#------------------------------------------------------------------------------
#$Date: 2020-09-11 02:51:29 +0300 (Fri, 11 Sep 2020) $
#$Revision: 256311 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/87/4038736.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_4038736
loop_
_publ_author_name
'Molenda, Ricardo'
'Boldt, Sebastian'
'Villinger, Alexander'
'Ehlers, Peter'
'Langer, Peter'
_publ_section_title
;
 Synthesis of 2-Azapyrenes and Their Photophysical and Electrochemical
 Properties.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01622
_journal_year                    2020
_chemical_formula_moiety         'C28 H19 N'
_chemical_formula_sum            'C28 H19 N'
_chemical_formula_weight         369.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   31.461(5)
_cell_length_b                   32.311(4)
_cell_length_c                   7.4331(9)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      24.10
_cell_measurement_theta_min      3.09
_cell_volume                     7556.0(18)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Apex Kappa-II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0990
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            157367
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         3.096
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7439
_exptl_absorpt_correction_T_min  0.7059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             3104
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     526
_refine_ls_number_reflns         9091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0461
_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)+(0.0470P)²+4.4463P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1248
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6423
_reflns_number_total             9091
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01622_si_002.cif
_cod_data_source_block           is_rm_cyhme
_cod_original_cell_volume        7556.2(17)
_cod_database_code               4038736
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.994
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'
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
N1 N 0.81491(5) 0.54942(5) 0.4947(2) 0.0294(3) Uani 1 1 d . . . . .
C1 C 0.82457(5) 0.51045(5) 0.5364(2) 0.0254(4) Uani 1 1 d . . . . .
H1 H 0.8538 0.5032 0.5416 0.030 Uiso 1 1 calc R U . . .
C2 C 0.79481(5) 0.47957(5) 0.5731(2) 0.0210(3) Uani 1 1 d . . . . .
C3 C 0.80620(5) 0.43815(5) 0.6152(2) 0.0219(3) Uani 1 1 d . . . . .
H3 H 0.8355 0.4309 0.6189 0.026 Uiso 1 1 calc R U . . .
C4 C 0.77659(5) 0.40849(5) 0.6504(2) 0.0200(3) Uani 1 1 d . . . . .
C5 C 0.73167(5) 0.41966(5) 0.6528(2) 0.0191(3) Uani 1 1 d . . . . .
C6 C 0.69985(5) 0.39235(5) 0.7087(2) 0.0207(3) Uani 1 1 d . . . . .
H6 H 0.7075 0.3652 0.7453 0.025 Uiso 1 1 calc R U . . .
C7 C 0.65733(5) 0.40380(5) 0.7122(2) 0.0213(3) Uani 1 1 d . . . . .
C8 C 0.64565(5) 0.44296(5) 0.6523(2) 0.0215(3) Uani 1 1 d . . . . .
H8 H 0.6163 0.4499 0.6465 0.026 Uiso 1 1 calc R U . . .
C9 C 0.67589(5) 0.47246(5) 0.6003(2) 0.0197(3) Uani 1 1 d . . . . .
C10 C 0.66516(5) 0.51458(5) 0.5450(2) 0.0214(3) Uani 1 1 d . . . . .
C11 C 0.69664(5) 0.54196(5) 0.5050(2) 0.0232(3) Uani 1 1 d . . . . .
H11 H 0.6892 0.5692 0.4687 0.028 Uiso 1 1 calc R U . . .
C12 C 0.74048(5) 0.53110(5) 0.5157(2) 0.0222(3) Uani 1 1 d . . . . .
C13 C 0.77363(5) 0.55896(5) 0.4836(2) 0.0267(4) Uani 1 1 d . . . . .
H13 H 0.7663 0.5865 0.4517 0.032 Uiso 1 1 calc R U . . .
C14 C 0.75138(5) 0.49026(5) 0.5636(2) 0.0197(3) Uani 1 1 d . . . . .
C15 C 0.71953(5) 0.46063(5) 0.6041(2) 0.0193(3) Uani 1 1 d . . . . .
