#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/76/2207661.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_2207661
loop_
_publ_author_name
'Zang, Hong-Jun'
'Guo, Ming-Lin'
'Cheng, Bo-Wen'
'Ren, Yuan-Lin'
_publ_section_title
;N-(3-Nitrophenyl)-1-oxo-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-4-carboxamide
 dimethylformamide solvate
;
_journal_coeditor_code           SU6238
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4195
_journal_page_last               o4197
_journal_paper_doi               10.1107/S1600536805037311
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C11 H11 N2 O7 P, C3 H7 N O'
_chemical_formula_moiety         'C11 H11 N2 O7 P, C3 H7 N O'
_chemical_formula_sum            'C14 H18 N3 O8 P'
_chemical_formula_weight         387.28
_chemical_name_systematic
;N-(3-Nitrophenyl)-1-oxo-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-4-carboxamide
dimethylformamide
 solvate
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 114.344(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.052(2)
_cell_length_b                   6.7210(15)
_cell_length_c                   13.204(3)
_cell_measurement_reflns_used    1715
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      3.13
_cell_volume                     893.6(3)
_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      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5100
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         1.69
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.261
_refine_ls_extinction_coef       0.061(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2006
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0427
_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)+(0.0619P)²+0.2629P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1281
_reflns_number_gt                1335
_reflns_number_total             2006
_reflns_threshold_expression     I>2σ
_cod_data_source_file            su6238.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2207661
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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 0.29102(9) 0.2500 0.64612(6) 0.0616(3) Uani d S 1 P
O1 0.1862(3) 0.2500 0.53511(19) 0.0904(9) Uani d S 1 O
O2 0.2420(2) 0.2500 0.74101(16) 0.0659(7) Uani d S 1 O
O3 0.38695(16) 0.4327(3) 0.67331(12) 0.0809(6) Uani d . 1 O
O5 0.55676(18) 0.2500 1.04475(14) 0.0529(6) Uani d S 1 O
O6 1.1947(3) 0.2500 1.0623(3) 0.1047(11) Uani d S 1 O
O7 1.2990(2) 0.2500 1.2386(2) 0.0851(8) Uani d S 1 O
N1 0.7166(2) 0.2500 0.97925(19) 0.0491(6) Uani d S 1 N
N2 1.1963(3) 0.2500 1.1541(3) 0.0665(8) Uani d S 1 N
C1 0.4937(2) 0.4348(3) 0.78379(15) 0.0490(5) Uani d . 1 C
H1C 0.4878 0.5540 0.8230 0.059 Uiso calc R 1 H
H1D 0.5787 0.4355 0.7786 0.059 Uiso calc R 1 H
C3 0.3466(3) 0.2500 0.8533(2) 0.0457(7) Uani d S 1 C
