#------------------------------------------------------------------------------
#$Date: 2021-04-05 18:17:23 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263839 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/78/7157871.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_7157871
loop_
_publ_author_name
'de Souza, Juliana M.'
'Abdiaj, Irini'
'Chen, Jiaqi'
'Hanson, Kenneth'
'de Oliveira, Kleber T.'
'McQuade, D. Tyler'
_publ_section_title
;
 Synthesis of multi-substituted pyridines from ylidenemalononitriles and
 their emission properties.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1991
_journal_page_last               1999
_journal_paper_doi               10.1039/d0ob02591g
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         '2(C14 H12 Cl N3)'
_chemical_formula_sum            'C28 H24 Cl2 N6'
_chemical_formula_weight         515.43
_chemical_name_systematic
2-(benzylamino)-5-chloro-4-methylnicotinonitrile
_chemical_properties_physical    Air-stable
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-19
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2020-04-28 deposited with the CCDC.	2021-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                77.320(2)
_cell_angle_beta                 82.364(2)
_cell_angle_gamma                74.894(3)
_cell_formula_units_Z            2
_cell_length_a                   7.6769(2)
_cell_length_b                   12.7598(4)
_cell_length_c                   13.4914(3)
_cell_measurement_reflns_used    6668
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      69.5180
_cell_measurement_theta_min      3.3250
_cell_volume                     1240.75(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -140.00   8.00   0.50    0.50    --  -51.00  60.00-150.00  296
  2  ω   -140.00   8.00   0.50    0.50    --  -51.00  40.00   0.00  296
  3  ω   -140.00   8.00   0.50    0.50    --  -51.00  60.00  60.00  296
  4  ω   -140.00   8.00   0.50    0.50    --  -51.00  20.00-180.00  296
  5  ω   -179.00 -31.00   0.50    0.50    --  -90.00  37.00 -13.99  296
  6  ω   -179.00 -31.00   0.50    0.50    --  -90.00  60.00 -67.10  296
  7  ω   -179.00 -31.00   0.50    0.50    --  -90.00  58.00-103.65  296
  8  ω   -179.00 -31.00   0.50    0.50    --  -90.00  30.00 -90.00  296
  9  ω   -179.00 -31.00   0.50    0.50    --  -90.00  58.00  29.72  296
 10  ω   -179.00 -31.00   0.50    0.50    --  -90.00  60.00 115.00  296
 11  ω   -179.00 -31.00   0.50    0.50    --  -90.00  60.00  -7.87  296
 12  ω   -179.00 -31.00   0.50    0.50    --  -90.00  60.00  48.17  296
 13  ω   -179.00 -31.00   0.50    0.50    --  -90.00  59.00  79.49  296
 14  ω    -60.00 -32.00   0.50    0.50    --  -90.00  60.00-174.52   56
 15  ω   -175.00 -77.00   0.50    0.50    --  -90.00  60.00-174.52  196
 16  ω   -179.00-154.00   0.50    0.50    --  -90.00  60.00-102.93   50
 17  ω   -179.00 -31.00   0.50    0.50    --  -90.00  20.00 -60.00  296
 18  ω   -110.00 -31.00   0.50    0.50    --  -90.00  56.00 152.15  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1285337000
_diffrn_orient_matrix_UB_12      0.0585930000
_diffrn_orient_matrix_UB_13      0.0327551000
_diffrn_orient_matrix_UB_21      0.1243668000
_diffrn_orient_matrix_UB_22      -0.0149730000
_diffrn_orient_matrix_UB_23      -0.0979050000
_diffrn_orient_matrix_UB_31      -0.1072260000
_diffrn_orient_matrix_UB_32      0.1121975000
_diffrn_orient_matrix_UB_33      -0.0559452000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21246
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.014
_diffrn_reflns_theta_min         3.369
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.587
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             536
_exptl_crystal_preparation       Re-crystallization
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform/Hexanes (1:20)'
_exptl_crystal_size_max          0.437
_exptl_crystal_size_mid          0.228
_exptl_crystal_size_min          0.205
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0607P)²+0.4427P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1053
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4327
_reflns_number_total             4575
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob02591g2.cif
_cod_data_source_block           juliana_c14h12cln3_111919
_cod_depositor_comments
'Adding full bibliography for 7157868--7157873.cif.'
