data_2203250
loop_
_publ_author_name
'Yoshikawa, Naokazu'
'Takemoto, Keiko'
'Sakamoto, Jun'
'Kanehisa, Nobuko'
'Kai, Yasushi'
'Takashima, Hiroshi'
'Tsukahara, Keiichi'
_publ_section_title
;
(11R)-(-)-N,N'-Dimethylcinchonidinium diiodide
;
_journal_issue                 2
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o281
_journal_page_last             o282
_journal_volume                60
_journal_year                  2004
_chemical_formula_iupac        'C21 H28 N2 O 2+, 2I 1-'
_chemical_formula_moiety       'C21 H28 N2 O 2+, 2I 1-'
_chemical_formula_sum          'C21 H28 I2 N2 O '
_chemical_formula_weight       578.27
_chemical_melting_point        ?
_symmetry_cell_setting         orthorhombic
_symmetry_space_group_name_Hall 'P 2ac 2ab'
_symmetry_space_group_name_H-M 'P 21 21 21'
_cell_angle_alpha              90
_cell_angle_beta               90
_cell_angle_gamma              90
_cell_formula_units_Z          4
_cell_length_a                 11.3103(4)
_cell_length_b                 13.3106(3)
_cell_length_c                 14.9280(5)
_cell_measurement_reflns_used  29792
_cell_measurement_temperature  296.2
_cell_measurement_theta_max    30.5
_cell_measurement_theta_min    1.4
_cell_volume                   2247.40(10)
_computing_cell_refinement     PROCESS-AUTO
_computing_data_collection     'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction      'TEXSAN (Molecular Structure Corporation, 2000)'
_computing_molecular_graphics  'ORTEPII (Johnson, 1976)'
_computing_publication_material TEXSAN
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution  'SIR92 (Altomare et al., 1992)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 30.5
_diffrn_measured_fraction_theta_max 30.5
_diffrn_measurement_device_type 'Rigaku R-AXIS RAPID Imaging Plate'
_diffrn_measurement_method     \w
_diffrn_radiation_type         'Mo K\a'
_diffrn_radiation_wavelength   0.7107
_diffrn_reflns_av_R_equivalents 0.046
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_l_max     21
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_number          26613
_diffrn_reflns_theta_full      30.5
_diffrn_reflns_theta_max       30.50
_diffrn_reflns_theta_min       1.7
_diffrn_standards_decay_%      0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time 0
_diffrn_standards_number       0
_exptl_absorpt_coefficient_mu  2.812
_exptl_absorpt_correction_T_max 0.755
_exptl_absorpt_correction_T_min 0.619
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour          yellow
_exptl_crystal_density_diffrn  1.709
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     prism
_exptl_crystal_F_000           1128
_exptl_crystal_size_max        0.200
_exptl_crystal_size_mid        0.1600
_exptl_crystal_size_min        0.100
_exptl_crystal_size_rad        ?
