# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2009


data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Bernhard W\"unsch'
'Roland Frohlich'
'Daniel Kracht'
'Elisabeth Rack'
'Dirk Schepmann'

_publ_contact_author_name        'Bernhard W\"unsch'
_publ_contact_author_email       WUENSCH@UNI-MUENSTER.DE

_publ_section_title              
;
Stereoselective Synthesis and Structure-Affinity Relationships of
Bicyclic ? Receptor Agonists
;

# Attachment '109-Kracht-3CIF.cif.txt'

data_fro3671
_database_code_depnum_ccdc_archive 'CCDC 748563'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H25 Cl2 N3 O'
_chemical_formula_weight         382.32

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.118(1)
_cell_length_b                   11.118(1)
_cell_length_c                   12.171(1)
_cell_angle_alpha                94.46(1)
_cell_angle_beta                 107.28(1)
_cell_angle_gamma                93.94(1)
_cell_volume                     912.65(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2608
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    3.293
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7342
_exptl_absorpt_correction_T_max  0.9077
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10437
_diffrn_reflns_av_R_equivalents  0.062
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.01
_diffrn_reflns_theta_max         69.02
_reflns_number_total             3119
_reflns_number_gt                2486
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SCHAKAL (Keller, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1258P)^2^+0.8293P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3119
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.2035
_refine_ls_wR_factor_gt          0.1826
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
Cl1 Cl 0.42475(13) 0.27446(9) 0.21067(8) 0.0480(3) Uani 1 1 d . . .
Cl2 Cl 0.46613(16) 0.31690(11) 0.47663(9) 0.0613(4) Uani 1 1 d . . .
O1 O 0.8158(4) -0.0924(2) 0.2217(2) 0.0451(6) Uani 1 1 d . . .
N1 N 1.1040(4) -0.1065(2) 0.1825(2) 0.0316(6) Uani 1 1 d . . .
N2 N 1.2777(4) -0.1653(3) 0.0036(2) 0.0386(7) Uani 1 1 d . . .
N3 N 1.0571(4) -0.3676(2) 0.2300(2) 0.0347(7) Uani 1 1 d . . .
C1 C 1.3109(5) -0.0662(3) 0.2018(3) 0.0382(8) Uani 1 1 d . . .
H1A H 1.3927 -0.1210 0.2485 0.046 Uiso 1 1 calc R . .
H1B H 1.3411 0.0138 0.2445 0.046 Uiso 1 1 calc R . .
C2 C 1.3607(5) -0.0613(3) 0.0885(3) 0.0409(8) Uani 1 1 d . . .
H2A H 1.3135 0.0113 0.0545 0.049 Uiso 1 1 calc R . .
H2B H 1.5033 -0.0542 0.1057 0.049 Uiso 1 1 calc R . .
C3 C 1.0646(5) -0.1811(3) -0.0158(3) 0.0377(8) Uani 1 1 d . . .
H3A H 1.0055 -0.2466 -0.0763 0.045 Uiso 1 1 calc R . .
H3B H 1.0071 -0.1076 -0.0412 0.045 Uiso 1 1 calc R . .
C4 C 1.0198(5) -0.2094(3) 0.0937(3) 0.0318(7) Uani 1 1 d . . .
H4A H 0.8759 -0.2168 0.0777 0.038 Uiso 1 1 calc R . .
C5 C 1.0939(5) -0.3321(3) 0.1255(3) 0.0340(7) Uani 1 1 d . . .
H5A H 1.0168 -0.3926 0.0624 0.041 Uiso 1 1 calc R . .
C6 C 1.3112(5) -0.3375(4) 0.1308(3) 0.0422(9) Uani 1 1 d . . .
H6A H 1.3949 -0.2969 0.2042 0.051 Uiso 1 1 calc R . .
H6B H 1.3396 -0.4216 0.1272 0.051 Uiso 1 1 calc R . .
C7 C 1.3608(6) -0.2787(3) 0.0330(3) 0.0421(9) Uani 1 1 d . . .
H7A H 1.5035 -0.2643 0.0532 0.050 Uiso 1 1 calc R . .
