#------------------------------------------------------------------------------
#$Date: 2022-10-05 04:19:18 +0300 (Wed, 05 Oct 2022) $
#$Revision: 278351 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/56/7245606.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_7245606
loop_
_publ_author_name
'Zhang, Jia-Hui'
'Cao, Mingming'
'Zhang, Yu'
'Li, Xiao-Hui'
'Gu, Yu-Cheng'
'Li, Xiao-Nian'
'Di, Ying-Tong'
'Hao, Xiao-Jiang'
_publ_section_title
;
 Scalemic myrionsumamide A, tetracyclic skeleton alkaloids from
 Myrioneuron effusum
;
_journal_issue                   43
_journal_name_full               'RSC Advances'
_journal_page_first              28147
_journal_page_last               28151
_journal_paper_doi               10.1039/D2RA05342J
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C15 H24 N2 O2'
_chemical_formula_sum            'C15 H24 N2 O2'
_chemical_formula_weight         264.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-07-14 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                92.7820(10)
_cell_angle_beta                 96.8930(10)
_cell_angle_gamma                108.4380(10)
_cell_formula_units_Z            4
_cell_length_a                   10.0436(5)
_cell_length_b                   11.4268(6)
_cell_length_c                   12.7535(6)
_cell_measurement_reflns_used    9805
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.22
_cell_measurement_theta_min      4.10
_cell_volume                     1372.67(12)
_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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.908
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.908
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17390
_diffrn_reflns_point_group_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.303
_diffrn_reflns_theta_min         3.505
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          1.650
_exptl_crystal_size_mid          1.170
_exptl_crystal_size_min          0.480
_exptl_transmission_factor_max   0.7533
_exptl_transmission_factor_min   0.2720
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       0.021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0744
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1396P)²+1.2148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2159
_refine_ls_wR_factor_ref         0.2165
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4598
_reflns_number_total             4629
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra05342j2.cif
_cod_data_source_block           cu_hmen50_0m
_cod_database_code               7245606
_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   0.402
_shelx_estimated_absorpt_t_max   0.737
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
O16 O 0.89642(16) 0.62120(14) -0.06014(11) 0.0160(4) Uani 1 1 d . . . . .
H16 H 0.9346 0.5690 -0.0778 0.024 Uiso 1 1 calc R U . . .
O17 O 0.97074(17) 0.52973(14) 0.14976(12) 0.0179(4) Uani 1 1 d . . . . .
O17' O -0.04869(16) 0.85652(15) 0.45151(11) 0.0181(4) Uani 1 1 d . . . . .
O16' O -0.00727(18) 0.95404(15) 0.68084(12) 0.0209(4) Uani 1 1 d . . . . .
H16' H -0.0031 1.0018 0.6324 0.031 Uiso 1 1 calc R U . . .
N1 N 0.81379(19) 0.62942(17) 0.17544(13) 0.0148(4) Uani 1 1 d . . . . .
N12 N 1.0418(2) 0.88808(18) 0.13907(15) 0.0188(5) Uani 1 1 d . . . . .
H12 H 1.0106 0.9112 0.1955 0.023 Uiso 1 1 calc R U . . .
N12' N -0.07243(19) 0.62036(17) 0.68306(14) 0.0163(4) Uani 1 1 d . . . . .
H12' H -0.0254 0.5696 0.6692 0.020 Uiso 1 1 calc R U . . .
N1' N 0.13080(19) 0.79756(18) 0.53053(14) 0.0164(4) Uani 1 1 d . . . . .
C14 C 1.2281(2) 0.8009(2) 0.12517(19) 0.0228(5) Uani 1 1 d . . . . .
H14A H 1.2154 0.7619 0.1925 0.027 Uiso 1 1 calc R U . . .
H14B H 1.3284 0.8191 0.1144 0.027 Uiso 1 1 calc R U . . .
C15 C 1.1321(2) 0.7129(2) 0.03395(17) 0.0181(5) Uani 1 1 d . . . . .
H15A H 1.1491 0.6322 0.0357 0.022 Uiso 1 1 calc R U . . .