_refine_diff_density_max       1.76
_refine_diff_density_min       -0.39
_refine_ls_abs_structure_details 'Flack (1983), 2857 Friedel pairs [CHECK]'
_refine_ls_abs_structure_Flack 0.01(2)
_refine_ls_extinction_coef     ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_ref 1.095
_refine_ls_hydrogen_treatment  constr
_refine_ls_number_parameters   235
_refine_ls_number_reflns       5056
_refine_ls_R_factor_gt         0.0498
_refine_ls_shift/su_max        0.01320
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^) + (0.1P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_ref       0.0843
_reflns_number_gt              5056
_reflns_number_total           6680
_reflns_threshold_expression   I>2\s(I)
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,-y,1/2+z
1/2+x,1/2-y,-z
-x,1/2+y,1/2-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
I1 -0.47477(3) 0.19712(2) 0.03022(2) 0.05140(9) Uani d . 1.00 . . I
I2 -0.49191(3) 0.22709(2) -0.46580(2) 0.05910(10) Uani d . 1.00 . . I
O1 -0.3889(3) -0.1533(2) -0.2192(2) 0.0476(7) Uani d . 1.00 . . O
N1 -0.6937(3) 0.0112(3) -0.4073(3) 0.0456(9) Uani d . 1.00 . . N
N2 -0.2413(3) 0.0067(3) -0.1359(2) 0.0397(8) Uani d . 1.00 . . N
C1 -0.6283(4) 0.0978(3) -0.1783(3) 0.0376(9) Uani d . 1.00 . . C
C2 -0.7162(4) 0.1646(3) -0.1657(3) 0.0433(10) Uani d . 1.00 . . C
C3 -0.8004(4) 0.1815(3) -0.2333(3) 0.0460(10) Uani d . 1.00 . . C
C4 -0.7932(4) 0.1331(3) -0.3135(3) 0.0460(10) Uani d . 1.00 . . C
C5 -0.7021(4) 0.0626(3) -0.3276(3) 0.0370(9) Uani d . 1.00 . . C
C6 -0.6178(4) 0.0430(3) -0.2598(3) 0.0340(8) Uani d . 1.00 . . C
C7 -0.5301(4) -0.0318(3) -0.2739(2) 0.0359(8) Uani d . 1.00 . . C
C8 -0.5303(4) -0.0829(3) -0.3538(3) 0.0449(9) Uani d . 1.00 . . C
C9 -0.6114(4) -0.0592(3) -0.4189(3) 0.0500(10) Uani d . 1.00 . . C
C10 -0.7745(5) 0.0362(4) -0.4817(4) 0.0680(10) Uani d . 1.00 . . C
C11 -0.4377(4) -0.0574(3) -0.2029(3) 0.0383(9) Uani d . 1.00 . . C
C12 -0.3414(4) 0.0235(3) -0.2049(3) 0.0340(8) Uani d . 1.00 . . C
C13 -0.2815(4) 0.0371(3) -0.2964(3) 0.0421(10) Uani d . 1.00 . . C
C14 -0.1554(4) 0.0737(4) -0.2835(3) 0.0500(10) Uani d . 1.00 . . C
C15 -0.0821(4) -0.0150(4) -0.2495(4) 0.0570(10) Uani d . 1.00 . . C
C16 -0.1470(4) -0.0651(4) -0.1720(3) 0.0510(10) Uani d . 1.00 . . C
C17 -0.2846(4) -0.0325(4) -0.0478(3) 0.0510(10) Uani d . 1.00 . . C
C18 -0.1856(4) 0.1079(3) -0.1221(3) 0.0480(10) Uani d . 1.00 . . C
C19 -0.1514(4) 0.1565(4) -0.2124(4) 0.0510(10) Uani d . 1.00 . . C
C20 -0.2242(5) 0.2469(4) -0.2349(4) 0.068(2) Uani d . 1.00 . . C
