# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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.
# 
#  For further information on the CCDC, data deposition and
#  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_knih98

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H27 N3 O3'
_chemical_formula_sum            'C21 H27 N3 O3'
_chemical_formula_weight         369.46
_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 0.0181 0.0091 '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 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   9.1670(2)
_cell_length_b                   13.2568(3)
_cell_length_c                   15.2701(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1855.70(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9980
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      67.84

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.218
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_max          0.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.719
##############################################################################
#                                                                            #
#  NOTE on absorbtion correction with SADABS:                                #
#                                                                            #
#  (Semi)empirical correction methods for absorption correction are more of  #
#  a problem in that they often specify only a relative correction range     #
#  [ Tmin(emp) & Tmax(emp)].                                                 #
#                                                                            #
#  Acta Cryst. procedures call in such cases for the multiplication of both  #
#  empirical values with Tmax(expected).                                     #
#                                                                            #
#  THIS RECOMMENDATION IS CURRENTLY UNDER REVIEW!  (George                   #
#  and Ton are agruing this point!)                                          #
#                                                                            #
##############################################################################
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000c)'
_exptl_absorpt_correction_T_min  0.7579
_exptl_absorpt_correction_T_max  0.8590


_exptl_special_details           
; 
The absolute configuration was evaluated using using likelihood methods 
in PLATON (Spek, 2010; Hooft, Straver & Spek, 2008).  Based on the 
analysis of 1183 Bvjot pairs this analysis indicated that the absolute 
structure had been correctly assigned. The method calculated that the 
probability that the structure is inverted is smaller than 6x10-27.

Details from analysis

Bijovet pairs = 1183 (82%)
P2(true) = 1.000
P3(true) = 1.000
P3(rac-twin) = 0.1 x 10⁻³
P3(false) = 0.6 x 10⁻²⁷
Hooft y = 0.15(7)

Absolute configuration as reported by PLATON: C5 = R, C6 = S, C9 = R, 
C10 = R, and C14 = S.
;

_diffrn_ambient_temperature      296(2)
# PLATINUM 135 parameters
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_measurement_device       'Bruker PLATINUM 135 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10711
_diffrn_reflns_av_R_equivalents  0.1150
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.42
_diffrn_reflns_theta_max         67.99
_reflns_number_total             3010
_reflns_number_gt                2997
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_cell_refinement       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_data_reduction        
;
Bruker SAINT v6.45A (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001)
;
_computing_structure_solution    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_structure_refinement  'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_molecular_graphics    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_publication_material  'Bruker SHELXTL v6.14 (Bruker, 2000b)'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0877P)²+0.3143P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   -0.1(2)
_refine_ls_number_reflns         3010
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1236
_refine_ls_wR_factor_gt          0.1232
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_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
C1 C 0.7521(2) 0.14372(15) 0.09220(12) 0.0301(4) Uani 1 1 d . . .
H1A H 0.7161 0.1040 0.0469 0.036 Uiso 1 1 calc R . .
C2 C 0.6613(2) 0.21463(15) 0.13063(13) 0.0307(4) Uani 1 1 d . . .
H2A H 0.5670 0.2227 0.1093 0.037 Uiso 1 1 calc R . .
C3 C 0.7081(2) 0.27458(15) 0.20100(13) 0.0274(4) Uani 1 1 d . . .
C4 C 0.8502(2) 0.25979(14) 0.22800(12) 0.0259(4) Uani 1 1 d . . .
O5 O 0.91272(15) 0.30145(10) 0.30187(8) 0.0267(3) Uani 1 1 d . . .
C5 C 1.0477(2) 0.24466(14) 0.31829(12) 0.0265(4) Uani 1 1 d . . .
H5A H 1.1258 0.2918 0.3340 0.032 Uiso 1 1 calc R . .
C6 C 1.0231(2) 0.17087(15) 0.39398(12) 0.0278(4) Uani 1 1 d . . .
H6A H 1.1186 0.1470 0.4139 0.033 Uiso 1 1 calc R . .
C7 C 0.9358(2) 0.07969(15) 0.36357(13) 0.0294(4) Uani 1 1 d . . .
H7A H 0.8436 0.1022 0.3392 0.035 Uiso 1 1 calc R . .
H7B H 0.9147 0.0367 0.4134 0.035 Uiso 1 1 calc R . .
C8 C 1.0195(2) 0.01854(15) 0.29407(12) 0.0306(4) Uani 1 1 d . . .
H8A H 0.9493 -0.0123 0.2548 0.037 Uiso 1 1 calc R . .
H8B H 1.0717 -0.0355 0.3233 0.037 Uiso 1 1 calc R . .
C9 C 1.1446(2) 0.04135(15) 0.14271(12) 0.0301(4) Uani 1 1 d . . .
H9A H 1.1729 -0.0299 0.1456 0.036 Uiso 1 1 calc R . .
C10 C 0.9982(2) 0.04714(16) 0.09045(14) 0.0304(4) Uani 1 1 d . . .
H10A H 1.0205 0.0569 0.0289 0.037 Uiso 1 1 calc R . .
H10B H 0.9481 -0.0170 0.0960 0.037 Uiso 1 1 calc R . .
C11 C 0.8958(2) 0.13028(14) 0.11961(12) 0.0270(4) Uani 1 1 d . . .
C12 C 0.9426(2) 0.19386(14) 0.18572(12) 0.0257(4) Uani 1 1 d . . .
C13 C 1.0870(2) 0.19147(14) 0.23141(12) 0.0256(4) Uani 1 1 d . . .
C14 C 1.1302(2) 0.08000(14) 0.23853(12) 0.0279(4) Uani 1 1 d . . .
H14A H 1.2261 0.0758 0.2667 0.034 Uiso 1 1 calc R . .
C15 C 1.2044(2) 0.25003(15) 0.18171(12) 0.0286(4) Uani 1 1 d . . .
H15A H 1.1730 0.3194 0.1744 0.034 Uiso 1 1 calc R . .
H15B H 1.2937 0.2504 0.2158 0.034 Uiso 1 1 calc R . .
C16 C 1.2345(2) 0.20407(16) 0.09237(13) 0.0307(4) Uani 1 1 d . . .
H16A H 1.1500 0.2127 0.0549 0.037 Uiso 1 1 calc R . .
H16B H 1.3165 0.2381 0.0653 0.037 Uiso 1 1 calc R . .
N17 N 1.26711(19) 0.09684(13) 0.10190(11) 0.0315(4) Uani 1 1 d . . .
C17 C 1.3140(3) 0.05279(18) 0.01967(15) 0.0389(5) Uani 1 1 d . . .
H17A H 1.3933 0.0915 -0.0039 0.058 Uiso 1 1 calc R . .
H17B H 1.2342 0.0530 -0.0210 0.058 Uiso 1 1 calc R . .
H17C H 1.3456 -0.0153 0.0295 0.058 Uiso 1 1 calc R . .
N18 N 0.61619(19) 0.34043(14) 0.24926(10) 0.0318(4) Uani 1 1 d . . .
H18A H 0.6230 0.3384 0.3054 0.038 Uiso 1 1 calc R . .
C19 C 0.5186(2) 0.40624(16) 0.21467(14) 0.0315(5) Uani 1 1 d . . .
O19 O 0.49566(19) 0.41387(12) 0.13606(10) 0.0428(4) Uani 1 1 d . . .
C20 C 0.4395(3) 0.46918(18) 0.28210(15) 0.0382(5) Uani 1 1 d . . .
H20A H 0.3726 0.5138 0.2532 0.057 Uiso 1 1 calc R . .
H20B H 0.5090 0.5080 0.3149 0.057 Uiso 1 1 calc R . .
H20C H 0.3867 0.4257 0.3211 0.057 Uiso 1 1 calc R . .
N21 N 0.95498(19) 0.22573(13) 0.46598(10) 0.0312(4) Uani 1 1 d . . .
H21A H 0.8652 0.2435 0.4609 0.037 Uiso 1 1 calc R . .
C22 C 1.0264(2) 0.24965(15) 0.53979(12) 0.0283(4) Uani 1 1 d . . .
O22 O 1.14788(16) 0.21459(12) 0.55794(9) 0.0341(3) Uani 1 1 d . . .
C23 C 0.9524(3) 0.32405(18) 0.59922(14) 0.0391(5) Uani 1 1 d . . .
H23D H 1.0123 0.3358 0.6497 0.059 Uiso 1 1 calc R . .
H23A H 0.8598 0.2975 0.6174 0.059 Uiso 1 1 calc R . .
H23B H 0.9377 0.3864 0.5685 0.059 Uiso 1 1 calc R . .


