# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


#######################################################################
#
#                 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 
#  on your local computer system.
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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 
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data_HHQ.HCl
_database_code_depnum_ccdc_archive 'CCDC 885400'
#TrackingRef 'McGlacken.cif'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H22 N O, Cl'
_chemical_formula_sum            'C16 H22 Cl N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         279.80

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.221(7)
_cell_length_b                   13.132(8)
_cell_length_c                   12.143(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.090(18)
_cell_angle_gamma                90
_cell_volume                     1566.0(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1799
_cell_measurement_theta_min      2.3111
_cell_measurement_theta_max      20.9993
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600

_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.6372
_exptl_absorpt_correction_T_max  0.7454

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II DUO'
_diffrn_measurement_method       '\f & \w scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            16548
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         26.51
_diffrn_reflns_theta_full        26.51
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_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.
;

_reflns_number_total             3226
_reflns_number_gt                1682
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1690
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.086
_refine_ls_number_reflns         3226
_refine_ls_number_parameters     177
_refine_ls_number_restraints     6
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0775P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.250
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2009, 3, 0, 0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 3.0 (Macrae et al, 2008)'
_computing_publication_material  ?
_iucr_refine_instructions_details 
;
TITL mo_GMG_TMS_Sample_001_vs2_0m in P2(1)/n
CELL 0.71073 10.2207 13.1325 12.1434 90.000 106.090 90.000
ZERR 4.00 0.0065 0.0084 0.0077 0.000 0.018 0.000
LATT 1
SYMM 0.5-X, 0.5+Y, 0.5-Z
SFAC C H N O Cl
UNIT 64 88 4 4 4
L.S. 10
ACTA
BOND $H
FMAP 2
PLAN 5
HTAB O11 Cl19_$1
EQIV $1_[ -x+3/2, y+1/2, -z+3/2 ]
HTAB
CONF
ISOR 0.05 C18
TEMP 23.000
WGHT 0.077500
FVAR 0.16641
MOLE 1
C1 1 0.873722 0.888839 0.664459 11.00000 0.05215 0.05277 =
0.06829 0.00060 0.01747 0.00059
C2 1 0.836586 0.867972 0.762475 11.00000 0.05715 0.05867 =
0.06422 -0.00574 0.01642 -0.00662
AFIX 43
H2 2 0.871071 0.907555 0.827573 11.00000 -1.20000
