# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_mo_2METHOXYNQ_0m
_database_code_depnum_ccdc_archive 'CCDC 1506931'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2017-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 N2 O2'
_chemical_formula_sum            'C16 H12 N2 O2'
_chemical_formula_weight         264.28

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.7063(4)
_cell_length_b                   8.4245(6)
_cell_length_c                   25.6881(19)
_cell_angle_alpha                90
_cell_angle_beta                 93.229(2)
_cell_angle_gamma                90
_cell_volume                     1232.94(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9182
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      28.35

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            RED
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48104
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.893
_diffrn_reflns_theta_max         28.388
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3076
_reflns_number_gt                2744
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0613P)²+0.5272P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    Riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3076
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.73937(14) 0.24107(10) 0.12857(3) 0.01789(19) Uani 1 1 d . . . . .
O2 O -0.05520(14) -0.09873(10) 0.11000(3) 0.0207(2) Uani 1 1 d . . . . .
N1 N 0.51288(15) 0.22622(11) 0.03477(3) 0.0144(2) Uani 1 1 d . . . . .
H1 H 0.6478 0.2754 0.0406 0.017 Uiso 1 1 calc R U . . .
N2 N 0.74226(16) 0.39418(11) -0.03246(4) 0.0150(2) Uani 1 1 d . . . . .
C1 C 0.56817(18) 0.15435(12) 0.12456(4) 0.0127(2) Uani 1 1 d . . . . .
C2 C 0.42324(18) 0.14570(12) 0.07377(4) 0.0129(2) Uani 1 1 d . . . . .
C3 C 0.21658(19) 0.06274(13) 0.07020(4) 0.0153(2) Uani 1 1 d . . . . .
H3 H 0.1254 0.0638 0.0381 0.018 Uiso 1 1 calc R U . . .
C4 C 0.13259(18) -0.02573(13) 0.11316(4) 0.0143(2) Uani 1 1 d . . . . .
C5 C 0.21281(19) -0.12357(13) 0.20439(4) 0.0161(2) Uani 1 1 d . . . . .
H5 H 0.0691 -0.1807 0.2013 0.019 Uiso 1 1 calc R U . . .
C6 C 0.3545(2) -0.13342(14) 0.25007(4) 0.0190(2) Uani 1 1 d . . . . .
H6 H 0.3083 -0.1984 0.2779 0.023 Uiso 1 1 calc R U . . .
C7 C 0.5642(2) -0.04838(14) 0.25515(4) 0.0199(2) Uani 1 1 d . . . . .
H7 H 0.6607 -0.0559 0.2864 0.024 Uiso 1 1 calc R U . . .
C8 C 0.63211(19) 0.04719(13) 0.21464(4) 0.0170(2) Uani 1 1 d . . . . .
H8 H 0.7736 0.1065 0.2183 0.020 Uiso 1 1 calc R U . . .
C9 C 0.49159(18) 0.05582(12) 0.16838(4) 0.0127(2) Uani 1 1 d . . . . .
C10 C 0.28143(18) -0.02990(12) 0.16314(4) 0.0131(2) Uani 1 1 d . . . . .
C11 C 0.39734(18) 0.23590(13) -0.01667(4) 0.0141(2) Uani 1 1 d . . . . .
H11A H 0.2411 0.2856 -0.0143 0.017 Uiso 1 1 calc R U . . .
H11B H 0.3741 0.1276 -0.0310 0.017 Uiso 1 1 calc R U . . .
C12 C 0.54166(18) 0.33253(12) -0.05276(4) 0.0126(2) Uani 1 1 d . . . . .
C13 C 0.46344(18) 0.35362(13) -0.10478(4) 0.0146(2) Uani 1 1 d . . . . .
H13 H 0.3194 0.3085 -0.1179 0.018 Uiso 1 1 calc R U . . .
C14 C 0.60123(19) 0.44205(13) -0.13682(4) 0.0153(2) Uani 1 1 d . . . . .
H14 H 0.5533 0.4579 -0.1725 0.018 Uiso 1 1 calc R U . . .
C15 C 0.80974(19) 0.50711(13) -0.11625(4) 0.0154(2) Uani 1 1 d . . . . .
H15 H 0.9069 0.5685 -0.1373 0.018 Uiso 1 1 calc R U . . .
C16 C 0.87238(19) 0.48013(13) -0.06416(4) 0.0161(2) Uani 1 1 d . . . . .
H16 H 1.0151 0.5248 -0.0501 0.019 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 C1 1.2196(13) . ?
O2 C4 1.2342(13) . ?
N1 C2 1.3354(13) . ?
N1 C11 1.4455(13) . ?
N1 H1 0.8800 . ?
N2 C12 1.3359(13) . ?
N2 C16 1.3442(14) . ?
C1 C9 1.4841(14) . ?
C1 C2 1.5066(14) . ?
C2 C3 1.3694(14) . ?
C3 C4 1.4363(15) . ?
C3 H3 0.9500 . ?
C4 C10 1.4994(15) . ?
C5 C6 1.3894(16) . ?
C5 C10 1.3948(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.3943(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.3882(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.3975(15) . ?
C8 H8 0.9500 . ?
C9 C10 1.3999(14) . ?
C11 C12 1.5120(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.3960(14) . ?
C13 C14 1.3870(15) . ?
C13 H13 0.9500 . ?
C14 C15 1.3873(15) . ?
C14 H14 0.9500 . ?
C15 C16 1.3842(15) . ?
C15 H15 0.9500 . ?
C16 H16 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
C2 N1 C11 122.70(9) . . ?
C2 N1 H1 118.6 . . ?
C11 N1 H1 118.6 . . ?
C12 N2 C16 117.60(9) . . ?
O1 C1 C9 122.66(10) . . ?
