# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_Ted1962
_database_code_depnum_ccdc_archive 'CCDC 1557879'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
anti-4,7-bis(methoxymethyl)-2-methylhexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione
_chemical_name_common            
anti-N-methyl-4,7-bis(methoxymethyl)norcantharimide
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H19 N O5'
_chemical_formula_sum            'C13 H19 N O5'
_chemical_formula_weight         269.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 '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 0.0130 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0210 0.0120 '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                   10.389(2)
_cell_length_b                   15.957(3)
_cell_length_c                   8.4911(17)
_cell_angle_alpha                90
_cell_angle_beta                 111.16(3)
_cell_angle_gamma                90
_cell_volume                     1312.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    500
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      31.8

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.223
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   'Scala (Evans, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96990
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10961
_diffrn_reflns_av_unetI/netI     0.1381
_diffrn_reflns_av_R_equivalents  0.0936
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.742
_diffrn_reflns_theta_max         38.407
_diffrn_reflns_theta_full        35.587
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             2578
_reflns_number_gt                1924
_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       'Marccd (Doyle, 2011)'
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  SHELXTL
_refine_special_details          
;
 Refined as a 2-component 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)+(0.0548P)²+0.7069P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.084(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2578
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0878
_refine_ls_wR_factor_ref         0.2168
_refine_ls_wR_factor_gt          0.2002
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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 0.3742(3) 0.62997(16) 0.9709(4) 0.0327(7) Uani 1 1 d . . . . .
O1 O 0.49098(19) 0.61449(12) 1.0701(2) 0.0389(6) Uani 1 1 d . . . . .
N2 N 0.2541(2) 0.60264(14) 0.9928(3) 0.0318(6) Uani 1 1 d . . . . .
C3 C 0.1339(3) 0.62783(16) 0.8614(4) 0.0322(7) Uani 1 1 d . . . . .
O3 O 0.01681(18) 0.61083(12) 0.8530(3) 0.0384(6) Uani 1 1 d . . . . .
C3A C 0.1750(2) 0.67858(16) 0.7374(3) 0.0308(6) Uani 1 1 d . . . . .
H3A H 0.1364 0.7366 0.7260 0.037 Uiso 1 1 calc R U . . .
C4 C 0.1455(2) 0.63779(15) 0.5601(3) 0.0289(6) Uani 1 1 d . . . . .
C5 C 0.1806(2) 0.54329(15) 0.5771(3) 0.0301(6) Uani 1 1 d . . . . .
H5A H 0.1451 0.5148 0.4661 0.036 Uiso 1 1 calc R U . . .
H5B H 0.1430 0.5153 0.6553 0.036 Uiso 1 1 calc R U . . .
C6 C 0.3418(2) 0.54494(15) 0.6506(3) 0.0302(6) Uani 1 1 d . . . . .
H6A H 0.3789 0.5178 0.7629 0.036 Uiso 1 1 calc R U . . .
H6B H 0.3810 0.5174 0.5736 0.036 Uiso 1 1 calc R U . . .
C7 C 0.3705(2) 0.64033(16) 0.6630(3) 0.0300(6) Uani 1 1 d . . . . .
C7A C 0.3345(2) 0.67996(15) 0.8094(3) 0.0299(7) Uani 1 1 d . . . . .
H7A H 0.3700 0.7387 0.8323 0.036 Uiso 1 1 calc R U . . .
O8 O 0.25852(16) 0.67276(11) 0.5175(2) 0.0289(5) Uani 1 1 d . . . . .
C9 C 0.2545(3) 0.55328(19) 1.1388(4) 0.0405(7) Uani 1 1 d . . . . .
H9A H 0.2892 0.5879 1.2409 0.061 Uiso 1 1 calc R U . . .
H9B H 0.3143 0.5042 1.1520 0.061 Uiso 1 1 calc R U . . .
H9C H 0.1604 0.5348 1.1210 0.061 Uiso 1 1 calc R U . . .
C10 C 0.0072(2) 0.66169(17) 0.4297(3) 0.0308(6) Uani 1 1 d . . . . .
