# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_km1294

# start Validation Reply Form
_vrf_PLAT731_km1294              
;
PROBLEM: PLAT731_ALERT_1_A Bond Calc 0.84(3),
Rep 0.84000(12) ...... 9.90 su-Ra
O1 -H1O 1.555 1.555
RESPONSE: The hydrogen atom H1O was refined in x,y,z with a hard O-H
distance restraint using instruction DFIX of program SHELXL97.
;
_vrf_PLAT736_km1294              
;
PROBLEM: PLAT736_ALERT_1_B H...A Calc 2.53(3),
Rep 2.529(5) ...... 6.00 su-Ra
H1O -I1 1.555 1.555
RESPONSE: The hydrogen atom H1O was refined in x,y,z with a hard O-H
distance restraint using instruction DFIX of program SHELXL97.
;
_vrf_PLAT094_km1294              
;
PROBLEM: Ratio of Maximum / Minimum Residual Density .... 2.31
RESPONSE: Contains two iodine atoms with high scattering power
and significant absorption. Most significant residual electron
densities near iodine.
;
_vrf_PLAT745_km1294              
;
PROBLEM: PLAT745_ALERT_1_C D-H Calc 0.84(3),
Rep 0.84000 ...... Missing su
O1 -H1O 1.555 1.555
RESPONSE: The hydrogen atom H1O was refined in x,y,z with a hard O-H
distance restraint using instruction DFIX of program SHELXL97.
;
_vrf_REFLT03_km1294              
;
PROBLEM: Please check that the estimate of the number of Friedel
pairs is correct.
RESPONSE: Estimate is correct.
;
_vrf_PLAT791_km1294              
;
PROBLEM: Confirm the Absolute Configuration of C7 = S, C8 = R
RESPONSE: Absolute Configuration of C7 is S, and C8 is R.
********************************************************
PLEASE NOTE that the crystal structure of the present compound,
a methiodide derivative, served to fix the absolute structure of
the parent compound, cystal structure km1291 given in previous
CIF.
********************************************************
;
# end Validation Reply Form




_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(N,N')-Bis-methyliodide adduct of
(1S,2R)-2-(Methyl-pyridin-3-ylmethyl-amino)-1-phenyl-propan-1-ol
;
_chemical_name_common            'Methiodide of km1291'
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H26 N2 O, 2(I)'
_chemical_formula_sum            'C18 H26 I2 N2 O'
_chemical_formula_weight         540.21
_chemical_absolute_configuration ad


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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.6242(6)
_cell_length_b                   14.6111(10)
_cell_length_c                   9.0040(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.1470(10)
_cell_angle_gamma                90.00
_cell_volume                     1027.05(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5921
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      29.99

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    3.068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.44
_exptl_absorpt_correction_T_max  0.69
_exptl_absorpt_process_details   'program SAINT'

_exptl_special_details           
;
Bruker Smart APEX CCD 3-axis diffractometer,
3/4 sphere data collection with omega scan frames of 0.3deg and 6sec
per frame.
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12666
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         30.00
_reflns_number_total             5686
_reflns_number_gt                5642
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT, SADABS, XPREP'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0356P)^2^+0.2842P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.018(15)
_refine_ls_number_reflns         5686
_refine_ls_number_parameters     215
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0209
_refine_ls_wR_factor_ref         0.0524
_refine_ls_wR_factor_gt          0.0523
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
I1 I 0.918721(19) 0.27564(2) 1.026700(17) 0.02152(4) Uani 1 1 d . . .
I2 I 0.168695(18) 0.51121(2) 0.615281(17) 0.01933(4) Uani 1 1 d . . .
O1 O 0.5785(2) 0.17879(11) 0.7213(2) 0.0208(3) Uani 1 1 d DU . .
H1O H 0.669(3) 0.198(3) 0.798(3) 0.031 Uiso 1 1 d D . .
N1 N 0.2366(3) 0.22102(14) 0.7156(2) 0.0155(3) Uani 1 1 d U . .
N2 N 0.0206(3) 0.02759(14) 0.9816(2) 0.0183(4) Uani 1 1 d U . .
