# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_SK_01_489
_database_code_depnum_ccdc_archive 'CCDC 1487921'
_audit_update_record             
;
2016-06-28 deposited with the CCDC.
2016-09-07 downloaded from the CCDC.
;
_audit_creation_date             2016-02-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'C19 H15 N O2 S2'
_chemical_formula_sum            'C19 H15 N O2 S2'
_chemical_formula_weight         353.44
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   16.385(2)
_cell_length_b                   13.037(2)
_cell_length_c                   8.2869(14)
_cell_angle_alpha                90
_cell_angle_beta                 103.740(6)
_cell_angle_gamma                90
_cell_volume                     1719.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2115
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      24.37
_cell_measurement_theta_min      2.97
_exptl_absorpt_coefficient_mu    0.320
_exptl_crystal_colour            yellow
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0917 before and 0.0545 after correction.
The Ratio of minimum to maximum transmission is 0.9242.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.3652
_exptl_crystal_description       plate
_exptl_crystal_F_000             736.0
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            8283
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         23.53
_diffrn_reflns_theta_min         2.56
_diffrn_ambient_temperature      140.0
_diffrn_measured_fraction_theta_full 0.9844
_diffrn_measured_fraction_theta_max 0.9844
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              17
_reflns_limit_h_min              -18
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                1906
_reflns_number_total             2559
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.3767
_refine_diff_density_min         -0.3779
_refine_diff_density_rms         0.0913
_refine_ls_d_res_high            0.8903
_refine_ls_d_res_low             7.9582
_refine_ls_goodness_of_fit_ref   1.0511
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2519
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.0511
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0313P)²+0.4103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0844
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C3(H3), C7(H7), C11(H11), C10(H10), C13(H13), C18(H18), C6(H6),
 C5(H5), C16(H16), C17(H17), C12(H12), C9(H9), C4(H4)
;
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_refinement_flags_posn
S1 S 0.86121(4) 0.90768(5) 0.14239(9) 0.0254(2) Uani 1.000000 .
S2 S 0.83257(4) 0.99737(6) 0.45689(9) 0.0288(2) Uani 1.000000 .
O1 O 0.54569(10) 1.04378(14) 0.1615(2) 0.0314(5) Uani 1.000000 .
O2 O 0.63176(10) 1.03033(14) -0.0010(2) 0.0282(5) Uani 1.000000 .
C15 C 0.62990(13) 0.89926(18) 0.1869(3) 0.0159(6) Uani 1.000000 .
C19 C 0.73663(15) 0.78307(19) 0.3122(3) 0.0213(6) Uani 1.000000 .
H19 H 0.79422(15) 0.76631(19) 0.3537(3) 0.0255(8) Uiso 1.000000 R
C14 C 0.71532(13) 0.87942(18) 0.2428(3) 0.0156(6) Uani 1.000000 .
N1 N 0.60086(12) 0.99849(16) 0.1112(3) 0.0197(5) Uani 1.000000 .
C1 C 0.78222(13) 0.95886(19) 0.2431(3) 0.0185(6) Uani 1.000000 .
H1 H 0.75559(13) 1.02048(19) 0.1801(3) 0.0221(7) Uiso 1.000000 R
C2 C 0.90850(14) 1.02443(19) 0.0995(3) 0.0207(6) Uani 1.000000 .
C8 C 0.74507(14) 1.0615(2) 0.5043(3) 0.0232(6) Uani 1.000000 .
C3 C 0.98075(14) 1.0598(2) 0.2081(3) 0.0263(7) Uani 1.000000 .
H3 H 1.00489(14) 1.0220(2) 0.3058(3) 0.0316(8) Uiso 1.000000 R
C7 C 0.87466(15) 1.0791(2) -0.0434(4) 0.0321(7) Uani 1.000000 .
H7 H 0.82534(15) 1.0549(2) -0.1187(4) 0.0385(9) Uiso 1.000000 R
C11 C 0.6067(2) 1.1601(3) 0.5701(4) 0.0504(9) Uani 1.000000 .
H11 H 0.5594(2) 1.1941(3) 0.5930(4) 0.0604(11) Uiso 1.000000 R
C10 C 0.61801(17) 1.0573(3) 0.6002(4) 0.0392(8) Uani 1.000000 .
