#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/74/1507434.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_1507434
loop_
_publ_author_name
'Hirose, Tomoyasu'
'Sunazuka, Toshiaki'
'Shirahata, Tatsuya'
'Yamamoto, Daisuke'
'Harigaya, Yoshihiro'
'Kuwajima, Isao'
'Ōmura, Satoshi'
_publ_section_title
;
 Short Total Synthesis of (+)-Madindolines A and B
;
_journal_issue                   4
_journal_name_full               'Organic Letters'
_journal_page_first              501
_journal_paper_doi               10.1021/ol017058i
_journal_volume                  4
_journal_year                    2002
_chemical_formula_moiety         'C22 H27 N O4 '
_chemical_formula_sum            'C22 H27 N O4'
_chemical_formula_weight         369.46
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90
_cell_angle_beta                 91.30(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.639(4)
_cell_length_b                   9.002(4)
_cell_length_c                   14.719(3)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      29.2
_cell_measurement_theta_min      28.2
_cell_volume                     1011.9(7)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan Ver. 1.10'
_computing_publication_material  'teXsan Ver. 1.10'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SHELXS97
_diffrn_measured_fraction_theta_full 0.9678
_diffrn_measured_fraction_theta_max 0.9678
_diffrn_measurement_device_type  'Rigaku AFC5R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2050
_diffrn_reflns_theta_full        67.63
_diffrn_reflns_theta_max         67.63
_diffrn_standards_decay_%        0.08
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.32
_refine_ls_abs_structure_Flack   4.86645
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   4.573
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     245
_refine_ls_number_reflns         1098
_refine_ls_R_factor_gt           0.0981
_refine_ls_shift/su_max          2.1344
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.00100(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1207
_reflns_number_gt                1098
_reflns_number_total             1894
_reflns_threshold_expression     F²>3.0σ(F²)
_cod_data_source_file            ol017058i_s2.cif
_cod_data_source_block           mdlb-2
_cod_original_cell_volume        1011.8(6)
_cod_original_formula_sum        'C22 H27 N O4 '
_cod_database_code               1507434
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+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_calc_flag
