# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_bo3034
_database_code_depnum_ccdc_archive 'CCDC 1448251'
_audit_update_record             
;
2016-01-19 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 N O4'
_chemical_formula_weight         309.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   7.339(2)
_cell_length_b                   19.964(6)
_cell_length_c                   10.771(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.306(5)
_cell_angle_gamma                90.00
_cell_volume                     1529.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    6031
_cell_measurement_theta_min      2.202
_cell_measurement_theta_max      31.497

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            18224
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         31.49
_reflns_number_total             5029
_reflns_number_gt                4516
_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    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0610P)²+0.6900P] 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     SHELXL
_refine_ls_extinction_coef       0.0074(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5029
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1400
_refine_ls_wR_factor_gt          0.1331
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.31181(15) 0.46936(5) 0.09646(9) 0.0293(2) Uani 1 1 d . . .
O2 O 0.24373(16) 0.55435(5) 0.21221(9) 0.0307(2) Uani 1 1 d . . .
O3 O 0.13589(14) 0.61455(5) 0.78501(9) 0.0260(2) Uani 1 1 d . . .
O4 O 0.10126(15) 0.65763(5) 0.55594(9) 0.0300(2) Uani 1 1 d . . .
N1 N 0.34674(18) 0.39839(6) 0.11027(11) 0.0291(3) Uani 1 1 d . . .
C1 C 0.28218(18) 0.46296(6) 0.64145(12) 0.0238(2) Uani 1 1 d . . .
H1 H 0.3215 0.4182 0.6631 0.029 Uiso 1 1 calc R . .
C2 C 0.24216(19) 0.50444(6) 0.73489(12) 0.0239(2) Uani 1 1 d . . .
H2 H 0.2556 0.4883 0.8196 0.029 Uiso 1 1 calc R . .
C3 C 0.18231(17) 0.56982(6) 0.70351(11) 0.0218(2) Uani 1 1 d . . .
C4 C 0.16523(18) 0.59347(6) 0.57685(12) 0.0218(2) Uani 1 1 d . . .
C5 C 0.20796(17) 0.55241(6) 0.48511(11) 0.0216(2) Uani 1 1 d . . .
H5 H 0.1985 0.5690 0.4011 0.026 Uiso 1 1 calc R . .
C6 C 0.26594(17) 0.48559(6) 0.51615(11) 0.0212(2) Uani 1 1 d . . .
C7 C 0.30415(17) 0.43725(6) 0.42638(12) 0.0219(2) Uani 1 1 d . . .
H7 H 0.3371 0.3944 0.4636 0.026 Uiso 1 1 calc R . .
C8 C 0.28037(19) 0.49543(6) 0.20781(12) 0.0236(2) Uani 1 1 d . . .
C9 C 0.30325(17) 0.43968(6) 0.29953(11) 0.0210(2) Uani 1 1 d . . .
C10 C 0.34146(18) 0.38261(6) 0.22607(12) 0.0228(2) Uani 1 1 d . . .
C11 C 0.37162(19) 0.31215(6) 0.26893(12) 0.0234(2) Uani 1 1 d . . .
C12 C 0.5231(2) 0.27596(7) 0.24688(14) 0.0301(3) Uani 1 1 d . . .
H12 H 0.6061 0.2962 0.2028 0.036 Uiso 1 1 calc R . .
C13 C 0.5524(2) 0.21013(7) 0.28967(15) 0.0334(3) Uani 1 1 d . . .
H13 H 0.6555 0.1854 0.2746 0.040 Uiso 1 1 calc R . .
C14 C 0.4316(2) 0.18037(7) 0.35427(13) 0.0301(3) Uani 1 1 d . . .
H14 H 0.4531 0.1356 0.3843 0.036 Uiso 1 1 calc R . .
C15 C 0.2795(2) 0.21593(7) 0.37493(14) 0.0308(3) Uani 1 1 d . . .
H15 H 0.1964 0.1953 0.4185 0.037 Uiso 1 1 calc R . .
C16 C 0.2481(2) 0.28160(7) 0.33208(13) 0.0275(3) Uani 1 1 d . . .
H16 H 0.1431 0.3057 0.3456 0.033 Uiso 1 1 calc R . .
C17 C 0.1610(2) 0.59399(7) 0.91603(12) 0.0294(3) Uani 1 1 d . . .
H17A H 0.0782 0.5560 0.9200 0.035 Uiso 1 1 calc R . .
H17B H 0.1299 0.6313 0.9662 0.035 Uiso 1 1 calc R . .
H17C H 0.2922 0.5807 0.9513 0.035 Uiso 1 1 calc R . .
C18 C 0.1018(3) 0.68671(8) 0.43563(16) 0.0501(5) Uani 1 1 d . . .
H18A H 0.2310 0.6886 0.4260 0.060 Uiso 1 1 calc R . .
H18B H 0.0500 0.7321 0.4313 0.060 Uiso 1 1 calc R . .
H18C H 0.0247 0.6594 0.3667 0.060 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.3782(16) . ?
O1 N1 1.4410(15) . ?
O2 C8 1.2101(16) . ?
O3 C3 1.3534(15) . ?
O3 C17 1.4371(16) . ?
O4 C4 1.3638(15) . ?
O4 C18 1.4208(18) . ?
N1 C10 1.2963(17) . ?
C1 C2 1.3896(18) . ?
C1 C6 1.4001(17) . ?
C1 H1 0.9500 . ?
C2 C3 1.3920(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.4196(17) . ?
C4 C5 1.3783(17) . ?
C5 C6 1.4150(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.4418(17) . ?
C7 C9 1.3655(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.4701(17) . ?
C9 C10 1.4534(17) . ?
C10 C11 1.4800(18) . ?
C11 C12 1.3946(19) . ?
C11 C16 1.4001(19) . ?
C12 C13 1.392(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.3902(19) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C8 O1 N1 110.20(9) . . ?
C3 O3 C17 117.17(11) . . ?
C4 O4 C18 117.13(11) . . ?
C10 N1 O1 106.95(10) . . ?
C2 C1 C6 121.53(12) . . ?
C2 C1 H1 119.2 . . ?
C6 C1 H1 119.2 . . ?
C1 C2 C3 119.57(11) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
O3 C3 C2 125.18(11) . . ?
O3 C3 C4 115.29(11) . . ?
C2 C3 C4 119.52(11) . . ?
O4 C4 C5 124.77(11) . . ?
O4 C4 C3 114.59(11) . . ?
C5 C4 C3 120.63(11) . . ?
C4 C5 C6 119.98(11) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 118.75(11) . . ?
C1 C6 C7 116.49(11) . . ?
C5 C6 C7 124.72(11) . . ?
C9 C7 C6 133.91(12) . . ?
C9 C7 H7 113.0 . . ?
C6 C7 H7 113.0 . . ?
O2 C8 O1 119.20(11) . . ?
O2 C8 C9 134.36(12) . . ?
O1 C8 C9 106.44(11) . . ?
C7 C9 C10 124.26(11) . . ?
C7 C9 C8 132.13(11) . . ?
C10 C9 C8 103.48(10) . . ?
N1 C10 C9 112.89(11) . . ?
N1 C10 C11 119.57(11) . . ?
C9 C10 C11 127.54(11) . . ?
C12 C11 C16 119.73(12) . . ?
C12 C11 C10 120.22(12) . . ?
C16 C11 C10 120.04(12) . . ?
C13 C12 C11 119.81(13) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 120.30(13) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 120.03(13) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.23(13) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 119.88(13) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C8 O1 N1 C10 -1.56(15) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
C17 O3 C3 C2 3.83(19) . . . . ?
C17 O3 C3 C4 -176.64(11) . . . . ?
C1 C2 C3 O3 178.74(12) . . . . ?
C1 C2 C3 C4 -0.77(19) . . . . ?
C18 O4 C4 C5 -8.4(2) . . . . ?
C18 O4 C4 C3 172.94(15) . . . . ?
O3 C3 C4 O4 -1.06(16) . . . . ?
C2 C3 C4 O4 178.50(12) . . . . ?
O3 C3 C4 C5 -179.80(11) . . . . ?
C2 C3 C4 C5 -0.24(19) . . . . ?
O4 C4 C5 C6 -177.35(12) . . . . ?
C3 C4 C5 C6 1.25(19) . . . . ?
C2 C1 C6 C5 0.23(19) . . . . ?
C2 C1 C6 C7 -177.66(12) . . . . ?
C4 C5 C6 C1 -1.24(18) . . . . ?
C4 C5 C6 C7 176.46(12) . . . . ?
C1 C6 C7 C9 179.89(14) . . . . ?
C5 C6 C7 C9 2.1(2) . . . . ?
N1 O1 C8 O2 -178.12(12) . . . . ?
N1 O1 C8 C9 2.30(14) . . . . ?
C6 C7 C9 C10 -177.83(13) . . . . ?
C6 C7 C9 C8 7.1(3) . . . . ?
O2 C8 C9 C7 -5.8(3) . . . . ?
O1 C8 C9 C7 173.70(13) . . . . ?
O2 C8 C9 C10 178.40(16) . . . . ?
O1 C8 C9 C10 -2.11(14) . . . . ?
O1 N1 C10 C9 0.10(15) . . . . ?
O1 N1 C10 C11 179.65(11) . . . . ?
C7 C9 C10 N1 -174.99(12) . . . . ?
C8 C9 C10 N1 1.25(15) . . . . ?
C7 C9 C10 C11 5.5(2) . . . . ?
C8 C9 C10 C11 -178.25(13) . . . . ?
N1 C10 C11 C12 48.20(19) . . . . ?
C9 C10 C11 C12 -132.32(14) . . . . ?
N1 C10 C11 C16 -131.92(14) . . . . ?
C9 C10 C11 C16 47.55(19) . . . . ?
C16 C11 C12 C13 -1.1(2) . . . . ?
C10 C11 C12 C13 178.79(13) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
C12 C13 C14 C15 0.9(2) . . . . ?
C13 C14 C15 C16 -0.5(2) . . . . ?
C14 C15 C16 C11 -0.6(2) . . . . ?
C12 C11 C16 C15 1.4(2) . . . . ?
C10 C11 C16 C15 -178.45(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        31.49
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.201
_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_bo2895
_database_code_depnum_ccdc_archive 'CCDC 1448252'
_audit_update_record             
;
2016-04-09 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 N2 O2'
_chemical_formula_weight         318.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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

_cell_length_a                   12.040(3)
_cell_length_b                   6.7907(14)
_cell_length_c                   19.562(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1599.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    5219
_cell_measurement_theta_min      1.986
_cell_measurement_theta_max      31.502

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.9565
_exptl_absorpt_correction_T_max  0.9966
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            18118
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.38
_diffrn_reflns_theta_max         31.49
_reflns_number_total             5043
_reflns_number_gt                4005
_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    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

During the refinement, the commond OMIT was used to omit some disagreeable
reflections. All the non-H atoms were anisotropically refined. The commond DFIX
was used to restrain the distance between two atoms.

The detailed restraint information are as follows:
OMIT 0 0 2 
DFIX 1.52 .003 C20 C19 C20 C19'
DFIX 1.47 .003 N2 C17 N2 C17'
;

_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)+(0.0396P)²+0.0960P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_number_reflns         5043
_refine_ls_number_parameters     245
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.89598(9) 0.98256(16) 0.47085(6) 0.0426(3) Uani 1 1 d . . .
O2 O 0.94837(9) 0.74607(16) 0.54346(6) 0.0403(3) Uani 1 1 d . . .
N1 N 0.80134(11) 1.03131(19) 0.42858(7) 0.0409(3) Uani 1 1 d . . .
N2 N 0.75128(9) -0.07962(18) 0.67376(7) 0.0340(3) Uani 1 1 d D . .
C1 C 0.74179(11) 0.0817(2) 0.63416(7) 0.0313(3) Uani 1 1 d . A .
C2 C 0.83439(12) 0.2011(3) 0.61819(10) 0.0443(4) Uani 1 1 d . . .
H2 H 0.9052 0.1675 0.6362 0.053 Uiso 1 1 calc R A .
C3 C 0.82441(11) 0.3644(3) 0.57722(10) 0.0427(4) Uani 1 1 d . A .
H3 H 0.8887 0.4400 0.5670 0.051 Uiso 1 1 calc R . .
C4 C 0.72115(11) 0.4223(2) 0.55006(8) 0.0304(3) Uani 1 1 d . . .
C5 C 0.62921(11) 0.3016(2) 0.56600(8) 0.0318(3) Uani 1 1 d . A .
H5 H 0.5585 0.3358 0.5481 0.038 Uiso 1 1 calc R . .
C6 C 0.63778(11) 0.1381(2) 0.60605(8) 0.0324(3) Uani 1 1 d . . .
H6 H 0.5736 0.0611 0.6153 0.039 Uiso 1 1 calc R A .
C7 C 0.70219(11) 0.5876(2) 0.50693(8) 0.0307(3) Uani 1 1 d . A .
H7 H 0.6286 0.5925 0.4895 0.037 Uiso 1 1 calc R . .
C8 C 0.87749(12) 0.8079(2) 0.50490(8) 0.0332(3) Uani 1 1 d . A .
C9 C 0.76687(11) 0.7414(2) 0.48505(7) 0.0293(3) Uani 1 1 d . . .
C10 C 0.72890(12) 0.8923(2) 0.43828(8) 0.0315(3) Uani 1 1 d . A .
C11 C 0.62142(12) 0.8975(2) 0.40173(7) 0.0322(3) Uani 1 1 d . . .
C12 C 0.55105(14) 1.0580(3) 0.40708(8) 0.0424(4) Uani 1 1 d . A .
H12 H 0.5727 1.1684 0.4338 0.051 Uiso 1 1 calc R . .
C13 C 0.44907(15) 1.0592(3) 0.37375(9) 0.0482(4) Uani 1 1 d . . .
H13 H 0.4006 1.1688 0.3786 0.058 Uiso 1 1 calc R A .
C14 C 0.41834(13) 0.9024(3) 0.33386(9) 0.0474(4) Uani 1 1 d . A .
H14 H 0.3489 0.9040 0.3108 0.057 Uiso 1 1 calc R . .
C15 C 0.48832(14) 0.7418(3) 0.32715(11) 0.0513(4) Uani 1 1 d . . .
H15 H 0.4674 0.6338 0.2991 0.062 Uiso 1 1 calc R A .
C16 C 0.58935(13) 0.7392(2) 0.36166(9) 0.0416(4) Uani 1 1 d . A .
H16 H 0.6367 0.6279 0.3577 0.050 Uiso 1 1 calc R . .
C17 C 0.8566(6) -0.151(2) 0.7025(6) 0.040(3) Uani 0.556(6) 1 d PD A 1
H17A H 0.9011 -0.0422 0.7223 0.048 Uiso 0.556(6) 1 calc PR A 1
H17B H 0.9015 -0.2223 0.6682 0.048 Uiso 0.556(6) 1 calc PR A 1
C18 C 0.8108(3) -0.2898(5) 0.75817(17) 0.0399(9) Uani 0.556(6) 1 d P A 1
H18A H 0.8657 -0.3944 0.7683 0.048 Uiso 0.556(6) 1 calc PR A 1
H18B H 0.7966 -0.2151 0.8008 0.048 Uiso 0.556(6) 1 calc PR A 1
C19 C 0.7036(12) -0.3807(18) 0.7323(7) 0.0411(19) Uani 0.556(6) 1 d PD A 1
H19A H 0.6524 -0.4124 0.7704 0.049 Uiso 0.556(6) 1 calc PR A 1
H19B H 0.7177 -0.5010 0.7051 0.049 Uiso 0.556(6) 1 calc PR A 1
C17' C 0.8551(8) -0.142(2) 0.7070(8) 0.040(4) Uani 0.444(6) 1 d PD A 2
H07A H 0.8664 -0.0671 0.7499 0.047 Uiso 0.444(6) 1 calc PR A 2
H07B H 0.9191 -0.1168 0.6765 0.047 Uiso 0.444(6) 1 calc PR A 2
C18' C 0.8452(3) -0.3595(6) 0.7221(3) 0.0427(13) Uani 0.444(6) 1 d P A 2
H18C H 0.8867 -0.3983 0.7636 0.051 Uiso 0.444(6) 1 calc PR A 2
H18D H 0.8687 -0.4420 0.6829 0.051 Uiso 0.444(6) 1 calc PR A 2
C19' C 0.7188(14) -0.363(2) 0.7330(9) 0.047(4) Uani 0.444(6) 1 d PD A 2
H09A H 0.6905 -0.4970 0.7226 0.056 Uiso 0.444(6) 1 calc PR A 2
H09B H 0.7023 -0.3350 0.7816 0.056 Uiso 0.444(6) 1 calc PR A 2
C20 C 0.65915(13) -0.2144(2) 0.68826(8) 0.0385(3) Uani 1 1 d D A .
H20A H 0.6286 -0.2677 0.6451 0.046 Uiso 1 1 calc R B 1
H20B H 0.5991 -0.1439 0.7126 0.046 Uiso 1 1 calc R B 1


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.3785(18) . ?
O1 N1 1.4462(18) . ?
O2 C8 1.2139(18) . ?
N1 C10 1.2989(19) . ?
N2 C1 1.3467(18) . ?
N2 C20 1.4659(19) . ?
N2 C17 1.469(3) . ?
N2 C17' 1.471(3) . ?
C1 C2 1.413(2) . ?
C1 C6 1.420(2) . ?
C2 C3 1.374(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.4080(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.4119(19) . ?
C4 C7 1.423(2) . ?
C5 C6 1.363(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C9 1.371(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.459(2) . ?
C9 C10 1.448(2) . ?
C10 C11 1.479(2) . ?
C11 C12 1.385(2) . ?
C11 C16 1.385(2) . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.371(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.543(14) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.518(16) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.518(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C17' C18' 1.513(18) . ?
C17' H07A 0.9900 . ?
C17' H07B 0.9900 . ?
C18' C19' 1.537(18) . ?
C18' H18C 0.9900 . ?
C18' H18D 0.9900 . ?
C19' C20 1.518(3) . ?
C19' H09A 0.9900 . ?
C19' H09B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?

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
C8 O1 N1 110.24(10) . . ?
C10 N1 O1 106.22(12) . . ?
C1 N2 C20 123.72(12) . . ?
C1 N2 C17 124.1(6) . . ?
C20 N2 C17 112.0(6) . . ?
C1 N2 C17' 124.0(7) . . ?
C20 N2 C17' 112.2(7) . . ?
C17 N2 C17' 4.2(11) . . ?
N2 C1 C2 121.78(13) . . ?
N2 C1 C6 121.12(13) . . ?
C2 C1 C6 117.10(13) . . ?
C3 C2 C1 121.53(14) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 121.52(14) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 116.55(13) . . ?
C3 C4 C7 125.85(13) . . ?
C5 C4 C7 117.58(12) . . ?
C6 C5 C4 122.70(13) . . ?
C6 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C5 C6 C1 120.59(13) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C9 C7 C4 134.02(13) . . ?
C9 C7 H7 113.0 . . ?
C4 C7 H7 113.0 . . ?
O2 C8 O1 118.97(13) . . ?
O2 C8 C9 134.44(14) . . ?
O1 C8 C9 106.57(12) . . ?
C7 C9 C10 123.85(13) . . ?
C7 C9 C8 132.15(14) . . ?
C10 C9 C8 103.73(12) . . ?
N1 C10 C9 113.23(13) . . ?
N1 C10 C11 119.99(13) . . ?
C9 C10 C11 126.76(13) . . ?
C12 C11 C16 118.88(14) . . ?
C12 C11 C10 121.17(14) . . ?
C16 C11 C10 119.94(13) . . ?
C11 C12 C13 120.65(16) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 120.04(16) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.11(16) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 119.75(17) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 120.55(15) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
N2 C17 C18 99.4(6) . . ?
N2 C17 H17A 111.9 . . ?
C18 C17 H17A 111.9 . . ?
N2 C17 H17B 111.9 . . ?
C18 C17 H17B 111.9 . . ?
H17A C17 H17B 109.6 . . ?
C19 C18 C17 108.6(5) . . ?
C19 C18 H18A 110.0 . . ?
C17 C18 H18A 110.0 . . ?
C19 C18 H18B 110.0 . . ?
C17 C18 H18B 110.0 . . ?
H18A C18 H18B 108.4 . . ?
C18 C19 C20 100.7(8) . . ?
C18 C19 H19A 111.6 . . ?
C20 C19 H19A 111.6 . . ?
C18 C19 H19B 111.6 . . ?
C20 C19 H19B 111.6 . . ?
H19A C19 H19B 109.4 . . ?
N2 C17' C18' 107.4(9) . . ?
N2 C17' H07A 110.2 . . ?
C18' C17' H07A 110.2 . . ?
N2 C17' H07B 110.2 . . ?
C18' C17' H07B 110.2 . . ?
H07A C17' H07B 108.5 . . ?
C17' C18' C19' 97.0(7) . . ?
C17' C18' H18C 112.4 . . ?
C19' C18' H18C 112.4 . . ?
C17' C18' H18D 112.4 . . ?
C19' C18' H18D 112.4 . . ?
H18C C18' H18D 109.9 . . ?
C20 C19' C18' 112.1(10) . . ?
C20 C19' H09A 109.2 . . ?
C18' C19' H09A 109.2 . . ?
C20 C19' H09B 109.2 . . ?
C18' C19' H09B 109.2 . . ?
H09A C19' H09B 107.9 . . ?
N2 C20 C19 107.9(6) . . ?
N2 C20 C19' 99.8(8) . . ?
C19 C20 C19' 8.2(13) . . ?
N2 C20 H20A 110.1 . . ?
C19 C20 H20A 110.1 . . ?
C19' C20 H20A 115.1 . . ?
N2 C20 H20B 110.1 . . ?
C19 C20 H20B 110.1 . . ?
C19' C20 H20B 113.0 . . ?
H20A C20 H20B 108.4 . . ?

