# Electronic Supplementary Material (ESI) for ChemComm.
# 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_ic16752

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N2 O2 S'
_chemical_formula_weight         348.41

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'
O O 0.0106 0.0060 '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   P2(1)/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                   7.2225(5)
_cell_length_b                   8.1395(6)
_cell_length_c                   27.359(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.373(2)
_cell_angle_gamma                90.00
_cell_volume                     1607.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3607
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      26.15

_exptl_crystal_description       rod
_exptl_crystal_colour            light-yellow
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8895
_exptl_absorpt_correction_T_max  0.9743
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11985
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3696
_reflns_number_gt                3148
_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)+(0.0555P)²+0.6011P] 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         3696
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
S1 S 0.61213(6) 0.73928(5) 0.152402(15) 0.02972(14) Uani 1 1 d . . .
O1 O 0.54585(18) 0.90133(15) 0.14072(5) 0.0373(3) Uani 1 1 d . . .
O2 O 0.49033(18) 0.62686(16) 0.17569(5) 0.0383(3) Uani 1 1 d . . .
N1 N 0.6754(2) 0.72527(17) 0.00765(5) 0.0291(3) Uani 1 1 d . . .
N2 N 0.6826(2) 0.66790(18) 0.10095(5) 0.0325(3) Uani 1 1 d . . .
H2 H 0.663(3) 0.728(3) 0.0756(9) 0.054(7) Uiso 1 1 d . . .
C1 C 0.6407(2) 0.8212(2) -0.03094(7) 0.0338(4) Uani 1 1 d . . .
H1 H 0.6061 0.9320 -0.0252 0.041 Uiso 1 1 calc R . .
C2 C 0.6521(3) 0.7693(2) -0.07893(7) 0.0382(4) Uani 1 1 d . . .
H2A H 0.6248 0.8420 -0.1053 0.046 Uiso 1 1 calc R . .
C3 C 0.7039(3) 0.6101(3) -0.08728(7) 0.0389(4) Uani 1 1 d . . .
H3 H 0.7136 0.5712 -0.1199 0.047 Uiso 1 1 calc R . .
C4 C 0.7423(2) 0.5051(2) -0.04811(6) 0.0314(4) Uani 1 1 d . . .
C5 C 0.7982(3) 0.3385(2) -0.05551(7) 0.0375(4) Uani 1 1 d . . .
H5 H 0.8093 0.2971 -0.0878 0.045 Uiso 1 1 calc R . .
C6 C 0.8349(3) 0.2404(2) -0.01706(7) 0.0373(4) Uani 1 1 d . . .
H6 H 0.8743 0.1309 -0.0228 0.045 Uiso 1 1 calc R . .
C7 C 0.8168(2) 0.2948(2) 0.03225(7) 0.0306(4) Uani 1 1 d . . .
C8 C 0.8491(3) 0.1858(2) 0.07118(7) 0.0366(4) Uani 1 1 d . . .
H8 H 0.8841 0.0756 0.0646 0.044 Uiso 1 1 calc R . .
C9 C 0.8308(3) 0.2365(2) 0.11855(7) 0.0378(4) Uani 1 1 d . . .
H9 H 0.8542 0.1616 0.1446 0.045 Uiso 1 1 calc R . .
C10 C 0.7782(3) 0.3966(2) 0.12876(7) 0.0348(4) Uani 1 1 d . . .
H10 H 0.7673 0.4308 0.1618 0.042 Uiso 1 1 calc R . .
C11 C 0.7414(2) 0.5067(2) 0.09134(6) 0.0282(4) Uani 1 1 d . . .
C12 C 0.7611(2) 0.4595(2) 0.04155(6) 0.0265(3) Uani 1 1 d . . .
C13 C 0.7258(2) 0.5662(2) 0.00013(6) 0.0258(3) Uani 1 1 d . . .
C14 C 0.8126(2) 0.7572(2) 0.18995(6) 0.0289(4) Uani 1 1 d . . .
C15 C 0.8164(3) 0.6936(2) 0.23681(6) 0.0367(4) Uani 1 1 d . . .
H15 H 0.7123 0.6364 0.2488 0.044 Uiso 1 1 calc R . .
C16 C 0.9750(3) 0.7146(3) 0.26616(7) 0.0400(4) Uani 1 1 d . . .
H16 H 0.9781 0.6720 0.2985 0.048 Uiso 1 1 calc R . .