H7B H 1.3169 -0.3363 -0.0357 0.050 Uiso 1 1 calc R . .
C8 C 0.9854(5) -0.0531(3) 0.2365(3) 0.0324(7) Uani 1 1 d . . .
C9 C 1.0705(5) 0.0634(3) 0.3158(3) 0.0351(7) Uani 1 1 d . . .
H9A H 1.1744 0.0446 0.3826 0.042 Uiso 1 1 calc R . .
H9B H 1.1295 0.1188 0.2749 0.042 Uiso 1 1 calc R . .
C10 C 0.9199(5) 0.1247(3) 0.3564(3) 0.0333(7) Uani 1 1 d . . .
C11 C 0.7572(5) 0.1647(3) 0.2762(3) 0.0333(7) Uani 1 1 d . . .
H11A H 0.7410 0.1506 0.1975 0.040 Uiso 1 1 calc R . .
C12 C 0.6218(5) 0.2246(3) 0.3133(3) 0.0361(8) Uani 1 1 d . . .
C13 C 0.6377(5) 0.2443(3) 0.4297(3) 0.0403(8) Uani 1 1 d . . .
C14 C 0.8007(6) 0.2064(3) 0.5098(3) 0.0427(9) Uani 1 1 d . . .
H14A H 0.8167 0.2203 0.5885 0.051 Uiso 1 1 calc R . .
C15 C 0.9389(6) 0.1481(3) 0.4722(3) 0.0384(8) Uani 1 1 d . . .
H15A H 1.0480 0.1239 0.5266 0.046 Uiso 1 1 calc R . .
C16 C 1.1275(6) -0.4837(3) 0.2632(3) 0.0452(9) Uani 1 1 d . . .
H16A H 1.2704 -0.4765 0.2954 0.054 Uiso 1 1 calc R . .
H16B H 1.0877 -0.5451 0.1974 0.054 Uiso 1 1 calc R . .
C17 C 1.0290(7) -0.5140(4) 0.3536(4) 0.0555(11) Uani 1 1 d . . .
H17A H 1.1132 -0.4835 0.4306 0.067 Uiso 1 1 calc R . .
H17B H 1.0002 -0.6009 0.3508 0.067 Uiso 1 1 calc R . .
C18 C 0.8390(7) -0.4518(4) 0.3227(4) 0.0573(11) Uani 1 1 d . . .
H18A H 0.7242 -0.5108 0.3019 0.069 Uiso 1 1 calc R . .
H18B H 0.8343 -0.3960 0.3870 0.069 Uiso 1 1 calc R . .
C19 C 0.8465(6) -0.3845(4) 0.2208(3) 0.0453(9) Uani 1 1 d . . .
H19A H 0.7719 -0.4315 0.1486 0.054 Uiso 1 1 calc R . .
H19B H 0.7930 -0.3070 0.2248 0.054 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0384(5) 0.0512(6) 0.0492(6) 0.0047(4) 0.0038(4) 0.0131(4)
Cl2 0.0553(6) 0.0717(7) 0.0588(6) -0.0120(5) 0.0218(5) 0.0201(5)
O1 0.0337(14) 0.0418(14) 0.0583(16) -0.0082(12) 0.0149(11) 0.0032(11)
N1 0.0282(14) 0.0328(14) 0.0307(14) -0.0015(11) 0.0043(11) 0.0070(11)
N2 0.0349(16) 0.0492(18) 0.0302(14) 0.0029(12) 0.0066(12) 0.0100(13)
N3 0.0358(16) 0.0309(14) 0.0329(14) 0.0007(11) 0.0039(12) 0.0046(12)
C1 0.0283(17) 0.0427(19) 0.0379(18) -0.0053(14) 0.0039(14) 0.0040(14)
C2 0.0310(18) 0.047(2) 0.044(2) 0.0030(16) 0.0100(15) 0.0048(15)
C3 0.0372(19) 0.0398(19) 0.0315(17) 0.0011(14) 0.0027(14) 0.0094(15)
C4 0.0247(16) 0.0324(17) 0.0322(16) -0.0025(13) 0.0008(12) 0.0026(13)
C5 0.0333(18) 0.0325(17) 0.0314(16) -0.0032(13) 0.0033(13) 0.0065(14)
C6 0.040(2) 0.046(2) 0.0409(19) 0.0064(15) 0.0082(15) 0.0186(16)
C7 0.042(2) 0.049(2) 0.0397(19) 0.0023(15) 0.0156(16) 0.0185(17)
C8 0.0298(18) 0.0325(17) 0.0337(17) 0.0049(13) 0.0063(13) 0.0080(13)
C9 0.0319(18) 0.0371(18) 0.0338(17) 0.0016(14) 0.0067(14) 0.0045(14)
C10 0.0375(18) 0.0295(16) 0.0305(16) 0.0019(12) 0.0066(14) 0.0037(14)
C11 0.0353(18) 0.0327(17) 0.0312(16) 0.0005(13) 0.0096(14) 0.0046(14)
C12 0.0289(17) 0.0359(18) 0.0397(18) 0.0012(14) 0.0059(14) 0.0018(14)
C13 0.039(2) 0.0349(18) 0.045(2) -0.0066(15) 0.0136(16) 0.0035(15)
C14 0.051(2) 0.045(2) 0.0317(18) -0.0012(15) 0.0123(16) 0.0108(17)
C15 0.046(2) 0.0347(18) 0.0322(17) 0.0014(13) 0.0070(15) 0.0098(15)
C16 0.051(2) 0.0363(19) 0.046(2) 0.0053(15) 0.0088(17) 0.0114(17)
C17 0.060(3) 0.043(2) 0.062(3) 0.0166(19) 0.014(2) 0.0016(19)
C18 0.055(3) 0.049(2) 0.070(3) 0.017(2) 0.021(2) -0.001(2)
C19 0.042(2) 0.043(2) 0.049(2) 0.0036(16) 0.0114(16) 0.0050(16)

