#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/87/7008778.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_7008778
loop_
_publ_author_name
'Albrecht, Markus'
'Osetska, Olga'
'Fröhlich, Roland'
_publ_section_title
;
 2-[(8-Hydroxyquinolinyl)methylene]hydrazinecarboxamide: expanding the
 coordination sphere of 8-hydroxyquinoline for coordination of
 rare-earth metal(iii) ions
;
_journal_issue                   23
_journal_name_full               'Dalton Transactions'
_journal_page_first              3757
_journal_paper_doi               10.1039/b507621h
_journal_year                    2005
_chemical_formula_sum            'C12 H15 Cl N4 O3'
_chemical_formula_weight         298.73
_chemical_name_systematic
;
?
;
_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   'at N from difmap, other geom'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.16(1)
_cell_angle_beta                 91.99(1)
_cell_angle_gamma                103.48(1)
_cell_formula_units_Z            2
_cell_length_a                   6.625(1)
_cell_length_b                   8.080(1)
_cell_length_c                   12.955(1)
_cell_measurement_temperature    198(2)
_cell_volume                     673.22(14)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SCHAKAL (Keller, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      198(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.075
_diffrn_reflns_av_sigmaI/netI    0.0614
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7086
_diffrn_reflns_theta_full        26.30
_diffrn_reflns_theta_max         26.30
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_correction_T_min  0.8655
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995 & 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         2.156
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.169
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.602
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2718
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.602
_refine_ls_R_factor_all          0.1306
_refine_ls_R_factor_gt           0.1014
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2423
_refine_ls_wR_factor_ref         0.2543
_reflns_number_gt                1874
_reflns_number_total             2718
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b507621h.txt
_cod_data_source_block           fro3131
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7008778
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
N1 N 0.7346(5) 1.4384(4) 0.4775(3) 0.0299(8) Uani 1 1 d . . .
H1 H 0.704(7) 1.337(6) 0.440(4) 0.044(13) Uiso 1 1 d . . .
C2 C 0.7287(6) 1.4423(5) 0.5838(3) 0.0284(9) Uani 1 1 d . . .
C3 C 0.6803(6) 1.2904(5) 0.6365(3) 0.0342(10) Uani 1 1 d . . .
O3 O 0.6424(5) 1.1448(4) 0.5767(2) 0.0411(8) Uani 1 1 d . . .
H3 H 0.5402 1.0747 0.5985 0.062 Uiso 1 1 calc R . .
C4 C 0.6743(6) 1.2996(5) 0.7414(3) 0.0344(10) Uani 1 1 d . . .
H4 H 0.6397 1.1971 0.7773 0.041 Uiso 1 1 calc R . .
C5 C 0.7176(6) 1.4556(6) 0.7977(4) 0.0410(11) Uani 1 1 d . . .
H5 H 0.7150 1.4581 0.8710 0.049 Uiso 1 1 calc R . .
C6 C 0.7635(7) 1.6040(6) 0.7477(4) 0.0411(11) Uani 1 1 d . . .
H6 H 0.7912 1.7098 0.7863 0.049 Uiso 1 1 calc R . .
C7 C 0.7704(6) 1.6021(5) 0.6390(3) 0.0347(10) Uani 1 1 d . . .
C8 C 0.8126(6) 1.7512(5) 0.5809(4) 0.0366(10) Uani 1 1 d . . .
H8 H 0.8407 1.8601 0.6160 0.044 Uiso 1 1 calc R . .
C9 C 0.8134(6) 1.7404(5) 0.4763(4) 0.0353(10) Uani 1 1 d . . .
H9 H 0.8396 1.8412 0.4386 0.042 Uiso 1 1 calc R . .
C10 C 0.7753(6) 1.5793(5) 0.4231(3) 0.0282(9) Uani 1 1 d . . .
C11 C 0.7791(6) 1.5585(5) 0.3129(3) 0.0316(9) Uani 1 1 d . . .
H11 H 0.7485 1.4486 0.2792 0.038 Uiso 1 1 calc R . .
N12 N 0.8255(5) 1.6947(4) 0.2613(3) 0.0304(8) Uani 1 1 d . . .
N13 N 0.8331(5) 1.6715(5) 0.1588(3) 0.0348(8) Uani 1 1 d . . .
H13 H 0.815(7) 1.569(7) 0.129(4) 0.050(14) Uiso 1 1 d . . .
C14 C 0.9004(6) 1.8093(5) 0.0989(4) 0.0361(10) Uani 1 1 d . . .
N15 N 0.9220(7) 1.9637(5) 0.1424(3) 0.0469(10) Uani 1 1 d . . .
H15A H 0.870(7) 1.982(6) 0.209(5) 0.056 Uiso 1 1 d . . .
