# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sgm_se_67_0m
_database_code_depnum_ccdc_archive 'CCDC 1057298'
_audit_update_record             
;
2015-04-01 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 N2 O4'
_chemical_formula_sum            'C23 H18 N2 O4'
_chemical_formula_weight         386.39

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                   10.8247(5)
_cell_length_b                   12.1491(5)
_cell_length_c                   14.0090(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.356(2)
_cell_angle_gamma                90.00
_cell_volume                     1831.00(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9869
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      35.53

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9576
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_process_details   'Bruker SADABS'

_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35378
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0102
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3226
_reflns_number_gt                2962
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0336P)²+0.8563P] 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         3226
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0802
_refine_ls_wR_factor_gt          0.0778
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.17732(8) 0.26298(7) 0.03315(6) 0.0235(2) Uani 1 1 d . . .
O2 O 0.31681(10) 0.13670(8) 0.09916(7) 0.0344(3) Uani 1 1 d . . .
O3 O 0.09345(10) 0.67329(9) 0.58778(7) 0.0347(3) Uani 1 1 d . . .
O4 O 0.11090(9) 0.81117(8) 0.49278(7) 0.0329(2) Uani 1 1 d . . .
N1 N 0.30638(10) 0.50757(9) -0.06504(8) 0.0243(3) Uani 1 1 d . . .
N2 N 0.11097(10) 0.71211(9) 0.50950(8) 0.0244(3) Uani 1 1 d . . .
C1 C 0.34184(11) 0.34499(10) 0.09592(8) 0.0200(3) Uani 1 1 d . . .
H1 H 0.4174 0.3583 0.0624 0.024 Uiso 1 1 calc R . .
C2 C 0.28752(13) 0.22973(11) 0.08211(9) 0.0235(3) Uani 1 1 d . . .
C3 C 0.21829(11) 0.38037(10) 0.03797(9) 0.0197(3) Uani 1 1 d . . .
C4 C 0.14585(12) 0.44546(10) 0.10552(8) 0.0207(3) Uani 1 1 d . . .
H4A H 0.0567 0.4255 0.0962 0.025 Uiso 1 1 calc R . .
H4B H 0.1540 0.5255 0.0945 0.025 Uiso 1 1 calc R . .
C5 C 0.20384(11) 0.41414(10) 0.20714(8) 0.0183(3) Uani 1 1 d . . .
H5 H 0.1713 0.3402 0.2235 0.022 Uiso 1 1 calc R . .
C6 C 0.34435(11) 0.40223(10) 0.19431(8) 0.0182(3) Uani 1 1 d . . .
H6 H 0.3755 0.4786 0.1851 0.022 Uiso 1 1 calc R . .
C7 C 0.22163(11) 0.42798(10) -0.06050(9) 0.0201(3) Uani 1 1 d . . .
C8 C 0.14045(12) 0.39414(11) -0.13878(9) 0.0246(3) Uani 1 1 d . . .
H8 H 0.0808 0.3380 -0.1322 0.029 Uiso 1 1 calc R . .
C9 C 0.14860(13) 0.44419(12) -0.22653(9) 0.0284(3) Uani 1 1 d . . .
H9 H 0.0946 0.4229 -0.2815 0.034 Uiso 1 1 calc R . .
C10 C 0.23627(13) 0.52548(12) -0.23305(10) 0.0288(3) Uani 1 1 d . . .
H10 H 0.2445 0.5607 -0.2926 0.035 Uiso 1 1 calc R . .
C11 C 0.31190(13) 0.55439(12) -0.15085(9) 0.0273(3) Uani 1 1 d . . .
H11 H 0.3714 0.6110 -0.1556 0.033 Uiso 1 1 calc R . .
C12 C 0.17934(11) 0.49403(10) 0.28558(8) 0.0181(3) Uani 1 1 d . . .
C13 C 0.17673(12) 0.60779(11) 0.27057(9) 0.0234(3) Uani 1 1 d . . .
H13 H 0.1913 0.6363 0.2097 0.028 Uiso 1 1 calc R . .
C14 C 0.15332(12) 0.67934(11) 0.34306(9) 0.0240(3) Uani 1 1 d . . .
H14 H 0.1504 0.7565 0.3322 0.029 Uiso 1 1 calc R . .
C15 C 0.13424(11) 0.63633(10) 0.43181(9) 0.0203(3) Uani 1 1 d . . .