C16 C 0.62434(5) 0.37402(5) 0.7817(3) 0.0290(4) Uani 1 1 d . . . . .
H16A H 0.6380 0.3536 0.8602 0.044 Uiso 0.65(2) 1 calc R U P A 1
H16B H 0.6108 0.3598 0.6801 0.044 Uiso 0.65(2) 1 calc R U P A 1
H16C H 0.6028 0.3893 0.8499 0.044 Uiso 0.65(2) 1 calc R U P A 1
H16D H 0.5966 0.3811 0.7306 0.044 Uiso 0.35(2) 1 calc R U P A 2
H16E H 0.6230 0.3758 0.9131 0.044 Uiso 0.35(2) 1 calc R U P A 2
H16F H 0.6320 0.3458 0.7464 0.044 Uiso 0.35(2) 1 calc R U P A 2
C17 C 0.79149(5) 0.36538(5) 0.6800(2) 0.0223(3) Uani 1 1 d . . . . .
C18 C 0.82686(5) 0.35863(6) 0.7899(2) 0.0285(4) Uani 1 1 d . . . . .
H18 H 0.8396 0.3813 0.8506 0.034 Uiso 1 1 calc R U . . .
C19 C 0.84361(6) 0.31938(6) 0.8116(3) 0.0374(5) Uani 1 1 d . . . . .
H19 H 0.8674 0.3153 0.8881 0.045 Uiso 1 1 calc R U . . .
C20 C 0.82582(6) 0.28620(6) 0.7226(3) 0.0425(5) Uani 1 1 d . . . . .
H20 H 0.8373 0.2592 0.7379 0.051 Uiso 1 1 calc R U . . .
C21 C 0.79112(6) 0.29239(6) 0.6106(3) 0.0374(5) Uani 1 1 d . . . . .
H21 H 0.7792 0.2697 0.5473 0.045 Uiso 1 1 calc R U . . .
C22 C 0.77382(5) 0.33154(5) 0.5905(2) 0.0268(4) Uani 1 1 d . . . . .
H22 H 0.7497 0.3354 0.5152 0.032 Uiso 1 1 calc R U . . .
C23 C 0.62040(5) 0.52898(5) 0.5249(2) 0.0223(3) Uani 1 1 d . . . . .
C24 C 0.58952(5) 0.52425(5) 0.6586(2) 0.0261(4) Uani 1 1 d . . . . .
H24 H 0.5965 0.5103 0.7671 0.031 Uiso 1 1 calc R U . . .
C25 C 0.54862(6) 0.53972(5) 0.6346(3) 0.0301(4) Uani 1 1 d . . . . .
H25 H 0.5279 0.5360 0.7261 0.036 Uiso 1 1 calc R U . . .
C26 C 0.53810(6) 0.56045(6) 0.4786(3) 0.0329(4) Uani 1 1 d . . . . .
H26 H 0.5101 0.5707 0.4617 0.039 Uiso 1 1 calc R U . . .
C27 C 0.56862(6) 0.56627(6) 0.3469(2) 0.0318(4) Uani 1 1 d . . . . .
H27 H 0.5617 0.5810 0.2404 0.038 Uiso 1 1 calc R U . . .
C28 C 0.60924(5) 0.55066(5) 0.3698(2) 0.0260(4) Uani 1 1 d . . . . .
H28 H 0.6299 0.5548 0.2782 0.031 Uiso 1 1 calc R U . . .
N2 N 0.55901(5) 0.30813(5) 0.5453(2) 0.0307(3) Uani 1 1 d . . . . .
C29 C 0.56756(5) 0.26764(5) 0.5498(2) 0.0280(4) Uani 1 1 d . . . . .
H29 H 0.5963 0.2593 0.5350 0.034 Uiso 1 1 calc R U . . .
C30 C 0.53713(5) 0.23672(5) 0.5747(2) 0.0229(3) Uani 1 1 d . . . . .
C31 C 0.54717(5) 0.19364(5) 0.5778(2) 0.0239(3) Uani 1 1 d . . . . .
