# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2003


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

loop_
_publ_author_name
L.Tom
'David B. Belanger'
D.J.R.O'Mahony

_publ_contact_author_name        'Prof Tom Livinghouse'
_publ_contact_author_address     
;
Department of Chemistry
Montana State University
Bozeman
MT
59717
UNITED STATES OF AMERICA
;

_publ_contact_author_email       LIVINGHOUSE@CHEMISTRY.MONTANA.EDU

_publ_section_title              
;
Substrate Control of Stereoselection in the Rhodium
(I) Catalyzed Intramolecular [4+2] Cycloaddition Reaction
;

data_B302426C
_database_code_CSD               206531

_computing_data_collection       'Siemens XSCANS'
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS'
_computing_structure_solution    'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'

_chemical_formula_weight         305.42
_chemical_formula_sum            'C17 H23 N1 O2 S1'

_cell_length_a                   26.112(3)
_cell_length_b                   9.913(1)
_cell_length_c                   16.461(2)
_cell_angle_alpha                90
_cell_angle_beta                 127.628(6)
_cell_angle_gamma                90
_cell_volume                     3374.4(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    298
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      20.3
_cell_measurement_theta_max      28.6

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_Int_Tables_number      15

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y,1/2-z
x,-y,1/2+z
1/2+x,1/2+y,z
1/2-x,1/2-y,-z
1/2-x,1/2+y,1/2-z
1/2+x,1/2-y,1/2+z
_exptl_crystal_description       parallelpiped
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          .14
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_meas      'not measured'
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   'face-indexed numerical'
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_T_max  0.986

_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Siemens P4 upgraded Nicolet R3'
_diffrn_measurement_method       \q/2\q
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
_diffrn_standards_decay_%        2.7
_diffrn_reflns_number            5280
_reflns_number_observed          1346
_reflns_number_total             4913
_reflns_observed_criterion       >5sigma(F)
_diffrn_reflns_av_R_equivalents  0.017
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_reduction_process 'Lp corrections applied'
_atom_sites_solution_primary     'direct methods'
_atom_sites_solution_secondary   'difference Fourier'