C17 C 1.1281(3) 0.7967(2) 0.24891(7) 0.0357(4) Uani 1 1 d . . .
C18 C 1.1216(3) 0.8572(2) 0.20148(7) 0.0349(4) Uani 1 1 d . . .
H18 H 1.2263 0.9127 0.1892 0.042 Uiso 1 1 calc R . .
C19 C 0.9657(3) 0.8381(2) 0.17192(6) 0.0315(4) Uani 1 1 d . . .
H19 H 0.9631 0.8800 0.1395 0.038 Uiso 1 1 calc R . .
C20 C 1.2999(3) 0.8191(3) 0.28053(8) 0.0488(5) Uani 1 1 d . . .
H20A H 1.3105 0.9344 0.2905 0.073 Uiso 1 1 calc R . .
H20B H 1.4090 0.7879 0.2620 0.073 Uiso 1 1 calc R . .
H20C H 1.2920 0.7495 0.3096 0.073 Uiso 1 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
S1 0.0337(2) 0.0280(2) 0.0275(2) -0.00329(16) 0.00161(16) 0.00357(17)
O1 0.0435(8) 0.0316(7) 0.0367(7) -0.0046(5) -0.0003(6) 0.0100(6)
O2 0.0367(7) 0.0398(7) 0.0386(7) -0.0018(6) 0.0052(6) -0.0035(6)
N1 0.0277(7) 0.0295(7) 0.0302(7) -0.0009(6) 0.0018(6) -0.0007(6)
N2 0.0457(9) 0.0265(7) 0.0252(7) -0.0016(6) 0.0001(6) 0.0060(6)
C1 0.0317(9) 0.0332(9) 0.0367(9) 0.0016(7) 0.0033(7) -0.0014(7)
C2 0.0388(10) 0.0453(11) 0.0304(9) 0.0068(8) 0.0008(8) -0.0072(8)
C3 0.0403(10) 0.0492(11) 0.0275(9) -0.0047(8) 0.0059(7) -0.0107(9)
C4 0.0248(8) 0.0380(10) 0.0314(9) -0.0063(7) 0.0040(7) -0.0072(7)
C5 0.0346(10) 0.0418(10) 0.0365(10) -0.0159(8) 0.0081(8) -0.0053(8)
C6 0.0311(9) 0.0317(9) 0.0492(11) -0.0151(8) 0.0062(8) -0.0006(7)
C7 0.0217(8) 0.0281(8) 0.0420(10) -0.0077(7) 0.0025(7) -0.0016(7)
C8 0.0320(10) 0.0262(8) 0.0515(11) -0.0043(8) 0.0000(8) 0.0049(7)
C9 0.0400(10) 0.0297(9) 0.0435(11) 0.0039(8) -0.0042(8) 0.0052(8)
C10 0.0400(10) 0.0334(9) 0.0308(9) -0.0009(7) -0.0023(7) 0.0032(8)
C11 0.0269(8) 0.0250(8) 0.0327(9) -0.0037(7) -0.0006(7) 0.0009(6)
C12 0.0191(8) 0.0268(8) 0.0336(8) -0.0053(7) 0.0010(6) -0.0026(6)
C13 0.0178(7) 0.0296(8) 0.0301(8) -0.0048(7) 0.0024(6) -0.0043(6)
C14 0.0343(9) 0.0267(8) 0.0258(8) -0.0036(6) 0.0014(7) 0.0033(7)
C15 0.0393(10) 0.0406(10) 0.0304(9) 0.0022(7) 0.0054(8) 0.0003(8)
C16 0.0475(11) 0.0473(11) 0.0252(9) 0.0016(8) 0.0017(8) 0.0075(9)
C17 0.0390(10) 0.0362(10) 0.0319(9) -0.0086(7) -0.0003(7) 0.0092(8)
C18 0.0336(10) 0.0328(9) 0.0385(10) -0.0021(8) 0.0046(7) 0.0016(7)
C19 0.0390(10) 0.0280(8) 0.0278(8) 0.0009(7) 0.0040(7) 0.0042(7)
C20 0.0434(12) 0.0641(14) 0.0385(11) -0.0096(10) -0.0055(9) 0.0072(10)

_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
S1 O2 1.4297(13) . ?
S1 O1 1.4365(13) . ?
S1 N2 1.6164(15) . ?
S1 C14 1.7615(18) . ?
N1 C1 1.332(2) . ?
N1 C13 1.362(2) . ?
N2 C11 1.405(2) . ?
C1 C2 1.384(3) . ?