H3A 0.3384 0.1331 0.8931 0.055 Uiso calc PR 0.50 H
H3B 0.3384 0.3669 0.8931 0.055 Uiso calc PR 0.50 H
C4 0.4829(2) 0.2500 0.8475(2) 0.0377(6) Uani d S 1 C
C5 0.5893(3) 0.2500 0.9673(2) 0.0393(6) Uani d S 1 C
C6 0.8331(3) 0.2500 1.0800(2) 0.0435(7) Uani d S 1 C
C7 0.8337(3) 0.2500 1.1853(2) 0.0510(7) Uani d S 1 C
H7 0.7539 0.2500 1.1932 0.061 Uiso calc SR 1 H
C8 0.9530(3) 0.2500 1.2787(2) 0.0583(8) Uani d S 1 C
H8 0.9521 0.2500 1.3488 0.070 Uiso calc SR 1 H
C9 1.0719(3) 0.2500 1.2700(2) 0.0541(8) Uani d S 1 C
H9 1.1517 0.2500 1.3329 0.065 Uiso calc SR 1 H
C10 1.0695(3) 0.2500 1.1656(3) 0.0505(7) Uani d S 1 C
C11 0.9534(3) 0.2500 1.0698(2) 0.0482(7) Uani d S 1 C
H11 0.9556 0.2500 1.0002 0.058 Uiso calc SR 1 H
O8 0.7895(2) 0.2500 0.79608(18) 0.0744(7) Uani d S 1 O
N3 0.8057(3) 0.2500 0.6311(2) 0.0586(7) Uani d S 1 N
C12 0.8541(3) 0.2500 0.7396(3) 0.0570(8) Uani d S 1 C
H12 0.9461 0.2500 0.7776 0.068 Uiso calc SR 1 H
C13 0.6638(4) 0.2500 0.5664(3) 0.1112(18) Uani d S 1 C
H13A 0.6439 0.3086 0.4950 0.167 Uiso calc PR 0.50 H
H13B 0.6217 0.3257 0.6046 0.167 Uiso calc PR 0.50 H
H13C 0.6314 0.1157 0.5568 0.167 Uiso calc PR 0.50 H
C14 0.8901(4) 0.2500 0.5707(3) 0.0872(13) Uani d S 1 C
H14A 0.8579 0.1532 0.5121 0.131 Uiso calc PR 0.50 H
H14B 0.9794 0.2174 0.6207 0.131 Uiso calc PR 0.50 H
H14C 0.8885 0.3795 0.5395 0.131 Uiso calc PR 0.50 H
H1 0.734(3) 0.2500 0.919(3) 0.065(10) Uiso d S 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 P1 O2 . . 114.63(14) y
O1 P1 O3 . . 114.62(8) y
O2 P1 O3 . . 104.07(9) y
O1 P1 O3 . 4_565 114.62(8) ?
O2 P1 O3 . 4_565 104.07(9) ?
O3 P1 O3 . 4_565 103.45(15) y
C3 O2 P1 . . 115.21(17) y
C1 O3 P1 . . 115.58(13) y
C5 N1 C6 . . 127.5(2) ?
C5 N1 H1 . . 120(2) ?
C6 N1 H1 . . 113(2) ?
O6 N2 O7 . . 122.8(3) ?
O6 N2 C10 . . 119.0(3) ?
O7 N2 C10 . . 118.2(3) ?
O3 C1 C4 . . 109.25(17) ?
O3 C1 H1C . . 109.8 ?
C4 C1 H1C . . 109.8 ?
O3 C1 H1D . . 109.8 ?
C4 C1 H1D . . 109.8 ?
H1C C1 H1D . . 108.3 ?
O2 C3 C4 . . 109.3(2) ?
O2 C3 H3A . . 109.8 ?
C4 C3 H3A . . 109.8 ?
O2 C3 H3B . . 109.8 ?
C4 C3 H3B . . 109.8 ?
H3A C3 H3B . . 108.3 ?
C1 C4 C1 4_565 . 108.3(2) ?
C1 C4 C5 4_565 . 111.47(14) ?
C1 C4 C5 . . 111.47(14) ?
C1 C4 C3 4_565 . 109.06(15) ?
C1 C4 C3 . . 109.06(14) ?
C5 C4 C3 . . 107.4(2) ?
O5 C5 N1 . . 123.8(2) ?
O5 C5 C4 . . 120.0(2) ?
N1 C5 C4 . . 116.1(2) ?
C7 C6 C11 . . 119.2(3) ?
C7 C6 N1 . . 124.5(2) ?
C11 C6 N1 . . 116.3(2) ?
C8 C7 C6 . . 120.1(3) ?
C8 C7 H7 . . 120.0 ?
C6 C7 H7 . . 120.0 ?
C9 C8 C7 . . 121.4(3) ?
C9 C8 H8 . . 119.3 ?
C7 C8 H8 . . 119.3 ?
C8 C9 C10 . . 117.7(3) ?
C8 C9 H9 . . 121.1 ?
C10 C9 H9 . . 121.1 ?
C9 C10 C11 . . 123.2(3) ?
C9 C10 N2 . . 118.8(3) ?
C11 C10 N2 . . 118.1(3) ?
C10 C11 C6 . . 118.4(3) ?
C10 C11 H11 . . 120.8 ?
C6 C11 H11 . . 120.8 ?
C12 N3 C13 . . 120.1(3) ?
C12 N3 C14 . . 122.4(3) ?
C13 N3 C14 . . 117.5(3) ?
O8 C12 N3 . . 126.1(3) ?
O8 C12 H12 . . 116.9 ?