C1 C 0.5369(3) 0.29697(16) 0.5135(3) 0.0166(4) Uani 1 1 d U . .
C2 C 0.4994(3) 0.38754(18) 0.4613(3) 0.0201(4) Uani 1 1 d U . .
H2 H 0.4430 0.4261 0.5078 0.024 Uiso 1 1 calc R . .
C3 C 0.5450(3) 0.4212(2) 0.3408(3) 0.0252(5) Uani 1 1 d U . .
H3 H 0.5210 0.4831 0.3065 0.030 Uiso 1 1 calc R . .
C4 C 0.6255(3) 0.3650(2) 0.2702(3) 0.0257(5) Uani 1 1 d U . .
H4 H 0.6573 0.3885 0.1887 0.031 Uiso 1 1 calc R . .
C5 C 0.6591(3) 0.2742(2) 0.3194(3) 0.0240(4) Uani 1 1 d U . .
H5 H 0.7113 0.2351 0.2695 0.029 Uiso 1 1 calc R . .
C6 C 0.6165(3) 0.24049(19) 0.4416(3) 0.0205(4) Uani 1 1 d U . .
H6 H 0.6417 0.1787 0.4764 0.025 Uiso 1 1 calc R . .
C7 C 0.4915(3) 0.26187(16) 0.6496(3) 0.0165(4) Uani 1 1 d U . .
H7 H 0.5247 0.3096 0.7374 0.020 Uiso 1 1 calc R . .
C8 C 0.2975(3) 0.24687(18) 0.5808(3) 0.0159(3) Uani 1 1 d U . .
H8 H 0.2419 0.3065 0.5326 0.019 Uiso 1 1 calc R . .
C9 C 0.2360(3) 0.17714(18) 0.4421(3) 0.0189(4) Uani 1 1 d U . .
H9A H 0.2421 0.2039 0.3449 0.028 Uiso 1 1 calc R . .
H9B H 0.1173 0.1600 0.4158 0.028 Uiso 1 1 calc R . .
H9C H 0.3089 0.1226 0.4762 0.028 Uiso 1 1 calc R . .
C10 C 0.0483(3) 0.24433(19) 0.6490(3) 0.0203(4) Uani 1 1 d U . .
H10A H 0.0088 0.2356 0.7353 0.030 Uiso 1 1 calc R . .
H10B H -0.0168 0.2042 0.5560 0.030 Uiso 1 1 calc R . .
H10C H 0.0309 0.3083 0.6127 0.030 Uiso 1 1 calc R . .
C11 C 0.2620(3) 0.11912(16) 0.7529(3) 0.0173(4) Uani 1 1 d U . .
H11A H 0.1884 0.0849 0.6528 0.021 Uiso 1 1 calc R . .
H11B H 0.3825 0.1034 0.7790 0.021 Uiso 1 1 calc R . .
C12 C 0.2225(3) 0.08709(16) 0.8920(3) 0.0169(4) Uani 1 1 d U . .
C13 C 0.0581(3) 0.06053(16) 0.8616(3) 0.0176(4) Uani 1 1 d U . .
H13 H -0.0302 0.0657 0.7536 0.021 Uiso 1 1 calc R . .
C14 C 0.1435(3) 0.0167(2) 1.1361(3) 0.0222(4) Uani 1 1 d U . .
H14 H 0.1150 -0.0077 1.2191 0.027 Uiso 1 1 calc R . .
C15 C 0.3101(3) 0.0411(2) 1.1728(3) 0.0238(4) Uani 1 1 d U . .
H15 H 0.3967 0.0337 1.2811 0.029 Uiso 1 1 calc R . .
C16 C 0.3510(3) 0.07657(18) 1.0516(3) 0.0203(4) Uani 1 1 d U . .
H16 H 0.4657 0.0937 1.0764 0.024 Uiso 1 1 calc R . .
C17 C 0.3287(3) 0.27646(18) 0.8689(3) 0.0193(4) Uani 1 1 d U . .
H17A H 0.2731 0.2677 0.9428 0.029 Uiso 1 1 calc R . .