C2 C3 1.369(3) . ?
C3 C4 1.394(3) . ?
C4 C13 1.418(2) . ?
C4 C5 1.430(3) . ?
C5 C6 1.342(3) . ?
C6 C7 1.429(3) . ?
C7 C8 1.401(3) . ?
C7 C12 1.424(2) . ?
C8 C9 1.370(3) . ?
C9 C10 1.388(2) . ?
C10 C11 1.382(2) . ?
C11 C12 1.426(2) . ?
C12 C13 1.446(2) . ?
C14 C15 1.382(2) . ?
C14 C19 1.388(2) . ?
C15 C16 1.393(3) . ?
C16 C17 1.384(3) . ?
C17 C18 1.388(3) . ?
C17 C20 1.507(3) . ?
C18 C19 1.379(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
O2 S1 O1 118.78(8) . . ?
O2 S1 N2 111.59(8) . . ?
O1 S1 N2 104.28(8) . . ?
O2 S1 C14 107.40(8) . . ?
O1 S1 C14 108.59(8) . . ?
N2 S1 C14 105.42(8) . . ?
C1 N1 C13 118.90(15) . . ?
C11 N2 S1 126.96(13) . . ?
N1 C1 C2 124.01(18) . . ?
C3 C2 C1 118.00(17) . . ?
C2 C3 C4 120.17(17) . . ?
C3 C4 C13 118.73(17) . . ?
C3 C4 C5 121.63(16) . . ?
C13 C4 C5 119.64(16) . . ?
C6 C5 C4 120.26(17) . . ?
C5 C6 C7 122.36(17) . . ?
C8 C7 C12 120.18(16) . . ?
C8 C7 C6 120.28(16) . . ?
C12 C7 C6 119.53(16) . . ?
C9 C8 C7 120.68(17) . . ?
C8 C9 C10 120.44(17) . . ?
C11 C10 C9 120.58(17) . . ?
C10 C11 N2 121.37(15) . . ?
C10 C11 C12 120.72(15) . . ?
N2 C11 C12 117.91(15) . . ?
C7 C12 C11 117.38(15) . . ?
C7 C12 C13 118.07(15) . . ?
C11 C12 C13 124.55(15) . . ?
N1 C13 C4 120.18(15) . . ?
N1 C13 C12 119.70(14) . . ?
C4 C13 C12 120.11(15) . . ?
C15 C14 C19 120.62(17) . . ?
C15 C14 S1 120.51(14) . . ?
C19 C14 S1 118.86(13) . . ?
C14 C15 C16 119.10(18) . . ?
C17 C16 C15 120.98(17) . . ?
C16 C17 C18 118.74(18) . . ?
C16 C17 C20 121.08(18) . . ?
C18 C17 C20 120.18(19) . . ?
C19 C18 C17 121.13(18) . . ?
C18 C19 C14 119.42(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 N1 0.86(2) 1.86(3) 2.594(2) 142(2) .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 1013475'
#######################################################################
#
#                 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_ic16664

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 N2'
_chemical_formula_weight         272.34

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   7.2642(8)
_cell_length_b                   11.9445(12)
_cell_length_c                   15.7830(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.804(3)
_cell_angle_gamma                90.00
_cell_volume                     1353.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    713
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      20.75

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9805
_exptl_absorpt_correction_T_max  0.9945
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 SMART APEXCCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8950
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_sigmaI/netI    0.0759
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3119
_reflns_number_gt                2040
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0494P)²+0.2118P] 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         3119
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1157
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.1487
_refine_ls_wR_factor_gt          0.1311
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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
N1 N 0.2331(3) 0.09503(16) 0.50985(12) 0.0276(5) Uani 1 1 d . . .
N2 N 0.2306(3) 0.03259(17) 0.67949(12) 0.0264(5) Uani 1 1 d . . .
H2 H 0.310(3) 0.028(2) 0.6398(16) 0.041(7) Uiso 1 1 d . . .
C1 C 0.3078(3) 0.0995(2) 0.43830(15) 0.0308(6) Uani 1 1 d . . .
H1 H 0.4267 0.0662 0.4387 0.037 Uiso 1 1 calc R . .
C2 C 0.2233(4) 0.1499(2) 0.36272(16) 0.0340(6) Uani 1 1 d . . .
H2A H 0.2845 0.1521 0.3137 0.041 Uiso 1 1 calc R . .
C3 C 0.0504(3) 0.1961(2) 0.36044(16) 0.0325(6) Uani 1 1 d . . .
