# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_cu_TG_CW62_13_8_0m
_database_code_depnum_ccdc_archive 'CCDC 1522636'
_audit_update_record             
;
2016-12-14 deposited with the CCDC.
2017-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1-tert-Butyl 2-methyl 7-oxoazepane-1,2-dicarboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H21 N O5'
_chemical_formula_sum            'C13 H21 N O5'
_chemical_formula_weight         271.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   10.8289(3)
_cell_length_b                   12.9518(4)
_cell_length_c                   20.3412(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2852.93(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9938
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      72.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.209
_exptl_absorpt_coefficient_mu    0.806
_shelx_estimated_absorpt_T_min   0.771
_shelx_estimated_absorpt_T_max   0.850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6615
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   
'Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51777
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.347
_diffrn_reflns_theta_max         72.471
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2819
_reflns_number_gt                2645
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0463P)²+1.2862P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00186(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2819
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 -1.00 -1.00 0.0680
-1.00 0.00 -1.00 0.1560
-1.00 0.00 0.00 0.1690
1.00 1.00 -1.00 0.0860
-1.00 -1.00 1.00 0.1290
0.00 1.00 1.00 0.0960
0.00 -1.00 -1.00 0.1060
1.00 0.00 -1.00 0.0450
0.00 -1.00 2.00 0.0600
0.00 1.00 -2.00 0.1100
-1.00 1.00 -2.00 0.1440
1.00 -1.00 2.00 0.0720
-1.00 1.00 -1.00 0.1560
1.00 -1.00 1.00 0.0670
1.00 2.00 -1.00 0.1030
-1.00 -2.00 1.00 0.1270
0.00 1.00 0.00 0.1160
-2.00 -1.00 -1.00 0.1680
2.00 1.00 1.00 0.0740
0.00 -2.00 -1.00 0.0910
0.00 0.00 -1.00 0.0980
-1.00 1.00 2.00 0.1350


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 0.02299(8) 0.25316(7) 0.65463(5) 0.0327(2) Uani 1 1 d . . . . .
O2 O 0.18157(8) 0.26705(7) 0.72511(4) 0.0311(2) Uani 1 1 d . . . . .
O3 O 0.42845(8) 0.43719(8) 0.72427(4) 0.0328(2) Uani 1 1 d . . . . .
O4 O 0.40685(8) 0.27476(7) 0.55523(5) 0.0331(2) Uani 1 1 d . . . . .
O5 O 0.52347(8) 0.38969(8) 0.61054(5) 0.0341(2) Uani 1 1 d . . . . .
N1 N 0.32081(9) 0.37665(8) 0.63483(5) 0.0224(2) Uani 1 1 d . . . . .
C1 C -0.04550(13) 0.19728(12) 0.70451(8) 0.0409(4) Uani 1 1 d . . . . .
H1A H -0.1279 0.1804 0.6877 0.061 Uiso 1 1 calc R U . . .
H1B H -0.0533 0.2402 0.7440 0.061 Uiso 1 1 calc R U . . .
H1C H -0.0016 0.1334 0.7155 0.061 Uiso 1 1 calc R U . . .
C2 C 0.13537(11) 0.28398(9) 0.67252(6) 0.0227(3) Uani 1 1 d . . . . .
C3 C 0.19891(11) 0.33722(9) 0.61507(6) 0.0224(3) Uani 1 1 d . . . . .
H3 H 0.2169 0.2807 0.5830 0.027 Uiso 1 1 calc R U . . .
C4 C 0.11970(12) 0.41462(10) 0.57687(6) 0.0267(3) Uani 1 1 d . . . . .
H4A H 0.1696 0.4422 0.5401 0.032 Uiso 1 1 calc R U . . .
H4B H 0.0489 0.3771 0.5575 0.032 Uiso 1 1 calc R U . . .
C5 C 0.06977(12) 0.50524(10) 0.61633(7) 0.0305(3) Uani 1 1 d . . . . .
H5A H 0.0255 0.5524 0.5861 0.037 Uiso 1 1 calc R U . . .
H5B H 0.0091 0.4789 0.6486 0.037 Uiso 1 1 calc R U . . .
C6 C 0.16807(12) 0.56645(9) 0.65281(6) 0.0286(3) Uani 1 1 d . . . . .
H6A H 0.1303 0.6306 0.6700 0.034 Uiso 1 1 calc R U . . .
H6B H 0.2333 0.5867 0.6212 0.034 Uiso 1 1 calc R U . . .