C16 C 0.13895(12) 0.52486(11) 0.44988(9) 0.0224(3) Uani 1 1 d . . .
H16 H 0.1274 0.4970 0.5116 0.027 Uiso 1 1 calc R . .
C17 C 0.16086(12) 0.45433(10) 0.37590(9) 0.0217(3) Uani 1 1 d . . .
H17 H 0.1633 0.3772 0.3872 0.026 Uiso 1 1 calc R . .
C18 C 0.42487(11) 0.35559(10) 0.28014(8) 0.0185(3) Uani 1 1 d . . .
C19 C 0.48746(12) 0.42873(11) 0.34514(9) 0.0236(3) Uani 1 1 d . . .
H19 H 0.4808 0.5056 0.3333 0.028 Uiso 1 1 calc R . .
C20 C 0.55930(13) 0.39139(12) 0.42681(9) 0.0275(3) Uani 1 1 d . . .
H20 H 0.6005 0.4426 0.4707 0.033 Uiso 1 1 calc R . .
C21 C 0.57111(12) 0.27984(12) 0.44447(9) 0.0256(3) Uani 1 1 d . . .
H21 H 0.6210 0.2540 0.5000 0.031 Uiso 1 1 calc R . .
C22 C 0.50986(12) 0.20595(11) 0.38071(9) 0.0259(3) Uani 1 1 d . . .
H22 H 0.5180 0.1292 0.3925 0.031 Uiso 1 1 calc R . .
C23 C 0.43645(12) 0.24325(11) 0.29939(9) 0.0242(3) Uani 1 1 d . . .
H23 H 0.3938 0.1917 0.2566 0.029 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
O1 C2 1.3694(16) . ?
O1 C3 1.4929(15) . ?
O2 C2 1.1910(16) . ?
O3 N2 1.2276(15) . ?
O4 N2 1.2261(15) . ?
N1 C11 1.3372(17) . ?
N1 C7 1.3393(17) . ?
N2 C15 1.4685(16) . ?
C1 C2 1.5227(18) . ?
C1 C6 1.5414(16) . ?
C1 C3 1.5466(17) . ?
C1 H1 1.0000 . ?
C3 C7 1.4999(17) . ?
C3 C4 1.5166(17) . ?
C4 C5 1.5386(16) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C12 1.5115(16) . ?
C5 C6 1.5579(17) . ?
C5 H5 1.0000 . ?
C6 C18 1.5148(16) . ?
C6 H6 1.0000 . ?
C7 C8 1.3894(18) . ?
C8 C9 1.3831(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.380(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C17 1.3890(17) . ?
C12 C13 1.3979(18) . ?
C13 C14 1.3812(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.3850(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3776(18) . ?
C16 C17 1.3853(18) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.3933(18) . ?
C18 C23 1.3942(18) . ?
C19 C20 1.3866(18) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.3828(19) . ?
C21 H21 0.9500 . ?
C22 C23 1.3907(18) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

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
C2 O1 C3 91.21(9) . . ?
C11 N1 C7 116.67(11) . . ?
O4 N2 O3 123.43(11) . . ?
O4 N2 C15 118.05(11) . . ?
O3 N2 C15 118.52(11) . . ?
C2 C1 C6 119.79(10) . . ?
C2 C1 C3 83.66(9) . . ?
C6 C1 C3 105.82(10) . . ?
C2 C1 H1 114.4 . . ?
C6 C1 H1 114.4 . . ?
C3 C1 H1 114.4 . . ?
O2 C2 O1 125.33(12) . . ?
O2 C2 C1 139.17(13) . . ?
O1 C2 C1 95.46(10) . . ?
O1 C3 C7 111.36(10) . . ?
O1 C3 C4 110.78(10) . . ?
C7 C3 C4 116.08(10) . . ?
O1 C3 C1 89.63(9) . . ?
C7 C3 C1 118.84(10) . . ?
C4 C3 C1 107.11(10) . . ?
C3 C4 C5 105.20(10) . . ?
C3 C4 H4A 110.7 . . ?
C5 C4 H4A 110.7 . . ?
C3 C4 H4B 110.7 . . ?
C5 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
C12 C5 C4 115.30(10) . . ?
C12 C5 C6 113.30(10) . . ?
C4 C5 C6 102.69(9) . . ?