H15B H 1.1575 0.7465 -0.0337 0.022 Uiso 1 1 calc R U . . .
C16 C 0.9736(2) 0.6913(2) 0.03630(15) 0.0141(5) Uani 1 1 d . . . . .
C17 C 0.9205(2) 0.61261(19) 0.12726(15) 0.0139(5) Uani 1 1 d . . . . .
C10 C 0.7706(2) 0.7418(2) 0.17057(16) 0.0148(5) Uani 1 1 d . . . . .
H10 H 0.8329 0.8038 0.2287 0.018 Uiso 1 1 calc R U . . .
C5 C 0.6166(2) 0.7172(2) 0.19138(17) 0.0185(5) Uani 1 1 d . . . . .
H5 H 0.6038 0.7999 0.2029 0.022 Uiso 1 1 calc R U . . .
C6 C 0.5082(2) 0.6473(2) 0.09645(19) 0.0224(5) Uani 1 1 d . . . . .
H6A H 0.5165 0.5641 0.0824 0.027 Uiso 1 1 calc R U . . .
H6B H 0.4113 0.6364 0.1127 0.027 Uiso 1 1 calc R U . . .
C13 C 1.1923(3) 0.9199(2) 0.13120(19) 0.0232(5) Uani 1 1 d . . . . .
H13A H 1.2492 0.9752 0.1940 0.028 Uiso 1 1 calc R U . . .
H13B H 1.2138 0.9635 0.0670 0.028 Uiso 1 1 calc R U . . .
C11 C 0.9463(2) 0.8152(2) 0.04669(16) 0.0160(5) Uani 1 1 d . . . . .
H11 H 0.9668 0.8592 -0.0184 0.019 Uiso 1 1 calc R U . . .
C2 C 0.7825(2) 0.5621(2) 0.27005(17) 0.0184(5) Uani 1 1 d . . . . .
H2A H 0.8464 0.6117 0.3330 0.022 Uiso 1 1 calc R U . . .
H2B H 0.8020 0.4828 0.2614 0.022 Uiso 1 1 calc R U . . .
C3 C 0.6297(2) 0.5356(2) 0.28898(17) 0.0194(5) Uani 1 1 d . . . . .
H3A H 0.6161 0.4970 0.3564 0.023 Uiso 1 1 calc R U . . .
H3B H 0.5656 0.4766 0.2309 0.023 Uiso 1 1 calc R U . . .
C4 C 0.5924(2) 0.6546(2) 0.29393(18) 0.0198(5) Uani 1 1 d . . . . .
H4A H 0.6520 0.7115 0.3550 0.024 Uiso 1 1 calc R U . . .
H4B H 0.4918 0.6356 0.3042 0.024 Uiso 1 1 calc R U . . .
C9 C 0.7951(2) 0.8003(2) 0.06589(16) 0.0170(5) Uani 1 1 d . . . . .
H9 H 0.7894 0.8858 0.0766 0.020 Uiso 1 1 calc R U . . .
C8 C 0.6802(3) 0.7324(2) -0.02774(17) 0.0205(5) Uani 1 1 d . . . . .
H8A H 0.6962 0.7796 -0.0907 0.025 Uiso 1 1 calc R U . . .
H8B H 0.6877 0.6496 -0.0453 0.025 Uiso 1 1 calc R U . . .
C7 C 0.5322(3) 0.7179(2) -0.00160(19) 0.0249(6) Uani 1 1 d . . . . .
H7A H 0.4604 0.6722 -0.0623 0.030 Uiso 1 1 calc R U . . .
H7B H 0.5221 0.8005 0.0117 0.030 Uiso 1 1 calc R U . . .
C4' C 0.3943(3) 0.7482(3) 0.51219(19) 0.0270(6) Uani 1 1 d . . . . .
H4'1 H 0.4987 0.7764 0.5152 0.032 Uiso 1 1 calc R U . . .
H4'2 H 0.3579 0.6579 0.4916 0.032 Uiso 1 1 calc R U . . .
