#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/24/8102427.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_8102427
loop_
_publ_author_name
'Dao-Xin Wu'
'Tian Lin'
'Jiong Sun'
'Ming-Zhi Huang'
_publ_section_title
;
 Crystal structure of
 [3,4]dioxole-N'-(2-chloro-5-nitrobenzylidene)benzohydrazide,
 C15H10ClN3O5
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              229
_journal_volume                  224
_journal_year                    2009
_chemical_formula_moiety         'C15 H10 Cl N3 O5'
_chemical_formula_sum            'C15 H10 Cl N3 O5'
_chemical_formula_weight         347.71
_space_group_IT_number           2
_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                96.08(3)
_cell_angle_beta                 90.56(3)
_cell_angle_gamma                90.05(3)
_cell_formula_units_Z            2
_cell_length_a                   4.890(2)
_cell_length_b                   10.271(2)
_cell_length_c                   14.804(3)
_cell_measurement_reflns_used    573
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.7
_cell_volume                     739.3(4)
_computing_cell_refinement       SAINT
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 [10]'
_computing_structure_solution    'SHELXS-97 [9]'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_diffrn_measurement_method       'ω 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  0.0544
_diffrn_reflns_av_sigmaI/netI    0.1025
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5929
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  0.9254
_exptl_absorpt_correction_T_min  0.9176
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3071
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.913
_refine_ls_R_factor_all          0.1364
_refine_ls_R_factor_gt           0.0596
_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)+(0.0488P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1313
_reflns_number_gt                1483
_reflns_number_total             3071
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2547.cff
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8102427
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.00472(19) -0.04206(9) 0.63064(6) 0.0623(3) Uani 1 1 d . . .
O1 O 0.9455(6) 0.2694(3) 0.88943(17) 0.0802(9) Uani 1 1 d . . .
O2 O 0.8009(6) 0.1418(3) 0.98154(17) 0.1047(12) Uani 1 1 d . . .
O3 O 0.9705(4) 0.3448(2) 0.47995(13) 0.0403(6) Uani 1 1 d . . .
O4 O 0.2549(5) 0.3066(3) 0.15136(16) 0.0705(8) Uani 1 1 d . . .
O5 O 0.5119(6) 0.4732(3) 0.10167(15) 0.0737(8) Uani 1 1 d . . .
N1 N 0.5719(5) 0.2427(2) 0.57410(16) 0.0386(7) Uani 1 1 d . . .
N2 N 0.5240(5) 0.2952(3) 0.49394(16) 0.0385(7) Uani 1 1 d D . .
N3 N 0.7944(6) 0.1832(3) 0.9085(2) 0.0589(9) Uani 1 1 d . . .
C1 C 0.3900(6) 0.1342(3) 0.6935(2) 0.0364(8) Uani 1 1 d . . .
C2 C 0.2321(6) 0.0276(3) 0.7124(2) 0.0430(9) Uani 1 1 d . . .
C3 C 0.2582(7) -0.0272(3) 0.7931(2) 0.0509(9) Uani 1 1 d . . .
H3 H 0.1507 -0.0987 0.8036 0.061 Uiso 1 1 calc R . .
C4 C 0.4412(7) 0.0233(3) 0.8573(2) 0.0562(10) Uani 1 1 d . . .
H4 H 0.4592 -0.0124 0.9122 0.067 Uiso 1 1 calc R . .
C5 C 0.5989(6) 0.1281(3) 0.8391(2) 0.0412(8) Uani 1 1 d . . .
C6 C 0.5759(6) 0.1836(3) 0.7593(2) 0.0409(8) Uani 1 1 d . . .
H6 H 0.6854 0.2547 0.7494 0.049 Uiso 1 1 calc R . .
C7 C 0.3639(7) 0.1921(3) 0.60732(19) 0.0393(8) Uani 1 1 d . . .
H7 H 0.1959 0.1916 0.5773 0.047 Uiso 1 1 calc R . .
C8 C 0.7381(6) 0.3407(3) 0.44879(19) 0.0299(7) Uani 1 1 d . . .
C9 C 0.6683(6) 0.3821(3) 0.35829(18) 0.0317(7) Uani 1 1 d . . .
C10 C 0.4641(6) 0.3189(3) 0.30314(19) 0.0395(8) Uani 1 1 d . . .
H10 H 0.3563 0.2534 0.3233 0.047 Uiso 1 1 calc R . .
