# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2035021'
loop_
_audit_author_name
_audit_author_address
'RASHMI SINGH'
;BANARAS HINDU UNIVERSITY
India
;
_audit_update_record             
;
2020-10-01 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H Cl N O S'
_chemical_formula_weight         110.54

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.0134(4)
_cell_length_b                   7.0858(5)
_cell_length_c                   15.5319(10)
_cell_angle_alpha                96.280(4)
_cell_angle_beta                 90.168(4)
_cell_angle_gamma                104.398(4)
_cell_volume                     742.77(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.977
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.372
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16157
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.320
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4138
_reflns_number_gt                2881
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1271P)²+0.2895P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4138
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1838
_refine_ls_wR_factor_gt          0.1578
_refine_ls_goodness_of_fit_ref   0.837
_refine_ls_restrained_S_all      0.837
_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
S001 S 0.32720(7) 0.60278(9) 0.21857(3) 0.0472(2) Uani 1 1 d . . . . .
O002 O 0.4767(2) 0.8410(2) 0.79056(9) 0.0499(4) Uani 1 1 d . . . . .
O003 O 0.0696(2) 0.5464(3) 0.33431(11) 0.0602(5) Uani 1 1 d . . . . .
N004 N 0.7229(2) 0.8139(2) 0.45403(10) 0.0375(4) Uani 1 1 d . . . . .
C005 C 0.5960(3) 0.7476(3) 0.38691(12) 0.0349(4) Uani 1 1 d . . . . .
C006 C 0.3896(3) 0.6777(3) 0.39859(12) 0.0352(4) Uani 1 1 d . . . . .
C007 C 0.5820(3) 0.7023(3) 0.22621(12) 0.0369(4) Uani 1 1 d . . . . .
C008 C 0.4497(3) 0.7471(3) 0.55253(12) 0.0359(4) Uani 1 1 d . . . . .
C009 C 0.6537(3) 0.8150(3) 0.53518(12) 0.0356(4) Uani 1 1 d . . . . .
C00A C 0.7883(3) 0.8863(3) 0.60631(13) 0.0431(5) Uani 1 1 d . . . . .
H00A H 0.922013 0.930038 0.596647 0.052 Uiso 1 1 calc R U . . .
C00B C 0.6766(3) 0.7204(3) 0.14114(12) 0.0386(4) Uani 1 1 d . . . . .
C00C C 0.6813(3) 0.7562(3) 0.30256(12) 0.0383(4) Uani 1 1 d . . . . .
C00D C 0.3187(3) 0.6785(3) 0.48074(13) 0.0392(4) Uani 1 1 d . . . . .
C00E C 0.2465(3) 0.6066(3) 0.32622(13) 0.0412(4) Uani 1 1 d . . . . .
C00F C 0.8711(3) 0.7111(3) 0.13238(14) 0.0483(5) Uani 1 1 d . . . . .
H00F H 0.941980 0.691797 0.179929 0.058 Uiso 1 1 calc R U . . .
C00G C 0.5200(3) 0.8249(3) 0.70533(12) 0.0409(4) Uani 1 1 d . . . . .
C00H C 0.3857(3) 0.7530(3) 0.63868(13) 0.0402(4) Uani 1 1 d . . . . .
H00H H 0.252819 0.708114 0.649863 0.048 Uiso 1 1 calc R U . . .
C00I C 0.7235(3) 0.8911(3) 0.68844(13) 0.0448(5) Uani 1 1 d . . . . .
H00I H 0.813692 0.938494 0.734550 0.054 Uiso 1 1 calc R U . . .
C00J C 0.5764(4) 0.7497(4) 0.06899(14) 0.0575(6) Uani 1 1 d . . . . .
H00J H 0.446239 0.757315 0.073413 0.069 Uiso 1 1 calc R U . . .
C00K C 0.2750(4) 0.7800(4) 0.81107(15) 0.0548(6) Uani 1 1 d . . . . .
H00B H 0.262526 0.797964 0.872765 0.082 Uiso 1 1 calc R U . . .
H00C H 0.201803 0.856761 0.784195 0.082 Uiso 1 1 calc R U . . .
H00D H 0.224467 0.643920 0.790102 0.082 Uiso 1 1 calc R U . . .
