# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sb042_hy_compound_2
_database_code_depnum_ccdc_archive 'CCDC 1035385'
_audit_update_record             
;
2014-11-21 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(R,Rp)/(S,Sp)-1-([2.2]paracyclophane-4-yl)-N,N-(dimethyl)-ethylamine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H25 N'
_chemical_formula_sum            'C20 H25 N'
_chemical_formula_weight         279.41

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'

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

_cell_length_a                   10.529(1)
_cell_length_b                   11.655(1)
_cell_length_c                   12.596(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1545.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    76
_cell_measurement_theta_min      1
_cell_measurement_theta_max      25

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 dx = 40 mm, 65 sec./deg., 2 deg., 11 sets, 512 frames
;

_diffrn_ambient_temperature      123(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-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in phi and omega, 2 deg.'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            37108
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.05
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3519
_reflns_number_gt                3333
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Collect
_computing_cell_refinement       'DIRAX, EVALCCD'
_computing_data_reduction        EVALCCD
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    XP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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.
 Absolute configuration (structure) cannot be determined reliably: C17:S(?)
;

_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)+(0.0489P)²+0.3641P] where P=(Fo²+2Fc²)/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       ?
_chemical_absolute_configuration syn
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_number_reflns         3519
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.51919(11) 0.47737(10) 0.51716(10) 0.0169(2) Uani 1 1 d . . .
C2 C 0.43019(11) 0.39841(10) 0.55352(10) 0.0181(2) Uani 1 1 d . . .
H2 H 0.4272 0.3814 0.6272 0.022 Uiso 1 1 calc R . .
C3 C 0.34493(12) 0.34317(10) 0.48528(11) 0.0202(2) Uani 1 1 d . . .
C4 C 0.36914(12) 0.35140(11) 0.37713(11) 0.0233(3) Uani 1 1 d . . .
H4 H 0.3277 0.3013 0.3288 0.028 Uiso 1 1 calc R . .
C5 C 0.45387(12) 0.43290(11) 0.34005(10) 0.0217(3) Uani 1 1 d . . .
H5 H 0.4684 0.4389 0.2658 0.026 Uiso 1 1 calc R . .
C6 C 0.51846(11) 0.50637(11) 0.40844(10) 0.0186(2) Uani 1 1 d . . .
C7 C 0.55703(12) 0.62373(12) 0.36813(11) 0.0224(3) Uani 1 1 d . . .
H7A H 0.5667 0.6201 0.2900 0.027 Uiso 1 1 calc R . .
H7B H 0.6408 0.6438 0.3986 0.027 Uiso 1 1 calc R . .
C8 C 0.45887(13) 0.72210(11) 0.39661(14) 0.0291(3) Uani 1 1 d . . .
H8A H 0.4965 0.7725 0.4515 0.035 Uiso 1 1 calc R . .
H8B H 0.4433 0.7693 0.3326 0.035 Uiso 1 1 calc R . .
C9 C 0.33404(12) 0.67619(10) 0.43672(11) 0.0222(3) Uani 1 1 d . . .
C10 C 0.24853(13) 0.62357(12) 0.36788(11) 0.0244(3) Uani 1 1 d . . .
H10 H 0.2483 0.6439 0.2949 0.029 Uiso 1 1 calc R . .
C11 C 0.16368(12) 0.54170(11) 0.40479(11) 0.0230(3) Uani 1 1 d . . .
H11 H 0.1061 0.5063 0.3569 0.028 Uiso 1 1 calc R . .
C12 C 0.16243(12) 0.51116(11) 0.51172(11) 0.0227(3) Uani 1 1 d . . .
C13 C 0.22864(12) 0.58051(11) 0.58226(11) 0.0235(3) Uani 1 1 d . . .
H13 H 0.2160 0.5717 0.6565 0.028 Uiso 1 1 calc R . .
C14 C 0.31304(12) 0.66240(11) 0.54503(11) 0.0230(3) Uani 1 1 d . . .
H14 H 0.3571 0.7098 0.5941 0.028 Uiso 1 1 calc R . .
C15 C 0.11739(14) 0.39383(12) 0.54572(13) 0.0297(3) Uani 1 1 d . . .
H15A H 0.0398 0.3738 0.5054 0.036 Uiso 1 1 calc R . .
H15B H 0.0949 0.3960 0.6220 0.036 Uiso 1 1 calc R . .
C16 C 0.22001(13) 0.29868(11) 0.52736(13) 0.0269(3) Uani 1 1 d . . .
H16A H 0.2357 0.2587 0.5954 0.032 Uiso 1 1 calc R . .
H16B H 0.1859 0.2416 0.4766 0.032 Uiso 1 1 calc R . .
C17 C 0.60703(11) 0.54171(11) 0.59278(10) 0.0175(2) Uani 1 1 d . . .
H17 H 0.5926 0.6253 0.5796 0.021 Uiso 1 1 calc R . .
C18 C 0.74721(12) 0.51805(12) 0.56539(11) 0.0236(3) Uani 1 1 d . . .
H18A H 0.8021 0.5603 0.6146 0.035 Uiso 1 1 calc R . .
H18B H 0.7644 0.5431 0.4925 0.035 Uiso 1 1 calc R . .
H18C H 0.7643 0.4357 0.5716 0.035 Uiso 1 1 calc R . .
N18 N 0.57521(10) 0.52109(10) 0.70524(8) 0.0200(2) Uani 1 1 d . . .
C19 C 0.61854(14) 0.61553(14) 0.77189(11) 0.0309(3) Uani 1 1 d . . .
H19A H 0.5937 0.6011 0.8457 0.046 Uiso 1 1 calc R . .
H19B H 0.5799 0.6873 0.7474 0.046 Uiso 1 1 calc R . .
H19C H 0.7112 0.6216 0.7674 0.046 Uiso 1 1 calc R . .
C20 C 0.62540(13) 0.41321(13) 0.74682(11) 0.0270(3) Uani 1 1 d . . .
H20A H 0.7179 0.4189 0.7539 0.041 Uiso 1 1 calc R . .
H20B H 0.6043 0.3506 0.6979 0.041 Uiso 1 1 calc R . .
