#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/52/2225258.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_2225258
loop_
_publ_author_name
'Boechat, Núbia'
'dos Santos Lages, Adriana'
'Kover, Warner B.'
'Tiekink, Edward R. T.'
'Wardell, James L.'
'Wardell, Solange M. S. V.'
_publ_section_title
;
 2-Chloro-6,6-dimethyl-5,6-dihydroindazolo[2,3-c]quinazoline
;
_journal_coeditor_code           HB5323
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o521
_journal_page_last               o522
_journal_paper_doi               10.1107/S1600536810003818
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H14 Cl N3'
_chemical_formula_moiety         'C16 H14 Cl N3'
_chemical_formula_sum            'C16 H14 Cl N3'
_chemical_formula_weight         283.75
_chemical_name_systematic
;
2-Chloro-6,6-dimethyl-5,6-dihydroindazolo[2,3-c]quinazoline
;
_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                93.4830(10)
_cell_angle_beta                 100.3910(10)
_cell_angle_gamma                104.4190(10)
_cell_formula_units_Z            4
_cell_length_a                   9.8636(2)
_cell_length_b                   10.7971(2)
_cell_length_c                   13.2387(3)
_cell_measurement_reflns_used    5954
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     1334.81(5)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material
'PLATON (Spek, 2003) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  '10 cm confocal mirrors'
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_av_sigmaI/netI    0.031
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27218
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.9
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         6102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.046
_refine_ls_R_factor_gt           0.036
_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)+(0.0459P)²+0.5871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.089
_refine_ls_wR_factor_ref         0.094
_reflns_number_gt                5108
_reflns_number_total             6102
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5323.cif
_cod_data_source_block           I
_cod_database_code               2225258
_cod_database_fobs_code          2225258
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.33159(4) -0.34794(3) 0.46107(3) 0.02533(10) Uani d . 1 . .
N N1 0.47189(12) 0.14829(11) 0.28749(9) 0.0170(2) Uani d . 1 . .
H H1N 0.5189(18) 0.1492(16) 0.2355(13) 0.020 Uiso d . 1 . .
N N2 0.30560(12) 0.22108(10) 0.36420(8) 0.0146(2) Uani d . 1 . .
N N3 0.25126(12) 0.31785(11) 0.39366(9) 0.0166(2) Uani d . 1 . .
C C1 0.37097(15) -0.20111(13) 0.41036(10) 0.0178(3) Uani d . 1 . .
C C2 0.46556(15) -0.18303(13) 0.34342(11) 0.0191(3) Uani d . 1 . .
H H2 0.5094 -0.2488 0.3275 0.023 Uiso calc R 1 . .
C C3 0.49562(14) -0.06863(13) 0.30000(11) 0.0180(3) Uani d . 1 . .
H H3 0.5592 -0.0565 0.2532 0.022 Uiso calc R 1 . .
C C4 0.43335(14) 0.02947(13) 0.32429(10) 0.0153(3) Uani d . 1 . .
C C5 0.33861(14) 0.01066(13) 0.39313(10) 0.0149(3) Uani d . 1 . .
C C6 0.30674(14) -0.10637(13) 0.43533(10) 0.0166(3) Uani d . 1 . .
H H6 0.2415 -0.1207 0.4808 0.020 Uiso calc R 1 . .
C C7 0.37046(14) 0.22740(13) 0.27162(10) 0.0160(3) Uani d . 1 . .
C C8 0.45339(16) 0.36485(14) 0.26594(12) 0.0215(3) Uani d . 1 . .
H H8A 0.5234 0.3969 0.3306 0.032 Uiso calc R 1 . .
H H8B 0.3871 0.4193 0.2555 0.032 Uiso calc R 1 . .
H H8C 0.5032 0.3670 0.2081 0.032 Uiso calc R 1 . .
C C9 0.25205(16) 0.17480(15) 0.17637(11) 0.0231(3) Uani d . 1 . .
H H9A 0.2939 0.1762 0.1146 0.035 Uiso calc R 1 . .