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
C8 O1 N1 C10 1.07(17) . . . . ?
C20 N2 C1 C2 -176.11(17) . . . . ?
C17 N2 C1 C2 -1.6(7) . . . . ?
C17' N2 C1 C2 3.5(8) . . . . ?
C20 N2 C1 C6 3.3(2) . . . . ?
C17 N2 C1 C6 177.8(6) . . . . ?
C17' N2 C1 C6 -177.1(7) . . . . ?
N2 C1 C2 C3 179.34(17) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C2 C3 C4 C7 -179.58(18) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C7 C4 C5 C6 179.13(14) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
N2 C1 C6 C5 -179.94(14) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
C3 C4 C7 C9 -7.3(3) . . . . ?
C5 C4 C7 C9 174.37(16) . . . . ?
N1 O1 C8 O2 -179.12(13) . . . . ?
N1 O1 C8 C9 -0.73(16) . . . . ?
C4 C7 C9 C10 177.92(15) . . . . ?
C4 C7 C9 C8 -9.1(3) . . . . ?
O2 C8 C9 C7 4.2(3) . . . . ?
O1 C8 C9 C7 -173.87(15) . . . . ?
O2 C8 C9 C10 178.18(17) . . . . ?
O1 C8 C9 C10 0.15(15) . . . . ?
O1 N1 C10 C9 -0.98(17) . . . . ?
O1 N1 C10 C11 -179.65(12) . . . . ?
C7 C9 C10 N1 175.21(15) . . . . ?
C8 C9 C10 N1 0.55(17) . . . . ?
C7 C9 C10 C11 -6.2(2) . . . . ?
C8 C9 C10 C11 179.11(14) . . . . ?
N1 C10 C11 C12 -56.5(2) . . . . ?
C9 C10 C11 C12 124.99(17) . . . . ?
N1 C10 C11 C16 123.92(17) . . . . ?
C9 C10 C11 C16 -54.6(2) . . . . ?
C16 C11 C12 C13 1.1(2) . . . . ?
C10 C11 C12 C13 -178.49(14) . . . . ?
C11 C12 C13 C14 -1.5(3) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C12 C11 C16 C15 0.3(2) . . . . ?
C10 C11 C16 C15 179.82(16) . . . . ?
C14 C15 C16 C11 -1.2(3) . . . . ?
C1 N2 C17 C18 163.2(3) . . . . ?
C20 N2 C17 C18 -21.7(8) . . . . ?
C17' N2 C17 C18 73(17) . . . . ?
N2 C17 C18 C19 33.5(10) . . . . ?
C17 C18 C19 C20 -32.1(11) . . . . ?
C1 N2 C17' C18' -158.0(6) . . . . ?
C20 N2 C17' C18' 21.6(11) . . . . ?
C17 N2 C17' C18' -66(17) . . . . ?
N2 C17' C18' C19' -31.0(12) . . . . ?
C17' C18' C19' C20 32.9(14) . . . . ?
C1 N2 C20 C19 178.0(7) . . . . ?
C17 N2 C20 C19 3.0(9) . . . . ?
C17' N2 C20 C19 -1.6(9) . . . . ?
C1 N2 C20 C19' 179.2(8) . . . . ?
C17 N2 C20 C19' 4.2(10) . . . . ?
C17' N2 C20 C19' -0.4(11) . . . . ?
C18 C19 C20 N2 17.7(10) . . . . ?
C18 C19 C20 C19' 9(9) . . . . ?
C18' C19' C20 N2 -21.2(13) . . . . ?
C18' C19' C20 C19 151(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        31.49
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1448253'
_audit_update_record             
;
2016-04-09 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 N2 O2'
_chemical_formula_weight         416.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   11.550(2)
_cell_length_b                   11.294(2)
_cell_length_c                   33.009(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4305.9(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2642
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      21.05

_exptl_crystal_description       slice
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1744
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9760
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_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            26448
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.23
_diffrn_reflns_theta_max         25.36
_reflns_number_total             3926
_reflns_number_gt                2384
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0593P)²+0.3951P] 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     SHELXL
_refine_ls_extinction_coef       0.0028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3926
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1273
_refine_ls_wR_factor_gt          0.1050
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.74891(14) 0.25398(15) 0.15268(5) 0.0744(5) Uani 1 1 d . . .
O2 O 0.87578(12) 0.18571(13) 0.19804(5) 0.0619(4) Uani 1 1 d . . .
N1 N 0.25595(16) 0.08786(19) 0.06631(6) 0.0688(6) Uani 1 1 d . . .
N2 N 0.88459(14) 0.08989(16) 0.22679(5) 0.0571(5) Uani 1 1 d . . .
C1 C 0.0944(2) 0.0596(3) 0.11314(8) 0.0863(9) Uani 1 1 d . . .
H1 H 0.1342 0.1027 0.1327 0.104 Uiso 1 1 calc R . .
C2 C -0.0131(2) 0.0137(3) 0.12216(9) 0.0919(9) Uani 1 1 d . . .
H2 H -0.0435 0.0233 0.1480 0.110 Uiso 1 1 calc R . .
C3 C -0.0744(2) -0.0448(3) 0.09394(10) 0.0819(8) Uani 1 1 d . . .
H3 H -0.1476 -0.0743 0.0999 0.098 Uiso 1 1 calc R . .
C4 C -0.0278(2) -0.0603(2) 0.05663(9) 0.0811(8) Uani 1 1 d . . .
H4 H -0.0705 -0.0996 0.0369 0.097 Uiso 1 1 calc R . .
C5 C 0.0818(2) -0.01914(19) 0.04719(7) 0.0622(6) Uani 1 1 d . . .
H5 H 0.1131 -0.0333 0.0217 0.075 Uiso 1 1 calc R . .
C6 C 0.14376(18) 0.04247(19) 0.07550(7) 0.0548(6) Uani 1 1 d . . .
C7 C 0.2744(2) 0.1469(2) 0.02887(7) 0.0640(6) Uani 1 1 d . . .
C8 C 0.2041(3) 0.2383(2) 0.01703(9) 0.0886(9) Uani 1 1 d . . .
H8 H 0.1448 0.2644 0.0339 0.106 Uiso 1 1 calc R . .
C9 C 0.2221(4) 0.2919(3) -0.02052(13) 0.1229(16) Uani 1 1 d . . .
H9 H 0.1753 0.3546 -0.0286 0.147 Uiso 1 1 calc R . .
C10 C 0.3083(5) 0.2527(5) -0.04552(12) 0.134(2) Uani 1 1 d . . .
H10 H 0.3197 0.2883 -0.0706 0.161 Uiso 1 1 calc R . .
C11 C 0.3765(3) 0.1623(4) -0.03377(11) 0.1289(15) Uani 1 1 d . . .
H11 H 0.4347 0.1353 -0.0509 0.155 Uiso 1 1 calc R . .
C12 C 0.3609(3) 0.1096(3) 0.00354(9) 0.0940(9) Uani 1 1 d . . .
H12 H 0.4096 0.0483 0.0115 0.113 Uiso 1 1 calc R . .
C13 C 0.34851(19) 0.0693(2) 0.09306(6) 0.0575(6) Uani 1 1 d . . .
C14 C 0.4377(2) 0.1514(2) 0.09616(7) 0.0657(6) Uani 1 1 d . . .
H14 H 0.4372 0.2179 0.0795 0.079 Uiso 1 1 calc R . .
C15 C 0.52656(19) 0.13625(19) 0.12325(7) 0.0595(6) Uani 1 1 d . . .
H15 H 0.5846 0.1931 0.1249 0.071 Uiso 1 1 calc R . .
C16 C 0.53156(16) 0.03713(17) 0.14841(6) 0.0480(5) Uani 1 1 d . . .
C17 C 0.44297(19) -0.0464(2) 0.14412(6) 0.0582(6) Uani 1 1 d . . .
H17 H 0.4451 -0.1146 0.1599 0.070 Uiso 1 1 calc R . .
C18 C 0.35334(19) -0.0312(2) 0.11751(7) 0.0611(6) Uani 1 1 d . . .
H18 H 0.2954 -0.0882 0.1157 0.073 Uiso 1 1 calc R . .
C19 C 0.61755(16) 0.01420(17) 0.17889(6) 0.0472(5) Uani 1 1 d . . .
H19 H 0.6043 -0.0561 0.1928 0.057 Uiso 1 1 calc R . .
C20 C 0.71392(16) 0.07206(17) 0.19197(6) 0.0441(5) Uani 1 1 d . . .
C21 C 0.77206(18) 0.1789(2) 0.17734(7) 0.0532(5) Uani 1 1 d . . .
C22 C 0.79138(16) 0.02774(17) 0.22301(6) 0.0447(5) Uani 1 1 d . . .
C23 C 0.77223(16) -0.07415(17) 0.25023(6) 0.0450(5) Uani 1 1 d . . .
C24 C 0.85561(17) -0.16177(19) 0.25490(7) 0.0582(6) Uani 1 1 d . . .
H24 H 0.9244 -0.1574 0.2403 0.070 Uiso 1 1 calc R . .
C25 C 0.8369(2) -0.2551(2) 0.28097(8) 0.0693(7) Uani 1 1 d . . .
H25 H 0.8932 -0.3134 0.2838 0.083 Uiso 1 1 calc R . .
C26 C 0.7363(2) -0.2630(2) 0.30276(8) 0.0699(7) Uani 1 1 d . . .
H26 H 0.7238 -0.3267 0.3201 0.084 Uiso 1 1 calc R . .
C27 C 0.6539(2) -0.1762(2) 0.29879(7) 0.0628(6) Uani 1 1 d . . .
H27 H 0.5861 -0.1805 0.3139 0.075 Uiso 1 1 calc R . .
C28 C 0.67072(18) -0.08268(18) 0.27260(6) 0.0531(6) Uani 1 1 d . . .
H28 H 0.6138 -0.0250 0.2699 0.064 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C21 1.206(3) . ?
O2 C21 1.381(3) . ?
O2 N2 1.443(2) . ?
N1 C13 1.402(3) . ?
N1 C7 1.420(3) . ?
N1 C6 1.426(3) . ?
N2 C22 1.291(2) . ?
C1 C2 1.378(4) . ?
C1 C6 1.381(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.344(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.356(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(3) . ?
C5 H5 0.9300 . ?
C7 C12 1.370(4) . ?
C7 C8 1.371(4) . ?
C8 C9 1.395(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.347(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.390(3) . ?
C13 C18 1.394(3) . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.395(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.399(3) . ?
C16 C19 1.438(3) . ?
C17 C18 1.369(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.361(3) . ?
C19 H19 0.9300 . ?
C20 C22 1.449(3) . ?
C20 C21 1.463(3) . ?
C22 C23 1.477(3) . ?
C23 C28 1.389(3) . ?
C23 C24 1.389(3) . ?
C24 C25 1.378(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.369(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.372(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.379(3) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?

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
C21 O2 N2 110.16(15) . . ?
C13 N1 C7 120.24(19) . . ?
C13 N1 C6 120.33(18) . . ?
C7 N1 C6 119.35(18) . . ?
C22 N2 O2 106.58(16) . . ?
C2 C1 C6 120.9(3) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.0(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 118.0(2) . . ?
C5 C6 N1 120.9(2) . . ?
C1 C6 N1 121.1(2) . . ?
C12 C7 C8 119.3(3) . . ?
C12 C7 N1 119.8(2) . . ?
C8 C7 N1 120.8(3) . . ?
C7 C8 C9 119.4(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 120.3(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 119.9(4) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.5(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C11 120.5(3) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C18 118.1(2) . . ?
C14 C13 N1 120.8(2) . . ?
C18 C13 N1 121.1(2) . . ?
C15 C14 C13 121.3(2) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 121.28(19) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 116.80(18) . . ?
C15 C16 C19 126.15(18) . . ?
C17 C16 C19 117.03(18) . . ?
C18 C17 C16 122.24(19) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C17 C18 C13 120.3(2) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
C20 C19 C16 134.48(19) . . ?
C20 C19 H19 112.8 . . ?
C16 C19 H19 112.8 . . ?
C19 C20 C22 124.28(18) . . ?
C19 C20 C21 131.82(19) . . ?
C22 C20 C21 103.58(17) . . ?
O1 C21 O2 119.15(19) . . ?
O1 C21 C20 134.5(2) . . ?
O2 C21 C20 106.31(19) . . ?
N2 C22 C20 113.29(18) . . ?
N2 C22 C23 119.32(18) . . ?
C20 C22 C23 127.36(17) . . ?
C28 C23 C24 118.5(2) . . ?
C28 C23 C22 120.26(17) . . ?
C24 C23 C22 121.24(19) . . ?
C25 C24 C23 120.3(2) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C24 120.8(2) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 119.4(2) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 H26 120.3 . . ?
C26 C27 C28 120.6(2) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C27 C28 C23 120.4(2) . . ?
C27 C28 H28 119.8 . . ?
C23 C28 H28 119.8 . . ?

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
C21 O2 N2 C22 0.9(2) . . . . ?
C6 C1 C2 C3 -2.7(5) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 C6 -2.3(4) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C4 C5 C6 N1 -178.8(2) . . . . ?
C2 C1 C6 C5 1.4(4) . . . . ?
C2 C1 C6 N1 -178.8(2) . . . . ?
C13 N1 C6 C5 -131.8(2) . . . . ?
C7 N1 C6 C5 45.0(3) . . . . ?
C13 N1 C6 C1 48.3(3) . . . . ?
C7 N1 C6 C1 -134.8(3) . . . . ?
C13 N1 C7 C12 51.4(3) . . . . ?
C6 N1 C7 C12 -125.5(3) . . . . ?
C13 N1 C7 C8 -130.9(3) . . . . ?
C6 N1 C7 C8 52.2(3) . . . . ?
C12 C7 C8 C9 -0.2(4) . . . . ?
N1 C7 C8 C9 -177.9(2) . . . . ?
C7 C8 C9 C10 0.8(5) . . . . ?
C8 C9 C10 C11 -0.4(6) . . . . ?
C9 C10 C11 C12 -0.6(6) . . . . ?
C8 C7 C12 C11 -0.8(4) . . . . ?
N1 C7 C12 C11 176.9(3) . . . . ?
C10 C11 C12 C7 1.2(5) . . . . ?
C7 N1 C13 C14 33.6(3) . . . . ?
C6 N1 C13 C14 -149.5(2) . . . . ?
C7 N1 C13 C18 -146.9(2) . . . . ?
C6 N1 C13 C18 29.9(3) . . . . ?
C18 C13 C14 C15 -1.8(4) . . . . ?
N1 C13 C14 C15 177.7(2) . . . . ?
C13 C14 C15 C16 0.8(4) . . . . ?
C14 C15 C16 C17 1.1(3) . . . . ?
C14 C15 C16 C19 -177.4(2) . . . . ?
C15 C16 C17 C18 -1.9(3) . . . . ?
C19 C16 C17 C18 176.7(2) . . . . ?
C16 C17 C18 C13 0.8(4) . . . . ?
C14 C13 C18 C17 1.0(3) . . . . ?
N1 C13 C18 C17 -178.4(2) . . . . ?
C15 C16 C19 C20 -1.5(4) . . . . ?
C17 C16 C19 C20 -179.9(2) . . . . ?
C16 C19 C20 C22 -177.5(2) . . . . ?
C16 C19 C20 C21 -5.1(4) . . . . ?
N2 O2 C21 O1 178.23(19) . . . . ?
N2 O2 C21 C20 -2.5(2) . . . . ?
C19 C20 C21 O1 8.5(4) . . . . ?
C22 C20 C21 O1 -177.9(3) . . . . ?
C19 C20 C21 O2 -170.6(2) . . . . ?
C22 C20 C21 O2 2.9(2) . . . . ?
O2 N2 C22 C20 1.1(2) . . . . ?
O2 N2 C22 C23 -176.82(16) . . . . ?
C19 C20 C22 N2 171.63(19) . . . . ?
C21 C20 C22 N2 -2.5(2) . . . . ?
C19 C20 C22 C23 -10.7(3) . . . . ?
C21 C20 C22 C23 175.18(18) . . . . ?
N2 C22 C23 C28 126.1(2) . . . . ?
C20 C22 C23 C28 -51.5(3) . . . . ?
N2 C22 C23 C24 -52.3(3) . . . . ?
C20 C22 C23 C24 130.1(2) . . . . ?
C28 C23 C24 C25 0.5(3) . . . . ?
C22 C23 C24 C25 178.90(19) . . . . ?
C23 C24 C25 C26 -0.2(3) . . . . ?
C24 C25 C26 C27 -0.7(4) . . . . ?
C25 C26 C27 C28 1.2(4) . . . . ?
C26 C27 C28 C23 -0.9(3) . . . . ?
C24 C23 C28 C27 0.1(3) . . . . ?
C22 C23 C28 C27 -178.38(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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_bo3035
_database_code_depnum_ccdc_archive 'CCDC 1448255'
_audit_update_record             
;
2016-01-19 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H15 N O2'
_chemical_formula_weight         337.36

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   Cc

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

_cell_length_a                   24.442(8)
_cell_length_b                   5.6023(19)
_cell_length_c                   11.966(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.638(3)
_cell_angle_gamma                90.00
_cell_volume                     1624.0(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3035
_cell_measurement_theta_min      2.558
_cell_measurement_theta_max      31.482