C5' C 0.3560(2) 0.7749(2) 0.62164(18) 0.0214(5) Uani 1 1 d . . . . .
H5' H 0.3851 0.7172 0.6687 0.026 Uiso 1 1 calc R U . . .
C10' C 0.1948(2) 0.7423(2) 0.61799(16) 0.0156(5) Uani 1 1 d . . . . .
H10' H 0.1529 0.6503 0.6032 0.019 Uiso 1 1 calc R U . . .
C9' C 0.1569(2) 0.7764(2) 0.72563(16) 0.0154(5) Uani 1 1 d . . . . .
H9' H 0.1784 0.7169 0.7745 0.019 Uiso 1 1 calc R U . . .
C11' C -0.0029(2) 0.7516(2) 0.71643(16) 0.0157(5) Uani 1 1 d . . . . .
H11' H -0.0278 0.7713 0.7873 0.019 Uiso 1 1 calc R U . . .
C13' C -0.2264(2) 0.5804(2) 0.67454(18) 0.0211(5) Uani 1 1 d . . . . .
H13C H -0.2551 0.6026 0.7423 0.025 Uiso 1 1 calc R U . . .
H13D H -0.2662 0.4894 0.6583 0.025 Uiso 1 1 calc R U . . .
C14' C -0.2814(2) 0.6449(2) 0.58594(18) 0.0236(6) Uani 1 1 d . . . . .
H14C H -0.2559 0.6198 0.5177 0.028 Uiso 1 1 calc R U . . .
H14D H -0.3860 0.6209 0.5792 0.028 Uiso 1 1 calc R U . . .
C2' C 0.1699(3) 0.7739(3) 0.42571(17) 0.0234(6) Uani 1 1 d . . . . .
H2'1 H 0.1293 0.8192 0.3734 0.028 Uiso 1 1 calc R U . . .
H2'2 H 0.1293 0.6843 0.4024 0.028 Uiso 1 1 calc R U . . .
C3' C 0.3300(3) 0.8151(3) 0.42954(19) 0.0288(6) Uani 1 1 d . . . . .
H3'1 H 0.3703 0.9058 0.4480 0.035 Uiso 1 1 calc R U . . .
H3'2 H 0.3539 0.7962 0.3589 0.035 Uiso 1 1 calc R U . . .
C6' C 0.4392(3) 0.9058(2) 0.6717(2) 0.0256(6) Uani 1 1 d . . . . .
H6'1 H 0.5420 0.9198 0.6748 0.031 Uiso 1 1 calc R U . . .
H6'2 H 0.4148 0.9669 0.6274 0.031 Uiso 1 1 calc R U . . .
C7' C 0.4050(3) 0.9242(2) 0.78294(19) 0.0253(6) Uani 1 1 d . . . . .
H7'1 H 0.4611 1.0086 0.8153 0.030 Uiso 1 1 calc R U . . .
H7'2 H 0.4294 0.8636 0.8278 0.030 Uiso 1 1 calc R U . . .
C8' C 0.2473(3) 0.9063(2) 0.77590(17) 0.0203(5) Uani 1 1 d . . . . .
H8'1 H 0.2246 0.9691 0.7329 0.024 Uiso 1 1 calc R U . . .
H8'2 H 0.2239 0.9187 0.8479 0.024 Uiso 1 1 calc R U . . .
C17' C 0.0109(2) 0.8263(2) 0.53143(16) 0.0152(5) Uani 1 1 d . . . . .
C16' C -0.0535(2) 0.8289(2) 0.63514(16) 0.0158(5) Uani 1 1 d . . . . .
C15' C -0.2159(3) 0.7843(2) 0.61165(18) 0.0221(5) Uani 1 1 d . . . . .
H15C H -0.2539 0.8094 0.6740 0.027 Uiso 1 1 calc R U . . .
H15D H -0.2450 0.8260 0.5510 0.027 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 0.0181 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
C16 O16 H16 109.5 . . ?
C16' O16' H16' 109.5 . . ?
C17 N1 C2 116.07(18) . . ?