_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
C1 C2 1.386(3) . ?
C1 C11 1.394(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.404(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.381(3) . ?
C3 N18 1.419(2) . ?
C4 C12 1.378(3) . ?
C4 O5 1.381(2) . ?
O5 C5 1.470(2) . ?
C5 C6 1.531(3) . ?
C5 C13 1.545(3) . ?
C5 H5A 0.9800 . ?
C6 N21 1.458(2) . ?
C6 C7 1.522(3) . ?
C6 H6A 0.9800 . ?
C7 C8 1.541(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C14 1.553(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N17 1.480(3) . ?
C9 C14 1.556(3) . ?
C9 C10 1.564(3) . ?
C9 H9A 0.9800 . ?
C10 C11 1.514(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.383(3) . ?
C12 C13 1.497(3) . ?
C13 C15 1.529(3) . ?
C13 C14 1.534(3) . ?
C14 H14A 0.9800 . ?
C15 C16 1.519(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N17 1.460(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
N17 C17 1.450(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N18 C19 1.357(3) . ?
N18 H18A 0.8600 . ?
C19 O19 1.223(3) . ?
C19 C20 1.510(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N21 C22 1.342(2) . ?
N21 H21A 0.8600 . ?
C22 O22 1.238(3) . ?
C22 C23 1.502(3) . ?
C23 H23D 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?

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
C2 C1 C11 121.81(18) . . ?
C2 C1 H1A 119.1 . . ?
C11 C1 H1A 119.1 . . ?
C1 C2 C3 121.66(19) . . ?
C1 C2 H2A 119.2 . . ?
C3 C2 H2A 119.2 . . ?
C4 C3 C2 115.87(19) . . ?
C4 C3 N18 119.49(18) . . ?
C2 C3 N18 124.37(18) . . ?
C12 C4 O5 112.43(17) . . ?
C12 C4 C3 122.03(18) . . ?
O5 C4 C3 125.38(18) . . ?
C4 O5 C5 106.49(13) . . ?
O5 C5 C6 109.40(15) . . ?
O5 C5 C13 106.49(15) . . ?
C6 C5 C13 113.03(15) . . ?
O5 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C13 C5 H5A 109.3 . . ?
N21 C6 C7 113.64(16) . . ?
N21 C6 C5 108.27(16) . . ?
C7 C6 C5 110.76(15) . . ?
N21 C6 H6A 108.0 . . ?
C7 C6 H6A 108.0 . . ?
C5 C6 H6A 108.0 . . ?
C6 C7 C8 111.46(16) . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C14 115.20(16) . . ?
C7 C8 H8A 108.5 . . ?
C14 C8 H8A 108.5 . . ?
C7 C8 H8B 108.5 . . ?
C14 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
N17 C9 C14 107.28(16) . . ?
N17 C9 C10 114.34(16) . . ?
C14 C9 C10 112.97(16) . . ?
N17 C9 H9A 107.3 . . ?
C14 C9 H9A 107.3 . . ?
C10 C9 H9A 107.3 . . ?
C11 C10 C9 114.70(17) . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C1 115.74(18) . . ?
C12 C11 C10 117.76(18) . . ?
C1 C11 C10 126.19(18) . . ?
C4 C12 C11 122.55(19) . . ?
C4 C12 C13 109.80(17) . . ?
C11 C12 C13 126.98(18) . . ?
C12 C13 C15 112.37(15) . . ?
C12 C13 C14 106.35(15) . . ?
C15 C13 C14 110.06(16) . . ?
C12 C13 C5 100.60(16) . . ?
C15 C13 C5 111.04(16) . . ?
C14 C13 C5 116.04(15) . . ?
C13 C14 C8 112.08(16) . . ?
C13 C14 C9 105.82(15) . . ?
C8 C14 C9 113.36(16) . . ?
C13 C14 H14A 108.5 . . ?
C8 C14 H14A 108.5 . . ?
C9 C14 H14A 108.5 . . ?
C16 C15 C13 111.72(16) . . ?
C16 C15 H15A 109.3 . . ?
C13 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C13 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
N17 C16 C15 109.77(16) . . ?
N17 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
N17 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C17 N17 C16 111.50(17) . . ?
C17 N17 C9 112.92(17) . . ?
C16 N17 C9 111.76(16) . . ?
N17 C17 H17A 109.5 . . ?
N17 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N17 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 N18 C3 125.78(16) . . ?
C19 N18 H18A 117.1 . . ?
C3 N18 H18A 117.1 . . ?
O19 C19 N18 123.27(19) . . ?
O19 C19 C20 122.76(19) . . ?
N18 C19 C20 113.97(18) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 N21 C6 122.85(17) . . ?
C22 N21 H21A 118.6 . . ?
C6 N21 H21A 118.6 . . ?
O22 C22 N21 122.57(18) . . ?
O22 C22 C23 121.16(18) . . ?
N21 C22 C23 116.25(19) . . ?
C22 C23 H23D 109.5 . . ?
C22 C23 H23A 109.5 . . ?
H23D C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23D C23 H23B 109.5 . . ?
H23A C23 H23B 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
C11 C1 C2 C3 -1.9(3) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C1 C2 C3 N18 -172.83(17) . . . . ?
C2 C3 C4 C12 3.1(3) . . . . ?
N18 C3 C4 C12 177.47(17) . . . . ?
C2 C3 C4 O5 -171.84(17) . . . . ?
N18 C3 C4 O5 2.5(3) . . . . ?
C12 C4 O5 C5 -10.76(19) . . . . ?
C3 C4 O5 C5 164.59(18) . . . . ?
C4 O5 C5 C6 -103.15(16) . . . . ?
C4 O5 C5 C13 19.31(18) . . . . ?
O5 C5 C6 N21 -48.7(2) . . . . ?
C13 C5 C6 N21 -167.16(16) . . . . ?
O5 C5 C6 C7 76.53(18) . . . . ?
C13 C5 C6 C7 -41.9(2) . . . . ?
N21 C6 C7 C8 -174.27(15) . . . . ?
C5 C6 C7 C8 63.6(2) . . . . ?
C6 C7 C8 C14 -27.2(2) . . . . ?
N17 C9 C10 C11 -94.1(2) . . . . ?
C14 C9 C10 C11 28.9(2) . . . . ?
C2 C1 C11 C12 -1.6(3) . . . . ?
C2 C1 C11 C10 171.87(18) . . . . ?
C9 C10 C11 C12 2.3(3) . . . . ?
C9 C10 C11 C1 -171.11(18) . . . . ?
O5 C4 C12 C11 168.49(16) . . . . ?
C3 C4 C12 C11 -7.0(3) . . . . ?
O5 C4 C12 C13 -2.7(2) . . . . ?
C3 C4 C12 C13 -178.20(16) . . . . ?
C1 C11 C12 C4 6.0(3) . . . . ?
C10 C11 C12 C4 -168.05(17) . . . . ?
C1 C11 C12 C13 175.61(17) . . . . ?
C10 C11 C12 C13 1.5(3) . . . . ?
C4 C12 C13 C15 -104.26(18) . . . . ?
C11 C12 C13 C15 85.1(2) . . . . ?
C4 C12 C13 C14 135.25(16) . . . . ?
C11 C12 C13 C14 -35.4(2) . . . . ?
C4 C12 C13 C5 13.9(2) . . . . ?
C11 C12 C13 C5 -156.77(18) . . . . ?
O5 C5 C13 C12 -19.76(18) . . . . ?
C6 C5 C13 C12 100.39(18) . . . . ?
O5 C5 C13 C15 99.37(18) . . . . ?
C6 C5 C13 C15 -140.48(17) . . . . ?
O5 C5 C13 C14 -133.97(16) . . . . ?
C6 C5 C13 C14 -13.8(2) . . . . ?
C12 C13 C14 C8 -61.97(19) . . . . ?
C15 C13 C14 C8 176.07(16) . . . . ?
C5 C13 C14 C8 48.9(2) . . . . ?
C12 C13 C14 C9 62.06(19) . . . . ?
C15 C13 C14 C9 -59.9(2) . . . . ?
C5 C13 C14 C9 172.96(16) . . . . ?
C7 C8 C14 C13 -27.1(2) . . . . ?
C7 C8 C14 C9 -146.77(17) . . . . ?
N17 C9 C14 C13 64.6(2) . . . . ?
C10 C9 C14 C13 -62.3(2) . . . . ?
N17 C9 C14 C8 -172.19(16) . . . . ?
C10 C9 C14 C8 60.9(2) . . . . ?
C12 C13 C15 C16 -63.0(2) . . . . ?
C14 C13 C15 C16 55.3(2) . . . . ?
C5 C13 C15 C16 -174.80(16) . . . . ?
C13 C15 C16 N17 -53.1(2) . . . . ?
C15 C16 N17 C17 -172.94(17) . . . . ?
C15 C16 N17 C9 59.6(2) . . . . ?
C14 C9 N17 C17 166.89(16) . . . . ?
C10 C9 N17 C17 -67.0(2) . . . . ?
C14 C9 N17 C16 -66.4(2) . . . . ?
C10 C9 N17 C16 59.7(2) . . . . ?
C4 C3 N18 C19 140.1(2) . . . . ?
C2 C3 N18 C19 -46.0(3) . . . . ?
C3 N18 C19 O19 2.3(3) . . . . ?
C3 N18 C19 C20 -178.04(19) . . . . ?
C7 C6 N21 C22 128.89(19) . . . . ?
C5 C6 N21 C22 -107.6(2) . . . . ?
C6 N21 C22 O22 -10.9(3) . . . . ?
C6 N21 C22 C23 167.7(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
N18 H18A O22 0.86 2.21 3.047(2) 163.1 2_456
N21 H21A O22 0.86 2.09 2.947(2) 177.2 2_456

