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

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

data_8900
_database_code_depnum_ccdc_archive 'CCDC 1039204'
_audit_update_record             
;
2014-12-15 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_audit_creation_date             2014-07-30
_audit_block_code                FNG-SX-501-06
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H11 N O S'
_chemical_formula_sum            'C17 H11 N O S'
_chemical_formula_weight         277.33

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   15.172(3)
_cell_length_b                   3.8385(8)
_cell_length_c                   22.105(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.902(9)
_cell_angle_gamma                90
_cell_volume                     1225.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    20766
_cell_measurement_theta_min      2.6823
_cell_measurement_theta_max      29.9999

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 1.00 0.0100
0.00 0.00 -1.00 0.0100
1.00 0.00 0.00 0.0100
-1.00 0.00 0.00 0.0100
0.00 1.00 0.00 0.2000
0.00 -1.00 0.00 0.2000

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.257
_shelx_estimated_absorpt_T_min   0.904
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_absorpt_correction_T_min  0.94895
_exptl_absorpt_correction_T_max  0.99571

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_monochromator  'Incoatec Helios focusing multilayer optics'
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_detector_area_resol_mean 18.02
_diffrn_reflns_number            15404
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.724
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3243
_reflns_number_gt                2479
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'DATCOL (Bruker AXS, 2006)'
_computing_cell_refinement       'REVALCCD V. 1.6, 2008'
_computing_data_reduction        'REVALCCD V. 1.6, 2008'
_computing_structure_solution    'SHELXS (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_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     
;
 w=1/[σ²(Fo²)+(0.0666P)²+2.0711P]
 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         3243
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.1659
_refine_ls_wR_factor_gt          0.1519
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.22341(14) 1.1543(6) -0.19762(9) 0.0264(5) Uani 1 1 d . . . . .
C2 C 0.21699(18) 1.1110(7) -0.14326(13) 0.0181(5) Uani 1 1 d . . . . .
C3 C 0.13202(18) 1.2156(7) -0.12877(13) 0.0179(5) Uani 1 1 d . . . . .
C4 C 0.05607(19) 1.3480(7) -0.17667(13) 0.0192(5) Uani 1 1 d . . . . .
H4 H 0.0601 1.3776 -0.2184 0.023 Uiso 1 1 calc R U . . .
C5 C -0.02499(19) 1.4365(7) -0.16380(13) 0.0205(5) Uani 1 1 d . . . . .
H5 H -0.0767 1.5224 -0.1967 0.025 Uiso 1 1 calc R U . . .
C6 C -0.02999(19) 1.3983(7) -0.10204(13) 0.0200(5) Uani 1 1 d . . . . .
H6 H -0.0854 1.4576 -0.0930 0.024 Uiso 1 1 calc R U . . .
C7 C 0.04540(18) 1.2747(7) -0.05414(12) 0.0182(5) Uani 1 1 d . . . . .
H7 H 0.0418 1.2553 -0.0121 0.022 Uiso 1 1 calc R U . . .
C8 C 0.12716(18) 1.1774(7) -0.06668(12) 0.0168(5) Uani 1 1 d . . . . .
C9 C 0.20723(17) 1.0428(6) -0.01505(12) 0.0155(5) Uani 1 1 d . . . . .
N10 N 0.19939(15) 1.0496(6) 0.04158(10) 0.0183(5) Uani 1 1 d . . . . .
C11 C 0.26863(18) 0.9331(7) 0.09505(13) 0.0173(5) Uani 1 1 d . . . . .
C12 C 0.25115(19) 0.9723(7) 0.15348(13) 0.0206(5) Uani 1 1 d . . . . .
H12 H 0.1955 1.0810 0.1547 0.025 Uiso 1 1 calc R U . . .
C13 C 0.3140(2) 0.8544(7) 0.20911(13) 0.0220(6) Uani 1 1 d . . . . .
H13 H 0.3013 0.8803 0.2484 0.026 Uiso 1 1 calc R U . . .
C14 C 0.39625(19) 0.6969(7) 0.20759(13) 0.0219(6) Uani 1 1 d . . . . .
H14 H 0.4393 0.6144 0.2459 0.026 Uiso 1 1 calc R U . . .
C15 C 0.41546(18) 0.6603(7) 0.15055(13) 0.0201(5) Uani 1 1 d . . . . .
H15 H 0.4718 0.5547 0.1499 0.024 Uiso 1 1 calc R U . . .
C16 C 0.35244(17) 0.7780(7) 0.09439(12) 0.0171(5) Uani 1 1 d . . . . .
S17 S 0.37978(4) 0.72289(17) 0.02403(3) 0.01866(18) Uani 1 1 d . . . . .
C18 C 0.28696(18) 0.9214(7) -0.03337(12) 0.0169(5) Uani 1 1 d . . . . .
C19 C 0.29379(18) 0.9551(7) -0.09294(12) 0.0183(5) Uani 1 1 d . . . . .
C21 C 0.37817(19) 0.8395(7) -0.10931(14) 0.0216(6) Uani 1 1 d . . . . .
H21A H 0.4339 0.9189 -0.0763 0.032 Uiso 1 1 calc R U . . .
H21B H 0.3770 0.9394 -0.1503 0.032 Uiso 1 1 calc R U . . .
H21C H 0.3787 0.5847 -0.1120 0.032 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.246(3) . ?
C2 C19 1.468(4) . ?
C2 C3 1.476(4) . ?
C3 C4 1.399(4) . ?
C3 C8 1.405(4) . ?
C4 C5 1.387(4) . ?
C5 C6 1.398(4) . ?
C6 C7 1.382(4) . ?
C7 C8 1.402(4) . ?
C8 C9 1.481(4) . ?
C9 N10 1.294(3) . ?
C9 C18 1.465(4) . ?
N10 C11 1.392(3) . ?
C11 C12 1.404(4) . ?
C11 C16 1.408(4) . ?
C12 C13 1.380(4) . ?
C13 C14 1.396(4) . ?
C14 C15 1.386(4) . ?
C15 C16 1.389(4) . ?
C16 S17 1.741(3) . ?
S17 C18 1.754(3) . ?
C18 C19 1.359(4) . ?
C19 C21 1.500(4) . ?

