# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 N2 O'
_chemical_formula_weight         264.32

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           orthorhombic
_symmetry_space_group_name_H-M   pbca

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

_cell_length_a                   10.802(2)
_cell_length_b                   8.0122(16)
_cell_length_c                   31.156(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2696.5(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    16819
_cell_measurement_theta_min      6.33
_cell_measurement_theta_max      55.02

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.000
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            22371
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3077
_reflns_number_gt                2457
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  SHELXL-97

_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)+(0.0811P)²+0.5673P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3077
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1440
_refine_ls_wR_factor_gt          0.1210
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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
O1 O 0.32389(9) 0.05232(14) 0.62578(3) 0.0251(3) Uani 1 1 d . . .
N2 N 0.50277(11) -0.04930(17) 0.65297(4) 0.0248(3) Uani 1 1 d . . .
N1 N 0.40991(13) -0.3476(2) 0.37572(4) 0.0323(3) Uani 1 1 d . . .
C1 C 0.31377(16) -0.3115(3) 0.34457(5) 0.0352(4) Uani 1 1 d . . .
H1C H 0.2357 -0.3513 0.3551 0.053 Uiso 1 1 calc R . .
H1B H 0.3328 -0.3661 0.3180 0.053 Uiso 1 1 calc R . .
H1A H 0.3092 -0.1932 0.3400 0.053 Uiso 1 1 calc RD . .
C2 C 0.39314(16) 0.1806(2) 0.75011(5) 0.0312(4) Uani 1 1 d . . .
H2A H 0.4123 0.2080 0.7783 0.037 Uiso 1 1 calc R . .
C3 C 0.50680(17) -0.4616(2) 0.36323(5) 0.0344(4) Uani 1 1 d . . .
H3C H 0.5857 -0.4157 0.3711 0.052 Uiso 1 1 calc R . .
H3B H 0.5040 -0.4784 0.3327 0.052 Uiso 1 1 calc R . .
H3A H 0.4952 -0.5664 0.3776 0.052 Uiso 1 1 calc R . .
C4 C 0.44269(13) 0.04444(19) 0.68454(5) 0.0230(3) Uani 1 1 d . . .
C5 C 0.47468(15) 0.0823(2) 0.72680(5) 0.0288(4) Uani 1 1 d . . .
H5A H 0.5479 0.0432 0.7389 0.035 Uiso 1 1 calc R . .
C6 C 0.28281(16) 0.2394(2) 0.73220(5) 0.0316(4) Uani 1 1 d . . .
H6A H 0.2308 0.3059 0.7487 0.038 Uiso 1 1 calc R . .
C7 C 0.30743(13) -0.1737(2) 0.42845(5) 0.0258(3) Uani 1 1 d . . .
H7A H 0.2497 -0.1401 0.4081 0.031 Uiso 1 1 calc RD . .
C8 C 0.37212(14) -0.0907(2) 0.54491(5) 0.0256(3) Uani 1 1 d . . .
H8A H 0.3033 -0.0238 0.5500 0.031 Uiso 1 1 calc R . .
C9 C 0.44965(14) -0.1128(2) 0.57803(5) 0.0247(3) Uani 1 1 d . . .
H9A H 0.5193 -0.1791 0.5739 0.030 Uiso 1 1 calc R . .
C10 C 0.24906(15) 0.2008(2) 0.69034(5) 0.0287(4) Uani 1 1 d . . .
H10A H 0.1750 0.2372 0.6784 0.034 Uiso 1 1 calc R . .
C11 C 0.48617(14) -0.3349(2) 0.44904(5) 0.0257(3) Uani 1 1 d . . .
H11A H 0.5492 -0.4098 0.4425 0.031 Uiso 1 1 calc R . .
C12 C 0.40125(13) -0.2873(2) 0.41675(5) 0.0239(3) Uani 1 1 d . . .
C13 C 0.47712(13) -0.2723(2) 0.49005(5) 0.0259(3) Uani 1 1 d . . .
H13A H 0.5347 -0.3057 0.5105 0.031 Uiso 1 1 calc R . .
C14 C 0.33242(13) 0.1052(2) 0.66773(5) 0.0238(3) Uani 1 1 d . . .
C16 C 0.43090(13) -0.03959(19) 0.61962(5) 0.0242(3) Uani 1 1 d . . .