H15B H 0.970(7) 2.057(7) 0.094(4) 0.056 Uiso 1 1 d . . .
O16 O 0.9366(5) 1.7810(4) 0.0075(2) 0.0439(8) Uani 1 1 d . . .
Cl1 Cl 0.33457(18) 0.87993(13) 0.67868(9) 0.0464(4) Uani 1 1 d . . .
O21 O 1.2390(5) 1.6407(4) -0.0585(3) 0.0572(10) Uani 1 1 d . . .
H21 H 1.1401 1.6813 -0.0393 0.086 Uiso 1 1 calc R . .
C22 C 1.4244(8) 1.7654(7) -0.0456(5) 0.0626(15) Uani 1 1 d . . .
H22A H 1.4157 1.8425 0.0135 0.094 Uiso 1 1 calc R . .
H22B H 1.4476 1.8303 -0.1082 0.094 Uiso 1 1 calc R . .
H22C H 1.5399 1.7110 -0.0329 0.094 Uiso 1 1 calc R . .
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
C10 N1 C2 123.1(3) . . ?
N1 C2 C3 120.6(4) . . ?
N1 C2 C7 119.0(4) . . ?
C3 C2 C7 120.4(4) . . ?
O3 C3 C4 125.3(4) . . ?
O3 C3 C2 115.8(4) . . ?
C4 C3 C2 118.8(4) . . ?
C3 C4 C5 121.8(4) . . ?
C6 C5 C4 120.1(4) . . ?
C5 C6 C7 120.5(4) . . ?
C6 C7 C2 118.3(4) . . ?
C6 C7 C8 124.0(4) . . ?
C2 C7 C8 117.7(4) . . ?
C9 C8 C7 121.0(4) . . ?
C8 C9 C10 120.2(4) . . ?
N1 C10 C9 119.0(4) . . ?
N1 C10 C11 117.8(3) . . ?
C9 C10 C11 123.1(4) . . ?
N12 C11 C10 117.5(4) . . ?
C11 N12 N13 116.2(3) . . ?
N12 N13 C14 120.0(4) . . ?
O16 C14 N15 124.0(4) . . ?
O16 C14 N13 117.9(4) . . ?
N15 C14 N13 118.0(4) . . ?
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
N1 C10 1.340(5) . ?
N1 C2 1.379(5) . ?
C2 C3 1.404(6) . ?
C2 C7 1.416(6) . ?
C3 O3 1.352(5) . ?
C3 C4 1.360(6) . ?
C4 C5 1.397(6) . ?
C5 C6 1.361(7) . ?
C6 C7 1.409(6) . ?
C7 C8 1.422(6) . ?
C8 C9 1.356(6) . ?
C9 C10 1.414(6) . ?
C10 C11 1.432(6) . ?
C11 N12 1.290(5) . ?
N12 N13 1.339(5) . ?
N13 C14 1.377(6) . ?
C14 O16 1.240(5) . ?
C14 N15 1.324(6) . ?
O21 C22 1.395(6) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C2 C3 178.5(4) . . . . ?
C10 N1 C2 C7 -1.0(5) . . . . ?
N1 C2 C3 O3 0.4(5) . . . . ?
C7 C2 C3 O3 179.8(3) . . . . ?
N1 C2 C3 C4 -179.5(4) . . . . ?
C7 C2 C3 C4 0.0(6) . . . . ?
O3 C3 C4 C5 179.3(4) . . . . ?
C2 C3 C4 C5 -0.9(6) . . . . ?
C3 C4 C5 C6 1.3(6) . . . . ?
C4 C5 C6 C7 -0.8(7) . . . . ?
C5 C6 C7 C2 -0.1(6) . . . . ?
C5 C6 C7 C8 178.6(4) . . . . ?
N1 C2 C7 C6 179.9(3) . . . . ?
C3 C2 C7 C6 0.5(6) . . . . ?
N1 C2 C7 C8 1.2(5) . . . . ?
C3 C2 C7 C8 -178.3(4) . . . . ?
C6 C7 C8 C9 -178.9(4) . . . . ?
C2 C7 C8 C9 -0.2(6) . . . . ?
C7 C8 C9 C10 -1.1(6) . . . . ?
C2 N1 C10 C9 -0.3(6) . . . . ?
C2 N1 C10 C11 179.4(3) . . . . ?
C8 C9 C10 N1 1.3(6) . . . . ?
C8 C9 C10 C11 -178.3(4) . . . . ?
N1 C10 C11 N12 -177.6(4) . . . . ?
C9 C10 C11 N12 2.0(6) . . . . ?
C10 C11 N12 N13 178.3(3) . . . . ?
C11 N12 N13 C14 -173.9(4) . . . . ?
N12 N13 C14 O16 168.7(3) . . . . ?
N12 N13 C14 N15 -11.4(6) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21175862