_cod_database_code               7157871
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C14H12ClN3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_diffrn_oxdiff_digest_frames
;
017a5355f394e0ab16bb84948923cf661f00046bbed
;
_diffrn_oxdiff_digest_hkl
;
018b2a9d081b22c267df52a22389322bf009b5
;
_reflns_odcompleteness_completeness 99.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 N25(H25), N7(H7), C32(H32), C28(H28), C30(H30), C10(H10), C31(H31), C5(H5),
 C29(H29), C23(H23), C14(H14), C13(H13), C12(H12), C11(H11)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C36(H36A,H36B,H36C)
;
_olex2_exptl_crystal_mounting_method 'MiTeGen Microloop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.133
_oxdiff_exptl_absorpt_empirical_full_min 0.111
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl15 Cl 0.01479(5) 0.71455(3) 0.31950(3) 0.02689(13) Uani 1 1 d . . . . .
Cl33 Cl 0.85513(5) -0.12280(3) 1.11568(3) 0.02884(13) Uani 1 1 d . . . . .
N25 N 0.67617(16) 0.08333(10) 0.70025(9) 0.0208(3) Uani 1 1 d . . . . .
H25 H 0.652025 0.154200 0.682083 0.025 Uiso 1 1 calc R . . . .
N6 N 0.08633(17) 0.66687(10) 0.61344(9) 0.0214(3) Uani 1 1 d . . . . .
N7 N 0.26287(16) 0.52811(10) 0.72493(9) 0.0210(3) Uani 1 1 d . . . . .
H7 H 0.357337 0.474181 0.733154 0.025 Uiso 1 1 calc R . . . .
N24 N 0.78841(16) -0.07145(10) 0.82057(10) 0.0216(3) Uani 1 1 d . . . . .
N17 N 0.46954(18) 0.30748(11) 0.59366(10) 0.0259(3) Uani 1 1 d . . . . .
N35 N 0.48221(19) 0.30569(11) 0.82868(10) 0.0282(3) Uani 1 1 d . . . . .
C32 C 0.3436(2) 0.03459(12) 0.64353(11) 0.0215(3) Uani 1 1 d . . . . .
H32 H 0.327883 0.110551 0.636491 0.026 Uiso 1 1 calc R . . . .
C27 C 0.51853(19) -0.03340(12) 0.63888(10) 0.0192(3) Uani 1 1 d . . . . .
C1 C 0.20108(19) 0.56605(12) 0.63081(11) 0.0188(3) Uani 1 1 d . . . . .
C9 C -0.0050(2) 0.54543(12) 0.84861(10) 0.0210(3) Uani 1 1 d . . . . .
C3 C 0.20377(18) 0.54620(12) 0.45381(11) 0.0188(3) Uani 1 1 d . . . . .
C20 C 0.66135(19) 0.10212(12) 0.87603(11) 0.0195(3) Uani 1 1 d . . . . .
C28 C 0.5392(2) -0.14660(12) 0.64847(11) 0.0228(3) Uani 1 1 d . . . . .
H28 H 0.654730 -0.192909 0.645723 0.027 Uiso 1 1 calc R . . . .
C30 C 0.2153(2) -0.12289(12) 0.66775(11) 0.0231(3) Uani 1 1 d . . . . .
H30 H 0.114587 -0.152776 0.677655 0.028 Uiso 1 1 calc R . . . .
C19 C 0.70855(18) 0.03763(12) 0.79836(11) 0.0192(3) Uani 1 1 d . . . . .
C2 C 0.25888(18) 0.50331(12) 0.55229(11) 0.0184(3) Uani 1 1 d . . . . .
C4 C 0.08891(19) 0.65211(12) 0.43919(11) 0.0203(3) Uani 1 1 d . . . . .
C10 C -0.1697(2) 0.62401(13) 0.84069(11) 0.0245(3) Uani 1 1 d . . . . .
H10 H -0.171275 0.698220 0.815836 0.029 Uiso 1 1 calc R . . . .
C31 C 0.1934(2) -0.00960(13) 0.65845(11) 0.0236(3) Uani 1 1 d . . . . .
H31 H 0.077824 0.036489 0.662257 0.028 Uiso 1 1 calc R . . . .
C5 C 0.0346(2) 0.70740(12) 0.51923(11) 0.0216(3) Uani 1 1 d . . . . .
