# 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 2019

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1851944'
loop_
_audit_author_name
_audit_author_address
'JInjian Liu'
;Shanxi Normal University
China
;
_audit_update_record             
;
2019-03-25 deposited with the CCDC.	2019-03-27 downloaded from the CCDC.
;
_audit_creation_date             2019-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H15 N, C5 H2 O4, C5 H3 O4, H2 O'
_chemical_formula_sum            'C20 H22 N O9'
_chemical_formula_weight         420.38
_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 0.0033 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'

_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           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0205(5)
_cell_length_b                   9.4323(5)
_cell_length_c                   13.8142(8)
_cell_angle_alpha                71.1010(10)
_cell_angle_beta                 73.0030(10)
_cell_angle_gamma                62.3490(10)
_cell_volume                     970.76(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9271
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9617
_exptl_absorpt_correction_T_min  0.9580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             442
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.34
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13079
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.586
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3371
_reflns_number_total             3784
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker D8 venture'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3784
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.030
_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)+(0.0494P)²+0.3297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1029
_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:
 O9(H9A,H9B)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C17(H17)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O6(H6A), O8(H8A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
N1 N 0.81907(15) 0.74908(15) 0.19118(9) 0.0331(3) Uani 1 1 d . . . . .
O1 O 0.19246(12) 0.74984(13) 0.73319(7) 0.0369(3) Uani 1 1 d . . . . .
O2 O 0.39098(12) 0.80827(14) 0.61454(8) 0.0404(3) Uani 1 1 d . . . . .
O3 O 0.42429(14) 0.96650(17) 0.36547(9) 0.0508(3) Uani 1 1 d . . . . .
O4 O 0.32854(12) 1.13945(13) 0.46911(9) 0.0375(3) Uani 1 1 d . . . . .
H4 H 0.4185 1.1489 0.4426 0.056 Uiso 1 1 calc GR . . . .
O5 O 0.20573(13) 0.28022(12) 0.17677(8) 0.0359(2) Uani 1 1 d . . . . .
O6 O 0.08247(13) 0.14186(14) 0.14998(8) 0.0399(3) Uani 1 1 d . . . . .
H6A H 0.0027 0.1917 0.1904 0.060 Uiso 1 1 calc GR . . . .
O7 O 0.25907(14) 0.44950(13) -0.04213(9) 0.0450(3) Uani 1 1 d . . . . .
O8 O 0.53809(13) 0.38553(12) -0.08100(9) 0.0425(3) Uani 1 1 d . . . . .
H8A H 0.5086 0.4836 -0.1083 0.064 Uiso 1 1 calc GR . . . .
O9 O 0.49547(14) 0.31922(13) 0.18244(8) 0.0386(3) Uani 1 1 d . . . . .
H9A H 0.5264 0.2917 0.2407 0.058 Uiso 1 1 d G . . . .
H9B H 0.4045 0.3071 0.1912 0.058 Uiso 1 1 d G . . . .
C1 C 0.7134(3) 0.3550(3) 0.65283(15) 0.0674(6) Uani 1 1 d . . . . .
H1A H 0.7002 0.2695 0.6378 0.101 Uiso 1 1 calc GR . . . .
H1B H 0.6036 0.4375 0.6720 0.101 Uiso 1 1 calc GR . . . .
H1C H 0.7759 0.3097 0.7091 0.101 Uiso 1 1 calc GR . . . .
C2 C 0.8091(2) 0.4315(2) 0.55749(13) 0.0486(4) Uani 1 1 d . . . . .
H2A H 0.8243 0.5158 0.5740 0.058 Uiso 1 1 calc R . . . .
H2B H 0.9209 0.3479 0.5398 0.058 Uiso 1 1 calc R . . . .
C3 C 0.7210(2) 0.5067(2) 0.46394(12) 0.0405(4) Uani 1 1 d . . . . .
H3A H 0.6091 0.5904 0.4811 0.049 Uiso 1 1 calc R . . . .
H3B H 0.7065 0.4226 0.4466 0.049 Uiso 1 1 calc R . . . .
C4 C 0.8205(2) 0.5828(2) 0.36996(12) 0.0424(4) Uani 1 1 d . . . . .
H4A H 0.8260 0.6735 0.3852 0.051 Uiso 1 1 calc R . . . .
H4B H 0.9357 0.5016 0.3567 0.051 Uiso 1 1 calc R . . . .
C5 C 0.7412(2) 0.6443(2) 0.27382(12) 0.0393(3) Uani 1 1 d . . . . .
H5A H 0.7583 0.5518 0.2490 0.047 Uiso 1 1 calc R . . . .
H5B H 0.6199 0.7074 0.2905 0.047 Uiso 1 1 calc R . . . .
C6 C 0.96105(19) 0.68167(18) 0.12570(12) 0.0378(3) Uani 1 1 d . . . . .
H6 H 1.0095 0.5689 0.1310 0.045 Uiso 1 1 calc R . . . .
C7 C 0.74924(19) 0.91130(19) 0.18556(12) 0.0401(4) Uani 1 1 d . . . . .
