#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/14/2201413.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_2201413
loop_
_publ_author_name
'S. Thinagar'
'D. Velmurugan'
'S. Shanmuga Sundara Raj'
'Hoong-Kun Fun'
'V. Raghukumar'
_publ_section_title
6-(4-Chlorophenyl)-4-[4-(dimethylamino)phenyl]-2-(pyrrolidin-1-yl)nicotinonitrile
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1452
_journal_page_last               o1454
_journal_paper_doi               10.1107/S1600536802019931
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C24 H23 Cl N4'
_chemical_formula_moiety         'C24 H23 Cl N4'
_chemical_formula_sum            'C24 H23 Cl N4'
_chemical_formula_weight         402.91
_chemical_name_systematic
;
6-(4-Chlorophenyl)-4-[4-(dimethylamino)phenyl]-2-(pyrrolidin-1-
yl)nicotinonitrile
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.4870(10)
_cell_angle_beta                 93.2400(10)
_cell_angle_gamma                107.0140(10)
_cell_formula_units_Z            4
_cell_length_a                   11.14900(10)
_cell_length_b                   13.73300(10)
_cell_length_c                   14.66660(10)
_cell_measurement_reflns_used    7711
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      1.42
_cell_volume                     2097.00(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1997)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1983, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.918
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_sigmaI/netI    0.0835
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14581
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.42
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.319
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         9579
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0793P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1604
_reflns_number_gt                6307
_reflns_number_total             9579
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6179.cif
_cod_data_source_block           I
_cod_original_cell_volume        2096.93(2)
_cod_database_code               2201413
_cod_database_fobs_code          2201413
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1A -0.02596(6) -0.38678(5) 0.59338(5) 0.0866(2) Uani d . 1 . . Cl
N1A 0.21081(13) 0.08918(11) 0.51050(9) 0.0431(3) Uani d . 1 . . N
N2A 0.28907(15) 0.26496(11) 0.55895(10) 0.0481(4) Uani d . 1 . . N
N3A 0.39956(18) 0.35530(13) 0.34391(12) 0.0628(4) Uani d . 1 . . N
N4A 0.15588(17) 0.09242(14) -0.06908(11) 0.0640(5) Uani d . 1 . . N
C2A 0.25494(16) 0.18186(13) 0.48645(11) 0.0407(4) Uani d . 1 . . C
C3A 0.26408(16) 0.18899(13) 0.39066(11) 0.0407(4) Uani d . 1 . . C
C4A 0.21067(16) 0.09795(13) 0.32108(11) 0.0404(4) Uani d . 1 . . C
C5A 0.16151(17) 0.00392(13) 0.34922(11) 0.0437(4) Uani d . 1 . . C
H5A 0.1256 -0.0573 0.3049 0.052 Uiso calc R 1 . . H
