# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_GSW_TBMP
_database_code_depnum_ccdc_archive 'CCDC 2275122'
loop_
_audit_author_name
_audit_author_address
GSW
;Southeast University
China
;
_audit_update_record             
;
2023-06-26 deposited with the CCDC.	2024-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H21 N O5'
_chemical_formula_sum            'C12 H21 N O5'
_chemical_formula_weight         259.30

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

_cell_length_a                   6.3761(8)
_cell_length_b                   9.9644(12)
_cell_length_c                   22.622(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1437.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2788
_cell_measurement_theta_min      3.32
_cell_measurement_theta_max      23.50

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6344
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            7203
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.233
_diffrn_reflns_theta_max         27.446
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             3202
_reflns_number_gt                1918
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_max     0.948
_reflns_Friedel_fraction_full    0.942

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0485P)²+0.0904P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 588 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(7)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3202
_refine_ls_number_parameters     331
_refine_ls_number_restraints     566
_refine_ls_R_factor_all          0.1084
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1204
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.002
_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
C1A C -0.192(4) 0.690(3) 0.3504(9) 0.090(4) Uani 0.5 1 d D U P A 1
H1A1 H -0.191052 0.624650 0.319374 0.134 Uiso 0.5 1 d R U P A 1
H1A2 H -0.104146 0.764552 0.339495 0.134 Uiso 0.5 1 d R U P A 1
H1A3 H -0.332860 0.721648 0.356513 0.134 Uiso 0.5 1 d R U P A 1
O1A O -0.1235(18) 0.6292(8) 0.4039(5) 0.074(2) Uani 0.5 1 d D U P A 1
C2A C 0.0205(14) 0.5110(10) 0.4198(4) 0.0793(19) Uani 0.5 1 d . U P A 1
H2A1 H -0.050608 0.445182 0.444239 0.095 Uiso 0.5 1 calc R U P A 1
H2A2 H 0.076464 0.467498 0.384831 0.095 Uiso 0.5 1 calc R U P A 1
C3A C 0.1793(13) 0.5812(9) 0.4519(4) 0.0689(17) Uani 0.5 1 d . U P A 1
H3A H 0.217548 0.661880 0.429585 0.083 Uiso 0.5 1 calc R U P A 1
C4A C 0.375(2) 0.4992(11) 0.4621(6) 0.062(2) Uani 0.5 1 d D U P A 1
H4A1 H 0.497850 0.557009 0.462637 0.074 Uiso 0.5 1 calc R U P A 1
H4A2 H 0.392710 0.433648 0.430771 0.074 Uiso 0.5 1 calc R U P A 1
C5A C 0.1171(19) 0.6228(10) 0.5134(6) 0.058(2) Uani 0.5 1 d D U P A 1