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 C19 120.4(2) . . ?
O1 C2 C3 120.3(2) . . ?
C19 C2 C3 119.3(2) . . ?
C4 C3 C8 119.9(2) . . ?
C4 C3 C2 120.4(2) . . ?
C8 C3 C2 119.7(2) . . ?
C5 C4 C3 120.7(2) . . ?
C4 C5 C6 119.5(3) . . ?
C7 C6 C5 120.2(2) . . ?
C6 C7 C8 120.9(2) . . ?
C7 C8 C3 118.7(2) . . ?
C7 C8 C9 120.4(2) . . ?
C3 C8 C9 120.8(2) . . ?
N10 C9 C18 127.1(2) . . ?
N10 C9 C8 116.2(2) . . ?
C18 C9 C8 116.7(2) . . ?
C9 N10 C11 123.1(2) . . ?
N10 C11 C12 116.1(2) . . ?
N10 C11 C16 125.1(2) . . ?
C12 C11 C16 118.8(2) . . ?
C13 C12 C11 120.7(3) . . ?
C12 C13 C14 119.9(3) . . ?
C15 C14 C13 120.3(3) . . ?
C14 C15 C16 120.1(3) . . ?
C15 C16 C11 120.2(2) . . ?
C15 C16 S17 118.1(2) . . ?
C11 C16 S17 121.6(2) . . ?
C16 S17 C18 103.57(13) . . ?
C19 C18 C9 123.6(2) . . ?
C19 C18 S17 117.3(2) . . ?
C9 C18 S17 119.08(19) . . ?
C18 C19 C2 119.6(2) . . ?
C18 C19 C21 122.0(3) . . ?
C2 C19 C21 118.4(2) . . ?