C7 C 0.22794(11) 0.50797(9) 0.70997(6) 0.0248(3) Uani 1 1 d . . . . .
H7A H 0.2572 0.5591 0.7426 0.030 Uiso 1 1 calc R U . . .
H7B H 0.1636 0.4655 0.7316 0.030 Uiso 1 1 calc R U . . .
C8 C 0.33482(11) 0.43836(9) 0.69223(6) 0.0228(3) Uani 1 1 d . . . . .
C9 C 0.42006(11) 0.34036(9) 0.59689(6) 0.0232(3) Uani 1 1 d . . . . .
C10 C 0.63989(11) 0.36030(12) 0.57736(7) 0.0327(3) Uani 1 1 d . . . . .
C11 C 0.66885(15) 0.24677(15) 0.58943(9) 0.0482(4) Uani 1 1 d . . . . .
H11A H 0.6101 0.2038 0.5651 0.072 Uiso 1 1 calc R U . . .
H11B H 0.6622 0.2318 0.6365 0.072 Uiso 1 1 calc R U . . .
H11C H 0.7530 0.2317 0.5744 0.072 Uiso 1 1 calc R U . . .
C12 C 0.63204(14) 0.38495(12) 0.50486(7) 0.0391(3) Uani 1 1 d . . . . .
H12A H 0.7120 0.3712 0.4841 0.059 Uiso 1 1 calc R U . . .
H12B H 0.6105 0.4579 0.4991 0.059 Uiso 1 1 calc R U . . .
H12C H 0.5685 0.3417 0.4844 0.059 Uiso 1 1 calc R U . . .
C13 C 0.73373(15) 0.42814(19) 0.61158(10) 0.0693(7) Uani 1 1 d . . . . .
H13A H 0.8157 0.4159 0.5927 0.104 Uiso 1 1 calc R U . . .
H13B H 0.7352 0.4116 0.6586 0.104 Uiso 1 1 calc R U . . .
H13C H 0.7111 0.5008 0.6057 0.104 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 C2 1.3314(15) . ?
O1 C1 1.4503(16) . ?
O2 C2 1.2011(16) . ?
O3 C8 1.2054(15) . ?
O4 C9 1.2086(15) . ?
O5 C9 1.3189(15) . ?
O5 C10 1.4798(14) . ?
N1 C9 1.4042(15) . ?
N1 C8 1.4230(15) . ?
N1 C3 1.4714(14) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.5213(16) . ?
C3 C4 1.5312(17) . ?
C3 H3 1.0000 . ?
C4 C5 1.5212(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5206(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5317(17) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5109(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C10 C12 1.511(2) . ?
C10 C13 1.513(2) . ?
C10 C11 1.523(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
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
C2 O1 C1 115.20(11) . . ?
C9 O5 C10 120.18(9) . . ?
C9 N1 C8 123.87(10) . . ?
C9 N1 C3 114.86(9) . . ?
C8 N1 C3 120.98(9) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 124.71(11) . . ?
O2 C2 C3 125.35(11) . . ?
O1 C2 C3 109.83(10) . . ?
N1 C3 C2 110.68(10) . . ?
N1 C3 C4 114.46(10) . . ?
C2 C3 C4 115.68(10) . . ?
N1 C3 H3 104.9 . . ?
C2 C3 H3 104.9 . . ?
C4 C3 H3 104.9 . . ?
C5 C4 C3 115.88(10) . . ?
C5 C4 H4A 108.3 . . ?
C3 C4 H4A 108.3 . . ?
C5 C4 H4B 108.3 . . ?
C3 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
C6 C5 C4 114.27(11) . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C5 C6 C7 114.14(10) . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C8 C7 C6 115.97(10) . . ?
C8 C7 H7A 108.3 . . ?
C6 C7 H7A 108.3 . . ?
C8 C7 H7B 108.3 . . ?
C6 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
O3 C8 N1 121.75(11) . . ?
O3 C8 C7 121.51(11) . . ?
N1 C8 C7 116.71(10) . . ?
O4 C9 O5 126.07(11) . . ?
O4 C9 N1 122.01(11) . . ?
O5 C9 N1 111.84(10) . . ?
O5 C10 C12 110.05(11) . . ?
O5 C10 C13 102.30(11) . . ?
C12 C10 C13 111.35(14) . . ?
O5 C10 C11 110.50(11) . . ?
C12 C10 C11 111.88(12) . . ?
C13 C10 C11 110.38(15) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 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
C1 O1 C2 O2 1.29(18) . . . . ?
