# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1049475'
_audit_update_record             
;
2015-02-14 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H26 N2 O3'
_chemical_formula_sum            'C28 H26 N2 O3'
_chemical_formula_weight         438.51

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)/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                   9.4797(19)
_cell_length_b                   27.330(6)
_cell_length_c                   9.775(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.10(3)
_cell_angle_gamma                90.00
_cell_volume                     2254.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7158
_cell_measurement_theta_min      1.4902
_cell_measurement_theta_max      27.4774

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6199
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15051
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5138
_reflns_number_gt                4505
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 2008)'

_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)+(0.1200P)²+1.2187P] 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         5138
_refine_ls_number_parameters     357
_refine_ls_number_restraints     568
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0823
_refine_ls_wR_factor_ref         0.2419
_refine_ls_wR_factor_gt          0.2255
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.009
_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 0.3632(2) 0.02018(7) 0.6050(2) 0.0446(5) Uani 1 1 d U A .
O2 O -0.0216(3) 0.18362(8) 0.5547(3) 0.0648(6) Uani 1 1 d U . .
O3 O 0.2417(3) 0.17809(8) 0.6468(3) 0.0628(6) Uani 1 1 d DU . .
N1 N 0.1241(2) 0.05699(7) 0.2246(2) 0.0323(4) Uani 1 1 d U A .
N2 N 0.2248(2) 0.05921(7) 0.3795(2) 0.0297(4) Uani 1 1 d U A .
C1 C 0.1827(3) 0.06232(8) 0.1177(2) 0.0303(5) Uani 1 1 d U . .
C2 C 0.3343(3) 0.04707(9) 0.1481(3) 0.0385(5) Uani 1 1 d U . .
H2 H 0.4045 0.0345 0.2465 0.046 Uiso 1 1 calc R . .
C3 C 0.3822(3) 0.05026(10) 0.0344(3) 0.0458(6) Uani 1 1 d U . .
H3 H 0.4856 0.0397 0.0553 0.055 Uiso 1 1 calc R . .
C4 C 0.2822(4) 0.06847(11) -0.1087(3) 0.0513(7) Uani 1 1 d U . .
H4 H 0.3149 0.0694 -0.1873 0.062 Uiso 1 1 calc R . .
C5 C 0.1347(4) 0.08531(10) -0.1369(3) 0.0454(6) Uani 1 1 d U . .
H5 H 0.0672 0.0985 -0.2352 0.054 Uiso 1 1 calc R . .
C6 C 0.0811(3) 0.08349(8) -0.0248(3) 0.0341(5) Uani 1 1 d U A .
C7 C -0.0706(3) 0.10396(9) -0.0466(3) 0.0402(6) Uani 1 1 d U . .
C8 C -0.1636(18) 0.1405(7) -0.1546(19) 0.048(2) Uani 0.56(2) 1 d PU A 1
H8 H -0.1089 0.1570 -0.2018 0.058 Uiso 0.56(2) 1 calc PR A 1
C9 C -0.2904(14) 0.1539(4) -0.1953(14) 0.057(2) Uani 0.56(2) 1 d PU A 1
H9 H -0.3428 0.1742 -0.2829 0.068 Uiso 0.56(2) 1 calc PR A 1
C10 C -0.3633(11) 0.1379(3) -0.1064(15) 0.0540(19) Uani 0.56(2) 1 d PU A 1
H10 H -0.4658 0.1493 -0.1270 0.065 Uiso 0.56(2) 1 calc PR A 1
C11 C -0.2825(13) 0.1054(4) 0.0117(14) 0.0469(19) Uani 0.56(2) 1 d PU A 1
H11 H -0.3343 0.0937 0.0687 0.056 Uiso 0.56(2) 1 calc PR A 1
C12 C -0.1345(3) 0.08912(9) 0.0512(3) 0.0386(5) Uani 1 1 d U A .
C13 C -0.0471(3) 0.05026(9) 0.1698(3) 0.0340(5) Uani 1 1 d U . .
H13 H -0.0766 0.0178 0.1171 0.041 Uiso 1 1 calc R A .
C14 C -0.0852(3) 0.04872(10) 0.3058(3) 0.0405(6) Uani 1 1 d U A .
H14B H -0.1995 0.0415 0.2665 0.049 Uiso 1 1 calc R . .
H14A H -0.0254 0.0214 0.3741 0.049 Uiso 1 1 calc R . .
C15 C -0.0477(3) 0.09482(10) 0.3997(3) 0.0432(6) Uani 1 1 d U . .
H15 H -0.1319 0.1080 0.4152 0.052 Uiso 1 1 calc R A .
C16 C 0.0882(3) 0.11957(9) 0.4639(3) 0.0378(5) Uani 1 1 d U A .
C17 C 0.2394(3) 0.10703(8) 0.4543(3) 0.0323(5) Uani 1 1 d U . .
H17 H 0.3265 0.1044 0.5618 0.039 Uiso 1 1 calc R A .
C18 C 0.2864(3) 0.01758(8) 0.4657(3) 0.0318(5) Uani 1 1 d U . .
C19 C 0.2565(3) -0.02991(9) 0.3809(3) 0.0425(6) Uani 1 1 d U A .
H19A H 0.1457 -0.0313 0.3023 0.064 Uiso 1 1 calc R . .
H19C H 0.2782 -0.0571 0.4532 0.064 Uiso 1 1 calc R . .
H19B H 0.3262 -0.0325 0.3318 0.064 Uiso 1 1 calc R . .
C20 C 0.2873(3) 0.14590(8) 0.3722(3) 0.0369(5) Uani 1 1 d U A .
C21 C 0.1782(3) 0.17544(9) 0.2609(3) 0.0422(6) Uani 1 1 d U . .
H21 H 0.0694 0.1727 0.2368 0.051 Uiso 1 1 calc R A .
C22 C 0.2243(5) 0.20944(11) 0.1825(4) 0.0610(8) Uani 1 1 d U A .
H22 H 0.1470 0.2293 0.1045 0.073 Uiso 1 1 calc R . .
C23 C 0.3813(5) 0.21421(14) 0.2181(5) 0.0775(11) Uani 1 1 d U . .
H23 H 0.4134 0.2374 0.1655 0.093 Uiso 1 1 calc R A .
C24 C 0.4924(5) 0.18503(14) 0.3311(5) 0.0754(10) Uani 1 1 d U A .
H24 H 0.6013 0.1884 0.3565 0.091 Uiso 1 1 calc R . .
C25 C 0.4462(4) 0.15074(11) 0.4080(4) 0.0573(8) Uani 1 1 d U . .
H25 H 0.5234 0.1306 0.4850 0.069 Uiso 1 1 calc R A .
C26 C 0.0926(4) 0.16380(10) 0.5566(3) 0.0458(6) Uani 1 1 d U A .
C27 C 0.2727(11) 0.2242(3) 0.7358(9) 0.0573(16) Uani 0.627(10) 1 d PDU B 1
H27A H 0.2021 0.2252 0.7854 0.069 Uiso 0.627(10) 1 calc PR B 1
H27B H 0.3832 0.2234 0.8185 0.069 Uiso 0.627(10) 1 calc PR B 1
C28 C 0.2509(8) 0.2676(2) 0.6504(8) 0.0694(18) Uani 0.627(10) 1 d PDU B 1
H28B H 0.1399 0.2702 0.5729 0.104 Uiso 0.627(10) 1 calc PR B 1
H28A H 0.3191 0.2670 0.5993 0.104 Uiso 0.627(10) 1 calc PR B 1
H28C H 0.2787 0.2959 0.7196 0.104 Uiso 0.627(10) 1 calc PR B 1
C27A C 0.2472(19) 0.2136(5) 0.7632(18) 0.073(3) Uani 0.373(10) 1 d PDU B 2
H27D H 0.3053 0.2011 0.8696 0.087 Uiso 0.373(10) 1 calc PR B 2
H27C H 0.1411 0.2256 0.7434 0.087 Uiso 0.373(10) 1 calc PR B 2
C28A C 0.3441(17) 0.2520(5) 0.7224(16) 0.085(3) Uani 0.373(10) 1 d PDU B 2
H28D H 0.2954 0.2564 0.6107 0.128 Uiso 0.373(10) 1 calc PR B 2
H28E H 0.4533 0.2404 0.7595 0.128 Uiso 0.373(10) 1 calc PR B 2
H28F H 0.3444 0.2833 0.7714 0.128 Uiso 0.373(10) 1 calc PR B 2
C11A C -0.2722(16) 0.1124(5) 0.0550(16) 0.043(2) Uani 0.44(2) 1 d PU A 2
H11A H -0.3044 0.1037 0.1307 0.052 Uiso 0.44(2) 1 calc PR A 2
C10A C -0.3525(14) 0.1471(5) -0.0538(18) 0.056(2) Uani 0.44(2) 1 d PU A 2
H10A H -0.4465 0.1611 -0.0588 0.067 Uiso 0.44(2) 1 calc PR A 2
C9A C -0.2982(17) 0.1620(6) -0.1568(17) 0.055(2) Uani 0.44(2) 1 d PU A 2
H9A H -0.3537 0.1876 -0.2264 0.067 Uiso 0.44(2) 1 calc PR A 2
C8A C -0.138(2) 0.1373(9) -0.167(3) 0.046(3) Uani 0.44(2) 1 d PU A 2
H8A H -0.1014 0.1448 -0.2403 0.055 Uiso 0.44(2) 1 calc PR A 2