_refine_diff_density_max         0.720
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.101

_shelxl_version_number           2013-2



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
####################################################################### 
# 
# 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_8901
_database_code_depnum_ccdc_archive 'CCDC 1039205'
_audit_update_record             
;
2014-12-15 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_audit_creation_date             2014-07-28
_audit_block_code                CEC-CA-094
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H10 Cl N O2'
_chemical_formula_weight         295.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

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

_cell_length_a                   4.7569(9)
_cell_length_b                   9.660(2)
_cell_length_c                   28.117(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1292.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5533
_cell_measurement_theta_min      2.5583
_cell_measurement_theta_max      29.4013

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2.00 0.00 -1.00 0.1300
-2.00 0.00 1.00 0.1300
0.00 1.00 2.00 0.0150
0.00 -1.00 -2.00 0.0150
0.00 -1.00 2.00 0.0050
0.00 1.00 -2.00 0.0050

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.012
_exptl_absorpt_coefficient_mu    0.299
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_absorpt_correction_T_min  0.95811
_exptl_absorpt_correction_T_max  0.99706

_exptl_special_details           
;
 Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   1\mS
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_detector_area_resol_mean 66.67
_diffrn_reflns_number            35695
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_av_R_equivalents  0.0956
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         3.028
_diffrn_reflns_theta_max         30.210
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3840
_reflns_number_gt                3275
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2005-2013)'
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS (G. M. Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2013)'
_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.