H20C H 0.5877 0.3977 0.8165 0.041 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 1.3910(17) . ?
C1 C6 1.4106(18) . ?
C1 C17 1.5249(16) . ?
C2 C3 1.3998(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3892(19) . ?
C3 C16 1.5099(19) . ?
C4 C5 1.3844(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3920(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.5144(18) . ?
C7 C8 1.5848(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5064(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.3915(19) . ?
C9 C10 1.392(2) . ?
C10 C11 1.3873(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.3932(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(2) . ?
C12 C15 1.5094(18) . ?
C13 C14 1.3858(19) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.565(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N18 1.4753(16) . ?
C17 C18 1.5407(17) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N18 C19 1.4575(17) . ?
N18 C20 1.4610(17) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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 C6 118.33(11) . . ?
C2 C1 C17 121.89(11) . . ?
C6 C1 C17 119.47(11) . . ?
C1 C2 C3 122.28(12) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 116.92(12) . . ?
C4 C3 C16 121.86(12) . . ?
C2 C3 C16 120.07(12) . . ?
C5 C4 C3 119.76(12) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.88(12) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 117.13(12) . . ?
C5 C6 C7 118.63(11) . . ?
C1 C6 C7 122.71(11) . . ?
C6 C7 C8 113.75(10) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C7 112.82(10) . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C14 C9 C10 117.20(12) . . ?
C14 C9 C8 120.56(13) . . ?
C10 C9 C8 120.78(13) . . ?
C11 C10 C9 120.70(13) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.39(13) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 117.71(12) . . ?
C13 C12 C15 120.23(13) . . ?
C11 C12 C15 120.58(13) . . ?
C14 C13 C12 120.41(13) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C9 120.87(13) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C12 C15 C16 112.52(11) . . ?
C12 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
C12 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C3 C16 C15 114.19(11) . . ?
C3 C16 H16A 108.7 . . ?
C15 C16 H16A 108.7 . . ?
C3 C16 H16B 108.7 . . ?
C15 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
N18 C17 C1 112.45(10) . . ?
N18 C17 C18 113.80(10) . . ?
C1 C17 C18 110.67(10) . . ?
N18 C17 H17 106.5 . . ?
C1 C17 H17 106.5 . . ?
C18 C17 H17 106.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 N18 C20 109.28(11) . . ?
C19 N18 C17 111.03(10) . . ?
C20 N18 C17 113.72(10) . . ?
N18 C19 H19A 109.5 . . ?
N18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N18 C20 H20A 109.5 . . ?
N18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 3.21(18) . . . . ?
C17 C1 C2 C3 176.76(11) . . . . ?
C1 C2 C3 C4 13.15(18) . . . . ?
C1 C2 C3 C16 -154.81(12) . . . . ?
C2 C3 C4 C5 -15.32(18) . . . . ?
C16 C3 C4 C5 152.41(12) . . . . ?
C3 C4 C5 C6 1.33(19) . . . . ?
C4 C5 C6 C1 15.19(17) . . . . ?
C4 C5 C6 C7 -151.12(12) . . . . ?
C2 C1 C6 C5 -17.10(17) . . . . ?
C17 C1 C6 C5 169.19(11) . . . . ?
C2 C1 C6 C7 148.60(11) . . . . ?
C17 C1 C6 C7 -25.11(17) . . . . ?
C5 C6 C7 C8 95.26(14) . . . . ?
C1 C6 C7 C8 -70.24(16) . . . . ?
C6 C7 C8 C9 -12.56(18) . . . . ?
C7 C8 C9 C14 93.23(16) . . . . ?
C7 C8 C9 C10 -72.62(17) . . . . ?
C14 C9 C10 C11 -13.47(18) . . . . ?
C8 C9 C10 C11 152.85(12) . . . . ?
C9 C10 C11 C12 0.26(19) . . . . ?
C10 C11 C12 C13 12.92(19) . . . . ?
C10 C11 C12 C15 -153.25(12) . . . . ?
C11 C12 C13 C14 -12.76(19) . . . . ?
C15 C12 C13 C14 153.45(12) . . . . ?
C12 C13 C14 C9 -0.58(19) . . . . ?
C10 C9 C14 C13 13.66(19) . . . . ?
C8 C9 C14 C13 -152.69(12) . . . . ?
C13 C12 C15 C16 -87.66(16) . . . . ?
C11 C12 C15 C16 78.16(17) . . . . ?
C4 C3 C16 C15 -90.47(16) . . . . ?
C2 C3 C16 C15 76.88(16) . . . . ?
C12 C15 C16 C3 3.08(19) . . . . ?
C2 C1 C17 N18 -7.08(16) . . . . ?
C6 C1 C17 N18 166.40(10) . . . . ?
C2 C1 C17 C18 121.43(13) . . . . ?
C6 C1 C17 C18 -65.10(14) . . . . ?
C1 C17 N18 C19 -155.35(11) . . . . ?
C18 C17 N18 C19 77.80(14) . . . . ?
C1 C17 N18 C20 80.91(13) . . . . ?
C18 C17 N18 C20 -45.94(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.035
# start Validation Reply Form
_vrf_PLAT910_sb042_hy_compound_2 
;
PROBLEM: Missing # of FCF Reflections Below Th(Min) .....         17 Report
RESPONSE: low-theta cutoff at theta = 5 deg.
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sb125_hy_compound_4e
_database_code_depnum_ccdc_archive 'CCDC 1035386'
_audit_update_record             
;
2014-11-21 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-(4-Phenylsulfanyl-[2.2]paracyclophane-16-yl)-N,N-(dimethyl)-ethylamine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H29 N S'
_chemical_formula_sum            'C26 H29 N S'
_chemical_formula_weight         387.56