_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 C18 1.219(3) . ?
O2 C26 1.203(3) . ?
O3 C26 1.339(4) . ?
O3 C27A 1.478(13) . ?
O3 C27 1.482(7) . ?
N1 N2 1.375(3) . ?
N1 C1 1.397(3) . ?
N1 C13 1.471(3) . ?
N2 C18 1.377(3) . ?
N2 C17 1.473(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.407(3) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.465(4) . ?
C7 C8A 1.39(2) . ?
C7 C12 1.404(4) . ?
C7 C8 1.429(18) . ?
C8 C9 1.14(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.403(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(12) . ?
C10 H10 0.9500 . ?
C11 C12 1.350(12) . ?
C11 H11 0.9500 . ?
C12 C11A 1.468(14) . ?
C12 C13 1.511(3) . ?
C13 C14 1.530(3) . ?
C13 H13 1.0000 . ?
C14 C15 1.502(4) . ?
C14 H14B 0.9900 . ?
C14 H14A 0.9900 . ?
C15 C16 1.332(4) . ?
C15 H15 0.9500 . ?
C16 C26 1.500(4) . ?
C16 C17 1.518(3) . ?
C17 C20 1.520(3) . ?
C17 H17 1.0000 . ?
C18 C19 1.496(3) . ?
C19 H19A 0.9800 . ?
C19 H19C 0.9800 . ?
C19 H19B 0.9800 . ?
C20 C21 1.371(4) . ?
C20 C25 1.389(4) . ?
C21 C22 1.395(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.372(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.391(5) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C27 C28 1.412(9) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28B 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28C 0.9800 . ?
C27A C28A 1.562(15) . ?
C27A H27D 0.9900 . ?
C27A H27C 0.9900 . ?
C28A H28D 0.9800 . ?
C28A H28E 0.9800 . ?
C28A H28F 0.9800 . ?
C11A C10A 1.368(15) . ?
C11A H11A 0.9500 . ?
C10A C9A 1.384(18) . ?
C10A H10A 0.9500 . ?
C9A C8A 1.71(3) . ?
C9A H9A 0.9500 . ?
C8A H8A 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
C26 O3 C27A 110.8(6) . . ?
C26 O3 C27 120.1(4) . . ?
C27A O3 C27 20.3(6) . . ?
N2 N1 C1 120.41(18) . . ?
N2 N1 C13 120.26(17) . . ?
C1 N1 C13 119.30(18) . . ?
N1 N2 C18 121.70(19) . . ?
N1 N2 C17 116.55(17) . . ?
C18 N2 C17 120.76(18) . . ?
C2 C1 N1 122.2(2) . . ?
C2 C1 C6 120.6(2) . . ?
N1 C1 C6 117.2(2) . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.9(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 117.3(2) . . ?
C5 C6 C7 123.6(2) . . ?
C1 C6 C7 119.0(2) . . ?
C8A C7 C12 126.2(9) . . ?
C8A C7 C8 13.4(13) . . ?
C12 C7 C8 113.1(7) . . ?
C8A C7 C6 114.5(9) . . ?
C12 C7 C6 119.3(2) . . ?
C8 C7 C6 127.5(7) . . ?
C9 C8 C7 132.8(18) . . ?
C9 C8 H8 113.6 . . ?
C7 C8 H8 113.6 . . ?
C8 C9 C10 115.0(14) . . ?
C8 C9 H9 122.5 . . ?
C10 C9 H9 122.5 . . ?
C11 C10 C9 118.4(8) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C12 C11 C10 124.0(9) . . ?
C12 C11 H11 118.0 . . ?
C10 C11 H11 118.0 . . ?
C11 C12 C7 115.1(6) . . ?
C11 C12 C11A 17.1(5) . . ?
C7 C12 C11A 123.8(6) . . ?
C11 C12 C13 125.9(6) . . ?
C7 C12 C13 118.0(2) . . ?
C11A C12 C13 117.9(6) . . ?
N1 C13 C12 108.67(18) . . ?
N1 C13 C14 110.19(19) . . ?
C12 C13 C14 115.0(2) . . ?
N1 C13 H13 107.6 . . ?
C12 C13 H13 107.6 . . ?
C14 C13 H13 107.6 . . ?
C15 C14 C13 115.1(2) . . ?
C15 C14 H14B 108.5 . . ?
C13 C14 H14B 108.5 . . ?
C15 C14 H14A 108.5 . . ?
C13 C14 H14A 108.5 . . ?
H14B C14 H14A 107.5 . . ?
C16 C15 C14 128.5(2) . . ?
C16 C15 H15 115.7 . . ?
C14 C15 H15 115.7 . . ?
C15 C16 C26 116.7(2) . . ?
C15 C16 C17 126.4(2) . . ?
C26 C16 C17 116.9(2) . . ?
N2 C17 C16 110.67(19) . . ?
N2 C17 C20 109.95(18) . . ?
C16 C17 C20 113.11(19) . . ?
N2 C17 H17 107.6 . . ?
C16 C17 H17 107.6 . . ?
C20 C17 H17 107.6 . . ?
O1 C18 N2 120.4(2) . . ?
O1 C18 C19 122.4(2) . . ?
N2 C18 C19 117.2(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19C C19 H19B 109.5 . . ?
C21 C20 C25 118.9(2) . . ?
C21 C20 C17 122.1(2) . . ?
C25 C20 C17 119.0(2) . . ?
C20 C21 C22 121.1(3) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C21 119.9(3) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 119.5(3) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C23 C24 C25 120.6(3) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C20 C25 C24 120.0(3) . . ?
C20 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
O2 C26 O3 123.5(3) . . ?
O2 C26 C16 125.2(3) . . ?
O3 C26 C16 111.3(2) . . ?
C28 C27 O3 115.6(5) . . ?
C28 C27 H27A 108.4 . . ?
O3 C27 H27A 108.4 . . ?
C28 C27 H27B 108.4 . . ?
O3 C27 H27B 108.4 . . ?
H27A C27 H27B 107.5 . . ?
O3 C27A C28A 93.6(9) . . ?
O3 C27A H27D 113.0 . . ?
C28A C27A H27D 113.0 . . ?
O3 C27A H27C 113.0 . . ?
C28A C27A H27C 113.0 . . ?
H27D C27A H27C 110.4 . . ?
C27A C28A H28D 109.5 . . ?
C27A C28A H28E 109.5 . . ?
H28D C28A H28E 109.5 . . ?
C27A C28A H28F 109.5 . . ?
H28D C28A H28F 109.5 . . ?
H28E C28A H28F 109.5 . . ?
C10A C11A C12 117.8(10) . . ?
C10A C11A H11A 121.1 . . ?
C12 C11A H11A 121.1 . . ?
C11A C10A C9A 120.6(10) . . ?
C11A C10A H10A 119.7 . . ?
C9A C10A H10A 119.7 . . ?
C10A C9A C8A 124.2(13) . . ?
C10A C9A H9A 117.9 . . ?
C8A C9A H9A 117.9 . . ?
C7 C8A C9A 106.7(16) . . ?
C7 C8A H8A 126.6 . . ?
C9A C8A H8A 126.6 . . ?

