#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/08/2220884.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_2220884
loop_
_publ_author_name
'Rouchal, Michal'
'Nečas, Marek'
'Carvalho, Fabiana Pires de'
'Vícha, Robert'
_publ_section_title
2-(1-Adamantyl)-1-{4-[(2-chloro-9-isopropyl-9H-purin-6-yl)aminomethyl]phenyl}ethanone
_journal_coeditor_code           PK2141
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o298
_journal_page_last               o299
_journal_paper_doi               10.1107/S160053680900052X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C27 H32 Cl N5 O'
_chemical_formula_moiety         'C27 H32 Cl N5 O'
_chemical_formula_sum            'C27 H32 Cl N5 O'
_chemical_formula_weight         478.03
_chemical_melting_point          148
_chemical_name_systematic
;
2-(1-Adamantyl)-1-{4-[(2-chloro-9-isopropyl-9H-purin-6-
yl)aminomethyl]phenyl}ethanone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 104.233(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.8778(5)
_cell_length_b                   20.2779(5)
_cell_length_c                   15.2225(5)
_cell_measurement_reflns_used    8353
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.75
_cell_volume                     4750.7(3)
_computing_cell_refinement       'Xcalibur (Oxford Diffraction, 2006)'
_computing_data_collection       'Xcalibur (Oxford Diffraction, 2006)'
_computing_data_reduction        'Xcalibur (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 0.06
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Kuma KM-4 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            47831
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.75
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Xcalibur; Oxford Diffraction, 2006)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.286
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     617
_refine_ls_number_reflns         8353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0761P)²+2.6597P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1504
_reflns_number_gt                5567
_reflns_number_total             8353
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2141.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220884
_cod_database_fobs_code          2220884
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
Cl Cl1 1.54371(4) 0.16850(4) 1.01111(5) 0.0416(2) Uani d . 1 . .
O O1 1.15991(12) 0.38506(9) 0.65047(14) 0.0418(5) Uani d . 1 . .
N N1 1.39808(13) 0.11570(10) 0.92710(14) 0.0265(5) Uani d . 1 . .
N N2 1.53027(13) 0.05913(10) 0.92127(14) 0.0278(5) Uani d . 1 . .
N N4 1.50180(14) -0.04121(10) 0.83228(14) 0.0289(5) Uani d . 1 . .
N N3 1.35644(14) -0.03462(10) 0.78459(15) 0.0306(5) Uani d . 1 . .
N N5 1.26108(13) 0.07666(10) 0.85571(14) 0.0261(5) Uani d . 1 . .
H H5A 1.2293 0.0495 0.8159 0.031 Uiso calc R 1 . .
C C1 0.95337(16) 0.38700(11) 0.59602(15) 0.0222(5) Uani d . 1 . .
C C2 0.98831(16) 0.39531(12) 0.51181(17) 0.0269(6) Uani d . 1 . .
H H2B 1.0340 0.3620 0.5123 0.032 Uiso calc R 1 . .
H H2C 1.0147 0.4396 0.5122 0.032 Uiso calc R 1 . .
C C3 0.91501(17) 0.38722(12) 0.42610(17) 0.0281(6) Uani d . 1 . .
H H3A 0.9391 0.3929 0.3717 0.034 Uiso calc R 1 . .
C C4 0.84508(17) 0.43886(13) 0.42383(18) 0.0321(6) Uani d . 1 . .
H H4B 0.7976 0.4333 0.3684 0.038 Uiso calc R 1 . .
H H4C 0.8699 0.4836 0.4228 0.038 Uiso calc R 1 . .
C C5 0.80936(17) 0.43108(13) 0.50779(17) 0.0285(6) Uani d . 1 . .
H H5B 0.7636 0.4651 0.5070 0.034 Uiso calc R 1 . .
C C6 0.77037(17) 0.36252(13) 0.50670(17) 0.0302(6) Uani d . 1 . .
H H6A 0.7225 0.3571 0.4516 0.036 Uiso calc R 1 . .
H H6B 0.7461 0.3569 0.5602 0.036 Uiso calc R 1 . .
C C7 0.83958(17) 0.31037(13) 0.50795(17) 0.0282(6) Uani d . 1 . .
H H7A 0.8132 0.2656 0.5074 0.034 Uiso calc R 1 . .
C C8 0.91320(16) 0.31812(12) 0.59364(16) 0.0254(6) Uani d . 1 . .
H H8A 0.9583 0.2842 0.5944 0.030 Uiso calc R 1 . .
H H8B 0.8902 0.3117 0.6479 0.030 Uiso calc R 1 . .
C C9 0.87618(17) 0.31819(13) 0.42455(17) 0.0308(6) Uani d . 1 . .
H H9A 0.9215 0.2845 0.4253 0.037 Uiso calc R 1 . .
H H9B 0.8294 0.3121 0.3687 0.037 Uiso calc R 1 . .
C C10 0.88214(17) 0.43880(12) 0.59306(17) 0.0284(6) Uani d . 1 . .
H H10A 0.8584 0.4338 0.6470 0.034 Uiso calc R 1 . .
H H10B 0.9075 0.4835 0.5946 0.034 Uiso calc R 1 . .
C C11 1.02429(17) 0.39841(12) 0.68438(17) 0.0291(6) Uani d . 1 . .
H H11A 1.0369 0.4462 0.6908 0.035 Uiso calc R 1 . .
H H11B 1.0011 0.3847 0.7363 0.035 Uiso calc R 1 . .
C C12 1.10835(17) 0.36200(13) 0.68945(17) 0.0287(6) Uani d . 1 . .
