#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/56/2205689.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_2205689
loop_
_publ_author_name
'Bolte, Michael'
_publ_section_title
;
 4,4'-Bis(di-n-butylaminostyryl)-2,2'-bipyridine: a space group
 revision
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1364
_journal_page_last               o1366
_journal_paper_doi               10.1107/S1600536805011414
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C42 H54 N4'
_chemical_formula_moiety         'C42 H54 N4'
_chemical_formula_sum            'C42 H54 N4'
_chemical_formula_weight         614.89
_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_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.67(2)
_cell_angle_beta                 99.141(10)
_cell_angle_gamma                93.40(2)
_cell_formula_units_Z            2
_cell_length_a                   11.915(3)
_cell_length_b                   12.050(4)
_cell_length_c                   13.544(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_volume                     1837.8(8)
_computing_cell_refinement       'Enraf--Nonius CAD-4'
_computing_data_collection       'Enraf--Nonius CAD-4'
_computing_data_reduction        'Enraf--Nonius CAD-4'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'coordinates were input directly'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       'φ or ω scans?'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0718
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8328
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.97
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.111
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         7957
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.2045
_refine_ls_R_factor_gt           0.0795
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1309P)²+0.0377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2159
_refine_ls_wR_factor_ref         0.2702
_reflns_number_gt                3290
_reflns_number_total             7957
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6490.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2205689
_cod_database_fobs_code          2205689
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
N51 0.0709(2) -0.1189(2) -0.0652(2) 0.0698(7) Uani d . 1 . . N
N52 0.7479(2) 0.5612(2) 0.3534(2) 0.0824(8) Uani d . 1 A . N
C62 0.0593(2) -0.0117(3) -0.0086(2) 0.0594(8) Uani d . 1 . . C
