#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/76/2017605.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_2017605
loop_
_publ_author_name
'de Sousa, Alvaro S.'
'Hlam, Zanele'
'Fernandes, Manuel A.'
'Marques, Helder M.'
_publ_section_title
;
 Hydrogen-bonding controls the solid-state and enantiomeric
 comformations of the amino alcohol ligand
 2-[(2-hydroxyethyl)amino]cyclohexanol
;
_journal_coeditor_code           FG3157
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o229
_journal_page_last               o232
_journal_paper_doi               10.1107/S0108270110009820
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C8 H17 N O2'
_chemical_formula_moiety         'C8 H17 N O2'
_chemical_formula_sum            'C8 H17 N O2'
_chemical_formula_weight         159.23
_chemical_name_systematic
;
2-[(2-hydroxyethyl)amino]cyclohexanol
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                112.9540(10)
_cell_angle_beta                 92.4290(10)
_cell_angle_gamma                102.0550(10)
_cell_formula_units_Z            4
_cell_length_a                   9.4334(2)
_cell_length_b                   10.0280(3)
_cell_length_c                   10.4651(3)
_cell_measurement_reflns_used    5097
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.23
_cell_volume                     883.02(4)
_computing_cell_refinement       'SMART [APEX2?] (Bruker, 2005)'
_computing_data_collection       'SMART [APEX2?] (Bruker, 2005)'
_computing_data_reduction        'SAINT [SAINT-Plus?] (Bruker, 2005)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1997)
;
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART [APEXII?] CCD area-detector'
_diffrn_measurement_method       'φ and ω 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  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20934
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.185
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         4253
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0369
_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)+(0.0496P)²+0.2058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1030
_reflns_number_gt                3495
_reflns_number_total             4253
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg3157.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2017605
_cod_database_fobs_code          2017605
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C C1 0.39086(10) 0.34950(11) 0.15841(10) 0.0200(2) Uani d . 1 . .
H H1A 0.4014 0.4098 0.2617 0.024 Uiso calc R 1 . .
C C2 0.28564(11) 0.19757(11) 0.12241(10) 0.0219(2) Uani d . 1 . .
H H2A 0.2781 0.1362 0.0196 0.026 Uiso calc R 1 . .
C C3 0.13388(11) 0.21742(13) 0.15719(12) 0.0277(2) Uani d . 1 . .
H H3A 0.0660 0.1183 0.1310 0.033 Uiso calc R 1 . .
H H3B 0.1390 0.2749 0.2593 0.033 Uiso calc R 1 . .
C C4 0.07589(12) 0.29927(14) 0.07892(12) 0.0301(3) Uani d . 1 . .
H H4A -0.0210 0.3139 0.1054 0.036 Uiso calc R 1 . .
H H4B 0.0632 0.2378 -0.0232 0.036 Uiso calc R 1 . .
C C5 0.18021(12) 0.45048(13) 0.11260(12) 0.0295(2) Uani d . 1 . .
H H5A 0.1838 0.5161 0.2126 0.035 Uiso calc R 1 . .
H H5B 0.1433 0.4981 0.0555 0.035 Uiso calc R 1 . .
C C6 0.33419(12) 0.43401(12) 0.08271(11) 0.0249(2) Uani d . 1 . .
H H6A 0.3329 0.3801 -0.0194 0.030 Uiso calc R 1 . .
H H6B 0.4011 0.5343 0.1131 0.030 Uiso calc R 1 . .
C C7 0.27026(12) -0.03677(12) 0.15081(13) 0.0318(3) Uani d D 1 . .
H H7A 0.2536 -0.0838 0.0471 0.038 Uiso calc R 1 . .
H H7B 0.1736 -0.0447 0.1845 0.038 Uiso calc R 1 . .
C C8 0.35789(14) -0.11912(13) 0.20404(13) 0.0347(3) Uani d D 1 . .
H H8A 0.3786 -0.0686 0.3075 0.042 Uiso calc R 1 . .
H H8B 0.2989 -0.2221 0.1788 0.042 Uiso calc R 1 . .
N N1 0.34610(10) 0.12143(10) 0.19865(9) 0.0238(2) Uani d . 1 . .
H H3 0.4434 0.1285 0.1883 0.029 Uiso calc R 1 . .
O O1 0.53151(8) 0.33006(8) 0.12066(8) 0.02352(17) Uani d . 1 . .
H H1 0.5906 0.3568 0.1935 0.035 Uiso calc R 1 . .
O O2 0.49166(9) -0.12558(10) 0.14837(9) 0.0385(2) Uani d D 1 . .
H H2 0.4752 -0.1892 0.0650 0.058 Uiso calc R 1 . .
C C11 0.32669(11) 0.30623(11) 0.58756(10) 0.0200(2) Uani d . 1 . .