C C13 1.12982(16) 0.29932(12) 0.74137(16) 0.0258(6) Uani d . 1 . .
C C14 1.20554(18) 0.26697(13) 0.73665(18) 0.0331(6) Uani d . 1 . .
H H14A 1.2396 0.2843 0.6987 0.040 Uiso calc R 1 . .
C C15 1.23249(17) 0.21078(13) 0.78510(18) 0.0327(6) Uani d . 1 . .
H H15A 1.2847 0.1898 0.7804 0.039 Uiso calc R 1 . .
C C16 1.18432(16) 0.18431(12) 0.84080(16) 0.0240(5) Uani d . 1 . .
C C17 1.10862(16) 0.21535(13) 0.84536(17) 0.0279(6) Uani d . 1 . .
H H17A 1.0745 0.1974 0.8828 0.033 Uiso calc R 1 . .
C C18 1.08111(16) 0.27234(12) 0.79635(17) 0.0280(6) Uani d . 1 . .
H H18A 1.0285 0.2930 0.8005 0.034 Uiso calc R 1 . .
C C19 1.21638(16) 0.12463(12) 0.89844(17) 0.0263(6) Uani d . 1 . .
H H19A 1.2563 0.1394 0.9557 0.032 Uiso calc R 1 . .
H H19B 1.1662 0.1029 0.9140 0.032 Uiso calc R 1 . .
C C20 1.34751(16) 0.07103(12) 0.87280(15) 0.0228(5) Uani d . 1 . .
C C21 1.48320(16) 0.10626(13) 0.94474(16) 0.0275(6) Uani d . 1 . .
C C22 1.47769(16) 0.01555(12) 0.86771(16) 0.0246(6) Uani d . 1 . .
C C23 1.38849(16) 0.01919(12) 0.83828(17) 0.0255(6) Uani d . 1 . .
C C24 1.42650(18) -0.06881(13) 0.78385(19) 0.0333(6) Uani d . 1 . .
H H24A 1.4248 -0.1094 0.7522 0.040 Uiso calc R 1 . .
C C25 1.59119(17) -0.06731(13) 0.84933(18) 0.0326(6) Uani d . 1 . .
H H25A 1.6181 -0.0638 0.9158 0.039 Uiso calc R 1 . .
C C26 1.64435(18) -0.02650(14) 0.8010(2) 0.0389(7) Uani d . 1 . .
H H26A 1.6197 -0.0295 0.7355 0.058 Uiso calc R 1 . .
H H26B 1.7043 -0.0428 0.8157 0.058 Uiso calc R 1 . .
H H26C 1.6438 0.0196 0.8202 0.058 Uiso calc R 1 . .
C C27 1.5911(2) -0.13913(15) 0.8235(3) 0.0566(10) Uani d . 1 . .
H H27A 1.5524 -0.1637 0.8528 0.085 Uiso calc R 1 . .
H H27B 1.6502 -0.1568 0.8433 0.085 Uiso calc R 1 . .
H H27C 1.5706 -0.1435 0.7575 0.085 Uiso calc R 1 . .
Cl Cl51 1.06711(4) 0.32556(3) 1.02370(4) 0.03138(18) Uani d . 1 . .
O O51 0.65672(14) 0.16100(11) 0.55786(14) 0.0508(6) Uani d . 1 . .
N N51 0.92396(13) 0.37756(10) 0.93336(13) 0.0251(5) Uani d . 1 . .
N N52 1.05595(13) 0.43726(10) 0.93901(13) 0.0231(5) Uani d . 1 . .
N N53 0.88368(13) 0.53117(10) 0.79834(13) 0.0237(5) Uani d . 1 . .
N N54 1.02812(13) 0.53960(10) 0.85313(13) 0.0223(5) Uani d . 1 . .
N N55 0.78821(13) 0.41714(10) 0.86172(13) 0.0264(5) Uani d . 1 . .
H H55A 0.7566 0.4474 0.8274 0.032 Uiso calc R 1 . .
C C51 0.47184(16) 0.11567(12) 0.58865(16) 0.0259(6) Uani d . 1 . .
C C52 0.43209(18) 0.16706(13) 0.63953(18) 0.0326(6) Uani d . 1 . .
H H52B 0.4403 0.1533 0.7035 0.039 Uiso calc R 1 . .
H H52C 0.4618 0.2099 0.6388 0.039 Uiso calc R 1 . .
C C53 0.33568(18) 0.17478(14) 0.5956(2) 0.0370(7) Uani d . 1 . .
H H53B 0.3103 0.2083 0.6298 0.044 Uiso calc R 1 . .
C C54 0.2906(2) 0.10865(16) 0.5982(2) 0.0478(8) Uani d . 1 . .
H H54A 0.2991 0.0938 0.6617 0.057 Uiso calc R 1 . .
H H54B 0.2274 0.1133 0.5712 0.057 Uiso calc R 1 . .
C C55 0.3289(2) 0.05839(15) 0.5449(2) 0.0496(8) Uani d . 1 . .
H H55B 0.2988 0.0151 0.5453 0.060 Uiso calc R 1 . .
C C56 0.3168(2) 0.08135(18) 0.4476(2) 0.0605(10) Uani d . 1 . .
H H56A 0.3407 0.0479 0.4129 0.073 Uiso calc R 1 . .
H H56B 0.2541 0.0867 0.4188 0.073 Uiso calc R 1 . .
C C57 0.3632(2) 0.14650(17) 0.44614(19) 0.0457(8) Uani d . 1 . .
H H57A 0.3556 0.1613 0.3820 0.055 Uiso calc R 1 . .