O(1) O 0.5139(5) 0.191(2) 0.6089(3) 0.045(1) Uani 1.00 d
O(2) O 0.3515(5) 0.405(2) 0.4308(3) 0.047(1) Uani 1.00 d
O(3) O 0.8996(5) 0.168(2) 0.6881(3) 0.062(1) Uani 1.00 d
O(4) O 0.6221(7) 0.511(2) 0.8746(3) 0.072(2) Uani 1.00 d
N(1) N 0.5642(6) 0.445(2) 0.6459(3) 0.043(1) Uani 1.00 d
C(1) C 0.5329(8) 0.340(2) 0.5728(4) 0.042(2) Uani 1.00 d
C(2) C 0.3324(8) 0.175(2) 0.6280(4) 0.053(2) Uani 1.00 d
C(3) C 0.2378(8) 0.242(2) 0.5489(4) 0.044(2) Uani 1.00 d
C(4) C 0.3489(7) 0.379(2) 0.5263(4) 0.044(2) Uani 1.00 d
C(5) C 0.2990(7) 0.517(2) 0.5809(4) 0.034(2) Uani 1.00 d
C(6) C 0.1523(8) 0.609(2) 0.5646(4) 0.048(2) Uani 1.00 d
C(7) C 0.1347(8) 0.729(2) 0.6240(4) 0.053(2) Uani 1.00 d
C(8) C 0.2600(8) 0.758(2) 0.6902(4) 0.050(2) Uani 1.00 d
C(9) C 0.4096(7) 0.671(2) 0.7044(4) 0.045(2) Uani 1.00 d
C(10) C 0.4269(8) 0.545(2) 0.6457(4) 0.037(2) Uani 1.00 d
C(11) C 0.8006(8) 0.393(2) 0.7610(4) 0.042(2) Uani 1.00 d
C(12) C 0.8093(8) 0.222(2) 0.7415(4) 0.051(2) Uani 1.00 d
C(13) C 0.6859(9) 0.149(2) 0.8057(5) 0.054(2) Uani 1.00 d
C(14) C 0.6029(9) 0.244(2) 0.8567(5) 0.054(2) Uani 1.00 d
C(15) C 0.6711(9) 0.401(2) 0.8371(4) 0.052(2) Uani 1.00 d
C(16) C 0.7435(8) 0.478(2) 0.6742(4) 0.042(2) Uani 1.00 d
C(17) C 0.9822(7) 0.443(2) 0.7908(4) 0.046(2) Uani 1.00 d
C(18) C 0.6634(10) -0.015(2) 0.8049(5) 0.077(3) Uani 1.00 d
C(19) C 0.815(2) -0.092(3) 0.8671(9) 0.208(7) Uani 1.00 d
C(20) C 0.943(2) -0.084(3) 0.894(1) 0.250(8) Uani 1.00 d
C(21) C 1.087(2) -0.158(3) 0.9434(8) 0.196(6) Uani 1.00 d
C(22) C 0.4678(10) 0.226(2) 0.9273(5) 0.093(3) Uani 1.00 d
H(1) H 0.6214 0.3422 0.5278 0.0524 Uiso 1.00 calc
H(2) H 0.3036 0.2229 0.6816 0.0698 Uiso 1.00 calc
H(3) H 0.3012 0.0719 0.6308 0.0698 Uiso 1.00 calc
H(4) H 0.1219 0.2735 0.5629 0.0585 Uiso 1.00 calc
H(5) H 0.2325 0.1804 0.4965 0.0585 Uiso 1.00 calc
H(6) H 0.0706 0.5864 0.5198 0.0592 Uiso 1.00 calc
H(7) H 0.0385 0.7933 0.6152 0.0703 Uiso 1.00 calc
H(8) H 0.2455 0.8426 0.7277 0.0691 Uiso 1.00 calc
H(9) H 0.4901 0.6931 0.7498 0.0614 Uiso 1.00 calc
H(10) H 0.8195 0.4570 0.6285 0.0558 Uiso 1.00 calc
H(11) H 0.7479 0.5822 0.6898 0.0558 Uiso 1.00 calc
H(12) H 1.0634 0.4282 0.7447 0.0776 Uiso 1.00 calc
H(13) H 0.9770 0.5518 0.8019 0.0776 Uiso 1.00 calc
H(14) H 1.0180 0.3982 0.8452 0.0776 Uiso 1.00 calc
H(15) H 0.6727 -0.0476 0.7436 0.0904 Uiso 1.00 calc
H(16) H 0.5534 -0.0353 0.8272 0.0904 Uiso 1.00 calc
H(17) H 0.8228 -0.1848 0.8236 0.2758 Uiso 1.00 calc
H(18) H 0.7332 -0.1331 0.9117 0.2758 Uiso 1.00 calc
H(19) H 0.9987 -0.0264 0.8454 0.2835 Uiso 1.00 calc
H(20) H 0.9121 0.0017 0.9382 0.2835 Uiso 1.00 calc
