# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_170116LT_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1893991'
loop_
_audit_author_name
_audit_author_address
'kishore pampana'
;National tsing hua university
Taiwan
;
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2019-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25

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           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

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

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

_cell_length_a                   11.241(3)
_cell_length_b                   5.7323(17)
_cell_length_c                   17.696(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.712(5)
_cell_angle_gamma                90
_cell_volume                     1129.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2857
_cell_measurement_theta_min      2.3229
_cell_measurement_theta_max      26.4418

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6076
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            7664
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.294
_diffrn_reflns_theta_max         26.576
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4061
_reflns_number_gt                3555
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.996

_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       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+0.0242P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.8(13)
_chemical_absolute_configuration RM
_refine_ls_number_reflns         4061
_refine_ls_number_parameters     310
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0945
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
C1 C 0.4055(3) 1.0194(5) 0.42256(17) 0.0189(6) Uani 1 1 d . . . . .
C2 C 0.5179(3) 1.1642(5) 0.41735(17) 0.0250(7) Uani 1 1 d . . . . .
H2A H 0.5078 1.3204 0.4395 0.030 Uiso 1 1 calc R U . . .
H2B H 0.5875 1.0881 0.4478 0.030 Uiso 1 1 calc R U . . .
C3 C 0.5433(2) 1.1919(5) 0.33583(17) 0.0212(6) Uani 1 1 d . . . . .
C4 C 0.5115(3) 1.3951(5) 0.29475(18) 0.0245(7) Uani 1 1 d . . . . .
H4 H 0.4752 1.5204 0.3183 0.029 Uiso 1 1 calc R U . . .
C5 C 0.5329(3) 1.4150(6) 0.21920(19) 0.0307(7) Uani 1 1 d . . . . .
H5 H 0.5100 1.5532 0.1914 0.037 Uiso 1 1 calc R U . . .
C6 C 0.5871(3) 1.2355(6) 0.18442(19) 0.0331(8) Uani 1 1 d . . . . .
H6 H 0.6026 1.2505 0.1332 0.040 Uiso 1 1 calc R U . . .
C7 C 0.6186(3) 1.0335(6) 0.2251(2) 0.0298(7) Uani 1 1 d . . . . .
H7 H 0.6555 0.9091 0.2015 0.036 Uiso 1 1 calc R U . . .
C8 C 0.5967(3) 1.0112(5) 0.29992(18) 0.0249(7) Uani 1 1 d . . . . .
H8 H 0.6184 0.8711 0.3270 0.030 Uiso 1 1 calc R U . . .
C9 C 0.3250(2) 0.7105(5) 0.49989(15) 0.0182(6) Uani 1 1 d . . . . .
C10 C 0.3678(2) 0.5175(5) 0.54478(16) 0.0193(6) Uani 1 1 d . . . . .
C11 C 0.2889(2) 0.3447(5) 0.56087(16) 0.0205(6) Uani 1 1 d . . . . .