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8992
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         31.52
_reflns_number_total             4177
_reflns_number_gt                3750
_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    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0526P)²+0.6360P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(12)
_refine_ls_number_reflns         4177
_refine_ls_number_parameters     235
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1111
_refine_ls_wR_factor_gt          0.1060
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.38762(5) 1.2953(2) 0.56477(11) 0.0289(3) Uani 1 1 d . . .
O2 O 0.32174(6) 1.0502(3) 0.60974(11) 0.0349(3) Uani 1 1 d . . .
N1 N 0.42530(7) 1.3102(3) 0.48152(13) 0.0277(3) Uani 1 1 d . . .
C1 C 0.17547(8) 0.1291(3) 0.39991(16) 0.0281(4) Uani 1 1 d . . .
C2 C 0.15159(9) -0.0609(4) 0.33535(17) 0.0354(4) Uani 1 1 d . . .
H2 H 0.1668 -0.1167 0.2711 0.042 Uiso 1 1 calc R . .
C3 C 0.10434(9) -0.1664(4) 0.36888(18) 0.0387(5) Uani 1 1 d . . .
H3 H 0.0870 -0.2961 0.3270 0.046 Uiso 1 1 calc R . .
C4 C 0.08275(8) -0.0820(4) 0.46310(18) 0.0363(5) Uani 1 1 d . . .
H4 H 0.0501 -0.1519 0.4836 0.044 Uiso 1 1 calc R . .
C5 C 0.10782(9) 0.1009(4) 0.52696(17) 0.0341(4) Uani 1 1 d . . .
H5 H 0.0933 0.1538 0.5924 0.041 Uiso 1 1 calc R . .
C6 C 0.15398(8) 0.2063(4) 0.49554(16) 0.0302(4) Uani 1 1 d . . .
C7 C 0.18875(9) 0.4129(4) 0.54956(16) 0.0330(4) Uani 1 1 d . . .
H7A H 0.1660 0.5577 0.5547 0.040 Uiso 1 1 calc R . .
H7B H 0.2069 0.3700 0.6259 0.040 Uiso 1 1 calc R . .
C8 C 0.23067(8) 0.4498(3) 0.46931(15) 0.0256(3) Uani 1 1 d . . .
C9 C 0.27175(8) 0.6209(3) 0.47312(15) 0.0260(4) Uani 1 1 d . . .
H9 H 0.2766 0.7352 0.5322 0.031 Uiso 1 1 calc R . .
C10 C 0.30608(7) 0.6222(3) 0.38801(14) 0.0239(3) Uani 1 1 d . . .
C11 C 0.29791(8) 0.4488(3) 0.30041(15) 0.0274(4) Uani 1 1 d . . .
H11 H 0.3211 0.4510 0.2427 0.033 Uiso 1 1 calc R . .
C12 C 0.25691(8) 0.2767(3) 0.29732(15) 0.0289(4) Uani 1 1 d . . .
H12 H 0.2521 0.1604 0.2390 0.035 Uiso 1 1 calc R . .
C13 C 0.22334(7) 0.2791(3) 0.38122(14) 0.0253(4) Uani 1 1 d . . .
C14 C 0.35075(7) 0.7881(3) 0.38141(14) 0.0221(3) Uani 1 1 d . . .
H14 H 0.3699 0.7601 0.3185 0.027 Uiso 1 1 calc R . .
C15 C 0.35533(8) 1.0937(3) 0.54684(14) 0.0257(3) Uani 1 1 d . . .
C16 C 0.37142(7) 0.9761(3) 0.44586(13) 0.0221(3) Uani 1 1 d . . .
C17 C 0.41573(7) 1.1264(3) 0.41606(14) 0.0219(3) Uani 1 1 d . . .
C18 C 0.44889(7) 1.0873(3) 0.32312(14) 0.0219(3) Uani 1 1 d . . .
C19 C 0.44888(7) 1.2573(3) 0.23776(15) 0.0253(3) Uani 1 1 d . . .
H19 H 0.4275 1.3987 0.2392 0.030 Uiso 1 1 calc R . .
C20 C 0.48019(8) 1.2187(3) 0.15066(15) 0.0279(4) Uani 1 1 d . . .
H20 H 0.4800 1.3335 0.0921 0.034 Uiso 1 1 calc R . .
C21 C 0.51164(8) 1.0145(3) 0.14876(15) 0.0285(4) Uani 1 1 d . . .
H21 H 0.5331 0.9898 0.0891 0.034 Uiso 1 1 calc R . .
C22 C 0.51211(8) 0.8448(3) 0.23357(16) 0.0291(4) Uani 1 1 d . . .
H22 H 0.5341 0.7051 0.2322 0.035 Uiso 1 1 calc R . .
C23 C 0.48048(8) 0.8798(3) 0.32015(14) 0.0252(3) Uani 1 1 d . . .
H23 H 0.4803 0.7627 0.3775 0.030 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.378(2) . ?
O1 N1 1.446(2) . ?
O2 C15 1.210(2) . ?
N1 C17 1.296(2) . ?
C1 C6 1.390(3) . ?
C1 C2 1.397(3) . ?
C1 C13 1.482(3) . ?
C2 C3 1.402(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.370(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.528(3) . ?
C7 C8 1.509(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.384(3) . ?
C8 C13 1.417(3) . ?
C9 C10 1.403(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.424(2) . ?
C10 C14 1.444(2) . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9500 . ?
C14 C16 1.362(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.475(3) . ?
C16 C17 1.453(2) . ?
C17 C18 1.477(2) . ?
C18 C19 1.397(2) . ?
C18 C23 1.399(2) . ?
C19 C20 1.390(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.380(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.390(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O1 N1 110.12(13) . . ?
C17 N1 O1 106.87(14) . . ?
C6 C1 C2 121.11(19) . . ?
C6 C1 C13 109.90(16) . . ?
C2 C1 C13 128.98(19) . . ?
C1 C2 C3 117.5(2) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 120.32(19) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 121.06(19) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 120.45(18) . . ?
C5 C6 C7 130.01(19) . . ?
C1 C6 C7 109.52(17) . . ?
C8 C7 C6 102.78(16) . . ?
C8 C7 H7A 111.2 . . ?
C6 C7 H7A 111.2 . . ?
C8 C7 H7B 111.2 . . ?
C6 C7 H7B 111.2 . . ?
H7A C7 H7B 109.1 . . ?
C9 C8 C13 120.73(18) . . ?
C9 C8 C7 128.68(18) . . ?
C13 C8 C7 110.59(16) . . ?
C8 C9 C10 118.76(16) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C9 C10 C11 119.45(16) . . ?
C9 C10 C14 124.95(16) . . ?
C11 C10 C14 115.59(17) . . ?
C12 C11 C10 121.60(18) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C13 C12 C11 118.12(17) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C12 C13 C8 121.33(17) . . ?
C12 C13 C1 131.52(16) . . ?
C8 C13 C1 107.14(17) . . ?
C16 C14 C10 133.85(17) . . ?
C16 C14 H14 113.1 . . ?
C10 C14 H14 113.1 . . ?
O2 C15 O1 119.35(16) . . ?
O2 C15 C16 134.14(18) . . ?
O1 C15 C16 106.50(16) . . ?
C14 C16 C17 122.78(16) . . ?
C14 C16 C15 133.63(17) . . ?
C17 C16 C15 103.34(15) . . ?
N1 C17 C16 113.11(16) . . ?
N1 C17 C18 120.01(16) . . ?
C16 C17 C18 126.88(15) . . ?
C19 C18 C23 119.64(17) . . ?
C19 C18 C17 120.19(16) . . ?
C23 C18 C17 120.17(15) . . ?
C20 C19 C18 119.74(17) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C21 C20 C19 120.31(17) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 120.37(18) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 119.85(18) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C18 120.08(16) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?

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
C15 O1 N1 C17 0.43(17) . . . . ?
C6 C1 C2 C3 1.7(3) . . . . ?
C13 C1 C2 C3 -176.87(18) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 -1.8(3) . . . . ?
C3 C4 C5 C6 1.9(3) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C4 C5 C6 C7 178.8(2) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
C13 C1 C6 C5 177.13(17) . . . . ?
C2 C1 C6 C7 179.20(18) . . . . ?
C13 C1 C6 C7 -2.0(2) . . . . ?
C5 C6 C7 C8 -176.36(19) . . . . ?
C1 C6 C7 C8 2.7(2) . . . . ?
C6 C7 C8 C9 177.18(19) . . . . ?
C6 C7 C8 C13 -2.4(2) . . . . ?
C13 C8 C9 C10 0.0(3) . . . . ?
C7 C8 C9 C10 -179.54(17) . . . . ?
C8 C9 C10 C11 0.0(2) . . . . ?
C8 C9 C10 C14 -179.52(17) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C14 C10 C11 C12 179.12(16) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C11 C12 C13 C8 -0.9(3) . . . . ?
C11 C12 C13 C1 177.51(18) . . . . ?
C9 C8 C13 C12 0.4(3) . . . . ?
C7 C8 C13 C12 -179.93(16) . . . . ?
C9 C8 C13 C1 -178.28(16) . . . . ?
C7 C8 C13 C1 1.3(2) . . . . ?
C6 C1 C13 C12 -178.12(18) . . . . ?
C2 C1 C13 C12 0.6(3) . . . . ?
C6 C1 C13 C8 0.4(2) . . . . ?
C2 C1 C13 C8 179.12(19) . . . . ?
C9 C10 C14 C16 -1.0(3) . . . . ?
C11 C10 C14 C16 179.50(17) . . . . ?
N1 O1 C15 O2 178.98(15) . . . . ?
N1 O1 C15 C16 -1.71(17) . . . . ?
C10 C14 C16 C17 -176.10(18) . . . . ?
C10 C14 C16 C15 -2.8(3) . . . . ?
O2 C15 C16 C14 7.1(3) . . . . ?
O1 C15 C16 C14 -172.04(17) . . . . ?
O2 C15 C16 C17 -178.64(19) . . . . ?
O1 C15 C16 C17 2.20(17) . . . . ?
O1 N1 C17 C16 1.10(18) . . . . ?
O1 N1 C17 C18 -178.51(13) . . . . ?
C14 C16 C17 N1 172.96(16) . . . . ?
C15 C16 C17 N1 -2.09(19) . . . . ?
C14 C16 C17 C18 -7.5(3) . . . . ?
C15 C16 C17 C18 177.49(15) . . . . ?
N1 C17 C18 C19 -60.5(2) . . . . ?
C16 C17 C18 C19 119.95(19) . . . . ?
N1 C17 C18 C23 119.48(18) . . . . ?
C16 C17 C18 C23 -60.1(2) . . . . ?
C23 C18 C19 C20 0.0(2) . . . . ?
C17 C18 C19 C20 -179.97(16) . . . . ?
C18 C19 C20 C21 -0.6(3) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C20 C21 C22 C23 0.5(3) . . . . ?
C21 C22 C23 C18 -1.1(3) . . . . ?
C19 C18 C23 C22 0.8(2) . . . . ?
C17 C18 C23 C22 -179.20(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        31.52
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_bo3106
_database_code_depnum_ccdc_archive 'CCDC 1448256'
_audit_update_record             
;
2016-01-19 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 N O2 S'
_chemical_formula_weight         295.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Cc

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

_cell_length_a                   20.924(6)
_cell_length_b                   5.5952(16)
_cell_length_c                   11.691(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.568(4)
_cell_angle_gamma                90.00
_cell_volume                     1368.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2812
_cell_measurement_theta_min      2.600
_cell_measurement_theta_max      31.497

_exptl_crystal_description       Chip
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.8998
_exptl_absorpt_correction_T_max  0.9764
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7355
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.49
_diffrn_reflns_theta_max         31.48
_reflns_number_total             3854
_reflns_number_gt                3584
_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    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0510P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(5)
_refine_ls_number_reflns         3854
_refine_ls_number_parameters     191
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0858
_refine_ls_wR_factor_gt          0.0833
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.58622(7) 1.2968(2) 0.49030(12) 0.0239(3) Uani 1 1 d . . .
S1 S 0.29170(2) 0.04468(7) 0.51060(3) 0.02737(10) Uani 1 1 d . . .
O1 O 0.54263(6) 1.2748(2) 0.39443(9) 0.0247(2) Uani 1 1 d . . .
O2 O 0.46814(6) 1.0196(2) 0.33082(10) 0.0281(3) Uani 1 1 d . . .
C1 C 0.35397(7) 0.2506(3) 0.53255(13) 0.0200(3) Uani 1 1 d . . .
C2 C 0.36479(7) 0.4171(3) 0.44429(13) 0.0214(3) Uani 1 1 d . . .
H2 H 0.3393 0.4114 0.3767 0.026 Uiso 1 1 calc R . .
C3 C 0.41213(7) 0.5886(3) 0.45490(13) 0.0205(3) Uani 1 1 d . . .
H3 H 0.4184 0.7006 0.3950 0.025 Uiso 1 1 calc R . .
C4 C 0.45112(7) 0.5989(3) 0.55381(12) 0.0180(3) Uani 1 1 d . . .
C5 C 0.44002(7) 0.4304(3) 0.64054(13) 0.0208(3) Uani 1 1 d . . .
H5 H 0.4659 0.4344 0.7078 0.025 Uiso 1 1 calc R . .
C6 C 0.39249(7) 0.2583(3) 0.63095(13) 0.0219(3) Uani 1 1 d . . .
H6 H 0.3862 0.1464 0.6909 0.026 Uiso 1 1 calc R . .
C7 C 0.50262(7) 0.7685(3) 0.57341(12) 0.0184(3) Uani 1 1 d . . .
H7 H 0.5248 0.7422 0.6436 0.022 Uiso 1 1 calc R . .
C8 C 0.50661(8) 1.0694(3) 0.40444(13) 0.0214(3) Uani 1 1 d . . .
C9 C 0.52602(7) 0.9562(3) 0.51338(12) 0.0179(3) Uani 1 1 d . . .
C10 C 0.57651(7) 1.1129(3) 0.55569(13) 0.0187(3) Uani 1 1 d . . .
C11 C 0.61601(7) 1.0822(3) 0.66045(13) 0.0188(3) Uani 1 1 d . . .
C12 C 0.61676(7) 1.2596(3) 0.74432(14) 0.0210(3) Uani 1 1 d . . .
H12 H 0.5914 1.3991 0.7347 0.025 Uiso 1 1 calc R . .
C13 C 0.65461(7) 1.2327(3) 0.84202(14) 0.0234(3) Uani 1 1 d . . .
H13 H 0.6549 1.3534 0.8991 0.028 Uiso 1 1 calc R . .
C14 C 0.69184(8) 1.0297(3) 0.85598(14) 0.0231(3) Uani 1 1 d . . .
H14 H 0.7179 1.0119 0.9224 0.028 Uiso 1 1 calc R . .
C15 C 0.69105(8) 0.8521(3) 0.77288(14) 0.0245(3) Uani 1 1 d . . .
H15 H 0.7165 0.7129 0.7829 0.029 Uiso 1 1 calc R . .
C16 C 0.65312(7) 0.8767(3) 0.67498(14) 0.0220(3) Uani 1 1 d . . .
H16 H 0.6525 0.7547 0.6185 0.026 Uiso 1 1 calc R . .
C17 C 0.29473(8) -0.1446(3) 0.63508(16) 0.0286(3) Uani 1 1 d . . .
H17A H 0.3367 -0.2219 0.6402 0.034 Uiso 1 1 calc R . .
H17B H 0.2614 -0.2669 0.6291 0.034 Uiso 1 1 calc R . .
H17C H 0.2878 -0.0479 0.7038 0.034 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
N1 C10 1.299(2) . ?
N1 O1 1.4433(18) . ?
S1 C1 1.7562(16) . ?
S1 C17 1.8005(18) . ?
O1 C8 1.3801(19) . ?
O2 C8 1.205(2) . ?
C1 C6 1.399(2) . ?
C1 C2 1.410(2) . ?
C2 C3 1.384(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.410(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.406(2) . ?
C4 C7 1.452(2) . ?
C5 C6 1.388(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C9 1.357(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.476(2) . ?
C9 C10 1.456(2) . ?
C10 C11 1.481(2) . ?
C11 C12 1.395(2) . ?
C11 C16 1.397(2) . ?
C12 C13 1.392(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.393(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C10 N1 O1 106.75(12) . . ?
C1 S1 C17 104.33(8) . . ?
C8 O1 N1 110.28(11) . . ?
C6 C1 C2 119.09(14) . . ?
C6 C1 S1 124.12(12) . . ?
C2 C1 S1 116.79(11) . . ?
C3 C2 C1 120.83(14) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.65(14) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 117.77(14) . . ?
C5 C4 C7 116.87(13) . . ?
C3 C4 C7 125.36(14) . . ?
C6 C5 C4 122.03(14) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C1 119.63(14) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C9 C7 C4 134.01(14) . . ?
C9 C7 H7 113.0 . . ?
C4 C7 H7 113.0 . . ?
O2 C8 O1 119.56(14) . . ?
O2 C8 C9 133.89(15) . . ?
O1 C8 C9 106.55(13) . . ?
C7 C9 C10 123.69(14) . . ?
C7 C9 C8 132.90(14) . . ?
C10 C9 C8 103.14(13) . . ?
N1 C10 C9 113.22(13) . . ?
N1 C10 C11 119.31(13) . . ?
C9 C10 C11 127.46(13) . . ?
C12 C11 C16 119.86(14) . . ?
C12 C11 C10 120.04(14) . . ?
C16 C11 C10 120.09(13) . . ?
C13 C12 C11 120.11(14) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 120.02(14) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.05(15) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.41(15) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 119.54(14) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
S1 C17 H17A 109.5 . . ?
S1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C10 N1 O1 C8 -0.40(17) . . . . ?
C17 S1 C1 C6 -2.94(16) . . . . ?
C17 S1 C1 C2 177.19(12) . . . . ?
C6 C1 C2 C3 -1.0(2) . . . . ?
S1 C1 C2 C3 178.90(12) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C2 C3 C4 C7 179.09(14) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C7 C4 C5 C6 -179.44(15) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C2 C1 C6 C5 0.7(2) . . . . ?
S1 C1 C6 C5 -179.19(13) . . . . ?
C5 C4 C7 C9 -177.78(16) . . . . ?
C3 C4 C7 C9 2.9(3) . . . . ?
N1 O1 C8 O2 -178.87(15) . . . . ?
N1 O1 C8 C9 1.85(16) . . . . ?
C4 C7 C9 C10 175.52(15) . . . . ?
C4 C7 C9 C8 2.5(3) . . . . ?
O2 C8 C9 C7 -7.5(3) . . . . ?
O1 C8 C9 C7 171.58(16) . . . . ?
O2 C8 C9 C10 178.43(18) . . . . ?
O1 C8 C9 C10 -2.44(15) . . . . ?
O1 N1 C10 C9 -1.31(17) . . . . ?
O1 N1 C10 C11 178.23(12) . . . . ?
C7 C9 C10 N1 -172.36(14) . . . . ?
C8 C9 C10 N1 2.38(17) . . . . ?
C7 C9 C10 C11 8.1(2) . . . . ?
C8 C9 C10 C11 -177.12(14) . . . . ?
N1 C10 C11 C12 58.4(2) . . . . ?
C9 C10 C11 C12 -122.17(17) . . . . ?
N1 C10 C11 C16 -120.95(17) . . . . ?
C9 C10 C11 C16 58.5(2) . . . . ?
C16 C11 C12 C13 0.3(2) . . . . ?
C10 C11 C12 C13 -179.01(14) . . . . ?
C11 C12 C13 C14 0.2(2) . . . . ?
C12 C13 C14 C15 -0.5(2) . . . . ?
C13 C14 C15 C16 0.2(2) . . . . ?
C14 C15 C16 C11 0.3(2) . . . . ?
C12 C11 C16 C15 -0.6(2) . . . . ?
C10 C11 C16 C15 178.74(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        31.48
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_bo2887
_database_code_depnum_ccdc_archive 'CCDC 1448257'
_audit_update_record             
;
2016-01-19 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 N O2 S'
_chemical_formula_weight         295.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   41.870(11)
_cell_length_b                   5.7143(13)
_cell_length_c                   11.597(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.235(4)
_cell_angle_gamma                90.00
_cell_volume                     2758.3(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    7114
_cell_measurement_theta_min      2.490
_cell_measurement_theta_max      29.127