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
C1 N1 N2 C18 -95.9(3) . . . . ?
C13 N1 N2 C18 85.7(3) . . . . ?
C1 N1 N2 C17 95.4(2) . . . . ?
C13 N1 N2 C17 -82.9(2) . . . . ?
N2 N1 C1 C2 31.4(3) . . . . ?
C13 N1 C1 C2 -150.2(2) . . . . ?
N2 N1 C1 C6 -149.2(2) . . . . ?
C13 N1 C1 C6 29.2(3) . . . . ?
N1 C1 C2 C3 175.7(2) . . . . ?
C6 C1 C2 C3 -3.6(4) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C5 2.3(4) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
C4 C5 C6 C1 -1.8(4) . . . . ?
C4 C5 C6 C7 175.8(2) . . . . ?
C2 C1 C6 C5 4.3(3) . . . . ?
N1 C1 C6 C5 -175.0(2) . . . . ?
C2 C1 C6 C7 -173.4(2) . . . . ?
N1 C1 C6 C7 7.3(3) . . . . ?
C5 C6 C7 C8A -17.5(10) . . . . ?
C1 C6 C7 C8A 160.0(10) . . . . ?
C5 C6 C7 C12 162.5(2) . . . . ?
C1 C6 C7 C12 -19.9(3) . . . . ?
C5 C6 C7 C8 -20.9(10) . . . . ?
C1 C6 C7 C8 156.7(9) . . . . ?
C8A C7 C8 C9 154(9) . . . . ?
C12 C7 C8 C9 -16(3) . . . . ?
C6 C7 C8 C9 167.3(17) . . . . ?
C7 C8 C9 C10 13(3) . . . . ?
C8 C9 C10 C11 -4.9(16) . . . . ?
C9 C10 C11 C12 2.5(11) . . . . ?
C10 C11 C12 C7 -5.9(10) . . . . ?
C10 C11 C12 C11A 118(4) . . . . ?
C10 C11 C12 C13 -174.2(5) . . . . ?
C8A C7 C12 C11 7.4(13) . . . . ?
C8 C7 C12 C11 10.3(10) . . . . ?
C6 C7 C12 C11 -172.6(6) . . . . ?
C8A C7 C12 C11A -9.5(14) . . . . ?
C8 C7 C12 C11A -6.6(11) . . . . ?
C6 C7 C12 C11A 170.4(7) . . . . ?
C8A C7 C12 C13 176.7(11) . . . . ?
C8 C7 C12 C13 179.6(8) . . . . ?
C6 C7 C12 C13 -3.4(3) . . . . ?
N2 N1 C13 C12 129.0(2) . . . . ?
C1 N1 C13 C12 -49.4(3) . . . . ?
N2 N1 C13 C14 2.2(3) . . . . ?
C1 N1 C13 C14 -176.2(2) . . . . ?
C11 C12 C13 N1 -157.0(7) . . . . ?
C7 C12 C13 N1 35.0(3) . . . . ?
C11A C12 C13 N1 -139.1(7) . . . . ?
C11 C12 C13 C14 -32.9(7) . . . . ?
C7 C12 C13 C14 159.1(2) . . . . ?
C11A C12 C13 C14 -15.1(7) . . . . ?
N1 C13 C14 C15 62.8(3) . . . . ?
C12 C13 C14 C15 -60.4(3) . . . . ?
C13 C14 C15 C16 -52.8(4) . . . . ?
C14 C15 C16 C26 -177.9(2) . . . . ?
C14 C15 C16 C17 1.2(4) . . . . ?
N1 N2 C17 C16 70.4(2) . . . . ?
C18 N2 C17 C16 -98.4(2) . . . . ?
N1 N2 C17 C20 -55.3(2) . . . . ?
C18 N2 C17 C20 135.9(2) . . . . ?
C15 C16 C17 N2 -7.4(3) . . . . ?
C26 C16 C17 N2 171.71(19) . . . . ?
C15 C16 C17 C20 116.5(3) . . . . ?
C26 C16 C17 C20 -64.4(3) . . . . ?
N1 N2 C18 O1 -173.1(2) . . . . ?
C17 N2 C18 O1 -4.9(3) . . . . ?
N1 N2 C18 C19 7.7(3) . . . . ?
C17 N2 C18 C19 175.9(2) . . . . ?
N2 C17 C20 C21 95.8(3) . . . . ?
C16 C17 C20 C21 -28.5(3) . . . . ?
N2 C17 C20 C25 -82.3(3) . . . . ?
C16 C17 C20 C25 153.4(3) . . . . ?
C25 C20 C21 C22 0.9(4) . . . . ?
C17 C20 C21 C22 -177.2(3) . . . . ?
C20 C21 C22 C23 -1.0(5) . . . . ?
C21 C22 C23 C24 0.4(6) . . . . ?
C22 C23 C24 C25 0.4(7) . . . . ?
C21 C20 C25 C24 -0.1(5) . . . . ?
C17 C20 C25 C24 178.1(3) . . . . ?
C23 C24 C25 C20 -0.5(6) . . . . ?
C27A O3 C26 O2 11.8(8) . . . . ?
C27 O3 C26 O2 -8.3(5) . . . . ?
C27A O3 C26 C16 -166.4(7) . . . . ?
C27 O3 C26 C16 173.5(4) . . . . ?
C15 C16 C26 O2 -14.3(4) . . . . ?
C17 C16 C26 O2 166.5(3) . . . . ?
C15 C16 C26 O3 163.8(2) . . . . ?
C17 C16 C26 O3 -15.3(3) . . . . ?
C26 O3 C27 C28 -76.2(8) . . . . ?
C27A O3 C27 C28 -144(3) . . . . ?
C26 O3 C27A C28A -127.9(8) . . . . ?
C27 O3 C27A C28A -6(2) . . . . ?
C11 C12 C11A C10A -57(3) . . . . ?
C7 C12 C11A C10A 7.1(12) . . . . ?
C13 C12 C11A C10A -179.1(7) . . . . ?
C12 C11A C10A C9A -4.5(15) . . . . ?
C11A C10A C9A C8A 3.8(19) . . . . ?
C12 C7 C8A C9A 7.4(18) . . . . ?
C8 C7 C8A C9A -4(6) . . . . ?
C6 C7 C8A C9A -172.6(9) . . . . ?
C10A C9A C8A C7 -5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.693
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.088
####################################################################### 
# 
# 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_sa3591
_database_code_depnum_ccdc_archive 'CCDC 1049476'
_audit_update_record             
;
2015-02-14 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;
_audit_creation_date             2014-09-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C28 H26 N2 O3'
_chemical_formula_sum            'C28 H26 N2 O3'
_chemical_formula_weight         438.51
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.5503(19)
_cell_length_b                   17.424(4)
_cell_length_c                   15.187(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.211(3)
_cell_angle_gamma                90
_cell_volume                     2244.6(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6359
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4851
_cell_measurement_theta_min      1.1687
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14344
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.787
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             5282
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0275
_diffrn_orient_matrix_UB_12      0.0802
_diffrn_orient_matrix_UB_13      -0.0819
_diffrn_orient_matrix_UB_21      -0.0469
_diffrn_orient_matrix_UB_22      0.0301
_diffrn_orient_matrix_UB_23      0.0137
_diffrn_orient_matrix_UB_31      0.0367
_diffrn_orient_matrix_UB_32      0.0394
_diffrn_orient_matrix_UB_33      0.0389
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4768
_reflns_number_total             5103
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution    
;
'SHELXS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5103
_refine_ls_number_restraints     116
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0606
_refine_ls_restrained_S_all      1.193
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0374P)²+1.0903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1298
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O3A-C20 = O3-C20
 1.34 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
O2 \\sim O3 \\sim C21 \\sim C22 \\sim O3A \\sim C21A \\sim C22A \\sim O2A:
within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(O2) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22)
\\sim Ueq, Uanis(O3A) \\sim Ueq, Uanis(C21A) \\sim Ueq, Uanis(C22A) \\sim Ueq,
Uanis(O2A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(O3A)=Sof(C21A)=Sof(H21C)=Sof(H21D)=Sof(C22A)=Sof(H22D)=Sof(H22E)=
 Sof(H22F)=Sof(O2A)=1-FVAR(1)
 Sof(O2)=Sof(O3)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22A)=Sof(H22B)=
 Sof(H22C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C5(H5)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C21(H21A,H21B), C21A(H21C,H21D)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17),
 C18(H18), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
5.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C22(H22A,H22B,H22C), C22A(H22D,H22E,H22F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.17407(14) 0.71337(8) 0.33129(8) 0.0380(3) Uani 1 1 d . . . . .
O2 O 0.9361(13) 0.6384(4) 0.5575(6) 0.074(2) Uani 0.637(7) 1 d . U P A 1
O3 O 0.6745(9) 0.5930(6) 0.5287(6) 0.0508(18) Uani 0.637(7) 1 d D U P A 1
N1 N 0.78067(15) 0.67240(8) 0.25030(9) 0.0229(3) Uani 1 1 d . . . . .
N2 N 0.91176(15) 0.69659(8) 0.30824(8) 0.0239(3) Uani 1 1 d . . . . .
C1 C 0.65140(18) 0.72823(10) 0.23663(11) 0.0249(3) Uani 1 1 d . . . . .
H1 H 0.6969 0.7784 0.2255 0.030 Uiso 1 1 calc R . . . .
C2 C 0.5559(2) 0.73689(11) 0.31715(11) 0.0319(4) Uani 1 1 d . . . . .
H2A H 0.5605 0.7901 0.3359 0.038 Uiso 1 1 calc R . . . .
H2B H 0.4463 0.7249 0.2973 0.038 Uiso 1 1 calc R . . . .
C3 C 0.6102(2) 0.68779(10) 0.39580(11) 0.0283(4) Uani 1 1 d . . . . .
H3 H 0.5344 0.6595 0.4205 0.034 Uiso 1 1 calc R . . . .
C4 C 0.7593(2) 0.68153(9) 0.43322(11) 0.0262(3) Uani 1 1 d . . . . .
C5 C 0.89334(19) 0.72386(9) 0.39868(10) 0.0245(3) Uani 1 1 d . . . . .
H5 H 0.9899 0.7096 0.4370 0.029 Uiso 1 1 calc R . . . .
C6 C 1.05807(19) 0.69497(10) 0.28033(11) 0.0280(4) Uani 1 1 d . . . . .
C7 C 1.0678(2) 0.67150(12) 0.18622(12) 0.0374(4) Uani 1 1 d . . . . .
H7A H 1.0186 0.7099 0.1467 0.056 Uiso 1 1 calc GR . . . .
H7B H 1.0146 0.6234 0.1745 0.056 Uiso 1 1 calc GR . . . .
H7C H 1.1764 0.6662 0.1772 0.056 Uiso 1 1 calc GR . . . .
C8 C 0.74085(18) 0.59377(9) 0.25172(10) 0.0233(3) Uani 1 1 d . . . . .
C9 C 0.8278(2) 0.54041(10) 0.30561(11) 0.0285(4) Uani 1 1 d . . . . .
H9 H 0.9133 0.5567 0.3452 0.034 Uiso 1 1 calc R . . . .
C10 C 0.7884(2) 0.46337(10) 0.30089(12) 0.0346(4) Uani 1 1 d . . . . .
H10 H 0.8466 0.4281 0.3375 0.042 Uiso 1 1 calc R . . . .
C11 C 0.6616(2) 0.43881(11) 0.24141(13) 0.0391(4) Uani 1 1 d . . . . .
H11 H 0.6351 0.3870 0.2379 0.047 Uiso 1 1 calc R . . . .
C12 C 0.5751(2) 0.49150(11) 0.18753(12) 0.0351(4) Uani 1 1 d . . . . .
H12 H 0.4901 0.4745 0.1481 0.042 Uiso 1 1 calc R . . . .
C13 C 0.61194(19) 0.56955(10) 0.19065(10) 0.0262(3) Uani 1 1 d . . . . .
C14 C 0.52557(19) 0.62736(10) 0.13246(10) 0.0269(4) Uani 1 1 d . . . . .
C15 C 0.4265(2) 0.60768(12) 0.05492(11) 0.0349(4) Uani 1 1 d . . . . .
H15 H 0.4163 0.5565 0.0378 0.042 Uiso 1 1 calc R . . . .
C16 C 0.3436(2) 0.66373(13) 0.00359(12) 0.0410(5) Uani 1 1 d . . . . .
H16 H 0.2775 0.6498 -0.0473 0.049 Uiso 1 1 calc R . . . .
C17 C 0.3587(2) 0.73992(13) 0.02758(12) 0.0405(5) Uani 1 1 d . . . . .
H17 H 0.3008 0.7772 -0.0060 0.049 Uiso 1 1 calc R . . . .
C18 C 0.4605(2) 0.76064(12) 0.10200(12) 0.0343(4) Uani 1 1 d . . . . .
H18 H 0.4728 0.8122 0.1173 0.041 Uiso 1 1 calc R . . . .
C19 C 0.54478(18) 0.70507(10) 0.15411(10) 0.0265(4) Uani 1 1 d . . . . .
C20 C 0.8034(3) 0.63223(12) 0.51166(14) 0.0428(5) Uani 1 1 d D . . . .
C21 C 0.6989(9) 0.5341(5) 0.6013(5) 0.0626(18) Uani 0.637(7) 1 d . U P A 1
H21A H 0.7842 0.5500 0.6457 0.075 Uiso 0.637(7) 1 calc R . P A 1
H21B H 0.6039 0.5294 0.6298 0.075 Uiso 0.637(7) 1 calc R . P A 1
C22 C 0.7368(5) 0.4603(2) 0.5640(3) 0.0655(16) Uani 0.637(7) 1 d . U P A 1
H22A H 0.6566 0.4469 0.5165 0.098 Uiso 0.637(7) 1 calc GR . P A 1
H22B H 0.7422 0.4217 0.6093 0.098 Uiso 0.637(7) 1 calc GR . P A 1
H22C H 0.8367 0.4638 0.5417 0.098 Uiso 0.637(7) 1 calc GR . P A 1
C23 C 0.87877(18) 0.81114(10) 0.40377(10) 0.0244(3) Uani 1 1 d . . . . .
C24 C 0.8135(2) 0.84442(10) 0.47406(11) 0.0290(4) Uani 1 1 d . . . . .
H24 H 0.7739 0.8131 0.5157 0.035 Uiso 1 1 calc R . . . .
C25 C 0.8066(2) 0.92347(10) 0.48302(12) 0.0326(4) Uani 1 1 d . . . . .
H25 H 0.7633 0.9447 0.5307 0.039 Uiso 1 1 calc R . . . .
C26 C 0.8639(2) 0.97090(11) 0.42158(12) 0.0334(4) Uani 1 1 d . . . . .
H26 H 0.8590 1.0240 0.4274 0.040 Uiso 1 1 calc R . . . .
C27 C 0.9282(2) 0.93870(11) 0.35158(13) 0.0360(4) Uani 1 1 d . . . . .
H27 H 0.9666 0.9703 0.3098 0.043 Uiso 1 1 calc R . . . .
C28 C 0.9364(2) 0.85956(11) 0.34269(12) 0.0322(4) Uani 1 1 d . . . . .
H28 H 0.9810 0.8387 0.2953 0.039 Uiso 1 1 calc R . . . .
O3A O 0.6995(16) 0.5870(10) 0.5441(11) 0.044(2) Uani 0.363(7) 1 d D U P A 2
C21A C 0.7462(15) 0.5457(9) 0.6208(9) 0.059(3) Uani 0.363(7) 1 d . U P A 2
H21C H 0.7341 0.5762 0.6729 0.070 Uiso 0.363(7) 1 calc R . P A 2
H21D H 0.8556 0.5302 0.6233 0.070 Uiso 0.363(7) 1 calc R . P A 2
C22A C 0.6432(11) 0.4786(4) 0.6161(6) 0.067(3) Uani 0.363(7) 1 d . U P A 2
H22D H 0.6559 0.4494 0.5638 0.101 Uiso 0.363(7) 1 calc GR . P A 2
H22E H 0.5355 0.4949 0.6137 0.101 Uiso 0.363(7) 1 calc GR . P A 2
H22F H 0.6704 0.4472 0.6677 0.101 Uiso 0.363(7) 1 calc GR . P A 2
O2A O 0.928(2) 0.6128(7) 0.5398(11) 0.058(2) Uani 0.363(7) 1 d . U P A 2


_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 C6 1.222(2) . ?
O2 C20 1.259(9) . ?
O3 C20 1.349(6) . ?
O3 C21 1.502(10) . ?
N1 N2 1.4003(17) . ?
N1 C1 1.467(2) . ?
N1 C8 1.413(2) . ?
N2 C5 1.480(2) . ?
N2 C6 1.371(2) . ?
C1 C2 1.561(2) . ?
C1 C19 1.509(2) . ?
C2 C3 1.495(2) . ?
C3 C4 1.333(2) . ?
C4 C5 1.511(2) . ?
C4 C20 1.479(2) . ?
C5 C23 1.529(2) . ?
C6 C7 1.499(2) . ?
C8 C9 1.391(2) . ?
C8 C13 1.413(2) . ?
C9 C10 1.384(3) . ?
C10 C11 1.388(3) . ?
C11 C12 1.381(3) . ?
C12 C13 1.395(2) . ?
C13 C14 1.476(2) . ?
C14 C15 1.404(2) . ?
C14 C19 1.398(2) . ?
C15 C16 1.387(3) . ?
C16 C17 1.378(3) . ?
C17 C18 1.385(3) . ?
C18 C19 1.393(2) . ?
C20 O3A 1.328(8) . ?
C20 O2A 1.147(18) . ?
C21 C22 1.458(9) . ?
C23 C24 1.392(2) . ?
C23 C28 1.389(2) . ?
C24 C25 1.386(3) . ?
C25 C26 1.381(3) . ?
C26 C27 1.376(3) . ?
C27 C28 1.388(3) . ?
O3A C21A 1.385(18) . ?
C21A C22A 1.460(14) . ?

