# Electronic Supplementary Material (ESI) for ChemComm.
# 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_lz321
_database_code_depnum_ccdc_archive 'CCDC 1581420'
_audit_update_record             
;
2017-10-23 deposited with the CCDC.
2017-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_formula_moiety         'C18 H19 N O4'
_chemical_formula_sum            'C18 H19 N O4'
_chemical_formula_weight         313.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   9.8925(4)
_cell_length_b                   12.4541(5)
_cell_length_c                   14.3675(6)
_cell_angle_alpha                96.459(2)
_cell_angle_beta                 109.369(2)
_cell_angle_gamma                103.883(2)
_cell_volume                     1585.09(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    9803
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      66.54

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.805
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_process_details   
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         micro-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            26459
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.841
_diffrn_reflns_theta_max         66.624
_diffrn_reflns_theta_full        66.500
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5569
_reflns_number_gt                5339
_reflns_threshold_expression     'I > 2σ(I)'

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²+0.4959P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5569
_refine_ls_number_parameters     420
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.044

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 0.22093(10) -0.10953(7) 0.20549(7) 0.0307(2) Uani 1 1 d . . . . .
H1A H 0.1908 -0.1385 0.2478 0.046 Uiso 1 1 calc R U . . .
O2 O 0.12614(10) -0.08039(8) -0.02949(6) 0.0351(2) Uani 1 1 d . . . . .
O3 O 0.36557(10) -0.07168(8) 0.05279(7) 0.0359(2) Uani 1 1 d . . . . .
O4 O 0.44645(10) 0.25483(7) 0.14163(8) 0.0381(2) Uani 1 1 d . . . . .
O5 O 0.73716(9) 0.39834(7) 0.23486(7) 0.0335(2) Uani 1 1 d . . . . .
H5 H 0.6439 0.3702 0.2160 0.050 Uiso 1 1 calc R U . . .
O6 O 1.06878(11) 0.42888(8) 0.41398(6) 0.0355(2) Uani 1 1 d . . . . .
O7 O 1.04808(10) 0.42606(8) 0.25360(6) 0.0339(2) Uani 1 1 d . . . . .
O8 O 1.14998(12) 0.75216(8) 0.33304(7) 0.0417(2) Uani 1 1 d . . . . .
N1 N 0.21231(11) 0.13981(8) 0.09547(7) 0.0248(2) Uani 1 1 d . . . . .
H1B H 0.1157 0.1326 0.0714 0.030 Uiso 1 1 calc R U . . .
N2 N 1.02262(11) 0.64601(8) 0.41090(7) 0.0257(2) Uani 1 1 d . . . . .
H2A H 0.9984 0.6429 0.4644 0.031 Uiso 1 1 calc R U . . .
C1 C 0.17102(13) -0.01195(9) 0.18974(9) 0.0243(2) Uani 1 1 d . . . . .
H1C H 0.0629 -0.0381 0.1441 0.029 Uiso 1 1 calc R U . . .
C2 C 0.26292(12) 0.04680(9) 0.13221(8) 0.0227(2) Uani 1 1 d . . . . .
H2B H 0.3713 0.0756 0.1773 0.027 Uiso 1 1 calc R U . . .
C3 C 0.24256(13) -0.04183(10) 0.04280(9) 0.0245(2) Uani 1 1 d . . . . .
C4 C 0.3512(2) -0.16273(16) -0.02546(13) 0.0593(5) Uani 1 1 d . . . . .
H4A H 0.2778 -0.2316 -0.0257 0.089 Uiso 1 1 calc R U . . .
H4B H 0.4486 -0.1765 -0.0124 0.089 Uiso 1 1 calc R U . . .
H4C H 0.3174 -0.1417 -0.0912 0.089 Uiso 1 1 calc R U . . .
C5 C 0.18540(13) 0.05989(10) 0.28652(9) 0.0254(2) Uani 1 1 d . . . . .
C6 C 0.31813(14) 0.14310(10) 0.34681(9) 0.0301(3) Uani 1 1 d . . . . .
