#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/52/2225253.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_2225253
loop_
_publ_author_name
'Jiang, Jin-He'
_publ_section_title
;
 N'-(4-Chlorobenzylidene)furan-2-carbohydrazide monohydrate
;
_journal_coeditor_code           HB5316
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o627
_journal_paper_doi               10.1107/S1600536810005532
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H9 Cl N2 O2, H2 O'
_chemical_formula_moiety         'C12 H9 Cl N2 O2, H2 O'
_chemical_formula_sum            'C12 H11 Cl N2 O3'
_chemical_formula_weight         266.68
_chemical_name_systematic
;
N'-(4-Chlorobenzylidene)furan-2-carbohydrazide monohydrate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 91.90(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.5480(9)
_cell_length_b                   12.423(3)
_cell_length_c                   10.971(2)
_cell_measurement_reflns_used    2022
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      3.26
_cell_volume                     619.5(2)
_computing_cell_refinement       'SAINT (Bruker 1997)'
_computing_data_collection       'SMART (Bruker 1997)'
_computing_data_reduction        'SAINT (Bruker 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD'
_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  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0620
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5979
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.335
_refine_ls_abs_structure_details 'Flack (1983), 1319 Friedel pairs'
_refine_ls_abs_structure_Flack   0.01(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2799
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0446
_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)+(0.0702P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1450
_reflns_number_gt                1708
_reflns_number_total             2799
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5316.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2225253
_cod_database_fobs_code          2225253
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.8615(3) 0.97667(10) 0.39621(9) 0.0713(4) Uani d . 1 . .
O O1 -0.3072(6) 0.94704(18) 1.0474(2) 0.0525(6) Uani d . 1 . .
O O2 -0.5944(6) 0.68010(17) 1.0623(2) 0.0457(6) Uani d . 1 . .
N N1 -0.1934(6) 0.7961(2) 0.9399(2) 0.0412(6) Uani d . 1 . .
H H1A -0.2136 0.7276 0.9323 0.049 Uiso calc R 1 . .
N N2 -0.0118(6) 0.8522(2) 0.8633(2) 0.0428(7) Uani d . 1 . .
C C1 0.6164(11) 0.8151(4) 0.5209(4) 0.0677(12) Uani d . 1 . .
H H1B 0.7036 0.7692 0.4657 0.081 Uiso calc R 1 . .
C C2 0.6554(8) 0.9240(3) 0.5124(3) 0.0527(10) Uani d . 1 . .
C C3 0.5303(9) 0.9909(3) 0.5956(3) 0.0568(9) Uani d . 1 . .
H H3A 0.5619 1.0647 0.5907 0.068 Uiso calc R 1 . .
C C4 0.3591(9) 0.9509(3) 0.6861(3) 0.0544(10) Uani d . 1 . .
H H4A 0.2762 0.9975 0.7417 0.065 Uiso calc R 1 . .
C C5 0.3098(8) 0.8405(3) 0.6946(3) 0.0466(8) Uani d . 1 . .
C C6 0.4448(10) 0.7733(3) 0.6129(4) 0.0616(11) Uani d . 1 . .
H H6A 0.4209 0.6992 0.6193 0.074 Uiso calc R 1 . .
C C7 -0.3375(7) 0.8492(3) 1.0262(3) 0.0409(7) Uani d . 1 . .
C C8 0.1202(8) 0.7935(3) 0.7861(3) 0.0466(8) Uani d . 1 . .
H H8A 0.0950 0.7192 0.7881 0.056 Uiso calc R 1 . .
C C9 -0.5355(7) 0.7844(3) 1.0984(3) 0.0398(7) Uani d . 1 . .
C C10 -0.6880(9) 0.8080(3) 1.1980(3) 0.0483(9) Uani d . 1 . .
H H10A -0.6893 0.8733 1.2393 0.058 Uiso calc R 1 . .
C C11 -0.8474(9) 0.7132(3) 1.2281(3) 0.0515(9) Uani d . 1 . .
H H11A -0.9722 0.7044 1.2928 0.062 Uiso calc R 1 . .
C C12 -0.7811(9) 0.6394(3) 1.1444(3) 0.0513(9) Uani d . 1 . .
H H12A -0.8536 0.5694 1.1428 0.062 Uiso calc R 1 . .
O O1W -0.1978(8) 0.5707(2) 0.8764(3) 0.0596(8) Uani d . 1 . .
H H1W -0.037(11) 0.526(4) 0.906(4) 0.084(15) Uiso d . 1 . .
H H2W -0.372(13) 0.537(4) 0.893(4) 0.093(18) Uiso d . 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
C12 O2 C9 . . 106.2(3) ?
C7 N1 N2 . . 119.7(3) ?
C7 N1 H1A . . 120.1 ?
N2 N1 H1A . . 120.1 ?
C8 N2 N1 . . 114.6(3) ?
C2 C1 C6 . . 119.6(4) ?