H31 H 0.5758 0.1851 0.5617 0.029 Uiso 1 1 calc R U . . .
C32 C 0.51653(5) 0.16450(5) 0.6035(2) 0.0209(3) Uani 1 1 d . . . . .
C33 C 0.47258(5) 0.17675(5) 0.6299(2) 0.0193(3) Uani 1 1 d . . . . .
C34 C 0.44039(5) 0.14832(5) 0.6705(2) 0.0204(3) Uani 1 1 d . . . . .
H34 H 0.4471 0.1197 0.6762 0.024 Uiso 1 1 calc R U . . .
C35 C 0.39882(5) 0.16102(5) 0.7027(2) 0.0208(3) Uani 1 1 d . . . . .
C36 C 0.38858(5) 0.20277(5) 0.6880(2) 0.0202(3) Uani 1 1 d . . . . .
H36 H 0.3599 0.2111 0.7059 0.024 Uiso 1 1 calc R U . . .
C37 C 0.41906(5) 0.23286(5) 0.6478(2) 0.0188(3) Uani 1 1 d . . . . .
C38 C 0.40949(5) 0.27698(5) 0.6388(2) 0.0206(3) Uani 1 1 d . . . . .
C39 C 0.44171(5) 0.30446(5) 0.6137(2) 0.0225(3) Uani 1 1 d . . . . .
H39 H 0.4352 0.3332 0.6093 0.027 Uiso 1 1 calc R U . . .
C40 C 0.48484(5) 0.29181(5) 0.5936(2) 0.0217(3) Uani 1 1 d . . . . .
C41 C 0.51857(6) 0.31942(5) 0.5674(2) 0.0275(4) Uani 1 1 d . . . . .
H41 H 0.5122 0.3482 0.5651 0.033 Uiso 1 1 calc R U . . .
C42 C 0.49450(5) 0.24926(5) 0.5962(2) 0.0195(3) Uani 1 1 d . . . . .
C43 C 0.46172(5) 0.21944(5) 0.6228(2) 0.0181(3) Uani 1 1 d . . . . .
C44 C 0.36523(5) 0.13027(5) 0.7569(3) 0.0272(4) Uani 1 1 d . . . . .
H44A H 0.3381 0.1446 0.7732 0.041 Uiso 1 1 calc R U . . .
H44B H 0.3735 0.1169 0.8700 0.041 Uiso 1 1 calc R U . . .
H44C H 0.3623 0.1092 0.6627 0.041 Uiso 1 1 calc R U . . .
C45 C 0.52907(5) 0.12001(5) 0.6037(2) 0.0214(3) Uani 1 1 d . . . . .
C46 C 0.55630(5) 0.10404(5) 0.7343(2) 0.0254(4) Uani 1 1 d . . . . .
H46 H 0.5664 0.1214 0.8282 0.030 Uiso 1 1 calc R U . . .
C47 C 0.56877(5) 0.06280(6) 0.7279(2) 0.0295(4) Uani 1 1 d . . . . .
H47 H 0.5872 0.0521 0.8178 0.035 Uiso 1 1 calc R U . . .
C48 C 0.55455(5) 0.03720(5) 0.5914(2) 0.0280(4) Uani 1 1 d . . . . .
H48 H 0.5630 0.0090 0.5880 0.034 Uiso 1 1 calc R U . . .
C49 C 0.52791(5) 0.05299(5) 0.4595(3) 0.0284(4) Uani 1 1 d . . . . .
H49 H 0.5183 0.0357 0.3646 0.034 Uiso 1 1 calc R U . . .
C50 C 0.51533(5) 0.09407(5) 0.4661(2) 0.0248(4) Uani 1 1 d . . . . .
H50 H 0.4971 0.1047 0.3754 0.030 Uiso 1 1 calc R U . . .
C51 C 0.36538(5) 0.29323(5) 0.6556(2) 0.0233(3) Uani 1 1 d . . . . .
C52 C 0.33091(5) 0.27666(5) 0.5613(2) 0.0272(4) Uani 1 1 d . . . . .