H6 H 0.4002 0.1584 0.3249 0.036 Uiso 1 1 calc R U . . .
C7 C 0.33240(17) 0.20389(11) 0.43818(10) 0.0376(3) Uani 1 1 d . . . . .
H7 H 0.4239 0.2600 0.4787 0.045 Uiso 1 1 calc R U . . .
C8 C 0.21339(18) 0.18279(12) 0.47024(10) 0.0415(3) Uani 1 1 d . . . . .
H8 H 0.2222 0.2250 0.5324 0.050 Uiso 1 1 calc R U . . .
C9 C 0.08181(17) 0.10013(12) 0.41159(11) 0.0404(3) Uani 1 1 d . . . . .
H9 H 0.0007 0.0856 0.4344 0.048 Uiso 1 1 calc R U . . .
C10 C 0.06481(15) 0.03730(11) 0.31958(10) 0.0321(3) Uani 1 1 d . . . . .
C11 C -0.08053(16) -0.05379(13) 0.25962(13) 0.0461(4) Uani 1 1 d . . . . .
H11A H -0.1439 -0.0641 0.2998 0.069 Uiso 1 1 calc R U . . .
H11B H -0.0595 -0.1249 0.2427 0.069 Uiso 1 1 calc R U . . .
H11C H -0.1327 -0.0316 0.1974 0.069 Uiso 1 1 calc R U . . .
C12 C 0.31072(13) 0.23706(9) 0.09753(8) 0.0245(2) Uani 1 1 d . . . . .
C13 C 0.24894(13) 0.32124(10) 0.04398(8) 0.0261(2) Uani 1 1 d . . . . .
C14 C 0.09967(14) 0.29854(11) -0.01871(10) 0.0328(3) Uani 1 1 d . . . . .
H14 H 0.0310 0.2264 -0.0289 0.039 Uiso 1 1 calc R U . . .
C15 C 0.05016(16) 0.38028(12) -0.06655(10) 0.0387(3) Uani 1 1 d . . . . .
H15 H -0.0523 0.3641 -0.1088 0.046 Uiso 1 1 calc R U . . .
C16 C 0.14921(18) 0.48492(12) -0.05294(10) 0.0420(3) Uani 1 1 d . . . . .
H16 H 0.1151 0.5413 -0.0850 0.050 Uiso 1 1 calc R U . . .
C17 C 0.29788(19) 0.50725(12) 0.00748(11) 0.0503(4) Uani 1 1 d . . . . .
H17 H 0.3666 0.5789 0.0161 0.060 Uiso 1 1 calc R U . . .
C18 C 0.34796(17) 0.42648(11) 0.05570(10) 0.0408(3) Uani 1 1 d . . . . .
H18 H 0.4508 0.4430 0.0972 0.049 Uiso 1 1 calc R U . . .
C19 C 0.78621(13) 0.49632(10) 0.31329(9) 0.0267(3) Uani 1 1 d . . . . .
H19 H 0.7891 0.4708 0.3773 0.032 Uiso 1 1 calc R U . . .
C20 C 0.94772(12) 0.55332(9) 0.32393(8) 0.0238(2) Uani 1 1 d . . . . .
H20 H 0.9475 0.5817 0.2615 0.029 Uiso 1 1 calc R U . . .
C21 C 1.02917(12) 0.46315(10) 0.33679(8) 0.0247(2) Uani 1 1 d . . . . .
C22 C 1.1030(2) 0.32812(14) 0.25214(12) 0.0494(4) Uani 1 1 d . . . . .
H22A H 1.1127 0.3082 0.1872 0.074 Uiso 0.5 1 calc R U P . .
H22B H 1.2012 0.3457 0.3067 0.074 Uiso 0.5 1 calc R U P . .
H22C H 1.0323 0.2642 0.2616 0.074 Uiso 0.5 1 calc R U P . .
H22D H 1.1182 0.3039 0.3165 0.074 Uiso 0.5 1 calc R U P . .
H22E H 1.0296 0.2664 0.1969 0.074 Uiso 0.5 1 calc R U P . .
