 0.0115(14) -0.0053(13) -0.0015(14)
    C10 0.0438(14) 0.0517(14) 0.0422(14) 0.0045(11) 0.0078(11) 0.0023(12)
    C11 0.0358(12) 0.0386(12) 0.0313(12) -0.0010(9) 0.0046(9) -0.0027(10)
    C12 0.0811(19) 0.0525(15) 0.0396(14) 0.0128(14) 0.0181(13) 0.0058(12)
    C13 0.104(3) 0.078(2) 0.0404(16) -0.0032(19) 0.0308(17) -0.0010(15)
    C14 0.0630(18) 0.082(2) 0.0546(18) -0.0031(16) 0.0253(14) -0.0256(16)
    C15 0.0553(16) 0.0576(16) 0.0591(18) 0.0106(13) 0.0122(14) -0.0158(14)
    C16 0.0478(14) 0.0424(13) 0.0443(14) 0.0025(11) 0.0089(11) -0.0008(11)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    Cl1 C1 . 1.727(2) ?
    Cl2 C2 . 1.717(2) ?
    O1 P1 . 1.4813(16) ?
    P1 C11 . 1.798(2) ?
    P1 C5 . 1.803(2) ?
    P1 C1 . 1.814(2) ?
    C1 C2 . 1.319(3) ?
    C2 H2 . 0.9300 ?
    C5 C6 . 1.388(3) ?
    C5 C10 . 1.397(3) ?
    C6 C7 . 1.380(4) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.379(5) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.364(4) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.391(4) ?
    C9 H9 . 0.9300 ?
    C10 H10 . 0.9300 ?
    C11 C16 . 1.385(3) ?
    C11 C12 . 1.390(3) ?
    C12 C13 . 1.382(4) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.371(5) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.366(4) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.384(4) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 P1 C11 . . 114.31(10) ?
    O1 P1 C5 . . 112.55(10) ?
    C11 P1 C5 . . 107.75(10) ?
    O1 P1 C1 . . 109.54(10) ?
    C11 P1 C1 . . 105.58(10) ?
    C5 P1 C1 . . 106.62(10) ?
    C2 C1 Cl1 . . 122.49(18) ?
    C2 C1 P1 . . 118.80(17) ?
    Cl1 C1 P1 . . 118.64(12) ?
    C1 C2 Cl2 . . 124.99(19) ?
    C1 C2 H2 . . 117.5 ?
    Cl2 C2 H2 . . 117.5 ?
    C6 C5 C10 . . 119.3(2) ?
    C6 C5 P1 . . 117.27(18) ?
    C10 C5 P1 . . 123.39(18) ?
    C7 C6 C5 . . 120.2(3) ?
    C7 C6 H6 . . 119.9 ?
    C5 C6 H6 . . 119.9 ?
    C8 C7 C6 . . 120.2(3) ?
    C8 C7 H7 . . 119.9 ?
    C6 C7 H7 . . 119.9 ?
    C9 C8 C7 . . 120.2(3) ?
    C9 C8 H8 . . 119.9 ?
    C7 C8 H8 . . 119.9 ?
    C8 C9 C10 . . 120.6(3) ?
    C8 C9 H9 . . 119.7 ?
    C10 C9 H9 . . 119.7 ?
    C9 C10 C5 . . 119.4(2) ?
    C9 C10 H10 . . 120.3 ?
    C5 C10 H10 . . 120.3 ?
    C16 C11 C12 . . 118.6(2) ?
    C16 C11 P1 . . 120.36(18) ?
    C12 C11 P1 . . 120.72(18) ?
    C13 C12 C11 . . 120.4(3) ?
    C13 C12 H12 . . 119.8 ?
    C11 C12 H12 . . 119.8 ?
    C14 C13 C12 . . 120.1(3) ?
    C14 C13 H13 . . 120.0 ?
    C12 C13 H13 . . 120.0 ?
    C15 C14 C13 . . 120.4(3) ?
    C15 C14 H14 . . 119.8 ?
    C13 C14 H14 . . 119.8 ?
    C14 C15 C16 . . 120.0(3) ?
    C14 C15 H15 . . 120.0 ?
    C16 C15 H15 . . 120.0 ?