C63 0.1498(2) 0.0739(3) 0.0333(2) 0.0613(8) Uani d . 1 . . C
H63 0.1372 0.1469 0.0724 0.074 Uiso calc R 1 . . H
C64 0.2596(3) 0.0515(3) 0.0172(2) 0.0629(8) Uani d . 1 . . C
C65 0.2711(3) -0.0581(3) -0.0429(3) 0.0726(9) Uani d . 1 . . C
H65 0.3421 -0.0773 -0.0582 0.087 Uiso calc R 1 . . H
C66 0.1765(3) -0.1386(3) -0.0800(3) 0.0767(9) Uani d . 1 . . C
H66 0.1872 -0.2126 -0.1184 0.092 Uiso calc R 1 . . H
C67 0.3593(3) 0.1375(3) 0.0612(3) 0.0691(9) Uani d . 1 . . C
H67 0.4215 0.1291 0.0272 0.083 Uiso calc R 1 . . H
C68 0.3681(3) 0.2264(3) 0.1456(3) 0.0694(9) Uani d . 1 . . C
H68 0.3045 0.2333 0.1778 0.083 Uiso calc R 1 . . H
C69 0.4642(3) 0.3146(3) 0.1945(2) 0.0617(8) Uani d . 1 . . C
C70 0.4675(3) 0.3889(3) 0.2927(3) 0.0767(10) Uani d . 1 . . C
H70 0.4052 0.3834 0.3254 0.092 Uiso calc R 1 . . H
C71 0.5586(3) 0.4710(3) 0.3450(3) 0.0817(10) Uani d . 1 . . C
H71 0.5559 0.5192 0.4108 0.098 Uiso calc R 1 . . H
C72 0.6550(3) 0.4825(3) 0.3000(3) 0.0697(9) Uani d . 1 . . C
C73 0.6491(3) 0.4119(3) 0.1988(3) 0.0699(9) Uani d . 1 . . C
H73 0.7093 0.4198 0.1642 0.084 Uiso calc R 1 . . H
C74 0.5579(3) 0.3313(3) 0.1485(2) 0.0670(8) Uani d . 1 . . C
H74 0.5586 0.2859 0.0811 0.080 Uiso calc R 1 . . H
C75 0.8452(3) 0.5764(3) 0.3047(3) 0.0933(12) Uani d . 1 . . C
H75A 0.8860 0.6527 0.3387 0.112 Uiso calc R 1 . . H
H75B 0.8188 0.5713 0.2320 0.112 Uiso calc R 1 . . H
C76 0.9282(4) 0.4816(4) 0.3126(4) 0.1174(15) Uani d . 1 . . C
H76A 0.9599 0.4923 0.3855 0.141 Uiso calc R 1 . . H
H76B 0.8845 0.4058 0.2861 0.141 Uiso calc R 1 . . H
C77 1.0174(5) 0.4839(6) 0.2582(4) 0.158(2) Uani d . 1 . . C
H77A 1.0625 0.5588 0.2879 0.190 Uiso calc R 1 . . H
H77B 0.9846 0.4792 0.1868 0.190 Uiso calc R 1 . . H
C78 1.0974(4) 0.3917(4) 0.2559(4) 0.1320(18) Uani d . 1 . . C
H78A 1.1551 0.4032 0.2165 0.198 Uiso calc R 1 . . H
H78B 1.0552 0.3168 0.2238 0.198 Uiso calc R 1 . . H
H78C 1.1330 0.3962 0.3258 0.198 Uiso calc R 1 . . H
C79 0.7629(4) 0.6195(3) 0.4633(3) 0.1028(13) Uani d D 1 . . C
H79A 0.8376 0.6045 0.4940 0.123 Uiso calc PR 0.464(13) A 1 H
H79B 0.7075 0.5791 0.4902 0.123 Uiso calc PR 0.464(13) A 1 H
H79C 0.8430 0.6401 0.4949 0.123 Uiso calc PR 0.536(13) A 2 H
H79D 0.7265 0.5734 0.5004 0.123 Uiso calc PR 0.536(13) A 2 H
C80 0.7554(10) 0.7461(8) 0.5086(10) 0.109(5) Uani d PD 0.464(13) A 1 C
H80A 0.7884 0.7689 0.5823 0.130 Uiso calc PR 0.464(13) A 1 H
H80B 0.7992 0.7902 0.4747 0.130 Uiso calc PR 0.464(13) A 1 H
