#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/42/1514267.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_1514267
loop_
_publ_author_name
'Levick, Matthew T'
'Grace, Iain'
'Dai, Sheng-Yao'
'Kasch, Nicholas'
'Muryn, Christopher'
'Lambert, Colin'
'Turner, Michael L'
'Procter, David J'
_publ_section_title
;
 A Sm(II)-Mediated Cascade Approach to Dibenzoindolo[3,2-b]carbazoles:
 Synthesis and Evaluation.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2292
_journal_page_last               2295
_journal_paper_doi               10.1021/ol500841b
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C50 H64 N2'
_chemical_formula_weight         693.03
_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_date
;
'Fri Nov 23 09:42:09 2012'
;
_audit_creation_method
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_cell_angle_alpha                95.482(9)
_cell_angle_beta                 94.572(7)
_cell_angle_gamma                97.856(9)
_cell_formula_units_Z            2
_cell_length_a                   5.9862(5)
_cell_length_b                   16.452(2)
_cell_length_c                   20.7760(18)
_cell_measurement_reflns_used    2891
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.7355
_cell_measurement_theta_min      2.1440
_cell_volume                     2008.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
  1 omega   52.00  222.00   2.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   73.8681  204.2088 85

  2 phi   -109.56  146.44   2.0000   25.0000
omega____ theta____ kappa____ phi______ frames
  91.3691   93.0000   73.8681     -     128

  3 phi    -25.79  334.10   1.9994   25.0000
omega____ theta____ kappa____ phi______ frames
 124.2091  112.0000   73.8681     -     180

  4 omega  107.96  227.96   2.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   73.8681  304.2081 60

  5 omega  152.71  268.71   2.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   73.8681   74.2094 58

  6 omega   81.21  269.21   2.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   73.8681  234.2075 94

  7 phi     61.91  243.91   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
 324.3291  -30.0000   73.8681     -     91

  8 omega   94.71  258.71   2.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   73.8681  184.2088 82

  9 omega  -83.79   -3.79   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -55.0000   73.8681  -10.7913 40

 10 omega  164.33  236.33   2.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   73.8681  -15.7900 36

 11 phi    -88.32  149.68   2.0000   10.0000
omega____ theta____ kappa____ phi______ frames
  60.3991  -72.0000   73.8681     -     119

 12 omega  165.21  269.21   2.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   73.8681  174.2081 52

 13 omega  110.47  212.47   2.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   73.8681  154.2088 51

 14 omega  -98.49    1.51   2.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -70.0000   73.8681  139.2088 50

 15 phi    -25.79  108.17   1.9994   10.0000
omega____ theta____ kappa____ phi______ frames
 -25.5006  -75.0000   73.8681     -     67

 16 omega  136.86  266.86   2.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   73.8681  184.2088 65