C00L C 0.8582(4) 0.7579(4) -0.01737(15) 0.0627(7) Uani 1 1 d . . . . .
H00L H 0.918962 0.769746 -0.070352 0.075 Uiso 1 1 calc R U . . .
C00M C 0.9600(4) 0.7304(4) 0.05355(17) 0.0620(6) Uani 1 1 d . . . . .
H00M H 1.090573 0.724515 0.048573 0.074 Uiso 1 1 calc R U . . .
C00N C 0.6674(4) 0.7679(4) -0.00987(15) 0.0664(7) Uani 1 1 d . . . . .
H00N H 0.597819 0.787089 -0.057869 0.080 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
S001 C007 1.749(2) . ?
S001 C00E 1.767(2) . ?
O002 C00G 1.358(2) . ?
O002 C00K 1.421(3) . ?
O003 C00E 1.219(2) . ?
N004 C005 1.334(2) . ?
N004 C009 1.352(2) . ?
C005 C006 1.428(3) . ?
C005 C00C 1.443(3) . ?
C006 C00D 1.370(3) . ?
C006 C00E 1.464(3) . ?
C007 C00C 1.342(3) . ?
C007 C00B 1.484(3) . ?
C008 C00D 1.406(3) . ?
C008 C00H 1.412(3) . ?
C008 C009 1.428(3) . ?
C009 C00A 1.415(3) . ?
C00A C00I 1.355(3) . ?
C00A H00A 0.9300 . ?
C00B C00F 1.389(3) . ?
C00B C00J 1.383(3) . ?
C00F C00M 1.380(3) . ?
C00F H00F 0.9300 . ?
C00G C00H 1.364(3) . ?
C00G C00I 1.422(3) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00J C00N 1.386(3) . ?
C00J H00J 0.9300 . ?
C00K H00B 0.9600 . ?
C00K H00C 0.9600 . ?
C00K H00D 0.9600 . ?
C00L C00N 1.363(4) . ?
C00L C00M 1.368(4) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00N H00N 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
C007 S001 C00E 105.88(9) . . ?
C00G O002 C00K 116.93(17) . . ?
C005 N004 C009 118.94(16) . . ?
N004 C005 C006 121.75(16) . . ?
N004 C005 C00C 115.41(16) . . ?
C006 C005 C00C 122.82(16) . . ?
C00D C006 C005 119.50(16) . . ?
C00D C006 C00E 117.50(17) . . ?
C005 C006 C00E 123.00(17) . . ?
C00C C007 C00B 123.61(17) . . ?
C00C C007 S001 122.46(15) . . ?
C00B C007 S001 113.93(13) . . ?
C00D C008 C00H 122.47(18) . . ?
C00D C008 C009 117.16(17) . . ?
C00H C008 C009 120.36(17) . . ?
N004 C009 C00A 118.90(17) . . ?
N004 C009 C008 122.85(17) . . ?
C00A C009 C008 118.25(17) . . ?
C00I C00A C009 120.40(19) . . ?
C00I C00A H00A 119.8 . . ?
C009 C00A H00A 119.8 . . ?
C00F C00B C00J 118.05(19) . . ?
C00F C00B C007 120.36(18) . . ?
C00J C00B C007 121.59(18) . . ?
C007 C00C C005 125.84(18) . . ?
C006 C00D C008 119.80(17) . . ?
O003 C00E C006 124.38(18) . . ?
O003 C00E S001 115.68(15) . . ?
C006 C00E S001 119.94(14) . . ?
C00M C00F C00B 120.4(2) . . ?
C00M C00F H00F 119.8 . . ?
C00B C00F H00F 119.8 . . ?
O002 C00G C00H 125.11(19) . . ?
O002 C00G C00I 114.56(18) . . ?
C00H C00G C00I 120.34(18) . . ?
C00G C00H C008 119.51(18) . . ?
C00G C00H H00H 120.2 . . ?
C008 C00H H00H 120.2 . . ?
C00A C00I C00G 121.13(19) . . ?
C00A C00I H00I 119.4 . . ?
C00G C00I H00I 119.4 . . ?
C00N C00J C00B 120.9(2) . . ?
C00N C00J H00J 119.6 . . ?
C00B C00J H00J 119.6 . . ?
O002 C00K H00B 109.5 . . ?
O002 C00K H00C 109.5 . . ?
