#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/62/7106215.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_7106215
loop_
_publ_author_name
'Govindasamy Jayamurugan'
'Jean-Paul Gisselbrecht'
'Corinne Boudon'
'Franziska Schoenebeck'
'W. Bernd Schweizer'
'Bruno Bernet'
'Francois Diederich'
_publ_section_title
;
 Expanding the chemical space for push-pull chromophores by non-concerted
 [2+2] and [4+2] cycloadditions: access to a highly functionalized
 6,6-dicyanofulvene with an intense, low-energy charge-transfer band;
;
_journal_name_full               Chem.Commun.
_journal_page_first              4520
_journal_paper_doi               10.1039/c1cc10247h
_journal_volume                  47
_journal_year                    2011
_chemical_compound_source        'LOC ETH Zurich'
_chemical_formula_moiety         '2(C25 H21 N5 ), 0.5( C2 H4 Cl2) '
_chemical_formula_sum            'C51 H44 Cl N10'
_chemical_formula_weight         832.436
_chemical_name_systematic
;
?
;
_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_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                93.245(5)
_cell_angle_beta                 91.748(5)
_cell_angle_gamma                109.113(3)
_cell_formula_units_Z            2
_cell_length_a                   9.8044(6)
_cell_length_b                   12.8651(10)
_cell_length_c                   18.011(2)
_cell_measurement_reflns_used    168410
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.753
_cell_volume                     2140.2(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.04421
_diffrn_orient_matrix_UB_12      0.09140
_diffrn_orient_matrix_UB_13      0.03710
_diffrn_orient_matrix_UB_21      -0.04176
_diffrn_orient_matrix_UB_22      0.06452
_diffrn_orient_matrix_UB_23      -0.02992
_diffrn_orient_matrix_UB_31      -0.03479
_diffrn_orient_matrix_UB_32      0.00263
_diffrn_orient_matrix_UB_33      0.04340
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11481
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             874
_exptl_crystal_size_max          .24
_exptl_crystal_size_mid          .075
_exptl_crystal_size_min          .009
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.532
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     570
_refine_ls_number_reflns         7214
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.532
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0742
_refine_ls_shift/su_max          0.050
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+ (0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2097
_refine_ls_wR_factor_ref         0.2206
_reflns_number_gt                5920
_reflns_number_total             7214
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc10247h.txt
_cod_data_source_block           7
_cod_original_cell_volume        2140.3(3)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C51 H44 Cl N10 '
_cod_database_code               7106215
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N10 N 0.1857(3) 0.5121(2) 0.03962(15) 0.0420(7) Uani 1 1 d . . .
N11 N 0.2219(3) 0.3586(2) 0.21615(15) 0.0432(7) Uani 1 1 d . . .
N12 N 0.0286(3) 0.9088(2) 0.26622(13) 0.0417(7) Uani 1 1 d . . .
N21 N 0.0832(3) 0.9428(2) -0.07222(13) 0.0333(6) Uani 1 1 d . . .
N30 N 0.1711(3) 0.8534(2) 0.61743(13) 0.0401(6) Uani 1 1 d . . .
N40 N 0.8071(4) 0.4819(3) 0.36775(17) 0.0546(8) Uani 1 1 d . . .
N41 N 0.8374(3) 0.3693(2) 0.17192(16) 0.0480(7) Uani 1 1 d . . .
N42 N 0.5314(3) 0.8675(2) 0.22891(14) 0.0424(7) Uani 1 1 d . . .
N51 N 0.6668(3) 0.8483(2) 0.56408(14) 0.0393(6) Uani 1 1 d . . .
N60 N 0.4852(3) 0.8271(2) -0.13148(13) 0.0380(6) Uani 1 1 d . . .
C1 C 0.1350(3) 0.7036(2) 0.17773(15) 0.0277(6) Uani 1 1 d . . .
C2 C 0.1586(3) 0.6023(2) 0.16835(15) 0.0289(6) Uani 1 1 d . . .
C3 C 0.1752(3) 0.5448(2) 0.23057(16) 0.0315(6) Uani 1 1 d . . .
C4 C 0.1732(3) 0.5897(2) 0.30213(15) 0.0304(6) Uani 1 1 d . . .