O1 C1 C2 120.01(9) . . ?
C9 C1 C2 117.32(9) . . ?
N1 C2 C3 125.01(10) . . ?
N1 C2 C1 114.23(9) . . ?
C3 C2 C1 120.76(9) . . ?
C2 C3 C4 122.46(10) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
O2 C4 C3 122.29(10) . . ?
O2 C4 C10 119.50(10) . . ?
C3 C4 C10 118.21(9) . . ?
C6 C5 C10 120.03(10) . . ?
C6 C5 H5 120.0 . . ?
C10 C5 H5 120.0 . . ?
C5 C6 C7 120.26(10) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.15(10) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 119.77(10) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C10 120.15(10) . . ?
C8 C9 C1 119.65(9) . . ?
C10 C9 C1 120.19(9) . . ?
C5 C10 C9 119.63(10) . . ?
C5 C10 C4 119.61(9) . . ?
C9 C10 C4 120.73(9) . . ?
N1 C11 C12 110.78(8) . . ?
N1 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
N2 C12 C13 123.01(9) . . ?
N2 C12 C11 117.02(9) . . ?
C13 C12 C11 119.97(9) . . ?
C14 C13 C12 118.36(9) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C14 C15 119.26(10) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 118.20(10) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
N2 C16 C15 123.55(10) . . ?
N2 C16 H16 118.2 . . ?
C15 C16 H16 118.2 . . ?

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
C11 N1 C2 C3 0.57(17) . . . . ?
C11 N1 C2 C1 -178.42(9) . . . . ?
O1 C1 C2 N1 6.24(14) . . . . ?
C9 C1 C2 N1 -174.47(9) . . . . ?
O1 C1 C2 C3 -172.80(10) . . . . ?
C9 C1 C2 C3 6.50(14) . . . . ?
N1 C2 C3 C4 178.05(10) . . . . ?
C1 C2 C3 C4 -3.02(16) . . . . ?
C2 C3 C4 O2 179.07(10) . . . . ?
C2 C3 C4 C10 -1.61(16) . . . . ?
C10 C5 C6 C7 0.79(17) . . . . ?
C5 C6 C7 C8 0.25(18) . . . . ?
C6 C7 C8 C9 -1.08(17) . . . . ?
C7 C8 C9 C10 0.87(16) . . . . ?
C7 C8 C9 C1 -178.20(10) . . . . ?
O1 C1 C9 C8 -7.03(16) . . . . ?
C2 C1 C9 C8 173.70(9) . . . . ?
O1 C1 C9 C10 173.91(10) . . . . ?
C2 C1 C9 C10 -5.37(14) . . . . ?
C6 C5 C10 C9 -1.00(16) . . . . ?
C6 C5 C10 C4 177.30(10) . . . . ?
C8 C9 C10 C5 0.17(15) . . . . ?
C1 C9 C10 C5 179.23(9) . . . . ?
C8 C9 C10 C4 -178.11(9) . . . . ?
C1 C9 C10 C4 0.95(15) . . . . ?
O2 C4 C10 C5 3.75(15) . . . . ?
C3 C4 C10 C5 -175.59(10) . . . . ?
O2 C4 C10 C9 -177.97(10) . . . . ?
C3 C4 C10 C9 2.69(15) . . . . ?
C2 N1 C11 C12 -179.10(9) . . . . ?
C16 N2 C12 C13 0.01(16) . . . . ?
C16 N2 C12 C11 179.89(9) . . . . ?
N1 C11 C12 N2 -1.24(13) . . . . ?
N1 C11 C12 C13 178.64(9) . . . . ?
N2 C12 C13 C14 0.32(16) . . . . ?
C11 C12 C13 C14 -179.56(10) . . . . ?
C12 C13 C14 C15 -0.45(16) . . . . ?
C13 C14 C15 C16 0.27(16) . . . . ?
C12 N2 C16 C15 -0.22(16) . . . . ?
C14 C15 C16 N2 0.07(17) . . . . ?

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
C16 H16 N2 0.95 2.56 3.3915(14) 146.5 3_765
C15 H15 O1 0.95 2.58 3.3634(13) 140.2 3_765
C13 H13 O2 0.95 2.34 3.1655(13) 145.1 3
C11 H11B O2 0.99 2.66 3.2198(13) 116.1 3
C11 H11B O2 0.99 2.66 3.2198(13) 116.1 3
C13 H13 O2 0.95 2.34 3.1655(13) 145.1 3
C15 H15 O1 0.95 2.58 3.3634(13) 140.2 3_765
C16 H16 N2 0.95 2.56 3.3915(14) 146.5 3_765

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.061

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_mo_Me_THYOPHINE_0m
_database_code_depnum_ccdc_archive 'CCDC 1506932'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2017-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 N O2 S'
_chemical_formula_sum            'C16 H13 N O2 S'
_chemical_formula_weight         283.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   5.4069(5)
_cell_length_b                   8.0971(7)
_cell_length_c                   29.735(3)
_cell_angle_alpha                92.338(4)
_cell_angle_beta                 91.024(4)
_cell_angle_gamma                98.992(4)
_cell_volume                     1284.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9581
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      28.26

_exptl_crystal_description       PLATE
_exptl_crystal_colour            RED
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.252
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24810
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.841
_diffrn_reflns_theta_max         28.611
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             6062
_reflns_number_gt                4647
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+11.7799P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    RIDING
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6062
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1233
_refine_ls_R_factor_gt           0.0926
_refine_ls_wR_factor_ref         0.2187
_refine_ls_wR_factor_gt          0.2044
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.155
_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
S1A S 0.5856(3) 0.30649(17) 0.31280(5) 0.0193(3) Uani 1 1 d . . . . .
S1 S 0.8601(2) 0.13123(17) 0.81186(4) 0.0192(3) Uani 1 1 d . . . . .