C C58 0.45957(18) 0.13811(15) 0.49055(18) 0.0373(7) Uani d . 1 . .
H H58A 0.4901 0.1805 0.4890 0.045 Uiso calc R 1 . .
H H58B 0.4849 0.1050 0.4567 0.045 Uiso calc R 1 . .
C C59 0.3243(2) 0.19791(16) 0.49812(19) 0.0437(8) Uani d . 1 . .
H H59A 0.3539 0.2408 0.4973 0.052 Uiso calc R 1 . .
H H59B 0.2618 0.2039 0.4690 0.052 Uiso calc R 1 . .
C C60 0.42482(18) 0.05001(13) 0.5893(2) 0.0380(7) Uani d . 1 . .
H H60A 0.4500 0.0164 0.5560 0.046 Uiso calc R 1 . .
H H60B 0.4324 0.0347 0.6525 0.046 Uiso calc R 1 . .
C C61 0.56868(17) 0.10361(13) 0.63550(19) 0.0329(6) Uani d . 1 . .
H H61A 0.5739 0.0958 0.7008 0.039 Uiso calc R 1 . .
H H61B 0.5877 0.0629 0.6101 0.039 Uiso calc R 1 . .
C C62 0.62922(17) 0.15816(14) 0.62633(19) 0.0344(7) Uani d . 1 . .
C C63 0.65636(16) 0.20984(13) 0.69797(17) 0.0279(6) Uani d . 1 . .
C C68 0.62858(17) 0.21168(13) 0.77775(17) 0.0311(6) Uani d . 1 . .
H H68A 0.5905 0.1786 0.7895 0.037 Uiso calc R 1 . .
C C67 0.65643(17) 0.26183(13) 0.84013(17) 0.0294(6) Uani d . 1 . .
H H67A 0.6364 0.2632 0.8940 0.035 Uiso calc R 1 . .
C C66 0.71300(16) 0.30974(12) 0.82460(16) 0.0247(6) Uani d . 1 . .
C C65 0.74072(16) 0.30712(13) 0.74527(17) 0.0281(6) Uani d . 1 . .
H H65A 0.7795 0.3399 0.7339 0.034 Uiso calc R 1 . .
C C64 0.71310(17) 0.25799(13) 0.68273(17) 0.0295(6) Uani d . 1 . .
H H64A 0.7330 0.2570 0.6288 0.035 Uiso calc R 1 . .
C C69 0.74333(17) 0.36378(13) 0.89382(16) 0.0276(6) Uani d . 1 . .
H H69A 0.6923 0.3819 0.9120 0.033 Uiso calc R 1 . .
H H69B 0.7826 0.3443 0.9484 0.033 Uiso calc R 1 . .
C C70 0.87432(15) 0.42347(11) 0.88074(15) 0.0218(5) Uani d . 1 . .
C C71 1.00903(16) 0.38826(12) 0.95686(15) 0.0230(5) Uani d . 1 . .
C C72 1.00400(16) 0.48160(11) 0.88524(15) 0.0216(5) Uani d . 1 . .
C C73 0.91542(16) 0.47738(11) 0.85193(15) 0.0214(5) Uani d . 1 . .
C C74 0.95342(16) 0.56661(12) 0.80151(16) 0.0259(6) Uani d . 1 . .
H H74A 0.9521 0.6075 0.7706 0.031 Uiso calc R 1 . .
C C75 1.11732(16) 0.56615(12) 0.87100(16) 0.0250(6) Uani d . 1 . .
H H75A 1.1462 0.5577 0.9362 0.030 Uiso calc R 1 . .
C C76 1.11638(17) 0.63973(12) 0.85592(18) 0.0311(6) Uani d . 1 . .
H H76A 1.0919 0.6492 0.7916 0.047 Uiso calc R 1 . .
H H76B 1.1759 0.6568 0.8743 0.047 Uiso calc R 1 . .
H H76C 1.0808 0.6609 0.8921 0.047 Uiso calc R 1 . .
C C77 1.16747(17) 0.52945(13) 0.81434(18) 0.0308(6) Uani d . 1 . .
H H77A 1.1671 0.4822 0.8277 0.046 Uiso calc R 1 . .
H H77B 1.2275 0.5455 0.8285 0.046 Uiso calc R 1 . .
H H77C 1.1404 0.5368 0.7500 0.046 Uiso calc R 1 . .
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C21 N1 C20 . . 116.8(2) ?
C21 N2 C22 . . 109.4(2) ?
C24 N4 C22 . . 105.5(2) ?
C24 N4 C25 . . 128.8(2) ?
C22 N4 C25 . . 125.7(2) ?
C24 N3 C23 . . 103.4(2) ?
C20 N5 C19 . . 124.2(2) ?
C20 N5 H5A . . 117.9 ?
C19 N5 H5A . . 117.9 ?
C2 C1 C8 . . 108.42(19) ?
C2 C1 C10 . . 108.5(2) ?
C8 C1 C10 . . 108.9(2) ?
C2 C1 C11 . . 112.2(2) ?
C8 C1 C11 . . 111.55(19) ?
C10 C1 C11 . . 107.27(19) ?
C1 C2 C3 . . 110.3(2) ?
C1 C2 H2B . . 109.6 ?
C3 C2 H2B . . 109.6 ?
C1 C2 H2C . . 109.6 ?
C3 C2 H2C . . 109.6 ?
H2B C2 H2C . . 108.1 ?
C4 C3 C9 . . 109.9(2) ?
C4 C3 C2 . . 110.1(2) ?
C9 C3 C2 . . 109.3(2) ?