C5 C 0.1502(3) 0.6912(2) 0.31537(15) 0.0276(6) Uani 1 1 d . . .
C6 C 0.1259(3) 0.7442(2) 0.25175(15) 0.0278(6) Uani 1 1 d . . .
C7 C 0.1720(3) 0.5537(3) 0.09614(17) 0.0351(7) Uani 1 1 d . . .
C8 C 0.2000(3) 0.4410(3) 0.22102(16) 0.0343(7) Uani 1 1 d . . .
C9 C 0.0756(3) 0.8370(3) 0.26033(15) 0.0310(7) Uani 1 1 d . . .
C13 C 0.1216(3) 0.7666(2) 0.11319(14) 0.0271(6) Uani 1 1 d . . .
C14 C 0.1999(3) 0.8793(2) 0.11207(15) 0.0290(6) Uani 1 1 d . . .
C15 C 0.1903(3) 0.9373(2) 0.05115(15) 0.0295(6) Uani 1 1 d . . .
C16 C 0.0985(3) 0.8861(2) -0.01206(15) 0.0282(6) Uani 1 1 d . . .
C17 C 0.0226(3) 0.7719(2) -0.01103(15) 0.0297(6) Uani 1 1 d . . .
C18 C 0.0341(3) 0.7145(2) 0.05010(15) 0.0301(6) Uani 1 1 d . . .
C19 C 0.1702(3) 1.0586(3) -0.07615(16) 0.0335(7) Uani 1 1 d . . .
C20 C -0.0042(3) 0.8847(3) -0.13781(15) 0.0346(7) Uani 1 1 d . . .
C22 C 0.1537(3) 0.7357(2) 0.39277(15) 0.0297(6) Uani 1 1 d . . .
C23 C 0.1090(3) 0.6641(3) 0.44986(15) 0.0333(7) Uani 1 1 d . . .
C24 C 0.1144(3) 0.7018(3) 0.52337(16) 0.0340(7) Uani 1 1 d . . .
C25 C 0.1653(3) 0.8152(3) 0.54454(15) 0.0325(7) Uani 1 1 d . . .
C26 C 0.2116(3) 0.8877(3) 0.48744(15) 0.0328(7) Uani 1 1 d . . .
C27 C 0.2055(3) 0.8476(3) 0.41387(15) 0.0311(6) Uani 1 1 d . . .
C28 C 0.1353(4) 0.7761(3) 0.67593(17) 0.0457(8) Uani 1 1 d . . .
C29 C 0.2176(4) 0.9710(3) 0.63857(17) 0.0463(8) Uani 1 1 d . . .
C31 C 0.6638(3) 0.6590(2) 0.27028(16) 0.0308(6) Uani 1 1 d . . .
C32 C 0.7190(3) 0.5714(3) 0.25955(17) 0.0360(7) Uani 1 1 d . . .
C33 C 0.7215(3) 0.5235(3) 0.18697(17) 0.0364(7) Uani 1 1 d . . .
C34 C 0.6682(3) 0.5593(3) 0.12577(17) 0.0349(7) Uani 1 1 d . . .
C35 C 0.6131(3) 0.6480(3) 0.13254(16) 0.0310(6) Uani 1 1 d . . .
C36 C 0.6125(3) 0.6958(3) 0.20510(16) 0.0321(7) Uani 1 1 d . . .
C37 C 0.7672(4) 0.5237(3) 0.32102(18) 0.0415(8) Uani 1 1 d . . .
C38 C 0.7832(4) 0.4359(3) 0.17779(18) 0.0404(7) Uani 1 1 d . . .
C39 C 0.5675(3) 0.7916(3) 0.21761(15) 0.0332(7) Uani 1 1 d . . .
C43 C 0.6638(3) 0.7104(2) 0.34528(16) 0.0314(6) Uani 1 1 d . . .
C44 C 0.7894(3) 0.7439(3) 0.39242(16) 0.0338(7) Uani 1 1 d . . .
C45 C 0.7908(3) 0.7889(3) 0.46417(17) 0.0367(7) Uani 1 1 d . . .
