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

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

data_131005lt_0m
_database_code_depnum_ccdc_archive 'CCDC 1437539'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H27 N3 O4 S2'
_chemical_formula_weight         521.64

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8347(3)
_cell_length_b                   10.7763(4)
_cell_length_c                   13.3710(4)
_cell_angle_alpha                77.323(2)
_cell_angle_beta                 76.332(2)
_cell_angle_gamma                67.333(2)
_cell_volume                     1257.50(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4853
_cell_measurement_theta_min      3.1685
_cell_measurement_theta_max      26.2574

_exptl_crystal_description       Tabullar
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             548
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8843
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_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            19210
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         26.44
_reflns_number_total             5143
_reflns_number_gt                4298
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0848P)²+0.1259P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5143
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1518
_refine_ls_wR_factor_gt          0.1182
_refine_ls_goodness_of_fit_ref   1.203
_refine_ls_restrained_S_all      1.203
_refine_ls_shift/su_max          0.005
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.22070(5) 0.31601(5) 0.70120(4) 0.01527(16) Uani 1 1 d . . .
S2 S 0.58023(6) 0.61207(5) 0.71944(4) 0.01868(17) Uani 1 1 d . . .
O1 O 0.19626(15) 0.45662(14) 0.69510(11) 0.0192(3) Uani 1 1 d . . .
O2 O 0.10734(16) 0.27852(15) 0.67947(12) 0.0214(4) Uani 1 1 d . . .
O3 O 0.59978(18) 0.74066(16) 0.68979(13) 0.0277(4) Uani 1 1 d . . .
O4 O 0.43320(16) 0.60606(16) 0.74853(12) 0.0234(4) Uani 1 1 d . . .
N1 N 0.37296(18) 0.24962(17) 0.61775(13) 0.0161(4) Uani 1 1 d . . .
N2 N 0.66571(18) 0.52766(18) 0.61912(13) 0.0162(4) Uani 1 1 d . . .
N3 N 0.62683(18) 0.15029(17) 0.62863(12) 0.0154(4) Uani 1 1 d . . .
C1 C 0.3415(3) 0.0541(4) 1.1344(2) 0.0563(9) Uani 1 1 d . . .
H1A H 0.4262 0.0695 1.1492 0.085 Uiso 1 1 calc R . .
H1B H 0.3619 -0.0437 1.1429 0.085 Uiso 1 1 calc R . .
H1C H 0.2510 0.0964 1.1826 0.085 Uiso 1 1 calc R . .
C2 C 0.3187(3) 0.1161(3) 1.02434(19) 0.0379(7) Uani 1 1 d . . .
C3 C 0.3452(3) 0.2343(3) 0.97929(18) 0.0335(6) Uani 1 1 d . . .
H3 H 0.3842 0.2745 1.0168 0.040 Uiso 1 1 calc R . .
C4 C 0.3161(2) 0.2953(3) 0.88088(17) 0.0251(5) Uani 1 1 d . . .
H4 H 0.3348 0.3768 0.8508 0.030 Uiso 1 1 calc R . .
C5 C 0.2589(2) 0.2358(2) 0.82594(16) 0.0198(5) Uani 1 1 d . . .
C6 C 0.5092(2) 0.2659(2) 0.62394(15) 0.0153(4) Uani 1 1 d . . .
C7 C 0.5152(2) 0.3929(2) 0.62003(15) 0.0154(4) Uani 1 1 d . . .
H7 H 0.4296 0.4730 0.6136 0.019 Uiso 1 1 calc R . .
C8 C 0.6515(2) 0.3983(2) 0.62592(15) 0.0148(4) Uani 1 1 d . . .
C9 C 0.6795(2) 0.5195(2) 0.82210(16) 0.0189(5) Uani 1 1 d . . .
