#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/06/2230683.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_2230683
loop_
_publ_author_name
'de Souza, Marcus V. N.'
'Pinheiro, Alessandra C.'
'Tiekink, Edward R. T.'
'Wardell, Solange M. S. V.'
'Wardell, James L.'
_publ_section_title
;
 Benzyl
 N-(1-{N'-[(E)-2-chlorobenzylidene]hydrazinecarbonyl}-2-hydroxyethyl)carbamate
;
_journal_coeditor_code           HB5927
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1868
_journal_page_last               o1869
_journal_paper_doi               10.1107/S1600536811024895
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H18 Cl N3 O4'
_chemical_formula_moiety         'C18 H18 Cl N3 O4'
_chemical_formula_sum            'C18 H18 Cl N3 O4'
_chemical_formula_weight         375.80
_chemical_name_systematic
;
Benzyl N-(1-{N'-[(E)-2-
chlorobenzylidene]hydrazinecarbonyl}-2-hydroxyethyl)carbamate
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.669(6)
_cell_angle_beta                 95.886(7)
_cell_angle_gamma                94.467(6)
_cell_formula_units_Z            1
_cell_length_a                   4.6804(4)
_cell_length_b                   5.6037(7)
_cell_length_c                   16.946(2)
_cell_measurement_reflns_used    13950
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     438.20(8)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type
'Bruker--Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_sigmaI/netI    0.1081
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6351
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.65
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             196
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.393
_refine_ls_abs_structure_details 'Flack (1983), 1476 Friedel pairs'
_refine_ls_abs_structure_Flack   0.15(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3438
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0704
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1959
_reflns_number_gt                2520
_reflns_number_total             3438
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5927.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 1 '
_cod_database_code               2230683
_cod_database_fobs_code          2230683
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl 1.3824(2) 1.3694(2) 0.28152(10) 0.0301(4) Uani d . 1 1 . .
O O1 0.5726(7) 0.6300(8) 0.4667(3) 0.0298(10) Uani d . 1 1 . .
O O2 1.2666(8) 0.1671(7) 0.5712(3) 0.0270(10) Uani d D 1 1 . .
H H2O 1.181(14) 0.079(11) 0.600(4) 0.041 Uiso d D 1 1 . .
O O3 0.9314(8) 0.8947(7) 0.6569(2) 0.0273(10) Uani d . 1 1 . .
O O4 0.5835(8) 0.6630(7) 0.7041(2) 0.0265(9) Uani d . 1 1 . .
N N1 0.8863(9) 0.7934(8) 0.3539(3) 0.0198(10) Uani d . 1 1 . .
N N2 1.0058(10) 0.6984(9) 0.4208(3) 0.0221(10) Uani d D 1 1 . .
H H2N 1.195(3) 0.713(11) 0.429(4) 0.026 Uiso d D 1 1 . .
N N3 0.8117(10) 0.4981(8) 0.6072(3) 0.0230(11) Uani d D 1 1 . .
H H3N 0.683(10) 0.377(7) 0.610(4) 0.028 Uiso d D 1 1 . .
C C1 0.9669(12) 0.9974(11) 0.2410(4) 0.0233(13) Uani d . 1 1 . .
C C2 1.1001(11) 1.2101(10) 0.2184(4) 0.0248(13) Uani d . 1 1 . .
C C3 0.9976(13) 1.3025(11) 0.1494(4) 0.0287(14) Uani d . 1 1 . .
H H3 1.0844 1.4498 0.1359 0.034 Uiso calc R 1 1 . .
C C4 0.7682(13) 1.1799(12) 0.1000(4) 0.0315(15) Uani d . 1 1 . .
H H4 0.6996 1.2419 0.0521 0.038 Uiso calc R 1 1 . .
C C5 0.6399(13) 0.9705(12) 0.1198(4) 0.0308(15) Uani d . 1 1 . .
H H5 0.4842 0.8866 0.0851 0.037 Uiso calc R 1 1 . .
C C6 0.7337(12) 0.8786(11) 0.1900(3) 0.0228(12) Uani d . 1 1 . .
H H6 0.6394 0.7344 0.2035 0.027 Uiso calc R 1 1 . .
C C7 1.0712(12) 0.9037(10) 0.3152(3) 0.0223(12) Uani d . 1 1 . .
H H7 1.2704 0.9233 0.3345 0.027 Uiso calc R 1 1 . .
C C8 0.8341(11) 0.6206(10) 0.4736(3) 0.0212(12) Uani d . 1 1 . .
C C9 0.9896(11) 0.5108(10) 0.5429(3) 0.0207(12) Uani d . 1 1 . .
H H9 1.1710 0.6148 0.5629 0.025 Uiso calc R 1 1 . .