_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
Cl1 C12 1.735(3) . ?
Cl2 C13 1.717(4) . ?
O1 C8 1.212(4) . ?
N1 C8 1.354(4) . ?
N1 C1 1.453(4) . ?
N1 C4 1.471(4) . ?
N2 C2 1.454(5) . ?
N2 C7 1.454(5) . ?
N2 C3 1.461(5) . ?
N3 C5 1.451(4) . ?
N3 C16 1.459(4) . ?
N3 C19 1.467(5) . ?
C1 C2 1.526(5) . ?
C3 C4 1.510(5) . ?
C4 C5 1.533(5) . ?
C5 C6 1.534(5) . ?
C6 C7 1.520(5) . ?
C8 C9 1.526(5) . ?
C9 C10 1.489(5) . ?
C10 C15 1.378(5) . ?
C10 C11 1.399(5) . ?
C11 C12 1.370(5) . ?
C12 C13 1.386(5) . ?
C13 C14 1.391(5) . ?
C14 C15 1.381(5) . ?
C16 C17 1.517(6) . ?
C17 C18 1.521(6) . ?
C18 C19 1.509(6) . ?

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
C8 N1 C1 124.6(3) . . ?
C8 N1 C4 119.2(3) . . ?
C1 N1 C4 116.2(3) . . ?
C2 N2 C7 115.5(3) . . ?
C2 N2 C3 108.5(3) . . ?
C7 N2 C3 109.3(3) . . ?
C5 N3 C16 114.1(3) . . ?
C5 N3 C19 113.7(3) . . ?
C16 N3 C19 103.2(3) . . ?
N1 C1 C2 112.0(3) . . ?
N2 C2 C1 114.8(3) . . ?
N2 C3 C4 110.7(3) . . ?
N1 C4 C3 108.4(3) . . ?
N1 C4 C5 115.5(2) . . ?
C3 C4 C5 108.5(3) . . ?
N3 C5 C4 112.7(3) . . ?
N3 C5 C6 111.9(3) . . ?
C4 C5 C6 112.3(3) . . ?
C7 C6 C5 112.5(3) . . ?
N2 C7 C6 116.9(3) . . ?
O1 C8 N1 122.7(3) . . ?
O1 C8 C9 119.7(3) . . ?
N1 C8 C9 117.6(3) . . ?
C10 C9 C8 113.2(3) . . ?
C15 C10 C11 118.0(3) . . ?
C15 C10 C9 121.9(3) . . ?
C11 C10 C9 120.1(3) . . ?
C12 C11 C10 120.2(3) . . ?
C11 C12 C13 121.6(3) . . ?
C11 C12 Cl1 118.5(3) . . ?
C13 C12 Cl1 119.9(3) . . ?
C12 C13 C14 118.3(3) . . ?
C12 C13 Cl2 121.9(3) . . ?
C14 C13 Cl2 119.8(3) . . ?
C15 C14 C13 119.8(3) . . ?
C10 C15 C14 121.9(3) . . ?
N3 C16 C17 103.5(3) . . ?
C16 C17 C18 105.0(3) . . ?
C19 C18 C17 104.5(4) . . ?
N3 C19 C18 104.8(3) . . ?