C10 C 0.6285(3) 0.4269(2) 0.89337(18) 0.0263(5) Uani 1 1 d . . .
H10 H 0.5416 0.4128 0.8867 0.032 Uiso 1 1 calc R . .
C11 C 0.7046(3) 0.3545(3) 0.97464(19) 0.0306(6) Uani 1 1 d . . .
H11 H 0.6680 0.2918 1.0242 0.037 Uiso 1 1 calc R . .
C12 C 0.8329(2) 0.3712(2) 0.98548(17) 0.0261(5) Uani 1 1 d . . .
C13 C 0.9098(3) 0.2967(3) 1.07670(19) 0.0393(7) Uani 1 1 d . . .
H13A H 0.8529 0.3393 1.1387 0.059 Uiso 1 1 calc R . .
H13B H 1.0108 0.3002 1.0625 0.059 Uiso 1 1 calc R . .
H13C H 0.9160 0.2017 1.0886 0.059 Uiso 1 1 calc R . .
C14 C 0.7601(2) 0.1568(2) 0.63086(14) 0.0145(4) Uani 1 1 d . . .
C15 C 0.7758(2) 0.2793(2) 0.63186(15) 0.0156(4) Uani 1 1 d . . .
H15 H 0.8696 0.2818 0.6365 0.019 Uiso 1 1 calc R . .
C16 C 0.8844(3) 0.4623(3) 0.91097(18) 0.0281(6) Uani 1 1 d . . .
H16 H 0.9740 0.4732 0.9156 0.034 Uiso 1 1 calc R . .
C17 C 0.8082(2) 0.5377(2) 0.82997(17) 0.0248(5) Uani 1 1 d . . .
H17 H 0.8439 0.6011 0.7806 0.030 Uiso 1 1 calc R . .
C18 C 0.8132(2) 0.5374(2) 0.57041(17) 0.0198(5) Uani 1 1 d . . .
H18A H 0.8837 0.4915 0.6193 0.030 Uiso 1 1 calc R . .
H18B H 0.8037 0.6332 0.5522 0.030 Uiso 1 1 calc R . .
H18C H 0.8501 0.4939 0.5073 0.030 Uiso 1 1 calc R . .
C19 C 0.8883(2) 0.0265(2) 0.63360(15) 0.0148(4) Uani 1 1 d . . .
C20 C 0.8748(2) -0.0895(2) 0.61365(16) 0.0184(5) Uani 1 1 d . . .
H20 H 0.7834 -0.0849 0.5981 0.022 Uiso 1 1 calc R . .
C21 C 0.9944(2) -0.2118(2) 0.61643(16) 0.0202(5) Uani 1 1 d . . .
H21 H 0.9840 -0.2903 0.6027 0.024 Uiso 1 1 calc R . .
C22 C 1.1282(2) -0.2211(2) 0.63878(16) 0.0205(5) Uani 1 1 d . . .
H22 H 1.2094 -0.3053 0.6407 0.025 Uiso 1 1 calc R . .
C23 C 1.1428(2) -0.1070(2) 0.65831(18) 0.0235(5) Uani 1 1 d . . .
H23 H 1.2348 -0.1124 0.6732 0.028 Uiso 1 1 calc R . .
C24 C 1.0239(2) 0.0158(2) 0.65635(17) 0.0212(5) Uani 1 1 d . . .
H24 H 1.0351 0.0936 0.6707 0.025 Uiso 1 1 calc R . .
C25 C 0.3915(3) 0.1203(2) 0.58642(18) 0.0228(5) Uani 1 1 d . . .
H25A H 0.4657 0.1051 0.5227 0.034 Uiso 1 1 calc R . .
H25B H 0.2956 0.1244 0.5737 0.034 Uiso 1 1 calc R . .
H25C H 0.4254 0.0456 0.6420 0.034 Uiso 1 1 calc R . .
C26 C 0.2321(3) 0.1164(2) 0.86817(18) 0.0288(6) Uani 1 1 d . . .
H26 H 0.1939 0.0761 0.8301 0.035 Uiso 1 1 calc R . .
C27 C 0.2625(3) 0.0568(3) 0.9678(2) 0.0398(7) Uani 1 1 d . . .
H27 H 0.2449 -0.0252 0.9979 0.048 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4265(15) . ?
S1 O2 1.4290(15) . ?
S1 N1 1.6535(17) . ?
S1 C5 1.756(2) . ?
S2 O3 1.4292(17) . ?
S2 O4 1.4288(15) . ?
S2 N2 1.6573(17) . ?
S2 C9 1.765(2) . ?
N1 C6 1.440(3) . ?
N1 C25 1.475(3) . ?
N2 C8 1.435(3) . ?
N2 C18 1.477(3) . ?
N3 C6 1.336(3) . ?
N3 C14 1.347(3) . ?
C1 C2 1.506(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.378(4) . ?
C2 C27 1.402(4) . ?
C3 C4 1.378(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(3) . ?
C4 H4 0.9500 . ?
C5 C26 1.383(3) . ?
C6 C7 1.381(3) . ?
C7 C8 1.386(3) . ?
C7 H7 0.9500 . ?
C8 C15 1.392(3) . ?
C9 C10 1.377(3) . ?
C9 C17 1.385(3) . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(3) . ?
C11 H11 0.9500 . ?
C12 C16 1.388(3) . ?