H00B C00K H00C 109.5 . . ?
O002 C00K H00D 109.5 . . ?
H00B C00K H00D 109.5 . . ?
H00C C00K H00D 109.5 . . ?
C00N C00L C00M 119.6(2) . . ?
C00N C00L H00L 120.2 . . ?
C00M C00L H00L 120.2 . . ?
C00L C00M C00F 120.8(2) . . ?
C00L C00M H00M 119.6 . . ?
C00F C00M H00M 119.6 . . ?
C00L C00N C00J 120.3(2) . . ?
C00L C00N H00N 119.9 . . ?
C00J C00N H00N 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C009 N004 C005 C006 -0.1(3) . . . . ?
C009 N004 C005 C00C 178.45(16) . . . . ?
N004 C005 C006 C00D 0.1(3) . . . . ?
C00C C005 C006 C00D -178.37(17) . . . . ?
N004 C005 C006 C00E 179.13(18) . . . . ?
C00C C005 C006 C00E 0.7(3) . . . . ?
C00E S001 C007 C00C 3.0(2) . . . . ?
C00E S001 C007 C00B -177.21(13) . . . . ?
C005 N004 C009 C00A -179.72(17) . . . . ?
C005 N004 C009 C008 0.3(3) . . . . ?
C00D C008 C009 N004 -0.5(3) . . . . ?
C00H C008 C009 N004 -179.58(17) . . . . ?
C00D C008 C009 C00A 179.52(17) . . . . ?
C00H C008 C009 C00A 0.5(3) . . . . ?
N004 C009 C00A C00I 179.39(18) . . . . ?
C008 C009 C00A C00I -0.7(3) . . . . ?
C00C C007 C00B C00F 28.6(3) . . . . ?
S001 C007 C00B C00F -151.26(17) . . . . ?
C00C C007 C00B C00J -150.5(2) . . . . ?
S001 C007 C00B C00J 29.7(2) . . . . ?
C00B C007 C00C C005 177.87(17) . . . . ?
S001 C007 C00C C005 -2.3(3) . . . . ?
N004 C005 C00C C007 -178.28(18) . . . . ?
C006 C005 C00C C007 0.2(3) . . . . ?
C005 C006 C00D C008 -0.3(3) . . . . ?
C00E C006 C00D C008 -179.38(17) . . . . ?
C00H C008 C00D C006 179.51(17) . . . . ?
C009 C008 C00D C006 0.5(3) . . . . ?
C00D C006 C00E O003 -0.8(3) . . . . ?
C005 C006 C00E O003 -179.91(19) . . . . ?
C00D C006 C00E S001 179.63(14) . . . . ?
C005 C006 C00E S001 0.5(3) . . . . ?
C007 S001 C00E O003 178.33(16) . . . . ?
C007 S001 C00E C006 -2.08(19) . . . . ?
C00J C00B C00F C00M -0.1(3) . . . . ?
C007 C00B C00F C00M -179.2(2) . . . . ?
C00K O002 C00G C00H -0.8(3) . . . . ?
C00K O002 C00G C00I 178.98(18) . . . . ?
O002 C00G C00H C008 178.95(17) . . . . ?
C00I C00G C00H C008 -0.9(3) . . . . ?
C00D C008 C00H C00G -178.71(18) . . . . ?
C009 C008 C00H C00G 0.3(3) . . . . ?
C009 C00A C00I C00G 0.1(3) . . . . ?
O002 C00G C00I C00A -179.15(18) . . . . ?
C00H C00G C00I C00A 0.7(3) . . . . ?
C00F C00B C00J C00N 0.4(4) . . . . ?
C007 C00B C00J C00N 179.5(2) . . . . ?
C00N C00L C00M C00F 0.5(4) . . . . ?
C00B C00F C00M C00L -0.3(4) . . . . ?
C00M C00L C00N C00J -0.2(4) . . . . ?
C00B C00J C00N C00L -0.3(4) . . . . ?