C6A 0.16631(15) 0.00203(13) 0.44416(11) 0.0397(4) Uani d . 1 . . C
C7A 0.2726(2) 0.24839(15) 0.65427(12) 0.0577(5) Uani d . 1 . . C
H7A 0.3256 0.2089 0.6727 0.069 Uiso calc R 1 . . H
H7B 0.1853 0.2116 0.6591 0.069 Uiso calc R 1 . . H
C8A 0.3119(3) 0.35634(18) 0.71363(16) 0.0777(7) Uani d . 1 . . C
H8A 0.3994 0.3765 0.7404 0.093 Uiso calc R 1 . . H
H8B 0.2595 0.3601 0.7639 0.093 Uiso calc R 1 . . H
C9A 0.2948(2) 0.42604(16) 0.64905(15) 0.0685(6) Uani d . 1 . . C
H9A 0.3542 0.4954 0.6696 0.082 Uiso calc R 1 . . H
H9B 0.2096 0.4309 0.6464 0.082 Uiso calc R 1 . . H
C10A 0.3198(2) 0.37435(14) 0.55470(13) 0.0545(5) Uani d . 1 . . C
H10A 0.2665 0.3840 0.5047 0.065 Uiso calc R 1 . . H
H10B 0.4075 0.4024 0.5450 0.065 Uiso calc R 1 . . H
C11A 0.33675(18) 0.28231(15) 0.36491(12) 0.0470(4) Uani d . 1 . . C
C12A 0.20264(16) 0.10013(13) 0.22023(11) 0.0425(4) Uani d . 1 . . C
C13A 0.16198(17) 0.17451(14) 0.18509(12) 0.0459(4) Uani d . 1 . . C
H13A 0.1461 0.2278 0.2266 0.055 Uiso calc R 1 . . H
C14A 0.14480(17) 0.17124(15) 0.09087(13) 0.0495(4) Uani d . 1 . . C
H14A 0.1159 0.2214 0.0703 0.059 Uiso calc R 1 . . H
C15A 0.16985(16) 0.09399(15) 0.02500(12) 0.0472(4) Uani d . 1 . . C
C16A 0.21283(19) 0.02003(15) 0.06020(12) 0.0517(4) Uani d . 1 . . C
H16A 0.2322 -0.0317 0.0190 0.062 Uiso calc R 1 . . H
C17A 0.22686(18) 0.02288(14) 0.15493(12) 0.0500(4) Uani d . 1 . . C
H17A 0.2533 -0.0284 0.1758 0.060 Uiso calc R 1 . . H
C18A 0.11896(15) -0.09523(13) 0.47940(11) 0.0400(4) Uani d . 1 . . C
C19A 0.09205(18) -0.19282(14) 0.42202(13) 0.0488(4) Uani d . 1 . . C
H19A 0.1034 -0.1980 0.3592 0.059 Uiso calc R 1 . . H
C20A 0.04842(19) -0.28293(15) 0.45645(14) 0.0559(5) Uani d . 1 . . C
H20A 0.0314 -0.3480 0.4173 0.067 Uiso calc R 1 . . H
C21A 0.03079(18) -0.27462(15) 0.54923(14) 0.0538(5) Uani d . 1 . . C
C22A 0.05682(19) -0.17883(16) 0.60837(14) 0.0566(5) Uani d . 1 . . C
H22A 0.0450 -0.1742 0.6711 0.068 Uiso calc R 1 . . H
C23A 0.10068(18) -0.08987(15) 0.57333(12) 0.0493(4) Uani d . 1 . . C
H23A 0.1184 -0.0251 0.6130 0.059 Uiso calc R 1 . . H
C24A 0.1804(3) 0.0111(2) -0.13572(15) 0.0832(7) Uani d . 1 . . C
H24A 0.2623 0.0063 -0.1181 0.125 Uiso calc R 1 . . H
H24B 0.1777 0.0272 -0.1967 0.125 Uiso calc R 1 . . H
H24C 0.1174 -0.0540 -0.1366 0.125 Uiso calc R 1 . . H
C25A 0.0992(2) 0.1623(2) -0.10475(16) 0.0761(7) Uani d . 1 . . C
H25A 0.1477 0.2330 -0.0777 0.114 Uiso calc R 1 . . H
H25B 0.0144 0.1495 -0.0888 0.114 Uiso calc R 1 . . H
H25C 0.0978 0.1507 -0.1714 0.114 Uiso calc R 1 . . H
Cl1B 0.56120(7) 0.11966(5) -0.06469(5) 0.0903(2) Uani d . 1 . . Cl
N1B 0.27692(14) 0.48400(11) 0.01936(10) 0.0450(3) Uani d . 1 . . N
N2B 0.16274(16) 0.58056(13) -0.03099(10) 0.0546(4) Uani d . 1 . . N
N3B 0.1058(2) 0.73715(19) 0.19077(13) 0.0944(8) Uani d . 1 . . N
N4B 0.40411(19) 0.80256(14) 0.58715(12) 0.0674(5) Uani d . 1 . . N