C4 C3 H3A . . 109.1 ?
C9 C3 H3A . . 109.1 ?
C2 C3 H3A . . 109.1 ?
C3 C4 C5 . . 109.2(2) ?
C3 C4 H4B . . 109.8 ?
C5 C4 H4B . . 109.8 ?
C3 C4 H4C . . 109.8 ?
C5 C4 H4C . . 109.8 ?
H4B C4 H4C . . 108.3 ?
C10 C5 C6 . . 109.0(2) ?
C10 C5 C4 . . 110.1(2) ?
C6 C5 C4 . . 108.6(2) ?
C10 C5 H5B . . 109.7 ?
C6 C5 H5B . . 109.7 ?
C4 C5 H5B . . 109.7 ?
C5 C6 C7 . . 110.1(2) ?
C5 C6 H6A . . 109.6 ?
C7 C6 H6A . . 109.6 ?
C5 C6 H6B . . 109.6 ?
C7 C6 H6B . . 109.6 ?
H6A C6 H6B . . 108.1 ?
C6 C7 C9 . . 109.8(2) ?
C6 C7 C8 . . 109.7(2) ?
C9 C7 C8 . . 109.3(2) ?
C6 C7 H7A . . 109.4 ?
C9 C7 H7A . . 109.4 ?
C8 C7 H7A . . 109.4 ?
C7 C8 C1 . . 109.88(19) ?
C7 C8 H8A . . 109.7 ?
C1 C8 H8A . . 109.7 ?
C7 C8 H8B . . 109.7 ?
C1 C8 H8B . . 109.7 ?
H8A C8 H8B . . 108.2 ?
C3 C9 C7 . . 108.5(2) ?
C3 C9 H9A . . 110.0 ?
C7 C9 H9A . . 110.0 ?
C3 C9 H9B . . 110.0 ?
C7 C9 H9B . . 110.0 ?
H9A C9 H9B . . 108.4 ?
C5 C10 C1 . . 110.76(19) ?
C5 C10 H10A . . 109.5 ?
C1 C10 H10A . . 109.5 ?
C5 C10 H10B . . 109.5 ?
C1 C10 H10B . . 109.5 ?
H10A C10 H10B . . 108.1 ?
C12 C11 C1 . . 114.6(2) ?
C12 C11 H11A . . 108.6 ?
C1 C11 H11A . . 108.6 ?
C12 C11 H11B . . 108.6 ?
C1 C11 H11B . . 108.6 ?
H11A C11 H11B . . 107.6 ?
O1 C12 C13 . . 119.5(2) ?
O1 C12 C11 . . 118.6(2) ?
C13 C12 C11 . . 121.8(2) ?
C18 C13 C14 . . 117.7(2) ?
C18 C13 C12 . . 124.6(2) ?
C14 C13 C12 . . 117.6(2) ?
C15 C14 C13 . . 121.8(2) ?
C15 C14 H14A . . 119.1 ?
C13 C14 H14A . . 119.1 ?
C14 C15 C16 . . 120.5(2) ?
C14 C15 H15A . . 119.8 ?
C16 C15 H15A . . 119.8 ?
C17 C16 C15 . . 118.4(2) ?
C17 C16 C19 . . 120.8(2) ?
C15 C16 C19 . . 120.7(2) ?
C16 C17 C18 . . 121.2(2) ?
C16 C17 H17A . . 119.4 ?
C18 C17 H17A . . 119.4 ?
C13 C18 C17 . . 120.4(2) ?
C13 C18 H18A . . 119.8 ?
C17 C18 H18A . . 119.8 ?
N5 C19 C16 . . 114.2(2) ?
N5 C19 H19A . . 108.7 ?
C16 C19 H19A . . 108.7 ?
N5 C19 H19B . . 108.7 ?
C16 C19 H19B . . 108.7 ?
H19A C19 H19B . . 107.6 ?
N5 C20 N1 . . 119.3(2) ?
N5 C20 C23 . . 122.6(2) ?
N1 C20 C23 . . 118.1(2) ?
N2 C21 N1 . . 132.0(2) ?
N2 C21 Cl1 . . 114.40(19) ?
N1 C21 Cl1 . . 113.63(19) ?
N2 C22 N4 . . 126.9(2) ?
N2 C22 C23 . . 126.7(2) ?
N4 C22 C23 . . 106.4(2) ?
C22 C23 N3 . . 110.4(2) ?
C22 C23 C20 . . 116.9(2) ?
N3 C23 C20 . . 132.4(2) ?
N3 C24 N4 . . 114.3(2) ?
N3 C24 H24A . . 122.9 ?
N4 C24 H24A . . 122.9 ?
N4 C25 C26 . . 110.4(2) ?
N4 C25 C27 . . 111.2(2) ?
C26 C25 C27 . . 111.7(2) ?
N4 C25 H25A . . 107.8 ?
C26 C25 H25A . . 107.8 ?
C27 C25 H25A . . 107.8 ?
C25 C26 H26A . . 109.5 ?
C25 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C25 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C25 C27 H27A . . 109.5 ?
C25 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C25 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C71 N51 C70 . . 117.0(2) ?
C71 N52 C72 . . 109.7(2) ?
C74 N53 C73 . . 103.2(2) ?
C72 N54 C74 . . 105.7(2) ?
C72 N54 C75 . . 126.1(2) ?
C74 N54 C75 . . 128.1(2) ?
C70 N55 C69 . . 124.3(2) ?
C70 N55 H55A . . 117.8 ?
C69 N55 H55A . . 117.8 ?
C52 C51 C58 . . 108.9(2) ?
