# Electronic Supplementary Material (ESI) for ChemComm.
# 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_cd16437
_database_code_depnum_ccdc_archive 'CCDC 1902836'
loop_
_audit_author_name
_audit_author_address
'Yongqiang Zhang'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2019-03-13 deposited with the CCDC.	2019-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 N O5 S'
_chemical_formula_weight         347.37

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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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'
'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                   20.250(3)
_cell_length_b                   21.622(3)
_cell_length_c                   15.041(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6585.5(15)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1347
_cell_measurement_theta_min      5.513
_cell_measurement_theta_max      36.934

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             2912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.224
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6600
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9205
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.932
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3023
_reflns_number_gt                2206
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.981

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0455P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 792 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.01(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3023
_refine_ls_number_parameters     223
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1023
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_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
S1 S 0.12761(7) 0.91082(6) 0.07736(9) 0.0675(4) Uani 1 1 d . . . . .
N1 N 0.2296(2) 0.83370(16) 0.3478(3) 0.0646(12) Uani 1 1 d . . . . .
O1 O 0.16245(17) 0.75225(13) 0.3644(3) 0.0721(10) Uani 1 1 d . . . . .
O2 O 0.11776(14) 0.84426(13) 0.3526(2) 0.0686(10) Uani 1 1 d . . . . .
O3 O 0.13244(15) 0.88877(12) 0.1767(2) 0.0611(8) Uani 1 1 d . . . . .
O4 O 0.1706(2) 0.87013(17) 0.0317(3) 0.0880(11) Uani 1 1 d . . . . .
O5 O 0.06004(18) 0.91440(17) 0.0528(2) 0.0848(11) Uani 1 1 d . . . . .
C1 C 0.1879(2) 0.93628(19) 0.3351(3) 0.0559(11) Uani 1 1 d . . . . .
C2 C 0.1994(3) 0.9990(2) 0.3298(4) 0.0810(16) Uani 1 1 d . . . . .
H2 H 0.1639 1.0260 0.3249 0.097 Uiso 1 1 calc R U . . .
C3 C 0.2621(3) 1.0221(2) 0.3318(5) 0.0931(19) Uani 1 1 d . . . . .
H3 H 0.2690 1.0645 0.3288 0.112 Uiso 1 1 calc R U . . .
C4 C 0.3145(3) 0.9829(2) 0.3382(5) 0.0855(17) Uani 1 1 d . . . . .
H4 H 0.3573 0.9985 0.3383 0.103 Uiso 1 1 calc R U . . .