N3 C12 H12 . . 116.9 ?
N3 C13 H13A . . 109.5 ?
N3 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
N3 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N3 C14 H14A . . 109.5 ?
N3 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
N3 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
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 O1 . 1.446(2) y
P1 O2 . 1.557(2) y
P1 O3 . 1.5646(18) y
P1 O3 4_565 1.5646(18) ?
O2 C3 . 1.457(3) ?
O3 C1 . 1.450(2) ?
O5 C5 . 1.217(3) ?
O6 N2 . 1.204(4) ?
O7 N2 . 1.221(4) ?
N1 C5 . 1.349(4) ?
N1 C6 . 1.420(3) ?
N1 H1 . 0.90(3) ?
N2 C10 . 1.471(4) ?
C1 C4 . 1.532(2) ?
C1 H1C . 0.9700 ?
C1 H1D . 0.9700 ?
C3 C4 . 1.540(4) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C1 4_565 1.532(2) ?
C4 C5 . 1.533(3) ?
C6 C7 . 1.388(4) ?
C6 C11 . 1.390(4) ?
C7 C8 . 1.385(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.365(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.368(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.381(4) ?
C11 H11 . 0.9300 ?
O8 C12 . 1.226(4) ?
N3 C12 . 1.307(4) ?
N3 C13 . 1.445(5) ?
N3 C14 . 1.455(4) ?
C12 H12 . 0.9300 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
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 O8 . 0.90(3) 1.95(3) 2.847(3) 175(3)
C1 H1C O5 2_657 0.97 2.40 3.311(3) 157
C1 H1D O8 . 0.97 2.57 3.439(3) 149
C1 H1D O7 2_757 0.97 2.57 3.222(3) 125
C7 H7 O5 . 0.93 2.25 2.851(3) 122
C9 H9 O1 1_656 0.93 2.54 3.194(4) 128
C11 H11 O8 . 0.93 2.56 3.309(4) 138
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_4
_geom_torsion
O1 P1 O2 C3 . . 180.0
O3 P1 O2 C3 . . -54.03(7)
O3 P1 O2 C3 4_565 . 54.03(7)
O1 P1 O3 C1 . . -179.38(17)
O2 P1 O3 C1 . . 54.65(18)
O3 P1 O3 C1 4_565 . -53.9(2)
P1 O3 C1 C4 . . -0.4(2)
P1 O2 C3 C4 . . 0.0
O3 C1 C4 C1 . 4_565 59.9(3)
O3 C1 C4 C5 . . -177.05(17)
O3 C1 C4 C3 . . -58.7(2)
O2 C3 C4 C1 . 4_565 -59.07(14)
O2 C3 C4 C1 . . 59.07(14)
O2 C3 C4 C5 . . 180.0000(10)
C6 N1 C5 O5 . . 0.0000(10)
C6 N1 C5 C4 . . 180.0000(10)
C1 C4 C5 O5 4_565 . -119.40(15)
C1 C4 C5 O5 . . 119.40(15)
C3 C4 C5 O5 . . 0.0000(10)
C1 C4 C5 N1 4_565 . 60.60(15)
C1 C4 C5 N1 . . -60.60(15)
C3 C4 C5 N1 . . 180.0000(10)
C5 N1 C6 C7 . . 0.000(2)
C5 N1 C6 C11 . . 180.0000(10)
C11 C6 C7 C8 . . 0.000(2)
N1 C6 C7 C8 . . 180.000(2)
C6 C7 C8 C9 . . 0.000(2)
C7 C8 C9 C10 . . 0.000(2)
C8 C9 C10 C11 . . 0.000(3)
C8 C9 C10 N2 . . 180.000(2)
O6 N2 C10 C9 . . 180.000(2)
O7 N2 C10 C9 . . 0.000(3)
O6 N2 C10 C11 . . 0.000(3)
O7 N2 C10 C11 . . 180.000(2)
C9 C10 C11 C6 . . 0.000(2)
N2 C10 C11 C6 . . 180.000(2)
C7 C6 C11 C10 . . 0.000(2)
N1 C6 C11 C10 . . 180.000(2)
C13 N3 C12 O8 . . 0.000(2)
C14 N3 C12 O8 . . 180.0000(10)