O2A O 1.5717(7) 0.4130(4) 0.56556(12) 0.0171(8) Uani 1 1 d . . . . .
O1A O 0.6728(6) 0.0224(4) 0.54872(12) 0.0151(7) Uani 1 1 d . . . . .
N1 N 0.6517(7) 0.2964(5) 0.97761(14) 0.0122(8) Uani 1 1 d . . . . .
H1 H 0.7952 0.3645 0.9770 0.015 Uiso 1 1 calc R U . . .
O1 O 0.8438(6) 0.4936(4) 1.04790(12) 0.0144(7) Uani 1 1 d . . . . .
O2 O -0.0489(6) 0.1102(4) 1.06626(12) 0.0168(7) Uani 1 1 d . . . . .
C11A C 0.9175(9) 0.2856(6) 0.43786(16) 0.0120(9) Uani 1 1 d . . . . .
H11A H 1.0704 0.2489 0.4258 0.014 Uiso 1 1 calc R U . . .
H11B H 0.9564 0.4070 0.4458 0.014 Uiso 1 1 calc R U . . .
N1A N 0.8420(7) 0.1942(5) 0.47806(14) 0.0125(8) Uani 1 1 d . . . . .
H1A H 0.6985 0.1257 0.4777 0.015 Uiso 1 1 calc R U . . .
C13 C 0.6741(9) 0.1165(6) 0.85885(16) 0.0129(9) Uani 1 1 d . . . . .
C16A C 0.7988(10) 0.4270(7) 0.28037(18) 0.0189(11) Uani 1 1 d . . . . .
H16A H 0.7710 0.4489 0.2497 0.023 Uiso 1 1 calc R U . . .
C13A C 0.7868(9) 0.3377(6) 0.35949(17) 0.0134(9) Uani 1 1 d . . . . .
C12A C 0.7071(9) 0.2537(6) 0.40207(17) 0.0130(9) Uani 1 1 d . . . . .
H12A H 0.6608 0.1317 0.3956 0.016 Uiso 1 1 calc R U . . .
H12B H 0.5577 0.2968 0.4136 0.016 Uiso 1 1 calc R U . . .
C2A C 0.9878(9) 0.2127(6) 0.51555(16) 0.0117(9) Uani 1 1 d . . . . .
C3A C 1.2191(9) 0.3109(6) 0.52026(16) 0.0135(9) Uani 1 1 d . . . . .
H3A H 1.2854 0.3722 0.4954 0.016 Uiso 1 1 calc R U . . .
C4A C 1.3623(9) 0.3236(6) 0.56133(17) 0.0125(9) Uani 1 1 d . . . . .
C10A C 1.2579(9) 0.2283(6) 0.60049(16) 0.0121(9) Uani 1 1 d . . . . .
C5A C 1.3933(10) 0.2386(6) 0.64101(17) 0.0150(10) Uani 1 1 d . . . . .
H5A H 1.5526 0.3074 0.6438 0.018 Uiso 1 1 calc R U . . .
C6A C 1.2974(10) 0.1490(7) 0.67744(17) 0.0173(10) Uani 1 1 d . . . . .
H6A H 1.3912 0.1565 0.7050 0.021 Uiso 1 1 calc R U . . .
C14A C 1.0008(10) 0.4351(6) 0.34962(18) 0.0165(10) Uani 1 1 d . . . . .
H14A H 1.1346 0.4675 0.3709 0.020 Uiso 1 1 calc R U . . .
C15A C 1.0091(11) 0.4856(7) 0.30432(18) 0.0223(11) Uani 1 1 d . . . . .
H15A H 1.1492 0.5538 0.2923 0.027 Uiso 1 1 calc R U . . .
C9A C 1.0207(9) 0.1285(6) 0.59699(16) 0.0118(9) Uani 1 1 d . . . . .
C1A C 0.8743(9) 0.1130(6) 0.55399(16) 0.0112(9) Uani 1 1 d . . . . .
C8A C 0.9261(9) 0.0380(6) 0.63387(17) 0.0137(10) Uani 1 1 d . . . . .
H8A H 0.7665 -0.0305 0.6315 0.016 Uiso 1 1 calc R U . . .
C7A C 1.0642(10) 0.0485(6) 0.67350(18) 0.0181(10) Uani 1 1 d . . . . .
H7A H 0.9997 -0.0135 0.6983 0.022 Uiso 1 1 calc R U . . .
C16 C 0.6365(10) 0.0010(7) 0.77941(18) 0.0193(11) Uani 1 1 d . . . . .
H16 H 0.6552 -0.0304 0.7487 0.023 Uiso 1 1 calc R U . . .
C12 C 0.7640(9) 0.2123(6) 0.90182(16) 0.0136(9) Uani 1 1 d . . . . .
H12C H 0.8105 0.3323 0.8957 0.016 Uiso 1 1 calc R U . . .
H12D H 0.9156 0.1717 0.9133 0.016 Uiso 1 1 calc R U . . .
C11 C 0.5644(9) 0.1931(6) 0.93766(16) 0.0124(9) Uani 1 1 d . . . . .
H11C H 0.4086 0.2269 0.9257 0.015 Uiso 1 1 calc R U . . .
H11D H 0.5263 0.0744 0.9456 0.015 Uiso 1 1 calc R U . . .
C2 C 0.5197(9) 0.2909(6) 1.01550(16) 0.0119(9) Uani 1 1 d . . . . .
C1 C 0.6395(9) 0.4044(6) 1.05344(16) 0.0116(9) Uani 1 1 d . . . . .
C9 C 0.5105(9) 0.4067(6) 1.09665(16) 0.0110(9) Uani 1 1 d . . . . .
