#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/45/2224595.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2224595
loop_
_publ_author_name
'Zhong, Jiangchun'
'Zheng, Bing'
'Hou, Shicong'
_publ_section_title
(1R,3S)-3-Hydroxymethyl-N-isopropyl-2,2-dimethylcyclopropanecarboxamide
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o118
_journal_paper_doi               10.1107/S1600536809051538
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C10 H19 N O2'
_chemical_formula_moiety         'C10 H19 N O2'
_chemical_formula_sum            'C10 H19 N O2'
_chemical_formula_weight         185.26
_chemical_name_systematic
;
(1R,3S)-3-Hydroxymethyl-N-isopropyl-2,2-
dimethylcyclopropanecarboxamide
;
_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            8
_cell_length_a                   9.4628(19)
_cell_length_b                   12.298(3)
_cell_length_c                   18.710(4)
_cell_measurement_reflns_used    426
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      2.17
_cell_volume                     2177.3(8)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2001)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 2001)'
_computing_data_reduction        'RAPID-AUTO (Rigaku, 2001)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS Rapid IP area-detector'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0818
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15043
_diffrn_reflns_theta_full        68.18
_diffrn_reflns_theta_max         68.18
_diffrn_reflns_theta_min         4.30
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  0.7935
_exptl_absorpt_correction_T_min  0.7340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.130
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.194
_refine_ls_extinction_coef       0.0058(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         2271
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0502P)²+1.0161P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1101
_reflns_number_gt                2129
_reflns_number_total             2271
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cv2626.cif
_cod_data_source_block           I
_cod_original_cell_volume        2177.4(8)
_cod_database_code               2224595
_cod_database_fobs_code          2224595
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_type_symbol
_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
O O1 0.6210(2) 1.20449(16) 0.05202(10) 0.0338(5) Uani d . 1 . .
H H1A 0.6936 1.2425 0.0454 0.041 Uiso d R 1 . .
O O2 0.5838(2) 0.94520(18) 0.20498(10) 0.0365(5) Uani d . 1 . .
O O3 1.1281(2) 0.81763(16) 0.47435(11) 0.0408(5) Uani d . 1 . .
H H3 1.0658 0.8016 0.5045 0.049 Uiso d R 1 . .
O O4 1.0762(2) 0.8858(2) 0.28306(11) 0.0440(6) Uani d . 1 . .
N N1 0.7727(2) 0.87180(18) 0.26112(11) 0.0273(5) Uani d . 1 . .
H H1 0.8639 0.8795 0.2689 0.033 Uiso d R 1 . .
N N2 1.2844(2) 0.88054(19) 0.22414(11) 0.0286(5) Uani d . 1 . .
H H2 1.3750 0.8966 0.2234 0.034 Uiso d R 1 . .
C C1 0.8241(3) 1.0016(2) 0.08897(14) 0.0287(6) Uani d . 1 . .
C C2 0.7827(3) 1.1031(2) 0.12682(14) 0.0281(6) Uani d . 1 . .
H H2A 0.8595 1.1589 0.1275 0.034 Uiso calc R 1 . .
C C3 0.8184(3) 1.0024(2) 0.17075(13) 0.0280(6) Uani d . 1 . .
H H3A 0.9138 1.0058 0.1936 0.034 Uiso calc R 1 . .
C C4 0.7151(4) 0.9388(2) 0.04695(15) 0.0370(7) Uani d . 1 . .
H H4A 0.6261 0.9369 0.0737 0.055 Uiso calc R 1 . .
H H4B 0.7487 0.8644 0.0391 0.055 Uiso calc R 1 . .
H H4C 0.6996 0.9744 0.0007 0.055 Uiso calc R 1 . .
C C5 0.9697(3) 0.9970(3) 0.05666(17) 0.0428(8) Uani d . 1 . .
H H5A 0.9664 1.0248 0.0076 0.064 Uiso calc R 1 . .
H H5B 1.0030 0.9215 0.0562 0.064 Uiso calc R 1 . .
H H5C 1.0345 1.0416 0.0851 0.064 Uiso calc R 1 . .
C C6 0.6372(3) 1.1523(2) 0.12027(14) 0.0320(6) Uani d . 1 . .
H H6A 0.5649 1.0947 0.1256 0.038 Uiso calc R 1 . .
H H6B 0.6228 1.2062 0.1589 0.038 Uiso calc R 1 . .