C81 0.6367(7) 0.7731(8) 0.4953(10) 0.087(4) Uani d PD 0.464(13) A 1 C
H81A 0.5925 0.7303 0.5300 0.104 Uiso calc PR 0.464(13) A 1 H
H81B 0.6030 0.7508 0.4218 0.104 Uiso calc PR 0.464(13) A 1 H
C80' 0.6995(11) 0.7302(8) 0.4586(8) 0.118(5) Uani d PD 0.536(13) A 2 C
H80C 0.7350 0.7709 0.4168 0.141 Uiso calc PR 0.536(13) A 2 H
H80D 0.6203 0.7059 0.4251 0.141 Uiso calc PR 0.536(13) A 2 H
C81' 0.7040(13) 0.8101(9) 0.5648(9) 0.171(7) Uani d PD 0.536(13) A 2 C
H81C 0.7823 0.8393 0.5983 0.205 Uiso calc PR 0.536(13) A 2 H
H81D 0.6692 0.7712 0.6082 0.205 Uiso calc PR 0.536(13) A 2 H
C82 0.6345(5) 0.9103(5) 0.5449(5) 0.161(2) Uani d D 1 . . C
H82A 0.5568 0.9275 0.5440 0.241 Uiso calc PR 0.464(13) A 1 H
H82B 0.6701 0.9519 0.5047 0.241 Uiso calc PR 0.464(13) A 1 H
H82C 0.6754 0.9334 0.6155 0.241 Uiso calc PR 0.464(13) A 1 H
H82D 0.6365 0.9683 0.6098 0.241 Uiso calc PR 0.536(13) A 2 H
H82E 0.5567 0.8799 0.5142 0.241 Uiso calc PR 0.536(13) A 2 H
H82F 0.6677 0.9444 0.4983 0.241 Uiso calc PR 0.536(13) A 2 H
N1 0.0696(2) -0.6286(2) -0.0418(2) 0.0729(7) Uani d . 1 . . N
N2 0.7652(2) 0.0539(2) 0.3227(2) 0.0769(8) Uani d . 1 B . N
C2 0.0599(3) -0.5164(3) 0.0012(2) 0.0629(8) Uani d . 1 . . C
C3 0.1532(3) -0.4341(3) 0.0455(2) 0.0676(9) Uani d . 1 . . C
H3 0.1424 -0.3568 0.0730 0.081 Uiso calc R 1 . . H
C4 0.2636(3) -0.4674(3) 0.0489(2) 0.0644(8) Uani d . 1 . . C
C5 0.2722(3) -0.5842(3) 0.0048(3) 0.0746(9) Uani d . 1 . . C
H5 0.3436 -0.6115 0.0050 0.089 Uiso calc R 1 . . H
C6 0.1749(3) -0.6588(3) -0.0390(3) 0.0782(10) Uani d . 1 . . C
H6 0.1833 -0.7362 -0.0690 0.094 Uiso calc R 1 . . H
C7 0.3679(3) -0.3873(3) 0.0959(3) 0.0737(9) Uani d . 1 . . C
H7 0.4356 -0.4204 0.1073 0.088 Uiso calc R 1 . . H
C8 0.3753(3) -0.2737(3) 0.1234(2) 0.0717(9) Uani d . 1 . . C
H8 0.3073 -0.2414 0.1110 0.086 Uiso calc R 1 . . H
C9 0.4785(3) -0.1906(3) 0.1717(2) 0.0660(8) Uani d . 1 . . C
C10 0.5861(3) -0.2246(3) 0.1975(3) 0.0733(9) Uani d . 1 . . C
H10 0.5948 -0.3032 0.1831 0.088 Uiso calc R 1 . . H
C11 0.6801(3) -0.1447(3) 0.2438(3) 0.0770(10) Uani d . 1 . . C
H11 0.7512 -0.1709 0.2577 0.092 Uiso calc R 1 . . H
C12 0.6716(3) -0.0260(3) 0.2706(2) 0.0654(8) Uani d . 1 . . C
C13 0.5635(3) 0.0079(3) 0.2430(3) 0.0715(9) Uani d . 1 . . C
H13 0.5541 0.0864 0.2571 0.086 Uiso calc R 1 . . H
C14 0.4716(3) -0.0728(3) 0.1956(3) 0.0731(9) Uani d . 1 . . C
H14 0.4010 -0.0469 0.1787 0.088 Uiso calc R 1 . . H
C15 0.8744(3) 0.0146(3) 0.3592(3) 0.0829(10) Uani d . 1 . . C