H11 H 0.3182 0.2120 0.5897 0.025 Uiso 1 1 calc R U . . .
C12 C 0.1671(2) 0.3643(5) 0.53496(16) 0.0218(6) Uani 1 1 d . . . . .
H12 H 0.1135 0.2445 0.5457 0.026 Uiso 1 1 calc R U . . .
C13 C 0.1236(2) 0.5586(5) 0.49343(17) 0.0220(6) Uani 1 1 d . . . . .
H13 H 0.0400 0.5736 0.4770 0.026 Uiso 1 1 calc R U . . .
C14 C 0.2023(2) 0.7315(5) 0.47576(16) 0.0206(6) Uani 1 1 d . . . . .
H14 H 0.1722 0.8643 0.4472 0.025 Uiso 1 1 calc R U . . .
C15 C 0.6545(2) 0.0502(5) 0.66938(17) 0.0187(6) Uani 1 1 d . . . . .
C16 C 0.7519(3) -0.1298(5) 0.66121(17) 0.0240(7) Uani 1 1 d . . . . .
H16A H 0.8241 -0.0933 0.6978 0.029 Uiso 1 1 calc R U . . .
H16B H 0.7231 -0.2864 0.6739 0.029 Uiso 1 1 calc R U . . .
C17 C 0.7853(2) -0.1333(5) 0.58106(16) 0.0194(6) Uani 1 1 d . . . . .
C18 C 0.7542(3) -0.3213(5) 0.53258(18) 0.0214(6) Uani 1 1 d . . . . .
H18 H 0.7122 -0.4501 0.5500 0.026 Uiso 1 1 calc R U . . .
C19 C 0.7843(3) -0.3222(5) 0.45889(18) 0.0233(6) Uani 1 1 d . . . . .
H19 H 0.7629 -0.4515 0.4263 0.028 Uiso 1 1 calc R U . . .
C20 C 0.8451(3) -0.1359(5) 0.43286(17) 0.0240(7) Uani 1 1 d . . . . .
H20 H 0.8657 -0.1370 0.3825 0.029 Uiso 1 1 calc R U . . .
C21 C 0.8764(3) 0.0536(5) 0.48065(18) 0.0247(7) Uani 1 1 d . . . . .
H21 H 0.9181 0.1824 0.4629 0.030 Uiso 1 1 calc R U . . .
C22 C 0.8465(3) 0.0538(5) 0.55391(17) 0.0235(6) Uani 1 1 d . . . . .
H22 H 0.8680 0.1835 0.5863 0.028 Uiso 1 1 calc R U . . .
C23 C 0.5755(2) 0.3164(5) 0.75851(15) 0.0176(6) Uani 1 1 d . . . . .
C24 C 0.6188(2) 0.5186(5) 0.79791(16) 0.0191(6) Uani 1 1 d . . . . .
C25 C 0.5372(3) 0.6854(5) 0.81656(16) 0.0214(6) Uani 1 1 d . . . . .
H25 H 0.5655 0.8231 0.8430 0.026 Uiso 1 1 calc R U . . .
C26 C 0.4151(3) 0.6508(5) 0.79670(17) 0.0231(7) Uani 1 1 d . . . . .
H26 H 0.3602 0.7663 0.8089 0.028 Uiso 1 1 calc R U . . .
C27 C 0.3723(3) 0.4488(5) 0.75909(17) 0.0230(6) Uani 1 1 d . . . . .
H27 H 0.2884 0.4259 0.7458 0.028 Uiso 1 1 calc R U . . .
C28 C 0.4525(2) 0.2812(5) 0.74105(16) 0.0197(6) Uani 1 1 d . . . . .
H28 H 0.4233 0.1411 0.7166 0.024 Uiso 1 1 calc R U . . .
N1 N 0.4129(2) 0.8711(4) 0.48204(13) 0.0203(5) Uani 1 1 d . . . . .
H1 H 0.4804 0.8745 0.5136 0.024 Uiso 1 1 calc R U . . .
N2 N 0.6612(2) 0.1524(4) 0.73821(13) 0.0186(5) Uani 1 1 d . . . . .
H2 H 0.7220 0.1159 0.7728 0.022 Uiso 1 1 calc R U . . .
O1 O 0.31516(17) 1.0396(3) 0.37485(11) 0.0228(5) Uani 1 1 d . . . . .
O2 O 0.48769(17) 0.5125(4) 0.56902(13) 0.0233(5) Uani 1 1 d . . . . .
H2C H 0.5075 0.3785 0.5853 0.035 Uiso 1 1 calc R U . . .
O3 O 0.57521(17) 0.0929(4) 0.61583(11) 0.0222(5) Uani 1 1 d . . . . .
O4 O 0.73966(17) 0.5395(3) 0.81421(12) 0.0224(4) Uani 1 1 d . . . . .
H4A H 0.7568 0.6722 0.8326 0.034 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
C1 O1 1.236(4) . ?
C1 N1 1.347(4) . ?
C1 C2 1.524(4) . ?
C2 C3 1.516(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C8 1.393(4) . ?
