#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/24/8102428.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_8102428
loop_
_publ_author_name
'Dao-Xin Wu'
'Jiong Sun'
'Ming-Zhi Huang'
_publ_section_title
;
 Crystal structure of
 [3,4]dioxole-N'-(3,5-dichloro-2-hydroxybenzylidene)benzohydrazide -
 methanol (1:1), C15H10Cl2N2O4 · CH3OH
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              227
_journal_volume                  224
_journal_year                    2009
_chemical_formula_moiety         'C15 H10 Cl2 N2 O4, C H4 O'
_chemical_formula_sum            'C16 H14 Cl2 N2 O5'
_chemical_formula_weight         385.19
_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                90.00
_cell_angle_beta                 100.201(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.041(1)
_cell_length_b                   13.744(2)
_cell_length_c                   15.530(2)
_cell_measurement_reflns_used    2669
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.2
_cell_measurement_theta_min      2.4
_cell_volume                     1689.2(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 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9443
_diffrn_reflns_theta_full        26.85
_diffrn_reflns_theta_max         26.85
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  0.9107
_exptl_absorpt_correction_T_min  0.8963
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3590
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0437
_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)+(0.0452P)²+0.3509P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1130
_reflns_number_gt                2508
_reflns_number_total             3590
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2548.cff
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               8102428
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 0.36993(9) 0.20619(4) 0.33429(4) 0.0672(2) Uani 1 1 d . . .
Cl2 Cl 0.23227(8) 0.53164(5) 0.14271(4) 0.0639(2) Uani 1 1 d . . .
O1 O 0.5965(2) 0.32836(10) 0.45101(10) 0.0534(4) Uani 1 1 d . . .
H1 H 0.6595 0.3650 0.4833 0.080 Uiso 1 1 calc R . .
O2 O 0.9374(2) 0.41301(11) 0.63698(10) 0.0574(4) Uani 1 1 d . . .
O3 O 1.3757(2) 0.70863(14) 0.88398(11) 0.0782(6) Uani 1 1 d . . .
O4 O 1.3541(2) 0.54224(14) 0.90088(11) 0.0786(6) Uani 1 1 d . . .
O5 O 0.0839(2) 0.27667(13) 0.53932(13) 0.0741(5) Uani 1 1 d . . .
H5 H 0.0273 0.3071 0.5692 0.111 Uiso 1 1 calc R . .
N1 N 0.7453(2) 0.49226(13) 0.49851(11) 0.0417(4) Uani 1 1 d . . .
N2 N 0.8538(2) 0.54699(12) 0.55725(11) 0.0430(4) Uani 1 1 d D . .
C1 C 0.5408(2) 0.47889(14) 0.36972(13) 0.0385(5) Uani 1 1 d . . .
C2 C 0.5174(2) 0.37821(14) 0.38118(12) 0.0381(5) Uani 1 1 d . . .
C3 C 0.4038(3) 0.32885(14) 0.31823(13) 0.0421(5) Uani 1 1 d . . .
C4 C 0.3180(3) 0.37462(16) 0.24513(13) 0.0452(5) Uani 1 1 d . . .
H4 H 0.2447 0.3398 0.2031 0.054 Uiso 1 1 calc R . .
C5 C 0.3420(3) 0.47308(16) 0.23492(13) 0.0437(5) Uani 1 1 d . . .
C6 C 0.4505(3) 0.52494(15) 0.29648(13) 0.0431(5) Uani 1 1 d . . .
H6 H 0.4635 0.5915 0.2891 0.052 Uiso 1 1 calc R . .
C7 C 0.6577(2) 0.53484(15) 0.43283(13) 0.0420(5) Uani 1 1 d . . .
H7 H 0.6686 0.6015 0.4253 0.050 Uiso 1 1 calc R . .
C8 C 0.9462(2) 0.50093(15) 0.62752(13) 0.0410(5) Uani 1 1 d . . .
C9 C 1.0562(2) 0.56339(15) 0.69245(13) 0.0390(5) Uani 1 1 d . . .
C10 C 1.1496(3) 0.51602(16) 0.76480(14) 0.0477(5) Uani 1 1 d . . .
H10 H 1.1424 0.4490 0.7717 0.057 Uiso 1 1 calc R . .
C11 C 1.2515(3) 0.57151(17) 0.82465(14) 0.0491(5) Uani 1 1 d . . .
C12 C 1.2642(3) 0.67034(18) 0.81582(14) 0.0527(6) Uani 1 1 d . . .
C13 C 1.1722(3) 0.71905(18) 0.74687(16) 0.0623(7) Uani 1 1 d . . .
H13 H 1.1794 0.7863 0.7416 0.075 Uiso 1 1 calc R . .