C12 C13 1.498(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.390(3) . ?
C14 C19 1.483(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C24 1.394(3) . ?
C19 C20 1.394(3) . ?
C20 C21 1.388(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.376(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.393(4) . ?
C26 H26 0.9500 . ?
C27 H27 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
O1 S1 O2 118.91(9) . . ?
O1 S1 N1 108.18(9) . . ?
O2 S1 N1 105.88(9) . . ?
O1 S1 C5 107.88(10) . . ?
O2 S1 C5 108.56(10) . . ?
N1 S1 C5 106.84(9) . . ?
O3 S2 O4 120.03(10) . . ?
O3 S2 N2 106.03(9) . . ?
O4 S2 N2 107.59(9) . . ?
O3 S2 C9 108.90(10) . . ?
O4 S2 C9 107.66(10) . . ?
N2 S2 C9 105.78(9) . . ?
C6 N1 C25 115.48(16) . . ?
C6 N1 S1 118.61(13) . . ?
C25 N1 S1 116.64(14) . . ?
C8 N2 C18 116.30(16) . . ?
C8 N2 S2 117.02(13) . . ?
C18 N2 S2 114.98(14) . . ?
C6 N3 C14 118.29(18) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C27 118.8(2) . . ?
C3 C2 C1 121.3(3) . . ?
C27 C2 C1 119.8(3) . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C26 C5 C4 121.2(2) . . ?
C26 C5 S1 120.28(18) . . ?
C4 C5 S1 118.51(18) . . ?
N3 C6 C7 124.26(19) . . ?
N3 C6 N1 114.36(18) . . ?
C7 C6 N1 121.30(18) . . ?
C6 C7 C8 117.07(19) . . ?
C6 C7 H7 121.5 . . ?
C8 C7 H7 121.5 . . ?
C7 C8 C15 119.90(19) . . ?
C7 C8 N2 119.58(18) . . ?
C15 C8 N2 120.40(18) . . ?
C10 C9 C17 120.4(2) . . ?
C10 C9 S2 119.05(17) . . ?
C17 C9 S2 120.55(17) . . ?
C9 C10 C11 119.6(2) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 121.5(2) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C16 117.8(2) . . ?
C11 C12 C13 120.7(2) . . ?
C16 C12 C13 121.5(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 121.59(18) . . ?
N3 C14 C19 116.50(18) . . ?
C15 C14 C19 121.91(19) . . ?
C14 C15 C8 118.80(19) . . ?
C14 C15 H15 120.6 . . ?
C8 C15 H15 120.6 . . ?
C17 C16 C12 121.6(2) . . ?
C17 C16 H16 119.2 . . ?
C12 C16 H16 119.2 . . ?
C9 C17 C16 119.1(2) . . ?
C9 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 118.34(19) . . ?
C24 C19 C14 121.63(19) . . ?
C20 C19 C14 120.04(19) . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 120.9(2) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C23 C22 C21 119.3(2) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C24 120.5(2) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C19 120.8(2) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C5 C26 C27 118.4(2) . . ?
C5 C26 H26 120.8 . . ?
C27 C26 H26 120.8 . . ?
C26 C27 C2 121.0(3) . . ?
C26 C27 H27 119.5 . . ?
C2 C27 H27 119.5 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.44
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.141
####################################################################### 
# 
# 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_150416LT_a
_database_code_depnum_ccdc_archive 'CCDC 1446058'
_audit_update_record             
;
2016-01-08 deposited with the CCDC.
2016-01-25 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            'C10 H12 N2 O5'
_chemical_formula_weight         240.22