;
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and π scans'
_diffrn_orient_matrix_UB_11      0.0571650000
_diffrn_orient_matrix_UB_12      0.0921871000
_diffrn_orient_matrix_UB_13      -0.0089039000
_diffrn_orient_matrix_UB_21      -0.0067164000
_diffrn_orient_matrix_UB_22      0.0225157000
_diffrn_orient_matrix_UB_23      0.0734495000
_diffrn_orient_matrix_UB_31      0.2545224000
_diffrn_orient_matrix_UB_32      -0.0059337000
_diffrn_orient_matrix_UB_33      0.0111555000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.2151
_diffrn_reflns_av_sigmaI/netI    0.3074
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21331
_diffrn_reflns_theta_full        66.58
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         2.1440
_exptl_absorpt_coefficient_mu    0.486
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         6838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.2047
_refine_ls_R_factor_gt           0.0886
_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)+(0.0343P)²+0.7648P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1750
_refine_ls_wR_factor_ref         0.2254
_reflns_number_gt                2923
_reflns_number_total             6838
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol500841b_si_003.cif
_cod_data_source_block           xdjp3na
_cod_depositor_comments
;Adding full bibliography for
 ./tmp-cod-update-bibliographies-8800/cifs/1514267.cif.
;
_cod_database_code               1514267
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
C1 C 0.1886(9) 0.1105(3) 0.5912(2) 0.0305(12) Uani 1 1 d .
C2 C 0.0597(9) 0.1526(3) 0.6316(3) 0.0326(12) Uani 1 1 d .
H2 H -0.0673 0.1748 0.6140 0.039 Uiso 1 1 calc R
C3 C 0.1196(10) 0.1618(3) 0.6987(3) 0.0333(13) Uani 1 1 d .
C4 C -0.0082(9) 0.2032(3) 0.7431(3) 0.0328(12) Uani 1 1 d .
H4 H -0.1397 0.2236 0.7264 0.039 Uiso 1 1 calc R
C5 C 0.0508(9) 0.2147(3) 0.8087(3) 0.0326(12) Uani 1 1 d .
C6 C 0.2458(10) 0.1827(4) 0.8349(3) 0.0383(13) Uani 1 1 d .
C7 C 0.3675(10) 0.1409(4) 0.7936(3) 0.0378(14) Uani 1 1 d .
H7 H 0.4958 0.1193 0.8110 0.045 Uiso 1 1 calc R
C8 C 0.3086(9) 0.1286(3) 0.7253(3) 0.0316(12) Uani 1 1 d .
C9 C 0.4376(9) 0.0845(3) 0.6827(3) 0.0330(13) Uani 1 1 d .
H9 H 0.5643 0.0615 0.6996 0.040 Uiso 1 1 calc R
C10 C 0.3752(9) 0.0759(3) 0.6170(2) 0.0306(12) Uani 1 1 d .
C11 C 0.4666(10) 0.0344(3) 0.5617(3) 0.0302(11) Uani 1 1 d .
C12 C 0.3322(9) 0.0486(3) 0.5050(2) 0.0302(12) Uani 1 1 d .
C13 C -0.0067(9) 0.1199(3) 0.4794(2) 0.0323(12) Uani 1 1 d .
H13A H -0.1417 0.1273 0.5027 0.039 Uiso 1 1 calc R
H13B H -0.0529 0.0750 0.4436 0.039 Uiso 1 1 calc R
C14 C 0.0700(10) 0.1982(3) 0.4506(3) 0.0360(13) Uani 1 1 d .