 The minimum and maximum estimated transmissions from the multi-scan scaling 
are 0.8767 and 1.0000 (SADABS).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0416P)²+0.2274P]
 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 x determined using 1213 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.04(3)
_chemical_absolute_configuration .
_refine_ls_number_reflns         3840
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.9732(4) -0.4392(2) 0.21970(6) 0.0238(4) Uani 1 1 d . . . . .
C2 C 1.8426(6) -0.3729(2) 0.18946(8) 0.0149(5) Uani 1 1 d . . . . .
C3 C 1.9028(5) -0.3943(2) 0.13797(8) 0.0135(5) Uani 1 1 d . . . . .
C4 C 2.1036(5) -0.4921(2) 0.12433(8) 0.0153(5) Uani 1 1 d . . . . .
H4 H 2.1981 -0.5454 0.1478 0.018 Uiso 1 1 calc R U . . .
C5 C 2.1651(6) -0.5113(2) 0.07675(9) 0.0171(5) Uani 1 1 d . . . . .
H5 H 2.3011 -0.5781 0.0675 0.021 Uiso 1 1 calc R U . . .
C6 C 2.0281(5) -0.4330(2) 0.04232(9) 0.0147(5) Uani 1 1 d . . . . .
H6 H 2.0727 -0.4462 0.0097 0.018 Uiso 1 1 calc R U . . .
C7 C 1.8285(6) -0.3365(2) 0.05502(8) 0.0134(4) Uani 1 1 d . . . . .
H7 H 1.7356 -0.2838 0.0312 0.016 Uiso 1 1 calc R U . . .
C8 C 1.7628(5) -0.3163(2) 0.10313(8) 0.0105(4) Uani 1 1 d . . . . .
C9 C 1.5490(5) -0.2154(3) 0.11742(8) 0.0116(4) Uani 1 1 d . . . . .
N10 N 1.4186(4) -0.1436(2) 0.08495(7) 0.0117(4) Uani 1 1 d . . . . .
C11 C 1.2165(5) -0.0491(2) 0.10046(8) 0.0118(4) Uani 1 1 d . . . . .
C12 C 1.0679(5) 0.0289(2) 0.06695(8) 0.0120(4) Uani 1 1 d . . . . .
H12 H 1.1041 0.0176 0.0339 0.014 Uiso 1 1 calc R U . . .
C13 C 0.8684(5) 0.1224(2) 0.08226(8) 0.0130(5) Uani 1 1 d . . . . .
C14 C 0.8110(6) 0.1408(2) 0.13056(8) 0.0147(5) Uani 1 1 d . . . . .
H14 H 0.6733 0.2060 0.1404 0.018 Uiso 1 1 calc R U . . .
C15 C 0.9556(6) 0.0634(2) 0.16409(8) 0.0147(5) Uani 1 1 d . . . . .
H15 H 0.9183 0.0746 0.1971 0.018 Uiso 1 1 calc R U . . .
C16 C 1.1552(6) -0.0303(2) 0.14857(8) 0.0128(4) Uani 1 1 d . . . . .
O17 O 1.2945(4) -0.10630(17) 0.18246(6) 0.0152(4) Uani 1 1 d . . . . .
C18 C 1.4936(5) -0.2003(2) 0.16851(8) 0.0131(5) Uani 1 1 d . . . . .
C19 C 1.6289(5) -0.2717(3) 0.20306(8) 0.0146(5) Uani 1 1 d . . . . .
Cl20 Cl 0.67837(13) 0.21482(6) 0.04038(2) 0.01526(13) Uani 1 1 d . . . . .
C21 C 1.5718(6) -0.2485(3) 0.25506(8) 0.0202(6) Uani 1 1 d . . . . .
H21A H 1.7212 -0.1910 0.2687 0.030 Uiso 1 1 calc R U . . .
H21B H 1.5665 -0.3378 0.2715 0.030 Uiso 1 1 calc R U . . .
H21C H 1.3905 -0.2015 0.2588 0.030 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.233(3) . ?
C2 C19 1.461(3) . ?
C2 C3 1.490(3) . ?
C3 C4 1.397(3) . ?
C3 C8 1.404(3) . ?
C4 C5 1.382(3) . ?
C5 C6 1.391(3) . ?
C6 C7 1.377(3) . ?
C7 C8 1.402(3) . ?
C8 C9 1.465(3) . ?
C9 N10 1.303(3) . ?
C9 C18 1.468(3) . ?
N10 C11 1.395(3) . ?
C11 C16 1.396(3) . ?
C11 C12 1.398(3) . ?
C12 C13 1.379(3) . ?
C13 C14 1.396(3) . ?
C13 Cl20 1.732(2) . ?
C14 C15 1.386(3) . ?
C15 C16 1.383(3) . ?
C16 O17 1.373(3) . ?
O17 C18 1.370(3) . ?
C18 C19 1.354(3) . ?
C19 C21 1.504(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
O1 C2 C19 121.2(2) . . ?
O1 C2 C3 120.1(2) . . ?
C19 C2 C3 118.7(2) . . ?
C4 C3 C8 119.7(2) . . ?
C4 C3 C2 119.5(2) . . ?
C8 C3 C2 120.8(2) . . ?
C5 C4 C3 120.1(2) . . ?
C4 C5 C6 120.1(2) . . ?
C7 C6 C5 120.7(2) . . ?
C6 C7 C8 119.9(2) . . ?
C7 C8 C3 119.5(2) . . ?
C7 C8 C9 120.8(2) . . ?
C3 C8 C9 119.7(2) . . ?
N10 C9 C8 119.5(2) . . ?
N10 C9 C18 123.2(2) . . ?
C8 C9 C18 117.3(2) . . ?
C9 N10 C11 117.19(19) . . ?
N10 C11 C16 122.1(2) . . ?
N10 C11 C12 119.3(2) . . ?
C16 C11 C12 118.5(2) . . ?
C13 C12 C11 119.4(2) . . ?
C12 C13 C14 121.4(2) . . ?
C12 C13 Cl20 118.98(18) . . ?
C14 C13 Cl20 119.56(19) . . ?
C15 C14 C13 119.7(2) . . ?
C16 C15 C14 118.6(2) . . ?
O17 C16 C15 117.5(2) . . ?
O17 C16 C11 120.1(2) . . ?
C15 C16 C11 122.3(2) . . ?
C18 O17 C16 119.30(18) . . ?
C19 C18 O17 117.4(2) . . ?
C19 C18 C9 124.5(2) . . ?
O17 C18 C9 118.0(2) . . ?
C18 C19 C2 118.9(2) . . ?
C18 C19 C21 122.4(2) . . ?
C2 C19 C21 118.7(2) . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.070