C46 C 0.6660(3) 0.8026(3) 0.49337(16) 0.0348(7) Uani 1 1 d . . .
C47 C 0.5393(3) 0.7696(3) 0.44534(16) 0.0330(7) Uani 1 1 d . . .
C48 C 0.5401(3) 0.7255(3) 0.37394(16) 0.0341(7) Uani 1 1 d . . .
C49 C 0.5347(4) 0.8558(3) 0.59366(18) 0.0496(9) Uani 1 1 d . . .
C50 C 0.7908(4) 0.8651(3) 0.61529(19) 0.0484(9) Uani 1 1 d . . .
C52 C 0.5684(3) 0.6881(2) 0.06395(16) 0.0306(6) Uani 1 1 d . . .
C53 C 0.4682(3) 0.7441(3) 0.06042(15) 0.0306(6) Uani 1 1 d . . .
C54 C 0.4370(3) 0.7872(3) -0.00347(15) 0.0317(7) Uani 1 1 d . . .
C55 C 0.5078(3) 0.7771(3) -0.06981(15) 0.0318(7) Uani 1 1 d . . .
C56 C 0.6018(3) 0.7144(3) -0.06838(16) 0.0336(7) Uani 1 1 d . . .
C57 C 0.6307(3) 0.6725(3) -0.00337(16) 0.0341(7) Uani 1 1 d . . .
C58 C 0.3944(4) 0.8957(3) -0.13013(18) 0.0428(8) Uani 1 1 d . . .
C59 C 0.5440(4) 0.8070(4) -0.20148(17) 0.0490(9) Uani 1 1 d . . .
Cl62 Cl 0.39385(14) 0.43475(9) 0.39352(6) 0.0744(4) Uani 1 1 d . . .
C61 C 0.4293(6) 0.4921(5) 0.5010(4) 0.107(2) Uani 1 1 d . . .
H4 H 0.1894 0.5464 0.3481 0.036 Uiso 1 1 calc R . .
H14 H 0.2678 0.9207 0.1590 0.035 Uiso 1 1 calc R . .
H15 H 0.2529 1.0219 0.0517 0.035 Uiso 1 1 calc R . .
H17 H -0.0443 0.7296 -0.0580 0.036 Uiso 1 1 calc R . .
H18 H -0.0247 0.6291 0.0491 0.036 Uiso 1 1 calc R . .
H19A H 0.1684 1.1036 -0.0239 0.040 Uiso 1 1 calc R . .
H19B H 0.1264 1.0931 -0.1206 0.040 Uiso 1 1 calc R . .
H19C H 0.2803 1.0646 -0.0869 0.040 Uiso 1 1 calc R . .
H20A H 0.0403 0.8241 -0.1609 0.041 Uiso 1 1 calc R . .
H20B H -0.0042 0.9428 -0.1788 0.041 Uiso 1 1 calc R . .
H20C H -0.1136 0.8439 -0.1226 0.041 Uiso 1 1 calc R . .
H23 H 0.0697 0.5779 0.4359 0.040 Uiso 1 1 calc R . .
H24 H 0.0796 0.6444 0.5645 0.041 Uiso 1 1 calc R . .
H26 H 0.2515 0.9740 0.5010 0.039 Uiso 1 1 calc R . .
H27 H 0.2417 0.9044 0.3724 0.037 Uiso 1 1 calc R . .
H28A H 0.0233 0.7248 0.6682 0.055 Uiso 1 1 calc R . .
H28B H 0.1529 0.8214 0.7297 0.055 Uiso 1 1 calc R . .
H28C H 0.2032 0.7248 0.6732 0.055 Uiso 1 1 calc R . .
H29A H 0.3301 1.0079 0.6271 0.056 Uiso 1 1 calc R . .
H29B H 0.2040 0.9837 0.6973 0.056 Uiso 1 1 calc R . .
H29C H 0.1533 1.0087 0.6070 0.056 Uiso 1 1 calc R . .
H34 H 0.6682 0.5198 0.0725 0.042 Uiso 1 1 calc R . .
H44 H 0.8856 0.7344 0.3726 0.041 Uiso 1 1 calc R . .
H45 H 0.8881 0.8137 0.4978 0.044 Uiso 1 1 calc R . .