H10A H -0.0679 0.6417 0.4661 0.037 Uiso 1 1 calc R U . . .
H10B H 0.0002 0.7234 0.4185 0.037 Uiso 1 1 calc R U . . .
O10 O -0.00699(17) 0.62522(12) 0.2716(2) 0.0343(5) Uani 1 1 d . . . . .
C11 C -0.1335(3) 0.64878(19) 0.1415(4) 0.0402(7) Uani 1 1 d . . . . .
H11A H -0.1381 0.6236 0.0343 0.060 Uiso 1 1 calc R U . . .
H11B H -0.1377 0.7100 0.1305 0.060 Uiso 1 1 calc R U . . .
H11C H -0.2114 0.6289 0.1705 0.060 Uiso 1 1 calc R U . . .
C12 C 0.5098(2) 0.66696(16) 0.6603(3) 0.0302(6) Uani 1 1 d . . . . .
H12A H 0.5154 0.7289 0.6589 0.036 Uiso 1 1 calc R U . . .
H12B H 0.5843 0.6462 0.7628 0.036 Uiso 1 1 calc R U . . .
O12 O 0.52608(18) 0.63316(11) 0.5130(3) 0.0361(6) Uani 1 1 d . . . . .
C13 C 0.6524(3) 0.66026(17) 0.4986(4) 0.0372(7) Uani 1 1 d . . . . .
H13A H 0.6594 0.6374 0.3949 0.056 Uiso 1 1 calc R U . . .
H13B H 0.7304 0.6404 0.5963 0.056 Uiso 1 1 calc R U . . .
H13C H 0.6540 0.7216 0.4945 0.056 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.227(3) . ?
C1 N2 1.395(3) . ?
C1 C7A 1.510(4) . ?
N2 C3 1.401(3) . ?
N2 C9 1.468(4) . ?
C3 O3 1.223(3) . ?
C3 C3A 1.507(4) . ?
C3A C7A 1.545(3) . ?
C3A C4 1.565(4) . ?
C3A H3A 1.0000 . ?
C4 O8 1.459(3) . ?
C4 C10 1.513(3) . ?
C4 C5 1.546(3) . ?
C5 C6 1.562(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.547(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O8 1.453(3) . ?
C7 C12 1.516(3) . ?
C7 C7A 1.556(4) . ?
C7A H7A 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 O10 1.421(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
O10 C11 1.428(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O12 1.427(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
O12 C13 1.428(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
O1 C1 N2 123.7(3) . . ?
O1 C1 C7A 127.5(2) . . ?
N2 C1 C7A 108.8(2) . . ?
C1 N2 C3 112.8(2) . . ?
C1 N2 C9 123.4(2) . . ?
C3 N2 C9 123.8(2) . . ?
O3 C3 N2 124.4(3) . . ?
O3 C3 C3A 127.3(2) . . ?
N2 C3 C3A 108.3(2) . . ?
C3 C3A C7A 105.4(2) . . ?
C3 C3A C4 116.2(2) . . ?
C7A C3A C4 101.30(19) . . ?
C3 C3A H3A 111.1 . . ?
C7A C3A H3A 111.1 . . ?
C4 C3A H3A 111.1 . . ?
O8 C4 C10 111.0(2) . . ?
O8 C4 C5 102.28(18) . . ?
C10 C4 C5 116.3(2) . . ?
O8 C4 C3A 100.61(19) . . ?
C10 C4 C3A 113.8(2) . . ?
C5 C4 C3A 111.0(2) . . ?
C4 C5 C6 101.73(17) . . ?
C4 C5 H5A 111.4 . . ?
C6 C5 H5A 111.4 . . ?
C4 C5 H5B 111.4 . . ?
C6 C5 H5B 111.4 . . ?
H5A C5 H5B 109.3 . . ?
C7 C6 C5 101.34(17) . . ?
C7 C6 H6A 111.5 . . ?
C5 C6 H6A 111.5 . . ?
C7 C6 H6B 111.5 . . ?
C5 C6 H6B 111.5 . . ?
