#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/26/2222626.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_2222626
loop_
_publ_author_name
'Bingöl Alpaslan, Yelda'
'Tanak, Hasan'
'Ağar, Erbil'
'Erşahin, Ferda'
_publ_section_title
;
 2-[(E)-(2-Morpholinoethyl)iminiomethyl]-4-nitro-1-oxocyclohexadienide
;
_journal_coeditor_code           CI2842
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1842
_journal_paper_doi               10.1107/S1600536809026191
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H17 N3 O4'
_chemical_formula_moiety         'C13 H17 N3 O4'
_chemical_formula_sum            'C13 H17 N3 O4'
_chemical_formula_weight         279.30
_chemical_name_systematic
;
2-[(E)-(2-morpholinoethyl)iminiomethyl]-4-nitro-1-oxocyclohexadienide
;
_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                102.329(7)
_cell_angle_beta                 97.143(6)
_cell_angle_gamma                104.173(9)
_cell_formula_units_Z            2
_cell_length_a                   5.3520(4)
_cell_length_b                   10.8972(9)
_cell_length_c                   12.4537(9)
_cell_measurement_reflns_used    23053
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.01
_cell_measurement_theta_min      1.70
_cell_volume                     675.91(10)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Stoe IPDSII'
_diffrn_measurement_method       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  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11340
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         1.70
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.70
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.167
_refine_ls_extinction_coef       0.077(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3094
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0400
_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)+(0.0512P)²+0.1309P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1097
_reflns_number_gt                2664
_reflns_number_total             3094
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2842.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2222626
_cod_database_fobs_code          2222626
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4611(2) 0.77887(11) 0.53094(9) 0.0335(2) Uani d . 1 . .
C C2 0.6439(2) 0.90243(11) 0.56526(9) 0.0341(2) Uani d . 1 . .
H H2 0.7896 0.9204 0.5315 0.041 Uiso calc R 1 . .
C C3 0.6067(2) 0.99713(10) 0.64924(9) 0.0348(3) Uani d . 1 . .
C C4 0.3899(3) 0.97257(12) 0.70256(10) 0.0396(3) Uani d . 1 . .
H H4 0.3692 1.0377 0.7597 0.048 Uiso calc R 1 . .
C C5 0.2112(3) 0.85348(12) 0.67033(11) 0.0426(3) Uani d . 1 . .
H H5 0.0698 0.8382 0.7069 0.051 Uiso calc R 1 . .
C C6 0.2318(2) 0.74989(11) 0.58183(10) 0.0363(3) Uani d . 1 . .
C C7 0.5074(2) 0.68324(11) 0.44412(9) 0.0358(3) Uani d . 1 . .
H H7 0.6566 0.7074 0.4138 0.043 Uiso calc R 1 . .
C C8 0.4146(3) 0.46932(12) 0.31724(10) 0.0430(3) Uani d . 1 . .
H H8A 0.3937 0.3878 0.3393 0.052 Uiso calc R 1 . .
H H8B 0.5956 0.5004 0.3093 0.052 Uiso calc R 1 . .
C C9 0.2370(3) 0.44450(12) 0.20590(10) 0.0437(3) Uani d . 1 . .
H H9A 0.0572 0.4050 0.2113 0.052 Uiso calc R 1 . .
H H9B 0.2453 0.5268 0.1865 0.052 Uiso calc R 1 . .
C C10 0.2038(3) 0.36092(15) 0.00679(11) 0.0513(3) Uani d . 1 . .
H H10A 0.2527 0.4500 -0.0009 0.062 Uiso calc R 1 . .
H H10B 0.0140 0.3307 -0.0047 0.062 Uiso calc R 1 . .
C C11 0.3025(3) 0.27445(17) -0.07913(12) 0.0640(4) Uani d . 1 . .
H H11A 0.2304 0.2783 -0.1534 0.077 Uiso calc R 1 . .
H H11B 0.4920 0.3062 -0.0681 0.077 Uiso calc R 1 . .
C C12 0.3364(4) 0.13651(16) 0.03730(15) 0.0665(5) Uani d . 1 . .
H H12A 0.5264 0.1645 0.0487 0.080 Uiso calc R 1 . .
H H12B 0.2834 0.0467 0.0429 0.080 Uiso calc R 1 . .