_diffrn_measured_fraction_theta_max 0.941
_diffrn_reflns_theta_full        67.99
_diffrn_measured_fraction_theta_full 0.940
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 1002920'
#######################################################################
#
#                 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.
# 
#  For further information on the CCDC, data deposition and
#  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_knih099



_audit_creation_date             2013-11-22

_audit_creation_method           'from SHELXTL CIF, local template and enCIFer'

_chemical_name_systematic        
; 

 ? 

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         
'C17 H17 Cl N2 O4'

_chemical_formula_sum            
'C17 H17 Cl N2 O4'

_chemical_formula_weight         348.78



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'




_symmetry_cell_setting           Orthorhombic

_symmetry_space_group_name_H-M   P2(1)2(1)2(1)



loop_

_symmetry_equiv_pos_as_xyz




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



_cell_length_a                   7.3581(12)

_cell_length_b                   9.1360(16)

_cell_length_c                   23.005(4)

_cell_angle_alpha                90

_cell_angle_beta                 90

_cell_angle_gamma                90

_cell_volume                     1546.5(5)

_cell_formula_units_Z            4

_cell_measurement_temperature    150(2)

_cell_measurement_reflns_used    ?

_cell_measurement_theta_min      ?

_cell_measurement_theta_max      ?



_exptl_crystal_description       plate

_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.51

_exptl_crystal_size_mid          0.43

_exptl_crystal_size_min          0.01

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.498

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             728

_exptl_absorpt_coefficient_mu    0.272

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_process_details   
'SADABS v2008/1 (Bruker, 2008)'

_exptl_absorpt_correction_T_min  0.8736


_exptl_absorpt_correction_T_max  0.9973



_exptl_special_details           
; 

 ? 

;



_diffrn_ambient_temperature      150(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  'Bruker SMART APEX II CCD'

_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            13822


_diffrn_reflns_av_R_equivalents  0.0355


_diffrn_reflns_av_sigmaI/netI    0.0295


_diffrn_reflns_limit_h_min       -8

_diffrn_reflns_limit_h_max       9

_diffrn_reflns_limit_k_min       -11

_diffrn_reflns_limit_k_max       11

_diffrn_reflns_limit_l_min       -28

_diffrn_reflns_limit_l_max       28

_diffrn_reflns_theta_min         1.77


_diffrn_reflns_theta_max         26.48


_reflns_number_total             3198

_reflns_number_gt                2949

_reflns_threshold_expression     I>2σ(I)



_computing_data_collection       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'

_computing_cell_refinement       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'

_computing_data_reduction        
;

Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008)

;

_computing_structure_solution    'Bruker SHELXTL v2008/4 (Bruker, 2008)'


_computing_structure_refinement  'Bruker SHELXTL v2008/4 (Bruker, 2008)'


_computing_molecular_graphics    'Bruker SHELXTL v2008/4 (Bruker, 2008)'

_computing_publication_material  'Bruker SHELXTL v2008/4 (Bruker, 2008)'




_refine_special_details          
; 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and


 goodness of fit S are based on F², conventional R-factors R are based


 on F, with F set to zero for negative F². The threshold expression of


 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is


 not relevant to the choice of reflections for refinement.  R-factors based


 on F² 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/[σ²(Fo²)+(0.0323P)²+0.3470P] where P=(Fo²+2Fc²)/3'


_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_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   -0.03(5)

_refine_ls_number_reflns         3198

_refine_ls_number_parameters     218

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0329

_refine_ls_R_factor_gt           0.0284

_refine_ls_wR_factor_ref         0.0702

_refine_ls_wR_factor_gt          0.0680

_refine_ls_goodness_of_fit_ref   1.045

_refine_ls_restrained_S_all      1.045

_refine_ls_shift/su_max          0.001

_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

































































C1 C 0.7316(2) 0.29231(18) 0.89545(7) 0.0252(4) Uani 1 1 d . . .
Cl1A Cl 0.66849(7) 0.14509(5) 0.85181(2) 0.03976(13) Uani 1 1 d . . .
C2 C 0.6919(2) 0.28738(18) 0.95390(7) 0.0261(4) Uani 1 1 d . . .
H2 H 0.6258 0.2070 0.9694 0.031 Uiso 1 1 calc R . .
C3 C 0.7489(2) 0.40071(18) 0.99055(7) 0.0236(3) Uani 1 1 d . . .
N3A N 0.7084(2) 0.39111(16) 1.05229(6) 0.0284(3) Uani 1 1 d . . .
O3A O 0.6447(2) 0.27691(16) 1.07094(6) 0.0476(4) Uani 1 1 d . . .
O3B O 0.7394(2) 0.49953(15) 1.08239(5) 0.0384(3) Uani 1 1 d . . .
C4 C 0.8462(2) 0.51665(16) 0.96703(6) 0.0195(3) Uani 1 1 d . . .
C5 C 1.0589(2) 0.68810(17) 0.95206(6) 0.0204(3) Uani 1 1 d . . .
H5 H 1.0769 0.7956 0.9580 0.024 Uiso 1 1 calc R . .
O5A O 0.92856(15) 0.63112(12) 0.99449(4) 0.0222(2) Uani 1 1 d . . .
C6 C 1.2394(2) 0.60681(17) 0.95982(7) 0.0227(3) Uani 1 1 d . . .
O6A O 1.27439(17) 0.53961(13) 1.00359(5) 0.0289(3) Uani 1 1 d . . .
C7 C 1.3621(2) 0.6098(2) 0.90776(7) 0.0269(4) Uani 1 1 d . . .
H7A H 1.4759 0.5561 0.9163 0.032 Uiso 1 1 calc R . .
H7B H 1.3937 0.7122 0.8979 0.032 Uiso 1 1 calc R . .
C8 C 1.2626(2) 0.53742(19) 0.85637(7) 0.0268(4) Uani 1 1 d . . .
H8A H 1.3458 0.5290 0.8227 0.032 Uiso 1 1 calc R . .
H8B H 1.2225 0.4378 0.8674 0.032 Uiso 1 1 calc R . .
C9 C 0.9781(2) 0.5674(2) 0.79130(7) 0.0275(4) Uani 1 1 d . . .
H9 H 1.0595 0.5465 0.7575 0.033 Uiso 1 1 calc R . .
C10 C 0.8844(2) 0.42055(19) 0.80765(7) 0.0274(4) Uani 1 1 d . . .
H10A H 0.7767 0.4071 0.7824 0.033 Uiso 1 1 calc R . .
H10B H 0.9697 0.3393 0.7994 0.033 Uiso 1 1 calc R . .
C11 C 0.8251(2) 0.41012(16) 0.87000(7) 0.0211(3) Uani 1 1 d . . .
C12 C 0.8737(2) 0.52023(17) 0.90763(6) 0.0183(3) Uani 1 1 d . . .
C13 C 0.9724(2) 0.65889(17) 0.89194(6) 0.0189(3) Uani 1 1 d . . .
C14 C 1.0991(2) 0.62991(18) 0.83996(6) 0.0234(3) Uani 1 1 d . . .
H14 H 1.1457 0.7268 0.8263 0.028 Uiso 1 1 calc R . .
C15 C 0.8365(2) 0.77879(17) 0.87383(7) 0.0240(3) Uani 1 1 d . . .
H15A H 0.7497 0.7966 0.9059 0.029 Uiso 1 1 calc R . .
H15B H 0.9028 0.8711 0.8662 0.029 Uiso 1 1 calc R . .
C16 C 0.7327(3) 0.7333(2) 0.81944(7) 0.0294(4) Uani 1 1 d . . .
H16A H 0.6477 0.6531 0.8294 0.035 Uiso 1 1 calc R . .
H16B H 0.6599 0.8173 0.8054 0.035 Uiso 1 1 calc R . .
N17 N 0.8536(2) 0.68443(16) 0.77302(6) 0.0302(3) Uani 1 1 d . . .
C17A C 0.7494(3) 0.6457(3) 0.72106(8) 0.0447(5) Uani 1 1 d . . .
H17A H 0.6867 0.7327 0.7063 0.067 Uiso 1 1 calc R . .
H17B H 0.6598 0.5703 0.7309 0.067 Uiso 1 1 calc R . .
H17C H 0.8320 0.6081 0.6912 0.067 Uiso 1 1 calc R . .