C C7 0.7133(3) 0.9388(2) 0.21314(13) 0.0264(6) Uani d . 1 . .
C C8 0.6914(3) 0.8114(2) 0.31424(14) 0.0297(6) Uani d . 1 . .
H H8A 0.5976 0.7929 0.2929 0.036 Uiso calc R 1 . .
C C9 0.7659(4) 0.7061(3) 0.33356(18) 0.0479(8) Uani d . 1 . .
H H9A 0.7639 0.6567 0.2925 0.072 Uiso calc R 1 . .
H H9B 0.7176 0.6720 0.3741 0.072 Uiso calc R 1 . .
H H9C 0.8641 0.7216 0.3466 0.072 Uiso calc R 1 . .
C C10 0.6663(3) 0.8800(3) 0.38007(15) 0.0389(7) Uani d . 1 . .
H H10A 0.6260 0.9502 0.3660 0.058 Uiso calc R 1 . .
H H10B 0.7561 0.8920 0.4049 0.058 Uiso calc R 1 . .
H H10C 0.6004 0.8423 0.4120 0.058 Uiso calc R 1 . .
C C11 1.2353(3) 1.0709(2) 0.37272(15) 0.0321(6) Uani d . 1 . .
C C12 1.2361(3) 0.9684(2) 0.41652(14) 0.0282(6) Uani d . 1 . .
H H12A 1.3165 0.9641 0.4511 0.034 Uiso calc R 1 . .
C C13 1.2821(3) 0.9638(2) 0.33829(13) 0.0279(6) Uani d . 1 . .
H H13A 1.3869 0.9586 0.3326 0.033 Uiso calc R 1 . .
C C14 1.0943(4) 1.1208(3) 0.35373(18) 0.0494(9) Uani d . 1 . .
H H14A 1.0811 1.1881 0.3809 0.074 Uiso calc R 1 . .
H H14B 1.0184 1.0696 0.3655 0.074 Uiso calc R 1 . .
H H14C 1.0918 1.1370 0.3025 0.074 Uiso calc R 1 . .
C C15 1.3528(4) 1.1522(3) 0.38644(18) 0.0465(8) Uani d . 1 . .
H H15A 1.3133 1.2176 0.4086 0.070 Uiso calc R 1 . .
H H15B 1.3979 1.1716 0.3411 0.070 Uiso calc R 1 . .
H H15C 1.4231 1.1198 0.4185 0.070 Uiso calc R 1 . .
C C16 1.1006(3) 0.9219(2) 0.44476(15) 0.0307(6) Uani d . 1 . .
H H16A 1.0611 0.9705 0.4819 0.037 Uiso calc R 1 . .
H H16B 1.0307 0.9156 0.4056 0.037 Uiso calc R 1 . .
C C17 1.2042(3) 0.9076(2) 0.28063(14) 0.0289(6) Uani d . 1 . .
C C18 1.2337(3) 0.8174(2) 0.16345(14) 0.0315(6) Uani d . 1 . .
H H18A 1.1303 0.8316 0.1576 0.038 Uiso calc R 1 . .
C C19 1.3086(3) 0.8541(3) 0.09619(15) 0.0442(8) Uani d . 1 . .
H H19A 1.2926 0.9321 0.0891 0.066 Uiso calc R 1 . .
H H19B 1.2714 0.8138 0.0551 0.066 Uiso calc R 1 . .
H H19C 1.4101 0.8403 0.1008 0.066 Uiso calc R 1 . .
C C20 1.2542(4) 0.6969(2) 0.17724(17) 0.0427(8) Uani d . 1 . .
H H20A 1.2034 0.6761 0.2208 0.064 Uiso calc R 1 . .
H H20B 1.3551 0.6814 0.1832 0.064 Uiso calc R 1 . .
H H20C 1.2174 0.6552 0.1366 0.064 Uiso calc R 1 . .
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 0.0000 '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 0.0311 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 O1 H1A . . 106.9 ?
C16 O3 H3 . . 110.2 ?
C7 N1 C8 . . 123.2(2) ?
C7 N1 H1 . . 117.1 ?
C8 N1 H1 . . 117.3 ?
C17 N2 C18 . . 124.0(2) ?
C17 N2 H2 . . 120.5 ?
C18 N2 H2 . . 115.3 ?