    C15 C16 C11 . . 120.6(2) ?
    C15 C16 H16 . . 119.7 ?
    C11 C16 H16 . . 119.7 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 P1 C1 C2 . . . . -6.2(2) ?
    C11 P1 C1 C2 . . . . -129.75(19) ?
    C5 P1 C1 C2 . . . . 115.8(2) ?
    O1 P1 C1 Cl1 . . . . 176.78(12) ?
    C11 P1 C1 Cl1 . . . . 53.24(16) ?
    C5 P1 C1 Cl1 . . . . -61.18(16) ?
    Cl1 C1 C2 Cl2 . . . . -1.4(3) ?
    P1 C1 C2 Cl2 . . . . -178.31(13) ?
    O1 P1 C5 C6 . . . . 5.5(2) ?
    C11 P1 C5 C6 . . . . 132.48(19) ?
    C1 P1 C5 C6 . . . . -114.6(2) ?
    O1 P1 C5 C10 . . . . -175.63(18) ?
    C11 P1 C5 C10 . . . . -48.7(2) ?
    C1 P1 C5 C10 . . . . 64.3(2) ?
    C10 C5 C6 C7 . . . . -0.4(4) ?
    P1 C5 C6 C7 . . . . 178.4(2) ?
    C5 C6 C7 C8 . . . . 0.0(5) ?
    C6 C7 C8 C9 . . . . 0.4(5) ?
    C7 C8 C9 C10 . . . . -0.3(5) ?
    C8 C9 C10 C5 . . . . -0.1(4) ?
    C6 C5 C10 C9 . . . . 0.5(4) ?
    P1 C5 C10 C9 . . . . -178.29(19) ?
    O1 P1 C11 C16 . . . . 88.7(2) ?
    C5 P1 C11 C16 . . . . -37.2(2) ?
    C1 P1 C11 C16 . . . . -150.85(19) ?
    O1 P1 C11 C12 . . . . -84.5(2) ?
    C5 P1 C11 C12 . . . . 149.6(2) ?
    C1 P1 C11 C12 . . . . 35.9(2) ?
    C16 C11 C12 C13 . . . . 0.8(4) ?
    P1 C11 C12 C13 . . . . 174.1(2) ?
    C11 C12 C13 C14 . . . . -0.6(5) ?
    C12 C13 C14 C15 . . . . -0.2(5) ?
    C13 C14 C15 C16 . . . . 0.8(5) ?
    C14 C15 C16 C11 . . . . -0.6(4) ?
    C12 C11 C16 C15 . . . . -0.2(4) ?
    P1 C11 C16 C15 . . . . -173.6(2) ?
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
    C2 H2 O1 3_766 0.93 2.51 3.138(3) 125.2
    C8 H8 O1 4_575 0.93 2.57 3.344(4) 140.6
data_global
_journal_date_recd_electronic     2011-07-15
_journal_date_accepted     2011-07-31
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      9
_journal_page_first     o2267
_journal_page_last     o2267
_journal_paper_category     QO
_journal_coeditor_code     LD2021
_publ_contact_author_name     'Ming-Shu Wu'
_publ_contact_author_address
;
College of Chemistry & Chemical Engineering, Hainan Normal University,Haikou,
571158, Peoples' Republic of China
;
_publ_contact_author_email     wumingshu@126.com
_publ_contact_author_fax     +86-0898-65883398
_publ_contact_author_phone     +86-0898-65883398
_publ_section_title
;
(Z)-(1,2-Dichlorovinyl)diphenylphosphine oxide
;
loop_
    _publ_author_name
    'Ma, Jing-Ya'
    'Feng, Qing-Qin'
    'Wu, Ming-Shu'
loop_
    _publ_author_footnote
    ' '
;
;
loop_
    _publ_author_address
;
College of Chemistry & Chemical Engineering,
Hainan Normal University
Haikou 571158
People's Republic of China
;
;
College of Chemistry & Chemical Engineering
Anyang Normal University
Anyang 455000, Henan,
People's Republic of China
;
;
College of Chemistry & Chemical Engineering,
Hainan Normal University
Haikou 571158
People's Republic of China
;
_publ_section_synopsis     .