H22F H 1.1985 0.3479 0.2421 0.074 Uiso 0.5 1 calc R U P . .
C23 C 0.68199(13) 0.56971(10) 0.29215(9) 0.0297(3) Uani 1 1 d . . . . .
C24 C 0.69699(15) 0.65247(11) 0.23554(11) 0.0382(3) Uani 1 1 d . . . . .
H24 H 0.7767 0.6657 0.2113 0.046 Uiso 1 1 calc R U . . .
C25 C 0.59662(17) 0.71579(12) 0.21420(14) 0.0523(4) Uani 1 1 d . . . . .
H25 H 0.6085 0.7724 0.1760 0.063 Uiso 1 1 calc R U . . .
C26 C 0.48031(17) 0.69675(14) 0.24821(14) 0.0591(5) Uani 1 1 d . . . . .
H26 H 0.4119 0.7402 0.2338 0.071 Uiso 1 1 calc R U . . .
C27 C 0.46344(17) 0.61432(15) 0.30330(13) 0.0537(4) Uani 1 1 d . . . . .
H27 H 0.3820 0.6011 0.3258 0.064 Uiso 1 1 calc R U . . .
C28 C 0.56292(15) 0.54969(12) 0.32694(11) 0.0401(3) Uani 1 1 d . . . . .
C29 C 0.53954(19) 0.45900(16) 0.38645(13) 0.0563(4) Uani 1 1 d . . . . .
H29A H 0.4489 0.4555 0.4012 0.084 Uiso 1 1 calc R U . . .
H29B H 0.6264 0.4769 0.4498 0.084 Uiso 1 1 calc R U . . .
H29C H 0.5282 0.3857 0.3469 0.084 Uiso 1 1 calc R U . . .
C30 C 1.12895(13) 0.73706(10) 0.41102(9) 0.0248(2) Uani 1 1 d . . . . .
C31 C 1.21983(13) 0.81805(9) 0.50965(9) 0.0245(2) Uani 1 1 d . . . . .
C32 C 1.30269(15) 0.92526(11) 0.50874(10) 0.0343(3) Uani 1 1 d . . . . .
H32 H 1.3008 0.9449 0.4464 0.041 Uiso 1 1 calc R U . . .
C33 C 1.38751(16) 1.00304(11) 0.59804(11) 0.0391(3) Uani 1 1 d . . . . .
H33 H 1.4431 1.0762 0.5968 0.047 Uiso 1 1 calc R U . . .
C34 C 1.39196(15) 0.97521(11) 0.68883(10) 0.0361(3) Uani 1 1 d . . . . .
H34 H 1.4488 1.0295 0.7500 0.043 Uiso 1 1 calc R U . . .
C35 C 1.31360(16) 0.86816(12) 0.69061(10) 0.0376(3) Uani 1 1 d . . . . .
H35 H 1.3189 0.8482 0.7533 0.045 Uiso 1 1 calc R U . . .
C36 C 1.22767(14) 0.79005(11) 0.60178(9) 0.0315(3) Uani 1 1 d . . . . .
H36 H 1.1735 0.7167 0.6036 0.038 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 1.4309(14) . ?
O2 C3 1.2102(15) . ?
O3 C3 1.3239(15) . ?
O3 C4 1.4491(17) . ?
O4 C12 1.2308(15) . ?
O5 C19 1.4276(14) . ?
O6 C21 1.2100(15) . ?
O7 C21 1.3200(14) . ?
O7 C22 1.4506(16) . ?
O8 C30 1.2318(15) . ?
N1 C12 1.3500(15) . ?
N1 C2 1.4532(14) . ?
N2 C30 1.3484(15) . ?
N2 C20 1.4470(14) . ?
C1 C5 1.5106(16) . ?
C1 C2 1.5364(15) . ?
C2 C3 1.5206(16) . ?
C5 C6 1.3925(17) . ?
C5 C10 1.4045(18) . ?
C6 C7 1.3850(18) . ?
C7 C8 1.381(2) . ?
C8 C9 1.378(2) . ?
C9 C10 1.3945(19) . ?
C10 C11 1.507(2) . ?