H10 H 0.57828(17) 1.0198(3) 0.6435(4) 0.0470(10) Uiso 1.000000 R
C13 C 0.73317(19) 1.1652(2) 0.4738(4) 0.0421(8) Uani 1.000000 .
H13 H 0.77256(19) 1.2031(2) 0.4303(4) 0.0506(10) Uiso 1.000000 R
C18 C 0.67625(15) 0.7113(2) 0.3222(3) 0.0251(6) Uani 1.000000 .
H18 H 0.69288(15) 0.6456(2) 0.3682(3) 0.0301(8) Uiso 1.000000 R
C6 C 0.91244(17) 1.1693(2) -0.0775(4) 0.0395(8) Uani 1.000000 .
H6 H 0.88933(17) 1.2065(2) -0.1763(4) 0.0474(10) Uiso 1.000000 R
C5 C 0.98385(17) 1.2048(2) 0.0331(4) 0.0363(8) Uani 1.000000 .
H5 H 1.00937(17) 1.2670(2) 0.0113(4) 0.0436(9) Uiso 1.000000 R
C16 C 0.56797(15) 0.8292(2) 0.1995(3) 0.0230(6) Uani 1.000000 .
H16 H 0.51027(15) 0.8468(2) 0.1628(3) 0.0277(8) Uiso 1.000000 R
C17 C 0.59133(15) 0.7338(2) 0.2660(3) 0.0267(7) Uani 1.000000 .
H17 H 0.54997(15) 0.6841(2) 0.2734(3) 0.0321(8) Uiso 1.000000 R
C12 C 0.6639(2) 1.2137(3) 0.5068(5) 0.0563(10) Uani 1.000000 .
H12 H 0.6559(2) 1.2851(3) 0.4853(5) 0.0676(12) Uiso 1.000000 R
C9 C 0.68678(16) 1.0078(2) 0.5679(3) 0.0289(7) Uani 1.000000 .
H9 H 0.69425(16) 0.9364(2) 0.5895(3) 0.0347(8) Uiso 1.000000 R
C4 C 1.01772(16) 1.1500(2) 0.1742(4) 0.0343(8) Uani 1.000000 .
H4 H 1.06707(16) 1.1742(2) 0.2495(4) 0.0412(9) Uiso 1.000000 R


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 1.825(2) . ?
S1 C2 1.782(3) . ?
S2 C1 1.838(3) . ?
S2 C8 1.782(3) . ?
O1 N1 1.232(2) . ?
O2 N1 1.232(3) . ?
C15 C14 1.390(3) . ?
C15 N1 1.467(3) . ?
C15 C16 1.387(3) . ?
C19 C14 1.391(3) . ?
C19 C18 1.379(3) . ?
C14 C1 1.508(3) . ?
C2 C3 1.385(3) . ?
C2 C7 1.380(4) . ?
C8 C13 1.381(4) . ?
C8 C9 1.386(3) . ?
C3 C4 1.381(4) . ?
C7 C6 1.389(4) . ?
C11 C10 1.368(4) . ?
C11 C12 1.369(5) . ?
C10 C9 1.379(4) . ?
C13 C12 1.382(4) . ?
C18 C17 1.390(3) . ?
C6 C5 1.383(4) . ?
C5 C4 1.370(4) . ?
C16 C17 1.377(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
C2 S1 C1 99.67(11) . . ?
C8 S2 C1 98.06(11) . . ?
N1 C15 C14 120.3(2) . . ?
C16 C15 C14 123.3(2) . . ?
C16 C15 N1 116.4(2) . . ?
C18 C19 C14 121.6(2) . . ?
C19 C14 C15 116.1(2) . . ?
C1 C14 C15 123.2(2) . . ?
C1 C14 C19 120.6(2) . . ?
O2 N1 O1 124.0(2) . . ?
C15 N1 O1 117.9(2) . . ?
C15 N1 O2 118.08(19) . . ?
S2 C1 S1 109.63(11) . . ?
C14 C1 S1 110.03(16) . . ?
C14 C1 S2 110.41(17) . . ?
C3 C2 S1 120.0(2) . . ?
C7 C2 S1 120.5(2) . . ?
C7 C2 C3 119.5(2) . . ?
C13 C8 S2 120.3(2) . . ?
C9 C8 S2 120.7(2) . . ?
C9 C8 C13 119.0(3) . . ?
C4 C3 C2 120.0(3) . . ?