H(21) H 1.1817 -0.0943 0.9533 0.1862 Uiso 1.00 calc
H(22) H 1.0435 -0.1962 0.9975 0.1862 Uiso 1.00 calc
H(23) H 1.1195 -0.2379 0.9040 0.1862 Uiso 1.00 calc
H(24) H 0.5234 0.1668 0.9750 0.1126 Uiso 1.00 calc
H(25) H 0.3734 0.1775 0.9025 0.1126 Uiso 1.00 calc
H(26) H 0.4402 0.3197 0.9517 0.1126 Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O O 0.049 0.032
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N N 0.031 0.018
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(1) O(1) C(2) 106.1(9) 1_555 1_555 yes
C(1) N(1) C(10) 109.0(8) 1_555 1_555 yes
C(1) N(1) C(16) 120.9(8) 1_555 1_555 yes
C(10) N(1) C(16) 123.4(9) 1_555 1_555 yes
O(1) C(1) N(1) 111.1(8) 1_555 1_555 yes
O(1) C(1) C(4) 106.3(8) 1_555 1_555 yes
O(1) C(1) H(1) 112.3 1_555 1_555 no
N(1) C(1) C(4) 106.3(8) 1_555 1_555 yes
N(1) C(1) H(1) 109.9 1_555 1_555 no
C(4) C(1) H(1) 110.7 1_555 1_555 no
O(1) C(2) C(3) 105.1(9) 1_555 1_555 yes
O(1) C(2) H(2) 109.9 1_555 1_555 no
O(1) C(2) H(3) 111.9 1_555 1_555 no
C(3) C(2) H(2) 109.2 1_555 1_555 no
C(3) C(2) H(3) 110.6 1_555 1_555 no
H(2) C(2) H(3) 110.1 1_555 1_555 no
C(2) C(3) C(4) 103.4(8) 1_555 1_555 yes
C(2) C(3) H(4) 112.4 1_555 1_555 no
C(2) C(3) H(5) 112.2 1_555 1_555 no
C(4) C(3) H(4) 109.0 1_555 1_555 no
C(4) C(3) H(5) 109.8 1_555 1_555 no
H(4) C(3) H(5) 109.9 1_555 1_555 no
O(2) C(4) C(1) 113.3(8) 1_555 1_555 yes
O(2) C(4) C(3) 109.7(9) 1_555 1_555 yes
O(2) C(4) C(5) 112.8(9) 1_555 1_555 yes
C(1) C(4) C(3) 102.7(8) 1_555 1_555 yes
C(1) C(4) C(5) 102.7(8) 1_555 1_555 yes
C(3) C(4) C(5) 115.1(7) 1_555 1_555 yes
C(4) C(5) C(6) 128.5(9) 1_555 1_555 yes
C(4) C(5) C(10) 109.8(8) 1_555 1_555 yes
C(6) C(5) C(10) 121.6(10) 1_555 1_555 yes
C(5) C(6) C(7) 118.2(10) 1_555 1_555 yes
C(5) C(6) H(6) 121.6 1_555 1_555 no
C(7) C(6) H(6) 120.2 1_555 1_555 no
C(6) C(7) C(8) 120(1) 1_555 1_555 yes
C(6) C(7) H(7) 120.4 1_555 1_555 no
C(8) C(7) H(7) 119.4 1_555 1_555 no
C(7) C(8) C(9) 122(1) 1_555 1_555 yes
C(7) C(8) H(8) 118.6 1_555 1_555 no
C(9) C(8) H(8) 118.8 1_555 1_555 no
C(8) C(9) C(10) 116(1) 1_555 1_555 yes
C(8) C(9) H(9) 120.3 1_555 1_555 no
C(10) C(9) H(9) 122.7 1_555 1_555 no
N(1) C(10) C(5) 112.1(9) 1_555 1_555 yes
N(1) C(10) C(9) 127.7(9) 1_555 1_555 yes
C(5) C(10) C(9) 120.3(10) 1_555 1_555 yes
C(12) C(11) C(15) 100.0(9) 1_555 1_555 yes
C(12) C(11) C(16) 111.9(9) 1_555 1_555 yes
C(12) C(11) C(17) 110.7(10) 1_555 1_555 yes
C(15) C(11) C(16) 112.9(9) 1_555 1_555 yes
C(15) C(11) C(17) 113.3(9) 1_555 1_555 yes
C(16) C(11) C(17) 107.9(9) 1_555 1_555 yes
O(3) C(12) C(11) 124(1) 1_555 1_555 yes
O(3) C(12) C(13) 123(1) 1_555 1_555 yes