C12 C13 1.4972(17) . ?
C13 C18 1.3895(18) . ?
C13 C14 1.3899(18) . ?
C14 C15 1.3865(19) . ?
C15 C16 1.378(2) . ?
C16 C17 1.377(2) . ?
C17 C18 1.380(2) . ?
C19 C23 1.5158(17) . ?
C19 C20 1.5327(16) . ?
C20 C21 1.5254(16) . ?
C23 C24 1.393(2) . ?
C23 C28 1.4061(19) . ?
C24 C25 1.389(2) . ?
C25 C26 1.374(3) . ?
C26 C27 1.377(3) . ?
C27 C28 1.397(2) . ?
C28 C29 1.511(2) . ?
C30 C31 1.4939(16) . ?
C31 C36 1.3888(17) . ?
C31 C32 1.3930(17) . ?
C32 C33 1.3801(19) . ?
C33 C34 1.376(2) . ?
C34 C35 1.380(2) . ?
C35 C36 1.3791(18) . ?

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
C3 O3 C4 115.87(11) . . ?
C21 O7 C22 116.58(10) . . ?
C12 N1 C2 121.27(9) . . ?
C30 N2 C20 120.89(9) . . ?
O1 C1 C5 112.82(9) . . ?
O1 C1 C2 103.50(9) . . ?
C5 C1 C2 115.44(9) . . ?
N1 C2 C3 109.10(9) . . ?
N1 C2 C1 112.02(9) . . ?
C3 C2 C1 106.99(9) . . ?
O2 C3 O3 124.02(11) . . ?
O2 C3 C2 123.27(11) . . ?
O3 C3 C2 112.71(10) . . ?
C6 C5 C10 119.17(11) . . ?
C6 C5 C1 121.71(11) . . ?
C10 C5 C1 119.00(11) . . ?
C7 C6 C5 121.04(12) . . ?
C8 C7 C6 119.89(13) . . ?
C9 C8 C7 119.62(12) . . ?
C8 C9 C10 121.63(13) . . ?
C9 C10 C5 118.65(12) . . ?
C9 C10 C11 119.33(12) . . ?
C5 C10 C11 122.01(12) . . ?
O4 C12 N1 120.66(11) . . ?
O4 C12 C13 121.61(10) . . ?
N1 C12 C13 117.73(10) . . ?
C18 C13 C14 118.60(12) . . ?
C18 C13 C12 117.77(11) . . ?
C14 C13 C12 123.60(11) . . ?
C15 C14 C13 120.58(12) . . ?
C16 C15 C14 120.15(13) . . ?
C17 C16 C15 119.59(13) . . ?
C16 C17 C18 120.62(13) . . ?
C17 C18 C13 120.44(13) . . ?
O5 C19 C23 112.50(9) . . ?
O5 C19 C20 104.04(9) . . ?
C23 C19 C20 115.44(10) . . ?
N2 C20 C21 109.52(9) . . ?
N2 C20 C19 111.32(9) . . ?
C21 C20 C19 106.85(9) . . ?
O6 C21 O7 124.55(11) . . ?
O6 C21 C20 123.42(11) . . ?
O7 C21 C20 112.01(10) . . ?
C24 C23 C28 119.39(12) . . ?
C24 C23 C19 121.84(11) . . ?
C28 C23 C19 118.71(12) . . ?
C25 C24 C23 120.67(14) . . ?
C26 C25 C24 120.18(16) . . ?
C25 C26 C27 119.65(14) . . ?
C26 C27 C28 121.75(15) . . ?
C27 C28 C23 118.36(15) . . ?
C27 C28 C29 120.18(14) . . ?
C23 C28 C29 121.44(13) . . ?
O8 C30 N2 121.17(11) . . ?
O8 C30 C31 121.75(10) . . ?
N2 C30 C31 117.08(10) . . ?
C36 C31 C32 118.88(11) . . ?
C36 C31 C30 122.82(10) . . ?
C32 C31 C30 118.29(11) . . ?
C33 C32 C31 120.26(12) . . ?
C34 C33 C32 120.37(12) . . ?