C12 C5 H5 108.4 . . ?
C4 C5 H5 108.4 . . ?
C6 C5 H5 108.4 . . ?
C18 C6 C1 119.52(10) . . ?
C18 C6 C5 115.24(10) . . ?
C1 C6 C5 102.96(9) . . ?
C18 C6 H6 106.0 . . ?
C1 C6 H6 106.0 . . ?
C5 C6 H6 106.0 . . ?
N1 C7 C8 123.56(12) . . ?
N1 C7 C3 114.11(11) . . ?
C8 C7 C3 122.29(12) . . ?
C9 C8 C7 118.32(13) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C10 C9 C8 119.05(12) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 118.36(12) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
N1 C11 C10 124.02(13) . . ?
N1 C11 H11 118.0 . . ?
C10 C11 H11 118.0 . . ?
C17 C12 C13 118.54(11) . . ?
C17 C12 C5 119.60(11) . . ?
C13 C12 C5 121.86(11) . . ?
C14 C13 C12 120.92(12) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 118.70(12) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 121.98(12) . . ?
C16 C15 N2 119.08(11) . . ?
C14 C15 N2 118.93(11) . . ?
C15 C16 C17 118.46(12) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
C16 C17 C12 121.37(12) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
C19 C18 C23 118.11(11) . . ?
C19 C18 C6 118.40(11) . . ?
C23 C18 C6 123.45(11) . . ?
C20 C19 C18 121.22(12) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C21 C20 C19 120.08(12) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 119.55(12) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C21 C22 C23 120.48(12) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 120.56(12) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?

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
C3 O1 C2 O2 -176.49(13) . . . . ?
C3 O1 C2 C1 1.58(9) . . . . ?
C6 C1 C2 O2 -79.3(2) . . . . ?
C3 C1 C2 O2 176.05(17) . . . . ?
C6 C1 C2 O1 103.09(11) . . . . ?
C3 C1 C2 O1 -1.53(9) . . . . ?
C2 O1 C3 C7 119.48(10) . . . . ?
C2 O1 C3 C4 -109.74(10) . . . . ?
C2 O1 C3 C1 -1.55(9) . . . . ?
C2 C1 C3 O1 1.40(8) . . . . ?
C6 C1 C3 O1 -117.81(9) . . . . ?
C2 C1 C3 C7 -112.94(11) . . . . ?
C6 C1 C3 C7 127.84(11) . . . . ?
C2 C1 C3 C4 113.07(10) . . . . ?
C6 C1 C3 C4 -6.15(13) . . . . ?
O1 C3 C4 C5 77.27(12) . . . . ?
C7 C3 C4 C5 -154.46(10) . . . . ?
C1 C3 C4 C5 -19.02(13) . . . . ?
C3 C4 C5 C12 160.21(10) . . . . ?
C3 C4 C5 C6 36.50(12) . . . . ?
C2 C1 C6 C18 65.95(15) . . . . ?
C3 C1 C6 C18 157.67(10) . . . . ?
C2 C1 C6 C5 -63.33(13) . . . . ?
C3 C1 C6 C5 28.38(12) . . . . ?
C12 C5 C6 C18 63.26(14) . . . . ?
C4 C5 C6 C18 -171.71(10) . . . . ?
C12 C5 C6 C1 -164.87(10) . . . . ?
C4 C5 C6 C1 -39.84(11) . . . . ?
C11 N1 C7 C8 -0.89(18) . . . . ?
C11 N1 C7 C3 -178.82(11) . . . . ?
O1 C3 C7 N1 -150.59(10) . . . . ?
C4 C3 C7 N1 81.43(14) . . . . ?
C1 C3 C7 N1 -48.62(15) . . . . ?
O1 C3 C7 C8 31.45(16) . . . . ?
C4 C3 C7 C8 -96.54(14) . . . . ?
C1 C3 C7 C8 133.42(13) . . . . ?
N1 C7 C8 C9 0.94(19) . . . . ?
C3 C7 C8 C9 178.71(12) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C8 C9 C10 C11 -0.6(2) . . . . ?
C7 N1 C11 C10 0.04(19) . . . . ?
C9 C10 C11 N1 0.7(2) . . . . ?
C4 C5 C12 C17 143.55(12) . . . . ?
C6 C5 C12 C17 -98.52(13) . . . . ?
C4 C5 C12 C13 -37.56(16) . . . . ?