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
C20 O3 C21 116.4(6) . . ?
N2 N1 C1 114.75(12) . . ?
N2 N1 C8 117.25(13) . . ?
C8 N1 C1 117.81(13) . . ?
N1 N2 C5 120.64(12) . . ?
C6 N2 N1 119.29(13) . . ?
C6 N2 C5 120.08(13) . . ?
N1 C1 C2 114.34(13) . . ?
N1 C1 C19 107.81(13) . . ?
C19 C1 C2 110.82(13) . . ?
C3 C2 C1 115.46(14) . . ?
C4 C3 C2 124.90(16) . . ?
C3 C4 C5 122.56(15) . . ?
C3 C4 C20 121.64(17) . . ?
C20 C4 C5 115.80(15) . . ?
N2 C5 C4 109.83(13) . . ?
N2 C5 C23 112.65(13) . . ?
C4 C5 C23 113.44(13) . . ?
O1 C6 N2 119.91(15) . . ?
O1 C6 C7 122.54(15) . . ?
N2 C6 C7 117.55(14) . . ?
N1 C8 C13 116.70(14) . . ?
C9 C8 N1 123.04(14) . . ?
C9 C8 C13 120.14(15) . . ?
C10 C9 C8 120.59(16) . . ?
C9 C10 C11 119.88(17) . . ?
C12 C11 C10 119.79(17) . . ?
C11 C12 C13 121.72(17) . . ?
C8 C13 C14 118.67(15) . . ?
C12 C13 C8 117.88(16) . . ?
C12 C13 C14 123.44(15) . . ?
C15 C14 C13 122.65(17) . . ?
C19 C14 C13 119.02(14) . . ?
C19 C14 C15 118.33(16) . . ?
C16 C15 C14 120.74(19) . . ?
C17 C16 C15 120.33(17) . . ?
C16 C17 C18 119.69(18) . . ?
C17 C18 C19 120.64(19) . . ?
C14 C19 C1 119.68(14) . . ?
C18 C19 C1 120.09(16) . . ?
C18 C19 C14 120.17(16) . . ?
O2 C20 O3 129.7(6) . . ?
O2 C20 C4 121.1(4) . . ?
O3 C20 C4 108.5(4) . . ?
O3A C20 C4 121.9(7) . . ?
O2A C20 C4 127.1(9) . . ?
O2A C20 O3A 108.6(11) . . ?
C22 C21 O3 109.6(7) . . ?
C24 C23 C5 119.76(14) . . ?
C28 C23 C5 122.17(15) . . ?
C28 C23 C24 117.98(16) . . ?
C25 C24 C23 121.03(16) . . ?
C26 C25 C24 120.35(17) . . ?
C27 C26 C25 119.19(17) . . ?
C26 C27 C28 120.66(17) . . ?
C27 C28 C23 120.79(16) . . ?
C20 O3A C21A 119.0(11) . . ?
O3A C21A C22A 105.5(9) . . ?

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
O2 C20 O3A C21A -5(2) . . . . ?
O3 C20 O3A C21A -177(8) . . . . ?
N1 N2 C5 C4 32.35(19) . . . . ?
N1 N2 C5 C23 -95.14(16) . . . . ?
N1 N2 C6 O1 -177.44(16) . . . . ?
N1 N2 C6 C7 3.6(2) . . . . ?
N1 C1 C2 C3 0.3(2) . . . . ?
N1 C1 C19 C14 32.71(19) . . . . ?
N1 C1 C19 C18 -150.16(15) . . . . ?
N1 C8 C9 C10 -176.53(15) . . . . ?
N1 C8 C13 C12 176.81(15) . . . . ?
N1 C8 C13 C14 -2.0(2) . . . . ?
N2 N1 C1 C2 -73.32(17) . . . . ?
N2 N1 C1 C19 162.96(13) . . . . ?
N2 N1 C8 C9 -1.8(2) . . . . ?
N2 N1 C8 C13 -177.72(13) . . . . ?
N2 C5 C23 C24 160.22(14) . . . . ?
N2 C5 C23 C28 -23.3(2) . . . . ?
C1 N1 N2 C5 53.86(19) . . . . ?
C1 N1 N2 C6 -126.01(16) . . . . ?
C1 N1 C8 C9 -145.30(15) . . . . ?
C1 N1 C8 C13 38.8(2) . . . . ?
C1 C2 C3 C4 49.0(2) . . . . ?
C2 C1 C19 C14 -93.12(18) . . . . ?
C2 C1 C19 C18 84.01(19) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C2 C3 C4 C20 179.35(17) . . . . ?
C3 C4 C5 N2 -64.3(2) . . . . ?
C3 C4 C5 C23 62.8(2) . . . . ?
C3 C4 C20 O2 -165.2(6) . . . . ?
C3 C4 C20 O3 5.9(6) . . . . ?
C3 C4 C20 O3A 5.7(12) . . . . ?
C3 C4 C20 O2A 166.1(8) . . . . ?
C4 C5 C23 C24 34.7(2) . . . . ?
C4 C5 C23 C28 -148.82(16) . . . . ?
C4 C20 O3A C21A -176.3(13) . . . . ?
C5 N2 C6 O1 2.7(3) . . . . ?
C5 N2 C6 C7 -176.24(16) . . . . ?
C5 C4 C20 O2 14.9(6) . . . . ?
C5 C4 C20 O3 -174.1(6) . . . . ?
C5 C4 C20 O3A -174.3(11) . . . . ?
C5 C4 C20 O2A -13.9(8) . . . . ?
C5 C23 C24 C25 176.45(15) . . . . ?
C5 C23 C28 C27 -176.85(16) . . . . ?
C6 N2 C5 C4 -147.79(15) . . . . ?
C6 N2 C5 C23 84.72(18) . . . . ?
C8 N1 N2 C5 -90.74(17) . . . . ?
C8 N1 N2 C6 89.39(18) . . . . ?
C8 N1 C1 C2 71.08(18) . . . . ?
C8 N1 C1 C19 -52.64(18) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
C8 C13 C14 C15 162.21(16) . . . . ?
C8 C13 C14 C19 -16.6(2) . . . . ?
C9 C8 C13 C12 0.8(2) . . . . ?
C9 C8 C13 C14 -178.00(15) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C12 C13 C8 -0.6(3) . . . . ?
C11 C12 C13 C14 178.13(17) . . . . ?
C12 C13 C14 C15 -16.5(3) . . . . ?
C12 C13 C14 C19 164.70(16) . . . . ?
C13 C8 C9 C10 -0.7(2) . . . . ?
C13 C14 C15 C16 177.96(16) . . . . ?
C13 C14 C19 C1 -0.7(2) . . . . ?
C13 C14 C19 C18 -177.81(15) . . . . ?
C14 C15 C16 C17 0.7(3) . . . . ?
C15 C14 C19 C1 -179.55(15) . . . . ?
C15 C14 C19 C18 3.3(2) . . . . ?
C15 C16 C17 C18 1.7(3) . . . . ?
C16 C17 C18 C19 -1.6(3) . . . . ?
C17 C18 C19 C1 -178.07(16) . . . . ?
C17 C18 C19 C14 -1.0(3) . . . . ?
C19 C1 C2 C3 122.42(16) . . . . ?
C19 C14 C15 C16 -3.2(3) . . . . ?
C20 O3 C21 C22 -89.7(10) . . . . ?
C20 C4 C5 N2 115.71(16) . . . . ?
C20 C4 C5 C23 -117.25(17) . . . . ?
C20 O3A C21A C22A -153.6(16) . . . . ?
C21 O3 C20 O2 -15.4(14) . . . . ?
C21 O3 C20 C4 174.5(7) . . . . ?
C21 O3 C20 O3A -6(6) . . . . ?
C21 O3 C20 O2A 13.0(15) . . . . ?
C23 C24 C25 C26 0.5(3) . . . . ?
C24 C23 C28 C27 -0.3(3) . . . . ?
C24 C25 C26 C27 -0.2(3) . . . . ?
C25 C26 C27 C28 -0.3(3) . . . . ?
C26 C27 C28 C23 0.5(3) . . . . ?
C28 C23 C24 C25 -0.2(2) . . . . ?
O2A C20 O3A C21A 20(2) . . . . ?