C11 C 0.4303(6) 0.3574(3) 0.2188(2) 0.0437(9) Uani 1 1 d . . .
C12 C 0.5831(7) 0.4545(3) 0.1890(2) 0.0442(9) Uani 1 1 d . . .
C13 C 0.7811(7) 0.5189(3) 0.2415(2) 0.0504(9) Uani 1 1 d . . .
H13 H 0.8829 0.5860 0.2206 0.060 Uiso 1 1 calc R . .
C14 C 0.8243(6) 0.4803(3) 0.3275(2) 0.0396(8) Uani 1 1 d . . .
H14 H 0.9600 0.5210 0.3649 0.048 Uiso 1 1 calc R . .
C15 C 0.2949(8) 0.3835(4) 0.0783(2) 0.0755(13) Uani 1 1 d . . .
H15A H 0.1287 0.4308 0.0668 0.091 Uiso 1 1 calc R . .
H15B H 0.3398 0.3274 0.0235 0.091 Uiso 1 1 calc R . .
H2 H 0.349(3) 0.308(3) 0.476(2) 0.080 Uiso 1 1 d D . .
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
_geom_angle_publ_flag
C11 O4 C15 105.4(3) . . ?
C12 O5 C15 105.1(3) . . ?
C7 N1 N2 114.8(3) . . ?
C8 N2 N1 119.2(2) . . ?
C8 N2 H2 121(2) . . ?
N1 N2 H2 120(2) . . ?
O2 N3 O1 122.4(3) . . ?
O2 N3 C5 119.6(3) . . ?
O1 N3 C5 118.0(3) . . ?
C6 C1 C2 117.2(3) . . ?
C6 C1 C7 120.8(3) . . ?
C2 C1 C7 122.0(3) . . ?
C3 C2 C1 122.0(3) . . ?
C3 C2 Cl1 118.9(3) . . ?
C1 C2 Cl1 119.1(2) . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 118.5(3) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C6 C5 C4 122.3(3) . . ?
C6 C5 N3 119.2(3) . . ?
C4 C5 N3 118.6(3) . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
N1 C7 C1 119.6(3) . . ?
N1 C7 H7 120.2 . . ?
C1 C7 H7 120.2 . . ?
O3 C8 N2 122.2(3) . . ?
O3 C8 C9 123.0(3) . . ?
N2 C8 C9 114.8(3) . . ?
C14 C9 C10 120.7(3) . . ?
C14 C9 C8 117.6(3) . . ?
C10 C9 C8 121.6(3) . . ?
C11 C10 C9 117.1(3) . . ?
C11 C10 H10 121.5 . . ?
C9 C10 H10 121.5 . . ?
C10 C11 C12 122.1(3) . . ?
C10 C11 O4 127.9(3) . . ?
C12 C11 O4 109.9(3) . . ?
C11 C12 C13 122.2(3) . . ?
C11 C12 O5 110.7(3) . . ?
C13 C12 O5 127.1(3) . . ?
C12 C13 C14 117.1(3) . . ?
C12 C13 H13 121.4 . . ?
C14 C13 H13 121.4 . . ?
C9 C14 C13 120.8(3) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
O4 C15 O5 108.7(3) . . ?
O4 C15 H15A 110.0 . . ?
O5 C15 H15A 110.0 . . ?
O4 C15 H15B 110.0 . . ?
O5 C15 H15B 110.0 . . ?
H15A C15 H15B 108.3 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.733(3) . ?
O1 N3 1.211(3) . ?
O2 N3 1.203(3) . ?
O3 C8 1.221(3) . ?
O4 C11 1.370(3) . ?
O4 C15 1.420(4) . ?
O5 C12 1.368(3) . ?
O5 C15 1.421(4) . ?
N1 C7 1.269(3) . ?
N1 N2 1.373(3) . ?
N2 C8 1.357(3) . ?
N2 H2 0.907(10) . ?
N3 C5 1.465(4) . ?
C1 C6 1.382(4) . ?
C1 C2 1.394(4) . ?
C1 C7 1.467(4) . ?
C2 C3 1.377(4) . ?
C3 C4 1.361(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.485(4) . ?
C9 C14 1.382(4) . ?
C9 C10 1.398(4) . ?
C10 C11 1.357(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.359(4) . ?
C12 C13 1.362(4) . ?
C13 C14 1.388(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O3 0.907(10) 1.891(15) 2.765(3) 161(3) 1_455
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7883106