H7 H 0.6523 0.9564 0.2323 0.048 Uiso 1 1 calc R . . . .
C8 C 0.81882(19) 1.01122(18) 0.11190(12) 0.0382(4) Uani 1 1 d . . . . .
H8 H 0.7688 1.1234 0.1089 0.046 Uiso 1 1 calc R . . . .
C9 C 1.03521(18) 0.77707(18) 0.05131(11) 0.0355(3) Uani 1 1 d . . . . .
H9 H 1.1342 0.7284 0.0070 0.043 Uiso 1 1 calc R . . . .
C10 C 0.96396(16) 0.94603(16) 0.04137(10) 0.0278(3) Uani 1 1 d . . . . .
C11 C 0.24307(15) 0.81942(15) 0.64397(10) 0.0243(3) Uani 1 1 d . . . . .
C12 C 0.11940(15) 0.91500(15) 0.56839(10) 0.0226(3) Uani 1 1 d . . . . .
C13 C 0.15481(15) 1.01346(15) 0.47245(10) 0.0226(3) Uani 1 1 d . . . . .
C14 C 0.03625(15) 1.09677(15) 0.40631(10) 0.0244(3) Uani 1 1 d . . . . .
H14 H 0.0615 1.1626 0.3430 0.029 Uiso 1 1 calc R . . . .
C15 C 0.31923(15) 1.03365(16) 0.43150(10) 0.0258(3) Uani 1 1 d . . . . .
C16 C 0.20612(16) 0.18527(16) 0.13449(10) 0.0267(3) Uani 1 1 d . . . . .
C17 C 0.40446(16) -0.07246(16) 0.07741(10) 0.0278(3) Uani 1 1 d . . . . .
H17 H 0.3398 -0.1216 0.1297 0.033 Uiso 1 1 calc R . . . .
C18 C 0.35693(16) 0.09482(16) 0.06149(10) 0.0254(3) Uani 1 1 d . . . . .
C19 C 0.45394(16) 0.16879(16) -0.01747(10) 0.0256(3) Uani 1 1 d . . . . .
C20 C 0.40401(17) 0.35095(16) -0.04656(10) 0.0286(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.4894(18) . ?
N1 C6 1.3425(18) . ?
N1 C7 1.3421(19) . ?
O1 C11 1.2583(16) . ?
O2 C11 1.2397(15) . ?
O3 C15 1.2013(17) . ?
O4 H4 0.8200 . ?
O4 C15 1.3084(17) . ?
O5 C16 1.2158(17) . ?
O6 H6A 0.8200 . ?
O6 C16 1.2981(16) . ?
O7 C20 1.1997(17) . ?
O8 H8A 0.8200 . ?
O8 C20 1.3134(17) . ?
O9 H9A 0.8499 . ?
O9 H9B 0.8499 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.516(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.513(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.523(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.511(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C9 1.368(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.368(2) . ?
C8 H8 0.9300 . ?
C8 C10 1.3916(18) . ?
C9 H9 0.9300 . ?
C9 C10 1.390(2) . ?
C10 C10 1.480(3) 2_775 ?
C11 C12 1.5116(18) . ?
C12 C13 1.3969(17) . ?
C12 C14 1.3923(17) 2_576 ?
C13 C14 1.3865(18) . ?
C13 C15 1.5026(16) . ?
C14 C12 1.3923(17) 2_576 ?
C14 H14 0.9300 . ?
C16 C18 1.5078(17) . ?
C17 H17 0.9300 . ?
C17 C18 1.3872(19) . ?
C17 C19 1.3908(18) 2_655 ?
C18 C19 1.3992(17) . ?
C19 C17 1.3908(18) 2_655 ?
C19 C20 1.5022(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C5 120.56(12) . . ?
C7 N1 C5 119.09(12) . . ?
C7 N1 C6 120.30(12) . . ?
C15 O4 H4 109.5 . . ?
C16 O6 H6A 109.5 . . ?
C20 O8 H8A 109.5 . . ?
H9A O9 H9B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 C1 113.68(17) . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C2 C3 C4 112.12(14) . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 C3 112.25(13) . . ?
C5 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
N1 C5 C4 110.11(12) . . ?
N1 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.2 . . ?
N1 C6 H6 119.6 . . ?
N1 C6 C9 120.72(13) . . ?
C9 C6 H6 119.6 . . ?
N1 C7 H7 119.6 . . ?
N1 C7 C8 120.83(13) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C10 120.43(13) . . ?
C10 C8 H8 119.8 . . ?
C6 C9 H9 119.7 . . ?
C6 C9 C10 120.59(13) . . ?
C10 C9 H9 119.7 . . ?
C8 C10 C10 120.82(15) . 2_775 ?
C9 C10 C8 117.10(13) . . ?
C9 C10 C10 122.07(14) . 2_775 ?
O1 C11 C12 118.28(11) . . ?
O2 C11 O1 122.84(12) . . ?
O2 C11 C12 118.83(11) . . ?
C13 C12 C11 123.03(11) . . ?
C14 C12 C11 119.16(11) 2_576 . ?
C14 C12 C13 117.79(12) 2_576 . ?