C17 N1 C10 123.92(18) . . ?
C2 N1 C10 114.95(16) . . ?
C13 N12 C11 115.26(17) . . ?
C13 N12 H12 122.4 . . ?
C11 N12 H12 122.4 . . ?
C13' N12' C11' 114.23(18) . . ?
C13' N12' H12' 122.9 . . ?
C11' N12' H12' 122.9 . . ?
C17' N1' C2' 116.73(18) . . ?
C17' N1' C10' 124.50(17) . . ?
C2' N1' C10' 114.58(18) . . ?
C13 C14 C15 109.6(2) . . ?
C13 C14 H14A 109.7 . . ?
C15 C14 H14A 109.7 . . ?
C13 C14 H14B 109.7 . . ?
C15 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C14 C15 C16 113.68(17) . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
O16 C16 C11 110.01(17) . . ?
O16 C16 C15 108.19(16) . . ?
C11 C16 C15 110.17(18) . . ?
O16 C16 C17 106.53(16) . . ?
C11 C16 C17 110.86(16) . . ?
C15 C16 C17 110.98(17) . . ?
O17 C17 N1 121.37(19) . . ?
O17 C17 C16 118.58(18) . . ?
N1 C17 C16 119.88(19) . . ?
N1 C10 C9 111.79(16) . . ?
N1 C10 C5 112.33(17) . . ?
C9 C10 C5 111.27(18) . . ?
N1 C10 H10 107.0 . . ?
C9 C10 H10 107.0 . . ?
C5 C10 H10 107.0 . . ?
C6 C5 C4 113.0(2) . . ?
C6 C5 C10 112.60(18) . . ?
C4 C5 C10 110.65(18) . . ?
C6 C5 H5 106.7 . . ?
C4 C5 H5 106.7 . . ?
C10 C5 H5 106.7 . . ?
C7 C6 C5 110.6(2) . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
N12 C13 C14 107.95(19) . . ?
N12 C13 H13A 110.1 . . ?
C14 C13 H13A 110.1 . . ?
N12 C13 H13B 110.1 . . ?
C14 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
N12 C11 C9 107.57(16) . . ?
N12 C11 C16 107.01(18) . . ?
C9 C11 C16 112.44(18) . . ?
N12 C11 H11 109.9 . . ?
C9 C11 H11 109.9 . . ?
C16 C11 H11 109.9 . . ?
N1 C2 C3 112.61(18) . . ?
N1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 110.53(18) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C3 C4 C5 110.19(17) . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C11 C9 C10 108.70(18) . . ?
C11 C9 C8 114.46(17) . . ?
C10 C9 C8 113.34(18) . . ?
C11 C9 H9 106.6 . . ?
C10 C9 H9 106.6 . . ?
C8 C9 H9 106.6 . . ?
C7 C8 C9 111.42(18) . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C8 C7 C6 109.47(19) . . ?
C8 C7 H7A 109.8 . . ?
C6 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
C3' C4' C5' 110.2(2) . . ?
C3' C4' H4'1 109.6 . . ?
C5' C4' H4'1 109.6 . . ?
C3' C4' H4'2 109.6 . . ?
C5' C4' H4'2 109.6 . . ?
H4'1 C4' H4'2 108.1 . . ?
C6' C5' C4' 112.8(2) . . ?
C6' C5' C10' 113.39(19) . . ?
C4' C5' C10' 111.14(18) . . ?
C6' C5' H5' 106.3 . . ?
C4' C5' H5' 106.3 . . ?
C10' C5' H5' 106.3 . . ?
N1' C10' C9' 111.95(18) . . ?
N1' C10' C5' 112.28(17) . . ?
C9' C10' C5' 111.24(17) . . ?
N1' C10' H10' 107.0 . . ?
C9' C10' H10' 107.0 . . ?
C5' C10' H10' 107.0 . . ?
C11' C9' C10' 109.57(17) . . ?
C11' C9' C8' 114.33(18) . . ?
C10' C9' C8' 113.75(18) . . ?