_refine_diff_density_max         0.743
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.055



####################################################################### 
# 
# 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_F1
_database_code_depnum_ccdc_archive 'CCDC 2034674'
loop_
_audit_author_name
_audit_author_address
'RASHMI SINGH'
;BANARAS HINDU UNIVERSITY
India
;
_audit_update_record             
;
2020-09-29 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H14 N2 O2'
_chemical_formula_weight         302.32

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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'

_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'
'-y+1/4, x+3/4, z+3/4'
'y+1/4, -x+1/4, z+1/4'
'-x, -y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+5/4'
'y+3/4, -x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-3/4'
'-y-1/4, x-1/4, -z-1/4'
'x, y-1/2, -z'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z-1/4'
'-y+1/4, x+1/4, -z+1/4'
'x+1/2, y, -z+1/2'

_cell_length_a                   29.725(2)
_cell_length_b                   29.725(2)
_cell_length_c                   7.0358(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6216.8(12)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             2528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22591
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.741
_diffrn_reflns_theta_max         30.587
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4755
_reflns_number_gt                2463
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4755
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1242
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1871
_refine_ls_wR_factor_gt          0.1524
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_restrained_S_all      0.942
_refine_ls_shift/su_max          0.057
_refine_ls_shift/su_mean         0.009

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 0.57883(5) 0.24840(5) -0.4314(2) 0.0717(4) Uani 1 1 d . . . . .
O2 O 0.74325(4) 0.28945(4) 0.56305(19) 0.0599(4) Uani 1 1 d . . . . .
N1 N 0.64532(5) 0.20674(5) 0.1612(2) 0.0470(4) Uani 1 1 d . . . . .
N2 N 0.71193(5) 0.21841(5) 0.5754(2) 0.0496(4) Uani 1 1 d . . . . .
H5 H 0.7235 0.2100 0.6815 0.060 Uiso 1 1 calc R U . . .
C1 C 0.55619(9) 0.20626(8) -0.4415(4) 0.0843(8) Uani 1 1 d . . . . .
H3 H 0.5776 0.1823 -0.4287 0.127 Uiso 1 1 calc R U . . .
H14 H 0.5412 0.2037 -0.5618 0.127 Uiso 1 1 calc R U . . .
H1 H 0.5345 0.2043 -0.3408 0.127 Uiso 1 1 calc R U . . .
C2 C 0.60494(6) 0.25639(6) -0.2760(3) 0.0519(5) Uani 1 1 d . . . . .
C3 C 0.61171(6) 0.22667(6) -0.1323(3) 0.0495(4) Uani 1 1 d . . . . .
H4 H 0.5978 0.1986 -0.1355 0.059 Uiso 1 1 calc R U . . .
C4 C 0.63968(5) 0.23815(6) 0.0213(2) 0.0430(4) Uani 1 1 d . . . . .
C5 C 0.67197(6) 0.21886(6) 0.3008(2) 0.0435(4) Uani 1 1 d . . . . .
C6 C 0.68357(6) 0.19113(6) 0.4668(2) 0.0450(4) Uani 1 1 d . . . . .
C7 C 0.66931(6) 0.14873(6) 0.4914(3) 0.0510(5) Uani 1 1 d . . . . .
H10 H 0.6518 0.1379 0.3920 0.061 Uiso 1 1 calc R U . . .
C8 C 0.67609(6) 0.11658(6) 0.6443(3) 0.0504(5) Uani 1 1 d . . . . .
C9 C 0.68866(7) 0.12821(7) 0.8269(3) 0.0611(5) Uani 1 1 d . . . . .
H9 H 0.6937 0.1583 0.8567 0.073 Uiso 1 1 calc R U . . .
C10 C 0.69382(8) 0.09587(9) 0.9655(4) 0.0819(7) Uani 1 1 d . . . . .
H6 H 0.7021 0.1042 1.0880 0.098 Uiso 1 1 calc R U . . .
C11 C 0.68669(9) 0.05127(10) 0.9228(5) 0.0973(10) Uani 1 1 d . . . . .
H2 H 0.6904 0.0294 1.0161 0.117 Uiso 1 1 calc R U . . .
C12 C 0.69377(6) 0.26054(6) 0.3179(2) 0.0440(4) Uani 1 1 d . . . . .
C13 C 0.71948(6) 0.25989(6) 0.4967(3) 0.0482(4) Uani 1 1 d . . . . .
C14 C 0.67400(9) 0.03897(8) 0.7418(5) 0.0932(9) Uani 1 1 d . . . . .
H8 H 0.6691 0.0088 0.7128 0.112 Uiso 1 1 calc R U . . .