H14A H 0.2083 0.1921 0.4285 0.043 Uiso 1 1 calc R
H14B H 0.1084 0.2442 0.4858 0.043 Uiso 1 1 calc R
C15 C -0.1153(11) 0.2188(4) 0.4015(3) 0.0447(15) Uani 1 1 d .
H15A H -0.2560 0.2212 0.4231 0.054 Uiso 1 1 calc R
H15B H -0.0668 0.2742 0.3880 0.054 Uiso 1 1 calc R
C16 C -0.1668(11) 0.1559(4) 0.3405(3) 0.0418(15) Uani 1 1 d .
H16A H -0.2050 0.1001 0.3544 0.050 Uiso 1 1 calc R
H16B H -0.3019 0.1684 0.3147 0.050 Uiso 1 1 calc R
C17 C 0.0247(13) 0.1545(4) 0.2973(3) 0.0540(18) Uani 1 1 d .
H17A H 0.1620 0.1443 0.3233 0.065 Uiso 1 1 calc R
H17B H 0.0584 0.2094 0.2815 0.065 Uiso 1 1 calc R
C18 C -0.0272(13) 0.0893(4) 0.2392(3) 0.0563(18) Uani 1 1 d .
H18A H -0.0587 0.0344 0.2550 0.068 Uiso 1 1 calc R
H18B H -0.1661 0.0990 0.2136 0.068 Uiso 1 1 calc R
C19 C 0.1621(14) 0.0884(5) 0.1951(3) 0.065(2) Uani 1 1 d .
H19A H 0.3031 0.0818 0.2211 0.078 Uiso 1 1 calc R
H19B H 0.1878 0.1423 0.1773 0.078 Uiso 1 1 calc R
C20 C 0.1146(14) 0.0199(5) 0.1389(3) 0.0592(19) Uani 1 1 d .
H20A H 0.0923 -0.0338 0.1570 0.071 Uiso 1 1 calc R
H20B H -0.0291 0.0257 0.1139 0.071 Uiso 1 1 calc R
C21 C 0.2975(18) 0.0182(5) 0.0925(4) 0.081(3) Uani 1 1 d .
H21A H 0.3171 0.0710 0.0730 0.098 Uiso 1 1 calc R
H21B H 0.4425 0.0134 0.1173 0.098 Uiso 1 1 calc R
C22 C 0.2445(17) -0.0521(5) 0.0389(4) 0.084(3) Uani 1 1 d .
H22A H 0.2345 -0.1047 0.0577 0.126 Uiso 1 1 calc R
H22B H 0.3649 -0.0489 0.0095 0.126 Uiso 1 1 calc R
H22C H 0.0997 -0.0484 0.0146 0.126 Uiso 1 1 calc R
C23 C -0.0910(10) 0.2608(4) 0.8532(3) 0.0413(14) Uani 1 1 d .
H23A H -0.0086 0.3158 0.8684 0.062 Uiso 1 1 calc R
H23B H -0.1205 0.2301 0.8905 0.062 Uiso 1 1 calc R
H23C H -0.2351 0.2662 0.8292 0.062 Uiso 1 1 calc R
C24 C 0.3164(11) 0.1969(4) 0.9066(3) 0.0512(17) Uani 1 1 d .
H24A H 0.4555 0.1732 0.9159 0.077 Uiso 1 1 calc R
H24B H 0.1959 0.1704 0.9301 0.077 Uiso 1 1 calc R
H24C H 0.3438 0.2563 0.9205 0.077 Uiso 1 1 calc R
C25 C 0.6350(9) -0.0151(3) 0.5566(2) 0.0327(12) Uani 1 1 d .
H25 H 0.7245 -0.0256 0.5939 0.039 Uiso 1 1 calc R
C26 C 1.1710(9) 0.4970(3) 0.1233(2) 0.0316(12) Uani 1 1 d .
C27 C 1.0388(9) 0.5003(3) 0.1748(2) 0.0318(12) Uani 1 1 d .
H27 H 0.8914 0.4695 0.1714 0.038 Uiso 1 1 calc R
C28 C 1.1274(9) 0.5506(3) 0.2327(2) 0.0298(12) Uani 1 1 d .
C29 C 1.0026(9) 0.5577(3) 0.2880(2) 0.0302(12) Uani 1 1 d .
H29 H 0.8537 0.5281 0.2855 0.036 Uiso 1 1 calc R
C30 C 1.0869(10) 0.6049(3) 0.3445(2) 0.0336(12) Uani 1 1 d .
C31 C 1.3097(9) 0.6491(3) 0.3495(2) 0.0335(12) Uani 1 1 d .
C32 C 1.4354(9) 0.6450(3) 0.2965(2) 0.0297(12) Uani 1 1 d .
H32 H 1.5830 0.6757 0.2998 0.036 Uiso 1 1 calc R
C33 C 1.3503(9) 0.5963(3) 0.2376(2) 0.0273(11) Uani 1 1 d .
C34 C 1.4792(9) 0.5940(3) 0.1834(2) 0.0305(12) Uani 1 1 d .