H6A C6 H6B 109.3 . . ?
O8 C7 C12 111.3(2) . . ?
O8 C7 C6 102.52(19) . . ?
C12 C7 C6 115.9(2) . . ?
O8 C7 C7A 100.66(19) . . ?
C12 C7 C7A 113.8(2) . . ?
C6 C7 C7A 111.0(2) . . ?
C1 C7A C3A 104.7(2) . . ?
C1 C7A C7 116.4(2) . . ?
C3A C7A C7 102.2(2) . . ?
C1 C7A H7A 111.0 . . ?
C3A C7A H7A 111.0 . . ?
C7 C7A H7A 111.0 . . ?
C7 O8 C4 96.99(18) . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O10 C10 C4 109.6(2) . . ?
O10 C10 H10A 109.8 . . ?
C4 C10 H10A 109.8 . . ?
O10 C10 H10B 109.8 . . ?
C4 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C10 O10 C11 112.0(2) . . ?
O10 C11 H11A 109.5 . . ?
O10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O12 C12 C7 108.9(2) . . ?
O12 C12 H12A 109.9 . . ?
C7 C12 H12A 109.9 . . ?
O12 C12 H12B 109.9 . . ?
C7 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C12 O12 C13 111.4(2) . . ?
O12 C13 H13A 109.5 . . ?
O12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
O1 C1 N2 C3 -179.4(2) . . . . ?
C7A C1 N2 C3 0.6(3) . . . . ?
O1 C1 N2 C9 1.0(4) . . . . ?
C7A C1 N2 C9 -179.0(2) . . . . ?
C1 N2 C3 O3 179.6(2) . . . . ?
C9 N2 C3 O3 -0.8(4) . . . . ?
C1 N2 C3 C3A -0.8(3) . . . . ?
C9 N2 C3 C3A 178.8(2) . . . . ?
O3 C3 C3A C7A -179.8(3) . . . . ?
N2 C3 C3A C7A 0.6(3) . . . . ?
O3 C3 C3A C4 -68.6(3) . . . . ?
N2 C3 C3A C4 111.8(2) . . . . ?
C3 C3A C4 O8 -148.8(2) . . . . ?
C7A C3A C4 O8 -35.2(2) . . . . ?
C3 C3A C4 C10 92.4(3) . . . . ?
C7A C3A C4 C10 -154.0(2) . . . . ?
C3 C3A C4 C5 -41.1(3) . . . . ?
C7A C3A C4 C5 72.4(2) . . . . ?
O8 C4 C5 C6 34.0(2) . . . . ?
C10 C4 C5 C6 155.2(2) . . . . ?
C3A C4 C5 C6 -72.6(2) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 O8 -34.3(2) . . . . ?
C5 C6 C7 C12 -155.7(2) . . . . ?
C5 C6 C7 C7A 72.4(2) . . . . ?
O1 C1 C7A C3A 179.8(3) . . . . ?
N2 C1 C7A C3A -0.2(3) . . . . ?
O1 C1 C7A C7 67.9(3) . . . . ?
N2 C1 C7A C7 -112.2(2) . . . . ?
C3 C3A C7A C1 -0.2(3) . . . . ?
C4 C3A C7A C1 -121.7(2) . . . . ?
C3 C3A C7A C7 121.6(2) . . . . ?
C4 C3A C7A C7 0.1(2) . . . . ?
O8 C7 C7A C1 148.6(2) . . . . ?
C12 C7 C7A C1 -92.3(3) . . . . ?
C6 C7 C7A C1 40.6(3) . . . . ?
O8 C7 C7A C3A 35.1(2) . . . . ?
C12 C7 C7A C3A 154.3(2) . . . . ?
C6 C7 C7A C3A -72.8(2) . . . . ?
C12 C7 O8 C4 -179.27(19) . . . . ?
C6 C7 O8 C4 56.2(2) . . . . ?
C7A C7 O8 C4 -58.3(2) . . . . ?
C10 C4 O8 C7 179.2(2) . . . . ?
C5 C4 O8 C7 -56.0(2) . . . . ?