C6 C5 C12 C13 80.36(14) . . . . ?
C17 C12 C13 C14 -1.56(19) . . . . ?
C5 C12 C13 C14 179.55(11) . . . . ?
C12 C13 C14 C15 0.98(19) . . . . ?
C13 C14 C15 C16 0.53(19) . . . . ?
C13 C14 C15 N2 179.19(11) . . . . ?
O4 N2 C15 C16 177.82(11) . . . . ?
O3 N2 C15 C16 -1.71(17) . . . . ?
O4 N2 C15 C14 -0.88(17) . . . . ?
O3 N2 C15 C14 179.59(11) . . . . ?
C14 C15 C16 C17 -1.40(19) . . . . ?
N2 C15 C16 C17 179.95(11) . . . . ?
C15 C16 C17 C12 0.78(19) . . . . ?
C13 C12 C17 C16 0.67(18) . . . . ?
C5 C12 C17 C16 179.58(11) . . . . ?
C1 C6 C18 C19 141.25(12) . . . . ?
C5 C6 C18 C19 -95.25(13) . . . . ?
C1 C6 C18 C23 -40.99(17) . . . . ?
C5 C6 C18 C23 82.50(15) . . . . ?
C23 C18 C19 C20 -0.04(19) . . . . ?
C6 C18 C19 C20 177.84(12) . . . . ?
C18 C19 C20 C21 0.8(2) . . . . ?
C19 C20 C21 C22 -0.6(2) . . . . ?
C20 C21 C22 C23 -0.2(2) . . . . ?
C21 C22 C23 C18 0.9(2) . . . . ?
C19 C18 C23 C22 -0.80(19) . . . . ?
C6 C18 C23 C22 -178.56(12) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.036
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate-Petroleum Ether'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sb_8
_database_code_depnum_ccdc_archive 'CCDC 1057299'
_audit_update_record             
;
2015-04-01 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H19 N O3, C H Cl3'
_chemical_formula_sum            'C24 H20 Cl3 N O3'
_chemical_formula_weight         476.76

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'
Cl Cl 0.1484 0.1585 '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                   15.3285(8)
_cell_length_b                   11.4221(6)
_cell_length_c                   12.7961(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.471(2)
_cell_angle_gamma                90.00
_cell_volume                     2230.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    8328
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      29.26

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.38
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8208
_exptl_absorpt_correction_T_max  0.8514
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13651
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3914
_reflns_number_gt                3515
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0327P)²+8.4930P] 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         3914
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.1618
_refine_ls_wR_factor_gt          0.1584
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.160
_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 0.95833(16) 0.1120(2) 0.3081(2) 0.0193(6) Uani 1 1 d . . .
O2 O 0.98251(18) 0.2119(2) 0.4634(2) 0.0266(6) Uani 1 1 d . . .
O3 O 0.69646(16) 0.0419(2) 0.23233(19) 0.0188(6) Uani 1 1 d . . .
N1 N 0.75156(19) -0.0457(3) 0.2431(2) 0.0144(6) Uani 1 1 d . . .
C1 C 0.8372(2) 0.1787(3) 0.3546(3) 0.0142(7) Uani 1 1 d . . .
H1 H 0.7987 0.1386 0.4023 0.017 Uiso 1 1 calc R . .
C2 C 0.9341(2) 0.1774(3) 0.3919(3) 0.0180(8) Uani 1 1 d . . .
C3 C 0.8650(2) 0.1020(3) 0.2636(3) 0.0153(7) Uani 1 1 d . . .
C4 C 0.8490(2) 0.1720(3) 0.1621(3) 0.0165(8) Uani 1 1 d . . .
H4A H 0.7945 0.1460 0.1209 0.020 Uiso 1 1 calc R . .
H4B H 0.8986 0.1630 0.1185 0.020 Uiso 1 1 calc R . .
C5 C 0.8408(2) 0.3002(3) 0.1983(3) 0.0161(8) Uani 1 1 d . . .
H5 H 0.9011 0.3333 0.2130 0.019 Uiso 1 1 calc R . .
C6 C 0.7987(2) 0.2916(3) 0.3033(3) 0.0159(7) Uani 1 1 d . . .
H6 H 0.7347 0.2770 0.2850 0.019 Uiso 1 1 calc R . .