C17 C 0.30017(13) -0.1119(2) 0.46969(5) 0.0255(3) Uani 1 1 d . . .
H17A H 0.2379 -0.0361 0.4764 0.031 Uiso 1 1 calc R . .
C18 C 0.38393(13) -0.1598(2) 0.50192(5) 0.0232(3) 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
O1 C14 1.3771(18) . ?
O1 C16 1.3838(18) . ?
N2 C16 1.299(2) . ?
N2 C4 1.397(2) . ?
N1 C12 1.370(2) . ?
N1 C3 1.442(2) . ?
N1 C1 1.451(2) . ?
C2 C5 1.387(2) . ?
C2 C6 1.398(3) . ?
C4 C14 1.389(2) . ?
C4 C5 1.395(2) . ?
C6 C10 1.389(2) . ?
C7 C17 1.379(2) . ?
C7 C12 1.410(2) . ?
C8 C9 1.341(2) . ?
C8 C18 1.455(2) . ?
C9 C16 1.437(2) . ?
C10 C14 1.376(2) . ?
C11 C13 1.376(2) . ?
C11 C12 1.414(2) . ?
C13 C18 1.401(2) . ?
C17 C18 1.405(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
C14 O1 C16 103.86(11) . . ?
C16 N2 C4 104.66(13) . . ?
C12 N1 C3 121.66(13) . . ?
C12 N1 C1 120.33(14) . . ?
C3 N1 C1 117.73(14) . . ?
C5 C2 C6 121.59(15) . . ?
C14 C4 C5 119.47(14) . . ?
C14 C4 N2 108.75(13) . . ?
C5 C4 N2 131.78(14) . . ?
C2 C5 C4 117.43(15) . . ?
C10 C6 C2 121.58(15) . . ?
C17 C7 C12 120.89(14) . . ?
C9 C8 C18 127.11(15) . . ?
C8 C9 C16 123.51(14) . . ?
C14 C10 C6 115.64(15) . . ?
C13 C11 C12 121.06(14) . . ?
N1 C12 C7 121.21(14) . . ?
N1 C12 C11 121.62(14) . . ?
C7 C12 C11 117.17(14) . . ?
C11 C13 C18 122.07(14) . . ?
C10 C14 O1 127.84(13) . . ?
C10 C14 C4 124.28(14) . . ?
O1 C14 C4 107.88(13) . . ?
N2 C16 O1 114.84(13) . . ?
N2 C16 C9 127.77(14) . . ?
O1 C16 C9 117.39(13) . . ?
C7 C17 C18 122.07(14) . . ?
C13 C18 C17 116.73(14) . . ?
C13 C18 C8 123.45(14) . . ?
C17 C18 C8 119.82(14) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 994905'
#######################################################################
#
#                 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_c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H20 N2 O'
_chemical_formula_weight         388.45

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   P21/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                   8.1562(16)
_cell_length_b                   14.302(3)
_cell_length_c                   16.983(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.22(3)
_cell_angle_gamma                90.00
_cell_volume                     1965.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.000
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18837
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4490
_reflns_number_gt                3386
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0512P)²+0.3208P] 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         4490
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
O1 O 0.03769(11) 0.32733(7) 0.47703(6) 0.0273(2) Uani 1 1 d . . .
N1 N 1.01839(14) 0.19073(8) 0.68828(7) 0.0265(3) Uani 1 1 d . . .
N2 N 0.12143(14) 0.45683(8) 0.41721(7) 0.0286(3) Uani 1 1 d . . .
C1 C -0.25688(17) 0.32852(11) 0.41739(9) 0.0309(3) Uani 1 1 d . . .
H1A H -0.2878 0.2750 0.4428 0.037 Uiso 1 1 calc R . .
C2 C -0.36811(18) 0.37903(11) 0.36493(9) 0.0333(3) Uani 1 1 d . . .
H2A H -0.4773 0.3590 0.3552 0.040 Uiso 1 1 calc R . .
C3 C -0.15931(19) 0.49180(11) 0.33910(10) 0.0359(4) Uani 1 1 d . . .
H3A H -0.1275 0.5447 0.3130 0.043 Uiso 1 1 calc R . .
C4 C 1.10804(16) 0.24957(9) 0.74536(8) 0.0220(3) Uani 1 1 d . . .
C5 C 1.36562(17) 0.31664(10) 0.80431(9) 0.0284(3) Uani 1 1 d . . .
