#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/88/2218833.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_2218833
loop_
_publ_author_name
'Cheng, Xiang-Wei'
_publ_section_title
;
 (E)-Methyl N'-(4-hydroxybenzylidene)hydrazinecarboxylate
;
_journal_coeditor_code           TK2273
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1302
_journal_paper_doi               10.1107/S1600536808018096
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C9 H10 N2 O3'
_chemical_formula_moiety         'C9 H10 N2 O3'
_chemical_formula_sum            'C9 H10 N2 O3'
_chemical_formula_weight         194.19
_chemical_name_systematic
;
(E)-Methyl N'-(4-hydroxybenzylidene)hydrazinecarboxylate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 111.970(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1943(8)
_cell_length_b                   12.0512(11)
_cell_length_c                   10.1067(9)
_cell_measurement_reflns_used    1628
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.0
_cell_volume                     925.57(15)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.021
_diffrn_reflns_av_sigmaI/netI    0.016
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9552
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.7
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.19
_refine_ls_extinction_coef       0.288(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.95
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1623
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.95
_refine_ls_R_factor_all          0.038
_refine_ls_R_factor_gt           0.035
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0871P)²+0.1838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.112
_refine_ls_wR_factor_ref         0.115
_reflns_number_gt                1487
_reflns_number_total             1623
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2273.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               2218833
_cod_database_fobs_code          2218833
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_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 0.38082(14) 0.30936(8) 0.37656(11) 0.0529(3) Uani d . 1
H H1 0.3162 0.3134 0.2897 0.079 Uiso calc R 1
O O2 0.97787(14) -0.29441(9) 0.29627(10) 0.0516(3) Uani d . 1
O O3 1.11604(14) -0.37383(8) 0.51277(11) 0.0520(3) Uani d . 1
N N2 0.94810(15) -0.22777(9) 0.49593(12) 0.0440(3) Uani d . 1
H H2A 0.9787 -0.2353 0.5887 0.053 Uiso calc R 1
N N1 0.83415(14) -0.14299(9) 0.42392(11) 0.0395(3) Uani d . 1
C C5 0.57987(17) 0.04812(11) 0.32350(13) 0.0396(4) Uani d . 1
H H5 0.5728 -0.0024 0.2494 0.047 Uiso calc R 1
C C6 0.69854(16) 0.02765(10) 0.46270(13) 0.0369(3) Uani d . 1
C C3 0.47278(17) 0.14106(11) 0.29260(13) 0.0408(4) Uani d . 1
H H3 0.3932 0.1538 0.1976 0.049 Uiso calc R 1
C C1 0.48094(16) 0.21605(10) 0.39995(14) 0.0390(4) Uani d . 1
C C2 0.59680(18) 0.19579(11) 0.53868(14) 0.0428(4) Uani d . 1
H H2 0.6028 0.2459 0.6129 0.051 Uiso calc R 1
C C4 0.70306(17) 0.10317(12) 0.56872(14) 0.0410(4) Uani d . 1
H H4 0.7815 0.0904 0.6641 0.049 Uiso calc R 1
