#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/02/2230222.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_2230222
loop_
_publ_author_name
'Chang, Liu-Shuan'
'Duan, Hong-Quan'
_publ_section_title
;
 (S,E)-N-Methyl-4-[(S)2,6,6-trimethyl-4-oxocyclohex-2-enyl]but-3-en-2-aminium
 chloride
;
_journal_coeditor_code           BH2347
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1289
_journal_paper_doi               10.1107/S1600536811015297
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H24 N O +, Cl -'
_chemical_formula_moiety         'C14 H24 N O +, Cl -'
_chemical_formula_sum            'C14 H24 Cl N O'
_chemical_formula_weight         257.79
_chemical_name_systematic
;
(S,E)-N-Methyl-4-[(S)2,6,6-trimethyl-
4-oxocyclohex-2-enyl]but-3-en-2-aminium chloride
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.46(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.547(3)
_cell_length_b                   12.247(2)
_cell_length_c                   19.035(4)
_cell_measurement_reflns_used    9688
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.507
_cell_measurement_theta_min      2.926
_cell_volume                     3134.0(13)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'CrystalStructure (Rigaku/MSC, 2005) and SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0731
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            30954
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.66
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.9772
_exptl_absorpt_correction_T_min  0.9552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.093
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.345
_refine_ls_abs_structure_details 'Flack (1983), 4816 Friedel pairs'
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     658
_refine_ls_number_reflns         12371
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0421P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0916
_reflns_number_gt                10363
_reflns_number_total             12371
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2347.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2230222
_cod_database_fobs_code          2230222
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.60208(7) 0.40656(9) 0.85070(5) 0.0284(3) Uani d . 1 1 . .
Cl Cl2 0.75173(7) 0.36146(9) 0.65009(5) 0.0254(3) Uani d . 1 1 . .
Cl Cl3 0.10038(7) 0.36764(9) 0.84472(5) 0.0276(3) Uani d . 1 1 . .
Cl Cl4 0.25369(7) 0.31672(9) 0.65341(6) 0.0290(3) Uani d . 1 1 . .
N N1 0.3768(2) 0.3827(3) -0.18164(19) 0.0237(8) Uani d D 1 1 . .
H H1A 0.4425(16) 0.392(3) -0.176(2) 0.028 Uiso d D 1 1 . .
H H1B 0.352(2) 0.355(3) -0.2308(13) 0.028 Uiso d D 1 1 . .
N N2 0.5596(3) 0.3447(3) 0.68389(19) 0.0226(8) Uani d D 1 1 . .
H H2A 0.615(2) 0.356(3) 0.671(2) 0.027 Uiso d D 1 1 . .
H H2B 0.572(3) 0.359(3) 0.7333(12) 0.027 Uiso d D 1 1 . .
N N3 0.8777(2) 0.3890(3) -0.17864(18) 0.0219(8) Uani d D 1 1 . .
H H3A 0.9452(15) 0.386(3) -0.169(2) 0.026 Uiso d D 1 1 . .
H H3B 0.847(2) 0.378(3) -0.2302(11) 0.026 Uiso d D 1 1 . .
N N4 1.0515(3) 0.3390(3) 0.6733(2) 0.0237(8) Uani d . 1 1 . .
H H4A 1.102(3) 0.329(3) 0.662(2) 0.028 Uiso d . 1 1 . .
H H4B 1.064(3) 0.355(3) 0.726(2) 0.028 Uiso d . 1 1 . .
O O1 0.1485(2) 0.2664(3) 0.13065(18) 0.0516(9) Uani d . 1 1 . .
O O2 0.0107(2) 0.3327(3) 0.3666(2) 0.0679(12) Uani d . 1 1 . .
O O3 0.6463(3) 0.3929(3) 0.1392(2) 0.0620(11) Uani d . 1 1 . .
O O4 0.5144(2) 0.4635(3) 0.36417(18) 0.0535(9) Uani d . 1 1 . .
C C1 0.4766(3) 0.1922(3) 0.1329(2) 0.0366(10) Uani d . 1 1 . .
H H1C 0.4704 0.1260 0.1598 0.055 Uiso calc R 1 1 . .
H H1D 0.5352 0.2336 0.1650 0.055 Uiso calc R 1 1 . .
H H1E 0.4837 0.1718 0.0855 0.055 Uiso calc R 1 1 . .
C C2 0.3856(3) 0.2610(3) 0.1153(2) 0.0264(9) Uani d . 1 1 . .
C C3 0.3091(3) 0.2310(4) 0.1332(2) 0.0330(10) Uani d . 1 1 . .
H H3 0.3130 0.1635 0.1588 0.040 Uiso calc R 1 1 . .
C C4 0.2191(3) 0.2975(4) 0.1151(2) 0.0332(10) Uani d . 1 1 . .
C C5 0.2141(3) 0.4036(3) 0.0735(2) 0.0288(9) Uani d . 1 1 . .
H H5A 0.1752 0.4568 0.0899 0.035 Uiso calc R 1 1 . .
H H5B 0.1778 0.3908 0.0184 0.035 Uiso calc R 1 1 . .
C C6 0.3160(3) 0.4543(3) 0.0858(2) 0.0269(9) Uani d . 1 1 . .
C C7 0.3836(3) 0.3657(4) 0.0718(2) 0.0240(8) Uani d . 1 1 . .
H H7 0.4529 0.3950 0.0889 0.029 Uiso calc R 1 1 . .
C C8 0.3653(3) 0.4953(4) 0.1683(2) 0.0388(11) Uani d . 1 1 . .