C52 C51 C60 . . 109.2(2) ?
C58 C51 C60 . . 108.7(2) ?
C52 C51 C61 . . 111.3(2) ?
C58 C51 C61 . . 111.8(2) ?
C60 C51 C61 . . 106.9(2) ?
C53 C52 C51 . . 110.2(2) ?
C53 C52 H52B . . 109.6 ?
C51 C52 H52B . . 109.6 ?
C53 C52 H52C . . 109.6 ?
C51 C52 H52C . . 109.6 ?
H52B C52 H52C . . 108.1 ?
C52 C53 C59 . . 109.0(2) ?
C52 C53 C54 . . 109.1(2) ?
C59 C53 C54 . . 110.6(3) ?
C52 C53 H53B . . 109.4 ?
C59 C53 H53B . . 109.4 ?
C54 C53 H53B . . 109.4 ?
C55 C54 C53 . . 108.9(2) ?
C55 C54 H54A . . 109.9 ?
C53 C54 H54A . . 109.9 ?
C55 C54 H54B . . 109.9 ?
C53 C54 H54B . . 109.9 ?
H54A C54 H54B . . 108.3 ?
C60 C55 C56 . . 110.0(3) ?
C60 C55 C54 . . 109.1(3) ?
C56 C55 C54 . . 110.1(3) ?
C60 C55 H55B . . 109.2 ?
C56 C55 H55B . . 109.2 ?
C54 C55 H55B . . 109.2 ?
C57 C56 C55 . . 109.7(2) ?
C57 C56 H56A . . 109.7 ?
C55 C56 H56A . . 109.7 ?
C57 C56 H56B . . 109.7 ?
C55 C56 H56B . . 109.7 ?
H56A C56 H56B . . 108.2 ?
C56 C57 C58 . . 109.6(3) ?
C56 C57 C59 . . 109.1(3) ?
C58 C57 C59 . . 109.6(2) ?
C56 C57 H57A . . 109.5 ?
C58 C57 H57A . . 109.5 ?
C59 C57 H57A . . 109.5 ?
C57 C58 C51 . . 109.9(2) ?
C57 C58 H58A . . 109.7 ?
C51 C58 H58A . . 109.7 ?
C57 C58 H58B . . 109.7 ?
C51 C58 H58B . . 109.7 ?
H58A C58 H58B . . 108.2 ?
C53 C59 C57 . . 109.1(2) ?
C53 C59 H59A . . 109.9 ?
C57 C59 H59A . . 109.9 ?
C53 C59 H59B . . 109.9 ?
C57 C59 H59B . . 109.9 ?
H59A C59 H59B . . 108.3 ?
C55 C60 C51 . . 109.8(2) ?
C55 C60 H60A . . 109.7 ?
C51 C60 H60A . . 109.7 ?
C55 C60 H60B . . 109.7 ?
C51 C60 H60B . . 109.7 ?
H60A C60 H60B . . 108.2 ?
C62 C61 C51 . . 115.4(2) ?
C62 C61 H61A . . 108.4 ?
C51 C61 H61A . . 108.4 ?
C62 C61 H61B . . 108.4 ?
C51 C61 H61B . . 108.4 ?
H61A C61 H61B . . 107.5 ?
O51 C62 C61 . . 119.1(2) ?
O51 C62 C63 . . 119.2(3) ?
C61 C62 C63 . . 121.8(2) ?
C64 C63 C68 . . 119.1(2) ?
C64 C63 C62 . . 117.0(2) ?
C68 C63 C62 . . 124.0(2) ?
C67 C68 C63 . . 120.1(2) ?
C67 C68 H68A . . 120.0 ?
C63 C68 H68A . . 120.0 ?
C66 C67 C68 . . 120.6(2) ?
C66 C67 H67A . . 119.7 ?
C68 C67 H67A . . 119.7 ?
C67 C66 C65 . . 118.8(2) ?
C67 C66 C69 . . 119.9(2) ?
C65 C66 C69 . . 121.3(2) ?
C64 C65 C66 . . 121.1(2) ?
C64 C65 H65A . . 119.4 ?
C66 C65 H65A . . 119.4 ?
C65 C64 C63 . . 120.3(2) ?
C65 C64 H64A . . 119.8 ?
C63 C64 H64A . . 119.8 ?
N55 C69 C66 . . 113.9(2) ?
N55 C69 H69A . . 108.8 ?
C66 C69 H69A . . 108.8 ?
N55 C69 H69B . . 108.8 ?
C66 C69 H69B . . 108.8 ?
H69A C69 H69B . . 107.7 ?
N55 C70 N51 . . 118.8(2) ?
N55 C70 C73 . . 122.7(2) ?
N51 C70 C73 . . 118.4(2) ?
N52 C71 N51 . . 131.4(2) ?
N52 C71 Cl51 . . 115.34(18) ?
N51 C71 Cl51 . . 113.28(18) ?
N52 C72 N54 . . 127.4(2) ?
N52 C72 C73 . . 126.8(2) ?
N54 C72 C73 . . 105.9(2) ?
C72 C73 N53 . . 111.1(2) ?
C72 C73 C70 . . 116.5(2) ?
N53 C73 C70 . . 132.3(2) ?
N53 C74 N54 . . 114.0(2) ?
N53 C74 H74A . . 123.0 ?
N54 C74 H74A . . 123.0 ?
N54 C75 C77 . . 109.4(2) ?
N54 C75 C76 . . 111.1(2) ?
C77 C75 C76 . . 112.8(2) ?
N54 C75 H75A . . 107.8 ?
C77 C75 H75A . . 107.8 ?
