# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_c2c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H19 N S'
_chemical_formula_weight         401.50

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   'C2/c  '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.0037(15)
_cell_length_b                   10.4097(6)
_cell_length_c                   15.2507(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.5990(10)
_cell_angle_gamma                90.00
_cell_volume                     4081.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    120
_cell_measurement_reflns_used    7583
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.56
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1680
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.8882
_exptl_absorpt_correction_T_max  0.9661
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11394
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         27.56
_reflns_number_total             4656
_reflns_number_gt                4253
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_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)+(0.0523P)²+4.4307P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4656
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1032
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
N1 N 0.93454(4) 0.52033(10) 0.25221(7) 0.0197(2) Uani 1 1 d . . .
S1 S 0.962454(12) 0.43397(3) 0.10134(2) 0.02332(10) Uani 1 1 d . . .
C6 C 0.86632(6) 0.73602(15) 0.39119(10) 0.0325(3) Uani 1 1 d . . .
H4 H 0.8619 0.7551 0.4505 0.039 Uiso 1 1 calc R . .
C5 C 0.84004(6) 0.80897(14) 0.32265(10) 0.0317(3) Uani 1 1 d . . .
H3 H 0.8196 0.8800 0.3360 0.038 Uiso 1 1 calc R . .
C20 C 0.84153(6) 0.86703(14) -0.26929(9) 0.0316(3) Uani 1 1 d . . .
H13 H 0.8389 0.9074 -0.3257 0.038 Uiso 1 1 calc R . .
C14 C 1.00895(6) 0.91138(15) 0.14079(10) 0.0307(3) Uani 1 1 d . . .
H9 H 1.0429 0.9006 0.1729 0.037 Uiso 1 1 calc R . .
C21 C 0.88849(6) 0.81561(14) -0.23042(9) 0.0292(3) Uani 1 1 d . . .
H14 H 0.9180 0.8203 -0.2602 0.035 Uiso 1 1 calc R . .
C19 C 0.79838(6) 0.85984(13) -0.22627(9) 0.0306(3) Uani 1 1 d . . .
H12 H 0.7661 0.8945 -0.2535 0.037 Uiso 1 1 calc R . .
C12 C 0.94216(6) 1.04778(13) 0.06663(9) 0.0287(3) Uani 1 1 d . . .
H7 H 0.9302 1.1311 0.0483 0.034 Uiso 1 1 calc R . .
C13 C 0.99146(6) 1.03263(14) 0.11431(9) 0.0289(3) Uani 1 1 d . . .
H8 H 1.0132 1.1053 0.1287 0.035 Uiso 1 1 calc R . .
C7 C 0.89899(6) 0.63554(15) 0.37512(9) 0.0275(3) Uani 1 1 d . . .
H5 H 0.9175 0.5863 0.4219 0.033 Uiso 1 1 calc R . .
C15 C 0.97700(5) 0.80518(13) 0.12050(9) 0.0265(3) Uani 1 1 d . . .
H10 H 0.9892 0.7222 0.1396 0.032 Uiso 1 1 calc R . .
C27 C 0.75106(5) 0.42807(13) -0.00796(10) 0.0269(3) Uani 1 1 d . . .
H18 H 0.7209 0.3904 -0.0409 0.032 Uiso 1 1 calc R . .
C26 C 0.76884(5) 0.38397(13) 0.07733(9) 0.0252(3) Uani 1 1 d . . .
H17 H 0.7512 0.3155 0.1013 0.030 Uiso 1 1 calc R . .
C4 C 0.84321(5) 0.77941(13) 0.23409(9) 0.0251(3) Uani 1 1 d . . .
H2 H 0.8244 0.8275 0.1870 0.030 Uiso 1 1 calc R . .
C18 C 0.80213(5) 0.80197(13) -0.14311(8) 0.0246(3) Uani 1 1 d . . .
H11 H 0.7725 0.7974 -0.1137 0.030 Uiso 1 1 calc R . .
C28 C 0.77665(5) 0.52658(13) -0.04591(9) 0.0237(3) Uani 1 1 d . . .
H19 H 0.7647 0.5552 -0.1046 0.028 Uiso 1 1 calc R . .
C11 C 0.91015(5) 0.94216(12) 0.04546(9) 0.0234(3) Uani 1 1 d . . .
H6 H 0.8765 0.9536 0.0125 0.028 Uiso 1 1 calc R . .
C22 C 0.89246(5) 0.75702(12) -0.14760(8) 0.0230(3) Uani 1 1 d . . .
H15 H 0.9247 0.7212 -0.1213 0.028 Uiso 1 1 calc R . .
C25 C 0.81233(5) 0.43928(12) 0.12793(9) 0.0218(3) Uani 1 1 d . . .
H16 H 0.8246 0.4097 0.1862 0.026 Uiso 1 1 calc R . .
C8 C 0.90297(5) 0.61140(12) 0.28717(8) 0.0200(2) Uani 1 1 d . . .
C17 C 0.84955(5) 0.75057(11) -0.10299(8) 0.0197(2) Uani 1 1 d . . .
C16 C 0.85469(5) 0.68643(11) -0.01540(8) 0.0180(2) Uani 1 1 d . . .
C23 C 0.82011(5) 0.58201(11) 0.00442(8) 0.0184(2) Uani 1 1 d . . .
C3 C 0.87456(5) 0.67827(11) 0.21741(8) 0.0182(2) Uani 1 1 d . . .
C24 C 0.83694(5) 0.53819(11) 0.09069(8) 0.0179(2) Uani 1 1 d . . .
C10 C 0.92720(5) 0.81889(12) 0.07243(7) 0.0179(2) Uani 1 1 d . . .
C1 C 0.92895(5) 0.52209(11) 0.16336(8) 0.0170(2) Uani 1 1 d . . .
C9 C 0.89109(5) 0.70918(11) 0.05649(7) 0.0171(2) Uani 1 1 d . . .
C2 C 0.88412(4) 0.61642(11) 0.13122(7) 0.0163(2) Uani 1 1 d . . .
H1 H 0.9586(7) 0.4716(17) 0.2848(12) 0.031(4) Uiso 1 1 d . . .