C3A C4 O8 C7 58.4(2) . . . . ?
O8 C4 C10 O10 64.4(3) . . . . ?
C5 C4 C10 O10 -52.0(3) . . . . ?
C3A C4 C10 O10 177.0(2) . . . . ?
C4 C10 O10 C11 -177.4(2) . . . . ?
O8 C7 C12 O12 -61.8(3) . . . . ?
C6 C7 C12 O12 54.7(3) . . . . ?
C7A C7 C12 O12 -174.7(2) . . . . ?
C7 C12 O12 C13 176.6(2) . . . . ?

_refine_diff_density_max         0.319
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.073

_shelxl_version_number           2014/6

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

data_Ted1937
_database_code_depnum_ccdc_archive 'CCDC 1557878'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
endo-4,7-bis(hydroxymethyl)hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione
_chemical_name_common            bis(hydroxymethyl)norcantharimide
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H13 N O5'
_chemical_formula_sum            'C10 H13 N O5'
_chemical_formula_weight         227.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 '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 0.0130 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0210 0.0120 '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                   11.602(2)
_cell_length_b                   7.6108(15)
_cell_length_c                   11.152(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.45(3)
_cell_angle_gamma                90
_cell_volume                     980.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      4.4
_cell_measurement_theta_max      34.0

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.269
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'Scala (Evans, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96990
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5203
_diffrn_reflns_av_unetI/netI     0.1699
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.431
_diffrn_reflns_theta_max         38.358
_diffrn_reflns_theta_full        35.587
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             1993
_reflns_number_gt                1373
_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       'Marccd (Doyle, 2011)'
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  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)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.010(1)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1993
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.1342
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   0.876
_refine_ls_restrained_S_all      0.876
_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 0.45705(15) 0.3873(3) 0.65057(18) 0.0147(5) Uani 1 1 d . . . . .
O1 O 0.52964(10) 0.50450(19) 0.65792(13) 0.0206(4) Uani 1 1 d . . . . .
N2 N 0.46494(12) 0.2332(2) 0.58533(16) 0.0159(5) Uani 1 1 d . . . . .
H2 H 0.5198(16) 0.206(3) 0.547(2) 0.019 Uiso 1 1 d . U . . .
C3 C 0.37200(15) 0.1214(3) 0.58908(19) 0.0165(5) Uani 1 1 d . . . . .
O3 O 0.36319(10) -0.02307(19) 0.54058(14) 0.0215(4) Uani 1 1 d . . . . .
C3A C 0.28540(14) 0.2085(2) 0.66287(18) 0.0136(5) Uani 1 1 d . . . . .
H3A H 0.2666 0.1314 0.7309 0.016 Uiso 1 1 calc R U . . .
C4 C 0.17321(14) 0.2802(3) 0.59167(18) 0.0140(5) Uani 1 1 d . . . . .
C5 C 0.20192(15) 0.3828(3) 0.47859(19) 0.0186(5) Uani 1 1 d . . . . .
H5A H 0.1319 0.4015 0.4221 0.022 Uiso 1 1 calc R U . . .
H5B H 0.2612 0.3211 0.4361 0.022 Uiso 1 1 calc R U . . .
C6 C 0.24934(16) 0.5600(3) 0.5337(2) 0.0187(5) Uani 1 1 d . . . . .
H6A H 0.3284 0.5847 0.5117 0.022 Uiso 1 1 calc R U . . .
H6B H 0.1978 0.6595 0.5081 0.022 Uiso 1 1 calc R U . . .
C7 C 0.24913(14) 0.5231(3) 0.66889(19) 0.0145(5) Uani 1 1 d . . . . .
C7A C 0.34426(14) 0.3811(3) 0.71009(18) 0.0142(5) Uani 1 1 d . . . . .
H7A H 0.3597 0.3789 0.7998 0.017 Uiso 1 1 calc R U . . .
O8 O 0.14448(10) 0.41839(17) 0.67218(12) 0.0155(4) Uani 1 1 d . . . . .