C76 C75 H75A . . 107.8 ?
C75 C76 H76A . . 109.5 ?
C75 C76 H76B . . 109.5 ?
H76A C76 H76B . . 109.5 ?
C75 C76 H76C . . 109.5 ?
H76A C76 H76C . . 109.5 ?
H76B C76 H76C . . 109.5 ?
C75 C77 H77A . . 109.5 ?
C75 C77 H77B . . 109.5 ?
H77A C77 H77B . . 109.5 ?
C75 C77 H77C . . 109.5 ?
H77A C77 H77C . . 109.5 ?
H77B C77 H77C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C21 . 1.749(3) ?
O1 C12 . 1.217(3) ?
N1 C21 . 1.326(3) ?
N1 C20 . 1.350(3) ?
N2 C21 . 1.316(3) ?
N2 C22 . 1.345(3) ?
N4 C24 . 1.361(3) ?
N4 C22 . 1.365(3) ?
N4 C25 . 1.477(3) ?
N3 C24 . 1.313(3) ?
N3 C23 . 1.383(3) ?
N5 C20 . 1.337(3) ?
N5 C19 . 1.449(3) ?
N5 H5A . 0.8800 ?
C1 C2 . 1.526(3) ?
C1 C8 . 1.532(3) ?
C1 C10 . 1.536(3) ?
C1 C11 . 1.545(3) ?
C2 C3 . 1.529(3) ?
C2 H2B . 0.9900 ?
C2 H2C . 0.9900 ?
C3 C4 . 1.520(4) ?
C3 C9 . 1.527(4) ?
C3 H3A . 1.0000 ?
C4 C5 . 1.528(4) ?
C4 H4B . 0.9900 ?
C4 H4C . 0.9900 ?
C5 C10 . 1.519(3) ?
C5 C6 . 1.520(4) ?
C5 H5B . 1.0000 ?
C6 C7 . 1.522(4) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C9 . 1.529(4) ?
C7 C8 . 1.531(3) ?
C7 H7A . 1.0000 ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.511(4) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.491(4) ?
C13 C18 . 1.384(4) ?
C13 C14 . 1.387(4) ?
C14 C15 . 1.368(4) ?
C14 H14A . 0.9500 ?
C15 C16 . 1.382(4) ?
C15 H15A . 0.9500 ?
C16 C17 . 1.374(3) ?
C16 C19 . 1.508(3) ?
C17 C18 . 1.386(4) ?
C17 H17A . 0.9500 ?
C18 H18A . 0.9500 ?
C19 H19A . 0.9900 ?
C19 H19B . 0.9900 ?
C20 C23 . 1.405(3) ?
C22 C23 . 1.378(4) ?
C24 H24A . 0.9500 ?
C25 C26 . 1.498(4) ?
C25 C27 . 1.508(4) ?
C25 H25A . 1.0000 ?
C26 H26A . 0.9800 ?
C26 H26B . 0.9800 ?
C26 H26C . 0.9800 ?
C27 H27A . 0.9800 ?
C27 H27B . 0.9800 ?
C27 H27C . 0.9800 ?
Cl51 C71 . 1.744(2) ?
O51 C62 . 1.226(3) ?
N51 C71 . 1.327(3) ?
N51 C70 . 1.349(3) ?
N52 C71 . 1.310(3) ?
N52 C72 . 1.351(3) ?
N53 C74 . 1.311(3) ?
N53 C73 . 1.381(3) ?
N54 C72 . 1.364(3) ?
N54 C74 . 1.366(3) ?
N54 C75 . 1.477(3) ?
N55 C70 . 1.332(3) ?
N55 C69 . 1.445(3) ?
N55 H55A . 0.8800 ?
C51 C52 . 1.525(4) ?
C51 C58 . 1.527(4) ?
C51 C60 . 1.528(4) ?
C51 C61 . 1.547(4) ?
C52 C53 . 1.521(4) ?
C52 H52B . 0.9900 ?
C52 H52C . 0.9900 ?
C53 C59 . 1.524(4) ?
C53 C54 . 1.525(4) ?
C53 H53B . 1.0000 ?
C54 C55 . 1.520(4) ?
C54 H54A . 0.9900 ?
C54 H54B . 0.9900 ?
C55 C60 . 1.516(4) ?
C55 C56 . 1.518(5) ?
C55 H55B . 1.0000 ?
C56 C57 . 1.515(5) ?
C56 H56A . 0.9900 ?
C56 H56B . 0.9900 ?
C57 C58 . 1.523(4) ?
C57 C59 . 1.528(4) ?
C57 H57A . 1.0000 ?
C58 H58A . 0.9900 ?
C58 H58B . 0.9900 ?
C59 H59A . 0.9900 ?
C59 H59B . 0.9900 ?
C60 H60A . 0.9900 ?
C60 H60B . 0.9900 ?
C61 C62 . 1.494(4) ?
C61 H61A . 0.9900 ?
C61 H61B . 0.9900 ?
C62 C63 . 1.497(4) ?
C63 C64 . 1.386(4) ?
C63 C68 . 1.391(4) ?
C68 C67 . 1.387(4) ?
C68 H68A . 0.9500 ?
C67 C66 . 1.383(3) ?
C67 H67A . 0.9500 ?
C66 C65 . 1.384(4) ?
C66 C69 . 1.514(3) ?
C65 C64 . 1.373(4) ?
C65 H65A . 0.9500 ?
C64 H64A . 0.9500 ?
C69 H69A . 0.9900 ?
C69 H69B . 0.9900 ?
C70 C73 . 1.398(3) ?
C72 C73 . 1.375(3) ?