H47 H 0.461(4) 0.774(3) 0.4629(18) 0.040 Uiso 1 1 d . . .
H48 H 0.4438 0.7023 0.3395 0.041 Uiso 1 1 calc R . .
H49A H 0.4858 0.8974 0.5559 0.060 Uiso 1 1 calc R . .
H49B H 0.5587 0.9016 0.6473 0.060 Uiso 1 1 calc R . .
H49C H 0.4608 0.7738 0.5999 0.060 Uiso 1 1 calc R . .
H50A H 0.8106 0.7879 0.6199 0.058 Uiso 1 1 calc R . .
H50B H 0.7691 0.8950 0.6694 0.058 Uiso 1 1 calc R . .
H50C H 0.8847 0.9248 0.5946 0.058 Uiso 1 1 calc R . .
H53 H 0.4141 0.7536 0.1090 0.037 Uiso 1 1 calc R . .
H54 H 0.3594 0.8284 -0.0032 0.038 Uiso 1 1 calc R . .
H56 H 0.6505 0.6995 -0.1178 0.040 Uiso 1 1 calc R . .
H57 H 0.7029 0.6266 -0.0040 0.041 Uiso 1 1 calc R . .
H58A H 0.2832 0.8450 -0.1254 0.051 Uiso 1 1 calc R . .
H58B H 0.4041 0.9378 -0.1809 0.051 Uiso 1 1 calc R . .
H58C H 0.4278 0.9557 -0.0830 0.051 Uiso 1 1 calc R . .
H59A H 0.6600 0.8452 -0.1975 0.059 Uiso 1 1 calc R . .
H59B H 0.4986 0.8414 -0.2454 0.059 Uiso 1 1 calc R . .
H59C H 0.5171 0.7192 -0.2138 0.059 Uiso 1 1 calc R . .
H61A H 0.4053 0.5676 0.5119 0.128 Uiso 1 1 calc R . .
H61B H 0.3751 0.4315 0.5389 0.128 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_
_diffrn_radiation_wavelength
0.71073
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
C16 N21 C20 120.2(3) . . ?
C16 N21 C19 120.8(2) . . ?
C20 N21 C19 118.4(2) . . ?
C25 N30 C29 121.0(3) . . ?
C25 N30 C28 120.2(3) . . ?
C29 N30 C28 118.7(2) . . ?
C46 N51 C49 120.3(3) . . ?
C46 N51 C50 119.5(3) . . ?
C49 N51 C50 118.6(3) . . ?
C55 N60 C58 121.0(2) . . ?
C55 N60 C59 120.7(2) . . ?
C58 N60 C59 118.1(2) . . ?
C2 C1 C6 117.3(2) . . ?
C2 C1 C13 121.4(2) . . ?
C6 C1 C13 121.3(2) . . ?
C1 C2 C3 120.6(2) . . ?
C1 C2 C7 122.3(2) . . ?
C3 C2 C7 117.0(2) . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 C8 118.8(3) . . ?
C2 C3 C8 120.7(2) . . ?
C3 C4 C5 121.7(3) . . ?
C4 C5 C6 116.6(2) . . ?
C4 C5 C22 118.9(2) . . ?
C6 C5 C22 124.5(2) . . ?
C5 C6 C1 123.1(2) . . ?
C5 C6 C9 119.8(2) . . ?
C1 C6 C9 116.8(2) . . ?
N10 C7 C2 177.2(3) . . ?
N11 C8 C3 177.4(3) . . ?
N12 C9 C6 176.8(3) . . ?
C18 C13 C14 117.8(3) . . ?
C18 C13 C1 120.9(3) . . ?
C14 C13 C1 121.3(3) . . ?
C15 C14 C13 121.3(3) . . ?
C14 C15 C16 121.4(3) . . ?
N21 C16 C17 120.7(3) . . ?
N21 C16 C15 122.5(3) . . ?
C17 C16 C15 116.8(3) . . ?
C18 C17 C16 121.2(3) . . ?
C17 C18 C13 121.5(3) . . ?
C27 C22 C23 116.7(3) . . ?
C27 C22 C5 123.0(3) . . ?