H H8A 0.3754 0.4336 0.2033 0.058 Uiso calc R 1 1 . .
H H8B 0.3222 0.5496 0.1782 0.058 Uiso calc R 1 1 . .
H H8C 0.4297 0.5286 0.1760 0.058 Uiso calc R 1 1 . .
C C9 0.3024(3) 0.5500(3) 0.0317(2) 0.0374(9) Uani d . 1 1 . .
H H9A 0.2632 0.6071 0.0434 0.056 Uiso calc R 1 1 . .
H H9B 0.2675 0.5251 -0.0207 0.056 Uiso calc R 1 1 . .
H H9C 0.3676 0.5793 0.0377 0.056 Uiso calc R 1 1 . .
C C10 0.3498(3) 0.3350(3) -0.0105(2) 0.0226(9) Uani d . 1 1 . .
H H10 0.2809 0.3207 -0.0366 0.027 Uiso calc R 1 1 . .
C C11 0.4069(3) 0.3259(3) -0.0505(2) 0.0232(9) Uani d . 1 1 . .
H H11 0.4756 0.3429 -0.0264 0.028 Uiso calc R 1 1 . .
C C12 0.3682(3) 0.2903(3) -0.1310(2) 0.0241(9) Uani d . 1 1 . .
H H12 0.2963 0.2715 -0.1465 0.029 Uiso calc R 1 1 . .
C C13 0.4215(3) 0.1921(4) -0.1461(2) 0.0346(10) Uani d . 1 1 . .
H H13A 0.4920 0.2095 -0.1320 0.052 Uiso calc R 1 1 . .
H H13B 0.3918 0.1734 -0.2002 0.052 Uiso calc R 1 1 . .
H H13C 0.4150 0.1300 -0.1159 0.052 Uiso calc R 1 1 . .
C C14 0.3322(3) 0.4880(4) -0.1721(3) 0.0301(10) Uani d . 1 1 . .
H H14A 0.3730 0.5202 -0.1229 0.045 Uiso calc R 1 1 . .
H H14B 0.2648 0.4751 -0.1740 0.045 Uiso calc R 1 1 . .
H H14C 0.3294 0.5381 -0.2130 0.045 Uiso calc R 1 1 . .
C C15 0.2916(3) 0.5499(3) 0.3735(2) 0.0402(11) Uani d . 1 1 . .
H H15A 0.3446 0.5748 0.4205 0.060 Uiso calc R 1 1 . .
H H15B 0.2413 0.6074 0.3541 0.060 Uiso calc R 1 1 . .
H H15C 0.3199 0.5335 0.3355 0.060 Uiso calc R 1 1 . .
C C16 0.2445(3) 0.4494(3) 0.3893(2) 0.0286(9) Uani d . 1 1 . .
C C17 0.1473(3) 0.4395(4) 0.3716(2) 0.0368(11) Uani d . 1 1 . .
H H17 0.1057 0.4996 0.3480 0.044 Uiso calc R 1 1 . .
C C18 0.1012(3) 0.3409(4) 0.3864(3) 0.0432(13) Uani d . 1 1 . .
C C19 0.1689(3) 0.2496(3) 0.4276(2) 0.0364(10) Uani d . 1 1 . .
H H19A 0.1330 0.1795 0.4117 0.044 Uiso calc R 1 1 . .
H H19B 0.1856 0.2581 0.4828 0.044 Uiso calc R 1 1 . .
C C20 0.2662(3) 0.2444(3) 0.4133(2) 0.0289(9) Uani d . 1 1 . .
C C21 0.3162(3) 0.3575(4) 0.4300(2) 0.0216(8) Uani d . 1 1 . .
H H21 0.3718 0.3574 0.4113 0.026 Uiso calc R 1 1 . .
C C22 0.2423(3) 0.2147(4) 0.3300(2) 0.0356(10) Uani d . 1 1 . .
H H22A 0.1941 0.2669 0.2969 0.053 Uiso calc R 1 1 . .
H H22B 0.2142 0.1409 0.3200 0.053 Uiso calc R 1 1 . .
H H22C 0.3035 0.2172 0.3198 0.053 Uiso calc R 1 1 . .
C C23 0.3339(3) 0.1579(3) 0.4649(2) 0.0340(9) Uani d . 1 1 . .
H H23A 0.3059 0.0853 0.4479 0.051 Uiso calc R 1 1 . .
H H23B 0.3393 0.1699 0.5173 0.051 Uiso calc R 1 1 . .
H H23C 0.4000 0.1629 0.4628 0.051 Uiso calc R 1 1 . .
C C24 0.3593(3) 0.3841(3) 0.5135(2) 0.0207(8) Uani d . 1 1 . .
H H24 0.3143 0.3850 0.5388 0.025 Uiso calc R 1 1 . .
C C25 0.4529(3) 0.4062(3) 0.5550(2) 0.0238(9) Uani d . 1 1 . .
H H25 0.4998 0.4066 0.5313 0.029 Uiso calc R 1 1 . .
C C26 0.4881(3) 0.4308(3) 0.6381(2) 0.0198(8) Uani d . 1 1 . .
H H26 0.4291 0.4307 0.6529 0.024 Uiso calc R 1 1 . .
C C27 0.5398(3) 0.5411(3) 0.6596(2) 0.0288(9) Uani d . 1 1 . .
H H27A 0.4941 0.5991 0.6317 0.043 Uiso calc R 1 1 . .
H H27B 0.5989 0.5421 0.6467 0.043 Uiso calc R 1 1 . .
H H27C 0.5598 0.5530 0.7144 0.043 Uiso calc R 1 1 . .
