#------------------------------------------------------------------------------
#$Date: 2023-02-13 10:33:40 +0200 (Mon, 13 Feb 2023) $
#$Revision: 280860 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/67/8106756.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106756
loop_
_publ_author_name
'Wang, Su'
'Liu, Han-Yu'
'Sun, Juan'
_publ_section_title
;
 The crystal structure of
 (Z)-2-(3-(2-(4-chlorobenzoyl)hydrazono)-2-oxoindolin-1-yl) acetic acid,
 C17H12ClN3O4
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1023
_journal_page_last               1024
_journal_paper_doi               10.1515/ncrs-2017-0149
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety
;
C17, H12, Cl, N3, 04
;
_chemical_formula_sum            'C17 H12 Cl N3 O4'
_chemical_formula_weight         357.75
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 101.144(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8425(7)
_cell_length_b                   14.1931(16)
_cell_length_c                   17.0132(17)
_cell_measurement_reflns_used    6606
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.99
_cell_measurement_theta_min      2.83
_cell_volume                     1621.1(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0482
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17955
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      1.466
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3951
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0522
_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)+(0.0345P)²+0.8903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1171
_reflns_number_gt                2688
_reflns_number_total             4016
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2017-0149_suppl.cif
_cod_data_source_block           mo
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               8106756
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.28395(9) 0.00012(5) 0.43180(4) 0.0721(2) Uani 1 1 d . . .
N2 N 0.2120(2) 0.25468(11) 0.31215(9) 0.0392(4) Uani 1 1 d . . .
N3 N -0.0960(2) 0.15407(11) 0.14138(10) 0.0405(4) Uani 1 1 d . . .
O1 O 0.5192(2) 0.29076(10) 0.43043(9) 0.0537(4) Uani 1 1 d . . .
C9 C -0.1187(3) 0.27454(13) 0.22948(11) 0.0367(4) Uani 1 1 d . . .
C7 C 0.5326(3) 0.22531(13) 0.38477(11) 0.0386(4) Uani 1 1 d . . .
O2 O 0.2173(2) 0.09554(10) 0.19296(9) 0.0536(4) Uani 1 1 d . . .
N1 N 0.3818(2) 0.20241(11) 0.32385(10) 0.0402(4) Uani 1 1 d . . .
H1 H 0.3932 0.1555 0.2930 0.048 Uiso 1 1 calc R . .
C8 C 0.0763(3) 0.23082(13) 0.25198(11) 0.0370(4) Uani 1 1 d . . .
C3 C 1.0647(3) 0.06428(16) 0.41666(13) 0.0469(5) Uani 1 1 d . . .
C6 C 0.7156(3) 0.16680(13) 0.39347(11) 0.0372(4) Uani 1 1 d . . .
O4 O -0.2618(3) -0.07061(11) 0.05616(10) 0.0699(5) Uani 1 1 d . . .
H4 H -0.3259 -0.1140 0.0706 0.105 Uiso 1 1 calc R . .
C15 C 0.0817(3) 0.15154(14) 0.19373(12) 0.0403(5) Uani 1 1 d . . .
C4 C 0.9090(3) 0.03775(16) 0.35745(13) 0.0502(5) Uani 1 1 d . . .
H4A H 0.9207 -0.0142 0.3254 0.060 Uiso 1 1 calc R . .
C10 C -0.2217(3) 0.22477(13) 0.16341(11) 0.0378(4) Uani 1 1 d . . .
C16 C -0.1504(3) 0.08332(14) 0.07943(11) 0.0429(5) Uani 1 1 d . . .
H16A H -0.0327 0.0648 0.0593 0.051 Uiso 1 1 calc R . .
H16B H -0.2448 0.1102 0.0352 0.051 Uiso 1 1 calc R . .
C1 C 1.0517(3) 0.14175(18) 0.46310(14) 0.0603(6) Uani 1 1 d . . .
H1A H 1.1597 0.1600 0.5021 0.072 Uiso 1 1 calc R . .
C2 C 0.8770(3) 0.19258(17) 0.45154(13) 0.0554(6) Uani 1 1 d . . .