C15 C 0.66865(7) 0.07110(7) 0.6053(4) 0.0660(6) Uani 1 1 d . . . . .
H7 H 0.6599 0.0626 0.4837 0.079 Uiso 1 1 calc R U . . .
C16 C 0.68868(6) 0.29229(6) 0.1795(3) 0.0470(4) Uani 1 1 d . . . . .
H13 H 0.7030 0.3201 0.1875 0.056 Uiso 1 1 calc R U . . .
C17 C 0.66101(6) 0.28134(6) 0.0244(2) 0.0436(4) Uani 1 1 d . . . . .
C18 C 0.65288(6) 0.31091(6) -0.1288(3) 0.0514(5) Uani 1 1 d . . . . .
H12 H 0.6666 0.3390 -0.1296 0.062 Uiso 1 1 calc R U . . .
C19 C 0.62568(6) 0.29920(6) -0.2741(3) 0.0547(5) Uani 1 1 d . . . . .
H11 H 0.6206 0.3193 -0.3731 0.066 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 1.362(2) . ?
O1 C1 1.424(3) . ?
O2 C13 1.220(2) . ?
N1 C5 1.312(2) . ?
N1 C4 1.367(2) . ?
N2 C13 1.370(2) . ?
N2 C6 1.397(2) . ?
N2 H5 0.8600 . ?
C1 H3 0.9600 . ?
C1 H14 0.9600 . ?
C1 H1 0.9600 . ?
C2 C3 1.358(2) . ?
C2 C19 1.414(3) . ?
C3 C4 1.406(2) . ?
C3 H4 0.9300 . ?
C4 C17 1.432(2) . ?
C5 C12 1.403(2) . ?
C5 C6 1.471(2) . ?
C6 C7 1.341(2) . ?
C7 C8 1.453(3) . ?
C7 H10 0.9300 . ?
C8 C9 1.382(3) . ?
C8 C15 1.397(3) . ?
C9 C10 1.378(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(4) . ?
C10 H6 0.9300 . ?
C11 C14 1.378(4) . ?
C11 H2 0.9300 . ?
C12 C16 1.364(2) . ?
C12 C13 1.472(2) . ?
C14 C15 1.364(3) . ?
C14 H8 0.9300 . ?
C15 H7 0.9300 . ?
C16 C17 1.404(2) . ?
C16 H13 0.9300 . ?
C17 C18 1.412(2) . ?
C18 C19 1.349(3) . ?
C18 H12 0.9300 . ?
C19 H11 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
C2 O1 C1 117.59(15) . . ?
C5 N1 C4 115.18(14) . . ?
C13 N2 C6 113.58(14) . . ?
C13 N2 H5 123.2 . . ?
C6 N2 H5 123.2 . . ?
O1 C1 H3 109.5 . . ?
O1 C1 H14 109.5 . . ?
H3 C1 H14 109.5 . . ?
O1 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
H14 C1 H1 109.5 . . ?
C3 C2 O1 124.67(17) . . ?
C3 C2 C19 120.92(17) . . ?
O1 C2 C19 114.41(16) . . ?
C2 C3 C4 120.14(17) . . ?
C2 C3 H4 119.9 . . ?
C4 C3 H4 119.9 . . ?
N1 C4 C3 117.39(15) . . ?
N1 C4 C17 123.17(15) . . ?
C3 C4 C17 119.43(15) . . ?
N1 C5 C12 125.80(15) . . ?
N1 C5 C6 125.61(15) . . ?
C12 C5 C6 108.58(14) . . ?
C7 C6 N2 131.74(16) . . ?
C7 C6 C5 123.72(16) . . ?
N2 C6 C5 104.51(14) . . ?
C6 C7 C8 132.06(18) . . ?
C6 C7 H10 114.0 . . ?
C8 C7 H10 114.0 . . ?
C9 C8 C15 117.85(18) . . ?
C9 C8 C7 124.15(17) . . ?
C15 C8 C7 117.99(19) . . ?
C10 C9 C8 120.9(2) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H6 120.0 . . ?
C9 C10 H6 120.0 . . ?
C10 C11 C14 120.0(2) . . ?
C10 C11 H2 120.0 . . ?
C14 C11 H2 120.0 . . ?
C16 C12 C5 119.89(15) . . ?
C16 C12 C13 132.59(16) . . ?