C7 C 0.8391(2) -0.0242(3) 0.2604(3) 0.0138(7) Uani 1 1 d . . .
C8 C 0.8971(2) -0.1172(3) 0.2751(3) 0.0174(8) Uani 1 1 d . . .
H8 H 0.9581 -0.1021 0.2884 0.021 Uiso 1 1 calc R . .
C9 C 0.8672(3) -0.2317(3) 0.2705(3) 0.0209(8) Uani 1 1 d . . .
H9 H 0.9071 -0.2954 0.2792 0.025 Uiso 1 1 calc R . .
C10 C 0.7780(3) -0.2512(3) 0.2531(3) 0.0201(8) Uani 1 1 d . . .
H10 H 0.7558 -0.3289 0.2505 0.024 Uiso 1 1 calc R . .
C11 C 0.7215(2) -0.1579(3) 0.2395(3) 0.0179(8) Uani 1 1 d . . .
H11 H 0.6602 -0.1719 0.2274 0.021 Uiso 1 1 calc R . .
C12 C 0.7891(2) 0.3799(3) 0.1205(3) 0.0172(8) Uani 1 1 d . . .
C13 C 0.7045(3) 0.3491(4) 0.0806(3) 0.0233(9) Uani 1 1 d . . .
H13 H 0.6806 0.2762 0.0995 0.028 Uiso 1 1 calc R . .
C14 C 0.6548(3) 0.4246(4) 0.0131(3) 0.0336(11) Uani 1 1 d . . .
H14 H 0.5968 0.4037 -0.0131 0.040 Uiso 1 1 calc R . .
C15 C 0.6894(3) 0.5290(4) -0.0154(3) 0.0360(11) Uani 1 1 d . . .
H15 H 0.6551 0.5802 -0.0611 0.043 Uiso 1 1 calc R . .
C16 C 0.7729(3) 0.5604(4) 0.0209(3) 0.0349(11) Uani 1 1 d . . .
H16 H 0.7966 0.6324 -0.0006 0.042 Uiso 1 1 calc R . .
C17 C 0.8237(3) 0.4861(3) 0.0902(3) 0.0251(9) Uani 1 1 d . . .
H17 H 0.8815 0.5082 0.1162 0.030 Uiso 1 1 calc R . .
C18 C 0.8060(2) 0.4002(3) 0.3714(3) 0.0153(7) Uani 1 1 d . . .
C19 C 0.7322(3) 0.4423(3) 0.4143(3) 0.0219(8) Uani 1 1 d . . .
H19 H 0.6775 0.4037 0.4000 0.026 Uiso 1 1 calc R . .
C20 C 0.7384(3) 0.5422(4) 0.4791(3) 0.0274(9) Uani 1 1 d . . .
H20 H 0.6879 0.5713 0.5080 0.033 Uiso 1 1 calc R . .
C21 C 0.8175(3) 0.5973(3) 0.5005(3) 0.0259(9) Uani 1 1 d . . .
H21 H 0.8215 0.6644 0.5445 0.031 Uiso 1 1 calc R . .
C22 C 0.8911(3) 0.5568(3) 0.4589(3) 0.0235(9) Uani 1 1 d . . .
H22 H 0.9458 0.5952 0.4745 0.028 Uiso 1 1 calc R . .
C23 C 0.8851(3) 0.4586(3) 0.3936(3) 0.0196(8) Uani 1 1 d . . .
H23 H 0.9358 0.4314 0.3638 0.024 Uiso 1 1 calc R . .
Cl1 Cl 0.43671(7) 0.07997(10) 0.30089(10) 0.0386(3) Uani 1 1 d . A .
Cl2 Cl 0.52876(8) 0.29201(11) 0.25821(17) 0.0704(6) Uani 1 1 d . A .
Cl3' Cl 0.4871(5) 0.1736(8) 0.0955(7) 0.080(3) Uani 0.30 1 d P A 1
Cl3 Cl 0.49480(19) 0.1055(3) 0.0976(2) 0.0586(8) Uani 0.70 1 d P A 2
C24 C 0.5179(3) 0.1427(4) 0.2314(3) 0.0306(10) Uani 1 1 d . . .
H24 H 0.5750 0.1000 0.2427 0.037 Uiso 1 1 calc R A 1


_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 C2 1.386(4) . ?
O1 C3 1.493(4) . ?
O2 C2 1.189(4) . ?