H15A 0.8590 -0.0528 0.3831 0.100 Uiso calc R 1 . . H
H15B 0.9165 0.0754 0.4184 0.100 Uiso calc R 1 . . H
C16 0.9486(3) -0.0162(3) 0.2763(3) 0.0812(10) Uani d . 1 . . C
H16A 0.9030 -0.0675 0.2128 0.097 Uiso calc R 1 . . H
H16B 0.9753 0.0538 0.2609 0.097 Uiso calc R 1 . . H
C17 1.0506(3) -0.0747(4) 0.3111(3) 0.0979(12) Uani d . 1 . . C
H17A 1.0951 -0.0238 0.3754 0.118 Uiso calc R 1 . . H
H17B 1.0235 -0.1452 0.3256 0.118 Uiso calc R 1 . . H
C18 1.1259(4) -0.1041(4) 0.2315(3) 0.1218(15) Uani d . 1 . . C
H18A 1.1889 -0.1411 0.2572 0.183 Uiso calc R 1 . . H
H18B 1.1545 -0.0345 0.2181 0.183 Uiso calc R 1 . . H
H18C 1.0828 -0.1557 0.1681 0.183 Uiso calc R 1 . . H
C19 0.7611(3) 0.1778(3) 0.3464(3) 0.0908(11) Uani d D 1 . . C
H19A 0.6937 0.1904 0.3020 0.109 Uiso calc PR 0.551(15) B 1 H
H19B 0.8267 0.2093 0.3246 0.109 Uiso calc PR 0.551(15) B 1 H
H19C 0.7148 0.1980 0.2894 0.109 Uiso calc PR 0.449(15) B 2 H
H19D 0.8373 0.2184 0.3603 0.109 Uiso calc PR 0.449(15) B 2 H
C20 0.7592(11) 0.2505(9) 0.4552(8) 0.126(5) Uani d PD 0.551(15) B 1 C
H20A 0.8229 0.2327 0.5005 0.152 Uiso calc PR 0.551(15) B 1 H
H20B 0.7755 0.3308 0.4565 0.152 Uiso calc PR 0.551(15) B 1 H
C21 0.6710(10) 0.2448(14) 0.4975(9) 0.175(8) Uani d PD 0.551(15) B 1 C
H21A 0.6484 0.1638 0.4898 0.210 Uiso calc PR 0.551(15) B 1 H
H21B 0.6091 0.2729 0.4584 0.210 Uiso calc PR 0.551(15) B 1 H
C21' 0.7539(12) 0.273(2) 0.5290(9) 0.255(14) Uani d PD 0.449(15) B 2 C
H21C 0.7875 0.3414 0.5159 0.306 Uiso calc PR 0.449(15) B 2 H
H21D 0.8165 0.2351 0.5563 0.306 Uiso calc PR 0.449(15) B 2 H
C20' 0.7064(13) 0.2067(14) 0.4442(11) 0.198(12) Uani d PD 0.449(15) B 2 C
H20C 0.6351 0.2372 0.4253 0.238 Uiso calc PR 0.449(15) B 2 H
H20D 0.6860 0.1333 0.4568 0.238 Uiso calc PR 0.449(15) B 2 H
C22 0.6832(5) 0.3139(5) 0.6172(4) 0.156(2) Uani d D 1 . . C
H22A 0.6118 0.3036 0.6396 0.234 Uiso calc PR 0.551(15) B 1 H
H22B 0.7033 0.3948 0.6264 0.234 Uiso calc PR 0.551(15) B 1 H
H22C 0.7417 0.2849 0.6578 0.234 Uiso calc PR 0.551(15) B 1 H
H22D 0.7337 0.3562 0.6805 0.234 Uiso calc PR 0.449(15) B 2 H
H22E 0.6435 0.2477 0.6281 0.234 Uiso calc PR 0.449(15) B 2 H
H22F 0.6287 0.3630 0.5972 0.234 Uiso calc PR 0.449(15) B 2 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
C66 N51 C62 . 115.7(3)
C72 N52 C79 . 123.1(3)
C72 N52 C75 . 120.7(3)
C79 N52 C75 . 115.6(3)
N51 C62 C63 . 123.2(3)
N51 C62 C62 2 116.2(3)
C63 C62 C62 2 120.5(4)
C62 C63 C64 . 120.2(3)
C62 C63 H63 . 119.9