H2 H 0.8676 0.2451 0.4833 0.067 Uiso 1 1 calc R . .
C11 C -0.2103(3) 0.34700(14) 0.26253(13) 0.0455(5) Uani 1 1 d . . .
H11 H -0.1420 0.3808 0.3061 0.055 Uiso 1 1 calc R . .
C17 C -0.2412(3) -0.00254(14) 0.11004(12) 0.0433(5) Uani 1 1 d . . .
C13 C -0.5054(3) 0.31775(18) 0.16452(14) 0.0559(6) Uani 1 1 d . . .
H13 H -0.6369 0.3333 0.1431 0.067 Uiso 1 1 calc R . .
C5 C 0.7347(3) 0.08918(15) 0.34606(12) 0.0453(5) Uani 1 1 d . . .
H5 H 0.6284 0.0715 0.3060 0.054 Uiso 1 1 calc R . .
O3 O -0.2863(3) -0.00781(12) 0.17362(10) 0.0692(5) Uani 1 1 d . . .
C14 C -0.4168(3) 0.24494(16) 0.13005(12) 0.0487(5) Uani 1 1 d . . .
H14 H -0.4858 0.2113 0.0865 0.058 Uiso 1 1 calc R . .
C12 C -0.4060(3) 0.36814(16) 0.22934(14) 0.0531(6) Uani 1 1 d . . .
H12 H -0.4709 0.4165 0.2508 0.064 Uiso 1 1 calc R . .
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C8 N2 N1 115.93(16) . .
C15 N3 C10 110.87(15) . .
C15 N3 C16 121.86(17) . .
C10 N3 C16 126.73(16) . .
C11 C9 C10 120.45(18) . .
C11 C9 C8 132.60(18) . .
C10 C9 C8 106.87(16) . .
O1 C7 N1 121.86(18) . .
O1 C7 C6 121.69(17) . .
N1 C7 C6 116.44(16) . .
C7 N1 N2 118.98(16) . .
N2 C8 C9 125.53(18) . .
N2 C8 C15 127.93(18) . .
C9 C8 C15 106.49(16) . .
C1 C3 C4 121.2(2) . .
C1 C3 Cl1 119.26(17) . .
C4 C3 Cl1 119.55(18) . .
C2 C6 C5 118.32(19) . .
C2 C6 C7 117.73(18) . .
C5 C6 C7 123.95(18) . .
O2 C15 N3 126.38(19) . .
O2 C15 C8 127.45(18) . .
N3 C15 C8 106.17(16) . .
C3 C4 C5 119.1(2) . .
C14 C10 C9 121.64(19) . .
C14 C10 N3 128.88(18) . .
C9 C10 N3 109.46(16) . .
N3 C16 C17 111.95(16) . .
C3 C1 C2 119.4(2) . .
C1 C2 C6 121.0(2) . .
C9 C11 C12 118.4(2) . .
O3 C17 O4 125.2(2) . .
O3 C17 C16 124.42(19) . .
O4 C17 C16 110.36(17) . .
C12 C13 C14 122.5(2) . .
C4 C5 C6 120.98(19) . .
C10 C14 C13 116.7(2) . .
C13 C12 C11 120.2(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C3 1.731(2) .
N2 C8 1.287(2) .
N2 N1 1.361(2) .
N3 C15 1.362(2) .
N3 C10 1.418(2) .
N3 C16 1.451(2) .
O1 C7 1.226(2) .
C9 C11 1.379(3) .
C9 C10 1.397(3) .
C9 C8 1.454(3) .
C7 N1 1.353(2) .
C7 C6 1.486(3) .
O2 C15 1.223(2) .
C8 C15 1.505(3) .
C3 C1 1.367(3) .
C3 C4 1.370(3) .
C6 C2 1.381(3) .
C6 C5 1.386(3) .
O4 C17 1.320(2) .
C4 C5 1.380(3) .
C10 C14 1.376(3) .
C16 C17 1.506(3) .
C1 C2 1.377(3) .
C11 C12 1.382(3) .
C17 O3 1.183(2) .
C13 C12 1.378(3) .
C13 C14 1.384(3) .