H5A1 H 0.187506 0.705062 0.524812 0.070 Uiso 0.5 1 calc R U P A 1
H5A2 H -0.033329 0.636135 0.516089 0.070 Uiso 0.5 1 calc R U P A 1
C6A C 0.350(3) 0.4292(17) 0.5212(6) 0.047(3) Uani 0.5 1 d D U P A 1
H6A H 0.296313 0.338492 0.514353 0.056 Uiso 0.5 1 calc R U P A 1
N1A N 0.184(4) 0.5102(19) 0.5506(7) 0.046(3) Uani 0.5 1 d D U P A 1
C7A C 0.542(5) 0.420(4) 0.5575(19) 0.050(4) Uani 0.5 1 d . U P A 1
C8A C 0.109(6) 0.480(3) 0.6041(12) 0.050(3) Uani 0.5 1 d . U P A 1
C9A C 0.148(6) 0.321(4) 0.6888(11) 0.072(3) Uani 0.5 1 d . U P A 1
C10A C 0.302(4) 0.210(2) 0.7107(6) 0.089(4) Uani 0.5 1 d . U P A 1
H10A H 0.443738 0.240466 0.706550 0.133 Uiso 0.5 1 calc R U P A 1
H10B H 0.282386 0.129968 0.687440 0.133 Uiso 0.5 1 calc R U P A 1
H10C H 0.273847 0.190022 0.751445 0.133 Uiso 0.5 1 calc R U P A 1
C11A C 0.251(3) 0.428(2) 0.7315(8) 0.096(4) Uani 0.5 1 d . U P A 1
H11A H 0.398952 0.432830 0.724280 0.144 Uiso 0.5 1 calc R U P A 1
H11B H 0.226175 0.402965 0.771795 0.144 Uiso 0.5 1 calc R U P A 1
H11C H 0.189129 0.514838 0.724204 0.144 Uiso 0.5 1 calc R U P A 1
C12A C -0.077(6) 0.275(4) 0.6905(12) 0.094(5) Uani 0.5 1 d . U P A 1
H12A H -0.105951 0.234510 0.728232 0.141 Uiso 0.5 1 calc R U P A 1
H12B H -0.100493 0.210052 0.659794 0.141 Uiso 0.5 1 calc R U P A 1
H12C H -0.168249 0.350296 0.684725 0.141 Uiso 0.5 1 calc R U P A 1
O2A O 0.704(4) 0.356(2) 0.5456(9) 0.061(3) Uani 0.5 1 d . U P A 1
O3A O 0.585(3) 0.547(3) 0.5853(13) 0.068(5) Uani 0.5 1 d . U P A 1
H3B H 0.702472 0.540898 0.599729 0.102 Uiso 0.5 1 d R U P A 1
O4A O 0.188(3) 0.368(2) 0.6270(7) 0.060(3) Uani 0.5 1 d . U P A 1
O5A O -0.022(5) 0.553(3) 0.6288(14) 0.058(5) Uani 0.5 1 d . U P A 1
C1B C -0.168(4) 0.669(2) 0.3640(10) 0.089(4) Uani 0.5 1 d D U P B 2
H1B1 H -0.076557 0.743376 0.372171 0.133 Uiso 0.5 1 d R U P B 2
H1B2 H -0.307933 0.701206 0.357874 0.133 Uiso 0.5 1 d R U P B 2
H1B3 H -0.120258 0.623229 0.329161 0.133 Uiso 0.5 1 d R U P B 2
O1B O -0.1683(17) 0.5761(9) 0.4121(5) 0.082(2) Uani 0.5 1 d D U P B 2
C2B C 0.0903(12) 0.5960(8) 0.4066(3) 0.0616(16) Uani 0.5 1 d . U P B 2
H2B1 H 0.149214 0.559825 0.370439 0.074 Uiso 0.5 1 calc R U P B 2
H2B2 H 0.136428 0.687658 0.412937 0.074 Uiso 0.5 1 calc R U P B 2
C3B C 0.1220(11) 0.5033(7) 0.4615(3) 0.0500(14) Uani 0.5 1 d . U P B 2
H3C H 0.028027 0.425921 0.457936 0.060 Uiso 0.5 1 calc R U P B 2
C4B C 0.3449(18) 0.4530(9) 0.4708(6) 0.051(2) Uani 0.5 1 d D U P B 2
H4B1 H 0.446135 0.524231 0.464485 0.062 Uiso 0.5 1 calc R U P B 2
H4B2 H 0.376644 0.379072 0.444341 0.062 Uiso 0.5 1 calc R U P B 2
C5B C 0.0765(17) 0.5752(9) 0.5199(5) 0.048(2) Uani 0.5 1 d D U P B 2
H5B1 H 0.134983 0.665064 0.520224 0.057 Uiso 0.5 1 calc R U P B 2