C3 C4 1.394(4) . ?
C4 C5 1.394(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.384(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C14 1.394(4) . ?
C9 C10 1.408(4) . ?
C9 N1 1.417(3) . ?
C10 O2 1.358(3) . ?
C10 C11 1.385(4) . ?
C11 C12 1.389(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 O3 1.235(3) . ?
C15 N2 1.345(4) . ?
C15 C16 1.525(4) . ?
C16 C17 1.515(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.393(4) . ?
C17 C22 1.394(4) . ?
C18 C19 1.390(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.380(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.392(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.382(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C28 1.391(4) . ?
C23 C24 1.406(4) . ?
C23 N2 1.425(3) . ?
C24 O4 1.355(3) . ?
C24 C25 1.395(4) . ?
C25 C26 1.384(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.389(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.384(4) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?
O2 H2C 0.8400 . ?
O4 H4A 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 123.5(3) . . ?
O1 C1 C2 121.3(3) . . ?
N1 C1 C2 115.2(3) . . ?
C3 C2 C1 112.2(2) . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C8 C3 C4 118.7(3) . . ?
C8 C3 C2 120.3(3) . . ?
C4 C3 C2 121.0(3) . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.2(3) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C6 C7 C8 120.6(3) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C3 120.7(3) . . ?
C7 C8 H8 119.7 . . ?
C3 C8 H8 119.7 . . ?
C14 C9 C10 119.4(3) . . ?
C14 C9 N1 124.5(3) . . ?
C10 C9 N1 116.1(2) . . ?
O2 C10 C11 123.7(3) . . ?
O2 C10 C9 116.4(2) . . ?
C11 C10 C9 119.9(3) . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.1(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 120.1(3) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
O3 C15 N2 123.7(2) . . ?
O3 C15 C16 121.0(3) . . ?
N2 C15 C16 115.3(3) . . ?
C17 C16 C15 111.6(2) . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C18 C17 C22 118.5(3) . . ?
C18 C17 C16 120.9(3) . . ?
C22 C17 C16 120.5(3) . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 119.8(3) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C17 121.1(3) . . ?
C21 C22 H22 119.5 . . ?
C17 C22 H22 119.5 . . ?
C28 C23 C24 119.8(2) . . ?
C28 C23 N2 122.2(2) . . ?
C24 C23 N2 117.9(2) . . ?
O4 C24 C25 124.2(3) . . ?
O4 C24 C23 116.6(2) . . ?
C25 C24 C23 119.2(3) . . ?
C26 C25 C24 120.2(3) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 120.6(3) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C28 C27 C26 119.6(3) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C27 C28 C23 120.5(3) . . ?
C27 C28 H28 119.8 . . ?
C23 C28 H28 119.8 . . ?
C1 N1 C9 127.8(2) . . ?
C1 N1 H1 116.1 . . ?
C9 N1 H1 116.1 . . ?
C15 N2 C23 123.9(2) . . ?
C15 N2 H2 118.0 . . ?
C23 N2 H2 118.0 . . ?
C10 O2 H2C 109.5 . . ?
C24 O4 H4A 109.5 . . ?