_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













































C1 C2 1.377(2) . ?
C1 C11 1.405(2) . ?
C1 Cl1A 1.7415(17) . ?
C2 C3 1.399(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(2) . ?
C3 N3A 1.454(2) . ?
N3A O3A 1.2218(19) . ?
N3A O3B 1.230(2) . ?
C4 O5A 1.3640(19) . ?
C4 C12 1.382(2) . ?
C5 O5A 1.4643(18) . ?
C5 C6 1.532(2) . ?
C5 C13 1.546(2) . ?
C5 H5 1.0000 . ?
C6 O6A 1.2072(19) . ?
C6 C7 1.500(2) . ?
C7 C8 1.540(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.518(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N17 1.469(2) . ?
C9 C14 1.540(2) . ?
C9 C10 1.554(2) . ?
C9 H9 1.0000 . ?
C10 C11 1.502(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.374(2) . ?
C12 C13 1.504(2) . ?
C13 C14 1.539(2) . ?
C13 C15 1.541(2) . ?
C14 H14 1.0000 . ?
C15 C16 1.524(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N17 1.460(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
N17 C17A 1.464(2) . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 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
























































































C2 C1 C11 122.41(15) . . ?
C2 C1 Cl1A 118.77(13) . . ?
C11 C1 Cl1A 118.81(13) . . ?
C1 C2 C3 120.04(15) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 118.96(14) . . ?
C4 C3 N3A 122.16(15) . . ?
C2 C3 N3A 118.86(15) . . ?
O3A N3A O3B 124.14(14) . . ?
O3A N3A C3 118.24(15) . . ?
O3B N3A C3 117.62(13) . . ?
O5A C4 C12 112.01(13) . . ?
O5A C4 C3 129.33(14) . . ?
C12 C4 C3 118.62(14) . . ?
O5A C5 C6 108.54(12) . . ?
O5A C5 C13 105.39(12) . . ?
C6 C5 C13 112.18(12) . . ?
O5A C5 H5 110.2 . . ?
C6 C5 H5 110.2 . . ?
C13 C5 H5 110.2 . . ?
C4 O5A C5 104.78(11) . . ?
O6A C6 C7 123.17(16) . . ?
O6A C6 C5 121.90(15) . . ?
C7 C6 C5 114.83(13) . . ?
C6 C7 C8 108.60(13) . . ?
C6 C7 H7A 110.0 . . ?
C8 C7 H7A 110.0 . . ?
C6 C7 H7B 110.0 . . ?
C8 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
C14 C8 C7 109.19(13) . . ?
C14 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
C14 C8 H8B 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
N17 C9 C14 107.34(14) . . ?
N17 C9 C10 114.91(14) . . ?
C14 C9 C10 113.60(13) . . ?
N17 C9 H9 106.8 . . ?
C14 C9 H9 106.8 . . ?
C10 C9 H9 106.8 . . ?
C11 C10 C9 114.50(13) . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C1 115.18(14) . . ?
C12 C11 C10 118.65(14) . . ?
C1 C11 C10 126.06(14) . . ?
C11 C12 C4 124.57(14) . . ?
C11 C12 C13 126.21(14) . . ?
C4 C12 C13 109.15(13) . . ?
C12 C13 C14 109.51(13) . . ?
C12 C13 C15 110.49(13) . . ?
C14 C13 C15 107.78(12) . . ?
C12 C13 C5 97.44(11) . . ?
C14 C13 C5 118.40(13) . . ?
C15 C13 C5 112.74(13) . . ?
C8 C14 C13 112.49(13) . . ?
C8 C14 C9 115.62(14) . . ?
C13 C14 C9 106.18(13) . . ?
C8 C14 H14 107.4 . . ?
C13 C14 H14 107.4 . . ?
C9 C14 H14 107.4 . . ?
C16 C15 C13 110.70(13) . . ?
C16 C15 H15A 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
N17 C16 C15 112.26(15) . . ?
N17 C16 H16A 109.2 . . ?
C15 C16 H16A 109.2 . . ?
N17 C16 H16B 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C16 N17 C17A 110.63(16) . . ?
C16 N17 C9 113.15(13) . . ?
C17A N17 C9 112.58(15) . . ?
N17 C17A H17A 109.5 . . ?
N17 C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
N17 C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 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









































































C11 C1 C2 C3 -1.5(3) . . . . ?
Cl1A C1 C2 C3 176.84(13) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C1 C2 C3 N3A -178.70(15) . . . . ?
C4 C3 N3A O3A -170.04(16) . . . . ?
C2 C3 N3A O3A 8.2(2) . . . . ?
C4 C3 N3A O3B 10.5(2) . . . . ?
C2 C3 N3A O3B -171.18(15) . . . . ?
C2 C3 C4 O5A -173.58(15) . . . . ?
N3A C3 C4 O5A 4.7(3) . . . . ?
C2 C3 C4 C12 3.9(2) . . . . ?
N3A C3 C4 C12 -177.86(14) . . . . ?
C12 C4 O5A C5 -16.56(17) . . . . ?
C3 C4 O5A C5 161.02(16) . . . . ?
C6 C5 O5A C4 -89.15(14) . . . . ?
C13 C5 O5A C4 31.19(15) . . . . ?
O5A C5 C6 O6A -18.1(2) . . . . ?
C13 C5 C6 O6A -134.09(15) . . . . ?
O5A C5 C6 C7 158.31(13) . . . . ?
C13 C5 C6 C7 42.27(18) . . . . ?
O6A C6 C7 C8 116.09(17) . . . . ?
C5 C6 C7 C8 -60.22(18) . . . . ?
C6 C7 C8 C14 65.36(18) . . . . ?
N17 C9 C10 C11 -87.47(18) . . . . ?
C14 C9 C10 C11 36.7(2) . . . . ?
C2 C1 C11 C12 -0.2(2) . . . . ?
Cl1A C1 C11 C12 -178.54(12) . . . . ?
C2 C1 C11 C10 175.90(17) . . . . ?
Cl1A C1 C11 C10 -2.5(2) . . . . ?
C9 C10 C11 C12 -6.6(2) . . . . ?
C9 C10 C11 C1 177.43(15) . . . . ?
C1 C11 C12 C4 4.0(2) . . . . ?
C10 C11 C12 C4 -172.38(15) . . . . ?
C1 C11 C12 C13 -179.30(14) . . . . ?
C10 C11 C12 C13 4.3(2) . . . . ?
O5A C4 C12 C11 171.92(14) . . . . ?
C3 C4 C12 C11 -5.9(2) . . . . ?
O5A C4 C12 C13 -5.27(18) . . . . ?
C3 C4 C12 C13 176.87(14) . . . . ?
C11 C12 C13 C14 -30.5(2) . . . . ?
C4 C12 C13 C14 146.62(13) . . . . ?
C11 C12 C13 C15 88.06(18) . . . . ?
C4 C12 C13 C15 -94.81(15) . . . . ?
C11 C12 C13 C5 -154.23(15) . . . . ?
C4 C12 C13 C5 22.90(15) . . . . ?
O5A C5 C13 C12 -32.07(14) . . . . ?
C6 C5 C13 C12 85.85(14) . . . . ?
O5A C5 C13 C14 -149.04(13) . . . . ?
C6 C5 C13 C14 -31.12(19) . . . . ?
O5A C5 C13 C15 83.87(15) . . . . ?
C6 C5 C13 C15 -158.20(13) . . . . ?
C7 C8 C14 C13 -54.37(18) . . . . ?
C7 C8 C14 C9 -176.58(13) . . . . ?
C12 C13 C14 C8 -71.70(16) . . . . ?
C15 C13 C14 C8 168.05(13) . . . . ?
C5 C13 C14 C8 38.64(19) . . . . ?
C12 C13 C14 C9 55.70(16) . . . . ?
C15 C13 C14 C9 -64.55(16) . . . . ?
C5 C13 C14 C9 166.04(13) . . . . ?
N17 C9 C14 C8 -167.84(13) . . . . ?
C10 C9 C14 C8 63.99(18) . . . . ?
N17 C9 C14 C13 66.65(16) . . . . ?
C10 C9 C14 C13 -61.52(18) . . . . ?
C12 C13 C15 C16 -62.96(17) . . . . ?
C14 C13 C15 C16 56.67(17) . . . . ?
C5 C13 C15 C16 -170.80(13) . . . . ?
C13 C15 C16 N17 -50.63(19) . . . . ?
C15 C16 N17 C17A -178.40(15) . . . . ?
C15 C16 N17 C9 54.21(19) . . . . ?
C14 C9 N17 C16 -62.14(17) . . . . ?
C10 C9 N17 C16 65.27(18) . . . . ?
C14 C9 N17 C17A 171.50(14) . . . . ?
C10 C9 N17 C17A -61.09(19) . . . . ?



