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#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/08/7200867.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_7200867
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         'C12 H13 Cl N2'
_chemical_formula_sum            'C12 H13 Cl N2'
_chemical_formula_weight         220.69
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 108.987(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.4386(3)
_cell_length_b                   17.9769(5)
_cell_length_c                   13.0512(3)
_cell_measurement_reflns_used    5401
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     2315.86(11)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.058
_diffrn_reflns_av_sigmaI/netI    0.039
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            33628
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.1
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.31
_refine_diff_density_min         -0.50
_refine_diff_density_rms         0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         5297
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.086
_refine_ls_R_factor_gt           0.059
_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)+(0.1031P)²+1.6308P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.165
_refine_ls_wR_factor_ref         0.189
_reflns_number_gt                3930
_reflns_number_total             5297
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            B823058G.txt
_cod_data_source_block           nPr
_cod_depositor_comments
;
 Replaced the incorrect bibliographical reference to the original
 publication with a proper one.
 
 Antanas Vaitkus,
 2019-09-17 
;
_cod_original_cell_volume        2315.85(11)
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7200867
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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 0.92021(7) 0.46245(4) 0.60977(6) 0.0384(2) Uani 1 1 d . . .
Cl1A Cl 0.76025(7) 0.01571(4) 0.63660(7) 0.0425(2) Uani 1 1 d . . .
N1 N 0.6077(2) 0.25218(13) 0.42238(15) 0.0267(5) Uani 1 1 d . . .
N2 N 0.5607(2) 0.17474(11) 0.71318(16) 0.0235(4) Uani 1 1 d D . .
H2N H 0.5872 0.2016 0.7727 0.028 Uiso 1 1 d D . .
N1A N 1.0547(2) 0.22809(12) 0.84096(15) 0.0267(5) Uani 1 1 d . . .
N2A N 1.1180(2) 0.31452(12) 0.56132(16) 0.0266(5) Uani 1 1 d D . .
H2NA H 1.0810 0.2949 0.4967 0.032 Uiso 1 1 d D . .
C1 C 0.5346(3) 0.19270(15) 0.42721(19) 0.0279(6) Uani 1 1 d . . .
H1 H 0.4924 0.1670 0.3612 0.033 Uiso 1 1 calc R . .
C2 C 0.5137(2) 0.16440(14) 0.51944(19) 0.0256(5) Uani 1 1 d . . .
H2 H 0.4587 0.1216 0.5148 0.031 Uiso 1 1 calc R . .
C3 C 0.5743(2) 0.19934(13) 0.61914(17) 0.0196(5) Uani 1 1 d . . .
C4 C 0.6569(2) 0.26374(13) 0.61910(17) 0.0183(5) Uani 1 1 d . . .
C5 C 0.7278(2) 0.30324(13) 0.71453(18) 0.0202(5) Uani 1 1 d . . .
H5 H 0.7202 0.2877 0.7819 0.024 Uiso 1 1 calc R . .
C6 C 0.8073(2) 0.36364(13) 0.71175(19) 0.0241(5) Uani 1 1 d . . .
H6 H 0.8544 0.3896 0.7764 0.029 Uiso 1 1 calc R . .
C7 C 0.8180(2) 0.38641(13) 0.6117(2) 0.0244(5) Uani 1 1 d . . .
C8 C 0.7514(2) 0.35017(14) 0.5177(2) 0.0252(5) Uani 1 1 d . . .
H8 H 0.7597 0.3669 0.4511 0.030 Uiso 1 1 calc R . .
C9 C 0.6698(2) 0.28768(13) 0.51911(18) 0.0207(5) Uani 1 1 d . . .
C10 C 0.4800(2) 0.11040(14) 0.7210(2) 0.0258(5) Uani 1 1 d . . .
H10A H 0.5136 0.0912 0.7962 0.031 Uiso 1 1 calc R . .
H10B H 0.4937 0.0709 0.6728 0.031 Uiso 1 1 calc R . .
C11 C 0.3288(3) 0.12589(15) 0.6912(2) 0.0307(6) Uani 1 1 d . . .
H11A H 0.3134 0.1635 0.7414 0.037 Uiso 1 1 calc R . .
H11B H 0.2944 0.1464 0.6168 0.037 Uiso 1 1 calc R . .
C12 C 0.2515(3) 0.05510(17) 0.6974(3) 0.0428(7) Uani 1 1 d . . .
H12A H 0.1544 0.0661 0.6761 0.064 Uiso 1 1 calc R . .
H12B H 0.2829 0.0360 0.7718 0.064 Uiso 1 1 calc R . .
H12C H 0.2676 0.0177 0.6484 0.064 Uiso 1 1 calc R . .
C1A C 1.1331(3) 0.28631(15) 0.84294(19) 0.0274(5) Uani 1 1 d . . .
H1A H 1.1748 0.3093 0.9113 0.033 Uiso 1 1 calc R . .
C2A C 1.1602(2) 0.31701(14) 0.75402(18) 0.0236(5) Uani 1 1 d . . .
