#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/63/2206337.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_2206337
loop_
_publ_author_name
'Zang, Hong-Jun'
'Guo, Ming-Lin'
_publ_section_title
N-(2-Nitrophenyl)-1-oxo-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-4-carboxamide
_journal_coeditor_code           AT6025
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2772
_journal_page_last               o2774
_journal_paper_doi               10.1107/S1600536805023974
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C11 H11 N2 O7 P'
_chemical_formula_moiety         'C11 H11 N2 O7 P'
_chemical_formula_sum            'C11 H11 N2 O7 P'
_chemical_formula_weight         314.19
_chemical_name_systematic
;
N-(2-Nitrophenyl)-1-oxo-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-
4-carboxamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 105.075(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2381(14)
_cell_length_b                   12.269(2)
_cell_length_c                   12.937(2)
_cell_measurement_reflns_used    2576
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.33
_cell_volume                     1262.6(4)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART 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  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7022
_diffrn_reflns_theta_full        26.43
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.31
_refine_ls_extinction_coef       0.043(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.065
_refine_ls_R_factor_gt           0.041
_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)+(0.0526P)²+0.5183P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.099
_refine_ls_wR_factor_ref         0.115
_reflns_number_gt                1865
_reflns_number_total             2597
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at6025.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2206337
_cod_database_fobs_code          2206337
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
P1 0.12937(8) 1.03092(5) 0.81475(5) 0.0426(2) Uani d . 1 P
O1 0.1010(2) 1.13965(13) 0.77038(15) 0.0613(5) Uani d . 1 O
O2 -0.0235(2) 0.98060(14) 0.84970(16) 0.0592(5) Uani d . 1 O
O3 0.1696(3) 0.94416(13) 0.73634(13) 0.0624(5) Uani d . 1 O
O4 0.2778(2) 1.02131(12) 0.91803(14) 0.0527(5) Uani d . 1 O
O5 0.1851(3) 0.71113(15) 1.03627(16) 0.0855(7) Uani d . 1 O
O6 0.3980(3) 0.58254(16) 0.74031(14) 0.0633(5) Uani d . 1 O
O7 0.4067(2) 0.41380(17) 0.69884(15) 0.0710(6) Uani d . 1 O
N1 0.2606(2) 0.63850(15) 0.89486(15) 0.0392(4) Uani d . 1 N
N2 0.3842(2) 0.48521(18) 0.75939(16) 0.0483(5) Uani d . 1 N
C1 0.0045(3) 0.8699(2) 0.8929(2) 0.0527(6) Uani d . 1 C
H1A -0.0785 0.8210 0.8498 0.063 Uiso calc R 1 H