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.041

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_170428lt_0m_a_sq
_database_code_depnum_ccdc_archive 'CCDC 1893992'
loop_
_audit_author_name
_audit_author_address
'kishore pampana'
;National tsing hua university
Taiwan
;
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2019-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 N O2'
_chemical_formula_weight         277.31

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/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   12.2746(8)
_cell_length_b                   9.2499(6)
_cell_length_c                   14.7510(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.612(2)
_cell_angle_gamma                90
_cell_volume                     1646.17(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2861
_cell_measurement_theta_min      2.6119
_cell_measurement_theta_max      26.4220

_exptl_crystal_description       TABULLAR
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8820
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            13871
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.688
_diffrn_reflns_theta_max         26.457
_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             3395
_reflns_number_gt                2617
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.0221P)²+3.2792P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3395
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1274
_refine_ls_wR_factor_gt          0.1182
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
C1 C 0.81321(19) 0.3537(3) 0.36659(15) 0.0187(5) Uani 1 1 d . . . . .
C2 C 0.8703(2) 0.4656(3) 0.41667(16) 0.0229(5) Uani 1 1 d . . . . .
H2 H 0.8611 0.4831 0.4783 0.027 Uiso 1 1 calc R U . . .
C3 C 0.9407(2) 0.5522(3) 0.37683(17) 0.0299(6) Uani 1 1 d . . . . .
H3 H 0.9799 0.6288 0.4113 0.036 Uiso 1 1 calc R U . . .
C4 C 0.9541(2) 0.5274(3) 0.28685(17) 0.0345(7) Uani 1 1 d . . . . .
H4 H 1.0030 0.5863 0.2600 0.041 Uiso 1 1 calc R U . . .
C5 C 0.8962(2) 0.4165(3) 0.23615(17) 0.0329(7) Uani 1 1 d . . . . .
H5 H 0.9052 0.4002 0.1744 0.040 Uiso 1 1 calc R U . . .
C6 C 0.8257(2) 0.3297(3) 0.27489(15) 0.0228(5) Uani 1 1 d . . . . .
C7 C 0.73066(19) 0.2270(3) 0.48616(15) 0.0206(5) Uani 1 1 d . . . . .
C8 C 0.6494(2) 0.1080(3) 0.49769(16) 0.0241(5) Uani 1 1 d . . . . .
H8A H 0.6901 0.0151 0.5069 0.029 Uiso 1 1 calc R U . . .
H8B H 0.6188 0.1276 0.5541 0.029 Uiso 1 1 calc R U . . .
C9 C 0.5544(2) 0.0922(3) 0.41721(16) 0.0219(5) Uani 1 1 d . . . . .
C10 C 0.4623(2) 0.1898(3) 0.40643(16) 0.0207(5) Uani 1 1 d . . . . .
C11 C 0.4507(2) 0.2975(3) 0.47243(18) 0.0266(6) Uani 1 1 d . . . . .
H11 H 0.5057 0.3067 0.5266 0.032 Uiso 1 1 calc R U . . .
C12 C 0.3615(2) 0.3882(3) 0.4592(2) 0.0343(6) Uani 1 1 d . . . . .
H12 H 0.3550 0.4594 0.5043 0.041 Uiso 1 1 calc R U . . .
C13 C 0.2791(2) 0.3776(3) 0.3796(2) 0.0376(7) Uani 1 1 d . . . . .
H13 H 0.2176 0.4418 0.3710 0.045 Uiso 1 1 calc R U . . .
C14 C 0.2873(2) 0.2754(3) 0.31489(19) 0.0330(6) Uani 1 1 d . . . . .
H14 H 0.2309 0.2683 0.2615 0.040 Uiso 1 1 calc R U . . .
C15 C 0.3785(2) 0.1794(3) 0.32583(17) 0.0245(5) Uani 1 1 d . . . . .
C16 C 0.3893(2) 0.0739(3) 0.25849(18) 0.0324(6) Uani 1 1 d . . . . .
H16 H 0.3344 0.0679 0.2040 0.039 Uiso 1 1 calc R U . . .
C17 C 0.4764(2) -0.0186(3) 0.27019(19) 0.0353(7) Uani 1 1 d . . . . .
H17 H 0.4817 -0.0896 0.2246 0.042 Uiso 1 1 calc R U . . .
C18 C 0.5592(2) -0.0094(3) 0.35030(18) 0.0293(6) Uani 1 1 d . . . . .
H18 H 0.6197 -0.0751 0.3580 0.035 Uiso 1 1 calc R U . . .
N1 N 0.73708(16) 0.2614(2) 0.39864(13) 0.0206(4) Uani 1 1 d . . . . .
H1 H 0.6871 0.2209 0.3557 0.025 Uiso 1 1 calc R U . . .
O1 O 0.79028(14) 0.2841(2) 0.55322(11) 0.0279(4) Uani 1 1 d . . . . .
O2 O 0.76484(15) 0.2201(2) 0.22960(11) 0.0291(4) Uani 1 1 d . . . . .
H2A H 0.7706 0.2215 0.1737 0.044 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
C1 C2 1.385(3) . ?
C1 C6 1.407(3) . ?
C1 N1 1.410(3) . ?
C2 C3 1.386(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(3) . ?
C5 H5 0.9500 . ?
C6 O2 1.359(3) . ?
C7 O1 1.235(3) . ?
C7 N1 1.346(3) . ?
C7 C8 1.516(3) . ?
C8 C9 1.510(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C18 1.372(4) . ?
C9 C10 1.432(3) . ?
C10 C11 1.419(3) . ?
C10 C15 1.425(3) . ?
C11 C12 1.365(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.404(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.361(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.415(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.416(4) . ?
C16 C17 1.356(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.412(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N1 H1 0.8800 . ?
O2 H2A 0.8400 . ?