C10 C 0.2764(9) 0.3087(6) 1.10071(16) 0.0124(9) Uani 1 1 d . . . . .
C5 C 0.1531(9) 0.3131(6) 1.14130(17) 0.0159(10) Uani 1 1 d . . . . .
H5 H -0.0041 0.2443 1.1446 0.019 Uiso 1 1 calc R U . . .
C6 C 0.2598(10) 0.4184(7) 1.17722(17) 0.0179(10) Uani 1 1 d . . . . .
H6 H 0.1738 0.4220 1.2047 0.021 Uiso 1 1 calc R U . . .
C14 C 0.4520(9) 0.0146(6) 0.84903(17) 0.0162(10) Uani 1 1 d . . . . .
H14 H 0.3240 -0.0105 0.8703 0.019 Uiso 1 1 calc R U . . .
C15 C 0.4323(10) -0.0502(7) 0.80345(18) 0.0194(11) Uani 1 1 d . . . . .
H15 H 0.2891 -0.1224 0.7913 0.023 Uiso 1 1 calc R U . . .
C8 C 0.6181(9) 0.5112(6) 1.13270(17) 0.0137(10) Uani 1 1 d . . . . .
H8 H 0.7776 0.5775 1.1297 0.016 Uiso 1 1 calc R U . . .
C7 C 0.4927(10) 0.5184(6) 1.17281(18) 0.0185(11) Uani 1 1 d . . . . .
H7 H 0.5646 0.5908 1.1971 0.022 Uiso 1 1 calc R U . . .
C4 C 0.1575(9) 0.1965(6) 1.06169(16) 0.0115(9) Uani 1 1 d . . . . .
C3 C 0.2899(9) 0.1966(6) 1.02034(16) 0.0129(9) Uani 1 1 d . . . . .
H3 H 0.2151 0.1286 0.9954 0.015 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
S1A C16A 1.725(6) . ?
S1A C13A 1.734(5) . ?
S1 C16 1.727(6) . ?
S1 C13 1.733(5) . ?
O2A C4A 1.246(6) . ?
O1A C1A 1.219(6) . ?
N1 C2 1.343(6) . ?
N1 C11 1.452(6) . ?
N1 H1 0.8800 . ?
O1 C1 1.239(6) . ?
O2 C4 1.234(6) . ?
C11A N1A 1.463(6) . ?
C11A C12A 1.528(6) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
N1A C2A 1.343(6) . ?
N1A H1A 0.8800 . ?
C13 C14 1.366(7) . ?
C13 C12 1.500(7) . ?
C16A C15A 1.342(8) . ?
C16A H16A 0.9500 . ?
C13A C14A 1.339(7) . ?
C13A C12A 1.500(7) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C2A C3A 1.375(7) . ?
C2A C1A 1.510(7) . ?
C3A C4A 1.426(7) . ?
C3A H3A 0.9500 . ?
C4A C10A 1.493(7) . ?
C10A C5A 1.391(7) . ?
C10A C9A 1.405(7) . ?
C5A C6A 1.391(7) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.390(8) . ?
C6A H6A 0.9500 . ?
C14A C15A 1.423(7) . ?
C14A H14A 0.9500 . ?
C15A H15A 0.9500 . ?
C9A C8A 1.403(7) . ?
C9A C1A 1.482(7) . ?
C8A C7A 1.376(7) . ?
C8A H8A 0.9500 . ?
C7A H7A 0.9500 . ?
C16 C15 1.346(8) . ?
C16 H16 0.9500 . ?
C12 C11 1.525(7) . ?
C12 H12C 0.9900 . ?
C12 H12D 0.9900 . ?
C11 H11C 0.9900 . ?
C11 H11D 0.9900 . ?
C2 C3 1.366(7) . ?
C2 C1 1.497(7) . ?
C1 C9 1.474(7) . ?
C9 C10 1.395(7) . ?
C9 C8 1.397(7) . ?
C10 C5 1.391(7) . ?
C10 C4 1.513(7) . ?
C5 C6 1.396(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.398(8) . ?
C6 H6 0.9500 . ?
C14 C15 1.429(7) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C8 C7 1.386(7) . ?
C8 H8 0.9500 . ?
C7 H7 0.9500 . ?
C4 C3 1.434(7) . ?
C3 H3 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
C16A S1A C13A 92.0(3) . . ?
C16 S1 C13 92.4(3) . . ?
C2 N1 C11 121.9(4) . . ?
C2 N1 H1 119.1 . . ?
C11 N1 H1 119.1 . . ?
N1A C11A C12A 110.1(4) . . ?
N1A C11A H11A 109.6 . . ?
C12A C11A H11A 109.6 . . ?
N1A C11A H11B 109.6 . . ?
C12A C11A H11B 109.6 . . ?
H11A C11A H11B 108.2 . . ?
C2A N1A C11A 121.2(4) . . ?
C2A N1A H1A 119.4 . . ?
C11A N1A H1A 119.4 . . ?
C14 C13 C12 129.6(5) . . ?
C14 C13 S1 110.2(4) . . ?
C12 C13 S1 120.2(4) . . ?
C15A C16A S1A 110.8(4) . . ?
C15A C16A H16A 124.6 . . ?
S1A C16A H16A 124.6 . . ?
C14A C13A C12A 130.6(5) . . ?
C14A C13A S1A 110.3(4) . . ?
C12A C13A S1A 119.0(4) . . ?
C13A C12A C11A 110.9(4) . . ?
C13A C12A H12A 109.5 . . ?
C11A C12A H12A 109.5 . . ?
C13A C12A H12B 109.5 . . ?
C11A C12A H12B 109.5 . . ?
H12A C12A H12B 108.0 . . ?
N1A C2A C3A 125.4(4) . . ?
N1A C2A C1A 113.5(4) . . ?