C2B 0.22383(17) 0.55999(14) 0.04215(12) 0.0448(4) Uani d . 1 . . C
C3B 0.23303(17) 0.61224(14) 0.13737(12) 0.0464(4) Uani d . 1 . . C
C4B 0.30233(16) 0.58518(13) 0.20667(11) 0.0427(4) Uani d . 1 . . C
C5B 0.35384(16) 0.50485(13) 0.18000(12) 0.0442(4) Uani d . 1 . . C
H5B 0.3966 0.4830 0.2246 0.053 Uiso calc R 1 . . H
C6B 0.34082(15) 0.45748(13) 0.08610(11) 0.0407(4) Uani d . 1 . . C
C7B 0.1653(2) 0.52465(18) -0.12654(13) 0.0652(6) Uani d . 1 . . C
H7C 0.1231 0.4506 -0.1342 0.078 Uiso calc R 1 . . H
H7D 0.2513 0.5354 -0.1413 0.078 Uiso calc R 1 . . H
C8B 0.0948(3) 0.5730(2) -0.18689(17) 0.0961(9) Uani d . 1 . . C
H8C 0.1318 0.5785 -0.2448 0.115 Uiso calc R 1 . . H
H8D 0.0068 0.5311 -0.2017 0.115 Uiso calc R 1 . . H
C9B 0.1053(4) 0.6731(3) -0.13448(19) 0.1218(14) Uani d . 1 . . C
H9C 0.0323 0.6935 -0.1517 0.146 Uiso calc R 1 . . H
H9D 0.1805 0.7240 -0.1465 0.146 Uiso calc R 1 . . H
C10B 0.1131(2) 0.66733(18) -0.03218(15) 0.0681(6) Uani d . 1 . . C
H10C 0.1697 0.7313 0.0061 0.082 Uiso calc R 1 . . H
H10D 0.0305 0.6537 -0.0103 0.082 Uiso calc R 1 . . H
C11B 0.1642(2) 0.68392(17) 0.16594(13) 0.0622(5) Uani d . 1 . . C
C12B 0.32554(17) 0.64203(13) 0.30520(12) 0.0435(4) Uani d . 1 . . C
C13B 0.37128(18) 0.74982(14) 0.32965(13) 0.0506(4) Uani d . 1 . . C
H13B 0.3836 0.7877 0.2826 0.061 Uiso calc R 1 . . H
C14B 0.39903(19) 0.80240(14) 0.42143(13) 0.0523(4) Uani d . 1 . . C
H14B 0.4316 0.8746 0.4348 0.063 Uiso calc R 1 . . H
C15B 0.37941(17) 0.74988(14) 0.49475(12) 0.0471(4) Uani d . 1 . . C
C16B 0.33469(19) 0.64076(14) 0.47045(12) 0.0521(4) Uani d . 1 . . C
H16B 0.3219 0.6028 0.5174 0.063 Uiso calc R 1 . . H
C17B 0.30930(18) 0.58880(14) 0.37856(12) 0.0480(4) Uani d . 1 . . C
H17B 0.2806 0.5164 0.3649 0.058 Uiso calc R 1 . . H
C18B 0.40065(15) 0.37612(13) 0.05188(11) 0.0401(4) Uani d . 1 . . C
C19B 0.44773(18) 0.32400(15) 0.11074(13) 0.0526(4) Uani d . 1 . . C
H19B 0.4461 0.3422 0.1748 0.063 Uiso calc R 1 . . H
C20B 0.4970(2) 0.24541(17) 0.07529(15) 0.0608(5) Uani d . 1 . . C
H20B 0.5267 0.2099 0.1151 0.073 Uiso calc R 1 . . H
C21B 0.50179(18) 0.22026(15) -0.01918(15) 0.0556(5) Uani d . 1 . . C
C22B 0.45904(19) 0.27182(15) -0.07922(14) 0.0555(5) Uani d . 1 . . C
H22B 0.4636 0.2547 -0.1430 0.067 Uiso calc R 1 . . H
C23B 0.40904(18) 0.34975(14) -0.04320(12) 0.0485(4) Uani d . 1 . . C
H23B 0.3804 0.3853 -0.0835 0.058 Uiso calc R 1 . . H
C24B 0.3554(2) 0.75155(19) 0.66077(15) 0.0736(6) Uani d . 1 . . C
H24D 0.2678 0.7128 0.6430 0.110 Uiso calc R 1 . . H
H24E 0.3641 0.8028 0.7169 0.110 Uiso calc R 1 . . H
H24F 0.4017 0.7050 0.6715 0.110 Uiso calc R 1 . . H
C25B 0.4560(3) 0.91400(17) 0.60971(17) 0.0794(7) Uani d . 1 . . C
H25D 0.5295 0.9351 0.5783 0.119 Uiso calc R 1 . . H
H25E 0.4789 0.9371 0.6759 0.119 Uiso calc R 1 . . H
H25F 0.3941 0.9443 0.5900 0.119 Uiso calc R 1 . . H
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_publ_flag
C6A N1A C2A 120.03(14) ?