AFIX 0
C3 1 0.748737 0.788985 0.765433 11.00000 0.05383 0.06127 =
0.06235 -0.00406 0.01937 -0.00165
H4 2 0.642261 0.693002 0.671255 11.00000 0.06726
N4 3 0.698299 0.733504 0.670686 11.00000 0.05221 0.05675 =
0.06949 0.00032 0.02095 -0.00862
C5 1 0.731617 0.749124 0.569291 11.00000 0.04828 0.05751 =
0.05783 0.00164 0.01283 0.00734
C6 1 0.822333 0.828290 0.564826 11.00000 0.04546 0.05052 =
0.06216 0.00229 0.01814 0.00282
C7 1 0.857319 0.842591 0.461720 11.00000 0.05922 0.06339 =
0.07278 0.00713 0.02190 0.00331
AFIX 43
H7 2 0.916742 0.894764 0.456281 11.00000 -1.20000
AFIX 0
C8 1 0.805360 0.781106 0.369918 11.00000 0.07113 0.08718 =
0.06216 -0.00015 0.02540 0.00574
AFIX 43
H8 2 0.829601 0.791189 0.302347 11.00000 -1.20000
AFIX 0
C9 1 0.715330 0.702579 0.377081 11.00000 0.06471 0.08302 =
0.07060 -0.01407 0.01591 0.00102
AFIX 43
H9 2 0.679790 0.661352 0.313551 11.00000 -1.20000
AFIX 0
C10 1 0.678627 0.685269 0.475387 11.00000 0.05201 0.07131 =
0.06740 -0.00808 0.01325 -0.00349
AFIX 43
H10 2 0.619845 0.632319 0.479746 11.00000 -1.20000
AFIX 0
O11 4 0.958943 0.963192 0.655492 11.00000 0.08386 0.06246 =
0.08375 -0.00451 0.03378 -0.02351
AFIX 147
H11 2 0.983704 0.994040 0.716457 11.00000 -1.50000
AFIX 0
C12 1 0.714596 0.755780 0.872619 11.00000 0.07573 0.08364 =
0.07212 -0.00793 0.03140 -0.01400
AFIX 23
H12A 2 0.622598 0.728946 0.852998 11.00000 -1.20000
H12B 2 0.718718 0.813931 0.922720 11.00000 -1.20000
AFIX 0
C13 1 0.815321 0.673273 0.935625 11.00000 0.08711 0.07512 =
0.07726 0.00104 0.03304 -0.00835
AFIX 23
H13A 2 0.806047 0.614174 0.886138 11.00000 -1.20000
H13B 2 0.907252 0.699026 0.948244 11.00000 -1.20000
AFIX 0
C14 1 0.797222 0.640020 1.048233 11.00000 0.08895 0.06965 =
0.08091 -0.00686 0.02880 -0.00791
AFIX 23
H14A 2 0.706636 0.611655 1.035652 11.00000 -1.20000
H14B 2 0.803674 0.699194 1.097259 11.00000 -1.20000
AFIX 0
C15 1 0.902370 0.560468 1.110523 11.00000 0.09219 0.07911 =
0.09623 -0.00100 0.03840 -0.00160
AFIX 23
H15A 2 0.896099 0.501848 1.060727 11.00000 -1.20000
H15B 2 0.992675 0.589248 1.122723 11.00000 -1.20000
AFIX 0
C16 1 0.887765 0.525078 1.222146 11.00000 0.09672 0.07856 =
0.09143 -0.00754 0.03102 0.00538
AFIX 23
H16A 2 0.795361 0.500512 1.210112 11.00000 -1.20000
H16B 2 0.898759 0.583552 1.272696 11.00000 -1.20000
AFIX 0
C17 1 0.982722 0.443593 1.283100 11.00000 0.08018 0.10840 =
0.11465 0.01115 0.02705 0.01895
AFIX 23
H17A 2 1.074308 0.471170 1.306817 11.00000 -1.20000
H17B 2 0.982235 0.388534 1.229743 11.00000 -1.20000
AFIX 0
C18 1 0.948579 0.400891 1.386346 11.00000 0.11555 0.14090 =
0.11890 0.01610 0.02645 0.02386
AFIX 3
H18A 2 0.868913 0.434316 1.395912 11.00000 -1.50000
H18B 2 1.023493 0.411887 1.453196 11.00000 -1.50000
H18C 2 0.931312 0.329182 1.375935 11.00000 -1.50000
AFIX 0
CL19 5 0.450063 0.586906 0.638365 11.00000 0.06259 0.05985 =
0.09038 0.00660 0.02384 -0.00136
HKLF 4