C9 C 0.07450(15) 0.1528(3) 0.5683(2) 0.0190(5) Uani 1 1 d . . . . .
H9A H 0.0094 0.2125 0.5209 0.023 Uiso 1 1 calc R U . . .
H9B H 0.0997 0.0537 0.5195 0.023 Uiso 1 1 calc R U . . .
O9 O 0.03528(11) 0.0858(2) 0.67640(14) 0.0219(4) Uani 1 1 d . . . . .
H9 H 0.0673(19) -0.008(4) 0.697(2) 0.033 Uiso 1 1 d . U . . .
C10 C 0.24230(15) 0.6783(3) 0.7527(2) 0.0179(5) Uani 1 1 d . . . . .
H10A H 0.2499 0.6365 0.8372 0.022 Uiso 1 1 calc R U . . .
H10B H 0.3073 0.7595 0.7426 0.022 Uiso 1 1 calc R U . . .
O10 O 0.13471(11) 0.7708(2) 0.72881(14) 0.0232(4) Uani 1 1 d . . . . .
H10 H 0.0814(18) 0.706(3) 0.747(2) 0.035 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.224(2) . ?
C1 N2 1.388(3) . ?
C1 C7A 1.523(3) . ?
N2 C3 1.378(2) . ?
N2 H2 0.83(2) . ?
C3 O3 1.225(2) . ?
C3 C3A 1.511(3) . ?
C3A C7A 1.550(3) . ?
C3A C4 1.558(2) . ?
C3A H3A 1.0000 . ?
C4 O8 1.442(2) . ?
C4 C9 1.504(2) . ?
C4 C5 1.546(3) . ?
C5 C6 1.560(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.534(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O8 1.456(2) . ?
C7 C10 1.513(3) . ?
C7 C7A 1.581(2) . ?
C7A H7A 1.0000 . ?
C9 O9 1.423(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
O9 H9 0.83(3) . ?
C10 O10 1.436(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
O10 H10 0.83(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N2 124.86(18) . . ?
O1 C1 C7A 127.41(18) . . ?
N2 C1 C7A 107.73(15) . . ?
C3 N2 C1 114.55(17) . . ?
C3 N2 H2 120.1(15) . . ?
C1 N2 H2 125.3(15) . . ?
O3 C3 N2 125.02(19) . . ?
O3 C3 C3A 127.02(17) . . ?
N2 C3 C3A 107.97(17) . . ?
C3 C3A C7A 105.22(14) . . ?
C3 C3A C4 116.28(16) . . ?
C7A C3A C4 101.30(14) . . ?
C3 C3A H3A 111.1 . . ?
C7A C3A H3A 111.1 . . ?
C4 C3A H3A 111.1 . . ?
O8 C4 C9 111.15(15) . . ?
O8 C4 C5 102.69(15) . . ?
C9 C4 C5 113.80(15) . . ?
O8 C4 C3A 99.76(14) . . ?
C9 C4 C3A 116.62(16) . . ?
C5 C4 C3A 111.00(14) . . ?
C4 C5 C6 102.15(16) . . ?
C4 C5 H5A 111.3 . . ?
C6 C5 H5A 111.3 . . ?
C4 C5 H5B 111.3 . . ?
C6 C5 H5B 111.3 . . ?
H5A C5 H5B 109.2 . . ?
C7 C6 C5 101.27(16) . . ?
C7 C6 H6A 111.5 . . ?
C5 C6 H6A 111.5 . . ?
C7 C6 H6B 111.5 . . ?
C5 C6 H6B 111.5 . . ?
H6A C6 H6B 109.3 . . ?
O8 C7 C10 108.61(15) . . ?
O8 C7 C6 101.79(13) . . ?
C10 C7 C6 117.98(18) . . ?
O8 C7 C7A 100.36(14) . . ?
C10 C7 C7A 115.46(15) . . ?
C6 C7 C7A 110.16(16) . . ?
C1 C7A C3A 104.31(16) . . ?
C1 C7A C7 117.21(16) . . ?
C3A C7A C7 101.98(12) . . ?
C1 C7A H7A 110.9 . . ?