H52 H 0.3349 0.2529 0.4882 0.033 Uiso 1 1 calc R U . . .
C53 C 0.29094(6) 0.29451(6) 0.5731(3) 0.0376(5) Uani 1 1 d . . . . .
H53 H 0.2679 0.2830 0.5073 0.045 Uiso 1 1 calc R U . . .
C54 C 0.28449(7) 0.32901(6) 0.6804(3) 0.0459(6) Uani 1 1 d . . . . .
H54 H 0.2570 0.3409 0.6898 0.055 Uiso 1 1 calc R U . . .
C55 C 0.31807(7) 0.34601(6) 0.7733(3) 0.0413(5) Uani 1 1 d . . . . .
H55 H 0.3138 0.3699 0.8456 0.050 Uiso 1 1 calc R U . . .
C56 C 0.35807(6) 0.32832(5) 0.7615(2) 0.0310(4) Uani 1 1 d . . . . .
H56 H 0.3810 0.3402 0.8267 0.037 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C13 116.99(15) . . ?
N1 C1 C2 124.64(15) . . ?
N1 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
C1 C2 C14 117.71(15) . . ?
C1 C2 C3 123.20(15) . . ?
C14 C2 C3 119.08(14) . . ?
C4 C3 C2 122.19(14) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 119.41(15) . . ?
C3 C4 C17 118.18(14) . . ?
C5 C4 C17 122.40(14) . . ?
C6 C5 C15 118.04(14) . . ?
C6 C5 C4 122.77(15) . . ?
C15 C5 C4 119.12(14) . . ?
C7 C6 C5 121.85(15) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C8 119.41(15) . . ?
C6 C7 C16 120.02(15) . . ?
C8 C7 C16 120.57(14) . . ?
C7 C8 C9 121.85(14) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C8 C9 C15 117.79(14) . . ?
C8 C9 C10 123.66(14) . . ?
C15 C9 C10 118.54(14) . . ?
C11 C10 C9 119.92(14) . . ?
C11 C10 C23 117.57(15) . . ?
C9 C10 C23 122.49(14) . . ?
C10 C11 C12 122.15(15) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C13 C12 C14 117.68(15) . . ?
C13 C12 C11 123.63(16) . . ?
C14 C12 C11 118.68(14) . . ?
N1 C13 C12 124.44(16) . . ?
N1 C13 H13 117.8 . . ?
C12 C13 H13 117.8 . . ?
C12 C14 C2 118.52(14) . . ?
C12 C14 C15 120.93(14) . . ?
C2 C14 C15 120.55(15) . . ?
C14 C15 C5 119.46(14) . . ?
C14 C15 C9 119.69(14) . . ?
C5 C15 C9 120.83(14) . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 C16 H16D 109.5 . . ?
C7 C16 H16E 109.5 . . ?
H16D C16 H16E 109.5 . . ?
C7 C16 H16F 109.5 . . ?
H16D C16 H16F 109.5 . . ?
H16E C16 H16F 109.5 . . ?
C22 C17 C18 118.26(16) . . ?
C22 C17 C4 122.57(15) . . ?
C18 C17 C4 118.95(15) . . ?
C19 C18 C17 120.98(18) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C18 120.17(18) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.69(18) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C22 C21 C20 120.37(19) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C17 120.52(17) . . ?
C21 C22 H22 119.7 . . ?
C17 C22 H22 119.7 . . ?
C28 C23 C24 117.90(15) . . ?
C28 C23 C10 118.51(15) . . ?
C24 C23 C10 123.46(15) . . ?
C25 C24 C23 120.81(16) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C26 C25 C24 120.24(17) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 119.62(16) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C26 C27 C28 120.26(17) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C27 C28 C23 121.14(16) . . ?
C27 C28 H28 119.4 . . ?
C23 C28 H28 119.4 . . ?
C41 N2 C29 117.19(15) . . ?
N2 C29 C30 124.46(16) . . ?
N2 C29 H29 117.8 . . ?
C30 C29 H29 117.8 . . ?
C29 C30 C42 117.49(15) . . ?