H H9B 0.1845 0.2282 0.1703 0.035 Uiso calc R 1 . .
H H9C 0.2017 0.0862 0.1831 0.035 Uiso calc R 1 . .
C C10 0.28291(14) 0.11864(13) 0.41894(10) 0.0148(3) Uani d . 1 . .
C C11 0.20930(14) 0.15069(13) 0.49425(10) 0.0150(3) Uani d . 1 . .
C C12 0.15553(15) 0.09112(13) 0.57641(10) 0.0177(3) Uani d . 1 . .
H H12 0.1643 0.0077 0.5897 0.021 Uiso calc R 1 . .
C C13 0.09056(15) 0.15635(14) 0.63631(11) 0.0211(3) Uani d . 1 . .
H H13 0.0535 0.1171 0.6915 0.025 Uiso calc R 1 . .
C C14 0.07742(16) 0.28172(14) 0.61761(11) 0.0219(3) Uani d . 1 . .
H H14 0.0322 0.3245 0.6608 0.026 Uiso calc R 1 . .
C C15 0.12848(15) 0.34197(13) 0.53880(11) 0.0194(3) Uani d . 1 . .
H H15 0.1199 0.4259 0.5271 0.023 Uiso calc R 1 . .
C C16 0.19440(14) 0.27539(13) 0.47525(10) 0.0160(3) Uani d . 1 . .
Cl Cl2 1.01515(4) 0.86179(3) 0.04959(3) 0.02812(11) Uani d . 1 . .
N N4 1.01094(12) 0.36108(11) 0.20762(9) 0.0162(2) Uani d . 1 . .
H H4N 1.0824(18) 0.3620(16) 0.2564(13) 0.019 Uiso d . 1 . .
N N5 0.76776(12) 0.28013(10) 0.13350(8) 0.0147(2) Uani d . 1 . .
N N6 0.64868(12) 0.18074(11) 0.10529(9) 0.0159(2) Uani d . 1 . .
C C17 1.01399(15) 0.71382(13) 0.09521(11) 0.0182(3) Uani d . 1 . .
C C18 1.13622(15) 0.69989(13) 0.15913(11) 0.0186(3) Uani d . 1 . .
H H18 1.2199 0.7697 0.1762 0.022 Uiso calc R 1 . .
C C19 1.13493(14) 0.58330(13) 0.19782(10) 0.0171(3) Uani d . 1 . .
H H19 1.2183 0.5733 0.2415 0.020 Uiso calc R 1 . .
C C20 1.01243(14) 0.48057(13) 0.17320(10) 0.0146(3) Uani d . 1 . .
C C21 0.88979(14) 0.49500(12) 0.10646(10) 0.0143(3) Uani d . 1 . .
C C22 0.89169(15) 0.61293(13) 0.06827(10) 0.0166(3) Uani d . 1 . .
H H22 0.8093 0.6239 0.0240 0.020 Uiso calc R 1 . .
C C23 0.87707(14) 0.27850(13) 0.22571(10) 0.0157(3) Uani d . 1 . .
C C24 0.89323(16) 0.14258(13) 0.23258(12) 0.0209(3) Uani d . 1 . .
H H24A 0.9129 0.1102 0.1675 0.031 Uiso calc R 1 . .
H H24B 0.8047 0.0865 0.2453 0.031 Uiso calc R 1 . .
H H24C 0.9725 0.1435 0.2894 0.031 Uiso calc R 1 . .
C C25 0.83271(15) 0.33020(15) 0.32098(11) 0.0215(3) Uani d . 1 . .
H H25A 0.9060 0.3329 0.3824 0.032 Uiso calc R 1 . .
H H25B 0.7414 0.2738 0.3288 0.032 Uiso calc R 1 . .
H H25C 0.8222 0.4172 0.3129 0.032 Uiso calc R 1 . .
C C26 0.76750(14) 0.38327(12) 0.08024(10) 0.0142(3) Uani d . 1 . .
C C27 0.63765(14) 0.34888(12) 0.00739(10) 0.0146(3) Uani d . 1 . .
