#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/74/2227480.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_2227480
loop_
_publ_author_name
'Zhao, Lin-xiu'
'Cui, Jian-lan'
'Cao, Duan-lin'
_publ_section_title
;
 3-Ethoxy-2-hydroxybenzaldehyde 2,4-dinitrophenylhydrazone
 N,N-dimethylformamide monosolvate
;
_journal_coeditor_code           HB5578
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2205
_journal_paper_doi               10.1107/S1600536810029983
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H14 N4 O6, C3 N7 N O'
_chemical_formula_moiety         'C15 H14 N4 O6, C3 N7 N O'
_chemical_formula_sum            'C18 H21 N5 O7'
_chemical_formula_weight         419.40
_chemical_name_systematic
;
3-Ethoxy-2-hydroxybenzaldehyde 2,4-dinitrophenylhydrazone
N,N-dimethylformamide monosolvate
;
_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
_cell_angle_alpha                84.677(7)
_cell_angle_beta                 81.562(7)
_cell_angle_gamma                68.707(8)
_cell_formula_units_Z            2
_cell_length_a                   7.1070(6)
_cell_length_b                   7.7200(7)
_cell_length_c                   19.4790(19)
_cell_measurement_reflns_used    1739
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      3.14
_cell_volume                     984.10(16)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'ω 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  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0927
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6788
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.234
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.738
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4011
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.738
_refine_ls_R_factor_all          0.1179
_refine_ls_R_factor_gt           0.0394
_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)+(0.0323P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0665
_refine_ls_wR_factor_ref         0.0760
_reflns_number_gt                1655
_reflns_number_total             4011
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5578.cif
_cod_data_source_block           I
_cod_database_code               2227480
_cod_database_fobs_code          2227480
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
N N2 0.7004(2) 0.1384(2) 0.44923(8) 0.0440(4) Uani d . 1 . .
H H2A 0.6798 0.2386 0.4699 0.053 Uiso calc R 1 . .
N N1 0.7508(2) -0.02993(19) 0.48584(9) 0.0428(4) Uani d . 1 . .
O O1 0.82321(18) -0.01826(15) 0.68544(7) 0.0526(4) Uani d . 1 . .
H H1B 0.8425 -0.0301 0.7264 0.079 Uiso calc R 1 . .
O O2 0.8899(2) -0.31145(17) 0.77409(7) 0.0581(4) Uani d . 1 . .
N N3 0.6101(2) 0.4898(2) 0.36575(11) 0.0510(5) Uani d . 1 . .
C C1 0.8135(3) -0.1943(2) 0.59413(10) 0.0375(5) Uani d . 1 . .
C C10 0.6832(3) 0.1462(2) 0.38088(10) 0.0350(5) Uani d . 1 . .
C C15 0.7047(3) -0.0166(2) 0.34804(10) 0.0412(5) Uani d . 1 . .
H H15A 0.7291 -0.1278 0.3743 0.049 Uiso calc R 1 . .
O O3 0.6142(2) 0.49976(17) 0.42849(8) 0.0680(5) Uani d . 1 . .
C C3 0.8759(3) -0.3431(3) 0.70742(11) 0.0429(5) Uani d . 1 . .
C C13 0.6554(3) 0.1492(3) 0.23938(10) 0.0442(5) Uani d . 1 . .
O O4 0.5797(2) 0.62599(17) 0.32584(8) 0.0748(5) Uani d . 1 . .
C C6 0.8332(2) -0.3652(2) 0.56975(10) 0.0435(5) Uani d . 1 . .
H H6A 0.8181 -0.3735 0.5237 0.052 Uiso calc R 1 . .
C C11 0.6432(3) 0.3112(2) 0.33864(11) 0.0380(5) Uani d . 1 . .
C C12 0.6307(3) 0.3106(3) 0.26862(11) 0.0455(5) Uani d . 1 . .
H H12A 0.6054 0.4204 0.2415 0.055 Uiso calc R 1 . .
C C2 0.8389(3) -0.1847(2) 0.66297(11) 0.0390(5) Uani d . 1 . .
C C9 0.7639(2) -0.0246(2) 0.54994(11) 0.0428(5) Uani d . 1 . .