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 C1 C6 119.8(2) . . ?
C2 C1 N1 125.1(2) . . ?
C6 C1 N1 115.0(2) . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 120.2(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
O2 C6 C5 124.1(2) . . ?
O2 C6 C1 116.3(2) . . ?
C5 C6 C1 119.6(2) . . ?
O1 C7 N1 122.5(2) . . ?
O1 C7 C8 121.7(2) . . ?
N1 C7 C8 115.8(2) . . ?
C9 C8 C7 114.2(2) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C18 C9 C10 119.3(2) . . ?
C18 C9 C8 120.2(2) . . ?
C10 C9 C8 120.4(2) . . ?
C11 C10 C15 118.1(2) . . ?
C11 C10 C9 123.0(2) . . ?
C15 C10 C9 118.9(2) . . ?
C12 C11 C10 120.9(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.8(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 121.0(3) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C16 121.8(2) . . ?
C14 C15 C10 119.2(2) . . ?
C16 C15 C10 119.1(2) . . ?
C17 C16 C15 121.3(2) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 119.8(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C9 C18 C17 121.6(3) . . ?
C9 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C7 N1 C1 128.6(2) . . ?
C7 N1 H1 115.7 . . ?
C1 N1 H1 115.7 . . ?
C6 O2 H2A 109.5 . . ?

_refine_diff_density_max         0.679
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.058

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_180710LT_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1893993'
loop_
_audit_author_name
_audit_author_address
'kishore pampana'
;National tsing hua university
Taiwan
;
_audit_update_record             
;
2019-01-28 deposited with the CCDC.	2019-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H13 N O2 S'
_chemical_formula_weight         247.30

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   14.568(2)
_cell_length_b                   5.0757(8)
_cell_length_c                   16.496(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.818(5)
_cell_angle_gamma                90
_cell_volume                     1189.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1562
_cell_measurement_theta_min      2.8679
_cell_measurement_theta_max      23.5320

