#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2203192.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2203192
loop_
_publ_author_name
'Fang, Hua'
'Wang, Jian-Feng'
'Liu, Xiao-Xia'
'Zhao, Yu-Fen'
'Ng, Seik Weng'
_publ_section_title
;
Diethyl phenyl(4-pyridylcarbonylamino)methylphosphonate
;
_journal_issue                 2
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o153
_journal_page_last             o154
_journal_volume                60
_journal_year                  2004
_chemical_formula_iupac        'C17 H21 N2 O4 P'
_chemical_formula_moiety       'C17 H21 N2 O4 P'
_chemical_formula_sum          'C17 H21 N2 O4 P'
_chemical_formula_weight       348.33
_chemical_melting_point        ?
_chemical_name_common          ?
_chemical_name_systematic
;
Diethyl phenyl(4-pyridylcarbonylamino)methylphosphonate
;
_symmetry_cell_setting         monoclinic
_symmetry_space_group_name_Hall '-C 2yc'
_symmetry_space_group_name_H-M 'C 2/c'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_audit_creation_method         SHELXL-97
_cell_angle_alpha              90
_cell_angle_beta               110.3250(10)
_cell_angle_gamma              90
_cell_formula_units_Z          8
_cell_length_a                 23.7140(10)
_cell_length_b                 8.0928(4)
_cell_length_c                 20.0120(10)
_cell_measurement_reflns_used  4335
_cell_measurement_temperature  293(2)
_cell_measurement_theta_max    27.5
_cell_measurement_theta_min    2.3
_cell_volume                   3601.4(3)
_computing_cell_refinement     SMART
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_data_reduction      'SAINT (Bruker, 2001)'
_computing_molecular_graphics  'ORTEPII (Johnson, 1976)'
_computing_publication_material SHELXL97
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution  'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature    293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 1.0
_diffrn_measurement_device_type 'Bruker APEX area-detector'
_diffrn_measurement_method     '\f and \w'
_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 0.022
_diffrn_reflns_av_sigmaI/netI  0.022
_diffrn_reflns_limit_h_max     28
_diffrn_reflns_limit_h_min     -28
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_l_max     23
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_number          12057
_diffrn_reflns_theta_full      25.0
_diffrn_reflns_theta_max       25.0
_diffrn_reflns_theta_min       1.8
_diffrn_standards_decay_%      0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time 0
_diffrn_standards_number       0
_exptl_absorpt_coefficient_mu  0.175
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_crystal_colour          colourless
_exptl_crystal_density_diffrn  1.285
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     block
_exptl_crystal_F_000           1472
_exptl_crystal_size_max        0.35
_exptl_crystal_size_mid        0.27
_exptl_crystal_size_min        0.26
_refine_diff_density_max       0.95
_refine_diff_density_min       -0.32
_refine_ls_extinction_coef     ?
