#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/65/2216545.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_2216545
loop_
_publ_author_name
'Muhammad Hanif'
'Ghulam Qadeer'
'Nasim Hasan Rama'
'Sauli Vuoti'
'Juho Autio'
_publ_section_title
;
 3-Hydroxy-4-methoxybenzohydrazide
;
_journal_coeditor_code           HK2352
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4506
_journal_page_last               o4506
_journal_paper_doi               10.1107/S1600536807053160
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C8 H10 N2 O3'
_chemical_formula_moiety         'C8 H10 N2 O3'
_chemical_formula_sum            'C8 H10 N2 O3'
_chemical_formula_weight         182.18
_chemical_melting_point          475(2)
_chemical_name_systematic
;
3-Hydroxy-4-methoxybenzohydrazide
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   mixed
_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                120.00
_cell_formula_units_Z            18
_cell_length_a                   19.4079(10)
_cell_length_b                   19.4079(10)
_cell_length_c                   11.5250(4)
_cell_measurement_reflns_used    13690
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     3759.5(3)
_computing_cell_refinement       'EVALCCD (Duisenberg et al., 2003)'
_computing_data_collection       'COLLECT (Bruker AXS, 2000)'
_computing_data_reduction        'EVALCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2007)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14714
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_correction_T_min  0.9772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         1920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0448
_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)+(0.0273P)²+5.5999P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0868
_reflns_number_gt                1362
_reflns_number_total             1920
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2352.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               2216545
_cod_database_fobs_code          2216545
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
O O1 0.09395(7) 0.93439(7) -0.22631(10) 0.0177(3) Uani d . 1
O O2 0.24707(7) 1.00363(7) -0.25462(9) 0.0166(3) Uani d . 1
H H2O 0.2983(15) 1.0281(14) -0.2516(19) 0.044(7) Uiso d . 1
O O3 0.35414(6) 0.92873(6) 0.09783(9) 0.0144(3) Uani d . 1
N N1 0.24700(9) 0.81514(8) 0.15538(11) 0.0143(3) Uani d . 1
H H1N 0.1958(12) 0.7796(12) 0.1509(16) 0.024(5) Uiso d . 1
N N2 0.29078(9) 0.78856(8) 0.22064(13) 0.0147(3) Uani d . 1
H H2N 0.3332(12) 0.7967(11) 0.1776(16) 0.019(5) Uiso d . 1
H H2M 0.3109(12) 0.8204(12) 0.2860(18) 0.027(5) Uiso d . 1
C C1 0.00948(10) 0.89463(11) -0.21621(16) 0.0229(4) Uani d . 1
H H1A -0.0118 0.8370 -0.2146 0.034 Uiso calc R 1
H H1B -0.0128 0.9083 -0.2828 0.034 Uiso calc R 1
H H1C -0.0051 0.9113 -0.1444 0.034 Uiso calc R 1
C C2 0.13430(10) 0.91959(10) -0.14269(13) 0.0132(4) Uani d . 1