C12 C13 C15 124.48(11) . . ?
C14 C13 C12 120.11(11) . . ?
C14 C13 C15 115.38(11) . . ?
C12 C14 H14 119.0 2_576 . ?
C13 C14 C12 122.09(11) . 2_576 ?
C13 C14 H14 119.0 . . ?
O3 C15 O4 124.58(12) . . ?
O3 C15 C13 121.99(12) . . ?
O4 C15 C13 113.23(11) . . ?
O5 C16 O6 125.07(12) . . ?
O5 C16 C18 123.49(12) . . ?
O6 C16 C18 111.34(11) . . ?
C18 C17 H17 119.0 . . ?
C18 C17 C19 121.91(12) . 2_655 ?
C19 C17 H17 119.0 2_655 . ?
C17 C18 C16 117.24(11) . . ?
C17 C18 C19 118.99(12) . . ?
C19 C18 C16 123.71(11) . . ?
C17 C19 C18 119.10(12) 2_655 . ?
C17 C19 C20 117.94(11) 2_655 . ?
C18 C19 C20 122.77(11) . . ?
O7 C20 O8 125.58(13) . . ?
O7 C20 C19 123.06(12) . . ?
O8 C20 C19 111.29(11) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1878324'
loop_
_audit_author_name
_audit_author_address
'JInjian Liu'
;Shanxi Normal University
China
;
_audit_update_record             
;
2019-03-25 deposited with the CCDC.	2019-03-27 downloaded from the CCDC.
;
_audit_creation_date             2019-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H11 N, C10 H4 O8, H2 O'
_chemical_formula_sum            'C18 H17 N O9'
_chemical_formula_weight         391.32
_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 0.0033 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'

_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           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4575(6)
_cell_length_b                   9.6725(6)
_cell_length_c                   9.7995(7)
_cell_angle_alpha                94.996(2)
_cell_angle_beta                 97.741(2)
_cell_angle_gamma                95.460(2)
_cell_volume                     879.69(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8867
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.9651
_exptl_absorpt_correction_T_min  0.9418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12180
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.328
_diffrn_reflns_theta_min         2.839
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3846
_reflns_number_total             4289
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker D8 venture'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4289
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0522
_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)+(0.0626P)²+0.3975P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1383
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 C2'-C3
 1.53 with sigma of 0.001
 C1-C2 = C2-C3 = C1'-C2'
 1.53 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C2) = Uanis(C2')
Uanis(C1) = Uanis(C1')
4. Others
 Sof(C1')=Sof(H1'a)=Sof(H1'b)=Sof(H1'c)=Sof(C2')=Sof(H2'a)=Sof(H2'b)=Sof(H3bc)=
 Sof(H3bd)=1-FVAR(1)
 Sof(C1)=Sof(H1a)=Sof(H1b)=Sof(H1c)=Sof(C2)=Sof(H2a)=Sof(H2b)=Sof(H3aa)=
 Sof(H3ab)=FVAR(1)
5.a Riding coordinates:
 C3(H3aa,H3ab,H3bc,H3bd)
5.b Free rotating group:
 O9(H9a,H9b)
5.c Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C2'(H2'a,H2'b)
5.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C13(H13), C18(H18)
5.e Tetrahedral OH refined with riding coordinates:
 O5(H5a), O7(H7a)
5.f Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C1'(H1'a,H1'b,H1'c)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
N1 N 0.30819(15) 0.73584(15) 0.60721(14) 0.0389(3) Uani 1 1 d . . . . .
O1 O 0.16720(14) 1.06607(11) 0.23472(16) 0.0499(3) Uani 1 1 d . . . . .
O2 O -0.06029(14) 1.01304(13) 0.1531(2) 0.0634(4) Uani 1 1 d . . . . .
O3 O -0.23798(12) 0.81636(13) 0.11368(16) 0.0495(3) Uani 1 1 d . . . . .
O4 O -0.25302(11) 0.59481(12) 0.14599(15) 0.0439(3) Uani 1 1 d . . . . .
O5 O 0.11337(12) 0.31188(11) 0.16641(14) 0.0424(3) Uani 1 1 d . . . . .
H5A H 0.1406 0.2358 0.1810 0.064 Uiso 1 1 calc R . . . .
O6 O 0.32246(12) 0.39292(12) 0.29389(15) 0.0454(3) Uani 1 1 d . . . . .
O7 O 0.47451(11) 0.59246(13) 0.13847(13) 0.0428(3) Uani 1 1 d . . . . .
H7A H 0.5614 0.5887 0.1531 0.064 Uiso 1 1 calc R . . . .
O8 O 0.51141(13) 0.71331(17) 0.34641(15) 0.0557(4) Uani 1 1 d . . . . .
O9 O 0.77556(17) 0.87538(17) 0.46459(18) 0.0640(4) Uani 1 1 d . . . . .
H9A H 0.6981 0.8264 0.4279 0.096 Uiso 1 1 d G . . . .
H9B H 0.7668 0.8895 0.5497 0.096 Uiso 1 1 d G . . . .