####################################################################### 
# 
# 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_sa3623
_database_code_depnum_ccdc_archive 'CCDC 1049477'
_audit_update_record             
;
2015-02-14 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;
_audit_creation_date             2014-09-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H23 Br N2 O3'
_chemical_formula_sum            'C24 H23 Br N2 O3'
_chemical_formula_weight         467.35
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3145(19)
_cell_length_b                   9.4037(19)
_cell_length_c                   12.365(3)
_cell_angle_alpha                103.68(3)
_cell_angle_beta                 92.51(3)
_cell_angle_gamma                95.23(3)
_cell_volume                     1045.6(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3547
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4808
_cell_measurement_theta_min      1.6989
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.995
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13133
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         1.699
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             4763
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0358
_diffrn_orient_matrix_UB_12      0.1010
_diffrn_orient_matrix_UB_13      0.0139
_diffrn_orient_matrix_UB_21      0.0244
_diffrn_orient_matrix_UB_22      -0.0111
_diffrn_orient_matrix_UB_23      0.1067
_diffrn_orient_matrix_UB_31      0.0803
_diffrn_orient_matrix_UB_32      -0.0224
_diffrn_orient_matrix_UB_33      0.0001
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4396
_reflns_number_total             4757
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2013)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2013)'
_computing_structure_solution    
;
 'XS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0257P)²+0.6813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0802
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C17(H17), C18(H18),
 C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.13993(3) 1.24957(2) 0.13647(2) 0.04039(9) Uani 1 1 d . . . . .
O1 O -0.10046(16) 0.57590(17) 0.35541(13) 0.0333(3) Uani 1 1 d . . . . .
O2 O 0.27022(15) 0.56696(15) 0.12615(11) 0.0258(3) Uani 1 1 d . . . . .
O3 O 0.48876(17) 0.5302(2) 0.19106(13) 0.0429(4) Uani 1 1 d . . . . .
N1 N 0.17908(18) 0.81583(17) 0.51866(13) 0.0239(3) Uani 1 1 d . . . . .
N2 N 0.10580(17) 0.72177(17) 0.42542(13) 0.0216(3) Uani 1 1 d . . . . .
C1 C 0.3570(2) 1.0338(3) 0.91043(18) 0.0373(5) Uani 1 1 d . . . . .
H1 H 0.3774 1.0954 0.9813 0.045 Uiso 1 1 calc R . . . .
C2 C 0.3397(2) 1.0937(2) 0.81927(18) 0.0317(5) Uani 1 1 d . . . . .
H2 H 0.3484 1.1953 0.8292 0.038 Uiso 1 1 calc R . . . .
C3 C 0.3090(2) 1.0022(2) 0.71221(17) 0.0258(4) Uani 1 1 d . . . . .
C4 C 0.3023(2) 0.8489(2) 0.69893(16) 0.0263(4) Uani 1 1 d . . . . .
C5 C 0.3189(2) 0.7902(3) 0.79114(18) 0.0336(5) Uani 1 1 d . . . . .
H5 H 0.3129 0.6887 0.7820 0.040 Uiso 1 1 calc R . . . .
C6 C 0.3442(2) 0.8829(3) 0.89671(19) 0.0394(5) Uani 1 1 d . . . . .
H6 H 0.3526 0.8434 0.9587 0.047 Uiso 1 1 calc R . . . .
C7 C 0.2796(2) 0.7504(2) 0.58192(16) 0.0263(4) Uani 1 1 d . . . . .
H7 H 0.2357 0.6532 0.5860 0.032 Uiso 1 1 calc R . . . .
C8 C 0.1958(2) 0.9657(2) 0.52735(16) 0.0254(4) Uani 1 1 d . . . . .
H8 H 0.1580 1.0027 0.4700 0.031 Uiso 1 1 calc R . . . .
C9 C 0.2658(2) 1.0587(2) 0.61740(17) 0.0284(4) Uani 1 1 d . . . . .
H9 H 0.2864 1.1579 0.6191 0.034 Uiso 1 1 calc R . . . .
C10 C 0.4231(2) 0.7331(2) 0.52745(18) 0.0318(5) Uani 1 1 d . . . . .
H10A H 0.4732 0.8306 0.5364 0.038 Uiso 1 1 calc R . . . .
H10B H 0.4812 0.6808 0.5689 0.038 Uiso 1 1 calc R . . . .
C11 C 0.4188(2) 0.6552(2) 0.40608(18) 0.0291(4) Uani 1 1 d . . . . .
H11 H 0.5009 0.6083 0.3864 0.035 Uiso 1 1 calc R . . . .
C12 C 0.3210(2) 0.6398(2) 0.32087(16) 0.0240(4) Uani 1 1 d . . . . .
C13 C 0.1722(2) 0.6926(2) 0.31748(15) 0.0213(4) Uani 1 1 d . . . . .
H13 H 0.1095 0.6127 0.2671 0.026 Uiso 1 1 calc R . . . .
C14 C -0.0312(2) 0.6585(2) 0.43552(16) 0.0246(4) Uani 1 1 d . . . . .
C15 C -0.0885(2) 0.6939(2) 0.54961(18) 0.0332(5) Uani 1 1 d . . . . .
H15A H -0.1882 0.6549 0.5447 0.050 Uiso 1 1 calc GR . . . .
H15B H -0.0804 0.7987 0.5784 0.050 Uiso 1 1 calc GR . . . .
H15C H -0.0336 0.6506 0.5986 0.050 Uiso 1 1 calc GR . . . .
C16 C 0.1706(2) 0.8262(2) 0.26729(15) 0.0207(4) Uani 1 1 d . . . . .
C17 C 0.0403(2) 0.8564(2) 0.22322(16) 0.0254(4) Uani 1 1 d . . . . .
H17 H -0.0424 0.7924 0.2217 0.031 Uiso 1 1 calc R . . . .
C18 C 0.0309(2) 0.9798(2) 0.18140(17) 0.0279(4) Uani 1 1 d . . . . .
H18 H -0.0567 0.9986 0.1516 0.033 Uiso 1 1 calc R . . . .
C19 C 0.1548(2) 1.0743(2) 0.18493(17) 0.0266(4) Uani 1 1 d . . . . .
C20 C 0.2870(2) 1.0470(2) 0.22637(17) 0.0287(4) Uani 1 1 d . . . . .
H20 H 0.3696 1.1107 0.2267 0.034 Uiso 1 1 calc R . . . .
C21 C 0.2937(2) 0.9219(2) 0.26760(17) 0.0257(4) Uani 1 1 d . . . . .
H21 H 0.3820 0.9021 0.2958 0.031 Uiso 1 1 calc R . . . .
C22 C 0.3710(2) 0.5718(2) 0.20796(17) 0.0273(4) Uani 1 1 d . . . . .
C23 C 0.3111(2) 0.5148(2) 0.01262(17) 0.0297(4) Uani 1 1 d . . . . .
H23A H 0.3449 0.4184 0.0028 0.036 Uiso 1 1 calc R . . . .
H23B H 0.3881 0.5819 -0.0034 0.036 Uiso 1 1 calc R . . . .
C24 C 0.1808(2) 0.5070(3) -0.06378(18) 0.0365(5) Uani 1 1 d . . . . .
H24A H 0.1064 0.4379 -0.0489 0.055 Uiso 1 1 calc GR . . . .
H24B H 0.2054 0.4757 -0.1397 0.055 Uiso 1 1 calc GR . . . .
H24C H 0.1466 0.6024 -0.0520 0.055 Uiso 1 1 calc GR . . . .


_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
Br1 C19 1.896(2) . ?
O1 C14 1.221(3) . ?
O2 C22 1.339(3) . ?
O2 C23 1.453(2) . ?
O3 C22 1.208(2) . ?
N1 N2 1.384(2) . ?
N1 C7 1.461(2) . ?
N1 C8 1.382(2) . ?
N2 C13 1.473(2) . ?
N2 C14 1.381(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.384(3) . ?
C1 C6 1.382(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.399(3) . ?
C3 C4 1.407(3) . ?
C3 C9 1.453(3) . ?
C4 C5 1.388(3) . ?
C4 C7 1.517(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C10 1.527(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.342(3) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.503(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.335(3) . ?
C12 C13 1.516(3) . ?
C12 C22 1.505(3) . ?
C13 H13 0.9800 . ?
C13 C16 1.528(3) . ?
C14 C15 1.504(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.388(3) . ?
C16 C21 1.391(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(3) . ?
C19 C20 1.382(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.393(3) . ?
C21 H21 0.9300 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.490(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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 O2 C23 116.61(15) . . ?
N2 N1 C7 116.18(15) . . ?
C8 N1 N2 120.08(16) . . ?
C8 N1 C7 119.82(16) . . ?
N1 N2 C13 120.32(15) . . ?
C14 N2 N1 118.63(16) . . ?
C14 N2 C13 121.04(16) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C6 C1 C2 120.4(2) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 118.6(2) . . ?
C2 C3 C9 122.12(19) . . ?
C4 C3 C9 118.78(18) . . ?
C3 C4 C7 118.52(18) . . ?
C5 C4 C3 120.39(19) . . ?
C5 C4 C7 121.08(19) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 120.3(2) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N1 C7 C4 107.45(16) . . ?
N1 C7 H7 108.9 . . ?
N1 C7 C10 111.74(16) . . ?
C4 C7 H7 108.9 . . ?
C4 C7 C10 110.91(17) . . ?
C10 C7 H7 108.9 . . ?
N1 C8 H8 119.5 . . ?
C9 C8 N1 120.95(19) . . ?
C9 C8 H8 119.5 . . ?
C3 C9 H9 120.5 . . ?
C8 C9 C3 119.01(18) . . ?
C8 C9 H9 120.5 . . ?
C7 C10 H10A 107.8 . . ?
C7 C10 H10B 107.8 . . ?
H10A C10 H10B 107.1 . . ?
C11 C10 C7 118.00(18) . . ?
C11 C10 H10A 107.8 . . ?
C11 C10 H10B 107.8 . . ?
C10 C11 H11 113.5 . . ?
C12 C11 C10 132.91(19) . . ?
C12 C11 H11 113.5 . . ?
C11 C12 C13 130.53(18) . . ?
C11 C12 C22 115.07(17) . . ?
C22 C12 C13 114.12(17) . . ?
N2 C13 C12 114.51(16) . . ?
N2 C13 H13 106.5 . . ?
N2 C13 C16 110.13(15) . . ?
C12 C13 H13 106.5 . . ?
C12 C13 C16 112.25(15) . . ?
C16 C13 H13 106.5 . . ?
O1 C14 N2 120.99(18) . . ?
O1 C14 C15 122.08(18) . . ?
N2 C14 C15 116.91(18) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C13 118.80(16) . . ?
C17 C16 C21 118.64(18) . . ?
C21 C16 C13 122.51(17) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.39(18) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 H18 120.7 . . ?
C19 C18 C17 118.55(19) . . ?
C19 C18 H18 120.7 . . ?
C18 C19 Br1 118.64(16) . . ?
C20 C19 Br1 119.47(15) . . ?
C20 C19 C18 121.85(18) . . ?
C19 C20 H20 120.7 . . ?
C19 C20 C21 118.51(18) . . ?
C21 C20 H20 120.7 . . ?
C16 C21 C20 121.03(19) . . ?
C16 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
O2 C22 C12 111.75(16) . . ?
O3 C22 O2 123.17(19) . . ?
O3 C22 C12 125.04(19) . . ?
O2 C23 H23A 110.2 . . ?
O2 C23 H23B 110.2 . . ?
O2 C23 C24 107.64(16) . . ?
H23A C23 H23B 108.5 . . ?
C24 C23 H23A 110.2 . . ?
C24 C23 H23B 110.2 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
Br1 C19 C20 C21 176.26(15) . . . . ?
N1 N2 C13 C12 54.0(2) . . . . ?
N1 N2 C13 C16 -73.6(2) . . . . ?
N1 N2 C14 O1 179.36(17) . . . . ?
N1 N2 C14 C15 -1.9(2) . . . . ?
N1 C7 C10 C11 -52.3(2) . . . . ?
N1 C8 C9 C3 -7.4(3) . . . . ?
N2 N1 C7 C4 -158.36(16) . . . . ?
N2 N1 C7 C10 79.8(2) . . . . ?
N2 N1 C8 C9 179.63(18) . . . . ?
N2 C13 C16 C17 -73.1(2) . . . . ?
N2 C13 C16 C21 104.6(2) . . . . ?
C1 C2 C3 C4 -2.6(3) . . . . ?
C1 C2 C3 C9 169.31(19) . . . . ?
C2 C1 C6 C5 2.3(3) . . . . ?
C2 C3 C4 C5 3.1(3) . . . . ?
C2 C3 C4 C7 -175.74(18) . . . . ?
C2 C3 C9 C8 -159.4(2) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C3 C4 C7 N1 -37.5(2) . . . . ?
C3 C4 C7 C10 84.9(2) . . . . ?
C4 C3 C9 C8 12.5(3) . . . . ?
C4 C5 C6 C1 -1.8(3) . . . . ?
C4 C7 C10 C11 -172.18(18) . . . . ?
C5 C4 C7 N1 143.60(19) . . . . ?
C5 C4 C7 C10 -94.0(2) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C7 N1 N2 C13 -85.5(2) . . . . ?
C7 N1 N2 C14 95.7(2) . . . . ?
C7 N1 C8 C9 -23.5(3) . . . . ?
C7 C4 C5 C6 177.9(2) . . . . ?
C7 C10 C11 C12 28.3(3) . . . . ?
C8 N1 N2 C13 72.2(2) . . . . ?
C8 N1 N2 C14 -106.6(2) . . . . ?
C8 N1 C7 C4 43.9(2) . . . . ?
C8 N1 C7 C10 -78.0(2) . . . . ?
C9 C3 C4 C5 -169.10(19) . . . . ?
C9 C3 C4 C7 12.0(3) . . . . ?
C10 C11 C12 C13 -2.7(4) . . . . ?
C10 C11 C12 C22 170.7(2) . . . . ?
C11 C12 C13 N2 -22.2(3) . . . . ?
C11 C12 C13 C16 104.3(2) . . . . ?
C11 C12 C22 O2 -176.70(17) . . . . ?
C11 C12 C22 O3 1.1(3) . . . . ?
C12 C13 C16 C17 158.03(17) . . . . ?
C12 C13 C16 C21 -24.3(2) . . . . ?
C13 N2 C14 O1 0.5(3) . . . . ?
C13 N2 C14 C15 179.27(17) . . . . ?
C13 C12 C22 O2 -2.1(2) . . . . ?
C13 C12 C22 O3 175.6(2) . . . . ?
C13 C16 C17 C18 176.92(18) . . . . ?
C13 C16 C21 C20 -176.62(18) . . . . ?
C14 N2 C13 C12 -127.21(18) . . . . ?
C14 N2 C13 C16 105.17(19) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C17 C16 C21 C20 1.0(3) . . . . ?
C17 C18 C19 Br1 -176.07(15) . . . . ?
C17 C18 C19 C20 1.5(3) . . . . ?
C18 C19 C20 C21 -1.3(3) . . . . ?
C19 C20 C21 C16 0.0(3) . . . . ?
C21 C16 C17 C18 -0.8(3) . . . . ?
C22 O2 C23 C24 175.54(17) . . . . ?
C22 C12 C13 N2 164.25(16) . . . . ?
C22 C12 C13 C16 -69.2(2) . . . . ?
C23 O2 C22 O3 -2.9(3) . . . . ?
C23 O2 C22 C12 174.94(16) . . . . ?