C(11) C(12) C(13) 111.7(9) 1_555 1_555 yes
C(12) C(13) C(14) 108(1) 1_555 1_555 yes
C(12) C(13) C(18) 124(1) 1_555 1_555 yes
C(14) C(13) C(18) 127(1) 1_555 1_555 yes
C(13) C(14) C(15) 109(1) 1_555 1_555 yes
C(13) C(14) C(22) 130(1) 1_555 1_555 yes
C(15) C(14) C(22) 120(1) 1_555 1_555 yes
O(4) C(15) C(11) 123(1) 1_555 1_555 yes
O(4) C(15) C(14) 125.8(10) 1_555 1_555 yes
C(11) C(15) C(14) 110(1) 1_555 1_555 yes
N(1) C(16) C(11) 113.7(9) 1_555 1_555 yes
N(1) C(16) H(10) 108.8 1_555 1_555 no
N(1) C(16) H(11) 107.8 1_555 1_555 no
C(11) C(16) H(10) 109.5 1_555 1_555 no
C(11) C(16) H(11) 108.7 1_555 1_555 no
H(10) C(16) H(11) 108.1 1_555 1_555 no
C(11) C(17) H(12) 110.6 1_555 1_555 no
C(11) C(17) H(13) 109.6 1_555 1_555 no
C(11) C(17) H(14) 109.8 1_555 1_555 no
H(12) C(17) H(13) 108.3 1_555 1_555 no
H(12) C(17) H(14) 110.8 1_555 1_555 no
H(13) C(17) H(14) 107.8 1_555 1_555 no
C(13) C(18) C(19) 116(1) 1_555 1_555 yes
C(13) C(18) H(15) 106.1 1_555 1_555 no
C(13) C(18) H(16) 106.2 1_555 1_555 no
C(19) C(18) H(15) 110.0 1_555 1_555 no
C(19) C(18) H(16) 108.1 1_555 1_555 no
H(15) C(18) H(16) 110.2 1_555 1_555 no
C(18) C(19) C(20) 133(4) 1_555 1_555 yes
C(18) C(19) H(17) 100.6 1_555 1_555 no
C(18) C(19) H(18) 103.3 1_555 1_555 no
C(20) C(19) H(17) 101.3 1_555 1_555 no
C(20) C(19) H(18) 106.1 1_555 1_555 no
H(17) C(19) H(18) 111.3 1_555 1_555 no
C(19) C(20) C(21) 135(4) 1_555 1_555 yes
C(19) C(20) H(19) 104.7 1_555 1_555 no
C(19) C(20) H(20) 100.5 1_555 1_555 no
C(21) C(20) H(19) 104.2 1_555 1_555 no
C(21) C(20) H(20) 102.7 1_555 1_555 no
H(19) C(20) H(20) 107.1 1_555 1_555 no
C(20) C(21) H(21) 109.0 1_555 1_555 no
C(20) C(21) H(22) 111.1 1_555 1_555 no
C(20) C(21) H(23) 110.1 1_555 1_555 no
H(21) C(21) H(22) 107.5 1_555 1_555 no
H(21) C(21) H(23) 107.8 1_555 1_555 no
H(22) C(21) H(23) 111.3 1_555 1_555 no
C(14) C(22) H(24) 109.5 1_555 1_555 no
C(14) C(22) H(25) 108.9 1_555 1_555 no
C(14) C(22) H(26) 107.9 1_555 1_555 no
H(24) C(22) H(25) 113.1 1_555 1_555 no
H(24) C(22) H(26) 109.2 1_555 1_555 no
H(25) C(22) H(26) 108.2 1_555 1_555 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(1) 1.43(2) yes
O(1) C(2) 1.41(1) yes
O(2) C(4) 1.42(1) yes
O(3) C(12) 1.23(1) yes
O(4) C(15) 1.23(2) yes
N(1) C(1) 1.45(1) yes
N(1) C(10) 1.40(1) yes
N(1) C(16) 1.47(1) yes
C(1) C(4) 1.57(1) yes
C(1) H(1) 0.971 no
C(2) C(3) 1.49(1) yes
C(2) H(2) 0.969 no
C(2) H(3) 0.923 no
C(3) C(4) 1.52(1) yes
C(3) H(4) 0.958 no
C(3) H(5) 0.938 no
C(4) C(5) 1.50(1) yes
C(5) C(6) 1.38(1) yes
C(5) C(10) 1.37(1) yes
C(6) C(7) 1.38(2) yes
C(6) H(6) 0.948 no
