#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/72/2207241.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_2207241
loop_
_publ_author_name
'Zhen, Xiao-Li'
'Han, Jian-Rong'
_publ_section_title
;
 (E)-1-(3-Ethoxy-4-hydroxybenzylidene)-2-(4-nitrophenyl)hydrazine
;
_journal_coeditor_code           HB6287
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3721
_journal_page_last               o3722
_journal_paper_doi               10.1107/S1600536805032617
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C15 H15 N3 O4'
_chemical_formula_moiety         'C15 H15 N3 O4'
_chemical_formula_sum            'C15 H15 N3 O4'
_chemical_formula_weight         301.30
_chemical_name_systematic
;
(E)-1-(3-Ethoxy-4-hydroxybenzylidene)-2-(4-nitrophenyl)hydrazine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   'difmap (O-H and N-H) and geom  (C-H)'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.868(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.148(2)
_cell_length_b                   9.0980(19)
_cell_length_c                   15.967(3)
_cell_measurement_reflns_used    2008
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.89
_cell_measurement_theta_min      2.60
_cell_volume                     1431.2(5)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL  (Bruker, 1999)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7792
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.168
_refine_ls_extinction_coef       0.0170(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0402
_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)+(0.0459P)²+0.2257P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                1758
_reflns_number_total             2904
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6287.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2207241
_cod_database_fobs_code          2207241
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_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_type_symbol
O1 0.53401(11) 0.13835(14) 1.09950(8) 0.0518(4) Uani d . 1 O
O2 0.73380(15) -0.04459(16) 1.17677(9) 0.0595(4) Uani d . 1 O
H2 0.658(3) -0.033(3) 1.1874(15) 0.091(9) Uiso d . 1 H
O3 1.44556(16) 0.65773(18) 0.70004(10) 0.0756(5) Uani d . 1 O
O4 1.54473(15) 0.49590(17) 0.79152(11) 0.0728(5) Uani d . 1 O
N1 0.94799(14) 0.37228(16) 0.91562(9) 0.0432(4) Uani d . 1 N
N2 0.96068(17) 0.48029(19) 0.85831(10) 0.0482(4) Uani d . 1 N
H2A 0.898(2) 0.537(2) 0.8385(13) 0.066(7) Uiso d . 1 H
N3 1.44349(18) 0.56781(19) 0.75697(11) 0.0527(4) Uani d . 1 N
C1 0.83267(18) 0.3609(2) 0.93394(11) 0.0436(5) Uani d . 1 C
H1 0.7632 0.4246 0.9079 0.052 Uiso calc R 1 H
C2 0.80658(17) 0.25120(19) 0.99452(11) 0.0392(4) Uani d . 1 C
C3 0.90503(17) 0.1512(2) 1.03484(11) 0.0455(5) Uani d . 1 C
H3 0.9894 0.1511 1.0216 0.055 Uiso calc R 1 H
C4 0.87906(17) 0.0522(2) 1.09430(12) 0.0475(5) Uani d . 1 C
H4 0.9457 -0.0146 1.1203 0.057 Uiso calc R 1 H
C5 0.75509(17) 0.0516(2) 1.11539(11) 0.0417(4) Uani d . 1 C
C6 0.65312(17) 0.1485(2) 1.07363(11) 0.0393(4) Uani d . 1 C
C7 0.67949(16) 0.2467(2) 1.01388(11) 0.0419(4) Uani d . 1 C
H7 0.6117 0.3109 0.9861 0.050 Uiso calc R 1 H
C8 0.42008(16) 0.2213(2) 1.05285(12) 0.0472(5) Uani d . 1 C
H8A 0.3974 0.1928 0.9926 0.057 Uiso calc R 1 H
H8B 0.4411 0.3255 1.0565 0.057 Uiso calc R 1 H
C9 0.30317(18) 0.1899(2) 1.09259(13) 0.0600(6) Uani d . 1 C
H9A 0.2818 0.0870 1.0873 0.090 Uiso calc R 1 H
H9B 0.2255 0.2459 1.0634 0.090 Uiso calc R 1 H
H9C 0.3274 0.2167 1.1525 0.090 Uiso calc R 1 H