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'
S S 0.1246 0.1234 '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/c'

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

_cell_length_a                   7.535(1)
_cell_length_b                   14.973(2)
_cell_length_c                   18.844(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.77(1)
_cell_angle_gamma                90.00
_cell_volume                     2115.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    114
_cell_measurement_theta_min      1
_cell_measurement_theta_max      25

_exptl_crystal_description       rods
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 dx = 35 mm, 90 sec./deg., 1 deg., 7 sets, 671 frames
;

_diffrn_ambient_temperature      123(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-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in phi and omega, 1 deg.'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            38450
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4847
_reflns_number_gt                3955
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius, 1998)'
_computing_cell_refinement       'EVALCCD (Duisenberg et al., 2003)'
_computing_data_reduction        'EVALCCD (Duisenberg et al., 2003)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    XP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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.
 NMe2-group is disordered. Refinement of disorder using constraints for
 displacement parameters (EADP) and restraints for  displacment parameters
 (SIMU) and geometry (SADI), s.o.f = 0.544(5).
;

_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)+(0.0460P)²+1.8900P] 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_number_reflns         4847
_refine_ls_number_parameters     252
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1258
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.105
_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 0.7414(3) 0.72600(13) 0.62105(11) 0.0330(5) Uani 1 1 d . . .
H1 H 0.7451 0.7866 0.6062 0.040 Uiso 1 1 calc R . .
C2 C 0.6254(3) 0.66720(14) 0.58381(10) 0.0289(4) Uani 1 1 d . . .
H2 H 0.5520 0.6879 0.5432 0.035 Uiso 1 1 calc R . .
C3 C 0.6137(2) 0.57786(12) 0.60455(9) 0.0224(4) Uani 1 1 d . . .
C4 C 0.7531(2) 0.54607(11) 0.65318(9) 0.0198(3) Uani 1 1 d . . .
S4 S 0.75986(8) 0.43379(3) 0.68356(2) 0.03275(15) Uani 1 1 d . . .
C41 C 0.8099(2) 0.37198(12) 0.60757(9) 0.0210(4) Uani 1 1 d . . .
C42 C 0.7467(3) 0.28494(13) 0.60084(10) 0.0269(4) Uani 1 1 d . . .
H42 H 0.6705 0.2623 0.6338 0.032 Uiso 1 1 calc R . .
C43 C 0.7948(3) 0.23115(13) 0.54598(11) 0.0303(4) Uani 1 1 d . . .
H43 H 0.7523 0.1714 0.5418 0.036 Uiso 1 1 calc R . .
C44 C 0.9043(3) 0.26405(13) 0.49731(10) 0.0284(4) Uani 1 1 d . . .
H44 H 0.9366 0.2272 0.4597 0.034 Uiso 1 1 calc R . .
C45 C 0.9663(3) 0.35080(13) 0.50379(10) 0.0268(4) Uani 1 1 d . . .
H45 H 1.0412 0.3736 0.4704 0.032 Uiso 1 1 calc R . .
C46 C 0.9199(2) 0.40486(12) 0.55880(9) 0.0230(4) Uani 1 1 d . . .
H46 H 0.9634 0.4644 0.5631 0.028 Uiso 1 1 calc R . .
C5 C 0.8708(2) 0.60556(13) 0.68997(9) 0.0236(4) Uani 1 1 d . . .
H5 H 0.9651 0.5831 0.7224 0.028 Uiso 1 1 calc R . .
C6 C 0.8529(3) 0.69742(13) 0.68012(11) 0.0299(4) Uani 1 1 d . . .
C7 C 0.9221(3) 0.76007(17) 0.73957(14) 0.0475(6) Uani 1 1 d . . .
H7A H 0.9643 0.8158 0.7185 0.057 Uiso 1 1 calc R . .
H7B H 1.0254 0.7320 0.7677 0.057 Uiso 1 1 calc R . .
C8 C 0.7767(3) 0.78407(15) 0.79101(13) 0.0408(5) Uani 1 1 d . . .
H8A H 0.8296 0.7776 0.8410 0.049 Uiso 1 1 calc R . .
H8B H 0.7414 0.8473 0.7836 0.049 Uiso 1 1 calc R . .
C9 C 0.6112(3) 0.72572(13) 0.77960(10) 0.0259(4) Uani 1 1 d . . .
C10 C 0.4723(3) 0.75493(14) 0.73073(10) 0.0314(5) Uani 1 1 d . . .
H10 H 0.4577 0.8171 0.7220 0.038 Uiso 1 1 calc R . .
C11 C 0.3561(3) 0.69601(16) 0.69484(10) 0.0337(5) Uani 1 1 d . . .
H11 H 0.2616 0.7177 0.6622 0.040 Uiso 1 1 calc R . .
C12 C 0.3763(2) 0.60490(15) 0.70609(10) 0.0294(4) Uani 1 1 d . . .
C13 C 0.4900(3) 0.57782(13) 0.76580(9) 0.0257(4) Uani 1 1 d . . .
H13 H 0.4874 0.5173 0.7808 0.031 Uiso 1 1 calc R . .
C14 C 0.6065(2) 0.63695(12) 0.80364(9) 0.0223(4) Uani 1 1 d D A .
C15 C 0.3120(3) 0.53846(18) 0.64906(11) 0.0423(6) Uani 1 1 d . . .
H15A H 0.1928 0.5572 0.6273 0.051 Uiso 1 1 calc R . .
H15B H 0.2986 0.4795 0.6716 0.051 Uiso 1 1 calc R . .
C16 C 0.4412(3) 0.52814(17) 0.58774(11) 0.0358(5) Uani 1 1 d . . .
H16A H 0.4672 0.4640 0.5812 0.043 Uiso 1 1 calc R . .
H16B H 0.3801 0.5509 0.5424 0.043 Uiso 1 1 calc R . .
C17 C 0.7411(3) 0.60437(15) 0.86392(10) 0.0321(5) Uani 1 1 d DU . .
H17 H 0.8638 0.6217 0.8532 0.038 Uiso 0.544(5) 1 calc PR A 1
H17' H 0.8536 0.6349 0.8534 0.038 Uiso 0.456(5) 1 calc PR A 2
C18 C 0.7041(3) 0.64599(16) 0.93548(10) 0.0358(5) Uani 1 1 d DU A .
H18A H 0.7925 0.6243 0.9733 0.054 Uiso 1 1 calc R . .
H18B H 0.5843 0.6290 0.9465 0.054 Uiso 1 1 calc R . .
H18C H 0.7119 0.7112 0.9323 0.054 Uiso 1 1 calc R . .
N18 N 0.7291(5) 0.5011(2) 0.86724(18) 0.0293(5) Uiso 0.544(5) 1 d PDU A 1
C19 C 0.9070(7) 0.4634(3) 0.8867(3) 0.0445(8) Uiso 0.544(5) 1 d PDU A 1
H19A H 0.9424 0.4740 0.9374 0.067 Uiso 0.544(5) 1 calc PR A 1
H19B H 0.9930 0.4920 0.8582 0.067 Uiso 0.544(5) 1 calc PR A 1
H19C H 0.9045 0.3990 0.8773 0.067 Uiso 0.544(5) 1 calc PR A 1
C20 C 0.5986(7) 0.4622(3) 0.9095(2) 0.0405(8) Uiso 0.544(5) 1 d PDU A 1
H20A H 0.5933 0.3975 0.9015 0.061 Uiso 0.544(5) 1 calc PR A 1
H20B H 0.4813 0.4885 0.8954 0.061 Uiso 0.544(5) 1 calc PR A 1
H20C H 0.6331 0.4741 0.9601 0.061 Uiso 0.544(5) 1 calc PR A 1
N18' N 0.7887(6) 0.5135(3) 0.8636(2) 0.0293(5) Uiso 0.456(5) 1 d PDU A 2
C19' C 0.9736(8) 0.4923(4) 0.8842(3) 0.0445(8) Uiso 0.456(5) 1 d PDU A 2
H19D H 1.0492 0.5266 0.8547 0.067 Uiso 0.456(5) 1 calc PR A 2
H19E H 0.9932 0.4283 0.8772 0.067 Uiso 0.456(5) 1 calc PR A 2
H19F H 1.0039 0.5075 0.9345 0.067 Uiso 0.456(5) 1 calc PR A 2
C20' C 0.6718(9) 0.4616(4) 0.9066(3) 0.0405(8) Uiso 0.456(5) 1 d PDU A 2
H20D H 0.7091 0.4710 0.9574 0.061 Uiso 0.456(5) 1 calc PR A 2
H20E H 0.6807 0.3980 0.8953 0.061 Uiso 0.456(5) 1 calc PR A 2
H20F H 0.5481 0.4815 0.8958 0.061 Uiso 0.456(5) 1 calc PR A 2


