# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2000
# CCDC Number: 188/227

data_product_3

_audit_creation_method              ?
_publ_requested_journal           'Perkin Transactions'
_chemical_name_systematic
;
2(ax)-benzoyloxy-3(ax)-(1,1,3,3-tetramethyl-2,3-dihydro-isoindol-2-ylo
xy)-trans-
decalin
;
_chemical_formula_moiety          'C29 H37 N O3'
_chemical_formula_sum             'C29 H37 N O3'
_chemical_formula_weight          111.90

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'

_symmetry_cell_setting            monoclinic
_symmetry_space_group_name_H-M    'P 1 2~1~/n 1 '

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                    14.904(6)
_cell_length_b                    10.0510(10)
_cell_length_c                    17.289(9)
_cell_angle_alpha                 90.00
_cell_angle_beta                  98.12(2)
_cell_angle_gamma                 90.00
_cell_volume                      2563.9(17)
_cell_formula_units_Z             4
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     25
_cell_measurement_theta_min       6
_cell_measurement_theta_max       14

_exptl_crystal_description        prism
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.36
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       'none'
_exptl_crystal_density_diffrn     1.160
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              968
_exptl_absorpt_coefficient_mu     0.7
_exptl_absorpt_correction_type    'none'
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?

_exptl_special_details            ?

_diffrn_ambient_temperature       296(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   'Enraf-Nonius CAD-4'
_diffrn_measurement_method        2\q/\w
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          3
_diffrn_standards_interval_count  200
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         1
_diffrn_reflns_number             4984
_diffrn_reflns_av_R_equivalents   ?
_diffrn_reflns_av_sigmaI/netI     ?
_diffrn_reflns_limit_h_min        0
_diffrn_reflns_limit_h_max        17
_diffrn_reflns_limit_k_min        0
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          1.0
_diffrn_reflns_theta_max          25.0
_reflns_number_total              4500
_reflns_number_gt                 1928
_reflns_threshold_expression      I>2.5\s(Io)

_computing_data_collection        'MolEN (Fair,1990)'
_computing_cell_refinement        'MolEN (Fair,1990)'
_computing_data_reduction         'MolEN (Fair,1990)'
_computing_structure_solution     'SHELXS-86(Sheldrick, 1986)'
_computing_structure_refinement   'SHELX-76(Sheldrick, 1976)'
_computing_molecular_graphics      ?
_computing_publication_material    ?

_refine_special_details           ?

_refine_ls_structure_factor_coef  F
_refine_ls_matrix_type            blocked
_refine_ls_weighting_scheme
 'calc w=1/[\s^2^(Fo)+0.002542xF^2^]'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    difmap
_refine_ls_hydrogen_treatment     refall
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_extinction_expression  ?
_refine_ls_number_reflns          4500
_refine_ls_number_parameters      446
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           ?
_refine_ls_R_factor_gt            0.040
_refine_ls_wR_factor_ref          ?
_refine_ls_wR_factor_gt           0.044
_refine_ls_goodness_of_fit_ref    ?
_refine_ls_restrained_S_all       0.95
_refine_ls_shift/su_max           0.16
_refine_ls_shift/su_mean          0.05