C3A C2A C1A 121.1(4) . . ?
C2A C3A C4A 121.9(4) . . ?
C2A C3A H3A 119.1 . . ?
C4A C3A H3A 119.1 . . ?
O2A C4A C3A 121.8(4) . . ?
O2A C4A C10A 119.0(4) . . ?
C3A C4A C10A 119.2(4) . . ?
C5A C10A C9A 119.2(4) . . ?
C5A C10A C4A 120.4(4) . . ?
C9A C10A C4A 120.4(4) . . ?
C10A C5A C6A 120.6(5) . . ?
C10A C5A H5A 119.7 . . ?
C6A C5A H5A 119.7 . . ?
C7A C6A C5A 119.9(5) . . ?
C7A C6A H6A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C13A C14A C15A 113.7(5) . . ?
C13A C14A H14A 123.1 . . ?
C15A C14A H14A 123.1 . . ?
C16A C15A C14A 113.1(5) . . ?
C16A C15A H15A 123.5 . . ?
C14A C15A H15A 123.5 . . ?
C8A C9A C10A 119.8(4) . . ?
C8A C9A C1A 119.9(4) . . ?
C10A C9A C1A 120.3(4) . . ?
O1A C1A C9A 122.7(4) . . ?
O1A C1A C2A 120.1(4) . . ?
C9A C1A C2A 117.1(4) . . ?
C7A C8A C9A 120.1(5) . . ?
C7A C8A H8A 120.0 . . ?
C9A C8A H8A 120.0 . . ?
C8A C7A C6A 120.4(5) . . ?
C8A C7A H7A 119.8 . . ?
C6A C7A H7A 119.8 . . ?
C15 C16 S1 111.0(4) . . ?
C15 C16 H16 124.5 . . ?
S1 C16 H16 124.5 . . ?
C13 C12 C11 111.8(4) . . ?
C13 C12 H12C 109.3 . . ?
C11 C12 H12C 109.3 . . ?
C13 C12 H12D 109.3 . . ?
C11 C12 H12D 109.3 . . ?
H12C C12 H12D 107.9 . . ?
N1 C11 C12 110.2(4) . . ?
N1 C11 H11C 109.6 . . ?
C12 C11 H11C 109.6 . . ?
N1 C11 H11D 109.6 . . ?
C12 C11 H11D 109.6 . . ?
H11C C11 H11D 108.1 . . ?
N1 C2 C3 125.0(4) . . ?
N1 C2 C1 114.6(4) . . ?
C3 C2 C1 120.4(4) . . ?
O1 C1 C9 121.6(4) . . ?
O1 C1 C2 119.5(4) . . ?
C9 C1 C2 118.8(4) . . ?
C10 C9 C8 120.3(4) . . ?
C10 C9 C1 119.5(4) . . ?
C8 C9 C1 120.1(4) . . ?
C5 C10 C9 119.4(5) . . ?
C5 C10 C4 119.9(4) . . ?
C9 C10 C4 120.7(4) . . ?
C10 C5 C6 120.2(5) . . ?
C10 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 120.2(5) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C13 C14 C15 113.0(5) . . ?
C13 C14 H14 123.5 . . ?
C15 C14 H14 123.5 . . ?
C16 C15 C14 113.4(5) . . ?
C16 C15 H15 123.3 . . ?
C14 C15 H15 123.3 . . ?
C7 C8 C9 120.2(5) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C7 C6 119.6(5) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
O2 C4 C3 122.5(5) . . ?
O2 C4 C10 119.4(4) . . ?
C3 C4 C10 118.1(4) . . ?
C2 C3 C4 122.4(4) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?

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
C12A C11A N1A C2A -174.7(4) . . . . ?
C16 S1 C13 C14 0.3(4) . . . . ?
C16 S1 C13 C12 -178.3(4) . . . . ?
C13A S1A C16A C15A 0.2(4) . . . . ?
C16A S1A C13A C14A 0.2(4) . . . . ?
C16A S1A C13A C12A -178.0(4) . . . . ?
C14A C13A C12A C11A -2.3(7) . . . . ?
S1A C13A C12A C11A 175.6(3) . . . . ?
N1A C11A C12A C13A -176.4(4) . . . . ?
C11A N1A C2A C3A -2.2(7) . . . . ?
C11A N1A C2A C1A 177.9(4) . . . . ?
N1A C2A C3A C4A -179.9(4) . . . . ?
C1A C2A C3A C4A 0.0(7) . . . . ?
C2A C3A C4A O2A -179.8(5) . . . . ?
C2A C3A C4A C10A -0.4(7) . . . . ?
O2A C4A C10A C5A -0.4(7) . . . . ?
C3A C4A C10A C5A -179.9(4) . . . . ?
O2A C4A C10A C9A 179.0(4) . . . . ?
C3A C4A C10A C9A -0.4(7) . . . . ?
C9A C10A C5A C6A 1.1(7) . . . . ?
C4A C10A C5A C6A -179.5(4) . . . . ?
C10A C5A C6A C7A -0.1(7) . . . . ?
C12A C13A C14A C15A 177.4(5) . . . . ?
S1A C13A C14A C15A -0.6(6) . . . . ?
S1A C16A C15A C14A -0.5(6) . . . . ?
C13A C14A C15A C16A 0.7(7) . . . . ?
C5A C10A C9A C8A -1.3(7) . . . . ?
C4A C10A C9A C8A 179.2(4) . . . . ?
C5A C10A C9A C1A -179.0(4) . . . . ?
C4A C10A C9A C1A 1.6(7) . . . . ?
C8A C9A C1A O1A -0.9(7) . . . . ?
C10A C9A C1A O1A 176.7(4) . . . . ?
C8A C9A C1A C2A -179.6(4) . . . . ?
