#------------------------------------------------------------------------------
#$Date: 2019-09-17 19:23:54 +0300 (Tue, 17 Sep 2019) $
#$Revision: 218397 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/55/7215595.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_7215595
loop_
_publ_author_name
'Kaiser, Carlos R.'
'Pais, Karla C.'
'de Souza, Marcus V. N.'
'Wardell, James L.'
'Wardell, Solange M. S. V.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Assessing the persistence of the N--H⋯N hydrogen bonding leading
 to supramolecular chains in molecules related to the anti-malarial drug,
 chloroquine
;
_journal_coden_ASTM              CRECF4
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              1133
_journal_page_last               1140
_journal_paper_doi               10.1039/b823058g
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C11 H10 Cl N5'
_chemical_formula_sum            'C11 H10 Cl N5'
_chemical_formula_weight         247.69
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.0426(5)
_cell_length_b                   7.8693(2)
_cell_length_c                   22.6276(9)
_cell_measurement_reflns_used    2928
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     2322.41(14)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_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
'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.060
_diffrn_reflns_av_sigmaI/netI    0.037
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16466
_diffrn_reflns_theta_full        27.4
_diffrn_reflns_theta_max         27.4
_diffrn_reflns_theta_min         3.1
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.28
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2630
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.08
_refine_ls_R_factor_all          0.067
_refine_ls_R_factor_gt           0.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0184P)²+3.7962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.096
_refine_ls_wR_factor_ref         0.105
_reflns_number_gt                2120
_reflns_number_total             2630
_reflns_threshold_expression     I>2σ(I)
_cod_duplicate_entry             7200870
_cod_data_source_file            b823058g.txt
_cod_data_source_block           azide
_cod_depositor_comments
;
 Updated bibliographic information.

 Antanas Vaitkus,
 2019-09-17

 Marked entry as a duplicate of entry 7200870.