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_ref 1.05
_refine_ls_hydrogen_treatment  mixed
_refine_ls_matrix_type         full
_refine_ls_number_parameters   221
_refine_ls_number_reflns       3162
_refine_ls_number_restraints   1
_refine_ls_restrained_S_all    1.05
_refine_ls_R_factor_all        0.079
_refine_ls_R_factor_gt         0.072
_refine_ls_shift/su_max        0.000
_refine_ls_shift/su_mean       0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.1172P)^2^+6.3036P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.200
_refine_ls_wR_factor_ref       0.207
_reflns_number_gt              2774
_reflns_number_total           3162
_reflns_threshold_expression   I>2\s(I)
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
P1 0.44530(10) 0.44600(10) 0.58710(10) 0.0457(3) Uani d . 1 . . P
N1 0.7627(2) 0.6298(6) 0.6720(3) 0.0940(10) Uani d . 1 . . N
N2 0.53740(10) 0.6483(3) 0.61780(10) 0.0460(10) Uani d D 1 . . N
O2 0.57880(10) 0.7240(4) 0.73170(10) 0.0800(10) Uani d . 1 . . O
O3 0.47520(10) 0.3332(3) 0.65310(10) 0.0750(10) Uani d . 1 . . O
O4 0.37630(10) 0.4501(3) 0.5741(2) 0.0700(10) Uani d . 1 . . O
O5 0.45360(10) 0.3961(3) 0.52170(10) 0.0610(10) Uani d . 1 . . O
C1 0.64540(10) 0.6638(4) 0.6710(2) 0.0510(10) Uani d . 1 . . C
C2 0.6583(2) 0.5617(5) 0.6232(2) 0.0630(10) Uani d . 1 . . C
C3 0.7173(2) 0.5495(6) 0.6265(2) 0.0810(10) Uani d . 1 . . C
C4 0.7492(2) 0.7287(8) 0.7164(3) 0.099(2) Uani d . 1 . . C
C5 0.6928(2) 0.7497(6) 0.7184(2) 0.0770(10) Uani d . 1 . . C
C6 0.58410(10) 0.6831(4) 0.6760(2) 0.0490(10) Uani d . 1 . . C
C7 0.47650(10) 0.6489(4) 0.6182(2) 0.0450(10) Uani d . 1 . . C
C8 0.43810(10) 0.7884(4) 0.5768(2) 0.0460(10) Uani d . 1 . . C
C9 0.4387(2) 0.8348(5) 0.5112(2) 0.0630(10) Uani d . 1 . . C
C10 0.4035(2) 0.9637(5) 0.4747(2) 0.0740(10) Uani d . 1 . . C
C11 0.3664(2) 1.0452(5) 0.5024(2) 0.0700(10) Uani d . 1 . . C
C12 0.3645(2) 1.0003(5) 0.5673(2) 0.0690(10) Uani d . 1 . . C
C13 0.4006(2) 0.8727(5) 0.6049(2) 0.0580(10) Uani d . 1 . . C
C14 0.5078(2) 0.1842(5) 0.6549(2) 0.0760(10) Uani d . 1 . . C
C15 0.5698(2) 0.1977(9) 0.6972(3) 0.117(2) Uani d . 1 . . C
C16 0.3501(2) 0.4646(7) 0.6271(3) 0.0860(10) Uani d . 1 . . C
C17 0.2901(2) 0.5394(9) 0.5959(3) 0.122(2) Uani d . 1 . . C
H1 0.5430(10) 0.630(4) 0.5790(9) 0.039(8) Uiso d D 1 . . H
H2 0.6281 0.5023 0.5896 0.076 Uiso calc R 1 . . H
H3 0.7255 0.4795 0.5942 0.097 Uiso calc R 1 . . H