H2A H 1.2191 0.3586 0.7632 0.028 Uiso 1 1 calc R . .
C3A C 1.0998(2) 0.28609(13) 0.65108(17) 0.0194(5) Uani 1 1 d . . .
C4A C 1.0152(2) 0.22172(13) 0.64481(17) 0.0185(5) Uani 1 1 d . . .
C5A C 0.9495(2) 0.18378(13) 0.54661(18) 0.0223(5) Uani 1 1 d . . .
H5A H 0.9592 0.2017 0.4811 0.027 Uiso 1 1 calc R . .
C6A C 0.8719(3) 0.12146(14) 0.5441(2) 0.0268(5) Uani 1 1 d . . .
H6A H 0.8289 0.0964 0.4777 0.032 Uiso 1 1 calc R . .
C7A C 0.8574(2) 0.09563(13) 0.6412(2) 0.0269(5) Uani 1 1 d . . .
C8A C 0.9163(2) 0.13082(14) 0.7375(2) 0.0256(5) Uani 1 1 d . . .
H8A H 0.9035 0.1124 0.8017 0.031 Uiso 1 1 calc R . .
C9A C 0.9968(2) 0.19528(13) 0.74170(18) 0.0214(5) Uani 1 1 d . . .
C10A C 1.2039(3) 0.37756(15) 0.5600(2) 0.0346(6) Uani 1 1 d . . .
H10C H 1.1980 0.4138 0.6154 0.041 Uiso 1 1 calc R . .
H10D H 1.1689 0.4022 0.4885 0.041 Uiso 1 1 calc R . .
C11A C 1.3482(3) 0.35800(16) 0.5811(2) 0.0368(6) Uani 1 1 d . . .
H11C H 1.3554 0.3215 0.5264 0.044 Uiso 1 1 calc R . .
H11D H 1.3851 0.3347 0.6535 0.044 Uiso 1 1 calc R . .
C12A C 1.4311(3) 0.42739(18) 0.5763(4) 0.0636(11) Uani 1 1 d . . .
H12D H 1.5263 0.4135 0.5917 0.095 Uiso 1 1 calc R . .
H12E H 1.4238 0.4635 0.6303 0.095 Uiso 1 1 calc R . .
H12F H 1.3964 0.4495 0.5039 0.095 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'
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
C1 N1 C9 115.92(19) . . ?
C3 N2 C10 123.9(2) . . ?
C3 N2 H2N 121.7 . . ?
C10 N2 H2N 113.4 . . ?
C1A N1A C9A 115.97(19) . . ?
C3A N2A C10A 124.8(2) . . ?
C3A N2A H2NA 122.6 . . ?
C10A N2A H2NA 112.6 . . ?
N1 C1 C2 126.3(2) . . ?
N1 C1 H1 116.9 . . ?
C2 C1 H1 116.9 . . ?
C1 C2 C3 119.5(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
N2 C3 C2 123.2(2) . . ?
N2 C3 C4 120.1(2) . . ?
C2 C3 C4 116.7(2) . . ?
C5 C4 C9 118.5(2) . . ?
C5 C4 C3 122.91(19) . . ?
C9 C4 C3 118.6(2) . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 119.0(2) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 121.7(2) . . ?
C8 C7 Cl1 119.90(18) . . ?
C6 C7 Cl1 118.42(19) . . ?
C7 C8 C9 120.1(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
N1 C9 C8 117.6(2) . . ?
N1 C9 C4 123.0(2) . . ?
C8 C9 C4 119.4(2) . . ?
N2 C10 C11 114.3(2) . . ?
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 . . ?
C12 C11 C10 110.9(2) . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1A C1A C2A 126.0(2) . . ?
N1A C1A H1A 117.0 . . ?
C2A C1A H1A 117.0 . . ?
C1A C2A C3A 119.4(2) . . ?
C1A C2A H2A 120.3 . . ?
C3A C2A H2A 120.3 . . ?
N2A C3A C2A 122.5(2) . . ?
N2A C3A C4A 120.8(2) . . ?
C2A C3A C4A 116.7(2) . . ?
C5A C4A C9A 118.6(2) . . ?
C5A C4A C3A 123.03(19) . . ?
C9A C4A C3A 118.4(2) . . ?
C6A C5A C4A 121.4(2) . . ?
C6A C5A H5A 119.3 . . ?
C4A C5A H5A 119.3 . . ?
C5A C6A C7A 118.9(2) . . ?
C5A C6A H6A 120.5 . . ?
C7A C6A H6A 120.5 . . ?
C8A C7A C6A 122.1(2) . . ?
C8A C7A Cl1A 119.71(19) . . ?
C6A C7A Cl1A 118.2(2) . . ?
C7A C8A C9A 119.8(2) . . ?
C7A C8A H8A 120.1 . . ?
C9A C8A H8A 120.1 . . ?
N1A C9A C4A 123.4(2) . . ?
N1A C9A C8A 117.4(2) . . ?
C4A C9A C8A 119.2(2) . . ?
N2A C10A C11A 114.0(2) . . ?
N2A C10A H10C 108.7 . . ?