C11' C9' H9' 106.2 . . ?
C10' C9' H9' 106.2 . . ?
C8' C9' H9' 106.2 . . ?
N12' C11' C9' 107.38(17) . . ?
N12' C11' C16' 109.45(17) . . ?
C9' C11' C16' 111.86(17) . . ?
N12' C11' H11' 109.4 . . ?
C9' C11' H11' 109.4 . . ?
C16' C11' H11' 109.4 . . ?
N12' C13' C14' 107.98(17) . . ?
N12' C13' H13C 110.1 . . ?
C14' C13' H13C 110.1 . . ?
N12' C13' H13D 110.1 . . ?
C14' C13' H13D 110.1 . . ?
H13C C13' H13D 108.4 . . ?
C15' C14' C13' 108.95(19) . . ?
C15' C14' H14C 109.9 . . ?
C13' C14' H14C 109.9 . . ?
C15' C14' H14D 109.9 . . ?
C13' C14' H14D 109.9 . . ?
H14C C14' H14D 108.3 . . ?
N1' C2' C3' 111.04(19) . . ?
N1' C2' H2'1 109.4 . . ?
C3' C2' H2'1 109.4 . . ?
N1' C2' H2'2 109.4 . . ?
C3' C2' H2'2 109.4 . . ?
H2'1 C2' H2'2 108.0 . . ?
C2' C3' C4' 109.9(2) . . ?
C2' C3' H3'1 109.7 . . ?
C4' C3' H3'1 109.7 . . ?
C2' C3' H3'2 109.7 . . ?
C4' C3' H3'2 109.7 . . ?
H3'1 C3' H3'2 108.2 . . ?
C7' C6' C5' 110.6(2) . . ?
C7' C6' H6'1 109.5 . . ?
C5' C6' H6'1 109.5 . . ?
C7' C6' H6'2 109.5 . . ?
C5' C6' H6'2 109.5 . . ?
H6'1 C6' H6'2 108.1 . . ?
C6' C7' C8' 108.58(19) . . ?
C6' C7' H7'1 110.0 . . ?
C8' C7' H7'1 110.0 . . ?
C6' C7' H7'2 110.0 . . ?
C8' C7' H7'2 110.0 . . ?
H7'1 C7' H7'2 108.4 . . ?
C7' C8' C9' 111.46(19) . . ?
C7' C8' H8'1 109.3 . . ?
C9' C8' H8'1 109.3 . . ?
C7' C8' H8'2 109.3 . . ?
C9' C8' H8'2 109.3 . . ?
H8'1 C8' H8'2 108.0 . . ?
O17' C17' N1' 122.08(19) . . ?
O17' C17' C16' 117.4(2) . . ?
N1' C17' C16' 120.47(19) . . ?
O16' C16' C15' 108.21(18) . . ?
O16' C16' C11' 107.62(17) . . ?
C15' C16' C11' 110.58(18) . . ?
O16' C16' C17' 108.01(17) . . ?
C15' C16' C17' 110.35(17) . . ?
C11' C16' C17' 111.93(18) . . ?
C14' C15' C16' 113.71(19) . . ?
C14' C15' H15C 108.8 . . ?
C16' C15' H15C 108.8 . . ?
C14' C15' H15D 108.8 . . ?
C16' C15' H15D 108.8 . . ?
H15C C15' H15D 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
O16 C16 1.428(2) . ?
O16 H16 0.8400 . ?
O17 C17 1.236(3) . ?
O17' C17' 1.239(3) . ?
O16' C16' 1.426(3) . ?
O16' H16' 0.8400 . ?
N1 C17 1.356(3) . ?
N1 C2 1.475(3) . ?
N1 C10 1.482(3) . ?
N12 C13 1.456(3) . ?
N12 C11 1.459(3) . ?
N12 H12 0.8800 . ?
N12' C13' 1.456(3) . ?
N12' C11' 1.457(3) . ?
N12' H12' 0.8800 . ?
N1' C17' 1.346(3) . ?
N1' C2' 1.474(3) . ?