C C8 1.01137(16) -0.29807(11) 0.42353(14) 0.0386(4) Uani d . 1
C C7 0.81502(16) -0.06805(11) 0.50677(14) 0.0398(4) Uani d . 1
H H7 0.8828 -0.0755 0.6058 0.048 Uiso calc R 1
C C9 1.1945(2) -0.45473(13) 0.4509(2) 0.0619(5) Uani d . 1
H H9A 1.2675 -0.5054 0.5253 0.093 Uiso calc R 1
H H9B 1.2678 -0.4171 0.4071 0.093 Uiso calc R 1
H H9C 1.1018 -0.4969 0.3778 0.093 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 0.0548(6) 0.0432(6) 0.0517(6) 0.0084(4) 0.0096(5) -0.0039(4)
O2 0.0574(6) 0.0589(7) 0.0365(6) 0.0024(5) 0.0154(5) -0.0063(4)
O3 0.0570(6) 0.0504(6) 0.0506(6) 0.0140(5) 0.0226(5) 0.0073(4)
N2 0.0520(7) 0.0473(7) 0.0344(6) 0.0110(5) 0.0181(5) 0.0068(5)
N1 0.0390(6) 0.0411(6) 0.0388(6) 0.0018(4) 0.0153(5) 0.0040(5)
C5 0.0446(7) 0.0398(7) 0.0358(7) -0.0025(5) 0.0168(5) -0.0020(5)
C6 0.0376(6) 0.0367(7) 0.0384(7) -0.0047(5) 0.0164(5) 0.0018(5)
C3 0.0416(7) 0.0423(7) 0.0357(7) -0.0026(5) 0.0111(5) 0.0022(5)
C1 0.0383(7) 0.0340(7) 0.0451(8) -0.0036(5) 0.0161(6) 0.0005(5)
C2 0.0464(7) 0.0408(7) 0.0405(7) -0.0039(6) 0.0155(6) -0.0063(6)
C4 0.0421(7) 0.0435(8) 0.0352(6) -0.0041(5) 0.0118(5) -0.0001(5)
C8 0.0372(7) 0.0407(7) 0.0381(7) -0.0041(5) 0.0141(5) -0.0006(5)
C7 0.0419(7) 0.0423(8) 0.0351(7) -0.0020(5) 0.0142(5) 0.0020(5)
C9 0.0611(10) 0.0503(9) 0.0785(12) 0.0113(7) 0.0311(8) -0.0005(8)
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
C1 O1 H1 109.5
C8 O3 C9 116.56(12)
N1 N2 C8 119.88(11)
C8 N2 H2A 120.1
N1 N2 H2A 120.1
N2 N1 C7 113.47(11)
C3 C5 C6 120.82(12)
C3 C5 H5 119.6
C6 C5 H5 119.6
C4 C6 C5 117.73(12)
C4 C6 C7 117.09(11)
C5 C6 C7 125.16(12)
C5 C3 C1 120.46(12)
C5 C3 H3 119.8
C1 C3 H3 119.8
O1 C1 C2 117.44(12)
O1 C1 C3 123.41(12)
C2 C1 C3 119.14(12)
C4 C2 C1 120.11(12)
C4 C2 H2 119.9
C1 C2 H2 119.9
C2 C4 C6 121.73(12)
C2 C4 H4 119.1
C6 C4 H4 119.1
O2 C8 O3 124.88(12)
O2 C8 N2 125.09(13)
O3 C8 N2 110.03(11)
N1 C7 C6 125.81(11)
N1 C7 H7 117.1
C6 C7 H7 117.1
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3595(16)
O1 H1 0.8400
O2 C8 1.2114(17)
O3 C8 1.3431(16)
O3 C9 1.4339(18)
N1 N2 1.3917(15)
N2 H2A 0.8800
N1 C7 1.2805(17)
N2 C8 1.3438(17)
C5 C3 1.3846(18)
C5 C6 1.4007(18)
C5 H5 0.9500
C6 C4 1.3958(18)
C6 C7 1.4565(18)
C3 C1 1.3943(19)
C3 H3 0.9500
C1 C2 1.3895(19)
C2 C4 1.3778(19)
C2 H2 0.9500
C4 H4 0.9500
C7 H7 0.9500
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
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 H1 O2 2_655 0.84 2.58 3.068(2) 118
O1 H1 N1 2_655 0.84 2.11 2.941(2) 169
N2 H2A O2 4_556 0.88 2.13 2.964(2) 158
C7 H7 O2 4_556 0.95 2.38 3.188(2) 143
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
C8 N2 N1 C7 -165.18(12)
C3 C5 C6 C4 0.84(18)
C3 C5 C6 C7 179.14(12)
C6 C5 C3 C1 -0.14(19)
C5 C3 C1 O1 179.33(12)
C5 C3 C1 C2 -0.60(19)
O1 C1 C2 C4 -179.31(12)
C3 C1 C2 C4 0.62(19)
C1 C2 C4 C6 0.1(2)
C5 C6 C4 C2 -0.82(19)
C7 C6 C4 C2 -179.27(11)
C9 O3 C8 O2 0.9(2)
C9 O3 C8 N2 -179.72(12)
N1 N2 C8 O2 0.3(2)
N1 N2 C8 O3 -179.11(10)
N2 N1 C7 C6 -177.08(11)
C4 C6 C7 N1 -176.85(12)
C5 C6 C7 N1 4.8(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12669351
