#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/87/2208701.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_2208701
loop_
_publ_author_name
'De-Suo Yang'
_publ_section_title
;
 5-Chlorosalicylaldehyde salicylhydrazone
;
_journal_coeditor_code           RZ2013
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1591
_journal_page_last               o1592
_journal_paper_doi               10.1107/S1600536806010798
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C14 H11 Cl N2 O3'
_chemical_formula_sum            'C14 H11 Cl N2 O3'
_chemical_formula_weight         290.70
_chemical_name_systematic
;
 ?
;
_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                 99.474(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.873(2)
_cell_length_b                   5.3910(10)
_cell_length_c                   12.851(3)
_cell_measurement_reflns_used    551
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.8
_cell_measurement_theta_min      2.6
_cell_volume                     1289.7(4)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX area-detector diffractometer'
_diffrn_measurement_method       'ω scan'
_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  0.0902
_diffrn_reflns_av_sigmaI/netI    0.1079
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9927
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.09
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_correction_T_min  0.9586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       flake
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.224
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2650
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1524
_refine_ls_R_factor_gt           0.0726
_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)+(0.0266P)²+0.8881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1533
_reflns_number_gt                1393
_reflns_number_total             2650
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            rz2013.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_cell_volume        1289.6(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2208701
_cod_database_fobs_code          2208701
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_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
Cl Cl1 0.03516(7) 1.3981(2) 0.82934(9) 0.0698(4) Uani d . 1
O O1 0.20247(19) 0.7032(7) 1.1218(2) 0.0773(11) Uani d . 1
H H1 0.2245 0.6026 1.0915 0.116 Uiso calc R 1
O O2 0.34974(16) 0.1630(5) 1.03772(19) 0.0587(9) Uani d . 1
O O3 0.30762(16) 0.1941(5) 0.70983(18) 0.0499(8) Uani d D 1
N N1 0.25516(17) 0.5195(6) 0.9530(2) 0.0412(8) Uani d . 1
N N2 0.29197(18) 0.3662(6) 0.8949(2) 0.0430(8) Uani d D 1
C C1 0.1714(2) 0.8570(7) 0.9427(3) 0.0426(10) Uani d . 1
C C2 0.1660(2) 0.8595(9) 1.0505(3) 0.0555(12) Uani d . 1
C C3 0.1208(3) 1.0289(10) 1.0863(3) 0.0743(15) Uani d . 1
H H3A 0.1174 1.0315 1.1576 0.089 Uiso calc R 1
C C4 0.0811(3) 1.1929(9) 1.0199(4) 0.0700(15) Uani d . 1
H H4 0.0511 1.3061 1.0458 0.084 Uiso calc R 1
C C5 0.0859(2) 1.1890(8) 0.9147(3) 0.0501(11) Uani d . 1
C C6 0.1307(2) 1.0260(7) 0.8762(3) 0.0484(11) Uani d . 1
H H6 0.1340 1.0282 0.8048 0.058 Uiso calc R 1
C C7 0.2164(2) 0.6836(7) 0.8981(3) 0.0429(10) Uani d . 1
H H7 0.2174 0.6913 0.8261 0.051 Uiso calc R 1
C C8 0.3367(2) 0.1901(7) 0.9418(3) 0.0391(10) Uani d . 1
C C9 0.3705(2) 0.0257(7) 0.8710(3) 0.0342(9) Uani d . 1
C C10 0.3555(2) 0.0264(7) 0.7604(3) 0.0358(9) Uani d . 1
C C11 0.3867(2) -0.1494(7) 0.7036(3) 0.0472(11) Uani d . 1