C6 C7 C2 120.3(3) . . ?
C12 C11 C10 119.7(3) . . ?
C9 C10 C11 120.3(3) . . ?
C12 C13 C8 120.0(3) . . ?
C17 C18 C19 120.8(2) . . ?
C5 C6 C7 119.7(3) . . ?
C4 C5 C6 119.9(3) . . ?
C17 C16 C15 119.1(2) . . ?
C16 C17 C18 119.1(2) . . ?
C13 C12 C11 120.7(3) . . ?
C10 C9 C8 120.4(3) . . ?
C5 C4 C3 120.6(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'

#
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared), status flag
#


####################################################################### 
# 
# 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_SK_543_P
_database_code_depnum_ccdc_archive 'CCDC 1487922'
_audit_update_record             
;
2016-06-28 deposited with the CCDC.
2016-09-07 downloaded from the CCDC.
;
_audit_creation_date             2016-02-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'C19 H13 Br2 N O2 S2'
_chemical_formula_sum            'C19 H13 Br2 N O2 S2'
_chemical_formula_weight         511.22
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   7.6546(8)
_cell_length_b                   29.982(3)
_cell_length_c                   8.7107(10)
_cell_angle_alpha                90
_cell_angle_beta                 108.845(4)
_cell_angle_gamma                90
_cell_volume                     1892.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    187(2)
_cell_measurement_theta_max      27.83
_cell_measurement_theta_min      2.56
_exptl_absorpt_coefficient_mu    4.519
_exptl_crystal_colour            colourless
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0997 before and 0.0586 after correction.
The Ratio of minimum to maximum transmission is 0.6958.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.7948
_exptl_crystal_description       needle
_exptl_crystal_F_000             1008.0
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4339
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.56
_diffrn_ambient_temperature      187.23
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -9
_reflns_limit_k_max              38
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              -5
_reflns_number_gt                3710
_reflns_number_total             4339
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.6281
_refine_diff_density_min         -0.5255
_refine_diff_density_rms         0.1338
_refine_ls_d_res_high            0.7701
_refine_ls_d_res_low             7.9488
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0694
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0318
_refine_ls_restrained_S_all      1.0694
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0167P)²+2.5101P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0571
_refine_ls_wR_factor_ref         0.0603
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C13(H13), C15(H15), C18(H18), C12(H12), C7(H7), C9(H9), C6(H6),
 C19(H19), C4(H4), C3(H3), C10(H10)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Br2 Br 0.74493(4) 0.318574(9) 0.31967(3) 0.02983(8) Uani 1.000000 .
Br1 Br 0.88901(4) 0.509529(10) -0.83633(4) 0.03327(8) Uani 1.000000 .
S1 S 0.20016(9) 0.33848(2) -0.41344(8) 0.02613(15) Uani 1.000000 .
S2 S 0.35461(9) 0.42273(2) -0.47703(8) 0.02480(14) Uani 1.000000 .
O1 O -0.2165(3) 0.34871(7) -1.2705(2) 0.0412(5) Uani 1.000000 .
C17 C 0.0074(3) 0.33258(8) -1.0250(3) 0.0220(5) Uani 1.000000 .
C5 C 0.7323(3) 0.48219(8) -0.7316(3) 0.0230(5) Uani 1.000000 .
N1 N -0.1034(3) 0.32094(7) -1.1930(3) 0.0270(5) Uani 1.000000 .
C2 C 0.5028(3) 0.44362(8) -0.5820(3) 0.0219(5) Uani 1.000000 .
C8 C 0.3672(3) 0.33529(8) -0.2162(3) 0.0218(5) Uani 1.000000 .
C16 C -0.0115(3) 0.37472(8) -0.9672(3) 0.0239(5) Uani 1.000000 .
H16 H -0.0950(3) 0.39572(8) -1.0339(3) 0.0287(6) Uiso 1.000000 R
O2 O -0.0799(3) 0.28479(7) -1.2457(2) 0.0396(5) Uani 1.000000 .
C13 C 0.3952(3) 0.37098(8) -0.1084(3) 0.0227(5) Uani 1.000000 .
H13 H 0.3334(3) 0.39846(8) -0.1434(3) 0.0272(6) Uiso 1.000000 R
C15 C 0.0944(3) 0.38560(8) -0.8098(3) 0.0231(5) Uani 1.000000 .