H3 H -0.0102 0.2305 0.3094 0.039 Uiso 1 1 calc R . .
C4 C -0.0370(3) 0.19262(19) 0.43344(15) 0.0274(6) Uani 1 1 d . . .
C5 C -0.2180(3) 0.2371(2) 0.43544(16) 0.0310(6) Uani 1 1 d . . .
H5 H -0.2845 0.2710 0.3855 0.037 Uiso 1 1 calc R . .
C6 C -0.2964(3) 0.23151(19) 0.50766(16) 0.0303(6) Uani 1 1 d . . .
H6 H -0.4170 0.2624 0.5073 0.036 Uiso 1 1 calc R . .
C7 C -0.2037(3) 0.18072(19) 0.58448(15) 0.0266(5) Uani 1 1 d . . .
C8 C -0.2908(3) 0.1737(2) 0.65861(16) 0.0305(6) Uani 1 1 d . . .
H8 H -0.4115 0.2049 0.6574 0.037 Uiso 1 1 calc R . .
C9 C -0.2054(3) 0.12314(19) 0.73210(16) 0.0290(6) Uani 1 1 d . . .
H9 H -0.2664 0.1193 0.7811 0.035 Uiso 1 1 calc R . .
C10 C -0.0262(3) 0.07680(19) 0.73449(15) 0.0254(5) Uani 1 1 d . . .
C11 C 0.0605(3) 0.08497(18) 0.66094(15) 0.0248(5) Uani 1 1 d . . .
C12 C -0.0234(3) 0.13533(18) 0.58416(15) 0.0244(5) Uani 1 1 d . . .
C13 C 0.0607(3) 0.14114(19) 0.50757(15) 0.0251(5) Uani 1 1 d . . .
C14 C 0.2500(3) -0.00992(19) 0.76153(15) 0.0265(5) Uani 1 1 d . . .
C15 C 0.0961(3) 0.01551(19) 0.79723(15) 0.0264(5) Uani 1 1 d . . .
C16 C 0.0717(3) -0.0196(2) 0.88603(15) 0.0312(6) Uani 1 1 d . . .
H16A H -0.0508 -0.0566 0.8844 0.037 Uiso 1 1 calc R . .
H16B H 0.0744 0.0472 0.9233 0.037 Uiso 1 1 calc R . .
C17 C 0.2267(3) -0.1004(2) 0.92299(16) 0.0351(6) Uani 1 1 d . . .
H17A H 0.2343 -0.1028 0.9861 0.042 Uiso 1 1 calc R . .
H17B H 0.1952 -0.1765 0.9006 0.042 Uiso 1 1 calc R . .
C18 C 0.4152(3) -0.0670(2) 0.90086(15) 0.0333(6) Uani 1 1 d . . .
H18A H 0.5120 -0.1179 0.9303 0.040 Uiso 1 1 calc R . .
H18B H 0.4457 0.0100 0.9216 0.040 Uiso 1 1 calc R . .
C19 C 0.4162(3) -0.0721(2) 0.80431(15) 0.0301(6) Uani 1 1 d . . .
H19A H 0.5315 -0.0377 0.7900 0.036 Uiso 1 1 calc R . .