N1' C10' 1.486(3) . ?
C14 C13 1.513(4) . ?
C14 C15 1.516(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.536(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C11 1.527(3) . ?
C16 C17 1.545(3) . ?
C10 C9 1.533(3) . ?
C10 C5 1.540(3) . ?
C10 H10 1.0000 . ?
C5 C6 1.526(3) . ?
C5 C4 1.529(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.523(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C11 C9 1.525(3) . ?
C11 H11 1.0000 . ?
C2 C3 1.519(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.521(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C9 C8 1.540(3) . ?
C9 H9 1.0000 . ?
C8 C7 1.522(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C4' C3' 1.530(4) . ?
C4' C5' 1.533(3) . ?
C4' H4'1 0.9900 . ?
C4' H4'2 0.9900 . ?
C5' C6' 1.527(3) . ?
C5' C10' 1.537(3) . ?
C5' H5' 1.0000 . ?
C10' C9' 1.533(3) . ?
C10' H10' 1.0000 . ?
C9' C11' 1.528(3) . ?
C9' C8' 1.534(3) . ?
C9' H9' 1.0000 . ?
C11' C16' 1.536(3) . ?
C11' H11' 1.0000 . ?
C13' C14' 1.521(3) . ?
C13' H13C 0.9900 . ?
C13' H13D 0.9900 . ?
C14' C15' 1.520(4) . ?
C14' H14C 0.9900 . ?
C14' H14D 0.9900 . ?
C2' C3' 1.521(3) . ?
C2' H2'1 0.9900 . ?
C2' H2'2 0.9900 . ?
C3' H3'1 0.9900 . ?
C3' H3'2 0.9900 . ?
C6' C7' 1.519(3) . ?
C6' H6'1 0.9900 . ?
C6' H6'2 0.9900 . ?
C7' C8' 1.522(3) . ?
C7' H7'1 0.9900 . ?
C7' H7'2 0.9900 . ?
C8' H8'1 0.9900 . ?
C8' H8'2 0.9900 . ?
C17' C16' 1.544(3) . ?
C16' C15' 1.534(3) . ?
C15' H15C 0.9900 . ?
C15' H15D 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
N12 H12 O16' 0.88 2.16 2.972(2) 153.1 2_676
O16' H16' O17' 0.84 1.95 2.768(2) 164.1 2_576
O16 H16 O17 0.84 1.95 2.773(2) 165.8 2_765
N12 H12 O16' 0.88 2.16 2.972(2) 153.1 2_676
O16' H16' O17' 0.84 1.95 2.768(2) 164.1 2_576
O16 H16 O17 0.84 1.95 2.773(2) 165.8 2_765
N12 H12 O16' 0.88 2.16 2.972(2) 153.1 2_676
O16' H16' O17' 0.84 1.95 2.768(2) 164.1 2_576
O16 H16 O17 0.84 1.95 2.773(2) 165.8 2_765
N12 H12 O16' 0.88 2.16 2.972(2) 153.1 2_676
O16' H16' O17' 0.84 1.95 2.768(2) 164.1 2_576
O16 H16 O17 0.84 1.95 2.773(2) 165.8 2_765
N12 H12 O16' 0.88 2.16 2.972(2) 153.1 2_676
O16' H16' O17' 0.84 1.95 2.768(2) 164.1 2_576
O16 H16 O17 0.84 1.95 2.773(2) 165.8 2_765
N12 H12 O16' 0.88 2.16 2.972(2) 153.1 2_676
O16' H16' O17' 0.84 1.95 2.768(2) 164.1 2_576
O16 H16 O17 0.84 1.95 2.773(2) 165.8 2_765
N12 H12 O16' 0.88 2.16 2.972(2) 153.1 2_676
