#------------------------------------------------------------------------------
#$Date: 2016-03-11 04:11:30 +0200 (Fri, 11 Mar 2016) $
#$Revision: 178112 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/15/2241596.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_2241596
loop_
_publ_author_name
'Li, Wen-Juan'
'Han, Hong-Fei'
_publ_section_title
;
 Crystal structure of (E,E)-2',4'-dihydroxyacetophenone
 azine dimethylformamide disolvate
;
_journal_coeditor_code           XU5885
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              467
_journal_page_last               469
_journal_paper_doi               10.1107/S2056989016003686
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C16 H16 N2 O4, 2C3 H7 N O'
_chemical_formula_moiety         'C16 H16 N2 O4, 2(C3 H7 N O)'
_chemical_formula_sum            'C22 H30 N4 O6'
_chemical_formula_weight         446.50
_chemical_name_common
;
(E,E)-2',4'-Dihydroxyacetophenone azine
dimethylformamide disolvate
;
_chemical_name_systematic
;
4,4'-[1,1'-(Hydrazinediylidene)bis(ethan-1-yl-1-ylidene)]bis(benzene-1,3-diol)
;
_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                96.7710(10)
_cell_angle_beta                 103.049(2)
_cell_angle_gamma                96.6070(10)
_cell_formula_units_Z            1
_cell_length_a                   6.1616(7)
_cell_length_b                   7.3109(8)
_cell_length_c                   13.4537(15)
_cell_measurement_reflns_used    1119
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.535
_cell_measurement_theta_min      3.032
_cell_volume                     579.96(11)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
SMART (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker SMART 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  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2902
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_correction_T_min  0.9563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             238
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.248
_refine_ls_extinction_coef       0.17(2)
_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   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0554
_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)+(0.1079P)²+0.0859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1551
_refine_ls_wR_factor_ref         0.1874
_reflns_number_gt                1313
_reflns_number_total             2001
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5885sup1.cif
_cod_data_source_block           I
_cod_database_code               2241596
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_symmetry_multiplicity
N N1 0.4279(3) 0.5237(2) 0.53085(13) 0.0391(5) Uani d . 1 1
N N2 0.5727(4) 0.1587(3) 0.91556(16) 0.0566(6) Uani d . 1 1
O O1 0.2575(3) 0.7659(2) 0.62846(12) 0.0537(5) Uani d . 1 1
H H1 0.3372 0.7270 0.5919 0.081 Uiso calc R 1 1
O O2 -0.2843(3) 0.5582(3) 0.80524(14) 0.0679(6) Uani d . 1 1
H H2 -0.2793 0.6712 0.8190 0.102 Uiso calc R 1 1
O O3 0.7469(4) -0.0813(3) 0.87057(18) 0.0899(8) Uani d . 1 1
C C1 0.3219(5) 0.1857(3) 0.5203(2) 0.0574(7) Uani d . 1 1
H H1A 0.2229 0.1462 0.4531 0.086 Uiso calc R 1 1
H H1B 0.2779 0.1098 0.5681 0.086 Uiso calc R 1 1
H H1C 0.4737 0.1732 0.5172 0.086 Uiso calc R 1 1