_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 C1 1.3411(15) . ?
N1 C8 1.4099(16) . ?
N1 H1 0.895(18) . ?
S1 C1 1.6557(13) . ?
C6 C7 1.392(2) . ?
C6 C5 1.387(2) . ?
C6 H4 0.9500 . ?
C5 C4 1.400(2) . ?
C5 H3 0.9500 . ?
C20 C21 1.383(2) . ?
C20 C19 1.384(2) . ?
C20 H13 0.9500 . ?
C14 C13 1.381(2) . ?
C14 C15 1.3898(19) . ?
C14 H9 0.9500 . ?
C21 C22 1.3925(18) . ?
C21 H14 0.9500 . ?
C19 C18 1.3943(18) . ?
C19 H12 0.9500 . ?
C12 C13 1.385(2) . ?
C12 C11 1.3877(18) . ?
C12 H7 0.9500 . ?
C13 H8 0.9500 . ?
C7 C8 1.3836(17) . ?
C7 H5 0.9500 . ?
C15 C10 1.3968(18) . ?
C15 H10 0.9500 . ?
C27 C26 1.392(2) . ?
C27 C28 1.3944(19) . ?
C27 H18 0.9500 . ?
C26 C25 1.3945(18) . ?
C26 H17 0.9500 . ?
C4 C3 1.3783(18) . ?
C4 H2 0.9500 . ?
C18 C17 1.3984(18) . ?
C18 H11 0.9500 . ?
C28 C23 1.3929(17) . ?
C28 H19 0.9500 . ?
C11 C10 1.3992(17) . ?
C11 H6 0.9500 . ?
C22 C17 1.3926(19) . ?
C22 H15 0.9500 . ?
C25 C24 1.3787(17) . ?
C25 H16 0.9500 . ?
C8 C3 1.3881(17) . ?
C17 C16 1.4815(16) . ?
C16 C9 1.3579(16) . ?
C16 C23 1.4705(17) . ?
C23 C24 1.3994(16) . ?
C3 C2 1.5172(16) . ?
C24 C2 1.5244(16) . ?
C10 C9 1.4755(16) . ?
C1 C2 1.5468(16) . ?
C9 C2 1.5251(15) . ?