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.260
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8631
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            16441
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.689
_diffrn_reflns_theta_max         26.644
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2516
_reflns_number_gt                1596
_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       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.0276P)²+0.4937P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2516
_refine_ls_number_parameters     201
_refine_ls_number_restraints     180
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0762
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.006
_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
S1 S 0.87475(13) 0.9039(4) 0.32775(12) 0.0238(3) Uani 0.764(3) 1 d D U P A 1
C1 C 0.8979(6) 0.635(2) 0.3898(7) 0.033(2) Uani 0.764(3) 1 d D U P A 1
H1 H 0.9588 0.5602 0.4077 0.040 Uiso 0.764(3) 1 calc R U P A 1
C2 C 0.8184(5) 0.5384(15) 0.4111(7) 0.0208(12) Uani 0.764(3) 1 d D U P A 1
H2 H 0.8182 0.3899 0.4461 0.025 Uiso 0.764(3) 1 calc R U P A 1
C3 C 0.7356(5) 0.686(3) 0.3746(13) 0.0167(12) Uani 0.764(3) 1 d D U P A 1
C4 C 0.7562(3) 0.8883(15) 0.3277(4) 0.0164(10) Uani 0.764(3) 1 d D U P A 1
H4 H 0.7105 1.0076 0.2981 0.020 Uiso 0.764(3) 1 calc R U P A 1
S1' S 0.9166(5) 0.6029(18) 0.3938(6) 0.0265(12) Uani 0.236(3) 1 d D U P A 2
C1' C 0.8729(16) 0.876(5) 0.3411(17) 0.028(3) Uani 0.236(3) 1 d D U P A 2
H1' H 0.9084 1.0021 0.3183 0.034 Uiso 0.236(3) 1 calc R U P A 2
C2' C 0.7781(13) 0.888(5) 0.3364(17) 0.025(3) Uani 0.236(3) 1 d D U P A 2
H2' H 0.7398 1.0296 0.3105 0.029 Uiso 0.236(3) 1 calc R U P A 2
C3' C 0.7415(18) 0.667(9) 0.374(4) 0.018(3) Uani 0.236(3) 1 d D U P A 2
C4' C 0.8104(15) 0.498(6) 0.410(2) 0.022(3) Uani 0.236(3) 1 d D U P A 2
H4' H 0.8011 0.3444 0.4399 0.026 Uiso 0.236(3) 1 calc R U P A 2
C5 C 0.63922(15) 0.6234(4) 0.38615(13) 0.0197(5) Uani 1 1 d . . . . .
C6 C 0.62846(14) 0.7167(4) 0.47107(14) 0.0170(5) Uani 1 1 d . . . . .
C7 C 0.61758(14) 0.5577(4) 0.61025(13) 0.0160(5) Uani 1 1 d . . . . .
C8 C 0.66208(15) 0.3750(4) 0.66872(14) 0.0198(5) Uani 1 1 d . . . . .
H8 H 0.6969 0.2351 0.6517 0.024 Uiso 1 1 calc R U . . .
C9 C 0.65658(15) 0.3936(4) 0.75167(13) 0.0190(5) Uani 1 1 d . . . . .
H9 H 0.6872 0.2675 0.7910 0.023 Uiso 1 1 calc R U . . .
C10 C 0.60594(14) 0.5979(5) 0.77618(13) 0.0185(5) Uani 1 1 d . . . . .
C11 C 0.56101(15) 0.7814(4) 0.71798(13) 0.0184(5) Uani 1 1 d . . . . .
H11 H 0.5262 0.9210 0.7351 0.022 Uiso 1 1 calc R U . . .
C12 C 0.56653(14) 0.7627(4) 0.63532(14) 0.0167(5) Uani 1 1 d . . . . .
H12 H 0.5357 0.8889 0.5960 0.020 Uiso 1 1 calc R U . . .
C13 C 0.62897(17) 0.4330(5) 0.91560(14) 0.0294(6) Uani 1 1 d . . . . .
H13A H 0.6032 0.2636 0.8926 0.044 Uiso 1 1 calc R U . . .
H13B H 0.6083 0.4689 0.9671 0.044 Uiso 1 1 calc R U . . .
H13C H 0.6979 0.4261 0.9274 0.044 Uiso 1 1 calc R U . . .
N1 N 0.62316(12) 0.5221(3) 0.52574(11) 0.0163(4) Uani 1 1 d . . . . .
O1 O 0.62733(10) 0.9541(3) 0.48774(9) 0.0208(4) Uani 1 1 d . . . . .
O2 O 0.59605(11) 0.6388(3) 0.85644(9) 0.0238(4) Uani 1 1 d . . . . .
H5A H 0.6248 0.4394 0.3724 0.050 Uiso 1 1 d . . . . .
H5B H 0.5901 0.7247 0.3439 0.050 Uiso 1 1 d . . . . .
H3 H 0.6294 0.3430 0.5106 0.050 Uiso 1 1 d . . . . .