C C28 0.57034(15) 0.40825(13) -0.07201(10) 0.0174(3) Uani d . 1 . .
H H28 0.6155 0.4920 -0.0863 0.021 Uiso calc R 1 . .
C C29 0.43847(15) 0.34197(14) -0.12786(11) 0.0200(3) Uani d . 1 . .
H H29 0.3911 0.3813 -0.1806 0.024 Uiso calc R 1 . .
C C30 0.37114(15) 0.21577(14) -0.10858(11) 0.0201(3) Uani d . 1 . .
H H30 0.2795 0.1727 -0.1486 0.024 Uiso calc R 1 . .
C C31 0.43480(15) 0.15426(13) -0.03367(10) 0.0175(3) Uani d . 1 . .
H H31 0.3900 0.0690 -0.0225 0.021 Uiso calc R 1 . .
C C32 0.56925(14) 0.22232(13) 0.02623(10) 0.0155(3) Uani d . 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 0.0000 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 N1 C7 . . 120.26(11) ?
C4 N1 H1N . . 114.6(11) ?
C7 N1 H1N . . 111.3(11) ?
C10 N2 N3 . . 115.05(11) ?
C10 N2 C7 . . 124.91(11) ?
N3 N2 C7 . . 119.74(11) ?
N2 N3 C16 . . 103.00(11) ?
C6 C1 C2 . . 121.31(13) ?
C6 C1 Cl1 . . 120.29(11) ?
C2 C1 Cl1 . . 118.39(10) ?
C3 C2 C1 . . 119.49(13) ?
C3 C2 H2 . . 120.3 ?
C1 C2 H2 . . 120.3 ?
C2 C3 C4 . . 120.61(13) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
N1 C4 C3 . . 120.82(12) ?
N1 C4 C5 . . 119.55(12) ?
C3 C4 C5 . . 119.45(12) ?
C6 C5 C4 . . 119.58(12) ?
C6 C5 C10 . . 123.71(12) ?
C4 C5 C10 . . 116.68(12) ?
C1 C6 C5 . . 119.54(13) ?
C1 C6 H6 . . 120.2 ?
C5 C6 H6 . . 120.2 ?
N1 C7 N2 . . 105.41(10) ?
N1 C7 C8 . . 108.36(11) ?
N2 C7 C8 . . 109.95(11) ?
N1 C7 C9 . . 112.12(11) ?
N2 C7 C9 . . 108.61(11) ?
C8 C7 C9 . . 112.17(12) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C7 C9 H9A . . 109.5 ?
C7 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C7 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
N2 C10 C11 . . 105.47(11) ?
N2 C10 C5 . . 118.79(12) ?
C11 C10 C5 . . 135.69(13) ?
C10 C11 C12 . . 135.86(13) ?
C10 C11 C16 . . 104.30(12) ?
C12 C11 C16 . . 119.84(12) ?
C13 C12 C11 . . 118.54(13) ?
C13 C12 H12 . . 120.7 ?
C11 C12 H12 . . 120.7 ?
C12 C13 C14 . . 121.35(13) ?
C12 C13 H13 . . 119.3 ?
C14 C13 H13 . . 119.3 ?
C15 C14 C13 . . 121.50(13) ?
C15 C14 H14 . . 119.3 ?
C13 C14 H14 . . 119.3 ?
C14 C15 C16 . . 117.97(13) ?
C14 C15 H15 . . 121.0 ?
C16 C15 H15 . . 121.0 ?
N3 C16 C15 . . 127.06(13) ?
N3 C16 C11 . . 112.13(12) ?
C15 C16 C11 . . 120.80(13) ?
C20 N4 C23 . . 119.47(11) ?
C20 N4 H4N . . 114.1(11) ?
C23 N4 H4N . . 111.7(11) ?
C26 N5 N6 . . 114.95(11) ?
C26 N5 C23 . . 124.25(11) ?
N6 N5 C23 . . 120.24(10) ?
N5 N6 C32 . . 103.14(10) ?
C22 C17 C18 . . 121.23(13) ?