H H9A 0.7416 0.0885 0.5688 0.051 Uiso calc R 1 . .
O O5 0.6626(2) 0.0037(2) 0.14012(8) 0.0852(5) Uani d . 1 . .
C C14 0.6907(3) -0.0156(2) 0.27938(10) 0.0448(5) Uani d . 1 . .
H H14A 0.7046 -0.1247 0.2591 0.054 Uiso calc R 1 . .
O O7 0.1362(3) -0.0784(2) 0.18791(8) 0.0778(5) Uani d . 1 . .
N N4 0.6425(3) 0.1503(3) 0.16536(10) 0.0631(5) Uani d . 1 . .
C C4 0.8958(3) -0.5105(3) 0.68260(11) 0.0491(6) Uani d . 1 . .
H H4A 0.9233 -0.6165 0.7120 0.059 Uiso calc R 1 . .
C C5 0.8748(3) -0.5210(3) 0.61339(11) 0.0494(5) Uani d . 1 . .
H H5A 0.8890 -0.6345 0.5966 0.059 Uiso calc R 1 . .
N N5 0.3469(3) -0.1964(2) 0.09163(11) 0.0652(5) Uani d . 1 . .
O O6 0.6127(3) 0.2979(2) 0.13149(8) 0.0938(6) Uani d . 1 . .
C C16 0.3049(4) -0.1592(3) 0.15849(13) 0.0624(6) Uani d . 1 . .
H H16A 0.4130 -0.1980 0.1849 0.075 Uiso calc R 1 . .
C C8 0.9158(4) -0.3863(3) 0.89285(12) 0.0870(8) Uani d . 1 . .
H H8A 0.9375 -0.4849 0.9280 0.131 Uiso calc R 1 . .
H H8B 0.7849 -0.2919 0.9041 0.131 Uiso calc R 1 . .
H H8C 1.0198 -0.3333 0.8905 0.131 Uiso calc R 1 . .
C C7 0.9238(3) -0.4618(3) 0.82428(11) 0.0698(7) Uani d . 1 . .
H H7A 1.0557 -0.5570 0.8122 0.084 Uiso calc R 1 . .
H H7B 0.8201 -0.5167 0.8261 0.084 Uiso calc R 1 . .
C C18 0.5516(4) -0.2863(3) 0.05946(14) 0.1133(10) Uani d . 1 . .
H H18A 0.6435 -0.3192 0.0941 0.170 Uiso calc R 1 . .
H H18B 0.5874 -0.2030 0.0248 0.170 Uiso calc R 1 . .
H H18C 0.5606 -0.3966 0.0381 0.170 Uiso calc R 1 . .
C C17 0.1878(4) -0.1365(4) 0.04773(13) 0.1068(9) Uani d . 1 . .
H H17A 0.0594 -0.0790 0.0751 0.160 Uiso calc R 1 . .
H H17B 0.1852 -0.2420 0.0259 0.160 Uiso calc R 1 . .
H H17C 0.2122 -0.0485 0.0127 0.160 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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
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
C10 N2 N1 . . 119.90(16) ?
C10 N2 H2A . . 120.1 ?
N1 N2 H2A . . 120.1 ?
C9 N1 N2 . . 115.76(16) ?
C2 O1 H1B . . 109.5 ?
C3 O2 C7 . . 118.68(16) ?
O4 N3 O3 . . 121.94(17) ?
O4 N3 C11 . . 118.91(18) ?
O3 N3 C11 . . 119.16(16) ?
C2 C1 C6 . . 119.10(17) ?
C2 C1 C9 . . 118.88(18) ?
C6 C1 C9 . . 122.02(19) ?
N2 C10 C11 . . 123.56(18) ?
N2 C10 C15 . . 119.93(16) ?
C11 C10 C15 . . 116.50(19) ?
C14 C15 C10 . . 121.93(17) ?
C14 C15 H15A . . 119.0 ?
C10 C15 H15A . . 119.0 ?
O2 C3 C4 . . 126.23(18) ?
O2 C3 C2 . . 113.64(18) ?
C4 C3 C2 . . 120.1(2) ?
C12 C13 C14 . . 120.79(19) ?