_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 1.381(3) . ?
C1 C6 1.393(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.399(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.406(2) . ?
C3 C16 1.504(3) . ?
C4 C5 1.392(3) . ?
C4 S4 1.7750(18) . ?
S4 C41 1.7768(18) . ?
C41 C46 1.388(2) . ?
C41 C42 1.389(3) . ?
C42 C43 1.387(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.385(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.382(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.388(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.513(3) . ?
C7 C8 1.576(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.520(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.393(3) . ?
C9 C14 1.406(3) . ?
C10 C11 1.372(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.404(3) . ?
C12 C15 1.508(3) . ?
C13 C14 1.391(3) . ?
C13 H13 0.9500 . ?
C14 C17 1.525(3) . ?
C15 C16 1.591(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N18' 1.408(4) . ?
C17 C18 1.536(3) . ?
C17 N18 1.550(4) . ?
C17 H17 1.0000 . ?
C17 H17' 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N18 C20 1.448(5) . ?
N18 C19 1.467(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N18' C19' 1.444(5) . ?
N18' C20' 1.476(5) . ?
C19' H19D 0.9800 . ?
C19' H19E 0.9800 . ?
C19' H19F 0.9800 . ?
C20' H20D 0.9800 . ?
C20' H20E 0.9800 . ?
C20' H20F 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 C6 120.68(18) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C1 C2 C3 121.47(18) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C4 116.23(17) . . ?
C2 C3 C16 119.48(18) . . ?
C4 C3 C16 122.88(18) . . ?
C5 C4 C3 120.33(16) . . ?
C5 C4 S4 116.69(14) . . ?
C3 C4 S4 121.77(14) . . ?
C4 S4 C41 103.60(8) . . ?
C46 C41 C42 119.63(16) . . ?
C46 C41 S4 122.54(14) . . ?
C42 C41 S4 117.63(14) . . ?
C43 C42 C41 120.00(18) . . ?
C43 C42 H42 120.0 . . ?
C41 C42 H42 120.0 . . ?
C44 C43 C42 120.31(18) . . ?
C44 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
C45 C44 C43 119.66(17) . . ?
C45 C44 H44 120.2 . . ?
C43 C44 H44 120.2 . . ?
C44 C45 C46 120.39(18) . . ?
C44 C45 H45 119.8 . . ?
C46 C45 H45 119.8 . . ?
C45 C46 C41 120.00(17) . . ?
C45 C46 H46 120.0 . . ?
C41 C46 H46 120.0 . . ?
C4 C5 C6 121.14(18) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 116.91(18) . . ?
C5 C6 C7 119.5(2) . . ?
C1 C6 C7 122.4(2) . . ?
C6 C7 C8 112.81(18) . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 113.16(16) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C14 117.91(19) . . ?
C10 C9 C8 117.66(19) . . ?
C14 C9 C8 123.01(19) . . ?
C11 C10 C9 121.57(19) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 120.15(18) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 117.10(18) . . ?
C11 C12 C15 121.17(19) . . ?
C13 C12 C15 120.5(2) . . ?
C14 C13 C12 121.98(18) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C13 C14 C9 118.13(17) . . ?
C13 C14 C17 121.08(18) . . ?
C9 C14 C17 120.39(17) . . ?
C12 C15 C16 113.92(17) . . ?
C12 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C12 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C3 C16 C15 112.20(16) . . ?
C3 C16 H16A 109.2 . . ?
C15 C16 H16A 109.2 . . ?
C3 C16 H16B 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N18' C17 C14 117.2(2) . . ?
N18' C17 C18 117.7(2) . . ?
C14 C17 C18 110.96(16) . . ?
N18' C17 N18 18.53(19) . . ?
C14 C17 N18 108.2(2) . . ?
C18 C17 N18 110.6(2) . . ?
N18' C17 H17 90.5 . . ?
C14 C17 H17 109.0 . . ?
C18 C17 H17 109.0 . . ?
N18 C17 H17 109.0 . . ?
N18' C17 H17' 102.7 . . ?
C14 C17 H17' 102.7 . . ?
C18 C17 H17' 102.7 . . ?
N18 C17 H17' 121.2 . . ?
H17 C17 H17' 12.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 N18 C19 111.2(3) . . ?
C20 N18 C17 118.0(3) . . ?
C19 N18 C17 109.8(3) . . ?
C17 N18' C19' 116.8(4) . . ?
C17 N18' C20' 109.9(3) . . ?
C19' N18' C20' 110.5(4) . . ?
N18' C19' H19D 109.5 . . ?
N18' C19' H19E 109.5 . . ?
H19D C19' H19E 109.5 . . ?
N18' C19' H19F 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 109.5 . . ?
N18' C20' H20D 109.5 . . ?
N18' C20' H20E 109.5 . . ?
H20D C20' H20E 109.5 . . ?
N18' C20' H20F 109.5 . . ?
H20D C20' H20F 109.5 . . ?
H20E C20' H20F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.1(3) . . . . ?
C1 C2 C3 C4 -15.0(3) . . . . ?
C1 C2 C3 C16 151.89(18) . . . . ?
C2 C3 C4 C5 14.1(2) . . . . ?
C16 C3 C4 C5 -152.30(17) . . . . ?
C2 C3 C4 S4 -178.90(13) . . . . ?
C16 C3 C4 S4 14.7(2) . . . . ?
C5 C4 S4 C41 -121.42(14) . . . . ?
C3 C4 S4 C41 71.10(16) . . . . ?
C4 S4 C41 C46 34.41(17) . . . . ?
C4 S4 C41 C42 -150.80(15) . . . . ?
C46 C41 C42 C43 0.6(3) . . . . ?
S4 C41 C42 C43 -174.39(16) . . . . ?
C41 C42 C43 C44 -0.6(3) . . . . ?
C42 C43 C44 C45 0.3(3) . . . . ?
C43 C44 C45 C46 0.2(3) . . . . ?
C44 C45 C46 C41 -0.3(3) . . . . ?
C42 C41 C46 C45 -0.1(3) . . . . ?
S4 C41 C46 C45 174.59(14) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
S4 C4 C5 C6 -167.10(14) . . . . ?
C4 C5 C6 C1 -14.6(3) . . . . ?
C4 C5 C6 C7 153.34(18) . . . . ?
C2 C1 C6 C5 13.8(3) . . . . ?
C2 C1 C6 C7 -153.75(19) . . . . ?
C5 C6 C7 C8 -91.2(3) . . . . ?
C1 C6 C7 C8 76.1(3) . . . . ?
C6 C7 C8 C9 11.6(3) . . . . ?
C7 C8 C9 C10 -90.4(2) . . . . ?
C7 C8 C9 C14 75.7(3) . . . . ?
C14 C9 C10 C11 -14.2(3) . . . . ?
C8 C9 C10 C11 152.58(18) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 C13 14.3(3) . . . . ?
C10 C11 C12 C15 -152.88(19) . . . . ?
C11 C12 C13 C14 -13.3(3) . . . . ?
C15 C12 C13 C14 154.00(18) . . . . ?
C12 C13 C14 C9 -1.4(3) . . . . ?
C12 C13 C14 C17 -174.14(17) . . . . ?
C10 C9 C14 C13 15.0(2) . . . . ?
C8 C9 C14 C13 -151.08(18) . . . . ?
C10 C9 C14 C17 -172.24(16) . . . . ?
C8 C9 C14 C17 21.7(3) . . . . ?
C11 C12 C15 C16 78.2(3) . . . . ?
C13 C12 C15 C16 -88.5(2) . . . . ?
C2 C3 C16 C15 -88.9(2) . . . . ?
C4 C3 C16 C15 77.0(2) . . . . ?
C12 C15 C16 C3 7.7(3) . . . . ?
C13 C14 C17 N18' 22.2(3) . . . . ?
C9 C14 C17 N18' -150.4(3) . . . . ?
C13 C14 C17 C18 -116.9(2) . . . . ?
C9 C14 C17 C18 70.5(2) . . . . ?
C13 C14 C17 N18 4.6(3) . . . . ?
C9 C14 C17 N18 -168.0(2) . . . . ?
N18' C17 N18 C20 150.9(9) . . . . ?
C14 C17 N18 C20 -86.9(3) . . . . ?
C18 C17 N18 C20 34.8(4) . . . . ?
N18' C17 N18 C19 22.1(7) . . . . ?
C14 C17 N18 C19 144.4(3) . . . . ?
C18 C17 N18 C19 -93.9(3) . . . . ?
C14 C17 N18' C19' 140.9(4) . . . . ?
C18 C17 N18' C19' -82.7(4) . . . . ?
N18 C17 N18' C19' -154.5(10) . . . . ?
C14 C17 N18' C20' -92.3(4) . . . . ?
C18 C17 N18' C20' 44.1(4) . . . . ?
N18 C17 N18' C20' -27.7(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.052
# start Validation Reply Form
_vrf_PLAT201_sb125_hy_compound_4e 
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          3 Report
RESPONSE: NMe2-group is disordered, disordered N and C-atoms refined
isotropically
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sb129_hy_compound_6
_database_code_depnum_ccdc_archive 'CCDC 1035387'
_audit_update_record             
;
2014-11-21 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (rac)-5-N,N-dimethylaminomethyl-4-Methylsulfanyl-[2.2]paracyclophane 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H25 N S'
_chemical_formula_sum            'C20 H25 N S'
_chemical_formula_weight         311.47