C(7) C(8) 1.37(1) yes
C(7) H(7) 0.965 no
C(8) C(9) 1.37(1) yes
C(8) H(8) 0.968 no
C(9) C(10) 1.41(1) yes
C(9) H(9) 0.953 no
C(11) C(12) 1.49(2) yes
C(11) C(15) 1.51(1) yes
C(11) C(16) 1.53(1) yes
C(11) C(17) 1.53(1) yes
C(12) C(13) 1.47(1) yes
C(13) C(14) 1.35(2) yes
C(13) C(18) 1.47(2) yes
C(14) C(15) 1.47(2) yes
C(14) C(22) 1.49(2) yes
C(16) H(10) 0.941 no
C(16) H(11) 0.975 no
C(17) H(12) 0.939 no
C(17) H(13) 0.975 no
C(17) H(14) 0.946 no
C(18) C(19) 1.52(4) yes
C(18) H(15) 0.947 no
C(18) H(16) 0.944 no
C(19) C(20) 1.20(4) yes
C(19) H(17) 0.963 no
C(19) H(18) 0.915 no
C(20) C(21) 1.48(4) yes
C(20) H(19) 0.951 no
C(20) H(20) 0.978 no
C(21) H(21) 0.982 no
C(21) H(22) 0.942 no
C(21) H(23) 0.938 no
C(22) H(24) 0.924 no
C(22) H(25) 0.936 no
C(22) H(26) 0.979 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O(1) O(2) 2.85(1) 2_646
O(1) C(5) 3.51(1) 2_646
O(2) C(9) 3.45(1) 2_646
O(2) O(3) 3.53(1) 2_656
O(2) C(2) 3.53(2) 2_656
O(2) C(18) 3.58(2) 2_656
O(3) C(3) 3.42(1) 1_655
O(3) C(2) 3.45(1) 1_655
O(4) C(22) 3.58(2) 2_657
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
O(1) C(1) N(1) C(10) -118.4(9) 1_555 1_555 1_555 1_555 yes
O(1) C(1) N(1) C(16) 89(1) 1_555 1_555 1_555 1_555 yes
O(1) C(1) C(4) O(2) -116(1) 1_555 1_555 1_555 1_555 yes
O(1) C(1) C(4) C(3) 1(1) 1_555 1_555 1_555 1_555 yes
O(1) C(1) C(4) C(5) 121.5(8) 1_555 1_555 1_555 1_555 yes
O(1) C(2) C(3) C(4) -38(1) 1_555 1_555 1_555 1_555 yes
O(1) C(2) C(3) H(4) -156(1) 1_555 1_555 1_555 1_555 no
O(1) C(2) C(3) H(5) 79(1) 1_555 1_555 1_555 1_555 no
O(2) C(4) C(1) N(1) 125(1) 1_555 1_555 1_555 1_555 yes
O(2) C(4) C(1) H(1) 5(2) 1_555 1_555 1_555 1_555 no
O(2) C(4) C(3) C(2) 142.2(9) 1_555 1_555 1_555 1_555 yes
O(2) C(4) C(3) H(4) -98(1) 1_555 1_555 1_555 1_555 no
O(2) C(4) C(3) H(5) 22(1) 1_555 1_555 1_555 1_555 no
O(2) C(4) C(5) C(6) 54(1) 1_555 1_555 1_555 1_555 yes
O(2) C(4) C(5) C(10) -124.3(9) 1_555 1_555 1_555 1_555 yes
O(3) C(12) C(11) C(15) -178.1(9) 1_555 1_555 1_555 1_555 yes
O(3) C(12) C(11) C(16) 62(1) 1_555 1_555 1_555 1_555 yes
O(3) C(12) C(11) C(17) -58(1) 1_555 1_555 1_555 1_555 yes
O(3) C(12) C(13) C(14) 179(1) 1_555 1_555 1_555 1_555 yes
O(3) C(12) C(13) C(18) -1(1) 1_555 1_555 1_555 1_555 yes
O(4) C(15) C(11) C(12) 179(1) 1_555 1_555 1_555 1_555 yes
O(4) C(15) C(11) C(16) -61(1) 1_555 1_555 1_555 1_555 yes
O(4) C(15) C(11) C(17) 61(1) 1_555 1_555 1_555 1_555 yes
O(4) C(15) C(14) C(13) -177(1) 1_555 1_555 1_555 1_555 yes
O(4) C(15) C(14) C(22) 0(1) 1_555 1_555 1_555 1_555 yes
N(1) C(1) O(1) C(2) 89.3(10) 1_555 1_555 1_555 1_555 yes