REM mo_GMG_TMS_Sample_001_vs2_0m in P2(1)/n
REM R1 = 0.0559 for 1682 Fo > 4sig(Fo) and 0.1238 for all 3226 data
REM 177 parameters refined using 6 restraints

END

WGHT 0.0793 0.2670
REM Highest difference peak 0.191, deepest hole -0.250, 1-sigma level 0.041
Q1 1 1.0114 0.4877 1.2181 11.00000 0.05 0.19
Q2 1 0.5364 0.5385 0.6841 11.00000 0.05 0.16
Q3 1 0.9578 0.5916 1.2073 11.00000 0.05 0.16
Q4 1 1.0737 0.5055 1.3388 11.00000 0.05 0.15
Q5 1 0.9939 1.0599 0.7627 11.00000 0.05 0.15

;
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 0.8737(3) 0.8888(2) 0.6645(3) 0.0576(7) Uani d . 1 . .
C C2 0.8366(3) 0.8680(2) 0.7625(3) 0.0601(8) Uani d . 1 . .
H H2 0.8711 0.9076 0.8276 0.072 Uiso calc R 1 . .
C C3 0.7487(3) 0.7890(2) 0.7654(2) 0.0585(7) Uani d . 1 . .
H H4 0.642(3) 0.693(2) 0.671(2) 0.067(11) Uiso d . 1 . .
N N4 0.6983(3) 0.7335(2) 0.6707(2) 0.0587(7) Uani d . 1 . .
C C5 0.7316(3) 0.7491(2) 0.5693(2) 0.0549(7) Uani d . 1 . .
C C6 0.8223(3) 0.8283(2) 0.5648(2) 0.0521(7) Uani d . 1 . .
C C7 0.8573(3) 0.8426(2) 0.4617(3) 0.0644(8) Uani d . 1 . .
H H7 0.9167 0.8948 0.4563 0.077 Uiso calc R 1 . .
C C8 0.8054(3) 0.7811(3) 0.3699(3) 0.0721(9) Uani d . 1 . .
H H8 0.8296 0.7912 0.3023 0.087 Uiso calc R 1 . .
C C9 0.7153(3) 0.7026(3) 0.3771(3) 0.0733(9) Uani d . 1 . .
H H9 0.6798 0.6614 0.3136 0.088 Uiso calc R 1 . .
C C10 0.6786(3) 0.6853(2) 0.4754(3) 0.0642(8) Uani d . 1 . .
H H10 0.6198 0.6323 0.4797 0.077 Uiso calc R 1 . .
O O11 0.9589(2) 0.96319(16) 0.65549(17) 0.0746(6) Uani d . 1 . .
H H11 0.9837 0.994 0.7165 0.112 Uiso calc R 1 . .
C C12 0.7146(3) 0.7558(3) 0.8726(3) 0.0750(9) Uani d . 1 . .
H H12A 0.6226 0.7289 0.853 0.09 Uiso calc R 1 . .
H H12B 0.7187 0.8139 0.9227 0.09 Uiso calc R 1 . .
C C13 0.8153(4) 0.6733(3) 0.9356(3) 0.0778(9) Uani d . 1 . .
H H13A 0.806 0.6142 0.8861 0.093 Uiso calc R 1 . .
H H13B 0.9073 0.699 0.9482 0.093 Uiso calc R 1 . .
C C14 0.7972(4) 0.6400(3) 1.0482(3) 0.0788(10) Uani d . 1 . .
H H14A 0.7066 0.6117 1.0357 0.095 Uiso calc R 1 . .
H H14B 0.8037 0.6992 1.0973 0.095 Uiso calc R 1 . .
C C15 0.9024(4) 0.5605(3) 1.1105(3) 0.0867(10) Uani d . 1 . .
H H15A 0.8961 0.5018 1.0607 0.104 Uiso calc R 1 . .
H H15B 0.9927 0.5892 1.1227 0.104 Uiso calc R 1 . .
C C16 0.8878(4) 0.5251(3) 1.2221(3) 0.0879(11) Uani d . 1 . .
H H16A 0.7954 0.5005 1.2101 0.105 Uiso calc R 1 . .
H H16B 0.8988 0.5836 1.2727 0.105 Uiso calc R 1 . .
C C17 0.9827(4) 0.4436(3) 1.2831(4) 0.1011(12) Uani d . 1 . .
H H17A 1.0743 0.4712 1.3068 0.121 Uiso calc R 1 . .
H H17B 0.9822 0.3885 1.2297 0.121 Uiso calc R 1 . .
C C18 0.9486(5) 0.4009(4) 1.3863(4) 0.1263(16) Uani d U 1 . .
H H18A 0.8689 0.4343 1.3959 0.189 Uiso d R 1 . .
H H18B 1.0235 0.4119 1.4532 0.189 Uiso d R 1 . .
H H18C 0.9313 0.3292 1.3759 0.189 Uiso d R 1 . .
Cl Cl19 0.45006(7) 0.58691(6) 0.63837(7) 0.0704(3) Uani d . 1 . .