C C28 0.5207(3) 0.2325(3) 0.6718(3) 0.0302(10) Uani d . 1 1 . .
H H28A 0.5089 0.2095 0.6198 0.045 Uiso calc R 1 1 . .
H H28B 0.4580 0.2297 0.6798 0.045 Uiso calc R 1 1 . .
H H28C 0.5691 0.1833 0.7079 0.045 Uiso calc R 1 1 . .
C C29 0.9222(3) 0.1765(4) 0.1326(3) 0.0425(11) Uani d . 1 1 . .
H H29A 0.8918 0.1190 0.1523 0.064 Uiso calc R 1 1 . .
H H29B 0.9880 0.1945 0.1707 0.064 Uiso calc R 1 1 . .
H H29C 0.9290 0.1509 0.0860 0.064 Uiso calc R 1 1 . .
C C30 0.8585(3) 0.2750(3) 0.1154(2) 0.0281(9) Uani d . 1 1 . .
C C31 0.7785(3) 0.2854(4) 0.1344(2) 0.0365(10) Uani d . 1 1 . .
H H31 0.7606 0.2254 0.1582 0.044 Uiso calc R 1 1 . .
C C32 0.7182(3) 0.3840(4) 0.1200(3) 0.0409(12) Uani d . 1 1 . .
C C33 0.7455(3) 0.4763(3) 0.0787(2) 0.0352(10) Uani d . 1 1 . .
H H33A 0.7268 0.5464 0.0956 0.042 Uiso calc R 1 1 . .
H H33B 0.7059 0.4689 0.0236 0.042 Uiso calc R 1 1 . .
C C34 0.8556(3) 0.4805(3) 0.0915(2) 0.0279(9) Uani d . 1 1 . .
C C35 0.8889(3) 0.3661(4) 0.0745(2) 0.0228(8) Uani d . 1 1 . .
H H35 0.9631 0.3660 0.0925 0.027 Uiso calc R 1 1 . .
C C36 0.9168(3) 0.5104(4) 0.1747(2) 0.0381(11) Uani d . 1 1 . .
H H36A 0.9871 0.5171 0.1824 0.057 Uiso calc R 1 1 . .
H H36B 0.9092 0.4532 0.2081 0.057 Uiso calc R 1 1 . .
H H36C 0.8931 0.5801 0.1868 0.057 Uiso calc R 1 1 . .
C C37 0.8720(3) 0.5684(3) 0.0399(2) 0.0345(9) Uani d . 1 1 . .
H H37A 0.9404 0.5639 0.0423 0.052 Uiso calc R 1 1 . .
H H37B 0.8605 0.6407 0.0570 0.052 Uiso calc R 1 1 . .
H H37C 0.8255 0.5566 -0.0126 0.052 Uiso calc R 1 1 . .
C C38 0.8472(3) 0.3421(3) -0.0090(2) 0.0219(9) Uani d . 1 1 . .
H H38 0.7768 0.3428 -0.0339 0.026 Uiso calc R 1 1 . .
C C39 0.8991(3) 0.3197(3) -0.0518(2) 0.0205(8) Uani d . 1 1 . .
H H39 0.9696 0.3167 -0.0282 0.025 Uiso calc R 1 1 . .
C C40 0.8508(3) 0.2994(4) -0.1352(2) 0.0231(9) Uani d . 1 1 . .
H H40 0.7771 0.3003 -0.1498 0.028 Uiso calc R 1 1 . .
C C41 0.8787(3) 0.1929(3) -0.1608(2) 0.0316(10) Uani d . 1 1 . .
H H41A 0.8606 0.1326 -0.1348 0.047 Uiso calc R 1 1 . .
H H41B 0.9506 0.1915 -0.1484 0.047 Uiso calc R 1 1 . .
H H41C 0.8432 0.1852 -0.2158 0.047 Uiso calc R 1 1 . .
C C42 0.8539(3) 0.5010(3) -0.1619(3) 0.0293(10) Uani d . 1 1 . .
H H42A 0.8986 0.5216 -0.1104 0.044 Uiso calc R 1 1 . .
H H42B 0.7849 0.5037 -0.1656 0.044 Uiso calc R 1 1 . .
H H42C 0.8624 0.5520 -0.1987 0.044 Uiso calc R 1 1 . .
C C43 0.8362(3) 0.5329(4) 0.3550(3) 0.0460(12) Uani d . 1 1 . .
H H43A 0.8966 0.5460 0.4002 0.069 Uiso calc R 1 1 . .
H H43B 0.8053 0.6030 0.3340 0.069 Uiso calc R 1 1 . .
H H43C 0.8534 0.4937 0.3168 0.069 Uiso calc R 1 1 . .
C C44 0.7644(3) 0.4655(3) 0.3766(2) 0.0273(9) Uani d . 1 1 . .
C C45 0.6707(3) 0.4961(4) 0.3592(2) 0.0325(10) Uani d . 1 1 . .
H H45 0.6487 0.5624 0.3321 0.039 Uiso calc R 1 1 . .
C C46 0.5998(3) 0.4324(4) 0.3800(2) 0.0334(10) Uani d . 1 1 . .
C C47 0.6372(3) 0.3269(3) 0.4227(2) 0.0300(10) Uani d . 1 1 . .
H H47A 0.5819 0.2735 0.4071 0.036 Uiso calc R 1 1 . .
H H47B 0.6566 0.3409 0.4777 0.036 Uiso calc R 1 1 . .
C C48 0.7266(3) 0.2755(3) 0.4099(2) 0.0262(9) Uani d . 1 1 . .