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.8803
_exptl_absorpt_correction_T_max  0.9835
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            23613
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0601
_diffrn_reflns_limit_h_min       -55
_diffrn_reflns_limit_h_max       55
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         28.00
_reflns_number_total             6437
_reflns_number_gt                4957
_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    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0798P)²+1.9600P] 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         6437
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1701
_refine_ls_wR_factor_gt          0.1518
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.220650(16) 0.69343(13) 0.52921(6) 0.03222(19) Uani 1 1 d . . .
S2 S 0.274501(16) 1.15119(13) 0.83124(7) 0.03470(19) Uani 1 1 d . . .
O1 O 0.09859(4) -0.5316(3) 0.59528(15) 0.0280(4) Uani 1 1 d . . .
O2 O 0.13592(4) -0.2822(4) 0.67297(16) 0.0318(4) Uani 1 1 d . . .
O3 O 0.40057(4) -0.0436(4) 1.01516(16) 0.0294(4) Uani 1 1 d . . .
O4 O 0.36238(5) 0.2025(4) 1.06020(16) 0.0339(5) Uani 1 1 d . . .
N1 N 0.07647(5) -0.5517(4) 0.49053(19) 0.0270(5) Uani 1 1 d . . .
N2 N 0.42316(5) -0.0620(4) 0.92919(19) 0.0284(5) Uani 1 1 d . . .
C1 C 0.19130(6) 0.4792(5) 0.4925(2) 0.0251(5) Uani 1 1 d . . .
C2 C 0.18624(6) 0.3141(5) 0.5787(2) 0.0270(5) Uani 1 1 d . . .
H2 H 0.1992 0.3194 0.6513 0.032 Uiso 1 1 calc R . .
C3 C 0.16289(6) 0.1455(5) 0.5594(2) 0.0249(5) Uani 1 1 d . . .
H3 H 0.1597 0.0363 0.6189 0.030 Uiso 1 1 calc R . .
C4 C 0.14356(5) 0.1331(5) 0.4520(2) 0.0217(5) Uani 1 1 d . . .
C5 C 0.14916(5) 0.2980(5) 0.3667(2) 0.0244(5) Uani 1 1 d . . .
H5 H 0.1365 0.2919 0.2937 0.029 Uiso 1 1 calc R . .
C6 C 0.17248(6) 0.4687(5) 0.3854(2) 0.0267(5) Uani 1 1 d . . .
H6 H 0.1757 0.5780 0.3261 0.032 Uiso 1 1 calc R . .
C7 C 0.11804(5) -0.0328(5) 0.4231(2) 0.0221(5) Uani 1 1 d . . .
H7 H 0.1068 -0.0071 0.3485 0.027 Uiso 1 1 calc R . .
C8 C 0.11661(6) -0.3305(5) 0.5918(2) 0.0242(5) Uani 1 1 d . . .
C9 C 0.10649(5) -0.2190(5) 0.4796(2) 0.0216(5) Uani 1 1 d . . .
C10 C 0.08122(5) -0.3713(5) 0.4276(2) 0.0218(5) Uani 1 1 d . . .
C11 C 0.06136(5) -0.3385(5) 0.3148(2) 0.0222(5) Uani 1 1 d . . .
C12 C 0.06048(6) -0.5104(5) 0.2296(2) 0.0256(5) Uani 1 1 d . . .
H12 H 0.0728 -0.6492 0.2432 0.031 Uiso 1 1 calc R . .
C13 C 0.04160(6) -0.4788(5) 0.1249(2) 0.0280(6) Uani 1 1 d . . .
H13 H 0.0413 -0.5949 0.0661 0.034 Uiso 1 1 calc R . .
C14 C 0.02321(6) -0.2781(5) 0.1058(2) 0.0278(6) Uani 1 1 d . . .
H14 H 0.0101 -0.2575 0.0344 0.033 Uiso 1 1 calc R . .
C15 C 0.02387(6) -0.1072(5) 0.1909(2) 0.0262(5) Uani 1 1 d . . .
H15 H 0.0111 0.0296 0.1777 0.031 Uiso 1 1 calc R . .
C16 C 0.04308(5) -0.1353(5) 0.2951(2) 0.0245(5) Uani 1 1 d . . .
H16 H 0.0438 -0.0168 0.3528 0.029 Uiso 1 1 calc R . .
C17 C 0.22071(7) 0.8637(5) 0.3992(3) 0.0350(6) Uani 1 1 d . . .
H17A H 0.2271 0.7644 0.3367 0.042 Uiso 1 1 calc R . .
H17B H 0.2360 0.9933 0.4130 0.042 Uiso 1 1 calc R . .
H17C H 0.1991 0.9262 0.3770 0.042 Uiso 1 1 calc R . .
C18 C 0.30597(6) 0.9514(5) 0.8274(2) 0.0254(5) Uani 1 1 d . . .
C19 C 0.31062(6) 0.7877(5) 0.9180(2) 0.0278(6) Uani 1 1 d . . .
H19 H 0.2969 0.7903 0.9782 0.033 Uiso 1 1 calc R . .
C20 C 0.33478(6) 0.6234(5) 0.9208(2) 0.0265(5) Uani 1 1 d . . .
H20 H 0.3375 0.5132 0.9825 0.032 Uiso 1 1 calc R . .
C21 C 0.35549(5) 0.6174(5) 0.8333(2) 0.0226(5) Uani 1 1 d . . .
C22 C 0.35074(6) 0.7837(5) 0.7435(2) 0.0259(5) Uani 1 1 d . . .
H22 H 0.3646 0.7831 0.6838 0.031 Uiso 1 1 calc R . .
C23 C 0.32651(6) 0.9470(5) 0.7401(2) 0.0270(5) Uani 1 1 d . . .
H23 H 0.3237 1.0570 0.6784 0.032 Uiso 1 1 calc R . .
C24 C 0.38162(5) 0.4548(4) 0.8271(2) 0.0214(5) Uani 1 1 d . . .
H24 H 0.3935 0.4830 0.7632 0.026 Uiso 1 1 calc R . .
C25 C 0.38235(6) 0.1556(5) 0.9962(2) 0.0255(5) Uani 1 1 d . . .
C26 C 0.39290(5) 0.2702(5) 0.8931(2) 0.0227(5) Uani 1 1 d . . .
C27 C 0.41861(5) 0.1187(5) 0.8625(2) 0.0223(5) Uani 1 1 d . . .
C28 C 0.43864(5) 0.1543(4) 0.7669(2) 0.0214(5) Uani 1 1 d . . .
C29 C 0.43971(6) -0.0141(5) 0.6809(2) 0.0262(5) Uani 1 1 d . . .
H29 H 0.4275 -0.1540 0.6833 0.031 Uiso 1 1 calc R . .
C30 C 0.45862(6) 0.0227(5) 0.5913(2) 0.0282(6) Uani 1 1 d . . .
H30 H 0.4591 -0.0915 0.5320 0.034 Uiso 1 1 calc R . .
C31 C 0.47683(6) 0.2246(5) 0.5878(2) 0.0271(5) Uani 1 1 d . . .
H31 H 0.4899 0.2479 0.5267 0.033 Uiso 1 1 calc R . .
C32 C 0.47592(6) 0.3923(5) 0.6735(2) 0.0273(5) Uani 1 1 d . . .
H32 H 0.4885 0.5303 0.6715 0.033 Uiso 1 1 calc R . .
C33 C 0.45664(6) 0.3594(5) 0.7626(2) 0.0240(5) Uani 1 1 d . . .
H33 H 0.4557 0.4763 0.8204 0.029 Uiso 1 1 calc R . .
C34 C 0.27812(7) 1.3338(6) 0.7076(3) 0.0388(7) Uani 1 1 d . . .
H34A H 0.2994 1.4070 0.7150 0.047 Uiso 1 1 calc R . .
H34B H 0.2616 1.4556 0.7032 0.047 Uiso 1 1 calc R . .
H34C H 0.2754 1.2386 0.6369 0.047 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.754(3) . ?
S1 C17 1.794(3) . ?
S2 C18 1.748(3) . ?
S2 C34 1.794(3) . ?
O1 C8 1.378(3) . ?
O1 N1 1.450(3) . ?
O2 C8 1.204(3) . ?
O3 C25 1.375(3) . ?
O3 N2 1.451(3) . ?
O4 C25 1.207(3) . ?
N1 C10 1.291(3) . ?
N2 C27 1.292(3) . ?
C1 C6 1.398(4) . ?
C1 C2 1.407(4) . ?
C2 C3 1.374(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.412(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(3) . ?
C4 C7 1.440(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C9 1.365(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.470(3) . ?
C9 C10 1.450(3) . ?
C10 C11 1.483(3) . ?
C11 C12 1.391(4) . ?
C11 C16 1.396(3) . ?
C12 C13 1.388(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C23 1.398(4) . ?
C18 C19 1.405(4) . ?
C19 C20 1.378(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.405(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.409(4) . ?
C21 C24 1.443(3) . ?
C22 C23 1.376(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C26 1.357(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.473(3) . ?
C26 C27 1.455(3) . ?
C27 C28 1.475(3) . ?
C28 C29 1.390(4) . ?
C28 C33 1.397(3) . ?
C29 C30 1.388(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.386(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.385(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.391(4) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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
C1 S1 C17 103.85(14) . . ?
C18 S2 C34 103.30(13) . . ?
C8 O1 N1 110.11(19) . . ?
C25 O3 N2 110.03(19) . . ?
C10 N1 O1 106.7(2) . . ?
C27 N2 O3 106.8(2) . . ?
C6 C1 C2 119.2(2) . . ?
C6 C1 S1 123.9(2) . . ?
C2 C1 S1 116.82(19) . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.6(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 117.7(2) . . ?
C5 C4 C7 117.0(2) . . ?
C3 C4 C7 125.3(2) . . ?
C6 C5 C4 122.2(2) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C9 C7 C4 133.9(2) . . ?
C9 C7 H7 113.0 . . ?
C4 C7 H7 113.0 . . ?
O2 C8 O1 119.5(2) . . ?
O2 C8 C9 134.2(2) . . ?
O1 C8 C9 106.3(2) . . ?
C7 C9 C10 123.3(2) . . ?
C7 C9 C8 132.8(2) . . ?
C10 C9 C8 103.6(2) . . ?
N1 C10 C9 113.2(2) . . ?
N1 C10 C11 119.6(2) . . ?
C9 C10 C11 127.2(2) . . ?
C12 C11 C16 120.0(2) . . ?
C12 C11 C10 120.4(2) . . ?
C16 C11 C10 119.6(2) . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 119.7(2) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
S1 C17 H17A 109.5 . . ?
S1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 118.9(2) . . ?
C23 C18 S2 123.7(2) . . ?
C19 C18 S2 117.36(19) . . ?
C20 C19 C18 120.9(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 120.6(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C22 118.0(2) . . ?
C20 C21 C24 125.6(2) . . ?
C22 C21 C24 116.4(2) . . ?
C23 C22 C21 121.5(2) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C22 C23 C18 120.1(2) . . ?
C22 C23 H23 119.9 . . ?
C18 C23 H23 119.9 . . ?
C26 C24 C21 133.7(2) . . ?
C26 C24 H24 113.1 . . ?
C21 C24 H24 113.1 . . ?
O4 C25 O3 119.7(2) . . ?
O4 C25 C26 133.6(3) . . ?
O3 C25 C26 106.7(2) . . ?
C24 C26 C27 123.1(2) . . ?
C24 C26 C25 133.4(2) . . ?
C27 C26 C25 103.2(2) . . ?
N2 C27 C26 113.2(2) . . ?
N2 C27 C28 120.1(2) . . ?
C26 C27 C28 126.7(2) . . ?
C29 C28 C33 119.7(2) . . ?
C29 C28 C27 120.6(2) . . ?
C33 C28 C27 119.7(2) . . ?
C30 C29 C28 119.8(2) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C31 C30 C29 120.6(3) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C32 C31 C30 119.8(2) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C31 C32 C33 120.2(3) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C32 C33 C28 119.9(2) . . ?
C32 C33 H33 120.0 . . ?
C28 C33 H33 120.0 . . ?
S2 C34 H34A 109.5 . . ?
S2 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
S2 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 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
C8 O1 N1 C10 0.2(3) . . . . ?
C25 O3 N2 C27 0.2(3) . . . . ?
C17 S1 C1 C6 -3.0(3) . . . . ?
C17 S1 C1 C2 178.8(2) . . . . ?
C6 C1 C2 C3 -0.8(4) . . . . ?
S1 C1 C2 C3 177.4(2) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C2 C3 C4 C7 -178.7(2) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C7 C4 C5 C6 178.5(2) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
S1 C1 C6 C5 -177.6(2) . . . . ?
C5 C4 C7 C9 177.2(3) . . . . ?
C3 C4 C7 C9 -4.0(4) . . . . ?
N1 O1 C8 O2 178.5(2) . . . . ?
N1 O1 C8 C9 -1.5(3) . . . . ?
C4 C7 C9 C10 -175.8(2) . . . . ?
C4 C7 C9 C8 -3.0(5) . . . . ?
O2 C8 C9 C7 8.2(5) . . . . ?
O1 C8 C9 C7 -171.7(3) . . . . ?
O2 C8 C9 C10 -178.0(3) . . . . ?
O1 C8 C9 C10 2.1(2) . . . . ?
O1 N1 C10 C9 1.3(3) . . . . ?
O1 N1 C10 C11 -178.4(2) . . . . ?
C7 C9 C10 N1 172.4(2) . . . . ?
C8 C9 C10 N1 -2.1(3) . . . . ?
C7 C9 C10 C11 -8.0(4) . . . . ?
C8 C9 C10 C11 177.5(2) . . . . ?
N1 C10 C11 C12 -57.3(3) . . . . ?
C9 C10 C11 C12 123.1(3) . . . . ?
N1 C10 C11 C16 121.7(3) . . . . ?
C9 C10 C11 C16 -57.9(3) . . . . ?
C16 C11 C12 C13 0.4(4) . . . . ?
C10 C11 C12 C13 179.4(2) . . . . ?
C11 C12 C13 C14 -1.1(4) . . . . ?
C12 C13 C14 C15 0.7(4) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C14 C15 C16 C11 -1.1(4) . . . . ?
C12 C11 C16 C15 0.6(4) . . . . ?
C10 C11 C16 C15 -178.3(2) . . . . ?
C34 S2 C18 C23 -2.7(3) . . . . ?
C34 S2 C18 C19 177.1(2) . . . . ?
C23 C18 C19 C20 -0.6(4) . . . . ?
S2 C18 C19 C20 179.6(2) . . . . ?
C18 C19 C20 C21 0.5(4) . . . . ?
C19 C20 C21 C22 0.0(4) . . . . ?
C19 C20 C21 C24 179.8(2) . . . . ?
C20 C21 C22 C23 -0.4(4) . . . . ?
C24 C21 C22 C23 179.8(2) . . . . ?
C21 C22 C23 C18 0.3(4) . . . . ?
C19 C18 C23 C22 0.2(4) . . . . ?
S2 C18 C23 C22 -180.0(2) . . . . ?
C20 C21 C24 C26 2.6(5) . . . . ?
C22 C21 C24 C26 -177.6(3) . . . . ?
N2 O3 C25 O4 -179.1(2) . . . . ?
N2 O3 C25 C26 1.0(3) . . . . ?
C21 C24 C26 C27 174.7(2) . . . . ?
C21 C24 C26 C25 2.3(5) . . . . ?
O4 C25 C26 C24 -8.1(5) . . . . ?
O3 C25 C26 C24 171.7(3) . . . . ?
O4 C25 C26 C27 178.5(3) . . . . ?
O3 C25 C26 C27 -1.7(3) . . . . ?
O3 N2 C27 C26 -1.4(3) . . . . ?
O3 N2 C27 C28 178.5(2) . . . . ?
C24 C26 C27 N2 -172.3(2) . . . . ?
C25 C26 C27 N2 2.0(3) . . . . ?
C24 C26 C27 C28 7.7(4) . . . . ?
C25 C26 C27 C28 -178.0(2) . . . . ?
N2 C27 C28 C29 58.1(3) . . . . ?
C26 C27 C28 C29 -121.9(3) . . . . ?
N2 C27 C28 C33 -122.0(3) . . . . ?
C26 C27 C28 C33 57.9(3) . . . . ?
C33 C28 C29 C30 -0.1(4) . . . . ?
C27 C28 C29 C30 179.8(2) . . . . ?
C28 C29 C30 C31 0.9(4) . . . . ?
C29 C30 C31 C32 -0.7(4) . . . . ?
C30 C31 C32 C33 -0.5(4) . . . . ?
C31 C32 C33 C28 1.3(4) . . . . ?
C29 C28 C33 C32 -1.0(4) . . . . ?
C27 C28 C33 C32 179.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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_bo2841
_database_code_depnum_ccdc_archive 'CCDC 1448258'
_audit_update_record             
;
2016-01-19 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 N O2 S'
_chemical_formula_weight         269.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Pc

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

_cell_length_a                   9.466(3)
_cell_length_b                   6.060(2)
_cell_length_c                   11.771(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.248(5)
_cell_angle_gamma                90.00
_cell_volume                     648.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    2267
_cell_measurement_theta_min      3.246
_cell_measurement_theta_max      29.105