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'
S S 0.1246 0.1234 '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/n'

loop_
_symmetry_equiv_pos_as_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                   8.104(1)
_cell_length_b                   8.358(1)
_cell_length_c                   24.688(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.20(1)
_cell_angle_gamma                90.00
_cell_volume                     1662.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    88
_cell_measurement_theta_min      1
_cell_measurement_theta_max      25

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 dx = 45 mm, 120 sec./deg., 1 deg., 7 sets, 582 frames
;

_diffrn_ambient_temperature      123(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-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in phi and omega, 1 deg.'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19143
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.35
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3803
_reflns_number_gt                3114
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius, 1998)'
_computing_cell_refinement       'EVALCCD (Duisenberg et al., 2003)'
_computing_data_reduction        'EVALCCD (Duisenberg et al., 2003)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    XP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0379P)²+1.3038P] 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_number_reflns         3803
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.5165(2) 0.1071(2) 0.07886(7) 0.0211(3) Uani 1 1 d . . .
H1 H 0.4496 0.0140 0.0733 0.025 Uiso 1 1 calc R . .
C2 C 0.6390(2) 0.1363(2) 0.04512(6) 0.0215(3) Uani 1 1 d . . .
H2 H 0.6544 0.0637 0.0165 0.026 Uiso 1 1 calc R . .
C3 C 0.7391(2) 0.2703(2) 0.05273(6) 0.0195(3) Uani 1 1 d . . .
C4 C 0.68661(19) 0.39230(19) 0.08619(6) 0.0177(3) Uani 1 1 d . . .
S4 S 0.80093(5) 0.57461(6) 0.091099(18) 0.02588(13) Uani 1 1 d . . .
C5 C 0.56149(19) 0.3648(2) 0.12025(6) 0.0175(3) Uani 1 1 d . . .
C6 C 0.49013(19) 0.2120(2) 0.12058(6) 0.0189(3) Uani 1 1 d . . .
C7 C 0.4156(2) 0.1477(2) 0.16977(7) 0.0244(4) Uani 1 1 d . . .
H7A H 0.3427 0.0559 0.1585 0.029 Uiso 1 1 calc R . .
H7B H 0.3462 0.2318 0.1841 0.029 Uiso 1 1 calc R . .
C8 C 0.5524(2) 0.0918(2) 0.21674(7) 0.0261(4) Uani 1 1 d . . .
H8A H 0.5507 0.1647 0.2483 0.031 Uiso 1 1 calc R . .
H8B H 0.5243 -0.0169 0.2288 0.031 Uiso 1 1 calc R . .
C9 C 0.7253(2) 0.0895(2) 0.19914(6) 0.0205(3) Uani 1 1 d . . .
C10 C 0.7788(2) -0.0325(2) 0.16671(7) 0.0221(4) Uani 1 1 d . . .
H10 H 0.7301 -0.1358 0.1674 0.027 Uiso 1 1 calc R . .
C11 C 0.9030(2) -0.0035(2) 0.13335(6) 0.0210(3) Uani 1 1 d . . .
H11 H 0.9392 -0.0877 0.1116 0.025 Uiso 1 1 calc R . .
C12 C 0.97499(19) 0.1473(2) 0.13134(6) 0.0197(3) Uani 1 1 d . . .
C13 C 0.9472(2) 0.2543(2) 0.17245(6) 0.0205(3) Uani 1 1 d . . .
H13 H 1.0135 0.3479 0.1777 0.025 Uiso 1 1 calc R . .
C14 C 0.8236(2) 0.2254(2) 0.20600(6) 0.0212(3) Uani 1 1 d . . .
H14 H 0.8060 0.2996 0.2340 0.025 Uiso 1 1 calc R . .
C15 C 1.0482(2) 0.2050(2) 0.08124(7) 0.0241(4) Uani 1 1 d . . .
H15A H 1.1129 0.1171 0.0669 0.029 Uiso 1 1 calc R . .
H15B H 1.1256 0.2943 0.0915 0.029 Uiso 1 1 calc R . .
C16 C 0.9113(2) 0.2637(2) 0.03463(7) 0.0257(4) Uani 1 1 d . . .
H16A H 0.9417 0.3715 0.0224 0.031 Uiso 1 1 calc R . .
H16B H 0.9103 0.1903 0.0031 0.031 Uiso 1 1 calc R . .
C17 C 0.7137(3) 0.6730(2) 0.03013(8) 0.0338(4) Uani 1 1 d . . .
H17A H 0.7299 0.6063 -0.0015 0.051 Uiso 1 1 calc R . .
H17B H 0.7687 0.7764 0.0268 0.051 Uiso 1 1 calc R . .
H17C H 0.5947 0.6901 0.0318 0.051 Uiso 1 1 calc R . .
C18 C 0.5128(2) 0.4870(2) 0.16075(7) 0.0223(4) Uani 1 1 d . . .
H18A H 0.5360 0.4433 0.1981 0.027 Uiso 1 1 calc R . .
H18B H 0.5810 0.5845 0.1584 0.027 Uiso 1 1 calc R . .
N18 N 0.33661(17) 0.52967(18) 0.15076(6) 0.0221(3) Uani 1 1 d . . .
C19 C 0.2860(3) 0.6175(3) 0.19701(8) 0.0359(5) Uani 1 1 d . . .
H19A H 0.3520 0.7156 0.2024 0.054 Uiso 1 1 calc R . .
H19B H 0.3038 0.5510 0.2298 0.054 Uiso 1 1 calc R . .
H19C H 0.1682 0.6453 0.1900 0.054 Uiso 1 1 calc R . .
C20 C 0.3046(2) 0.6248(2) 0.10179(7) 0.0297(4) Uani 1 1 d . . .
H20A H 0.1852 0.6450 0.0945 0.045 Uiso 1 1 calc R . .
H20B H 0.3432 0.5668 0.0710 0.045 Uiso 1 1 calc R . .
H20C H 0.3639 0.7268 0.1067 0.045 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(2) . ?
C1 C6 1.386(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.407(2) . ?
C3 C16 1.512(2) . ?
