#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/92/2239247.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_2239247
loop_
_publ_author_name
'Sow, Mouhamadou Moustapha'
'Diouf, Ousmane'
'Seck, Matar'
'Barry, Aliou Hamady'
'Gaye, Mohamed'
_publ_section_title
;
 1,5-Bis(2-hydroxy-3-methoxybenzylidene)carbonohydrazide methanol
 0.47-solvate
;
_journal_coeditor_code           GK2603
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o423
_journal_paper_doi               10.1107/S1600536814004802
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C17 H18 N4 O5, 0.47C1 H4 O'
_chemical_formula_moiety         'C17 H18 N4 O5, 0.47(C1 H4 O)'
_chemical_formula_sum            'C17.47 H19.87 N4 O5.47'
_chemical_formula_weight         373.40
_chemical_name_systematic
;
1,5-Bis(2-hydroxy-3-methoxybenzylidene)carbonohydrazide methanol 0.47-solvate
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.4470(7)
_cell_length_b                   17.5850(9)
_cell_length_c                   22.8714(12)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      11
_cell_volume                     3799.5(4)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick,2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'non-profiled omega/2theta 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  0.1049
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9573
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.60
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1571.4
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.186
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.247
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         862
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.246
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0436
_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)+(0.0306P)²+5.2614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.1105
_reflns_number_gt                658
_reflns_number_total             862
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gk2603sup1.cif
_cod_data_source_block           I
_cod_database_code               2239247
_cod_database_fobs_code          2239247
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+3/4, -y+5/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+5/4, -y+3/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+5/4, -y+5/4, z+1/4'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.6805(4) 0.1635(2) 0.02775(15) 0.0559(10) Uani d . 1 1 A 1
O O2 1.0000 0.0000 0.0525(2) 0.0641(14) Uani d S 1 2 B 1
O O3 0.4920(4) 0.2637(2) -0.00424(17) 0.0680(12) Uani d . 1 1 A 1
N N1 0.8123(4) 0.0896(2) 0.11591(18) 0.0471(10) Uani d . 1 1 A 1
N N2 0.9127(5) 0.0436(2) 0.1418(2) 0.0533(11) Uani d . 1 1 A 1
C C1 0.6048(5) 0.1974(3) 0.0728(2) 0.0459(12) Uani d . 1 1 A 1
C C2 0.5016(5) 0.2512(3) 0.0560(2) 0.0512(13) Uani d . 1 1 A 1
C C3 0.4200(5) 0.2864(3) 0.0996(3) 0.0567(14) Uani d . 1 1 A 1
H H3 0.3505 0.3211 0.0888 0.068 Uiso calc R 1 1 A 1
C C4 0.4409(5) 0.2704(3) 0.1594(3) 0.0595(15) Uani d . 1 1 A 1