C29 C30 C31 123.24(15) . . ?
C42 C30 C31 119.27(14) . . ?
C32 C31 C30 121.34(15) . . ?
C32 C31 H31 119.3 . . ?
C30 C31 H31 119.3 . . ?
C31 C32 C33 120.33(15) . . ?
C31 C32 C45 118.68(14) . . ?
C33 C32 C45 120.98(14) . . ?
C34 C33 C43 118.07(14) . . ?
C34 C33 C32 122.64(14) . . ?
C43 C33 C32 119.22(14) . . ?
C35 C34 C33 121.56(15) . . ?
C35 C34 H34 119.2 . . ?
C33 C34 H34 119.2 . . ?
C36 C35 C34 119.34(14) . . ?
C36 C35 C44 119.91(14) . . ?
C34 C35 C44 120.73(14) . . ?
C35 C36 C37 122.17(14) . . ?
C35 C36 H36 118.9 . . ?
C37 C36 H36 118.9 . . ?
C36 C37 C43 117.59(14) . . ?
C36 C37 C38 123.22(14) . . ?
C43 C37 C38 119.12(14) . . ?
C39 C38 C37 119.35(15) . . ?
C39 C38 C51 118.41(14) . . ?
C37 C38 C51 122.23(14) . . ?
C38 C39 C40 122.47(15) . . ?
C38 C39 H39 118.8 . . ?
C40 C39 H39 118.8 . . ?
C41 C40 C42 117.43(15) . . ?
C41 C40 C39 123.61(15) . . ?
C42 C40 C39 118.94(14) . . ?
N2 C41 C40 124.47(16) . . ?
N2 C41 H41 117.8 . . ?
C40 C41 H41 117.8 . . ?
C40 C42 C30 118.96(14) . . ?
C40 C42 C43 120.40(14) . . ?
C30 C42 C43 120.63(15) . . ?
C33 C43 C37 121.15(14) . . ?
C33 C43 C42 119.16(14) . . ?
C37 C43 C42 119.65(14) . . ?
C35 C44 H44A 109.5 . . ?
C35 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C35 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C50 C45 C46 118.67(15) . . ?
C50 C45 C32 119.88(14) . . ?
C46 C45 C32 121.36(15) . . ?
C47 C46 C45 120.30(16) . . ?
C47 C46 H46 119.9 . . ?
C45 C46 H46 119.9 . . ?
C48 C47 C46 120.49(16) . . ?
C48 C47 H47 119.8 . . ?
C46 C47 H47 119.8 . . ?
C47 C48 C49 119.59(16) . . ?
C47 C48 H48 120.2 . . ?
C49 C48 H48 120.2 . . ?
C50 C49 C48 119.97(17) . . ?
C50 C49 H49 120.0 . . ?
C48 C49 H49 120.0 . . ?
C49 C50 C45 120.97(16) . . ?
C49 C50 H50 119.5 . . ?
C45 C50 H50 119.5 . . ?
C52 C51 C56 117.70(16) . . ?
C52 C51 C38 123.08(15) . . ?
C56 C51 C38 119.09(16) . . ?
C53 C52 C51 120.85(17) . . ?
C53 C52 H52 119.6 . . ?
C51 C52 H52 119.6 . . ?
C54 C53 C52 120.3(2) . . ?
C54 C53 H53 119.9 . . ?
C52 C53 H53 119.9 . . ?
C55 C54 C53 119.83(18) . . ?
C55 C54 H54 120.1 . . ?
C53 C54 H54 120.1 . . ?
C54 C55 C56 120.05(19) . . ?
C54 C55 H55 120.0 . . ?
C56 C55 H55 120.0 . . ?
C55 C56 C51 121.30(19) . . ?
C55 C56 H56 119.3 . . ?
C51 C56 H56 119.3 . . ?
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
N1 C1 1.332(2) . ?
N1 C13 1.338(2) . ?
C1 C2 1.395(2) . ?
C1 H1 0.9500 . ?
C2 C14 1.411(2) . ?
C2 C3 1.420(2) . ?