C4 C5 1.404(2) . ?
C4 S4 1.7806(16) . ?
S4 C17 1.7924(19) . ?
C5 C6 1.403(2) . ?
C5 C18 1.511(2) . ?
C6 C7 1.512(2) . ?
C7 C8 1.586(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.511(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.387(2) . ?
C9 C10 1.394(2) . ?
C10 C11 1.389(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(2) . ?
C12 C15 1.508(2) . ?
C13 C14 1.389(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.587(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N18 1.467(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N18 C20 1.447(2) . ?
N18 C19 1.453(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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 C6 120.88(15) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 120.60(15) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 117.13(15) . . ?
C2 C3 C16 118.50(16) . . ?
C4 C3 C16 123.19(15) . . ?
C5 C4 C3 121.12(15) . . ?
C5 C4 S4 120.21(13) . . ?
C3 C4 S4 118.18(12) . . ?
C4 S4 C17 100.39(8) . . ?
C6 C5 C4 118.50(15) . . ?
C6 C5 C18 118.32(15) . . ?
C4 C5 C18 122.87(15) . . ?
C1 C6 C5 118.36(15) . . ?
C1 C6 C7 118.59(15) . . ?
C5 C6 C7 121.94(15) . . ?
C6 C7 C8 112.58(13) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 112.94(13) . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C14 C9 C10 117.31(15) . . ?
C14 C9 C8 119.52(16) . . ?
C10 C9 C8 121.99(16) . . ?
C11 C10 C9 120.22(16) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.83(16) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 117.07(15) . . ?
C13 C12 C15 120.19(16) . . ?
C11 C12 C15 121.49(15) . . ?
C14 C13 C12 120.56(16) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C9 C14 C13 120.76(16) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C12 C15 C16 112.81(13) . . ?
C12 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C12 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C3 C16 C15 113.09(13) . . ?
C3 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
C3 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
S4 C17 H17A 109.5 . . ?
S4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N18 C18 C5 111.85(13) . . ?
N18 C18 H18A 109.2 . . ?
C5 C18 H18A 109.2 . . ?
N18 C18 H18B 109.2 . . ?
C5 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C20 N18 C19 109.81(15) . . ?
C20 N18 C18 110.93(14) . . ?
C19 N18 C18 110.05(14) . . ?
N18 C19 H19A 109.5 . . ?
N18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N18 C20 H20A 109.5 . . ?
N18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.7(2) . . . . ?
C1 C2 C3 C4 -15.1(2) . . . . ?
C1 C2 C3 C16 152.87(15) . . . . ?
C2 C3 C4 C5 14.5(2) . . . . ?
C16 C3 C4 C5 -152.84(15) . . . . ?
C2 C3 C4 S4 -173.58(11) . . . . ?
C16 C3 C4 S4 19.1(2) . . . . ?
C5 C4 S4 C17 -106.55(14) . . . . ?
C3 C4 S4 C17 81.47(14) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
S4 C4 C5 C6 -171.29(11) . . . . ?
C3 C4 C5 C18 173.93(14) . . . . ?
S4 C4 C5 C18 2.2(2) . . . . ?
C2 C1 C6 C5 14.7(2) . . . . ?
C2 C1 C6 C7 -153.51(15) . . . . ?
C4 C5 C6 C1 -15.0(2) . . . . ?
C18 C5 C6 C1 171.23(14) . . . . ?
C4 C5 C6 C7 152.80(15) . . . . ?
C18 C5 C6 C7 -21.0(2) . . . . ?
C1 C6 C7 C8 91.54(19) . . . . ?
C5 C6 C7 C8 -76.2(2) . . . . ?
C6 C7 C8 C9 -9.3(2) . . . . ?
C7 C8 C9 C14 90.19(19) . . . . ?
C7 C8 C9 C10 -77.1(2) . . . . ?
C14 C9 C10 C11 -14.1(2) . . . . ?
C8 C9 C10 C11 153.43(15) . . . . ?
C9 C10 C11 C12 -0.5(2) . . . . ?
C10 C11 C12 C13 14.8(2) . . . . ?
C10 C11 C12 C15 -152.44(16) . . . . ?
C11 C12 C13 C14 -14.5(2) . . . . ?
C15 C12 C13 C14 152.89(15) . . . . ?
C10 C9 C14 C13 14.4(2) . . . . ?
C8 C9 C14 C13 -153.43(15) . . . . ?
C12 C13 C14 C9 0.0(2) . . . . ?
C13 C12 C15 C16 -88.60(19) . . . . ?
C11 C12 C15 C16 78.3(2) . . . . ?
C2 C3 C16 C15 -91.07(19) . . . . ?
C4 C3 C16 C15 76.1(2) . . . . ?
C12 C15 C16 C3 7.6(2) . . . . ?
C6 C5 C18 N18 -64.73(19) . . . . ?
C4 C5 C18 N18 121.78(16) . . . . ?
C5 C18 N18 C20 -71.25(19) . . . . ?
C5 C18 N18 C19 167.03(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.050
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sb128_hy_compound_7
_database_code_depnum_ccdc_archive 'CCDC 1035388'
_audit_update_record             
;
2014-11-21 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(Rp,R)/(Sp,S)-5-N,N-dimethylaminomethyl-4-Methylsulfanyl-[2.2]paracyclophane
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H25 N S'
_chemical_formula_sum            'C20 H25 N S'
_chemical_formula_weight         311.47