H5A H 1.4796 0.3220 0.8060 0.034 Uiso 1 1 calc R . .
C6 C 1.11570(18) 0.35567(10) 0.85610(9) 0.0302(3) Uani 1 1 d . . .
H6A H 1.0604 0.3886 0.8920 0.036 Uiso 1 1 calc R . .
C7 C -0.32027(18) 0.45874(12) 0.32672(10) 0.0364(4) Uani 1 1 d . . .
H7A H -0.3982 0.4906 0.2920 0.044 Uiso 1 1 calc R . .
C8 C 1.09953(15) 0.11049(9) 0.66127(8) 0.0227(3) Uani 1 1 d . . .
C9 C 0.81643(16) 0.30926(10) 0.63618(8) 0.0256(3) Uani 1 1 d . . .
H9A H 0.8954 0.3556 0.6485 0.031 Uiso 1 1 calc R . .
C10 C 0.73716(17) 0.14725(9) 0.63348(9) 0.0271(3) Uani 1 1 d . . .
H10A H 0.7621 0.0847 0.6441 0.033 Uiso 1 1 calc R . .
C11 C 1.18546(16) 0.05000(9) 0.71636(8) 0.0253(3) Uani 1 1 d . . .
H11A H 1.1845 0.0601 0.7704 0.030 Uiso 1 1 calc R . .
C12 C -0.04705(16) 0.44244(10) 0.39221(8) 0.0257(3) Uani 1 1 d . . .
C13 C 0.65948(17) 0.33357(10) 0.60206(8) 0.0254(3) Uani 1 1 d . . .
H13A H 0.6343 0.3963 0.5924 0.031 Uiso 1 1 calc R . .
C14 C 1.28556(18) 0.36524(10) 0.85868(9) 0.0309(3) Uani 1 1 d . . .
H14A H 1.3446 0.4037 0.8963 0.037 Uiso 1 1 calc R . .
C15 C 0.58005(17) 0.17223(10) 0.59887(9) 0.0272(3) Uani 1 1 d . . .
H15A H 0.5010 0.1259 0.5867 0.033 Uiso 1 1 calc R . .
C16 C 0.37239(16) 0.28876(10) 0.54204(8) 0.0255(3) Uani 1 1 d . . .
H16A H 0.2918 0.2427 0.5417 0.031 Uiso 1 1 calc R . .
C17 C 1.27880(16) 0.26020(9) 0.74755(8) 0.0252(3) Uani 1 1 d . . .
H17A H 1.3343 0.2292 0.7107 0.030 Uiso 1 1 calc R . .
C18 C 0.85803(16) 0.21555(9) 0.65248(8) 0.0234(3) Uani 1 1 d . . .
C19 C 1.18589(16) 0.01786(10) 0.55541(8) 0.0245(3) Uani 1 1 d . . .
H19A H 1.1855 0.0069 0.5014 0.029 Uiso 1 1 calc R . .
C20 C -0.09776(16) 0.36296(10) 0.42922(8) 0.0242(3) Uani 1 1 d . . .
C21 C 1.27200(16) -0.02495(10) 0.69075(9) 0.0269(3) Uani 1 1 d . . .
H21A H 1.3299 -0.0647 0.7277 0.032 Uiso 1 1 calc R . .
C22 C 0.16321(16) 0.38805(9) 0.46561(8) 0.0246(3) Uani 1 1 d . . .
C23 C 1.09885(16) 0.09380(9) 0.58060(8) 0.0232(3) Uani 1 1 d . . .
H23A H 1.0405 0.1332 0.5435 0.028 Uiso 1 1 calc R . .
C24 C 1.02736(16) 0.29769(10) 0.80076(8) 0.0255(3) Uani 1 1 d . . .
H24A H 0.9139 0.2908 0.8005 0.031 Uiso 1 1 calc R . .
C25 C 1.27284(16) -0.04125(9) 0.60998(9) 0.0262(3) Uani 1 1 d . . .
H25A H 1.3315 -0.0915 0.5929 0.031 Uiso 1 1 calc R . .
C26 C 0.32672(17) 0.36938(10) 0.50627(8) 0.0264(3) Uani 1 1 d . . .
H26A H 0.4052 0.4167 0.5075 0.032 Uiso 1 1 calc R . .