C1 C 0.4079(11) 0.8027(6) 0.8993(8) 0.091(2) Uani 0.635(4) 1 d D U P A 1
H1A H 0.3132 0.7538 0.8781 0.137 Uiso 0.635(4) 1 calc GR . P A 1
H1B H 0.4197 0.8517 0.9903 0.137 Uiso 0.635(4) 1 calc GR . P A 1
H1C H 0.4778 0.7372 0.8960 0.137 Uiso 0.635(4) 1 calc GR . P A 1
C2 C 0.4286(4) 0.9063(3) 0.7943(3) 0.0545(7) Uani 0.635(4) 1 d D U P A 1
H2A H 0.3485 0.9621 0.7861 0.065 Uiso 0.635(4) 1 calc R . P A 1
H2B H 0.5156 0.9686 0.8259 0.065 Uiso 0.635(4) 1 calc R . P A 1
C1' C 0.3759(17) 0.8566(15) 0.9134(15) 0.091(2) Uani 0.365(4) 1 d D . P A 2
H1'A H 0.3507 0.9496 0.9048 0.137 Uiso 0.365(4) 1 calc GR . P A 2
H1'B H 0.4188 0.8498 1.0068 0.137 Uiso 0.365(4) 1 calc GR . P A 2
H1'C H 0.2911 0.7913 0.8908 0.137 Uiso 0.365(4) 1 calc GR . P A 2
C2' C 0.4825(6) 0.8233(6) 0.8145(3) 0.0545(7) Uani 0.365(4) 1 d D . P A 2
H2'A H 0.5054 0.7287 0.8245 0.065 Uiso 0.365(4) 1 calc R . P A 2
H2'B H 0.5703 0.8849 0.8449 0.065 Uiso 0.365(4) 1 calc R . P A 2
C3 C 0.4385(2) 0.8350(2) 0.6599(2) 0.0499(4) Uani 1 1 d D . . . .
H3AA H 0.5224 0.7841 0.6671 0.060 Uiso 0.635(4) 1 d R . P A 1
H3AB H 0.4505 0.9034 0.5944 0.060 Uiso 0.635(4) 1 d R . P A 1
H3BC H 0.4186 0.9296 0.6459 0.060 Uiso 0.365(4) 1 d R . P A 2
H3BD H 0.5163 0.8132 0.6093 0.060 Uiso 0.365(4) 1 d R . P A 2
C4 C 0.1803(2) 0.78408(19) 0.5748(2) 0.0458(4) Uani 1 1 d . . . . .
H4 H 0.1745 0.8798 0.5813 0.055 Uiso 1 1 calc R . . . .
C5 C 0.31856(18) 0.59806(18) 0.59862(18) 0.0414(4) Uani 1 1 d . . . . .
H5 H 0.4076 0.5659 0.6205 0.050 Uiso 1 1 calc R . . . .
C6 C 0.19934(18) 0.50436(18) 0.55801(17) 0.0400(4) Uani 1 1 d . . . . .
H6 H 0.2080 0.4092 0.5535 0.048 Uiso 1 1 calc R . . . .
C7 C 0.05857(18) 0.69403(18) 0.53247(19) 0.0424(4) Uani 1 1 d . . . . .
H7 H -0.0289 0.7290 0.5097 0.051 Uiso 1 1 calc R . . . .
C8 C 0.06513(16) 0.55016(16) 0.52337(14) 0.0334(3) Uani 1 1 d . . . . .
C9 C -0.18041(14) 0.70610(15) 0.14105(15) 0.0288(3) Uani 1 1 d . . . . .
C10 C -0.01834(13) 0.70811(13) 0.16904(13) 0.0227(2) Uani 1 1 d . . . . .
C11 C 0.08616(14) 0.82497(13) 0.19423(14) 0.0252(3) Uani 1 1 d . . . . .
C12 C 0.06164(17) 0.97823(14) 0.19413(17) 0.0350(3) Uani 1 1 d . . . . .
C13 C 0.23056(14) 0.80180(13) 0.22235(15) 0.0279(3) Uani 1 1 d . . . . .
H13 H 0.2998 0.8786 0.2406 0.033 Uiso 1 1 calc R . . . .
C14 C 0.27472(13) 0.66966(13) 0.22413(14) 0.0244(3) Uani 1 1 d . . . . .
C15 C 0.43392(14) 0.65886(14) 0.24421(16) 0.0300(3) Uani 1 1 d . . . . .
C16 C 0.17142(13) 0.55402(12) 0.20134(13) 0.0222(2) Uani 1 1 d . . . . .
C17 C 0.21229(14) 0.41099(13) 0.22307(14) 0.0263(3) Uani 1 1 d . . . . .
C18 C 0.02766(13) 0.57517(13) 0.17354(13) 0.0225(2) Uani 1 1 d . . . . .
H18 H -0.0409 0.4978 0.1573 0.027 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C3 1.491(2) . ?
N1 C4 1.346(2) . ?
N1 C5 1.342(2) . ?
O1 C12 1.2448(19) . ?
O2 C12 1.256(2) . ?
O3 C9 1.2755(17) . ?