H34 H 1.6253 0.6256 0.1858 0.037 Uiso 1 1 calc R
C35 C 1.3899(9) 0.5450(3) 0.1265(2) 0.0288(11) Uani 1 1 d .
C36 C 1.4747(10) 0.5281(3) 0.0636(2) 0.0274(11) Uani 1 1 d .
C37 C 1.3041(9) 0.4698(3) 0.0265(2) 0.0276(11) Uani 1 1 d .
C38 C 0.9280(9) 0.3885(3) 0.0449(2) 0.0300(11) Uani 1 1 d .
H38A H 0.8967 0.3806 -0.0029 0.036 Uiso 1 1 calc R
H38B H 0.7931 0.4065 0.0634 0.036 Uiso 1 1 calc R
C39 C 0.9653(9) 0.3069(3) 0.0687(2) 0.0327(12) Uani 1 1 d .
H39A H 1.0334 0.3169 0.1143 0.039 Uiso 1 1 calc R
H39B H 1.0742 0.2820 0.0423 0.039 Uiso 1 1 calc R
C40 C 0.7466(10) 0.2460(3) 0.0650(3) 0.0375(13) Uani 1 1 d .
H40A H 0.7840 0.1930 0.0787 0.045 Uiso 1 1 calc R
H40B H 0.6808 0.2354 0.0193 0.045 Uiso 1 1 calc R
C41 C 0.5675(10) 0.2753(4) 0.1071(3) 0.0442(15) Uani 1 1 d .
H41A H 0.5282 0.3276 0.0926 0.053 Uiso 1 1 calc R
H41B H 0.4290 0.2339 0.0991 0.053 Uiso 1 1 calc R
C42 C 0.6363(11) 0.2893(4) 0.1803(3) 0.0422(14) Uani 1 1 d .
H42A H 0.6421 0.2351 0.1968 0.051 Uiso 1 1 calc R
H42B H 0.7907 0.3209 0.1879 0.051 Uiso 1 1 calc R
C43 C 0.4797(11) 0.3345(4) 0.2183(3) 0.0425(14) Uani 1 1 d .
H43A H 0.3235 0.3049 0.2084 0.051 Uiso 1 1 calc R
H43B H 0.4818 0.3902 0.2038 0.051 Uiso 1 1 calc R
C44 C 0.5393(12) 0.3434(4) 0.2907(3) 0.0479(16) Uani 1 1 d .
H44A H 0.6983 0.3703 0.3004 0.058 Uiso 1 1 calc R
H44B H 0.5289 0.2877 0.3056 0.058 Uiso 1 1 calc R
C45 C 0.3878(12) 0.3935(4) 0.3293(3) 0.0470(15) Uani 1 1 d .
H45A H 0.4092 0.4508 0.3176 0.056 Uiso 1 1 calc R
H45B H 0.2275 0.3698 0.3167 0.056 Uiso 1 1 calc R
C46 C 0.4359(11) 0.3954(4) 0.4025(3) 0.0451(15) Uani 1 1 d .
H46A H 0.4175 0.3380 0.4140 0.054 Uiso 1 1 calc R
H46B H 0.5955 0.4201 0.4151 0.054 Uiso 1 1 calc R
C47 C 0.2851(13) 0.4433(5) 0.4410(3) 0.0565(17) Uani 1 1 d .
H47A H 0.3041 0.5005 0.4305 0.085 Uiso 1 1 calc R
H47B H 0.3262 0.4422 0.4875 0.085 Uiso 1 1 calc R
H47C H 0.1269 0.4182 0.4300 0.085 Uiso 1 1 calc R
C48 C 0.9417(10) 0.6096(4) 0.4010(3) 0.0402(14) Uani 1 1 d .
H48A H 0.8072 0.5676 0.3920 0.060 Uiso 1 1 calc R
H48B H 0.8950 0.6644 0.4068 0.060 Uiso 1 1 calc R
H48C H 1.0293 0.5998 0.4407 0.060 Uiso 1 1 calc R
C49 C 1.4067(10) 0.7003(4) 0.4127(3) 0.0369(13) Uani 1 1 d .
H49A H 1.4341 0.6636 0.4460 0.055 Uiso 1 1 calc R
H49B H 1.2989 0.7365 0.4268 0.055 Uiso 1 1 calc R
H49C H 1.5497 0.7338 0.4060 0.055 Uiso 1 1 calc R
C50 C 1.6715(9) 0.5601(3) 0.0368(2) 0.0319(12) Uani 1 1 d .
H50 H 1.7832 0.6005 0.0609 0.038 Uiso 1 1 calc R
N1 N 0.1649(8) 0.0949(3) 0.5241(2) 0.0345(11) Uani 1 1 d .
N2 N 1.1215(8) 0.4530(3) 0.0627(2) 0.0327(10) Uani 1 1 d .
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'
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