C27 C 0.53758(16) 0.26588(9) 0.58178(8) 0.0238(3) 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
O1 C22 1.3747(16) . ?
O1 C20 1.3835(17) . ?
N1 C4 1.4158(17) . ?
N1 C18 1.4165(17) . ?
N1 C8 1.4289(17) . ?
N2 C22 1.2996(18) . ?
N2 C12 1.4016(18) . ?
C1 C20 1.3791(19) . ?
C1 C2 1.391(2) . ?
C2 C7 1.392(2) . ?
C3 C7 1.386(2) . ?
C3 C12 1.394(2) . ?
C4 C24 1.3956(19) . ?
C4 C17 1.3969(18) . ?
C5 C17 1.382(2) . ?
C5 C14 1.383(2) . ?
C6 C24 1.386(2) . ?
C6 C14 1.387(2) . ?
C8 C23 1.3898(19) . ?
C8 C11 1.3966(19) . ?
C9 C13 1.3816(19) . ?
C9 C18 1.4016(19) . ?
C10 C15 1.388(2) . ?
C10 C18 1.3965(19) . ?
C11 C21 1.3833(19) . ?
C12 C20 1.3869(19) . ?
C13 C27 1.3994(19) . ?
C15 C27 1.4046(19) . ?
C16 C26 1.334(2) . ?
C16 C27 1.4661(19) . ?
C19 C25 1.383(2) . ?
C19 C23 1.3938(19) . ?
C21 C25 1.392(2) . ?
C22 C26 1.4476(19) . ?

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
C22 O1 C20 103.79(10) . . ?
C4 N1 C18 120.97(11) . . ?
C4 N1 C8 118.49(11) . . ?
C18 N1 C8 120.22(11) . . ?
C22 N2 C12 104.46(12) . . ?
C20 C1 C2 115.71(14) . . ?
C1 C2 C7 121.70(14) . . ?
C7 C3 C12 117.26(14) . . ?
C24 C4 C17 118.77(12) . . ?
C24 C4 N1 120.53(12) . . ?
C17 C4 N1 120.69(12) . . ?
C17 C5 C14 121.03(13) . . ?
C24 C6 C14 120.84(13) . . ?
C3 C7 C2 121.62(14) . . ?
C23 C8 C11 119.57(12) . . ?
C23 C8 N1 120.65(12) . . ?
C11 C8 N1 119.74(12) . . ?
C13 C9 C18 120.79(12) . . ?
C15 C10 C18 120.35(13) . . ?
C21 C11 C8 120.15(13) . . ?
C20 C12 C3 119.96(13) . . ?
C20 C12 N2 108.66(12) . . ?
C3 C12 N2 131.38(13) . . ?
C9 C13 C27 121.43(13) . . ?
C5 C14 C6 118.86(13) . . ?
C10 C15 C27 121.57(13) . . ?
C26 C16 C27 126.18(13) . . ?
C5 C17 C4 120.26(13) . . ?
C10 C18 C9 118.48(12) . . ?
C10 C18 N1 120.72(12) . . ?
C9 C18 N1 120.79(12) . . ?
C25 C19 C23 120.59(13) . . ?
C1 C20 O1 128.42(13) . . ?
C1 C20 C12 123.74(13) . . ?
O1 C20 C12 107.83(11) . . ?
C11 C21 C25 120.36(13) . . ?
N2 C22 O1 115.25(12) . . ?
N2 C22 C26 126.44(13) . . ?
O1 C22 C26 118.29(12) . . ?
C8 C23 C19 119.82(13) . . ?
C6 C24 C4 120.22(13) . . ?
C19 C25 C21 119.50(13) . . ?
C16 C26 C22 124.36(13) . . ?
C13 C27 C15 117.37(12) . . ?
C13 C27 C16 122.84(12) . . ?
C15 C27 C16 119.77(12) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 973275'
#######################################################################
#
#                 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_c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H18 N2 O S'
_chemical_formula_weight         370.45

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   P21/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                   13.690(3)
_cell_length_b                   21.558(4)
_cell_length_c                   6.2444(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.33(3)
_cell_angle_gamma                90.00
_cell_volume                     1834.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4310
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9755
_exptl_absorpt_correction_T_max  0.9792
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295
_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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.000
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17671
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4187
_reflns_number_gt                2909
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  SHELXL-97

_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)+(0.0686P)²+0.2787P] 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         4187
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1343
_refine_ls_wR_factor_gt          0.1214
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
S1 S 0.06403(4) 0.53828(3) 0.79973(10) 0.0543(2) Uani 1 1 d . . .