C11A C10A H10C 108.7 . . ?
N2A C10A H10D 108.7 . . ?
C11A C10A H10D 108.7 . . ?
H10C C10A H10D 107.6 . . ?
C10A C11A C12A 110.7(2) . . ?
C10A C11A H11C 109.5 . . ?
C12A C11A H11C 109.5 . . ?
C10A C11A H11D 109.5 . . ?
C12A C11A H11D 109.5 . . ?
H11C C11A H11D 108.1 . . ?
C11A C12A H12D 109.5 . . ?
C11A C12A H12E 109.5 . . ?
H12D C12A H12E 109.5 . . ?
C11A C12A H12F 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
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 1.739(2) . ?
Cl1A C7A 1.748(2) . ?
N1 C1 1.327(3) . ?
N1 C9 1.374(3) . ?
N2 C3 1.355(3) . ?
N2 C10 1.453(3) . ?
N2 H2N 0.8800 . ?
N1A C1A 1.324(3) . ?
N1A C9A 1.372(3) . ?
N2A C3A 1.347(3) . ?
N2A C10A 1.448(3) . ?
N2A H2NA 0.8800 . ?
C1 C2 1.388(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.397(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.443(3) . ?
C4 C5 1.415(3) . ?
C4 C9 1.422(3) . ?
C5 C6 1.375(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.407(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.363(4) . ?
C8 C9 1.413(3) . ?
C8 H8 0.9500 . ?
C10 C11 1.524(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.523(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C1A C2A 1.394(3) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.400(3) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.442(3) . ?
C4A C5A 1.416(3) . ?
C4A C9A 1.421(3) . ?
C5A C6A 1.376(3) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.403(4) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.362(4) . ?
C8A C9A 1.422(3) . ?
C8A H8A 0.9500 . ?
C10A C11A 1.483(4) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C11A C12A 1.531(4) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
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
C9 N1 C1 C2 1.1(4) . . . . ?
N1 C1 C2 C3 -0.7(4) . . . . ?
C10 N2 C3 C2 -1.1(4) . . . . ?
C10 N2 C3 C4 -179.8(2) . . . . ?
C1 C2 C3 N2 -179.1(2) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
N2 C3 C4 C5 0.8(3) . . . . ?
C2 C3 C4 C5 -178.0(2) . . . . ?
N2 C3 C4 C9 179.5(2) . . . . ?
C2 C3 C4 C9 0.7(3) . . . . ?
C9 C4 C5 C6 0.2(3) . . . . ?
C3 C4 C5 C6 178.9(2) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
C5 C6 C7 Cl1 -179.47(18) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
Cl1 C7 C8 C9 179.05(17) . . . . ?
C1 N1 C9 C8 178.5(2) . . . . ?
C1 N1 C9 C4 -0.7(3) . . . . ?
C7 C8 C9 N1 -178.4(2) . . . . ?
C7 C8 C9 C4 0.8(3) . . . . ?
C5 C4 C9 N1 178.5(2) . . . . ?
C3 C4 C9 N1 -0.2(3) . . . . ?
C5 C4 C9 C8 -0.6(3) . . . . ?
C3 C4 C9 C8 -179.4(2) . . . . ?
C3 N2 C10 C11 -81.3(3) . . . . ?
N2 C10 C11 C12 177.8(2) . . . . ?
C9A N1A C1A C2A 0.7(4) . . . . ?
N1A C1A C2A C3A 1.0(4) . . . . ?
C10A N2A C3A C2A 2.1(4) . . . . ?
C10A N2A C3A C4A -178.2(2) . . . . ?
C1A C2A C3A N2A 177.8(2) . . . . ?
C1A C2A C3A C4A -1.9(3) . . . . ?
N2A C3A C4A C5A 1.5(3) . . . . ?
C2A C3A C4A C5A -178.8(2) . . . . ?
N2A C3A C4A C9A -178.4(2) . . . . ?
C2A C3A C4A C9A 1.2(3) . . . . ?
C9A C4A C5A C6A -1.6(3) . . . . ?
C3A C4A C5A C6A 178.5(2) . . . . ?
C4A C5A C6A C7A 0.4(4) . . . . ?
C5A C6A C7A C8A 0.8(4) . . . . ?
C5A C6A C7A Cl1A -179.20(19) . . . . ?
C6A C7A C8A C9A -0.9(4) . . . . ?
Cl1A C7A C8A C9A 179.17(18) . . . . ?
C1A N1A C9A C4A -1.4(3) . . . . ?
C1A N1A C9A C8A 177.6(2) . . . . ?
C5A C4A C9A N1A -179.5(2) . . . . ?
C3A C4A C9A N1A 0.4(3) . . . . ?
C5A C4A C9A C8A 1.5(3) . . . . ?
C3A C4A C9A C8A -178.6(2) . . . . ?
C7A C8A C9A N1A -179.4(2) . . . . ?
C7A C8A C9A C4A -0.3(3) . . . . ?
C3A N2A C10A C11A 85.4(3) . . . . ?
N2A C10A C11A C12A 179.0(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168353933