H15 H 0.0837(3) 0.41445(8) -0.7686(3) 0.0277(6) Uiso 1.000000 R
C18 C 0.1272(3) 0.30115(8) -0.9312(3) 0.0226(5) Uani 1.000000 .
H18 H 0.1383(3) 0.27246(8) -0.9734(3) 0.0272(6) Uiso 1.000000 R
C12 C 0.5125(3) 0.36660(8) 0.0493(3) 0.0227(5) Uani 1.000000 .
H12 H 0.5346(3) 0.39111(8) 0.1222(3) 0.0272(6) Uiso 1.000000 R
C1 C 0.3276(3) 0.36425(8) -0.5362(3) 0.0210(5) Uani 1.000000 .
H1 H 0.4520(3) 0.35002(8) -0.5102(3) 0.0252(6) Uiso 1.000000 R
C7 C 0.4318(3) 0.47345(8) -0.7090(3) 0.0240(5) Uani 1.000000 .
H7 H 0.3038(3) 0.48036(8) -0.7446(3) 0.0288(6) Uiso 1.000000 R
C9 C 0.4580(3) 0.29507(8) -0.1649(3) 0.0247(5) Uani 1.000000 .
H9 H 0.4410(3) 0.27095(8) -0.2389(3) 0.0297(6) Uiso 1.000000 R
C14 C 0.2159(3) 0.35481(8) -0.7117(3) 0.0198(5) Uani 1.000000 .
C6 C 0.5472(3) 0.49324(8) -0.7842(3) 0.0238(5) Uani 1.000000 .
H6 H 0.4995(3) 0.51396(8) -0.8702(3) 0.0286(6) Uiso 1.000000 R
C11 C 0.5977(3) 0.32565(8) 0.0993(3) 0.0213(5) Uani 1.000000 .
C19 C 0.2303(3) 0.31260(8) -0.7742(3) 0.0223(5) Uani 1.000000 .
H19 H 0.3125(3) 0.29134(8) -0.7077(3) 0.0268(6) Uiso 1.000000 R
C4 C 0.8064(4) 0.45276(8) -0.6066(3) 0.0256(5) Uani 1.000000 .
H4 H 0.9341(4) 0.44563(8) -0.5727(3) 0.0308(7) Uiso 1.000000 R
C3 C 0.6902(4) 0.43364(8) -0.5307(3) 0.0256(5) Uani 1.000000 .
H3 H 0.7395(4) 0.41356(8) -0.4430(3) 0.0307(7) Uiso 1.000000 R
C10 C 0.5731(3) 0.29000(8) -0.0061(3) 0.0242(5) Uani 1.000000 .
H10 H 0.6341(3) 0.26246(8) 0.0295(3) 0.0291(6) Uiso 1.000000 R


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
Br2 C11 1.898(2) . ?
Br1 C5 1.911(2) . ?
S1 C8 1.783(2) . ?
S1 C1 1.835(2) . ?
S2 C2 1.784(3) . ?
S2 C1 1.820(2) . ?
O1 N1 1.233(3) . ?
C17 N1 1.477(3) . ?
C17 C16 1.385(3) . ?
C17 C18 1.383(3) . ?
C5 C6 1.381(3) . ?
C5 C4 1.374(4) . ?
N1 O2 1.213(3) . ?
C2 C7 1.390(3) . ?
C2 C3 1.390(4) . ?
C8 C13 1.393(3) . ?
C8 C9 1.391(4) . ?
C16 H16 0.9500 . ?
C16 C15 1.387(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.383(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.391(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.392(3) . ?
C1 H1 1.0000 . ?
C1 C14 1.517(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.391(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.387(4) . ?
C14 C19 1.396(3) . ?
C6 H6 0.9500 . ?
C11 C10 1.382(3) . ?
C19 H19 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.391(4) . ?
C3 H3 0.9500 . ?
C10 H10 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
C1 S1 C8 103.51(11) . . ?
C1 S2 C2 103.03(11) . . ?
C16 C17 N1 118.8(2) . . ?
C18 C17 N1 118.9(2) . . ?
C18 C17 C16 122.3(2) . . ?
C6 C5 Br1 118.28(19) . . ?
C4 C5 Br1 119.45(19) . . ?
C4 C5 C6 122.3(2) . . ?
