# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_ss-skp-92
_database_code_depnum_ccdc_archive 'CCDC 910216'
_audit_update_record             
;
2012-11-09 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;
#TrackingRef 'CIF_Bridge compound_ss-92.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          517.6K
_chemical_formula_moiety         'C22 H15 N O2'
_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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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                   9.795(5)
_cell_length_b                   22.599(5)
_cell_length_c                   7.252(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 105.001(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1550.6(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2078
_cell_measurement_theta_min      0.95447
_cell_measurement_theta_max      1.00000

_exptl_crystal_description       rectangular
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95447
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_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  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7504
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         29.03
_reflns_number_total             3543
_reflns_number_gt                2652
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0458P)²+0.3831P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3543
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1123
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 1.04065(11) 0.15459(5) 0.17095(14) 0.0322(3) Uani 1 1 d . . .
C9 C 0.84136(14) 0.06788(6) 0.3378(2) 0.0271(3) Uani 1 1 d . . .
O2 O 1.07054(11) 0.16946(5) 0.68440(14) 0.0333(3) Uani 1 1 d . . .
O004 C 1.36367(16) 0.17668(6) 0.5632(2) 0.0281(3) Uani 1 1 d . . .
C7 C 0.92579(15) 0.11836(6) 0.4105(2) 0.0264(3) Uani 1 1 d . . .
N1 N 0.98074(14) 0.22040(6) 0.3994(2) 0.0353(3) Uani 1 1 d . . .
C007 C 1.46486(16) 0.15412(7) 0.4722(2) 0.0325(4) Uani 1 1 d . . .
C21 C 1.10882(16) 0.20661(7) 0.5430(2) 0.0312(3) Uani 1 1 d . . .
H008 H 1.1487 0.2436 0.6048 0.037 Uiso 1 1 calc R . .
C11 C 1.27968(17) 0.13366(7) 0.1865(2) 0.0355(4) Uani 1 1 d . . .
H009 H 1.2513 0.1199 0.0615 0.043 Uiso 1 1 calc R . .
C17 C 1.21807(15) 0.17735(6) 0.4607(2) 0.0267(3) Uani 1 1 d . . .
C16 C 1.41262(18) 0.19804(7) 0.7520(2) 0.0380(4) Uani 1 1 d . . .
H011 H 1.3479 0.2120 0.8154 0.046 Uiso 1 1 calc R . .
C14 C 1.65282(19) 0.17712(8) 0.7523(3) 0.0485(5) Uani 1 1 d . . .
H012 H 1.7485 0.1780 0.8149 0.058 Uiso 1 1 calc R . .
C10 C 0.81627(16) 0.02468(7) 0.4675(2) 0.0298(3) Uani 1 1 d . . .
C8 C 0.98629(15) 0.12250(7) 0.6038(2) 0.0275(3) Uani 1 1 d . . .
C3 C 0.72726(18) -0.02379(7) 0.3971(3) 0.0402(4) Uani 1 1 d . . .
H015 H 0.7092 -0.0517 0.4820 0.048 Uiso 1 1 calc R . .
C2 C 0.88001(17) 0.03210(7) 0.6656(2) 0.0350(4) Uani 1 1 d . . .
H016 H 0.8641 0.0039 0.7511 0.042 Uiso 1 1 calc R . .
C22 C 0.94021(16) 0.16926(7) 0.2826(2) 0.0308(3) Uani 1 1 d . . .
H017 H 0.8477 0.1768 0.1941 0.037 Uiso 1 1 calc R . .
C6 C 0.77820(17) 0.05921(7) 0.1406(2) 0.0355(4) Uani 1 1 d . . .
H018 H 0.7947 0.0864 0.0526 0.043 Uiso 1 1 calc R . .
C5 C 0.69351(18) 0.01144(8) 0.0779(3) 0.0433(4) Uani 1 1 d . . .
H019 H 0.6528 0.0066 -0.0521 0.052 Uiso 1 1 calc R . .
C4 C 0.66733(19) -0.03025(8) 0.2065(3) 0.0456(4) Uani 1 1 d . . .
H020 H 0.6090 -0.0625 0.1621 0.055 Uiso 1 1 calc R . .
C1 C 0.96348(16) 0.07927(7) 0.7328(2) 0.0335(4) Uani 1 1 d . . .
H021 H 1.0053 0.0831 0.8629 0.040 Uiso 1 1 calc R . .
C18 C 1.17840(15) 0.15547(6) 0.2774(2) 0.0274(3) Uani 1 1 d . . .
C15 C 1.5533(2) 0.19852(8) 0.8429(3) 0.0468(5) Uani 1 1 d . . .
H023 H 1.5832 0.2133 0.9665 0.056 Uiso 1 1 calc R . .
C12 C 1.41806(18) 0.13292(8) 0.2819(2) 0.0396(4) Uani 1 1 d . . .
H024 H 1.4839 0.1182 0.2215 0.047 Uiso 1 1 calc R . .
C13 C 1.60939(18) 0.15493(8) 0.5718(3) 0.0443(4) Uani 1 1 d . . .
H025 H 1.6761 0.1401 0.5131 0.053 Uiso 1 1 calc R . .
H50 H 0.989(2) 0.2524(9) 0.338(3) 0.052(6) Uiso 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 C18 1.3703(18) . ?
O1 C22 1.4648(18) . ?
C9 C6 1.417(2) . ?
