# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2001

data_hm8

_database_code_CSD	163627

_journal_coden_Cambridge      188

_publ_requested_journal       'Perkin Transactions 2'

loop_
_publ_author_name
'Clegg, W.'
'Demirtas, Ibrahim'
'Elsegood, Mark R. J.'
'Maskill, H.'

_publ_contact_author_name     	'Dr H Maskill'  
_publ_contact_author_address 
;
Dr H Maskill
Department of Chemistry
University of Newcastle upon Tyne
Newcastle upon Tyne
NE1 7RU
England
;

_publ_contact_author_email       'H.MASKILL@NEWCASTLE.AC.UK'
_audit_creation_method            SHELXL
_chemical_name_systematic
;
?
;
_chemical_name_common             ?
_chemical_formula_moiety          ?
_chemical_formula_structural      ?
_chemical_formula_analytical      ?
_chemical_formula_sum
'C38 H31 N O'
_chemical_formula_weight          517.64
_chemical_melting_point           ?
_chemical_compound_source         ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C'  'C'   0.0181   0.0091
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H'  'H'   0.0000   0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N'  'N'   0.0311   0.0180
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O'  'O'   0.0492   0.0322
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting            triclinic
_symmetry_space_group_name_H-M    P-1

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

_cell_length_a                    8.677(6)
_cell_length_b                    9.042(6)
_cell_length_c                    10.769(7)
_cell_angle_alpha                 113.29(4)
_cell_angle_beta                  90.24(4)
_cell_angle_gamma                 115.20(3)
_cell_volume                      686.9(8)
_cell_formula_units_Z             1
_cell_measurement_temperature     160(2)
_cell_measurement_reflns_used     29
_cell_measurement_theta_min       20.06
_cell_measurement_theta_max       24.60

_exptl_crystal_description        'triangular prism'
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.27
_exptl_crystal_size_mid           0.23
_exptl_crystal_size_min           0.11
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.251
_exptl_crystal_density_method     ?
_exptl_crystal_F_000              274
_exptl_absorpt_coefficient_mu     0.570
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?

_exptl_special_details
;
?
;

_diffrn_ambient_temperature       160(2)
_diffrn_radiation_wavelength      1.54184
_diffrn_radiation_type            CuK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device        'Stoe-Siemens diffractometer'
_diffrn_measurement_method        '\w/\q scans with on-line profile fitting'
_diffrn_standards_number          5
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   60
_diffrn_standards_decay_%         0
_diffrn_reflns_number             4757
_diffrn_reflns_av_R_equivalents   0.0420
_diffrn_reflns_av_sigmaI/netI     0.0445
_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        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          4.57
_diffrn_reflns_theta_max          67.50
_reflns_number_total              2409
_reflns_number_observed           2074
_reflns_observed_criterion        >2sigma(I)

_computing_data_collection        'Stoe DIF4'
_computing_cell_refinement        'Stoe DIF4'
_computing_data_reduction         'local programs'
_computing_structure_solution     'Siemens SHELXTL'
_computing_structure_refinement   'Siemens SHELXTL'
_computing_molecular_graphics     'Siemens SHELXTL'
_computing_publication_material   'SHELXTL and local programs'