C C10 1.0689(11) 0.2567(11) 0.5148(3) 0.0218(12) Uani d . 1 1 . .
H H10A 0.8910 0.1454 0.5048 0.026 Uiso calc R 1 1 . .
H H10B 1.1540 0.2613 0.4638 0.026 Uiso calc R 1 1 . .
C C11 0.7900(11) 0.7019(10) 0.6551(3) 0.0190(11) Uani d . 1 1 . .
C C12 0.5549(12) 0.8631(11) 0.7614(3) 0.0236(13) Uani d . 1 1 . .
H H12A 0.4789 0.9962 0.7337 0.028 Uiso calc R 1 1 . .
H H12B 0.7465 0.9217 0.7900 0.028 Uiso calc R 1 1 . .
C C13 0.3567(11) 0.7911(11) 0.8197(4) 0.0244(13) Uani d . 1 1 . .
C C14 0.2025(12) 0.5668(11) 0.8127(4) 0.0286(14) Uani d . 1 1 . .
H H14 0.2219 0.4510 0.7691 0.034 Uiso calc R 1 1 . .
C C15 0.0196(14) 0.5110(13) 0.8693(5) 0.0373(16) Uani d . 1 1 . .
H H15 -0.0830 0.3563 0.8648 0.045 Uiso calc R 1 1 . .
C C16 -0.0126(13) 0.6770(13) 0.9310(4) 0.0363(16) Uani d . 1 1 . .
H H16 -0.1406 0.6383 0.9688 0.044 Uiso calc R 1 1 . .
C C17 0.1389(13) 0.9020(13) 0.9394(4) 0.0336(15) Uani d . 1 1 . .
H H17 0.1162 1.0166 0.9830 0.040 Uiso calc R 1 1 . .
C C18 0.3217(12) 0.9584(11) 0.8845(4) 0.0275(13) Uani d . 1 1 . .
H H18 0.4261 1.1127 0.8903 0.033 Uiso calc R 1 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 O2 H2O . . 111(5) ?
C11 O4 C12 . . 114.7(4) ?
C7 N1 N2 . . 114.6(4) ?
C8 N2 N1 . . 119.6(4) ?
C8 N2 H2N . . 124(4) ?
N1 N2 H2N . . 115(4) ?
C11 N3 C9 . . 118.3(5) ?
C11 N3 H3N . . 117(4) ?
C9 N3 H3N . . 123(4) ?
C6 C1 C2 . . 117.8(5) ?
C6 C1 C7 . . 121.4(5) ?
C2 C1 C7 . . 120.7(5) ?
C3 C2 C1 . . 120.9(5) ?
C3 C2 Cl . . 119.5(5) ?
C1 C2 Cl . . 119.4(5) ?
C2 C3 C4 . . 119.8(6) ?
C2 C3 H3 . . 120.1 ?
C4 C3 H3 . . 120.1 ?
C5 C4 C3 . . 120.3(6) ?
C5 C4 H4 . . 119.9 ?
C3 C4 H4 . . 119.9 ?
C4 C5 C6 . . 120.8(6) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C5 C6 C1 . . 120.3(6) ?
C5 C6 H6 . . 119.9 ?
C1 C6 H6 . . 119.9 ?
N1 C7 C1 . . 118.5(5) ?
N1 C7 H7 . . 120.7 ?
C1 C7 H7 . . 120.7 ?
O1 C8 N2 . . 123.7(5) ?
O1 C8 C9 . . 121.7(5) ?
N2 C8 C9 . . 114.6(4) ?
N3 C9 C8 . . 110.6(4) ?
N3 C9 C10 . . 109.7(5) ?
C8 C9 C10 . . 110.2(5) ?
N3 C9 H9 . . 108.7 ?
C8 C9 H9 . . 108.7 ?
C10 C9 H9 . . 108.7 ?
O2 C10 C9 . . 112.6(4) ?
O2 C10 H10A . . 109.1 ?
C9 C10 H10A . . 109.1 ?
O2 C10 H10B . . 109.1 ?
C9 C10 H10B . . 109.1 ?
H10A C10 H10B . . 107.8 ?
O3 C11 N3 . . 127.3(5) ?
O3 C11 O4 . . 122.9(5) ?
N3 C11 O4 . . 109.8(5) ?
O4 C12 C13 . . 110.4(5) ?
O4 C12 H12A . . 109.6 ?
C13 C12 H12A . . 109.6 ?
O4 C12 H12B . . 109.6 ?
C13 C12 H12B . . 109.6 ?
H12A C12 H12B . . 108.1 ?
C14 C13 C18 . . 118.4(5) ?
C14 C13 C12 . . 123.1(5) ?
C18 C13 C12 . . 118.5(5) ?
C13 C14 C15 . . 120.2(6) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C16 C15 C14 . . 120.2(7) ?
