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

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

data_IFuran
_database_code_depnum_ccdc_archive 'CCDC 1415044'
_audit_update_record             
;
2016-09-05 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;
_audit_creation_date             2015-07-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H7 N3 O2'
_chemical_formula_sum            'C9 H7 N3 O2'
_chemical_formula_weight         189.18
_chemical_absolute_configuration unk
_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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   30.656(3)
_cell_length_b                   27.727(5)
_cell_length_c                   3.7908(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3222.2(7)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    3586
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.9370
_cell_measurement_theta_min      3.2160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            7656
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.279
_diffrn_reflns_theta_min         3.964
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'SuperNova, Dual, Atlas'
_diffrn_measurement_device_type  'SuperNova, Dual, Atlas'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova, Dual, Atlas'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.666
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.884
_reflns_number_gt                1679
_reflns_number_total             1861
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1861
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.073
_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)+(0.0709P)²+5.9313P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1282
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O1 O 0.48218(6) 0.62371(7) 0.7285(7) 0.0201(5) Uani 1 1 d . . . . .
N1 N 0.54390(7) 0.55560(8) 0.6350(7) 0.0184(6) Uani 1 1 d . . . . .
H1 H 0.5156 0.5516 0.6105 0.022 Uiso 1 1 calc R . . . .
C1 C 0.45737(9) 0.66329(11) 0.8052(9) 0.0221(7) Uani 1 1 d . . . . .
H1A H 0.4272 0.6664 0.7517 0.027 Uiso 1 1 calc R . . . .
O2 O 0.59525(6) 0.60537(7) 0.8830(7) 0.0232(5) Uani 1 1 d . . . . .
N2 N 0.63901(8) 0.48915(10) 0.2929(8) 0.0248(6) Uani 1 1 d . . . . .
C2 C 0.48153(9) 0.69741(11) 0.9674(9) 0.0216(6) Uani 1 1 d . . . . .
H2 H 0.4718 0.7281 1.0467 0.026 Uiso 1 1 calc R . . . .
N3 N 0.55040(7) 0.47708(8) 0.4417(7) 0.0182(5) Uani 1 1 d . . . . .
C3 C 0.52461(9) 0.67825(10) 0.9962(9) 0.0215(6) Uani 1 1 d . . . . .
H3 H 0.5493 0.6936 1.0982 0.026 Uiso 1 1 calc R . . . .
C4 C 0.52335(9) 0.63388(10) 0.8495(9) 0.0184(6) Uani 1 1 d . . . . .
C5 C 0.55730(9) 0.59722(10) 0.7914(8) 0.0178(6) Uani 1 1 d . . . . .
C6 C 0.57081(9) 0.51842(10) 0.5088(8) 0.0172(6) Uani 1 1 d . . . . .
C7 C 0.61561(9) 0.52423(11) 0.4387(9) 0.0213(7) Uani 1 1 d . . . . .
H7 H 0.6294 0.5539 0.4969 0.026 Uiso 1 1 calc R . . . .
C8 C 0.61833(9) 0.44803(11) 0.2191(9) 0.0223(7) Uani 1 1 d . . . . .
H8 H 0.6340 0.4224 0.1116 0.027 Uiso 1 1 calc R . . . .
C9 C 0.57474(10) 0.44212(10) 0.2957(8) 0.0201(7) Uani 1 1 d . . . . .
H9 H 0.5613 0.4121 0.2432 0.024 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.366(3) . ?
O1 C4 1.372(3) . ?
N1 H1 0.8800 . ?
N1 C5 1.361(4) . ?
N1 C6 1.404(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.350(4) . ?
O2 C5 1.235(3) . ?
N2 C7 1.329(4) . ?
N2 C8 1.334(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.428(4) . ?
N3 C6 1.330(4) . ?
N3 C9 1.343(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.350(4) . ?
C4 C5 1.471(4) . ?
C6 C7 1.408(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.377(4) . ?
C9 H9 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 O1 C4 106.0(2) . . ?
C5 N1 H1 116.8 . . ?
