#------------------------------------------------------------------------------
#$Date: 2020-04-29 23:33:43 +0300 (Wed, 29 Apr 2020) $
#$Revision: 251290 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038309.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_4038309
loop_
_publ_author_name
'Wu, Xing-De'
'Li, Xiao-Nian'
'Peng, Li-Yan'
'Zhao, Qin-Shi'
_publ_section_title
;
 Huperserratines A and B, Two Macrocyclic Lycopodium Alkaloids with
 an Unusual Skeleton from Huperzia serrata.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00623
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H28 N2 O3'
_chemical_formula_sum            'C17 H28 N2 O3'
_chemical_formula_weight         308.41
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 91.2610(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.2918(6)
_cell_length_b                   8.0470(2)
_cell_length_c                   17.8937(5)
_cell_measurement_reflns_used    9885
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.22
_cell_measurement_theta_min      3.64
_cell_volume                     3496.94(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14701
_diffrn_reflns_theta_full        69.22
_diffrn_reflns_theta_max         69.22
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  0.9099
_exptl_absorpt_correction_T_min  0.6447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.703
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         5203
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0366
_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)+(0.0356P)²+2.0464P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.0976
_reflns_number_gt                5070
_reflns_number_total             5203
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00623_si_003.cif
_cod_data_source_block           cu_fwa_145_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4038309
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O13 O 0.32321(6) 0.5904(3) 0.80929(8) 0.0512(5) Uani 1 1 d . . .
O5 O 0.30541(6) 0.9931(2) 0.87842(7) 0.0469(4) Uani 1 1 d . . .
H5 H 0.2720 1.0021 0.8657 0.070 Uiso 1 1 calc R . .
O4 O 0.41219(6) 0.9934(2) 1.09118(8) 0.0434(4) Uani 1 1 d . . .
O5' O 0.31003(6) 0.5675(2) 0.36823(7) 0.0388(4) Uani 1 1 d . . .
H5' H 0.2766 0.5802 0.3566 0.058 Uiso 1 1 calc R . .
O4' O 0.41806(6) 0.5359(2) 0.57985(8) 0.0411(4) Uani 1 1 d . . .
O13' O 0.32146(5) 0.1196(2) 0.31289(7) 0.0395(4) Uani 1 1 d . . .
N5 N 0.31079(7) 1.0060(2) 0.95489(8) 0.0370(4) Uani 1 1 d . . .
N5' N 0.31681(7) 0.5764(2) 0.44475(8) 0.0326(4) Uani 1 1 d . . .
C16 C 0.51652(9) 0.6650(3) 0.76779(13) 0.0468(6) Uani 1 1 d . . .
H16A H 0.5441 0.7507 0.7794 0.070 Uiso 1 1 calc R . .
H16B H 0.5082 0.6648 0.7139 0.070 Uiso 1 1 calc R . .
H16C H 0.5309 0.5560 0.7828 0.070 Uiso 1 1 calc R . .
C15 C 0.46409(8) 0.7016(3) 0.81014(10) 0.0342(4) Uani 1 1 d . . .
H15 H 0.4495 0.8120 0.7932 0.041 Uiso 1 1 calc R . .
C8 C 0.47587(7) 0.7105(3) 0.89406(10) 0.0311(4) Uani 1 1 d . . .
H8A H 0.5035 0.7986 0.9040 0.037 Uiso 1 1 calc R . .
H8B H 0.4921 0.6036 0.9108 0.037 Uiso 1 1 calc R . .
C7 C 0.42490(7) 0.7465(3) 0.94017(10) 0.0288(4) Uani 1 1 d . . .
H7 H 0.4356 0.7274 0.9938 0.035 Uiso 1 1 calc R . .
C12 C 0.37731(7) 0.6245(3) 0.92114(10) 0.0294(4) Uani 1 1 d . . .
H12 H 0.3426 0.6726 0.9410 0.035 Uiso 1 1 calc R . .