H1B -0.0081 0.8688 0.9654 0.063 Uiso calc R 1 H
C2 0.3099(3) 0.91067(17) 0.95989(19) 0.0485(6) Uani d . 1 C
H2A 0.3031 0.9089 1.0336 0.058 Uiso calc R 1 H
H2B 0.4224 0.8886 0.9585 0.058 Uiso calc R 1 H
C3 0.1962(3) 0.83318(17) 0.77724(17) 0.0479(6) Uani d . 1 C
H3A 0.3068 0.8080 0.7748 0.057 Uiso calc R 1 H
H3B 0.1129 0.7850 0.7333 0.057 Uiso calc R 1 H
C4 0.1816(3) 0.83142(16) 0.89286(16) 0.0352(5) Uani d . 1 C
C5 0.2087(3) 0.71979(18) 0.94850(17) 0.0411(5) Uani d . 1 C
C6 0.2811(3) 0.52788(17) 0.92200(16) 0.0365(5) Uani d . 1 C
C7 0.2408(3) 0.48648(18) 1.01246(18) 0.0453(6) Uani d . 1 C
H7 0.2023 0.5336 1.0572 0.054 Uiso calc R 1 H
C8 0.2568(3) 0.37693(19) 1.0370(2) 0.0523(6) Uani d . 1 C
H8 0.2306 0.3516 1.0985 0.063 Uiso calc R 1 H
C9 0.3113(3) 0.3044(2) 0.9716(2) 0.0572(7) Uani d . 1 C
H9 0.3203 0.2305 0.9881 0.069 Uiso calc R 1 H
C10 0.3519(3) 0.3424(2) 0.8822(2) 0.0531(6) Uani d . 1 C
H10 0.3890 0.2940 0.8379 0.064 Uiso calc R 1 H
C11 0.3383(3) 0.45231(18) 0.85702(17) 0.0410(5) Uani d . 1 C
H1 0.288(3) 0.654(2) 0.840(2) 0.050(7) Uiso d . 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'
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
_geom_angle_publ_flag
O1 P1 O4 114.72(10) yes
O1 P1 O3 114.18(10) yes
O4 P1 O3 104.62(10) yes
O1 P1 O2 114.69(11) yes
O4 P1 O2 103.41(10) yes
O3 P1 O2 103.90(11) yes
C1 O2 P1 114.59(14) yes
C3 O3 P1 115.97(13) yes
C2 O4 P1 114.39(13) yes
C5 N1 C6 128.45(19) ?
C5 N1 H1 118.0(18) ?
C6 N1 H1 113.5(18) ?
O7 N2 O6 122.0(2) yes
O7 N2 C11 118.1(2) yes
O6 N2 C11 119.86(18) yes
O2 C1 C4 109.92(18) ?
O2 C1 H1A 109.7 ?
C4 C1 H1A 109.7 ?
O2 C1 H1B 109.7 ?
C4 C1 H1B 109.7 ?
H1A C1 H1B 108.2 ?
O4 C2 C4 110.44(17) ?
O4 C2 H2A 109.6 ?
C4 C2 H2A 109.6 ?
O4 C2 H2B 109.6 ?
C4 C2 H2B 109.6 ?
H2A C2 H2B 108.1 ?
O3 C3 C4 108.98(17) ?
O3 C3 H3A 109.9 ?
C4 C3 H3A 109.9 ?
O3 C3 H3B 109.9 ?
C4 C3 H3B 109.9 ?
H3A C3 H3B 108.3 ?
C2 C4 C3 109.06(19) ?
C2 C4 C1 108.74(19) ?
C3 C4 C1 108.22(19) ?
C2 C4 C5 107.84(17) ?
C3 C4 C5 115.55(17) ?
C1 C4 C5 107.26(17) ?
O5 C5 N1 124.8(2) ?
O5 C5 C4 118.71(19) ?
N1 C5 C4 116.47(18) ?
C7 C6 N1 121.63(19) ?
C7 C6 C11 116.8(2) ?
N1 C6 C11 121.6(2) ?
C8 C7 C6 121.3(2) ?
C8 C7 H7 119.4 ?
C6 C7 H7 119.4 ?
C7 C8 C9 120.9(2) ?
C7 C8 H8 119.6 ?
C9 C8 H8 119.6 ?
C10 C9 C8 119.3(2) ?
C10 C9 H9 120.4 ?
C8 C9 H9 120.4 ?
C9 C10 C11 120.6(2) ?
C9 C10 H10 119.7 ?
C11 C10 H10 119.7 ?
C10 C11 C6 121.2(2) ?
C10 C11 N2 116.6(2) ?
C6 C11 N2 122.2(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O1 1.4472(18) yes
P1 O4 1.5637(17) yes
P1 O3 1.5643(18) yes
P1 O2 1.5710(19) yes
O2 C1 1.464(3) ?
O3 C3 1.457(3) ?
O4 C2 1.460(3) ?
O5 C5 1.206(3) ?
O6 N2 1.231(3) yes
O7 N2 1.221(2) yes
N1 C5 1.347(3) ?
N1 C6 1.401(3) ?
N1 H1 0.82(3) ?