H5B2 H -0.072862 0.579937 0.527690 0.057 Uiso 0.5 1 calc R U P B 2
C6B C 0.345(4) 0.4068(19) 0.5354(6) 0.049(3) Uani 0.5 1 d D U P B 2
H6B H 0.309361 0.311268 0.538144 0.058 Uiso 0.5 1 calc R U P B 2
N1B N 0.183(4) 0.4878(19) 0.5621(7) 0.046(2) Uani 0.5 1 d D U P B 2
C7B C 0.572(5) 0.433(4) 0.5591(19) 0.049(4) Uani 0.5 1 d . U P B 2
C8B C 0.106(6) 0.470(4) 0.6159(11) 0.049(3) Uani 0.5 1 d . U P B 2
C9B C 0.160(6) 0.325(4) 0.7011(10) 0.072(3) Uani 0.5 1 d . U P B 2
C10B C 0.285(5) 0.190(2) 0.6887(7) 0.098(4) Uani 0.5 1 d . U P B 2
H10D H 0.298057 0.140320 0.724773 0.148 Uiso 0.5 1 calc R U P B 2
H10E H 0.422245 0.211760 0.673912 0.148 Uiso 0.5 1 calc R U P B 2
H10F H 0.210897 0.137852 0.659984 0.148 Uiso 0.5 1 calc R U P B 2
C11B C 0.173(2) 0.431(3) 0.7449(8) 0.094(4) Uani 0.5 1 d . U P B 2
H11D H 0.310974 0.469148 0.744322 0.141 Uiso 0.5 1 calc R U P B 2
H11E H 0.145321 0.393986 0.783390 0.141 Uiso 0.5 1 calc R U P B 2
H11F H 0.071289 0.498891 0.736149 0.141 Uiso 0.5 1 calc R U P B 2
C12B C -0.073(6) 0.293(4) 0.7066(12) 0.098(5) Uani 0.5 1 d . U P B 2
H12D H -0.095780 0.239376 0.741372 0.148 Uiso 0.5 1 calc R U P B 2
H12E H -0.117478 0.243227 0.672366 0.148 Uiso 0.5 1 calc R U P B 2
H12F H -0.151532 0.374360 0.709431 0.148 Uiso 0.5 1 calc R U P B 2
O2B O 0.673(4) 0.329(2) 0.5585(10) 0.066(4) Uani 0.5 1 d . U P B 2
O3B O 0.584(3) 0.525(2) 0.5938(12) 0.056(4) Uani 0.5 1 d . U P B 2
H3D H 0.704486 0.529769 0.606528 0.084 Uiso 0.5 1 d R U P B 2
O4B O 0.215(3) 0.369(2) 0.6418(7) 0.056(3) Uani 0.5 1 d . U P B 2
O5B O -0.039(5) 0.531(3) 0.6385(14) 0.052(4) Uani 0.5 1 d . U P B 2


_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
C1A O1A 1.425(10) . ?
C1A H1A1 0.9600 . ?
C1A H1A2 0.9600 . ?
C1A H1A3 0.9600 . ?
O1A C2A 1.536(15) . ?
C2A C3A 1.429(13) . ?
C2A H2A1 0.9700 . ?
C2A H2A2 0.9700 . ?
C3A C5A 1.504(14) . ?
C3A C4A 1.512(14) . ?
C3A H3A 0.9800 . ?
C4A C6A 1.517(13) . ?
C4A H4A1 0.9700 . ?
C4A H4A2 0.9700 . ?
C5A N1A 1.467(14) . ?
C5A H5A1 0.9700 . ?
C5A H5A2 0.9700 . ?
C6A C7A 1.47(4) . ?
C6A N1A 1.49(2) . ?
C6A H6A 0.9800 . ?
N1A C8A 1.34(3) . ?
C7A O2A 1.24(5) . ?
C7A O3A 1.44(5) . ?
C8A O5A 1.24(4) . ?
C8A O4A 1.33(3) . ?
C9A O4A 1.50(2) . ?
C9A C12A 1.51(4) . ?
C9A C10A 1.56(5) . ?
C9A C11A 1.58(3) . ?
C10A H10A 0.9600 . ?
C10A H10B 0.9600 . ?
C10A H10C 0.9600 . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
O3A H3B 0.8200 . ?
C1B O1B 1.427(11) . ?
C1B H1B1 0.9600 . ?
C1B H1B2 0.9600 . ?
C1B H1B3 0.9600 . ?
O1B C2B 1.665(14) . ?
C2B C3B 1.559(10) . ?
C2B H2B1 0.9700 . ?
C2B H2B2 0.9700 . ?
C3B C4B 1.522(13) . ?
C3B C5B 1.531(13) . ?
C3B H3C 0.9800 . ?
C4B C6B 1.533(12) . ?
C4B H4B1 0.9700 . ?
C4B H4B2 0.9700 . ?