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
C1 N1 C8 113.06(10) . . ?
C1 N1 H1 121.9(11) . . ?
C8 N1 H1 124.7(11) . . ?
C7 C6 C5 121.59(13) . . ?
C7 C6 H4 119.2 . . ?
C5 C6 H4 119.2 . . ?
C6 C5 C4 120.90(13) . . ?
C6 C5 H3 119.6 . . ?
C4 C5 H3 119.6 . . ?
C21 C20 C19 120.16(12) . . ?
C21 C20 H13 119.9 . . ?
C19 C20 H13 119.9 . . ?
C13 C14 C15 120.13(13) . . ?
C13 C14 H9 119.9 . . ?
C15 C14 H9 119.9 . . ?
C20 C21 C22 119.95(14) . . ?
C20 C21 H14 120.0 . . ?
C22 C21 H14 120.0 . . ?
C20 C19 C18 120.21(13) . . ?
C20 C19 H12 119.9 . . ?
C18 C19 H12 119.9 . . ?
C13 C12 C11 120.52(13) . . ?
C13 C12 H7 119.7 . . ?
C11 C12 H7 119.7 . . ?
C12 C13 C14 119.74(13) . . ?
C12 C13 H8 120.1 . . ?
C14 C13 H8 120.1 . . ?
C8 C7 C6 116.31(13) . . ?
C8 C7 H5 121.8 . . ?
C6 C7 H5 121.8 . . ?
C10 C15 C14 120.80(13) . . ?
C10 C15 H10 119.6 . . ?
C14 C15 H10 119.6 . . ?
C26 C27 C28 121.21(12) . . ?
C26 C27 H18 119.4 . . ?
C28 C27 H18 119.4 . . ?
C27 C26 C25 120.64(12) . . ?
C27 C26 H17 119.7 . . ?
C25 C26 H17 119.7 . . ?
C3 C4 C5 117.89(13) . . ?
C3 C4 H2 121.1 . . ?
C5 C4 H2 121.1 . . ?
C17 C18 C19 120.03(13) . . ?
C17 C18 H11 120.0 . . ?
C19 C18 H11 120.0 . . ?
C27 C28 C23 118.30(12) . . ?
C27 C28 H19 120.9 . . ?
C23 C28 H19 120.9 . . ?
C12 C11 C10 120.36(12) . . ?
C12 C11 H6 119.8 . . ?
C10 C11 H6 119.8 . . ?
C17 C22 C21 120.54(13) . . ?
C17 C22 H15 119.7 . . ?
C21 C22 H15 119.7 . . ?
C24 C25 C26 117.93(12) . . ?
C24 C25 H16 121.0 . . ?
C26 C25 H16 121.0 . . ?
C7 C8 C3 122.93(12) . . ?
C7 C8 N1 128.38(12) . . ?
C3 C8 N1 108.69(10) . . ?
C22 C17 C18 119.10(11) . . ?
C22 C17 C16 119.44(11) . . ?
C18 C17 C16 121.44(12) . . ?
C9 C16 C23 109.68(10) . . ?
C9 C16 C17 127.40(11) . . ?
C23 C16 C17 122.89(10) . . ?
C28 C23 C24 119.80(12) . . ?
C28 C23 C16 131.58(11) . . ?
C24 C23 C16 108.62(10) . . ?
C4 C3 C8 120.21(12) . . ?
C4 C3 C2 131.46(11) . . ?
C8 C3 C2 108.29(10) . . ?
C25 C24 C23 122.11(11) . . ?
C25 C24 C2 128.82(11) . . ?
C23 C24 C2 109.07(10) . . ?
C15 C10 C11 118.44(12) . . ?
C15 C10 C9 121.64(11) . . ?
C11 C10 C9 119.70(11) . . ?
N1 C1 C2 106.95(10) . . ?
N1 C1 S1 125.65(9) . . ?
C2 C1 S1 127.35(9) . . ?
C16 C9 C10 128.14(11) . . ?
C16 C9 C2 110.28(10) . . ?
C10 C9 C2 120.72(10) . . ?
C3 C2 C24 110.60(10) . . ?
C3 C2 C9 115.59(10) . . ?
C24 C2 C9 102.33(9) . . ?
C3 C2 C1 102.02(9) . . ?
C24 C2 C1 108.19(9) . . ?
C9 C2 C1 118.07(10) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.081
_database_code_depnum_ccdc_archive 'CCDC 995430'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2621

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 N O'
_chemical_formula_weight         211.25

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   P2(1)/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                   10.8131(16)
_cell_length_b                   6.5022(10)
_cell_length_c                   16.577(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.352(2)
_cell_angle_gamma                90.00
_cell_volume                     1123.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    291
_cell_measurement_reflns_used    1646
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      25.91