_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        26.48

_diffrn_measured_fraction_theta_full 0.999

_refine_diff_density_max         0.218

_refine_diff_density_min         -0.177

_refine_diff_density_rms         0.038



_database_code_depnum_ccdc_archive 'CCDC 975660'
#######################################################################
#
#                 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.
# 
#  For further information on the CCDC, data deposition and
#  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_knih86

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H23 N O2'
_chemical_formula_sum            'C18 H23 N O2'
_chemical_formula_weight         285.37

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 0.0091 '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 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   6.8411(3)
_cell_length_b                   12.9417(6)
_cell_length_c                   16.7006(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1478.60(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    175(2)
_cell_measurement_reflns_used    8381
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      67.71

_exptl_crystal_description       prisim
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.207
_exptl_crystal_size_mid          0.307
_exptl_crystal_size_max          0.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.653
##############################################################################
#                                                                            #
#  NOTE on absorbtion correction with SADABS:                                #
#                                                                            #
#  (Semi)empirical correction methods for absorption correction are more of  #
#  a problem in that they often specify only a relative correction range     #
#  [ Tmin(emp) & Tmax(emp)].                                                 #
#                                                                            #
#  Acta Cryst. procedures call in such cases for the multiplication of both  #
#  empirical values with Tmax(expected).                                     #
#                                                                            #
#  THIS RECOMMENDATION IS CURRENTLY UNDER REVIEW!  (George                   #
#  and Ton are agruing this point!)                                          #
#                                                                            #
##############################################################################
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000c)'
_exptl_absorpt_correction_T_min  0.7656
_exptl_absorpt_correction_T_max  0.8767


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      175(2)
# Platimnum-135 parameters
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  'helios mirros'
_diffrn_measurement_device_type  'Bruker Platinum-135 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4592
_diffrn_reflns_av_R_equivalents  0.1088
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.32
_diffrn_reflns_theta_max         67.85
_reflns_number_total             1649
_reflns_number_gt                1648
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_cell_refinement       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_data_reduction        
;
Bruker SAINT v6.45A (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001)
;
_computing_structure_solution    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_structure_refinement  'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_molecular_graphics    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_publication_material  'Bruker SHELXTL v6.14 (Bruker, 2000b)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0954P)²+0.3600P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   0.9(4)
_refine_ls_number_reflns         1649
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1320
_refine_ls_wR_factor_gt          0.1320
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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
C1 C 1.0737(4) -0.2028(2) 0.92545(19) 0.0339(7) Uani 1 1 d . . .
H1A H 1.1815 -0.2470 0.9358 0.041 Uiso 1 1 calc R . .
C2 C 0.9394(4) -0.2278(2) 0.86653(18) 0.0361(7) Uani 1 1 d . . .
H2A H 0.9534 -0.2919 0.8394 0.043 Uiso 1 1 calc R . .
C3 C 0.7840(4) -0.1632(2) 0.8451(2) 0.0357(7) Uani 1 1 d . . .
H3A H 0.6968 -0.1801 0.8029 0.043 Uiso 1 1 calc R . .
C4 C 0.7651(4) -0.0734(2) 0.88911(18) 0.0297(7) Uani 1 1 d . . .
O5 O 0.6396(2) 0.00770(16) 0.87336(12) 0.0352(5) Uani 1 1 d . . .
C5 C 0.7045(4) 0.0964(2) 0.92301(17) 0.0266(6) Uani 1 1 d . . .
H5A H 0.5879 0.1279 0.9496 0.032 Uiso 1 1 calc R . .
C6 C 0.8044(3) 0.1783(2) 0.87111(17) 0.0249(6) Uani 1 1 d . . .
H6A H 0.8198 0.2415 0.9050 0.030 Uiso 1 1 calc R . .
C6A C 0.6841(4) 0.2092(2) 0.79827(17) 0.0293(6) Uani 1 1 d . . .
H6AA H 0.7561 0.2626 0.7677 0.035 Uiso 1 1 calc R . .
H6AB H 0.6677 0.1483 0.7631 0.035 Uiso 1 1 calc R . .
O6 O 0.4966(2) 0.24829(15) 0.81905(11) 0.0303(5) Uani 1 1 d . . .
H6B H 0.4379 0.2673 0.7774 0.045 Uiso 1 1 calc R . .
C7 C 1.0102(3) 0.1429(2) 0.84731(18) 0.0298(7) Uani 1 1 d . . .
H7A H 1.0696 0.1959 0.8121 0.036 Uiso 1 1 calc R . .
H7B H 0.9999 0.0780 0.8162 0.036 Uiso 1 1 calc R . .
C8 C 1.1453(4) 0.1247(2) 0.91933(17) 0.0293(7) Uani 1 1 d . . .
H8A H 1.2283 0.0637 0.9083 0.035 Uiso 1 1 calc R . .
H8B H 1.2328 0.1852 0.9253 0.035 Uiso 1 1 calc R . .
C9 C 1.1568(3) 0.0421(2) 1.05823(18) 0.0266(7) Uani 1 1 d . . .
H9A H 1.2858 0.0773 1.0651 0.032 Uiso 1 1 calc R . .
C10 C 1.1997(4) -0.0691(2) 1.02687(18) 0.0306(7) Uani 1 1 d . . .
H10A H 1.3284 -0.0688 0.9997 0.037 Uiso 1 1 calc R . .
H10B H 1.2094 -0.1163 1.0734 0.037 Uiso 1 1 calc R . .
C11 C 1.0493(4) -0.1114(2) 0.96970(17) 0.0279(7) Uani 1 1 d . . .
C12 C 0.8876(3) -0.0523(2) 0.95282(17) 0.0242(6) Uani 1 1 d . . .
C13 C 0.8409(3) 0.0517(2) 0.98775(16) 0.0237(6) Uani 1 1 d . . .
C14 C 1.0370(3) 0.1073(2) 0.99876(16) 0.0247(6) Uani 1 1 d . . .
H14A H 1.0112 0.1762 1.0237 0.030 Uiso 1 1 calc R . .
C15 C 0.7369(3) 0.0441(2) 1.06912(17) 0.0267(6) Uani 1 1 d . . .
H15A H 0.6982 0.1143 1.0866 0.032 Uiso 1 1 calc R . .
H15B H 0.6163 0.0027 1.0628 0.032 Uiso 1 1 calc R . .
C16 C 0.8644(3) -0.0049(2) 1.13354(19) 0.0282(7) Uani 1 1 d . . .
H16A H 0.7992 0.0016 1.1862 0.034 Uiso 1 1 calc R . .
H16B H 0.8816 -0.0793 1.1219 0.034 Uiso 1 1 calc R . .
N17 N 1.0566(3) 0.04565(18) 1.13673(14) 0.0270(6) Uani 1 1 d . . .
C17 C 1.1743(4) 0.0036(2) 1.20239(18) 0.0355(7) Uani 1 1 d . . .
H17A H 1.1094 0.0178 1.2535 0.053 Uiso 1 1 calc R . .
H17B H 1.3038 0.0361 1.2021 0.053 Uiso 1 1 calc R . .
H17C H 1.1886 -0.0712 1.1955 0.053 Uiso 1 1 calc R . .