C17 N1 O1 117.4(2) . . ?
O2 N1 O1 124.1(2) . . ?
O2 N1 C17 118.6(2) . . ?
C7 C2 S2 118.94(19) . . ?
C3 C2 S2 121.37(19) . . ?
C3 C2 C7 119.5(2) . . ?
C13 C8 S1 120.97(19) . . ?
C9 C8 S1 118.97(19) . . ?
C9 C8 C13 119.8(2) . . ?
H16 C16 C17 120.73(14) . . ?
C15 C16 C17 118.5(2) . . ?
C15 C16 H16 120.73(14) . . ?
H13 C13 C8 119.83(14) . . ?
C12 C13 C8 120.3(2) . . ?
C12 C13 H13 119.83(15) . . ?
H15 C15 C16 119.59(14) . . ?
C14 C15 C16 120.8(2) . . ?
C14 C15 H15 119.59(14) . . ?
H18 C18 C17 120.89(14) . . ?
C19 C18 C17 118.2(2) . . ?
C19 C18 H18 120.89(14) . . ?
H12 C12 C13 120.57(14) . . ?
C11 C12 C13 118.9(2) . . ?
C11 C12 H12 120.57(14) . . ?
S2 C1 S1 105.87(12) . . ?
H1 C1 S1 109.53(8) . . ?
H1 C1 S2 109.53(8) . . ?
C14 C1 S1 106.00(16) . . ?
C14 C1 S2 116.14(17) . . ?
C14 C1 H1 109.53(13) . . ?
H7 C7 C2 119.82(15) . . ?
C6 C7 C2 120.4(2) . . ?
C6 C7 H7 119.82(15) . . ?
H9 C9 C8 119.81(14) . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.81(15) . . ?
C1 C14 C15 122.9(2) . . ?
C19 C14 C15 118.9(2) . . ?
C19 C14 C1 118.2(2) . . ?
C7 C6 C5 118.7(2) . . ?
H6 C6 C5 120.64(15) . . ?
H6 C6 C7 120.64(15) . . ?
C12 C11 Br2 118.70(18) . . ?
C10 C11 Br2 119.65(18) . . ?
C10 C11 C12 121.6(2) . . ?
C14 C19 C18 121.3(2) . . ?
H19 C19 C18 119.36(14) . . ?
H19 C19 C14 119.36(14) . . ?
H4 C4 C5 120.74(15) . . ?
C3 C4 C5 118.5(2) . . ?
C3 C4 H4 120.74(15) . . ?
C4 C3 C2 120.7(2) . . ?
H3 C3 C2 119.66(15) . . ?
H3 C3 C4 119.66(15) . . ?
C11 C10 C9 118.9(2) . . ?
H10 C10 C9 120.53(15) . . ?
H10 C10 C11 120.53(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'

#
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared), status flag
#


####################################################################### 
# 
# 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_SK_01_439
_database_code_depnum_ccdc_archive 'CCDC 1500695'
_audit_update_record             
;
2016-08-23 deposited with the CCDC.
2016-09-07 downloaded from the CCDC.
;
_audit_creation_date             2016-06-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10 N2 O5'
_chemical_formula_sum            'C14 H10 N2 O5'
_chemical_formula_weight         286.24
_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'

_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 21/c'
_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                   13.122(6)
_cell_length_b                   12.993(6)
_cell_length_c                   7.922(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.660(12)
_cell_angle_gamma                90
_cell_volume                     1312.5(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2667
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      24.87
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7984
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0813 before and 0.0498 after correction.
The Ratio of minimum to maximum transmission is 0.7984.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0967
_diffrn_reflns_av_unetI/netI     0.0729
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14834
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.801
_diffrn_reflns_theta_max         25.801
_diffrn_reflns_theta_min         2.238
_diffrn_ambient_temperature      140.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1431
_reflns_number_total             2517
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2482
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1293
_refine_ls_R_factor_gt           0.0590
_refine_ls_restrained_S_all      1.062
_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)+(0.0390P)²+0.9068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1284
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C10(H10), C11(H11), C7(H7), C13(H13), C8(H8), C5(H5), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O5 O 0.78036(14) 0.60457(19) 0.0424(3) 0.0434(6) Uani 1 1 d . . . . .
O1 O 1.31940(14) 0.66496(19) -0.0088(3) 0.0452(6) Uani 1 1 d . . . . .