C3 C4 1.362(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.459(2) . ?
C4 C17 1.486(2) . ?
C5 C6 1.398(2) . ?
C5 C15 1.424(2) . ?
C6 C7 1.388(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(2) . ?
C7 C16 1.507(2) . ?
C8 C9 1.401(2) . ?
C8 H8 0.9500 . ?
C9 C15 1.426(2) . ?
C9 C10 1.461(2) . ?
C10 C11 1.361(2) . ?
C10 C23 1.491(2) . ?
C11 C12 1.425(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.398(2) . ?
C12 C14 1.409(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.418(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 H16D 0.9800 . ?
C16 H16E 0.9800 . ?
C16 H16F 0.9800 . ?
C17 C22 1.395(2) . ?
C17 C18 1.398(2) . ?
C18 C19 1.383(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.378(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.385(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C28 1.394(2) . ?
C23 C24 1.398(2) . ?
C24 C25 1.392(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.380(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.384(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.384(2) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
N2 C41 1.334(2) . ?
N2 C29 1.336(2) . ?
C29 C30 1.396(2) . ?
C29 H29 0.9500 . ?
C30 C42 1.410(2) . ?
C30 C31 1.427(2) . ?
C31 C32 1.361(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.452(2) . ?
C32 C45 1.491(2) . ?
C33 C34 1.400(2) . ?
C33 C43 1.422(2) . ?
C34 C35 1.391(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.391(2) . ?
C35 C44 1.505(2) . ?
C36 C37 1.398(2) . ?
C36 H36 0.9500 . ?
C37 C43 1.423(2) . ?
C37 C38 1.459(2) . ?
C38 C39 1.360(2) . ?
C38 C51 1.489(2) . ?
C39 C40 1.425(2) . ?
C39 H39 0.9500 . ?
C40 C41 1.400(2) . ?
C40 C42 1.408(2) . ?
C41 H41 0.9500 . ?
C42 C43 1.425(2) . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 C50 1.391(2) . ?
C45 C46 1.394(2) . ?
C46 C47 1.390(2) . ?
C46 H46 0.9500 . ?
C47 C48 1.383(3) . ?
C47 H47 0.9500 . ?
C48 C49 1.387(2) . ?
C48 H48 0.9500 . ?
C49 C50 1.386(2) . ?
C49 H49 0.9500 . ?
C50 H50 0.9500 . ?
C51 C52 1.398(2) . ?
C51 C56 1.399(2) . ?
C52 C53 1.386(2) . ?
C52 H52 0.9500 . ?
C53 C54 1.386(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.377(3) . ?
C54 H54 0.9500 . ?
C55 C56 1.385(3) . ?
C55 H55 0.9500 . ?
C56 H56 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N1 C1 C2 -1.6(3) . . . . ?
N1 C1 C2 C14 0.6(2) . . . . ?
N1 C1 C2 C3 179.25(16) . . . . ?
C1 C2 C3 C4 -179.95(15) . . . . ?
C14 C2 C3 C4 -1.3(2) . . . . ?
C2 C3 C4 C5 -2.7(2) . . . . ?
C2 C3 C4 C17 175.64(14) . . . . ?
C3 C4 C5 C6 -172.10(15) . . . . ?
C17 C4 C5 C6 9.7(2) . . . . ?
C3 C4 C5 C15 5.0(2) . . . . ?
C17 C4 C5 C15 -173.26(14) . . . . ?
C15 C5 C6 C7 2.0(2) . . . . ?
C4 C5 C6 C7 179.13(15) . . . . ?
C5 C6 C7 C8 2.5(2) . . . . ?
C5 C6 C7 C16 -177.15(15) . . . . ?
C6 C7 C8 C9 -4.7(2) . . . . ?
C16 C7 C8 C9 174.91(15) . . . . ?
C7 C8 C9 C15 2.3(2) . . . . ?
C7 C8 C9 C10 -176.89(15) . . . . ?
C8 C9 C10 C11 176.76(15) . . . . ?
C15 C9 C10 C11 -2.4(2) . . . . ?