C9 C10 1.421(2) . ?
C9 C7 1.427(2) . ?
O2 C8 1.3783(17) . ?
O2 C21 1.4478(19) . ?
O004 C16 1.413(2) . ?
O004 C007 1.420(2) . ?
O004 C17 1.428(2) . ?
C7 C8 1.376(2) . ?
C7 C22 1.507(2) . ?
N1 C22 1.427(2) . ?
N1 C21 1.442(2) . ?
N1 H50 0.863(19) . ?
C007 C13 1.413(2) . ?
C007 C12 1.420(2) . ?
C21 C17 1.506(2) . ?
C21 H008 0.9800 . ?
C11 C12 1.353(2) . ?
C11 C18 1.415(2) . ?
C11 H009 0.9300 . ?
C17 C18 1.377(2) . ?
C16 C15 1.365(2) . ?
C16 H011 0.9300 . ?
C14 C13 1.363(3) . ?
C14 C15 1.395(3) . ?
C14 H012 0.9300 . ?
C10 C3 1.411(2) . ?
C10 C2 1.420(2) . ?
C8 C1 1.410(2) . ?
C3 C4 1.363(3) . ?
C3 H015 0.9300 . ?
C2 C1 1.355(2) . ?
C2 H016 0.9300 . ?
C22 H017 0.9800 . ?
C6 C5 1.366(2) . ?
C6 H018 0.9300 . ?
C5 C4 1.395(3) . ?
C5 H019 0.9300 . ?
C4 H020 0.9300 . ?
C1 H021 0.9300 . ?
C15 H023 0.9300 . ?
C12 H024 0.9300 . ?
C13 H025 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
C18 O1 C22 112.93(12) . . ?
C6 C9 C10 117.92(14) . . ?
C6 C9 C7 122.89(14) . . ?
C10 C9 C7 119.18(14) . . ?
C8 O2 C21 112.47(11) . . ?
C16 O004 C007 118.05(14) . . ?
C16 O004 C17 122.92(14) . . ?
C007 O004 C17 119.03(14) . . ?
C8 C7 C9 119.07(13) . . ?
C8 C7 C22 119.38(13) . . ?
C9 C7 C22 121.36(13) . . ?
C22 N1 C21 108.05(12) . . ?
C22 N1 H50 114.9(13) . . ?
C21 N1 H50 111.9(13) . . ?
C13 C007 O004 119.01(15) . . ?
C13 C007 C12 122.00(15) . . ?
O004 C007 C12 118.96(14) . . ?
N1 C21 O2 107.49(12) . . ?
N1 C21 C17 112.54(13) . . ?
O2 C21 C17 111.52(12) . . ?
N1 C21 H008 108.4 . . ?
O2 C21 H008 108.4 . . ?
C17 C21 H008 108.4 . . ?
C12 C11 C18 119.77(15) . . ?
C12 C11 H009 120.1 . . ?
C18 C11 H009 120.1 . . ?
C18 C17 O004 119.55(13) . . ?
C18 C17 C21 119.22(13) . . ?
O004 C17 C21 120.99(13) . . ?
C15 C16 O004 121.15(16) . . ?
C15 C16 H011 119.4 . . ?
O004 C16 H011 119.4 . . ?
C13 C14 C15 119.83(17) . . ?
C13 C14 H012 120.1 . . ?
C15 C14 H012 120.1 . . ?
C3 C10 C2 121.77(15) . . ?
C3 C10 C9 119.38(15) . . ?
C2 C10 C9 118.85(14) . . ?
C7 C8 O2 122.48(13) . . ?
C7 C8 C1 121.90(14) . . ?
O2 C8 C1 115.61(13) . . ?
C4 C3 C10 120.92(16) . . ?
C4 C3 H015 119.5 . . ?
C10 C3 H015 119.5 . . ?
C1 C2 C10 121.56(14) . . ?
C1 C2 H016 119.2 . . ?
C10 C2 H016 119.2 . . ?
N1 C22 O1 112.82(12) . . ?
N1 C22 C7 107.99(13) . . ?
O1 C22 C7 110.53(12) . . ?
N1 C22 H017 108.5 . . ?
O1 C22 H017 108.5 . . ?
C7 C22 H017 108.5 . . ?
C5 C6 C9 120.92(16) . . ?
C5 C6 H018 119.5 . . ?
C9 C6 H018 119.5 . . ?
C6 C5 C4 120.82(16) . . ?
C6 C5 H019 119.6 . . ?
C4 C5 H019 119.6 . . ?
C3 C4 C5 120.02(16) . . ?
C3 C4 H020 120.0 . . ?
C5 C4 H020 120.0 . . ?
C2 C1 C8 119.37(15) . . ?
C2 C1 H021 120.3 . . ?
C8 C1 H021 120.3 . . ?
O1 C18 C17 122.68(13) . . ?
O1 C18 C11 116.06(14) . . ?
C17 C18 C11 121.24(14) . . ?
C16 C15 C14 120.72(17) . . ?
C16 C15 H023 119.6 . . ?
C14 C15 H023 119.6 . . ?
C11 C12 C007 121.43(14) . . ?
C11 C12 H024 119.3 . . ?
C007 C12 H024 119.3 . . ?
C14 C13 C007 121.21(16) . . ?
C14 C13 H025 119.4 . . ?
C007 C13 H025 119.4 . . ?

_diffrn_measured_fraction_theta_max 0.856
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.042