N2 N 0.82693(17) 0.6173(2) -0.0732(3) 0.0310(6) Uani 1 1 d . . . . .
C12 C 0.94200(19) 0.6264(2) -0.0244(4) 0.0265(7) Uani 1 1 d . . . . .
C14 C 1.1016(2) 0.6230(2) 0.1908(4) 0.0287(7) Uani 1 1 d . . . . .
H14 H 1.1386 0.6171 0.3090 0.034 Uiso 1 1 calc R . . . .
O2 O 1.81703(15) 0.4947(2) 0.4069(3) 0.0453(7) Uani 1 1 d . . . . .
C10 C 1.1025(2) 0.6447(2) -0.1093(4) 0.0310(8) Uani 1 1 d . . . . .
H10 H 1.1401 0.6541 -0.1970 0.037 Uiso 1 1 calc R . . . .
O4 O 0.78258(14) 0.62106(19) -0.2272(3) 0.0444(7) Uani 1 1 d . . . . .
O3 O 1.83318(14) 0.65978(19) 0.4306(3) 0.0410(6) Uani 1 1 d . . . . .
C1 C 1.2748(2) 0.6402(2) 0.1040(4) 0.0297(8) Uani 1 1 d . . . . .
C11 C 0.9943(2) 0.6399(2) -0.1551(4) 0.0303(8) Uani 1 1 d . . . . .
H11 H 0.9569 0.6457 -0.2730 0.036 Uiso 1 1 calc R . . . .
N1 N 1.78041(18) 0.5815(2) 0.4024(3) 0.0347(7) Uani 1 1 d . . . . .
C9 C 1.15692(19) 0.6361(2) 0.0629(4) 0.0257(7) Uani 1 1 d . . . . .
C6 C 1.6650(2) 0.5914(3) 0.3641(3) 0.0289(8) Uani 1 1 d . . . . .
C7 C 1.6225(2) 0.6792(3) 0.4142(4) 0.0359(8) Uani 1 1 d . . . . .
H7 H 1.6662 0.7343 0.4675 0.043 Uiso 1 1 calc R . . . .
C13 C 0.99270(19) 0.6184(2) 0.1476(4) 0.0288(7) Uani 1 1 d . . . . .
H13 H 0.9545 0.6099 0.2346 0.035 Uiso 1 1 calc R . . . .
C8 C 1.5143(2) 0.6860(3) 0.3854(4) 0.0349(8) Uani 1 1 d . . . . .
H8 H 1.4834 0.7463 0.4193 0.042 Uiso 1 1 calc R . . . .
C3 C 1.4509(2) 0.6059(3) 0.3079(4) 0.0308(8) Uani 1 1 d . . . . .
C5 C 1.6045(2) 0.5110(3) 0.2851(4) 0.0382(9) Uani 1 1 d . . . . .
H5 H 1.6358 0.4509 0.2510 0.046 Uiso 1 1 calc R . . . .
C4 C 1.4962(2) 0.5196(3) 0.2560(4) 0.0397(9) Uani 1 1 d . . . . .
H4 H 1.4528 0.4652 0.1996 0.048 Uiso 1 1 calc R . . . .
C2 C 1.33322(19) 0.6122(3) 0.2840(4) 0.0356(8) Uani 1 1 d . . . . .
H2A H 1.3074 0.5447 0.3145 0.043 Uiso 1 1 calc R . . . .
H2B H 1.3174 0.6639 0.3660 0.043 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
O5 N2 1.226(3) . ?
O1 C1 1.222(3) . ?
N2 C12 1.472(3) . ?
N2 O4 1.222(3) . ?
C12 C11 1.381(4) . ?
C12 C13 1.372(4) . ?
C14 H14 0.9500 . ?
C14 C9 1.389(4) . ?
C14 C13 1.390(4) . ?
O2 N1 1.223(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(4) . ?
C10 C9 1.387(4) . ?
O3 N1 1.221(3) . ?
C1 C9 1.504(4) . ?
C1 C2 1.496(4) . ?
C11 H11 0.9500 . ?
N1 C6 1.478(3) . ?
C6 C7 1.370(4) . ?
C6 C5 1.371(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(4) . ?
C13 H13 0.9500 . ?
C8 H8 0.9500 . ?
C8 C3 1.382(4) . ?
