##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 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. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(SP)-Menthyl benzyl(phenyl)phosphonate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H31 O2 P'
_chemical_formula_sum     'C23 H31 O2 P'
_chemical_formula_iupac     'C23 H31 O2 P'
_chemical_formula_weight     370.45
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     12.4777(11)
_cell_length_b     5.7970(7)
_cell_length_c     15.4190(19)
_cell_angle_alpha     90.00
_cell_angle_beta     100.7270(10)
_cell_angle_gamma     90.00
_cell_volume     1095.8(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1629
_cell_measurement_theta_min     2.689
_cell_measurement_theta_max     25.040
_cell_measurement_temperature     298(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.43
_exptl_crystal_size_mid     0.11
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.123
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     400
_exptl_absorpt_coefficient_mu     0.138
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9428
_exptl_absorpt_correction_T_max     0.9863
_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     'Siemens SMART CCD area-detector'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5541
_diffrn_reflns_av_R_equivalents     0.0846
_diffrn_reflns_av_sigmaI/netI     0.0988
_diffrn_reflns_theta_min     1.34
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     3576
_reflns_number_gt     2596
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0877
_refine_ls_R_factor_gt     0.0658
_refine_ls_wR_factor_gt     0.1567
_refine_ls_wR_factor_ref     0.1697
_refine_ls_goodness_of_fit_ref     0.890
_refine_ls_restrained_S_all     0.889
_refine_ls_number_reflns     3576
_refine_ls_number_parameters     238
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1052P)²+0.0000P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.283
_refine_diff_density_min     -0.230
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 1432 Friedel pairs'
_refine_ls_abs_structure_Flack     -0.17(16)
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'
    'N' 'N' 0.0061 0.0033
                         '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'
_computing_data_collection     'SMART (Siemens, 1996)'
_computing_cell_refinement     'SAINT (Siemens, 1996)'
_computing_data_reduction     'SAINT (Siemens, 1996)'
_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_disorder_assembly
    _atom_site_disorder_group
    P P1 0.14134(8) 0.32764(18) 0.12780(6) 0.0440(3) Uani d . 1 . .
    O O1 0.2011(2) 0.2676(5) 0.22583(18) 0.0495(7) Uani d . 1 . .
    O O2 0.1092(2) 0.5709(5) 0.11455(18) 0.0539(8) Uani d . 1 . .
    C C1 0.2811(3) 0.3635(8) 0.3776(3) 0.0513(11) Uani d . 1 . .
    H H1 0.3316 0.2327 0.3810 0.062 Uiso calc R 1 . .
    C C2 0.2606(3) 0.4484(9) 0.2817(3) 0.0494(10) Uani d . 1 . .
    H H2 0.2140 0.5856 0.2776 0.059 Uiso calc R 1 . .
    C C3 0.3653(4) 0.5136(9) 0.2527(3) 0.0604(13) Uani d . 1 . .
    H H3A 0.3492 0.5651 0.1918 0.072 Uiso calc R 1 . .
    H H3B 0.4119 0.3788 0.2556 0.072 Uiso calc R 1 . .
    C C4 0.4259(4) 0.7041(10) 0.3099(3) 0.0736(15) Uani d . 1 . .
    H H4 0.3776 0.8387 0.3045 0.088 Uiso calc R 1 . .
    C C5 0.4456(4) 0.6286(13) 0.4061(3) 0.0831(17) Uani d . 1 . .
    H H5A 0.4964 0.5004 0.4142 0.100 Uiso calc R 1 . .
    H H5B 0.4786 0.7548 0.4430 0.100 Uiso calc R 1 . .
    C C6 0.3419(4) 0.5571(10) 0.4352(3) 0.0694(14) Uani d . 1 . .
    H H6A 0.2942 0.6901 0.4329 0.083 Uiso calc R 1 . .
    H H6B 0.3590 0.5049 0.4959 0.083 Uiso calc R 1 . .