O4 C9 1.2288(18) . ?
O5 C17 1.3035(17) . ?
O6 C17 1.2078(17) . ?
O7 C15 1.2929(19) . ?
O8 C15 1.2060(19) . ?
C1 C2 1.515(7) . ?
C2 C3 1.451(4) . ?
C1' C2' 1.527(9) . ?
C2' C3 1.5331(10) . ?
C4 C7 1.369(3) . ?
C5 C6 1.368(3) . ?
C6 C8 1.393(2) . ?
C7 C8 1.394(2) . ?
C8 C8 1.487(3) 2_566 ?
C9 C10 1.5183(17) . ?
C10 C11 1.4102(17) . ?
C10 C18 1.3985(17) . ?
C11 C12 1.5221(18) . ?
C11 C13 1.3996(18) . ?
C13 C14 1.3827(18) . ?
C14 C15 1.5067(17) . ?
C14 C16 1.3947(17) . ?
C16 C17 1.4965(17) . ?
C16 C18 1.3884(16) . ?

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
C4 N1 C3 120.20(15) . . ?
C5 N1 C3 119.30(14) . . ?
C5 N1 C4 120.42(15) . . ?
C3 C2 C1 111.0(3) . . ?
C1' C2' C3 118.2(8) . . ?
N1 C3 C2' 109.4(2) . . ?
C2 C3 N1 111.71(18) . . ?
N1 C4 C7 120.84(16) . . ?
N1 C5 C6 120.64(15) . . ?
C5 C6 C8 120.65(15) . . ?
C4 C7 C8 120.30(15) . . ?
C6 C8 C7 117.13(15) . . ?
C6 C8 C8 121.37(17) . 2_566 ?
C7 C8 C8 121.49(17) . 2_566 ?
O3 C9 C10 120.79(12) . . ?
O4 C9 O3 121.72(13) . . ?
O4 C9 C10 117.48(12) . . ?
C11 C10 C9 128.16(11) . . ?
C18 C10 C9 113.48(11) . . ?
C18 C10 C11 118.32(11) . . ?
C10 C11 C12 127.54(12) . . ?
C13 C11 C10 118.25(11) . . ?
C13 C11 C12 114.21(11) . . ?
O1 C12 O2 122.06(13) . . ?
O1 C12 C11 117.22(13) . . ?
O2 C12 C11 120.71(13) . . ?
C14 C13 C11 122.82(12) . . ?
C13 C14 C15 117.45(11) . . ?
C13 C14 C16 119.00(11) . . ?
C16 C14 C15 123.48(11) . . ?
O7 C15 C14 112.28(12) . . ?
O8 C15 O7 125.94(13) . . ?
O8 C15 C14 121.70(13) . . ?
C14 C16 C17 120.79(11) . . ?
C18 C16 C14 118.88(11) . . ?
C18 C16 C17 119.92(11) . . ?
O5 C17 C16 113.09(11) . . ?
O6 C17 O5 124.79(12) . . ?
O6 C17 C16 121.96(12) . . ?
C16 C18 C10 122.69(11) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1865385'
loop_
_audit_author_name
_audit_author_address
'JInjian Liu'
;Shanxi Normal University
China
;
_audit_update_record             
;
2019-03-25 deposited with the CCDC.	2019-03-27 downloaded from the CCDC.
;
_audit_creation_date             2019-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C5 H2 O4), C16 H22 N2, H2 O'
_chemical_formula_sum            'C26 H28 N2 O9'
_chemical_formula_weight         512.50
_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 0.0033 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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.8941(5)
_cell_length_b                   16.4507(9)
_cell_length_c                   15.2172(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.2200(10)
_cell_angle_gamma                90
_cell_volume                     2466.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9951
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9791
_exptl_absorpt_correction_T_min  0.9688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32767
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.666
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4291
_reflns_number_total             4817
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker D8 venture'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4817
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.021
_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)+(0.0589P)²+0.9103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1153
_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:
 O9(H9A,H9B)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C2(H2A,H2B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C13(H13), C10(H10), C11(H11), C7(H7), C5(H5), C6(H6), C12(H12),
 C4(H4), C20(H20)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C1(H1A,H1B,H1C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A), O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O5 O -0.13502(10) 0.20243(5) 0.53742(6) 0.0344(2) Uani 1 1 d . . . . .
H5A H -0.1808 0.2420 0.5208 0.052 Uiso 1 1 calc GR . . . .
O7 O 0.31115(10) 0.09826(6) 0.44265(9) 0.0466(3) Uani 1 1 d . . . . .
O8 O 0.17949(11) 0.19246(6) 0.49500(8) 0.0442(3) Uani 1 1 d . . . . .
N2 N 1.15571(13) 0.32237(8) 0.26315(8) 0.0387(3) Uani 1 1 d . . . . .
O6 O -0.10174(12) 0.19277(6) 0.39501(7) 0.0442(3) Uani 1 1 d . . . . .
C25 C 0.09609(12) 0.05898(7) 0.48288(8) 0.0220(2) Uani 1 1 d . . . . .