N2 C11 1.466(3) ?
C1 C4 1.534(3) ?
C1 H1A 0.9700 ?
C1 H1B 0.9700 ?
C2 C4 1.529(3) ?
C2 H2A 0.9700 ?
C2 H2B 0.9700 ?
C3 C4 1.532(3) ?
C3 H3A 0.9700 ?
C3 H3B 0.9700 ?
C4 C5 1.536(3) ?
C6 C7 1.393(3) ?
C6 C11 1.412(3) ?
C7 C8 1.379(3) ?
C7 H7 0.9300 ?
C8 C9 1.382(4) ?
C8 H8 0.9300 ?
C9 C10 1.366(4) ?
C9 H9 0.9300 ?
C10 C11 1.385(3) ?
C10 H10 0.9300 ?
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
N1 H1 O6 . 0.82(3) 1.97(3) 2.632(3) 138(2)
N1 H1 N2 . 0.82(3) 2.54(2) 2.928(3) 111(2)
C2 H2A O6 4_576 0.97 2.59 3.511(3) 159
C3 H3B O1 2_546 0.97 2.50 3.351(3) 147
C7 H7 O5 . 0.93 2.19 2.824(3) 124
C7 H7 O3 4_576 0.93 2.42 3.216(3) 144
C10 H10 O7 . 0.93 2.36 2.675(3) 100
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
_geom_torsion_publ_flag
O1 P1 O2 C1 179.05(17) ?
O4 P1 O2 C1 -55.31(19) ?
O3 P1 O2 C1 53.73(19) ?
O1 P1 O3 C3 -179.01(17) ?
O4 P1 O3 C3 54.8(2) ?
O2 P1 O3 C3 -53.4(2) ?
O1 P1 O4 C2 -177.69(17) ?
O3 P1 O4 C2 -51.81(19) ?
O2 P1 O4 C2 56.69(18) ?
P1 O2 C1 C4 0.2(3) ?
P1 O4 C2 C4 -2.5(3) ?
P1 O3 C3 C4 -1.5(3) ?
O4 C2 C4 C3 60.5(2) ?
O4 C2 C4 C1 -57.3(2) ?
O4 C2 C4 C5 -173.34(18) ?
O3 C3 C4 C2 -57.7(2) ?
O3 C3 C4 C1 60.5(2) ?
O3 C3 C4 C5 -179.30(19) ?
O2 C1 C4 C2 58.5(2) ?
O2 C1 C4 C3 -59.9(2) ?
O2 C1 C4 C5 174.83(18) ?
C6 N1 C5 O5 7.2(4) ?
C6 N1 C5 C4 -174.01(19) ?
C2 C4 C5 O5 63.8(3) ?
C3 C4 C5 O5 -173.9(2) ?
C1 C4 C5 O5 -53.1(3) ?
C2 C4 C5 N1 -115.1(2) ?
C3 C4 C5 N1 7.2(3) ?
C1 C4 C5 N1 128.0(2) ?
C5 N1 C6 C7 2.6(3) ?
C5 N1 C6 C11 -179.6(2) ?
N1 C6 C7 C8 178.2(2) ?
C11 C6 C7 C8 0.2(3) ?
C6 C7 C8 C9 -0.9(4) ?
C7 C8 C9 C10 0.9(4) ?
C8 C9 C10 C11 -0.2(4) ?
C9 C10 C11 C6 -0.5(4) ?
C9 C10 C11 N2 -179.8(2) ?
C7 C6 C11 C10 0.5(3) ?
N1 C6 C11 C10 -177.5(2) ?
C7 C6 C11 N2 179.77(19) ?
N1 C6 C11 N2 1.8(3) ?
O7 N2 C11 C10 10.7(3) yes
O6 N2 C11 C10 -169.7(2) yes
O7 N2 C11 C6 -168.6(2) yes
O6 N2 C11 C6 11.0(3) yes