C5B N1B 1.460(14) . ?
C5B H5B1 0.9700 . ?
C5B H5B2 0.9700 . ?
C6B N1B 1.44(2) . ?
C6B C7B 1.57(4) . ?
C6B H6B 0.9800 . ?
N1B C8B 1.32(3) . ?
C7B O3B 1.21(5) . ?
C7B O2B 1.22(5) . ?
C8B O5B 1.22(4) . ?
C8B O4B 1.35(3) . ?
C9B C11B 1.45(3) . ?
C9B O4B 1.46(2) . ?
C9B C12B 1.52(4) . ?
C9B C10B 1.59(5) . ?
C10B H10D 0.9600 . ?
C10B H10E 0.9600 . ?
C10B H10F 0.9600 . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?
O3B H3D 0.8200 . ?

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
O1A C1A H1A1 109.1 . . ?
O1A C1A H1A2 111.6 . . ?
H1A1 C1A H1A2 109.5 . . ?
O1A C1A H1A3 107.6 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?
C1A O1A C2A 135.2(15) . . ?
C3A C2A O1A 99.6(8) . . ?
C3A C2A H2A1 111.9 . . ?
O1A C2A H2A1 111.9 . . ?
C3A C2A H2A2 111.9 . . ?
O1A C2A H2A2 111.9 . . ?
H2A1 C2A H2A2 109.6 . . ?
C2A C3A C5A 114.7(8) . . ?
C2A C3A C4A 113.5(8) . . ?
C5A C3A C4A 103.1(8) . . ?
C2A C3A H3A 108.4 . . ?
C5A C3A H3A 108.4 . . ?
C4A C3A H3A 108.4 . . ?
C3A C4A C6A 107.2(10) . . ?
C3A C4A H4A1 110.3 . . ?
C6A C4A H4A1 110.3 . . ?
C3A C4A H4A2 110.3 . . ?
C6A C4A H4A2 110.3 . . ?
H4A1 C4A H4A2 108.5 . . ?
N1A C5A C3A 104.0(9) . . ?
N1A C5A H5A1 111.0 . . ?
C3A C5A H5A1 111.0 . . ?
N1A C5A H5A2 111.0 . . ?
C3A C5A H5A2 111.0 . . ?
H5A1 C5A H5A2 109.0 . . ?
C7A C6A N1A 112.0(19) . . ?
C7A C6A C4A 116(2) . . ?
N1A C6A C4A 102.7(10) . . ?
C7A C6A H6A 108.7 . . ?
N1A C6A H6A 108.7 . . ?
C4A C6A H6A 108.7 . . ?
C8A N1A C5A 126(2) . . ?
C8A N1A C6A 122.5(19) . . ?
C5A N1A C6A 111.6(11) . . ?
O2A C7A O3A 113(3) . . ?
O2A C7A C6A 127(3) . . ?
O3A C7A C6A 110(3) . . ?
O5A C8A O4A 125(2) . . ?
O5A C8A N1A 121(3) . . ?
O4A C8A N1A 114(3) . . ?
O4A C9A C12A 106.4(18) . . ?
O4A C9A C10A 114(2) . . ?
C12A C9A C10A 112(3) . . ?
O4A C9A C11A 107(2) . . ?
C12A C9A C11A 126(2) . . ?
C10A C9A C11A 92(2) . . ?
C9A C10A H10A 109.5 . . ?
C9A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
C9A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C9A C11A H11A 109.5 . . ?
C9A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C9A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C9A C12A H12A 109.5 . . ?
C9A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C9A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C7A O3A H3B 106.1 . . ?
C8A O4A C9A 124.3(19) . . ?
O1B C1B H1B1 110.9 . . ?
O1B C1B H1B2 109.0 . . ?
H1B1 C1B H1B2 109.5 . . ?
O1B C1B H1B3 108.6 . . ?
H1B1 C1B H1B3 109.5 . . ?
H1B2 C1B H1B3 109.5 . . ?
C1B O1B C2B 82.2(12) . . ?
C3B C2B O1B 89.9(6) . . ?
C3B C2B H2B1 113.7 . . ?
O1B C2B H2B1 113.7 . . ?