C2A N2A C10A 127.52(15) ?
C2A N2A C7A 119.42(15) ?
C10A N2A C7A 112.01(14) ?
C15A N4A C24A 120.53(19) ?
C15A N4A C25A 120.97(18) ?
C24A N4A C25A 117.89(18) ?
N1A C2A N2A 114.81(14) y
N1A C2A C3A 121.00(14) ?
N2A C2A C3A 124.19(16) y
C4A C3A C11A 119.50(14) ?
C4A C3A C2A 118.41(15) ?
C11A C3A C2A 121.74(15) ?
C5A C4A C3A 118.23(14) ?
C5A C4A C12A 119.65(15) ?
C3A C4A C12A 122.10(15) ?
C4A C5A C6A 119.77(15) ?
C4A C5A H5A 120.1 ?
C6A C5A H5A 120.1 ?
N1A C6A C5A 122.09(16) ?
N1A C6A C18A 114.99(14) y
C5A C6A C18A 122.89(15) y
N2A C7A C8A 104.21(17) ?
N2A C7A H7A 110.9 ?
C8A C7A H7A 110.9 ?
N2A C7A H7B 110.9 ?
C8A C7A H7B 110.9 ?
H7A C7A H7B 108.9 ?
C7A C8A C9A 105.59(18) ?
C7A C8A H8A 110.6 ?
C9A C8A H8A 110.6 ?
C7A C8A H8B 110.6 ?
C9A C8A H8B 110.6 ?
H8A C8A H8B 108.8 ?
C8A C9A C10A 104.69(17) ?
C8A C9A H9A 110.8 ?
C10A C9A H9A 110.8 ?
C8A C9A H9B 110.8 ?
C10A C9A H9B 110.8 ?
H9A C9A H9B 108.9 ?
N2A C10A C9A 104.13(16) ?
N2A C10A H10A 110.9 ?
C9A C10A H10A 110.9 ?
N2A C10A H10B 110.9 ?
C9A C10A H10B 110.9 ?
H10A C10A H10B 108.9 ?
N3A C11A C3A 176.9(2) ?
C17A C12A C13A 116.61(15) ?
C17A C12A C4A 121.11(15) ?
C13A C12A C4A 122.12(15) ?
C14A C13A C12A 121.95(16) ?
C14A C13A H13A 119.0 ?
C12A C13A H13A 119.0 ?
C13A C14A C15A 121.57(17) ?
C13A C14A H14A 119.2 ?
C15A C14A H14A 119.2 ?
N4A C15A C14A 121.53(18) ?
N4A C15A C16A 121.83(17) ?
C14A C15A C16A 116.62(16) ?
C17A C16A C15A 121.15(16) ?
C17A C16A H16A 119.4 ?
C15A C16A H16A 119.4 ?
C16A C17A C12A 122.06(17) ?
C16A C17A H17A 119.0 ?
C12A C17A H17A 119.0 ?
C19A C18A C23A 118.05(16) ?
C19A C18A C6A 122.17(15) ?
C23A C18A C6A 119.77(15) ?
C18A C19A C20A 121.30(17) ?
C18A C19A H19A 119.3 ?
C20A C19A H19A 119.3 ?
C21A C20A C19A 119.02(18) ?
