#------------------------------------------------------------------------------
#$Date: 2018-09-09 15:05:24 +0300 (Sun, 09 Sep 2018) $
#$Revision: 210631 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/47/7104783.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_7104783
loop_
_publ_author_name
'Yin, Zhenming'
'Jiang, Ling'
'He, Jiaqi'
'Cheng, Jin-Pei'
_publ_section_title
;
 The first observation of nitrogen--carbonyl bonding: self-assembly of
 N-oxalyl 2,4-dinitroanilide assisted by a weak N⋯O=C interaction
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   18
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              2326
_journal_page_last               2327
_journal_paper_doi               10.1039/b306012h
_journal_year                    2003
_chemical_formula_sum            'C9 H7 N3 O7'
_chemical_formula_weight         269.18
_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                 99.330(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.810(3)
_cell_length_b                   4.645(2)
_cell_length_c                   18.340(5)
_cell_measurement_reflns_used    501
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.10
_cell_measurement_theta_min      3.22
_cell_volume                     1076.8(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0822
_diffrn_reflns_av_sigmaI/netI    0.1478
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4643
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.805236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2145
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.913
_refine_ls_R_factor_all          0.2132
_refine_ls_R_factor_gt           0.0496
_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/[σ²(Fo²)+(0.0125P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0883
_reflns_number_gt                742
_reflns_number_total             2145
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b306012h.txt
_cod_data_source_block           N-oxaly_dinitroanilide
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7104783
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1363(3) 0.6691(7) 0.08666(17) 0.0495(9) Uani 1 1 d . . .
H1A H 0.0809 0.6020 0.0516 0.059 Uiso 1 1 calc R . .
C2 C 0.2338(3) 0.5582(7) 0.08852(19) 0.0534(10) Uani 1 1 d . . .
H2A H 0.2455 0.4154 0.0552 0.064 Uiso 1 1 calc R . .
C3 C 0.3143(3) 0.6560(8) 0.1391(2) 0.0556(10) Uani 1 1 d . . .
C4 C 0.2991(3) 0.8606(8) 0.18869(19) 0.0573(10) Uani 1 1 d . . .
H4A H 0.3553 0.9250 0.2234 0.069 Uiso 1 1 calc R . .
C5 C 0.2000(3) 0.9715(7) 0.18704(19) 0.0453(9) Uani 1 1 d . . .
C6 C 0.1170(3) 0.8792(7) 0.13538(18) 0.0401(8) Uani 1 1 d . . .
C7 C -0.0706(3) 0.9349(8) 0.0847(2) 0.0483(10) Uani 1 1 d . . .
C8 C -0.1620(3) 1.1173(9) 0.1017(2) 0.0539(10) Uani 1 1 d . . .
C9 C -0.3436(3) 1.1866(9) 0.0747(2) 0.0995(15) Uani 1 1 d . . .
H9A H -0.4039 1.1106 0.0425 0.149 Uiso 1 1 calc R . .
H9B H -0.3363 1.3877 0.0645 0.149 Uiso 1 1 calc R . .
H9C H -0.3532 1.1623 0.1252 0.149 Uiso 1 1 calc R . .
N1 N 0.4203(3) 0.5373(9) 0.1418(2) 0.0880(13) Uani 1 1 d . . .
N2 N 0.1905(3) 1.1907(7) 0.24144(17) 0.0616(9) Uani 1 1 d . . .
N3 N 0.0172(2) 0.9940(5) 0.13251(14) 0.0476(8) Uani 1 1 d . . .
H3A H 0.0106 1.1202 0.1658 0.057 Uiso 1 1 calc R . .
O1 O 0.4299(3) 0.3525(8) 0.0976(2) 0.1315(15) Uani 1 1 d . . .
O2 O 0.4900(2) 0.6313(8) 0.1852(2) 0.1407(15) Uani 1 1 d . . .
O3 O 0.2697(2) 1.2706(6) 0.28021(14) 0.0862(9) Uani 1 1 d . . .
O4 O 0.1041(2) 1.2916(6) 0.24426(14) 0.0791(9) Uani 1 1 d . . .