C5 C 0.3041(2) 0.9203(2) 0.3447(4) 0.0719(14) Uani 1 1 d . . . . .
H5 H 0.3398 0.8936 0.3509 0.086 Uiso 1 1 calc R U . . .
C6 C 0.2406(2) 0.89721(19) 0.3420(3) 0.0558(11) Uani 1 1 d . . . . .
C7 C 0.1704(2) 0.8073(2) 0.3546(3) 0.0559(11) Uani 1 1 d . . . . .
C8 C 0.1187(2) 0.91041(16) 0.3320(3) 0.0571(11) Uani 1 1 d . . . . .
C9 C 0.0885(2) 0.9170(2) 0.2407(3) 0.0608(12) Uani 1 1 d . . . . .
H9A H 0.0457 0.8968 0.2391 0.073 Uiso 1 1 calc R U . . .
H9B H 0.0823 0.9604 0.2267 0.073 Uiso 1 1 calc R U . . .
C10 C 0.0720(3) 0.9393(3) 0.3986(4) 0.0791(16) Uani 1 1 d . . . . .
H10A H 0.0888 0.9332 0.4577 0.119 Uiso 1 1 calc R U . . .
H10B H 0.0293 0.9203 0.3936 0.119 Uiso 1 1 calc R U . . .
H10C H 0.0682 0.9828 0.3869 0.119 Uiso 1 1 calc R U . . .
C11 C 0.1605(2) 0.9857(2) 0.0792(3) 0.0634(12) Uani 1 1 d . . . . .
C12 C 0.1201(3) 1.0363(2) 0.0723(4) 0.0745(14) Uani 1 1 d . . . . .
H12 H 0.0747 1.0316 0.0655 0.089 Uiso 1 1 calc R U . . .
C13 C 0.1482(3) 1.0945(3) 0.0755(4) 0.0854(17) Uani 1 1 d . . . . .
H13 H 0.1210 1.1291 0.0724 0.102 Uiso 1 1 calc R U . . .
C14 C 0.2149(3) 1.1026(2) 0.0830(4) 0.0758(14) Uani 1 1 d . . . . .
C15 C 0.2539(2) 1.0512(2) 0.0901(4) 0.0791(14) Uani 1 1 d . . . . .
H15 H 0.2993 1.0559 0.0963 0.095 Uiso 1 1 calc R U . . .
C16 C 0.2273(2) 0.9927(2) 0.0884(4) 0.0766(15) Uani 1 1 d . . . . .
H16 H 0.2545 0.9582 0.0934 0.092 Uiso 1 1 calc R U . . .
C17 C 0.2442(3) 1.1670(2) 0.0864(5) 0.104(2) Uani 1 1 d . . . . .
H17A H 0.2867 1.1669 0.0582 0.156 Uiso 1 1 calc R U . . .
H17B H 0.2489 1.1796 0.1473 0.156 Uiso 1 1 calc R U . . .
H17C H 0.2155 1.1953 0.0560 0.156 Uiso 1 1 calc R U . . .
H1 H 0.264(2) 0.810(2) 0.349(3) 0.076(16) 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 O4 1.415(4) . ?
S1 O5 1.419(4) . ?
S1 O3 1.572(3) . ?
S1 C11 1.751(5) . ?
N1 C7 1.333(6) . ?
N1 C6 1.394(5) . ?
N1 H1 0.87(5) . ?
O1 C7 1.211(5) . ?
O2 C7 1.332(5) . ?
O2 C8 1.464(4) . ?
O3 C9 1.446(5) . ?
C1 C6 1.365(6) . ?
C1 C2 1.379(6) . ?
C1 C8 1.509(6) . ?
C2 C3 1.364(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.361(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(6) . ?
C5 H5 0.9300 . ?
C8 C9 1.510(7) . ?
C8 C10 1.514(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C16 1.368(7) . ?
C11 C12 1.371(6) . ?
C12 C13 1.382(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.367(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.366(7) . ?
C14 C17 1.515(7) . ?
C15 C16 1.375(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
O4 S1 O5 120.1(2) . . ?
O4 S1 O3 103.6(2) . . ?
O5 S1 O3 108.9(2) . . ?
O4 S1 C11 110.4(2) . . ?
O5 S1 C11 108.7(2) . . ?
O3 S1 C11 104.0(2) . . ?
C7 N1 C6 124.8(4) . . ?
C7 N1 H1 118(3) . . ?
C6 N1 H1 117(3) . . ?
C7 O2 C8 125.5(3) . . ?
C9 O3 S1 117.8(3) . . ?