C2 C1 N1 129.2(5) . .
C2 C1 C10 121.0(5) . .
N1 C1 C10 109.8(5) . .
C1 C2 C3 118.9(5) . .
C1 C2 H2 120.6 . .
C3 C2 H2 120.6 . .
C2 C3 C8 120.9(5) . .
C2 C3 C4 121.7(5) . .
C8 C3 C4 117.4(5) . .
C5 C4 C3 122.7(5) . .
C5 C4 H4 118.7 . .
C3 C4 H4 118.7 . .
C4 C5 C6 119.5(5) . .
C4 C5 C23 119.9(5) . .
C6 C5 C23 120.6(5) . .
C7 C6 C5 119.0(5) . .
C7 C6 C24 120.9(5) . .
C5 C6 C24 120.1(5) . .
C6 C7 C8 122.2(5) . .
C6 C7 H7 118.9 . .
C8 C7 H7 118.9 . .
C3 C8 C7 119.3(5) . .
C3 C8 C9 119.2(5) . .
C7 C8 C9 121.5(5) . .
C10 C9 C8 118.9(5) . .
C10 C9 H9 120.5 . .
C8 C9 H9 120.5 . .
C9 C10 C1 121.1(5) . .
C9 C10 C11 132.5(5) . .
C1 C10 C11 106.4(4) . .
C25 C11 C12 120.4(5) . .
C25 C11 C10 133.2(5) . .
C12 C11 C10 106.3(5) . .
C25 C12 N1 128.9(4) 2_656 .
C25 C12 C11 122.3(5) 2_656 .
N1 C12 C11 108.6(4) . .
N1 C13 C14 114.1(4) . .
N1 C13 H13A 108.7 . .
C14 C13 H13A 108.7 . .
N1 C13 H13B 108.7 . .
C14 C13 H13B 108.7 . .
H13A C13 H13B 107.6 . .
C13 C14 C15 111.3(5) . .
C13 C14 H14A 109.4 . .
C15 C14 H14A 109.4 . .
C13 C14 H14B 109.4 . .
C15 C14 H14B 109.4 . .
H14A C14 H14B 108.0 . .
C16 C15 C14 113.4(5) . .
C16 C15 H15A 108.9 . .
C14 C15 H15A 108.9 . .
C16 C15 H15B 108.9 . .
C14 C15 H15B 108.9 . .
H15A C15 H15B 107.7 . .
C17 C16 C15 114.7(5) . .
C17 C16 H16A 108.6 . .
C15 C16 H16A 108.6 . .
C17 C16 H16B 108.6 . .
C15 C16 H16B 108.6 . .
H16A C16 H16B 107.6 . .
C16 C17 C18 113.4(6) . .
C16 C17 H17A 108.9 . .
C18 C17 H17A 108.9 . .
C16 C17 H17B 108.9 . .
C18 C17 H17B 108.9 . .
H17A C17 H17B 107.7 . .
C19 C18 C17 113.7(6) . .
C19 C18 H18A 108.8 . .
C17 C18 H18A 108.8 . .
C19 C18 H18B 108.8 . .
C17 C18 H18B 108.8 . .
H18A C18 H18B 107.7 . .
C18 C19 C20 113.6(6) . .
C18 C19 H19A 108.9 . .
C20 C19 H19A 108.9 . .
C18 C19 H19B 108.9 . .
C20 C19 H19B 108.9 . .
H19A C19 H19B 107.7 . .
C21 C20 C19 115.2(7) . .
C21 C20 H20A 108.5 . .
C19 C20 H20A 108.5 . .
C21 C20 H20B 108.5 . .
C19 C20 H20B 108.5 . .
H20A C20 H20B 107.5 . .
C22 C21 C20 113.0(8) . .
C22 C21 H21A 109.0 . .
C20 C21 H21A 109.0 . .
C22 C21 H21B 109.0 . .
C20 C21 H21B 109.0 . .
H21A C21 H21B 107.8 . .
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 . .
C5 C23 H23A 109.5 . .
C5 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C5 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C6 C24 H24A 109.5 . .
C6 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C6 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C11 C25 C12 117.3(4) . 2_656
C11 C25 H25 121.3 . .
C12 C25 H25 121.3 2_656 .
N2 C26 C27 129.1(5) . .
N2 C26 C35 109.3(5) . .
C27 C26 C35 121.6(5) . .
C26 C27 C28 118.7(5) . .
C26 C27 H27 120.6 . .
C28 C27 H27 120.6 . .
C27 C28 C29 122.3(5) . .
C27 C28 C33 120.2(5) . .