C23 C22 C5 120.3(3) . . ?
C24 C23 C22 122.4(3) . . ?
C23 C24 C25 120.9(3) . . ?
N30 C25 C24 121.3(3) . . ?
N30 C25 C26 121.6(3) . . ?
C24 C25 C26 117.0(3) . . ?
C27 C26 C25 120.9(3) . . ?
C26 C27 C22 122.1(3) . . ?
C32 C31 C36 116.7(3) . . ?
C32 C31 C43 120.6(2) . . ?
C36 C31 C43 122.7(3) . . ?
C31 C32 C33 120.4(3) . . ?
C31 C32 C37 121.8(3) . . ?
C33 C32 C37 117.7(3) . . ?
C34 C33 C32 121.3(3) . . ?
C34 C33 C38 119.8(3) . . ?
C32 C33 C38 118.9(3) . . ?
C33 C34 C35 121.1(3) . . ?
C34 C35 C36 117.0(3) . . ?
C34 C35 C52 118.3(3) . . ?
C36 C35 C52 124.6(3) . . ?
C35 C36 C31 123.4(3) . . ?
C35 C36 C39 121.4(2) . . ?
C31 C36 C39 115.1(2) . . ?
N40 C37 C32 176.6(4) . . ?
N41 C38 C33 177.2(4) . . ?
N42 C39 C36 178.8(3) . . ?
C48 C43 C44 116.9(3) . . ?
C48 C43 C31 122.5(3) . . ?
C44 C43 C31 120.6(3) . . ?
C45 C44 C43 121.7(3) . . ?
C44 C45 C46 121.4(3) . . ?
N51 C46 C45 121.8(3) . . ?
N51 C46 C47 121.3(3) . . ?
C45 C46 C47 116.8(3) . . ?
C48 C47 C46 121.0(3) . . ?
C47 C48 C43 122.2(3) . . ?
C53 C52 C57 116.0(3) . . ?
C53 C52 C35 124.4(2) . . ?
C57 C52 C35 119.6(2) . . ?
C54 C53 C52 122.7(3) . . ?
C53 C54 C55 120.6(3) . . ?
N60 C55 C56 122.2(2) . . ?
N60 C55 C54 120.6(3) . . ?
C56 C55 C54 117.2(3) . . ?
C57 C56 C55 120.5(3) . . ?
C56 C57 C52 122.7(3) . . ?
C61 C61 Cl62 92.1(6) 2_666 . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
N21 C19 H19A 109.5 . . ?
N21 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N21 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N21 C20 H20A 109.5 . . ?
N21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C24 C23 H23 118.8 . . ?
C22 C23 H23 118.8 . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 H27 118.9 . . ?
C22 C27 H27 118.9 . . ?
N30 C28 H28A 109.5 . . ?
N30 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N30 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N30 C29 H29A 109.5 . . ?
N30 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N30 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C33 C34 H34 119.5 . . ?
C35 C34 H34 119.5 . . ?
C45 C44 H44 119.2 . . ?
C43 C44 H44 119.2 . . ?
C44 C45 H45 119.3 . . ?
C46 C45 H45 119.3 . . ?
C48 C47 H47 121(2) . . ?
C46 C47 H47 118(2) . . ?
C47 C48 H48 118.9 . . ?
C43 C48 H48 118.9 . . ?
N51 C49 H49A 109.5 . . ?
N51 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
N51 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
N51 C50 H50A 109.5 . . ?
N51 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
N51 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C54 C53 H53 118.6 . . ?
C52 C53 H53 118.6 . . ?
C53 C54 H54 119.7 . . ?
C55 C54 H54 119.7 . . ?
C57 C56 H56 119.7 . . ?
C55 C56 H56 119.7 . . ?
C56 C57 H57 118.6 . . ?
C52 C57 H57 118.6 . . ?
N60 C58 H58A 109.5 . . ?
N60 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
N60 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
N60 C59 H59A 109.5 . . ?
N60 C59 H59B 109.5 . . ?
H59A C59 H59B 109.5 . . ?
N60 C59 H59C 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
C61 C61 H61A 113.3 2_666 . ?
Cl62 C61 H61A 113.3 . . ?
