#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/51/2015162.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_2015162
loop_
_publ_author_name
'Pelosi, G.'
'Pelizzi, C.'
'Belicchi Ferrari, M.'
'Rodríguez Argüelles, M.C.'
'Vieito, C.'
'Sanmartín, J.'
_publ_section_title
;
 Isatin 3-semicarbazone and 1-methylisatin 3-semicarbazone
;
_journal_coeditor_code           HJ1061
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o589
_journal_page_last               o592
_journal_paper_doi               10.1107/S0108270105024959
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C10 H10 N4 O2'
_chemical_formula_moiety         'C10 H10 N4 O2'
_chemical_formula_sum            'C10 H10 N4 O2'
_chemical_formula_weight         218.22
_chemical_melting_point          249
_chemical_name_common            N-methylisatin-3-semicarbazone
_chemical_name_systematic
;
1-methylindole-2,3-dione 3-semicarbazone
;
_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                   3.984(2)
_cell_length_b                   20.930(6)
_cell_length_c                   12.122(2)
_cell_measurement_reflns_used    3118
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.05
_cell_volume                     1010.8(6)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       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  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9231
_diffrn_reflns_theta_full        23.28
_diffrn_reflns_theta_max         23.28
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.98000
_exptl_absorpt_correction_T_min  0.93890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1999)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.100
_refine_diff_density_min         -0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         910
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0278
_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)+(0.0557P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0768
_reflns_number_gt                782
_reflns_number_total             910
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hj1061.cif
_cod_data_source_block           II
_cod_database_code               2015162
_cod_database_fobs_code          2015162
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_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.7991(6) 0.16810(8) 0.98208(13) 0.0716(6) Uani d . 1 . . O
O2 1.1174(5) 0.03955(8) 0.71768(13) 0.0646(6) Uani d . 1 . . O
N1 0.5444(6) 0.23666(11) 0.86358(17) 0.0652(7) Uani d . 1 . . N
H1 0.4848 0.2629 0.9146 0.078 Uiso calc R 1 . . H
H2 0.4941 0.2445 0.7959 0.078 Uiso calc R 1 . . H
N2 0.8028(7) 0.14554(10) 0.80117(14) 0.0589(6) Uani d . 1 . . N
H3 0.9091 0.1105 0.8133 0.071 Uiso calc R 1 . . H
N3 0.7246(6) 0.16223(9) 0.69678(14) 0.0488(5) Uani d . 1 . . N
N4 1.0444(5) 0.03808(9) 0.52878(15) 0.0486(5) Uani d . 1 . . N
C1 0.7134(7) 0.18433(11) 0.8892(2) 0.0550(7) Uani d . 1 . . C
C2 0.8210(6) 0.12407(10) 0.61916(18) 0.0435(6) Uani d . 1 . . C
C3 0.7599(6) 0.13253(10) 0.50235(17) 0.0422(6) Uani d . 1 . . C
C4 0.6054(7) 0.17950(11) 0.44031(19) 0.0484(6) Uani d . 1 . . C
H4 0.5100 0.2150 0.4741 0.058 Uiso calc R 1 . . H
C5 0.5958(7) 0.17263(13) 0.3271(2) 0.0569(7) Uani d . 1 . . C
H5 0.4943 0.2040 0.2842 0.068 Uiso calc R 1 . . H
C6 0.7346(7) 0.11983(12) 0.2768(2) 0.0602(7) Uani d . 1 . . C