C C49 0.8074(3) 0.3643(4) 0.4227(2) 0.0228(8) Uani d . 1 1 . .
H H49 0.8594 0.3341 0.4057 0.027 Uiso calc R 1 1 . .
C C50 0.6942(3) 0.2327(4) 0.3283(2) 0.0372(10) Uani d . 1 1 . .
H H50A 0.6652 0.2925 0.2925 0.056 Uiso calc R 1 1 . .
H H50B 0.6447 0.1748 0.3200 0.056 Uiso calc R 1 1 . .
H H50C 0.7522 0.2034 0.3203 0.056 Uiso calc R 1 1 . .
C C51 0.7669(3) 0.1809(3) 0.4647(2) 0.0343(9) Uani d . 1 1 . .
H H51A 0.7173 0.1224 0.4520 0.051 Uiso calc R 1 1 . .
H H51B 0.7816 0.2060 0.5168 0.051 Uiso calc R 1 1 . .
H H51C 0.8280 0.1534 0.4607 0.051 Uiso calc R 1 1 . .
C C52 0.8574(3) 0.3972(3) 0.5053(2) 0.0238(9) Uani d . 1 1 . .
H H52 0.8153 0.4150 0.5314 0.029 Uiso calc R 1 1 . .
C C53 0.9535(3) 0.4034(3) 0.5440(2) 0.0249(9) Uani d . 1 1 . .
H H53 0.9977 0.3878 0.5193 0.030 Uiso calc R 1 1 . .
C C54 0.9954(3) 0.4344(4) 0.6264(2) 0.0253(9) Uani d . 1 1 . .
H H54 0.9389 0.4526 0.6421 0.030 Uiso calc R 1 1 . .
C C55 1.0666(3) 0.5323(3) 0.6449(3) 0.0337(10) Uani d . 1 1 . .
H H55A 1.0318 0.5958 0.6152 0.051 Uiso calc R 1 1 . .
H H55B 1.1239 0.5145 0.6320 0.051 Uiso calc R 1 1 . .
H H55C 1.0894 0.5492 0.6992 0.051 Uiso calc R 1 1 . .
C C56 0.9936(3) 0.2359(4) 0.6599(3) 0.0304(10) Uani d . 1 1 . .
H H56A 0.9828 0.2078 0.6092 0.046 Uiso calc R 1 1 . .
H H56B 0.9292 0.2500 0.6635 0.046 Uiso calc R 1 1 . .
H H56C 1.0305 0.1818 0.6983 0.046 Uiso calc R 1 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
C14 N1 C12 . . 115.0(3) ?
C14 N1 H1A . . 111(2) ?
C12 N1 H1A . . 110(2) ?
C14 N1 H1B . . 115(2) ?
C12 N1 H1B . . 106(2) ?
H1A N1 H1B . . 99(3) ?
C28 N2 C26 . . 115.1(3) ?
C28 N2 H2A . . 115(2) ?
C26 N2 H2A . . 102(2) ?
C28 N2 H2B . . 105(3) ?
C26 N2 H2B . . 107(3) ?
H2A N2 H2B . . 114(3) ?
C42 N3 C40 . . 115.1(3) ?
C42 N3 H3A . . 108(2) ?
C40 N3 H3A . . 110(2) ?
C42 N3 H3B . . 108(2) ?
C40 N3 H3B . . 111(2) ?
H3A N3 H3B . . 105(3) ?
C56 N4 C54 . . 114.5(3) ?
C56 N4 H4A . . 109(3) ?
C54 N4 H4A . . 107(3) ?
C56 N4 H4B . . 103(2) ?
C54 N4 H4B . . 108(2) ?
H4A N4 H4B . . 117(3) ?
C2 C1 H1C . . 109.5 ?
C2 C1 H1D . . 109.5 ?
H1C C1 H1D . . 109.5 ?
C2 C1 H1E . . 109.5 ?
H1C C1 H1E . . 109.5 ?
H1D C1 H1E . . 109.5 ?
C3 C2 C1 . . 122.8(4) ?
C3 C2 C7 . . 121.9(4) ?
C1 C2 C7 . . 115.3(3) ?
C2 C3 C4 . . 122.9(4) ?
C2 C3 H3 . . 118.5 ?
C4 C3 H3 . . 118.5 ?
O1 C4 C3 . . 121.5(4) ?
O1 C4 C5 . . 121.0(4) ?
C3 C4 C5 . . 117.5(3) ?
C4 C5 C6 . . 114.7(3) ?
C4 C5 H5A . . 108.6 ?
C6 C5 H5A . . 108.6 ?
C4 C5 H5B . . 108.6 ?
C6 C5 H5B . . 108.6 ?
H5A C5 H5B . . 107.6 ?
C9 C6 C8 . . 109.2(3) ?
C9 C6 C5 . . 109.8(3) ?
C8 C6 C5 . . 109.5(3) ?
C9 C6 C7 . . 110.4(3) ?
C8 C6 C7 . . 108.9(3) ?
C5 C6 C7 . . 109.0(3) ?
C10 C7 C2 . . 106.8(3) ?
C10 C7 C6 . . 112.2(3) ?
C2 C7 C6 . . 112.1(3) ?
C10 C7 H7 . . 108.5 ?
C2 C7 H7 . . 108.5 ?
C6 C7 H7 . . 108.5 ?
C6 C8 H8A . . 109.5 ?
C6 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C6 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C6 C9 H9A . . 109.5 ?
C6 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C6 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C11 C10 C7 . . 126.3(4) ?
C11 C10 H10 . . 116.8 ?
C7 C10 H10 . . 116.8 ?