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_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O 0.03543(15) 0.1918(2) 0.33195(12) 0.0456(8) Uani 1 d . . .
O2 O 0.06297(16) 0.2929(3) 0.53419(12) 0.0517(9) Uani 1 d . . .
O3 O -0.08011(18) 0.3650(3) 0.50460(15) 0.0733(11) Uani 1 d . . .
N1 N -0.00854(18) 0.0848(3) 0.28586(15) 0.0423(10) Uani 1 d . . .
C2 C -0.1077(2) 0.1140(4) 0.2600(2) 0.0497(14) Uani 1 d . . .
C211 C -0.1312(4) 0.2607(5) 0.2459(4) 0.076(2) Uani 1 d . . .
C212 C -0.1632(3) 0.0583(7) 0.3208(3) 0.076(2) Uani 1 d . . .
C3 C -0.1211(3) 0.0350(4) 0.18543(19) 0.0475(14) Uani 1 d . . .
C4 C -0.2016(3) -0.0128(4) 0.1439(3) 0.0622(17) Uani 1 d . . .
C5 C -0.1982(4) -0.0841(5) 0.0757(3) 0.0705(19) Uani 1 d . . .
C6 C -0.1171(4) -0.1073(5) 0.0503(3) 0.0710(19) Uani 1 d . . .
C7 C -0.0369(3) -0.0616(4) 0.0912(2) 0.0608(17) Uani 1 d . . .
C8 C -0.0393(3) 0.0094(4) 0.1598(2) 0.0464(14) Uani 1 d . . .
C9 C 0.0384(3) 0.0655(4) 0.2154(2) 0.0489(12) Uani 1 d . . .
C911 C 0.0754(5) 0.1937(6) 0.1835(3) 0.078(2) Uani 1 d . . .
C912 C 0.1134(3) -0.0369(6) 0.2358(3) 0.074(2) Uani 1 d . . .
C10 C 0.0395(3) 0.1648(4) 0.41414(19) 0.0441(14) Uani 1 d . . .
C11 C 0.0985(3) 0.0466(4) 0.4414(3) 0.0472(16) Uani 1 d . . .
C12 C 0.1999(2) 0.0699(4) 0.4407(2) 0.0432(12) Uani 1 d . . .
C13 C 0.2562(3) -0.0514(4) 0.4717(3) 0.0592(17) Uani 1 d . . .
C14 C 0.3569(3) -0.0278(5) 0.4723(3) 0.0695(19) Uani 1 d . . .
C15 C 0.3881(3) 0.0980(5) 0.5161(3) 0.077(2) Uani 1 d . . .
C16 C 0.3325(3) 0.2176(5) 0.4847(3) 0.0644(17) Uani 1 d . . .
C17 C 0.2315(2) 0.1954(4) 0.4851(2) 0.0468(12) Uani 1 d . . .
C18 C 0.1750(3) 0.3132(4) 0.4507(3) 0.0492(16) Uani 1 d . . .
C19 C 0.0752(3) 0.2950(4) 0.4517(2) 0.0466(14) Uani 1 d . . .
C20 C -0.0160(3) 0.3366(4) 0.5527(2) 0.0513(14) Uani 1 d . . .
C21 C -0.0152(3) 0.3497(4) 0.6383(2) 0.0486(14) Uani 1 d . . .
C22 C 0.0621(3) 0.3225(4) 0.6910(2) 0.0578(17) Uani 1 d . . .
C23 C 0.0612(3) 0.3393(5) 0.7701(3) 0.0731(19) Uani 1 d . . .
C24 C -0.0154(4) 0.3851(5) 0.7971(3) 0.081(2) Uani 1 d . . .
C25 C -0.0919(4) 0.4126(5) 0.7452(3) 0.080(2) Uani 1 d . . .
C26 C -0.0923(3) 0.3930(4) 0.6666(3) 0.0669(17) Uani 1 d . . .