C6 C1 C2 118.8(4) . . ?
C6 C1 C8 119.9(4) . . ?
C2 C1 C8 121.3(4) . . ?
C3 C2 C1 121.0(5) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C4 C3 C2 119.9(5) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0(5) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 119.8(4) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 120.4(4) . . ?
C1 C6 N1 119.3(4) . . ?
C5 C6 N1 120.3(4) . . ?
O1 C7 O2 119.1(4) . . ?
O1 C7 N1 123.4(4) . . ?
O2 C7 N1 117.5(4) . . ?
O2 C8 C1 111.6(3) . . ?
O2 C8 C9 106.2(3) . . ?
C1 C8 C9 111.7(4) . . ?
O2 C8 C10 104.8(4) . . ?
C1 C8 C10 114.0(4) . . ?
C9 C8 C10 108.0(4) . . ?
O3 C9 C8 108.4(3) . . ?
O3 C9 H9A 110.0 . . ?
C8 C9 H9A 110.0 . . ?
O3 C9 H9B 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 120.7(4) . . ?
C16 C11 S1 118.7(4) . . ?
C12 C11 S1 120.6(4) . . ?
C11 C12 C13 118.6(5) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C14 C13 C12 121.7(5) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C15 C14 C13 118.3(5) . . ?
C15 C14 C17 121.2(5) . . ?
C13 C14 C17 120.5(5) . . ?
C14 C15 C16 121.4(5) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C11 C16 C15 119.4(5) . . ?
C11 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
O4 S1 O3 C9 -173.6(3) . . . . ?
O5 S1 O3 C9 -44.8(3) . . . . ?
C11 S1 O3 C9 71.0(3) . . . . ?
C6 C1 C2 C3 -0.3(9) . . . . ?
C8 C1 C2 C3 -179.4(6) . . . . ?
C1 C2 C3 C4 0.6(10) . . . . ?
C2 C3 C4 C5 -1.4(11) . . . . ?
C3 C4 C5 C6 1.9(10) . . . . ?
C2 C1 C6 C5 0.8(8) . . . . ?
C8 C1 C6 C5 179.8(5) . . . . ?
C2 C1 C6 N1 179.7(5) . . . . ?
C8 C1 C6 N1 -1.2(7) . . . . ?
C4 C5 C6 C1 -1.6(8) . . . . ?
C4 C5 C6 N1 179.4(5) . . . . ?
C7 N1 C6 C1 -6.0(8) . . . . ?
C7 N1 C6 C5 173.0(5) . . . . ?
C8 O2 C7 O1 -173.2(4) . . . . ?
C8 O2 C7 N1 8.4(6) . . . . ?
C6 N1 C7 O1 -175.8(5) . . . . ?
C6 N1 C7 O2 2.6(7) . . . . ?
C7 O2 C8 C1 -14.0(6) . . . . ?
C7 O2 C8 C9 107.9(5) . . . . ?
C7 O2 C8 C10 -137.9(4) . . . . ?
C6 C1 C8 O2 9.9(6) . . . . ?
C2 C1 C8 O2 -171.1(5) . . . . ?
C6 C1 C8 C9 -108.9(5) . . . . ?
C2 C1 C8 C9 70.2(6) . . . . ?
C6 C1 C8 C10 128.3(5) . . . . ?
C2 C1 C8 C10 -52.6(7) . . . . ?
S1 O3 C9 C8 -156.8(3) . . . . ?
O2 C8 C9 O3 -67.3(4) . . . . ?
C1 C8 C9 O3 54.6(4) . . . . ?
C10 C8 C9 O3 -179.2(4) . . . . ?
O4 S1 C11 C16 -36.9(5) . . . . ?
O5 S1 C11 C16 -170.5(4) . . . . ?
O3 S1 C11 C16 73.6(5) . . . . ?
O4 S1 C11 C12 143.6(4) . . . . ?
O5 S1 C11 C12 10.0(5) . . . . ?
O3 S1 C11 C12 -105.9(4) . . . . ?
C16 C11 C12 C13 -0.5(8) . . . . ?
S1 C11 C12 C13 179.0(5) . . . . ?
C11 C12 C13 C14 1.7(9) . . . . ?
C12 C13 C14 C15 -2.0(10) . . . . ?
C12 C13 C14 C17 -179.9(6) . . . . ?
C13 C14 C15 C16 1.1(9) . . . . ?
C17 C14 C15 C16 179.0(6) . . . . ?
C12 C11 C16 C15 -0.3(8) . . . . ?
S1 C11 C16 C15 -179.9(5) . . . . ?
C14 C15 C16 C11 0.1(9) . . . . ?