C61 C61 H61B 113.3 2_666 . ?
Cl62 C61 H61B 113.3 . . ?
H61A C61 H61B 110.6 . . ?
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
N10 C7 1.155(4) . ?
N11 C8 1.149(4) . ?
N12 C9 1.161(4) . ?
N21 C16 1.371(4) . ?
N21 C20 1.451(4) . ?
N21 C19 1.461(4) . ?
N30 C25 1.368(4) . ?
N30 C29 1.454(4) . ?
N30 C28 1.462(4) . ?
N40 C37 1.150(4) . ?
N41 C38 1.149(4) . ?
N42 C39 1.153(4) . ?
N51 C46 1.371(4) . ?
N51 C49 1.445(4) . ?
N51 C50 1.454(4) . ?
N60 C55 1.362(4) . ?
N60 C58 1.445(4) . ?
N60 C59 1.447(4) . ?
C1 C2 1.399(4) . ?
C1 C6 1.420(4) . ?
C1 C13 1.481(4) . ?
C2 C3 1.410(4) . ?
C2 C7 1.439(4) . ?
C3 C4 1.386(4) . ?
C3 C8 1.436(4) . ?
C4 C5 1.404(4) . ?
C5 C6 1.419(4) . ?
C5 C22 1.472(4) . ?
C6 C9 1.436(4) . ?
C13 C18 1.398(4) . ?
C13 C14 1.402(4) . ?
C14 C15 1.379(4) . ?
C15 C16 1.415(4) . ?
C16 C17 1.414(4) . ?
C17 C18 1.382(4) . ?
C22 C27 1.387(4) . ?
C22 C23 1.402(4) . ?
C23 C24 1.377(4) . ?
C24 C25 1.404(4) . ?
C25 C26 1.412(4) . ?
C26 C27 1.387(4) . ?
C31 C32 1.407(4) . ?
C31 C36 1.428(4) . ?
C31 C43 1.470(4) . ?
C32 C33 1.418(4) . ?
C32 C37 1.435(4) . ?
C33 C34 1.371(4) . ?
C33 C38 1.448(4) . ?
C34 C35 1.414(4) . ?
C35 C36 1.414(4) . ?
C35 C52 1.474(4) . ?
C36 C39 1.447(4) . ?
C43 C48 1.398(4) . ?
C43 C44 1.404(4) . ?
C44 C45 1.384(4) . ?
C45 C46 1.405(4) . ?
C46 C47 1.421(4) . ?
C47 C48 1.377(4) . ?
C52 C53 1.397(4) . ?
C52 C57 1.408(4) . ?
C53 C54 1.374(4) . ?
C54 C55 1.421(4) . ?
C55 C56 1.409(4) . ?
C56 C57 1.376(4) . ?
Cl62 C61 2.011(8) . ?
C61 C61 1.337(11) 2_666 ?
C4 H4 1.0600 . ?
C14 H14 1.0600 . ?
C15 H15 1.0600 . ?
C17 H17 1.0600 . ?
C18 H18 1.0600 . ?
C19 H19A 1.0800 . ?
C19 H19B 1.0800 . ?
C19 H19C 1.0800 . ?
C20 H20A 1.0800 . ?
C20 H20B 1.0800 . ?
C20 H20C 1.0800 . ?
C23 H23 1.0600 . ?
C24 H24 1.0600 . ?
C26 H26 1.0600 . ?
C27 H27 1.0600 . ?
C28 H28A 1.0800 . ?
C28 H28B 1.0800 . ?
C28 H28C 1.0800 . ?
C29 H29A 1.0800 . ?
C29 H29B 1.0800 . ?
C29 H29C 1.0800 . ?
C34 H34 1.0600 . ?
C44 H44 1.0600 . ?
C45 H45 1.0600 . ?
C47 H47 0.86(3) . ?
C48 H48 1.0600 . ?
C49 H49A 1.0800 . ?
C49 H49B 1.0800 . ?
C49 H49C 1.0800 . ?
C50 H50A 1.0800 . ?
C50 H50B 1.0800 . ?
C50 H50C 1.0800 . ?
C53 H53 1.0600 . ?
C54 H54 1.0600 . ?