C21 -0.2050(9) 0.3099(7) -0.2923(7) 0.132(4) Uani d . 1.00 . . C
H1 -0.5730 0.0863 -0.1311 0.0436 Uiso calc . 1.00 . . H
H2 -0.7198 0.2016 -0.1102 0.0485 Uiso calc . 1.00 . . H
H3 -0.8631 0.2285 -0.2231 0.0531 Uiso calc . 1.00 . . H
H4 -0.8497 0.1479 -0.3600 0.0558 Uiso calc . 1.00 . . H
H5 -0.4709 -0.1343 -0.3631 0.0533 Uiso calc . 1.00 . . H
H6 -0.6106 -0.0949 -0.4749 0.0594 Uiso calc . 1.00 . . H
H7 -0.7748 0.1076 -0.4909 0.0760 Uiso calc . 1.00 . . H
H8 -0.7483 0.0033 -0.5353 0.0760 Uiso calc . 1.00 . . H
H9 -0.8530 0.0141 -0.4672 0.0760 Uiso calc . 1.00 . . H
H10 -0.4738 -0.0584 -0.1438 0.0448 Uiso calc . 1.00 . . H
H11 -0.4506 -0.2020 -0.2178 0.0539 Uiso calc . 1.00 . . H
H12 -0.3790 0.0853 -0.1894 0.0410 Uiso calc . 1.00 . . H
H13 -0.2835 -0.0238 -0.3282 0.0497 Uiso calc . 1.00 . . H
H14 -0.3269 0.0867 -0.3300 0.0497 Uiso calc . 1.00 . . H
H15 -0.1239 0.1003 -0.3383 0.0587 Uiso calc . 1.00 . . H
H16 -0.0695 -0.0626 -0.2969 0.0679 Uiso calc . 1.00 . . H
H17 -0.0053 0.0074 -0.2295 0.0679 Uiso calc . 1.00 . . H
H18 -0.1852 -0.1258 -0.1915 0.0581 Uiso calc . 1.00 . . H
H19 -0.0941 -0.0821 -0.1243 0.0581 Uiso calc . 1.00 . . H
H20 -0.2191 -0.0395 -0.0079 0.0576 Uiso calc . 1.00 . . H
H21 -0.3203 -0.0966 -0.0560 0.0576 Uiso calc . 1.00 . . H
H22 -0.3402 0.0126 -0.0231 0.0576 Uiso calc . 1.00 . . H
H23 -0.1160 0.0996 -0.0854 0.0546 Uiso calc . 1.00 . . H
H24 -0.2395 0.1501 -0.0909 0.0546 Uiso calc . 1.00 . . H
H25 -0.0692 0.1764 -0.2060 0.0614 Uiso calc . 1.00 . . H
H26 -0.2919 0.2610 -0.1973 0.0779 Uiso calc . 1.00 . . H
H27 -0.1408 0.3011 -0.3338 0.1405 Uiso calc . 1.00 . . H
H28 -0.2583 0.3653 -0.3030 0.1405 Uiso calc . 1.00 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
I1 0.0691(2) 0.04500(10) 0.04000(10) 0.00060(10) -0.0026(2) -0.00720(10)
I2 0.0593(2) 0.0541(2) 0.0638(2) 0.00090(10) 0.0125(2) -0.00880(10)
O1 0.052(2) 0.0330(10) 0.058(2) 0.0040(10) 0.001(2) -0.0010(10)
N1 0.049(2) 0.047(2) 0.040(2) -0.010(2) -0.012(2) -0.003(2)
N2 0.047(2) 0.040(2) 0.032(2) 0.006(2) -0.0050(10) -0.0040(10)
C1 0.044(2) 0.036(2) 0.033(2) -0.001(2) 0.001(2) 0.001(2)
C2 0.047(2) 0.041(2) 0.042(2) 0.001(2) 0.015(2) -0.001(2)
C3 0.035(2) 0.041(2) 0.063(3) 0.001(2) 0.008(2) 0.006(2)
C4 0.038(2) 0.044(2) 0.058(3) -0.005(2) -0.004(2) 0.010(2)
C5 0.037(2) 0.033(2) 0.041(2) -0.011(2) -0.001(2) 0.004(2)
C6 0.038(2) 0.032(2) 0.032(2) -0.007(2) 0.001(2) 0.002(2)
C7 0.040(2) 0.033(2) 0.035(2) -0.004(2) 0.004(2) 0.0010(10)
C8 0.054(2) 0.038(2) 0.042(2) 0.001(2) 0.001(2) -0.010(2)
C9 0.064(3) 0.046(2) 0.040(2) -0.005(2) -0.006(2) -0.017(2)