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
C8 N1 C1 C2 -134.1(3) . . . . ?
C4 N1 C1 C2 43.0(4) . . . . ?
C7 N2 C2 C1 -68.8(4) . . . . ?
C3 N2 C2 C1 54.2(4) . . . . ?
N1 C1 C2 N2 -44.1(4) . . . . ?
C2 N2 C3 C4 -63.2(4) . . . . ?
C7 N2 C3 C4 63.5(4) . . . . ?
C8 N1 C4 C3 125.7(3) . . . . ?
C1 N1 C4 C3 -51.6(4) . . . . ?
C8 N1 C4 C5 -112.3(3) . . . . ?
C1 N1 C4 C5 70.4(4) . . . . ?
N2 C3 C4 N1 61.4(3) . . . . ?
N2 C3 C4 C5 -64.7(4) . . . . ?
C16 N3 C5 C4 -179.5(3) . . . . ?
C19 N3 C5 C4 62.5(4) . . . . ?
C16 N3 C5 C6 -51.8(4) . . . . ?
C19 N3 C5 C6 -169.8(3) . . . . ?
N1 C4 C5 N3 58.2(4) . . . . ?
C3 C4 C5 N3 -179.9(3) . . . . ?
N1 C4 C5 C6 -69.2(4) . . . . ?
C3 C4 C5 C6 52.7(4) . . . . ?
N3 C5 C6 C7 -169.3(3) . . . . ?
C4 C5 C6 C7 -41.4(4) . . . . ?
C2 N2 C7 C6 70.4(4) . . . . ?
C3 N2 C7 C6 -52.2(4) . . . . ?
C5 C6 C7 N2 41.8(5) . . . . ?
C1 N1 C8 O1 -176.8(3) . . . . ?
C4 N1 C8 O1 6.1(5) . . . . ?
C1 N1 C8 C9 5.1(5) . . . . ?
C4 N1 C8 C9 -171.9(3) . . . . ?
O1 C8 C9 C10 -7.0(4) . . . . ?
N1 C8 C9 C10 171.1(3) . . . . ?
C8 C9 C10 C15 121.9(3) . . . . ?
C8 C9 C10 C11 -60.7(4) . . . . ?
C15 C10 C11 C12 -0.4(5) . . . . ?
C9 C10 C11 C12 -177.9(3) . . . . ?
C10 C11 C12 C13 -1.9(5) . . . . ?
C10 C11 C12 Cl1 179.0(3) . . . . ?
C11 C12 C13 C14 2.8(5) . . . . ?
Cl1 C12 C13 C14 -178.0(3) . . . . ?
C11 C12 C13 Cl2 -178.9(3) . . . . ?
Cl1 C12 C13 Cl2 0.3(4) . . . . ?
C12 C13 C14 C15 -1.6(6) . . . . ?
Cl2 C13 C14 C15 -179.9(3) . . . . ?
C11 C10 C15 C14 1.6(5) . . . . ?
C9 C10 C15 C14 179.1(3) . . . . ?
C13 C14 C15 C10 -0.6(6) . . . . ?
C5 N3 C16 C17 -166.6(3) . . . . ?
C19 N3 C16 C17 -42.7(4) . . . . ?
N3 C16 C17 C18 27.9(4) . . . . ?
C16 C17 C18 C19 -3.0(4) . . . . ?
C5 N3 C19 C18 165.4(3) . . . . ?
C16 N3 C19 C18 41.3(4) . . . . ?
C17 C18 C19 N3 -23.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.917
_diffrn_reflns_theta_full        69.02
_diffrn_measured_fraction_theta_full 0.917
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.080