C33 C34 C35 119.76(12) . . ?
C36 C35 C34 120.32(12) . . ?
C35 C36 C31 120.37(12) . . ?

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1581422'
_audit_update_record             
;
2017-10-23 deposited with the CCDC.
2017-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N O4 S'
_chemical_formula_sum            'C15 H15 N O4 S'
_chemical_formula_weight         305.34

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.9135(2)
_cell_length_b                   9.8740(2)
_cell_length_c                   19.0229(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1486.41(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9061
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      30.13

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.232
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.719
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS, Bruker AXS Inc., Madison,
Wisconsin, USA
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13266
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.324
_diffrn_reflns_theta_max         30.126
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4353
_reflns_number_gt                4182
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.999

_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    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.0474P)²+0.1881P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1756 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.023(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4353
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0770
_refine_ls_wR_factor_gt          0.0758
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.04834(6) 0.43775(5) 0.17024(3) 0.04307(13) Uani 1 1 d . . . . .
O1 O 0.28641(18) 0.27926(11) 0.09218(6) 0.0344(3) Uani 1 1 d . . . . .
O2 O 0.58170(13) 0.57452(10) 0.25071(5) 0.0250(2) Uani 1 1 d . . . . .
O3 O 0.6630(2) 0.32230(15) 0.03514(6) 0.0483(4) Uani 1 1 d . . . . .
O4 O 0.72215(13) 0.22774(11) 0.13932(5) 0.0256(2) Uani 1 1 d . . . . .
N1 N 0.49789(14) 0.36902(11) 0.20998(5) 0.0183(2) Uani 1 1 d . . . . .
C1 C 0.35238(19) 0.41277(13) 0.09695(6) 0.0233(3) Uani 1 1 d . . . . .
H1B H 0.3726 0.4490 0.0486 0.028 Uiso 1 1 calc R U . . .
C2 C 0.52158(17) 0.40626(13) 0.13718(6) 0.0206(2) Uani 1 1 d . . . . .
H2 H 0.5715 0.4993 0.1365 0.025 Uiso 1 1 calc R U . . .
C3 C 0.52357(15) 0.46067(12) 0.26178(6) 0.0170(2) Uani 1 1 d . . . . .
C4 C 0.47937(16) 0.41539(12) 0.33442(6) 0.0195(2) Uani 1 1 d . . . . .
C5 C 0.35086(19) 0.32284(14) 0.34719(7) 0.0262(3) Uani 1 1 d . . . . .
H5 H 0.2862 0.2877 0.3093 0.031 Uiso 1 1 calc R U . . .
C6 C 0.3170(3) 0.28170(17) 0.41580(9) 0.0396(4) Uani 1 1 d . . . . .
H6 H 0.2300 0.2177 0.4248 0.048 Uiso 1 1 calc R U . . .
C7 C 0.4107(3) 0.3344(2) 0.47089(8) 0.0477(5) Uani 1 1 d . . . . .
H7 H 0.3888 0.3051 0.5176 0.057 Uiso 1 1 calc R U . . .
C8 C 0.5347(3) 0.42854(19) 0.45863(8) 0.0434(4) Uani 1 1 d . . . . .
H8 H 0.5965 0.4654 0.4969 0.052 Uiso 1 1 calc R U . . .
C9 C 0.5705(2) 0.47036(15) 0.39035(7) 0.0289(3) Uani 1 1 d . . . . .
H9 H 0.6562 0.5357 0.3819 0.035 Uiso 1 1 calc R U . . .
C10 C 0.64280(19) 0.31352(15) 0.09797(7) 0.0258(3) Uani 1 1 d . . . . .
C11 C 0.8434(2) 0.13928(17) 0.10573(9) 0.0340(3) Uani 1 1 d . . . . .
H11A H 0.7842 0.0770 0.0741 0.051 Uiso 1 1 calc R U . . .
H11B H 0.9040 0.0872 0.1416 0.051 Uiso 1 1 calc R U . . .
H11C H 0.9242 0.1937 0.0787 0.051 Uiso 1 1 calc R U . . .