C10 0.077(3) 0.076(4) 0.052(3) -0.006(3) -0.026(3) -0.004(3)
C11 0.043(2) 0.038(2) 0.034(2) 0.005(2) -0.001(2) -0.001(2)
C12 0.034(2) 0.036(2) 0.032(2) 0.007(2) 0.000(2) 0.004(2)
C13 0.053(3) 0.045(2) 0.028(2) -0.007(2) -0.001(2) -0.003(2)
C14 0.049(3) 0.058(3) 0.042(3) 0.002(2) 0.013(2) 0.000(2)
C15 0.046(3) 0.064(3) 0.062(3) 0.007(2) 0.008(2) -0.016(2)
C16 0.047(3) 0.047(3) 0.057(3) 0.014(2) -0.009(2) -0.003(2)
C17 0.068(3) 0.057(3) 0.028(2) 0.004(2) -0.004(2) 0.005(2)
C18 0.051(3) 0.047(2) 0.045(3) -0.003(2) -0.001(2) -0.008(2)
C19 0.044(2) 0.049(3) 0.061(3) -0.008(2) 0.002(2) -0.002(2)
C20 0.065(3) 0.049(3) 0.088(4) 0.000(3) 0.017(3) 0.010(3)
C21 0.145(8) 0.116(6) 0.136(7) 0.057(6) 0.057(6) 0.059(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
I I -0.474 1.812
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, 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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O1 H11 . . . 109.0 yes
C5 N1 C9 . . . 120.7(4) yes
C5 N1 C10 . . . 119.7(4) yes
C9 N1 C10 . . . 119.6(4) yes
C12 N2 C16 . . . 111.5(3) yes
C12 N2 C17 . . . 113.3(3) yes
C12 N2 C18 . . . 105.6(3) yes
C16 N2 C17 . . . 108.6(3) yes
C16 N2 C18 . . . 108.4(3) yes
C17 N2 C18 . . . 109.2(3) yes
C2 C1 C6 . . . 121.3(4) no
C2 C1 H1 . . . 119.1 no
C6 C1 H1 . . . 119.6 no
C1 C2 C3 . . . 120.4(4) no
C1 C2 H2 . . . 119.2 no
C3 C2 H2 . . . 120.4 no
C2 C3 C4 . . . 121.0(4) no
C2 C3 H3 . . . 119.5 no
C4 C3 H3 . . . 119.5 no
C3 C4 C5 . . . 119.3(4) no
C3 C4 H4 . . . 119.9 no
C5 C4 H4 . . . 120.8 no
N1 C5 C4 . . . 120.7(4) no
N1 C5 C6 . . . 118.7(4) no
C4 C5 C6 . . . 120.5(4) no
C1 C6 C5 . . . 117.4(4) no
C1 C6 C7 . . . 123.0(3) no
C5 C6 C7 . . . 119.6(3) no
C6 C7 C8 . . . 118.4(4) no
C6 C7 C11 . . . 122.1(3) no
C8 C7 C11 . . . 119.5(4) no
C7 C8 C9 . . . 120.1(4) no
C7 C8 H5 . . . 118.3 no
C9 C8 H5 . . . 121.6 no
N1 C9 C8 . . . 122.5(4) no
N1 C9 H6 . . . 117.9 no
C8 C9 H6 . . . 119.7 no
N1 C10 H7 . . . 109.5 no
N1 C10 H8 . . . 109.5 no
N1 C10 H9 . . . 109.5 no
H7 C10 H8 . . . 109.5 no
H7 C10 H9 . . . 109.5 no
H8 C10 H9 . . . 109.5 no
O1 C11 C7 . . . 110.5(3) no
O1 C11 C12 . . . 110.8(3) no
O1 C11 H10 . . . 108.0 no
C7 C11 C12 . . . 108.4(3) no
C7 C11 H10 . . . 110.1 no
C12 C11 H10 . . . 109.0 no
N2 C12 C11 . . . 114.0(3) no
N2 C12 C13 . . . 106.6(3) no
N2 C12 H12 . . . 106.8 no
C11 C12 C13 . . . 114.5(3) no
C11 C12 H12 . . . 106.5 no
C13 C12 H12 . . . 108.1 no
C12 C13 C14 . . . 109.8(3) no
C12 C13 H13 . . . 109.7 no
C12 C13 H14 . . . 107.7 no
C14 C13 H13 . . . 111.3 no