C C13 0.2450(3) 0.22200(13) 0.12725(12) 0.0504(3) Uani d . 1 . .
H H13A 0.0561 0.1904 0.1194 0.060 Uiso calc R 1 . .
H H13B 0.3244 0.2177 0.2002 0.060 Uiso calc R 1 . .
N N1 0.7884(2) 1.12600(10) 0.68031(9) 0.0410(3) Uani d . 1 . .
N N2 0.3567(2) 0.56554(9) 0.40467(8) 0.0378(2) Uani d . 1 . .
N N3 0.3171(2) 0.35764(10) 0.11888(8) 0.0422(3) Uani d . 1 . .
O O1 0.06162(19) 0.64042(9) 0.55030(9) 0.0513(3) Uani d . 1 . .
O O2 0.7384(2) 1.21314(9) 0.74731(9) 0.0600(3) Uani d . 1 . .
O O3 0.9854(2) 1.14568(9) 0.63771(9) 0.0549(3) Uani d . 1 . .
O O4 0.2302(3) 0.14272(12) -0.07115(9) 0.0727(4) Uani d . 1 . .
H H1 0.214(4) 0.5433(18) 0.4335(15) 0.065(5) Uiso d . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C7 . . 117.84(10) ?
C2 C1 C6 . . 120.88(10) ?
C7 C1 C6 . . 121.27(10) ?
C3 C2 C1 . . 119.54(10) ?
C3 C2 H2 . . 120.2 ?
C1 C2 H2 . . 120.2 ?
C2 C3 C4 . . 121.54(10) ?
C2 C3 N1 . . 119.24(10) ?
C4 C3 N1 . . 119.18(10) ?
C5 C4 C3 . . 119.65(11) ?
C5 C4 H4 . . 120.2 ?
C3 C4 H4 . . 120.2 ?
C4 C5 C6 . . 122.50(11) ?
C4 C5 H5 . . 118.8 ?
C6 C5 H5 . . 118.8 ?
O1 C6 C5 . . 122.23(11) ?
O1 C6 C1 . . 121.91(10) ?
C5 C6 C1 . . 115.86(10) ?
N2 C7 C1 . . 124.56(11) ?
N2 C7 H7 . . 117.7 ?
C1 C7 H7 . . 117.7 ?
N2 C8 C9 . . 111.99(10) ?
N2 C8 H8A . . 109.2 ?
C9 C8 H8A . . 109.2 ?
N2 C8 H8B . . 109.2 ?
C9 C8 H8B . . 109.2 ?
H8A C8 H8B . . 107.9 ?
N3 C9 C8 . . 110.22(10) ?
N3 C9 H9A . . 109.6 ?
C8 C9 H9A . . 109.6 ?
N3 C9 H9B . . 109.6 ?
C8 C9 H9B . . 109.6 ?
H9A C9 H9B . . 108.1 ?
N3 C10 C11 . . 109.46(13) ?
N3 C10 H10A . . 109.8 ?
C11 C10 H10A . . 109.8 ?
N3 C10 H10B . . 109.8 ?
C11 C10 H10B . . 109.8 ?
H10A C10 H10B . . 108.2 ?
O4 C11 C10 . . 111.17(13) ?
O4 C11 H11A . . 109.4 ?
C10 C11 H11A . . 109.4 ?
O4 C11 H11B . . 109.4 ?
C10 C11 H11B . . 109.4 ?
H11A C11 H11B . . 108.0 ?
O4 C12 C13 . . 111.48(14) ?
O4 C12 H12A . . 109.3 ?
C13 C12 H12A . . 109.3 ?
O4 C12 H12B . . 109.3 ?
C13 C12 H12B . . 109.3 ?
H12A C12 H12B . . 108.0 ?
N3 C13 C12 . . 110.35(13) ?
N3 C13 H13A . . 109.6 ?
C12 C13 H13A . . 109.6 ?
N3 C13 H13B . . 109.6 ?
C12 C13 H13B . . 109.6 ?
H13A C13 H13B . . 108.1 ?
O2 N1 O3 . . 122.35(11) ?
O2 N1 C3 . . 118.53(11) ?
O3 N1 C3 . . 119.11(10) ?
C7 N2 C8 . . 122.84(11) ?
C7 N2 H1 . . 117.3(12) ?
C8 N2 H1 . . 119.8(12) ?