C10A C9A C1A C2A -2.0(6) . . . . ?
N1A C2A C1A O1A 2.3(6) . . . . ?
C3A C2A C1A O1A -177.6(4) . . . . ?
N1A C2A C1A C9A -178.9(4) . . . . ?
C3A C2A C1A C9A 1.2(6) . . . . ?
C10A C9A C8A C7A 0.6(7) . . . . ?
C1A C9A C8A C7A 178.3(4) . . . . ?
C9A C8A C7A C6A 0.3(7) . . . . ?
C5A C6A C7A C8A -0.6(8) . . . . ?
C13 S1 C16 C15 -0.1(4) . . . . ?
C14 C13 C12 C11 -2.8(7) . . . . ?
S1 C13 C12 C11 175.4(3) . . . . ?
C2 N1 C11 C12 -174.1(4) . . . . ?
C13 C12 C11 N1 -176.2(4) . . . . ?
C11 N1 C2 C3 -3.0(7) . . . . ?
C11 N1 C2 C1 179.3(4) . . . . ?
N1 C2 C1 O1 0.4(6) . . . . ?
C3 C2 C1 O1 -177.3(4) . . . . ?
N1 C2 C1 C9 -179.5(4) . . . . ?
C3 C2 C1 C9 2.7(6) . . . . ?
O1 C1 C9 C10 177.6(4) . . . . ?
C2 C1 C9 C10 -2.5(6) . . . . ?
O1 C1 C9 C8 -0.1(7) . . . . ?
C2 C1 C9 C8 179.9(4) . . . . ?
C8 C9 C10 C5 -1.4(7) . . . . ?
C1 C9 C10 C5 -179.0(4) . . . . ?
C8 C9 C10 C4 179.4(4) . . . . ?
C1 C9 C10 C4 1.8(6) . . . . ?
C9 C10 C5 C6 1.8(7) . . . . ?
C4 C10 C5 C6 -179.0(4) . . . . ?
C10 C5 C6 C7 -0.9(7) . . . . ?
C12 C13 C14 C15 177.9(5) . . . . ?
S1 C13 C14 C15 -0.4(6) . . . . ?
S1 C16 C15 C14 -0.2(6) . . . . ?
C13 C14 C15 C16 0.4(7) . . . . ?
C10 C9 C8 C7 0.0(7) . . . . ?
C1 C9 C8 C7 177.5(4) . . . . ?
C9 C8 C7 C6 1.0(7) . . . . ?
C5 C6 C7 C8 -0.6(7) . . . . ?
C5 C10 C4 O2 0.3(7) . . . . ?
C9 C10 C4 O2 179.5(4) . . . . ?
C5 C10 C4 C3 179.6(4) . . . . ?
C9 C10 C4 C3 -1.2(6) . . . . ?
N1 C2 C3 C4 -179.7(4) . . . . ?
C1 C2 C3 C4 -2.2(7) . . . . ?
O2 C4 C3 C2 -179.3(4) . . . . ?
C10 C4 C3 C2 1.5(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
C3 H3 O2 0.95 2.65 3.584(6) 168.1 2_557
C14 H14 O2 0.95 2.50 3.440(6) 168.1 2_557
C12 H12D O2 0.99 2.59 3.392(6) 138.0 2_657
C16 H16 S1A 0.95 2.95 3.681(5) 134.7 2_656
C14A H14A O2A 0.95 2.51 3.445(6) 168.5 2_866
C3A H3A O2A 0.95 2.61 3.545(6) 168.9 2_866
C12A H12B O2A 0.99 2.61 3.405(6) 137.5 2_766
N1A H1A O1A 0.88 2.28 3.120(5) 159.8 2_656
N1 H1 O1 0.88 2.26 3.105(5) 161.4 2_767
C3 H3 O2 0.95 2.65 3.584(6) 168.1 2_557
C14 H14 O2 0.95 2.50 3.440(6) 168.1 2_557
C12 H12D O2 0.99 2.59 3.392(6) 138.0 2_657
N1 H1 O1 0.88 2.26 3.105(5) 161.4 2_767
C3 H3 O2 0.95 2.65 3.584(6) 168.1 2_557
C14 H14 O2 0.95 2.50 3.440(6) 168.1 2_557
C12 H12D O2 0.99 2.59 3.392(6) 138.0 2_657
C16 H16 S1A 0.95 2.95 3.681(5) 134.7 2_656
C14A H14A O2A 0.95 2.51 3.445(6) 168.5 2_866
C3A H3A O2A 0.95 2.61 3.545(6) 168.9 2_866
C12A H12B O2A 0.99 2.61 3.405(6) 137.5 2_766
N1A H1A O1A 0.88 2.28 3.120(5) 159.8 2_656
N1 H1 O1 0.88 2.26 3.105(5) 161.4 2_767
C3 H3 O2 0.95 2.65 3.584(6) 168.1 2_557
C14 H14 O2 0.95 2.50 3.440(6) 168.1 2_557
C12 H12D O2 0.99 2.59 3.392(6) 138.0 2_657
N1 H1 O1 0.88 2.26 3.105(5) 161.4 2_767
N1 H1 O1 0.88 2.26 3.105(5) 161.4 2_767
N1A H1A O1A 0.88 2.28 3.120(5) 159.8 2_656
C12A H12B O2A 0.99 2.61 3.405(6) 137.5 2_766
C3A H3A O2A 0.95 2.61 3.545(6) 168.9 2_866
C14A H14A O2A 0.95 2.51 3.445(6) 168.5 2_866
C16 H16 S1A 0.95 2.95 3.681(5) 134.7 2_656
C12 H12D O2 0.99 2.59 3.392(6) 138.0 2_657
C14 H14 O2 0.95 2.50 3.440(6) 168.1 2_557
C3 H3 O2 0.95 2.65 3.584(6) 168.1 2_557
N1 H1 O1 0.88 2.26 3.105(5) 161.4 2_767
N1A H1A O1A 0.88 2.28 3.120(5) 159.8 2_656
C12A H12B O2A 0.99 2.61 3.405(6) 137.5 2_766
C3A H3A O2A 0.95 2.61 3.545(6) 168.9 2_866
C14A H14A O2A 0.95 2.51 3.445(6) 168.5 2_866
C16 H16 S1A 0.95 2.95 3.681(5) 134.7 2_656
C12 H12D O2 0.99 2.59 3.392(6) 138.0 2_657
C14 H14 O2 0.95 2.50 3.440(6) 168.1 2_557
C3 H3 O2 0.95 2.65 3.584(6) 168.1 2_557
N1 H1 O1 0.88 2.26 3.105(5) 161.4 2_767
N1A H1A O1A 0.88 2.28 3.120(5) 159.8 2_656
C12A H12B O2A 0.99 2.61 3.405(6) 137.5 2_766
C3A H3A O2A 0.95 2.61 3.545(6) 168.9 2_866