C14 C13 H14 . . . 110.0 no
H13 C13 H14 . . . 108.2 no
C13 C14 C15 . . . 107.6(4) no
C13 C14 C19 . . . 110.3(4) no
C13 C14 H15 . . . 111.1 no
C15 C14 C19 . . . 108.0(4) no
C15 C14 H15 . . . 111.5 no
C19 C14 H15 . . . 108.3 no
C14 C15 C16 . . . 109.2(4) no
C14 C15 H16 . . . 110.2 no
C14 C15 H17 . . . 110.6 no
C16 C15 H16 . . . 110.0 no
C16 C15 H17 . . . 109.5 no
H16 C15 H17 . . . 107.3 no
N2 C16 C15 . . . 109.3(4) no
N2 C16 H18 . . . 108.6 no
N2 C16 H19 . . . 108.7 no
C15 C16 H18 . . . 110.7 no
C15 C16 H19 . . . 111.5 no
H18 C16 H19 . . . 107.9 no
N2 C17 H20 . . . 109.2 no
N2 C17 H21 . . . 109.8 no
N2 C17 H22 . . . 109.8 no
H20 C17 H21 . . . 108.8 no
H20 C17 H22 . . . 109.5 no
H21 C17 H22 . . . 109.7 no
N2 C18 C19 . . . 111.2(4) no
N2 C18 H23 . . . 108.5 no
N2 C18 H24 . . . 109.2 no
C19 C18 H23 . . . 109.8 no
C19 C18 H24 . . . 110.0 no
H23 C18 H24 . . . 108.1 no
C14 C19 C18 . . . 107.3(4) no
C14 C19 C20 . . . 114.0(4) no
C14 C19 H25 . . . 107.0 no
C18 C19 C20 . . . 113.3(4) no
C18 C19 H25 . . . 105.5 no
C20 C19 H25 . . . 109.2 no
C19 C20 C21 . . . 127.8(7) no
C19 C20 H26 . . . 117.4 no
C21 C20 H26 . . . 114.6 no
C20 C21 H27 . . . 120.2 no
C20 C21 H28 . . . 122.0 no
H27 C21 H28 . . . 117.3 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 . . 1.411(5) yes
O1 H11 . . 0.953 no
N1 C5 . . 1.376(6) yes
N1 C9 . . 1.332(6) yes
N1 C10 . . 1.476(7) yes
N2 C12 . . 1.547(5) yes
N2 C16 . . 1.529(6) yes
N2 C17 . . 1.497(6) yes
N2 C18 . . 1.501(6) yes
C1 C2 . . 1.347(6) no
C1 C6 . . 1.423(5) no
C1 H1 . . 0.954 no
C2 C3 . . 1.406(6) no
C2 H2 . . 0.965 no
C3 C4 . . 1.362(7) no
C3 H3 . . 0.958 no
C4 C5 . . 1.410(6) no
C4 H4 . . 0.964 no
C5 C6 . . 1.415(6) no
C6 C7 . . 1.421(5) no
C7 C8 . . 1.373(5) no
C7 C11 . . 1.527(6) no
C8 C9 . . 1.373(6) no
C8 H5 . . 0.969 no
C9 H6 . . 0.962 no
C10 H7 . . 0.960 no
C10 H8 . . 0.960 no
C10 H9 . . 0.960 no
C11 C12 . . 1.531(6) no
C11 H10 . . 0.973 no
C12 C13 . . 1.536(6) no
C12 H12 . . 0.956 no
C13 C14 . . 1.520(7) no
C13 H13 . . 0.939 no
C13 H14 . . 0.976 no
C14 C15 . . 1.530(7) no
C14 C19 . . 1.530(7) no
C14 H15 . . 0.959 no
C15 C16 . . 1.524(7) no
C15 H16 . . 0.960 no
C15 H17 . . 0.966 no
C16 H18 . . 0.961 no
C16 H19 . . 0.958 no
C17 H20 . . 0.955 no
C17 H21 . . 0.952 no
C17 H22 . . 0.945 no
C18 C19 . . 1.544(7) no
C18 H23 . . 0.965 no
C18 H24 . . 0.951 no
C19 C20 . . 1.497(7) no
C19 H25 . . 0.972 no
C20 C21 . . 1.220(10) no
C20 H26 . . 0.968 no
C21 H27 . . 0.962 no
C21 H28 . . 0.965 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
I2 O1 3.461(3) . 4_454 ?