C12 C 0.22977(17) 0.50307(14) 0.13484(7) 0.0218(2) Uani 1 1 d . . . . .
C13 C 0.2433(2) 0.63752(15) 0.14903(9) 0.0296(3) Uani 1 1 d . . . . .
H13 H 0.3354 0.6919 0.1339 0.036 Uiso 1 1 calc R U . . .
C14 C 0.1055(2) 0.6881(2) 0.18869(10) 0.0406(4) Uani 1 1 d . . . . .
H14 H 0.0951 0.7800 0.2028 0.049 Uiso 1 1 calc R U . . .
C15 C -0.0093(2) 0.5918(2) 0.20424(11) 0.0462(4) Uani 1 1 d . . . . .
H15 H -0.1093 0.6074 0.2307 0.055 Uiso 1 1 calc R U . . .
H1A H 0.472(3) 0.290(2) 0.2183(9) 0.025(4) Uiso 1 1 d . . . . .
H1 H 0.262(3) 0.259(3) 0.0490(13) 0.053(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
S1 C12 1.7120(14) . ?
S1 C15 1.715(2) . ?
O1 C1 1.4208(16) . ?
O1 H1 0.87(3) . ?
O2 C3 1.2328(15) . ?
O3 C10 1.2090(17) . ?
O4 C10 1.3154(18) . ?
O4 C11 1.4464(17) . ?
N1 C3 1.3532(15) . ?
N1 C2 1.4452(15) . ?
N1 H1A 0.82(2) . ?
C1 C12 1.5020(19) . ?
C1 C2 1.5436(19) . ?
C1 H1B 1.0000 . ?
C2 C10 1.5216(18) . ?
C2 H2 1.0000 . ?
C3 C4 1.4939(16) . ?
C4 C5 1.3886(19) . ?
C4 C9 1.3950(18) . ?
C5 C6 1.393(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.372(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.3590(19) . ?
C13 C14 1.417(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.348(3) . ?
C14 H14 0.9500 . ?
C15 H15 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
C12 S1 C15 92.13(8) . . ?
C1 O1 H1 110.6(17) . . ?
C10 O4 C11 116.19(11) . . ?
C3 N1 C2 120.54(10) . . ?
C3 N1 H1A 122.2(13) . . ?
C2 N1 H1A 117.2(13) . . ?
O1 C1 C12 110.13(12) . . ?
O1 C1 C2 108.17(11) . . ?
C12 C1 C2 110.31(10) . . ?
O1 C1 H1B 109.4 . . ?
C12 C1 H1B 109.4 . . ?
C2 C1 H1B 109.4 . . ?
N1 C2 C10 113.48(11) . . ?
N1 C2 C1 111.91(11) . . ?
C10 C2 C1 109.20(10) . . ?
N1 C2 H2 107.3 . . ?
C10 C2 H2 107.3 . . ?
C1 C2 H2 107.3 . . ?
O2 C3 N1 122.79(11) . . ?
O2 C3 C4 121.22(11) . . ?
N1 C3 C4 115.99(11) . . ?
C5 C4 C9 120.07(12) . . ?
C5 C4 C3 122.02(11) . . ?
C9 C4 C3 117.90(12) . . ?
C4 C5 C6 119.79(15) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 119.76(17) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C8 C7 C6 120.59(14) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.34(16) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C4 119.41(16) . . ?
C8 C9 H9 120.3 . . ?
C4 C9 H9 120.3 . . ?
O3 C10 O4 125.04(14) . . ?
O3 C10 C2 121.67(14) . . ?
O4 C10 C2 113.28(11) . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C1 128.65(13) . . ?
C13 C12 S1 110.84(12) . . ?
C1 C12 S1 120.46(10) . . ?
C12 C13 C14 112.93(15) . . ?
C12 C13 H13 123.5 . . ?
C14 C13 H13 123.5 . . ?
C15 C14 C13 112.77(17) . . ?
C15 C14 H14 123.6 . . ?
C13 C14 H14 123.6 . . ?
C14 C15 S1 111.32(13) . . ?