C12 C13 N4 . . 119.36(18) ?
C14 C13 N4 . . 119.8(2) ?
C5 C6 C1 . . 120.36(19) ?
C5 C6 H6A . . 119.8 ?
C1 C6 H6A . . 119.8 ?
C12 C11 C10 . . 121.16(19) ?
C12 C11 N3 . . 116.24(17) ?
C10 C11 N3 . . 122.59(19) ?
C13 C12 C11 . . 119.91(18) ?
C13 C12 H12A . . 120.0 ?
C11 C12 H12A . . 120.0 ?
O1 C2 C1 . . 118.32(16) ?
O1 C2 C3 . . 121.61(19) ?
C1 C2 C3 . . 120.06(18) ?
N1 C9 C1 . . 120.57(19) ?
N1 C9 H9A . . 119.7 ?
C1 C9 H9A . . 119.7 ?
C15 C14 C13 . . 119.69(19) ?
C15 C14 H14A . . 120.2 ?
C13 C14 H14A . . 120.2 ?
O6 N4 O5 . . 123.4(2) ?
O6 N4 C13 . . 118.2(2) ?
O5 N4 C13 . . 118.40(19) ?
C3 C4 C5 . . 119.78(18) ?
C3 C4 H4A . . 120.1 ?
C5 C4 H4A . . 120.1 ?
C6 C5 C4 . . 120.52(19) ?
C6 C5 H5A . . 119.7 ?
C4 C5 H5A . . 119.7 ?
C16 N5 C17 . . 120.2(2) ?
C16 N5 C18 . . 122.2(2) ?
C17 N5 C18 . . 117.5(2) ?
O7 C16 N5 . . 125.1(2) ?
O7 C16 H16A . . 117.4 ?
N5 C16 H16A . . 117.4 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O2 C7 C8 . . 107.53(18) ?
O2 C7 H7A . . 110.2 ?
C8 C7 H7A . . 110.2 ?
O2 C7 H7B . . 110.2 ?
C8 C7 H7B . . 110.2 ?
H7A C7 H7B . . 108.5 ?
N5 C18 H18A . . 109.5 ?
N5 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
N5 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
N5 C17 H17A . . 109.5 ?
N5 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
N5 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 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
N2 C10 . 1.348(2) ?
N2 N1 . 1.3751(17) ?
N2 H2A . 0.8600 ?
N1 C9 . 1.271(2) ?
O1 C2 . 1.3569(19) ?
O1 H1B . 0.8200 ?
O2 C3 . 1.368(2) ?
O2 C7 . 1.4200(19) ?
N3 O4 . 1.2204(16) ?
N3 O3 . 1.2369(19) ?
N3 C11 . 1.448(2) ?
C1 C2 . 1.391(2) ?
C1 C6 . 1.395(2) ?
C1 C9 . 1.458(2) ?
C10 C11 . 1.411(2) ?
C10 C15 . 1.412(2) ?
C15 C14 . 1.355(2) ?
C15 H15A . 0.9300 ?
C3 C4 . 1.374(2) ?
C3 C2 . 1.397(2) ?
C13 C12 . 1.361(2) ?
C13 C14 . 1.389(2) ?
C13 N4 . 1.457(2) ?
C6 C5 . 1.372(2) ?
C6 H6A . 0.9300 ?
C11 C12 . 1.380(3) ?
C12 H12A . 0.9300 ?
C9 H9A . 0.9300 ?
O5 N4 . 1.228(2) ?
C14 H14A . 0.9300 ?
O7 C16 . 1.215(2) ?
N4 O6 . 1.2263(18) ?
C4 C5 . 1.391(3) ?
C4 H4A . 0.9300 ?
C5 H5A . 0.9300 ?
N5 C16 . 1.327(3) ?
N5 C17 . 1.433(3) ?
N5 C18 . 1.439(3) ?
C16 H16A . 0.9300 ?
C8 C7 . 1.492(3) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 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
N2 H2A O3 . 0.86 2.01 2.6349(19) 128
O1 H1B O2 . 0.82 2.21 2.6581(15) 115
O1 H1B O7 2_656 0.82 1.98 2.726(2) 150