_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
C1 C2 1.385(4) . ?
C1 C11 1.404(4) . ?
C1 H1A 0.9500 . ?
C2 C3 1.399(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.381(4) . ?
C3 H3A 0.9500 . ?
C4 C12 1.382(4) . ?
C4 O5 1.381(3) . ?
O5 C5 1.484(3) . ?
C5 C6 1.530(4) . ?
C5 C13 1.541(3) . ?
C5 H5A 1.0000 . ?
C6 C6A 1.522(4) . ?
C6 C7 1.533(3) . ?
C6 H6A 1.0000 . ?
C6A O6 1.422(3) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
O6 H6B 0.8400 . ?
C7 C8 1.535(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.536(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N17 1.480(4) . ?
C9 C14 1.540(4) . ?
C9 C10 1.559(4) . ?
C9 H9A 1.0000 . ?
C10 C11 1.507(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.374(4) . ?
C12 C13 1.501(4) . ?
C13 C15 1.537(4) . ?
C13 C14 1.534(3) . ?
C14 H14A 1.0000 . ?
C15 C16 1.524(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N17 1.469(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
N17 C17 1.465(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C2 C1 C11 119.5(3) . . ?
C2 C1 H1A 120.3 . . ?
C11 C1 H1A 120.3 . . ?
C1 C2 C3 123.0(3) . . ?
C1 C2 H2A 118.5 . . ?
C3 C2 H2A 118.5 . . ?
C4 C3 C2 116.0(3) . . ?
C4 C3 H3A 122.0 . . ?
C2 C3 H3A 122.0 . . ?
C12 C4 C3 121.2(3) . . ?
C12 C4 O5 111.9(3) . . ?
C3 C4 O5 126.6(3) . . ?
C4 O5 C5 107.17(19) . . ?
O5 C5 C6 110.7(2) . . ?
O5 C5 C13 106.4(2) . . ?
C6 C5 C13 112.8(2) . . ?
O5 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
C13 C5 H5A 109.0 . . ?
C6A C6 C5 113.2(2) . . ?
C6A C6 C7 111.6(2) . . ?
C5 C6 C7 110.5(2) . . ?
C6A C6 H6A 107.1 . . ?
C5 C6 H6A 107.1 . . ?
C7 C6 H6A 107.1 . . ?
O6 C6A C6 112.7(2) . . ?
O6 C6A H6AA 109.0 . . ?
C6 C6A H6AA 109.0 . . ?
O6 C6A H6AB 109.0 . . ?
C6 C6A H6AB 109.0 . . ?
H6AA C6A H6AB 107.8 . . ?
C6A O6 H6B 109.5 . . ?
C6 C7 C8 113.3(2) . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C14 C8 C7 114.1(2) . . ?
C14 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C14 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N17 C9 C14 107.91(19) . . ?
N17 C9 C10 114.4(2) . . ?
C14 C9 C10 112.9(2) . . ?
N17 C9 H9A 107.0 . . ?
C14 C9 H9A 107.0 . . ?
C10 C9 H9A 107.0 . . ?
C11 C10 C9 114.8(2) . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 C1 117.2(3) . . ?
C12 C11 C10 118.5(2) . . ?
C1 C11 C10 124.0(2) . . ?
C11 C12 C4 122.4(3) . . ?
C11 C12 C13 126.2(2) . . ?
C4 C12 C13 110.3(2) . . ?
C12 C13 C15 112.7(2) . . ?
C12 C13 C14 106.33(19) . . ?
C15 C13 C14 109.2(2) . . ?
C12 C13 C5 101.1(2) . . ?
C15 C13 C5 111.33(19) . . ?
C14 C13 C5 115.9(2) . . ?
C13 C14 C8 112.8(2) . . ?
C13 C14 C9 106.6(2) . . ?
C8 C14 C9 112.4(2) . . ?
C13 C14 H14A 108.3 . . ?
C8 C14 H14A 108.3 . . ?
C9 C14 H14A 108.3 . . ?
C16 C15 C13 112.7(2) . . ?
C16 C15 H15A 109.1 . . ?
C13 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C13 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
N17 C16 C15 110.7(2) . . ?
N17 C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
N17 C16 H16B 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C17 N17 C16 110.7(2) . . ?
C17 N17 C9 113.4(2) . . ?
C16 N17 C9 111.6(2) . . ?
N17 C17 H17A 109.5 . . ?
N17 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N17 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C11 C1 C2 C3 3.8(4) . . . . ?
C1 C2 C3 C4 -3.0(4) . . . . ?
C2 C3 C4 C12 -3.1(4) . . . . ?
C2 C3 C4 O5 171.6(3) . . . . ?
C12 C4 O5 C5 9.1(3) . . . . ?
C3 C4 O5 C5 -166.0(3) . . . . ?
C4 O5 C5 C6 106.4(2) . . . . ?
C4 O5 C5 C13 -16.5(3) . . . . ?
O5 C5 C6 C6A 50.8(3) . . . . ?
C13 C5 C6 C6A 169.9(2) . . . . ?
O5 C5 C6 C7 -75.2(3) . . . . ?
C13 C5 C6 C7 43.9(3) . . . . ?
C5 C6 C6A O6 58.2(3) . . . . ?
C7 C6 C6A O6 -176.4(2) . . . . ?
C6A C6 C7 C8 172.4(2) . . . . ?
C5 C6 C7 C8 -60.8(3) . . . . ?
C6 C7 C8 C14 20.5(3) . . . . ?
N17 C9 C10 C11 95.7(3) . . . . ?
C14 C9 C10 C11 -28.3(3) . . . . ?
C2 C1 C11 C12 1.5(4) . . . . ?
C2 C1 C11 C10 -171.2(3) . . . . ?
C9 C10 C11 C12 -2.5(4) . . . . ?
C9 C10 C11 C1 170.1(3) . . . . ?
C1 C11 C12 C4 -7.6(4) . . . . ?
C10 C11 C12 C4 165.5(3) . . . . ?
C1 C11 C12 C13 -174.8(3) . . . . ?
C10 C11 C12 C13 -1.7(4) . . . . ?
C3 C4 C12 C11 8.6(4) . . . . ?
O5 C4 C12 C11 -166.8(2) . . . . ?
C3 C4 C12 C13 177.7(2) . . . . ?
O5 C4 C12 C13 2.3(3) . . . . ?
C11 C12 C13 C15 -84.4(3) . . . . ?
C4 C12 C13 C15 107.0(2) . . . . ?
C11 C12 C13 C14 35.1(4) . . . . ?
C4 C12 C13 C14 -133.4(2) . . . . ?
C11 C12 C13 C5 156.6(3) . . . . ?
C4 C12 C13 C5 -11.9(3) . . . . ?
O5 C5 C13 C12 16.7(2) . . . . ?
C6 C5 C13 C12 -104.8(2) . . . . ?
O5 C5 C13 C15 -103.2(2) . . . . ?
C6 C5 C13 C15 135.3(2) . . . . ?
O5 C5 C13 C14 131.2(2) . . . . ?
C6 C5 C13 C14 9.7(3) . . . . ?
C12 C13 C14 C8 61.9(3) . . . . ?
C15 C13 C14 C8 -176.2(2) . . . . ?
C5 C13 C14 C8 -49.5(3) . . . . ?
C12 C13 C14 C9 -61.8(3) . . . . ?
C15 C13 C14 C9 60.0(3) . . . . ?
C5 C13 C14 C9 -173.3(2) . . . . ?
C7 C8 C14 C13 32.9(3) . . . . ?
C7 C8 C14 C9 153.3(2) . . . . ?
N17 C9 C14 C13 -65.9(3) . . . . ?
C10 C9 C14 C13 61.6(3) . . . . ?
N17 C9 C14 C8 170.0(2) . . . . ?
C10 C9 C14 C8 -62.4(3) . . . . ?
C12 C13 C15 C16 64.3(3) . . . . ?
C14 C13 C15 C16 -53.6(3) . . . . ?
C5 C13 C15 C16 177.1(2) . . . . ?
C13 C15 C16 N17 50.7(3) . . . . ?
C15 C16 N17 C17 176.0(2) . . . . ?
C15 C16 N17 C9 -56.7(3) . . . . ?
C14 C9 N17 C17 -168.8(2) . . . . ?
C10 C9 N17 C17 64.6(3) . . . . ?
C14 C9 N17 C16 65.4(3) . . . . ?
C10 C9 N17 C16 -61.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.742
_diffrn_reflns_theta_full        67.85
_diffrn_measured_fraction_theta_full 0.741
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.122
_database_code_depnum_ccdc_archive 'CCDC 954929'
#######################################################################
#
#                 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.
# 
#  For further information on the CCDC, data deposition and
#  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_knih94

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H24 N2 O, 0.89(C H4 O), 2(Br)'
_chemical_formula_sum            'C17.90 H27.58 Br2 N2 O1.90'
_chemical_formula_weight         460.86
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'