H21 H -0.194(3) 0.279(5) 0.227(2) 0.094(15) Uiso 1 d . . .
H22 H -0.096(3) 0.297(4) 0.206(2) 0.075(14) Uiso 1 d . . .
H23 H -0.112(3) 0.309(5) 0.291(3) 0.106(18) Uiso 1 d . . .
H24 H -0.155(3) 0.118(4) 0.368(3) 0.092(15) Uiso 1 d . . .
H25 H -0.139(3) -0.032(5) 0.334(2) 0.080(17) Uiso 1 d . . .
H26 H -0.227(3) 0.056(4) 0.297(2) 0.081(13) Uiso 1 d . . .
H41 H -0.258(3) 0.011(4) 0.164(2) 0.084(15) Uiso 1 d . . .
H51 H -0.257(3) -0.114(4) 0.047(2) 0.084(14) Uiso 1 d . . .
H61 H -0.116(3) -0.148(4) 0.006(3) 0.071(14) Uiso 1 d . . .
H71 H 0.021(3) -0.077(4) 0.075(2) 0.056(11) Uiso 1 d . . .
H91 H 0.105(3) 0.177(5) 0.146(3) 0.101(19) Uiso 1 d . . .
H92 H 0.024(4) 0.261(6) 0.169(3) 0.13(2) Uiso 1 d . . .
H93 H 0.124(3) 0.232(5) 0.224(3) 0.100(17) Uiso 1 d . . .
H94 H 0.143(3) -0.059(4) 0.192(3) 0.084(14) Uiso 1 d . . .
H95 H 0.163(3) 0.000(4) 0.270(3) 0.085(15) Uiso 1 d . . .
H96 H 0.089(3) -0.119(5) 0.263(3) 0.102(18) Uiso 1 d . . .
H101 H -0.021(2) 0.149(3) 0.4292(17) 0.041(9) Uiso 1 d . . .
H111 H 0.0910(19) 0.027(3) 0.4945(19) 0.033(9) Uiso 1 d . . .
H112 H 0.079(2) -0.029(3) 0.4096(18) 0.044(10) Uiso 1 d . . .
H121 H 0.2069(19) 0.081(3) 0.3869(19) 0.035(9) Uiso 1 d . . .
H131 H 0.234(2) -0.135(4) 0.439(2) 0.063(11) Uiso 1 d . . .
H132 H 0.241(3) -0.075(4) 0.526(3) 0.093(15) Uiso 1 d . . .
H141 H 0.393(3) -0.102(4) 0.500(2) 0.075(13) Uiso 1 d . . .
H142 H 0.371(3) -0.021(4) 0.416(3) 0.075(13) Uiso 1 d . . .
H151 H 0.457(3) 0.116(4) 0.514(2) 0.082(13) Uiso 1 d . . .
H152 H 0.379(2) 0.087(4) 0.573(2) 0.067(13) Uiso 1 d . . .
H161 H 0.343(3) 0.238(4) 0.432(2) 0.068(14) Uiso 1 d . . .
H171 H 0.221(2) 0.180(3) 0.543(2) 0.048(9) Uiso 1 d . . .
H181 H 0.186(3) 0.329(4) 0.395(3) 0.080(13) Uiso 1 d . . .
H182 H 0.192(2) 0.397(4) 0.4773(19) 0.050(10) Uiso 1 d . . .
H191 H 0.036(2) 0.368(3) 0.4264(18) 0.046(10) Uiso 1 d . . .
H221 H 0.116(3) 0.289(4) 0.672(2) 0.071(13) Uiso 1 d . . .
H231 H 0.120(3) 0.315(4) 0.806(2) 0.083(13) Uiso 1 d . . .
H241 H -0.012(3) 0.396(5) 0.851(3) 0.094(16) Uiso 1 d . . .
H251 H -0.146(3) 0.445(4) 0.765(2) 0.083(14) Uiso 1 d . . .
H261 H -0.143(2) 0.419(3) 0.630(2) 0.051(11) Uiso 1 d . . .