C21A C20A H20A 120.5 ?
C19A C20A H20A 120.5 ?
C20A C21A C22A 121.25(18) ?
C20A C21A Cl1A 119.70(16) ?
C22A C21A Cl1A 119.05(16) ?
C21A C22A C23A 119.14(18) ?
C21A C22A H22A 120.4 ?
C23A C22A H22A 120.4 ?
C22A C23A C18A 121.24(17) ?
C22A C23A H23A 119.4 ?
C18A C23A H23A 119.4 ?
N4A C24A H24A 109.5 ?
N4A C24A H24B 109.5 ?
H24A C24A H24B 109.5 ?
N4A C24A H24C 109.5 ?
H24A C24A H24C 109.5 ?
H24B C24A H24C 109.5 ?
N4A C25A H25A 109.5 ?
N4A C25A H25B 109.5 ?
H25A C25A H25B 109.5 ?
N4A C25A H25C 109.5 ?
H25A C25A H25C 109.5 ?
H25B C25A H25C 109.5 ?
C6B N1B C2B 119.91(14) ?
C2B N2B C10B 128.03(16) ?
C2B N2B C7B 119.39(15) ?
C10B N2B C7B 111.36(15) ?
C15B N4B C25B 120.12(18) ?
C15B N4B C24B 121.23(18) ?
C25B N4B C24B 117.40(19) ?
N1B C2B N2B 114.66(15) y
N1B C2B C3B 120.71(15) ?
N2B C2B C3B 124.62(16) y
C4B C3B C2B 118.92(15) ?
C4B C3B C11B 118.55(16) ?
C2B C3B C11B 122.26(16) ?
C5B C4B C3B 118.28(15) ?
C5B C4B C12B 119.68(15) ?
C3B C4B C12B 121.99(15) ?
C6B C5B C4B 119.50(16) ?
C6B C5B H5B 120.3 ?
C4B C5B H5B 120.3 ?
N1B C6B C5B 122.60(15) ?
N1B C6B C18B 115.00(14) y
C5B C6B C18B 122.37(15) y
N2B C7B C8B 103.24(17) ?
N2B C7B H7C 111.1 ?
C8B C7B H7C 111.1 ?
N2B C7B H7D 111.1 ?
C8B C7B H7D 111.1 ?
H7C C7B H7D 109.1 ?
C9B C8B C7B 106.3(2) ?
C9B C8B H8C 110.5 ?
C7B C8B H8C 110.5 ?
C9B C8B H8D 110.5 ?
C7B C8B H8D 110.5 ?
H8C C8B H8D 108.7 ?
C8B C9B C10B 107.5(2) ?
C8B C9B H9C 110.2 ?
C10B C9B H9C 110.2 ?
C8B C9B H9D 110.2 ?
C10B C9B H9D 110.2 ?
H9C C9B H9D 108.5 ?
N2B C10B C9B 102.85(17) ?
N2B C10B H10C 111.2 ?
C9B C10B H10C 111.2 ?
N2B C10B H10D 111.2 ?
C9B C10B H10D 111.2 ?
H10C C10B H10D 109.1 ?
N3B C11B C3B 176.5(3) ?
C13B C12B C17B 116.67(16) ?
C13B C12B C4B 122.05(15) ?
C17B C12B C4B 121.18(15) ?
C14B C13B C12B 122.01(17) ?
C14B C13B H13B 119.0 ?
C12B C13B H13B 119.0 ?
C13B C14B C15B 121.53(17) ?
C13B C14B H14B 119.2 ?
C15B C14B H14B 119.2 ?
N4B C15B C14B 121.75(17) ?
N4B C15B C16B 121.56(17) ?
C14B C15B C16B 116.69(16) ?
C17B C16B C15B 121.35(17) ?
C17B C16B H16B 119.3 ?
C15B C16B H16B 119.3 ?
C16B C17B C12B 121.71(17) ?
C16B C17B H17B 119.1 ?
C12B C17B H17B 119.1 ?
C19B C18B C23B 118.05(16) ?