C22 C17 Cl2 . . 119.69(11) ?
C18 C17 Cl2 . . 119.08(11) ?
C19 C18 C17 . . 119.40(13) ?
C19 C18 H18 . . 120.3 ?
C17 C18 H18 . . 120.3 ?
C18 C19 C20 . . 120.59(13) ?
C18 C19 H19 . . 119.7 ?
C20 C19 H19 . . 119.7 ?
N4 C20 C19 . . 121.43(12) ?
N4 C20 C21 . . 118.93(12) ?
C19 C20 C21 . . 119.51(12) ?
C22 C21 C20 . . 119.53(12) ?
C22 C21 C26 . . 123.40(12) ?
C20 C21 C26 . . 117.06(12) ?
C17 C22 C21 . . 119.71(13) ?
C17 C22 H22 . . 120.1 ?
C21 C22 H22 . . 120.1 ?
N4 C23 N5 . . 105.27(10) ?
N4 C23 C24 . . 108.66(11) ?
N5 C23 C24 . . 109.72(11) ?
N4 C23 C25 . . 112.27(11) ?
N5 C23 C25 . . 108.52(11) ?
C24 C23 C25 . . 112.16(12) ?
C23 C24 H24A . . 109.5 ?
C23 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C23 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
C23 C25 H25A . . 109.5 ?
C23 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C23 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
N5 C26 C27 . . 105.54(11) ?
N5 C26 C21 . . 118.71(12) ?
C27 C26 C21 . . 135.74(12) ?
C26 C27 C28 . . 135.70(13) ?
C26 C27 C32 . . 104.40(11) ?
C28 C27 C32 . . 119.90(12) ?
C29 C28 C27 . . 118.35(13) ?
C29 C28 H28 . . 120.8 ?
C27 C28 H28 . . 120.8 ?
C28 C29 C30 . . 121.35(13) ?
C28 C29 H29 . . 119.3 ?
C30 C29 H29 . . 119.3 ?
C31 C30 C29 . . 121.81(13) ?
C31 C30 H30 . . 119.1 ?
C29 C30 H30 . . 119.1 ?
C30 C31 C32 . . 117.58(13) ?
C30 C31 H31 . . 121.2 ?
C32 C31 H31 . . 121.2 ?
N6 C32 C31 . . 127.08(12) ?
N6 C32 C27 . . 111.93(12) ?
C31 C32 C27 . . 120.99(12) ?
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
Cl1 C1 . 1.7411(14) ?
N1 C4 . 1.3884(17) ?
N1 C7 . 1.4649(17) ?
N1 H1N . 0.896(18) ?
N2 C10 . 1.3532(17) ?
N2 N3 . 1.3550(15) ?
N2 C7 . 1.4791(17) ?
N3 C16 . 1.3573(18) ?
C1 C6 . 1.3835(19) ?
C1 C2 . 1.387(2) ?
C2 C3 . 1.382(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.3987(19) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.4072(19) ?
C5 C6 . 1.3995(19) ?
C5 C10 . 1.4548(18) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.5194(19) ?
C7 C9 . 1.5258(19) ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 C11 . 1.4090(19) ?
C11 C12 . 1.4147(19) ?
C11 C16 . 1.4227(18) ?
C12 C13 . 1.370(2) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.424(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.369(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.4156(19) ?
C15 H15 . 0.9500 ?
Cl2 C17 . 1.7401(14) ?
N4 C20 . 1.3917(17) ?
N4 C23 . 1.4662(17) ?
N4 H4N . 0.863(17) ?
N5 C26 . 1.3540(17) ?
N5 N6 . 1.3551(15) ?
N5 C23 . 1.4800(17) ?
N6 C32 . 1.3591(17) ?
C17 C22 . 1.3828(19) ?
C17 C18 . 1.389(2) ?
C18 C19 . 1.3855(19) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.3939(19) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.4118(18) ?
C21 C22 . 1.3954(18) ?
C21 C26 . 1.4506(18) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.5214(18) ?
C23 C25 . 1.5261(19) ?
C24 H24A . 0.9800 ?