C2 C1 H1B . . 120.2 ?
C6 C1 H1B . . 120.2 ?
C1 C2 C3 . . 119.7(4) ?
C1 C2 Cl1 . . 119.8(3) ?
C3 C2 Cl1 . . 120.5(3) ?
C2 C3 C4 . . 121.3(4) ?
C2 C3 H3A . . 119.4 ?
C4 C3 H3A . . 119.4 ?
C3 C4 C5 . . 120.0(4) ?
C3 C4 H4A . . 120.0 ?
C5 C4 H4A . . 120.0 ?
C6 C5 C4 . . 118.4(4) ?
C6 C5 C8 . . 119.1(3) ?
C4 C5 C8 . . 122.5(3) ?
C5 C6 C1 . . 121.0(4) ?
C5 C6 H6A . . 119.5 ?
C1 C6 H6A . . 119.5 ?
O1 C7 N1 . . 123.9(3) ?
O1 C7 C9 . . 120.2(3) ?
N1 C7 C9 . . 115.8(3) ?
N2 C8 C5 . . 121.7(3) ?
N2 C8 H8A . . 119.2 ?
C5 C8 H8A . . 119.2 ?
C10 C9 O2 . . 109.7(3) ?
C10 C9 C7 . . 131.6(3) ?
O2 C9 C7 . . 118.6(3) ?
C9 C10 C11 . . 106.7(3) ?
C9 C10 H10A . . 126.6 ?
C11 C10 H10A . . 126.6 ?
C12 C11 C10 . . 106.2(3) ?
C12 C11 H11A . . 126.9 ?
C10 C11 H11A . . 126.9 ?
C11 C12 O2 . . 111.1(3) ?
C11 C12 H12A . . 124.4 ?
O2 C12 H12A . . 124.4 ?
H1W O1W H2W . . 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
Cl1 C2 . 1.735(4) ?
O1 C7 . 1.244(4) ?
O2 C12 . 1.356(4) ?
O2 C9 . 1.379(4) ?
N1 C7 . 1.342(4) ?
N1 N2 . 1.386(4) ?
N1 H1A . 0.8600 ?
N2 C8 . 1.282(4) ?
C1 C2 . 1.368(6) ?
C1 C6 . 1.396(6) ?
C1 H1B . 0.9300 ?
C2 C3 . 1.372(5) ?
C3 C4 . 1.375(5) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.393(5) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.384(5) ?
C5 C8 . 1.466(5) ?
C6 H6A . 0.9300 ?
C7 C9 . 1.461(5) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.346(5) ?
C10 C11 . 1.427(6) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.339(5) ?
C11 H11A . 0.9300 ?
C12 H12A . 0.9300 ?
O1W H1W . 0.97(5) ?
O1W H2W . 0.92(6) ?
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
O1W H1W O1 2_547 0.97(5) 1.90(5) 2.865(4) 174(5)
O1W H2W O1 2_447 0.92(6) 1.97(6) 2.873(4) 168(5)
N1 H1A O2 . 0.86 2.36 2.715(4) 106
N1 H1A O1W . 0.86 2.05 2.886(4) 165
C8 H8A O1W . 0.93 2.49 3.290(5) 144
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 . . . . 178.5(3) ?
C6 C1 C2 C3 . . . . 1.2(7) ?
C6 C1 C2 Cl1 . . . . -178.5(3) ?
C1 C2 C3 C4 . . . . -1.7(6) ?
Cl1 C2 C3 C4 . . . . 178.0(3) ?
C2 C3 C4 C5 . . . . 0.0(6) ?
C3 C4 C5 C6 . . . . 2.1(6) ?
C3 C4 C5 C8 . . . . -177.6(3) ?
C4 C5 C6 C1 . . . . -2.6(6) ?
C8 C5 C6 C1 . . . . 177.1(4) ?
C2 C1 C6 C5 . . . . 1.0(7) ?
N2 N1 C7 O1 . . . . -4.2(5) ?
N2 N1 C7 C9 . . . . 176.9(3) ?
N1 N2 C8 C5 . . . . 177.2(3) ?
C6 C5 C8 N2 . . . . -179.5(3) ?
C4 C5 C8 N2 . . . . 0.2(6) ?
C12 O2 C9 C10 . . . . -1.6(4) ?
C12 O2 C9 C7 . . . . 180.0(3) ?
O1 C7 C9 C10 . . . . -6.7(6) ?
N1 C7 C9 C10 . . . . 172.3(4) ?
O1 C7 C9 O2 . . . . 171.4(3) ?
N1 C7 C9 O2 . . . . -9.6(4) ?
O2 C9 C10 C11 . . . . 1.1(4) ?
C7 C9 C10 C11 . . . . 179.3(3) ?
C9 C10 C11 C12 . . . . -0.3(4) ?
C10 C11 C12 O2 . . . . -0.7(4) ?
C9 O2 C12 C11 . . . . 1.4(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656017