####################################################################### 
# 
# 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_sa3074a
_database_code_depnum_ccdc_archive 'CCDC 1049478'
_audit_update_record             
;
2015-02-14 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 F N2 O3'
_chemical_formula_sum            'C24 H21 F N2 O3'
_chemical_formula_weight         404.43

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'
F F 0.0171 0.0103 '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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.5283(17)
_cell_length_b                   11.326(2)
_cell_length_c                   11.349(2)
_cell_angle_alpha                112.58(3)
_cell_angle_beta                 97.17(3)
_cell_angle_gamma                97.42(3)
_cell_volume                     985.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3389
_cell_measurement_theta_min      1.98
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.56725
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8769
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4483
_reflns_number_gt                3981
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'Olex2 ver 1.1'
_computing_molecular_graphics    'Olex2 ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'

_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)+(0.0448P)²+0.4380P] 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         4483
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1294
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_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
F1 F 0.11149(14) 0.59189(11) 0.49542(12) 0.0409(3) Uani 1 1 d . . .
N1 N -0.40289(17) 0.87005(14) 0.69286(14) 0.0253(3) Uani 1 1 d . . .
N2 N -0.34603(18) 0.98413(14) 0.67977(14) 0.0255(3) Uani 1 1 d . . .
O3 O 0.03653(16) 1.30697(12) 1.02015(12) 0.0335(3) Uani 1 1 d . . .
O2 O 0.08639(17) 1.24934(14) 0.81776(13) 0.0382(3) Uani 1 1 d . . .
O1 O -0.39621(18) 1.17681(14) 0.68802(15) 0.0424(4) Uani 1 1 d . . .
C8 C -0.4678(2) 0.76164(17) 0.57812(17) 0.0284(4) Uani 1 1 d . . .
H8 H -0.4593 0.7656 0.4970 0.034 Uiso 1 1 calc R . .
C13 C -0.1681(2) 1.03160(17) 0.71054(16) 0.0258(4) Uani 1 1 d . . .
H13 H -0.1435 1.0893 0.6644 0.031 Uiso 1 1 calc R . .
C7 C -0.5419(2) 0.65215(18) 0.58095(18) 0.0315(4) Uani 1 1 d . . .
H7 H -0.5844 0.5780 0.5019 0.038 Uiso 1 1 calc R . .
C14 C -0.0870(2) 0.91555(17) 0.65652(16) 0.0257(4) Uani 1 1 d . . .
C5 C -0.4885(2) 0.75511(17) 0.82055(17) 0.0267(4) Uani 1 1 d . . .
C9 C -0.3969(2) 0.87243(17) 0.81632(17) 0.0252(4) Uani 1 1 d . . .
C22 C 0.0092(2) 1.22796(17) 0.89290(17) 0.0278(4) Uani 1 1 d . . .
C10 C -0.3132(2) 0.97739(17) 0.92602(17) 0.0277(4) Uani 1 1 d . . .
H10 H -0.3391 0.9773 1.0050 0.033 Uiso 1 1 calc R . .
C17 C 0.0465(2) 0.69914(18) 0.54899(18) 0.0301(4) Uani 1 1 d . . .
C15 C -0.0237(2) 0.85625(19) 0.73312(18) 0.0313(4) Uani 1 1 d . . .
H15 H -0.0267 0.8909 0.8233 0.038 Uiso 1 1 calc R . .
C19 C -0.0812(2) 0.86332(18) 0.52441(17) 0.0302(4) Uani 1 1 d . . .
H19 H -0.1242 0.9032 0.4711 0.036 Uiso 1 1 calc R . .
C12 C -0.1195(2) 1.11354(17) 0.85426(17) 0.0261(4) Uani 1 1 d . . .
C20 C -0.4488(2) 1.07005(18) 0.68479(17) 0.0304(4) Uani 1 1 d . . .
C11 C -0.1938(2) 1.08671(17) 0.94243(17) 0.0268(4) Uani 1 1 d . . .
H11 H -0.1615 1.1507 1.0291 0.032 Uiso 1 1 calc R . .
C18 C -0.0143(2) 0.75495(18) 0.46957(18) 0.0318(4) Uani 1 1 d . . .
H18 H -0.0103 0.7200 0.3796 0.038 Uiso 1 1 calc R . .
C4 C -0.5578(2) 0.64556(17) 0.70310(18) 0.0293(4) Uani 1 1 d . . .
C16 C 0.0442(2) 0.74676(19) 0.67971(19) 0.0343(4) Uani 1 1 d . . .
H16 H 0.0876 0.7061 0.7321 0.041 Uiso 1 1 calc R . .
C6 C -0.5086(2) 0.74705(19) 0.93832(19) 0.0338(4) Uani 1 1 d . . .
H6 H -0.4631 0.8195 1.0180 0.041 Uiso 1 1 calc R . .
C3 C -0.6424(2) 0.53322(19) 0.7082(2) 0.0362(4) Uani 1 1 d . . .
H3 H -0.6883 0.4596 0.6296 0.043 Uiso 1 1 calc R . .
C1 C -0.5933(3) 0.6358(2) 0.9404(2) 0.0391(5) Uani 1 1 d . . .
H1 H -0.6063 0.6327 1.0211 0.047 Uiso 1 1 calc R . .
C23 C 0.1623(2) 1.42204(18) 1.06233(19) 0.0332(4) Uani 1 1 d . . .
H23A H 0.1343 1.4779 1.0170 0.040 Uiso 1 1 calc R . .
H23B H 0.2660 1.3967 1.0428 0.040 Uiso 1 1 calc R . .
C21 C -0.6238(2) 1.0234(2) 0.6798(2) 0.0372(5) Uani 1 1 d . . .
H21A H -0.6729 0.9590 0.5919 0.056 Uiso 1 1 calc R . .
H21B H -0.6792 1.0974 0.7023 0.056 Uiso 1 1 calc R . .
H21C H -0.6332 0.9833 0.7419 0.056 Uiso 1 1 calc R . .
C2 C -0.6599(3) 0.5279(2) 0.8247(2) 0.0400(5) Uani 1 1 d . . .
H2 H -0.7171 0.4511 0.8265 0.048 Uiso 1 1 calc R . .
C24 C 0.1750(3) 1.4938(2) 1.2063(2) 0.0494(6) Uani 1 1 d . . .
H24A H 0.0700 1.5141 1.2246 0.074 Uiso 1 1 calc R . .
H24B H 0.2548 1.5750 1.2379 0.074 Uiso 1 1 calc R . .
H24C H 0.2085 1.4393 1.2503 0.074 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
F1 C17 1.358(2) . ?
N1 C9 1.385(2) . ?
N1 C8 1.388(2) . ?
N1 N2 1.3894(19) . ?
N2 C20 1.382(2) . ?
N2 C13 1.492(2) . ?
O3 C22 1.345(2) . ?
O3 C23 1.452(2) . ?
O2 C22 1.215(2) . ?
O1 C20 1.219(2) . ?
C8 C7 1.331(3) . ?
C8 H8 0.9500 . ?
C13 C12 1.504(2) . ?
C13 C14 1.518(2) . ?
C13 H13 1.0000 . ?
C7 C4 1.439(3) . ?
C7 H7 0.9500 . ?
C14 C15 1.387(2) . ?
C14 C19 1.395(2) . ?
C5 C6 1.404(3) . ?
C5 C4 1.417(3) . ?
C5 C9 1.473(2) . ?
C9 C10 1.377(3) . ?
C22 C12 1.467(3) . ?
C10 C11 1.433(2) . ?
C10 H10 0.9500 . ?
C17 C18 1.373(3) . ?
C17 C16 1.374(3) . ?
C15 C16 1.391(3) . ?
C15 H15 0.9500 . ?
C19 C18 1.379(3) . ?
C19 H19 0.9500 . ?
C12 C11 1.355(2) . ?
C20 C21 1.504(3) . ?
C11 H11 0.9500 . ?
C18 H18 0.9500 . ?
C4 C3 1.405(3) . ?
C16 H16 0.9500 . ?
C6 C1 1.379(3) . ?
C6 H6 0.9500 . ?
C3 C2 1.371(3) . ?
C3 H3 0.9500 . ?
C1 C2 1.393(3) . ?
C1 H1 0.9500 . ?
C23 C24 1.502(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C2 H2 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
C9 N1 C8 124.77(15) . . ?
C9 N1 N2 119.10(14) . . ?
C8 N1 N2 116.08(14) . . ?
C20 N2 N1 118.53(15) . . ?
C20 N2 C13 120.03(14) . . ?
N1 N2 C13 117.47(14) . . ?
C22 O3 C23 115.78(15) . . ?
C7 C8 N1 120.46(17) . . ?
C7 C8 H8 119.8 . . ?
N1 C8 H8 119.8 . . ?
N2 C13 C12 108.15(14) . . ?
N2 C13 C14 108.73(14) . . ?
C12 C13 C14 116.33(14) . . ?
N2 C13 H13 107.8 . . ?
C12 C13 H13 107.8 . . ?
C14 C13 H13 107.8 . . ?
C8 C7 C4 120.30(17) . . ?
C8 C7 H7 119.9 . . ?
C4 C7 H7 119.9 . . ?
C15 C14 C19 118.64(17) . . ?
C15 C14 C13 122.21(16) . . ?
C19 C14 C13 119.10(16) . . ?
C6 C5 C4 118.23(17) . . ?
C6 C5 C9 122.02(17) . . ?
C4 C5 C9 119.75(16) . . ?
C10 C9 N1 122.23(16) . . ?
C10 C9 C5 123.02(16) . . ?
N1 C9 C5 114.74(15) . . ?
O2 C22 O3 122.55(17) . . ?
O2 C22 C12 123.44(17) . . ?
O3 C22 C12 114.01(16) . . ?
C9 C10 C11 131.54(16) . . ?
C9 C10 H10 114.2 . . ?
C11 C10 H10 114.2 . . ?
F1 C17 C18 118.28(17) . . ?
F1 C17 C16 118.71(17) . . ?
C18 C17 C16 123.01(18) . . ?
C14 C15 C16 120.90(17) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C18 C19 C14 121.38(17) . . ?
C18 C19 H19 119.3 . . ?
C14 C19 H19 119.3 . . ?
C11 C12 C22 121.89(16) . . ?
C11 C12 C13 122.33(16) . . ?
C22 C12 C13 115.73(15) . . ?
O1 C20 N2 119.40(18) . . ?
O1 C20 C21 123.18(18) . . ?
N2 C20 C21 117.36(16) . . ?
C12 C11 C10 130.44(17) . . ?
C12 C11 H11 114.8 . . ?
C10 C11 H11 114.8 . . ?
C17 C18 C19 117.99(17) . . ?
C17 C18 H18 121.0 . . ?
C19 C18 H18 121.0 . . ?
C3 C4 C5 119.33(17) . . ?
C3 C4 C7 121.29(18) . . ?
C5 C4 C7 119.38(17) . . ?
C17 C16 C15 118.07(18) . . ?
C17 C16 H16 121.0 . . ?
C15 C16 H16 121.0 . . ?
C1 C6 C5 121.19(19) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C2 C3 C4 121.21(19) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C6 C1 C2 120.35(19) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
O3 C23 C24 106.92(16) . . ?
O3 C23 H23A 110.3 . . ?
C24 C23 H23A 110.3 . . ?
O3 C23 H23B 110.3 . . ?
C24 C23 H23B 110.3 . . ?
H23A C23 H23B 108.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 C2 C1 119.69(18) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
C9 N1 N2 C20 -84.9(2) . . . . ?
C8 N1 N2 C20 92.87(19) . . . . ?
C9 N1 N2 C13 72.7(2) . . . . ?
C8 N1 N2 C13 -109.53(17) . . . . ?
C9 N1 C8 C7 5.3(3) . . . . ?
N2 N1 C8 C7 -172.28(16) . . . . ?