    C C7 0.1778(4) 0.2749(10) 0.4090(3) 0.0665(14) Uani d . 1 . .
    H H7 0.1455 0.1554 0.3672 0.080 Uiso calc R 1 . .
    C C8 0.0910(5) 0.4614(15) 0.4086(4) 0.104(2) Uani d . 1 . .
    H H8A 0.0268 0.3938 0.4239 0.157 Uiso calc R 1 . .
    H H8B 0.0731 0.5286 0.3508 0.157 Uiso calc R 1 . .
    H H8C 0.1187 0.5787 0.4508 0.157 Uiso calc R 1 . .
    C C9 0.2060(5) 0.1607(12) 0.4997(3) 0.0865(18) Uani d . 1 . .
    H H9A 0.2317 0.2756 0.5435 0.130 Uiso calc R 1 . .
    H H9B 0.2620 0.0472 0.4992 0.130 Uiso calc R 1 . .
    H H9C 0.1422 0.0876 0.5134 0.130 Uiso calc R 1 . .
    C C10 0.5316(5) 0.7791(15) 0.2790(4) 0.113(3) Uani d . 1 . .
    H H10A 0.5812 0.6511 0.2838 0.170 Uiso calc R 1 . .
    H H10B 0.5649 0.9037 0.3153 0.170 Uiso calc R 1 . .
    H H10C 0.5143 0.8289 0.2186 0.170 Uiso calc R 1 . .
    C C11 0.2347(3) 0.2350(7) 0.0575(3) 0.0445(10) Uani d . 1 . .
    C C12 0.2528(4) 0.3793(9) -0.0106(3) 0.0615(14) Uani d . 1 . .
    H H12 0.2167 0.5200 -0.0204 0.074 Uiso calc R 1 . .
    C C13 0.3260(4) 0.3096(13) -0.0641(3) 0.0790(15) Uani d . 1 . .
    H H13 0.3387 0.4050 -0.1097 0.095 Uiso calc R 1 . .
    C C14 0.3790(4) 0.1029(11) -0.0502(4) 0.0762(15) Uani d . 1 . .
    H H14 0.4277 0.0581 -0.0859 0.091 Uiso calc R 1 . .
    C C15 0.3601(4) -0.0387(11) 0.0170(4) 0.0776(15) Uani d . 1 . .
    H H15 0.3964 -0.1791 0.0267 0.093 Uiso calc R 1 . .
    C C16 0.2876(4) 0.0258(9) 0.0701(3) 0.0652(13) Uani d . 1 . .
    H H16 0.2744 -0.0724 0.1146 0.078 Uiso calc R 1 . .
    C C17 0.0306(3) 0.1248(8) 0.1089(3) 0.0511(10) Uani d . 1 . .
    H H17A -0.0110 0.1479 0.0498 0.061 Uiso calc R 1 . .
    H H17B 0.0603 -0.0303 0.1117 0.061 Uiso calc R 1 . .
    C C18 -0.0457(3) 0.1452(8) 0.1747(3) 0.0490(10) Uani d . 1 . .
    C C19 -0.1144(4) 0.3305(10) 0.1742(3) 0.0668(12) Uani d . 1 . .
    H H19 -0.1153 0.4478 0.1329 0.080 Uiso calc R 1 . .
    C C20 -0.1828(4) 0.3417(13) 0.2360(4) 0.0828(16) Uani d . 1 . .
    H H20 -0.2284 0.4684 0.2363 0.099 Uiso calc R 1 . .
    C C21 -0.1837(5) 0.1675(13) 0.2966(4) 0.0861(18) Uani d . 1 . .
    H H21 -0.2302 0.1752 0.3371 0.103 Uiso calc R 1 . .
    C C22 -0.1159(5) -0.0153(12) 0.2966(4) 0.0910(19) Uani d . 1 . .
    H H22 -0.1155 -0.1324 0.3379 0.109 Uiso calc R 1 . .