C5 C12 C13 107.52(15) . . ?
O2 C13 N2 126.03(17) . . ?
O2 C13 C12 128.16(17) . . ?
N2 C13 C12 105.81(15) . . ?
C15 C14 C11 119.8(2) . . ?
C15 C14 H8 120.1 . . ?
C11 C14 H8 120.1 . . ?
C14 C15 C8 121.4(2) . . ?
C14 C15 H7 119.3 . . ?
C8 C15 H7 119.3 . . ?
C12 C16 C17 117.33(15) . . ?
C12 C16 H13 121.3 . . ?
C17 C16 H13 121.3 . . ?
C16 C17 C18 123.30(16) . . ?
C16 C17 C4 118.61(15) . . ?
C18 C17 C4 118.09(15) . . ?
C19 C18 C17 121.37(17) . . ?
C19 C18 H12 119.3 . . ?
C17 C18 H12 119.3 . . ?
C18 C19 C2 120.04(17) . . ?
C18 C19 H11 120.0 . . ?
C2 C19 H11 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
C1 O1 C2 C3 1.6(3) . . . . ?
C1 O1 C2 C19 -178.9(2) . . . . ?
O1 C2 C3 C4 179.47(18) . . . . ?
C19 C2 C3 C4 -0.1(3) . . . . ?
C5 N1 C4 C3 179.52(16) . . . . ?
C5 N1 C4 C17 0.0(2) . . . . ?
C2 C3 C4 N1 -179.73(17) . . . . ?
C2 C3 C4 C17 -0.2(3) . . . . ?
C4 N1 C5 C12 1.0(3) . . . . ?
C4 N1 C5 C6 -179.68(16) . . . . ?
C13 N2 C6 C7 177.83(19) . . . . ?
C13 N2 C6 C5 -0.1(2) . . . . ?
N1 C5 C6 C7 2.7(3) . . . . ?
C12 C5 C6 C7 -177.89(17) . . . . ?
N1 C5 C6 N2 -179.14(17) . . . . ?
C12 C5 C6 N2 0.25(19) . . . . ?
N2 C6 C7 C8 3.9(4) . . . . ?
C5 C6 C7 C8 -178.55(18) . . . . ?
C6 C7 C8 C9 20.2(3) . . . . ?
C6 C7 C8 C15 -161.0(2) . . . . ?
C15 C8 C9 C10 0.2(3) . . . . ?
C7 C8 C9 C10 179.01(19) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C9 C10 C11 C14 -0.6(4) . . . . ?
N1 C5 C12 C16 -1.3(3) . . . . ?
C6 C5 C12 C16 179.35(16) . . . . ?
N1 C5 C12 C13 179.08(17) . . . . ?
C6 C5 C12 C13 -0.30(19) . . . . ?
C6 N2 C13 O2 -179.29(17) . . . . ?
C6 N2 C13 C12 -0.1(2) . . . . ?
C16 C12 C13 O2 -0.2(3) . . . . ?
C5 C12 C13 O2 179.42(18) . . . . ?
C16 C12 C13 N2 -179.34(19) . . . . ?
C5 C12 C13 N2 0.24(19) . . . . ?
C10 C11 C14 C15 0.1(4) . . . . ?
C11 C14 C15 C8 0.5(4) . . . . ?
C9 C8 C15 C14 -0.7(3) . . . . ?
C7 C8 C15 C14 -179.52(19) . . . . ?
C5 C12 C16 C17 0.4(3) . . . . ?
C13 C12 C16 C17 179.93(17) . . . . ?
C12 C16 C17 C18 -179.82(17) . . . . ?
C12 C16 C17 C4 0.5(2) . . . . ?
N1 C4 C17 C16 -0.7(2) . . . . ?
C3 C4 C17 C16 179.73(16) . . . . ?
N1 C4 C17 C18 179.58(16) . . . . ?
C3 C4 C17 C18 0.0(2) . . . . ?
C16 C17 C18 C19 -179.33(18) . . . . ?
C4 C17 C18 C19 0.3(3) . . . . ?
C17 C18 C19 C2 -0.6(3) . . . . ?
C3 C2 C19 C18 0.5(3) . . . . ?
O1 C2 C19 C18 -179.13(18) . . . . ?

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.034

_shelxl_version_number           2014-3