C2 C1 C5 . . 117.7(3) ?
C2 C1 C4 . . 119.8(2) ?
C5 C1 C4 . . 113.4(3) ?
C2 C1 C3 . . 60.66(17) ?
C5 C1 C3 . . 115.7(2) ?
C4 C1 C3 . . 120.0(2) ?
C1 C2 C6 . . 122.6(2) ?
C1 C2 C3 . . 61.09(17) ?
C6 C2 C3 . . 124.9(2) ?
C1 C2 H2A . . 112.9 ?
C6 C2 H2A . . 112.9 ?
C3 C2 H2A . . 112.9 ?
C7 C3 C2 . . 124.3(2) ?
C7 C3 C1 . . 123.5(2) ?
C2 C3 C1 . . 58.25(17) ?
C7 C3 H3A . . 113.3 ?
C2 C3 H3A . . 113.3 ?
C1 C3 H3A . . 113.3 ?
C1 C4 H4A . . 109.5 ?
C1 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C1 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C1 C5 H5A . . 109.5 ?
C1 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C1 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
O1 C6 C2 . . 110.4(2) ?
O1 C6 H6A . . 109.6 ?
C2 C6 H6A . . 109.6 ?
O1 C6 H6B . . 109.6 ?
C2 C6 H6B . . 109.6 ?
H6A C6 H6B . . 108.1 ?
O2 C7 N1 . . 122.4(2) ?
O2 C7 C3 . . 124.1(2) ?
N1 C7 C3 . . 113.4(2) ?
N1 C8 C10 . . 110.7(2) ?
N1 C8 C9 . . 110.6(2) ?
C10 C8 C9 . . 110.8(2) ?
N1 C8 H8A . . 108.2 ?
C10 C8 H8A . . 108.2 ?
C9 C8 H8A . . 108.2 ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C8 C10 H10A . . 109.5 ?
C8 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C8 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C12 C11 C14 . . 118.2(2) ?
C12 C11 C15 . . 117.1(3) ?
C14 C11 C15 . . 114.8(3) ?
C12 C11 C13 . . 60.44(17) ?
C14 C11 C13 . . 120.3(3) ?
C15 C11 C13 . . 115.2(2) ?
C16 C12 C11 . . 120.5(2) ?
C16 C12 C13 . . 124.5(2) ?
C11 C12 C13 . . 60.68(17) ?
C16 C12 H12A . . 113.7 ?
C11 C12 H12A . . 113.7 ?
C13 C12 H12A . . 113.7 ?
C17 C13 C12 . . 125.1(2) ?
C17 C13 C11 . . 124.4(2) ?
C12 C13 C11 . . 58.88(17) ?
C17 C13 H13A . . 112.8 ?
C12 C13 H13A . . 112.8 ?
C11 C13 H13A . . 112.8 ?
C11 C14 H14A . . 109.5 ?
C11 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C11 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C11 C15 H15A . . 109.5 ?
C11 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C11 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O3 C16 C12 . . 109.0(2) ?
O3 C16 H16A . . 109.9 ?
C12 C16 H16A . . 109.9 ?
O3 C16 H16B . . 109.9 ?
C12 C16 H16B . . 109.9 ?
H16A C16 H16B . . 108.3 ?
O4 C17 N2 . . 121.8(3) ?
O4 C17 C13 . . 124.1(3) ?
N2 C17 C13 . . 114.1(2) ?
N2 C18 C19 . . 109.6(2) ?
N2 C18 C20 . . 110.3(2) ?
C19 C18 C20 . . 111.9(3) ?
N2 C18 H18A . . 108.3 ?
C19 C18 H18A . . 108.3 ?
C20 C18 H18A . . 108.3 ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C18 C20 H20A . . 109.5 ?
C18 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C18 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C6 . 1.437(3) ?
O1 H1A . 0.8400 ?
O2 C7 . 1.237(3) ?
O3 C16 . 1.421(3) ?
O3 H3 . 0.8400 ?
O4 C17 . 1.242(3) ?
N1 C7 . 1.342(3) ?
N1 C8 . 1.460(3) ?
N1 H1 . 0.8800 ?
N2 C17 . 1.343(3) ?
N2 C18 . 1.457(3) ?
N2 H2 . 0.8800 ?
C1 C2 . 1.488(4) ?
C1 C5 . 1.506(4) ?
C1 C4 . 1.510(4) ?