H4 0.7804 0.7886 0.7486 0.118 Uiso calc R 1 . . H
H5 0.6862 0.8211 0.7514 0.092 Uiso calc R 1 . . H
H7 0.4788 0.6598 0.6679 0.054 Uiso calc R 1 . . H
H9 0.4631 0.7786 0.4912 0.075 Uiso calc R 1 . . H
H10 0.4051 0.9954 0.4307 0.088 Uiso calc R 1 . . H
H11 0.3424 1.1313 0.4771 0.084 Uiso calc R 1 . . H
H12 0.3390 1.0553 0.5862 0.083 Uiso calc R 1 . . H
H13 0.3996 0.8434 0.6495 0.069 Uiso calc R 1 . . H
H14a 0.4899 0.0960 0.6737 0.091 Uiso calc R 1 . . H
H14b 0.5042 0.1546 0.6066 0.091 Uiso calc R 1 . . H
H15a 0.5895 0.0945 0.6965 0.175 Uiso calc R 1 . . H
H15b 0.5737 0.2245 0.7453 0.175 Uiso calc R 1 . . H
H15c 0.5880 0.2832 0.6782 0.175 Uiso calc R 1 . . H
H16a 0.3752 0.5330 0.6658 0.103 Uiso calc R 1 . . H
H16b 0.3467 0.3563 0.6461 0.103 Uiso calc R 1 . . H
H17a 0.2722 0.5498 0.6319 0.183 Uiso calc R 1 . . H
H17b 0.2653 0.4704 0.5580 0.183 Uiso calc R 1 . . H
H17c 0.2938 0.6467 0.5773 0.183 Uiso calc R 1 . . H
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
P1 0.0460(10) 0.0500(10) 0.0430(10) -0.0030(10) 0.0170(10) 0.0030(10)
N1 0.055(2) 0.126(4) 0.103(3) 0.000(2) 0.029(2) 0.008(3)
N2 0.0440(10) 0.060(2) 0.0360(10) -0.0020(10) 0.0140(10) -0.0040(10)
O2 0.059(2) 0.133(3) 0.0450(10) -0.008(2) 0.0150(10) -0.027(2)
O3 0.102(2) 0.067(2) 0.058(2) 0.019(2) 0.0310(10) 0.0100(10)
O4 0.062(2) 0.073(2) 0.082(2) -0.0120(10) 0.0320(10) -0.0040(10)
O5 0.072(2) 0.065(2) 0.0470(10) -0.0170(10) 0.0220(10) -0.0080(10)
C1 0.047(2) 0.060(2) 0.044(2) -0.0010(10) 0.0120(10) 0.0080(10)
C2 0.054(2) 0.078(3) 0.056(2) 0.006(2) 0.018(2) 0.005(2)
C3 0.069(3) 0.102(3) 0.078(3) 0.017(2) 0.034(2) 0.008(2)
C4 0.054(2) 0.129(4) 0.102(4) -0.022(3) 0.013(2) -0.010(3)
C5 0.053(2) 0.097(3) 0.073(2) -0.015(2) 0.013(2) -0.015(2)
C6 0.048(2) 0.056(2) 0.040(2) -0.0020(10) 0.0110(10) -0.0010(10)
C7 0.044(2) 0.056(2) 0.036(2) -0.0050(10) 0.0150(10) -0.0020(10)
C8 0.045(2) 0.048(2) 0.045(2) -0.0090(10) 0.0150(10) -0.0030(10)
C9 0.072(2) 0.066(2) 0.056(2) 0.008(2) 0.029(2) 0.006(2)
C10 0.082(3) 0.072(3) 0.066(2) 0.010(2) 0.026(2) 0.023(2)
C11 0.060(2) 0.055(2) 0.086(3) 0.004(2) 0.014(2) 0.016(2)
C12 0.059(2) 0.061(2) 0.095(3) 0.006(2) 0.035(2) 0.002(2)
C13 0.055(2) 0.062(2) 0.062(2) -0.002(2) 0.028(2) 0.001(2)
C14 0.088(3) 0.064(2) 0.065(2) 0.008(2) 0.014(2) 0.004(2)
C15 0.082(3) 0.152(6) 0.102(4) 0.024(3) 0.013(3) -0.016(4)
C16 0.077(3) 0.098(3) 0.093(3) -0.011(2) 0.043(2) -0.002(3)
C17 0.065(3) 0.174(6) 0.141(5) 0.014(3) 0.053(3) 0.003(5)