C3B C2B H2B2 113.7 . . ?
O1B C2B H2B2 113.7 . . ?
H2B1 C2B H2B2 110.9 . . ?
C4B C3B C5B 102.2(7) . . ?
C4B C3B C2B 115.2(6) . . ?
C5B C3B C2B 112.7(6) . . ?
C4B C3B H3C 108.8 . . ?
C5B C3B H3C 108.8 . . ?
C2B C3B H3C 108.8 . . ?
C3B C4B C6B 103.4(10) . . ?
C3B C4B H4B1 111.1 . . ?
C6B C4B H4B1 111.1 . . ?
C3B C4B H4B2 111.1 . . ?
C6B C4B H4B2 111.1 . . ?
H4B1 C4B H4B2 109.1 . . ?
N1B C5B C3B 101.4(10) . . ?
N1B C5B H5B1 111.5 . . ?
C3B C5B H5B1 111.5 . . ?
N1B C5B H5B2 111.5 . . ?
C3B C5B H5B2 111.5 . . ?
H5B1 C5B H5B2 109.3 . . ?
N1B C6B C4B 103.4(11) . . ?
N1B C6B C7B 115.2(19) . . ?
C4B C6B C7B 106(2) . . ?
N1B C6B H6B 110.6 . . ?
C4B C6B H6B 110.6 . . ?
C7B C6B H6B 110.6 . . ?
C8B N1B C6B 125.1(19) . . ?
C8B N1B C5B 121(2) . . ?
C6B N1B C5B 113.1(12) . . ?
O3B C7B O2B 128(4) . . ?
O3B C7B C6B 114(3) . . ?
O2B C7B C6B 110(3) . . ?
O5B C8B N1B 127(3) . . ?
O5B C8B O4B 125(2) . . ?
N1B C8B O4B 108(3) . . ?
C11B C9B O4B 113(2) . . ?
C11B C9B C12B 99(2) . . ?
O4B C9B C12B 111.9(19) . . ?
C11B C9B C10B 135(3) . . ?
O4B C9B C10B 88.4(19) . . ?
C12B C9B C10B 109(3) . . ?
C9B C10B H10D 109.5 . . ?
C9B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C9B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C9B C11B H11D 109.5 . . ?
C9B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C9B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C9B C12B H12D 109.5 . . ?
C9B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C9B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C7B O3B H3D 109.3 . . ?
C8B O4B C9B 120.1(19) . . ?

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
C1A O1A C2A C3A 118(2) . . . . ?
O1A C2A C3A C5A 75.6(10) . . . . ?
O1A C2A C3A C4A -166.3(8) . . . . ?
C2A C3A C4A C6A -92.0(12) . . . . ?
C5A C3A C4A C6A 32.7(11) . . . . ?
C2A C3A C5A N1A 91.5(13) . . . . ?
C4A C3A C5A N1A -32.4(13) . . . . ?
C3A C4A C6A C7A -142(2) . . . . ?
C3A C4A C6A N1A -19.4(14) . . . . ?
C3A C5A N1A C8A -158(3) . . . . ?
C3A C5A N1A C6A 21.6(16) . . . . ?
C7A C6A N1A C8A -57(3) . . . . ?
C4A C6A N1A C8A 178(3) . . . . ?
C7A C6A N1A C5A 123(2) . . . . ?
C4A C6A N1A C5A -1.5(17) . . . . ?
N1A C6A C7A O2A 178(3) . . . . ?
C4A C6A C7A O2A -65(4) . . . . ?
N1A C6A C7A O3A -40(3) . . . . ?
C4A C6A C7A O3A 77(3) . . . . ?
C5A N1A C8A O5A -5(5) . . . . ?
C6A N1A C8A O5A 176(3) . . . . ?
C5A N1A C8A O4A 176(2) . . . . ?
C6A N1A C8A O4A -3(4) . . . . ?
O5A C8A O4A C9A -6(5) . . . . ?
N1A C8A O4A C9A 173(2) . . . . ?
C12A C9A O4A C8A 71(3) . . . . ?
C10A C9A O4A C8A -165(3) . . . . ?
C11A C9A O4A C8A -65(3) . . . . ?