C10 C11 C12 . . 123.0(4) ?
C10 C11 H11 . . 118.5 ?
C12 C11 H11 . . 118.5 ?
C11 C12 C13 . . 114.2(4) ?
C11 C12 N1 . . 110.3(3) ?
C13 C12 N1 . . 107.3(3) ?
C11 C12 H12 . . 108.3 ?
C13 C12 H12 . . 108.3 ?
N1 C12 H12 . . 108.3 ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N1 C14 H14A . . 109.5 ?
N1 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
N1 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C16 C15 H15A . . 109.5 ?
C16 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C16 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C17 C16 C15 . . 123.4(4) ?
C17 C16 C21 . . 121.0(4) ?
C15 C16 C21 . . 115.6(4) ?
C16 C17 C18 . . 123.4(4) ?
C16 C17 H17 . . 118.3 ?
C18 C17 H17 . . 118.3 ?
O2 C18 C17 . . 121.8(5) ?
O2 C18 C19 . . 120.8(4) ?
C17 C18 C19 . . 117.4(4) ?
C18 C19 C20 . . 113.7(4) ?
C18 C19 H19A . . 108.8 ?
C20 C19 H19A . . 108.8 ?
C18 C19 H19B . . 108.8 ?
C20 C19 H19B . . 108.8 ?
H19A C19 H19B . . 107.7 ?
C23 C20 C22 . . 109.7(3) ?
C23 C20 C21 . . 110.8(3) ?
C22 C20 C21 . . 109.2(3) ?
C23 C20 C19 . . 109.0(3) ?
C22 C20 C19 . . 109.4(3) ?
C21 C20 C19 . . 108.7(3) ?
C24 C21 C16 . . 107.7(3) ?
C24 C21 C20 . . 112.7(3) ?
C16 C21 C20 . . 112.4(3) ?
C24 C21 H21 . . 108.0 ?
C16 C21 H21 . . 108.0 ?
C20 C21 H21 . . 108.0 ?
C20 C22 H22A . . 109.5 ?
C20 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C20 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C20 C23 H23A . . 109.5 ?
C20 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C20 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C25 C24 C21 . . 126.6(3) ?
C25 C24 H24 . . 116.7 ?
C21 C24 H24 . . 116.7 ?
C24 C25 C26 . . 122.3(3) ?
C24 C25 H25 . . 118.9 ?
C26 C25 H25 . . 118.9 ?
C25 C26 N2 . . 110.7(3) ?
C25 C26 C27 . . 113.4(3) ?
N2 C26 C27 . . 107.7(3) ?
C25 C26 H26 . . 108.3 ?
N2 C26 H26 . . 108.3 ?
C27 C26 H26 . . 108.3 ?
C26 C27 H27A . . 109.5 ?
C26 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C26 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
N2 C28 H28A . . 109.5 ?
N2 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
N2 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C30 C29 H29A . . 109.5 ?
C30 C29 H29B . . 109.5 ?
H29A C29 H29B . . 109.5 ?
C30 C29 H29C . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?
C31 C30 C29 . . 123.4(4) ?
C31 C30 C35 . . 121.2(4) ?
C29 C30 C35 . . 115.5(3) ?
C30 C31 C32 . . 123.2(4) ?
C30 C31 H31 . . 118.4 ?
C32 C31 H31 . . 118.4 ?
O3 C32 C31 . . 122.3(4) ?
O3 C32 C33 . . 120.5(4) ?
C31 C32 C33 . . 117.3(3) ?
C32 C33 C34 . . 114.2(3) ?
C32 C33 H33A . . 108.7 ?
C34 C33 H33A . . 108.7 ?
C32 C33 H33B . . 108.7 ?
C34 C33 H33B . . 108.7 ?
H33A C33 H33B . . 107.6 ?
C33 C34 C37 . . 109.4(3) ?
C33 C34 C36 . . 109.3(3) ?
C37 C34 C36 . . 108.8(3) ?
C33 C34 C35 . . 109.1(3) ?
C37 C34 C35 . . 111.2(3) ?
C36 C34 C35 . . 109.0(3) ?
C38 C35 C30 . . 108.7(3) ?
C38 C35 C34 . . 111.4(3) ?
C30 C35 C34 . . 112.3(3) ?
C38 C35 H35 . . 108.1 ?
C30 C35 H35 . . 108.1 ?
C34 C35 H35 . . 108.1 ?
C34 C36 H36A . . 109.5 ?
C34 C36 H36B . . 109.5 ?
H36A C36 H36B . . 109.5 ?
C34 C36 H36C . . 109.5 ?
H36A C36 H36C . . 109.5 ?
H36B C36 H36C . . 109.5 ?
C34 C37 H37A . . 109.5 ?
C34 C37 H37B . . 109.5 ?
H37A C37 H37B . . 109.5 ?
C34 C37 H37C . . 109.5 ?
H37A C37 H37C . . 109.5 ?
H37B C37 H37C . . 109.5 ?
C39 C38 C35 . . 126.4(4) ?
C39 C38 H38 . . 116.8 ?
C35 C38 H38 . . 116.8 ?
C38 C39 C40 . . 122.5(4) ?
C38 C39 H39 . . 118.7 ?
C40 C39 H39 . . 118.7 ?
C39 C40 C41 . . 114.5(4) ?
C39 C40 N3 . . 110.2(3) ?
C41 C40 N3 . . 107.1(3) ?
C39 C40 H40 . . 108.3 ?
C41 C40 H40 . . 108.3 ?
N3 C40 H40 . . 108.3 ?
C40 C41 H41A . . 109.5 ?
