#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:07:09 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178421 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/42/4024289.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_4024289
loop_
_publ_author_name
'Yan Huang'
'Qiong Li'
'Tian-Liang Liu'
'Peng-Fei Xu'
_publ_contact_author_email       huangyan03@lzu.cn
_publ_contact_author_name        'Pengfei Xu'
_publ_section_title
;
Diastereoselective Synthesis of β-Substituted-α,γ-Diaminobutyric Acids
and Pyrrolidines Containing Multichiral Centers
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1252
_journal_page_last               1258
_journal_paper_doi               10.1021/jo8023076
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration rm
_chemical_formula_sum            'C21 H26 N2 O4'
_chemical_formula_weight         370.44
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2892(11)
_cell_length_b                   12.2674(19)
_cell_length_c                   22.715(4)
_cell_measurement_reflns_used    3138
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22.14
_cell_measurement_theta_min      2.44
_cell_volume                     2031.1(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11479
_diffrn_reflns_theta_full        26.45
_diffrn_reflns_theta_max         26.45
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.108
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0429P)²+0.2813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.1014
_reflns_number_gt                1650
_reflns_number_total             2399
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8023076_si_004.cif
_cod_data_source_block           050822a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'NONE' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4024289
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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
O1 O -0.0426(2) 0.14256(16) 0.85198(7) 0.0553(5) Uani 1 1 d . . .
O2 O -0.2125(3) 0.2005(2) 0.92566(9) 0.0811(7) Uani 1 1 d . . .
O3 O -0.1677(5) -0.0139(3) 1.11327(14) 0.1275(12) Uani 1 1 d . . .
O4 O 0.1227(6) -0.0107(4) 1.10466(13) 0.1520(16) Uani 1 1 d . . .
N1 N 0.2802(3) 0.18227(17) 0.91925(9) 0.0477(5) Uani 1 1 d . . .
N2 N -0.0285(6) 0.0145(3) 1.08875(12) 0.0829(9) Uani 1 1 d . . .
C1 C 0.2855(4) 0.1406(2) 0.86800(11) 0.0448(6) Uani 1 1 d . . .
C2 C 0.4366(4) 0.1521(2) 0.82346(12) 0.0566(7) Uani 1 1 d . . .
H2 H 0.5401 0.1980 0.8354 0.068 Uiso 1 1 calc R . .
C3 C 0.4868(4) 0.0369(3) 0.80237(14) 0.0706(9) Uani 1 1 d . . .
H3A H 0.5980 0.0380 0.7789 0.085 Uiso 1 1 calc R . .
H3B H 0.5042 -0.0119 0.8355 0.085 Uiso 1 1 calc R . .
C4 C 0.3216(4) 0.0020(2) 0.76519(13) 0.0641(8) Uani 1 1 d . . .
H4A H 0.2689 -0.0651 0.7801 0.077 Uiso 1 1 calc R . .
H4B H 0.3567 -0.0086 0.7244 0.077 Uiso 1 1 calc R . .
C5 C 0.1852(4) 0.0970(2) 0.77118(11) 0.0492(7) Uani 1 1 d . . .
C6 C 0.1277(3) 0.0881(2) 0.83665(10) 0.0439(6) Uani 1 1 d . . .
H6 H 0.1202 0.0111 0.8479 0.053 Uiso 1 1 calc R . .
C7 C 0.3199(4) 0.1964(2) 0.77123(12) 0.0554(7) Uani 1 1 d . . .
C8 C 0.4309(5) 0.2090(3) 0.71447(13) 0.0818(10) Uani 1 1 d . . .
H8A H 0.3503 0.2286 0.6828 0.123 Uiso 1 1 calc R . .
H8B H 0.4907 0.1413 0.7054 0.123 Uiso 1 1 calc R . .
H8C H 0.5215 0.2650 0.7196 0.123 Uiso 1 1 calc R . .