C1B O1B C2B C3B 176.6(13) . . . . ?
O1B C2B C3B C4B 165.5(7) . . . . ?
O1B C2B C3B C5B -77.8(8) . . . . ?
C5B C3B C4B C6B 39.7(10) . . . . ?
C2B C3B C4B C6B 162.2(9) . . . . ?
C4B C3B C5B N1B -37.2(11) . . . . ?
C2B C3B C5B N1B -161.4(11) . . . . ?
C3B C4B C6B N1B -26.4(13) . . . . ?
C3B C4B C6B C7B -148.0(18) . . . . ?
C4B C6B N1B C8B 170(3) . . . . ?
C7B C6B N1B C8B -75(3) . . . . ?
C4B C6B N1B C5B 2.6(17) . . . . ?
C7B C6B N1B C5B 118(2) . . . . ?
C3B C5B N1B C8B -146(3) . . . . ?
C3B C5B N1B C6B 21.9(16) . . . . ?
N1B C6B C7B O3B -5(4) . . . . ?
C4B C6B C7B O3B 108(3) . . . . ?
N1B C6B C7B O2B 147(3) . . . . ?
C4B C6B C7B O2B -100(3) . . . . ?
C6B N1B C8B O5B -175(3) . . . . ?
C5B N1B C8B O5B -8(5) . . . . ?
C6B N1B C8B O4B 4(4) . . . . ?
C5B N1B C8B O4B 170(2) . . . . ?
O5B C8B O4B C9B 0(5) . . . . ?
N1B C8B O4B C9B -178(2) . . . . ?
C11B C9B O4B C8B -59(3) . . . . ?
C12B C9B O4B C8B 52(3) . . . . ?
C10B C9B O4B C8B 162(3) . . . . ?

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
_geom_hbond_publ_flag
O3B^b H3D^b O5B^b 0.82 1.79 2.61(4) 175.6 1_655 yes
C11B^b H11F^b O5B^b 0.96 2.34 2.94(4) 119.6 . yes
C4B^b H4B2^b O2B^b 0.97 2.44 3.08(3) 123.2 2_456 yes
C1B^b H1B1^b O3B^b 0.96 2.64 3.58(3) 165.1 2_466 yes
O3A^a H3B^a O5A^a 0.82 1.88 2.69(4) 171.1 1_655 yes
C12A^a H12C^a O5A^a 0.96 2.56 3.13(5) 117.9 . yes
C6A^a H6A^a O2A^a 0.98 2.44 3.35(3) 155.0 2_456 yes
C5A^a H5A1^a O1A^a 0.97 2.60 3.513(16) 156.3 2_566 yes
C1A^a H1A3^a O5A^a 0.96 2.57 3.34(4) 137.9 2_466 yes

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.030

####################################################################### 
# 
# 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_GSW_TBMP_Monohydrate
_database_code_depnum_ccdc_archive 'CCDC 2275123'
loop_
_audit_author_name
_audit_author_address
GSW
;Southeast University
China
;
_audit_update_record             
;
2023-06-26 deposited with the CCDC.	2024-01-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H21 N O5, H2 O'
_chemical_formula_sum            'C12 H23 N O6'
_chemical_formula_weight         277.31
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.8953(2)
_cell_length_b                   7.8109(2)
_cell_length_c                   8.5294(2)
_cell_angle_alpha                71.6660(10)
_cell_angle_beta                 86.2690(10)
_cell_angle_gamma                86.1690(10)
_cell_volume                     371.586(18)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    7688
_cell_measurement_temperature    170
_cell_measurement_theta_max      79.974
_cell_measurement_theta_min      9.539
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.907
_exptl_absorpt_coefficient_mu    0.832
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0935 before and 0.0512 after correction. The Ratio of minimum to maximum transmission is 0.9223. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             150
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7140
_diffrn_reflns_point_group_measured_fraction_full 0.903
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        66.577
_diffrn_reflns_theta_max         66.577
_diffrn_reflns_theta_min         9.539
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.841
_reflns_Friedel_fraction_max     0.841
_reflns_number_gt                2355
_reflns_number_total             2362
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.107
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 1084 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2362
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0243
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0243P)²+0.0464P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0619
_refine_ls_wR_factor_ref         0.0619
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
2.c Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C2(H2A,H2B), C5(H5A,H5B)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C6(H6A,H6B,H6C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O2 O 0.6096(2) 0.66511(17) 0.47751(17) 0.0291(3) Uani 1 1 d . . . . .