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
O1 0.0529(15) 0.0442(15) 0.0390(14) -0.0033(12) 0.0040(11) -0.0069(12)
O2 0.0493(16) 0.0648(17) 0.0401(14) -0.0076(12) 0.0033(11) 0.0149(13)
O3 0.0533(17) 0.103(2) 0.0609(18) -0.0017(16) -0.0012(14) 0.0237(17)
N1 0.0437(17) 0.0423(18) 0.0402(16) -0.0038(13) 0.0036(13) -0.0012(15)
C2 0.042(2) 0.059(3) 0.047(2) 0.0030(18) 0.0021(17) 0.0038(19)
C211 0.074(4) 0.072(4) 0.077(4) -0.010(3) -0.002(3) 0.025(3)
C212 0.049(3) 0.117(5) 0.062(3) -0.009(3) 0.012(2) -0.009(3)
C3 0.053(3) 0.047(2) 0.040(2) 0.0040(17) -0.0026(18) 0.0021(19)
C4 0.059(3) 0.065(3) 0.058(3) 0.005(2) -0.008(2) 0.001(2)
C5 0.081(4) 0.061(3) 0.061(3) 0.005(2) -0.019(3) -0.015(3)
C6 0.105(4) 0.058(3) 0.043(3) -0.004(2) -0.014(3) -0.004(3)
C7 0.070(3) 0.060(3) 0.052(3) -0.001(2) 0.007(2) 0.004(2)
C8 0.060(3) 0.041(2) 0.038(2) -0.0016(17) 0.0067(18) -0.001(2)
C9 0.050(2) 0.054(2) 0.044(2) -0.0080(18) 0.0107(18) -0.002(2)
C911 0.088(4) 0.091(4) 0.062(3) -0.010(3) 0.033(3) -0.036(4)
C912 0.055(3) 0.101(5) 0.064(3) -0.027(3) 0.003(3) 0.010(3)
C10 0.045(2) 0.050(3) 0.037(2) 0.0042(17) 0.0049(16) 0.001(2)
C11 0.052(3) 0.046(3) 0.043(2) 0.006(2) 0.0045(19) -0.008(2)
C12 0.048(2) 0.045(2) 0.037(2) 0.0043(17) 0.0078(17) -0.0011(18)
C13 0.055(3) 0.052(3) 0.071(3) 0.011(2) 0.010(2) 0.007(2)
C14 0.055(3) 0.068(3) 0.087(4) 0.004(3) 0.015(3) 0.013(2)
C15 0.047(3) 0.092(4) 0.091(4) -0.011(3) 0.007(3) 0.008(3)
C16 0.055(3) 0.059(3) 0.080(3) -0.017(3) 0.012(2) -0.009(2)
C17 0.039(2) 0.052(2) 0.050(2) -0.004(2) 0.0086(17) -0.0007(19)
C18 0.054(3) 0.037(2) 0.056(3) -0.010(2) 0.0055(19) -0.005(2)
C19 0.050(2) 0.048(3) 0.041(2) -0.0016(18) 0.0039(17) 0.003(2)
C20 0.052(3) 0.050(2) 0.051(2) -0.0030(19) 0.004(2) 0.008(2)
C21 0.056(3) 0.040(2) 0.051(2) -0.0028(18) 0.0121(19) 0.0070(19)
C22 0.059(3) 0.063(3) 0.051(3) -0.005(2) 0.006(2) 0.002(2)
C23 0.076(3) 0.090(4) 0.053(3) -0.003(2) 0.008(3) -0.004(3)
C24 0.109(5) 0.079(4) 0.057(3) -0.008(3) 0.022(3) -0.002(3)
C25 0.093(4) 0.087(4) 0.068(4) -0.001(3) 0.039(3) 0.027(3)
C26 0.070(3) 0.065(3) 0.068(3) 0.008(2) 0.018(3) 0.029(2)

