#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/46/2234600.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_2234600
loop_
_publ_author_name
'Bouacida, Sofiane'
'Bouraiou, Abdelmalek'
'Benhamoud, Nassima'
'Roisnel, Thierry'
'Belfaitah, Ali'
_publ_section_title
;
 2-Chloro-3-[(E)-(hydrazin-1-ylidene)methyl]-6-methoxyquinoline
;
_journal_coeditor_code           FJ2545
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1548
_journal_paper_doi               10.1107/S1600536812017977
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C11 H10 Cl N3 O'
_chemical_formula_moiety         'C11 H10 Cl N3 O'
_chemical_formula_sum            'C11 H10 Cl N3 O'
_chemical_formula_weight         235.67
_chemical_name_systematic
;
2-Chloro-3-[(E)-(hydrazin-1-ylidene)methyl]-6-methoxyquinoline
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8949(2)
_cell_length_b                   12.0510(5)
_cell_length_c                   21.9910(9)
_cell_measurement_reflns_used    26476
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.91
_cell_volume                     1032.20(8)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15777
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.25
_exptl_absorpt_coefficient_mu    0.35
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2002)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.259
_refine_ls_abs_structure_details 'Flack (1983), 922 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0395P)²+0.2196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0732
_reflns_number_gt                2044
_reflns_number_total             2352
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fj2545.cif
_cod_data_source_block           I
_cod_database_code               2234600
_cod_database_fobs_code          2234600
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
_atom_site_symmetry_multiplicity
C C1 0.4493(5) 0.15128(15) 0.87535(8) 0.0170(4) Uani d . 1 1
C C3 0.3425(5) 0.16948(14) 0.77399(8) 0.0168(4) Uani d . 1 1
C C4 0.3615(5) 0.23375(14) 0.72037(8) 0.0187(4) Uani d . 1 1
H H4 0.4634 0.3053 0.7216 0.022 Uiso calc R 1 1
C C5 0.2342(5) 0.19378(14) 0.66667(8) 0.0201(4) Uani d . 1 1
H H5 0.2468 0.2378 0.6309 0.024 Uiso calc R 1 1
C C6 0.0840(5) 0.08694(15) 0.66430(8) 0.0179(4) Uani d . 1 1
C C7 0.0598(5) 0.02243(15) 0.71528(8) 0.0173(4) Uani d . 1 1
H H7 -0.0414 -0.0492 0.7131 0.021 Uiso calc R 1 1
C C8 0.1864(5) 0.06299(13) 0.77136(8) 0.0160(4) Uani d . 1 1
C C9 0.1641(5) 0.00226(13) 0.82624(8) 0.0156(4) Uani d . 1 1
H H9 0.0595 -0.069 0.8261 0.019 Uiso calc R 1 1
C C10 0.2916(5) 0.04468(14) 0.87986(8) 0.0165(4) Uani d . 1 1
C C11 0.2622(5) -0.01392(14) 0.93795(8) 0.0179(4) Uani d . 1 1
H H11 0.3884 0.0114 0.9722 0.021 Uiso calc R 1 1
C C15 -0.1868(5) -0.05136(14) 0.60289(8) 0.0219(4) Uani d . 1 1
H H15A -0.0198 -0.1085 0.6143 0.033 Uiso calc R 1 1
H H15B -0.2623 -0.0637 0.5609 0.033 Uiso calc R 1 1