C14A H14A O2A 0.95 2.51 3.445(6) 168.5 2_866
C16 H16 S1A 0.95 2.95 3.681(5) 134.7 2_656
C12 H12D O2 0.99 2.59 3.392(6) 138.0 2_657
C14 H14 O2 0.95 2.50 3.440(6) 168.1 2_557
C3 H3 O2 0.95 2.65 3.584(6) 168.1 2_557

_refine_diff_density_max         0.756
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.130

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_mo_ETHYL_PICO_0m
_database_code_depnum_ccdc_archive 'CCDC 1575689'
_audit_update_record             
;
2017-09-20 deposited with the CCDC.
2017-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 N2 O2'
_chemical_formula_sum            'C17 H14 N2 O2'
_chemical_formula_weight         278.30

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.4000(4)
_cell_length_b                   30.026(2)
_cell_length_c                   8.0578(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.278(2)
_cell_angle_gamma                90
_cell_volume                     1289.39(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9217
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.369
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51719
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.713
_diffrn_reflns_theta_max         28.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3213
_reflns_number_gt                2652
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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    RIDING
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3213
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0634
_refine_ls_wR_factor_ref         0.1659
_refine_ls_wR_factor_gt          0.1569
_refine_ls_goodness_of_fit_ref   1.226
_refine_ls_restrained_S_all      1.226
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1638(2) -0.04693(4) 0.51681(14) 0.0107(3) Uani 1 1 d . . . . .
O2 O 1.0656(2) -0.06379(4) 0.90550(15) 0.0130(3) Uani 1 1 d . . . . .
N1 N 0.3474(2) 0.02325(4) 0.69917(17) 0.0090(3) Uani 1 1 d . . . . .
H1 H 0.2038 0.0236 0.6298 0.011 Uiso 1 1 calc R U . . .
N2 N 0.0961(3) 0.17284(5) 0.81684(18) 0.0123(3) Uani 1 1 d . . . . .
C1 C 0.3676(3) -0.05191(5) 0.60634(19) 0.0072(3) Uani 1 1 d . . . . .
C2 C 0.4858(3) -0.01404(5) 0.71219(19) 0.0076(3) Uani 1 1 d . . . . .
C3 C 0.7177(3) -0.01848(5) 0.8096(2) 0.0084(3) Uani 1 1 d . . . . .
H3 H 0.7882 0.0063 0.8740 0.010 Uiso 1 1 calc R U . . .
C4 C 0.8569(3) -0.05939(5) 0.8170(2) 0.0081(3) Uani 1 1 d . . . . .
C5 C 0.8755(3) -0.13796(5) 0.7164(2) 0.0109(4) Uani 1 1 d . . . . .
H5 H 1.0358 -0.1405 0.7844 0.013 Uiso 1 1 calc R U . . .
C6 C 0.7747(3) -0.17391(6) 0.6202(2) 0.0127(4) Uani 1 1 d . . . . .
H6 H 0.8660 -0.2010 0.6226 0.015 Uiso 1 1 calc R U . . .
C7 C 0.5394(3) -0.17031(5) 0.5200(2) 0.0118(4) Uani 1 1 d . . . . .
H7 H 0.4715 -0.1949 0.4534 0.014 Uiso 1 1 calc R U . . .
C8 C 0.4049(3) -0.13098(5) 0.5175(2) 0.0092(3) Uani 1 1 d . . . . .
H8 H 0.2439 -0.1287 0.4502 0.011 Uiso 1 1 calc R U . . .
C9 C 0.5058(3) -0.09467(5) 0.61379(19) 0.0073(3) Uani 1 1 d . . . . .
C10 C 0.7432(3) -0.09820(5) 0.71379(19) 0.0077(3) Uani 1 1 d . . . . .
C11 C 0.4261(3) 0.06329(5) 0.7958(2) 0.0082(3) Uani 1 1 d . . . . .
H11A H 0.5803 0.0754 0.7609 0.010 Uiso 1 1 calc R U . . .
H11B H 0.4641 0.0559 0.9169 0.010 Uiso 1 1 calc R U . . .
C12 C 0.2194(3) 0.09786(5) 0.76665(19) 0.0085(4) Uani 1 1 d . . . . .
H12A H 0.1745 0.1028 0.6440 0.010 Uiso 1 1 calc R U . . .
H12B H 0.0695 0.0855 0.8066 0.010 Uiso 1 1 calc R U . . .
C13 C 0.2797(3) 0.14234(5) 0.85066(19) 0.0081(3) Uani 1 1 d . . . . .
C14 C 0.5061(3) 0.15143(5) 0.9548(2) 0.0113(4) Uani 1 1 d . . . . .