C1 C3 . 1.531(4) ?
C2 C6 . 1.509(4) ?
C2 C3 . 1.525(4) ?
C2 H2A . 1.0000 ?
C3 C7 . 1.493(4) ?
C3 H3A . 1.0000 ?
C4 H4A . 0.9800 ?
C4 H4B . 0.9800 ?
C4 H4C . 0.9800 ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5C . 0.9800 ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C8 C10 . 1.512(4) ?
C8 C9 . 1.518(4) ?
C8 H8A . 1.0000 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 C12 . 1.504(4) ?
C11 C14 . 1.511(4) ?
C11 C15 . 1.517(4) ?
C11 C13 . 1.531(4) ?
C12 C16 . 1.500(4) ?
C12 C13 . 1.528(4) ?
C12 H12A . 1.0000 ?
C13 C17 . 1.478(4) ?
C13 H13A . 1.0000 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C18 C19 . 1.513(4) ?
C18 C20 . 1.516(4) ?
C18 H18A . 1.0000 ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C20 H20C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1A O3 3_755 0.84 1.96 2.796(3) 174.1
O3 H3 O1 2_675 0.84 1.98 2.782(3) 159.6
N1 H1 O4 . 0.88 2.03 2.906(3) 175.5
N2 H2 O2 1_655 0.88 2.09 2.964(3) 170.7
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
C5 C1 C2 C6 . . . . 139.5(3) ?
C4 C1 C2 C6 . . . . -5.2(4) ?
C3 C1 C2 C6 . . . . -115.0(3) ?
C5 C1 C2 C3 . . . . -105.5(3) ?
C4 C1 C2 C3 . . . . 109.8(3) ?
C1 C2 C3 C7 . . . . -111.2(3) ?
C6 C2 C3 C7 . . . . 0.1(4) ?
C6 C2 C3 C1 . . . . 111.4(3) ?
C2 C1 C3 C7 . . . . 112.7(3) ?
C5 C1 C3 C7 . . . . -138.6(3) ?
C4 C1 C3 C7 . . . . 3.2(4) ?
C5 C1 C3 C2 . . . . 108.7(3) ?
C4 C1 C3 C2 . . . . -109.5(3) ?
C1 C2 C6 O1 . . . . -74.7(3) ?
C3 C2 C6 O1 . . . . -150.0(2) ?
C8 N1 C7 O2 . . . . -8.4(4) ?
C8 N1 C7 C3 . . . . 172.5(2) ?
C2 C3 C7 O2 . . . . 16.9(4) ?
C1 C3 C7 O2 . . . . -54.9(4) ?
C2 C3 C7 N1 . . . . -164.0(2) ?
C1 C3 C7 N1 . . . . 124.3(3) ?
C7 N1 C8 C10 . . . . -85.8(3) ?
C7 N1 C8 C9 . . . . 151.0(3) ?
C14 C11 C12 C16 . . . . -4.3(4) ?
C15 C11 C12 C16 . . . . 139.9(3) ?
C13 C11 C12 C16 . . . . -115.0(3) ?
C14 C11 C12 C13 . . . . 110.8(3) ?
C15 C11 C12 C13 . . . . -105.0(3) ?
C16 C12 C13 C17 . . . . -3.9(4) ?
C11 C12 C13 C17 . . . . -112.5(3) ?
C16 C12 C13 C11 . . . . 108.6(3) ?
C12 C11 C13 C17 . . . . 113.6(3) ?
C14 C11 C13 C17 . . . . 6.2(4) ?
C15 C11 C13 C17 . . . . -138.2(3) ?
C14 C11 C13 C12 . . . . -107.3(3) ?
C15 C11 C13 C12 . . . . 108.2(3) ?
C11 C12 C16 O3 . . . . 171.1(2) ?
C13 C12 C16 O3 . . . . 97.7(3) ?
C18 N2 C17 O4 . . . . -4.6(4) ?
C18 N2 C17 C13 . . . . 175.1(2) ?
C12 C13 C17 O4 . . . . 22.4(4) ?
C11 C13 C17 O4 . . . . -51.1(4) ?
C12 C13 C17 N2 . . . . -157.3(2) ?
C11 C13 C17 N2 . . . . 129.2(3) ?
C17 N2 C18 C19 . . . . 147.4(3) ?
C17 N2 C18 C20 . . . . -89.0(3) ?
