#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/85/2238512.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_2238512
loop_
_publ_author_name
'Saravanan, B.'
'Jayamani, A.'
'Sengottuvelan, N.'
'Chakkaravarthi, G.'
'Manivannan, V.'
_publ_section_title
;
 1,2-Bis(2-hydroxy-5-methylbenzylidene)hydrazine
;
_journal_coeditor_code           IS5296
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1394
_journal_page_last               o1395
_journal_paper_doi               10.1107/S160053681302148X
_journal_volume                  69
_journal_year                    2013
_chemical_formula_moiety         'C16 H16 N2 O2'
_chemical_formula_sum            'C16 H16 N2 O2'
_chemical_formula_weight         268.31
_chemical_name_common
;
1,2-Bis(2-hydroxy-5-methylbenzylidene)hydrazine
;
_chemical_name_systematic
;
2-{[2-(2-Hydroxy-5-methylbenzylidene)hydrazin-1-ylidene]methyl}-4-methylphenol
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   6.0108(5)
_cell_length_b                   7.3394(5)
_cell_length_c                   31.674(2)
_cell_measurement_reflns_used    2658
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      2.4
_cell_volume                     1397.32(17)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker Kappa APEXII'
_diffrn_measurement_method       'ω and φ '
_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  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            5699
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.16
_diffrn_reflns_theta_min         2.57
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_correction_T_min  0.9815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.166
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2952
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0503
_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)+(0.0788P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1541
_reflns_number_gt                1780
_reflns_number_total             2952
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is5296.cif
_cod_data_source_block           I
_cod_database_code               2238512
_cod_database_fobs_code          2238512
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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
C C1 -0.1393(4) 0.8872(3) 0.28106(7) 0.0424(6) Uani d . 1 1
C C2 -0.0535(4) 0.9211(3) 0.24097(7) 0.0467(6) Uani d . 1 1
H H2 0.0874 0.9726 0.2387 0.056 Uiso calc R 1 1
C C3 -0.1689(5) 0.8812(4) 0.20427(8) 0.0528(7) Uani d . 1 1
C C4 -0.3790(5) 0.8051(4) 0.20879(8) 0.0558(7) Uani d . 1 1
H H4 -0.4604 0.7765 0.1847 0.067 Uiso calc R 1 1
C C5 -0.4700(5) 0.7708(3) 0.24753(9) 0.0540(7) Uani d . 1 1
H H5 -0.6106 0.7185 0.2493 0.065 Uiso calc R 1 1
C C6 -0.3559(4) 0.8129(4) 0.28389(8) 0.0474(7) Uani d . 1 1
C C7 -0.0682(6) 0.9219(4) 0.16150(7) 0.0766(10) Uani d . 1 1
H H7A -0.0947 0.8212 0.1428 0.115 Uiso calc R 1 1
H H7B 0.0891 0.9405 0.1645 0.115 Uiso calc R 1 1
H H7C -0.1352 1.0299 0.1500 0.115 Uiso calc R 1 1
C C8 -0.0071(4) 0.9275(3) 0.31799(7) 0.0454(6) Uani d . 1 1
H H8 0.1363 0.9726 0.3145 0.055 Uiso calc R 1 1
C C9 -0.0019(4) 0.9213(3) 0.42464(7) 0.0451(6) Uani d . 1 1
H H9 -0.1451 0.8758 0.4282 0.054 Uiso calc R 1 1
C C10 0.1302(5) 0.9612(3) 0.46142(7) 0.0429(6) Uani d . 1 1
C C11 0.0395(5) 0.9322(3) 0.50158(7) 0.0478(7) Uani d . 1 1
H H11 -0.1016 0.8810 0.5035 0.057 Uiso calc R 1 1
C C12 0.1501(5) 0.9762(3) 0.53841(8) 0.0527(7) Uani d . 1 1
C C13 0.3625(6) 1.0501(4) 0.53396(8) 0.0578(8) Uani d . 1 1