C11 C 0.38629(8) 0.4532(3) 0.95799(10) 0.0336(4) Uani 1 1 d . . .
H11A H 0.3604 0.3725 0.9346 0.040 Uiso 1 1 calc R . .
H11B H 0.4242 0.4151 0.9480 0.040 Uiso 1 1 calc R . .
C10 C 0.37793(8) 0.4533(3) 1.04309(10) 0.0358(5) Uani 1 1 d . . .
H10A H 0.3930 0.3494 1.0650 0.043 Uiso 1 1 calc R . .
H10B H 0.3982 0.5480 1.0660 0.043 Uiso 1 1 calc R . .
C9 C 0.31709(8) 0.4674(3) 1.06037(10) 0.0342(5) Uani 1 1 d . . .
H9A H 0.3000 0.5451 1.0238 0.041 Uiso 1 1 calc R . .
H9B H 0.3000 0.3571 1.0519 0.041 Uiso 1 1 calc R . .
N1 N 0.30259(7) 0.5239(2) 1.13653(8) 0.0347(4) Uani 1 1 d . . .
C17 C 0.32289(10) 0.4080(3) 1.19406(11) 0.0453(6) Uani 1 1 d . . .
H17A H 0.3630 0.3993 1.1916 0.068 Uiso 1 1 calc R . .
H17B H 0.3064 0.2983 1.1855 0.068 Uiso 1 1 calc R . .
H17C H 0.3128 0.4488 1.2435 0.068 Uiso 1 1 calc R . .
C1 C 0.32019(8) 0.6959(3) 1.15265(10) 0.0359(5) Uani 1 1 d . . .
H1A H 0.3593 0.7086 1.1392 0.043 Uiso 1 1 calc R . .
H1B H 0.3175 0.7166 1.2070 0.043 Uiso 1 1 calc R . .
C14 C 0.42014(8) 0.5702(3) 0.79343(10) 0.0397(5) Uani 1 1 d . . .
H14A H 0.4105 0.5727 0.7394 0.048 Uiso 1 1 calc R . .
H14B H 0.4354 0.4590 0.8052 0.048 Uiso 1 1 calc R . .
C13 C 0.36870(8) 0.5968(3) 0.83765(10) 0.0343(5) Uani 1 1 d . . .
C6 C 0.40844(8) 0.9311(3) 0.93278(11) 0.0351(5) Uani 1 1 d . . .
H6A H 0.4402 1.0012 0.9481 0.042 Uiso 1 1 calc R . .
H6B H 0.3994 0.9557 0.8797 0.042 Uiso 1 1 calc R . .
C5 C 0.36003(8) 0.9758(3) 0.97934(10) 0.0329(4) Uani 1 1 d . . .
C4 C 0.36638(8) 0.9898(3) 1.06272(11) 0.0334(4) Uani 1 1 d . . .
C3 C 0.31489(9) 0.9933(3) 1.10888(10) 0.0367(5) Uani 1 1 d . . .
H3A H 0.2891 1.0774 1.0878 0.044 Uiso 1 1 calc R . .
H3B H 0.3248 1.0271 1.1606 0.044 Uiso 1 1 calc R . .
C2 C 0.28607(8) 0.8250(3) 1.11059(10) 0.0355(5) Uani 1 1 d . . .
H2A H 0.2501 0.8374 1.1348 0.043 Uiso 1 1 calc R . .
H2B H 0.2791 0.7863 1.0587 0.043 Uiso 1 1 calc R . .
C17' C 0.31718(9) -0.0051(3) 0.70176(10) 0.0432(5) Uani 1 1 d . . .
H17D H 0.3574 -0.0152 0.7009 0.065 Uiso 1 1 calc R . .
H17E H 0.3005 -0.1149 0.6945 0.065 Uiso 1 1 calc R . .
H17F H 0.3063 0.0402 0.7501 0.065 Uiso 1 1 calc R . .
N1' N 0.29828(6) 0.1072(2) 0.64134(8) 0.0348(4) Uani 1 1 d . . .