C3 C4 1.377(4) . ?
C3 C2 1.513(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.390(4) . ?
C4 H4 0.9500 . ?
C2 H2A 0.9900 . ?
C2 H2B 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
O5 N2 C12 118.4(2) . . ?
O4 N2 O5 123.2(2) . . ?
O4 N2 C12 118.4(2) . . ?
C11 C12 N2 118.3(2) . . ?
C13 C12 N2 118.8(2) . . ?
C13 C12 C11 122.9(2) . . ?
C9 C14 H14 119.7 . . ?
C9 C14 C13 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C11 C10 H10 119.6 . . ?
C11 C10 C9 120.9(3) . . ?
C9 C10 H10 119.6 . . ?
O1 C1 C9 119.8(3) . . ?
O1 C1 C2 122.4(2) . . ?
C2 C1 C9 117.9(2) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 C12 118.1(3) . . ?
C10 C11 H11 121.0 . . ?
O2 N1 C6 117.5(3) . . ?
O3 N1 O2 124.1(3) . . ?
O3 N1 C6 118.3(3) . . ?
C14 C9 C1 122.3(3) . . ?
C10 C9 C14 119.4(2) . . ?
C10 C9 C1 118.3(2) . . ?
C7 C6 N1 118.7(3) . . ?
C7 C6 C5 122.4(3) . . ?
C5 C6 N1 118.8(3) . . ?
C6 C7 H7 120.8 . . ?
C6 C7 C8 118.4(3) . . ?
C8 C7 H7 120.8 . . ?
C12 C13 C14 118.1(2) . . ?
C12 C13 H13 121.0 . . ?
C14 C13 H13 121.0 . . ?
C7 C8 H8 119.6 . . ?
C3 C8 C7 120.7(3) . . ?
C3 C8 H8 119.6 . . ?
C8 C3 C2 120.3(3) . . ?
C4 C3 C8 119.3(3) . . ?
C4 C3 C2 120.4(3) . . ?
C6 C5 H5 120.9 . . ?
C6 C5 C4 118.3(3) . . ?
C4 C5 H5 120.9 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C1 C2 C3 114.3(2) . . ?
C1 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?

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
O5 N2 C12 C11 179.5(3) . . . . ?
O5 N2 C12 C13 1.1(4) . . . . ?
O1 C1 C9 C14 -170.6(3) . . . . ?
O1 C1 C9 C10 10.1(4) . . . . ?
O1 C1 C2 C3 -6.3(5) . . . . ?
N2 C12 C11 C10 -177.8(3) . . . . ?
N2 C12 C13 C14 177.5(3) . . . . ?
O2 N1 C6 C7 158.1(3) . . . . ?
O2 N1 C6 C5 -19.7(4) . . . . ?
O4 N2 C12 C11 0.8(4) . . . . ?
O4 N2 C12 C13 -177.6(3) . . . . ?
O3 N1 C6 C7 -20.5(4) . . . . ?
O3 N1 C6 C5 161.7(3) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C11 C10 C9 C14 -0.3(5) . . . . ?
C11 C10 C9 C1 179.0(3) . . . . ?
N1 C6 C7 C8 -177.0(3) . . . . ?
N1 C6 C5 C4 177.5(3) . . . . ?
C9 C14 C13 C12 0.5(5) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C9 C1 C2 C3 173.0(3) . . . . ?
C6 C7 C8 C3 0.0(5) . . . . ?
C6 C5 C4 C3 -1.1(5) . . . . ?
C7 C6 C5 C4 -0.3(5) . . . . ?
C7 C8 C3 C4 -1.3(5) . . . . ?
C7 C8 C3 C2 177.4(3) . . . . ?
C13 C12 C11 C10 0.5(5) . . . . ?
C13 C14 C9 C10 0.0(5) . . . . ?
C13 C14 C9 C1 -179.2(3) . . . . ?
C8 C3 C4 C5 1.8(5) . . . . ?
C8 C3 C2 C1 101.1(3) . . . . ?
C5 C6 C7 C8 0.8(5) . . . . ?
C4 C3 C2 C1 -80.2(4) . . . . ?
C2 C1 C9 C14 10.0(4) . . . . ?
C2 C1 C9 C10 -169.2(3) . . . . ?
C2 C3 C4 C5 -176.8(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

#
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared), status flag
#