C8 C9 C10 C23 -5.0(2) . . . . ?
C15 C9 C10 C23 175.82(14) . . . . ?
C9 C10 C11 C12 -0.3(2) . . . . ?
C23 C10 C11 C12 -178.59(14) . . . . ?
C10 C11 C12 C13 -176.96(16) . . . . ?
C10 C11 C12 C14 2.1(2) . . . . ?
C1 N1 C13 C12 1.2(3) . . . . ?
C14 C12 C13 N1 0.2(3) . . . . ?
C11 C12 C13 N1 179.33(16) . . . . ?
C13 C12 C14 C2 -1.2(2) . . . . ?
C11 C12 C14 C2 179.63(14) . . . . ?
C13 C12 C14 C15 177.87(14) . . . . ?
C11 C12 C14 C15 -1.3(2) . . . . ?
C1 C2 C14 C12 0.8(2) . . . . ?
C3 C2 C14 C12 -177.86(14) . . . . ?
C1 C2 C14 C15 -178.25(14) . . . . ?
C3 C2 C14 C15 3.1(2) . . . . ?
C12 C14 C15 C5 -179.75(14) . . . . ?
C2 C14 C15 C5 -0.7(2) . . . . ?
C12 C14 C15 C9 -1.4(2) . . . . ?
C2 C14 C15 C9 177.67(14) . . . . ?
C6 C5 C15 C14 173.93(14) . . . . ?
C4 C5 C15 C14 -3.3(2) . . . . ?
C6 C5 C15 C9 -4.4(2) . . . . ?
C4 C5 C15 C9 178.36(14) . . . . ?
C8 C9 C15 C14 -176.01(14) . . . . ?
C10 C9 C15 C14 3.2(2) . . . . ?
C8 C9 C15 C5 2.3(2) . . . . ?
C10 C9 C15 C5 -178.46(13) . . . . ?
C3 C4 C17 C22 -130.07(17) . . . . ?
C5 C4 C17 C22 48.2(2) . . . . ?
C3 C4 C17 C18 44.4(2) . . . . ?
C5 C4 C17 C18 -137.34(16) . . . . ?
C22 C17 C18 C19 -0.9(2) . . . . ?
C4 C17 C18 C19 -175.59(16) . . . . ?
C17 C18 C19 C20 0.8(3) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C19 C20 C21 C22 -1.2(3) . . . . ?
C20 C21 C22 C17 1.1(3) . . . . ?
C18 C17 C22 C21 -0.1(2) . . . . ?
C4 C17 C22 C21 174.40(16) . . . . ?
C11 C10 C23 C28 45.6(2) . . . . ?
C9 C10 C23 C28 -132.69(16) . . . . ?
C11 C10 C23 C24 -130.16(17) . . . . ?
C9 C10 C23 C24 51.6(2) . . . . ?
C28 C23 C24 C25 1.8(2) . . . . ?
C10 C23 C24 C25 177.59(15) . . . . ?
C23 C24 C25 C26 -0.7(3) . . . . ?
C24 C25 C26 C27 -0.9(3) . . . . ?
C25 C26 C27 C28 1.3(3) . . . . ?
C26 C27 C28 C23 -0.2(3) . . . . ?
C24 C23 C28 C27 -1.4(2) . . . . ?
C10 C23 C28 C27 -177.34(16) . . . . ?
C41 N2 C29 C30 0.4(3) . . . . ?
N2 C29 C30 C42 0.1(3) . . . . ?
N2 C29 C30 C31 179.62(16) . . . . ?
C29 C30 C31 C32 179.62(16) . . . . ?
C42 C30 C31 C32 -0.9(2) . . . . ?
C30 C31 C32 C33 -0.5(2) . . . . ?
C30 C31 C32 C45 179.44(15) . . . . ?
C31 C32 C33 C34 -174.99(15) . . . . ?
C45 C32 C33 C34 5.1(2) . . . . ?
C31 C32 C33 C43 2.0(2) . . . . ?
C45 C32 C33 C43 -177.91(14) . . . . ?