_refine_special_details
;
Refinement of F^2^ against ALL reflections.  Weighted R-factors wR and all
goodnesses 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 observed
criterion
of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0257P)^2^+0.2022P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    'geom except H1 coords freely refined'
_refine_ls_hydrogen_treatment     ?
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.0145(9)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns          2409
_refine_ls_number_parameters      185
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0444
_refine_ls_R_factor_obs           0.0370
_refine_ls_wR_factor_all          0.0947
_refine_ls_wR_factor_obs          0.0885
_refine_ls_goodness_of_fit_all    1.070
_refine_ls_goodness_of_fit_obs    1.084
_refine_ls_restrained_S_all       1.071
_refine_ls_restrained_S_obs       1.085
_refine_ls_shift/esd_max          0.000
_refine_ls_shift/esd_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
N1_a N 0.41604(13) 0.41996(13) 0.47468(12) 0.0300(3) Uani 0.50 d PD 1
H1_a H 0.344(4) 0.455(5) 0.516(4) 0.045 Uiso 0.50 d PD 1
O1_b O 0.41604(13) 0.41996(13) 0.47468(12) 0.0300(3) Uani 0.50 d P 2
C1 C 0.34475(16) 0.37154(17) 0.33209(14) 0.0224(3) Uani 1 d . .
C2 C 0.17401(16) 0.19470(17) 0.29424(14) 0.0228(3) Uani 1 d . .
C3 C 0.0709(2) 0.1759(2) 0.39102(17) 0.0357(4) Uani 1 d . .
H3 H 0.1063 0.2728 0.4813 0.043 Uiso 1 calc R .
C4 C -0.0832(2) 0.0168(2) 0.35717(18) 0.0394(4) Uani 1 d . .
H4 H -0.1521 0.0058 0.4245 0.047 Uiso 1 calc R .
C5 C -0.13663(18) -0.1247(2) 0.22664(18) 0.0354(4) Uani 1 d . .
H5 H -0.2417 -0.2335 0.2038 0.043 Uiso 1 calc R .
C6 C -0.03688(18) -0.10755(19) 0.12961(17) 0.0327(4) Uani 1 d . .
H6 H -0.0735 -0.2046 0.0393 0.039 Uiso 1 calc R .
C7 C 0.11785(17) 0.05155(18) 0.16302(15) 0.0266(3) Uani 1 d . .
H7 H 0.1856 0.0620 0.0950 0.032 Uiso 1 calc R .
C8 C 0.46990(16) 0.33176(16) 0.24073(15) 0.0253(3) Uani 1 d . .
C9 C 0.48733(18) 0.36352(18) 0.12418(16) 0.0304(3) Uani 1 d . .
H9 H 0.4249 0.4178 0.1027 0.036 Uiso 1 calc R .
C10 C 0.5949(2) 0.3170(2) 0.03863(19) 0.0408(4) Uani 1 d . .
H10 H 0.6060 0.3403 -0.0404 0.049 Uiso 1 calc R .
C11 C 0.6853(2) 0.2373(2) 0.0680(2) 0.0473(5) Uani 1 d . .
H11 H 0.7595 0.2064 0.0099 0.057 Uiso 1 calc R .
C12 C 0.66759(19) 0.2025(2) 0.1823(2) 0.0464(5) Uani 1 d . .
H12 H 0.7287 0.1461 0.2022 0.056 Uiso 1 calc R .
C13 C 0.56093(18) 0.24942(19) 0.26841(19) 0.0353(4) Uani 1 d . .
H13 H 0.5499 0.2252 0.3470 0.042 Uiso 1 calc R .
C14 C 0.30965(16) 0.52119(17) 0.32392(14) 0.0224(3) Uani 1 d . .
C15 C 0.14238(18) 0.49515(19) 0.29152(17) 0.0325(4) Uani 1 d . .
H15 H 0.0457 0.3821 0.2744 0.039 Uiso 1 calc R .
C16 C 0.1135(2) 0.6315(2) 0.28366(19) 0.0404(4) Uani 1 d . .
H16 H -0.0021 0.6108 0.2614 0.048 Uiso 1 calc R .
C17 C 0.2524(2) 0.7970(2) 0.30804(17) 0.0353(4) Uani 1 d . .
H17 H 0.2330 0.8903 0.3028 0.042 Uiso 1 calc R .
C18 C 0.41921(19) 0.82461(19) 0.34008(16) 0.0309(3) Uani 1 d . .
H18 H 0.5152 0.9382 0.3574 0.037 Uiso 1 calc R .
C19 C 0.44895(18) 0.68933(18) 0.34738(15) 0.0275(3) Uani 1 d . .
H19 H 0.5651 0.7106 0.3685 0.033 Uiso 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
N1_a 0.0271(6) 0.0220(5) 0.0294(7) 0.0126(5) -0.0076(5) 0.0006(5)
O1_b 0.0271(6) 0.0220(5) 0.0294(7) 0.0126(5) -0.0076(5) 0.0006(5)
C1 0.0227(6) 0.0189(6) 0.0227(7) 0.0102(5) -0.0012(5) 0.0062(5)
C2 0.0228(6) 0.0204(6) 0.0256(8) 0.0125(6) 0.0004(5) 0.0084(5)
C3 0.0413(8) 0.0304(8) 0.0279(9) 0.0124(7) 0.0091(7) 0.0107(7)
C4 0.0359(8) 0.0412(9) 0.0420(10) 0.0263(8) 0.0158(7) 0.0113(7)
C5 0.0240(7) 0.0298(8) 0.0471(10) 0.0215(7) 0.0021(7) 0.0039(6)
C6 0.0274(7) 0.0240(7) 0.0341(9) 0.0079(6) -0.0029(6) 0.0058(6)
C7 0.0238(6) 0.0248(7) 0.0283(8) 0.0115(6) 0.0037(6) 0.0091(6)
C8 0.0188(6) 0.0165(6) 0.0326(8) 0.0087(6) -0.0005(5) 0.0033(5)
C9 0.0291(7) 0.0260(7) 0.0333(9) 0.0109(6) 0.0052(6) 0.0125(6)
C10 0.0398(8) 0.0343(8) 0.0420(10) 0.0128(7) 0.0151(7) 0.0154(7)
C11 0.0333(8) 0.0335(8) 0.0670(13) 0.0131(8) 0.0197(8) 0.0167(7)
C12 0.0271(7) 0.0319(8) 0.0815(15) 0.0239(9) 0.0091(8) 0.0158(7)
C13 0.0244(7) 0.0277(7) 0.0550(11) 0.0221(7) 0.0039(7) 0.0095(6)
C14 0.0270(6) 0.0215(6) 0.0196(7) 0.0097(5) 0.0048(5) 0.0113(5)
C15 0.0277(7) 0.0287(7) 0.0426(10) 0.0176(7) 0.0073(6) 0.0126(6)
C16 0.0354(8) 0.0408(9) 0.0547(11) 0.0230(8) 0.0083(7) 0.0242(7)
C17 0.0491(9) 0.0301(8) 0.0370(9) 0.0169(7) 0.0108(7) 0.0252(7)
C18 0.0405(8) 0.0234(7) 0.0288(8) 0.0137(6) 0.0052(6) 0.0127(6)
C19 0.0275(7) 0.0245(7) 0.0293(8) 0.0139(6) 0.0015(6) 0.0092(6)