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 O1 0.87(5) 2.02(5) 2.879(5) 172(5) 14_565
C16 H16 O2 0.93 2.56 3.416(6) 152.8 7_564
C9 H9A O4 0.97 2.64 3.548(6) 156.0 15_465

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.031

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v17224_0m
_database_code_depnum_ccdc_archive 'CCDC 1902837'
loop_
_audit_author_name
_audit_author_address
'Yongqiang Zhang-a'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2019-03-13 deposited with the CCDC.	2019-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 N O3'
_chemical_formula_weight         233.26

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                   6.3499(4)
_cell_length_b                   20.1527(14)
_cell_length_c                   9.1657(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.921(2)
_cell_angle_gamma                90
_cell_volume                     1164.37(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7626
_cell_measurement_theta_min      4.912
_cell_measurement_theta_max      54.958

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6836
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 ?
_diffrn_reflns_number            14539
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.232
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             2026
_reflns_number_gt                1741
_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-2013 (Sheldrick, 2013)'
_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)+(0.0283P)²+0.8024P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.032(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2026
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1190
_refine_ls_wR_factor_gt          0.1137
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.162
_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
N1 N 0.2909(3) 0.55362(10) 0.5528(2) 0.0386(5) Uani 1 1 d . . . . .
O1 O 0.6201(2) 0.53855(8) 0.67226(17) 0.0456(5) Uani 1 1 d . . . . .
O2 O 0.4174(2) 0.61597(8) 0.75225(16) 0.0389(4) Uani 1 1 d . . . . .
O3 O -0.0916(2) 0.59914(10) 0.90265(18) 0.0510(5) Uani 1 1 d . . . . .
H3 H -0.1776 0.5856 0.8353 0.077 Uiso 1 1 calc R U . . .
C1 C 0.4489(3) 0.56719(11) 0.6589(2) 0.0341(5) Uani 1 1 d . . . . .
C2 C 0.1136(3) 0.59502(11) 0.5214(2) 0.0338(5) Uani 1 1 d . . . . .
C3 C -0.0083(4) 0.59122(13) 0.3863(3) 0.0449(6) Uani 1 1 d . . . . .
H3A H 0.0249 0.5607 0.3165 0.054 Uiso 1 1 calc R U . . .
C4 C -0.1786(4) 0.63289(15) 0.3558(3) 0.0575(8) Uani 1 1 d . . . . .
H4 H -0.2613 0.6308 0.2649 0.069 Uiso 1 1 calc R U . . .
C5 C -0.2271(5) 0.67776(16) 0.4595(3) 0.0637(8) Uani 1 1 d . . . . .
H5 H -0.3427 0.7060 0.4385 0.076 Uiso 1 1 calc R U . . .
C6 C -0.1058(4) 0.68132(13) 0.5948(3) 0.0510(7) Uani 1 1 d . . . . .
H6 H -0.1402 0.7121 0.6639 0.061 Uiso 1 1 calc R U . . .
C7 C 0.0669(3) 0.63960(11) 0.6290(2) 0.0352(5) Uani 1 1 d . . . . .
C8 C 0.1993(3) 0.63583(11) 0.7761(2) 0.0328(5) Uani 1 1 d . . . . .
C9 C 0.2294(4) 0.70150(11) 0.8583(3) 0.0426(6) Uani 1 1 d . . . . .
H9A H 0.2954 0.7331 0.7982 0.051 Uiso 1 1 calc R U . . .
H9B H 0.0916 0.7189 0.8741 0.051 Uiso 1 1 calc R U . . .
C10 C 0.3656(4) 0.69451(12) 1.0057(3) 0.0474(7) Uani 1 1 d . . . . .
H10A H 0.5080 0.6813 0.9900 0.057 Uiso 1 1 calc R U . . .
H10B H 0.3745 0.7370 1.0559 0.057 Uiso 1 1 calc R U . . .
C11 C 0.2721(4) 0.64325(13) 1.1004(3) 0.0473(7) Uani 1 1 d . . . . .
H11A H 0.1331 0.6577 1.1212 0.057 Uiso 1 1 calc R U . . .
H11B H 0.3623 0.6386 1.1931 0.057 Uiso 1 1 calc R U . . .
C12 C 0.2533(4) 0.57682(12) 1.0215(3) 0.0464(6) Uani 1 1 d . . . . .
H12A H 0.3935 0.5615 1.0057 0.056 Uiso 1 1 calc R U . . .
H12B H 0.1923 0.5445 1.0826 0.056 Uiso 1 1 calc R U . . .
C13 C 0.1157(3) 0.58207(11) 0.8748(2) 0.0362(6) Uani 1 1 d . . . . .
H13 H 0.1125 0.5391 0.8245 0.043 Uiso 1 1 calc R U . . .
H1 H 0.315(4) 0.5243(12) 0.485(3) 0.043(7) 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
N1 C1 1.338(3) . ?
N1 C2 1.403(3) . ?
N1 H1 0.88(3) . ?
O1 C1 1.224(3) . ?
O2 C1 1.334(2) . ?
O2 C8 1.483(2) . ?
O3 C13 1.413(3) . ?
O3 H3 0.8200 . ?
C2 C3 1.381(3) . ?
C2 C7 1.392(3) . ?
C3 C4 1.371(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.387(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.503(3) . ?
C8 C9 1.523(3) . ?
C8 C13 1.546(3) . ?
C9 C10 1.520(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.516(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.520(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.516(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13 0.9800 . ?