O16' H16' O17' 0.84 1.95 2.768(2) 164.1 2_576
O16 H16 O17 0.84 1.95 2.773(2) 165.8 2_765
O16 H16 O17 0.84 1.95 2.773(2) 165.8 2_765
O16' H16' O17' 0.84 1.95 2.768(2) 164.1 2_576
N12 H12 O16' 0.88 2.16 2.972(2) 153.1 2_676
O16 H16 O17 0.84 1.95 2.773(2) 165.8 2_765
O16' H16' O17' 0.84 1.95 2.768(2) 164.1 2_576
N12 H12 O16' 0.88 2.16 2.972(2) 153.1 2_676
O16 H16 O17 0.84 1.95 2.773(2) 165.8 2_765
O16' H16' O17' 0.84 1.95 2.768(2) 164.1 2_576
N12 H12 O16' 0.88 2.16 2.972(2) 153.1 2_676
O16 H16 O17 0.84 1.95 2.773(2) 165.8 2_765
O16' H16' O17' 0.84 1.95 2.768(2) 164.1 2_576
N12 H12 O16' 0.88 2.16 2.972(2) 153.1 2_676
O16 H16 O17 0.84 1.95 2.773(2) 165.8 2_765
O16' H16' O17' 0.84 1.95 2.768(2) 164.1 2_576
N12 H12 O16' 0.88 2.16 2.972(2) 153.1 2_676
O16 H16 O17 0.84 1.95 2.773(2) 165.8 2_765
O16' H16' O17' 0.84 1.95 2.768(2) 164.1 2_576
N12 H12 O16' 0.88 2.16 2.972(2) 153.1 2_676
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 C14 C15 C16 -52.3(3) . . . . ?
C14 C15 C16 O16 172.27(19) . . . . ?
C14 C15 C16 C11 52.0(2) . . . . ?
C14 C15 C16 C17 -71.2(2) . . . . ?
C2 N1 C17 O17 12.3(3) . . . . ?
C10 N1 C17 O17 165.81(19) . . . . ?
C2 N1 C17 C16 -172.42(18) . . . . ?
C10 N1 C17 C16 -18.9(3) . . . . ?
O16 C16 C17 O17 82.0(2) . . . . ?
C11 C16 C17 O17 -158.32(19) . . . . ?
C15 C16 C17 O17 -35.5(3) . . . . ?
O16 C16 C17 N1 -93.4(2) . . . . ?
C11 C16 C17 N1 26.3(3) . . . . ?
C15 C16 C17 N1 149.06(19) . . . . ?
C17 N1 C10 C9 31.1(3) . . . . ?
C2 N1 C10 C9 -175.17(18) . . . . ?
C17 N1 C10 C5 156.99(19) . . . . ?
C2 N1 C10 C5 -49.3(2) . . . . ?
N1 C10 C5 C6 -75.8(2) . . . . ?
C9 C10 C5 C6 50.4(3) . . . . ?
N1 C10 C5 C4 51.7(2) . . . . ?
C9 C10 C5 C4 177.93(18) . . . . ?
C4 C5 C6 C7 176.58(19) . . . . ?
C10 C5 C6 C7 -57.1(3) . . . . ?
C11 N12 C13 C14 -64.7(3) . . . . ?
C15 C14 C13 N12 55.2(2) . . . . ?
C13 N12 C11 C9 -175.49(18) . . . . ?
C13 N12 C11 C16 63.5(2) . . . . ?
O16 C16 C11 N12 -172.79(15) . . . . ?
C15 C16 C11 N12 -53.6(2) . . . . ?
C17 C16 C11 N12 69.6(2) . . . . ?
O16 C16 C11 C9 69.3(2) . . . . ?
C15 C16 C11 C9 -171.51(16) . . . . ?
C17 C16 C11 C9 -48.3(2) . . . . ?
C17 N1 C2 C3 -153.46(19) . . . . ?
C10 N1 C2 C3 50.7(2) . . . . ?
N1 C2 C3 C4 -54.3(2) . . . . ?
C2 C3 C4 C5 57.7(2) . . . . ?
C6 C5 C4 C3 70.8(2) . . . . ?
C10 C5 C4 C3 -56.5(2) . . . . ?
N12 C11 C9 C10 -56.0(2) . . . . ?
C16 C11 C9 C10 61.6(2) . . . . ?