C26 C 0.20545(12) 0.12082(7) 0.47198(9) 0.0260(3) Uani 1 1 d . . . . .
C24 C -0.13332(12) 0.02230(7) 0.50639(8) 0.0234(3) Uani 1 1 d . . . . .
H24 H -0.2230 0.0373 0.5110 0.028 Uiso 1 1 calc R . . . .
C22 C -0.09200(12) 0.16580(7) 0.46941(9) 0.0256(3) Uani 1 1 d . . . . .
C13 C 1.18266(16) 0.37628(9) 0.20115(10) 0.0404(3) Uani 1 1 d . . . . .
H13 H 1.2347 0.3605 0.1562 0.048 Uiso 1 1 calc R . . . .
C9 C 1.05833(14) 0.47905(9) 0.27045(9) 0.0354(3) Uani 1 1 d . . . . .
C10 C 1.13467(16) 0.45437(9) 0.20296(10) 0.0397(3) Uani 1 1 d . . . . .
H10 H 1.1532 0.4909 0.1590 0.048 Uiso 1 1 calc R . . . .
C11 C 1.03619(16) 0.42229(10) 0.33579(10) 0.0423(4) Uani 1 1 d . . . . .
H11 H 0.9883 0.4372 0.3831 0.051 Uiso 1 1 calc R . . . .
C8 C 0.99758(14) 0.56140(9) 0.27083(10) 0.0365(3) Uani 1 1 d . . . . .
C23 C -0.03899(12) 0.08138(7) 0.48885(8) 0.0217(2) Uani 1 1 d . . . . .
C7 C 0.95725(17) 0.60072(10) 0.19210(10) 0.0416(4) Uani 1 1 d . . . . .
H7 H 0.9724 0.5763 0.1387 0.050 Uiso 1 1 calc R . . . .
N1 N 0.87148(13) 0.71082(8) 0.26861(9) 0.0429(3) Uani 1 1 d . . . . .
C14 C 1.19580(17) 0.23593(10) 0.25504(11) 0.0462(4) Uani 1 1 d . . . . .
H14A H 1.2276 0.2148 0.3128 0.055 Uiso 1 1 calc R . . . .
H14B H 1.2696 0.2320 0.2174 0.055 Uiso 1 1 calc R . . . .
C15 C 1.07704(18) 0.18592(10) 0.21638(11) 0.0455(4) Uani 1 1 d . . . . .
H15A H 1.0501 0.2041 0.1567 0.055 Uiso 1 1 calc R . . . .
H15B H 1.0007 0.1935 0.2512 0.055 Uiso 1 1 calc R . . . .
C5 C 0.91447(18) 0.67629(12) 0.34610(11) 0.0521(4) Uani 1 1 d . . . . .
H5 H 0.9018 0.7032 0.3985 0.062 Uiso 1 1 calc R . . . .
C2 C 0.89755(18) 0.86084(11) 0.28014(12) 0.0497(4) Uani 1 1 d . . . . .
H2A H 0.9592 0.8603 0.2341 0.060 Uiso 1 1 calc R . . . .
H2B H 0.9509 0.8553 0.3365 0.060 Uiso 1 1 calc R . . . .
C3 C 0.80027(17) 0.79085(11) 0.26709(13) 0.0506(4) Uani 1 1 d . . . . .
H3A H 0.7389 0.7918 0.3133 0.061 Uiso 1 1 calc R . . . .
H3B H 0.7465 0.7971 0.2110 0.061 Uiso 1 1 calc R . . . .
C6 C 0.97664(18) 0.60202(11) 0.34889(11) 0.0496(4) Uani 1 1 d . . . . .
H6 H 1.0051 0.5785 0.4030 0.059 Uiso 1 1 calc R . . . .
C12 C 1.08471(17) 0.34481(10) 0.33037(11) 0.0448(4) Uani 1 1 d . . . . .
H12 H 1.0684 0.3071 0.3737 0.054 Uiso 1 1 calc R . . . .
C16 C 1.1144(2) 0.09665(11) 0.21518(13) 0.0620(5) Uani 1 1 d . . . . .
H16A H 1.1915 0.0894 0.1820 0.093 Uiso 1 1 calc GR . . . .
H16B H 1.0391 0.0660 0.1882 0.093 Uiso 1 1 calc GR . . . .
H16C H 1.1362 0.0780 0.2745 0.093 Uiso 1 1 calc GR . . . .
C1 C 0.8208(2) 0.94079(12) 0.27761(14) 0.0645(5) Uani 1 1 d . . . . .
H1A H 0.7801 0.9504 0.2188 0.097 Uiso 1 1 calc GR . . . .
H1B H 0.8825 0.9842 0.2948 0.097 Uiso 1 1 calc GR . . . .
H1C H 0.7513 0.9384 0.3176 0.097 Uiso 1 1 calc GR . . . .
C4 C 0.89517(16) 0.67522(10) 0.19241(11) 0.0442(4) Uani 1 1 d . . . . .
H4 H 0.8693 0.7012 0.1393 0.053 Uiso 1 1 calc R . . . .
C18 C -0.03726(12) 0.08084(7) 0.98430(8) 0.0239(3) Uani 1 1 d . . . . .