C40 C41 H41B . . 109.5 ?
H41A C41 H41B . . 109.5 ?
C40 C41 H41C . . 109.5 ?
H41A C41 H41C . . 109.5 ?
H41B C41 H41C . . 109.5 ?
N3 C42 H42A . . 109.5 ?
N3 C42 H42B . . 109.5 ?
H42A C42 H42B . . 109.5 ?
N3 C42 H42C . . 109.5 ?
H42A C42 H42C . . 109.5 ?
H42B C42 H42C . . 109.5 ?
C44 C43 H43A . . 109.5 ?
C44 C43 H43B . . 109.5 ?
H43A C43 H43B . . 109.5 ?
C44 C43 H43C . . 109.5 ?
H43A C43 H43C . . 109.5 ?
H43B C43 H43C . . 109.5 ?
C45 C44 C43 . . 122.0(4) ?
C45 C44 C49 . . 122.3(4) ?
C43 C44 C49 . . 115.6(3) ?
C44 C45 C46 . . 123.0(4) ?
C44 C45 H45 . . 118.5 ?
C46 C45 H45 . . 118.5 ?
O4 C46 C45 . . 121.5(4) ?
O4 C46 C47 . . 121.4(4) ?
C45 C46 C47 . . 117.0(4) ?
C46 C47 C48 . . 114.5(3) ?
C46 C47 H47A . . 108.6 ?
C48 C47 H47A . . 108.6 ?
C46 C47 H47B . . 108.6 ?
C48 C47 H47B . . 108.6 ?
H47A C47 H47B . . 107.6 ?
C51 C48 C50 . . 108.8(3) ?
C51 C48 C47 . . 109.3(3) ?
C50 C48 C47 . . 110.3(3) ?
C51 C48 C49 . . 110.9(3) ?
C50 C48 C49 . . 108.6(3) ?
C47 C48 C49 . . 108.9(3) ?
C44 C49 C52 . . 108.3(3) ?
C44 C49 C48 . . 111.3(3) ?
C52 C49 C48 . . 112.6(3) ?
C44 C49 H49 . . 108.2 ?
C52 C49 H49 . . 108.2 ?
C48 C49 H49 . . 108.2 ?
C48 C50 H50A . . 109.5 ?
C48 C50 H50B . . 109.5 ?
H50A C50 H50B . . 109.5 ?
C48 C50 H50C . . 109.5 ?
H50A C50 H50C . . 109.5 ?
H50B C50 H50C . . 109.5 ?
C48 C51 H51A . . 109.5 ?
C48 C51 H51B . . 109.5 ?
H51A C51 H51B . . 109.5 ?
C48 C51 H51C . . 109.5 ?
H51A C51 H51C . . 109.5 ?
H51B C51 H51C . . 109.5 ?
C53 C52 C49 . . 126.0(4) ?
C53 C52 H52 . . 117.0 ?
C49 C52 H52 . . 117.0 ?
C52 C53 C54 . . 121.6(3) ?
C52 C53 H53 . . 119.2 ?
C54 C53 H53 . . 119.2 ?
C53 C54 N4 . . 109.5(3) ?
C53 C54 C55 . . 114.0(3) ?
N4 C54 C55 . . 107.8(3) ?
C53 C54 H54 . . 108.5 ?
N4 C54 H54 . . 108.5 ?
C55 C54 H54 . . 108.5 ?
C54 C55 H55A . . 109.5 ?
C54 C55 H55B . . 109.5 ?
H55A C55 H55B . . 109.5 ?
C54 C55 H55C . . 109.5 ?
H55A C55 H55C . . 109.5 ?
H55B C55 H55C . . 109.5 ?
N4 C56 H56A . . 109.5 ?
N4 C56 H56B . . 109.5 ?
H56A C56 H56B . . 109.5 ?
N4 C56 H56C . . 109.5 ?
H56A C56 H56C . . 109.5 ?
H56B C56 H56C . . 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
N1 C14 . 1.486(5) ?
N1 C12 . 1.522(5) ?
N1 H1A . 0.928(18) ?
N1 H1B . 0.927(18) ?
N2 C28 . 1.471(5) ?
N2 C26 . 1.504(5) ?
N2 H2A . 0.940(18) ?
N2 H2B . 0.905(18) ?
N3 C42 . 1.479(5) ?
N3 C40 . 1.512(5) ?
N3 H3A . 0.929(18) ?
N3 H3B . 0.921(18) ?
N4 C56 . 1.485(5) ?
N4 C54 . 1.507(5) ?
N4 H4A . 0.85(3) ?
N4 H4B . 0.96(4) ?
O1 C4 . 1.234(4) ?
O2 C18 . 1.228(5) ?
O3 C32 . 1.237(5) ?
O4 C46 . 1.222(5) ?
C1 C2 . 1.496(6) ?
C1 H1C . 0.9800 ?
C1 H1D . 0.9800 ?
C1 H1E . 0.9800 ?
C2 C3 . 1.333(5) ?
C2 C7 . 1.521(6) ?
C3 C4 . 1.467(6) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.508(6) ?
C5 C6 . 1.540(5) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C9 . 1.522(5) ?
C6 C8 . 1.539(5) ?
C6 C7 . 1.555(6) ?
C7 C10 . 1.499(5) ?
C7 H7 . 1.0000 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 C11 . 1.328(5) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.482(6) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.516(6) ?
C12 H12 . 1.0000 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 C16 . 1.495(6) ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 C17 . 1.327(6) ?
C16 C21 . 1.529(6) ?
C17 C18 . 1.460(7) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.499(6) ?
C19 C20 . 1.542(5) ?