C C3 0.21694(10) 0.95706(9) -0.15902(13) 0.0126(4) Uani d . 1
C C4 0.26263(10) 0.94487(9) -0.07985(13) 0.0130(4) Uani d . 1
H H4 0.3185 0.9699 -0.0910 0.016 Uiso calc R 1
C C5 0.22816(9) 0.89622(9) 0.01679(13) 0.0123(3) Uani d . 1
C C6 0.28099(9) 0.88187(9) 0.09396(13) 0.0118(3) Uani d . 1
C C7 0.14684(10) 0.86073(10) 0.03336(14) 0.0157(4) Uani d . 1
H H7 0.1229 0.8281 0.0994 0.019 Uiso calc R 1
C C8 0.10022(10) 0.87259(10) -0.04603(14) 0.0160(4) Uani d . 1
H H8 0.0445 0.8483 -0.0339 0.019 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0116(6) 0.0231(7) 0.0181(6) 0.0085(5) -0.0025(5) 0.0038(5)
O2 0.0117(6) 0.0203(7) 0.0145(6) 0.0057(6) 0.0019(5) 0.0062(5)
O3 0.0126(6) 0.0125(6) 0.0172(6) 0.0056(5) 0.0002(5) 0.0016(5)
N1 0.0118(8) 0.0130(7) 0.0168(7) 0.0051(7) -0.0025(6) 0.0022(6)
N2 0.0147(8) 0.0159(8) 0.0157(7) 0.0093(7) -0.0025(6) 0.0016(6)
C1 0.0138(9) 0.0299(11) 0.0250(10) 0.0109(8) -0.0036(7) 0.0019(8)
C2 0.0148(9) 0.0132(8) 0.0135(8) 0.0084(7) -0.0026(7) -0.0019(7)
C3 0.0164(9) 0.0098(8) 0.0111(8) 0.0061(7) 0.0002(7) -0.0009(6)
C4 0.0109(8) 0.0127(8) 0.0148(8) 0.0055(7) 0.0002(6) -0.0019(7)
C5 0.0151(8) 0.0098(8) 0.0128(8) 0.0069(7) -0.0013(7) -0.0020(6)
C6 0.0142(9) 0.0114(8) 0.0107(8) 0.0071(7) 0.0010(6) -0.0022(6)
C7 0.0166(9) 0.0150(9) 0.0145(8) 0.0072(7) 0.0019(7) 0.0024(7)
C8 0.0109(8) 0.0166(9) 0.0194(8) 0.0060(7) 0.0009(7) -0.0003(7)
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 O1 C1 117.11(13)
C3 O2 H2O 109.1(15)
C6 N1 N2 123.02(14)
C6 N1 H1N 123.1(12)
N2 N1 H1N 113.2(12)
N1 N2 H2N 107.8(12)
N1 N2 H2M 108.6(12)
H2N N2 H2M 106.6(17)
O1 C1 H1A 109.5
O1 C1 H1B 109.5
H1A C1 H1B 109.5
O1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O1 C2 C8 125.10(15)
O1 C2 C3 115.15(14)
C8 C2 C3 119.75(15)
O2 C3 C4 123.62(15)
O2 C3 C2 116.99(14)
C4 C3 C2 119.39(14)
C3 C4 C5 120.97(15)
C3 C4 H4 119.5
C5 C4 H4 119.5
C7 C5 C4 119.24(15)
C7 C5 C6 123.13(14)
C4 C5 C6 117.55(14)
O3 C6 N1 121.49(15)
O3 C6 C5 121.73(14)
N1 C6 C5 116.74(14)
C5 C7 C8 120.24(15)
C5 C7 H7 119.9
C8 C7 H7 119.9
C2 C8 C7 120.39(15)
C2 C8 H8 119.8
C7 C8 H8 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.3599(19)
O1 C1 1.425(2)
O2 C3 1.3580(19)
O2 H2O 0.86(2)
O3 C6 1.2464(19)
N1 C6 1.326(2)
N1 N2 1.4114(19)
N1 H1N 0.88(2)
N2 H2N 0.91(2)
N2 H2M 0.93(2)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C8 1.381(2)
C2 C3 1.404(2)
C3 C4 1.373(2)
C4 C5 1.396(2)
C4 H4 0.9500
C5 C7 1.384(2)
C5 C6 1.485(2)
C7 C8 1.385(2)
C7 H7 0.9500
C8 H8 0.9500
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
N2 H2N N2 14_455 0.91(2) 2.24(2) 3.1274(19) 165.3(16) yes
N2 H2N N1 14_455 0.91(2) 2.567(19) 3.266(2) 134.5(15) yes
N2 H2M O2 8_665 0.93(2) 2.15(2) 3.0364(19) 158.6(17) yes
N2 H2M O1 8_665 0.93(2) 2.43(2) 3.1335(18) 132.6(15) yes
N1 H1N O3 15 0.88(2) 2.15(2) 2.9296(18) 147.6(16) yes
O2 H2O O3 8_664 0.86(2) 1.81(2) 2.6635(16) 171(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21120368