_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 1.693(9) . ?
S1 C4 1.729(5) . ?
C1 C2 1.374(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.434(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.358(9) . ?
C3 C5 1.493(7) . ?
C4 H4 0.9500 . ?
S1' C1' 1.687(16) . ?
S1' C4' 1.712(19) . ?
C1' C2' 1.37(2) . ?
C1' H1' 0.9500 . ?
C2' C3' 1.44(2) . ?
C2' H2' 0.9500 . ?
C3' C4' 1.35(2) . ?
C3' C5 1.56(2) . ?
C4' H4' 0.9500 . ?
C5 C6 1.519(3) . ?
C5 H5A 0.9730 . ?
C5 H5B 1.0203 . ?
C6 O1 1.237(3) . ?
C6 N1 1.351(3) . ?
C7 C8 1.390(3) . ?
C7 C12 1.394(3) . ?
C7 N1 1.426(3) . ?
C8 C9 1.392(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C10 O2 1.379(3) . ?
C10 C11 1.392(3) . ?
C11 C12 1.387(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 O2 1.437(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N1 H3 0.9524 . ?

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 91.6(4) . . ?
C2 C1 S1 112.1(6) . . ?
C2 C1 H1 124.0 . . ?
S1 C1 H1 124.0 . . ?
C1 C2 C3 112.6(6) . . ?
C1 C2 H2 123.7 . . ?
C3 C2 H2 123.7 . . ?
C4 C3 C2 111.3(5) . . ?
C4 C3 C5 124.5(7) . . ?
C2 C3 C5 124.2(8) . . ?
C3 C4 S1 112.4(4) . . ?
C3 C4 H4 123.8 . . ?
S1 C4 H4 123.8 . . ?
C1' S1' C4' 94.8(11) . . ?
C2' C1' S1' 109.1(15) . . ?
C2' C1' H1' 125.5 . . ?
S1' C1' H1' 125.5 . . ?
C1' C2' C3' 114.0(16) . . ?
C1' C2' H2' 123.0 . . ?
C3' C2' H2' 123.0 . . ?
C4' C3' C2' 111.9(15) . . ?
C4' C3' C5 119(2) . . ?
C2' C3' C5 128(2) . . ?
C3' C4' S1' 110.1(15) . . ?
C3' C4' H4' 125.0 . . ?
S1' C4' H4' 125.0 . . ?
C3 C5 C6 110.1(9) . . ?
C6 C5 C3' 112(3) . . ?
C3 C5 H5A 109.6 . . ?
C6 C5 H5A 116.9 . . ?
C3' C5 H5A 105.7 . . ?
C3 C5 H5B 110.0 . . ?
C6 C5 H5B 105.8 . . ?
C3' C5 H5B 112.6 . . ?
H5A C5 H5B 104.0 . . ?
O1 C6 N1 123.9(2) . . ?
O1 C6 C5 121.2(2) . . ?
N1 C6 C5 114.86(19) . . ?
C8 C7 C12 119.3(2) . . ?
C8 C7 N1 118.34(19) . . ?
C12 C7 N1 122.32(19) . . ?
C7 C8 C9 121.1(2) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 119.3(2) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
O2 C10 C9 124.7(2) . . ?
O2 C10 C11 115.4(2) . . ?
C9 C10 C11 119.9(2) . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C7 119.6(2) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 N1 C7 125.73(18) . . ?
C6 N1 H3 120.0 . . ?
C7 N1 H3 114.0 . . ?
C10 O2 C13 116.90(18) . . ?

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.059

_shelxl_version_number           2014/6