C24 H24B . 0.9800 ?
C24 H24C . 0.9800 ?
C25 H25A . 0.9800 ?
C25 H25B . 0.9800 ?
C25 H25C . 0.9800 ?
C26 C27 . 1.4080(18) ?
C27 C28 . 1.4137(19) ?
C27 C32 . 1.4240(18) ?
C28 C29 . 1.370(2) ?
C28 H28 . 0.9500 ?
C29 C30 . 1.420(2) ?
C29 H29 . 0.9500 ?
C30 C31 . 1.372(2) ?
C30 H30 . 0.9500 ?
C31 C32 . 1.4114(19) ?
C31 H31 . 0.9500 ?
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
N1 H1n N6 1_555 0.896(18) 2.319(18) 3.2090(17) 172.5(15)
N4 H4n N3 1_655 0.863(18) 2.390(17) 3.2384(17) 167.5(15)
C9 H9b N4 1_455 0.98 2.58 3.537(2) 164
C25 H25b N1 1_555 0.98 2.61 3.545(2) 160
C24 H24c Cg1 1_655 0.98 2.90 3.8431(17) 162
C8 H8c Cg2 1_555 0.98 2.97 3.8929(17) 157
C18 H18 Cg3 1_665 0.95 2.92 3.6630(15) 135
C14 H14 Cg4 2_666 0.95 2.95 3.8062(16) 151
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 N2 N3 C16 . . . . 2.18(14) ?
C7 N2 N3 C16 . . . . 176.26(11) ?
C6 C1 C2 C3 . . . . -0.5(2) ?
Cl1 C1 C2 C3 . . . . 178.29(10) ?
C1 C2 C3 C4 . . . . 1.0(2) ?
C7 N1 C4 C3 . . . . 152.54(13) ?
C7 N1 C4 C5 . . . . -32.29(18) ?
C2 C3 C4 N1 . . . . 174.78(12) ?
C2 C3 C4 C5 . . . . -0.4(2) ?
N1 C4 C5 C6 . . . . -175.99(12) ?
C3 C4 C5 C6 . . . . -0.75(19) ?
N1 C4 C5 C10 . . . . 1.91(18) ?
C3 C4 C5 C10 . . . . 177.16(12) ?
C2 C1 C6 C5 . . . . -0.6(2) ?
Cl1 C1 C6 C5 . . . . -179.41(10) ?
C4 C5 C6 C1 . . . . 1.3(2) ?
C10 C5 C6 C1 . . . . -176.50(12) ?
C4 N1 C7 N2 . . . . 44.02(15) ?
C4 N1 C7 C8 . . . . 161.69(12) ?
C4 N1 C7 C9 . . . . -73.97(16) ?
C10 N2 C7 N1 . . . . -31.81(16) ?
N3 N2 C7 N1 . . . . 154.73(11) ?
C10 N2 C7 C8 . . . . -148.40(13) ?
N3 N2 C7 C8 . . . . 38.14(16) ?
C10 N2 C7 C9 . . . . 88.52(15) ?
N3 N2 C7 C9 . . . . -84.94(14) ?
N3 N2 C10 C11 . . . . -1.57(15) ?
C7 N2 C10 C11 . . . . -175.31(11) ?
N3 N2 C10 C5 . . . . -179.50(11) ?
C7 N2 C10 C5 . . . . 6.77(19) ?
C6 C5 C10 N2 . . . . -171.72(12) ?
C4 C5 C10 N2 . . . . 10.47(18) ?
C6 C5 C10 C11 . . . . 11.1(2) ?
C4 C5 C10 C11 . . . . -166.67(14) ?
N2 C10 C11 C12 . . . . -178.65(15) ?
C5 C10 C11 C12 . . . . -1.3(3) ?
N2 C10 C11 C16 . . . . 0.26(14) ?
C5 C10 C11 C16 . . . . 177.66(14) ?
C10 C11 C12 C13 . . . . 178.45(15) ?
C16 C11 C12 C13 . . . . -0.33(19) ?