H H11 0.3748 -0.1531 0.6305 0.057 Uiso calc R 1
C C12 0.4346(2) -0.3169(8) 0.7540(3) 0.0511(11) Uani d . 1
H H12 0.4557 -0.4322 0.7148 0.061 Uiso calc R 1
C C13 0.4521(2) -0.3168(8) 0.8629(3) 0.0534(12) Uani d . 1
H H13 0.4849 -0.4309 0.8971 0.064 Uiso calc R 1
C C14 0.4205(2) -0.1468(7) 0.9196(3) 0.0426(10) Uani d . 1
H H14 0.4326 -0.1459 0.9927 0.051 Uiso calc R 1
H H3 0.322(2) 0.225(8) 0.6478(18) 0.080 Uiso d D 1
H H2 0.290(2) 0.387(8) 0.8250(10) 0.080 Uiso d D 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0757(9) 0.0669(8) 0.0684(8) 0.0169(7) 0.0169(6) 0.0047(6)
O1 0.092(3) 0.102(3) 0.0396(17) 0.040(2) 0.0156(17) 0.0028(18)
O2 0.078(2) 0.075(2) 0.0227(14) 0.0151(17) 0.0095(14) -0.0033(14)
O3 0.069(2) 0.0591(19) 0.0234(14) 0.0144(16) 0.0123(14) 0.0014(13)
N1 0.042(2) 0.052(2) 0.0329(17) -0.0003(18) 0.0151(15) -0.0070(16)
N2 0.052(2) 0.051(2) 0.0286(17) 0.0001(18) 0.0149(17) -0.0054(17)
C1 0.045(2) 0.050(3) 0.033(2) -0.003(2) 0.0068(19) -0.008(2)
C2 0.059(3) 0.072(3) 0.036(2) 0.011(3) 0.010(2) -0.006(2)
C3 0.084(4) 0.103(4) 0.038(2) 0.031(3) 0.016(3) -0.010(3)
C4 0.071(4) 0.084(4) 0.058(3) 0.024(3) 0.020(3) -0.013(3)
C5 0.044(3) 0.058(3) 0.050(3) 0.005(2) 0.013(2) -0.004(2)
C6 0.053(3) 0.053(3) 0.043(2) -0.005(2) 0.016(2) -0.007(2)
C7 0.047(3) 0.052(3) 0.032(2) -0.007(2) 0.010(2) -0.008(2)
C8 0.044(2) 0.047(3) 0.029(2) -0.008(2) 0.0119(18) -0.0063(19)
C9 0.041(2) 0.037(2) 0.0260(19) -0.0094(19) 0.0086(16) 0.0003(17)
C10 0.042(2) 0.038(2) 0.0276(19) -0.0028(19) 0.0068(17) 0.0040(18)
C11 0.056(3) 0.056(3) 0.030(2) 0.004(2) 0.009(2) -0.010(2)
C12 0.057(3) 0.052(3) 0.047(3) 0.007(2) 0.016(2) -0.004(2)
C13 0.062(3) 0.050(3) 0.048(3) 0.008(2) 0.007(2) 0.014(2)
C14 0.051(3) 0.050(3) 0.027(2) -0.005(2) 0.0064(19) 0.0049(19)
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
C2 O1 H1 109.5
C10 O3 H3 106(3)
C7 N1 N2 114.1(3)
C8 N2 N1 121.0(3)
C8 N2 H2 117(3)
N1 N2 H2 122(3)
C6 C1 C2 118.6(4)
C6 C1 C7 118.7(3)
C2 C1 C7 122.7(4)
O1 C2 C3 117.6(4)
O1 C2 C1 123.5(4)
C3 C2 C1 118.9(4)
C4 C3 C2 121.8(4)
C4 C3 H3A 119.1
C2 C3 H3A 119.1
C3 C4 C5 119.2(4)
C3 C4 H4 120.4
C5 C4 H4 120.4
C6 C5 C4 120.9(4)
C6 C5 Cl1 119.7(3)
C4 C5 Cl1 119.4(3)
C5 C6 C1 120.6(4)
C5 C6 H6 119.7
C1 C6 H6 119.7
N1 C7 C1 123.2(3)
N1 C7 H7 118.4
C1 C7 H7 118.4
O2 C8 N2 122.8(4)
O2 C8 C9 120.6(4)
N2 C8 C9 116.6(3)
C14 C9 C10 117.6(3)
C14 C9 C8 116.7(3)
C10 C9 C8 125.7(3)
O3 C10 C11 120.5(3)
O3 C10 C9 119.4(3)
C11 C10 C9 120.0(4)
C12 C11 C10 120.6(4)
C12 C11 H11 119.7
C10 C11 H11 119.7
C11 C12 C13 120.6(4)
C11 C12 H12 119.7
C13 C12 H12 119.7
C14 C13 C12 119.2(4)
C14 C13 H13 120.4
C12 C13 H13 120.4
C13 C14 C9 122.0(3)
C13 C14 H14 119.0
C9 C14 H14 119.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C5 1.746(4)
O1 C2 1.347(5)
O1 H1 0.8200
O2 C8 1.226(4)
O3 C10 1.365(4)
O3 H3 0.90(3)
N1 C7 1.283(4)
N1 N2 1.376(4)
N2 C8 1.345(5)
N2 H2 0.900(10)
C1 C6 1.391(5)
C1 C2 1.406(5)
C1 C7 1.445(5)
C2 C3 1.379(6)
C3 C4 1.364(6)
C3 H3A 0.9300
C4 C5 1.370(6)
C4 H4 0.9300
C5 C6 1.367(5)
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.487(5)
C9 C14 1.397(5)
C9 C10 1.402(5)
C10 C11 1.385(5)
C11 C12 1.364(5)
C11 H11 0.9300
C12 C13 1.384(5)
C12 H12 0.9300
C13 C14 1.368(5)
C13 H13 0.9300
C14 H14 0.9300
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
N2 H2 O3 . 0.900(10) 1.88(3) 2.614(4) 137(4)
O3 H3 O2 4_565 0.90(3) 1.70(3) 2.588(3) 170(4)
O1 H1 O3 4_566 0.82 2.56 3.011(4) 116.1
O1 H1 N1 . 0.82 2.01 2.717(4) 144.1
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17979195