N(1) C(1) C(4) C(3) -116.7(8) 1_555 1_555 1_555 1_555 yes
N(1) C(1) C(4) C(5) 3.1(10) 1_555 1_555 1_555 1_555 yes
N(1) C(10) C(5) C(4) 0(1) 1_555 1_555 1_555 1_555 yes
N(1) C(10) C(5) C(6) -178.5(9) 1_555 1_555 1_555 1_555 yes
N(1) C(10) C(9) C(8) 179(1) 1_555 1_555 1_555 1_555 yes
N(1) C(10) C(9) H(9) 0(2) 1_555 1_555 1_555 1_555 no
N(1) C(16) C(11) C(12) 62(1) 1_555 1_555 1_555 1_555 yes
N(1) C(16) C(11) C(15) -49(1) 1_555 1_555 1_555 1_555 yes
N(1) C(16) C(11) C(17) -175.1(9) 1_555 1_555 1_555 1_555 yes
C(1) O(1) C(2) C(3) 40(1) 1_555 1_555 1_555 1_555 yes
C(1) O(1) C(2) H(2) -76(1) 1_555 1_555 1_555 1_555 no
C(1) O(1) C(2) H(3) 160.7(10) 1_555 1_555 1_555 1_555 no
C(1) N(1) C(10) C(5) 1(1) 1_555 1_555 1_555 1_555 yes
C(1) N(1) C(10) C(9) -179.3(9) 1_555 1_555 1_555 1_555 yes
C(1) N(1) C(16) C(11) -96(1) 1_555 1_555 1_555 1_555 yes
C(1) N(1) C(16) H(10) 25(2) 1_555 1_555 1_555 1_555 no
C(1) N(1) C(16) H(11) 142(1) 1_555 1_555 1_555 1_555 no
C(1) C(4) C(3) C(2) 21(1) 1_555 1_555 1_555 1_555 yes
C(1) C(4) C(3) H(4) 141.2(9) 1_555 1_555 1_555 1_555 no
C(1) C(4) C(3) H(5) -98(1) 1_555 1_555 1_555 1_555 no
C(1) C(4) C(5) C(6) 176.5(10) 1_555 1_555 1_555 1_555 yes
C(1) C(4) C(5) C(10) -2.1(10) 1_555 1_555 1_555 1_555 yes
C(2) O(1) C(1) C(4) -25.9(10) 1_555 1_555 1_555 1_555 yes
C(2) O(1) C(1) H(1) -147(1) 1_555 1_555 1_555 1_555 no
C(2) C(3) C(4) C(5) -89.3(10) 1_555 1_555 1_555 1_555 yes
C(3) C(4) C(1) H(1) 123(2) 1_555 1_555 1_555 1_555 no
C(3) C(4) C(5) C(6) -72(1) 1_555 1_555 1_555 1_555 yes
C(3) C(4) C(5) C(10) 108.7(9) 1_555 1_555 1_555 1_555 yes
C(4) C(1) N(1) C(10) -3(1) 1_555 1_555 1_555 1_555 yes
C(4) C(1) N(1) C(16) -155.4(9) 1_555 1_555 1_555 1_555 yes
C(4) C(3) C(2) H(2) 79(1) 1_555 1_555 1_555 1_555 no
C(4) C(3) C(2) H(3) -159(1) 1_555 1_555 1_555 1_555 no
C(4) C(5) C(6) C(7) 179.9(10) 1_555 1_555 1_555 1_555 yes
C(4) C(5) C(6) H(6) -1(2) 1_555 1_555 1_555 1_555 no
C(4) C(5) C(10) C(9) -178.6(9) 1_555 1_555 1_555 1_555 yes
C(5) C(4) C(1) H(1) -116(2) 1_555 1_555 1_555 1_555 no
C(5) C(4) C(3) H(4) 30(1) 1_555 1_555 1_555 1_555 no
C(5) C(4) C(3) H(5) 150(1) 1_555 1_555 1_555 1_555 no
C(5) C(6) C(7) C(8) 0(1) 1_555 1_555 1_555 1_555 yes
C(5) C(6) C(7) H(7) 179(1) 1_555 1_555 1_555 1_555 no
C(5) C(10) N(1) C(16) 153.3(9) 1_555 1_555 1_555 1_555 yes
C(5) C(10) C(9) C(8) -2(1) 1_555 1_555 1_555 1_555 yes
C(5) C(10) C(9) H(9) 178(1) 1_555 1_555 1_555 1_555 no
C(6) C(5) C(10) C(9) 2(1) 1_555 1_555 1_555 1_555 yes
C(6) C(7) C(8) C(9) 0(1) 1_555 1_555 1_555 1_555 yes
C(6) C(7) C(8) H(8) -179(1) 1_555 1_555 1_555 1_555 no