H17B H 0.3247 0.3414 0.8401 0.029 Uiso 1 1 calc R . .
H17C H 0.4483 0.2564 0.9237 0.029 Uiso 1 1 calc R . .
C18 C -0.1566(3) -0.0002(2) 0.9432(3) 0.0253(5) Uani 1 1 d U . .
H18A H -0.2365 0.0387 0.8553 0.038 Uiso 1 1 calc R . .
H18B H -0.1777 0.0066 1.0413 0.038 Uiso 1 1 calc R . .
H18C H -0.1733 -0.0642 0.9075 0.038 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.02207(7) 0.02128(7) 0.01974(7) -0.00016(5) 0.00745(5) 0.00000(6)
I2 0.02241(7) 0.01575(7) 0.02185(7) 0.00236(5) 0.01137(5) 0.00315(5)
O1 0.0176(8) 0.0198(8) 0.0214(8) 0.0047(6) 0.0049(6) 0.0025(6)
N1 0.0169(8) 0.0143(8) 0.0158(7) 0.0000(6) 0.0075(6) 0.0002(7)
N2 0.0239(8) 0.0148(10) 0.0198(8) 0.0006(7) 0.0127(6) -0.0006(7)
C1 0.0135(9) 0.0167(10) 0.0198(9) 0.0005(7) 0.0072(7) -0.0013(8)
C2 0.0198(10) 0.0169(9) 0.0249(11) 0.0004(8) 0.0108(8) -0.0019(8)
C3 0.0238(11) 0.0231(11) 0.0303(12) 0.0075(9) 0.0129(10) -0.0013(10)
C4 0.0212(11) 0.0335(13) 0.0251(11) 0.0049(9) 0.0125(9) -0.0034(10)
C5 0.0211(10) 0.0298(11) 0.0248(10) -0.0009(10) 0.0134(8) -0.0004(10)
C6 0.0185(10) 0.0202(10) 0.0246(10) -0.0007(8) 0.0110(8) 0.0004(9)
C7 0.0156(8) 0.0160(10) 0.0167(8) 0.0010(7) 0.0057(7) -0.0003(7)
C8 0.0152(8) 0.0186(9) 0.0145(8) 0.0010(7) 0.0069(7) -0.0006(8)
C9 0.0190(10) 0.0244(12) 0.0130(9) -0.0008(7) 0.0065(7) -0.0031(8)
C10 0.0176(9) 0.0200(10) 0.0254(10) 0.0037(9) 0.0111(8) 0.0019(8)
C11 0.0231(10) 0.0142(8) 0.0178(9) 0.0014(7) 0.0118(8) 0.0020(8)
C12 0.0219(10) 0.0139(9) 0.0158(8) 0.0014(7) 0.0090(7) 0.0009(8)
C13 0.0208(9) 0.0164(10) 0.0152(8) 0.0019(7) 0.0074(7) 0.0005(8)
C14 0.0310(10) 0.0196(11) 0.0185(8) 0.0027(9) 0.0129(7) 0.0010(10)
C15 0.0285(10) 0.0261(12) 0.0146(9) 0.0017(9) 0.0071(8) 0.0010(10)
C16 0.0221(10) 0.0206(11) 0.0176(9) -0.0005(8) 0.0079(7) 0.0005(9)
C17 0.0250(10) 0.0172(10) 0.0161(8) -0.0017(8) 0.0092(7) 0.0008(10)
C18 0.0244(9) 0.0231(13) 0.0320(12) 0.0042(10) 0.0155(8) -0.0004(10)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C7 1.429(3) . ?
O1 H1O 0.84000(12) . ?
N1 C17 1.503(3) . ?
N1 C10 1.512(3) . ?
N1 C11 1.522(3) . ?
N1 C8 1.560(3) . ?
N2 C13 1.342(3) . ?
N2 C14 1.353(3) . ?
N2 C18 1.473(3) . ?
C1 C2 1.396(3) . ?
C1 C6 1.396(3) . ?
C1 C7 1.525(3) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.533(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.522(3) . ?
