#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/84/2208423.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_2208423
loop_
_publ_author_name
'Ming-Li Liu'
'Jian-Min Dou'
'Da-Cheng Li'
'Da-Qi Wang'
_publ_section_title
;
 2'-Acetyl-2-hydroxynaphthohydrazide
;
_journal_coeditor_code           SG6059
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1009
_journal_page_last               o1010
_journal_paper_doi               10.1107/S1600536806002285
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C13 H12 N2 O3'
_chemical_formula_moiety         'C13 H12 N2 O3'
_chemical_formula_sum            'C13 H12 N2 O3'
_chemical_formula_weight         244.25
_chemical_name_systematic
;
2'-Acetyl-2-hydroxynaphthohydrazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.329(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.266(2)
_cell_length_b                   22.987(8)
_cell_length_c                   8.503(3)
_cell_measurement_reflns_used    1313
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.074
_cell_measurement_theta_min      2.598
_cell_volume                     1200.9(7)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Siemens 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  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0690
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7738
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         2.60
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_correction_T_min  0.9694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.223
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.1370
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.047
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.079P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1727
_reflns_number_gt                1283
_reflns_number_total             2934
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sg6059.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2208423
_cod_database_fobs_code          2208423
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
N N2 0.2466(3) 0.00993(9) 0.2198(2) 0.0463(6) Uani d . 1
O O3 -0.0894(3) 0.04576(7) 0.3333(2) 0.0510(5) Uani d . 1
N N1 0.4219(3) -0.02753(9) 0.2311(2) 0.0449(5) Uani d . 1
C C3 0.1907(3) 0.04474(10) 0.0934(3) 0.0374(5) Uani d . 1
C C6 -0.3053(4) 0.12221(10) 0.1955(3) 0.0421(6) Uani d . 1
H H6 -0.3940 0.1212 0.2712 0.051 Uiso calc R 1
C C4 0.0021(3) 0.08477(9) 0.0942(2) 0.0359(5) Uani d . 1
O O2 0.2901(3) 0.04441(8) -0.01718(19) 0.0541(5) Uani d . 1
C C1 0.4633(4) -0.06334(11) 0.3560(3) 0.0465(6) Uani d . 1
C C5 -0.1343(3) 0.08462(10) 0.2098(3) 0.0376(6) Uani d . 1
C C13 -0.0404(4) 0.12420(10) -0.0287(3) 0.0453(6) Uani d . 1
H H13 0.0488 0.1247 -0.1042 0.054 Uiso calc R 1
C C12 -0.2134(4) 0.16386(10) -0.0450(3) 0.0449(6) Uani d . 1
O O1 0.3459(3) -0.06341(9) 0.4566(2) 0.0749(7) Uani d . 1
C C7 -0.3507(4) 0.16258(10) 0.0689(3) 0.0426(6) Uani d . 1
C C8 -0.5263(4) 0.20211(11) 0.0500(3) 0.0571(7) Uani d . 1
H H8 -0.6209 0.2009 0.1217 0.069 Uiso calc R 1
C C2 0.6579(4) -0.10168(13) 0.3672(3) 0.0628(8) Uani d . 1
H H2A 0.7784 -0.0849 0.4404 0.094 Uiso calc R 1
H H2B 0.6944 -0.1054 0.2632 0.094 Uiso calc R 1
H H2C 0.6260 -0.1394 0.4053 0.094 Uiso calc R 1
C C11 -0.2537(4) 0.20553(13) -0.1694(4) 0.0669(8) Uani d . 1
H H11 -0.1634 0.2071 -0.2440 0.080 Uiso calc R 1
C C9 -0.5600(5) 0.24172(13) -0.0701(4) 0.0716(9) Uani d . 1
H H9 -0.6749 0.2679 -0.0787 0.086 Uiso calc R 1
C C10 -0.4229(5) 0.24347(14) -0.1815(4) 0.0807(10) Uani d . 1
H H10 -0.4474 0.2706 -0.2641 0.097 Uiso calc R 1
H H15 0.503(4) -0.0262(11) 0.145(3) 0.071(8) Uiso d . 1
H H16 0.165(4) 0.0054(10) 0.300(3) 0.065(8) Uiso d . 1
H H14 -0.190(4) 0.0504(11) 0.400(3) 0.074(9) Uiso d . 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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 N2 N1 120.61(19)
C3 N2 H16 124.1(15)
N1 N2 H16 114.9(15)
C5 O3 H14 109.4(17)
C1 N1 N2 117.95(19)
C1 N1 H15 124.9(15)
N2 N1 H15 117.2(15)
O2 C3 N2 121.6(2)
O2 C3 C4 121.8(2)
N2 C3 C4 116.61(19)
C5 C6 C7 121.5(2)
C5 C6 H6 119.2
C7 C6 H6 119.2
C13 C4 C5 118.4(2)
C13 C4 C3 115.98(19)
C5 C4 C3 125.6(2)
O1 C1 N1 120.4(2)
O1 C1 C2 123.1(2)
N1 C1 C2 116.5(2)
C6 C5 O3 121.5(2)
C6 C5 C4 120.3(2)
O3 C5 C4 118.14(19)
C4 C13 C12 122.4(2)
C4 C13 H13 118.8
C12 C13 H13 118.8
C13 C12 C11 122.4(2)
C13 C12 C7 118.7(2)
C11 C12 C7 118.9(2)
C6 C7 C8 123.1(2)
C6 C7 C12 118.6(2)
C8 C7 C12 118.3(2)
C9 C8 C7 121.4(2)
C9 C8 H8 119.3
C7 C8 H8 119.3
C1 C2 H2A 109.5
C1 C2 H2B 109.5
H2A C2 H2B 109.5
C1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
C10 C11 C12 120.9(3)
C10 C11 H11 119.6
C12 C11 H11 119.6
C8 C9 C10 120.3(3)
C8 C9 H9 119.8
C10 C9 H9 119.8
C11 C10 C9 120.2(3)
C11 C10 H10 119.9
C9 C10 H10 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 C3 1.331(3)
N2 N1 1.384(3)
N2 H16 0.94(2)
O3 C5 1.366(3)
O3 H14 0.94(3)
N1 C1 1.328(3)
N1 H15 0.97(3)
C3 O2 1.226(2)
C3 C4 1.499(3)
C6 C5 1.363(3)
C6 C7 1.408(3)
C6 H6 0.9300
C4 C13 1.369(3)
C4 C5 1.424(3)
C1 O1 1.233(3)
C1 C2 1.492(3)
C13 C12 1.403(3)
C13 H13 0.9300
C12 C11 1.413(3)
C12 C7 1.415(3)
C7 C8 1.412(3)
C8 C9 1.354(4)
C8 H8 0.9300
C2 H2A 0.9600
C2 H2B 0.9600
C2 H2C 0.9600
C11 C10 1.361(4)
C11 H11 0.9300
C9 C10 1.399(4)
C9 H9 0.9300
C10 H10 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
N2 H16 O3 . 0.94(2) 1.91(2) 2.615(3) 130(2)
O3 H14 O1 3_556 0.94(3) 1.73(3) 2.658(3) 172(2)
N1 H15 O2 3_655 0.97(3) 1.90(3) 2.829(3) 161(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126331