_shelxl_version_number           2013-2



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

data_8902
_database_code_depnum_ccdc_archive 'CCDC 1039206'
_audit_update_record             
;
2014-12-15 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_audit_creation_date             2014-07-24
_audit_block_code                FNG-SX-502-08
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_compound_source        toluene
_chemical_formula_moiety         'C18 H13 N O2'
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   7.1715(6)
_cell_length_b                   21.816(2)
_cell_length_c                   8.9610(9)
_cell_angle_alpha                90
_cell_angle_beta                 112.283(4)
_cell_angle_gamma                90
_cell_volume                     1297.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6891
_cell_measurement_theta_min      4.0527
_cell_measurement_theta_max      67.0696

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 -2.00 0.0600
0.00 -1.00 2.00 0.0600
2.00 -1.00 -1.00 0.1600
-2.00 1.00 1.00 0.1600
0.00 -1.00 0.00 0.0400
0.00 1.00 0.00 0.0400

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.742
_shelx_estimated_absorpt_T_min   0.797
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_absorpt_correction_T_min  0.84701
_exptl_absorpt_correction_T_max  0.94601

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           Cu-K\a
_diffrn_source                   '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_monochromator  'MONTEL graded multilayer optic'
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_detector_area_resol_mean 66.67
_diffrn_reflns_number            30049
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.053
_diffrn_reflns_theta_max         67.383
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             2298
_reflns_number_gt                1846
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2005-2013)'
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS (G. M. Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2013)'
_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.