H19B H 0.4112 -0.1510 0.7847 0.036 Uiso 1 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 0.0285(10) 0.0275(11) 0.0280(11) -0.0020(9) 0.0078(9) -0.0020(9)
N2 0.0260(10) 0.0304(11) 0.0237(11) 0.0006(9) 0.0073(9) 0.0012(9)
C1 0.0315(13) 0.0296(14) 0.0329(15) -0.0062(12) 0.0105(11) -0.0065(11)
C2 0.0437(15) 0.0338(14) 0.0276(14) -0.0027(12) 0.0156(12) -0.0075(12)
C3 0.0413(14) 0.0290(14) 0.0258(14) 0.0007(11) 0.0006(11) -0.0085(11)
C4 0.0331(13) 0.0224(12) 0.0262(13) -0.0035(10) 0.0029(10) -0.0054(10)
C5 0.0339(13) 0.0255(13) 0.0306(14) 0.0022(11) -0.0050(11) -0.0006(11)
C6 0.0272(12) 0.0254(13) 0.0374(15) -0.0004(12) 0.0019(11) 0.0018(10)
C7 0.0283(12) 0.0212(12) 0.0298(14) -0.0023(11) 0.0023(10) -0.0012(10)
C8 0.0240(12) 0.0302(14) 0.0384(15) -0.0030(12) 0.0083(11) 0.0013(10)
C9 0.0307(13) 0.0259(13) 0.0329(15) -0.0028(11) 0.0123(11) -0.0005(11)
C10 0.0281(12) 0.0212(12) 0.0273(13) -0.0038(10) 0.0057(10) -0.0016(10)
C11 0.0234(12) 0.0227(12) 0.0286(13) -0.0025(10) 0.0056(10) -0.0013(9)
C12 0.0276(12) 0.0191(12) 0.0268(13) -0.0014(10) 0.0049(10) -0.0032(9)
C13 0.0266(12) 0.0213(12) 0.0273(13) -0.0031(10) 0.0040(10) -0.0056(10)
C14 0.0300(12) 0.0265(13) 0.0227(13) -0.0014(10) 0.0028(10) -0.0017(10)
C15 0.0311(12) 0.0232(12) 0.0253(13) -0.0027(10) 0.0054(10) -0.0032(10)
C16 0.0372(13) 0.0278(13) 0.0295(14) -0.0006(11) 0.0077(11) -0.0022(11)
C17 0.0415(15) 0.0366(15) 0.0272(14) 0.0048(12) 0.0054(11) -0.0003(12)
C18 0.0372(14) 0.0321(14) 0.0284(14) 0.0024(12) -0.0016(11) 0.0036(11)
C19 0.0286(12) 0.0310(13) 0.0304(14) 0.0026(11) 0.0036(10) 0.0010(11)

_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 1.327(3) . ?
N1 C13 1.363(3) . ?
N2 C11 1.375(3) . ?
N2 C14 1.378(3) . ?
C1 C2 1.392(3) . ?
C2 C3 1.367(3) . ?
C3 C4 1.399(3) . ?
C4 C13 1.413(3) . ?
C4 C5 1.423(3) . ?
C5 C6 1.351(3) . ?
C6 C7 1.429(3) . ?
C7 C8 1.415(3) . ?
C7 C12 1.418(3) . ?
C8 C9 1.369(3) . ?
C9 C10 1.409(3) . ?
C10 C11 1.407(3) . ?
C10 C15 1.427(3) . ?
C11 C12 1.406(3) . ?
C12 C13 1.437(3) . ?
C14 C15 1.361(3) . ?
C14 C19 1.489(3) . ?
C15 C16 1.499(3) . ?
C16 C17 1.529(3) . ?
C17 C18 1.517(3) . ?
C18 C19 1.526(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
C1 N1 C13 117.1(2) . . ?
C11 N2 C14 109.11(19) . . ?
N1 C1 C2 124.2(2) . . ?
C3 C2 C1 118.7(2) . . ?
C2 C3 C4 119.8(2) . . ?
C3 C4 C13 117.4(2) . . ?
C3 C4 C5 123.0(2) . . ?
C13 C4 C5 119.5(2) . . ?
C6 C5 C4 120.7(2) . . ?
C5 C6 C7 122.1(2) . . ?
C8 C7 C12 120.7(2) . . ?
C8 C7 C6 120.9(2) . . ?
C12 C7 C6 118.3(2) . . ?
C9 C8 C7 121.6(2) . . ?
C8 C9 C10 119.5(2) . . ?
C11 C10 C9 118.6(2) . . ?
C11 C10 C15 107.35(19) . . ?
C9 C10 C15 134.0(2) . . ?
N2 C11 C12 129.4(2) . . ?
N2 C11 C10 107.1(2) . . ?
C12 C11 C10 123.4(2) . . ?
C11 C12 C7 116.1(2) . . ?
C11 C12 C13 124.2(2) . . ?
C7 C12 C13 119.8(2) . . ?
N1 C13 C4 122.7(2) . . ?
N1 C13 C12 117.7(2) . . ?
C4 C13 C12 119.5(2) . . ?
C15 C14 N2 109.5(2) . . ?
C15 C14 C19 125.7(2) . . ?
N2 C14 C19 124.7(2) . . ?
C14 C15 C10 106.9(2) . . ?
C14 C15 C16 123.2(2) . . ?
C10 C15 C16 129.9(2) . . ?
C15 C16 C17 110.3(2) . . ?
C18 C17 C16 112.6(2) . . ?
C17 C18 C19 111.2(2) . . ?
C14 C19 C18 107.78(19) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 N1 0.92(2) 2.19(2) 2.782(3) 122(2) .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 1013476'