C5 N1 C6 126.4(2) . . ?
C6 N1 H1 116.8 . . ?
O1 C1 H1A 124.6 . . ?
C2 C1 O1 110.8(2) . . ?
C2 C1 H1A 124.6 . . ?
C7 N2 C8 117.1(2) . . ?
C1 C2 H2 126.8 . . ?
C1 C2 C3 106.3(3) . . ?
C3 C2 H2 126.8 . . ?
C6 N3 C9 116.1(2) . . ?
C2 C3 H3 126.8 . . ?
C4 C3 C2 106.3(3) . . ?
C4 C3 H3 126.8 . . ?
O1 C4 C5 117.3(3) . . ?
C3 C4 O1 110.5(2) . . ?
C3 C4 C5 132.1(3) . . ?
N1 C5 C4 115.9(2) . . ?
O2 C5 N1 124.2(2) . . ?
O2 C5 C4 119.9(3) . . ?
N1 C6 C7 123.6(3) . . ?
N3 C6 N1 114.9(2) . . ?
N3 C6 C7 121.4(3) . . ?
N2 C7 C6 121.4(3) . . ?
N2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
N2 C8 H8 119.4 . . ?
N2 C8 C9 121.2(3) . . ?
C9 C8 H8 119.4 . . ?
N3 C9 C8 122.7(3) . . ?
N3 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?

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
O1 C1 C2 C3 0.0(4) . . . . ?
O1 C4 C5 N1 -2.7(4) . . . . ?
O1 C4 C5 O2 177.2(3) . . . . ?
N1 C6 C7 N2 -174.5(3) . . . . ?
C1 O1 C4 C3 -0.2(4) . . . . ?
C1 O1 C4 C5 -178.5(3) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
N2 C8 C9 N3 1.2(5) . . . . ?
C2 C3 C4 O1 0.1(4) . . . . ?
C2 C3 C4 C5 178.1(3) . . . . ?
N3 C6 C7 N2 2.1(5) . . . . ?
C3 C4 C5 N1 179.5(3) . . . . ?
C3 C4 C5 O2 -0.6(5) . . . . ?
C4 O1 C1 C2 0.1(4) . . . . ?
C5 N1 C6 N3 165.2(3) . . . . ?
C5 N1 C6 C7 -18.0(5) . . . . ?
C6 N1 C5 O2 -9.3(5) . . . . ?
C6 N1 C5 C4 170.6(3) . . . . ?
C6 N3 C9 C8 0.2(5) . . . . ?
C7 N2 C8 C9 -0.9(5) . . . . ?
C8 N2 C7 C6 -0.6(5) . . . . ?
C9 N3 C6 N1 175.1(3) . . . . ?
C9 N3 C6 C7 -1.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_IIThiophene
_database_code_depnum_ccdc_archive 'CCDC 1415045'
_audit_update_record             
;
2016-09-05 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;
_audit_creation_date             2015-07-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H7 N3 O S'
_chemical_formula_sum            'C9 H7 N3 O S'
_chemical_formula_weight         205.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H7 N3 S1 O1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.9507(4)
_cell_length_b                   11.7608(5)
_cell_length_c                   10.1981(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.216(5)
_cell_angle_gamma                90
_cell_volume                     894.84(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3185
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.1430
_cell_measurement_theta_min      3.9880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies, Version 1.171.36.28 
(release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897).
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.19
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4546
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.246
_diffrn_reflns_theta_min         3.312
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.3620
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -100.00  -74.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.3196  178.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -43.00   14.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.3196  -57.0000 -120.0000 57

#__ type_ start__ end____ width___ exp.time_
  3 omega  -70.00   45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       11.6321  -19.0000   30.0000 115
;
_diffrn_measurement_device       'SuperNova, Dual, Atlas'
_diffrn_measurement_device_type  'SuperNova, Dual, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0350239000
_diffrn_orient_matrix_UB_12      -0.0448716000
_diffrn_orient_matrix_UB_13      -0.0294622000
_diffrn_orient_matrix_UB_21      -0.0660154000
_diffrn_orient_matrix_UB_22      -0.0373505000
_diffrn_orient_matrix_UB_23      0.0076628000
_diffrn_orient_matrix_UB_31      -0.0587941000
_diffrn_orient_matrix_UB_32      0.0152768000
_diffrn_orient_matrix_UB_33      -0.0675025000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova, Dual, Atlas'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1952
_reflns_number_total             2091
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2091
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0312
_refine_ls_restrained_S_all      1.075
_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)+(0.0317P)²+0.5035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0787
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
S1 S 0.22130(5) 0.61510(3) 0.18022(3) 0.02024(11) Uani 1 1 d . . . . .