 The minimum and maximum estimated transmissions from the multi-scan
 scaling are 0.7992 and 0.9690 (SADABS).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1049P)²+0.3627P]
 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       0.0032(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2298
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1611
_refine_ls_wR_factor_gt          0.1482
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5094(2) 0.71674(6) 0.49443(16) 0.0308(4) Uani 1 1 d . . . . .
C2 C 0.4397(2) 0.66450(8) 0.4712(2) 0.0247(4) Uani 1 1 d . . . . .
C3 C 0.3396(3) 0.63998(8) 0.3041(2) 0.0247(4) Uani 1 1 d . . . . .
C4 C 0.3269(3) 0.67654(9) 0.1725(2) 0.0291(5) Uani 1 1 d . . . . .
H4 H 0.3784 0.7172 0.1895 0.035 Uiso 1 1 calc R U . . .
C5 C 0.2392(3) 0.65352(9) 0.0171(2) 0.0304(5) Uani 1 1 d . . . . .
H5 H 0.2270 0.6789 -0.0723 0.036 Uiso 1 1 calc R U . . .
C6 C 0.1690(3) 0.59357(9) -0.0084(2) 0.0298(5) Uani 1 1 d . . . . .
H6 H 0.1126 0.5776 -0.1149 0.036 Uiso 1 1 calc R U . . .
C7 C 0.1810(3) 0.55700(9) 0.1211(2) 0.0269(4) Uani 1 1 d . . . . .
H7 H 0.1326 0.5160 0.1034 0.032 Uiso 1 1 calc R U . . .
C8 C 0.2643(2) 0.58029(8) 0.2780(2) 0.0235(4) Uani 1 1 d . . . . .
C9 C 0.2690(2) 0.54230(8) 0.4145(2) 0.0225(4) Uani 1 1 d . . . . .
N10 N 0.1944(2) 0.48744(7) 0.38811(17) 0.0234(4) Uani 1 1 d . . . . .
C11 C 0.2020(2) 0.45278(8) 0.5212(2) 0.0231(4) Uani 1 1 d . . . . .
C12 C 0.1279(2) 0.39297(8) 0.4991(2) 0.0240(4) Uani 1 1 d . . . . .
H12 H 0.0708 0.3767 0.3930 0.029 Uiso 1 1 calc R U . . .
C13 C 0.1359(3) 0.35679(8) 0.6286(2) 0.0257(4) Uani 1 1 d . . . . .
C14 C 0.2176(3) 0.38254(8) 0.7831(2) 0.0268(4) Uani 1 1 d . . . . .
H14 H 0.2221 0.3586 0.8730 0.032 Uiso 1 1 calc R U . . .
C15 C 0.2920(3) 0.44177(8) 0.8090(2) 0.0261(4) Uani 1 1 d . . . . .
H15 H 0.3459 0.4585 0.9148 0.031 Uiso 1 1 calc R U . . .
C16 C 0.2862(2) 0.47621(8) 0.6776(2) 0.0228(4) Uani 1 1 d . . . . .
O17 O 0.36705(18) 0.53419(5) 0.70485(14) 0.0247(3) Uani 1 1 d . . . . .
C18 C 0.3636(2) 0.56893(8) 0.5759(2) 0.0223(4) Uani 1 1 d . . . . .
C19 C 0.4520(3) 0.62458(8) 0.6060(2) 0.0242(4) Uani 1 1 d . . . . .
C20 C 0.0661(3) 0.29139(9) 0.6041(2) 0.0317(5) Uani 1 1 d . . . . .
H20A H -0.0661 0.2891 0.5155 0.048 Uiso 1 1 calc R U . . .
H20B H 0.0556 0.2758 0.7032 0.048 Uiso 1 1 calc R U . . .
H20C H 0.1632 0.2665 0.5776 0.048 Uiso 1 1 calc R U . . .
C21 C 0.5653(3) 0.64695(9) 0.7749(2) 0.0308(5) Uani 1 1 d . . . . .
H21A H 0.5304 0.6216 0.8508 0.046 Uiso 1 1 calc R U . . .
H21B H 0.5288 0.6897 0.7840 0.046 Uiso 1 1 calc R U . . .
H21C H 0.7104 0.6442 0.8002 0.046 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.230(2) . ?
C2 C19 1.464(3) . ?
C2 C3 1.493(3) . ?
C3 C8 1.395(3) . ?
C3 C4 1.398(3) . ?
C4 C5 1.386(3) . ?
C5 C6 1.389(3) . ?
C6 C7 1.384(3) . ?
C7 C8 1.398(3) . ?
C8 C9 1.467(2) . ?
C9 N10 1.296(2) . ?
C9 C18 1.464(3) . ?
N10 C11 1.396(2) . ?
C11 C12 1.394(2) . ?
C11 C16 1.395(3) . ?
C12 C13 1.387(3) . ?
C13 C14 1.401(3) . ?
C13 C20 1.500(2) . ?
C14 C15 1.384(3) . ?
C15 C16 1.384(3) . ?
C16 O17 1.374(2) . ?
O17 C18 1.375(2) . ?
C18 C19 1.349(3) . ?
C19 C21 1.503(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
O1 C2 C19 121.19(17) . . ?
O1 C2 C3 120.77(17) . . ?
C19 C2 C3 118.04(16) . . ?
C8 C3 C4 119.62(17) . . ?
C8 C3 C2 120.70(16) . . ?
C4 C3 C2 119.65(17) . . ?
C5 C4 C3 120.01(18) . . ?
C4 C5 C6 120.30(18) . . ?
C7 C6 C5 120.08(18) . . ?
C6 C7 C8 120.06(18) . . ?
C3 C8 C7 119.88(17) . . ?
C3 C8 C9 120.18(16) . . ?
C7 C8 C9 119.93(16) . . ?
N10 C9 C18 123.45(16) . . ?
N10 C9 C8 119.49(16) . . ?
C18 C9 C8 117.04(16) . . ?
C9 N10 C11 117.70(15) . . ?
C12 C11 C16 118.83(16) . . ?
C12 C11 N10 119.73(16) . . ?
C16 C11 N10 121.42(16) . . ?
C13 C12 C11 121.40(17) . . ?
C12 C13 C14 117.92(16) . . ?
C12 C13 C20 120.89(17) . . ?
C14 C13 C20 121.15(17) . . ?
C15 C14 C13 122.04(17) . . ?
C14 C15 C16 118.63(17) . . ?
O17 C16 C15 118.29(16) . . ?
O17 C16 C11 120.56(16) . . ?
C15 C16 C11 121.15(17) . . ?
C16 O17 C18 119.09(14) . . ?
C19 C18 O17 118.09(16) . . ?
C19 C18 C9 124.14(16) . . ?
O17 C18 C9 117.74(15) . . ?
C18 C19 C2 119.58(16) . . ?
C18 C19 C21 121.84(16) . . ?
C2 C19 C21 118.58(16) . . ?

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.065

_shelxl_version_number           2013-2