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   13.782(4)
_cell_length_b                   18.539(5)
_cell_length_c                   3.9890(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1019.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1661
_cell_measurement_theta_min      3.1538
_cell_measurement_theta_max      24.3426

_exptl_crystal_description       Acicular
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7676
_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            5305
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         1.841
_diffrn_reflns_theta_max         26.645
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1680
_reflns_number_gt                1465
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_max     0.966
_reflns_Friedel_fraction_full    0.990

_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       'APEX2 (Bruker AXS, 2010)'
_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    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0411P)²+0.2789P] 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   -1(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1680
_refine_ls_number_parameters     156
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0880
_refine_ls_wR_factor_gt          0.0837
_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
C1 C 0.6329(2) 0.10234(16) 0.0316(8) 0.0178(7) Uani 1 1 d . . . . .
C2 C 0.4692(2) 0.10290(15) 0.1488(9) 0.0206(7) Uani 1 1 d . . . . .
H2A H 0.4499 0.0728 0.3429 0.025 Uiso 1 1 calc R U . . .
H2B H 0.4119 0.1103 0.0029 0.025 Uiso 1 1 calc R U . . .
C3 C 0.51058(18) 0.17472(14) 0.2647(9) 0.0169(7) Uani 1 1 d . . . . .
H3A H 0.4877 0.2149 0.1217 0.020 Uiso 1 1 calc R U . . .
H3B H 0.4932 0.1848 0.5009 0.020 Uiso 1 1 calc R U . . .
C4 C 0.68415(19) 0.21306(15) 0.3429(8) 0.0156(6) Uani 1 1 d . . . . .
C5 C 0.78940(19) 0.19307(17) 0.3069(10) 0.0229(7) Uani 1 1 d . . . . .
H5A H 0.8295 0.2284 0.4259 0.034 Uiso 1 1 calc R U . . .
H5B H 0.8070 0.1927 0.0689 0.034 Uiso 1 1 calc R U . . .
H5C H 0.8002 0.1450 0.4024 0.034 Uiso 1 1 calc R U . . .
C6 C 0.65002(19) 0.27366(16) 0.4862(8) 0.0166(7) Uani 1 1 d . . . . .
H6 H 0.5816 0.2793 0.4948 0.020 Uiso 1 1 calc R U . . .
C7 C 0.7086(2) 0.33155(15) 0.6295(9) 0.0156(6) Uani 1 1 d . . . . .
C8 C 0.71034(19) 0.44768(14) 0.9403(9) 0.0179(7) Uani 1 1 d . . . . .
H8A H 0.7520 0.4719 0.7724 0.022 Uiso 1 1 calc R U . . .
H8B H 0.7507 0.4317 1.1318 0.022 Uiso 1 1 calc R U . . .
C9 C 0.62753(18) 0.49645(16) 1.0544(9) 0.0188(7) Uani 1 1 d . . . . .
H9A H 0.6421 0.5183 1.2752 0.023 Uiso 1 1 calc R U . . .
H9B H 0.6160 0.5355 0.8898 0.023 Uiso 1 1 calc R U . . .
C10 C 0.55939(19) 0.38822(15) 0.8959(9) 0.0162(7) Uani 1 1 d . . . . .
N1 N 0.61555(16) 0.16306(13) 0.2265(7) 0.0160(6) Uani 1 1 d . . . . .
N2 N 0.65641(15) 0.38714(12) 0.7917(7) 0.0154(6) Uani 1 1 d . . . . .
O1 O 0.54803(13) 0.06920(11) -0.0364(6) 0.0219(5) Uani 1 1 d . . . . .
O2 O 0.70873(14) 0.08002(11) -0.0742(7) 0.0228(5) Uani 1 1 d . . . . .
O3 O 0.79713(13) 0.33864(10) 0.6168(7) 0.0215(5) Uani 1 1 d . . . . .
O4 O 0.49636(13) 0.34448(10) 0.8473(6) 0.0220(5) Uani 1 1 d . . . . .
O5 O 0.54370(13) 0.44874(10) 1.0761(7) 0.0195(5) Uani 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
C1 O2 1.201(3) . ?
C1 O1 1.349(3) . ?
C1 N1 1.389(4) . ?
C2 O1 1.455(3) . ?
C2 C3 1.521(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N1 1.471(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C6 1.345(4) . ?
C4 N1 1.403(4) . ?
C4 C5 1.504(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.460(4) . ?
C6 H6 0.9500 . ?
C7 O3 1.228(3) . ?
C7 N2 1.414(4) . ?
C8 N2 1.471(4) . ?
C8 C9 1.525(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O5 1.458(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O4 1.204(3) . ?
C10 O5 1.350(4) . ?
C10 N2 1.400(4) . ?