C16 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C15 C16 C17 . . 120.8(6) ?
C15 C16 H16 . . 119.6 ?
C17 C16 H16 . . 119.6 ?
C18 C17 C16 . . 119.6(6) ?
C18 C17 H17 . . 120.2 ?
C16 C17 H17 . . 120.2 ?
C17 C18 C13 . . 120.8(6) ?
C17 C18 H18 . . 119.6 ?
C13 C18 H18 . . 119.6 ?
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
Cl C2 . 1.739(6) ?
O1 C8 . 1.223(6) ?
O2 C10 . 1.417(7) ?
O2 H2O . 0.842(10) ?
O3 C11 . 1.218(7) ?
O4 C11 . 1.357(6) ?
O4 C12 . 1.433(6) ?
N1 C7 . 1.294(7) ?
N1 N2 . 1.385(6) ?
N2 C8 . 1.343(7) ?
N2 H2N . 0.877(10) ?
N3 C11 . 1.351(7) ?
N3 C9 . 1.441(7) ?
N3 H3N . 0.878(10) ?
C1 C6 . 1.400(8) ?
C1 C2 . 1.407(8) ?
C1 C7 . 1.462(8) ?
C2 C3 . 1.381(8) ?
C3 C4 . 1.383(9) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.364(9) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.386(9) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 C9 . 1.525(8) ?
C9 C10 . 1.541(8) ?
C9 H9 . 1.0000 ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C12 C13 . 1.485(8) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.388(9) ?
C13 C18 . 1.403(8) ?
C14 C15 . 1.391(9) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.357(10) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.385(10) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.371(8) ?
C17 H17 . 0.9500 ?
C18 H18 . 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
O2 H2o O3 1_545 0.84(8) 1.89(9) 2.728(7) 171(9)
N3 H3n O2 1_455 0.88(6) 2.20(6) 3.006(8) 153(7)
N2 H2n O1 1_655 0.88(3) 1.93(4) 2.758(8) 158(7)
C6 H6 Cl 1_445 0.95 2.81 3.734(8) 166
C12 H12b Cg1 1_655 0.99 2.69 3.474(8) 137
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 N2 C8 . . . . 167.6(5) ?
C6 C1 C2 C3 . . . . 2.1(8) ?
C7 C1 C2 C3 . . . . -178.3(5) ?
C6 C1 C2 Cl . . . . 177.8(4) ?
C7 C1 C2 Cl . . . . -2.6(7) ?
C1 C2 C3 C4 . . . . -2.6(8) ?
Cl C2 C3 C4 . . . . -178.3(5) ?
C2 C3 C4 C5 . . . . 1.1(9) ?
C3 C4 C5 C6 . . . . 0.9(10) ?
C4 C5 C6 C1 . . . . -1.4(9) ?
C2 C1 C6 C5 . . . . -0.1(8) ?
C7 C1 C6 C5 . . . . -179.7(5) ?
N2 N1 C7 C1 . . . . 176.4(5) ?
C6 C1 C7 N1 . . . . -33.8(8) ?
C2 C1 C7 N1 . . . . 146.7(5) ?
N1 N2 C8 O1 . . . . -0.6(8) ?
N1 N2 C8 C9 . . . . 177.6(5) ?
C11 N3 C9 C8 . . . . -77.4(6) ?
C11 N3 C9 C10 . . . . 160.8(5) ?
O1 C8 C9 N3 . . . . -18.6(7) ?
N2 C8 C9 N3 . . . . 163.1(5) ?
O1 C8 C9 C10 . . . . 102.9(6) ?
N2 C8 C9 C10 . . . . -75.4(6) ?
N3 C9 C10 O2 . . . . -70.8(5) ?
C8 C9 C10 O2 . . . . 167.1(4) ?
C9 N3 C11 O3 . . . . -9.6(8) ?
C9 N3 C11 O4 . . . . 171.2(5) ?
C12 O4 C11 O3 . . . . -3.2(7) ?
C12 O4 C11 N3 . . . . 176.0(4) ?
C11 O4 C12 C13 . . . . -171.5(5) ?
O4 C12 C13 C14 . . . . -6.0(7) ?
O4 C12 C13 C18 . . . . 174.6(5) ?
C18 C13 C14 C15 . . . . -0.4(8) ?
C12 C13 C14 C15 . . . . -179.8(6) ?
C13 C14 C15 C16 . . . . 1.0(10) ?
C14 C15 C16 C17 . . . . -1.1(10) ?
C15 C16 C17 C18 . . . . 0.5(10) ?
C16 C17 C18 C13 . . . . 0.2(9) ?
C14 C13 C18 C17 . . . . -0.2(8) ?
C12 C13 C18 C17 . . . . 179.3(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656773