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

_cell_length_a                   8.1091(2)
_cell_length_b                   11.2247(3)
_cell_length_c                   11.0425(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.1160(10)
_cell_angle_gamma                90.00
_cell_volume                     965.61(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7606
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      29.12

_exptl_crystal_description       prisim
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.167
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_max          0.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             468.2
_exptl_absorpt_coefficient_mu    4.210
##############################################################################
#                                                                            #
# NOTE on absorbtion correction with SADABS:                                 #
#                                                                            #
# (Semi)empirical correction methods for absorption correction are more of   #
# a problem in that they often specify only a relative correction range      #
# [ Tmin(emp) & Tmax(emp)].                                                  #
#                                                                            #
# Acta Cryst. procedures call in such cases for the multiplication of both   #
# empirical values with Tmax(expected).                                      # 
#                                                                            #
# THIS RECOMMENDATION IS CURRENTLY UNDER REVIEW! (George                     #
# and Ton are agruing this point!)                                           #
#                                                                            #
##############################################################################
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000c)'
_exptl_absorpt_correction_T_min  0.4039
_exptl_absorpt_correction_T_max  0.5399

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
# APEX 2 parameters
_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  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11213
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         29.14
_reflns_number_total             5047
_reflns_number_gt                4728
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_cell_refinement       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_data_reduction        
;
Bruker SAINT v6.45A (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001)
;
_computing_structure_solution    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_structure_refinement  'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_molecular_graphics    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_publication_material  'Bruker SHELXTL v6.14 (Bruker, 2000b)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0747P)²+0.0000P] where P=(Fo²+2Fc²)/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   -0.002(8)
_refine_ls_number_reflns         5047
_refine_ls_number_parameters     222
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1051
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.126
_refine_ls_shift/su_mean         0.003

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
Br1 Br -0.50124(4) 0.58825(3) 0.47253(3) 0.02301(7) Uani 1 1 d . . .
Br2 Br -0.56895(5) 0.92645(3) 0.85276(3) 0.03209(10) Uani 1 1 d . . .
C1 C -1.2113(5) 1.1143(3) 0.1995(3) 0.0233(7) Uani 1 1 d . . .
H1A H -1.3073 1.1664 0.1776 0.028 Uiso 1 1 calc R . .
C2 C -1.0489(5) 1.1575(3) 0.2044(3) 0.0286(8) Uani 1 1 d . . .
H2A H -1.0373 1.2384 0.1827 0.034 Uiso 1 1 calc R . .
C3 C -0.9007(4) 1.0854(3) 0.2404(3) 0.0257(6) Uani 1 1 d . . .
H3A H -0.7895 1.1158 0.2460 0.031 Uiso 1 1 calc R . .
C4 C -0.9277(4) 0.9675(3) 0.2671(3) 0.0193(6) Uani 1 1 d . . .
O5 O -0.8026(3) 0.8837(2) 0.3179(2) 0.0202(4) Uani 1 1 d . . .
C5 C -0.8877(4) 0.7858(3) 0.3656(3) 0.0157(5) Uani 1 1 d . . .
H5A H -0.8427 0.7075 0.3453 0.019 Uiso 1 1 calc R . .
C6 C -0.8532(4) 0.7986(3) 0.5093(3) 0.0165(6) Uani 1 1 d . . .
H6A H -0.8784 0.7207 0.5442 0.020 Uiso 1 1 calc R . .
N6 N -0.6672(3) 0.8265(2) 0.5643(3) 0.0194(5) Uiso 1 1 d . . .
H6B H -0.6441 0.8337 0.6494 0.029 Uiso 1 1 calc R . .
H6C H -0.6417 0.8962 0.5313 0.029 Uiso 1 1 calc R . .
H6D H -0.6025 0.7668 0.5455 0.029 Uiso 1 1 calc R . .
C7 C -0.9640(4) 0.8943(3) 0.5454(3) 0.0201(6) Uani 1 1 d . . .
H7A H -0.9453 0.9712 0.5071 0.024 Uiso 1 1 calc R . .
H7B H -0.9294 0.9043 0.6381 0.024 Uiso 1 1 calc R . .
C8 C -1.1553(4) 0.8614(3) 0.5004(3) 0.0212(7) Uani 1 1 d . . .
H8A H -1.2238 0.9356 0.4837 0.025 Uiso 1 1 calc R . .
H8B H -1.1867 0.8183 0.5690 0.025 Uiso 1 1 calc R . .
C9 C -1.2042(4) 0.7830(3) 0.3797(3) 0.0165(6) Uani 1 1 d . . .
H9A H -1.2054 0.6976 0.4053 0.020 Uiso 1 1 calc R . .
C10 C -1.3850(4) 0.8164(3) 0.2953(3) 0.0165(6) Uani 1 1 d . . .
H10A H -1.4668 0.8107 0.3483 0.020 Uiso 1 1 calc R . .
C11 C -1.4011(4) 0.9433(3) 0.2379(3) 0.0191(6) Uani 1 1 d . . .
H11A H -1.4841 0.9411 0.1532 0.023 Uiso 1 1 calc R . .
H11B H -1.4484 0.9971 0.2911 0.023 Uiso 1 1 calc R . .
C12 C -1.2344(4) 0.9947(3) 0.2265(3) 0.0186(6) Uani 1 1 d . . .
C13 C -1.0904(4) 0.9230(3) 0.2543(2) 0.0159(5) Uani 1 1 d . . .
C14 C -1.0803(4) 0.7964(3) 0.2968(3) 0.0145(5) Uani 1 1 d . . .
C15 C -1.1322(4) 0.7074(3) 0.1865(3) 0.0166(6) Uani 1 1 d . . .
H15A H -1.0560 0.7183 0.1311 0.020 Uiso 1 1 calc R . .
H15B H -1.1159 0.6252 0.2202 0.020 Uiso 1 1 calc R . .
C16 C -1.3178(4) 0.7233(3) 0.1091(3) 0.0187(6) Uani 1 1 d . . .
H16A H -1.3306 0.8000 0.0632 0.022 Uiso 1 1 calc R . .
H16B H -1.3501 0.6583 0.0463 0.022 Uiso 1 1 calc R . .
N17 N -1.4346(3) 0.7214(2) 0.1939(2) 0.0175(5) Uiso 1 1 d . . .
H17D H -1.4185 0.6482 0.2350 0.021 Uiso 1 1 calc R . .
C17 C -1.6177(4) 0.7264(3) 0.1189(3) 0.0232(7) Uani 1 1 d . . .
H17A H -1.6454 0.6557 0.0650 0.035 Uiso 1 1 calc R . .
H17B H -1.6373 0.7981 0.0663 0.035 Uiso 1 1 calc R . .
H17C H -1.6911 0.7285 0.1761 0.035 Uiso 1 1 calc R . .
O1S O -0.8538(3) 0.4699(5) 0.2072(4) 0.0670(15) Uani 0.888(9) 1 d PD . .
H1S H -0.7468(7) 0.4498(17) 0.2413(5) 0.100 Uiso 0.888(9) 1 d PD . .
C1S C -0.9197(2) 0.45030(19) 0.0875(3) 0.0443(13) Uani 0.888(9) 1 d PD . .
H1SA H -0.8930(7) 0.4909(5) 0.0188(5) 0.053 Uiso 0.888(9) 1 d PD . .
H1SB H -1.0380(3) 0.4270(6) 0.0583(8) 0.053 Uiso 0.888(9) 1 d PD . .
H1SC H -0.8534(7) 0.3782(4) 0.1014(9) 0.053 Uiso 0.888(9) 1 d PD . .


_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
C1 C2 1.390(5) . ?
C1 C12 1.399(4) . ?
C1 H1A 0.9500 . ?
C2 C3 1.412(5) . ?
C2 H2A 0.9500 . ?
C3 C4 1.387(5) . ?
C3 H3A 0.9500 . ?
C4 C13 1.381(4) . ?
C4 O5 1.383(4) . ?
O5 C5 1.470(4) . ?
C5 C6 1.539(4) . ?
C5 C14 1.541(4) . ?
C5 H5A 1.0000 . ?
C6 N6 1.495(4) . ?
C6 C7 1.523(4) . ?
C6 H6A 1.0000 . ?
N6 H6B 0.9100 . ?
N6 H6C 0.9100 . ?
N6 H6D 0.9100 . ?
C7 C8 1.537(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.554(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.543(4) . ?
C9 C10 1.549(4) . ?
C9 H9A 1.0000 . ?
C10 N17 1.517(4) . ?
C10 C11 1.551(4) . ?
C10 H10A 1.0000 . ?
C11 C12 1.506(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.381(4) . ?
C13 C14 1.492(4) . ?
C14 C15 1.541(4) . ?
C15 C16 1.521(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N17 1.506(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
N17 C17 1.487(4) . ?
N17 H17D 0.9300 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O1S C1S 1.299(5) . ?
O1S H1S 0.8741(10) . ?
C1S H1SA 0.9599(10) . ?
C1S H1SB 0.9599(10) . ?
C1S H1SC 0.9601(10) . ?