C56 H56 1.0600 . ?
C57 H57 1.0600 . ?
C58 H58A 1.0800 . ?
C58 H58B 1.0800 . ?
C58 H58C 1.0800 . ?
C59 H59A 1.0800 . ?
C59 H59B 1.0800 . ?
C59 H59C 1.0800 . ?
C61 H61A 1.0800 . ?
C61 H61B 1.0800 . ?
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
C6 C1 C2 C3 -1.1(4) . . . . ?
C13 C1 C2 C3 178.2(3) . . . . ?
C6 C1 C2 C7 -179.0(3) . . . . ?
C13 C1 C2 C7 0.3(4) . . . . ?
C1 C2 C3 C4 -2.2(4) . . . . ?
C7 C2 C3 C4 175.8(3) . . . . ?
C1 C2 C3 C8 -179.7(3) . . . . ?
C7 C2 C3 C8 -1.7(4) . . . . ?
C2 C3 C4 C5 2.1(4) . . . . ?
C8 C3 C4 C5 179.7(3) . . . . ?
C3 C4 C5 C6 1.4(4) . . . . ?
C3 C4 C5 C22 -178.2(3) . . . . ?
C4 C5 C6 C1 -4.9(4) . . . . ?
C22 C5 C6 C1 174.6(3) . . . . ?
C4 C5 C6 C9 168.6(3) . . . . ?
C22 C5 C6 C9 -11.9(4) . . . . ?
C2 C1 C6 C5 4.8(4) . . . . ?
C13 C1 C6 C5 -174.6(3) . . . . ?
C2 C1 C6 C9 -168.9(3) . . . . ?
C13 C1 C6 C9 11.8(4) . . . . ?
C1 C2 C7 N10 159(7) . . . . ?
C3 C2 C7 N10 -19(7) . . . . ?
C4 C3 C8 N11 -17(8) . . . . ?
C2 C3 C8 N11 161(7) . . . . ?
C5 C6 C9 N12 -102(5) . . . . ?
C1 C6 C9 N12 72(5) . . . . ?
C2 C1 C13 C18 46.4(4) . . . . ?
C6 C1 C13 C18 -134.3(3) . . . . ?
C2 C1 C13 C14 -131.2(3) . . . . ?
C6 C1 C13 C14 48.1(4) . . . . ?
C18 C13 C14 C15 0.5(4) . . . . ?
C1 C13 C14 C15 178.2(2) . . . . ?
C13 C14 C15 C16 1.5(4) . . . . ?
C20 N21 C16 C17 -4.0(4) . . . . ?
C19 N21 C16 C17 -174.9(2) . . . . ?
C20 N21 C16 C15 175.5(2) . . . . ?
C19 N21 C16 C15 4.6(4) . . . . ?
C14 C15 C16 N21 177.6(2) . . . . ?
C14 C15 C16 C17 -2.8(4) . . . . ?
N21 C16 C17 C18 -178.2(2) . . . . ?
C15 C16 C17 C18 2.3(4) . . . . ?
C16 C17 C18 C13 -0.3(4) . . . . ?
C14 C13 C18 C17 -1.1(4) . . . . ?
C1 C13 C18 C17 -178.8(2) . . . . ?
C4 C5 C22 C27 145.9(3) . . . . ?
C6 C5 C22 C27 -33.6(4) . . . . ?
C4 C5 C22 C23 -31.4(4) . . . . ?
C6 C5 C22 C23 149.0(3) . . . . ?
C27 C22 C23 C24 0.6(4) . . . . ?
C5 C22 C23 C24 178.0(3) . . . . ?
C22 C23 C24 C25 0.2(4) . . . . ?
C29 N30 C25 C24 -177.1(3) . . . . ?
C28 N30 C25 C24 5.1(4) . . . . ?
C29 N30 C25 C26 3.6(4) . . . . ?
C28 N30 C25 C26 -174.2(3) . . . . ?
C23 C24 C25 N30 -179.9(3) . . . . ?
C23 C24 C25 C26 -0.6(4) . . . . ?
N30 C25 C26 C27 179.7(3) . . . . ?
C24 C25 C26 C27 0.4(4) . . . . ?