C19B C18B C6B 122.85(15) ?
C23B C18B C6B 119.10(15) ?
C20B C19B C18B 120.82(18) ?
C20B C19B H19B 119.6 ?
C18B C19B H19B 119.6 ?
C21B C20B C19B 119.47(18) ?
C21B C20B H20B 120.3 ?
C19B C20B H20B 120.3 ?
C22B C21B C20B 121.33(17) ?
C22B C21B Cl1B 118.91(16) ?
C20B C21B Cl1B 119.75(16) ?
C21B C22B C23B 118.78(18) ?
C21B C22B H22B 120.6 ?
C23B C22B H22B 120.6 ?
C22B C23B C18B 121.50(17) ?
C22B C23B H23B 119.2 ?
C18B C23B H23B 119.2 ?
N4B C24B H24D 109.5 ?
N4B C24B H24E 109.5 ?
H24D C24B H24E 109.5 ?
N4B C24B H24F 109.5 ?
H24D C24B H24F 109.5 ?
H24E C24B H24F 109.5 ?
N4B C25B H25D 109.5 ?
N4B C25B H25E 109.5 ?
H25D C25B H25E 109.5 ?
N4B C25B H25F 109.5 ?
H25D C25B H25F 109.5 ?
H25E C25B H25F 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1A C21A . 1.741(2) ?
N1A C6A . 1.341(2) ?
N1A C2A . 1.343(2) ?
N2A C2A . 1.355(2) y
N2A C10A . 1.454(2) y
N2A C7A . 1.470(2) y
N3A C11A . 1.147(2) ?
N4A C15A . 1.375(2) y
N4A C24A . 1.445(3) y
N4A C25A . 1.447(3) y
C2A C3A . 1.433(2) ?
C3A C4A . 1.411(2) ?
C3A C11A . 1.430(2) ?
C4A C5A . 1.394(2) ?
C4A C12A . 1.483(2) ?
C5A C6A . 1.396(2) ?
C5A H5A . 0.93 ?
C6A C18A . 1.483(2) ?
C7A C8A . 1.502(3) ?
C7A H7A . 0.97 ?
C7A H7B . 0.97 ?
C8A C9A . 1.505(3) ?
C8A H8A . 0.97 ?
C8A H8B . 0.97 ?
C9A C10A . 1.516(3) ?
C9A H9A . 0.97 ?
C9A H9B . 0.97 ?
C10A H10A . 0.97 ?
C10A H10B . 0.97 ?
C12A C17A . 1.394(2) ?
C12A C13A . 1.397(2) ?
C13A C14A . 1.375(2) ?
C13A H13A . 0.93 ?
C14A C15A . 1.403(3) ?
C14A H14A . 0.93 ?
C15A C16A . 1.406(3) ?
C16A C17A . 1.381(2) ?
C16A H16A . 0.93 ?
C17A H17A . 0.93 ?
C18A C19A . 1.386(2) ?
C18A C23A . 1.396(2) ?
C19A C20A . 1.388(3) ?
C19A H19A . 0.93 ?
C20A C21A . 1.375(3) ?
C20A H20A . 0.93 ?
C21A C22A . 1.378(3) ?
C22A C23A . 1.380(3) ?
C22A H22A . 0.93 ?
C23A H23A . 0.93 ?
C24A H24A . 0.96 ?
C24A H24B . 0.96 ?
C24A H24C . 0.96 ?
C25A H25A . 0.96 ?
C25A H25B . 0.96 ?
C25A H25C . 0.96 ?
Cl1B C21B . 1.7444(19) ?
N1B C6B . 1.342(2) ?
N1B C2B . 1.345(2) ?
N2B C2B . 1.354(2) y
N2B C10B . 1.455(2) y
N2B C7B . 1.476(2) y
N3B C11B . 1.140(3) ?
N4B C15B . 1.386(2) y
N4B C25B . 1.436(3) y
N4B C24B . 1.439(3) y
C2B C3B . 1.432(2) ?
C3B C4B . 1.409(2) ?
C3B C11B . 1.436(3) ?