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'
S S 0.1246 0.1234 '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/n'

loop_
_symmetry_equiv_pos_as_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                   7.812(1)
_cell_length_b                   11.736(1)
_cell_length_c                   18.668(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.49(1)
_cell_angle_gamma                90.00
_cell_volume                     1700.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    108
_cell_measurement_theta_min      1
_cell_measurement_theta_max      25

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 dx = 40 mm, 40 sec./deg., 2 deg., 4 sets, 179 frames
;

_diffrn_ambient_temperature      123(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-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in phi and omega, 2 deg.'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13865
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3870
_reflns_number_gt                2923
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius, 1998)'
_computing_cell_refinement       'EVALCCD (Duisenberg et al., 2003)'
_computing_data_reduction        'EVALCCD (Duisenberg et al., 2003)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    XP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0462P)²+0.8950P] 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_number_reflns         3870
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.73146(19) 0.57399(15) 0.73287(9) 0.0182(4) Uani 1 1 d . . .
H1 H 0.8285 0.5262 0.7297 0.022 Uiso 1 1 calc R . .
C2 C 0.6973(2) 0.61449(15) 0.79940(9) 0.0192(4) Uani 1 1 d . . .
H2 H 0.7708 0.5939 0.8414 0.023 Uiso 1 1 calc R . .
C3 C 0.5560(2) 0.68536(15) 0.80545(9) 0.0186(4) Uani 1 1 d . . .
C4 C 0.4766(2) 0.73346(15) 0.74205(9) 0.0175(3) Uani 1 1 d . . .
H4 H 0.3990 0.7952 0.7449 0.021 Uiso 1 1 calc R . .
C5 C 0.50818(19) 0.69321(14) 0.67461(9) 0.0157(3) Uani 1 1 d . . .
C6 C 0.62461(19) 0.60267(14) 0.67042(9) 0.0152(3) Uani 1 1 d . . .
C7 C 0.6058(2) 0.52291(15) 0.60615(9) 0.0186(4) Uani 1 1 d . . .
H7 H 0.5273 0.5599 0.5669 0.022 Uiso 1 1 calc R . .
S7 S 0.80811(6) 0.49046(4) 0.57034(3) 0.02786(14) Uani 1 1 d . . .
C8 C 0.5241(2) 0.40414(16) 0.62397(10) 0.0233(4) Uani 1 1 d . . .
H8A H 0.4513 0.3759 0.5807 0.028 Uiso 1 1 calc R . .
H8B H 0.6173 0.3480 0.6365 0.028 Uiso 1 1 calc R . .
C9 C 0.4160(2) 0.41419(15) 0.68599(10) 0.0211(4) Uani 1 1 d . . .
C10 C 0.4820(2) 0.37881(16) 0.75487(10) 0.0227(4) Uani 1 1 d . . .
H10 H 0.5654 0.3196 0.7604 0.027 Uiso 1 1 calc R . .
C11 C 0.4270(2) 0.42909(16) 0.81535(10) 0.0238(4) Uani 1 1 d . . .
H11 H 0.4720 0.4034 0.8620 0.029 Uiso 1 1 calc R . .
C12 C 0.3063(2) 0.51695(16) 0.80861(10) 0.0234(4) Uani 1 1 d . . .
C13 C 0.2150(2) 0.53307(16) 0.74080(10) 0.0241(4) Uani 1 1 d . . .
H13 H 0.1155 0.5802 0.7360 0.029 Uiso 1 1 calc R . .
C14 C 0.2677(2) 0.48120(15) 0.68011(10) 0.0224(4) Uani 1 1 d . . .
H14 H 0.2024 0.4914 0.6344 0.027 Uiso 1 1 calc R . .
C15 C 0.3017(2) 0.60675(18) 0.86616(11) 0.0296(4) Uani 1 1 d . . .
H15A H 0.2933 0.5690 0.9131 0.036 Uiso 1 1 calc R . .
H15B H 0.1975 0.6543 0.8548 0.036 Uiso 1 1 calc R . .
C16 C 0.4667(2) 0.68634(17) 0.87296(9) 0.0256(4) Uani 1 1 d . . .
H16A H 0.4319 0.7653 0.8830 0.031 Uiso 1 1 calc R . .
H16B H 0.5484 0.6604 0.9141 0.031 Uiso 1 1 calc R . .
C17 C 0.8827(2) 0.63186(18) 0.55278(11) 0.0317(5) Uani 1 1 d . . .
H17A H 0.7924 0.6731 0.5225 0.048 Uiso 1 1 calc R . .
H17B H 0.9862 0.6269 0.5278 0.048 Uiso 1 1 calc R . .
H17C H 0.9100 0.6725 0.5985 0.048 Uiso 1 1 calc R . .
C18 C 0.3985(2) 0.73879(15) 0.60925(9) 0.0179(4) Uani 1 1 d . . .
H18A H 0.3238 0.6768 0.5875 0.021 Uiso 1 1 calc R . .
H18B H 0.3229 0.7997 0.6246 0.021 Uiso 1 1 calc R . .
N18 N 0.50032(17) 0.78450(13) 0.55459(7) 0.0194(3) Uani 1 1 d . . .
C19 C 0.3840(2) 0.82209(17) 0.49260(9) 0.0259(4) Uani 1 1 d . . .
H19A H 0.3092 0.7587 0.4748 0.039 Uiso 1 1 calc R . .
H19B H 0.4512 0.8476 0.4544 0.039 Uiso 1 1 calc R . .
H19C H 0.3131 0.8852 0.5069 0.039 Uiso 1 1 calc R . .
C20 C 0.6056(2) 0.87951(17) 0.58363(11) 0.0291(4) Uani 1 1 d . . .
H20A H 0.5310 0.9405 0.5981 0.044 Uiso 1 1 calc R . .
H20B H 0.6744 0.9082 0.5467 0.044 Uiso 1 1 calc R . .
H20C H 0.6825 0.8539 0.6257 0.044 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 1.384(2) . ?