C25 C26 C27 C22 0.3(4) . . . . ?
C23 C22 C27 C26 -0.8(4) . . . . ?
C5 C22 C27 C26 -178.2(3) . . . . ?
C36 C31 C32 C33 -0.3(4) . . . . ?
C43 C31 C32 C33 -178.7(3) . . . . ?
C36 C31 C32 C37 -176.9(3) . . . . ?
C43 C31 C32 C37 4.6(5) . . . . ?
C31 C32 C33 C34 -1.3(5) . . . . ?
C37 C32 C33 C34 175.5(3) . . . . ?
C31 C32 C33 C38 178.1(3) . . . . ?
C37 C32 C33 C38 -5.1(4) . . . . ?
C32 C33 C34 C35 2.2(5) . . . . ?
C38 C33 C34 C35 -177.1(3) . . . . ?
C33 C34 C35 C36 -1.5(4) . . . . ?
C33 C34 C35 C52 175.1(3) . . . . ?
C34 C35 C36 C31 0.0(4) . . . . ?
C52 C35 C36 C31 -176.5(3) . . . . ?
C34 C35 C36 C39 175.8(3) . . . . ?
C52 C35 C36 C39 -0.6(4) . . . . ?
C32 C31 C36 C35 0.9(4) . . . . ?
C43 C31 C36 C35 179.3(3) . . . . ?
C32 C31 C36 C39 -175.2(3) . . . . ?
C43 C31 C36 C39 3.2(4) . . . . ?
C31 C32 C37 N40 177(6) . . . . ?
C33 C32 C37 N40 0(7) . . . . ?
C34 C33 C38 N41 123(7) . . . . ?
C32 C33 C38 N41 -57(7) . . . . ?
C35 C36 C39 N42 165(15) . . . . ?
C31 C36 C39 N42 -19(15) . . . . ?
C32 C31 C43 C48 -129.0(3) . . . . ?
C36 C31 C43 C48 52.6(4) . . . . ?
C32 C31 C43 C44 49.1(4) . . . . ?
C36 C31 C43 C44 -129.3(3) . . . . ?
C48 C43 C44 C45 0.5(4) . . . . ?
C31 C43 C44 C45 -177.7(3) . . . . ?
C43 C44 C45 C46 0.4(5) . . . . ?
C49 N51 C46 C45 -176.7(3) . . . . ?
C50 N51 C46 C45 -11.3(4) . . . . ?
C49 N51 C46 C47 5.0(4) . . . . ?
C50 N51 C46 C47 170.4(3) . . . . ?
C44 C45 C46 N51 -179.3(3) . . . . ?
C44 C45 C46 C47 -0.9(4) . . . . ?
N51 C46 C47 C48 178.9(3) . . . . ?
C45 C46 C47 C48 0.5(4) . . . . ?
C46 C47 C48 C43 0.4(5) . . . . ?
C44 C43 C48 C47 -0.9(4) . . . . ?
C31 C43 C48 C47 177.2(3) . . . . ?
C34 C35 C52 C53 156.0(3) . . . . ?
C36 C35 C52 C53 -27.7(5) . . . . ?
C34 C35 C52 C57 -25.4(4) . . . . ?
C36 C35 C52 C57 151.0(3) . . . . ?
C57 C52 C53 C54 -3.5(5) . . . . ?
C35 C52 C53 C54 175.2(3) . . . . ?
C52 C53 C54 C55 -0.5(5) . . . . ?
C58 N60 C55 C56 -176.6(3) . . . . ?
C59 N60 C55 C56 7.4(5) . . . . ?
C58 N60 C55 C54 2.9(5) . . . . ?
C59 N60 C55 C54 -173.0(3) . . . . ?
C53 C54 C55 N60 -174.9(3) . . . . ?
C53 C54 C55 C56 4.7(5) . . . . ?
N60 C55 C56 C57 174.8(3) . . . . ?
C54 C55 C56 C57 -4.8(5) . . . . ?
C55 C56 C57 C52 0.8(5) . . . . ?
C53 C52 C57 C56 3.4(5) . . . . ?
C35 C52 C57 C56 -175.4(3) . . . . ?