C9 C 0.2262(5) 0.3062(2) 0.78383(14) 0.0750(10) Uani 1 1 d . . .
H9A H 0.1518 0.2999 0.8185 0.112 Uiso 1 1 calc R . .
H9B H 0.1504 0.3261 0.7510 0.112 Uiso 1 1 calc R . .
H9C H 0.3180 0.3613 0.7898 0.112 Uiso 1 1 calc R . .
C10 C 0.0291(5) 0.0969(3) 0.72748(11) 0.0726(9) Uani 1 1 d . . .
H10A H 0.0777 0.0969 0.6882 0.109 Uiso 1 1 calc R . .
H10B H -0.0449 0.1608 0.7332 0.109 Uiso 1 1 calc R . .
H10C H -0.0446 0.0330 0.7332 0.109 Uiso 1 1 calc R . .
C11 C -0.0640(4) 0.1711(2) 0.90893(12) 0.0519(7) Uani 1 1 d . . .
C12 C 0.1031(4) 0.1733(2) 0.94901(11) 0.0451(6) Uani 1 1 d . . .
H12 H 0.0911 0.2403 0.9722 0.054 Uiso 1 1 calc R . .
C13 C 0.1095(4) 0.07931(19) 0.99482(10) 0.0446(6) Uani 1 1 d . . .
H13 H 0.2215 0.0901 1.0180 0.054 Uiso 1 1 calc R . .
C14 C -0.0500(4) 0.0895(2) 1.03742(11) 0.0630(8) Uani 1 1 d . . .
H14A H -0.0577 0.1640 1.0514 0.076 Uiso 1 1 calc R . .
H14B H -0.1634 0.0726 1.0170 0.076 Uiso 1 1 calc R . .
C15 C 0.1247(4) -0.03358(19) 0.96693(10) 0.0444(6) Uani 1 1 d . . .
C16 C -0.0295(4) -0.0815(2) 0.94277(11) 0.0582(7) Uani 1 1 d . . .
H16 H -0.1420 -0.0461 0.9456 0.070 Uiso 1 1 calc R . .
C17 C -0.0197(6) -0.1815(3) 0.91436(15) 0.0838(11) Uani 1 1 d . . .
H17 H -0.1244 -0.2131 0.8984 0.101 Uiso 1 1 calc R . .
C18 C 0.1451(8) -0.2327(3) 0.91026(18) 0.0978(14) Uani 1 1 d . . .
H18 H 0.1537 -0.2989 0.8905 0.117 Uiso 1 1 calc R . .
C19 C 0.2969(6) -0.1879(3) 0.93466(17) 0.0881(12) Uani 1 1 d . . .
H19 H 0.4077 -0.2252 0.9320 0.106 Uiso 1 1 calc R . .
C20 C 0.2925(4) -0.0873(2) 0.96374(13) 0.0632(8) Uani 1 1 d . . .
C21 C 0.4650(4) -0.0427(3) 0.99104(18) 0.0955(12) Uani 1 1 d . . .
H21A H 0.4971 0.0247 0.9722 0.143 Uiso 1 1 calc R . .
H21B H 0.5630 -0.0942 0.9860 0.143 Uiso 1 1 calc R . .
H21C H 0.4451 -0.0303 1.0323 0.143 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 0.0033 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C11 O1 C6 116.61(19) . . ?
C1 N1 C12 114.8(2) . . ?
O4 N2 O3 123.9(4) . . ?
O4 N2 C14 119.4(3) . . ?
O3 N2 C14 116.7(4) . . ?
N1 C1 C6 125.8(2) . . ?
N1 C1 C2 126.9(2) . . ?
C6 C1 C2 106.4(2) . . ?
C1 C2 C3 107.3(2) . . ?
C1 C2 C7 98.4(2) . . ?
C3 C2 C7 102.3(2) . . ?
C1 C2 H2 115.6 . . ?
C3 C2 H2 115.6 . . ?
C7 C2 H2 115.6 . . ?
