#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/72/2217216.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_2217216
loop_
_publ_author_name
'Mohammadi Ziarani, Ghodsi'
'Abbasi, Alireza'
'Badiei, Alireza'
'Ghorbi, Shima'
'Shahjafari, Fatemeh'
_publ_section_title
;
 (3-Nitrophenyl)methanediyl diacetate
;
_journal_coeditor_code           NG2384
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o16
_journal_page_last               o16
_journal_paper_doi               10.1107/S1600536807060990
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C11 H11 N O6'
_chemical_formula_moiety         'C11 H11 N O6'
_chemical_formula_sum            'C11 H11 N O6'
_chemical_formula_weight         253.21
_chemical_name_systematic
;
(3-Nitrophenyl)methanediyl diacetate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.094(11)
_cell_angle_beta                 98.031(10)
_cell_angle_gamma                99.963(10)
_cell_formula_units_Z            2
_cell_length_a                   7.8959(9)
_cell_length_b                   8.4779(10)
_cell_length_c                   9.7788(13)
_cell_measurement_reflns_used    1543
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      25.5
_cell_measurement_theta_min      3.5
_cell_volume                     595.55(14)
_computing_cell_refinement       'IPDS Software (Stoe & Cie, 1997)'
_computing_data_collection       'IPDS Software (Stoe & Cie, 1997)'
_computing_data_reduction        'IPDS Software (Stoe & Cie, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2001)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'Area detector - phi oscillation'
_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  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0563
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3869
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         3.76
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'block shape'
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.143
_refine_ls_extinction_coef       0.100(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.912
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0364
_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)+(0.0565P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0977
_reflns_number_gt                1224
_reflns_number_total             2149
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2384.cif
_cod_data_source_block           I
_cod_original_cell_volume        595.55(13)
_cod_database_code               2217216
_cod_database_fobs_code          2217216
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O O1 0.30507(14) 0.16974(14) -0.04836(12) 0.0445(3) Uani d . 1
O O2 0.59909(14) 0.22011(14) 0.05498(12) 0.0457(4) Uani d . 1
O O3 0.16732(19) 0.6263(2) 0.60185(17) 0.0836(5) Uani d . 1
O O4 0.43191(18) 0.23344(17) -0.22188(14) 0.0668(4) Uani d . 1
O O5 0.75926(17) 0.47383(18) 0.07041(18) 0.0791(5) Uani d . 1
O O6 0.1787(2) 0.7027(2) 0.4140(2) 0.1013(6) Uani d . 1
N N1 0.2009(2) 0.6066(2) 0.4801(2) 0.0651(5) Uani d . 1
C C1 0.4464(2) 0.2888(2) 0.06532(17) 0.0404(4) Uani d . 1
H H1 0.4676 0.4004 0.0533 0.048 Uiso calc R 1