H H4 0.3856 0.2946 0.1874 0.071 Uiso calc R 1 1 A 1
C C5 0.5434(5) 0.2189(3) 0.1765(2) 0.0528(13) Uani d . 1 1 A 1
H H5 0.5580 0.2087 0.2159 0.063 Uiso calc R 1 1 A 1
C C6 0.6269(5) 0.1813(3) 0.1329(2) 0.0423(11) Uani d . 1 1 A 1
C C7 0.7364(5) 0.1284(3) 0.1531(2) 0.0459(12) Uani d . 1 1 A 1
H H7 0.7519 0.1223 0.1930 0.055 Uiso calc R 1 1 A 1
C C8 1.0000 0.0000 0.1068(3) 0.0467(17) Uani d S 1 2 . 1
C C9 0.4052(7) 0.3261(4) -0.0244(3) 0.0779(19) Uani d . 1 1 A 1
H H9A 0.4081 0.3283 -0.0663 0.117 Uiso calc R 1 1 A 1
H H9B 0.4405 0.3729 -0.0086 0.117 Uiso calc R 1 1 A 1
H H9C 0.3093 0.3185 -0.0118 0.117 Uiso calc R 1 1 A 1
O O4 0.579(2) 0.1913(12) 0.3182(9) 0.098(9) Uani d P 0.234(11) 1 C 2
H H1M 0.5601 0.1599 0.3453 0.148 Uiso d PR 0.234(11) 1 C 2
C C10 0.703(3) 0.2337(18) 0.3207(10) 0.075(10) Uani d P 0.234(11) 1 . 2
H H10A 0.7221 0.2638 0.3554 0.113 Uiso d PR 0.234(11) 1 C 2
H H10B 0.7221 0.2638 0.2861 0.113 Uiso d PR 0.234(11) 1 C 2
H H10C 0.7632 0.1890 0.3207 0.113 Uiso d PR 0.234(11) 1 C 2
H H1O 0.743(5) 0.134(3) 0.048(2) 0.057(15) Uiso d . 1 1 D 1
H H2N 0.916(5) 0.040(3) 0.183(3) 0.052(15) Uiso d . 1 1 E 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
-2 2 7
-2 -2 7
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
C1 O1 H1O . . 102(3)
C2 O3 C9 . . 118.1(4)
C7 N1 N2 . . 113.9(4)
N1 N2 C8 . . 119.1(5)
N1 N2 H2N . . 120(3)
C8 N2 H2N . . 121(3)
O1 C1 C2 . . 116.1(5)
O1 C1 C6 . . 123.9(4)
C2 C1 C6 . . 120.0(5)
O3 C2 C3 . . 126.5(5)
O3 C2 C1 . . 114.8(5)
C3 C2 C1 . . 118.7(5)
C2 C3 C4 . . 121.7(5)
C2 C3 H3 . . 119.2
C4 C3 H3 . . 119.2
C5 C4 C3 . . 120.2(5)
C5 C4 H4 . . 119.9
C3 C4 H4 . . 119.9
C4 C5 C6 . . 119.4(5)
C4 C5 H5 . . 120.3
C6 C5 H5 . . 120.3
C1 C6 C5 . . 120.1(4)
C1 C6 C7 . . 122.3(4)
C5 C6 C7 . . 117.5(4)
N1 C7 C6 . . 121.0(4)
N1 C7 H7 . . 119.5
C6 C7 H7 . . 119.5
O2 C8 N2 . . 125.4(3)
O2 C8 N2 . 2_755 125.4(3)
N2 C8 N2 . 2_755 109.2(7)
O3 C9 H9A . . 109.5
O3 C9 H9B . . 109.5
H9A C9 H9B . . 109.5
O3 C9 H9C . . 109.5
H9A C9 H9C . . 109.5
H9B C9 H9C . . 109.5
C10 O4 H1M . . 119.9
C10 C10 O4 14_655 . 177.6(17)
C10 C10 H10A 14_655 . 63.1
O4 C10 H10A . . 118.9
C10 C10 H10B 14_655 . 63.1
O4 C10 H10B . . 114.5
H10A C10 H10B . . 109.6
C10 C10 H10C 14_655 . 87.1
O4 C10 H10C . . 93.3
H10A C10 H10C . . 109.6
H10B C10 H10C . . 109.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.389(6)
O1 H1O . 0.91(5)
O2 C8 . 1.243(8)
O3 C2 . 1.397(6)
O3 C9 . 1.445(6)
N1 C7 . 1.305(6)
N1 N2 . 1.381(5)
N2 C8 . 1.381(6)
N2 H2N . 0.94(6)
C1 C2 . 1.413(6)
C1 C6 . 1.418(7)
C2 C3 . 1.405(8)
C3 C4 . 1.411(8)
C3 H3 . 0.9300
C4 C5 . 1.382(7)
C4 H4 . 0.9300
C5 C6 . 1.433(7)
C5 H5 . 0.9300
C6 C7 . 1.466(6)
C7 H7 . 0.9300
C8 N2 2_755 1.381(6)
C9 H9A . 0.9600
C9 H9B . 0.9600
C9 H9C . 0.9600
O4 C10 . 1.39(3)
O4 H1M . 0.8500
C10 C10 14_655 1.06(5)
C10 H10A . 0.9700
C10 H10B . 0.9700
C10 H10C . 0.9700
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 H1O N1 . 0.91(5) 1.86(5) 2.703(5) 152(5)
N2 H2N O3 16_445 0.94(6) 2.38(5) 3.044(6) 128(4)
N2 H2N O1 16_445 0.94(6) 2.33(6) 3.204(6) 155(4)