O3 N1 1.308(4) . ?
N1 C7 1.361(4) . ?
N1 C11 1.362(5) . ?
C1 C2 1.517(5) . ?
C1 C6 1.538(5) . ?
C1 C3 1.549(5) . ?
C1 H1 1.0000 . ?
C3 C7 1.495(5) . ?
C3 C4 1.525(5) . ?
C4 C5 1.545(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C12 1.515(5) . ?
C5 C6 1.548(5) . ?
C5 H5 1.0000 . ?
C6 C18 1.515(5) . ?
C6 H6 1.0000 . ?
C7 C8 1.386(5) . ?
C8 C9 1.386(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.374(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.392(5) . ?
C12 C17 1.394(5) . ?
C13 C14 1.396(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.369(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.367(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.408(6) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.389(5) . ?
C18 C19 1.389(5) . ?
C19 C20 1.408(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.370(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.373(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.396(5) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
Cl1 C24 1.750(4) . ?
Cl2 C24 1.744(5) . ?
Cl3' C24 1.794(9) . ?
Cl3 C24 1.768(5) . ?
C24 H24 1.0000 . ?

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
C2 O1 C3 91.1(2) . . ?
O3 N1 C7 119.7(3) . . ?
O3 N1 C11 120.2(3) . . ?
C7 N1 C11 120.0(3) . . ?
C2 C1 C6 117.8(3) . . ?
C2 C1 C3 84.2(3) . . ?
C6 C1 C3 106.0(3) . . ?
C2 C1 H1 114.9 . . ?
C6 C1 H1 114.9 . . ?
C3 C1 H1 114.9 . . ?
O2 C2 O1 125.5(3) . . ?
O2 C2 C1 139.4(4) . . ?
O1 C2 C1 95.1(3) . . ?
O1 C3 C7 109.1(3) . . ?
O1 C3 C4 110.8(3) . . ?
C7 C3 C4 117.5(3) . . ?
O1 C3 C1 89.6(2) . . ?
C7 C3 C1 118.3(3) . . ?
C4 C3 C1 108.1(3) . . ?
C3 C4 C5 104.6(3) . . ?
C3 C4 H4A 110.8 . . ?
C5 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
C5 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
C12 C5 C4 115.2(3) . . ?
C12 C5 C6 111.9(3) . . ?
C4 C5 C6 104.6(3) . . ?
C12 C5 H5 108.3 . . ?
C4 C5 H5 108.3 . . ?
C6 C5 H5 108.3 . . ?
C18 C6 C1 115.9(3) . . ?
C18 C6 C5 115.7(3) . . ?
C1 C6 C5 104.4(3) . . ?
C18 C6 H6 106.7 . . ?
C1 C6 H6 106.7 . . ?
C5 C6 H6 106.7 . . ?
N1 C7 C8 119.6(3) . . ?
N1 C7 C3 115.7(3) . . ?
C8 C7 C3 124.7(3) . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 118.5(3) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C11 C10 C9 119.8(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N1 C11 C10 121.2(3) . . ?
N1 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C17 119.0(4) . . ?
C13 C12 C5 119.9(3) . . ?
C17 C12 C5 121.1(3) . . ?
C12 C13 C14 120.3(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 120.0(4) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 120.9(4) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 120.0(4) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 119.8(4) . . ?
C12 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C23 C18 C19 118.7(3) . . ?
C23 C18 C6 121.7(3) . . ?
C19 C18 C6 119.5(3) . . ?
C18 C19 C20 120.1(4) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 119.9(4) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.8(4) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C23 119.5(4) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C18 C23 C22 120.9(4) . . ?
C18 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
Cl2 C24 Cl1 111.1(2) . . ?
Cl2 C24 Cl3 115.6(3) . . ?
Cl1 C24 Cl3 107.9(2) . . ?
Cl2 C24 Cl3' 90.5(4) . . ?
Cl1 C24 Cl3' 116.0(4) . . ?
Cl3 C24 Cl3' 25.5(3) . . ?
Cl2 C24 H24 112.5 . . ?
Cl1 C24 H24 112.5 . . ?
Cl3 C24 H24 96.6 . . ?
Cl3' C24 H24 112.5 . . ?

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
C3 O1 C2 O2 177.0(4) . . . . ?
C3 O1 C2 C1 -2.0(3) . . . . ?