O1 O 0.27258(9) 0.40609(7) -0.1660(2) 0.0407(3) Uani 1 1 d . . .
N2 N 0.43750(12) 0.40564(8) -0.1685(3) 0.0415(4) Uani 1 1 d . . .
C1 C 0.04547(18) 0.71273(13) 1.1925(4) 0.0596(6) Uani 1 1 d . . .
H1A H 0.0411 0.7475 1.2794 0.072 Uiso 1 1 calc R . .
C2 C 0.43864(17) 0.33795(10) -0.5013(3) 0.0467(5) Uani 1 1 d . . .
H2A H 0.5063 0.3367 -0.5055 0.056 Uiso 1 1 calc R . .
C3 C -0.03877(17) 0.68339(12) 1.1086(4) 0.0574(6) Uani 1 1 d . . .
H3A H -0.1000 0.6981 1.1378 0.069 Uiso 1 1 calc R . .
C4 C 0.36517(18) 0.70150(11) 1.0030(4) 0.0516(6) Uani 1 1 d . . .
H4A H 0.4225 0.7153 1.0902 0.077 Uiso 1 1 calc R . .
H4B H 0.3155 0.7330 0.9997 0.077 Uiso 1 1 calc R . .
H4C H 0.3817 0.6936 0.8594 0.077 Uiso 1 1 calc R . .
C5 C 0.23108(17) 0.34200(11) -0.4918(3) 0.0497(6) Uani 1 1 d . . .
H5A H 0.1634 0.3438 -0.4884 0.060 Uiso 1 1 calc R . .
C6 C 0.3763(2) 0.30759(11) -0.6541(4) 0.0535(6) Uani 1 1 d . . .
H6A H 0.4027 0.2851 -0.7620 0.064 Uiso 1 1 calc R . .
C7 C 0.27504(19) 0.30992(11) -0.6498(4) 0.0536(6) Uani 1 1 d . . .
H7A H 0.2355 0.2893 -0.7563 0.064 Uiso 1 1 calc R . .
C8 C -0.03133(15) 0.63210(12) 0.9813(4) 0.0523(6) Uani 1 1 d . . .
H8A H -0.0881 0.6124 0.9227 0.063 Uiso 1 1 calc R . .
C9 C 0.13696(16) 0.69098(11) 1.1487(4) 0.0494(5) Uani 1 1 d . . .
H9A H 0.1930 0.7117 1.2056 0.059 Uiso 1 1 calc R . .
C10 C 0.34449(13) 0.57633(9) 0.7091(3) 0.0349(4) Uani 1 1 d . . .
H10A H 0.3985 0.5961 0.7805 0.042 Uiso 1 1 calc R . .
C11 C 0.14646(14) 0.63835(10) 1.0205(3) 0.0371(4) Uani 1 1 d . . .
C12 C 0.32697(14) 0.64233(10) 1.0974(3) 0.0383(4) Uani 1 1 d . . .
H12A H 0.3788 0.6115 1.1054 0.046 Uiso 1 1 calc R . .
H12B H 0.3117 0.6508 1.2432 0.046 Uiso 1 1 calc R . .
C13 C 0.18635(14) 0.51840(10) 0.4906(3) 0.0404(5) Uani 1 1 d . . .
H13A H 0.1319 0.5004 0.4147 0.048 Uiso 1 1 calc R . .
C14 C 0.05976(14) 0.60901(10) 0.9381(3) 0.0418(5) Uani 1 1 d . . .
C15 C 0.36324(14) 0.42512(9) -0.0724(3) 0.0372(4) Uani 1 1 d . . .
C16 C 0.27772(14) 0.51345(9) 0.4088(3) 0.0349(4) Uani 1 1 d . . .
C17 C 0.17436(13) 0.54914(9) 0.6803(3) 0.0375(4) Uani 1 1 d . . .
C18 C 0.39620(14) 0.37045(9) -0.3414(3) 0.0376(4) Uani 1 1 d . . .
C19 C 0.25259(13) 0.58186(9) 0.7901(3) 0.0324(4) Uani 1 1 d . . .