C19 C 0.09956(12) 0.05934(7) 0.98810(8) 0.0234(3) Uani 1 1 d . . . . .
C20 C 0.13404(12) -0.02179(7) 1.00313(9) 0.0259(3) Uani 1 1 d . . . . .
H20 H 0.2248 -0.0370 1.0048 0.031 Uiso 1 1 calc R . . . .
O2 O -0.15861(12) 0.19456(6) 1.02268(7) 0.0445(3) Uani 1 1 d . . . . .
H2 H -0.2002 0.2349 1.0037 0.067 Uiso 1 1 calc GR . . . .
O1 O -0.07914(13) 0.19583(7) 0.89108(7) 0.0486(3) Uani 1 1 d . . . . .
C17 C -0.09075(12) 0.16422(7) 0.96131(9) 0.0268(3) Uani 1 1 d . . . . .
O9 O 0.56308(15) 0.14654(9) 0.51747(11) 0.0668(4) Uani 1 1 d . . . . .
H9A H 0.4817 0.1345 0.4996 0.100 Uiso 1 1 d G . . . .
H9B H 0.5731 0.1979 0.5162 0.100 Uiso 1 1 d G . . . .
C21 C 0.21468(12) 0.11967(7) 0.98537(9) 0.0262(3) Uani 1 1 d . . . . .
O3 O 0.18706(10) 0.19270(6) 1.00376(9) 0.0464(3) Uani 1 1 d . . . . .
O4 O 0.32717(10) 0.09460(6) 0.97073(8) 0.0441(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 H5A 0.8200 . ?
O5 C22 1.3021(16) . ?
O7 C26 1.2309(16) . ?
O8 C26 1.2627(15) . ?
N2 C13 1.3393(19) . ?
N2 C14 1.484(2) . ?
N2 C12 1.344(2) . ?
O6 C22 1.2117(16) . ?
C25 C26 1.5052(16) . ?
C25 C24 1.3927(16) 3_556 ?
C25 C23 1.3972(16) . ?
C24 C25 1.3927(16) 3_556 ?
C24 H24 0.9300 . ?
C24 C23 1.3900(16) . ?
C22 C23 1.5044(16) . ?
C13 H13 0.9300 . ?
C13 C10 1.371(2) . ?
C9 C10 1.390(2) . ?
C9 C11 1.396(2) . ?
C9 C8 1.482(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.367(2) . ?
C8 C7 1.388(2) . ?
C8 C6 1.395(2) . ?
C7 H7 0.9300 . ?
C7 C4 1.371(2) . ?
N1 C5 1.343(2) . ?
N1 C3 1.492(2) . ?
N1 C4 1.339(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.509(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.515(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.367(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.502(2) . ?
C2 C1 1.517(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C6 H6 0.9300 . ?
C12 H12 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C4 H4 0.9300 . ?
C18 C19 1.3952(17) . ?
C18 C20 1.3894(17) 3_557 ?
C18 C17 1.5001(16) . ?
C19 C20 1.3914(17) . ?
C19 C21 1.5141(16) . ?
C20 C18 1.3894(17) 3_557 ?
C20 H20 0.9300 . ?
O2 H2 0.8200 . ?
O2 C17 1.2985(16) . ?
O1 C17 1.2034(17) . ?
O9 H9A 0.8497 . ?
O9 H9B 0.8506 . ?
C21 O3 1.2689(16) . ?
C21 O4 1.2262(16) . ?

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
C22 O5 H5A 109.5 . . ?
C13 N2 C14 120.26(13) . . ?
C13 N2 C12 120.38(14) . . ?
C12 N2 C14 119.24(13) . . ?
C24 C25 C26 118.47(11) 3_556 . ?
C24 C25 C23 119.33(11) 3_556 . ?
C23 C25 C26 122.03(10) . . ?
O7 C26 O8 125.66(11) . . ?
O7 C26 C25 118.63(11) . . ?
O8 C26 C25 115.70(11) . . ?
C25 C24 H24 119.4 3_556 . ?
C23 C24 C25 121.25(11) . 3_556 ?
C23 C24 H24 119.4 . . ?
O5 C22 C23 113.85(10) . . ?
O6 C22 O5 124.70(12) . . ?
O6 C22 C23 121.22(11) . . ?
N2 C13 H13 119.5 . . ?
N2 C13 C10 120.99(14) . . ?
C10 C13 H13 119.5 . . ?
C10 C9 C11 117.52(14) . . ?
C10 C9 C8 121.18(13) . . ?
C11 C9 C8 121.24(13) . . ?
C13 C10 C9 120.09(14) . . ?
C13 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C9 C11 H11 119.9 . . ?
C12 C11 C9 120.13(14) . . ?
C12 C11 H11 119.9 . . ?
C7 C8 C9 120.49(13) . . ?
C7 C8 C6 117.30(15) . . ?
C6 C8 C9 122.20(14) . . ?
C25 C23 C22 123.30(10) . . ?
C24 C23 C25 119.41(11) . . ?
C24 C23 C22 117.06(10) . . ?