C6 C1 C2 O2 78.1(6) . . . . ?
C3 C1 C2 O2 -176.9(5) . . . . ?
C6 C1 C2 O1 -103.1(3) . . . . ?
C3 C1 C2 O1 1.9(3) . . . . ?
C2 O1 C3 C7 -118.0(3) . . . . ?
C2 O1 C3 C4 111.1(3) . . . . ?
C2 O1 C3 C1 1.9(3) . . . . ?
C2 C1 C3 O1 -1.7(2) . . . . ?
C6 C1 C3 O1 115.6(3) . . . . ?
C2 C1 C3 C7 109.8(3) . . . . ?
C6 C1 C3 C7 -132.9(3) . . . . ?
C2 C1 C3 C4 -113.6(3) . . . . ?
C6 C1 C3 C4 3.8(4) . . . . ?
O1 C3 C4 C5 -78.9(3) . . . . ?
C7 C3 C4 C5 154.8(3) . . . . ?
C1 C3 C4 C5 17.8(4) . . . . ?
C3 C4 C5 C12 -155.7(3) . . . . ?
C3 C4 C5 C6 -32.5(3) . . . . ?
C2 C1 C6 C18 -60.4(4) . . . . ?
C3 C1 C6 C18 -152.2(3) . . . . ?
C2 C1 C6 C5 68.1(4) . . . . ?
C3 C1 C6 C5 -23.7(3) . . . . ?
C12 C5 C6 C18 -71.1(4) . . . . ?
C4 C5 C6 C18 163.5(3) . . . . ?
C12 C5 C6 C1 160.3(3) . . . . ?
C4 C5 C6 C1 34.9(3) . . . . ?
O3 N1 C7 C8 178.0(3) . . . . ?
C11 N1 C7 C8 -0.5(5) . . . . ?
O3 N1 C7 C3 -1.1(4) . . . . ?
C11 N1 C7 C3 -179.6(3) . . . . ?
O1 C3 C7 N1 166.5(3) . . . . ?
C4 C3 C7 N1 -66.4(4) . . . . ?
C1 C3 C7 N1 66.3(4) . . . . ?
O1 C3 C7 C8 -12.6(5) . . . . ?
C4 C3 C7 C8 114.5(4) . . . . ?
C1 C3 C7 C8 -112.8(4) . . . . ?
N1 C7 C8 C9 1.1(5) . . . . ?
C3 C7 C8 C9 -179.8(3) . . . . ?
C7 C8 C9 C10 -1.3(5) . . . . ?
C8 C9 C10 C11 0.8(5) . . . . ?
O3 N1 C11 C10 -178.5(3) . . . . ?
C7 N1 C11 C10 0.0(5) . . . . ?
C9 C10 C11 N1 -0.2(5) . . . . ?
C4 C5 C12 C13 53.9(4) . . . . ?
C6 C5 C12 C13 -65.4(4) . . . . ?
C4 C5 C12 C17 -128.0(4) . . . . ?
C6 C5 C12 C17 112.7(4) . . . . ?
C17 C12 C13 C14 -1.3(5) . . . . ?
C5 C12 C13 C14 176.8(3) . . . . ?
C12 C13 C14 C15 0.9(6) . . . . ?
C13 C14 C15 C16 0.4(6) . . . . ?
C14 C15 C16 C17 -1.2(6) . . . . ?
C13 C12 C17 C16 0.5(5) . . . . ?
C5 C12 C17 C16 -177.6(3) . . . . ?
C15 C16 C17 C12 0.7(6) . . . . ?
C1 C6 C18 C23 74.4(4) . . . . ?
C5 C6 C18 C23 -48.4(5) . . . . ?
C1 C6 C18 C19 -104.8(4) . . . . ?
C5 C6 C18 C19 132.5(3) . . . . ?
C23 C18 C19 C20 -0.1(5) . . . . ?
C6 C18 C19 C20 179.0(3) . . . . ?
C18 C19 C20 C21 -0.5(6) . . . . ?
C19 C20 C21 C22 0.4(6) . . . . ?
C20 C21 C22 C23 0.4(6) . . . . ?
C19 C18 C23 C22 0.9(5) . . . . ?
C6 C18 C23 C22 -178.2(3) . . . . ?
C21 C22 C23 C18 -1.1(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.141
_refine_diff_density_min         -0.993
_refine_diff_density_rms         0.081
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