C29 C28 C33 117.5(5) . .
C30 C29 C28 123.0(5) . .
C30 C29 H29 118.5 . .
C28 C29 H29 118.5 . .
C29 C30 C31 119.4(5) . .
C29 C30 C48 119.7(5) . .
C31 C30 C48 121.0(5) . .
C32 C31 C30 119.5(5) . .
C32 C31 C49 120.8(5) . .
C30 C31 C49 119.7(5) . .
C31 C32 C33 121.8(5) . .
C31 C32 H32 119.1 . .
C33 C32 H32 119.1 . .
C34 C33 C32 121.2(5) . .
C34 C33 C28 119.9(5) . .
C32 C33 C28 118.8(5) . .
C35 C34 C33 119.4(5) . .
C35 C34 H34 120.3 . .
C33 C34 H34 120.3 . .
C34 C35 C26 120.1(5) . .
C34 C35 C36 133.5(5) . .
C26 C35 C36 106.4(4) . .
C50 C36 C37 121.3(5) . .
C50 C36 C35 132.7(5) . .
C37 C36 C35 105.9(5) . .
C50 C37 N2 128.7(5) 2_865 .
C50 C37 C36 121.6(5) 2_865 .
N2 C37 C36 109.7(4) . .
N2 C38 C39 112.9(4) . .
N2 C38 H38A 109.0 . .
C39 C38 H38A 109.0 . .
N2 C38 H38B 109.0 . .
C39 C38 H38B 109.0 . .
H38A C38 H38B 107.8 . .
C38 C39 C40 112.8(4) . .
C38 C39 H39A 109.0 . .
C40 C39 H39A 109.0 . .
C38 C39 H39B 109.0 . .
C40 C39 H39B 109.0 . .
H39A C39 H39B 107.8 . .
C39 C40 C41 114.3(5) . .
C39 C40 H40A 108.7 . .
C41 C40 H40A 108.7 . .
C39 C40 H40B 108.7 . .
C41 C40 H40B 108.7 . .
H40A C40 H40B 107.6 . .
C42 C41 C40 115.7(5) . .
C42 C41 H41A 108.4 . .
C40 C41 H41A 108.4 . .
C42 C41 H41B 108.4 . .
C40 C41 H41B 108.4 . .
H41A C41 H41B 107.4 . .
C43 C42 C41 114.1(5) . .
C43 C42 H42A 108.7 . .
C41 C42 H42A 108.7 . .
C43 C42 H42B 108.7 . .
C41 C42 H42B 108.7 . .
H42A C42 H42B 107.6 . .
C42 C43 C44 113.9(5) . .
C42 C43 H43A 108.8 . .
C44 C43 H43A 108.8 . .
C42 C43 H43B 108.8 . .
C44 C43 H43B 108.8 . .
H43A C43 H43B 107.7 . .
C43 C44 C45 114.0(5) . .
C43 C44 H44A 108.7 . .
C45 C44 H44A 108.7 . .
C43 C44 H44B 108.7 . .
C45 C44 H44B 108.7 . .
H44A C44 H44B 107.6 . .
C46 C45 C44 113.4(5) . .
C46 C45 H45A 108.9 . .
C44 C45 H45A 108.9 . .
C46 C45 H45B 108.9 . .
C44 C45 H45B 108.9 . .
H45A C45 H45B 107.7 . .
C47 C46 C45 113.9(5) . .
C47 C46 H46A 108.8 . .
C45 C46 H46A 108.8 . .
C47 C46 H46B 108.8 . .
C45 C46 H46B 108.8 . .
H46A C46 H46B 107.7 . .
C46 C47 H47A 109.5 . .
C46 C47 H47B 109.5 . .
H47A C47 H47B 109.5 . .
C46 C47 H47C 109.5 . .
H47A C47 H47C 109.5 . .
H47B C47 H47C 109.5 . .
C30 C48 H48A 109.5 . .
C30 C48 H48B 109.5 . .
H48A C48 H48B 109.5 . .
C30 C48 H48C 109.5 . .
H48A C48 H48C 109.5 . .
H48B C48 H48C 109.5 . .
C31 C49 H49A 109.5 . .
C31 C49 H49B 109.5 . .
H49A C49 H49B 109.5 . .
C31 C49 H49C 109.5 . .
H49A C49 H49C 109.5 . .
H49B C49 H49C 109.5 . .
C37 C50 C36 117.1(4) 2_865 .
C37 C50 H50 121.5 2_865 .
C36 C50 H50 121.5 . .
C1 N1 C12 108.8(4) . .
C1 N1 C13 127.0(5) . .
C12 N1 C13 124.2(4) . .
C26 N2 C37 108.7(4) . .
C26 N2 C38 124.5(5) . .
C37 N2 C38 125.9(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.384(8) .
C1 N1 1.386(7) .