C14 C15 H15 124.3 . . ?
S1 C15 H15 124.3 . . ?

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_lz374
_database_code_depnum_ccdc_archive 'CCDC 1581421'
_audit_update_record             
;
2017-10-23 deposited with the CCDC.
2017-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_formula_moiety         'C16 H16 N2 O4, H2 O'
_chemical_formula_sum            'C16 H18 N2 O5'
_chemical_formula_weight         318.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.0313(4)
_cell_length_b                   11.8519(4)
_cell_length_c                   14.6499(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1568.10(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    8114
_cell_measurement_theta_min      4.80
_cell_measurement_theta_max      66.63

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.771
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_process_details   
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         micro-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            9671
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.799
_diffrn_reflns_theta_max         66.628
_diffrn_reflns_theta_full        66.500
_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 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2769
_reflns_number_gt                2730
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.997

_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    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+0.1932P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0086(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1136 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2769
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.052

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 0.36959(16) 0.73023(11) 0.74992(9) 0.0272(3) Uani 1 1 d . . . . .
H1A H 0.3611 0.7977 0.7666 0.041 Uiso 1 1 calc R U . . .
O2 O 0.09336(17) 0.77417(14) 0.58497(14) 0.0443(4) Uani 1 1 d . . . . .
O3 O 0.28468(17) 0.89301(11) 0.57189(11) 0.0323(4) Uani 1 1 d . . . . .
O4 O 0.26189(19) 0.56834(13) 0.44164(10) 0.0365(4) Uani 1 1 d . . . . .
O5 O 0.33019(19) 0.44487(14) 0.28335(10) 0.0376(4) Uani 1 1 d . . . . .
H5A H 0.3052 0.4896 0.3326 0.045 Uiso 1 1 d R U . . .
H5B H 0.2698 0.3846 0.2861 0.045 Uiso 1 1 d R U . . .
N1 N 0.27307(18) 0.59092(13) 0.59423(10) 0.0226(3) Uani 1 1 d . . . . .
H1B H 0.2576 0.5613 0.6485 0.027 Uiso 1 1 calc R U . . .
N2 N 0.6597(2) 0.45330(14) 0.70716(12) 0.0301(4) Uani 1 1 d . . . . .
C1 C 0.4498(2) 0.72566(16) 0.66644(12) 0.0223(4) Uani 1 1 d . . . . .
H1C H 0.4943 0.8017 0.6557 0.027 Uiso 1 1 calc R U . . .
C2 C 0.3429(2) 0.70046(15) 0.58663(12) 0.0219(4) Uani 1 1 d . . . . .
H2 H 0.4009 0.7023 0.5285 0.026 Uiso 1 1 calc R U . . .
C3 C 0.2238(2) 0.79184(16) 0.58169(13) 0.0252(4) Uani 1 1 d . . . . .
C4 C 0.1817(3) 0.98680(19) 0.56595(19) 0.0408(5) Uani 1 1 d . . . . .
H4A H 0.1179 0.9769 0.5124 0.061 Uiso 1 1 calc R U . . .
H4B H 0.2371 1.0576 0.5602 0.061 Uiso 1 1 calc R U . . .
H4C H 0.1206 0.9892 0.6212 0.061 Uiso 1 1 calc R U . . .
C5 C 0.5750(2) 0.64113(16) 0.67291(12) 0.0222(4) Uani 1 1 d . . . . .
C6 C 0.7183(2) 0.67178(16) 0.64926(13) 0.0265(4) Uani 1 1 d . . . . .
H6 H 0.7389 0.7464 0.6293 0.032 Uiso 1 1 calc R U . . .
C7 C 0.8312(2) 0.59263(19) 0.65499(15) 0.0333(5) Uani 1 1 d . . . . .
H7 H 0.9301 0.6122 0.6396 0.040 Uiso 1 1 calc R U . . .
C8 C 0.7966(2) 0.48513(19) 0.68348(16) 0.0345(5) Uani 1 1 d . . . . .
H8 H 0.8738 0.4308 0.6865 0.041 Uiso 1 1 calc R U . . .