C1 O1 C2 C3 177.58(11) . . . . ?
C9 N1 C3 C2 123.47(11) . . . . ?
C8 N1 C3 C2 -50.59(14) . . . . ?
C9 N1 C3 C4 -103.65(12) . . . . ?
C8 N1 C3 C4 82.29(13) . . . . ?
O2 C2 C3 N1 -6.67(16) . . . . ?
O1 C2 C3 N1 177.07(9) . . . . ?
O2 C2 C3 C4 -138.93(12) . . . . ?
O1 C2 C3 C4 44.81(13) . . . . ?
N1 C3 C4 C5 -70.47(13) . . . . ?
C2 C3 C4 C5 60.01(14) . . . . ?
C3 C4 C5 C6 54.37(15) . . . . ?
C4 C5 C6 C7 -68.90(14) . . . . ?
C5 C6 C7 C8 85.07(14) . . . . ?
C9 N1 C8 O3 -24.17(18) . . . . ?
C3 N1 C8 O3 149.34(12) . . . . ?
C9 N1 C8 C7 154.05(11) . . . . ?
C3 N1 C8 C7 -32.44(15) . . . . ?
C6 C7 C8 O3 135.20(12) . . . . ?
C6 C7 C8 N1 -43.03(15) . . . . ?
C10 O5 C9 O4 -5.3(2) . . . . ?
C10 O5 C9 N1 177.89(11) . . . . ?
C8 N1 C9 O4 167.52(12) . . . . ?
C3 N1 C9 O4 -6.34(17) . . . . ?
C8 N1 C9 O5 -15.48(16) . . . . ?
C3 N1 C9 O5 170.66(10) . . . . ?
C9 O5 C10 C12 66.55(16) . . . . ?
C9 O5 C10 C13 -175.02(14) . . . . ?
C9 O5 C10 C11 -57.50(16) . . . . ?

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate, n-hexane'
####################################################################### 
# 
# 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_cu_TG_CWLR_019_8_2_0m
_database_code_depnum_ccdc_archive 'CCDC 1528320'
_audit_update_record             
;
2017-01-18 deposited with the CCDC.
2017-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'tert-Butyl 7,8-dioxo-6-azabicyclo[3.2.1]octane-6-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H19 N O5'
_chemical_formula_sum            'C12 H19 N O5'
_chemical_formula_weight         257.28

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                   6.1511(6)
_cell_length_b                   6.3794(7)
_cell_length_c                   17.5260(18)
_cell_angle_alpha                88.877(5)
_cell_angle_beta                 80.145(5)
_cell_angle_gamma                82.187(5)
_cell_volume                     671.28(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5983
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      73.16

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    0.830
_shelx_estimated_absorpt_T_min   0.749
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6019
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   
'Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7972
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.559
_diffrn_reflns_theta_max         74.382
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2624
_reflns_number_gt                2422
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 2-component twin., 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)+(0.0839P)²+0.7946P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2624
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.1859
_refine_ls_wR_factor_gt          0.1764
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 0.00 0.1040
0.00 1.00 0.00 0.0040
-1.00 0.00 0.00 0.0700
1.00 1.00 -1.00 0.1200
0.00 1.00 -1.00 0.0080
0.00 -1.00 1.00 0.0900
1.00 0.00 -1.00 0.1580
1.00 -1.00 0.00 0.1620
-1.00 1.00 -1.00 0.0270
-1.00 0.00 -1.00 0.0780
-1.00 -1.00 0.00 0.1180
1.00 1.00 0.00 0.1290
0.00 0.00 1.00 0.0140
0.00 0.00 -1.00 0.0240

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 1.1657(4) 0.3991(4) 0.34377(16) 0.0351(6) Uani 1 1 d . . . . .
O2 O 0.5474(4) 0.4003(4) 0.40861(14) 0.0313(5) Uani 1 1 d . . . . .
H2O H 0.420(9) 0.397(8) 0.389(3) 0.047 Uiso 1 1 d . U . . .
O3 O 0.4388(4) 0.7529(4) 0.44195(16) 0.0358(6) Uani 1 1 d . . . . .
H3O H 0.447(9) 0.715(9) 0.488(3) 0.054 Uiso 1 1 d . U . . .
O4 O 0.8027(7) 0.5350(7) 0.16348(18) 0.0664(10) Uani 1 1 d . . . . .
O5 O 1.1015(5) 0.3359(5) 0.19854(16) 0.0490(7) Uani 1 1 d . . . . .