C1 C10 1.412(7) .
C2 C3 1.401(7) .
C2 H2 0.9500 .
C3 C8 1.417(7) .
C3 C4 1.426(8) .
C4 C5 1.369(8) .
C4 H4 0.9500 .
C5 C6 1.435(8) .
C5 C23 1.522(8) .
C6 C7 1.365(9) .
C6 C24 1.503(8) .
C7 C8 1.423(8) .
C7 H7 0.9500 .
C8 C9 1.430(8) .
C9 C10 1.376(7) .
C9 H9 0.9500 .
C10 C11 1.462(8) .
C11 C25 1.383(8) .
C11 C12 1.429(7) .
C12 C25 1.384(8) 2_656
C12 N1 1.399(7) .
C13 N1 1.458(6) .
C13 C14 1.501(7) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.542(7) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.539(8) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.513(9) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C18 1.517(9) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.514(10) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C20 1.524(9) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.516(11) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 C22 1.510(11) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
C25 C12 1.384(8) 2_656
C25 H25 0.9500 .
C26 N2 1.380(7) .
C26 C27 1.382(8) .
C26 C35 1.428(8) .
C27 C28 1.415(7) .
C27 H27 0.9500 .
C28 C29 1.424(8) .
C28 C33 1.430(7) .
C29 C30 1.363(8) .
C29 H29 0.9500 .
C30 C31 1.420(8) .
C30 C48 1.518(8) .
C31 C32 1.383(8) .
C31 C49 1.518(7) .
C32 C33 1.415(7) .
C32 H32 0.9500 .
C33 C34 1.415(8) .
C34 C35 1.389(7) .
C34 H34 0.9500 .
C35 C36 1.455(8) .
C36 C50 1.403(8) .
C36 C37 1.422(7) .
C37 C50 1.386(7) 2_865
C37 N2 1.386(7) .
C38 N2 1.458(6) .
C38 C39 1.512(7) .
C38 H38A 0.9900 .
C38 H38B 0.9900 .
C39 C40 1.528(8) .
C39 H39A 0.9900 .
C39 H39B 0.9900 .
C40 C41 1.535(9) .
C40 H40A 0.9900 .
C40 H40B 0.9900 .
C41 C42 1.531(8) .
C41 H41A 0.9900 .
C41 H41B 0.9900 .
C42 C43 1.501(9) .
C42 H42A 0.9900 .
C42 H42B 0.9900 .
C43 C44 1.507(8) .
C43 H43A 0.9900 .
C43 H43B 0.9900 .
C44 C45 1.529(9) .
C44 H44A 0.9900 .
C44 H44B 0.9900 .
C45 C46 1.521(8) .
C45 H45A 0.9900 .
C45 H45B 0.9900 .
C46 C47 1.504(9) .
C46 H46A 0.9900 .
C46 H46B 0.9900 .
C47 H47A 0.9800 .
C47 H47B 0.9800 .
C47 H47C 0.9800 .
C48 H48A 0.9800 .
C48 H48B 0.9800 .
C48 H48C 0.9800 .
C49 H49A 0.9800 .
C49 H49B 0.9800 .
C49 H49C 0.9800 .
C50 C37 1.386(7) 2_865
C50 H50 0.9500 .
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_4
N1 C1 C2 C3 -178.8(5) . .
C10 C1 C2 C3 1.2(8) . .
C1 C2 C3 C8 -0.1(8) . .
C1 C2 C3 C4 -178.9(6) . .
C2 C3 C4 C5 -178.3(6) . .
C8 C3 C4 C5 2.9(8) . .
C3 C4 C5 C6 -1.4(8) . .
C3 C4 C5 C23 178.9(6) . .
C4 C5 C6 C7 -0.4(9) . .
C23 C5 C6 C7 179.3(5) . .
C4 C5 C6 C24 178.3(6) . .
C23 C5 C6 C24 -2.0(9) . .
C5 C6 C7 C8 0.6(9) . .
C24 C6 C7 C8 -178.2(6) . .
C2 C3 C8 C7 178.5(5) . .
C4 C3 C8 C7 -2.7(8) . .
C2 C3 C8 C9 -0.6(8) . .
C4 C3 C8 C9 178.2(5) . .
