#------------------------------------------------------------------------------
#$Date: 2019-09-17 19:15:12 +0300 (Tue, 17 Sep 2019) $
#$Revision: 218395 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/08/7200870.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_7200870
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_data_source_file            B823058G.txt
_cod_data_source_block           azide
_cod_depositor_comments
;
 Replaced the incorrect bibliographical reference to the original
 publication with a proper one.
 
 Antanas Vaitkus,
 2019-09-17 
;
_cod_original_sg_symbol_Hall     '-P 2ac 2ab '
_cod_database_code               7200870
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
_atom_site_disorder_assembly
_atom_site_disorder_group
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
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
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24693544