_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
N1_a N1_a 1.445(2) 2_666 ?
N1_a C1 1.470(2) . ?
C1 C8 1.529(2) . ?
C1 C14 1.5416(19) . ?
C1 C2 1.543(2) . ?
C2 C7 1.386(2) . ?
C2 C3 1.390(2) . ?
C3 C4 1.391(2) . ?
C4 C5 1.377(3) . ?
C5 C6 1.373(2) . ?
C6 C7 1.394(2) . ?
C8 C9 1.389(2) . ?
C8 C13 1.393(2) . ?
C9 C10 1.390(2) . ?
C10 C11 1.377(3) . ?
C11 C12 1.380(3) . ?
C12 C13 1.388(2) . ?
C14 C15 1.387(2) . ?
C14 C19 1.402(2) . ?
C15 C16 1.391(2) . ?
C16 C17 1.382(2) . ?
C17 C18 1.377(2) . ?
C18 C19 1.383(2) . ?

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_a N1_a C1 110.25(13) 2_666 . ?
N1_a C1 C8 108.67(12) . . ?
N1_a C1 C14 111.61(11) . . ?
C8 C1 C14 112.19(11) . . ?
N1_a C1 C2 102.55(11) . . ?
C8 C1 C2 109.94(12) . . ?
C14 C1 C2 111.43(11) . . ?
C7 C2 C3 118.17(13) . . ?
C7 C2 C1 121.21(13) . . ?
C3 C2 C1 120.61(13) . . ?
C2 C3 C4 120.77(15) . . ?
C5 C4 C3 120.35(16) . . ?
C6 C5 C4 119.54(14) . . ?
C5 C6 C7 120.35(15) . . ?
C2 C7 C6 120.81(14) . . ?
C9 C8 C13 118.26(14) . . ?
C9 C8 C1 122.00(12) . . ?
C13 C8 C1 119.59(14) . . ?
C8 C9 C10 120.89(14) . . ?
C11 C10 C9 120.22(17) . . ?
C10 C11 C12 119.63(16) . . ?
C11 C12 C13 120.36(15) . . ?
C12 C13 C8 120.64(16) . . ?
C15 C14 C19 117.68(13) . . ?
C15 C14 C1 122.14(12) . . ?
C19 C14 C1 120.17(12) . . ?
C14 C15 C16 121.24(13) . . ?
C17 C16 C15 120.32(15) . . ?
C18 C17 C16 119.07(14) . . ?
C17 C18 C19 120.94(13) . . ?
C18 C19 C14 120.74(14) . . ?

_refine_diff_density_max    0.255
_refine_diff_density_min   -0.154
_refine_diff_density_rms    0.034