N1 N 0.8564(5) 0.5276(5) 0.28814(17) 0.0309(6) Uani 1 1 d . . . . .
C1 C 0.9795(5) 0.4939(5) 0.3481(2) 0.0279(7) Uani 1 1 d . . . . .
C2 C 0.8366(5) 0.6037(5) 0.4191(2) 0.0301(7) Uani 1 1 d . . . . .
H2 H 0.8550 0.5241 0.4678 0.036 Uiso 1 1 calc R U . . .
C3 C 0.6030(5) 0.6079(5) 0.39982(19) 0.0292(7) Uani 1 1 d . . . . .
C4 C 0.8892(6) 0.8317(6) 0.4223(3) 0.0472(11) Uani 1 1 d . . . . .
H4A H 0.7795 0.9121 0.4629 0.057 Uiso 1 1 calc R U . . .
H4B H 1.0391 0.8304 0.4359 0.057 Uiso 1 1 calc R U . . .
C5 C 0.8811(8) 0.9394(6) 0.3442(4) 0.0580(13) Uani 1 1 d . . . . .
H5A H 1.0198 0.8884 0.3082 0.070 Uiso 1 1 calc R U . . .
H5B H 0.8765 1.0937 0.3510 0.070 Uiso 1 1 calc R U . . .
C6 C 0.6808(8) 0.8998(7) 0.3072(3) 0.0526(11) Uani 1 1 d . . . . .
H6A H 0.5454 0.9900 0.3330 0.063 Uiso 1 1 calc R U . . .
H6B H 0.7071 0.9390 0.2518 0.063 Uiso 1 1 calc R U . . .
C7 C 0.6449(6) 0.6686(6) 0.3147(2) 0.0365(8) Uani 1 1 d . . . . .
H7A H 0.5227 0.6373 0.2875 0.044 Uiso 1 1 calc R U . . .
C8 C 0.9161(6) 0.4696(7) 0.2103(2) 0.0389(8) Uani 1 1 d . . . . .
C9 C 1.2041(7) 0.2542(10) 0.1198(2) 0.0602(13) Uani 1 1 d . . . . .
C10 C 1.2685(15) 0.4389(16) 0.0715(4) 0.110(3) Uani 1 1 d . . . . .
H10A H 1.1351 0.5392 0.0677 0.165 Uiso 1 1 calc R U . . .
H10B H 1.3406 0.3896 0.0195 0.165 Uiso 1 1 calc R U . . .
H10C H 1.3721 0.5091 0.0955 0.165 Uiso 1 1 calc R U . . .
C11 C 1.0501(9) 0.1305(12) 0.0877(4) 0.0791(19) Uani 1 1 d . . . . .
H11A H 0.9986 0.0259 0.1259 0.119 Uiso 1 1 calc R U . . .
H11B H 1.1290 0.0578 0.0401 0.119 Uiso 1 1 calc R U . . .
H11C H 0.9218 0.2268 0.0760 0.119 Uiso 1 1 calc R U . . .
C12 C 1.4055(11) 0.1101(16) 0.1361(4) 0.108(3) Uani 1 1 d . . . . .
H12A H 1.4903 0.0482 0.0874 0.162 Uiso 1 1 calc R U . . .
H12B H 1.3578 -0.0032 0.1710 0.162 Uiso 1 1 calc R U . . .
H12C H 1.4994 0.1913 0.1605 0.162 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 1.211(4) . ?
O2 C3 1.411(4) . ?
O2 H2O 0.91(5) . ?
O3 C3 1.393(4) . ?
O3 H3O 0.84(5) . ?
O4 C8 1.199(5) . ?
O5 C8 1.316(5) . ?
O5 C9 1.489(5) . ?
N1 C8 1.395(5) . ?
N1 C1 1.395(4) . ?
N1 C7 1.486(4) . ?
C1 C2 1.517(5) . ?
C2 C3 1.528(4) . ?
C2 C4 1.537(5) . ?
C2 H2 1.0000 . ?
C3 C7 1.521(5) . ?
C4 C5 1.525(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.538(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.521(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 1.0000 . ?
C9 C10 1.495(10) . ?
C9 C11 1.496(8) . ?
C9 C12 1.505(9) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C3 O2 H2O 108(3) . . ?
C3 O3 H3O 101(4) . . ?
C8 O5 C9 121.6(3) . . ?
C8 N1 C1 129.5(3) . . ?
C8 N1 C7 119.8(3) . . ?