H2 H 0.667868 0.761946 0.472786 0.044 Uiso 1 1 calc GR . . . .
O4 O 0.5418(2) 0.55002(16) 0.17862(15) 0.0284(3) Uani 1 1 d . . . . .
O5 O 0.6957(2) 0.26483(17) 0.28851(16) 0.0339(3) Uani 1 1 d . . . . .
O1 O 0.8319(2) 0.92911(17) 0.49036(17) 0.0305(3) Uani 1 1 d . . . . .
H1A H 0.976154 0.909049 0.470516 0.046 Uiso 1 1 d G . . . .
H1B H 0.791296 1.039491 0.434351 0.046 Uiso 1 1 d G . . . .
O3 O 0.2898(2) 0.83734(17) 0.44724(18) 0.0323(3) Uani 1 1 d . . . . .
O6 O 0.2166(3) 0.17159(19) 0.91079(17) 0.0400(4) Uani 1 1 d . . . . .
N1 N 0.4198(3) 0.38412(19) 0.42698(18) 0.0243(3) Uani 1 1 d . . . . .
C7 C 0.3928(3) 0.6951(2) 0.4543(2) 0.0206(3) Uani 1 1 d . . . . .
C12 C 0.5639(3) 0.3900(2) 0.2972(2) 0.0244(4) Uani 1 1 d . . . . .
C4 C 0.3854(3) 0.2183(2) 0.5657(2) 0.0261(4) Uani 1 1 d . . . . .
H4A H 0.493606 0.205169 0.653218 0.031 Uiso 1 1 calc R . . . .
H4B H 0.401582 0.110002 0.528454 0.031 Uiso 1 1 calc R . . . .
C2 C 0.1268(3) 0.4520(2) 0.6031(2) 0.0249(4) Uani 1 1 d . . . . .
H2A H 0.190633 0.476852 0.697887 0.030 Uiso 1 1 calc R . . . .
H2B H -0.032788 0.500727 0.592327 0.030 Uiso 1 1 calc R . . . .
C1 C 0.2700(3) 0.5352(2) 0.4425(2) 0.0211(4) Uani 1 1 d . . . . .
H1 H 0.168071 0.576083 0.347088 0.025 Uiso 1 1 calc R . . . .
C8 C 0.6724(3) 0.5850(2) 0.0188(2) 0.0270(4) Uani 1 1 d . . . . .
C5 C 0.0785(4) 0.1315(3) 0.7992(3) 0.0304(4) Uani 1 1 d . . . . .
H5A H -0.083911 0.154613 0.827051 0.037 Uiso 1 1 calc R . . . .
H5B H 0.102252 0.002578 0.806584 0.037 Uiso 1 1 calc R . . . .
C3 C 0.1411(3) 0.2495(2) 0.6255(2) 0.0253(4) Uani 1 1 d . . . . .
H3 H 0.035890 0.226172 0.548010 0.030 Uiso 1 1 calc R . . . .
C11 C 0.5865(4) 0.7746(3) -0.0759(3) 0.0400(5) Uani 1 1 d . . . . .
H11A H 0.424090 0.774316 -0.093930 0.060 Uiso 1 1 calc GR . . . .
H11B H 0.670907 0.815638 -0.182781 0.060 Uiso 1 1 calc GR . . . .
H11C H 0.609121 0.856197 -0.011987 0.060 Uiso 1 1 calc GR . . . .
C9 C 0.6114(4) 0.4513(3) -0.0660(3) 0.0391(5) Uani 1 1 d . . . . .
H9A H 0.671776 0.330316 -0.004931 0.059 Uiso 1 1 calc GR . . . .
H9B H 0.677517 0.486668 -0.179311 0.059 Uiso 1 1 calc GR . . . .
H9C H 0.445500 0.450549 -0.068371 0.059 Uiso 1 1 calc GR . . . .