C9' C 0.31190(8) 0.0390(3) 0.56721(9) 0.0323(4) Uani 1 1 d . . .
H9'1 H 0.2964 0.1147 0.5285 0.039 Uiso 1 1 calc R . .
H9'2 H 0.2929 -0.0692 0.5613 0.039 Uiso 1 1 calc R . .
C10' C 0.37283(8) 0.0125(3) 0.55110(10) 0.0327(4) Uani 1 1 d . . .
H10C H 0.3860 -0.0896 0.5766 0.039 Uiso 1 1 calc R . .
H10D H 0.3945 0.1074 0.5711 0.039 Uiso 1 1 calc R . .
C11' C 0.38189(8) -0.0033(3) 0.46646(10) 0.0297(4) Uani 1 1 d . . .
H11C H 0.3550 -0.0839 0.4453 0.036 Uiso 1 1 calc R . .
H11D H 0.4193 -0.0481 0.4585 0.036 Uiso 1 1 calc R . .
C12' C 0.37576(7) 0.1628(2) 0.42392(10) 0.0267(4) Uani 1 1 d . . .
H12' H 0.3418 0.2194 0.4418 0.032 Uiso 1 1 calc R . .
C13' C 0.36690(7) 0.1216(3) 0.34160(10) 0.0288(4) Uani 1 1 d . . .
C14' C 0.41772(8) 0.0773(3) 0.29933(10) 0.0349(5) Uani 1 1 d . . .
H14C H 0.4082 0.0710 0.2453 0.042 Uiso 1 1 calc R . .
H14D H 0.4307 -0.0339 0.3155 0.042 Uiso 1 1 calc R . .
C15' C 0.46428(7) 0.2027(3) 0.31125(10) 0.0313(4) Uani 1 1 d . . .
H15' H 0.4522 0.3115 0.2895 0.038 Uiso 1 1 calc R . .
C16' C 0.51603(9) 0.1477(3) 0.27181(12) 0.0433(5) Uani 1 1 d . . .
H16D H 0.5453 0.2299 0.2805 0.065 Uiso 1 1 calc R . .
H16E H 0.5082 0.1382 0.2180 0.065 Uiso 1 1 calc R . .
H16F H 0.5280 0.0396 0.2915 0.065 Uiso 1 1 calc R . .
C1' C 0.31889(8) 0.2761(3) 0.65338(10) 0.0347(5) Uani 1 1 d . . .
H1'1 H 0.3586 0.2792 0.6419 0.042 Uiso 1 1 calc R . .
H1'2 H 0.3152 0.3053 0.7068 0.042 Uiso 1 1 calc R . .
C7' C 0.42518(7) 0.2808(2) 0.43837(9) 0.0264(4) Uani 1 1 d . . .
H7' H 0.4353 0.2723 0.4927 0.032 Uiso 1 1 calc R . .
C6' C 0.41096(8) 0.4644(3) 0.42250(10) 0.0312(4) Uani 1 1 d . . .
H6'1 H 0.4441 0.5330 0.4325 0.037 Uiso 1 1 calc R . .
H6'2 H 0.4008 0.4766 0.3689 0.037 Uiso 1 1 calc R . .
C5' C 0.36465(8) 0.5295(3) 0.46860(10) 0.0301(4) Uani 1 1 d . . .
C4' C 0.37191(8) 0.5453(2) 0.55202(11) 0.0323(4) Uani 1 1 d . . .
C3' C 0.32143(8) 0.5669(3) 0.59853(10) 0.0352(5) Uani 1 1 d . . .
H3'1 H 0.2975 0.6534 0.5755 0.042 Uiso 1 1 calc R . .
H3'2 H 0.3328 0.6058 0.6491 0.042 Uiso 1 1 calc R . .
C2' C 0.28862(8) 0.4061(3) 0.60556(10) 0.0351(5) Uani 1 1 d . . .