C64 C63 H63 . 119.9
C65 C64 C63 . 116.4(3)
C65 C64 C67 . 120.6(3)
C63 C64 C67 . 122.9(3)
C66 C65 C64 . 119.4(3)
C66 C65 H65 . 120.3
C64 C65 H65 . 120.3
N51 C66 C65 . 125.0(3)
N51 C66 H66 . 117.5
C65 C66 H66 . 117.5
C68 C67 C64 . 125.3(3)
C68 C67 H67 . 117.3
C64 C67 H67 . 117.3
C67 C68 C69 . 128.5(3)
C67 C68 H68 . 115.7
C69 C68 H68 . 115.7
C70 C69 C74 . 115.1(3)
C70 C69 C68 . 120.8(3)
C74 C69 C68 . 124.1(3)
C71 C70 C69 . 123.4(3)
C71 C70 H70 . 118.3
C69 C70 H70 . 118.3
C70 C71 C72 . 120.8(3)
C70 C71 H71 . 119.6
C72 C71 H71 . 119.6
N52 C72 C73 . 123.1(3)
N52 C72 C71 . 121.0(3)
C73 C72 C71 . 115.9(3)
C74 C73 C72 . 122.2(3)
C74 C73 H73 . 118.9
C72 C73 H73 . 118.9
C73 C74 C69 . 122.4(3)
C73 C74 H74 . 118.8
C69 C74 H74 . 118.8
N52 C75 C76 . 110.9(3)
N52 C75 H75A . 109.5
C76 C75 H75A . 109.5
N52 C75 H75B . 109.5
C76 C75 H75B . 109.5
H75A C75 H75B . 108.1
C77 C76 C75 . 113.8(4)
C77 C76 H76A . 108.8
C75 C76 H76A . 108.8
C77 C76 H76B . 108.8
C75 C76 H76B . 108.8
H76A C76 H76B . 107.7
C76 C77 C78 . 117.7(5)
C76 C77 H77A . 107.9
C78 C77 H77A . 107.9
C76 C77 H77B . 107.9
C78 C77 H77B . 107.9
H77A C77 H77B . 107.2
C77 C78 H78A . 109.5
C77 C78 H78B . 109.5
H78A C78 H78B . 109.5
C77 C78 H78C . 109.5
H78A C78 H78C . 109.5
H78B C78 H78C . 109.5
N52 C79 C80 . 124.8(6)
N52 C79 C80' . 99.6(5)
N52 C79 H79A . 106.1
C80 C79 H79A . 106.1
N52 C79 H79B . 106.1
C80 C79 H79B . 106.1
H79A C79 H79B . 106.3
N52 C79 H79C . 111.8
C80' C79 H79C . 111.8
N52 C79 H79D . 111.8
C80' C79 H79D . 111.8
H79C C79 H79D . 109.6
C81 C80 C79 . 111.3(9)
C81 C80 H80A . 109.4
C79 C80 H80A . 109.4
C81 C80 H80B . 109.4
C79 C80 H80B . 109.4
H80A C80 H80B . 108.0
C80 C81 C82 . 108.9(8)
C80 C81 H81A . 109.9
C82 C81 H81A . 109.9
C80 C81 H81B . 109.9
C82 C81 H81B . 109.9
H81A C81 H81B . 108.3
C81' C80' C79 . 111.4(9)
C81' C80' H80C . 109.3
C79 C80' H80C . 109.3
C81' C80' H80D . 109.3
C79 C80' H80D . 109.3
H80C C80' H80D . 108.0
C80' C81' C82 . 104.1(9)
C80' C81' H81C . 110.9
C82 C81' H81C . 110.9
C80' C81' H81D . 110.9
C82 C81' H81D . 110.9
H81C C81' H81D . 109.0
C81 C82 H82A . 109.5
C81 C82 H82B . 109.5
H82A C82 H82B . 109.5
C81' C82 H82C . 70.8
C81' C82 H82D . 109.5
C81' C82 H82E . 109.5
C81 C82 H82E . 74.2
H82D C82 H82E . 109.5
C81' C82 H82F . 109.5
H82D C82 H82F . 109.5
H82E C82 H82F . 109.5
C6 N1 C2 . 116.4(3)
C12 N2 C19 . 123.1(3)
C12 N2 C15 . 120.4(3)
C19 N2 C15 . 116.5(3)
N1 C2 C3 . 123.1(3)
N1 C2 C2 2_545 115.9(3)
C3 C2 C2 2_545 121.0(4)