C20 N2 C13 C12 71.06(19) . . . . ?
N1 N2 C13 C12 -86.19(17) . . . . ?
C20 N2 C13 C14 -161.78(15) . . . . ?
N1 N2 C13 C14 40.96(19) . . . . ?
N1 C8 C7 C4 1.0(3) . . . . ?
N2 C13 C14 C15 -97.77(19) . . . . ?
C12 C13 C14 C15 24.6(2) . . . . ?
N2 C13 C14 C19 79.69(19) . . . . ?
C12 C13 C14 C19 -157.98(16) . . . . ?
C8 N1 C9 C10 171.54(17) . . . . ?
N2 N1 C9 C10 -10.9(2) . . . . ?
C8 N1 C9 C5 -9.2(2) . . . . ?
N2 N1 C9 C5 168.30(14) . . . . ?
C6 C5 C9 C10 5.8(3) . . . . ?
C4 C5 C9 C10 -173.47(17) . . . . ?
C6 C5 C9 N1 -173.39(16) . . . . ?
C4 C5 C9 N1 7.3(2) . . . . ?
C23 O3 C22 O2 1.4(3) . . . . ?
C23 O3 C22 C12 -179.54(15) . . . . ?
N1 C9 C10 C11 -14.9(3) . . . . ?
C5 C9 C10 C11 165.99(18) . . . . ?
C19 C14 C15 C16 -0.1(3) . . . . ?
C13 C14 C15 C16 177.38(17) . . . . ?
C15 C14 C19 C18 0.0(3) . . . . ?
C13 C14 C19 C18 -177.55(16) . . . . ?
O2 C22 C12 C11 174.20(18) . . . . ?
O3 C22 C12 C11 -4.8(3) . . . . ?
O2 C22 C12 C13 -8.3(3) . . . . ?
O3 C22 C12 C13 172.68(15) . . . . ?
N2 C13 C12 C11 34.6(2) . . . . ?
C14 C13 C12 C11 -88.0(2) . . . . ?
N2 C13 C12 C22 -142.87(15) . . . . ?
C14 C13 C12 C22 94.50(19) . . . . ?
N1 N2 C20 O1 171.90(16) . . . . ?
C13 N2 C20 O1 14.9(3) . . . . ?
N1 N2 C20 C21 -10.8(2) . . . . ?
C13 N2 C20 C21 -167.83(15) . . . . ?
C22 C12 C11 C10 -175.59(18) . . . . ?
C13 C12 C11 C10 7.1(3) . . . . ?
C9 C10 C11 C12 -5.6(3) . . . . ?
F1 C17 C18 C19 179.53(16) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C14 C19 C18 C17 0.2(3) . . . . ?
C6 C5 C4 C3 -0.5(3) . . . . ?
C9 C5 C4 C3 178.81(17) . . . . ?
C6 C5 C4 C7 178.72(17) . . . . ?
C9 C5 C4 C7 -1.9(3) . . . . ?
C8 C7 C4 C3 176.82(18) . . . . ?
C8 C7 C4 C5 -2.4(3) . . . . ?
F1 C17 C16 C15 -179.62(17) . . . . ?
C18 C17 C16 C15 0.3(3) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C9 C5 C6 C1 -179.25(18) . . . . ?
C5 C4 C3 C2 0.4(3) . . . . ?
C7 C4 C3 C2 -178.84(19) . . . . ?
C5 C6 C1 C2 0.6(3) . . . . ?
C22 O3 C23 C24 -178.77(17) . . . . ?
C4 C3 C2 C1 0.2(3) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_sa3361
_database_code_depnum_ccdc_archive 'CCDC 1049479'
_audit_update_record             
;
2015-02-14 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;
_audit_creation_date             2014-05-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C26 H22 N2 O3, C2 H6 O S'
_chemical_formula_sum            'C28 H28 N2 O4 S'
_chemical_formula_weight         488.58
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4629(19)
_cell_length_b                   10.003(2)
_cell_length_c                   14.426(3)
_cell_angle_alpha                97.33(3)
_cell_angle_beta                 104.20(3)
_cell_angle_gamma                110.31(3)
_cell_volume                     1207.1(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3987
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4855
_cell_measurement_theta_min      1.4977
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15687
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_min         1.498
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             5523
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0886
_diffrn_orient_matrix_UB_12      -0.0461
_diffrn_orient_matrix_UB_13      0.0638
_diffrn_orient_matrix_UB_21      -0.0390
_diffrn_orient_matrix_UB_22      0.0689
_diffrn_orient_matrix_UB_23      0.0758
_diffrn_orient_matrix_UB_31      -0.0635
_diffrn_orient_matrix_UB_32      0.0232
_diffrn_orient_matrix_UB_33      -0.0289
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4878
_reflns_number_total             5523
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2013)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2013)'
_computing_structure_solution    
;
 'XS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0553
_refine_ls_restrained_S_all      1.151
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0333P)²+0.6801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1145
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C15(H15), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.65965(17) 1.52421(15) 0.85716(11) 0.0369(4) Uani 1 1 d . . . . .
O2 O 0.13986(17) 1.37279(16) 0.64971(11) 0.0339(3) Uani 1 1 d . . . . .
O3 O 0.00346(16) 1.32734(17) 0.75593(11) 0.0318(3) Uani 1 1 d . . . . .
H3 H -0.0585 1.3492 0.7164 0.048 Uiso 1 1 calc GR . . . .
N1 N 0.47234(18) 1.14958(17) 0.84883(11) 0.0235(3) Uani 1 1 d . . . . .
N2 N 0.50951(18) 1.28213(16) 0.82159(11) 0.0218(3) Uani 1 1 d . . . . .
C1 C 0.2680(2) 0.9795(2) 0.89749(13) 0.0222(4) Uani 1 1 d . . . . .
C2 C 0.1277(2) 0.9501(2) 0.92060(15) 0.0294(4) Uani 1 1 d . . . . .
H2 H 0.1125 1.0254 0.9563 0.035 Uiso 1 1 calc R . . . .
C3 C 0.0100(2) 0.8097(2) 0.89095(16) 0.0335(5) Uani 1 1 d . . . . .
H3A H -0.0824 0.7907 0.9081 0.040 Uiso 1 1 calc R . . . .
C4 C 0.0301(2) 0.6981(2) 0.83611(15) 0.0318(5) Uani 1 1 d . . . . .
H4 H -0.0495 0.6043 0.8154 0.038 Uiso 1 1 calc R . . . .
C5 C 0.1688(2) 0.7259(2) 0.81187(14) 0.0278(4) Uani 1 1 d . . . . .
H5 H 0.1810 0.6506 0.7741 0.033 Uiso 1 1 calc R . . . .
C6 C 0.2904(2) 0.8655(2) 0.84350(13) 0.0220(4) Uani 1 1 d . . . . .
C7 C 0.4395(2) 0.8989(2) 0.81866(13) 0.0222(4) Uani 1 1 d . . . . .
C8 C 0.5233(2) 1.0436(2) 0.81416(13) 0.0226(4) Uani 1 1 d . . . . .
C9 C 0.4033(2) 1.1287(2) 0.92971(13) 0.0219(4) Uani 1 1 d . . . . .
H9 H 0.4845 1.1274 0.9863 0.026 Uiso 1 1 calc R . . . .
C10 C 0.4975(2) 0.7926(2) 0.79568(14) 0.0271(4) Uani 1 1 d . . . . .
H10 H 0.4456 0.6974 0.8010 0.033 Uiso 1 1 calc R . . . .
C11 C 0.6306(2) 0.8263(2) 0.76518(14) 0.0315(5) Uani 1 1 d . . . . .
H11 H 0.6701 0.7552 0.7523 0.038 Uiso 1 1 calc R . . . .
C12 C 0.7051(2) 0.9670(2) 0.75398(15) 0.0329(5) Uani 1 1 d . . . . .
H12 H 0.7917 0.9885 0.7305 0.039 Uiso 1 1 calc R . . . .
C13 C 0.6519(2) 1.0753(2) 0.77741(14) 0.0283(4) Uani 1 1 d . . . . .
H13 H 0.7015 1.1689 0.7688 0.034 Uiso 1 1 calc R . . . .
C14 C 0.3591(2) 1.2566(2) 0.96005(13) 0.0246(4) Uani 1 1 d . . . . .
H14A H 0.3156 1.2399 1.0138 0.029 Uiso 1 1 calc R . . . .
H14B H 0.4553 1.3451 0.9850 0.029 Uiso 1 1 calc R . . . .
C15 C 0.2420(2) 1.28298(19) 0.88057(14) 0.0243(4) Uani 1 1 d . . . . .
H15 H 0.1537 1.2884 0.8956 0.029 Uiso 1 1 calc R . . . .
C16 C 0.2490(2) 1.29954(19) 0.79130(13) 0.0222(4) Uani 1 1 d . . . . .
C17 C 0.3784(2) 1.29432(19) 0.74848(13) 0.0215(4) Uani 1 1 d . . . . .
H17 H 0.4215 1.3876 0.7300 0.026 Uiso 1 1 calc R . . . .
C18 C 0.3213(2) 1.1725(2) 0.65652(13) 0.0224(4) Uani 1 1 d . . . . .
C19 C 0.4111(2) 1.1880(2) 0.59237(14) 0.0285(4) Uani 1 1 d . . . . .
H19 H 0.5031 1.2717 0.6063 0.034 Uiso 1 1 calc R . . . .
C20 C 0.3648(3) 1.0801(2) 0.50796(16) 0.0348(5) Uani 1 1 d . . . . .
H20 H 0.4252 1.0920 0.4652 0.042 Uiso 1 1 calc R . . . .
C21 C 0.2293(3) 0.9552(2) 0.48712(16) 0.0393(5) Uani 1 1 d . . . . .
H21 H 0.1976 0.8828 0.4302 0.047 Uiso 1 1 calc R . . . .
C22 C 0.1412(3) 0.9381(2) 0.55108(17) 0.0418(6) Uani 1 1 d . . . . .
H22 H 0.0502 0.8535 0.5374 0.050 Uiso 1 1 calc R . . . .
C23 C 0.1868(2) 1.0460(2) 0.63573(15) 0.0317(5) Uani 1 1 d . . . . .
H23 H 0.1266 1.0331 0.6786 0.038 Uiso 1 1 calc R . . . .
C24 C 0.1259(2) 1.3359(2) 0.72511(14) 0.0242(4) Uani 1 1 d . . . . .
C25 C 0.6428(2) 1.4046(2) 0.87485(15) 0.0274(4) Uani 1 1 d . . . . .
C26 C 0.7651(3) 1.3833(3) 0.95341(17) 0.0406(5) Uani 1 1 d . . . . .
H26A H 0.8651 1.4178 0.9408 0.061 Uiso 1 1 calc GR . . . .
H26B H 0.7326 1.2811 0.9532 0.061 Uiso 1 1 calc GR . . . .
H26C H 0.7756 1.4375 1.0164 0.061 Uiso 1 1 calc GR . . . .
S1 S -0.15342(6) 1.48679(6) 0.56551(4) 0.02896(13) Uani 1 1 d . . . . .
O4 O -0.19557(16) 1.40338(16) 0.64225(10) 0.0314(3) Uani 1 1 d . . . . .
C27 C -0.2921(3) 1.3729(3) 0.45124(16) 0.0470(6) Uani 1 1 d . . . . .
H27A H -0.2709 1.2870 0.4357 0.071 Uiso 1 1 calc GR . . . .
H27B H -0.2828 1.4259 0.4005 0.071 Uiso 1 1 calc GR . . . .
H27C H -0.3976 1.3445 0.4558 0.071 Uiso 1 1 calc GR . . . .
C28 C -0.2316(3) 1.6242(3) 0.5744(2) 0.0463(6) Uani 1 1 d . . . . .
H28A H -0.3378 1.5814 0.5774 0.069 Uiso 1 1 calc GR . . . .
H28B H -0.2328 1.6654 0.5178 0.069 Uiso 1 1 calc GR . . . .
H28C H -0.1666 1.7000 0.6328 0.069 Uiso 1 1 calc GR . . . .