    C C23 -0.0479(4) -0.0298(10) 0.2365(3) 0.0689(13) Uani d . 1 . .
    H H23 -0.0028 -0.1576 0.2369 0.083 Uiso calc R 1 . .
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
    P1 O2 . 1.470(3) Y
    P1 O1 . 1.595(3) Y
    P1 C17 . 1.796(4) Y
    P1 C11 . 1.814(4) Y
    O1 C2 . 1.467(5) ?
    C1 C2 . 1.533(5) ?
    C1 C6 . 1.540(6) ?
    C1 C7 . 1.548(6) ?
    C1 H1 . 0.9800 ?
    C2 C3 . 1.507(6) ?
    C2 H2 . 0.9800 ?
    C3 C4 . 1.524(7) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 C5 . 1.522(7) ?
    C4 C10 . 1.546(7) ?
    C4 H4 . 0.9800 ?
    C5 C6 . 1.504(7) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 C8 . 1.529(8) ?
    C7 C9 . 1.528(7) ?
    C7 H7 . 0.9800 ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C8 H8C . 0.9600 ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
    C11 C16 . 1.377(6) ?
    C11 C12 . 1.394(6) ?
    C12 C13 . 1.400(7) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.366(8) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.377(8) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.380(7) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.519(6) ?
    C17 H17A . 0.9700 ?
    C17 H17B . 0.9700 ?
    C18 C19 . 1.374(6) ?
    C18 C23 . 1.396(6) ?
    C19 C20 . 1.395(7) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.377(9) ?
    C20 H20 . 0.9300 ?
    C21 C22 . 1.356(9) ?
    C21 H21 . 0.9300 ?
    C22 C23 . 1.370(7) ?
    C22 H22 . 0.9300 ?
    C23 H23 . 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
    O2 P1 O1 . . 114.13(15) Y
    O2 P1 C17 . . 115.1(2) Y
    O1 P1 C17 . . 102.76(18) Y
    O2 P1 C11 . . 112.96(18) Y
    O1 P1 C11 . . 105.23(17) Y
    C17 P1 C11 . . 105.6(2) Y
    C2 O1 P1 . . 119.8(3) ?
    C2 C1 C6 . . 107.3(4) ?
    C2 C1 C7 . . 114.1(3) ?
    C6 C1 C7 . . 114.2(4) ?
    C2 C1 H1 . . 106.9 ?
    C6 C1 H1 . . 106.9 ?
    C7 C1 H1 . . 106.9 ?
    O1 C2 C3 . . 112.1(3) ?
    O1 C2 C1 . . 108.2(4) ?
    C3 C2 C1 . . 111.6(3) ?
    O1 C2 H2 . . 108.3 ?
    C3 C2 H2 . . 108.3 ?
    C1 C2 H2 . . 108.3 ?
    C2 C3 C4 . . 111.9(4) ?
    C2 C3 H3A . . 109.2 ?
    C4 C3 H3A . . 109.2 ?
    C2 C3 H3B . . 109.2 ?
    C4 C3 H3B . . 109.2 ?
    H3A C3 H3B . . 107.9 ?
    C5 C4 C3 . . 109.2(5) ?
    C5 C4 C10 . . 112.9(4) ?
    C3 C4 C10 . . 112.6(5) ?
    C5 C4 H4 . . 107.3 ?
    C3 C4 H4 . . 107.3 ?
    C10 C4 H4 . . 107.3 ?
    C6 C5 C4 . . 112.2(4) ?
    C6 C5 H5A . . 109.2 ?
    C4 C5 H5A . . 109.2 ?
    C6 C5 H5B . . 109.2 ?
    C4 C5 H5B . . 109.2 ?
    H5A C5 H5B . . 107.9 ?
    C5 C6 C1 . . 112.8(4) ?
    C5 C6 H6A . . 109.0 ?
    C1 C6 H6A . . 109.0 ?
    C5 C6 H6B . . 109.0 ?
    C1 C6 H6B . . 109.0 ?