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'
N N 0.0061 0.0033 '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'
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
O3 P1 O4 . . 107.1(2) yes
O3 P1 O5 . . 116.0(2) yes
O3 P1 C7 . . 103.2(2) yes
O4 P1 O5 . . 108.6(2) yes
O4 P1 C7 . . 108.30(10) yes
O5 P1 C7 . . 113.20(10) yes
C3 N1 C4 . . 115.9(4) yes
C6 N2 C7 . . 121.6(3) yes
C14 O3 P1 . . 126.8(3) yes
C16 O4 P1 . . 125.9(3) yes
C2 C1 C5 . . 117.1(3) no
C2 C1 C6 . . 124.3(3) no
C5 C1 C6 . . 118.5(3) no
C1 C2 C3 . . 118.4(4) no
N1 C3 C2 . . 124.7(4) no
N1 C4 C5 . . 124.5(5) no
C4 C5 C1 . . 119.3(4) no
O2 C6 N2 . . 122.9(3) no
O2 C6 C1 . . 120.2(3) no
N2 C6 C1 . . 116.8(3) no
N2 C7 C8 . . 114.4(2) no
N2 C7 P1 . . 106.4(2) no
C8 C7 P1 . . 113.1(2) no
C9 C8 C13 . . 118.4(3) no
C9 C8 C7 . . 121.8(3) no
C13 C8 C7 . . 119.8(3) no
C8 C9 C10 . . 120.7(4) no
C11 C10 C9 . . 120.6(4) no
C10 C11 C12 . . 119.9(4) no
C11 C12 C13 . . 119.8(4) no
C12 C13 C8 . . 120.6(3) no
C15 C14 O3 . . 112.9(4) no
O4 C16 C17 . . 109.2(4) no
C6 N2 H1 . . 120(2) no
C7 N2 H1 . . 119(2) no
C1 C2 H2 . . 120.8 no
C3 C2 H2 . . 120.8 no
N1 C3 H3 . . 117.6 no
C2 C3 H3 . . 117.6 no
N1 C4 H4 . . 117.7 no
C5 C4 H4 . . 117.7 no
C4 C5 H5 . . 120.3 no
C1 C5 H5 . . 120.3 no
N2 C7 H7 . . 107.5 no
C8 C7 H7 . . 107.5 no
P1 C7 H7 . . 107.5 no
C8 C9 H9 . . 119.7 no
C10 C9 H9 . . 119.7 no
C11 C10 H10 . . 119.7 no
C9 C10 H10 . . 119.7 no
C10 C11 H11 . . 120.0 no
C12 C11 H11 . . 120.0 no
C11 C12 H12 . . 120.1 no
C13 C12 H12 . . 120.1 no
C12 C13 H13 . . 119.7 no
C8 C13 H13 . . 119.7 no
C15 C14 H14a . . 109.0 no
O3 C14 H14a . . 109.0 no
C15 C14 H14b . . 109.0 no
O3 C14 H14b . . 109.0 no
H14a C14 H14b . . 107.8 no
C14 C15 H15a . . 109.5 no
C14 C15 H15b . . 109.5 no
H15a C15 H15b . . 109.5 no
C14 C15 H15c . . 109.5 no
H15a C15 H15c . . 109.5 no
H15b C15 H15c . . 109.5 no
O4 C16 H16a . . 109.8 no
C17 C16 H16a . . 109.8 no
O4 C16 H16b . . 109.8 no
C17 C16 H16b . . 109.8 no
H16a C16 H16b . . 108.3 no
C16 C17 H17a . . 109.5 no
C16 C17 H17b . . 109.5 no
H17a C17 H17b . . 109.5 no
C16 C17 H17c . . 109.5 no
H17a C17 H17c . . 109.5 no
H17b C17 H17c . . 109.5 no
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 O3 . 1.559(3) yes
P1 O4 . 1.565(3) yes
P1 O5 . 1.448(2) yes
P1 C7 . 1.819(3) yes
N1 C3 . 1.314(6) yes
N1 C4 . 1.314(7) yes
N2 C6 . 1.330(4) yes
N2 C7 . 1.447(4) yes
O2 C6 . 1.210(4) yes
O3 C14 . 1.425(5) yes