C10 1.08024(17) 0.49957(19) 0.83417(10) 0.0378(4) Uani d . 1 C
C11 1.18909(18) 0.4025(2) 0.86025(11) 0.0452(5) Uani d . 1 C
H11 1.1810 0.3222 0.8947 0.054 Uiso calc R 1 H
C12 1.30770(18) 0.4252(2) 0.83541(11) 0.0469(5) Uani d . 1 C
H12 1.3802 0.3608 0.8531 0.056 Uiso calc R 1 H
C13 1.31866(18) 0.5447(2) 0.78386(11) 0.0409(4) Uani d . 1 C
C14 1.21158(19) 0.6407(2) 0.75676(11) 0.0449(5) Uani d . 1 C
H14 1.2200 0.7199 0.7216 0.054 Uiso calc R 1 H
C15 1.09325(18) 0.6192(2) 0.78166(11) 0.0436(5) Uani d . 1 C
H15 1.0213 0.6842 0.7637 0.052 Uiso calc R 1 H
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
C6 O1 C8 117.91(13)
C5 O2 H2 112.1(17)
C1 N1 N2 116.70(16)
C10 N2 N1 120.76(16)
C10 N2 H2A 118.1(15)
N1 N2 H2A 121.1(15)
O3 N3 O4 121.71(17)
O3 N3 C13 119.23(18)
O4 N3 C13 119.06(17)
N1 C1 C2 122.00(17)
N1 C1 H1 119.0
C2 C1 H1 119.0
C3 C2 C7 118.54(17)
C3 C2 C1 122.06(16)
C7 C2 C1 119.40(16)
C4 C3 C2 120.76(16)
C4 C3 H3 119.6
C2 C3 H3 119.6
C5 C4 C3 120.47(17)
C5 C4 H4 119.8
C3 C4 H4 119.8
O2 C5 C4 119.16(17)
O2 C5 C6 121.19(16)
C4 C5 C6 119.65(17)
O1 C6 C7 125.69(16)
O1 C6 C5 114.71(16)
C7 C6 C5 119.56(16)
C6 C7 C2 120.96(16)
C6 C7 H7 119.5
C2 C7 H7 119.5
O1 C8 C9 107.54(15)
O1 C8 H8A 110.2
C9 C8 H8A 110.2
O1 C8 H8B 110.2
C9 C8 H8B 110.2
H8A C8 H8B 108.5
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
N2 C10 C11 121.71(16)
N2 C10 C15 119.04(16)
C11 C10 C15 119.26(16)
C12 C11 C10 120.34(17)
C12 C11 H11 119.8
C10 C11 H11 119.8
C11 C12 C13 119.46(17)
C11 C12 H12 120.3
C13 C12 H12 120.3
C14 C13 C12 120.93(17)
C14 C13 N3 119.63(17)
C12 C13 N3 119.44(17)
C15 C14 C13 119.93(17)
C15 C14 H14 120.0
C13 C14 H14 120.0
C14 C15 C10 120.08(17)
C14 C15 H15 120.0
C10 C15 H15 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.371(2)
O1 C8 1.431(2)
O2 C5 1.369(2)
O2 H2 0.83(3)
O3 N3 1.227(2)
O4 N3 1.231(2)
N1 C1 1.277(2)
N1 N2 1.370(2)
N2 C10 1.370(2)
N2 H2A 0.82(2)
N3 C13 1.447(2)
C1 C2 1.458(2)
C1 H1 0.9300
C2 C3 1.390(2)
C2 C7 1.397(2)
C3 C4 1.379(2)
C3 H3 0.9300
C4 C5 1.378(2)
C4 H4 0.9300
C5 C6 1.401(2)
C6 C7 1.379(2)
C7 H7 0.9300
C8 C9 1.501(2)
C8 H8A 0.9700
C8 H8B 0.9700
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 C11 1.397(2)
C10 C15 1.399(2)
C11 C12 1.370(2)
C11 H11 0.9300
C12 C13 1.384(2)
C12 H12 0.9300
C13 C14 1.380(2)
C14 C15 1.366(2)
C14 H14 0.9300
C15 H15 0.9300
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
_geom_hbond_publ_flag
O2 H2 O1 . 0.83(3) 2.27(2) 2.6840(19) 111(2) yes
O2 H2 O4 4_466 0.83(3) 2.26(3) 2.987(2) 146(2) yes
O2 H2 O3 4_466 0.83(3) 2.49(3) 3.205(2) 145(2) yes
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
C1 N1 N2 C10 -179.31(16)
N2 N1 C1 C2 -179.51(15)
N1 C1 C2 C3 -1.0(3)
N1 C1 C2 C7 178.21(17)
C7 C2 C3 C4 -1.6(3)
C1 C2 C3 C4 177.57(16)
C2 C3 C4 C5 -0.6(3)
C3 C4 C5 O2 -177.81(16)
C3 C4 C5 C6 2.5(3)
C8 O1 C6 C7 9.3(3)
C8 O1 C6 C5 -172.81(15)
O2 C5 C6 O1 0.2(2)
C4 C5 C6 O1 179.89(16)
O2 C5 C6 C7 178.20(16)
C4 C5 C6 C7 -2.1(3)
O1 C6 C7 C2 177.63(16)
C5 C6 C7 C2 -0.2(3)
C3 C2 C7 C6 2.0(3)
C1 C2 C7 C6 -177.22(16)
C6 O1 C8 C9 179.21(16)
N1 N2 C10 C11 6.1(3)
N1 N2 C10 C15 -174.27(15)
N2 C10 C11 C12 -179.65(17)
C15 C10 C11 C12 0.7(3)
C10 C11 C12 C13 -0.3(3)
C11 C12 C13 C14 -0.4(3)
C11 C12 C13 N3 -179.42(16)
O3 N3 C13 C14 -11.4(3)
O4 N3 C13 C14 169.09(16)
O3 N3 C13 C12 167.68(17)
O4 N3 C13 C12 -11.9(3)
C12 C13 C14 C15 0.7(3)
N3 C13 C14 C15 179.77(16)
C13 C14 C15 C10 -0.4(3)
N2 C10 C15 C14 180.00(16)
C11 C10 C15 C14 -0.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 29341022