    H6A C6 H6B . . 107.8 ?
    C8 C7 C9 . . 110.6(4) ?
    C8 C7 C1 . . 113.2(5) ?
    C9 C7 C1 . . 111.5(4) ?
    C8 C7 H7 . . 107.0 ?
    C9 C7 H7 . . 107.0 ?
    C1 C7 H7 . . 107.0 ?
    C7 C8 H8A . . 109.5 ?
    C7 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C7 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C7 C9 H9A . . 109.5 ?
    C7 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C7 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C4 C10 H10A . . 109.5 ?
    C4 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C4 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C16 C11 C12 . . 119.6(4) ?
    C16 C11 P1 . . 121.4(3) ?
    C12 C11 P1 . . 119.0(3) ?
    C11 C12 C13 . . 119.1(5) ?
    C11 C12 H12 . . 120.5 ?
    C13 C12 H12 . . 120.5 ?
    C14 C13 C12 . . 120.7(5) ?
    C14 C13 H13 . . 119.7 ?
    C12 C13 H13 . . 119.7 ?
    C13 C14 C15 . . 119.7(5) ?
    C13 C14 H14 . . 120.2 ?
    C15 C14 H14 . . 120.2 ?
    C14 C15 C16 . . 120.5(6) ?
    C14 C15 H15 . . 119.7 ?
    C16 C15 H15 . . 119.7 ?
    C11 C16 C15 . . 120.4(5) ?
    C11 C16 H16 . . 119.8 ?
    C15 C16 H16 . . 119.8 ?
    C18 C17 P1 . . 113.5(3) ?
    C18 C17 H17A . . 108.9 ?
    P1 C17 H17A . . 108.9 ?
    C18 C17 H17B . . 108.9 ?
    P1 C17 H17B . . 108.9 ?
    H17A C17 H17B . . 107.7 ?
    C19 C18 C23 . . 118.7(4) ?
    C19 C18 C17 . . 121.7(4) ?
    C23 C18 C17 . . 119.6(4) ?
    C18 C19 C20 . . 119.6(5) ?
    C18 C19 H19 . . 120.2 ?
    C20 C19 H19 . . 120.2 ?
    C21 C20 C19 . . 120.9(6) ?
    C21 C20 H20 . . 119.6 ?
    C19 C20 H20 . . 119.6 ?
    C22 C21 C20 . . 119.3(5) ?
    C22 C21 H21 . . 120.4 ?
    C20 C21 H21 . . 120.4 ?
    C21 C22 C23 . . 120.8(5) ?
    C21 C22 H22 . . 119.6 ?
    C23 C22 H22 . . 119.6 ?
    C22 C23 C18 . . 120.7(5) ?
    C22 C23 H23 . . 119.6 ?
    C18 C23 H23 . . 119.6 ?
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
    C7 H7 O1 . 0.98 2.49 2.893(5) 104
data_global
_journal_date_recd_electronic     2010-03-09
_journal_date_accepted     2010-03-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      4
_journal_page_first     o863
_journal_page_last     o863
_journal_paper_category     QO
_journal_coeditor_code     BX2269
_publ_contact_author_name     'Prof. Chang-Qiu Zhao'
_publ_contact_author_address
;
  College of Chemistry and Chemical Engineering
  Liaocheng University
  Shandong 252059
  People's Republic of China
;
_publ_contact_author_email     literabc@hotmail.com
_publ_contact_author_fax     '86 635 8239659'
_publ_contact_author_phone     '86 635 8239659'
_publ_section_title
;
(SP)-Menthyl benzyl(phenyl)phosphonate
;
loop_
    _publ_author_name
    _publ_author_address
    'Wei-Min Wang'
;
  College of Chemistry and Chemical Engineering
  Liaocheng University
  Shandong 252059
  People's Republic of China
;
    'Chang-Qiu Zhao'
;
  College of Chemistry and Chemical Engineering
  Liaocheng University
  Shandong 252059
  People's Republic of China
;