H2'1 H 0.2813 0.3598 0.5551 0.042 Uiso 1 1 calc R . .
H2'2 H 0.2527 0.4311 0.6281 0.042 Uiso 1 1 calc R . .
C8' C 0.47564(7) 0.2273(3) 0.39478(10) 0.0292(4) Uani 1 1 d . . .
H8'1 H 0.5047 0.3125 0.4015 0.035 Uiso 1 1 calc R . .
H8'2 H 0.4899 0.1220 0.4162 0.035 Uiso 1 1 calc R . .
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'
O O 0.0492 0.0322 '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
N5 O5 H5 109.5 . . ?
N5' O5' H5' 109.5 . . ?
C5 N5 O5 113.03(16) . . ?
C5' N5' O5' 113.70(15) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 C15 C16 110.97(16) . . ?
C8 C15 C14 109.92(16) . . ?
C16 C15 C14 110.90(18) . . ?
C8 C15 H15 108.3 . . ?
C16 C15 H15 108.3 . . ?
C14 C15 H15 108.3 . . ?
C15 C8 C7 113.79(15) . . ?
C15 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
C15 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C8 C7 C6 110.30(16) . . ?
C8 C7 C12 111.75(15) . . ?
C6 C7 C12 113.61(15) . . ?
C8 C7 H7 106.9 . . ?
C6 C7 H7 106.9 . . ?
C12 C7 H7 106.9 . . ?
C13 C12 C11 107.74(17) . . ?
C13 C12 C7 113.24(15) . . ?
C11 C12 C7 112.01(15) . . ?
C13 C12 H12 107.9 . . ?
C11 C12 H12 107.9 . . ?
C7 C12 H12 107.9 . . ?
C10 C11 C12 113.68(17) . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C9 C10 C11 110.55(15) . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N1 C9 C10 117.40(16) . . ?
N1 C9 H9A 108.0 . . ?
C10 C9 H9A 108.0 . . ?
N1 C9 H9B 108.0 . . ?
C10 C9 H9B 108.0 . . ?
H9A C9 H9B 107.2 . . ?
C17 N1 C1 111.60(16) . . ?
C17 N1 C9 111.46(17) . . ?
C1 N1 C9 113.14(15) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C1 C2 113.09(16) . . ?
N1 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C13 C14 C15 112.48(18) . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
O13 C13 C14 122.31(17) . . ?
O13 C13 C12 121.63(18) . . ?
C14 C13 C12 116.00(16) . . ?
C5 C6 C7 112.84(17) . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
N5 C5 C6 126.17(17) . . ?
N5 C5 C4 113.46(17) . . ?
C6 C5 C4 120.37(17) . . ?
O4 C4 C5 119.47(18) . . ?
O4 C4 C3 122.09(17) . . ?
C5 C4 C3 118.40(16) . . ?
C4 C3 C2 112.30(17) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C1 C2 C3 111.82(16) . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
N1' C17' H17D 109.5 . . ?
N1' C17' H17E 109.5 . . ?
H17D C17' H17E 109.5 . . ?
N1' C17' H17F 109.5 . . ?
H17D C17' H17F 109.5 . . ?
H17E C17' H17F 109.5 . . ?
C1' N1' C17' 111.19(16) . . ?
C1' N1' C9' 113.22(15) . . ?
C17' N1' C9' 110.96(17) . . ?
N1' C9' C10' 117.19(15) . . ?
N1' C9' H9'1 108.0 . . ?
C10' C9' H9'1 108.0 . . ?
N1' C9' H9'2 108.0 . . ?
C10' C9' H9'2 108.0 . . ?
H9'1 C9' H9'2 107.2 . . ?
C9' C10' C11' 110.90(15) . . ?
C9' C10' H10C 109.5 . . ?
C11' C10' H10C 109.5 . . ?
C9' C10' H10D 109.5 . . ?
C11' C10' H10D 109.5 . . ?
H10C C10' H10D 108.0 . . ?
C10' C11' C12' 113.53(16) . . ?