C14 C 1.0674(3) 0.66368(16) 0.68478(14) 0.0510(6) Uani 1 1 d . . .
H14 H 1.0031 0.6946 0.6369 0.061 Uiso 1 1 calc R . .
C15 C 1.4364(4) 0.6279(2) 0.93835(17) 0.0746(8) Uani 1 1 d . . .
H15A H 1.5577 0.6216 0.9424 0.090 Uiso 1 1 calc R . .
H15B H 1.4125 0.6377 0.9968 0.090 Uiso 1 1 calc R . .
C16 C 0.0065(4) 0.18708(18) 0.51546(18) 0.0726(8) Uani 1 1 d . . .
H16A H -0.0002 0.1500 0.5671 0.109 Uiso 1 1 calc R . .
H16B H 0.0718 0.1519 0.4797 0.109 Uiso 1 1 calc R . .
H16C H -0.1053 0.1979 0.4832 0.109 Uiso 1 1 calc R . .
H2 H 0.868(3) 0.6084(9) 0.5413(16) 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
C2 O1 H1 109.5 . . ?
C12 O3 C15 105.5(2) . . ?
C11 O4 C15 105.91(19) . . ?
C16 O5 H5 109.5 . . ?
C7 N1 N2 118.50(17) . . ?
C8 N2 N1 118.08(17) . . ?
C8 N2 H2 125.6(17) . . ?
N1 N2 H2 115.7(17) . . ?
C6 C1 C2 119.18(18) . . ?
C6 C1 C7 119.58(18) . . ?
C2 C1 C7 121.24(18) . . ?
O1 C2 C3 118.48(17) . . ?
O1 C2 C1 123.13(17) . . ?
C3 C2 C1 118.37(18) . . ?
C4 C3 C2 121.98(19) . . ?
C4 C3 Cl1 119.73(16) . . ?
C2 C3 Cl1 118.29(15) . . ?
C3 C4 C5 118.95(19) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 120.90(19) . . ?
C6 C5 Cl2 119.97(17) . . ?
C4 C5 Cl2 119.13(16) . . ?
C5 C6 C1 120.59(19) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
N1 C7 C1 119.80(19) . . ?
N1 C7 H7 120.1 . . ?
C1 C7 H7 120.1 . . ?
O2 C8 N2 121.42(18) . . ?
O2 C8 C9 121.93(19) . . ?
N2 C8 C9 116.64(18) . . ?
C14 C9 C10 119.88(19) . . ?
C14 C9 C8 123.63(19) . . ?
C10 C9 C8 116.49(18) . . ?
C11 C10 C9 117.5(2) . . ?
C11 C10 H10 121.3 . . ?
C9 C10 H10 121.3 . . ?
C10 C11 C12 122.3(2) . . ?
C10 C11 O4 128.4(2) . . ?
C12 C11 O4 109.4(2) . . ?
C13 C12 O3 127.5(2) . . ?
C13 C12 C11 121.7(2) . . ?
O3 C12 C11 110.8(2) . . ?
C12 C13 C14 117.0(2) . . ?
C12 C13 H13 121.5 . . ?
C14 C13 H13 121.5 . . ?
C9 C14 C13 121.7(2) . . ?
C9 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
O4 C15 O3 108.40(19) . . ?
O4 C15 H15A 110.0 . . ?
O3 C15 H15A 110.0 . . ?
O4 C15 H15B 110.0 . . ?
O3 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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 C3 1.733(2) . ?
Cl2 C5 1.741(2) . ?
O1 C2 1.344(2) . ?
O1 H1 0.8200 . ?
O2 C8 1.221(2) . ?
O3 C12 1.366(3) . ?
O3 C15 1.427(3) . ?
O4 C11 1.378(3) . ?
O4 C15 1.423(3) . ?
O5 C16 1.400(3) . ?
O5 H5 0.8200 . ?
N1 C7 1.275(3) . ?
N1 N2 1.370(2) . ?
N2 C8 1.362(3) . ?
N2 H2 0.894(10) . ?
C1 C6 1.389(3) . ?
C1 C2 1.412(3) . ?
C1 C7 1.452(3) . ?
C2 C3 1.390(3) . ?
C3 C4 1.373(3) . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.490(3) . ?
C9 C14 1.388(3) . ?
C9 C10 1.397(3) . ?
C10 C11 1.359(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(3) . ?
C12 C13 1.364(3) . ?
C13 C14 1.390(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
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 O5 0.894(10) 2.093(13) 2.940(3) 158(2) 3_666
O5 H5 O2 0.82 2.00 2.799(2) 162.9 1_455
O1 H1 N1 0.82 1.88 2.596(2) 145.3 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653960
