#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/42/2224268.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_2224268
loop_
_publ_author_name
'de Ferreira, Marcelle L.'
'de Souza, Marcus V. N.'
'Howie, R. Alan'
'Tiekink, Edward R. T.'
'Wardell, James L.'
'Wardell, Solange M. S. V.'
_publ_section_title
;
 3-[(E)-(7-Chloro-4-quinolyl)hydrazonomethyl]benzonitrile
 monohydrate
;
_journal_coeditor_code           HB5242
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3239
_journal_page_last               o3240
_journal_paper_doi               10.1107/S1600536809050120
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C17 H11 Cl N4, H2 O'
_chemical_formula_moiety         'C17 H11 Cl N4, H2 O'
_chemical_formula_sum            'C17 H13 Cl N4 O'
_chemical_formula_weight         324.76
_chemical_name_systematic
;
3-[(E)-(7-Chloro-4-quinolyl)hydrazonomethyl]benzonitrile
mono hydrate
;
_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                110.8897(15)
_cell_angle_beta                 93.4341(16)
_cell_angle_gamma                110.6766(15)
_cell_formula_units_Z            2
_cell_length_a                   8.7406(2)
_cell_length_b                   9.8587(3)
_cell_length_c                   10.2301(2)
_cell_measurement_reflns_used    11816
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     752.93(4)
_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    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  '10 cm confocal mirrors'
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_av_sigmaI/netI    0.041
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14600
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.0
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.10
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3425
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.10
_refine_ls_R_factor_all          0.060
_refine_ls_R_factor_gt           0.047
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0230P)²+0.7336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.100
_refine_ls_wR_factor_ref         0.109
_reflns_number_gt                2902
_reflns_number_total             3425
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5242.cif
_cod_data_source_block           I
_cod_original_cell_volume        752.93(3)
_cod_database_code               2224268
_cod_database_fobs_code          2224268
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.19140(6) 0.44486(6) -0.08216(5) 0.02503(14) Uani d . 1 . .
N N1 0.0883(2) 0.39813(19) 0.38535(17) 0.0215(3) Uani d . 1 . .
N N2 0.49296(19) 0.27107(18) 0.43632(17) 0.0181(3) Uani d . 1 . .
H H2N 0.559(3) 0.270(3) 0.377(2) 0.022 Uiso d . 1 . .
N N3 0.52218(19) 0.23502(18) 0.55031(16) 0.0181(3) Uani d . 1 . .
N N4 1.1329(2) 0.0074(2) 0.7938(2) 0.0357(5) Uani d . 1 . .
C C1 0.1296(2) 0.3704(2) 0.4975(2) 0.0217(4) Uani d . 1 . .
H H1 0.0635 0.3806 0.5679 0.026 Uiso calc R 1 . .
C C2 0.2613(2) 0.3278(2) 0.5209(2) 0.0204(4) Uani d . 1 . .
H H2 0.2816 0.3086 0.6036 0.024 Uiso calc R 1 . .
C C3 0.3625(2) 0.3139(2) 0.42154(19) 0.0164(4) Uani d . 1 . .
C C4 0.3262(2) 0.3449(2) 0.29879(19) 0.0160(4) Uani d . 1 . .
C C5 0.4207(2) 0.3368(2) 0.1905(2) 0.0191(4) Uani d . 1 . .
H H5 0.5150 0.3113 0.1983 0.023 Uiso calc R 1 . .
C C6 0.3779(2) 0.3654(2) 0.0746(2) 0.0203(4) Uani d . 1 . .
H H6 0.4411 0.3583 0.0019 0.024 Uiso calc R 1 . .
C C7 0.2398(2) 0.4052(2) 0.0646(2) 0.0194(4) Uani d . 1 . .
C C8 0.1449(2) 0.4147(2) 0.1657(2) 0.0193(4) Uani d . 1 . .
H H8 0.0515 0.4409 0.1557 0.023 Uiso calc R 1 . .
C C9 0.1869(2) 0.3852(2) 0.28647(19) 0.0178(4) Uani d . 1 . .
C C10 0.6454(2) 0.1947(2) 0.5564(2) 0.0197(4) Uani d . 1 . .