 Antanas Vaitkus,
 2019-09-17
;
_cod_original_sg_symbol_Hall     '-P 2ac 2ab '
_cod_database_code               7215595
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'
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
Cl1 Cl 0.18786(5) 0.15546(8) 0.55167(2) 0.02836(16) Uani 1 1 d .
N1 N 0.04322(14) 0.4454(2) 0.73332(8) 0.0221(4) Uani 1 1 d .
N2 N 0.33271(14) 0.4890(2) 0.81559(8) 0.0195(4) Uani 1 1 d D
H2N H 0.3893 0.4582 0.7973 0.023 Uiso 1 1 d D
N3 N 0.38215(17) 0.3364(3) 0.93286(8) 0.0300(5) Uani 1 1 d .
N4 N 0.42405(16) 0.3219(3) 0.98157(9) 0.0280(5) Uani 1 1 d .
N5 N 0.46696(18) 0.2953(3) 1.02406(10) 0.0420(6) Uani 1 1 d .
C1 C 0.05692(17) 0.5176(3) 0.78566(10) 0.0222(5) Uani 1 1 d .
H1 H -0.0024 0.5601 0.8050 0.027 Uiso 1 1 calc R
C2 C 0.15004(17) 0.5371(3) 0.81489(10) 0.0202(5) Uani 1 1 d .
H2 H 0.1524 0.5929 0.8521 0.024 Uiso 1 1 calc R
C3 C 0.24005(16) 0.4747(3) 0.78950(9) 0.0161(4) Uani 1 1 d .
C4 C 0.22938(16) 0.3926(3) 0.73261(9) 0.0159(4) Uani 1 1 d .
C5 C 0.31378(16) 0.3258(3) 0.70103(9) 0.0184(4) Uani 1 1 d .
H5 H 0.3802 0.3299 0.7182 0.022 Uiso 1 1 calc R
C6 C 0.30170(17) 0.2550(3) 0.64600(10) 0.0211(5) Uani 1 1 d .
H6 H 0.3590 0.2116 0.6250 0.025 Uiso 1 1 calc R
C7 C 0.20268(18) 0.2482(3) 0.62136(9) 0.0203(5) Uani 1 1 d .
C8 C 0.11901(17) 0.3108(3) 0.64994(9) 0.0197(4) Uani 1 1 d .
H8 H 0.0533 0.3053 0.6319 0.024 Uiso 1 1 calc R
C9 C 0.13036(16) 0.3843(3) 0.70677(9) 0.0180(4) Uani 1 1 d .
C10 C 0.34908(18) 0.5853(3) 0.86968(10) 0.0225(5) Uani 1 1 d .
H10A H 0.3093 0.6923 0.8673 0.027 Uiso 1 1 calc R
H10B H 0.4225 0.6160 0.8723 0.027 Uiso 1 1 calc R
C11 C 0.31863(18) 0.4918(3) 0.92580(10) 0.0237(5) Uani 1 1 d .
H11A H 0.3284 0.5672 0.9604 0.028 Uiso 1 1 calc R
H11B H 0.2453 0.4601 0.9238 0.028 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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C9 115.44(19)
C3 N2 C10 122.86(18)
C3 N2 H2N 121.5
C10 N2 H2N 114.5
N4 N3 C11 114.76(19)
N5 N4 N3 173.4(3)
N1 C1 C2 126.1(2)
N1 C1 H1 116.9
C2 C1 H1 116.9
C1 C2 C3 120.0(2)
C1 C2 H2 120.0
C3 C2 H2 120.0
N2 C3 C2 122.92(19)
N2 C3 C4 120.83(19)
C2 C3 C4 116.25(19)
C5 C4 C9 118.90(19)
C5 C4 C3 122.74(19)
C9 C4 C3 118.33(19)
C6 C5 C4 121.3(2)
C6 C5 H5 119.3
C4 C5 H5 119.3
C5 C6 C7 118.7(2)
C5 C6 H6 120.7
C7 C6 H6 120.7
C8 C7 C6 122.2(2)
C8 C7 Cl1 119.42(17)
C6 C7 Cl1 118.34(17)
C7 C8 C9 119.7(2)
C7 C8 H8 120.2
C9 C8 H8 120.2
N1 C9 C8 116.97(19)
N1 C9 C4 123.86(19)
C8 C9 C4 119.17(19)
N2 C10 C11 114.31(19)
N2 C10 H10A 108.7
C11 C10 H10A 108.7
N2 C10 H10B 108.7
C11 C10 H10B 108.7
H10A C10 H10B 107.6
N3 C11 C10 110.04(19)
N3 C11 H11A 109.7
C10 C11 H11A 109.7
N3 C11 H11B 109.7
C10 C11 H11B 109.7
H11A C11 H11B 108.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C7 1.748(2)
N1 C1 1.326(3)
N1 C9 1.372(3)
N2 C3 1.350(3)
N2 C10 1.456(3)
N2 H2N 0.8800
N3 N4 1.235(3)
N3 C11 1.486(3)
N4 N5 1.132(3)
C1 C2 1.391(3)
C1 H1 0.9500
C2 C3 1.396(3)
C2 H2 0.9500
C3 C4 1.447(3)
C4 C5 1.414(3)
C4 C9 1.419(3)
C5 C6 1.373(3)
C5 H5 0.9500
C6 C7 1.408(3)
C6 H6 0.9500
C7 C8 1.361(3)
C8 C9 1.418(3)
C8 H8 0.9500
C10 C11 1.520(3)
C10 H10A 0.9900
C10 H10B 0.9900
C11 H11A 0.9900
C11 H11B 0.9900
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
C11 N3 N4 N5 -175(2)
C9 N1 C1 C2 0.5(3)
N1 C1 C2 C3 -1.3(4)
C10 N2 C3 C2 -6.3(3)
C10 N2 C3 C4 173.50(19)
C1 C2 C3 N2 -179.8(2)
C1 C2 C3 C4 0.4(3)
N2 C3 C4 C5 -0.9(3)
C2 C3 C4 C5 178.9(2)
N2 C3 C4 C9 -178.74(19)
C2 C3 C4 C9 1.1(3)
C9 C4 C5 C6 0.6(3)
C3 C4 C5 C6 -177.2(2)
C4 C5 C6 C7 -0.7(3)
C5 C6 C7 C8 0.7(3)
C5 C6 C7 Cl1 -179.21(17)
C6 C7 C8 C9 -0.7(3)
Cl1 C7 C8 C9 179.26(16)
C1 N1 C9 C8 -178.2(2)
C1 N1 C9 C4 1.2(3)
C7 C8 C9 N1 179.9(2)
C7 C8 C9 C4 0.6(3)
C5 C4 C9 N1 -179.9(2)
C3 C4 C9 N1 -1.9(3)
C5 C4 C9 C8 -0.5(3)
C3 C4 C9 C8 177.38(19)
C3 N2 C10 C11 80.0(3)
N4 N3 C11 C10 128.5(2)
N2 C10 C11 N3 62.3(3)