_geom_special_details             ?

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
O1 N1 1.440(4) . ?
O1 C10 1.440(4) . ?
O2 C19 1.463(4) . ?
O2 C20 1.337(5) . ?
O3 C20 1.209(5) . ?
N1 C2 1.511(4) . ?
N1 C9 1.501(5) . ?
C2 C3 1.503(5) . ?
C2 C211 1.527(7) . ?
C2 C212 1.532(6) . ?
C3 C4 1.394(6) . ?
C3 C8 1.379(6) . ?
C4 C5 1.387(7) . ?
C5 C6 1.363(8) . ?
C6 C7 1.379(7) . ?
C7 C8 1.389(5) . ?
C8 C9 1.506(6) . ?
C9 C91 1.534(7) . ?
C9 C92 1.524(7) . ?
C10 C11 1.513(6) . ?
C10 C19 1.523(6) . ?
C11 C12 1.531(6) . ?
C12 C13 1.533(6) . ?
C12 C17 1.517(5) . ?
C13 C14 1.518(6) . ?
C14 C15 1.513(7) . ?
C15 C16 1.516(7) . ?
C16 C17 1.523(6) . ?
C17 C18 1.524(6) . ?
C18 C19 1.501(6) . ?
C20 C21 1.484(5) . ?
C23 C24 1.372(7) . ?
C23 C22 1.380(6) . ?
C24 C25 1.376(8) . ?
C25 C26 1.372(7) . ?
C26 C21 1.381(6) . ?
C21 C22 1.391(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
N1 O1 C10 111.0(2) . . ?
C19 O2 C20 117.6(3) . . ?
O1 N1 C2 111.6(3) . . ?
O1 N1 C9 108.5(3) . . ?
C2 N1 C9 109.5(3) . . ?
N1 C2 C3 99.0(3) . . ?
N1 C2 C211 115.3(3) . . ?
N1 C2 C212 109.0(3) . . ?
C3 C2 C211 111.9(4) . . ?
C3 C2 C212 112.1(4) . . ?
C211 C2 C212 109.2(4) . . ?
C2 C3 C4 128.6(4) . . ?
C2 C3 C8 111.0(3) . . ?
C4 C3 C8 120.4(4) . . ?
C3 C4 C5 118.9(4) . . ?
C4 C5 C6 120.2(5) . . ?
C5 C6 C7 121.4(5) . . ?
C6 C7 C8 119.0(4) . . ?
C3 C8 C7 120.1(4) . . ?
C3 C8 C9 111.1(3) . . ?
C7 C8 C9 128.8(4) . . ?
N1 C9 C8 99.3(3) . . ?
N1 C9 C91 114.6(4) . . ?
N1 C9 C92 108.1(3) . . ?
C8 C9 C91 111.6(3) . . ?
C8 C9 C92 111.6(4) . . ?
C91 C9 C92 111.2(4) . . ?
O1 C10 C11 113.4(3) . . ?
O1 C10 C19 102.8(3) . . ?
C11 C10 C19 112.9(3) . . ?
C10 C11 C12 114.1(3) . . ?
C11 C12 C13 111.6(3) . . ?
C11 C12 C17 111.1(3) . . ?
C13 C12 C17 111.7(3) . . ?
C12 C13 C14 111.7(3) . . ?
C13 C14 C15 111.6(4) . . ?
C14 C15 C16 111.7(4) . . ?
C15 C16 C17 111.9(4) . . ?
C12 C17 C16 110.9(3) . . ?
C12 C17 C18 109.5(3) . . ?
C16 C17 C18 112.1(3) . . ?
C17 C18 C19 113.2(3) . . ?
O2 C19 C10 108.6(3) . . ?
O2 C19 C18 105.8(3) . . ?
C10 C19 C18 112.8(4) . . ?
O2 C20 O3 123.4(3) . . ?
O2 C20 C21 112.6(3) . . ?
O3 C20 C21 124.0(4) . . ?
C24 C23 C22 120.2(5) . . ?
C23 C24 C25 119.9(5) . . ?
C24 C25 C26 120.3(5) . . ?
C25 C26 C21 120.6(4) . . ?
C20 C21 C26 119.4(4) . . ?
C20 C21 C22 121.7(4) . . ?
C26 C21 C22 118.9(4) . . ?
C23 C22 C21 120.1(4) . . ?

_diffrn_measured_fraction_theta_max    ?
_diffrn_reflns_theta_full              25.0
_diffrn_measured_fraction_theta_full   ?
_refine_diff_density_max               0.14
_refine_diff_density_min               -0.16
_refine_diff_density_rms               ?