C4 C3 C2 104.0(2) . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C3 C4 C5 104.3(2) . . ?
C3 C4 H4A 110.9 . . ?
C5 C4 H4A 110.9 . . ?
C3 C4 H4B 110.9 . . ?
C5 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
C10 C5 C4 115.4(2) . . ?
C10 C5 C6 115.3(2) . . ?
C4 C5 C6 101.9(2) . . ?
C10 C5 C7 118.3(2) . . ?
C4 C5 C7 100.6(2) . . ?
C6 C5 C7 103.0(2) . . ?
O1 C6 C1 110.13(19) . . ?
O1 C6 C5 115.4(2) . . ?
C1 C6 C5 102.6(2) . . ?
O1 C6 H6 109.5 . . ?
C1 C6 H6 109.5 . . ?
C5 C6 H6 109.5 . . ?
C8 C7 C9 107.6(2) . . ?
C8 C7 C2 112.9(3) . . ?
C9 C7 C2 114.0(2) . . ?
C8 C7 C5 114.2(2) . . ?
C9 C7 C5 113.8(2) . . ?
C2 C7 C5 94.1(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 O1 119.0(2) . . ?
O2 C11 C12 121.8(2) . . ?
O1 C11 C12 119.1(2) . . ?
N1 C12 C11 115.58(19) . . ?
N1 C12 C13 109.8(2) . . ?
C11 C12 C13 114.3(2) . . ?
N1 C12 H12 105.4 . . ?
C11 C12 H12 105.4 . . ?
C13 C12 H12 105.4 . . ?
C14 C13 C15 113.2(2) . . ?
C14 C13 C12 110.1(2) . . ?
C15 C13 C12 113.41(19) . . ?
C14 C13 H13 106.5 . . ?
C15 C13 H13 106.5 . . ?
C12 C13 H13 106.5 . . ?
N2 C14 C13 111.5(3) . . ?
N2 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
N2 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C20 119.5(2) . . ?
C16 C15 C13 119.4(2) . . ?
C20 C15 C13 121.0(3) . . ?
C15 C16 C17 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 119.1(4) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 122.1(4) . . ?
C18 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C15 C20 C19 117.5(3) . . ?
C15 C20 C21 122.7(3) . . ?
C19 C20 C21 119.7(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
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
O1 C11 1.349(3) . ?
O1 C6 1.452(3) . ?
O2 C11 1.203(3) . ?
O3 N2 1.209(4) . ?
O4 N2 1.200(4) . ?
N1 C1 1.272(3) . ?
N1 C12 1.461(3) . ?
N2 C14 1.493(4) . ?
C1 C6 1.499(3) . ?
C1 C2 1.502(4) . ?
C2 C3 1.537(4) . ?
C2 C7 1.557(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.532(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.538(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.510(4) . ?
C5 C6 1.549(3) . ?
C5 C7 1.565(4) . ?
C6 H6 0.9800 . ?
C7 C8 1.530(4) . ?
C7 C9 1.538(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.521(4) . ?
C12 C13 1.554(3) . ?
C12 H12 0.9800 . ?
C13 C14 1.518(4) . ?
C13 C15 1.527(3) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.383(4) . ?
C15 C20 1.391(4) . ?
C16 C17 1.388(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.358(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.354(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.400(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.505(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
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
C12 N1 C1 C6 1.8(4) . . . . ?
C12 N1 C1 C2 169.8(2) . . . . ?
N1 C1 C2 C3 129.3(3) . . . . ?
C6 C1 C2 C3 -60.9(3) . . . . ?
N1 C1 C2 C7 -125.0(3) . . . . ?
C6 C1 C2 C7 44.9(2) . . . . ?
C1 C2 C3 C4 70.9(3) . . . . ?
C7 C2 C3 C4 -32.1(3) . . . . ?
C2 C3 C4 C5 -3.4(3) . . . . ?