C11 C12 C13 C14 . . . . -0.4(2) ?
C12 C13 C14 C15 . . . . 0.3(2) ?
C13 C14 C15 C16 . . . . 0.5(2) ?
N2 N3 C16 C15 . . . . 177.09(13) ?
N2 N3 C16 C11 . . . . -1.92(14) ?
C14 C15 C16 N3 . . . . 179.89(13) ?
C14 C15 C16 C11 . . . . -1.2(2) ?
C10 C11 C16 N3 . . . . 1.08(15) ?
C12 C11 C16 N3 . . . . -179.79(12) ?
C10 C11 C16 C15 . . . . -178.01(12) ?
C12 C11 C16 C15 . . . . 1.12(19) ?
C26 N5 N6 C32 . . . . 2.02(14) ?
C23 N5 N6 C32 . . . . 173.79(11) ?
C22 C17 C18 C19 . . . . -0.9(2) ?
Cl2 C17 C18 C19 . . . . 178.41(10) ?
C17 C18 C19 C20 . . . . 0.0(2) ?
C23 N4 C20 C19 . . . . 150.56(13) ?
C23 N4 C20 C21 . . . . -33.59(17) ?
C18 C19 C20 N4 . . . . 177.17(12) ?
C18 C19 C20 C21 . . . . 1.4(2) ?
N4 C20 C21 C22 . . . . -177.61(12) ?
C19 C20 C21 C22 . . . . -1.68(19) ?
N4 C20 C21 C26 . . . . 1.62(18) ?
C19 C20 C21 C26 . . . . 177.55(12) ?
C18 C17 C22 C21 . . . . 0.6(2) ?
Cl2 C17 C22 C21 . . . . -178.75(10) ?
C20 C21 C22 C17 . . . . 0.7(2) ?
C26 C21 C22 C17 . . . . -178.46(13) ?
C20 N4 C23 N5 . . . . 46.66(15) ?
C20 N4 C23 C24 . . . . 164.13(12) ?
C20 N4 C23 C25 . . . . -71.22(15) ?
C26 N5 C23 N4 . . . . -34.21(16) ?
N6 N5 C23 N4 . . . . 154.83(11) ?
C26 N5 C23 C24 . . . . -150.96(12) ?
N6 N5 C23 C24 . . . . 38.07(16) ?
C26 N5 C23 C25 . . . . 86.17(15) ?
N6 N5 C23 C25 . . . . -84.79(14) ?
N6 N5 C26 C27 . . . . -1.68(15) ?
C23 N5 C26 C27 . . . . -173.07(11) ?
N6 N5 C26 C21 . . . . 179.01(11) ?
C23 N5 C26 C21 . . . . 7.62(19) ?
C22 C21 C26 N5 . . . . -169.74(12) ?
C20 C21 C26 N5 . . . . 11.07(18) ?
C22 C21 C26 C27 . . . . 11.2(2) ?
C20 C21 C26 C27 . . . . -167.98(14) ?
N5 C26 C27 C28 . . . . -178.92(15) ?
C21 C26 C27 C28 . . . . 0.2(3) ?
N5 C26 C27 C32 . . . . 0.58(14) ?
C21 C26 C27 C32 . . . . 179.71(14) ?
C26 C27 C28 C29 . . . . -179.44(14) ?
C32 C27 C28 C29 . . . . 1.13(19) ?
C27 C28 C29 C30 . . . . -1.2(2) ?
C28 C29 C30 C31 . . . . -0.2(2) ?
C29 C30 C31 C32 . . . . 1.6(2) ?
N5 N6 C32 C31 . . . . 178.35(13) ?
N5 N6 C32 C27 . . . . -1.56(14) ?
C30 C31 C32 N6 . . . . 178.42(13) ?
C30 C31 C32 C27 . . . . -1.69(19) ?
C26 C27 C32 N6 . . . . 0.64(15) ?
C28 C27 C32 N6 . . . . -179.77(12) ?
C26 C27 C32 C31 . . . . -179.27(12) ?
C28 C27 C32 C31 . . . . 0.32(19) ?