C9 C 0.5521(2) 0.53056(16) 0.70268(13) 0.0254(4) Uani 1 1 d . . . . .
H9 H 0.4550 0.5091 0.7207 0.030 Uiso 1 1 calc R U . . .
C10 C 0.2317(2) 0.53416(16) 0.51912(13) 0.0238(4) Uani 1 1 d . . . . .
C11 C 0.1476(2) 0.42676(15) 0.53313(13) 0.0237(4) Uani 1 1 d . . . . .
C12 C 0.1521(2) 0.36501(16) 0.61408(14) 0.0272(4) Uani 1 1 d . . . . .
H12 H 0.2108 0.3909 0.6637 0.033 Uiso 1 1 calc R U . . .
C13 C 0.0715(2) 0.26617(17) 0.62248(15) 0.0330(5) Uani 1 1 d . . . . .
H13 H 0.0743 0.2248 0.6780 0.040 Uiso 1 1 calc R U . . .
C14 C -0.0131(2) 0.22755(18) 0.55018(16) 0.0346(5) Uani 1 1 d . . . . .
H14 H -0.0685 0.1598 0.5561 0.042 Uiso 1 1 calc R U . . .
C15 C -0.0169(3) 0.2878(2) 0.46922(17) 0.0401(5) Uani 1 1 d . . . . .
H15 H -0.0746 0.2612 0.4195 0.048 Uiso 1 1 calc R U . . .
C16 C 0.0633(3) 0.38675(18) 0.46061(14) 0.0340(5) Uani 1 1 d . . . . .
H16 H 0.0607 0.4276 0.4048 0.041 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 1.422(2) . ?
O2 C3 1.198(3) . ?
O3 C3 1.327(2) . ?
O3 C4 1.452(3) . ?
O4 C10 1.236(3) . ?
N1 C10 1.343(3) . ?
N1 C2 1.448(2) . ?
N2 C9 1.337(3) . ?
N2 C8 1.338(3) . ?
C1 C5 1.514(3) . ?
C1 C2 1.545(3) . ?
C2 C3 1.528(3) . ?
C5 C6 1.388(3) . ?
C5 C9 1.397(3) . ?
C6 C7 1.388(3) . ?
C7 C8 1.377(3) . ?
C10 C11 1.496(2) . ?
C11 C16 1.390(3) . ?
C11 C12 1.394(3) . ?
C12 C13 1.385(3) . ?
C13 C14 1.384(3) . ?
C14 C15 1.385(4) . ?
C15 C16 1.384(3) . ?

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
C3 O3 C4 115.66(16) . . ?
C10 N1 C2 120.49(15) . . ?
C9 N2 C8 117.77(18) . . ?
O1 C1 C5 110.59(14) . . ?
O1 C1 C2 109.87(14) . . ?
C5 C1 C2 112.71(15) . . ?
N1 C2 C3 109.44(15) . . ?
N1 C2 C1 112.78(14) . . ?
C3 C2 C1 109.78(15) . . ?
O2 C3 O3 124.73(19) . . ?
O2 C3 C2 124.50(19) . . ?
O3 C3 C2 110.75(16) . . ?
C6 C5 C9 117.51(17) . . ?
C6 C5 C1 120.50(16) . . ?
C9 C5 C1 121.99(17) . . ?
C5 C6 C7 119.52(18) . . ?
C8 C7 C6 118.51(19) . . ?
N2 C8 C7 123.29(19) . . ?
N2 C9 C5 123.37(19) . . ?
O4 C10 N1 121.81(17) . . ?
O4 C10 C11 121.12(17) . . ?
N1 C10 C11 117.06(17) . . ?
C16 C11 C12 119.15(18) . . ?
C16 C11 C10 117.59(17) . . ?
C12 C11 C10 123.25(17) . . ?
C13 C12 C11 120.28(19) . . ?
C14 C13 C12 120.1(2) . . ?
C13 C14 C15 119.9(2) . . ?
C16 C15 C14 120.1(2) . . ?
C15 C16 C11 120.38(19) . . ?