O1 O 0.42739(14) 0.40436(9) 0.24168(10) 0.0232(2) Uani 1 1 d . . . . .
N1 N 0.39825(14) 0.35188(10) 0.01927(11) 0.0160(2) Uani 1 1 d . . . . .
H1 H 0.3434 0.3687 -0.0694 0.019 Uiso 1 1 calc R . . . .
C1 C 0.08989(18) 0.70122(12) 0.05087(14) 0.0198(3) Uani 1 1 d . . . . .
H1A H 0.0354 0.7690 0.0674 0.024 Uiso 1 1 calc R . . . .
N2 N 0.50656(15) 0.19720(10) -0.06457(11) 0.0175(2) Uani 1 1 d . . . . .
C2 C 0.07195(18) 0.66186(12) -0.07874(14) 0.0180(3) Uani 1 1 d . . . . .
H2 H 0.0034 0.6991 -0.1629 0.022 Uiso 1 1 calc R . . . .
N3 N 0.72453(15) 0.13219(10) 0.20186(12) 0.0183(2) Uani 1 1 d . . . . .
C3 C 0.16672(17) 0.55930(11) -0.07416(13) 0.0155(3) Uani 1 1 d . . . . .
H3 H 0.1691 0.5201 -0.1550 0.019 Uiso 1 1 calc R . . . .
C4 C 0.25483(17) 0.52258(11) 0.05976(13) 0.0156(3) Uani 1 1 d . . . . .
C5 C 0.36670(17) 0.42203(12) 0.11522(13) 0.0165(3) Uani 1 1 d . . . . .
C6 C 0.50949(16) 0.25579(12) 0.04842(13) 0.0150(3) Uani 1 1 d . . . . .
C7 C 0.61996(17) 0.22294(12) 0.18307(13) 0.0183(3) Uani 1 1 d . . . . .
H7 H 0.6197 0.2663 0.2616 0.022 Uiso 1 1 calc R . . . .
C8 C 0.72541(18) 0.07442(12) 0.08930(14) 0.0198(3) Uani 1 1 d . . . . .
H8 H 0.8010 0.0100 0.1000 0.024 Uiso 1 1 calc R . . . .
C9 C 0.61669(19) 0.10808(12) -0.04287(14) 0.0202(3) Uani 1 1 d . . . . .
H9 H 0.6206 0.0660 -0.1213 0.024 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7044(15) . ?
S1 C4 1.7293(13) . ?
O1 C5 1.2285(16) . ?
N1 H1 0.8800 . ?
N1 C5 1.3677(17) . ?
N1 C6 1.4021(17) . ?
C1 H1A 0.9500 . ?
C1 C2 1.3606(19) . ?
N2 C6 1.3359(17) . ?
N2 C9 1.3343(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.4144(19) . ?
N3 C7 1.3255(19) . ?
N3 C8 1.3360(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.3716(18) . ?
C4 C5 1.4703(19) . ?
C6 C7 1.4045(17) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.3840(19) . ?
C9 H9 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 C4 91.59(7) . . ?
C5 N1 H1 116.8 . . ?
C5 N1 C6 126.35(11) . . ?
C6 N1 H1 116.8 . . ?
S1 C1 H1A 123.8 . . ?
C2 C1 S1 112.34(11) . . ?
C2 C1 H1A 123.8 . . ?
C9 N2 C6 116.57(11) . . ?
C1 C2 H2 123.8 . . ?