C10' C11' H11C 108.9 . . ?
C12' C11' H11C 108.9 . . ?
C10' C11' H11D 108.9 . . ?
C12' C11' H11D 108.9 . . ?
H11C C11' H11D 107.7 . . ?
C13' C12' C11' 107.41(15) . . ?
C13' C12' C7' 112.84(14) . . ?
C11' C12' C7' 112.51(14) . . ?
C13' C12' H12' 108.0 . . ?
C11' C12' H12' 108.0 . . ?
C7' C12' H12' 108.0 . . ?
O13' C13' C14' 122.37(17) . . ?
O13' C13' C12' 121.59(17) . . ?
C14' C13' C12' 116.00(15) . . ?
C13' C14' C15' 112.73(17) . . ?
C13' C14' H14C 109.0 . . ?
C15' C14' H14C 109.0 . . ?
C13' C14' H14D 109.0 . . ?
C15' C14' H14D 109.0 . . ?
H14C C14' H14D 107.8 . . ?
C16' C15' C8' 111.01(16) . . ?
C16' C15' C14' 111.11(18) . . ?
C8' C15' C14' 109.87(15) . . ?
C16' C15' H15' 108.3 . . ?
C8' C15' H15' 108.3 . . ?
C14' C15' H15' 108.3 . . ?
C15' C16' H16D 109.5 . . ?
C15' C16' H16E 109.5 . . ?
H16D C16' H16E 109.5 . . ?
C15' C16' H16F 109.5 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 109.5 . . ?
N1' C1' C2' 113.23(16) . . ?
N1' C1' H1'1 108.9 . . ?
C2' C1' H1'1 108.9 . . ?
N1' C1' H1'2 108.9 . . ?
C2' C1' H1'2 108.9 . . ?
H1'1 C1' H1'2 107.7 . . ?
C8' C7' C6' 110.75(15) . . ?
C8' C7' C12' 111.70(15) . . ?
C6' C7' C12' 112.79(14) . . ?
C8' C7' H7' 107.1 . . ?
C6' C7' H7' 107.1 . . ?
C12' C7' H7' 107.1 . . ?
C5' C6' C7' 113.56(16) . . ?
C5' C6' H6'1 108.9 . . ?
C7' C6' H6'1 108.9 . . ?
C5' C6' H6'2 108.9 . . ?
C7' C6' H6'2 108.9 . . ?
H6'1 C6' H6'2 107.7 . . ?
N5' C5' C6' 127.00(17) . . ?
N5' C5' C4' 112.93(16) . . ?
C6' C5' C4' 120.07(16) . . ?
O4' C4' C5' 119.12(17) . . ?
O4' C4' C3' 122.25(17) . . ?
C5' C4' C3' 118.60(16) . . ?
C4' C3' C2' 112.34(16) . . ?
C4' C3' H3'1 109.1 . . ?
C2' C3' H3'1 109.1 . . ?
C4' C3' H3'2 109.1 . . ?
C2' C3' H3'2 109.1 . . ?
H3'1 C3' H3'2 107.9 . . ?
C3' C2' C1' 112.37(16) . . ?
C3' C2' H2'1 109.1 . . ?
C1' C2' H2'1 109.1 . . ?
C3' C2' H2'2 109.1 . . ?
C1' C2' H2'2 109.1 . . ?
H2'1 C2' H2'2 107.9 . . ?
C15' C8' C7' 113.97(14) . . ?
C15' C8' H8'1 108.8 . . ?
C7' C8' H8'1 108.8 . . ?
C15' C8' H8'2 108.8 . . ?
C7' C8' H8'2 108.8 . . ?
H8'1 C8' H8'2 107.7 . . ?
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
O13 C13 1.207(2) . ?
O5 N5 1.3756(19) . ?
O5 H5 0.8400 . ?
O4 C4 1.214(2) . ?
O5' N5' 1.3774(19) . ?
O5' H5' 0.8400 . ?
O4' C4' 1.219(2) . ?