H H11A 0.3878 0.3497 0.6814 0.024 Uiso calc R 1 . .
C C12 0.21699(10) 0.40040(11) 0.59533(10) 0.0185(2) Uani d . 1 B .
H H12A 0.1521 0.3562 0.5035 0.022 Uiso calc R 1 . .
C C13 0.12302(11) 0.39830(11) 0.70980(11) 0.0227(2) Uani d . 1 . .
H H13A 0.0511 0.4585 0.7138 0.027 Uiso calc R 1 . .
H H13B 0.1860 0.4440 0.8016 0.027 Uiso calc R 1 . .
C C14 0.04220(12) 0.23922(12) 0.68246(12) 0.0263(2) Uani d . 1 . .
H H14A -0.0144 0.2408 0.7603 0.032 Uiso calc R 1 . .
H H14B -0.0276 0.1967 0.5950 0.032 Uiso calc R 1 . .
C C15 0.14871(12) 0.14127(12) 0.66941(12) 0.0270(2) Uani d . 1 . .
H H15A 0.0932 0.0370 0.6436 0.032 Uiso calc R 1 . .
H H15B 0.2096 0.1758 0.7610 0.032 Uiso calc R 1 . .
C C16 0.24777(12) 0.14630(11) 0.55875(12) 0.0263(2) Uani d . 1 . .
H H16A 0.3208 0.0881 0.5580 0.032 Uiso calc R 1 . .
H H16B 0.1882 0.0995 0.4652 0.032 Uiso calc R 1 . .
N N11 0.29472(9) 0.55411(9) 0.62213(9) 0.01932(18) Uani d D 1 . .
H H13 0.3728 0.5518 0.5722 0.023 Uiso calc R 1 A 1
O O11 0.42248(8) 0.31328(8) 0.48741(8) 0.02631(18) Uani d . 1 . .
H H11 0.3815 0.2520 0.4069 0.039 Uiso calc R 1 . .
C C17 0.1977(2) 0.63305(17) 0.5819(2) 0.0227(5) Uani d PD 0.736(2) B 1
H H17A 0.1068 0.6233 0.6250 0.027 Uiso calc PR 0.736(2) B 1
H H17B 0.1707 0.5871 0.4789 0.027 Uiso calc PR 0.736(2) B 1
C C18 0.2728(7) 0.7966(2) 0.6294(2) 0.0268(7) Uani d PD 0.736(2) B 1
H H8C 0.3696 0.8062 0.5963 0.032 Uiso calc PR 0.736(2) B 1
H H8D 0.2135 0.8439 0.5877 0.032 Uiso calc PR 0.736(2) B 1
O O12 0.29099(14) 0.87110(12) 0.77732(11) 0.0360(3) Uani d PD 0.736(2) B 1
H H12 0.3499 0.9551 0.8028 0.054 Uiso calc PR 0.736(2) B 1
C C27 0.1984(5) 0.6517(6) 0.6199(6) 0.0188(13) Uani d PDU 0.264(2) B 2
H H27A 0.1557 0.6820 0.7087 0.023 Uiso calc PR 0.264(2) B 2
H H27B 0.1168 0.5934 0.5426 0.023 Uiso calc PR 0.264(2) B 2
C C28 0.273(2) 0.7909(5) 0.6017(10) 0.0309(16) Uani d PDU 0.264(2) B 2
H H28A 0.2036 0.8554 0.6128 0.037 Uiso calc PR 0.264(2) B 2
H H28B 0.3579 0.8474 0.6756 0.037 Uiso calc PR 0.264(2) B 2
O O22 0.3202(4) 0.7557(5) 0.4685(4) 0.0497(12) Uani d PDU 0.264(2) B 2
H H2D 0.4005 0.7322 0.4701 0.075 Uiso calc PR 0.264(2) B 2
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 0.0016 '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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
O1 C1 C6 . . 109.13(8) ?
O1 C1 C2 . . 110.00(8) ?
C6 C1 C2 . . 111.32(8) ?
O1 C1 H1A . . 108.8 ?
C6 C1 H1A . . 108.8 ?
C2 C1 H1A . . 108.8 ?
N1 C2 C3 . . 112.09(9) ?
N1 C2 C1 . . 108.79(8) ?
C3 C2 C1 . . 110.17(8) ?
N1 C2 H2A . . 108.6 ?
C3 C2 H2A . . 108.6 ?
C1 C2 H2A . . 108.6 ?
C4 C3 C2 . . 110.73(9) ?
C4 C3 H3A . . 109.5 ?
C2 C3 H3A . . 109.5 ?
C4 C3 H3B . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 108.1 ?
C3 C4 C5 . . 111.12(9) ?
C3 C4 H4A . . 109.4 ?