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9737
_exptl_absorpt_correction_T_max  0.9969
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      291
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6089
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2526
_reflns_number_gt                1683
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1000P)²+0.6403P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2526
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0659
_refine_ls_wR_factor_ref         0.1829
_refine_ls_wR_factor_gt          0.1605
_refine_ls_goodness_of_fit_ref   0.895
_refine_ls_restrained_S_all      0.895
_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 0.5711(2) 1.2471(4) 0.96044(14) 0.0411(5) Uani 1 1 d . . .
C2 C 0.5823(2) 1.0408(3) 0.92328(13) 0.0388(5) Uani 1 1 d . . .
C3 C 0.4700(2) 1.0258(3) 0.85062(13) 0.0406(5) Uani 1 1 d . . .
C4 C 0.4254(2) 0.8722(4) 0.79236(15) 0.0503(6) Uani 1 1 d . . .
C5 C 0.3143(3) 0.9086(5) 0.72910(17) 0.0593(7) Uani 1 1 d . . .
C6 C 0.2503(3) 1.0940(5) 0.72418(17) 0.0603(7) Uani 1 1 d . . .
C7 C 0.2931(2) 1.2489(4) 0.78187(16) 0.0527(6) Uani 1 1 d . . .
C8 C 0.4029(2) 1.2105(3) 0.84471(13) 0.0420(5) Uani 1 1 d . . .
C9 C 0.6715(2) 0.8918(4) 0.94940(15) 0.0437(5) Uani 1 1 d . . .
C10 C 0.7889(2) 0.8805(4) 1.01608(15) 0.0469(6) Uani 1 1 d . . .
C11 C 0.8536(3) 0.7025(5) 1.0318(2) 0.0647(8) Uani 1 1 d . . .
C12 C 0.9717(3) 0.7168(6) 1.1024(2) 0.0805(10) Uani 1 1 d . . .
C13 C 0.9814(3) 0.9430(6) 1.1240(3) 0.0795(10) Uani 1 1 d . . .
C14 C 0.8564(3) 1.0443(5) 1.07455(19) 0.0591(7) Uani 1 1 d . . .
H1 H 0.435(2) 1.447(5) 0.9265(17) 0.064(8) Uiso 1 1 d . . .
H4 H 0.475(2) 0.741(4) 0.7943(16) 0.061(7) Uiso 1 1 d . . .
H5 H 0.282(3) 0.804(4) 0.6884(17) 0.065(8) Uiso 1 1 d . . .
H6 H 0.179(2) 1.115(4) 0.6821(16) 0.048(7) Uiso 1 1 d . . .
H7 H 0.251(3) 1.378(5) 0.7797(17) 0.068(8) Uiso 1 1 d . . .
H9 H 0.656(2) 0.771(4) 0.9161(14) 0.043(6) Uiso 1 1 d . . .
H11 H 0.823(3) 0.587(5) 1.0014(19) 0.075(10) Uiso 1 1 d . . .
H12A H 1.044(4) 0.669(6) 1.084(2) 0.115(13) Uiso 1 1 d . . .
H13A H 1.050(4) 1.005(6) 1.104(3) 0.120(14) Uiso 1 1 d . . .
H14A H 0.870(3) 1.171(6) 1.043(2) 0.099(11) Uiso 1 1 d . . .
H12B H 0.961(4) 0.634(7) 1.152(3) 0.132(16) Uiso 1 1 d . . .
H13B H 0.997(3) 0.966(6) 1.183(3) 0.114(14) Uiso 1 1 d . . .
H14B H 0.805(3) 1.099(5) 1.1098(18) 0.074(9) Uiso 1 1 d . . .
N1 N 0.46595(19) 1.3398(3) 0.90980(12) 0.0454(5) Uani 1 1 d . . .
O1 O 0.63862(16) 1.3234(3) 1.02465(11) 0.0565(5) Uani 1 1 d . . .


_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 O1 1.225(3) . ?
C1 N1 1.362(3) . ?
C1 C2 1.494(3) . ?
C2 C9 1.355(3) . ?
C2 C3 1.470(3) . ?
C3 C4 1.384(3) . ?
C3 C8 1.393(3) . ?
C4 C5 1.390(4) . ?
C4 H4 1.00(3) . ?
C5 C6 1.382(4) . ?
C5 H5 0.96(3) . ?
C6 C7 1.382(4) . ?
C6 H6 0.91(3) . ?
C7 C8 1.379(3) . ?
C7 H7 0.95(3) . ?
C8 N1 1.395(3) . ?
C9 C10 1.448(3) . ?
C9 H9 0.95(3) . ?
C10 C11 1.342(4) . ?
C10 C14 1.494(4) . ?
C11 C12 1.490(5) . ?
C11 H11 0.92(3) . ?
C12 C13 1.511(6) . ?
C12 H12A 0.96(4) . ?
C12 H12B 1.01(5) . ?
C13 C14 1.532(4) . ?
C13 H13A 0.98(4) . ?
C13 H13B 0.95(4) . ?
C14 H14A 1.01(4) . ?
C14 H14B 0.97(3) . ?
N1 H1 0.85(3) . ?