C4B C5B . 1.392(2) ?
C4B C12B . 1.481(2) ?
C5B C6B . 1.392(2) ?
C5B H5B . 0.93 ?
C6B C18B . 1.488(2) ?
C7B C8B . 1.511(3) y
C7B H7C . 0.97 ?
C7B H7D . 0.97 ?
C8B C9B . 1.416(4) y
C8B H8C . 0.97 ?
C8B H8D . 0.97 ?
C9B C10B . 1.516(3) y
C9B H9C . 0.97 ?
C9B H9D . 0.97 ?
C10B H10C . 0.97 ?
C10B H10D . 0.97 ?
C12B C13B . 1.387(2) ?
C12B C17B . 1.398(2) ?
C13B C14B . 1.377(3) ?
C13B H13B . 0.93 ?
C14B C15B . 1.393(3) ?
C14B H14B . 0.93 ?
C15B C16B . 1.403(3) ?
C16B C17B . 1.376(2) ?
C16B H16B . 0.93 ?
C17B H17B . 0.93 ?
C18B C19B . 1.388(2) ?
C18B C23B . 1.391(2) ?
C19B C20B . 1.383(3) ?
C19B H19B . 0.93 ?
C20B C21B . 1.374(3) ?
C20B H20B . 0.93 ?
C21B C22B . 1.371(3) ?
C22B C23B . 1.383(2) ?
C22B H22B . 0.93 ?
C23B H23B . 0.93 ?
C24B H24D . 0.96 ?
C24B H24E . 0.96 ?
C24B H24F . 0.96 ?
C25B H25D . 0.96 ?
C25B H25E . 0.96 ?
C25B H25F . 0.96 ?
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
C19B H19B N3A . 0.93 2.55 3.461(3) 167 y
C19A H19A N3B 1_545 0.93 2.47 3.378(3) 164 y
C24B H24F N3A 2_666 0.96 2.59 3.457(3) 150 y
C23A H23A N1A . 0.93 2.42 2.755(2) 101 y
C23B H23B N1B . 0.93 2.41 2.745(3) 101 y
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
C6A N1A C2A N2A 175.55(15)
C6A N1A C2A C3A -4.6(2)
C10A N2A C2A N1A -168.95(17)
C7A N2A C2A N1A -1.7(2)
C10A N2A C2A C3A 11.2(3)
C7A N2A C2A C3A 178.52(16)
N1A C2A C3A C4A 8.1(2)
N2A C2A C3A C4A -172.10(16)
N1A C2A C3A C11A -165.16(15)
N2A C2A C3A C11A 14.7(3)
C11A C3A C4A C5A 167.86(16)
C2A C3A C4A C5A -5.5(2)
C11A C3A C4A C12A -13.7(2)
C2A C3A C4A C12A 172.88(15)
C3A C4A C5A C6A -0.1(2)
C12A C4A C5A C6A -178.52(15)
C2A N1A C6A C5A -1.3(2)
C2A N1A C6A C18A -179.35(14)
C4A C5A C6A N1A 3.7(2)
C4A C5A C6A C18A -178.42(15)
C2A N2A C7A C8A -176.48(18)
C10A N2A C7A C8A -7.3(2)
N2A C7A C8A C9A 23.7(2)
C7A C8A C9A C10A -31.2(3)
C2A N2A C10A C9A 156.24(18)
C7A N2A C10A C9A -11.8(2)
C8A C9A C10A N2A 26.2(2)
C5A C4A C12A C17A -42.0(2)
C3A C4A C12A C17A 139.55(18)
C5A C4A C12A C13A 133.25(18)
C3A C4A C12A C13A -45.2(2)
C17A C12A C13A C14A 0.9(3)
C4A C12A C13A C14A -174.58(16)
C12A C13A C14A C15A -1.4(3)
C24A N4A C15A C14A -179.0(2)
C25A N4A C15A C14A -8.1(3)
C24A N4A C15A C16A 2.6(3)
C25A N4A C15A C16A 173.49(19)
C13A C14A C15A N4A -178.23(17)