C3A C7A H7A 110.9 . . ?
C7 C7A H7A 110.9 . . ?
C4 O8 C7 98.10(13) . . ?
O9 C9 C4 112.54(16) . . ?
O9 C9 H9A 109.1 . . ?
C4 C9 H9A 109.1 . . ?
O9 C9 H9B 109.1 . . ?
C4 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C9 O9 H9 112.2(18) . . ?
O10 C10 C7 111.32(14) . . ?
O10 C10 H10A 109.4 . . ?
C7 C10 H10A 109.4 . . ?
O10 C10 H10B 109.4 . . ?
C7 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C10 O10 H10 108.5(16) . . ?

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
O1 C1 N2 C3 -179.24(17) . . . . ?
C7A C1 N2 C3 1.2(2) . . . . ?
C1 N2 C3 O3 -177.91(18) . . . . ?
C1 N2 C3 C3A 1.9(2) . . . . ?
O3 C3 C3A C7A 175.72(19) . . . . ?
N2 C3 C3A C7A -4.1(2) . . . . ?
O3 C3 C3A C4 -73.1(3) . . . . ?
N2 C3 C3A C4 107.05(17) . . . . ?
C3 C3A C4 O8 -153.20(16) . . . . ?
C7A C3A C4 O8 -39.79(17) . . . . ?
C3 C3A C4 C9 87.1(2) . . . . ?
C7A C3A C4 C9 -159.51(17) . . . . ?
C3 C3A C4 C5 -45.5(2) . . . . ?
C7A C3A C4 C5 67.96(19) . . . . ?
O8 C4 C5 C6 29.75(16) . . . . ?
C9 C4 C5 C6 149.99(15) . . . . ?
C3A C4 C5 C6 -76.07(18) . . . . ?
C4 C5 C6 C7 4.45(17) . . . . ?
C5 C6 C7 O8 -36.99(17) . . . . ?
C5 C6 C7 C10 -155.67(15) . . . . ?
C5 C6 C7 C7A 68.80(16) . . . . ?
O1 C1 C7A C3A 176.79(17) . . . . ?
N2 C1 C7A C3A -3.66(19) . . . . ?
O1 C1 C7A C7 65.0(2) . . . . ?
N2 C1 C7A C7 -115.50(17) . . . . ?
C3 C3A C7A C1 4.62(18) . . . . ?
C4 C3A C7A C1 -116.87(15) . . . . ?
C3 C3A C7A C7 127.06(16) . . . . ?
C4 C3A C7A C7 5.57(18) . . . . ?
O8 C7 C7A C1 143.02(16) . . . . ?
C10 C7 C7A C1 -100.5(2) . . . . ?
C6 C7 C7A C1 36.3(2) . . . . ?
O8 C7 C7A C3A 29.87(18) . . . . ?
C10 C7 C7A C3A 146.37(17) . . . . ?
C6 C7 C7A C3A -76.89(18) . . . . ?
C9 C4 O8 C7 -175.68(14) . . . . ?
C5 C4 O8 C7 -53.63(14) . . . . ?
C3A C4 O8 C7 60.67(15) . . . . ?
C10 C7 O8 C4 -177.92(15) . . . . ?
C6 C7 O8 C4 56.91(16) . . . . ?
C7A C7 O8 C4 -56.41(15) . . . . ?
O8 C4 C9 O9 -53.2(2) . . . . ?
C5 C4 C9 O9 -168.55(16) . . . . ?
C3A C4 C9 O9 60.2(2) . . . . ?
O8 C7 C10 O10 -51.0(2) . . . . ?
C6 C7 C10 O10 64.0(2) . . . . ?
C7A C7 C10 O10 -162.74(16) . . . . ?

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
N2 H2 O3 0.83(2) 2.23(2) 3.006(2) 156(2) 3_656
O9 H9 O10 0.83(3) 1.87(3) 2.701(2) 174(3) 1_545
O10 H10 O9 0.83(2) 1.90(3) 2.717(2) 167(3) 2_556

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.080

_shelxl_version_number           2014/6