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
C2 C1 C12 120.5(3) . . ?
C2 C1 H1A 119.7 . . ?
C12 C1 H1A 119.7 . . ?
C1 C2 C3 122.3(3) . . ?
C1 C2 H2A 118.9 . . ?
C3 C2 H2A 118.9 . . ?
C4 C3 C2 115.8(3) . . ?
C4 C3 H3A 122.1 . . ?
C2 C3 H3A 122.1 . . ?
C13 C4 O5 111.6(3) . . ?
C13 C4 C3 121.7(3) . . ?
O5 C4 C3 126.5(3) . . ?
C4 O5 C5 106.8(2) . . ?
O5 C5 C6 109.3(2) . . ?
O5 C5 C14 106.1(2) . . ?
C6 C5 C14 111.7(2) . . ?
O5 C5 H5A 109.9 . . ?
C6 C5 H5A 109.9 . . ?
C14 C5 H5A 109.9 . . ?
N6 C6 C7 110.4(3) . . ?
N6 C6 C5 108.2(3) . . ?
C7 C6 C5 112.6(2) . . ?
N6 C6 H6A 108.5 . . ?
C7 C6 H6A 108.5 . . ?
C5 C6 H6A 108.5 . . ?
C6 N6 H6B 109.5 . . ?
C6 N6 H6C 109.5 . . ?
H6B N6 H6C 109.5 . . ?
C6 N6 H6D 109.5 . . ?
H6B N6 H6D 109.5 . . ?
H6C N6 H6D 109.5 . . ?
C6 C7 C8 111.2(3) . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C9 114.1(3) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C14 C9 C10 106.5(2) . . ?
C14 C9 C8 113.6(3) . . ?
C10 C9 C8 110.6(2) . . ?
C14 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
N17 C10 C9 106.7(2) . . ?
N17 C10 C11 111.7(2) . . ?
C9 C10 C11 115.2(2) . . ?
N17 C10 H10A 107.7 . . ?
C9 C10 H10A 107.7 . . ?
C11 C10 H10A 107.7 . . ?
C12 C11 C10 114.2(2) . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C1 116.8(3) . . ?
C13 C12 C11 118.8(3) . . ?
C1 C12 C11 124.2(3) . . ?
C12 C13 C4 122.5(3) . . ?
C12 C13 C14 126.5(3) . . ?
C4 C13 C14 110.2(3) . . ?
C13 C14 C15 112.9(2) . . ?
C13 C14 C5 100.9(2) . . ?
C15 C14 C5 110.9(2) . . ?
C13 C14 C9 106.9(2) . . ?
C15 C14 C9 109.0(2) . . ?
C5 C14 C9 116.0(2) . . ?
C16 C15 C14 112.3(2) . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
N17 C16 C15 110.1(2) . . ?
N17 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
N17 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C17 N17 C16 110.9(2) . . ?
C17 N17 C10 113.8(2) . . ?
C16 N17 C10 111.5(2) . . ?
C17 N17 H17D 106.7 . . ?
C16 N17 H17D 106.7 . . ?
C10 N17 H17D 106.7 . . ?
N17 C17 H17A 109.5 . . ?
N17 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N17 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1S O1S H1S 118.2(5) . . ?
O1S C1S H1SA 127.2(5) . . ?
O1S C1S H1SB 118.6(6) . . ?
H1SA C1S H1SB 106.7(2) . . ?
O1S C1S H1SC 85.8(6) . . ?
H1SA C1S H1SC 106.7(2) . . ?
H1SB C1S H1SC 106.7(2) . . ?

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 C1 C2 C3 -2.2(5) . . . . ?
C1 C2 C3 C4 1.9(5) . . . . ?
C2 C3 C4 C13 2.4(4) . . . . ?
C2 C3 C4 O5 -172.0(3) . . . . ?
C13 C4 O5 C5 -12.2(3) . . . . ?
C3 C4 O5 C5 162.7(3) . . . . ?
C4 O5 C5 C6 -100.3(3) . . . . ?
C4 O5 C5 C14 20.3(3) . . . . ?
O5 C5 C6 N6 -44.9(3) . . . . ?
C14 C5 C6 N6 -162.1(2) . . . . ?
O5 C5 C6 C7 77.3(3) . . . . ?
C14 C5 C6 C7 -39.8(3) . . . . ?
N6 C6 C7 C8 -174.6(2) . . . . ?
C5 C6 C7 C8 64.4(3) . . . . ?
C6 C7 C8 C9 -29.3(4) . . . . ?
C7 C8 C9 C14 -24.7(4) . . . . ?
C7 C8 C9 C10 -144.3(3) . . . . ?
C14 C9 C10 N17 66.4(3) . . . . ?
C8 C9 C10 N17 -169.7(3) . . . . ?
C14 C9 C10 C11 -58.1(3) . . . . ?
C8 C9 C10 C11 65.7(3) . . . . ?
N17 C10 C11 C12 -97.9(3) . . . . ?
C9 C10 C11 C12 24.0(4) . . . . ?
C2 C1 C12 C13 -1.7(4) . . . . ?
C2 C1 C12 C11 172.8(3) . . . . ?
C10 C11 C12 C13 6.5(4) . . . . ?
C10 C11 C12 C1 -167.9(3) . . . . ?
C1 C12 C13 C4 6.0(4) . . . . ?
C11 C12 C13 C4 -168.8(3) . . . . ?
C1 C12 C13 C14 174.3(3) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
O5 C4 C13 C12 168.6(3) . . . . ?
C3 C4 C13 C12 -6.6(4) . . . . ?
O5 C4 C13 C14 -1.4(3) . . . . ?
C3 C4 C13 C14 -176.5(3) . . . . ?
C12 C13 C14 C15 85.5(3) . . . . ?
C4 C13 C14 C15 -105.0(3) . . . . ?
C12 C13 C14 C5 -156.1(3) . . . . ?
C4 C13 C14 C5 13.4(3) . . . . ?
C12 C13 C14 C9 -34.4(4) . . . . ?
C4 C13 C14 C9 135.0(2) . . . . ?
O5 C5 C14 C13 -20.0(3) . . . . ?
C6 C5 C14 C13 99.1(3) . . . . ?
O5 C5 C14 C15 99.9(3) . . . . ?
C6 C5 C14 C15 -141.1(3) . . . . ?
O5 C5 C14 C9 -135.0(2) . . . . ?
C6 C5 C14 C9 -16.0(3) . . . . ?
C10 C9 C14 C13 59.7(3) . . . . ?
C8 C9 C14 C13 -62.3(3) . . . . ?
C10 C9 C14 C15 -62.7(3) . . . . ?
C8 C9 C14 C15 175.3(3) . . . . ?
C10 C9 C14 C5 171.3(2) . . . . ?
C8 C9 C14 C5 49.3(3) . . . . ?
C13 C14 C15 C16 -62.4(3) . . . . ?
C5 C14 C15 C16 -174.8(2) . . . . ?
C9 C14 C15 C16 56.3(3) . . . . ?
C14 C15 C16 N17 -52.2(3) . . . . ?
C15 C16 N17 C17 -175.1(3) . . . . ?
C15 C16 N17 C10 56.9(3) . . . . ?
C9 C10 N17 C17 169.0(2) . . . . ?
C11 C10 N17 C17 -64.3(3) . . . . ?
C9 C10 N17 C16 -64.7(3) . . . . ?
C11 C10 N17 C16 62.0(3) . . . . ?

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
N6 H6B Br2 0.91 2.40 3.261(3) 158.9 .
N6 H6C Br1 0.91 2.45 3.312(3) 157.3 2_456
N6 H6D Br1 0.91 2.39 3.278(3) 165.7 .
N17 H17D Br2 0.93 2.66 3.352(3) 131.5 2_346
N17 H17D Br1 0.93 2.96 3.594(3) 126.7 1_455
O1S H1S Br1 0.8741(10) 3.175(10) 3.725(4) 123.1(10) .
O1S H1S Br2 0.8741(10) 3.030(7) 3.700(3) 135.0(8) 2_446

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        29.14
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         1.622
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.111
_database_code_depnum_ccdc_archive 'CCDC 955757'