C9 N3 C10 . . 111.82(10) ?
C9 N3 C13 . . 112.22(10) ?
C10 N3 C13 . . 108.56(11) ?
C12 O4 C11 . . 109.63(11) ?
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
C1 C2 . 1.3994(16) ?
C1 C7 . 1.4241(15) ?
C1 C6 . 1.4478(16) ?
C2 C3 . 1.3748(15) ?
C2 H2 . 0.93 ?
C3 C4 . 1.4051(17) ?
C3 N1 . 1.4398(15) ?
C4 C5 . 1.3543(18) ?
C4 H4 . 0.93 ?
C5 C6 . 1.4357(16) ?
C5 H5 . 0.93 ?
C6 O1 . 1.2594(14) ?
C7 N2 . 1.2894(15) ?
C7 H7 . 0.93 ?
C8 N2 . 1.4615(14) ?
C8 C9 . 1.5117(18) ?
C8 H8A . 0.97 ?
C8 H8B . 0.97 ?
C9 N3 . 1.4596(15) ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
C10 N3 . 1.4625(17) ?
C10 C11 . 1.505(2) ?
C10 H10A . 0.97 ?
C10 H10B . 0.97 ?
C11 O4 . 1.421(2) ?
C11 H11A . 0.97 ?
C11 H11B . 0.97 ?
C12 O4 . 1.421(2) ?
C12 C13 . 1.5086(19) ?
C12 H12A . 0.97 ?
C12 H12B . 0.97 ?
C13 N3 . 1.4632(18) ?
C13 H13A . 0.97 ?
C13 H13B . 0.97 ?
N1 O2 . 1.2293(14) ?
N1 O3 . 1.2315(14) ?
N2 H1 . 0.887(19) ?
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
N2 H1 O1 . 0.89(2) 1.99(2) 2.6760(14) 133(2)
N2 H1 O1 2_566 0.89(2) 2.24(2) 2.9587(14) 138(2)
C4 H4 O4 1_566 0.93 2.47 3.3547(16) 160
C7 H7 O3 2_776 0.93 2.43 3.3020(15) 157
C13 H13B Cg2 2_666 0.97 2.9908 3.9254 162.14
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
C7 C1 C2 C3 . . . . -179.68(10) ?
C6 C1 C2 C3 . . . . 0.69(17) ?
C1 C2 C3 C4 . . . . 0.62(18) ?
C1 C2 C3 N1 . . . . -176.92(10) ?
C2 C3 C4 C5 . . . . -0.61(18) ?
N1 C3 C4 C5 . . . . 176.93(11) ?
C3 C4 C5 C6 . . . . -0.7(2) ?
C4 C5 C6 O1 . . . . -178.16(12) ?
C4 C5 C6 C1 . . . . 1.93(19) ?
C2 C1 C6 O1 . . . . 178.21(11) ?
C7 C1 C6 O1 . . . . -1.41(18) ?
C2 C1 C6 C5 . . . . -1.89(17) ?
C7 C1 C6 C5 . . . . 178.49(11) ?
C2 C1 C7 N2 . . . . 179.62(11) ?
C6 C1 C7 N2 . . . . -0.75(18) ?
N2 C8 C9 N3 . . . . 174.64(11) ?
N3 C10 C11 O4 . . . . 60.36(17) ?
O4 C12 C13 N3 . . . . -57.64(18) ?
C2 C3 N1 O2 . . . . 172.71(11) ?
C4 C3 N1 O2 . . . . -4.89(17) ?
C2 C3 N1 O3 . . . . -6.09(17) ?
C4 C3 N1 O3 . . . . 176.31(11) ?
C1 C7 N2 C8 . . . . -178.52(11) ?
C9 C8 N2 C7 . . . . -106.90(14) ?
C8 C9 N3 C10 . . . . -163.51(11) ?
C8 C9 N3 C13 . . . . 74.22(14) ?
C11 C10 N3 C9 . . . . 177.47(12) ?
C11 C10 N3 C13 . . . . -58.19(15) ?
C12 C13 N3 C9 . . . . -178.84(12) ?
C12 C13 N3 C10 . . . . 57.05(16) ?
C13 C12 O4 C11 . . . . 57.82(18) ?
C10 C11 O4 C12 . . . . -59.34(18) ?