C43 C33 C34 C35 0.2(2) . . . . ?
C32 C33 C34 C35 177.23(15) . . . . ?
C33 C34 C35 C36 2.3(2) . . . . ?
C33 C34 C35 C44 -176.36(15) . . . . ?
C34 C35 C36 C37 -2.2(2) . . . . ?
C44 C35 C36 C37 176.45(15) . . . . ?
C35 C36 C37 C43 -0.4(2) . . . . ?
C35 C36 C37 C38 -177.43(15) . . . . ?
C36 C37 C38 C39 174.52(15) . . . . ?
C43 C37 C38 C39 -2.5(2) . . . . ?
C36 C37 C38 C51 -5.7(2) . . . . ?
C43 C37 C38 C51 177.28(14) . . . . ?
C37 C38 C39 C40 0.7(2) . . . . ?
C51 C38 C39 C40 -179.10(15) . . . . ?
C38 C39 C40 C41 179.92(16) . . . . ?
C38 C39 C40 C42 1.3(2) . . . . ?
C29 N2 C41 C40 -0.4(3) . . . . ?
C42 C40 C41 N2 -0.2(3) . . . . ?
C39 C40 C41 N2 -178.81(16) . . . . ?
C41 C40 C42 C30 0.7(2) . . . . ?
C39 C40 C42 C30 179.42(14) . . . . ?
C41 C40 C42 C43 179.83(14) . . . . ?
C39 C40 C42 C43 -1.5(2) . . . . ?
C29 C30 C42 C40 -0.7(2) . . . . ?
C31 C30 C42 C40 179.77(14) . . . . ?
C29 C30 C42 C43 -179.80(15) . . . . ?
C31 C30 C42 C43 0.7(2) . . . . ?
C34 C33 C43 C37 -2.9(2) . . . . ?
C32 C33 C43 C37 179.97(14) . . . . ?
C34 C33 C43 C42 174.96(14) . . . . ?
C32 C33 C43 C42 -2.2(2) . . . . ?
C36 C37 C43 C33 3.0(2) . . . . ?
C38 C37 C43 C33 -179.85(14) . . . . ?
C36 C37 C43 C42 -174.87(14) . . . . ?
C38 C37 C43 C42 2.3(2) . . . . ?
C40 C42 C43 C33 -178.23(14) . . . . ?
C30 C42 C43 C33 0.9(2) . . . . ?
C40 C42 C43 C37 -0.3(2) . . . . ?
C30 C42 C43 C37 178.75(14) . . . . ?
C31 C32 C45 C50 -112.78(18) . . . . ?
C33 C32 C45 C50 67.1(2) . . . . ?
C31 C32 C45 C46 63.8(2) . . . . ?
C33 C32 C45 C46 -116.33(17) . . . . ?
C50 C45 C46 C47 -1.0(2) . . . . ?
C32 C45 C46 C47 -177.62(15) . . . . ?
C45 C46 C47 C48 0.4(3) . . . . ?
C46 C47 C48 C49 0.5(3) . . . . ?
C47 C48 C49 C50 -0.7(3) . . . . ?
C48 C49 C50 C45 0.1(3) . . . . ?
C46 C45 C50 C49 0.8(2) . . . . ?
C32 C45 C50 C49 177.45(15) . . . . ?
C39 C38 C51 C52 132.66(17) . . . . ?
C37 C38 C51 C52 -47.1(2) . . . . ?
C39 C38 C51 C56 -43.2(2) . . . . ?
C37 C38 C51 C56 137.02(16) . . . . ?
C56 C51 C52 C53 -0.1(2) . . . . ?
C38 C51 C52 C53 -175.98(16) . . . . ?
C51 C52 C53 C54 -0.6(3) . . . . ?
C52 C53 C54 C55 1.0(3) . . . . ?
C53 C54 C55 C56 -0.9(3) . . . . ?
C54 C55 C56 C51 0.3(3) . . . . ?
C52 C51 C56 C55 0.2(2) . . . . ?
C38 C51 C56 C55 176.31(16) . . . . ?