C1 C2 C3 112.48(12) . . ?
C3 C2 H2 123.8 . . ?
C7 N3 C8 118.32(12) . . ?
C2 C3 H3 123.7 . . ?
C4 C3 C2 112.60(12) . . ?
C4 C3 H3 123.7 . . ?
C3 C4 S1 110.99(10) . . ?
C3 C4 C5 132.00(12) . . ?
C5 C4 S1 117.01(9) . . ?
O1 C5 N1 123.12(13) . . ?
O1 C5 C4 120.38(12) . . ?
N1 C5 C4 116.50(11) . . ?
N1 C6 C7 124.37(12) . . ?
N2 C6 N1 114.28(11) . . ?
N2 C6 C7 121.33(13) . . ?
N3 C7 C6 120.80(13) . . ?
N3 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
N3 C8 H8 119.9 . . ?
N3 C8 C9 120.30(13) . . ?
C9 C8 H8 119.9 . . ?
N2 C9 C8 122.64(13) . . ?
N2 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N3 0.88 2.19 3.0546(15) 166.0 4_565

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
S1 C1 C2 C3 -0.02(15) . . . . ?
S1 C4 C5 O1 2.28(17) . . . . ?
S1 C4 C5 N1 -177.45(9) . . . . ?
N1 C6 C7 N3 -178.47(12) . . . . ?
C1 S1 C4 C3 0.18(10) . . . . ?
C1 S1 C4 C5 -179.43(10) . . . . ?
C1 C2 C3 C4 0.16(17) . . . . ?
N2 C6 C7 N3 -0.2(2) . . . . ?
C2 C3 C4 S1 -0.22(14) . . . . ?
C2 C3 C4 C5 179.32(13) . . . . ?
N3 C8 C9 N2 -0.6(2) . . . . ?
C3 C4 C5 O1 -177.23(13) . . . . ?
C3 C4 C5 N1 3.0(2) . . . . ?
C4 S1 C1 C2 -0.09(11) . . . . ?
C5 N1 C6 N2 175.28(12) . . . . ?
C5 N1 C6 C7 -6.3(2) . . . . ?
C6 N1 C5 O1 -4.0(2) . . . . ?
C6 N1 C5 C4 175.71(11) . . . . ?
C6 N2 C9 C8 2.0(2) . . . . ?
C7 N3 C8 C9 -1.2(2) . . . . ?
C8 N3 C7 C6 1.60(19) . . . . ?
C9 N2 C6 N1 176.89(12) . . . . ?
C9 N2 C6 C7 -1.54(19) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1 -1 0 0.1906 -1.0000 -1.0000 -0.0000 0.0098 0.1034 0.0435
1 1 0 0.1906 1.0000 1.0000 0.0000 -0.0098 -0.1034 -0.0435
0 -1 1 0.1576 0.0000 -1.0000 1.0000 0.0154 0.0450 -0.0828
0 1 -1 0.1576 -0.0000 1.0000 -1.0000 -0.0154 -0.0450 0.0828
1 2 -1 0.1313 1.0000 2.0000 -1.0000 -0.0253 -0.1484 0.0393
-1 0 -2 0.2092 -1.0000 -0.0000 -2.0000 0.0239 0.0507 0.1938
1 0 -1 0.1422 1.0000 0.0000 -1.0000 0.0645 -0.0737 0.0087
-1 0 1 0.0432 -1.0000 -0.0000 1.0000 -0.0645 0.0737 -0.0087
0 0 1 0.1723 0.0000 0.0000 1.0000 -0.0295 0.0077 -0.0675
0 -1 -1 0.1900 0.0000 -1.0000 -1.0000 0.0743 0.0297 0.0522
0 1 1 0.1900 -0.0000 1.0000 1.0000 -0.0743 -0.0297 -0.0522
0 -1 0 0.1941 0.0000 -1.0000 -0.0000 0.0449 0.0374 -0.0153
0 1 0 0.1574 -0.0000 1.0000 0.0000 -0.0449 -0.0374 0.0153

_olex2_submission_special_instructions 'No special instructions were received'