C2 C3 C4 . 119.9(3)
C2 C3 H3 . 120.1
C4 C3 H3 . 120.1
C5 C4 C3 . 116.4(3)
C5 C4 C7 . 119.6(3)
C3 C4 C7 . 124.0(3)
C6 C5 C4 . 119.5(3)
C6 C5 H5 . 120.2
C4 C5 H5 . 120.2
N1 C6 C5 . 124.7(3)
N1 C6 H6 . 117.6
C5 C6 H6 . 117.6
C8 C7 C4 . 126.5(3)
C8 C7 H7 . 116.7
C4 C7 H7 . 116.7
C7 C8 C9 . 127.9(3)
C7 C8 H8 . 116.0
C9 C8 H8 . 116.0
C14 C9 C10 . 116.1(3)
C14 C9 C8 . 120.7(3)
C10 C9 C8 . 123.2(3)
C11 C10 C9 . 121.6(3)
C11 C10 H10 . 119.2
C9 C10 H10 . 119.2
C10 C11 C12 . 121.8(3)
C10 C11 H11 . 119.1
C12 C11 H11 . 119.1
N2 C12 C11 . 121.6(3)
N2 C12 C13 . 122.1(3)
C11 C12 C13 . 116.3(3)
C14 C13 C12 . 120.9(3)
C14 C13 H13 . 119.6
C12 C13 H13 . 119.6
C13 C14 C9 . 123.2(3)
C13 C14 H14 . 118.4
C9 C14 H14 . 118.4
N2 C15 C16 . 113.5(3)
N2 C15 H15A . 108.9
C16 C15 H15A . 108.9
N2 C15 H15B . 108.9
C16 C15 H15B . 108.9
H15A C15 H15B . 107.7
C17 C16 C15 . 111.8(3)
C17 C16 H16A . 109.3
C15 C16 H16A . 109.3
C17 C16 H16B . 109.3
C15 C16 H16B . 109.3
H16A C16 H16B . 107.9
C18 C17 C16 . 112.8(3)
C18 C17 H17A . 109.0
C16 C17 H17A . 109.0
C18 C17 H17B . 109.0
C16 C17 H17B . 109.0
H17A C17 H17B . 107.8
C17 C18 H18A . 109.5
C17 C18 H18B . 109.5
H18A C18 H18B . 109.5
C17 C18 H18C . 109.5
H18A C18 H18C . 109.5
H18B C18 H18C . 109.5
N2 C19 C20 . 121.3(5)
N2 C19 C20' . 103.4(8)
N2 C19 H19A . 107.0
C20 C19 H19A . 107.0
N2 C19 H19B . 107.0
C20 C19 H19B . 107.0
H19A C19 H19B . 106.7
N2 C19 H19C . 111.1
C20 C19 H19C . 117.4
C20' C19 H19C . 111.1
N2 C19 H19D . 111.1
C20' C19 H19D . 111.1
H19C C19 H19D . 109.0
C21 C20 C19 . 121.4(11)
C21 C20 H20A . 107.0
C19 C20 H20A . 107.0
C21 C20 H20B . 107.0
C19 C20 H20B . 107.0
H20A C20 H20B . 106.7
C20 C21 C22 . 117.2(11)
C20 C21 H21A . 108.0
C22 C21 H21A . 108.0
C20 C21 H21B . 108.0
C22 C21 H21B . 108.0
H21A C21 H21B . 107.2
C20' C21' C22 . 119.6(11)
C20' C21' H21C . 107.4
C22 C21' H21C . 107.4
C20' C21' H21D . 107.4
C22 C21' H21D . 107.4
H21C C21' H21D . 107.0
C21' C20' C19 . 124.0(10)
C21' C20' H20C . 106.3
C19 C20' H20C . 106.3
C21' C20' H20D . 106.3
C19 C20' H20D . 106.3
H20C C20' H20D . 106.4
C21 C22 H22A . 109.5
C21 C22 H22B . 109.5
H22A C22 H22B . 109.5
C21 C22 H22C . 109.5
H22A C22 H22C . 109.5
H22B C22 H22C . 109.5
C21' C22 H22D . 109.5
C21' C22 H22E . 109.5
H22D C22 H22E . 109.5
C21' C22 H22F . 109.5
H22D C22 H22F . 109.5
H22E C22 H22F . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N51 C66 . 1.330(4)
N51 C62 . 1.340(4)
N52 C72 . 1.378(4)
N52 C79 . 1.440(4)