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.8809
_exptl_absorpt_correction_T_max  0.9606
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6251
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         29.11
_reflns_number_total             2797
_reflns_number_gt                2378
_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    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0139P)²+0.1060P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(6)
_refine_ls_number_reflns         2797
_refine_ls_number_parameters     172
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0631
_refine_ls_wR_factor_gt          0.0613
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.43980(5) 0.80545(8) 0.55811(4) 0.03617(13) Uani 1 1 d . . .
O1 O 0.75147(16) 0.1701(2) 0.61542(12) 0.0393(4) Uani 1 1 d . . .
O2 O 0.58703(16) 0.4033(2) 0.65515(12) 0.0427(4) Uani 1 1 d . . .
N1 N 0.84482(18) 0.1617(3) 0.53662(15) 0.0365(4) Uani 1 1 d . . .
C1 C 0.3477(2) 1.0436(4) 0.50305(18) 0.0389(5) Uani 1 1 d . . .
C2 C 0.3840(2) 1.1179(4) 0.40588(18) 0.0418(6) Uani 1 1 d . . .
H2 H 0.3435 1.2473 0.3636 0.050 Uiso 1 1 calc R . .
C3 C 0.4873(2) 0.9833(3) 0.37491(17) 0.0360(5) Uani 1 1 d . . .
H3 H 0.5236 1.0119 0.3088 0.043 Uiso 1 1 calc R . .
C4 C 0.5316(2) 0.8051(3) 0.44920(16) 0.0297(4) Uani 1 1 d . . .
C5 C 0.6427(2) 0.6571(3) 0.43708(16) 0.0299(4) Uani 1 1 d . . .
H5 H 0.6812 0.6921 0.3729 0.036 Uiso 1 1 calc R . .
C6 C 0.7049(2) 0.4761(3) 0.49841(16) 0.0288(4) Uani 1 1 d . . .
C7 C 0.6695(2) 0.3616(3) 0.59639(17) 0.0346(5) Uani 1 1 d . . .
C8 C 0.8165(2) 0.3389(3) 0.47193(16) 0.0286(4) Uani 1 1 d . . .
C9 C 0.8996(2) 0.3828(3) 0.38521(15) 0.0278(4) Uani 1 1 d . . .
C10 C 0.9089(2) 0.2225(3) 0.30316(17) 0.0321(4) Uani 1 1 d . . .
H10 H 0.8581 0.0866 0.3005 0.039 Uiso 1 1 calc R . .
C11 C 0.9922(2) 0.2610(3) 0.22520(18) 0.0373(5) Uani 1 1 d . . .
H11 H 0.9981 0.1519 0.1688 0.045 Uiso 1 1 calc R . .
C12 C 1.0663(2) 0.4576(3) 0.22973(18) 0.0364(5) Uani 1 1 d . . .
H12 H 1.1245 0.4823 0.1771 0.044 Uiso 1 1 calc R . .
C13 C 1.0569(2) 0.6195(3) 0.30994(19) 0.0371(5) Uani 1 1 d . . .
H13 H 1.1082 0.7549 0.3123 0.045 Uiso 1 1 calc R . .
C14 C 0.9719(2) 0.5832(3) 0.38723(17) 0.0328(4) Uani 1 1 d . . .
H14 H 0.9631 0.6952 0.4414 0.039 Uiso 1 1 calc R . .
C15 C 0.2450(3) 1.1479(4) 0.5640(2) 0.0587(7) Uani 1 1 d . . .
H15A H 0.2403 1.0565 0.6316 0.070 Uiso 0.50 1 calc PR . .
H15B H 0.1466 1.1599 0.5084 0.070 Uiso 0.50 1 calc PR . .
H15C H 0.2811 1.2953 0.5920 0.070 Uiso 0.50 1 calc PR . .
H15D H 0.2051 1.2846 0.5231 0.070 Uiso 0.50 1 calc PR . .
H15E H 0.2987 1.1812 0.6463 0.070 Uiso 0.50 1 calc PR . .
H15F H 0.1642 1.0458 0.5626 0.070 Uiso 0.50 1 calc PR . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.717(2) . ?
S1 C4 1.738(2) . ?
O1 C7 1.379(2) . ?
O1 N1 1.450(2) . ?
O2 C7 1.206(2) . ?
N1 C8 1.300(2) . ?
C1 C2 1.360(3) . ?
C1 C15 1.500(3) . ?
C2 C3 1.398(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.419(3) . ?
C5 C6 1.354(3) . ?
C5 H5 0.9500 . ?
C6 C8 1.445(3) . ?
C6 C7 1.463(3) . ?
C8 C9 1.477(3) . ?
C9 C10 1.390(2) . ?
C9 C14 1.391(3) . ?
C10 C11 1.387(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.375(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 H15D 0.9800 . ?
C15 H15E 0.9800 . ?
C15 H15F 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
C1 S1 C4 91.63(10) . . ?
C7 O1 N1 109.97(14) . . ?
C8 N1 O1 106.44(16) . . ?
C2 C1 C15 127.8(2) . . ?
C2 C1 S1 112.01(16) . . ?
C15 C1 S1 120.14(18) . . ?
C1 C2 C3 112.7(2) . . ?
C1 C2 H2 123.6 . . ?
C3 C2 H2 123.6 . . ?
C4 C3 C2 113.7(2) . . ?
C4 C3 H3 123.1 . . ?
C2 C3 H3 123.1 . . ?
C3 C4 C5 122.25(19) . . ?
C3 C4 S1 109.92(16) . . ?
C5 C4 S1 127.74(15) . . ?
C6 C5 C4 133.03(19) . . ?
C6 C5 H5 113.5 . . ?
C4 C5 H5 113.5 . . ?
C5 C6 C8 125.90(18) . . ?
C5 C6 C7 130.0(2) . . ?
C8 C6 C7 103.87(17) . . ?
O2 C7 O1 120.55(19) . . ?
O2 C7 C6 132.9(2) . . ?
O1 C7 C6 106.53(18) . . ?
N1 C8 C6 113.09(18) . . ?
N1 C8 C9 119.42(18) . . ?
C6 C8 C9 127.47(17) . . ?
C10 C9 C14 119.73(18) . . ?
C10 C9 C8 120.27(17) . . ?
C14 C9 C8 119.99(16) . . ?
C11 C10 C9 120.03(18) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C14 119.62(18) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C9 119.92(18) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
C1 C15 H15A 109.5 . . ?
C1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C15 H15D 109.5 . . ?
H15A C15 H15D 141.1 . . ?
H15B C15 H15D 56.3 . . ?
H15C C15 H15D 56.3 . . ?
C1 C15 H15E 109.5 . . ?
H15A C15 H15E 56.3 . . ?
H15B C15 H15E 141.1 . . ?
H15C C15 H15E 56.3 . . ?
H15D C15 H15E 109.5 . . ?
C1 C15 H15F 109.5 . . ?
H15A C15 H15F 56.3 . . ?
H15B C15 H15F 56.3 . . ?
H15C C15 H15F 141.1 . . ?
H15D C15 H15F 109.5 . . ?
H15E C15 H15F 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
C7 O1 N1 C8 -1.34(19) . . . . ?
C4 S1 C1 C2 0.58(17) . . . . ?
C4 S1 C1 C15 -177.71(18) . . . . ?
C15 C1 C2 C3 177.9(2) . . . . ?
S1 C1 C2 C3 -0.2(2) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 -175.89(19) . . . . ?
C2 C3 C4 S1 0.8(2) . . . . ?
C1 S1 C4 C3 -0.80(15) . . . . ?
C1 S1 C4 C5 175.70(18) . . . . ?
C3 C4 C5 C6 179.1(2) . . . . ?
S1 C4 C5 C6 3.0(3) . . . . ?
C4 C5 C6 C8 178.44(19) . . . . ?
C4 C5 C6 C7 4.7(3) . . . . ?
N1 O1 C7 O2 -178.18(17) . . . . ?
N1 O1 C7 C6 2.85(19) . . . . ?
C5 C6 C7 O2 -7.1(4) . . . . ?
C8 C6 C7 O2 178.1(2) . . . . ?
C5 C6 C7 O1 171.65(18) . . . . ?
C8 C6 C7 O1 -3.14(19) . . . . ?
O1 N1 C8 C6 -0.8(2) . . . . ?
O1 N1 C8 C9 177.54(14) . . . . ?
C5 C6 C8 N1 -172.58(18) . . . . ?
C7 C6 C8 N1 2.5(2) . . . . ?
C5 C6 C8 C9 9.2(3) . . . . ?
C7 C6 C8 C9 -175.70(17) . . . . ?
N1 C8 C9 C10 52.3(2) . . . . ?
C6 C8 C9 C10 -129.6(2) . . . . ?
N1 C8 C9 C14 -126.24(19) . . . . ?
C6 C8 C9 C14 51.9(2) . . . . ?
C14 C9 C10 C11 1.2(3) . . . . ?
C8 C9 C10 C11 -177.27(17) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C13 -1.1(3) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C9 1.4(3) . . . . ?
C10 C9 C14 C13 -2.1(3) . . . . ?
C8 C9 C14 C13 176.37(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        29.11
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1448260'
_audit_update_record             
;
2016-04-09 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H14 N2 O2'
_chemical_formula_weight         230.26

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                   13.975(14)
_cell_length_b                   6.227(7)
_cell_length_c                   15.099(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.12(2)
_cell_angle_gamma                90.00
_cell_volume                     1190(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2456
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9826
_exptl_absorpt_correction_T_max  0.9826
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_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            7120
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         25.18
_reflns_number_total             2126
_reflns_number_gt                1707
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0682P)²+0.2039P] 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         2126
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1275
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.71009(14) 0.7907(3) -0.14714(12) 0.0595(5) Uani 1 1 d . . .
H1A H 0.7600 0.6782 -0.1155 0.089 Uiso 1 1 calc R . .
H1B H 0.7153 0.8324 -0.2061 0.089 Uiso 1 1 calc R . .
H1C H 0.6399 0.7400 -0.1628 0.089 Uiso 1 1 calc R . .
C2 C 0.80352(17) 1.1353(4) -0.09114(15) 0.0719(6) Uani 1 1 d . . .
H2A H 0.7677 1.2711 -0.1079 0.108 Uiso 1 1 calc R . .
H2B H 0.8245 1.0929 -0.1414 0.108 Uiso 1 1 calc R . .
H2C H 0.8650 1.1482 -0.0301 0.108 Uiso 1 1 calc R . .
C3 C 0.69820(11) 0.9869(2) -0.01074(10) 0.0427(4) Uani 1 1 d . . .
C4 C 0.71994(14) 1.1688(3) 0.05103(12) 0.0544(4) Uani 1 1 d . . .
H4 H 0.7578 1.2830 0.0420 0.065 Uiso 1 1 calc R . .
C5 C 0.68629(13) 1.1789(3) 0.12352(12) 0.0527(4) Uani 1 1 d . . .
H5 H 0.7017 1.3011 0.1626 0.063 Uiso 1 1 calc R . .
C6 C 0.62911(11) 1.0117(2) 0.14149(11) 0.0415(4) Uani 1 1 d . . .
C7 C 0.60687(12) 0.8313(2) 0.07928(11) 0.0460(4) Uani 1 1 d . . .
H7 H 0.5690 0.7174 0.0884 0.055 Uiso 1 1 calc R . .
C8 C 0.63955(12) 0.8197(3) 0.00595(11) 0.0465(4) Uani 1 1 d . . .
H8 H 0.6228 0.6987 -0.0339 0.056 Uiso 1 1 calc R . .
C9 C 0.59797(11) 1.0405(2) 0.21890(11) 0.0425(4) Uani 1 1 d . . .
H9 H 0.6207 1.1706 0.2514 0.051 Uiso 1 1 calc R . .
C10 C 0.54180(11) 0.9191(3) 0.25654(10) 0.0424(4) Uani 1 1 d . . .
C11 C 0.49082(15) 0.7110(3) 0.22889(13) 0.0575(5) Uani 1 1 d . . .
C12 C 0.52136(12) 0.9825(3) 0.33872(11) 0.0466(4) Uani 1 1 d . . .
C13 C 0.55821(15) 1.1812(3) 0.39821(13) 0.0641(5) Uani 1 1 d . . .
H13A H 0.5403 1.1745 0.4529 0.096 Uiso 1 1 calc R . .
H13B H 0.5247 1.3038 0.3586 0.096 Uiso 1 1 calc R . .
H13C H 0.6335 1.1937 0.4215 0.096 Uiso 1 1 calc R . .
N1 N 0.73293(11) 0.9745(2) -0.08199(10) 0.0511(4) Uani 1 1 d . . .
N2 N 0.46534(12) 0.8457(3) 0.36007(11) 0.0624(4) Uani 1 1 d . . .
O1 O 0.48383(13) 0.5778(2) 0.16834(11) 0.0879(5) Uani 1 1 d . . .
O2 O 0.44291(11) 0.6716(2) 0.29044(10) 0.0736(4) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.453(2) . ?
C2 N1 1.453(2) . ?
C3 N1 1.357(2) . ?
C3 C8 1.412(2) . ?
C3 C4 1.416(2) . ?
C4 C5 1.364(3) . ?
C5 C6 1.407(2) . ?
C6 C7 1.412(2) . ?
C6 C9 1.421(2) . ?
C7 C8 1.367(2) . ?
C9 C10 1.375(2) . ?
C10 C12 1.441(2) . ?
C10 C11 1.452(3) . ?
C11 O1 1.207(2) . ?
C11 O2 1.378(2) . ?
C12 N2 1.287(2) . ?
C12 C13 1.487(3) . ?
N2 O2 1.448(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
N1 C3 C8 121.95(14) . . ?
N1 C3 C4 121.26(14) . . ?
C8 C3 C4 116.80(15) . . ?
C5 C4 C3 121.01(15) . . ?
C4 C5 C6 122.54(15) . . ?
C5 C6 C7 116.30(15) . . ?
C5 C6 C9 117.54(14) . . ?
C7 C6 C9 126.15(14) . . ?
C8 C7 C6 121.75(14) . . ?
C7 C8 C3 121.60(14) . . ?
C10 C9 C6 134.32(15) . . ?
C9 C10 C12 124.19(16) . . ?
C9 C10 C11 131.95(15) . . ?
C12 C10 C11 103.86(14) . . ?
O1 C11 O2 118.81(17) . . ?
O1 C11 C10 134.66(16) . . ?
O2 C11 C10 106.52(15) . . ?
N2 C12 C10 113.46(16) . . ?
N2 C12 C13 119.41(16) . . ?
C10 C12 C13 127.13(15) . . ?
C3 N1 C2 121.45(14) . . ?
C3 N1 C1 122.12(14) . . ?
C2 N1 C1 116.19(14) . . ?
C12 N2 O2 106.30(14) . . ?
C11 O2 N2 109.81(14) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.18
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1448261'
_audit_update_record             
;
2016-04-09 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 N O3'
_chemical_formula_weight         217.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   12.8234(7)
_cell_length_b                   6.9230(4)
_cell_length_c                   12.7631(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.8740(10)
_cell_angle_gamma                90.00
_cell_volume                     1051.49(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2920
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      25.21

_exptl_crystal_description       bar
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_T_max  0.9823
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_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            6669
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.34
_reflns_number_total             1930
_reflns_number_gt                1660
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0656P)²+0.1339P] 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     SHELXL
_refine_ls_extinction_coef       0.044(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1930
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.1037
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.54996(13) 0.0844(3) 0.67852(16) 0.0675(5) Uani 1 1 d . . .
H1A H 0.5759 -0.0186 0.7324 0.101 Uiso 1 1 calc R . .
H1B H 0.4733 0.0608 0.6301 0.101 Uiso 1 1 calc R . .
H1C H 0.5547 0.2045 0.7176 0.101 Uiso 1 1 calc R . .
C2 C 0.73098(11) 0.10963(17) 0.66656(12) 0.0420(3) Uani 1 1 d . . .
C3 C 0.78549(11) 0.13158(18) 0.78253(12) 0.0449(3) Uani 1 1 d . . .
H3 H 0.7443 0.1405 0.8288 0.054 Uiso 1 1 calc R . .
C4 C 0.90128(11) 0.14006(18) 0.82832(11) 0.0415(3) Uani 1 1 d . . .
H4 H 0.9373 0.1537 0.9060 0.050 Uiso 1 1 calc R . .
C5 C 0.96617(10) 0.12877(16) 0.76115(10) 0.0356(3) Uani 1 1 d . . .
C6 C 0.90884(11) 0.11013(17) 0.64422(11) 0.0398(3) Uani 1 1 d . . .
H6 H 0.9494 0.1037 0.5972 0.048 Uiso 1 1 calc R . .
C7 C 0.79420(11) 0.10122(18) 0.59833(11) 0.0437(3) Uani 1 1 d . . .
H7 H 0.7578 0.0894 0.5205 0.052 Uiso 1 1 calc R . .
C8 C 1.08648(10) 0.12683(16) 0.81850(10) 0.0368(3) Uani 1 1 d . . .
H8 H 1.1093 0.1298 0.8967 0.044 Uiso 1 1 calc R . .
C9 C 1.17362(11) 0.12161(16) 0.78234(10) 0.0360(3) Uani 1 1 d . . .
C10 C 1.17866(11) 0.13573(18) 0.66980(11) 0.0425(3) Uani 1 1 d . . .
C11 C 1.29030(11) 0.10215(18) 0.85638(11) 0.0419(3) Uani 1 1 d . . .
C12 C 1.33527(12) 0.0833(2) 0.98137(12) 0.0586(4) Uani 1 1 d . . .
H12A H 1.4159 0.0816 1.0093 0.088 Uiso 1 1 calc R . .
H12B H 1.3085 -0.0347 1.0020 0.088 Uiso 1 1 calc R . .
H12C H 1.3104 0.1908 1.0136 0.088 Uiso 1 1 calc R . .
N1 N 1.35799(10) 0.09814(18) 0.80313(11) 0.0544(3) Uani 1 1 d . . .
O1 O 0.61838(8) 0.09392(15) 0.61231(9) 0.0585(3) Uani 1 1 d . . .
O2 O 1.10976(8) 0.16122(16) 0.57636(8) 0.0576(3) Uani 1 1 d . . .
O3 O 1.28962(8) 0.11951(15) 0.68459(9) 0.0564(3) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.4286(19) . ?
C2 O1 1.3532(16) . ?
C2 C3 1.3897(19) . ?
C2 C7 1.3948(19) . ?
C3 C4 1.3794(19) . ?
C4 C5 1.4019(18) . ?
C5 C6 1.4025(17) . ?
C5 C8 1.4403(17) . ?
C6 C7 1.3661(18) . ?
C8 C9 1.3592(18) . ?
C9 C11 1.4478(18) . ?
C9 C10 1.4649(18) . ?
C10 O2 1.2037(16) . ?
C10 O3 1.3685(16) . ?
C11 N1 1.2868(18) . ?
C11 C12 1.4863(19) . ?
N1 O3 1.4461(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C2 C3 124.84(13) . . ?
O1 C2 C7 115.77(12) . . ?
C3 C2 C7 119.39(12) . . ?
C4 C3 C2 119.40(12) . . ?
C3 C4 C5 121.94(12) . . ?
C6 C5 C4 117.42(11) . . ?
C6 C5 C8 125.28(11) . . ?
C4 C5 C8 117.21(11) . . ?
C7 C6 C5 120.94(12) . . ?
C6 C7 C2 120.89(12) . . ?
C9 C8 C5 133.48(12) . . ?
C8 C9 C11 124.15(12) . . ?
C8 C9 C10 132.32(12) . . ?
C11 C9 C10 103.52(11) . . ?
O2 C10 O3 119.36(12) . . ?
O2 C10 C9 134.19(13) . . ?
O3 C10 C9 106.42(11) . . ?
N1 C11 C9 113.19(12) . . ?
N1 C11 C12 119.78(13) . . ?
C9 C11 C12 127.02(12) . . ?
C11 N1 O3 106.56(11) . . ?
C2 O1 C1 118.32(12) . . ?
C10 O3 N1 110.29(10) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1448262'
_audit_update_record             
;
2016-04-09 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 N2 O2'
_chemical_formula_weight         256.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   11.971(5)
_cell_length_b                   6.692(3)
_cell_length_c                   17.466(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.810(8)
_cell_angle_gamma                90.00
_cell_volume                     1324.3(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1171
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      21.78

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9812
_exptl_absorpt_correction_T_max  0.9846
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6687
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.46
_reflns_number_total             2379
_reflns_number_gt                1506
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0852P)²+0.0606P] 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         2379
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1633
_refine_ls_wR_factor_gt          0.1404
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2130(2) 0.7474(4) 0.17935(15) 0.0704(8) Uani 1 1 d . . .
H1A H 0.1671 0.7000 0.2124 0.084 Uiso 1 1 calc R . .
H1B H 0.2675 0.6434 0.1757 0.084 Uiso 1 1 calc R . .
C2 C 0.1340(3) 0.8089(5) 0.09648(17) 0.0911(10) Uani 1 1 d . . .
H2A H 0.1731 0.7884 0.0564 0.109 Uiso 1 1 calc R . .
H2B H 0.0612 0.7327 0.0809 0.109 Uiso 1 1 calc R . .
C3 C 0.1101(3) 1.0236(5) 0.10401(18) 0.1010(11) Uani 1 1 d . . .
H3A H 0.0445 1.0413 0.1245 0.121 Uiso 1 1 calc R . .
H3B H 0.0918 1.0901 0.0521 0.121 Uiso 1 1 calc R . .
C4 C 0.2236(2) 1.1063(4) 0.16346(14) 0.0705(8) Uani 1 1 d . . .
H4A H 0.2753 1.1586 0.1354 0.085 Uiso 1 1 calc R . .
H4B H 0.2070 1.2112 0.1966 0.085 Uiso 1 1 calc R . .
C5 C 0.3691(2) 0.9412(3) 0.28152(13) 0.0515(6) Uani 1 1 d . . .
C6 C 0.4106(2) 0.7709(3) 0.32993(14) 0.0588(6) Uani 1 1 d . . .
H6 H 0.3717 0.6499 0.3144 0.071 Uiso 1 1 calc R . .
C7 C 0.5051(2) 0.7775(3) 0.39832(13) 0.0534(6) Uani 1 1 d . . .
H7 H 0.5293 0.6613 0.4283 0.064 Uiso 1 1 calc R . .
C8 C 0.56818(19) 0.9576(3) 0.42521(12) 0.0460(5) Uani 1 1 d . . .
C9 C 0.5247(2) 1.1282(3) 0.37815(12) 0.0535(6) Uani 1 1 d . . .
H9 H 0.5619 1.2500 0.3951 0.064 Uiso 1 1 calc R . .
C10 C 0.4301(2) 1.1236(3) 0.30864(14) 0.0564(6) Uani 1 1 d . . .
H10 H 0.4056 1.2402 0.2790 0.068 Uiso 1 1 calc R . .
C11 C 0.66841(19) 0.9781(3) 0.49544(12) 0.0479(6) Uani 1 1 d . . .
H11 H 0.6941 1.1097 0.5051 0.057 Uiso 1 1 calc R . .
C12 C 0.73596(19) 0.8481(3) 0.55231(12) 0.0467(5) Uani 1 1 d . . .
C13 C 0.7288(2) 0.6327(4) 0.56216(15) 0.0618(7) Uani 1 1 d . . .
C14 C 0.8340(2) 0.9055(3) 0.62115(13) 0.0524(6) Uani 1 1 d . . .
C15 C 0.8873(2) 1.1093(4) 0.63962(15) 0.0721(8) Uani 1 1 d . . .
H15A H 0.9485 1.1074 0.6911 0.108 Uiso 1 1 calc R . .
H15B H 0.8275 1.2033 0.6412 0.108 Uiso 1 1 calc R . .
H15C H 0.9200 1.1481 0.5984 0.108 Uiso 1 1 calc R . .
N1 N 0.27598(18) 0.9322(3) 0.21238(12) 0.0626(6) Uani 1 1 d . . .
N2 N 0.8801(2) 0.7610(3) 0.66985(13) 0.0721(7) Uani 1 1 d . . .
O1 O 0.66853(17) 0.4998(3) 0.52199(11) 0.0846(6) Uani 1 1 d . . .
O2 O 0.81310(17) 0.5843(3) 0.63422(11) 0.0818(6) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.466(3) . ?
C1 C2 1.509(4) . ?
C2 C3 1.478(4) . ?
C3 C4 1.523(4) . ?
C4 N1 1.461(3) . ?
C5 N1 1.355(3) . ?
C5 C6 1.410(3) . ?
C5 C10 1.423(3) . ?
C6 C7 1.356(3) . ?
C7 C8 1.419(3) . ?
C8 C9 1.405(3) . ?
C8 C11 1.419(3) . ?
C9 C10 1.367(3) . ?
C11 C12 1.371(3) . ?
C12 C14 1.436(3) . ?
C12 C13 1.458(3) . ?
C13 O1 1.215(3) . ?
C13 O2 1.374(3) . ?
C14 N2 1.288(3) . ?
C14 C15 1.496(3) . ?
N2 O2 1.452(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 103.4(2) . . ?
C3 C2 C1 105.0(2) . . ?
C2 C3 C4 105.0(3) . . ?
N1 C4 C3 103.2(2) . . ?
N1 C5 C6 121.8(2) . . ?
N1 C5 C10 121.4(2) . . ?
C6 C5 C10 116.7(2) . . ?
C7 C6 C5 122.3(2) . . ?
C6 C7 C8 121.5(2) . . ?
C9 C8 C7 116.05(19) . . ?
C9 C8 C11 118.5(2) . . ?
C7 C8 C11 125.4(2) . . ?
C10 C9 C8 123.1(2) . . ?
C9 C10 C5 120.3(2) . . ?
C12 C11 C8 134.6(2) . . ?
C11 C12 C14 124.7(2) . . ?
C11 C12 C13 132.0(2) . . ?
C14 C12 C13 103.24(19) . . ?
O1 C13 O2 118.7(2) . . ?
O1 C13 C12 134.6(2) . . ?
O2 C13 C12 106.7(2) . . ?
N2 C14 C12 114.4(2) . . ?
N2 C14 C15 118.7(2) . . ?
C12 C14 C15 126.9(2) . . ?
C5 N1 C4 124.1(2) . . ?
C5 N1 C1 124.0(2) . . ?
C4 N1 C1 111.91(19) . . ?
C14 N2 O2 105.57(19) . . ?
C13 O2 N2 109.98(18) . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        25.46
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1448263'
_audit_update_record             
;
2016-04-09 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 N O2'
_chemical_formula_weight         275.29

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.6405(18)
_cell_length_b                   12.712(2)
_cell_length_c                   16.534(3)
_cell_angle_alpha                107.075(4)
_cell_angle_beta                 90.263(4)
_cell_angle_gamma                105.029(4)
_cell_volume                     2056.8(6)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1068
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      20.34

_exptl_crystal_description       slice
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9810
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_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            13022
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0779
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.29
_diffrn_reflns_theta_max         25.05
_reflns_number_total             7257
_reflns_number_gt                3462
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

During the refinement, the commond OMIT was used to omit some disagreeable
reflections. All the non-H atoms were anisotropically refined. The commond DELU
was used to restrain some non-H atoms with large hirshield problems.