H H10 0.7095 0.1919 0.4844 0.024 Uiso calc R 1 . .
C C11 0.6892(2) 0.1527(2) 0.67264(19) 0.0192(4) Uani d . 1 . .
C C12 0.8252(2) 0.1113(2) 0.6757(2) 0.0216(4) Uani d . 1 . .
H H12 0.8867 0.1086 0.6020 0.026 Uiso calc R 1 . .
C C13 0.8715(2) 0.0735(2) 0.7873(2) 0.0231(4) Uani d . 1 . .
C C14 0.7821(3) 0.0759(2) 0.8950(2) 0.0286(5) Uani d . 1 . .
H H14 0.8144 0.0508 0.9708 0.034 Uiso calc R 1 . .
C C15 0.6451(3) 0.1154(3) 0.8908(2) 0.0298(5) Uani d . 1 . .
H H15 0.5829 0.1166 0.9640 0.036 Uiso calc R 1 . .
C C16 0.5979(3) 0.1531(2) 0.7807(2) 0.0240(4) Uani d . 1 . .
H H16 0.5034 0.1792 0.7786 0.029 Uiso calc R 1 . .
C C17 1.0162(3) 0.0351(2) 0.7902(2) 0.0275(5) Uani d . 1 . .
O O1W 0.74203(19) 0.2487(2) 0.26148(16) 0.0261(3) Uani d . 1 . .
H H1W 0.746(3) 0.160(3) 0.231(3) 0.039 Uiso d . 1 . .
H H2W 0.845(4) 0.311(3) 0.302(3) 0.039 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'
Cl Cl 0.1484 0.1585 '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'
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
C1 N1 C9 . . 116.07(16) ?
C3 N2 N3 . . 119.16(15) ?
C3 N2 H2N . . 121.4(14) ?
N3 N2 H2N . . 119.4(14) ?
C10 N3 N2 . . 115.64(16) ?
N1 C1 C2 . . 125.78(18) ?
N1 C1 H1 . . 117.1 ?
C2 C1 H1 . . 117.1 ?
C3 C2 C1 . . 118.91(17) ?
C3 C2 H2 . . 120.5 ?
C1 C2 H2 . . 120.5 ?
N2 C3 C2 . . 122.36(16) ?
N2 C3 C4 . . 119.55(16) ?
C2 C3 C4 . . 118.09(16) ?
C5 C4 C9 . . 118.81(16) ?
C5 C4 C3 . . 123.77(16) ?
C9 C4 C3 . . 117.42(16) ?
C6 C5 C4 . . 120.96(17) ?
C6 C5 H5 . . 119.5 ?
C4 C5 H5 . . 119.5 ?
C5 C6 C7 . . 119.30(18) ?
C5 C6 H6 . . 120.4 ?
C7 C6 H6 . . 120.4 ?
C8 C7 C6 . . 122.12(17) ?
C8 C7 Cl1 . . 119.72(14) ?
C6 C7 Cl1 . . 118.16(15) ?
C7 C8 C9 . . 119.46(16) ?
C7 C8 H8 . . 120.3 ?
C9 C8 H8 . . 120.3 ?
N1 C9 C4 . . 123.72(16) ?
N1 C9 C8 . . 116.93(16) ?
C4 C9 C8 . . 119.35(16) ?
N3 C10 C11 . . 120.96(17) ?
N3 C10 H10 . . 119.5 ?
C11 C10 H10 . . 119.5 ?
C12 C11 C16 . . 119.17(17) ?
C12 C11 C10 . . 118.91(17) ?
C16 C11 C10 . . 121.92(17) ?
C11 C12 C13 . . 120.01(18) ?
C11 C12 H12 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C14 C13 C12 . . 120.63(18) ?
C14 C13 C17 . . 120.38(17) ?
C12 C13 C17 . . 118.98(19) ?
C13 C14 C15 . . 119.29(18) ?
C13 C14 H14 . . 120.4 ?
C15 C14 H14 . . 120.4 ?
C14 C15 C16 . . 120.6(2) ?
C14 C15 H15 . . 119.7 ?
C16 C15 H15 . . 119.7 ?