N12 C11 C9 C8 176.17(19) . . . . ?
C16 C11 C9 C8 -66.3(2) . . . . ?
N1 C10 C9 C11 -50.2(2) . . . . ?
C5 C10 C9 C11 -176.66(17) . . . . ?
N1 C10 C9 C8 78.3(2) . . . . ?
C5 C10 C9 C8 -48.2(2) . . . . ?
C11 C9 C8 C7 178.40(19) . . . . ?
C10 C9 C8 C7 53.0(3) . . . . ?
C9 C8 C7 C6 -58.0(3) . . . . ?
C5 C6 C7 C8 60.3(3) . . . . ?
C3' C4' C5' C6' -74.0(3) . . . . ?
C3' C4' C5' C10' 54.6(3) . . . . ?
C17' N1' C10' C9' -27.1(3) . . . . ?
C2' N1' C10' C9' 176.78(18) . . . . ?
C17' N1' C10' C5' -153.0(2) . . . . ?
C2' N1' C10' C5' 50.8(3) . . . . ?
C6' C5' C10' N1' 78.1(2) . . . . ?
C4' C5' C10' N1' -50.2(3) . . . . ?
C6' C5' C10' C9' -48.2(3) . . . . ?
C4' C5' C10' C9' -176.5(2) . . . . ?
N1' C10' C9' C11' 49.2(2) . . . . ?
C5' C10' C9' C11' 175.77(18) . . . . ?
N1' C10' C9' C8' -80.1(2) . . . . ?
C5' C10' C9' C8' 46.4(3) . . . . ?
C13' N12' C11' C9' 177.71(16) . . . . ?
C13' N12' C11' C16' -60.7(2) . . . . ?
C10' C9' C11' N12' 59.6(2) . . . . ?
C8' C9' C11' N12' -171.40(17) . . . . ?
C10' C9' C11' C16' -60.5(2) . . . . ?
C8' C9' C11' C16' 68.5(2) . . . . ?
C11' N12' C13' C14' 65.1(2) . . . . ?
N12' C13' C14' C15' -58.4(2) . . . . ?
C17' N1' C2' C3' 147.3(2) . . . . ?
C10' N1' C2' C3' -54.6(3) . . . . ?
N1' C2' C3' C4' 57.7(3) . . . . ?
C5' C4' C3' C2' -58.4(3) . . . . ?
C4' C5' C6' C7' -176.0(2) . . . . ?
C10' C5' C6' C7' 56.6(3) . . . . ?
C5' C6' C7' C8' -61.0(3) . . . . ?
C6' C7' C8' C9' 59.4(2) . . . . ?
C11' C9' C8' C7' 179.77(18) . . . . ?
C10' C9' C8' C7' -53.3(2) . . . . ?
C2' N1' C17' O17' -14.4(3) . . . . ?
C10' N1' C17' O17' -170.13(19) . . . . ?
C2' N1' C17' C16' 168.68(19) . . . . ?
C10' N1' C17' C16' 13.0(3) . . . . ?
N12' C11' C16' O16' 168.08(16) . . . . ?
C9' C11' C16' O16' -73.0(2) . . . . ?
N12' C11' C16' C15' 50.1(2) . . . . ?
C9' C11' C16' C15' 168.96(17) . . . . ?
N12' C11' C16' C17' -73.4(2) . . . . ?
C9' C11' C16' C17' 45.5(2) . . . . ?
O17' C17' C16' O16' -80.3(2) . . . . ?
N1' C17' C16' O16' 96.8(2) . . . . ?
O17' C17' C16' C15' 37.9(3) . . . . ?
N1' C17' C16' C15' -145.1(2) . . . . ?
O17' C17' C16' C11' 161.45(19) . . . . ?
N1' C17' C16' C11' -21.5(3) . . . . ?
C13' C14' C15' C16' 53.5(2) . . . . ?
O16' C16' C15' C14' -167.04(17) . . . . ?
C11' C16' C15' C14' -49.4(2) . . . . ?
C17' C16' C15' C14' 75.0(2) . . . . ?