The detailed restraint information are as follows:
OMIT -1 1 0 
OMIT 1 1 0 
OMIT 1 -1 1 
OMIT 0 0 2 
OMIT 0 0 3 
OMIT -2 1 1 
OMIT 0 -1 2 
OMIT 1 -1 2 
OMIT 4 -5 2 
DELU 0.01 0.02 C5 C9 C12 C13
;

_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)+(0.0956P)²+0.2690P] 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         7257
_refine_ls_number_parameters     571
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1577
_refine_ls_R_factor_gt           0.0760
_refine_ls_wR_factor_ref         0.2317
_refine_ls_wR_factor_gt          0.1868
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.2108(4) 0.3492(3) 0.6024(3) 0.1078(12) Uani 1 1 d . . .
O2 O -0.1387(4) 0.2554(3) 0.4850(3) 0.1179(14) Uani 1 1 d . . .
N1 N -0.1898(4) 0.3726(4) 0.6926(3) 0.0956(13) Uani 1 1 d . . .
C1 C 0.3932(5) -0.0832(4) 0.3518(4) 0.0971(17) Uani 1 1 d . . .
H1 H 0.4300 -0.0950 0.3984 0.116 Uiso 1 1 calc R . .
C2 C 0.4290(6) -0.1257(5) 0.2703(6) 0.119(2) Uani 1 1 d . . .
H2 H 0.4904 -0.1674 0.2615 0.143 Uiso 1 1 calc R . .
C3 C 0.3742(7) -0.1061(5) 0.2030(5) 0.123(3) Uani 1 1 d . . .
H3 H 0.4005 -0.1340 0.1491 0.148 Uiso 1 1 calc R . .
C4 C 0.2831(6) -0.0476(4) 0.2123(4) 0.0987(17) Uani 1 1 d . . .
H4 H 0.2459 -0.0363 0.1655 0.118 Uiso 1 1 calc R . .
C5 C 0.2467(5) -0.0052(4) 0.2919(4) 0.0782(14) Uani 1 1 d U . .
C6 C 0.3000(5) -0.0225(4) 0.3607(4) 0.0769(14) Uani 1 1 d . . .
C7 C 0.2410(4) 0.0344(3) 0.4369(3) 0.0653(12) Uani 1 1 d . . .
C8 C 0.1539(4) 0.0829(3) 0.4108(3) 0.0644(11) Uani 1 1 d . . .
C9 C 0.1464(5) 0.0619(4) 0.3180(3) 0.0855(14) Uani 1 1 d U . .
H9A H 0.1699 0.1330 0.3038 0.103 Uiso 1 1 calc R . .
H9B H 0.0598 0.0173 0.2915 0.103 Uiso 1 1 calc R . .
C10 C 0.0816(4) 0.1440(3) 0.4702(3) 0.0644(11) Uani 1 1 d . . .
H10 H 0.0220 0.1767 0.4527 0.077 Uiso 1 1 calc R . .
C11 C 0.1031(4) 0.1531(3) 0.5550(3) 0.0564(10) Uani 1 1 d . . .
C12 C 0.1937(4) 0.1014(3) 0.5784(3) 0.0713(12) Uani 1 1 d U . .
H12 H 0.2082 0.1081 0.6354 0.086 Uiso 1 1 calc R . .
C13 C 0.2611(5) 0.0416(4) 0.5201(4) 0.0800(14) Uani 1 1 d U . .
H13 H 0.3191 0.0067 0.5369 0.096 Uiso 1 1 calc R . .
C14 C 0.0387(4) 0.2134(3) 0.6231(3) 0.0569(10) Uani 1 1 d . . .
H14 H 0.0684 0.2141 0.6763 0.068 Uiso 1 1 calc R . .
C15 C -0.0544(4) 0.2686(3) 0.6270(3) 0.0577(10) Uani 1 1 d . . .
C16 C -0.1319(5) 0.2854(4) 0.5618(4) 0.0841(15) Uani 1 1 d . . .
C17 C -0.1017(4) 0.3252(4) 0.7045(3) 0.0679(12) Uani 1 1 d . . .
C18 C -0.0597(5) 0.3336(4) 0.7915(3) 0.0860(15) Uani 1 1 d . . .
H18A H -0.1033 0.3808 0.8311 0.129 Uiso 1 1 calc R . .
H18B H 0.0331 0.3670 0.8020 0.129 Uiso 1 1 calc R . .
H18C H -0.0812 0.2586 0.7981 0.129 Uiso 1 1 calc R . .
O3 O 0.5593(4) 0.1482(3) 0.1306(2) 0.0916(10) Uani 1 1 d . . .
O4 O 0.4169(4) 0.2395(3) 0.1916(2) 0.0988(11) Uani 1 1 d . . .
N2 N 0.6616(4) 0.1063(3) 0.1561(3) 0.0795(11) Uani 1 1 d . . .
C19 C 0.1630(5) 0.5198(4) 0.5848(4) 0.0855(15) Uani 1 1 d . . .
H19 H 0.1285 0.5237 0.5343 0.103 Uiso 1 1 calc R . .
C20 C 0.1175(5) 0.5692(4) 0.6642(5) 0.0934(17) Uani 1 1 d . . .
H20 H 0.0524 0.6065 0.6674 0.112 Uiso 1 1 calc R . .
C21 C 0.1739(6) 0.5596(4) 0.7366(4) 0.0876(16) Uani 1 1 d . . .
H21 H 0.1469 0.5921 0.7894 0.105 Uiso 1 1 calc R . .
C22 C 0.2672(5) 0.5040(4) 0.7319(3) 0.0835(15) Uani 1 1 d . . .
H22 H 0.3025 0.4976 0.7812 0.100 Uiso 1 1 calc R . .
C23 C 0.3085(5) 0.4589(4) 0.6585(4) 0.0777(13) Uani 1 1 d . . .
C24 C 0.2605(5) 0.4659(3) 0.5856(3) 0.0705(13) Uani 1 1 d . . .
C25 C 0.3257(4) 0.4062(3) 0.5116(3) 0.0662(12) Uani 1 1 d . . .
C26 C 0.4126(5) 0.3646(4) 0.5483(3) 0.0746(13) Uani 1 1 d . . .
C27 C 0.4139(5) 0.3898(4) 0.6392(3) 0.0882(15) Uani 1 1 d . . .
H27A H 0.4990 0.4358 0.6674 0.106 Uiso 1 1 calc R . .
H27B H 0.3884 0.3205 0.6557 0.106 Uiso 1 1 calc R . .
C28 C 0.4934(4) 0.3034(3) 0.4955(3) 0.0713(12) Uani 1 1 d . . .
H28 H 0.5527 0.2751 0.5182 0.086 Uiso 1 1 calc R . .
C29 C 0.4793(4) 0.2887(3) 0.4099(3) 0.0619(11) Uani 1 1 d . . .
C30 C 0.3893(4) 0.3343(3) 0.3775(3) 0.0727(13) Uani 1 1 d . . .
H30 H 0.3813 0.3236 0.3194 0.087 Uiso 1 1 calc R . .
C31 C 0.3136(5) 0.3938(4) 0.4286(4) 0.0850(14) Uani 1 1 d . . .
H31 H 0.2562 0.4244 0.4063 0.102 Uiso 1 1 calc R . .
C32 C 0.5628(4) 0.2274(3) 0.3576(3) 0.0592(11) Uani 1 1 d . . .
H32 H 0.6218 0.2091 0.3892 0.071 Uiso 1 1 calc R . .
C33 C 0.5734(4) 0.1914(3) 0.2739(3) 0.0556(10) Uani 1 1 d . . .
C34 C 0.6677(4) 0.1314(3) 0.2371(3) 0.0620(11) Uani 1 1 d . . .
C35 C 0.7635(5) 0.0983(4) 0.2811(3) 0.0840(14) Uani 1 1 d . . .
H35A H 0.8158 0.0625 0.2406 0.126 Uiso 1 1 calc R . .
H35B H 0.7188 0.0455 0.3097 0.126 Uiso 1 1 calc R . .
H35C H 0.8186 0.1650 0.3219 0.126 Uiso 1 1 calc R . .
C36 C 0.5051(5) 0.1998(4) 0.2006(3) 0.0713(13) Uani 1 1 d . . .
O5 O 0.8937(3) 0.8673(2) 0.16520(19) 0.0729(8) Uani 1 1 d . . .
O6 O 0.7391(3) 0.7344(3) 0.1954(2) 0.0905(10) Uani 1 1 d . . .
N3 N 0.9119(4) 0.9308(3) 0.1038(2) 0.0716(10) Uani 1 1 d . . .
C37 C 0.1145(4) 0.2979(3) 0.1581(3) 0.0689(12) Uani 1 1 d . . .
H37 H 0.1427 0.2806 0.2047 0.083 Uiso 1 1 calc R . .
C38 C -0.0083(5) 0.2419(4) 0.1167(3) 0.0777(14) Uani 1 1 d . . .
H38 H -0.0626 0.1857 0.1359 0.093 Uiso 1 1 calc R . .
C39 C -0.0527(4) 0.2663(4) 0.0485(3) 0.0753(13) Uani 1 1 d . . .
H39 H -0.1365 0.2277 0.0224 0.090 Uiso 1 1 calc R . .
C40 C 0.0269(4) 0.3485(3) 0.0181(3) 0.0682(12) Uani 1 1 d . . .
H40 H -0.0021 0.3659 -0.0283 0.082 Uiso 1 1 calc R . .
C41 C 0.1525(4) 0.4051(3) 0.0590(3) 0.0530(10) Uani 1 1 d . . .
C42 C 0.1943(4) 0.3805(3) 0.1284(3) 0.0586(11) Uani 1 1 d . . .
C43 C 0.3304(4) 0.4536(3) 0.1613(3) 0.0619(11) Uani 1 1 d . . .
H43A H 0.3331 0.5015 0.2194 0.074 Uiso 1 1 calc R . .
H43B H 0.3908 0.4074 0.1585 0.074 Uiso 1 1 calc R . .
C44 C 0.3604(4) 0.5240(3) 0.1014(2) 0.0497(9) Uani 1 1 d . . .
C45 C 0.2550(4) 0.4952(3) 0.0412(2) 0.0504(10) Uani 1 1 d . . .
C46 C 0.2617(4) 0.5487(3) -0.0203(3) 0.0606(11) Uani 1 1 d . . .
H46 H 0.1920 0.5285 -0.0610 0.073 Uiso 1 1 calc R . .
C47 C 0.3730(4) 0.6324(3) -0.0208(3) 0.0577(10) Uani 1 1 d . . .
H47 H 0.3770 0.6697 -0.0618 0.069 Uiso 1 1 calc R . .
C48 C 0.4805(4) 0.6632(3) 0.0386(2) 0.0515(10) Uani 1 1 d . . .
C49 C 0.4736(4) 0.6071(3) 0.1006(2) 0.0518(10) Uani 1 1 d . . .
H49 H 0.5440 0.6255 0.1405 0.062 Uiso 1 1 calc R . .
C50 C 0.5913(4) 0.7527(3) 0.0317(2) 0.0521(10) Uani 1 1 d . . .
H50 H 0.5787 0.7804 -0.0130 0.063 Uiso 1 1 calc R . .
C51 C 0.7095(4) 0.8053(3) 0.0758(2) 0.0509(10) Uani 1 1 d . . .
C52 C 0.8068(4) 0.8946(3) 0.0548(3) 0.0549(10) Uani 1 1 d . . .
C53 C 0.7932(4) 0.9445(3) -0.0143(3) 0.0692(12) Uani 1 1 d . . .
H53A H 0.7252 0.9825 -0.0037 0.104 Uiso 1 1 calc R . .
H53B H 0.7714 0.8846 -0.0676 0.104 Uiso 1 1 calc R . .
H53C H 0.8741 0.9985 -0.0164 0.104 Uiso 1 1 calc R . .
C54 C 0.7719(4) 0.7929(4) 0.1494(3) 0.0624(11) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C16 1.360(5) . ?
O1 N1 1.437(5) . ?
O2 C16 1.209(6) . ?
N1 C17 1.281(5) . ?
C1 C6 1.390(7) . ?
C1 C2 1.393(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.351(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(7) . ?
C5 C9 1.522(6) . ?
C6 C7 1.487(6) . ?
C7 C13 1.364(6) . ?
C7 C8 1.369(6) . ?
C8 C10 1.424(6) . ?
C8 C9 1.477(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.386(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.408(5) . ?
C11 C14 1.449(5) . ?
C12 C13 1.372(6) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.346(5) . ?
C14 H14 0.9300 . ?
C15 C17 1.438(6) . ?
C15 C16 1.452(6) . ?
C17 C18 1.469(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O3 C36 1.363(5) . ?
O3 N2 1.440(5) . ?
O4 C36 1.202(5) . ?
N2 C34 1.280(5) . ?
C19 C24 1.386(6) . ?
C19 C20 1.425(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.387(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.351(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.312(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.343(6) . ?
C23 C27 1.575(6) . ?
C24 C25 1.514(6) . ?
C25 C31 1.336(6) . ?
C25 C26 1.393(6) . ?
C26 C28 1.436(6) . ?
C26 C27 1.441(6) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.374(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.416(6) . ?
C29 C32 1.455(5) . ?
C30 C31 1.372(6) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 C33 1.339(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.445(5) . ?
C33 C36 1.456(6) . ?
C34 C35 1.463(6) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
O5 C54 1.362(5) . ?
O5 N3 1.457(4) . ?
O6 C54 1.206(5) . ?
N3 C52 1.274(5) . ?
C37 C42 1.382(5) . ?
C37 C38 1.380(6) . ?
C37 H37 0.9300 . ?
C38 C39 1.368(6) . ?
C38 H38 0.9300 . ?
C39 C40 1.385(6) . ?
C39 H39 0.9300 . ?
C40 C41 1.403(5) . ?
C40 H40 0.9300 . ?
C41 C42 1.375(5) . ?
C41 C45 1.463(5) . ?
C42 C43 1.501(5) . ?
C43 C44 1.502(5) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 C49 1.385(5) . ?
C44 C45 1.395(5) . ?
C45 C46 1.372(5) . ?
C46 C47 1.374(5) . ?
C46 H46 0.9300 . ?
C47 C48 1.399(5) . ?
C47 H47 0.9300 . ?
C48 C49 1.403(5) . ?
C48 C50 1.442(5) . ?
C49 H49 0.9300 . ?
C50 C51 1.353(5) . ?
C50 H50 0.9300 . ?
C51 C54 1.452(6) . ?
C51 C52 1.451(5) . ?
C52 C53 1.483(5) . ?
C53 H53A 0.9600 . ?
C53 H53B 0.9600 . ?
C53 H53C 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
C16 O1 N1 109.9(4) . . ?
C17 N1 O1 106.6(4) . . ?
C6 C1 C2 117.2(6) . . ?
C6 C1 H1 121.4 . . ?
C2 C1 H1 121.4 . . ?
C3 C2 C1 120.2(6) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 122.1(6) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 118.5(6) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 121.0(5) . . ?
C6 C5 C9 110.9(5) . . ?
C4 C5 C9 128.1(6) . . ?
C5 C6 C1 121.0(5) . . ?
C5 C6 C7 107.6(4) . . ?
C1 C6 C7 131.4(6) . . ?
C13 C7 C8 121.6(4) . . ?
C13 C7 C6 130.4(5) . . ?
C8 C7 C6 108.0(5) . . ?
C7 C8 C10 120.9(4) . . ?
C7 C8 C9 112.0(4) . . ?
C10 C8 C9 127.1(4) . . ?
C8 C9 C5 101.6(4) . . ?
C8 C9 H9A 111.5 . . ?
C5 C9 H9A 111.5 . . ?
C8 C9 H9B 111.5 . . ?
C5 C9 H9B 111.5 . . ?
H9A C9 H9B 109.3 . . ?
C11 C10 C8 117.7(4) . . ?
C11 C10 H10 121.1 . . ?
C8 C10 H10 121.1 . . ?
C10 C11 C12 119.1(4) . . ?
C10 C11 C14 124.4(4) . . ?
C12 C11 C14 116.5(4) . . ?
C13 C12 C11 122.3(5) . . ?
C13 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C7 C13 C12 118.3(4) . . ?
C7 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C15 C14 C11 134.6(4) . . ?
C15 C14 H14 112.7 . . ?
C11 C14 H14 112.7 . . ?
C14 C15 C17 124.2(4) . . ?
C14 C15 C16 132.4(4) . . ?
C17 C15 C16 103.3(4) . . ?
O2 C16 O1 119.0(5) . . ?
O2 C16 C15 134.1(5) . . ?
O1 C16 C15 106.9(5) . . ?
N1 C17 C15 113.2(4) . . ?
N1 C17 C18 119.4(4) . . ?
C15 C17 C18 127.4(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C36 O3 N2 109.6(3) . . ?
C34 N2 O3 107.3(4) . . ?
C24 C19 C20 117.6(5) . . ?
C24 C19 H19 121.2 . . ?
C20 C19 H19 121.2 . . ?
C21 C20 C19 117.6(5) . . ?
C21 C20 H20 121.2 . . ?
C19 C20 H20 121.2 . . ?
C22 C21 C20 121.2(5) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C23 C22 C21 120.7(5) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 121.8(5) . . ?
C22 C23 C27 128.7(6) . . ?
C24 C23 C27 109.5(5) . . ?
C23 C24 C19 121.0(5) . . ?
C23 C24 C25 110.2(5) . . ?
C19 C24 C25 128.8(5) . . ?
C31 C25 C26 123.5(5) . . ?
C31 C25 C24 132.0(5) . . ?
C26 C25 C24 104.4(5) . . ?
C25 C26 C28 119.5(4) . . ?
C25 C26 C27 115.1(5) . . ?
C28 C26 C27 125.4(5) . . ?
C26 C27 C23 100.8(4) . . ?
C26 C27 H27A 111.6 . . ?
C23 C27 H27A 111.6 . . ?
C26 C27 H27B 111.6 . . ?
C23 C27 H27B 111.6 . . ?
H27A C27 H27B 109.4 . . ?
C29 C28 C26 117.0(4) . . ?
C29 C28 H28 121.5 . . ?
C26 C28 H28 121.5 . . ?
C28 C29 C30 120.0(4) . . ?
C28 C29 C32 116.2(4) . . ?
C30 C29 C32 123.8(4) . . ?
C31 C30 C29 122.5(5) . . ?
C31 C30 H30 118.7 . . ?
C29 C30 H30 118.7 . . ?
C25 C31 C30 117.4(5) . . ?
C25 C31 H31 121.3 . . ?
C30 C31 H31 121.3 . . ?
C33 C32 C29 134.0(4) . . ?
C33 C32 H32 113.0 . . ?
C29 C32 H32 113.0 . . ?
C32 C33 C34 123.2(4) . . ?
C32 C33 C36 133.2(4) . . ?
C34 C33 C36 103.5(4) . . ?
N2 C34 C33 112.7(4) . . ?
N2 C34 C35 119.4(4) . . ?
C33 C34 C35 127.9(4) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O4 C36 O3 119.2(5) . . ?
O4 C36 C33 133.9(5) . . ?
O3 C36 C33 106.9(4) . . ?
C54 O5 N3 109.3(3) . . ?
C52 N3 O5 106.9(3) . . ?
C42 C37 C38 118.2(4) . . ?
C42 C37 H37 120.9 . . ?
C38 C37 H37 120.9 . . ?
C39 C38 C37 122.1(4) . . ?
C39 C38 H38 118.9 . . ?
C37 C38 H38 118.9 . . ?
C38 C39 C40 120.0(4) . . ?
C38 C39 H39 120.0 . . ?
C40 C39 H39 120.0 . . ?
C39 C40 C41 118.4(4) . . ?
C39 C40 H40 120.8 . . ?
C41 C40 H40 120.8 . . ?
C42 C41 C40 120.6(4) . . ?
C42 C41 C45 109.5(4) . . ?
C40 C41 C45 129.9(4) . . ?
C41 C42 C37 120.7(4) . . ?
C41 C42 C43 110.3(3) . . ?
C37 C42 C43 129.0(4) . . ?
C44 C43 C42 102.2(3) . . ?
C44 C43 H43A 111.3 . . ?
C42 C43 H43A 111.3 . . ?
C44 C43 H43B 111.3 . . ?
C42 C43 H43B 111.3 . . ?
H43A C43 H43B 109.2 . . ?
C49 C44 C45 120.8(3) . . ?
C49 C44 C43 128.5(4) . . ?
C45 C44 C43 110.7(3) . . ?
C46 C45 C44 120.5(4) . . ?
C46 C45 C41 132.2(4) . . ?
C44 C45 C41 107.3(3) . . ?
C45 C46 C47 119.0(4) . . ?
C45 C46 H46 120.5 . . ?
C47 C46 H46 120.5 . . ?
C46 C47 C48 121.9(4) . . ?
C46 C47 H47 119.1 . . ?
C48 C47 H47 119.1 . . ?
C49 C48 C47 118.8(3) . . ?
C49 C48 C50 124.5(4) . . ?
C47 C48 C50 116.7(4) . . ?
C44 C49 C48 119.0(4) . . ?
C44 C49 H49 120.5 . . ?
C48 C49 H49 120.5 . . ?
C51 C50 C48 134.2(4) . . ?
C51 C50 H50 112.9 . . ?
C48 C50 H50 112.9 . . ?
C50 C51 C54 133.0(4) . . ?
C50 C51 C52 123.5(4) . . ?
C54 C51 C52 103.5(3) . . ?
N3 C52 C51 113.0(4) . . ?
N3 C52 C53 120.3(4) . . ?
C51 C52 C53 126.7(4) . . ?
C52 C53 H53A 109.5 . . ?
C52 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C52 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
O6 C54 O5 118.3(4) . . ?
O6 C54 C51 134.5(4) . . ?
O5 C54 C51 107.2(4) . . ?