H5 H -0.043155 0.777395 0.506780 0.026 Uiso 1 1 calc R . . . .
C29 C 0.3885(2) -0.19125(13) 0.66216(12) 0.0253(3) Uani 1 1 d . . . . .
H29 H 0.403673 -0.266973 0.667571 0.030 Uiso 1 1 calc R . . . .
C21 C 0.70432(19) 0.05631(13) 0.97635(11) 0.0205(3) Uani 1 1 d . . . . .
C8 C 0.1733(2) 0.57639(13) 0.81282(11) 0.0224(3) Uani 1 1 d . . . . .
H8A H 0.152130 0.656308 0.794547 0.027 Uiso 1 1 calc R . . . .
H8B H 0.252170 0.550980 0.868145 0.027 Uiso 1 1 calc R . . . .
C26 C 0.68049(19) 0.01739(12) 0.62400(11) 0.0209(3) Uani 1 1 d . . . . .
H26A H 0.790551 -0.041200 0.627422 0.025 Uiso 1 1 calc R . . . .
H26B H 0.683141 0.063875 0.556730 0.025 Uiso 1 1 calc R . . . .
C23 C 0.8286(2) -0.11458(13) 0.91670(12) 0.0228(3) Uani 1 1 d . . . . .
H23 H 0.884797 -0.189497 0.932262 0.027 Uiso 1 1 calc R . . . .
C14 C -0.0051(2) 0.43452(13) 0.88667(11) 0.0232(3) Uani 1 1 d . . . . .
H14 H 0.104120 0.381688 0.893502 0.028 Uiso 1 1 calc R . . . .
C13 C -0.1665(2) 0.40254(14) 0.91429(12) 0.0266(3) Uani 1 1 d . . . . .
H13 H -0.165401 0.328333 0.938699 0.032 Uiso 1 1 calc R . . . .
C34 C 0.5631(2) 0.21588(13) 0.85038(11) 0.0216(3) Uani 1 1 d . . . . .
C18 C 0.2645(2) 0.48313(13) 0.36920(12) 0.0234(3) Uani 1 1 d . . . . .
H18A H 0.339398 0.520392 0.318342 0.035 Uiso 1 1 calc GR . . . .
H18B H 0.160747 0.478584 0.339233 0.035 Uiso 1 1 calc GR . . . .
H18C H 0.332469 0.409909 0.395686 0.035 Uiso 1 1 calc GR . . . .
C22 C 0.7927(2) -0.05588(13) 0.99425(11) 0.0222(3) Uani 1 1 d . . . . .
C16 C 0.37583(19) 0.39414(12) 0.57473(11) 0.0201(3) Uani 1 1 d . . . . .
C36 C 0.6579(2) 0.12225(13) 1.05955(12) 0.0249(3) Uani 1 1 d . . . . .
H36A H 0.767275 0.126928 1.083670 0.037 Uiso 1 1 calc GR . . . .
H36B H 0.587820 0.086703 1.114703 0.037 Uiso 1 1 calc GR . . . .
H36C H 0.588933 0.195339 1.033554 0.037 Uiso 1 1 calc GR . . . .
C12 C -0.3300(2) 0.48120(14) 0.90560(12) 0.0280(4) Uani 1 1 d . . . . .
H12 H -0.438484 0.459619 0.923791 0.034 Uiso 1 1 calc R . . . .
C11 C -0.3316(2) 0.59173(14) 0.86987(12) 0.0281(4) Uani 1 1 d . . . . .
H11 H -0.441127 0.644524 0.865354 0.034 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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
C19 N25 H25 118.7 . . ?
C19 N25 C26 122.67(12) . . ?
C26 N25 H25 118.7 . . ?
C5 N6 C1 117.73(12) . . ?
C1 N7 H7 119.1 . . ?
C1 N7 C8 121.86(12) . . ?
C8 N7 H7 119.1 . . ?
C23 N24 C19 117.37(13) . . ?
C27 C32 H32 119.5 . . ?
C31 C32 H32 119.5 . . ?
C31 C32 C27 120.91(14) . . ?
C32 C27 C26 119.64(13) . . ?
C28 C27 C32 118.71(13) . . ?
C28 C27 C26 121.65(13) . . ?
N6 C1 N7 117.60(12) . . ?
N6 C1 C2 121.01(13) . . ?
N7 C1 C2 121.36(13) . . ?