C(7) C(6) C(5) C(10) -1(1) 1_555 1_555 1_555 1_555 yes
C(7) C(8) C(9) C(10) 0(1) 1_555 1_555 1_555 1_555 yes
C(7) C(8) C(9) H(9) 179(1) 1_555 1_555 1_555 1_555 no
C(8) C(7) C(6) H(6) -178(1) 1_555 1_555 1_555 1_555 no
C(9) C(8) C(7) H(7) -178(1) 1_555 1_555 1_555 1_555 no
C(9) C(10) N(1) C(16) -27(1) 1_555 1_555 1_555 1_555 yes
C(10) N(1) C(1) H(1) 116(1) 1_555 1_555 1_555 1_555 no
C(10) N(1) C(16) C(11) 114(1) 1_555 1_555 1_555 1_555 yes
C(10) N(1) C(16) H(10) -122(2) 1_555 1_555 1_555 1_555 no
C(10) N(1) C(16) H(11) -5(1) 1_555 1_555 1_555 1_555 no
C(10) C(5) C(6) H(6) 177(1) 1_555 1_555 1_555 1_555 no
C(10) C(9) C(8) H(8) -179(1) 1_555 1_555 1_555 1_555 no
C(11) C(12) C(13) C(14) 2(1) 1_555 1_555 1_555 1_555 yes
C(11) C(12) C(13) C(18) -178(1) 1_555 1_555 1_555 1_555 yes
C(11) C(15) C(14) C(13) 2(1) 1_555 1_555 1_555 1_555 yes
C(11) C(15) C(14) C(22) 179(1) 1_555 1_555 1_555 1_555 yes
C(12) C(11) C(15) C(14) 0(1) 1_555 1_555 1_555 1_555 yes
C(12) C(11) C(16) H(10) -59(1) 1_555 1_555 1_555 1_555 no
C(12) C(11) C(16) H(11) -177.0(9) 1_555 1_555 1_555 1_555 no
C(12) C(11) C(17) H(12) 61(2) 1_555 1_555 1_555 1_555 no
C(12) C(11) C(17) H(13) -179(1) 1_555 1_555 1_555 1_555 no
C(12) C(11) C(17) H(14) -61(2) 1_555 1_555 1_555 1_555 no
C(12) C(13) C(14) C(15) -2(1) 1_555 1_555 1_555 1_555 yes
C(12) C(13) C(14) C(22) -179(1) 1_555 1_555 1_555 1_555 yes
C(12) C(13) C(18) C(19) 85(1) 1_555 1_555 1_555 1_555 yes
C(12) C(13) C(18) H(15) -36(1) 1_555 1_555 1_555 1_555 no
C(12) C(13) C(18) H(16) -154(1) 1_555 1_555 1_555 1_555 no
C(13) C(12) C(11) C(15) 0(1) 1_555 1_555 1_555 1_555 yes
C(13) C(12) C(11) C(16) -120.6(9) 1_555 1_555 1_555 1_555 yes
C(13) C(12) C(11) C(17) 119.0(10) 1_555 1_555 1_555 1_555 yes
C(13) C(14) C(22) H(24) 61(2) 1_555 1_555 1_555 1_555 no
C(13) C(14) C(22) H(25) -62(2) 1_555 1_555 1_555 1_555 no
C(13) C(14) C(22) H(26) -179(1) 1_555 1_555 1_555 1_555 no
C(13) C(18) C(19) C(20) -20(4) 1_555 1_555 1_555 1_555 yes
C(13) C(18) C(19) H(17) -137(2) 1_555 1_555 1_555 1_555 no
C(13) C(18) C(19) H(18) 107(3) 1_555 1_555 1_555 1_555 no
C(14) C(13) C(18) C(19) -95(1) 1_555 1_555 1_555 1_555 yes
C(14) C(13) C(18) H(15) 141(1) 1_555 1_555 1_555 1_555 no
C(14) C(13) C(18) H(16) 24(2) 1_555 1_555 1_555 1_555 no
C(14) C(15) C(11) C(16) 118(1) 1_555 1_555 1_555 1_555 yes
C(14) C(15) C(11) C(17) -118(1) 1_555 1_555 1_555 1_555 yes
C(15) C(11) C(16) H(10) -171(1) 1_555 1_555 1_555 1_555 no
C(15) C(11) C(16) H(11) 70(1) 1_555 1_555 1_555 1_555 no
C(15) C(11) C(17) H(12) 172(2) 1_555 1_555 1_555 1_555 no