C1 C6 1.396(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.397(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(2) . ?
C3 C16 1.508(2) . ?
C4 C5 1.393(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.407(2) . ?
C5 C18 1.508(2) . ?
C6 C7 1.516(2) . ?
C7 C8 1.584(3) . ?
C7 S7 1.8243(16) . ?
C7 H7 1.0000 . ?
S7 C17 1.801(2) . ?
C8 C9 1.513(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.394(2) . ?
C9 C14 1.394(2) . ?
C10 C11 1.384(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.394(3) . ?
C12 C15 1.508(3) . ?
C13 C14 1.389(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.586(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N18 1.465(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N18 C20 1.454(2) . ?
N18 C19 1.457(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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 C6 120.58(15) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C1 C2 C3 120.78(15) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 116.92(16) . . ?
C4 C3 C16 120.27(15) . . ?
C2 C3 C16 121.09(16) . . ?
C3 C4 C5 121.58(16) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 119.23(15) . . ?
C4 C5 C18 117.96(14) . . ?
C6 C5 C18 122.34(15) . . ?
C1 C6 C5 117.71(15) . . ?
C1 C6 C7 120.48(15) . . ?
C5 C6 C7 120.35(14) . . ?
C6 C7 C8 112.49(14) . . ?
C6 C7 S7 114.12(11) . . ?
C8 C7 S7 106.24(11) . . ?
C6 C7 H7 107.9 . . ?
C8 C7 H7 107.9 . . ?
S7 C7 H7 107.9 . . ?
C17 S7 C7 100.70(9) . . ?
C9 C8 C7 111.42(14) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C14 117.27(17) . . ?
C10 C9 C8 120.18(15) . . ?
C14 C9 C8 120.96(16) . . ?
C11 C10 C9 120.59(17) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.73(17) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 117.00(18) . . ?
C11 C12 C15 121.56(17) . . ?
C13 C12 C15 120.06(17) . . ?
C14 C13 C12 120.87(17) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C9 120.20(17) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C12 C15 C16 112.57(14) . . ?
C12 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
C12 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C3 C16 C15 112.16(15) . . ?
C3 C16 H16A 109.2 . . ?
C15 C16 H16A 109.2 . . ?
C3 C16 H16B 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
S7 C17 H17A 109.5 . . ?
S7 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S7 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N18 C18 C5 112.96(13) . . ?
N18 C18 H18A 109.0 . . ?
C5 C18 H18A 109.0 . . ?
N18 C18 H18B 109.0 . . ?
C5 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C20 N18 C19 109.87(14) . . ?
C20 N18 C18 110.50(14) . . ?
C19 N18 C18 108.97(13) . . ?
N18 C19 H19A 109.5 . . ?
N18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N18 C20 H20A 109.5 . . ?
N18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(3) . . . . ?
C1 C2 C3 C4 -14.2(2) . . . . ?
C1 C2 C3 C16 150.93(17) . . . . ?
C2 C3 C4 C5 14.7(2) . . . . ?
C16 C3 C4 C5 -150.48(16) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C3 C4 C5 C18 171.51(15) . . . . ?
C2 C1 C6 C5 14.6(2) . . . . ?
C2 C1 C6 C7 -151.70(16) . . . . ?
C4 C5 C6 C1 -13.9(2) . . . . ?
C18 C5 C6 C1 174.16(15) . . . . ?
C4 C5 C6 C7 152.37(15) . . . . ?
C18 C5 C6 C7 -19.6(2) . . . . ?
C1 C6 C7 C8 62.77(19) . . . . ?
C5 C6 C7 C8 -103.14(17) . . . . ?
C1 C6 C7 S7 -58.36(19) . . . . ?
C5 C6 C7 S7 135.73(14) . . . . ?
C6 C7 S7 C17 -55.71(14) . . . . ?
C8 C7 S7 C17 179.75(12) . . . . ?
C6 C7 C8 C9 24.74(19) . . . . ?
S7 C7 C8 C9 150.28(12) . . . . ?
C7 C8 C9 C10 -101.22(19) . . . . ?
C7 C8 C9 C14 64.0(2) . . . . ?
C14 C9 C10 C11 -14.4(2) . . . . ?
C8 C9 C10 C11 151.33(16) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 C13 14.8(2) . . . . ?
C10 C11 C12 C15 -151.86(17) . . . . ?
C11 C12 C13 C14 -13.6(2) . . . . ?
C15 C12 C13 C14 153.28(17) . . . . ?
C12 C13 C14 C9 -1.6(3) . . . . ?
C10 C9 C14 C13 15.6(2) . . . . ?
C8 C9 C14 C13 -150.05(17) . . . . ?
C11 C12 C15 C16 67.0(2) . . . . ?
C13 C12 C15 C16 -99.26(19) . . . . ?
C4 C3 C16 C15 68.0(2) . . . . ?
C2 C3 C16 C15 -96.58(19) . . . . ?
C12 C15 C16 C3 21.4(2) . . . . ?
C4 C5 C18 N18 126.91(16) . . . . ?
C6 C5 C18 N18 -61.1(2) . . . . ?
C5 C18 N18 C20 -61.46(19) . . . . ?
C5 C18 N18 C19 177.73(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.052

#==============================================================================

#_eof # End of Crystallographic Information File