N52 C75 . 1.447(4)
C62 C63 . 1.381(4)
C62 C62 2 1.498(6)
C63 C64 . 1.391(4)
C63 H63 . 0.9300
C64 C65 . 1.378(4)
C64 C67 . 1.461(4)
C65 C66 . 1.375(4)
C65 H65 . 0.9300
C66 H66 . 0.9300
C67 C68 . 1.323(4)
C67 H67 . 0.9300
C68 C69 . 1.453(4)
C68 H68 . 0.9300
C69 C70 . 1.383(4)
C69 C74 . 1.392(4)
C70 C71 . 1.382(4)
C70 H70 . 0.9300
C71 C72 . 1.399(4)
C71 H71 . 0.9300
C72 C73 . 1.394(4)
C73 C74 . 1.368(4)
C73 H73 . 0.9300
C74 H74 . 0.9300
C75 C76 . 1.569(5)
C75 H75A . 0.9700
C75 H75B . 0.9700
C76 C77 . 1.389(6)
C76 H76A . 0.9700
C76 H76B . 0.9700
C77 C78 . 1.504(6)
C77 H77A . 0.9700
C77 H77B . 0.9700
C78 H78A . 0.9600
C78 H78B . 0.9600
C78 H78C . 0.9600
C79 C80 . 1.497(9)
C79 C80' . 1.582(11)
C79 H79A . 0.9700
C79 H79B . 0.9700
C79 H79C . 0.9700
C79 H79D . 0.9700
C80 C81 . 1.464(11)
C80 H80A . 0.9700
C80 H80B . 0.9700
C81 C82 . 1.611(10)
C81 H81A . 0.9700
C81 H81B . 0.9700
C80' C81' . 1.490(12)
C80' H80C . 0.9700
C80' H80D . 0.9700
C81' C82 . 1.562(12)
C81' H81C . 0.9700
C81' H81D . 0.9700
C82 H82A . 0.9600
C82 H82B . 0.9600
C82 H82C . 0.9600
C82 H82D . 0.9600
C82 H82E . 0.9600
C82 H82F . 0.9600
N1 C6 . 1.325(4)
N1 C2 . 1.339(4)
N2 C12 . 1.387(4)
N2 C19 . 1.446(4)
N2 C15 . 1.469(4)
C2 C3 . 1.384(4)
C2 C2 2_545 1.501(6)
C3 C4 . 1.395(4)
C3 H3 . 0.9300
C4 C5 . 1.389(4)
C4 C7 . 1.468(4)
C5 C6 . 1.369(4)
C5 H5 . 0.9300
C6 H6 . 0.9300
C7 C8 . 1.312(4)
C7 H7 . 0.9300
C8 C9 . 1.479(4)
C8 H8 . 0.9300
C9 C14 . 1.379(4)
C9 C10 . 1.389(4)
C10 C11 . 1.377(4)
C10 H10 . 0.9300
C11 C12 . 1.392(4)
C11 H11 . 0.9300
C12 C13 . 1.399(4)
C13 C14 . 1.367(4)
C13 H13 . 0.9300
C14 H14 . 0.9300
C15 C16 . 1.519(4)
C15 H15A . 0.9700
C15 H15B . 0.9700
C16 C17 . 1.515(5)
C16 H16A . 0.9700
C16 H16B . 0.9700
C17 C18 . 1.494(5)
C17 H17A . 0.9700
C17 H17B . 0.9700
C18 H18A . 0.9600
C18 H18B . 0.9600
C18 H18C . 0.9600
C19 C20 . 1.501(8)
C19 C20' . 1.534(11)
C19 H19A . 0.9700
C19 H19B . 0.9700
C19 H19C . 0.9700
C19 H19D . 0.9700
C20 C21 . 1.281(13)
C20 H20A . 0.9700
C20 H20B . 0.9700
C21 C22 . 1.589(11)
C21 H21A . 0.9700
C21 H21B . 0.9700
C21' C20' . 1.233(12)
C21' C22 . 1.559(11)
C21' H21C . 0.9700
C21' H21D . 0.9700
C20' H20C . 0.9700
C20' H20D . 0.9700
C22 H22A . 0.9600
C22 H22B . 0.9600
C22 H22C . 0.9600
C22 H22D . 0.9600
C22 H22E . 0.9600
C22 H22F . 0.9600
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_4
_geom_torsion
C66 N51 C62 C63 . . -0.5(4)
C66 N51 C62 C62 . 2 179.9(3)
N51 C62 C63 C64 . . 0.4(5)
C62 C62 C63 C64 2 . 179.9(3)