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
C1 0.0521(16) 0.0528(17) 0.0683(19) 0.0006(14) 0.0175(15) 0.0006(14)
C2 0.0571(17) 0.0587(18) 0.0642(19) -0.0066(15) 0.0164(15) -0.0057(14)
C3 0.0538(17) 0.0613(18) 0.0623(18) -0.0016(15) 0.0194(15) -0.0041(15)
N4 0.0522(15) 0.0568(16) 0.0695(18) -0.0086(13) 0.0210(13) 0.0003(13)
C5 0.0483(15) 0.0575(18) 0.0578(17) 0.0073(14) 0.0128(14) 0.0016(14)
C6 0.0455(15) 0.0505(16) 0.0622(18) 0.0028(13) 0.0181(14) 0.0023(14)
C7 0.0592(18) 0.0634(19) 0.073(2) 0.0033(15) 0.0219(16) 0.0071(17)
C8 0.071(2) 0.087(2) 0.0622(19) 0.0057(19) 0.0254(17) -0.0002(18)
C9 0.065(2) 0.083(2) 0.071(2) 0.0010(18) 0.0159(17) -0.0141(18)
C10 0.0520(17) 0.071(2) 0.067(2) -0.0035(15) 0.0132(15) -0.0081(16)
O11 0.0839(15) 0.0625(13) 0.0838(15) -0.0235(12) 0.0338(13) -0.0045(11)
C12 0.076(2) 0.084(2) 0.072(2) -0.0140(18) 0.0314(18) -0.0079(17)
C13 0.087(2) 0.075(2) 0.077(2) -0.0083(19) 0.0330(19) 0.0010(18)
C14 0.089(2) 0.070(2) 0.081(2) -0.0079(19) 0.0288(19) -0.0069(18)
C15 0.092(2) 0.079(2) 0.096(3) -0.002(2) 0.038(2) -0.001(2)
C16 0.097(3) 0.079(2) 0.091(3) 0.005(2) 0.031(2) -0.008(2)
C17 0.080(2) 0.108(3) 0.115(3) 0.019(2) 0.027(2) 0.011(3)
C18 0.116(3) 0.141(4) 0.119(3) 0.024(3) 0.026(3) 0.016(3)
Cl19 0.0626(5) 0.0598(5) 0.0904(6) -0.0014(4) 0.0238(4) 0.0066(4)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O11 . 1.333(3) ?
C1 C2 . 1.373(4) ?
C1 C6 . 1.421(4) ?
C2 C3 . 1.379(4) ?
C2 H2 . 0.93 ?
C3 N4 . 1.339(4) ?
C3 C12 . 1.503(4) ?
N4 C5 . 1.381(4) ?
N4 H4 . 0.78(3) ?
C5 C10 . 1.398(4) ?
C5 C6 . 1.404(4) ?
C6 C7 . 1.407(4) ?
C7 C8 . 1.360(4) ?
C7 H7 . 0.93 ?
C8 C9 . 1.401(4) ?
C8 H8 . 0.93 ?
C9 C10 . 1.366(4) ?
C9 H9 . 0.93 ?
C10 H10 . 0.93 ?
O11 H11 . 0.82 ?
C12 C13 . 1.544(5) ?
C12 H12A . 0.97 ?
C12 H12B . 0.97 ?
C13 C14 . 1.495(4) ?
C13 H13A . 0.97 ?
C13 H13B . 0.97 ?
C14 C15 . 1.539(5) ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C15 C16 . 1.479(5) ?
C15 H15A . 0.97 ?
C15 H15B . 0.97 ?
C16 C17 . 1.496(5) ?
C16 H16A . 0.97 ?
C16 H16B . 0.97 ?
C17 C18 . 1.500(6) ?
C17 H17A . 0.97 ?
C17 H17B . 0.97 ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?