C1 N1 C7 110.2(3) . . ?
O1 C1 N1 126.5(3) . . ?
O1 C1 C2 126.9(3) . . ?
N1 C1 C2 106.5(3) . . ?
C1 C2 C3 101.5(3) . . ?
C1 C2 C4 109.0(3) . . ?
C3 C2 C4 109.1(3) . . ?
C1 C2 H2 112.2 . . ?
C3 C2 H2 112.2 . . ?
C4 C2 H2 112.2 . . ?
O3 C3 O2 111.3(3) . . ?
O3 C3 C7 110.9(3) . . ?
O2 C3 C7 110.8(3) . . ?
O3 C3 C2 115.4(3) . . ?
O2 C3 C2 107.6(3) . . ?
C7 C3 C2 100.4(3) . . ?
C5 C4 C2 110.3(3) . . ?
C5 C4 H4A 109.6 . . ?
C2 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C2 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C6 114.0(3) . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C7 C6 C5 110.8(3) . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
N1 C7 C3 99.9(3) . . ?
N1 C7 C6 110.8(3) . . ?
C3 C7 C6 109.7(3) . . ?
N1 C7 H7A 111.9 . . ?
C3 C7 H7A 111.9 . . ?
C6 C7 H7A 111.9 . . ?
O4 C8 O5 127.5(4) . . ?
O4 C8 N1 121.4(4) . . ?
O5 C8 N1 111.1(3) . . ?
O5 C9 C10 107.5(5) . . ?
O5 C9 C11 110.5(4) . . ?
C10 C9 C11 114.4(6) . . ?
O5 C9 C12 101.8(4) . . ?
C10 C9 C12 111.5(6) . . ?
C11 C9 C12 110.4(6) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C8 N1 C1 O1 -2.4(6) . . . . ?
C7 N1 C1 O1 -174.5(3) . . . . ?
C8 N1 C1 C2 176.3(3) . . . . ?
C7 N1 C1 C2 4.2(4) . . . . ?
O1 C1 C2 C3 -157.1(3) . . . . ?
N1 C1 C2 C3 24.2(3) . . . . ?
O1 C1 C2 C4 87.8(4) . . . . ?
N1 C1 C2 C4 -90.9(3) . . . . ?
C1 C2 C3 O3 -161.5(3) . . . . ?
C4 C2 C3 O3 -46.5(4) . . . . ?
C1 C2 C3 O2 73.6(3) . . . . ?
C4 C2 C3 O2 -171.5(3) . . . . ?
C1 C2 C3 C7 -42.2(3) . . . . ?
C4 C2 C3 C7 72.7(3) . . . . ?
C1 C2 C4 C5 49.5(4) . . . . ?
C3 C2 C4 C5 -60.5(4) . . . . ?
C2 C4 C5 C6 44.0(4) . . . . ?
C4 C5 C6 C7 -43.6(5) . . . . ?
C8 N1 C7 C3 156.1(3) . . . . ?
C1 N1 C7 C3 -30.9(4) . . . . ?
C8 N1 C7 C6 -88.2(4) . . . . ?
C1 N1 C7 C6 84.7(4) . . . . ?
O3 C3 C7 N1 166.6(3) . . . . ?
O2 C3 C7 N1 -69.4(3) . . . . ?
C2 C3 C7 N1 44.1(3) . . . . ?
O3 C3 C7 C6 50.1(4) . . . . ?
O2 C3 C7 C6 174.2(3) . . . . ?
C2 C3 C7 C6 -72.4(3) . . . . ?
C5 C6 C7 N1 -49.9(5) . . . . ?
C5 C6 C7 C3 59.5(4) . . . . ?
C9 O5 C8 O4 3.5(7) . . . . ?
C9 O5 C8 N1 -178.3(4) . . . . ?
C1 N1 C8 O4 -169.7(4) . . . . ?
C7 N1 C8 O4 1.7(6) . . . . ?
C1 N1 C8 O5 12.0(5) . . . . ?
C7 N1 C8 O5 -176.6(3) . . . . ?
C8 O5 C9 C10 63.1(6) . . . . ?
C8 O5 C9 C11 -62.4(6) . . . . ?
C8 O5 C9 C12 -179.6(5) . . . . ?

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
O2 H2O O1 0.91(5) 1.87(5) 2.779(3) 177(4) 1_455
O3 H3O O2 0.84(5) 1.95(5) 2.789(4) 174(5) 2_666

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.068


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane, ethyl acetate'