C74 H74A . 0.9500 ?
C75 C77 . 1.507(4) ?
C75 C76 . 1.509(3) ?
C75 H75A . 1.0000 ?
C76 H76A . 0.9800 ?
C76 H76B . 0.9800 ?
C76 H76C . 0.9800 ?
C77 H77A . 0.9800 ?
C77 H77B . 0.9800 ?
C77 H77C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N5 H5A N53 2_746 0.88 2.20 2.997(3) 150.1
N55 H55A N3 2_756 0.88 2.18 2.946(3) 145.2
C27 H27A Cl1 3_857 0.98 2.86 3.732(3) 148.5
C54 H54B Cl51 4_465 0.99 2.76 3.698(3) 157.6
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 C1 C2 C3 . . . . 59.4(3) ?
C10 C1 C2 C3 . . . . -58.7(3) ?
C11 C1 C2 C3 . . . . -177.0(2) ?
C1 C2 C3 C4 . . . . 60.1(3) ?
C1 C2 C3 C9 . . . . -60.8(3) ?
C9 C3 C4 C5 . . . . 61.4(3) ?
C2 C3 C4 C5 . . . . -59.2(3) ?
C3 C4 C5 C10 . . . . 58.8(3) ?
C3 C4 C5 C6 . . . . -60.5(3) ?
C10 C5 C6 C7 . . . . -59.8(3) ?
C4 C5 C6 C7 . . . . 60.1(3) ?
C5 C6 C7 C9 . . . . -60.2(3) ?
C5 C6 C7 C8 . . . . 59.9(3) ?
C6 C7 C8 C1 . . . . -59.3(3) ?
C9 C7 C8 C1 . . . . 61.1(3) ?
C2 C1 C8 C7 . . . . -59.5(3) ?
C10 C1 C8 C7 . . . . 58.3(3) ?
C11 C1 C8 C7 . . . . 176.5(2) ?
C4 C3 C9 C7 . . . . -60.3(3) ?
C2 C3 C9 C7 . . . . 60.7(3) ?
C6 C7 C9 C3 . . . . 59.3(3) ?
C8 C7 C9 C3 . . . . -61.1(3) ?
C6 C5 C10 C1 . . . . 59.7(3) ?
C4 C5 C10 C1 . . . . -59.3(3) ?
C2 C1 C10 C5 . . . . 58.6(3) ?
C8 C1 C10 C5 . . . . -59.2(3) ?
C11 C1 C10 C5 . . . . 180.0(2) ?
C2 C1 C11 C12 . . . . -48.3(3) ?
C8 C1 C11 C12 . . . . 73.5(3) ?
C10 C1 C11 C12 . . . . -167.4(2) ?
C1 C11 C12 O1 . . . . 80.4(3) ?
C1 C11 C12 C13 . . . . -100.2(3) ?
O1 C12 C13 C18 . . . . 172.5(2) ?
C11 C12 C13 C18 . . . . -6.9(4) ?
O1 C12 C13 C14 . . . . -5.2(4) ?
C11 C12 C13 C14 . . . . 175.4(2) ?
C18 C13 C14 C15 . . . . -0.8(4) ?
C12 C13 C14 C15 . . . . 177.1(2) ?
C13 C14 C15 C16 . . . . 0.0(4) ?
C14 C15 C16 C17 . . . . 0.7(4) ?
C14 C15 C16 C19 . . . . -176.5(2) ?
C15 C16 C17 C18 . . . . -0.7(4) ?
C19 C16 C17 C18 . . . . 176.4(2) ?
C14 C13 C18 C17 . . . . 0.8(4) ?
C12 C13 C18 C17 . . . . -176.9(2) ?
C16 C17 C18 C13 . . . . 0.0(4) ?
C20 N5 C19 C16 . . . . 100.3(3) ?
C17 C16 C19 N5 . . . . 146.3(2) ?
C15 C16 C19 N5 . . . . -36.6(3) ?
C19 N5 C20 N1 . . . . -6.0(3) ?
C19 N5 C20 C23 . . . . 172.3(2) ?
C21 N1 C20 N5 . . . . 177.3(2) ?
C21 N1 C20 C23 . . . . -1.1(3) ?
C22 N2 C21 N1 . . . . 2.1(4) ?
C22 N2 C21 Cl1 . . . . -177.54(17) ?
C20 N1 C21 N2 . . . . -2.5(4) ?
C20 N1 C21 Cl1 . . . . 177.14(17) ?
C21 N2 C22 N4 . . . . -177.5(2) ?
C21 N2 C22 C23 . . . . 1.9(3) ?
C24 N4 C22 N2 . . . . 179.4(2) ?
C25 N4 C22 N2 . . . . 2.7(4) ?
C24 N4 C22 C23 . . . . -0.2(3) ?
C25 N4 C22 C23 . . . . -176.9(2) ?
N2 C22 C23 N3 . . . . -179.7(2) ?
N4 C22 C23 N3 . . . . -0.1(3) ?
N2 C22 C23 C20 . . . . -5.0(4) ?
N4 C22 C23 C20 . . . . 174.6(2) ?
C24 N3 C23 C22 . . . . 0.4(3) ?
C24 N3 C23 C20 . . . . -173.2(3) ?
N5 C20 C23 C22 . . . . -174.1(2) ?
N1 C20 C23 C22 . . . . 4.2(3) ?
N5 C20 C23 N3 . . . . -0.8(4) ?
N1 C20 C23 N3 . . . . 177.5(2) ?
C23 N3 C24 N4 . . . . -0.5(3) ?