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 N1 C2 122.70(19) . . ?
C1 N1 H1 118.0(15) . . ?
C2 N1 H1 117.1(15) . . ?
C1 O2 C8 120.54(16) . . ?
C13 O3 H3 109.5 . . ?
O1 C1 O2 118.88(19) . . ?
O1 C1 N1 123.7(2) . . ?
O2 C1 N1 117.35(19) . . ?
C3 C2 C7 121.8(2) . . ?
C3 C2 N1 120.0(2) . . ?
C7 C2 N1 118.20(19) . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 120.8(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C2 117.5(2) . . ?
C6 C7 C8 125.1(2) . . ?
C2 C7 C8 117.32(19) . . ?
O2 C8 C7 108.24(16) . . ?
O2 C8 C9 104.10(17) . . ?
C7 C8 C9 115.03(19) . . ?
O2 C8 C13 106.83(17) . . ?
C7 C8 C13 111.47(18) . . ?
C9 C8 C13 110.55(17) . . ?
C10 C9 C8 112.52(19) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 110.6(2) . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 C12 109.95(19) . . ?
C10 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C13 C12 C11 111.4(2) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
O3 C13 C12 107.84(19) . . ?
O3 C13 C8 109.15(18) . . ?
C12 C13 C8 111.47(18) . . ?
O3 C13 H13 109.4 . . ?
C12 C13 H13 109.4 . . ?
C8 C13 H13 109.4 . . ?

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
C8 O2 C1 O1 -158.4(2) . . . . ?
C8 O2 C1 N1 23.3(3) . . . . ?
C2 N1 C1 O1 -167.1(2) . . . . ?
C2 N1 C1 O2 11.2(3) . . . . ?
C1 N1 C2 C3 159.5(2) . . . . ?
C1 N1 C2 C7 -20.0(3) . . . . ?
C7 C2 C3 C4 0.8(4) . . . . ?
N1 C2 C3 C4 -178.7(2) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C5 C6 C7 C2 0.8(4) . . . . ?
C5 C6 C7 C8 -175.2(2) . . . . ?
C3 C2 C7 C6 -1.1(3) . . . . ?
N1 C2 C7 C6 178.4(2) . . . . ?
C3 C2 C7 C8 175.3(2) . . . . ?
N1 C2 C7 C8 -5.3(3) . . . . ?
C1 O2 C8 C7 -44.2(2) . . . . ?
C1 O2 C8 C9 -167.01(18) . . . . ?
C1 O2 C8 C13 76.0(2) . . . . ?
C6 C7 C8 O2 -150.6(2) . . . . ?
C2 C7 C8 O2 33.4(3) . . . . ?
C6 C7 C8 C9 -34.7(3) . . . . ?
C2 C7 C8 C9 149.3(2) . . . . ?
C6 C7 C8 C13 92.2(3) . . . . ?
C2 C7 C8 C13 -83.9(2) . . . . ?
O2 C8 C9 C10 -61.4(2) . . . . ?
C7 C8 C9 C10 -179.69(19) . . . . ?
C13 C8 C9 C10 53.0(3) . . . . ?
C8 C9 C10 C11 -56.4(3) . . . . ?
C9 C10 C11 C12 58.1(3) . . . . ?
C10 C11 C12 C13 -58.6(3) . . . . ?
C11 C12 C13 O3 -63.8(2) . . . . ?
C11 C12 C13 C8 56.0(3) . . . . ?
O2 C8 C13 O3 179.22(16) . . . . ?
C7 C8 C13 O3 -62.7(2) . . . . ?
C9 C8 C13 O3 66.6(2) . . . . ?
O2 C8 C13 C12 60.2(2) . . . . ?
C7 C8 C13 C12 178.27(18) . . . . ?
C9 C8 C13 C12 -52.5(2) . . . . ?

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 O1 0.88(3) 2.00(3) 2.882(2) 177(2) 3_666
O3 H3 O1 0.82 2.08 2.893(2) 172.3 1_455

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-4