H H15C -0.3852 -0.0552 0.6302 0.033 Uiso calc R 1 1
N N2 0.4745(4) 0.21203(13) 0.82682(6) 0.0176(3) Uani d . 1 1
N N12 0.0681(4) -0.09888(12) 0.94285(7) 0.0202(3) Uani d . 1 1
N N13 0.0692(5) -0.15224(13) 0.99808(7) 0.0240(4) Uani d . 1 1
H H13A 0.1995 -0.1275 1.0278 0.029 Uiso calc R 1 1
H H13B -0.0603 -0.2112 1.0037 0.029 Uiso calc R 1 1
Cl Cl1 0.62727(12) 0.20978(3) 0.941458(19) 0.02055(12) Uani d . 1 1
O O14 -0.0299(4) 0.05616(10) 0.60762(5) 0.0210(3) Uani d . 1 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 0 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 3 0.069
0 1 -3 0.025
8 -1 3 0.138
-10 1 -3 0.128
0 1 0 0.025
0 -1 0 0.074
0 0 -1 0.025
0 0 1 0.074
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 C1 C10 126.68(16)
N2 C1 Cl1 115.08(13)
C10 C1 Cl1 118.23(13)
N2 C3 C4 118.87(16)
N2 C3 C8 122.21(15)
C4 C3 C8 118.92(16)
C5 C4 C3 120.56(16)
C5 C4 H4 119.7
C3 C4 H4 119.7
C4 C5 C6 120.12(16)
C4 C5 H5 119.9
C6 C5 H5 119.9
C7 C6 O14 124.60(16)
C7 C6 C5 121.03(16)
O14 C6 C5 114.37(15)
C6 C7 C8 119.60(16)
C6 C7 H7 120.2
C8 C7 H7 120.2
C9 C8 C7 122.92(16)
C9 C8 C3 117.32(16)
C7 C8 C3 119.76(16)
C10 C9 C8 121.08(15)
C10 C9 H9 119.5
C8 C9 H9 119.5
C9 C10 C1 115.43(15)
C9 C10 C11 122.66(15)
C1 C10 C11 121.89(15)
N12 C11 C10 120.43(17)
N12 C11 H11 119.8
C10 C11 H11 119.8
O14 C15 H15A 109.5
O14 C15 H15B 109.5
H15A C15 H15B 109.5
O14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C1 N2 C3 117.24(15)
C11 N12 N13 116.60(16)
N12 N13 H13A 120
N12 N13 H13B 120
H13A N13 H13B 120
C6 O14 C15 116.53(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.298(2)
C1 C10 1.428(2)
C1 Cl1 1.7581(17)
C3 N2 1.370(2)
C3 C4 1.413(2)
C3 C8 1.421(2)
C4 C5 1.368(3)
C4 H4 0.95
C5 C6 1.415(3)
C5 H5 0.95
C6 C7 1.368(2)
C6 O14 1.374(2)
C7 C8 1.415(2)
C7 H7 0.95
C8 C9 1.414(2)
C9 C10 1.378(2)
C9 H9 0.95
C10 C11 1.464(2)
C11 N12 1.277(2)
C11 H11 0.95
C15 O14 1.436(2)
C15 H15A 0.98
C15 H15B 0.98
C15 H15C 0.98
N12 N13 1.374(2)
N13 H13A 0.88
N13 H13B 0.88
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
_geom_hbond_publ_flag
N13 H13A O14 2_555 0.8800 2.3400 3.219(2) 178.00 yes
N13 H13B N13 3_447 0.8800 2.1900 3.058(2) 169.00 yes
C11 H11 Cl1 . 0.9500 2.6500 3.0488(18) 106.00 ?
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
N2 C3 C4 C5 179.61(17)
C8 C3 C4 C5 -0.5(3)
C3 C4 C5 C6 -0.4(3)
C4 C5 C6 C7 0.7(3)
C4 C5 C6 O14 -179.26(17)
O14 C6 C7 C8 179.99(18)
C5 C6 C7 C8 0.1(3)
C6 C7 C8 C9 178.61(17)
C6 C7 C8 C3 -1.0(3)
N2 C3 C8 C9 1.4(3)
C4 C3 C8 C9 -178.41(18)
N2 C3 C8 C7 -178.88(17)
C4 C3 C8 C7 1.3(3)
C7 C8 C9 C10 179.82(18)
C3 C8 C9 C10 -0.5(3)
C8 C9 C10 C1 -1.1(3)
C8 C9 C10 C11 177.74(17)
N2 C1 C10 C9 2.1(3)
Cl1 C1 C10 C9 -178.57(14)
N2 C1 C10 C11 -176.71(17)
Cl1 C1 C10 C11 2.6(2)
C9 C10 C11 N12 -11.3(3)
C1 C10 C11 N12 167.39(17)
C10 C1 N2 C3 -1.3(3)
Cl1 C1 N2 C3 179.38(13)
C4 C3 N2 C1 179.25(17)
C8 C3 N2 C1 -0.6(3)
C10 C11 N12 N13 176.74(15)
C7 C6 O14 C15 0.5(3)
C5 C6 O14 C15 -179.58(15)