C(15) C(11) C(17) H(13) -68(1) 1_555 1_555 1_555 1_555 no
C(15) C(11) C(17) H(14) 50(2) 1_555 1_555 1_555 1_555 no
C(15) C(14) C(13) C(18) 178(1) 1_555 1_555 1_555 1_555 yes
C(15) C(14) C(22) H(24) -114(2) 1_555 1_555 1_555 1_555 no
C(15) C(14) C(22) H(25) 121(2) 1_555 1_555 1_555 1_555 no
C(15) C(14) C(22) H(26) 3(1) 1_555 1_555 1_555 1_555 no
C(16) N(1) C(1) H(1) -35(1) 1_555 1_555 1_555 1_555 no
C(16) C(11) C(17) H(12) -61(2) 1_555 1_555 1_555 1_555 no
C(16) C(11) C(17) H(13) 57(1) 1_555 1_555 1_555 1_555 no
C(16) C(11) C(17) H(14) 175(1) 1_555 1_555 1_555 1_555 no
C(17) C(11) C(16) H(10) 62(1) 1_555 1_555 1_555 1_555 no
C(17) C(11) C(16) H(11) -55(1) 1_555 1_555 1_555 1_555 no
C(18) C(13) C(14) C(22) 1(2) 1_555 1_555 1_555 1_555 yes
C(18) C(19) C(20) C(21) -171(2) 1_555 1_555 1_555 1_555 yes
C(18) C(19) C(20) H(19) -42(6) 1_555 1_555 1_555 1_555 no
C(18) C(19) C(20) H(20) 68(5) 1_555 1_555 1_555 1_555 no
C(19) C(20) C(21) H(21) 178(3) 1_555 1_555 1_555 1_555 no
C(19) C(20) C(21) H(22) -63(5) 1_555 1_555 1_555 1_555 no
C(19) C(20) C(21) H(23) 60(5) 1_555 1_555 1_555 1_555 no
C(20) C(19) C(18) H(15) 99(4) 1_555 1_555 1_555 1_555 no
C(20) C(19) C(18) H(16) -139(4) 1_555 1_555 1_555 1_555 no
C(21) C(20) C(19) H(17) -54(5) 1_555 1_555 1_555 1_555 no
C(21) C(20) C(19) H(18) 61(6) 1_555 1_555 1_555 1_555 no
H(2) C(2) C(3) H(4) -38(1) 1_555 1_555 1_555 1_555 no
H(2) C(2) C(3) H(5) -162(2) 1_555 1_555 1_555 1_555 no
H(3) C(2) C(3) H(4) 83(1) 1_555 1_555 1_555 1_555 no
H(3) C(2) C(3) H(5) -41(1) 1_555 1_555 1_555 1_555 no
H(6) C(6) C(7) H(7) 0(1) 1_555 1_555 1_555 1_555 no
H(7) C(7) C(8) H(8) 1(1) 1_555 1_555 1_555 1_555 no
H(8) C(8) C(9) H(9) 0(1) 1_555 1_555 1_555 1_555 no
H(15) C(18) C(19) H(17) -17(3) 1_555 1_555 1_555 1_555 no
H(15) C(18) C(19) H(18) -132(4) 1_555 1_555 1_555 1_555 no
H(16) C(18) C(19) H(17) 103(3) 1_555 1_555 1_555 1_555 no
H(16) C(18) C(19) H(18) -11(3) 1_555 1_555 1_555 1_555 no
H(17) C(19) C(20) H(19) 74(4) 1_555 1_555 1_555 1_555 no
H(17) C(19) C(20) H(20) -174(3) 1_555 1_555 1_555 1_555 no
H(18) C(19) C(20) H(19) -169(4) 1_555 1_555 1_555 1_555 no
H(18) C(19) C(20) H(20) -58(5) 1_555 1_555 1_555 1_555 no
H(19) C(20) C(21) H(21) 49(3) 1_555 1_555 1_555 1_555 no
H(19) C(20) C(21) H(22) 167(4) 1_555 1_555 1_555 1_555 no
H(19) C(20) C(21) H(23) -68(3) 1_555 1_555 1_555 1_555 no
H(20) C(20) C(21) H(21) -61(3) 1_555 1_555 1_555 1_555 no
H(20) C(20) C(21) H(22) 56(3) 1_555 1_555 1_555 1_555 no
H(20) C(20) C(21) H(23) 179(3) 1_555 1_555 1_555 1_555 no
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 9156686 ChemSpider