C19 H19A . 0.9900 ?
C19 H19B . 0.9900 ?
C20 C23 . 1.523(5) ?
C20 C22 . 1.532(5) ?
C20 C21 . 1.540(6) ?
C21 C24 . 1.506(5) ?
C21 H21 . 1.0000 ?
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 C25 . 1.315(6) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.495(5) ?
C25 H25 . 0.9500 ?
C26 C27 . 1.524(6) ?
C26 H26 . 1.0000 ?
C27 H27A . 0.9800 ?
C27 H27B . 0.9800 ?
C27 H27C . 0.9800 ?
C28 H28A . 0.9800 ?
C28 H28B . 0.9800 ?
C28 H28C . 0.9800 ?
C29 C30 . 1.480(6) ?
C29 H29A . 0.9800 ?
C29 H29B . 0.9800 ?
C29 H29C . 0.9800 ?
C30 C31 . 1.349(6) ?
C30 C35 . 1.520(5) ?
C31 C32 . 1.456(7) ?
C31 H31 . 0.9500 ?
C32 C33 . 1.513(6) ?
C33 C34 . 1.527(6) ?
C33 H33A . 0.9900 ?
C33 H33B . 0.9900 ?
C34 C37 . 1.536(5) ?
C34 C36 . 1.537(5) ?
C34 C35 . 1.556(6) ?
C35 C38 . 1.497(5) ?
C35 H35 . 1.0000 ?
C36 H36A . 0.9800 ?
C36 H36B . 0.9800 ?
C36 H36C . 0.9800 ?
C37 H37A . 0.9800 ?
C37 H37B . 0.9800 ?
C37 H37C . 0.9800 ?
C38 C39 . 1.335(5) ?
C38 H38 . 0.9500 ?
C39 C40 . 1.491(5) ?
C39 H39 . 0.9500 ?
C40 C41 . 1.501(6) ?
C40 H40 . 1.0000 ?
C41 H41A . 0.9800 ?
C41 H41B . 0.9800 ?
C41 H41C . 0.9800 ?
C42 H42A . 0.9800 ?
C42 H42B . 0.9800 ?
C42 H42C . 0.9800 ?
C43 C44 . 1.506(6) ?
C43 H43A . 0.9800 ?
C43 H43B . 0.9800 ?
C43 H43C . 0.9800 ?
C44 C45 . 1.328(5) ?
C44 C49 . 1.509(6) ?
C45 C46 . 1.464(6) ?
C45 H45 . 0.9500 ?
C46 C47 . 1.512(6) ?
C47 C48 . 1.545(5) ?
C47 H47A . 0.9900 ?
C47 H47B . 0.9900 ?
C48 C51 . 1.519(5) ?
C48 C50 . 1.533(5) ?
C48 C49 . 1.551(6) ?
C49 C52 . 1.512(5) ?
C49 H49 . 1.0000 ?
C50 H50A . 0.9800 ?
C50 H50B . 0.9800 ?
C50 H50C . 0.9800 ?
C51 H51A . 0.9800 ?
C51 H51B . 0.9800 ?
C51 H51C . 0.9800 ?
C52 C53 . 1.309(6) ?
C52 H52 . 0.9500 ?
C53 C54 . 1.499(6) ?
C53 H53 . 0.9500 ?
C54 C55 . 1.535(6) ?
C54 H54 . 1.0000 ?
C55 H55A . 0.9800 ?
C55 H55B . 0.9800 ?
C55 H55C . 0.9800 ?
C56 H56A . 0.9800 ?
C56 H56B . 0.9800 ?
C56 H56C . 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
N1 H1A Cl1 1_554 0.928(18) 2.185(19) 3.109(3) 173(3)
N1 H1B Cl4 1_554 0.927(18) 2.17(2) 3.069(4) 163(3)
N2 H2A Cl2 . 0.940(18) 2.172(19) 3.105(3) 171(3)
N2 H2B Cl1 . 0.905(18) 2.186(19) 3.089(4) 175(4)
N3 H3A Cl3 1_654 0.929(18) 2.182(19) 3.108(3) 175(3)
N3 H3B Cl2 1_554 0.921(18) 2.176(19) 3.088(4) 171(3)
N4 H4A Cl4 1_655 0.85(3) 2.28(4) 3.117(4) 169(4)
N4 H4B Cl3 1_655 0.96(4) 2.13(4) 3.083(4) 172(4)
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
C1 C2 C3 C4 . . . . -179.1(4) ?
C7 C2 C3 C4 . . . . -2.3(6) ?
C2 C3 C4 O1 . . . . 178.2(4) ?
C2 C3 C4 C5 . . . . 0.8(6) ?
O1 C4 C5 C6 . . . . 156.5(4) ?
C3 C4 C5 C6 . . . . -26.1(5) ?
C4 C5 C6 C9 . . . . 171.0(3) ?
C4 C5 C6 C8 . . . . -69.2(4) ?
C4 C5 C6 C7 . . . . 49.9(4) ?
C3 C2 C7 C10 . . . . -95.1(4) ?
C1 C2 C7 C10 . . . . 81.9(4) ?
C3 C2 C7 C6 . . . . 28.2(5) ?
C1 C2 C7 C6 . . . . -154.8(3) ?
C9 C6 C7 C10 . . . . -50.5(4) ?
C8 C6 C7 C10 . . . . -170.4(3) ?
C5 C6 C7 C10 . . . . 70.2(4) ?
C9 C6 C7 C2 . . . . -170.7(3) ?
C8 C6 C7 C2 . . . . 69.4(4) ?