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
O2 C1 O1 121.8(3) . . ?
O2 C1 N1 128.7(3) . . ?
O1 C1 N1 109.4(2) . . ?
O1 C2 C3 104.5(2) . . ?
O1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
O1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
N1 C3 C2 102.1(2) . . ?
N1 C3 H3A 111.4 . . ?
C2 C3 H3A 111.4 . . ?
N1 C3 H3B 111.4 . . ?
C2 C3 H3B 111.4 . . ?
H3A C3 H3B 109.2 . . ?
C6 C4 N1 117.2(2) . . ?
C6 C4 C5 125.7(3) . . ?
N1 C4 C5 117.1(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 C7 125.9(2) . . ?
C4 C6 H6 117.0 . . ?
C7 C6 H6 117.0 . . ?
O3 C7 N2 116.5(3) . . ?
O3 C7 C6 127.7(3) . . ?
N2 C7 C6 115.7(2) . . ?
N2 C8 C9 101.2(2) . . ?
N2 C8 H8A 111.5 . . ?
C9 C8 H8A 111.5 . . ?
N2 C8 H8B 111.5 . . ?
C9 C8 H8B 111.5 . . ?
H8A C8 H8B 109.3 . . ?
O5 C9 C8 104.5(2) . . ?
O5 C9 H9A 110.8 . . ?
C8 C9 H9A 110.8 . . ?
O5 C9 H9B 110.8 . . ?
C8 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
O4 C10 O5 122.0(3) . . ?
O4 C10 N2 129.2(3) . . ?
O5 C10 N2 108.8(2) . . ?
C1 N1 C4 127.2(2) . . ?
C1 N1 C3 110.3(2) . . ?
C4 N1 C3 122.1(2) . . ?
C10 N2 C7 129.2(2) . . ?
C10 N2 C8 110.6(2) . . ?
C7 N2 C8 118.9(2) . . ?
C1 O1 C2 110.5(2) . . ?
C10 O5 C9 110.2(2) . . ?

_refine_diff_density_max         0.179
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.047

_shelxl_version_number           2014/6