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
O11 C1 C2 . . 124.1(3) ?
O11 C1 C6 . . 115.9(3) ?
C2 C1 C6 . . 120.0(3) ?
C1 C2 C3 . . 120.7(3) ?
C1 C2 H2 . . 119.6 ?
C3 C2 H2 . . 119.6 ?
N4 C3 C2 . . 119.0(3) ?
N4 C3 C12 . . 117.4(3) ?
C2 C3 C12 . . 123.4(3) ?
C3 N4 C5 . . 123.7(3) ?
C3 N4 H4 . . 118.(2) ?
C5 N4 H4 . . 118.(2) ?
N4 C5 C10 . . 120.2(3) ?
N4 C5 C6 . . 118.2(3) ?
C10 C5 C6 . . 121.6(3) ?
C5 C6 C7 . . 117.8(3) ?
C5 C6 C1 . . 118.3(3) ?
C7 C6 C1 . . 123.9(3) ?
C8 C7 C6 . . 120.8(3) ?
C8 C7 H7 . . 119.6 ?
C6 C7 H7 . . 119.6 ?
C7 C8 C9 . . 120.0(3) ?
C7 C8 H8 . . 120.0 ?
C9 C8 H8 . . 120.0 ?
C10 C9 C8 . . 121.4(3) ?
C10 C9 H9 . . 119.3 ?
C8 C9 H9 . . 119.3 ?
C9 C10 C5 . . 118.4(3) ?
C9 C10 H10 . . 120.8 ?
C5 C10 H10 . . 120.8 ?
C1 O11 H11 . . 109.5 ?
C3 C12 C13 . . 110.5(3) ?
C3 C12 H12A . . 109.6 ?
C13 C12 H12A . . 109.6 ?
C3 C12 H12B . . 109.6 ?
C13 C12 H12B . . 109.6 ?
H12A C12 H12B . . 108.1 ?
C14 C13 C12 . . 115.1(3) ?
C14 C13 H13A . . 108.5 ?
C12 C13 H13A . . 108.5 ?
C14 C13 H13B . . 108.5 ?
C12 C13 H13B . . 108.5 ?
H13A C13 H13B . . 107.5 ?
C13 C14 C15 . . 113.7(3) ?
C13 C14 H14A . . 108.8 ?
C15 C14 H14A . . 108.8 ?
C13 C14 H14B . . 108.8 ?
C15 C14 H14B . . 108.8 ?
H14A C14 H14B . . 107.7 ?
C16 C15 C14 . . 115.4(3) ?
C16 C15 H15A . . 108.4 ?
C14 C15 H15A . . 108.4 ?
C16 C15 H15B . . 108.4 ?
C14 C15 H15B . . 108.4 ?
H15A C15 H15B . . 107.5 ?
C15 C16 C17 . . 117.5(3) ?
C15 C16 H16A . . 107.9 ?
C17 C16 H16A . . 107.9 ?
C15 C16 H16B . . 107.9 ?
C17 C16 H16B . . 107.9 ?
H16A C16 H16B . . 107.2 ?
C16 C17 C18 . . 114.3(3) ?
C16 C17 H17A . . 108.7 ?
C18 C17 H17A . . 108.7 ?
C16 C17 H17B . . 108.7 ?
C18 C17 H17B . . 108.7 ?
H17A C17 H17B . . 107.6 ?
C17 C18 H18A . . 109.4 ?
C17 C18 H18B . . 109.6 ?
H18A C18 H18B . . 109.5 ?
C17 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O11 C1 C2 C3 . . . . -179.4(3) ?
C6 C1 C2 C3 . . . . -0.5(4) ?
C1 C2 C3 N4 . . . . -0.9(4) ?
C1 C2 C3 C12 . . . . 173.9(3) ?
C2 C3 N4 C5 . . . . 1.6(4) ?
C12 C3 N4 C5 . . . . -173.6(3) ?
C3 N4 C5 C10 . . . . 177.5(3) ?
C3 N4 C5 C6 . . . . -0.7(4) ?
N4 C5 C6 C7 . . . . 179.0(2) ?
C10 C5 C6 C7 . . . . 0.9(4) ?
N4 C5 C6 C1 . . . . -0.7(4) ?
C10 C5 C6 C1 . . . . -178.9(3) ?
O11 C1 C6 C5 . . . . -179.7(2) ?
C2 C1 C6 C5 . . . . 1.3(4) ?
O11 C1 C6 C7 . . . . 0.5(4) ?
C2 C1 C6 C7 . . . . -178.4(3) ?
C5 C6 C7 C8 . . . . -0.4(4) ?
C1 C6 C7 C8 . . . . 179.3(3) ?
C6 C7 C8 C9 . . . . 0.3(4) ?
C7 C8 C9 C10 . . . . -0.6(5) ?
C8 C9 C10 C5 . . . . 1.0(4) ?
N4 C5 C10 C9 . . . . -179.3(3) ?
C6 C5 C10 C9 . . . . -1.1(4) ?
N4 C3 C12 C13 . . . . 85.0(3) ?
C2 C3 C12 C13 . . . . -89.9(4) ?
C3 C12 C13 C14 . . . . 175.7(3) ?
C12 C13 C14 C15 . . . . -178.0(3) ?
C13 C14 C15 C16 . . . . -179.7(3) ?
C14 C15 C16 C17 . . . . 176.7(3) ?
C15 C16 C17 C18 . . . . -171.3(4) ?

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
O11 H11 Cl19 2_656 0.82 2.10 2.912(3) 173.7 ?