C5 C6 C7 C2 . . . . -50.0(4) ?
C2 C7 C10 C11 . . . . -103.9(5) ?
C6 C7 C10 C11 . . . . 132.9(4) ?
C7 C10 C11 C12 . . . . 177.2(4) ?
C10 C11 C12 C13 . . . . -124.1(4) ?
C10 C11 C12 N1 . . . . 115.0(4) ?
C14 N1 C12 C11 . . . . -52.5(5) ?
C14 N1 C12 C13 . . . . -177.5(3) ?
C15 C16 C17 C18 . . . . 179.4(4) ?
C21 C16 C17 C18 . . . . -2.3(6) ?
C16 C17 C18 O2 . . . . -177.1(4) ?
C16 C17 C18 C19 . . . . 3.5(6) ?
O2 C18 C19 C20 . . . . 150.8(4) ?
C17 C18 C19 C20 . . . . -29.8(5) ?
C18 C19 C20 C23 . . . . 173.3(3) ?
C18 C19 C20 C22 . . . . -66.7(4) ?
C18 C19 C20 C21 . . . . 52.5(4) ?
C17 C16 C21 C24 . . . . -97.4(5) ?
C15 C16 C21 C24 . . . . 80.9(4) ?
C17 C16 C21 C20 . . . . 27.3(5) ?
C15 C16 C21 C20 . . . . -154.4(3) ?
C23 C20 C21 C24 . . . . -48.3(4) ?
C22 C20 C21 C24 . . . . -169.3(3) ?
C19 C20 C21 C24 . . . . 71.4(4) ?
C23 C20 C21 C16 . . . . -170.2(3) ?
C22 C20 C21 C16 . . . . 68.8(4) ?
C19 C20 C21 C16 . . . . -50.5(4) ?
C16 C21 C24 C25 . . . . -114.8(4) ?
C20 C21 C24 C25 . . . . 120.7(4) ?
C21 C24 C25 C26 . . . . -179.5(4) ?
C24 C25 C26 N2 . . . . 115.7(4) ?
C24 C25 C26 C27 . . . . -123.1(4) ?
C28 N2 C26 C25 . . . . -57.2(4) ?
C28 N2 C26 C27 . . . . 178.3(3) ?
C29 C30 C31 C32 . . . . 177.6(4) ?
C35 C30 C31 C32 . . . . -2.3(7) ?
C30 C31 C32 O3 . . . . -178.4(4) ?
C30 C31 C32 C33 . . . . 2.7(7) ?
O3 C32 C33 C34 . . . . 152.3(4) ?
C31 C32 C33 C34 . . . . -28.8(5) ?
C32 C33 C34 C37 . . . . 173.5(3) ?
C32 C33 C34 C36 . . . . -67.5(4) ?
C32 C33 C34 C35 . . . . 51.6(4) ?
C31 C30 C35 C38 . . . . -96.7(5) ?
C29 C30 C35 C38 . . . . 83.4(4) ?
C31 C30 C35 C34 . . . . 27.1(5) ?
C29 C30 C35 C34 . . . . -152.9(4) ?
C33 C34 C35 C38 . . . . 72.2(4) ?
C37 C34 C35 C38 . . . . -48.6(4) ?
C36 C34 C35 C38 . . . . -168.5(3) ?
C33 C34 C35 C30 . . . . -50.1(4) ?
C37 C34 C35 C30 . . . . -170.8(3) ?
C36 C34 C35 C30 . . . . 69.2(4) ?
C30 C35 C38 C39 . . . . -114.5(4) ?
C34 C35 C38 C39 . . . . 121.2(4) ?
C35 C38 C39 C40 . . . . -178.5(4) ?
C38 C39 C40 C41 . . . . -124.9(4) ?
C38 C39 C40 N3 . . . . 114.2(4) ?
C42 N3 C40 C39 . . . . -55.9(4) ?
C42 N3 C40 C41 . . . . 179.0(3) ?
C43 C44 C45 C46 . . . . -179.6(4) ?
C49 C44 C45 C46 . . . . -2.9(6) ?
C44 C45 C46 O4 . . . . 178.9(4) ?
C44 C45 C46 C47 . . . . -0.4(6) ?
O4 C46 C47 C48 . . . . 156.0(4) ?
C45 C46 C47 C48 . . . . -24.6(5) ?
C46 C47 C48 C51 . . . . 171.2(3) ?
C46 C47 C48 C50 . . . . -69.1(4) ?
C46 C47 C48 C49 . . . . 50.0(4) ?
C45 C44 C49 C52 . . . . -94.0(5) ?
C43 C44 C49 C52 . . . . 82.8(4) ?
C45 C44 C49 C48 . . . . 30.3(5) ?
C43 C44 C49 C48 . . . . -152.9(3) ?
C51 C48 C49 C44 . . . . -171.9(3) ?
C50 C48 C49 C44 . . . . 68.6(4) ?
C47 C48 C49 C44 . . . . -51.6(4) ?
C51 C48 C49 C52 . . . . -50.1(4) ?
C50 C48 C49 C52 . . . . -169.6(3) ?
C47 C48 C49 C52 . . . . 70.2(4) ?
C44 C49 C52 C53 . . . . -106.0(5) ?
C48 C49 C52 C53 . . . . 130.5(4) ?
C49 C52 C53 C54 . . . . -178.5(4) ?
C52 C53 C54 N4 . . . . 114.6(4) ?
C52 C53 C54 C55 . . . . -124.7(4) ?
C56 N4 C54 C53 . . . . -53.5(4) ?
C56 N4 C54 C55 . . . . -178.0(3) ?