C3 C4 C5 C10 165.9(2) . . . . ?
C3 C4 C5 C6 -68.5(3) . . . . ?
C3 C4 C5 C7 37.4(3) . . . . ?
C11 O1 C6 C1 -41.1(3) . . . . ?
C11 O1 C6 C5 -156.6(2) . . . . ?
N1 C1 C6 O1 34.0(3) . . . . ?
C2 C1 C6 O1 -136.0(2) . . . . ?
N1 C1 C6 C5 157.4(3) . . . . ?
C2 C1 C6 C5 -12.6(3) . . . . ?
C10 C5 C6 O1 -35.0(3) . . . . ?
C4 C5 C6 O1 -160.7(2) . . . . ?
C7 C5 C6 O1 95.3(2) . . . . ?
C10 C5 C6 C1 -154.7(2) . . . . ?
C4 C5 C6 C1 79.6(2) . . . . ?
C7 C5 C6 C1 -24.4(2) . . . . ?
C1 C2 C7 C8 -175.1(2) . . . . ?
C3 C2 C7 C8 -65.2(3) . . . . ?
C1 C2 C7 C9 61.8(3) . . . . ?
C3 C2 C7 C9 171.7(2) . . . . ?
C1 C2 C7 C5 -56.6(2) . . . . ?
C3 C2 C7 C5 53.3(2) . . . . ?
C10 C5 C7 C8 -64.2(3) . . . . ?
C4 C5 C7 C8 62.4(3) . . . . ?
C6 C5 C7 C8 167.4(3) . . . . ?
C10 C5 C7 C9 60.0(3) . . . . ?
C4 C5 C7 C9 -173.4(2) . . . . ?
C6 C5 C7 C9 -68.5(3) . . . . ?
C10 C5 C7 C2 178.5(2) . . . . ?
C4 C5 C7 C2 -55.0(2) . . . . ?
C6 C5 C7 C2 50.0(2) . . . . ?
C6 O1 C11 O2 -168.4(3) . . . . ?
C6 O1 C11 C12 16.1(3) . . . . ?
C1 N1 C12 C11 -29.6(3) . . . . ?
C1 N1 C12 C13 101.6(2) . . . . ?
O2 C11 C12 N1 -154.4(3) . . . . ?
O1 C11 C12 N1 21.0(3) . . . . ?
O2 C11 C12 C13 76.7(3) . . . . ?
O1 C11 C12 C13 -108.0(3) . . . . ?
N1 C12 C13 C14 163.9(2) . . . . ?
C11 C12 C13 C14 -64.3(3) . . . . ?
N1 C12 C13 C15 -68.1(3) . . . . ?
C11 C12 C13 C15 63.8(3) . . . . ?
O4 N2 C14 C13 28.6(5) . . . . ?
O3 N2 C14 C13 -154.2(3) . . . . ?
C15 C13 C14 N2 63.1(3) . . . . ?
C12 C13 C14 N2 -168.8(2) . . . . ?
C14 C13 C15 C16 48.6(3) . . . . ?
C12 C13 C15 C16 -77.7(3) . . . . ?
C14 C13 C15 C20 -133.5(3) . . . . ?
C12 C13 C15 C20 100.1(3) . . . . ?
C20 C15 C16 C17 -1.2(4) . . . . ?
C13 C15 C16 C17 176.7(2) . . . . ?
C15 C16 C17 C18 -0.2(5) . . . . ?
C16 C17 C18 C19 1.5(6) . . . . ?
C17 C18 C19 C20 -1.4(6) . . . . ?
C16 C15 C20 C19 1.3(4) . . . . ?
C13 C15 C20 C19 -176.6(2) . . . . ?
C16 C15 C20 C21 -177.5(3) . . . . ?
C13 C15 C20 C21 4.7(4) . . . . ?
C18 C19 C20 C15 0.0(5) . . . . ?
C18 C19 C20 C21 178.8(4) . . . . ?