O1 C3 3.151(5) . 4_444 ?
O1 C2 3.200(5) . 4_444 ?
O1 C4 3.545(5) . 4_444 ?
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
O1 C11 C7 C6 . . . . 160.0(3) no
O1 C11 C7 C8 . . . . -19.2(5) no
O1 C11 C12 N2 . . . . -58.5(4) no
O1 C11 C12 C13 . . . . 64.6(4) no
N1 C5 C4 C3 . . . . 178.8(4) no
N1 C5 C6 C1 . . . . 179.6(4) no
N1 C5 C6 C7 . . . . -2.5(6) no
N1 C9 C8 C7 . . . . -1.5(7) no
N2 C12 C11 C7 . . . . -179.9(3) no
N2 C12 C13 C14 . . . . -24.2(4) no
N2 C16 C15 C14 . . . . -17.2(5) no
N2 C18 C19 C14 . . . . -14.9(5) no
N2 C18 C19 C20 . . . . 111.8(4) no
C1 C2 C3 C4 . . . . -1.9(7) no
C1 C6 C5 C4 . . . . -0.9(6) no
C1 C6 C7 C8 . . . . 177.7(4) no
C1 C6 C7 C11 . . . . -1.5(6) no
C2 C1 C6 C5 . . . . 1.2(6) no
C2 C1 C6 C7 . . . . -176.7(4) no
C2 C3 C4 C5 . . . . 2.1(7) no
C3 C2 C1 C6 . . . . 0.2(6) no
C3 C4 C5 C6 . . . . -0.7(6) no
C4 C5 N1 C9 . . . . -176.4(4) no
C4 C5 N1 C10 . . . . 5.4(6) no
C4 C5 C6 C7 . . . . 177.0(4) no
C5 N1 C9 C8 . . . . -1.1(7) no
C5 C6 C7 C8 . . . . 0.0(6) no
C5 C6 C7 C11 . . . . -179.3(4) no
C6 C5 N1 C9 . . . . 3.1(6) no
C6 C5 N1 C10 . . . . -175.1(4) no
C6 C7 C8 C9 . . . . 2.0(6) no
C6 C7 C11 C12 . . . . -78.4(4) no
C7 C11 C12 C13 . . . . -56.9(4) no
C8 C7 C11 C12 . . . . 102.3(4) no
C8 C9 N1 C10 . . . . 177.1(4) no
C9 C8 C7 C11 . . . . -178.7(4) no
C11 C12 N2 C16 . . . . 84.2(4) no
C11 C12 N2 C17 . . . . -38.7(4) no
C11 C12 N2 C18 . . . . -158.2(3) no
C11 C12 C13 C14 . . . . -151.1(4) no
C12 N2 C16 C15 . . . . 67.5(4) no
C12 N2 C18 C19 . . . . -51.8(4) no
C12 C13 C14 C15 . . . . 73.8(5) no
C12 C13 C14 C19 . . . . -43.8(5) no
C13 C12 N2 C16 . . . . -43.0(4) no
C13 C12 N2 C17 . . . . -165.9(3) no
C13 C12 N2 C18 . . . . 74.5(4) no
C13 C14 C15 C16 . . . . -48.6(5) no
C13 C14 C19 C18 . . . . 66.2(5) no
C13 C14 C19 C20 . . . . -60.1(5) no
C14 C19 C20 C21 . . . . -70.8(9) no
C15 C14 C19 C18 . . . . -51.2(5) no
C15 C14 C19 C20 . . . . -177.4(4) no
C15 C16 N2 C17 . . . . -167.0(4) no
C15 C16 N2 C18 . . . . -48.4(5) no
C16 N2 C18 C19 . . . . 67.8(4) no
C16 C15 C14 C19 . . . . 70.5(5) no
C17 N2 C18 C19 . . . . -174.0(4) no
C18 C19 C20 C21 . . . . 166.1(8) no
C18 C19 C20 C21 . . . . 166.1(8) no