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
C16 O1 N1 C17 0.4(5) . . . . ?
C6 C1 C2 C3 0.7(8) . . . . ?
C1 C2 C3 C4 -1.1(10) . . . . ?
C2 C3 C4 C5 1.1(9) . . . . ?
C3 C4 C5 C6 -0.7(7) . . . . ?
C3 C4 C5 C9 -179.4(5) . . . . ?
C4 C5 C6 C1 0.3(7) . . . . ?
C9 C5 C6 C1 179.2(4) . . . . ?
C4 C5 C6 C7 179.7(4) . . . . ?
C9 C5 C6 C7 -1.4(5) . . . . ?
C2 C1 C6 C5 -0.3(7) . . . . ?
C2 C1 C6 C7 -179.5(5) . . . . ?
C5 C6 C7 C13 179.8(4) . . . . ?
C1 C6 C7 C13 -1.0(8) . . . . ?
C5 C6 C7 C8 0.4(5) . . . . ?
C1 C6 C7 C8 179.7(4) . . . . ?
C13 C7 C8 C10 0.6(6) . . . . ?
C6 C7 C8 C10 -180.0(3) . . . . ?
C13 C7 C8 C9 -178.7(4) . . . . ?
C6 C7 C8 C9 0.7(5) . . . . ?
C7 C8 C9 C5 -1.5(5) . . . . ?
C10 C8 C9 C5 179.3(4) . . . . ?
C6 C5 C9 C8 1.8(5) . . . . ?
C4 C5 C9 C8 -179.4(4) . . . . ?
C7 C8 C10 C11 0.4(6) . . . . ?
C9 C8 C10 C11 179.6(4) . . . . ?
C8 C10 C11 C12 -0.5(6) . . . . ?
C8 C10 C11 C14 179.3(3) . . . . ?
C10 C11 C12 C13 -0.4(6) . . . . ?
C14 C11 C12 C13 179.8(4) . . . . ?
C8 C7 C13 C12 -1.5(6) . . . . ?
C6 C7 C13 C12 179.3(4) . . . . ?
C11 C12 C13 C7 1.4(6) . . . . ?
C10 C11 C14 C15 3.2(7) . . . . ?
C12 C11 C14 C15 -177.0(4) . . . . ?
C11 C14 C15 C17 -178.6(4) . . . . ?
C11 C14 C15 C16 2.9(8) . . . . ?
N1 O1 C16 O2 178.3(5) . . . . ?
N1 O1 C16 C15 -1.4(5) . . . . ?
C14 C15 C16 O2 0.8(10) . . . . ?
C17 C15 C16 O2 -177.9(6) . . . . ?
C14 C15 C16 O1 -179.6(4) . . . . ?
C17 C15 C16 O1 1.7(5) . . . . ?
O1 N1 C17 C15 0.8(5) . . . . ?
O1 N1 C17 C18 -179.5(4) . . . . ?
C14 C15 C17 N1 179.5(4) . . . . ?
C16 C15 C17 N1 -1.6(5) . . . . ?
C14 C15 C17 C18 -0.1(7) . . . . ?
C16 C15 C17 C18 178.7(4) . . . . ?
C36 O3 N2 C34 0.2(5) . . . . ?
C24 C19 C20 C21 -0.1(6) . . . . ?
C19 C20 C21 C22 -0.9(7) . . . . ?
C20 C21 C22 C23 1.1(7) . . . . ?
C21 C22 C23 C24 0.0(7) . . . . ?
C21 C22 C23 C27 -179.0(4) . . . . ?
C22 C23 C24 C19 -1.1(7) . . . . ?
C27 C23 C24 C19 178.1(4) . . . . ?
C22 C23 C24 C25 -179.8(4) . . . . ?
C27 C23 C24 C25 -0.6(5) . . . . ?
C20 C19 C24 C23 1.1(6) . . . . ?
C20 C19 C24 C25 179.5(4) . . . . ?
C23 C24 C25 C31 -177.6(5) . . . . ?
C19 C24 C25 C31 3.8(8) . . . . ?
C23 C24 C25 C26 0.5(5) . . . . ?
C19 C24 C25 C26 -178.1(4) . . . . ?
C31 C25 C26 C28 -0.9(6) . . . . ?
C24 C25 C26 C28 -179.2(3) . . . . ?
C31 C25 C26 C27 178.1(4) . . . . ?
C24 C25 C26 C27 -0.2(5) . . . . ?
C25 C26 C27 C23 -0.2(5) . . . . ?
C28 C26 C27 C23 178.8(4) . . . . ?
C22 C23 C27 C26 179.6(5) . . . . ?
C24 C23 C27 C26 0.5(5) . . . . ?
C25 C26 C28 C29 -0.4(6) . . . . ?
C27 C26 C28 C29 -179.3(4) . . . . ?
C26 C28 C29 C30 0.9(6) . . . . ?
C26 C28 C29 C32 179.5(3) . . . . ?
C28 C29 C30 C31 -0.1(6) . . . . ?
C32 C29 C30 C31 -178.6(4) . . . . ?
C26 C25 C31 C30 1.7(7) . . . . ?
C24 C25 C31 C30 179.4(4) . . . . ?
C29 C30 C31 C25 -1.2(7) . . . . ?
C28 C29 C32 C33 175.9(4) . . . . ?
C30 C29 C32 C33 -5.6(7) . . . . ?
C29 C32 C33 C34 179.5(4) . . . . ?
C29 C32 C33 C36 0.4(8) . . . . ?
O3 N2 C34 C33 -0.1(5) . . . . ?
O3 N2 C34 C35 179.6(4) . . . . ?
C32 C33 C34 N2 -179.3(4) . . . . ?
C36 C33 C34 N2 0.1(5) . . . . ?
C32 C33 C34 C35 1.0(7) . . . . ?
C36 C33 C34 C35 -179.7(4) . . . . ?
N2 O3 C36 O4 -179.4(4) . . . . ?
N2 O3 C36 C33 -0.1(4) . . . . ?
C32 C33 C36 O4 -1.5(9) . . . . ?
C34 C33 C36 O4 179.2(5) . . . . ?
C32 C33 C36 O3 179.3(4) . . . . ?
C34 C33 C36 O3 0.0(4) . . . . ?
C54 O5 N3 C52 -0.4(4) . . . . ?
C42 C37 C38 C39 -0.5(6) . . . . ?
C37 C38 C39 C40 0.9(7) . . . . ?
C38 C39 C40 C41 -0.1(6) . . . . ?
C39 C40 C41 C42 -1.0(6) . . . . ?
C39 C40 C41 C45 -179.2(4) . . . . ?
C40 C41 C42 C37 1.4(6) . . . . ?
C45 C41 C42 C37 179.9(3) . . . . ?
C40 C41 C42 C43 -179.0(3) . . . . ?
C45 C41 C42 C43 -0.4(4) . . . . ?
C38 C37 C42 C41 -0.6(6) . . . . ?
C38 C37 C42 C43 179.8(4) . . . . ?
C41 C42 C43 C44 0.3(4) . . . . ?
C37 C42 C43 C44 180.0(4) . . . . ?
C42 C43 C44 C49 -179.8(3) . . . . ?
C42 C43 C44 C45 -0.1(4) . . . . ?
C49 C44 C45 C46 0.1(5) . . . . ?
C43 C44 C45 C46 -179.6(3) . . . . ?
C49 C44 C45 C41 179.6(3) . . . . ?
C43 C44 C45 C41 -0.1(4) . . . . ?
C42 C41 C45 C46 179.7(4) . . . . ?
C40 C41 C45 C46 -1.9(7) . . . . ?
C42 C41 C45 C44 0.4(4) . . . . ?
C40 C41 C45 C44 178.7(4) . . . . ?
C44 C45 C46 C47 -1.1(5) . . . . ?
C41 C45 C46 C47 179.7(4) . . . . ?
C45 C46 C47 C48 1.2(6) . . . . ?
C46 C47 C48 C49 -0.4(6) . . . . ?
C46 C47 C48 C50 -179.7(3) . . . . ?
C45 C44 C49 C48 0.7(5) . . . . ?
C43 C44 C49 C48 -179.7(3) . . . . ?
C47 C48 C49 C44 -0.5(5) . . . . ?
C50 C48 C49 C44 178.7(3) . . . . ?
C49 C48 C50 C51 0.3(6) . . . . ?
C47 C48 C50 C51 179.6(4) . . . . ?
C48 C50 C51 C54 -0.8(7) . . . . ?
C48 C50 C51 C52 179.4(4) . . . . ?
O5 N3 C52 C51 -0.6(4) . . . . ?
O5 N3 C52 C53 178.8(3) . . . . ?
C50 C51 C52 N3 -178.9(4) . . . . ?
C54 C51 C52 N3 1.3(4) . . . . ?
C50 C51 C52 C53 1.8(6) . . . . ?
C54 C51 C52 C53 -178.1(4) . . . . ?
N3 O5 C54 O6 -178.7(4) . . . . ?
N3 O5 C54 C51 1.2(4) . . . . ?
C50 C51 C54 O6 -1.5(8) . . . . ?
C52 C51 C54 O6 178.4(5) . . . . ?
C50 C51 C54 O5 178.7(4) . . . . ?
C52 C51 C54 O5 -1.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.787
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1448264'
_audit_update_record             
;
2016-04-09 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 N O2 S'
_chemical_formula_weight         233.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   12.125(2)
_cell_length_b                   7.2540(14)
_cell_length_c                   12.888(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.581(5)
_cell_angle_gamma                90.00
_cell_volume                     1123.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3140
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      25.05

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9428
_exptl_absorpt_correction_T_max  0.9528
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_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            6759
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         25.20
_reflns_number_total             1998
_reflns_number_gt                1782
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1343P)²+5.9691P] 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         1998
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0958
_refine_ls_wR_factor_ref         0.2829
_refine_ls_wR_factor_gt          0.2799
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7308(4) 0.1458(7) 0.5308(4) 0.0351(12) Uani 1 1 d . . .
C2 C 0.6819(4) 0.1772(8) 0.6215(4) 0.0406(13) Uani 1 1 d . . .
H2 H 0.7239 0.1646 0.6870 0.049 Uiso 1 1 calc R . .
C3 C 0.5712(4) 0.2270(8) 0.6138(4) 0.0399(13) Uani 1 1 d . . .
H3 H 0.5395 0.2463 0.6747 0.048 Uiso 1 1 calc R . .
C4 C 0.5057(4) 0.2491(7) 0.5175(4) 0.0308(11) Uani 1 1 d . . .
C5 C 0.5552(4) 0.2167(8) 0.4275(4) 0.0382(12) Uani 1 1 d . . .
H5 H 0.5131 0.2304 0.3622 0.046 Uiso 1 1 calc R . .
C6 C 0.6654(4) 0.1648(8) 0.4333(4) 0.0405(13) Uani 1 1 d . . .
H6 H 0.6964 0.1424 0.3722 0.049 Uiso 1 1 calc R . .
C7 C 0.3906(4) 0.3031(7) 0.5186(4) 0.0337(11) Uani 1 1 d . . .
H7 H 0.3717 0.3119 0.5860 0.040 Uiso 1 1 calc R . .
C8 C 0.3046(4) 0.3435(7) 0.4447(4) 0.0321(11) Uani 1 1 d . . .
C9 C 0.1952(4) 0.3968(7) 0.4668(4) 0.0370(12) Uani 1 1 d . . .
C10 C 0.1580(5) 0.4136(9) 0.5694(5) 0.0476(15) Uani 1 1 d . . .
H10A H 0.0806 0.4462 0.5611 0.071 Uiso 1 1 calc R . .
H10B H 0.2005 0.5076 0.6090 0.071 Uiso 1 1 calc R . .
H10C H 0.1684 0.2981 0.6058 0.071 Uiso 1 1 calc R . .
C11 C 0.2954(4) 0.3502(8) 0.3304(4) 0.0398(13) Uani 1 1 d . . .
C12 C 0.9282(5) 0.0754(11) 0.6630(5) 0.0581(18) Uani 1 1 d . . .
H12A H 0.9227 0.1950 0.6938 0.087 Uiso 1 1 calc R . .
H12B H 1.0049 0.0398 0.6683 0.087 Uiso 1 1 calc R . .
H12C H 0.8882 -0.0127 0.6993 0.087 Uiso 1 1 calc R . .
N1 N 0.1278(4) 0.4324(7) 0.3833(4) 0.0493(13) Uani 1 1 d . . .
O1 O 0.3586(4) 0.3179(8) 0.2667(3) 0.0617(14) Uani 1 1 d . . .
O2 O 0.1891(3) 0.4033(6) 0.2958(3) 0.0512(12) Uani 1 1 d . . .
S1 S 0.86979(11) 0.0831(2) 0.52848(12) 0.0469(5) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.401(8) . ?
C1 C2 1.398(8) . ?
C1 S1 1.749(5) . ?
C2 C3 1.381(7) . ?
C3 C4 1.391(7) . ?
C4 C5 1.395(7) . ?
C4 C7 1.451(7) . ?
C5 C6 1.381(7) . ?
C7 C8 1.349(7) . ?
C8 C9 1.446(7) . ?
C8 C11 1.463(7) . ?
C9 N1 1.289(7) . ?
C9 C10 1.458(8) . ?
C11 O1 1.216(7) . ?
C11 O2 1.363(7) . ?
C12 S1 1.785(7) . ?
N1 O2 1.446(7) . ?