C10 C9 C8 121.75(14) . . ?
C10 C9 C14 119.11(14) . . ?
C14 C9 C8 119.09(13) . . ?
C2 C3 C18 122.21(13) . . ?
C4 C3 C2 115.78(13) . . ?
C4 C3 C18 122.01(13) . . ?
C19 C20 C34 118.84(13) . . ?
C21 C20 C19 121.31(13) . . ?
C21 C20 C34 119.83(13) . . ?
C27 C28 H28 119.7 . . ?
C27 C28 C29 120.58(13) . . ?
C29 C28 H28 119.7 . . ?
C31 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C29 C30 C31 119.67(14) . . ?
N25 C19 C20 121.34(13) . . ?
N24 C19 N25 117.83(13) . . ?
N24 C19 C20 120.82(13) . . ?
C1 C2 C16 119.44(13) . . ?
C3 C2 C1 120.90(13) . . ?
C3 C2 C16 119.66(13) . . ?
C3 C4 Cl15 119.80(11) . . ?
C5 C4 Cl15 119.82(11) . . ?
C5 C4 C3 120.38(13) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.19(15) . . ?
C11 C10 H10 119.9 . . ?
C32 C31 C30 120.00(14) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
N6 C5 C4 124.15(13) . . ?
N6 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
C28 C29 H29 119.9 . . ?
C30 C29 C28 120.12(14) . . ?
C30 C29 H29 119.9 . . ?
C20 C21 C22 115.38(13) . . ?
C20 C21 C36 122.56(13) . . ?
C22 C21 C36 122.05(13) . . ?
N7 C8 C9 111.88(12) . . ?
N7 C8 H8A 109.2 . . ?
N7 C8 H8B 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N25 C26 C27 112.45(12) . . ?
N25 C26 H26A 109.1 . . ?
N25 C26 H26B 109.1 . . ?
C27 C26 H26A 109.1 . . ?
C27 C26 H26B 109.1 . . ?
H26A C26 H26B 107.8 . . ?
N24 C23 H23 117.7 . . ?
N24 C23 C22 124.53(14) . . ?
C22 C23 H23 117.7 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.53(14) . . ?
C13 C14 H14 119.7 . . ?
C14 C13 H13 120.0 . . ?
C14 C13 C12 120.03(15) . . ?
C12 C13 H13 120.0 . . ?
N35 C34 C20 178.34(15) . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C22 Cl33 120.03(12) . . ?
C23 C22 Cl33 119.48(12) . . ?
C23 C22 C21 120.48(14) . . ?
N17 C16 C2 179.17(15) . . ?
C21 C36 H36A 109.5 . . ?
C21 C36 H36B 109.5 . . ?
C21 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 119.99(15) . . ?
C11 C12 H12 120.0 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.13(14) . . ?
C12 C11 H11 119.9 . . ?
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
Cl15 C4 1.7347(15) . ?
Cl33 C22 1.7389(15) . ?
N25 H25 0.8600 . ?
N25 C19 1.3516(19) . ?
N25 C26 1.4573(18) . ?
N6 C1 1.3482(19) . ?
N6 C5 1.3340(19) . ?
N7 H7 0.8600 . ?
N7 C1 1.3574(19) . ?
N7 C8 1.4634(18) . ?
N24 C19 1.3505(19) . ?
N24 C23 1.336(2) . ?
N17 C16 1.147(2) . ?
N35 C34 1.147(2) . ?
C32 H32 0.9300 . ?
C32 C27 1.398(2) . ?
C32 C31 1.384(2) . ?
C27 C28 1.390(2) . ?
C27 C26 1.518(2) . ?
C1 C2 1.422(2) . ?
C9 C10 1.394(2) . ?
C9 C8 1.511(2) . ?
C9 C14 1.396(2) . ?
C3 C2 1.398(2) . ?
C3 C4 1.397(2) . ?
C3 C18 1.4948(19) . ?
C20 C19 1.424(2) . ?
C20 C21 1.398(2) . ?
C20 C34 1.440(2) . ?
C28 H28 0.9300 . ?
C28 C29 1.392(2) . ?
C30 H30 0.9300 . ?
C30 C31 1.390(2) . ?
C30 C29 1.390(2) . ?
C2 C16 1.440(2) . ?
C4 C5 1.378(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.391(2) . ?
C31 H31 0.9300 . ?