C6 C7 C8 C3 1.0(8) . .
C6 C7 C8 C9 -179.8(6) . .
C3 C8 C9 C10 0.4(8) . .
C7 C8 C9 C10 -178.8(6) . .
C8 C9 C10 C1 0.6(8) . .
C8 C9 C10 C11 -179.0(6) . .
C2 C1 C10 C9 -1.5(8) . .
N1 C1 C10 C9 178.6(5) . .
C2 C1 C10 C11 178.2(5) . .
N1 C1 C10 C11 -1.8(6) . .
C9 C10 C11 C25 5.5(11) . .
C1 C10 C11 C25 -174.2(6) . .
C9 C10 C11 C12 -178.7(6) . .
C1 C10 C11 C12 1.7(6) . .
C25 C11 C12 C25 -0.7(9) . 2_656
C10 C11 C12 C25 -177.2(5) . 2_656
C25 C11 C12 N1 175.5(5) . .
C10 C11 C12 N1 -1.0(6) . .
N1 C13 C14 C15 177.4(5) . .
C13 C14 C15 C16 -66.0(7) . .
C14 C15 C16 C17 -66.9(7) . .
C15 C16 C17 C18 177.5(5) . .
C16 C17 C18 C19 179.1(6) . .
C17 C18 C19 C20 176.9(6) . .
C18 C19 C20 C21 178.5(7) . .
C19 C20 C21 C22 178.5(7) . .
C12 C11 C25 C12 0.7(8) . 2_656
C10 C11 C25 C12 176.1(6) . 2_656
N2 C26 C27 C28 -179.9(5) . .
C35 C26 C27 C28 -2.2(8) . .
C26 C27 C28 C29 180.0(5) . .
C26 C27 C28 C33 -0.5(7) . .
C27 C28 C29 C30 179.0(5) . .
C33 C28 C29 C30 -0.5(8) . .
C28 C29 C30 C31 -0.5(8) . .
C28 C29 C30 C48 179.5(5) . .
C29 C30 C31 C32 1.5(8) . .
C48 C30 C31 C32 -178.5(5) . .
C29 C30 C31 C49 -178.7(5) . .
C48 C30 C31 C49 1.4(8) . .
C30 C31 C32 C33 -1.5(8) . .
C49 C31 C32 C33 178.7(5) . .
C31 C32 C33 C34 178.7(5) . .
C31 C32 C33 C28 0.4(7) . .
C27 C28 C33 C34 2.7(8) . .
C29 C28 C33 C34 -177.7(5) . .
C27 C28 C33 C32 -179.0(5) . .
C29 C28 C33 C32 0.6(7) . .
C32 C33 C34 C35 179.6(5) . .
C28 C33 C34 C35 -2.1(7) . .
C33 C34 C35 C26 -0.6(7) . .
C33 C34 C35 C36 -179.4(6) . .
N2 C26 C35 C34 -179.1(5) . .
C27 C26 C35 C34 2.8(8) . .
N2 C26 C35 C36 0.0(6) . .
C27 C26 C35 C36 -178.1(5) . .
C34 C35 C36 C50 -5.2(10) . .
C26 C35 C36 C50 175.8(5) . .
C34 C35 C36 C37 177.9(5) . .
C26 C35 C36 C37 -1.0(6) . .
C50 C36 C37 C50 2.4(9) . 2_865
C35 C36 C37 C50 179.7(5) . 2_865
C50 C36 C37 N2 -175.5(5) . .
C35 C36 C37 N2 1.7(6) . .
N2 C38 C39 C40 166.0(5) . .
C38 C39 C40 C41 -61.9(6) . .
C39 C40 C41 C42 -62.2(6) . .
C40 C41 C42 C43 167.7(5) . .
C41 C42 C43 C44 176.3(6) . .
C42 C43 C44 C45 176.9(6) . .
C43 C44 C45 C46 174.8(6) . .
C44 C45 C46 C47 -179.0(6) . .
C37 C36 C50 C37 -2.3(8) . 2_865
C35 C36 C50 C37 -178.7(5) . 2_865
C2 C1 N1 C12 -178.8(6) . .
C10 C1 N1 C12 1.2(6) . .
C2 C1 N1 C13 -0.1(9) . .
C10 C1 N1 C13 179.9(5) . .
C25 C12 N1 C1 175.8(5) 2_656 .
C11 C12 N1 C1 0.0(6) . .
C25 C12 N1 C13 -3.0(8) 2_656 .
C11 C12 N1 C13 -178.8(5) . .
C14 C13 N1 C1 96.4(6) . .
C14 C13 N1 C12 -85.0(6) . .
C27 C26 N2 C37 179.0(5) . .
C35 C26 N2 C37 1.1(6) . .
C27 C26 N2 C38 -11.5(9) . .
C35 C26 N2 C38 170.6(5) . .
C50 C37 N2 C26 -179.6(5) 2_865 .
C36 C37 N2 C26 -1.8(6) . .
C50 C37 N2 C38 11.1(8) 2_865 .
C36 C37 N2 C38 -171.1(5) . .
C39 C38 N2 C26 -78.9(6) . .
C39 C38 N2 C37 88.8(6) . .