C13A C14A C15A C16A 0.3(3)
N4A C15A C16A C17A 179.74(17)
C14A C15A C16A C17A 1.3(3)
C15A C16A C17A C12A -1.7(3)
C13A C12A C17A C16A 0.6(3)
C4A C12A C17A C16A 176.17(17)
N1A C6A C18A C19A -167.70(15)
C5A C6A C18A C19A 14.3(2)
N1A C6A C18A C23A 12.1(2)
C5A C6A C18A C23A -165.89(16)
C23A C18A C19A C20A -0.1(3)
C6A C18A C19A C20A 179.66(16)
C18A C19A C20A C21A 0.5(3)
C19A C20A C21A C22A -0.7(3)
C19A C20A C21A Cl1A 179.11(15)
C20A C21A C22A C23A 0.4(3)
Cl1A C21A C22A C23A -179.40(15)
C21A C22A C23A C18A 0.0(3)
C19A C18A C23A C22A -0.2(3)
C6A C18A C23A C22A -179.97(16)
C6B N1B C2B N2B 179.49(16)
C6B N1B C2B C3B -0.9(3)
C10B N2B C2B N1B -169.62(19)
C7B N2B C2B N1B -3.4(3)
C10B N2B C2B C3B 10.8(3)
C7B N2B C2B C3B 177.07(18)
N1B C2B C3B C4B 2.1(3)
N2B C2B C3B C4B -178.35(18)
N1B C2B C3B C11B -171.72(19)
N2B C2B C3B C11B 7.8(3)
C2B C3B C4B C5B -3.1(3)
C11B C3B C4B C5B 170.93(18)
C2B C3B C4B C12B 174.50(15)
C11B C3B C4B C12B -11.4(3)
C3B C4B C5B C6B 3.1(3)
C12B C4B C5B C6B -174.62(15)
C2B N1B C6B C5B 0.9(3)
C2B N1B C6B C18B -177.10(15)
C4B C5B C6B N1B -2.0(3)
C4B C5B C6B C18B 175.85(15)
C2B N2B C7B C8B -176.8(2)
C10B N2B C7B C8B -8.4(3)
N2B C7B C8B C9B 24.0(3)
C7B C8B C9B C10B -30.8(4)
C2B N2B C10B C9B 158.1(2)
C7B N2B C10B C9B -9.1(3)
C8B C9B C10B N2B 24.7(4)
C5B C4B C12B C13B 128.23(19)
C3B C4B C12B C13B -49.4(3)
C5B C4B C12B C17B -47.9(2)
C3B C4B C12B C17B 134.50(19)
C17B C12B C13B C14B -0.3(3)
C4B C12B C13B C14B -176.56(17)
C12B C13B C14B C15B -1.7(3)
C25B N4B C15B C14B -2.5(3)
C24B N4B C15B C14B 164.4(2)
C25B N4B C15B C16B 176.8(2)
C24B N4B C15B C16B -16.4(3)
C13B C14B C15B N4B -178.31(19)
C13B C14B C15B C16B 2.4(3)
N4B C15B C16B C17B 179.46(19)
C14B C15B C16B C17B -1.2(3)
C15B C16B C17B C12B -0.7(3)
C13B C12B C17B C16B 1.4(3)
C4B C12B C17B C16B 177.76(17)
N1B C6B C18B C19B -166.42(17)
C5B C6B C18B C19B 15.6(3)
N1B C6B C18B C23B 12.9(2)
C5B C6B C18B C23B -165.10(16)
C23B C18B C19B C20B -2.5(3)
C6B C18B C19B C20B 176.84(17)
C18B C19B C20B C21B 1.4(3)
C19B C20B C21B C22B 0.2(3)
C19B C20B C21B Cl1B -178.85(17)
C20B C21B C22B C23B -0.7(3)
Cl1B C21B C22B C23B 178.37(15)
C21B C22B C23B C18B -0.4(3)
C19B C18B C23B C22B 2.0(3)
C6B C18B C23B C22B -177.35(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9421691