C5 C4 H4A . . 109.4 ?
C3 C4 H4B . . 109.4 ?
C5 C4 H4B . . 109.4 ?
H4A C4 H4B . . 108.0 ?
C4 C5 C6 . . 111.20(9) ?
C4 C5 H5A . . 109.4 ?
C6 C5 H5A . . 109.4 ?
C4 C5 H5B . . 109.4 ?
C6 C5 H5B . . 109.4 ?
H5A C5 H5B . . 108.0 ?
C1 C6 C5 . . 111.48(9) ?
C1 C6 H6A . . 109.3 ?
C5 C6 H6A . . 109.3 ?
C1 C6 H6B . . 109.3 ?
C5 C6 H6B . . 109.3 ?
H6A C6 H6B . . 108.0 ?
N1 C7 C8 . . 111.38(9) ?
N1 C7 H7A . . 109.4 ?
C8 C7 H7A . . 109.4 ?
N1 C7 H7B . . 109.4 ?
C8 C7 H7B . . 109.4 ?
H7A C7 H7B . . 108.0 ?
O2 C8 C7 . . 112.50(9) ?
O2 C8 H8A . . 109.1 ?
C7 C8 H8A . . 109.1 ?
O2 C8 H8B . . 109.1 ?
C7 C8 H8B . . 109.1 ?
H8A C8 H8B . . 107.8 ?
C7 N1 C2 . . 113.46(8) ?
C7 N1 H3 . . 108.9 ?
C2 N1 H3 . . 108.9 ?
C1 O1 H1 . . 109.5 ?
C8 O2 H2 . . 109.5 ?
O11 C11 C16 . . 112.33(8) ?
O11 C11 C12 . . 111.09(8) ?
C16 C11 C12 . . 110.59(8) ?
O11 C11 H11A . . 107.5 ?
C16 C11 H11A . . 107.5 ?
C12 C11 H11A . . 107.5 ?
N11 C12 C13 . . 110.96(8) ?
N11 C12 C11 . . 109.96(8) ?
C13 C12 C11 . . 109.62(8) ?
N11 C12 H12A . . 108.8 ?
C13 C12 H12A . . 108.8 ?
C11 C12 H12A . . 108.8 ?
C12 C13 C14 . . 111.16(8) ?
C12 C13 H13A . . 109.4 ?
C14 C13 H13A . . 109.4 ?
C12 C13 H13B . . 109.4 ?
C14 C13 H13B . . 109.4 ?
H13A C13 H13B . . 108.0 ?
C15 C14 C13 . . 111.01(9) ?
C15 C14 H14A . . 109.4 ?
C13 C14 H14A . . 109.4 ?
C15 C14 H14B . . 109.4 ?
C13 C14 H14B . . 109.4 ?
H14A C14 H14B . . 108.0 ?
C14 C15 C16 . . 111.26(9) ?
C14 C15 H15A . . 109.4 ?
C16 C15 H15A . . 109.4 ?
C14 C15 H15B . . 109.4 ?
C16 C15 H15B . . 109.4 ?
H15A C15 H15B . . 108.0 ?
C11 C16 C15 . . 111.40(8) ?
C11 C16 H16A . . 109.3 ?
C15 C16 H16A . . 109.3 ?
C11 C16 H16B . . 109.3 ?
C15 C16 H16B . . 109.3 ?
H16A C16 H16B . . 108.0 ?
C12 N11 C17 . . 111.51(10) ?
C12 N11 C27 . . 114.4(2) ?
C12 N11 H13 . . 109.3 ?
C17 N11 H13 . . 109.3 ?
C27 N11 H13 . . 118.9 ?
C11 O11 H11 . . 109.5 ?
N11 C17 C18 . . 110.7(3) ?
N11 C17 H17A . . 109.5 ?
C18 C17 H17A . . 109.5 ?
N11 C17 H17B . . 109.5 ?
C18 C17 H17B . . 109.5 ?
H17A C17 H17B . . 108.1 ?
O12 C18 C17 . . 110.83(13) ?
O12 C18 H8C . . 109.5 ?
C17 C18 H8C . . 109.5 ?
O12 C18 H8D . . 109.5 ?
C17 C18 H8D . . 109.5 ?
H8C C18 H8D . . 108.1 ?
N11 C27 C28 . . 114.8(9) ?
N11 C27 H27A . . 108.6 ?
C28 C27 H27A . . 108.6 ?
N11 C27 H27B . . 108.6 ?
C28 C27 H27B . . 108.6 ?
H27A C27 H27B . . 107.5 ?
O22 C28 C27 . . 111.51(17) ?
O22 C28 H28A . . 109.3 ?
C27 C28 H28A . . 109.3 ?
O22 C28 H28B . . 109.3 ?