C22 N4 C24 N3 . . . . 0.4(3) ?
C25 N4 C24 N3 . . . . 177.0(2) ?
C24 N4 C25 C26 . . . . 111.6(3) ?
C22 N4 C25 C26 . . . . -72.5(3) ?
C24 N4 C25 C27 . . . . -13.0(4) ?
C22 N4 C25 C27 . . . . 162.9(3) ?
C58 C51 C52 C53 . . . . 59.9(3) ?
C60 C51 C52 C53 . . . . -58.6(3) ?
C61 C51 C52 C53 . . . . -176.4(2) ?
C51 C52 C53 C59 . . . . -60.9(3) ?
C51 C52 C53 C54 . . . . 59.9(3) ?
C52 C53 C54 C55 . . . . -61.1(3) ?
C59 C53 C54 C55 . . . . 58.7(3) ?
C53 C54 C55 C60 . . . . 61.8(3) ?
C53 C54 C55 C56 . . . . -59.0(3) ?
C60 C55 C56 C57 . . . . -59.5(3) ?
C54 C55 C56 C57 . . . . 60.7(3) ?
C55 C56 C57 C58 . . . . 59.4(3) ?
C55 C56 C57 C59 . . . . -60.7(3) ?
C56 C57 C58 C51 . . . . -60.0(3) ?
C59 C57 C58 C51 . . . . 59.7(3) ?
C52 C51 C58 C57 . . . . -59.1(3) ?
C60 C51 C58 C57 . . . . 59.8(3) ?
C61 C51 C58 C57 . . . . 177.6(2) ?
C52 C53 C59 C57 . . . . 60.5(3) ?
C54 C53 C59 C57 . . . . -59.4(3) ?
C56 C57 C59 C53 . . . . 59.8(3) ?
C58 C57 C59 C53 . . . . -60.2(3) ?
C56 C55 C60 C51 . . . . 59.9(3) ?
C54 C55 C60 C51 . . . . -61.0(3) ?
C52 C51 C60 C55 . . . . 59.0(3) ?
C58 C51 C60 C55 . . . . -59.6(3) ?
C61 C51 C60 C55 . . . . 179.5(2) ?
C52 C51 C61 C62 . . . . -72.2(3) ?
C58 C51 C61 C62 . . . . 49.8(3) ?
C60 C51 C61 C62 . . . . 168.7(2) ?
C51 C61 C62 O51 . . . . -83.7(3) ?
C51 C61 C62 C63 . . . . 95.6(3) ?
O51 C62 C63 C64 . . . . -1.0(4) ?
C61 C62 C63 C64 . . . . 179.7(2) ?
O51 C62 C63 C68 . . . . 179.4(3) ?
C61 C62 C63 C68 . . . . 0.2(4) ?
C64 C63 C68 C67 . . . . 1.1(4) ?
C62 C63 C68 C67 . . . . -179.4(2) ?
C63 C68 C67 C66 . . . . -1.1(4) ?
C68 C67 C66 C65 . . . . 0.6(4) ?
C68 C67 C66 C69 . . . . -179.5(2) ?
C67 C66 C65 C64 . . . . -0.1(4) ?
C69 C66 C65 C64 . . . . 179.9(2) ?
C66 C65 C64 C63 . . . . 0.1(4) ?
C68 C63 C64 C65 . . . . -0.6(4) ?
C62 C63 C64 C65 . . . . 179.8(2) ?
C70 N55 C69 C66 . . . . -99.6(3) ?
C67 C66 C69 N55 . . . . -168.7(2) ?
C65 C66 C69 N55 . . . . 11.3(3) ?
C69 N55 C70 N51 . . . . 0.0(3) ?
C69 N55 C70 C73 . . . . -177.0(2) ?
C71 N51 C70 N55 . . . . -174.7(2) ?
C71 N51 C70 C73 . . . . 2.3(3) ?
C72 N52 C71 N51 . . . . -1.8(4) ?
C72 N52 C71 Cl51 . . . . 178.53(16) ?
C70 N51 C71 N52 . . . . 1.0(4) ?
C70 N51 C71 Cl51 . . . . -179.33(16) ?
C71 N52 C72 N54 . . . . 178.9(2) ?
C71 N52 C72 C73 . . . . -0.8(3) ?
C74 N54 C72 N52 . . . . 179.4(2) ?
C75 N54 C72 N52 . . . . -0.1(4) ?
C74 N54 C72 C73 . . . . -0.8(2) ?
C75 N54 C72 C73 . . . . 179.7(2) ?
N52 C72 C73 N53 . . . . -179.3(2) ?
N54 C72 C73 N53 . . . . 1.0(3) ?
N52 C72 C73 C70 . . . . 3.8(3) ?
N54 C72 C73 C70 . . . . -176.0(2) ?
C74 N53 C73 C72 . . . . -0.7(3) ?
C74 N53 C73 C70 . . . . 175.6(2) ?
N55 C70 C73 C72 . . . . 172.5(2) ?
N51 C70 C73 C72 . . . . -4.4(3) ?
N55 C70 C73 N53 . . . . -3.6(4) ?
N51 C70 C73 N53 . . . . 179.5(2) ?
C73 N53 C74 N54 . . . . 0.1(3) ?
C72 N54 C74 N53 . . . . 0.4(3) ?
C75 N54 C74 N53 . . . . 179.9(2) ?
C72 N54 C75 C77 . . . . 76.2(3) ?
C74 N54 C75 C77 . . . . -103.2(3) ?
C72 N54 C75 C76 . . . . -158.6(2) ?
C74 N54 C75 C76 . . . . 22.0(3) ?