C8 H8 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 1.505(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.380(3) . ?
C12 C16 1.402(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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
C7 O1 H1O 102(3) . . ?
C17 N1 C10 107.56(18) . . ?
C17 N1 C11 110.74(18) . . ?
C10 N1 C11 109.72(19) . . ?
C17 N1 C8 111.29(18) . . ?
C10 N1 C8 107.28(17) . . ?
C11 N1 C8 110.15(17) . . ?
C13 N2 C14 121.2(2) . . ?
C13 N2 C18 119.4(2) . . ?
C14 N2 C18 119.3(2) . . ?
C2 C1 C6 119.6(2) . . ?
C2 C1 C7 119.2(2) . . ?
C6 C1 C7 121.2(2) . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.3(3) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O1 C7 C1 112.61(18) . . ?
O1 C7 C8 109.51(19) . . ?
C1 C7 C8 109.41(17) . . ?
O1 C7 H7 108.4 . . ?
C1 C7 H7 108.4 . . ?
C8 C7 H7 108.4 . . ?
C9 C8 C7 111.54(19) . . ?
C9 C8 N1 111.19(19) . . ?
C7 C8 N1 113.00(17) . . ?
C9 C8 H8 106.9 . . ?
C7 C8 H8 106.9 . . ?
N1 C8 H8 106.9 . . ?
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 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N1 115.21(18) . . ?
C12 C11 H11A 108.5 . . ?
N1 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
N1 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C13 C12 C16 118.0(2) . . ?
C13 C12 C11 119.9(2) . . ?
C16 C12 C11 121.8(2) . . ?
N2 C13 C12 121.3(2) . . ?
N2 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
N2 C14 C15 119.8(2) . . ?
N2 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 119.9(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C12 119.7(2) . . ?
C15 C16 H16 120.2 . . ?
C12 C16 H16 120.2 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
C6 C1 C2 C3 -1.4(4) . . . . ?
C7 C1 C2 C3 178.0(2) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 -1.7(4) . . . . ?
C4 C5 C6 C1 1.2(4) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C7 C1 C6 C5 -179.0(2) . . . . ?
C2 C1 C7 O1 -163.4(2) . . . . ?
C6 C1 C7 O1 16.0(3) . . . . ?
C2 C1 C7 C8 74.6(3) . . . . ?
C6 C1 C7 C8 -106.1(2) . . . . ?
O1 C7 C8 C9 -63.8(2) . . . . ?
C1 C7 C8 C9 60.1(3) . . . . ?
O1 C7 C8 N1 62.3(2) . . . . ?
C1 C7 C8 N1 -173.78(19) . . . . ?
C17 N1 C8 C9 167.10(19) . . . . ?
C10 N1 C8 C9 -75.5(3) . . . . ?
C11 N1 C8 C9 43.9(2) . . . . ?
C17 N1 C8 C7 40.8(3) . . . . ?
C10 N1 C8 C7 158.18(19) . . . . ?
C11 N1 C8 C7 -82.4(2) . . . . ?
C17 N1 C11 C12 51.3(3) . . . . ?
C10 N1 C11 C12 -67.3(2) . . . . ?
C8 N1 C11 C12 174.83(19) . . . . ?
N1 C11 C12 C13 88.5(3) . . . . ?
N1 C11 C12 C16 -96.4(3) . . . . ?
C14 N2 C13 C12 -1.9(4) . . . . ?
C18 N2 C13 C12 -179.8(2) . . . . ?
C16 C12 C13 N2 1.6(4) . . . . ?
C11 C12 C13 N2 176.8(2) . . . . ?
C13 N2 C14 C15 1.1(4) . . . . ?
C18 N2 C14 C15 179.0(2) . . . . ?
N2 C14 C15 C16 0.0(4) . . . . ?
C14 C15 C16 C12 -0.2(4) . . . . ?
C13 C12 C16 C15 -0.5(4) . . . . ?
C11 C12 C16 C15 -175.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O I1 0.84 2.529(5) 3.3639(18) 173(4) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.000
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.081
_database_code_depnum_ccdc_archive 'CCDC 667736'