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
C(1) 0.4003(2) 0.3489(4) 0.1436(3) 0.055(3) Uani ?
N(2) 0.3448(2) 0.3315(3) 0.1465(3) 0.057(2) Uani ?
C(3) 0.2885(2) 0.4119(5) 0.0646(3) 0.065(3) Uani ?
C(4) 0.2699(2) 0.5645(6) -0.0736(3) 0.076(3) Uani ?
C(5) 0.2986(3) 0.6780(6) -0.0605(4) 0.078(4) Uani ?
C(6) 0.3693(2) 0.7039(5) 0.0211(4) 0.068(4) Uani ?
C(7) 0.3972(2) 0.5979(4) 0.1053(3) 0.054(3) Uani ?
C(8) 0.3824(3) 0.8471(5) 0.0642(4) 0.113(5) Uani ?
C(9) 0.4169(2) 0.2145(4) 0.1198(4) 0.081(4) Uani ?
C(10) 0.3774(2) 0.4563(4) 0.0615(3) 0.050(3) Uani ?
C(11) 0.3039(2) 0.4429(5) -0.0093(3) 0.058(3) Uani ?
S 0.35778(7) 0.3180(1) 0.2561(1) 0.0699(9) Uani ?
O(1) 0.4145(2) 0.2354(3) 0.3209(2) 0.090(3) Uani ?
O(2) 0.2973(2) 0.2808(3) 0.2332(2) 0.094(3) Uani ?
C(12) 0.3765(2) 0.4821(4) 0.3085(3) 0.049(3) Uani ?
C(13) 0.3287(2) 0.5686(5) 0.2861(3) 0.058(3) Uani ?
C(14) 0.3432(3) 0.7014(5) 0.3172(3) 0.065(3) Uani ?
C(15) 0.4053(3) 0.7500(5) 0.3706(3) 0.066(4) Uani ?
C(16) 0.4533(2) 0.6600(6) 0.3964(3) 0.069(3) Uani ?
C(17) 0.4396(2) 0.5271(5) 0.3654(3) 0.058(3) Uani ?
C(18) 0.4208(3) 0.8968(5) 0.4008(4) 0.116(5) Uani ?
H(1) 0.4369 0.3820 0.2087 0.066 Uiso calc
H(3a) 0.2849 0.4944 0.0912 0.077 Uiso calc
H(3b) 0.2493 0.3610 0.0323 0.077 Uiso calc
H(4) 0.2243 0.5581 -0.1276 0.091 Uiso calc
H(5) 0.2723 0.7520 -0.1038 0.094 Uiso calc
H(6) 0.3907 0.6941 -0.0096 0.082 Uiso calc
H(7a) 0.3802 0.6149 0.1420 0.065 Uiso calc
H(7b) 0.4434 0.6053 0.1524 0.065 Uiso calc
H(8a) 0.3656 0.9126 0.0106 0.135 Uiso calc
H(8b) 0.3611 0.8566 0.0951 0.135 Uiso calc
H(8c) 0.4280 0.8612 0.1152 0.135 Uiso calc
H(9a) 0.4308 0.1515 0.1739 0.097 Uiso calc
H(9b) 0.3792 0.1800 0.0564 0.097 Uiso calc
H(9c) 0.4508 0.2272 0.1135 0.097 Uiso calc
H(10) 0.3946 0.4373 0.0252 0.060 Uiso calc
H(11) 0.2917 0.3663 -0.0532 0.069 Uiso calc
H(13) 0.2852 0.5363 0.2491 0.070 Uiso calc
H(14) 0.3096 0.7620 0.3014 0.078 Uiso calc
H(16) 0.4972 0.6910 0.4374 0.083 Uiso calc
H(17) 0.4734 0.4665 0.3818 0.069 Uiso calc
H(18a) 0.4588 0.9034 0.4708 0.140 Uiso calc
H(18b) 0.4284 0.9412 0.3573 0.140 Uiso calc
H(18c) 0.3852 0.9393 0.3935 0.140 Uiso calc

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C(1) 0.058(3) 0.054(3) 0.051(3) -0.010(2) 0.033(3) -0.007(2)
N(2) 0.063(2) 0.061(2) 0.052(2) -0.016(2) 0.038(2) -0.008(2)
C(3) 0.049(3) 0.089(4) 0.052(3) -0.024(3) 0.029(3) -0.018(3)
C(4) 0.052(3) 0.117(5) 0.044(3) 0.009(4) 0.023(3) 0.010(4)
C(5) 0.081(5) 0.097(5) 0.065(3) 0.028(4) 0.048(4) 0.028(3)
C(6) 0.077(4) 0.066(4) 0.075(3) 0.003(3) 0.054(3) 0.011(3)
C(7) 0.045(3) 0.061(3) 0.056(3) -0.004(2) 0.031(2) 0.001(3)
C(8) 0.135(5) 0.064(4) 0.141(5) -0.002(5) 0.085(5) 0.011(4)
C(9) 0.100(4) 0.069(4) 0.086(3) 0.008(3) 0.062(3) -0.003(3)
C(10) 0.052(3) 0.059(3) 0.044(3) -0.008(2) 0.032(2) -0.007(2)
C(11) 0.049(3) 0.080(4) 0.042(3) -0.012(3) 0.026(3) -0.013(3)
S 0.095(1) 0.0632(9) 0.0624(8) -0.0200(9) 0.0533(8) -0.0065(8)
O(1) 0.129(3) 0.061(2) 0.076(2) 0.017(2) 0.060(2) 0.022(2)
O(2) 0.114(3) 0.106(3) 0.095(3) -0.062(2) 0.081(2) -0.033(2)
C(12) 0.047(3) 0.064(3) 0.035(2) -0.004(3) 0.024(2) 0.000(2)
C(13) 0.045(3) 0.083(4) 0.044(3) -0.010(3) 0.026(2) -0.005(3)
C(14) 0.067(4) 0.074(4) 0.051(3) 0.016(3) 0.035(3) 0.006(3)
C(15) 0.082(4) 0.062(4) 0.053(3) -0.012(4) 0.041(3) -0.010(3)
C(16) 0.056(3) 0.090(4) 0.052(3) -0.021(3) 0.028(3) -0.015(3)
C(17) 0.046(3) 0.073(4) 0.043(3) 0.005(3) 0.021(3) 0.000(3)
C(18) 0.173(6) 0.077(4) 0.112(5) -0.021(4) 0.093(5) -0.019(4)