C15 C16 C11 . . 120.31(19) ?
C15 C16 H16 . . 119.8 ?
C11 C16 H16 . . 119.8 ?
N4 C17 C13 . . 178.8(2) ?
H1W O1W H2W . . 102(2) ?
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 C7 . 1.7454(18) ?
N1 C1 . 1.328(2) ?
N1 C9 . 1.368(2) ?
N2 C3 . 1.366(2) ?
N2 N3 . 1.369(2) ?
N2 H2N . 0.86(2) ?
N3 C10 . 1.278(2) ?
N4 C17 . 1.147(3) ?
C1 C2 . 1.393(3) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.389(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.437(2) ?
C4 C5 . 1.417(3) ?
C4 C9 . 1.419(2) ?
C5 C6 . 1.373(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.403(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.362(3) ?
C8 C9 . 1.423(2) ?
C8 H8 . 0.9500 ?
C10 C11 . 1.462(2) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.388(3) ?
C11 C16 . 1.401(3) ?
C12 C13 . 1.401(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.386(3) ?
C13 C17 . 1.444(3) ?
C14 C15 . 1.387(3) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.389(3) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
O1W H1W . 0.83(3) ?
O1W H2W . 0.86(3) ?
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 N4 2_756 0.83(3) 2.21(3) 2.982(3) 155(3)
O1w H2w N1 1_655 0.86(3) 1.99(3) 2.828(3) 164(3)
N2 H2n O1w 1_555 0.86(3) 2.07(3) 2.917(2) 167(3)
C5 H5 O1w 1_555 0.95 2.39 3.331(3) 169
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
C3 N2 N3 C10 . . . . 179.41(16) ?
C9 N1 C1 C2 . . . . -1.0(3) ?
N1 C1 C2 C3 . . . . 0.9(3) ?
N3 N2 C3 C2 . . . . 2.4(3) ?
N3 N2 C3 C4 . . . . -177.19(15) ?
C1 C2 C3 N2 . . . . -179.34(17) ?
C1 C2 C3 C4 . . . . 0.2(3) ?
N2 C3 C4 C5 . . . . -1.2(3) ?
C2 C3 C4 C5 . . . . 179.21(17) ?
N2 C3 C4 C9 . . . . 178.48(16) ?
C2 C3 C4 C9 . . . . -1.1(2) ?
C9 C4 C5 C6 . . . . -0.7(3) ?
C3 C4 C5 C6 . . . . 178.94(17) ?
C4 C5 C6 C7 . . . . 0.8(3) ?
C5 C6 C7 C8 . . . . -0.8(3) ?
C5 C6 C7 Cl1 . . . . 178.69(14) ?
C6 C7 C8 C9 . . . . 0.6(3) ?
Cl1 C7 C8 C9 . . . . -178.84(14) ?
C1 N1 C9 C4 . . . . 0.0(3) ?
C1 N1 C9 C8 . . . . -179.86(17) ?
C5 C4 C9 N1 . . . . -179.23(17) ?
C3 C4 C9 N1 . . . . 1.1(3) ?
C5 C4 C9 C8 . . . . 0.6(3) ?
C3 C4 C9 C8 . . . . -179.14(16) ?
C7 C8 C9 N1 . . . . 179.30(17) ?
C7 C8 C9 C4 . . . . -0.5(3) ?
N2 N3 C10 C11 . . . . -179.76(16) ?
N3 C10 C11 C12 . . . . -179.33(17) ?
N3 C10 C11 C16 . . . . 0.7(3) ?
C16 C11 C12 C13 . . . . -1.2(3) ?
C10 C11 C12 C13 . . . . 178.81(17) ?
C11 C12 C13 C14 . . . . 0.4(3) ?
C11 C12 C13 C17 . . . . -178.30(17) ?
C12 C13 C14 C15 . . . . 0.4(3) ?
C17 C13 C14 C15 . . . . 179.10(19) ?
C13 C14 C15 C16 . . . . -0.4(3) ?
C14 C15 C16 C11 . . . . -0.4(3) ?
C12 C11 C16 C15 . . . . 1.2(3) ?
C10 C11 C16 C15 . . . . -178.82(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655946