C62 C63 C64 C65 . . 0.9(4)
C62 C63 C64 C67 . . -178.6(3)
C63 C64 C65 C66 . . -2.0(5)
C67 C64 C65 C66 . . 177.5(3)
C62 N51 C66 C65 . . -0.7(5)
C64 C65 C66 N51 . . 2.1(5)
C65 C64 C67 C68 . . -155.0(3)
C63 C64 C67 C68 . . 24.5(5)
C64 C67 C68 C69 . . 179.4(3)
C67 C68 C69 C70 . . -168.0(3)
C67 C68 C69 C74 . . 11.9(5)
C74 C69 C70 C71 . . -2.8(5)
C68 C69 C70 C71 . . 177.1(3)
C69 C70 C71 C72 . . -0.5(5)
C79 N52 C72 C73 . . -168.9(3)
C75 N52 C72 C73 . . 1.5(5)
C79 N52 C72 C71 . . 12.4(5)
C75 N52 C72 C71 . . -177.2(3)
C70 C71 C72 N52 . . -177.5(3)
C70 C71 C72 C73 . . 3.8(5)
N52 C72 C73 C74 . . 177.5(3)
C71 C72 C73 C74 . . -3.8(5)
C72 C73 C74 C69 . . 0.5(5)
C70 C69 C74 C73 . . 2.8(4)
C68 C69 C74 C73 . . -177.1(3)
C72 N52 C75 C76 . . -82.7(4)
C79 N52 C75 C76 . . 88.4(4)
N52 C75 C76 C77 . . 173.8(4)
C75 C76 C77 C78 . . -176.4(4)
C72 N52 C79 C80 . . -110.7(7)
C75 N52 C79 C80 . . 78.5(7)
C72 N52 C79 C80' . . -89.7(6)
C75 N52 C79 C80' . . 99.4(6)
N52 C79 C80 C81 . . 74.5(12)
C80' C79 C80 C81 . . 32.3(11)
C79 C80 C81 C82 . . -179.6(7)
N52 C79 C80' C81' . . -178.7(10)
C80 C79 C80' C81' . . -32.7(12)
C79 C80' C81' C82 . . -178.1(8)
C80' C81' C82 C81 . . 31.6(8)
C80 C81 C82 C81' . . -34.2(10)
C6 N1 C2 C3 . . 0.9(4)
C6 N1 C2 C2 . 2_545 -179.3(3)
N1 C2 C3 C4 . . -1.6(5)
C2 C2 C3 C4 2_545 . 178.5(3)
C2 C3 C4 C5 . . 1.0(4)
C2 C3 C4 C7 . . -178.8(3)
C3 C4 C5 C6 . . 0.3(5)
C7 C4 C5 C6 . . -179.9(3)
C2 N1 C6 C5 . . 0.5(5)
C4 C5 C6 N1 . . -1.1(5)
C5 C4 C7 C8 . . 167.0(3)
C3 C4 C7 C8 . . -13.3(5)
C4 C7 C8 C9 . . 179.3(3)
C7 C8 C9 C14 . . 179.8(3)
C7 C8 C9 C10 . . -1.6(5)
C14 C9 C10 C11 . . -0.3(5)
C8 C9 C10 C11 . . -179.0(3)
C9 C10 C11 C12 . . 2.3(5)
C19 N2 C12 C11 . . 176.4(3)
C15 N2 C12 C11 . . -5.3(5)
C19 N2 C12 C13 . . -4.3(5)
C15 N2 C12 C13 . . 174.0(3)
C10 C11 C12 N2 . . 176.2(3)
C10 C11 C12 C13 . . -3.1(5)
N2 C12 C13 C14 . . -177.2(3)
C11 C12 C13 C14 . . 2.1(5)
C12 C13 C14 C9 . . -0.3(5)
C10 C9 C14 C13 . . -0.7(5)
C8 C9 C14 C13 . . 178.1(3)
C12 N2 C15 C16 . . 84.7(4)
C19 N2 C15 C16 . . -96.8(4)
N2 C15 C16 C17 . . -170.5(3)
C15 C16 C17 C18 . . -179.1(3)
C12 N2 C19 C20 . . 105.6(7)
C15 N2 C19 C20 . . -72.8(7)
C12 N2 C19 C20' . . 80.6(8)
C15 N2 C19 C20' . . -97.9(8)
N2 C19 C20 C21 . . -70.9(14)
C20' C19 C20 C21 . . -13(2)
C19 C20 C21 C22 . . 172.9(8)
C22 C21' C20' C19 . . 168.7(15)
N2 C19 C20' C21' . . 119(3)
C20 C19 C20' C21' . . -13.0(18)
C20' C21' C22 C21 . . -7.7(18)
C20 C21 C22 C21' . . -11.1(17)