C27 C28 H28B . . 109.3 ?
H28A C28 H28B . . 108.0 ?
C28 O22 H2D . . 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
C1 O1 . 1.4307(12) ?
C1 C6 . 1.5194(14) ?
C1 C2 . 1.5289(13) ?
C1 H1A . 1.0000 ?
C2 N1 . 1.4708(13) ?
C2 C3 . 1.5258(14) ?
C2 H2A . 1.0000 ?
C3 C4 . 1.5224(16) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C5 . 1.5239(16) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C6 . 1.5276(15) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 N1 . 1.4681(13) ?
C7 C8 . 1.5101(14) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 O2 . 1.4152(14) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
N1 H3 . 0.9200 ?
O1 H1 . 0.8400 ?
O2 H2 . 0.8400 ?
C11 O11 . 1.4253(12) ?
C11 C16 . 1.5240(14) ?
C11 C12 . 1.5247(13) ?
C11 H11A . 1.0000 ?
C12 N11 . 1.4716(12) ?
C12 C13 . 1.5243(14) ?
C12 H12A . 1.0000 ?
C13 C14 . 1.5249(14) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C15 . 1.5206(16) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C16 . 1.5279(15) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
N11 C17 . 1.4733(15) ?
N11 C27 . 1.4736(17) ?
N11 H13 . 0.9200 ?
O11 H11 . 0.8400 ?
C17 C18 . 1.5126(15) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C18 O12 . 1.4161(17) ?
C18 H8C . 0.9900 ?
C18 H8D . 0.9900 ?
O12 H12 . 0.8400 ?
C27 C28 . 1.5117(16) ?
C27 H27A . 0.9900 ?
C27 H27B . 0.9900 ?
C28 O22 . 1.4158(17) ?
C28 H28A . 0.9900 ?
C28 H28B . 0.9900 ?
O22 H2D . 0.8400 ?
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
_geom_hbond_publ_flag
O2 H2 O1 2_655 0.84 1.89 2.7270(11) 172 y
N11 H13 O11 2_666 0.92 2.37 3.1884(11) 148 y
O12 H12 O2 2_666 0.84 1.90 2.7299(14) 170 y
O11 H11 N1 1_555 0.84 2.03 2.8379(12) 162 y
O1 H1 N11 2_666 0.84 1.94 2.7701(11) 169 y
N1 H3 O12 2_666 0.92 2.52 3.4051(16) 163 y
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 C1 C2 N1 . . . . 58.98(10) ?
C6 C1 C2 N1 . . . . -179.93(8) ?
O1 C1 C2 C3 . . . . -177.78(8) ?
C6 C1 C2 C3 . . . . -56.69(11) ?
N1 C2 C3 C4 . . . . 178.85(8) ?
C1 C2 C3 C4 . . . . 57.55(11) ?
C2 C3 C4 C5 . . . . -57.19(12) ?
C3 C4 C5 C6 . . . . 55.21(12) ?
O1 C1 C6 C5 . . . . 176.79(8) ?
C2 C1 C6 C5 . . . . 55.19(12) ?
C4 C5 C6 C1 . . . . -54.22(12) ?
N1 C7 C8 O2 . . . . -65.06(13) ?
C8 C7 N1 C2 . . . . 165.35(9) ?
C3 C2 N1 C7 . . . . 69.67(11) ?
C1 C2 N1 C7 . . . . -168.25(8) ?
O11 C11 C12 N11 . . . . -54.15(10) ?
C16 C11 C12 N11 . . . . -179.58(8) ?
O11 C11 C12 C13 . . . . -176.38(8) ?
C16 C11 C12 C13 . . . . 58.18(11) ?
N11 C12 C13 C14 . . . . 179.99(8) ?
C11 C12 C13 C14 . . . . -58.38(11) ?
C12 C13 C14 C15 . . . . 56.64(12) ?
C13 C14 C15 C16 . . . . -54.18(12) ?
O11 C11 C16 C15 . . . . 178.58(9) ?
C12 C11 C16 C15 . . . . -56.69(12) ?
C14 C15 C16 C11 . . . . 54.54(12) ?
C13 C12 N11 C17 . . . . -78.63(13) ?
C11 C12 N11 C17 . . . . 159.93(12) ?
C13 C12 N11 C27 . . . . -63.4(3) ?
C11 C12 N11 C27 . . . . 175.1(2) ?
C12 N11 C17 C18 . . . . 171.76(15) ?
C27 N11 C17 C18 . . . . 67.1(10) ?
N11 C17 C18 O12 . . . . -68.9(5) ?
C12 N11 C27 C28 . . . . -161.7(5) ?
C17 N11 C27 C28 . . . . -80.4(10) ?
N11 C27 C28 O22 . . . . 65.7(16) ?