C C2 0.3243(2) 0.4433(2) 0.27690(19) 0.0440(5) Uani d . 1
H H2 0.3153 0.5260 0.2347 0.053 Uiso calc R 1
C C3 0.2703(2) 0.4571(2) 0.40713(19) 0.0479(5) Uani d . 1
C C4 0.3077(3) 0.1635(2) -0.1894(2) 0.0485(5) Uani d . 1
C C5 0.3922(2) 0.3050(2) 0.20946(17) 0.0394(4) Uani d . 1
C C6 0.4043(2) 0.1838(2) 0.2739(2) 0.0501(5) Uani d . 1
H H6 0.4494 0.0901 0.2287 0.060 Uiso calc R 1
C C7 0.7489(2) 0.3270(3) 0.0531(2) 0.0500(5) Uani d . 1
C C8 0.2821(2) 0.3387(3) 0.4739(2) 0.0580(5) Uani d . 1
H H8 0.2456 0.3512 0.5625 0.070 Uiso calc R 1
C C9 0.3497(2) 0.2009(3) 0.4059(2) 0.0595(5) Uani d . 1
H H9 0.3587 0.1188 0.4487 0.071 Uiso calc R 1
C C10 0.1372(3) 0.0604(3) -0.2909(2) 0.0687(6) Uani d . 1
H H10A 0.1573 0.0030 -0.3875 0.103 Uiso calc R 1
H H10B 0.0600 0.1348 -0.2973 0.103 Uiso calc R 1
H H10C 0.0842 -0.0233 -0.2535 0.103 Uiso calc R 1
C C11 0.8926(2) 0.2351(3) 0.0284(3) 0.0726(7) Uani d . 1
H H11A 0.9436 0.2246 0.1192 0.109 Uiso calc R 1
H H11B 0.9812 0.2985 -0.0039 0.109 Uiso calc R 1
H H11C 0.8457 0.1228 -0.0459 0.109 Uiso calc R 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C4 O1 C1 116.57(13)
C7 O2 C1 116.69(13)
O6 N1 O3 123.62(18)
O6 N1 C3 117.60(17)
O3 N1 C3 118.8(2)
O1 C1 O2 107.75(12)
O1 C1 C5 106.49(12)
O2 C1 C5 111.36(13)
O1 C1 H1 110.4
O2 C1 H1 110.4
C5 C1 H1 110.4
C3 C2 C5 119.16(16)
C3 C2 H2 120.4
C5 C2 H2 120.4
C8 C3 C2 122.43(17)
C8 C3 N1 118.60(18)
C2 C3 N1 118.95(18)
O4 C4 O1 122.89(18)
O4 C4 C10 126.65(18)
O1 C4 C10 110.46(16)
C6 C5 C2 119.45(16)
C6 C5 C1 121.85(15)
C2 C5 C1 118.68(15)
C5 C6 C9 120.38(18)
C5 C6 H6 119.8
C9 C6 H6 119.8
O5 C7 O2 122.99(17)
O5 C7 C11 125.89(18)
O2 C7 C11 111.12(17)
C3 C8 C9 118.09(17)
C3 C8 H8 121.0
C9 C8 H8 121.0
C8 C9 C6 120.49(18)
C8 C9 H9 119.8
C6 C9 H9 119.8
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
C7 C11 H11A 109.5
C7 C11 H11B 109.5
H11A C11 H11B 109.5
C7 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 1.366(2) yes
O1 C1 1.4249(19) yes
O2 C7 1.367(2) yes
O2 C1 1.4287(18) yes
O3 N1 1.221(2) yes
O4 C4 1.193(2) yes
O5 C7 1.187(2) yes
O6 N1 1.215(2) yes
N1 C3 1.474(2) yes
C1 C5 1.500(2) ?
C1 H1 0.9800 ?
C2 C3 1.374(2) ?
C2 C5 1.381(2) ?
C2 H2 0.9300 ?
C3 C8 1.374(3) ?
C4 C10 1.488(3) ?
C5 C6 1.380(2) ?
C6 C9 1.388(2) ?
C6 H6 0.9300 ?
C7 C11 1.487(2) ?
C8 C9 1.378(2) ?
C8 H8 0.9300 ?
C9 H9 0.9300 ?
C10 H10A 0.9600 ?
C10 H10B 0.9600 ?
C10 H10C 0.9600 ?
C11 H11A 0.9600 ?
C11 H11B 0.9600 ?
C11 H11C 0.9600 ?
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
C4 O1 C1 O2 -74.57(15)
C4 O1 C1 C5 165.86(13)
C7 O2 C1 O1 129.88(14)
C7 O2 C1 C5 -113.68(15)
C5 C2 C3 C8 0.4(3)
C5 C2 C3 N1 178.90(15)
O6 N1 C3 C8 -174.42(18)
O3 N1 C3 C8 4.8(3)
O6 N1 C3 C2 7.1(3)
O3 N1 C3 C2 -173.74(16)
C1 O1 C4 O4 10.7(2)
C1 O1 C4 C10 -169.00(14)
C3 C2 C5 C6 0.0(2)
C3 C2 C5 C1 178.43(15)
O1 C1 C5 C6 79.55(18)
O2 C1 C5 C6 -37.7(2)
O1 C1 C5 C2 -98.83(16)
O2 C1 C5 C2 143.97(14)
C2 C5 C6 C9 -0.3(2)
C1 C5 C6 C9 -178.70(16)
C1 O2 C7 O5 5.7(3)
C1 O2 C7 C11 -174.89(14)
C2 C3 C8 C9 -0.5(3)
N1 C3 C8 C9 -179.01(15)
C3 C8 C9 C6 0.2(3)
C5 C6 C9 C8 0.2(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 88161