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
C6 C1 C2 118.8(5) . . ?
C6 C1 S1 116.3(4) . . ?
C2 C1 S1 124.9(4) . . ?
C3 C2 C1 119.8(5) . . ?
C2 C3 C4 122.0(5) . . ?
C3 C4 C5 117.6(5) . . ?
C3 C4 C7 117.4(5) . . ?
C5 C4 C7 125.0(5) . . ?
C6 C5 C4 121.4(5) . . ?
C5 C6 C1 120.3(5) . . ?
C8 C7 C4 135.0(5) . . ?
C7 C8 C9 124.3(5) . . ?
C7 C8 C11 131.8(5) . . ?
C9 C8 C11 103.9(4) . . ?
N1 C9 C8 112.7(5) . . ?
N1 C9 C10 120.2(5) . . ?
C8 C9 C10 127.1(5) . . ?
O1 C11 O2 119.1(5) . . ?
O1 C11 C8 134.6(5) . . ?
O2 C11 C8 106.3(4) . . ?
C9 N1 O2 106.7(4) . . ?
C11 O2 N1 110.4(4) . . ?
C1 S1 C12 104.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.20
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.876
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.122
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1448265'
_audit_update_record             
;
2016-04-09 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;
_audit_creation_date             2016-04-07
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H9 N O2 S'
_chemical_formula_sum            'C10 H9 N O2 S'
_chemical_formula_weight         207.24
_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      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                   6.581(5)
_cell_length_b                   21.472(17)
_cell_length_c                   7.066(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.36(2)
_cell_angle_gamma                90
_cell_volume                     967.2(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    609
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.09
_cell_measurement_theta_min      3.33
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  0.9760
_exptl_absorpt_correction_T_min  0.9643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6478
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.956
_diffrn_reflns_theta_min         1.897
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1134
_reflns_number_total             1864
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1864
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0682
_refine_ls_restrained_S_all      0.976
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1085P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1645
_refine_ls_wR_factor_ref         0.1977
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C)
;
_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
C1 C 0.3692(8) 0.4503(2) 0.6909(6) 0.0908(16) Uani 1 1 d . . . . .
H1A H 0.2869 0.4863 0.6408 0.136 Uiso 1 1 calc GR . . . .
H1B H 0.4767 0.4447 0.6221 0.136 Uiso 1 1 calc GR . . . .
H1C H 0.4328 0.4560 0.8275 0.136 Uiso 1 1 calc GR . . . .
C2 C 0.2316(7) 0.3942(2) 0.6635(6) 0.0641(11) Uani 1 1 d . . . . .
C3 C 0.0217(7) 0.3910(2) 0.6201(6) 0.0698(12) Uani 1 1 d . . . . .
H3 H -0.0646 0.4259 0.6023 0.084 Uiso 1 1 calc R . . . .
C4 C -0.0540(7) 0.3306(2) 0.6042(6) 0.0632(11) Uani 1 1 d . . . . .
H4 H -0.1965 0.3212 0.5736 0.076 Uiso 1 1 calc R . . . .
C5 C 0.0984(5) 0.28573(19) 0.6375(5) 0.0488(9) Uani 1 1 d . . . . .
C6 C 0.0580(5) 0.22163(19) 0.6277(5) 0.0516(9) Uani 1 1 d . . . . .
H6 H -0.0845 0.2125 0.5975 0.062 Uiso 1 1 calc R . . . .
C7 C 0.1795(6) 0.17015(18) 0.6521(5) 0.0517(9) Uani 1 1 d . . . . .
C8 C 0.4023(7) 0.1667(2) 0.7033(6) 0.0582(10) Uani 1 1 d . . . . .
C9 C 0.1105(7) 0.1072(2) 0.6373(6) 0.0624(11) Uani 1 1 d . . . . .
C10 C -0.1069(8) 0.0854(2) 0.5840(8) 0.0849(15) Uani 1 1 d . . . . .
H10A H -0.1090 0.0409 0.5709 0.127 Uiso 1 1 calc GR . . . .
H10B H -0.1792 0.1039 0.4622 0.127 Uiso 1 1 calc GR . . . .
H10C H -0.1752 0.0971 0.6840 0.127 Uiso 1 1 calc GR . . . .
N1 N 0.2625(6) 0.06803(19) 0.6746(5) 0.0798(11) Uani 1 1 d . . . . .
O1 O 0.5419(5) 0.20416(15) 0.7304(4) 0.0740(9) Uani 1 1 d . . . . .
O2 O 0.4521(5) 0.10407(16) 0.7199(5) 0.0813(10) Uani 1 1 d . . . . .
S1 S 0.34242(15) 0.32185(5) 0.68843(14) 0.0573(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.490(6) . ?
C2 C3 1.341(6) . ?
C2 S1 1.707(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.368(5) . ?
C5 C6 1.400(6) . ?
C5 S1 1.739(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.350(5) . ?
C7 C8 1.422(6) . ?
C7 C9 1.421(6) . ?
C8 O1 1.200(5) . ?
C8 O2 1.382(5) . ?
C9 C10 1.463(6) . ?
C9 N1 1.284(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N1 O2 1.435(5) . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 S1 119.5(4) . . ?
C3 C2 C1 129.1(4) . . ?
C3 C2 S1 111.5(3) . . ?
C2 C3 H3 123.3 . . ?
C2 C3 C4 113.4(4) . . ?
C4 C3 H3 123.3 . . ?
C3 C4 H4 122.8 . . ?
C5 C4 C3 114.3(4) . . ?
C5 C4 H4 122.8 . . ?
C4 C5 C6 124.1(4) . . ?
C4 C5 S1 108.8(3) . . ?
C6 C5 S1 127.1(3) . . ?
C5 C6 H6 112.8 . . ?
C7 C6 C5 134.4(4) . . ?
C7 C6 H6 112.8 . . ?
C6 C7 C8 128.0(4) . . ?
C6 C7 C9 126.9(4) . . ?
C9 C7 C8 105.0(4) . . ?
O1 C8 C7 134.9(4) . . ?
O1 C8 O2 118.9(4) . . ?
O2 C8 C7 106.3(4) . . ?
C7 C9 C10 126.7(4) . . ?
N1 C9 C7 112.9(4) . . ?
N1 C9 C10 120.4(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 N1 O2 106.4(4) . . ?
C8 O2 N1 109.4(3) . . ?
C2 S1 C5 92.1(2) . . ?

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 C2 C3 C4 179.6(4) . . . . ?
C1 C2 S1 C5 -179.8(3) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C2 S1 C5 0.3(3) . . . . ?
C3 C4 C5 C6 -179.4(3) . . . . ?
C3 C4 C5 S1 -0.3(4) . . . . ?
C4 C5 C6 C7 179.2(4) . . . . ?
C4 C5 S1 C2 0.0(3) . . . . ?
C5 C6 C7 C8 1.6(6) . . . . ?
C5 C6 C7 C9 179.7(4) . . . . ?
C6 C5 S1 C2 179.1(3) . . . . ?
C6 C7 C8 O1 -3.7(7) . . . . ?
C6 C7 C8 O2 177.1(3) . . . . ?
C6 C7 C9 C10 2.9(6) . . . . ?
C6 C7 C9 N1 -177.8(3) . . . . ?
C7 C8 O2 N1 1.5(4) . . . . ?
C7 C9 N1 O2 0.3(4) . . . . ?
C8 C7 C9 C10 -178.7(4) . . . . ?
C8 C7 C9 N1 0.7(5) . . . . ?
C9 C7 C8 O1 177.9(4) . . . . ?
C9 C7 C8 O2 -1.3(4) . . . . ?
C9 N1 O2 C8 -1.1(4) . . . . ?
C10 C9 N1 O2 179.7(4) . . . . ?
O1 C8 O2 N1 -177.9(3) . . . . ?
S1 C2 C3 C4 -0.6(5) . . . . ?
S1 C5 C6 C7 0.3(6) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_bo2888
_database_code_depnum_ccdc_archive 'CCDC 1448267'
_audit_update_record             
;
2016-04-09 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H15 N O2'
_chemical_formula_weight         325.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   24.695(7)
_cell_length_b                   5.6676(15)
_cell_length_c                   11.644(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.552(4)
_cell_angle_gamma                90.00
_cell_volume                     1619.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4162
_cell_measurement_theta_min      2.490
_cell_measurement_theta_max      29.131

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15032
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         29.12
_reflns_number_total             4306
_reflns_number_gt                3023
_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    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.

During the refinement, the commond OMIT was used to omit some disagreeable 
reflections. All the non-H atoms were anisotropically refined. The commond DFIX
was used to restrain the distance between two atoms. The commond EADP was used 
to restrain the same isotropic or anisotropic displacement parameters for two or more atoms

The detailed restraint information are as follows:
OMIT 3 0 0 
DFIX 1.48 .003 C1 C17 C1 C17'
EADP C17 C17' 
;

_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)+(0.0463P)²+0.2820P] 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         4306
_refine_ls_number_parameters     269
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1146
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.33238(4) -0.0412(2) 0.51109(9) 0.0388(3) Uani 1 1 d . A .
O2 O 0.26810(5) 0.2061(2) 0.55909(10) 0.0485(3) Uani 1 1 d . A .
N1 N 0.37012(5) -0.0579(2) 0.42506(11) 0.0351(3) Uani 1 1 d . A .
C1 C 0.16728(6) 0.9559(3) 0.33431(13) 0.0340(4) Uani 1 1 d D . .
C2 C 0.17858(8) 0.7900(4) 0.42194(18) 0.0657(7) Uani 1 1 d . A .
H2 H 0.1570 0.7899 0.4845 0.079 Uiso 1 1 calc R . .
C3 C 0.21954(8) 0.6265(4) 0.42176(16) 0.0587(6) Uani 1 1 d . . .
H3 H 0.2254 0.5157 0.4831 0.070 Uiso 1 1 calc R A .
C4 C 0.25270(6) 0.6212(3) 0.33271(12) 0.0292(3) Uani 1 1 d . A .
C5 C 0.24198(6) 0.7880(3) 0.24516(14) 0.0394(4) Uani 1 1 d . . .
H5 H 0.2638 0.7894 0.1830 0.047 Uiso 1 1 calc R A .
C6 C 0.20057(7) 0.9511(3) 0.24622(14) 0.0418(4) Uani 1 1 d . A .
H6 H 0.1947 1.0627 0.1852 0.050 Uiso 1 1 calc R . .
C7 C 0.29733(6) 0.4601(3) 0.32454(12) 0.0286(3) Uani 1 1 d . . .
H7 H 0.3164 0.4896 0.2597 0.034 Uiso 1 1 calc R A .
C8 C 0.30107(6) 0.1602(3) 0.49321(13) 0.0349(4) Uani 1 1 d . . .
C9 C 0.31787(6) 0.2750(3) 0.38998(12) 0.0284(3) Uani 1 1 d . A .
C10 C 0.36137(6) 0.1246(3) 0.35899(12) 0.0282(3) Uani 1 1 d . . .
C11 C 0.39522(6) 0.1618(3) 0.26311(12) 0.0276(3) Uani 1 1 d . A .
C12 C 0.39685(6) -0.0083(3) 0.17701(13) 0.0323(3) Uani 1 1 d . . .
H12 H 0.3757 -0.1480 0.1788 0.039 Uiso 1 1 calc R A .
C13 C 0.42920(6) 0.0263(3) 0.08893(13) 0.0356(4) Uani 1 1 d . A .
H13 H 0.4299 -0.0888 0.0298 0.043 Uiso 1 1 calc R . .
C14 C 0.46053(6) 0.2282(3) 0.08680(13) 0.0355(4) Uani 1 1 d . . .
H14 H 0.4831 0.2500 0.0268 0.043 Uiso 1 1 calc R A .
C15 C 0.45924(6) 0.3986(3) 0.17161(13) 0.0336(4) Uani 1 1 d . A .
H15 H 0.4809 0.5367 0.1700 0.040 Uiso 1 1 calc R . .
C16 C 0.42603(6) 0.3667(3) 0.25909(12) 0.0302(3) Uani 1 1 d . . .
H16 H 0.4244 0.4851 0.3163 0.036 Uiso 1 1 calc R A .
C17 C 0.12166(12) 1.1271(5) 0.3358(3) 0.0357(4) Uani 0.530(5) 1 d PD A 1
C18 C 0.12041(15) 1.3336(6) 0.2685(3) 0.0431(11) Uani 0.530(5) 1 d PD A 1
H18 H 0.1495 1.3661 0.2240 0.052 Uiso 0.530(5) 1 calc PR A 1
C19 C 0.07709(17) 1.4908(7) 0.2665(4) 0.0457(13) Uani 0.530(5) 1 d PD A 1
H19 H 0.0756 1.6240 0.2167 0.055 Uiso 0.530(5) 1 calc PR A 1
C20 C 0.0364(4) 1.4554(16) 0.3358(7) 0.052(4) Uani 0.530(5) 1 d PD A 1
H20 H 0.0073 1.5651 0.3356 0.062 Uiso 0.530(5) 1 calc PR A 1
C21 C 0.03835(15) 1.2578(8) 0.4058(4) 0.0485(13) Uani 0.530(5) 1 d PD A 1
H21 H 0.0103 1.2313 0.4537 0.058 Uiso 0.530(5) 1 calc PR A 1
C22 C 0.08107(9) 1.0975(4) 0.40660(19) 0.0422(11) Uani 0.530(5) 1 d PD A 1
H22 H 0.0823 0.9652 0.4569 0.051 Uiso 0.530(5) 1 calc PR A 1
C17' C 0.12301(9) 1.1317(4) 0.33599(19) 0.0357(4) Uani 0.470(5) 1 d PRD A 2
C18' C 0.10375(9) 1.2615(4) 0.23681(19) 0.0462(13) Uani 0.470(5) 1 d PRD A 2
H18' H 0.1186 1.2342 0.1662 0.055 Uiso 0.470(5) 1 calc PR A 2
C19' C 0.0630(2) 1.4297(10) 0.2415(4) 0.061(2) Uani 0.470(5) 1 d PD A 2
H19' H 0.0518 1.5231 0.1753 0.073 Uiso 0.470(5) 1 calc PR A 2
C20' C 0.0389(5) 1.462(2) 0.3410(9) 0.067(5) Uani 0.470(5) 1 d PD A 2
H20' H 0.0104 1.5738 0.3431 0.081 Uiso 0.470(5) 1 calc PR A 2
C21' C 0.0566(3) 1.3299(12) 0.4377(5) 0.073(2) Uani 0.470(5) 1 d PD A 2
H21' H 0.0407 1.3539 0.5074 0.088 Uiso 0.470(5) 1 calc PR A 2
C22' C 0.0975(2) 1.1621(9) 0.4342(4) 0.0564(18) Uani 0.470(5) 1 d PD A 2
H22' H 0.1080 1.0674 0.5003 0.068 Uiso 0.470(5) 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 C8 1.3811(19) . ?
O1 N1 1.4472(15) . ?
O2 C8 1.2091(17) . ?
N1 C10 1.2924(18) . ?
C1 C6 1.3861(19) . ?
C1 C2 1.392(2) . ?
C1 C17' 1.481(2) . ?
C1 C17 1.488(2) . ?
C2 C3 1.372(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(2) . ?
C4 C7 1.4427(19) . ?
C5 C6 1.380(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C9 1.360(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.468(2) . ?
C9 C10 1.4492(19) . ?
C10 C11 1.4841(19) . ?
C11 C16 1.392(2) . ?
C11 C12 1.395(2) . ?
C12 C13 1.384(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.3905(19) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.379(3) . ?
C17 C18 1.407(3) . ?
C18 C19 1.390(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.374(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.392(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C17' C22' 1.378(3) . ?
C17' C18' 1.4057 . ?
C18' C19' 1.391(3) . ?
C18' H18' 0.9500 . ?
C19' C20' 1.374(5) . ?
C19' H19' 0.9500 . ?
C20' C21' 1.382(5) . ?
C20' H20' 0.9500 . ?
C21' C22' 1.392(3) . ?
C21' H21' 0.9500 . ?
C22' H22' 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
C8 O1 N1 110.08(11) . . ?
C10 N1 O1 106.42(12) . . ?
C6 C1 C2 116.29(14) . . ?
C6 C1 C17' 121.61(14) . . ?
C2 C1 C17' 122.09(14) . . ?
C6 C1 C17 122.34(16) . . ?
C2 C1 C17 121.38(16) . . ?
C17' C1 C17 1.6(2) . . ?
C3 C2 C1 122.77(15) . . ?
C3 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
C2 C3 C4 120.80(16) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 116.82(14) . . ?
C3 C4 C7 125.54(14) . . ?
C5 C4 C7 117.63(12) . . ?
C6 C5 C4 121.81(14) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 121.51(15) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
C9 C7 C4 133.62(13) . . ?
C9 C7 H7 113.2 . . ?
C4 C7 H7 113.2 . . ?
O2 C8 O1 119.22(14) . . ?
O2 C8 C9 134.26(15) . . ?
O1 C8 C9 106.52(12) . . ?
C7 C9 C10 123.64(13) . . ?
C7 C9 C8 132.73(13) . . ?
C10 C9 C8 103.29(13) . . ?
N1 C10 C9 113.64(13) . . ?
N1 C10 C11 119.44(13) . . ?
C9 C10 C11 126.92(13) . . ?
C16 C11 C12 119.44(13) . . ?
C16 C11 C10 120.06(13) . . ?
C12 C11 C10 120.49(13) . . ?
C13 C12 C11 120.09(14) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 120.12(14) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.40(14) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C16 119.70(15) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 120.22(14) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C22 C17 C18 117.6(2) . . ?
C22 C17 C1 122.0(2) . . ?
C18 C17 C1 120.3(2) . . ?
C19 C18 C17 120.7(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 119.0(3) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C20 C21 C22 120.6(3) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C17 C22 C21 121.3(2) . . ?
C17 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22' C17' C18' 118.2(2) . . ?
C22' C17' C1 120.2(2) . . ?
C18' C17' C1 121.49(9) . . ?
C19' C18' C17' 120.3(2) . . ?
C19' C18' H18' 119.8 . . ?
C17' C18' H18' 119.8 . . ?
C20' C19' C18' 120.6(3) . . ?
C20' C19' H19' 119.7 . . ?
C18' C19' H19' 119.7 . . ?
C19' C20' C21' 119.2(3) . . ?
C19' C20' H20' 120.4 . . ?
C21' C20' H20' 120.4 . . ?
C20' C21' C22' 120.6(3) . . ?
C20' C21' H21' 119.7 . . ?
C22' C21' H21' 119.7 . . ?
C17' C22' C21' 120.8(3) . . ?
C17' C22' H22' 119.6 . . ?
C21' C22' H22' 119.6 . . ?

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
C8 O1 N1 C10 -0.29(16) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
C17' C1 C2 C3 -179.8(2) . . . . ?
C17 C1 C2 C3 178.5(3) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C3 C4 C7 179.01(19) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C7 C4 C5 C6 -179.22(15) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C17' C1 C6 C5 179.66(19) . . . . ?
C17 C1 C6 C5 -178.7(2) . . . . ?
C3 C4 C7 C9 3.3(3) . . . . ?
C5 C4 C7 C9 -177.49(17) . . . . ?
N1 O1 C8 O2 -178.15(14) . . . . ?
N1 O1 C8 C9 1.68(15) . . . . ?
C4 C7 C9 C10 174.91(14) . . . . ?
C4 C7 C9 C8 2.8(3) . . . . ?
O2 C8 C9 C7 -9.2(3) . . . . ?
O1 C8 C9 C7 170.99(16) . . . . ?
O2 C8 C9 C10 177.51(18) . . . . ?
O1 C8 C9 C10 -2.28(15) . . . . ?
O1 N1 C10 C9 -1.31(16) . . . . ?
O1 N1 C10 C11 178.27(12) . . . . ?
C7 C9 C10 N1 -171.78(14) . . . . ?
C8 C9 C10 N1 2.29(17) . . . . ?
C7 C9 C10 C11 8.7(2) . . . . ?
C8 C9 C10 C11 -177.25(14) . . . . ?
N1 C10 C11 C16 -120.85(16) . . . . ?
C9 C10 C11 C16 58.7(2) . . . . ?
N1 C10 C11 C12 58.59(19) . . . . ?
C9 C10 C11 C12 -121.89(16) . . . . ?
C16 C11 C12 C13 0.5(2) . . . . ?
C10 C11 C12 C13 -178.98(14) . . . . ?
C11 C12 C13 C14 0.8(2) . . . . ?
C12 C13 C14 C15 -0.9(2) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C14 C15 C16 C11 1.6(2) . . . . ?
C12 C11 C16 C15 -1.7(2) . . . . ?
C10 C11 C16 C15 177.78(13) . . . . ?
C6 C1 C17 C22 164.3(3) . . . . ?
C2 C1 C17 C22 -15.4(5) . . . . ?
C17' C1 C17 C22 -132(7) . . . . ?
C6 C1 C17 C18 -19.3(5) . . . . ?
C2 C1 C17 C18 161.0(3) . . . . ?
C17' C1 C17 C18 44(6) . . . . ?
C22 C17 C18 C19 -5.5(7) . . . . ?
C1 C17 C18 C19 177.9(3) . . . . ?
C17 C18 C19 C20 4.2(9) . . . . ?
C18 C19 C20 C21 -1.5(14) . . . . ?
C19 C20 C21 C22 0.3(14) . . . . ?
C18 C17 C22 C21 4.3(7) . . . . ?
C1 C17 C22 C21 -179.2(3) . . . . ?
C20 C21 C22 C17 -1.8(9) . . . . ?
C6 C1 C17' C22' -167.6(4) . . . . ?
C2 C1 C17' C22' 11.0(5) . . . . ?
C17 C1 C17' C22' 75(6) . . . . ?
C6 C1 C17' C18' 16.1(2) . . . . ?
C2 C1 C17' C18' -165.33(15) . . . . ?
C17 C1 C17' C18' -101(6) . . . . ?
C22' C17' C18' C19' 5.2(5) . . . . ?
C1 C17' C18' C19' -178.4(4) . . . . ?
C17' C18' C19' C20' -3.7(11) . . . . ?
C18' C19' C20' C21' 1.8(18) . . . . ?
C19' C20' C21' C22' -1.5(19) . . . . ?
C18' C17' C22' C21' -4.8(6) . . . . ?
C1 C17' C22' C21' 178.7(5) . . . . ?
C20' C21' C22' C17' 3.0(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        29.12
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.040