O13' C13' 1.207(2) . ?
N5 C5 1.288(3) . ?
N5' C5' 1.286(2) . ?
C16 C15 1.525(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C15 C8 1.524(3) . ?
C15 C14 1.527(3) . ?
C15 H15 1.0000 . ?
C8 C7 1.530(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C7 C6 1.543(3) . ?
C7 C12 1.549(3) . ?
C7 H7 1.0000 . ?
C12 C13 1.520(2) . ?
C12 C11 1.541(3) . ?
C12 H12 1.0000 . ?
C11 C10 1.541(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C10 C9 1.521(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C9 N1 1.487(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N1 C17 1.467(3) . ?
N1 C1 1.475(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C1 C2 1.518(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C14 C13 1.509(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C6 C5 1.500(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C5 C4 1.501(3) . ?
C4 C3 1.514(3) . ?
C3 C2 1.525(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C17' N1' 1.475(3) . ?
C17' H17D 0.9800 . ?
C17' H17E 0.9800 . ?
C17' H17F 0.9800 . ?
N1' C1' 1.463(3) . ?
N1' C9' 1.480(2) . ?
C9' C10' 1.529(3) . ?
C9' H9'1 0.9900 . ?
C9' H9'2 0.9900 . ?
C10' C11' 1.541(2) . ?
C10' H10C 0.9900 . ?
C10' H10D 0.9900 . ?
C11' C12' 1.543(3) . ?
C11' H11C 0.9900 . ?
C11' H11D 0.9900 . ?
C12' C13' 1.521(2) . ?
C12' C7' 1.548(3) . ?
C12' H12' 1.0000 . ?
C13' C14' 1.505(3) . ?
C14' C15' 1.527(3) . ?
C14' H14C 0.9900 . ?
C14' H14D 0.9900 . ?
C15' C16' 1.521(3) . ?
C15' C8' 1.527(2) . ?
C15' H15' 1.0000 . ?
C16' H16D 0.9800 . ?
C16' H16E 0.9800 . ?
C16' H16F 0.9800 . ?
C1' C2' 1.530(3) . ?
C1' H1'1 0.9900 . ?
C1' H1'2 0.9900 . ?
C7' C8' 1.529(2) . ?
C7' C6' 1.542(3) . ?
C7' H7' 1.0000 . ?
C6' C5' 1.504(3) . ?
C6' H6'1 0.9900 . ?
C6' H6'2 0.9900 . ?
C5' C4' 1.505(2) . ?
C4' C3' 1.507(3) . ?
C3' C2' 1.527(3) . ?
C3' H3'1 0.9900 . ?
C3' H3'2 0.9900 . ?
C2' H2'1 0.9900 . ?
C2' H2'2 0.9900 . ?
C8' H8'1 0.9900 . ?
C8' H8'2 0.9900 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5 N1 0.84 1.82 2.643(2) 165.5 4_557
O5' H5' N1' 0.84 1.83 2.652(2) 164.5 4_556
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
C16 C15 C8 C7 -179.82(19) . . . . ?
C14 C15 C8 C7 -56.8(2) . . . . ?
C15 C8 C7 C6 -75.0(2) . . . . ?
C15 C8 C7 C12 52.4(2) . . . . ?
C8 C7 C12 C13 -44.6(2) . . . . ?
C6 C7 C12 C13 81.0(2) . . . . ?
C8 C7 C12 C11 77.54(19) . . . . ?
C6 C7 C12 C11 -156.87(16) . . . . ?
C13 C12 C11 C10 -162.24(16) . . . . ?
C7 C12 C11 C10 72.6(2) . . . . ?
C12 C11 C10 C9 73.1(2) . . . . ?
C11 C10 C9 N1 -160.56(18) . . . . ?
C10 C9 N1 C17 -62.1(2) . . . . ?
C10 C9 N1 C1 64.6(2) . . . . ?
C17 N1 C1 C2 -161.34(17) . . . . ?