H H13 0.4417 1.0814 0.5581 0.069 Uiso calc R 1 1
C C14 0.4593(5) 1.0786(4) 0.49519(8) 0.0556(7) Uani d . 1 1
H H14 0.6019 1.1271 0.4935 0.067 Uiso calc R 1 1
C C15 0.3451(5) 1.0352(3) 0.45871(8) 0.0460(6) Uani d . 1 1
C C16 0.0438(6) 0.9530(4) 0.58087(8) 0.0718(9) Uani d . 1 1
H H16A -0.0435 1.0588 0.5874 0.108 Uiso calc R 1 1
H H16B 0.1573 0.9378 0.6019 0.108 Uiso calc R 1 1
H H16C -0.0504 0.8474 0.5805 0.108 Uiso calc R 1 1
N N1 -0.0818(3) 0.9027(3) 0.35543(6) 0.0498(6) Uani d . 1 1
N N2 0.0716(4) 0.9465(3) 0.38727(6) 0.0498(6) Uani d . 1 1
O O1 -0.4551(3) 0.7801(3) 0.32150(5) 0.0680(6) Uani d . 1 1
H H1 -0.3751 0.8171 0.3406 0.102 Uiso calc R 1 1
O O2 0.4451(3) 1.0657(3) 0.42094(6) 0.0650(6) Uani d . 1 1
H H2A 0.3623 1.0328 0.4018 0.098 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
C2 C1 C6 117.9(2)
C2 C1 C8 119.9(2)
C6 C1 C8 122.3(2)
C3 C2 C1 122.8(2)
C3 C2 H2 118.6
C1 C2 H2 118.6
C2 C3 C4 117.0(2)
C2 C3 C7 120.6(3)
C4 C3 C7 122.4(3)
C5 C4 C3 122.0(3)
C5 C4 H4 119.0
C3 C4 H4 119.0
C4 C5 C6 120.7(3)
C4 C5 H5 119.6
C6 C5 H5 119.6
O1 C6 C5 118.5(2)
O1 C6 C1 122.0(2)
C5 C6 C1 119.5(2)
C3 C7 H7A 109.5
C3 C7 H7B 109.5
H7A C7 H7B 109.5
C3 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
N1 C8 C1 121.8(2)
N1 C8 H8 119.1
C1 C8 H8 119.1
N2 C9 C10 122.0(2)
N2 C9 H9 119.0
C10 C9 H9 119.0
C11 C10 C15 118.2(2)
C11 C10 C9 119.3(3)
C15 C10 C9 122.5(2)
C12 C11 C10 123.0(3)
C12 C11 H11 118.5
C10 C11 H11 118.5
C11 C12 C13 116.5(3)
C11 C12 C16 121.8(3)
C13 C12 C16 121.7(3)
C14 C13 C12 122.5(3)
C14 C13 H13 118.8
C12 C13 H13 118.8
C13 C14 C15 120.1(3)
C13 C14 H14 119.9
C15 C14 H14 119.9
O2 C15 C14 118.6(3)
O2 C15 C10 121.7(2)
C14 C15 C10 119.7(2)
C12 C16 H16A 109.5
C12 C16 H16B 109.5
H16A C16 H16B 109.5
C12 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C8 N1 N2 113.7(2)
C9 N2 N1 113.9(2)
C6 O1 H1 109.5
C15 O2 H2A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.393(3)
C1 C6 1.415(3)
C1 C8 1.445(3)
C2 C3 1.385(3)
C2 H2 0.9300
C3 C4 1.388(4)
C3 C7 1.514(3)
C4 C5 1.367(4)
C4 H4 0.9300
C5 C6 1.376(3)
C5 H5 0.9300
C6 O1 1.354(3)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 N1 1.281(3)
C8 H8 0.9300
C9 N2 1.277(3)
C9 C10 1.440(3)
C9 H9 0.9300
C10 C11 1.400(3)
C10 C15 1.404(3)
C11 C12 1.381(3)
C11 H11 0.9300
C12 C13 1.395(4)
C12 C16 1.499(3)
C13 C14 1.375(4)
C13 H13 0.9300
C14 C15 1.381(3)
C14 H14 0.9300
C15 O2 1.357(3)
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
N1 N2 1.404(3)
O1 H1 0.8200
O2 H2A 0.8200
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 H2A N2 . 0.82 1.91 2.635(3) 146 y
O1 H1 N1 . 0.82 1.93 2.646(3) 145 y
C5 H5 Cg1 4_445 0.93 2.84 3.519(3) 130 y
C14 H14 Cg2 3_576 0.93 2.85 3.519(3) 130 y
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
C6 C1 C2 C3 -1.5(4)
C8 C1 C2 C3 178.2(2)
C1 C2 C3 C4 0.3(4)
C1 C2 C3 C7 179.6(2)
C2 C3 C4 C5 0.2(4)
C7 C3 C4 C5 -179.1(3)
C3 C4 C5 C6 0.7(4)
C4 C5 C6 O1 178.5(2)
C4 C5 C6 C1 -1.9(4)
C2 C1 C6 O1 -178.2(2)
C8 C1 C6 O1 2.1(4)
C2 C1 C6 C5 2.3(4)
C8 C1 C6 C5 -177.4(2)
C2 C1 C8 N1 178.2(2)
C6 C1 C8 N1 -2.0(4)
N2 C9 C10 C11 179.4(2)
N2 C9 C10 C15 2.0(4)
C15 C10 C11 C12 1.3(4)
C9 C10 C11 C12 -176.3(2)
C10 C11 C12 C13 -0.9(4)
C10 C11 C12 C16 176.6(2)
C11 C12 C13 C14 0.0(4)
C16 C12 C13 C14 -177.6(2)
C12 C13 C14 C15 0.6(4)
C13 C14 C15 O2 179.7(2)
C13 C14 C15 C10 -0.3(4)
C11 C10 C15 O2 179.4(2)
C9 C10 C15 O2 -3.1(4)
C11 C10 C15 C14 -0.6(3)
C9 C10 C15 C14 176.9(2)
C1 C8 N1 N2 179.0(2)
C10 C9 N2 N1 -179.07(19)
C8 N1 N2 C9 -179.7(2)