C C2 0.3080(3) 0.3858(3) 0.55569(15) 0.0374(6) Uani d . 1 1
C C3 0.1542(3) 0.4334(3) 0.62014(15) 0.0368(6) Uani d . 1 1
C C4 0.1368(4) 0.6208(3) 0.65420(16) 0.0403(6) Uani d . 1 1
C C5 -0.0090(4) 0.6624(3) 0.71594(16) 0.0458(6) Uani d . 1 1
H H5 -0.0180 0.7861 0.7380 0.055 Uiso calc R 1 1
C C6 -0.1404(4) 0.5221(4) 0.74482(17) 0.0479(6) Uani d . 1 1
C C7 -0.1270(4) 0.3382(4) 0.71238(18) 0.0528(7) Uani d . 1 1
H H7 -0.2153 0.2431 0.7316 0.063 Uiso calc R 1 1
C C8 0.0176(4) 0.2968(3) 0.65154(17) 0.0472(6) Uani d . 1 1
H H8 0.0249 0.1723 0.6304 0.057 Uiso calc R 1 1
C C9 0.5795(5) -0.0016(5) 0.8617(2) 0.0696(9) Uani d . 1 1
H H9 0.4489 -0.0589 0.8136 0.084 Uiso calc R 1 1
C C10 0.7669(5) 0.2551(5) 0.9909(2) 0.0808(9) Uani d . 1 1
H H10A 0.8729 0.1706 1.0084 0.121 Uiso calc R 1 1
H H10B 0.7228 0.3039 1.0516 0.121 Uiso calc R 1 1
H H10C 0.8355 0.3556 0.9632 0.121 Uiso calc R 1 1
C C11 0.3699(5) 0.2460(5) 0.8988(3) 0.0889(10) Uani d . 1 1
H H11A 0.2480 0.1611 0.8530 0.133 Uiso calc R 1 1
H H11B 0.3951 0.3568 0.8687 0.133 Uiso calc R 1 1
H H11C 0.3324 0.2778 0.9635 0.133 Uiso calc R 1 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_3
_geom_angle
C2 N1 N1 2_666 116.3(2)
C9 N2 C10 . 120.9(2)
C9 N2 C11 . 121.2(3)
C10 N2 C11 . 117.9(3)
C4 O1 H1 . 109.5
C6 O2 H2 . 109.5
C2 C1 H1A . 109.5
C2 C1 H1B . 109.5
H1A C1 H1B . 109.5
C2 C1 H1C . 109.5
H1A C1 H1C . 109.5
H1B C1 H1C . 109.5
N1 C2 C3 . 116.96(19)
N1 C2 C1 . 122.62(19)
C3 C2 C1 . 120.4(2)
C8 C3 C4 . 116.5(2)
C8 C3 C2 . 121.9(2)
C4 C3 C2 . 121.6(2)
O1 C4 C5 . 117.0(2)
O1 C4 C3 . 122.42(19)
C5 C4 C3 . 120.6(2)
C6 C5 C4 . 120.7(2)
C6 C5 H5 . 119.7
C4 C5 H5 . 119.7
O2 C6 C5 . 122.1(2)
O2 C6 C7 . 118.0(2)
C5 C6 C7 . 119.9(2)
C8 C7 C6 . 119.6(2)
C8 C7 H7 . 120.2
C6 C7 H7 . 120.2
C7 C8 C3 . 122.9(2)
C7 C8 H8 . 118.6
C3 C8 H8 . 118.6
O3 C9 N2 . 124.5(3)
O3 C9 H9 . 117.8
N2 C9 H9 . 117.8
N2 C10 H10A . 109.5
N2 C10 H10B . 109.5
H10A C10 H10B . 109.5
N2 C10 H10C . 109.5
H10A C10 H10C . 109.5
H10B C10 H10C . 109.5
N2 C11 H11A . 109.5
N2 C11 H11B . 109.5
H11A C11 H11B . 109.5
N2 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_site_symmetry_2
_geom_bond_distance
N1 C2 . 1.301(3)
N1 N1 2_666 1.391(3)
N2 C9 . 1.313(4)
N2 C10 . 1.430(4)
N2 C11 . 1.453(3)
O1 C4 . 1.349(3)
O1 H1 . 0.8200
O2 C6 . 1.358(3)
O2 H2 . 0.8200
O3 C9 . 1.232(3)
C1 C2 . 1.503(3)
C1 H1A . 0.9600
C1 H1B . 0.9600
C1 H1C . 0.9600
C2 C3 . 1.465(3)
C3 C8 . 1.396(3)
C3 C4 . 1.417(3)
C4 C5 . 1.389(3)
C5 C6 . 1.380(3)
C5 H5 . 0.9300
C6 C7 . 1.381(3)
C7 C8 . 1.374(3)
C7 H7 . 0.9300
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_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
O1 H1 N1 . 0.82 1.82 2.543(2) 146.5
O2 H2 O3 1_465 0.82 1.84 2.649(3) 171.2
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
N1 N1 C2 C3 2_666 -179.63(19)
N1 N1 C2 C1 2_666 -0.1(3)
N1 C2 C3 C8 . -179.94(18)
C1 C2 C3 C8 . 0.5(3)
N1 C2 C3 C4 . -0.2(3)
C1 C2 C3 C4 . -179.69(19)
C8 C3 C4 O1 . -179.28(19)
C2 C3 C4 O1 . 0.9(3)
C8 C3 C4 C5 . 0.3(3)
C2 C3 C4 C5 . -179.47(19)
O1 C4 C5 C6 . 179.3(2)
C3 C4 C5 C6 . -0.3(3)
C4 C5 C6 O2 . 179.9(2)
C4 C5 C6 C7 . 0.2(3)
O2 C6 C7 C8 . -179.7(2)
C5 C6 C7 C8 . 0.0(4)
C6 C7 C8 C3 . -0.1(4)
C4 C3 C8 C7 . -0.1(3)
C2 C3 C8 C7 . 179.7(2)
C10 N2 C9 O3 . 0.1(4)
C11 N2 C9 O3 . 178.5(3)

_cod_database_fobs_code 2241596