H14 H 0.6327 0.1293 0.9762 0.014 Uiso 1 1 calc R U . . .
C15 C 0.5437(3) 0.19335(6) 1.0268(2) 0.0140(4) Uani 1 1 d . . . . .
H15 H 0.6964 0.2003 1.0984 0.017 Uiso 1 1 calc R U . . .
C16 C 0.3560(3) 0.22490(6) 0.9931(2) 0.0132(4) Uani 1 1 d . . . . .
H16 H 0.3765 0.2539 1.0406 0.016 Uiso 1 1 calc R U . . .
C17 C 0.1369(3) 0.21309(6) 0.8879(2) 0.0132(4) Uani 1 1 d . . . . .
H17 H 0.0081 0.2348 0.8648 0.016 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 C1 1.2239(18) . ?
O2 C4 1.2398(19) . ?
N1 C2 1.341(2) . ?
N1 C11 1.4577(19) . ?
N1 H1 0.8800 . ?
N2 C17 1.340(2) . ?
N2 C13 1.345(2) . ?
C1 C9 1.482(2) . ?
C1 C2 1.501(2) . ?
C2 C3 1.373(2) . ?
C3 C4 1.436(2) . ?
C3 H3 0.9500 . ?
C4 C10 1.504(2) . ?
C5 C6 1.388(2) . ?
C5 C10 1.389(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.385(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.397(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.404(2) . ?
C11 C12 1.515(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.509(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.394(2) . ?
C14 C15 1.387(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(2) . ?
C16 H16 0.9500 . ?
C17 H17 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
C2 N1 C11 122.41(13) . . ?
C2 N1 H1 118.8 . . ?
C11 N1 H1 118.8 . . ?
C17 N2 C13 117.53(14) . . ?
O1 C1 C9 121.94(14) . . ?
O1 C1 C2 120.13(14) . . ?
C9 C1 C2 117.93(13) . . ?
N1 C2 C3 124.84(15) . . ?
N1 C2 C1 114.05(14) . . ?
C3 C2 C1 121.10(14) . . ?
C2 C3 C4 122.00(15) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
O2 C4 C3 122.43(15) . . ?
O2 C4 C10 119.18(14) . . ?
C3 C4 C10 118.39(13) . . ?
C6 C5 C10 120.35(15) . . ?
C6 C5 H5 119.8 . . ?
C10 C5 H5 119.8 . . ?
C5 C6 C7 120.08(15) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.08(15) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.05(15) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 119.88(14) . . ?
C8 C9 C1 120.34(14) . . ?
C10 C9 C1 119.74(14) . . ?
C5 C10 C9 119.56(14) . . ?
C5 C10 C4 119.62(14) . . ?
C9 C10 C4 120.82(14) . . ?
N1 C11 C12 109.77(12) . . ?
N1 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
N1 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C13 C12 C11 115.89(13) . . ?
C13 C12 H12A 108.3 . . ?
C11 C12 H12A 108.3 . . ?
C13 C12 H12B 108.3 . . ?
C11 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
N2 C13 C14 122.34(15) . . ?
N2 C13 C12 114.39(14) . . ?
C14 C13 C12 123.27(14) . . ?
C15 C14 C13 119.00(15) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C16 C15 C14 119.09(16) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 118.15(16) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
N2 C17 C16 123.89(15) . . ?
N2 C17 H17 118.1 . . ?
C16 C17 H17 118.1 . . ?

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
C11 N1 C2 C3 -3.0(2) . . . . ?
C11 N1 C2 C1 178.12(13) . . . . ?
O1 C1 C2 N1 0.9(2) . . . . ?
C9 C1 C2 N1 -179.42(13) . . . . ?
O1 C1 C2 C3 -178.01(14) . . . . ?
C9 C1 C2 C3 1.7(2) . . . . ?
N1 C2 C3 C4 -179.60(14) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
C2 C3 C4 O2 -179.51(14) . . . . ?
C2 C3 C4 C10 0.2(2) . . . . ?
C10 C5 C6 C7 0.0(2) . . . . ?
C5 C6 C7 C8 -0.6(3) . . . . ?
C6 C7 C8 C9 0.7(2) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
C7 C8 C9 C1 177.48(14) . . . . ?
O1 C1 C9 C8 -0.1(2) . . . . ?
C2 C1 C9 C8 -179.79(14) . . . . ?
O1 C1 C9 C10 177.67(14) . . . . ?
C2 C1 C9 C10 -2.0(2) . . . . ?
C6 C5 C10 C9 0.4(2) . . . . ?
C6 C5 C10 C4 -179.18(14) . . . . ?
C8 C9 C10 C5 -0.2(2) . . . . ?
C1 C9 C10 C5 -178.04(14) . . . . ?
C8 C9 C10 C4 179.30(14) . . . . ?
C1 C9 C10 C4 1.5(2) . . . . ?
O2 C4 C10 C5 -1.3(2) . . . . ?
C3 C4 C10 C5 178.95(14) . . . . ?
O2 C4 C10 C9 179.16(14) . . . . ?
C3 C4 C10 C9 -0.6(2) . . . . ?
C2 N1 C11 C12 -174.37(14) . . . . ?
N1 C11 C12 C13 -176.48(13) . . . . ?
C17 N2 C13 C14 -0.2(2) . . . . ?
C17 N2 C13 C12 179.78(14) . . . . ?
C11 C12 C13 N2 177.46(13) . . . . ?
C11 C12 C13 C14 -2.6(2) . . . . ?
N2 C13 C14 C15 0.2(2) . . . . ?
C12 C13 C14 C15 -179.78(15) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C13 N2 C17 C16 0.1(2) . . . . ?
C15 C16 C17 N2 0.0(3) . . . . ?

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.070

_shelxl_version_number           2014-3