H6 0.7241 0.1163 0.2004 0.072 Uiso calc R 1 . . H
C7 0.8886(7) 0.07211(12) 0.33672(18) 0.0545(7) Uani d . 1 . . C
H7 0.9812 0.0365 0.3023 0.065 Uiso calc R 1 . . H
C8 0.8998(6) 0.07924(10) 0.44936(18) 0.0427(6) Uani d . 1 . . C
C9 1.0115(7) 0.06289(11) 0.63179(19) 0.0481(6) Uani d . 1 . . C
C10 1.2050(8) -0.02279(10) 0.5055(2) 0.0622(8) Uani d . 1 . . C
H10A 1.3533 -0.0181 0.4436 0.093 Uiso calc R 1 . . H
H10B 1.0369 -0.0542 0.4887 0.093 Uiso calc R 1 . . H
H10C 1.3311 -0.0363 0.5688 0.093 Uiso calc R 1 . . H
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 0.1081(17) 0.0666(11) 0.0401(10) -0.0106(13) -0.0094(10) -0.0006(8)
O2 0.0830(14) 0.0571(10) 0.0537(10) 0.0084(11) -0.0110(10) 0.0082(8)
N1 0.0911(19) 0.0614(13) 0.0432(12) 0.0067(14) 0.0079(12) -0.0058(10)
N2 0.0807(17) 0.0510(11) 0.0450(12) 0.0046(13) -0.0035(12) -0.0043(9)
N3 0.0595(13) 0.0498(11) 0.0370(11) -0.0035(11) -0.0023(10) -0.0037(9)
N4 0.0529(13) 0.0404(10) 0.0526(11) 0.0022(11) 0.0012(11) -0.0051(9)
C1 0.0713(19) 0.0505(14) 0.0432(15) -0.0132(15) 0.0050(16) -0.0035(12)
C2 0.0478(15) 0.0404(12) 0.0423(13) -0.0051(12) 0.0022(12) -0.0019(10)
C3 0.0410(14) 0.0405(11) 0.0451(13) -0.0053(12) 0.0000(12) -0.0019(9)
C4 0.0453(14) 0.0458(13) 0.0540(15) -0.0004(12) -0.0003(13) -0.0006(11)
C5 0.0554(17) 0.0622(16) 0.0530(15) -0.0035(15) -0.0089(14) 0.0101(12)
C6 0.0649(18) 0.0719(17) 0.0437(14) -0.0091(17) -0.0025(15) -0.0022(13)
C7 0.0583(17) 0.0559(14) 0.0492(14) -0.0049(16) 0.0046(13) -0.0108(12)
C8 0.0404(14) 0.0412(12) 0.0465(13) -0.0049(12) 0.0020(12) -0.0015(10)
C9 0.0501(15) 0.0440(13) 0.0500(14) -0.0050(12) -0.0015(13) 0.0030(11)
C10 0.0656(19) 0.0429(14) 0.0781(18) 0.0068(16) 0.0051(17) -0.0040(12)
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 N1 H1 120.0
C1 N1 H2 120.0
H1 N1 H2 120.0
N3 N2 C1 120.7(2)
N3 N2 H3 119.7
C1 N2 H3 119.7
C2 N3 N2 117.0(2)
C9 N4 C8 110.70(18)
C9 N4 C10 123.8(2)
C8 N4 C10 125.53(19)
O1 C1 N1 126.0(2)
O1 C1 N2 118.2(2)
N1 C1 N2 115.8(2)
N3 C2 C3 125.9(2)
N3 C2 C9 127.2(2)
C3 C2 C9 106.87(19)
C4 C3 C8 119.6(2)
C4 C3 C2 134.0(2)
C8 C3 C2 106.49(19)
C5 C4 C3 118.6(2)
C5 C4 H4 120.7
C3 C4 H4 120.7
C6 C5 C4 120.8(2)
C6 C5 H5 119.6
C4 C5 H5 119.6
C5 C6 C7 121.8(2)
C5 C6 H6 119.1
C7 C6 H6 119.1
C8 C7 C6 117.3(2)
C8 C7 H7 121.3
C6 C7 H7 121.3
C7 C8 C3 121.9(2)
C7 C8 N4 128.6(2)
C3 C8 N4 109.54(19)
O2 C9 N4 126.5(2)
O2 C9 C2 127.1(2)
N4 C9 C2 106.37(19)
N4 C10 H10A 109.5
N4 C10 H10B 109.5
H10A C10 H10B 109.5
N4 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.225(3) ?
O2 C9 . 1.225(3) ?
N1 C1 . 1.323(3) ?
N1 H1 . 0.86 ?
N1 H2 . 0.86 ?
N2 N3 . 1.349(3) ?
N2 C1 . 1.387(3) ?
N2 H3 . 0.86 ?
N3 C2 . 1.293(3) ?
N4 C9 . 1.359(3) ?
N4 C8 . 1.414(3) ?
N4 C10 . 1.453(3) ?
C2 C3 . 1.448(3) ?
C2 C9 . 1.496(3) ?
C3 C4 . 1.382(3) ?
C3 C8 . 1.403(3) ?
C4 C5 . 1.381(3) ?
C4 H4 . 0.93 ?
C5 C6 . 1.378(4) ?
C5 H5 . 0.93 ?
C6 C7 . 1.379(4) ?
C6 H6 . 0.93 ?
C7 C8 . 1.374(3) ?
C7 H7 . 0.93 ?
C10 H10A . 0.96 ?
C10 H10B . 0.96 ?
C10 H10C . 0.96 ?
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
N1 H1 O1 3_457 0.86 2.05 2.903(3) 171 yes
N1 H2 N3 . 0.86 2.29 2.652(3) 105 yes
N2 H3 O2 . 0.86 2.06 2.742(3) 136 yes
C7 H7 O2 2_754 0.93 2.48 3.379(4) 163 yes
C10 H10C O2 . 0.96 2.55 2.905(3) 102 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4495098