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
O1 C1 N1 124.4(2) . . ?
O1 C1 C2 128.9(2) . . ?
N1 C1 C2 106.74(19) . . ?
C9 C2 C3 125.3(2) . . ?
C9 C2 C1 129.7(2) . . ?
C3 C2 C1 104.97(18) . . ?
C4 C3 C8 119.6(2) . . ?
C4 C3 C2 132.8(2) . . ?
C8 C3 C2 107.60(19) . . ?
C3 C4 C5 118.4(2) . . ?
C3 C4 H4 120.4(15) . . ?
C5 C4 H4 121.2(15) . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6(17) . . ?
C4 C5 H5 119.6(17) . . ?
C7 C6 C5 121.6(2) . . ?
C7 C6 H6 119.0(16) . . ?
C5 C6 H6 119.4(16) . . ?
C8 C7 C6 117.0(3) . . ?
C8 C7 H7 119.7(17) . . ?
C6 C7 H7 123.3(17) . . ?
C7 C8 C3 122.5(2) . . ?
C7 C8 N1 128.4(2) . . ?
C3 C8 N1 109.04(19) . . ?
C2 C9 C10 133.4(2) . . ?
C2 C9 H9 113.6(14) . . ?
C10 C9 H9 113.0(14) . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 C14 110.5(2) . . ?
C9 C10 C14 129.6(2) . . ?
C10 C11 C12 113.1(3) . . ?
C10 C11 H11 121(2) . . ?
C12 C11 H11 126.2(19) . . ?
C11 C12 C13 103.8(3) . . ?
C11 C12 H12A 109(2) . . ?
C13 C12 H12A 112(2) . . ?
C11 C12 H12B 110(3) . . ?
C13 C12 H12B 110(3) . . ?
H12A C12 H12B 111(3) . . ?
C12 C13 C14 107.2(3) . . ?
C12 C13 H13A 109(2) . . ?
C14 C13 H13A 106(2) . . ?
C12 C13 H13B 112(3) . . ?
C14 C13 H13B 112(2) . . ?
H13A C13 H13B 110(3) . . ?
C10 C14 C13 104.5(3) . . ?
C10 C14 H14A 111(2) . . ?
C13 C14 H14A 113(2) . . ?
C10 C14 H14B 112.8(18) . . ?
C13 C14 H14B 113.5(17) . . ?
H14A C14 H14B 102(3) . . ?
C1 N1 C8 111.57(19) . . ?
C1 N1 H1 120.0(18) . . ?
C8 N1 H1 126.2(18) . . ?

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
O1 C1 C2 C9 -2.7(4) . . . . ?
N1 C1 C2 C9 179.0(2) . . . . ?
O1 C1 C2 C3 175.4(2) . . . . ?
N1 C1 C2 C3 -2.9(2) . . . . ?
C9 C2 C3 C4 -0.3(4) . . . . ?
C1 C2 C3 C4 -178.6(2) . . . . ?
C9 C2 C3 C8 -179.7(2) . . . . ?
C1 C2 C3 C8 2.0(2) . . . . ?
C8 C3 C4 C5 0.2(3) . . . . ?
C2 C3 C4 C5 -179.1(2) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C7 -0.6(4) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
C6 C7 C8 C3 0.6(4) . . . . ?
C6 C7 C8 N1 179.6(2) . . . . ?
C4 C3 C8 C7 -0.8(3) . . . . ?
C2 C3 C8 C7 178.7(2) . . . . ?
C4 C3 C8 N1 -180.0(2) . . . . ?
C2 C3 C8 N1 -0.5(2) . . . . ?
C3 C2 C9 C10 177.2(2) . . . . ?
C1 C2 C9 C10 -5.0(4) . . . . ?
C2 C9 C10 C11 174.2(3) . . . . ?
C2 C9 C10 C14 -6.2(5) . . . . ?
C9 C10 C11 C12 -179.8(3) . . . . ?
C14 C10 C11 C12 0.6(4) . . . . ?
C10 C11 C12 C13 -6.3(4) . . . . ?
C11 C12 C13 C14 9.2(4) . . . . ?
C11 C10 C14 C13 5.3(4) . . . . ?
C9 C10 C14 C13 -174.3(3) . . . . ?
C12 C13 C14 C10 -9.0(4) . . . . ?
O1 C1 N1 C8 -175.6(2) . . . . ?
C2 C1 N1 C8 2.8(2) . . . . ?
C7 C8 N1 C1 179.4(2) . . . . ?
C3 C8 N1 C1 -1.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 995431'