C10 C 0.9245(4) 0.5798(3) 0.0436(3) 0.0409(5) Uani 1 1 d . . . . .
H10A H 0.953093 0.659230 0.108359 0.061 Uiso 1 1 calc GR . . . .
H10B H 1.006661 0.620743 -0.064182 0.061 Uiso 1 1 calc GR . . . .
H10C H 0.977177 0.455894 0.102824 0.061 Uiso 1 1 calc GR . . . .
C6 C 0.1658(5) 0.0712(3) 1.0777(3) 0.0502(7) Uani 1 1 d . . . . .
H6A H 0.183752 -0.058141 1.090797 0.075 Uiso 1 1 calc GR . . . .
H6B H 0.008678 0.101038 1.108597 0.075 Uiso 1 1 calc GR . . . .
H6C H 0.269927 0.101207 1.149085 0.075 Uiso 1 1 calc GR . . . .


_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
O2 H2 0.8400 . ?
O2 C7 1.300(2) . ?
O4 C12 1.342(2) . ?
O4 C8 1.478(2) . ?
O5 C12 1.225(2) . ?
O1 H1A 0.8699 . ?
O1 H1B 0.8700 . ?
O3 C7 1.216(2) . ?
O6 C5 1.411(3) . ?
O6 C6 1.416(3) . ?
N1 C12 1.342(2) . ?
N1 C4 1.469(2) . ?
N1 C1 1.461(2) . ?
C7 C1 1.518(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.526(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.541(2) . ?
C2 C3 1.530(2) . ?
C1 H1 1.0000 . ?
C8 C11 1.517(3) . ?
C8 C9 1.517(3) . ?
C8 C10 1.511(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C3 1.515(3) . ?
C3 H3 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 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
C7 O2 H2 109.5 . . ?
C12 O4 C8 120.93(13) . . ?
H1A O1 H1B 109.5 . . ?
C5 O6 C6 112.97(18) . . ?
C12 N1 C4 122.80(14) . . ?
C12 N1 C1 124.73(14) . . ?
C1 N1 C4 112.36(14) . . ?
O2 C7 C1 115.05(14) . . ?
O3 C7 O2 123.96(16) . . ?
O3 C7 C1 120.95(16) . . ?
O5 C12 O4 125.02(16) . . ?
O5 C12 N1 124.16(16) . . ?
N1 C12 O4 110.82(14) . . ?
N1 C4 H4A 111.4 . . ?
N1 C4 H4B 111.4 . . ?
N1 C4 C3 102.02(14) . . ?
H4A C4 H4B 109.2 . . ?
C3 C4 H4A 111.4 . . ?
C3 C4 H4B 111.4 . . ?
H2A C2 H2B 108.9 . . ?
C1 C2 H2A 110.9 . . ?
C1 C2 H2B 110.9 . . ?
C3 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C3 C2 C1 104.26(13) . . ?
N1 C1 C7 114.54(14) . . ?
N1 C1 C2 103.55(13) . . ?
N1 C1 H1 109.4 . . ?
C7 C1 C2 110.27(14) . . ?
C7 C1 H1 109.4 . . ?
C2 C1 H1 109.4 . . ?
O4 C8 C11 102.43(14) . . ?
O4 C8 C9 109.40(15) . . ?
O4 C8 C10 110.55(15) . . ?
C9 C8 C11 110.61(17) . . ?
C10 C8 C11 110.73(17) . . ?
C10 C8 C9 112.65(17) . . ?
O6 C5 H5A 109.9 . . ?
O6 C5 H5B 109.9 . . ?
O6 C5 C3 108.79(15) . . ?
H5A C5 H5B 108.3 . . ?
C3 C5 H5A 109.9 . . ?
C3 C5 H5B 109.9 . . ?
C4 C3 C2 102.62(14) . . ?
C4 C3 H3 108.3 . . ?
C2 C3 H3 108.3 . . ?
C5 C3 C4 114.54(16) . . ?
C5 C3 C2 114.35(16) . . ?
C5 C3 H3 108.3 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O6 C6 H6A 109.5 . . ?
O6 C6 H6B 109.5 . . ?
O6 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