C20 C 0.28475(14) 0.47785(9) 0.2124(3) 0.0371(4) Uani 1 1 d . . .
H20A H 0.2257 0.4637 0.1440 0.045 Uiso 1 1 calc R . .
C21 C 0.29495(15) 0.37112(9) -0.3397(3) 0.0380(4) Uani 1 1 d . . .
C22 C 0.36510(15) 0.46294(9) 0.1180(3) 0.0385(4) Uani 1 1 d . . .
H22A H 0.4253 0.4777 0.1783 0.046 Uiso 1 1 calc R . .
N1 N 0.23940(11) 0.61578(8) 0.9768(2) 0.0367(4) Uani 1 1 d . . .
C23 C 0.35686(13) 0.54238(9) 0.5260(3) 0.0359(4) Uani 1 1 d . . .
H23A H 0.4192 0.5387 0.4797 0.043 Uiso 1 1 calc R . .


_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 C14 1.756(2) . ?
S1 C17 1.761(2) . ?
O1 C21 1.379(2) . ?
O1 C15 1.384(2) . ?
N2 C15 1.297(2) . ?
N2 C18 1.396(2) . ?
C1 C3 1.376(3) . ?
C1 C9 1.388(3) . ?
C2 C6 1.384(3) . ?
C2 C18 1.390(3) . ?
C3 C8 1.371(3) . ?
C4 C12 1.518(3) . ?
C5 C21 1.380(3) . ?
C5 C7 1.388(3) . ?
C6 C7 1.389(3) . ?
C8 C14 1.392(3) . ?
C9 C11 1.402(3) . ?
C10 C23 1.381(3) . ?
C10 C19 1.404(3) . ?
C11 C14 1.400(3) . ?
C11 N1 1.412(2) . ?
C12 N1 1.471(2) . ?
C13 C17 1.380(3) . ?
C13 C16 1.398(3) . ?
C15 C22 1.440(3) . ?
C16 C23 1.397(3) . ?
C16 C20 1.458(3) . ?
C17 C19 1.407(3) . ?
C18 C21 1.387(3) . ?
C19 N1 1.402(2) . ?
C20 C22 1.334(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
C14 S1 C17 99.33(10) . . ?
C21 O1 C15 103.79(15) . . ?
C15 N2 C18 104.77(16) . . ?
C3 C1 C9 120.6(2) . . ?
C6 C2 C18 117.4(2) . . ?
C8 C3 C1 119.1(2) . . ?
C21 C5 C7 115.3(2) . . ?
C2 C6 C7 121.5(2) . . ?
C5 C7 C6 122.1(2) . . ?
C3 C8 C14 121.1(2) . . ?
C1 C9 C11 121.3(2) . . ?
C23 C10 C19 121.76(17) . . ?
C14 C11 C9 117.07(18) . . ?
C14 C11 N1 121.45(18) . . ?
C9 C11 N1 121.48(17) . . ?
N1 C12 C4 114.95(16) . . ?
C17 C13 C16 122.12(17) . . ?
C8 C14 C11 120.8(2) . . ?
C8 C14 S1 118.49(16) . . ?
C11 C14 S1 120.47(15) . . ?
N2 C15 O1 114.80(17) . . ?
N2 C15 C22 127.62(18) . . ?
O1 C15 C22 117.58(17) . . ?
C23 C16 C13 116.82(17) . . ?
C23 C16 C20 124.56(18) . . ?
C13 C16 C20 118.60(17) . . ?
C13 C17 C19 120.89(18) . . ?
C13 C17 S1 118.34(15) . . ?
C19 C17 S1 120.28(15) . . ?
C21 C18 C2 119.68(19) . . ?
C21 C18 N2 108.77(17) . . ?
C2 C18 N2 131.55(19) . . ?
N1 C19 C10 122.22(16) . . ?
N1 C19 C17 121.06(17) . . ?
C10 C19 C17 116.66(17) . . ?
C22 C20 C16 128.30(18) . . ?
O1 C21 C5 128.09(19) . . ?
O1 C21 C18 107.87(16) . . ?
C5 C21 C18 124.0(2) . . ?
C20 C22 C15 123.28(18) . . ?
C19 N1 C11 121.89(15) . . ?
C19 N1 C12 117.83(15) . . ?
C11 N1 C12 118.23(16) . . ?
C10 C23 C16 121.44(17) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 978631'