O5 O -0.07957(17) 0.7729(6) 0.03458(13) 0.0733(8) Uani 1 1 d . . .
O6 O -0.2492(2) 1.0344(5) 0.06232(14) 0.0723(8) Uani 1 1 d . . .
O7 O -0.1507(2) 1.3029(6) 0.14568(15) 0.0762(9) Uani 1 1 d . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.3(3) . . ?
C2 C1 H1A 119.3 . . ?
C6 C1 H1A 119.3 . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 H2A 120.3 . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 N1 120.0(4) . . ?
C4 C3 N1 118.5(4) . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
C4 C5 C6 120.7(4) . . ?
C4 C5 N2 115.6(4) . . ?
C6 C5 N2 123.7(3) . . ?
C1 C6 C5 118.0(3) . . ?
C1 C6 N3 121.0(3) . . ?
C5 C6 N3 121.0(3) . . ?
O5 C7 N3 127.4(3) . . ?
O5 C7 C8 122.4(4) . . ?
N3 C7 C8 110.2(3) . . ?
O7 C8 O6 127.2(4) . . ?
O7 C8 C7 122.6(4) . . ?
O6 C8 C7 110.2(4) . . ?
O6 C9 H9A 109.5 . . ?
O6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 N1 O1 124.8(4) . . ?
O2 N1 C3 118.8(4) . . ?
O1 N1 C3 116.4(4) . . ?
O3 N2 O4 123.1(4) . . ?
O3 N2 C5 118.0(3) . . ?
O4 N2 C5 118.8(3) . . ?
C7 N3 C6 128.5(3) . . ?
C7 N3 H3A 115.8 . . ?
C6 N3 H3A 115.8 . . ?
C8 O6 C9 115.9(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.346(4) . ?
C1 C6 1.373(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.349(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.351(4) . ?
C3 N1 1.459(5) . ?
C4 C5 1.366(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.373(4) . ?
C5 N2 1.444(4) . ?
C6 N3 1.377(4) . ?
C7 O5 1.179(4) . ?
C7 N3 1.338(4) . ?
C7 C8 1.518(5) . ?
C8 O7 1.173(4) . ?
C8 O6 1.287(4) . ?
C9 O6 1.451(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
N1 O2 1.180(4) . ?
N1 O1 1.201(4) . ?
N2 O3 1.200(3) . ?
N2 O4 1.211(3) . ?
N3 H3A 0.8600 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.2(5) . . . . ?
C1 C2 C3 C4 0.9(5) . . . . ?
C1 C2 C3 N1 179.9(3) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
N1 C3 C4 C5 -179.5(3) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C3 C4 C5 N2 -179.5(3) . . . . ?
C2 C1 C6 C5 -0.8(4) . . . . ?
C2 C1 C6 N3 179.2(3) . . . . ?
C4 C5 C6 C1 1.2(4) . . . . ?
N2 C5 C6 C1 -180.0(3) . . . . ?
C4 C5 C6 N3 -178.7(3) . . . . ?
N2 C5 C6 N3 0.1(5) . . . . ?
O5 C7 C8 O7 -170.5(4) . . . . ?
N3 C7 C8 O7 7.7(5) . . . . ?
O5 C7 C8 O6 10.3(5) . . . . ?
N3 C7 C8 O6 -171.6(3) . . . . ?
C2 C3 N1 O2 178.1(4) . . . . ?
C4 C3 N1 O2 -2.9(6) . . . . ?
C2 C3 N1 O1 -0.3(5) . . . . ?
C4 C3 N1 O1 178.7(4) . . . . ?
C4 C5 N2 O3 4.5(4) . . . . ?
C6 C5 N2 O3 -174.4(3) . . . . ?
C4 C5 N2 O4 -177.9(3) . . . . ?
C6 C5 N2 O4 3.3(5) . . . . ?
O5 C7 N3 C6 -0.9(6) . . . . ?
C8 C7 N3 C6 -179.0(3) . . . . ?
C1 C6 N3 C7 -2.2(5) . . . . ?
C5 C6 N3 C7 177.8(3) . . . . ?
O7 C8 O6 C9 -0.8(6) . . . . ?
C7 C8 O6 C9 178.4(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4418264