_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 C25 1.220(2) . ?
O2 C24 1.215(2) . ?
O3 C24 1.319(2) . ?
N1 N2 1.383(2) . ?
N1 C8 1.394(2) . ?
N1 C9 1.474(2) . ?
N2 C17 1.470(2) . ?
N2 C25 1.376(3) . ?
C1 C2 1.390(3) . ?
C1 C6 1.405(3) . ?
C1 C9 1.512(3) . ?
C2 C3 1.387(3) . ?
C3 C4 1.379(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.396(3) . ?
C6 C7 1.477(3) . ?
C7 C8 1.408(3) . ?
C7 C10 1.395(3) . ?
C8 C13 1.398(3) . ?
C9 C14 1.523(3) . ?
C10 C11 1.382(3) . ?
C11 C12 1.389(3) . ?
C12 C13 1.383(3) . ?
C14 C15 1.507(3) . ?
C15 C16 1.334(3) . ?
C16 C17 1.514(3) . ?
C16 C24 1.496(3) . ?
C17 C18 1.522(3) . ?
C18 C19 1.391(3) . ?
C18 C23 1.382(3) . ?
C19 C20 1.383(3) . ?
C20 C21 1.378(3) . ?
C21 C22 1.376(3) . ?
C22 C23 1.387(3) . ?
C25 C26 1.502(3) . ?
S1 O4 1.5173(15) . ?
S1 C27 1.777(3) . ?
S1 C28 1.778(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
N2 N1 C8 121.60(15) . . ?
N2 N1 C9 119.69(15) . . ?
C8 N1 C9 117.75(15) . . ?
N1 N2 C17 114.76(15) . . ?
C25 N2 N1 122.50(16) . . ?
C25 N2 C17 120.88(16) . . ?
C2 C1 C6 119.48(18) . . ?
C2 C1 C9 123.67(17) . . ?
C6 C1 C9 116.83(16) . . ?
C3 C2 C1 120.69(19) . . ?
C4 C3 C2 120.04(19) . . ?
C3 C4 C5 119.98(19) . . ?
C4 C5 C6 120.80(18) . . ?
C1 C6 C7 118.84(17) . . ?
C5 C6 C1 118.96(17) . . ?
C5 C6 C7 122.14(17) . . ?
C8 C7 C6 118.29(16) . . ?
C10 C7 C6 123.06(17) . . ?
C10 C7 C8 118.60(17) . . ?
N1 C8 C7 116.68(16) . . ?
N1 C8 C13 123.36(17) . . ?
C13 C8 C7 119.96(17) . . ?
N1 C9 C1 107.65(15) . . ?
N1 C9 C14 110.56(15) . . ?
C1 C9 C14 115.06(16) . . ?
C11 C10 C7 121.10(19) . . ?
C10 C11 C12 119.61(19) . . ?
C13 C12 C11 120.67(19) . . ?
C12 C13 C8 119.71(19) . . ?
C15 C14 C9 115.93(15) . . ?
C16 C15 C14 128.12(18) . . ?
C15 C16 C17 126.49(17) . . ?
C15 C16 C24 120.02(17) . . ?
C24 C16 C17 113.39(15) . . ?
N2 C17 C16 111.53(15) . . ?
N2 C17 C18 109.11(15) . . ?
C16 C17 C18 114.10(15) . . ?
C19 C18 C17 118.31(17) . . ?
C23 C18 C17 122.77(17) . . ?
C23 C18 C19 118.90(18) . . ?
C20 C19 C18 120.64(19) . . ?
C21 C20 C19 120.1(2) . . ?
C22 C21 C20 119.6(2) . . ?
C21 C22 C23 120.6(2) . . ?
C18 C23 C22 120.2(2) . . ?
O2 C24 O3 122.96(18) . . ?
O2 C24 C16 122.14(17) . . ?
O3 C24 C16 114.89(16) . . ?
O1 C25 N2 120.46(19) . . ?
O1 C25 C26 122.30(19) . . ?
N2 C25 C26 117.24(18) . . ?
O4 S1 C27 105.23(10) . . ?
O4 S1 C28 105.06(11) . . ?
C27 S1 C28 97.67(13) . . ?

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
N1 N2 C17 C16 68.72(19) . . . . ?
N1 N2 C17 C18 -58.24(19) . . . . ?
N1 N2 C25 O1 -169.13(17) . . . . ?
N1 N2 C25 C26 11.7(3) . . . . ?
N1 C8 C13 C12 173.31(18) . . . . ?
N1 C9 C14 C15 58.9(2) . . . . ?
N2 N1 C8 C7 -159.72(16) . . . . ?
N2 N1 C8 C13 21.1(3) . . . . ?
N2 N1 C9 C1 135.75(16) . . . . ?
N2 N1 C9 C14 9.3(2) . . . . ?
N2 C17 C18 C19 -77.4(2) . . . . ?
N2 C17 C18 C23 100.9(2) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C1 C6 C7 C8 -24.6(2) . . . . ?
C1 C6 C7 C10 158.08(17) . . . . ?
C1 C9 C14 C15 -63.3(2) . . . . ?
C2 C1 C6 C5 1.8(3) . . . . ?
C2 C1 C6 C7 179.39(17) . . . . ?
C2 C1 C9 N1 -142.94(18) . . . . ?
C2 C1 C9 C14 -19.2(3) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C4 C5 C6 C1 -2.3(3) . . . . ?
C4 C5 C6 C7 -179.79(18) . . . . ?
C5 C6 C7 C8 152.92(18) . . . . ?
C5 C6 C7 C10 -24.4(3) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C6 C1 C9 N1 38.8(2) . . . . ?
C6 C1 C9 C14 162.54(16) . . . . ?
C6 C7 C8 N1 9.9(2) . . . . ?
C6 C7 C8 C13 -170.86(17) . . . . ?
C6 C7 C10 C11 174.73(18) . . . . ?
C7 C8 C13 C12 -5.8(3) . . . . ?
C7 C10 C11 C12 -2.2(3) . . . . ?
C8 N1 N2 C17 104.20(19) . . . . ?
C8 N1 N2 C25 -91.2(2) . . . . ?
C8 N1 C9 C1 -55.3(2) . . . . ?
C8 N1 C9 C14 178.28(15) . . . . ?
C8 C7 C10 C11 -2.6(3) . . . . ?
C9 N1 N2 C17 -87.26(19) . . . . ?
C9 N1 N2 C25 77.3(2) . . . . ?
C9 N1 C8 C7 31.5(2) . . . . ?
C9 N1 C8 C13 -147.63(18) . . . . ?
C9 C1 C2 C3 -178.22(18) . . . . ?
C9 C1 C6 C5 -179.83(16) . . . . ?
C9 C1 C6 C7 -2.3(2) . . . . ?
C9 C14 C15 C16 -52.6(3) . . . . ?
C10 C7 C8 N1 -172.59(16) . . . . ?
C10 C7 C8 C13 6.6(3) . . . . ?
C10 C11 C12 C13 3.1(3) . . . . ?
C11 C12 C13 C8 1.0(3) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C14 C15 C16 C24 -175.57(17) . . . . ?
C15 C16 C17 N2 -5.5(3) . . . . ?
C15 C16 C17 C18 118.7(2) . . . . ?
C15 C16 C24 O2 169.04(19) . . . . ?
C15 C16 C24 O3 -9.7(3) . . . . ?
C16 C17 C18 C19 157.16(17) . . . . ?
C16 C17 C18 C23 -24.6(3) . . . . ?
C17 N2 C25 O1 -5.5(3) . . . . ?
C17 N2 C25 C26 175.35(17) . . . . ?
C17 C16 C24 O2 -7.5(3) . . . . ?
C17 C16 C24 O3 173.72(16) . . . . ?
C17 C18 C19 C20 179.70(18) . . . . ?
C17 C18 C23 C22 -179.49(19) . . . . ?
C18 C19 C20 C21 -0.6(3) . . . . ?
C19 C18 C23 C22 -1.3(3) . . . . ?
C19 C20 C21 C22 -0.4(3) . . . . ?
C20 C21 C22 C23 0.6(4) . . . . ?
C21 C22 C23 C18 0.3(4) . . . . ?
C23 C18 C19 C20 1.4(3) . . . . ?
C24 C16 C17 N2 170.78(14) . . . . ?
C24 C16 C17 C18 -65.0(2) . . . . ?
C25 N2 C17 C16 -96.1(2) . . . . ?
C25 N2 C17 C18 136.91(17) . . . . ?