O4 C16 . 1.407(5) yes
C1 C2 . 1.375(5) no
C1 C5 . 1.380(5) no
C1 C6 . 1.500(4) no
C2 C3 . 1.381(5) no
C4 C5 . 1.364(6) no
C7 C8 . 1.506(4) no
C4 C5 . 1.364(6) no
C7 C8 . 1.506(4) no
C8 C13 . 1.386(5) no
C9 C10 . 1.377(5) no
C10 C11 . 1.362(6) no
C11 C12 . 1.364(6) no
C12 C13 . 1.385(5) no
C14 C15 . 1.424(6) no
C16 C17 . 1.470(7) no
C8 C9 . 1.370(5) no
C8 C13 . 1.386(5) no
C9 C10 . 1.377(5) no
C10 C11 . 1.362(6) no
C11 C12 . 1.364(6) no
C12 C13 . 1.385(5) no
C14 C15 . 1.424(6) no
C16 C17 . 1.470(7) no
N2 H1 . 0.840(10) no
C2 H2 . 0.93 no
C3 H3 . 0.93 no
C4 H4 . 0.93 no
C5 H5 . 0.93 no
C7 H7 . 0.98 no
C9 H9 . 0.93 no
C10 H10 . 0.93 no
C11 H11 . 0.93 no
C12 H12 . 0.93 no
C13 H13 . 0.93 no
C14 H14a . 0.97 no
C14 H14b . 0.97 no
C15 H15a . 0.96 no
C15 H15b . 0.96 no
C15 H15c . 0.96 no
C16 H16a . 0.97 no
C16 H16b . 0.97 no
C17 H17a . 0.96 no
C17 H17b . 0.96 no
C17 H17c . 0.96 no
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
_geom_hbond_publ_flag
N2 H1 O5 5_666 0.840(10) 2.060(10) 2.894(3) 173(3) yes
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
O5 P1 O3 C14 . . . . -2.4(4) no
O4 P1 O3 C14 . . . . 119.1(4) no
C7 P1 O3 C14 . . . . -126.7(3) no
O5 P1 O4 C16 . . . . 168.3(3) no
O3 P1 O4 C16 . . . . 42.3(4) no
C7 P1 O4 C16 . . . . -68.3(4) no
C5 C1 C2 C3 . . . . 1.1(5) no
C6 C1 C2 C3 . . . . -176.9(3) no
C4 N1 C3 C2 . . . . -0.6(8) no
C1 C2 C3 N1 . . . . -0.5(7) no
C3 N1 C4 C5 . . . . 1.1(8) no
N1 C4 C5 C1 . . . . -0.5(8) no
C2 C1 C5 C4 . . . . -0.6(6) no
C6 C1 C5 C4 . . . . 177.5(4) no
C7 N2 C6 O2 . . . . -3.3(5) no
C7 N2 C6 C1 . . . . 174.6(3) no
C2 C1 C6 O2 . . . . 153.6(4) no
C5 C1 C6 O2 . . . . -24.3(5) no
C2 C1 C6 N2 . . . . -24.4(5) no
C5 C1 C6 N2 . . . . 157.6(3) no
C6 N2 C7 C8 . . . . 110.2(3) no
C6 N2 C7 P1 . . . . -124.1(3) no
O5 P1 C7 N2 . . . . -49.9(2) no
O3 P1 C7 N2 . . . . 76.3(2) no
O4 P1 C7 N2 . . . . -170.4(2) no
O5 P1 C7 C8 . . . . 76.5(2) no
O3 P1 C7 C8 . . . . -157.3(2) no
O4 P1 C7 C8 . . . . -44.0(2) no
N2 C7 C8 C9 . . . . 43.0(4) no
P1 C7 C8 C9 . . . . -79.1(3) no
N2 C7 C8 C13 . . . . -137.3(3) no
P1 C7 C8 C13 . . . . 100.6(3) no
C13 C8 C9 C10 . . . . 0.9(5) no
C7 C8 C9 C10 . . . . -179.4(3) no
C8 C9 C10 C11 . . . . -1.4(6) no
C9 C10 C11 C12 . . . . 0.8(7) no
C10 C11 C12 C13 . . . . 0.4(6) no
C11 C12 C13 C8 . . . . -1.0(6) no
C9 C8 C13 C12 . . . . 0.3(5) no
C7 C8 C13 C12 . . . . -179.4(3) no
P1 O3 C14 C15 . . . . 113.8(4) no
P1 O4 C16 C17 . . . . 153.9(4) no