C5 H5 0.9300 . ?
C29 H29 0.9300 . ?
C21 C22 1.398(2) . ?
C21 C36 1.499(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C23 H23 0.9300 . ?
C23 C22 1.375(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.383(2) . ?
C13 H13 0.9300 . ?
C13 C12 1.389(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C12 H12 0.9300 . ?
C12 C11 1.384(2) . ?
C11 H11 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N25 H25 N17 0.86 2.28 3.0332(18) 146.1 .
N7 H7 N35 0.86 2.29 3.0399(18) 145.9 .
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
Cl15 C4 C5 N6 -179.04(12) . . . . ?
N6 C1 C2 C3 2.5(2) . . . . ?
N6 C1 C2 C16 -177.56(13) . . . . ?
N7 C1 C2 C3 -175.77(13) . . . . ?
N7 C1 C2 C16 4.2(2) . . . . ?
N24 C23 C22 Cl33 -179.27(12) . . . . ?
N24 C23 C22 C21 1.6(2) . . . . ?
C32 C27 C28 C29 0.2(2) . . . . ?
C32 C27 C26 N25 54.72(18) . . . . ?
C27 C32 C31 C30 -0.8(2) . . . . ?
C27 C28 C29 C30 -0.9(2) . . . . ?
C1 N6 C5 C4 1.0(2) . . . . ?
C1 N7 C8 C9 72.50(17) . . . . ?
C9 C10 C11 C12 -0.9(2) . . . . ?
C9 C14 C13 C12 -0.9(2) . . . . ?
C3 C4 C5 N6 0.8(2) . . . . ?
C20 C21 C22 Cl33 179.56(11) . . . . ?
C20 C21 C22 C23 -1.4(2) . . . . ?
C28 C27 C26 N25 -125.05(14) . . . . ?
C19 N25 C26 C27 72.56(17) . . . . ?
C19 N24 C23 C22 0.7(2) . . . . ?
C19 C20 C21 C22 -1.0(2) . . . . ?
C19 C20 C21 C36 179.46(13) . . . . ?
C2 C3 C4 Cl15 178.97(10) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C4 C3 C2 C1 -0.7(2) . . . . ?
C4 C3 C2 C16 179.33(13) . . . . ?
C10 C9 C8 N7 -113.23(15) . . . . ?
C10 C9 C14 C13 1.3(2) . . . . ?
C31 C32 C27 C28 0.7(2) . . . . ?
C31 C32 C27 C26 -179.10(13) . . . . ?
C31 C30 C29 C28 0.7(2) . . . . ?
C5 N6 C1 N7 175.78(13) . . . . ?
C5 N6 C1 C2 -2.5(2) . . . . ?
C29 C30 C31 C32 0.1(2) . . . . ?
C21 C20 C19 N25 -176.24(13) . . . . ?
C21 C20 C19 N24 3.4(2) . . . . ?
C8 N7 C1 N6 17.4(2) . . . . ?
C8 N7 C1 C2 -164.29(13) . . . . ?
C8 C9 C10 C11 176.89(13) . . . . ?
C8 C9 C14 C13 -176.08(13) . . . . ?
C26 N25 C19 N24 15.9(2) . . . . ?
C26 N25 C19 C20 -164.52(13) . . . . ?
C26 C27 C28 C29 179.95(13) . . . . ?
C23 N24 C19 N25 176.52(13) . . . . ?
C23 N24 C19 C20 -3.1(2) . . . . ?
C14 C9 C10 C11 -0.4(2) . . . . ?
C14 C9 C8 N7 64.05(17) . . . . ?
C14 C13 C12 C11 -0.4(2) . . . . ?
C13 C12 C11 C10 1.3(2) . . . . ?
C34 C20 C19 N25 5.4(2) . . . . ?
C34 C20 C19 N24 -174.95(13) . . . . ?
C34 C20 C21 C22 177.28(13) . . . . ?
C34 C20 C21 C36 -2.2(2) . . . . ?
C18 C3 C2 C1 178.98(13) . . . . ?
C18 C3 C2 C16 -1.0(2) . . . . ?
C18 C3 C4 Cl15 -0.7(2) . . . . ?
C18 C3 C4 C5 179.47(14) . . . . ?
C36 C21 C22 Cl33 -0.9(2) . . . . ?
C36 C21 C22 C23 178.17(14) . . . . ?