C9 N1 C1 C2 72.0(2) . . . . ?
C8 C15 C14 C13 53.7(2) . . . . ?
C16 C15 C14 C13 176.81(18) . . . . ?
C15 C14 C13 O13 133.5(2) . . . . ?
C15 C14 C13 C12 -49.3(3) . . . . ?
C11 C12 C13 O13 97.2(2) . . . . ?
C7 C12 C13 O13 -138.4(2) . . . . ?
C11 C12 C13 C14 -80.1(2) . . . . ?
C7 C12 C13 C14 44.3(3) . . . . ?
C8 C7 C6 C5 -177.61(15) . . . . ?
C12 C7 C6 C5 56.0(2) . . . . ?
O5 N5 C5 C6 0.1(3) . . . . ?
O5 N5 C5 C4 179.89(17) . . . . ?
C7 C6 C5 N5 -107.1(2) . . . . ?
C7 C6 C5 C4 73.2(2) . . . . ?
N5 C5 C4 O4 -167.1(2) . . . . ?
C6 C5 C4 O4 12.7(3) . . . . ?
N5 C5 C4 C3 14.9(3) . . . . ?
C6 C5 C4 C3 -165.30(19) . . . . ?
O4 C4 C3 C2 -106.9(2) . . . . ?
C5 C4 C3 C2 71.1(2) . . . . ?
N1 C1 C2 C3 -162.54(16) . . . . ?
C4 C3 C2 C1 67.3(2) . . . . ?
C1' N1' C9' C10' 64.4(2) . . . . ?
C17' N1' C9' C10' -61.4(2) . . . . ?
N1' C9' C10' C11' -161.61(18) . . . . ?
C9' C10' C11' C12' 72.8(2) . . . . ?
C10' C11' C12' C13' -161.72(15) . . . . ?
C10' C11' C12' C7' 73.51(19) . . . . ?
C11' C12' C13' O13' 98.4(2) . . . . ?
C7' C12' C13' O13' -137.04(19) . . . . ?
C11' C12' C13' C14' -79.3(2) . . . . ?
C7' C12' C13' C14' 45.3(2) . . . . ?
O13' C13' C14' C15' 132.8(2) . . . . ?
C12' C13' C14' C15' -49.6(2) . . . . ?
C13' C14' C15' C16' 176.28(17) . . . . ?
C13' C14' C15' C8' 53.0(2) . . . . ?
C17' N1' C1' C2' -164.30(16) . . . . ?
C9' N1' C1' C2' 70.0(2) . . . . ?
C13' C12' C7' C8' -45.4(2) . . . . ?
C11' C12' C7' C8' 76.31(18) . . . . ?
C13' C12' C7' C6' 80.08(19) . . . . ?
C11' C12' C7' C6' -158.19(14) . . . . ?
C8' C7' C6' C5' -175.08(15) . . . . ?
C12' C7' C6' C5' 58.9(2) . . . . ?
O5' N5' C5' C6' -1.8(3) . . . . ?
O5' N5' C5' C4' 178.14(16) . . . . ?
C7' C6' C5' N5' -114.1(2) . . . . ?
C7' C6' C5' C4' 66.0(2) . . . . ?
N5' C5' C4' O4' -165.94(19) . . . . ?
C6' C5' C4' O4' 14.0(3) . . . . ?
N5' C5' C4' C3' 15.9(3) . . . . ?
C6' C5' C4' C3' -164.15(18) . . . . ?
O4' C4' C3' C2' -103.9(2) . . . . ?
C5' C4' C3' C2' 74.1(2) . . . . ?
C4' C3' C2' C1' 69.3(2) . . . . ?
N1' C1' C2' C3' -160.92(15) . . . . ?
C16' C15' C8' C7' -179.30(19) . . . . ?
C14' C15' C8' C7' -56.0(2) . . . . ?
C6' C7' C8' C15' -74.1(2) . . . . ?
C12' C7' C8' C15' 52.6(2) . . . . ?