_refine_special_details          
;
Difference maps showed peaks at reasonable positions for the hydrogen atoms.
Calculated hydrogen positions were used for structure refinement with
isotropic temperature factors fixed at 1.2 times the refined values for
the carbons atoms.
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      'w = 1/(\s^2^(F) + 0.0003F^2^)'
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     'no extinction correction used'
_refine_ls_number_reflns         1346
_refine_ls_number_parameters     190
_refine_ls_R_factor_obs          0.0528
_refine_ls_wR_factor_obs         0.0481
_refine_ls_wR_factor_all         0.0763
_refine_ls_goodness_of_fit_ref   1.371
_refine_ls_shift/esd_max         <0.0005
_refine_diff_density_min         -0.24
_refine_diff_density_max         0.26

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C(1) N(2) 1.488(8)
C(1) C(9) 1.524(7)
C(1) C(10) 1.526(6)
N(2) C(3) 1.481(5)
N(2) S 1.624(5)
C(3) C(11) 1.525(9)
C(4) C(5) 1.295(9)
C(4) C(11) 1.488(7)
C(5) C(6) 1.500(7)
C(6) C(7) 1.524(6)
C(6) C(8) 1.530(7)
C(7) C(10) 1.518(6)
C(10) C(11) 1.527(6)
S O(1) 1.439(4)
S O(2) 1.430(5)
S C(12) 1.765(5)
C(12) C(13) 1.366(8)
C(12) C(17) 1.382(7)
C(13) C(14) 1.379(7)
C(14) C(15) 1.375(8)
C(15) C(16) 1.378(9)
C(15) C(18) 1.511(7)
C(16) C(17) 1.378(8)

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N(2) C(1) C(9) 110.1(4)
N(2) C(1) C(10) 104.3(3)
C(9) C(1) C(10) 113.6(5)
C(1) N(2) C(3) 110.6(4)
C(1) N(2) S 119.9(2)
C(3) N(2) S 118.3(4)
N(2) C(3) C(11) 103.7(4)
C(5) C(4) C(11) 123.5(4)
C(4) C(5) C(6) 124.7(5)
C(5) C(6) C(7) 109.8(5)
C(5) C(6) C(8) 112.2(5)
C(7) C(6) C(8) 111.7(4)
C(6) C(7) C(10) 111.8(3)
C(1) C(10) C(7) 112.9(3)
C(1) C(10) C(11) 104.2(4)
C(7) C(10) C(11) 110.3(4)
C(3) C(11) C(4) 113.4(5)
C(3) C(11) C(10) 103.3(3)
C(4) C(11) C(10) 113.5(4)
N(2) S O(1) 107.1(3)
N(2) S O(2) 106.3(2)
N(2) S C(12) 105.9(2)
O(1) S O(2) 121.3(2)
O(1) S C(12) 108.0(2)
O(2) S C(12) 107.3(3)
S C(12) C(13) 120.8(3)
S C(12) C(17) 119.2(4)
C(13) C(12) C(17) 119.7(4)
C(12) C(13) C(14) 120.0(5)
C(13) C(14) C(15) 121.4(6)
C(14) C(15) C(16) 117.8(5)
C(14) C(15) C(18) 121.5(6)
C(16) C(15) C(18) 120.7(5)
C(15) C(16) C(17) 121.5(5)
C(12) C(17) C(16) 119.4(5)

#==END