C8 C7 H7 119.8 . . ?
C4 C7 C8 120.49(14) . . ?
C4 C7 H7 119.8 . . ?
C5 N1 C3 119.89(14) . . ?
C4 N1 C5 120.61(14) . . ?
C4 N1 C3 119.48(14) . . ?
N2 C14 H14A 109.6 . . ?
N2 C14 H14B 109.6 . . ?
N2 C14 C15 110.49(13) . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 C16 110.56(15) . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
N1 C5 H5 119.6 . . ?
N1 C5 C6 120.75(15) . . ?
C6 C5 H5 119.6 . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C3 C2 C1 110.36(15) . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
N1 C3 C2 112.22(13) . . ?
N1 C3 H3A 109.2 . . ?
N1 C3 H3B 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C8 C6 H6 119.9 . . ?
C5 C6 C8 120.21(15) . . ?
C5 C6 H6 119.9 . . ?
N2 C12 C11 120.84(14) . . ?
N2 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C4 H4 119.7 . . ?
N1 C4 C7 120.52(15) . . ?
N1 C4 H4 119.7 . . ?
C19 C18 C17 124.18(11) . . ?
C20 C18 C19 119.69(11) 3_557 . ?
C20 C18 C17 116.00(11) 3_557 . ?
C18 C19 C21 124.21(11) . . ?
C20 C19 C18 118.19(11) . . ?
C20 C19 C21 117.35(11) . . ?
C18 C20 C19 122.11(11) 3_557 . ?
C18 C20 H20 118.9 3_557 . ?
C19 C20 H20 118.9 . . ?
C17 O2 H2 109.5 . . ?
O2 C17 C18 112.23(11) . . ?
O1 C17 C18 122.82(12) . . ?
O1 C17 O2 124.75(12) . . ?
H9A O9 H9B 109.4 . . ?
O3 C21 C19 115.91(11) . . ?
O4 C21 C19 118.81(11) . . ?
O4 C21 O3 125.15(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_o7
_database_code_depnum_ccdc_archive 'CCDC 1851945'
loop_
_audit_author_name
_audit_author_address
'JInjian Liu'
;Shanxi Normal University
China
;
_audit_update_record             
;
2019-03-25 deposited with the CCDC.	2019-03-27 downloaded from the CCDC.
;
_audit_creation_date             2019-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'N O3, C8 H11 N, C5 H3 O4'
_chemical_formula_sum            'C13 H14 N2 O7'
_chemical_formula_weight         310.26
_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 0.0033 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'

_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           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.380(3)
_cell_length_b                   9.417(3)
_cell_length_c                   9.554(3)
_cell_angle_alpha                87.314(7)
_cell_angle_beta                 69.762(8)
_cell_angle_gamma                83.089(8)
_cell_volume                     702.2(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6012
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.398
_cell_measurement_theta_min      2.607
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.9648
_exptl_absorpt_correction_T_min  0.9601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8373
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.810
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2397
_reflns_number_total             2719
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker D8 venture'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.061
_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)+(0.0719P)²+0.2091P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1303
_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
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C11(H11)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
N1 N 0.98606(18) 0.31859(14) 0.33269(14) 0.0396(3) Uani 1 1 d . . . . .
N2 N 0.48568(17) 0.30903(14) 0.78455(14) 0.0379(3) Uani 1 1 d . . . . .
O1 O 0.2486(2) 0.01309(19) 0.59597(16) 0.0779(5) Uani 1 1 d . . . . .
O2 O -0.00509(16) 0.14083(14) 0.64507(12) 0.0482(3) Uani 1 1 d . . . . .
H2 H 0.0320 0.1606 0.5559 0.072 Uiso 1 1 calc GR . . . .
O3 O -0.22414(18) 0.35415(14) 0.96756(17) 0.0643(4) Uani 1 1 d . . . . .
O4 O 0.05235(16) 0.34906(12) 0.82867(14) 0.0474(3) Uani 1 1 d . . . . .
H4A H 0.0235 0.4313 0.8075 0.071 Uiso 1 1 calc GR . . . .
O5 O 0.8585(2) 0.37058(19) 0.42859(18) 0.0888(6) Uani 1 1 d . . . . .
O6 O 1.03952(19) 0.37670(13) 0.20765(13) 0.0567(4) Uani 1 1 d . . . . .
O7 O 1.06334(18) 0.20167(13) 0.35386(13) 0.0536(4) Uani 1 1 d . . . . .
C1 C 0.5729(4) 0.6870(2) 0.6399(3) 0.0738(7) Uani 1 1 d . . . . .
H1A H 0.6436 0.6676 0.5382 0.111 Uiso 1 1 calc GR . . . .
H1B H 0.6149 0.7618 0.6776 0.111 Uiso 1 1 calc GR . . . .
H1C H 0.4574 0.7164 0.6449 0.111 Uiso 1 1 calc GR . . . .
C2 C 0.5773(3) 0.5528(2) 0.7332(2) 0.0566(5) Uani 1 1 d . . . . .
H2A H 0.6952 0.5140 0.7153 0.068 Uiso 1 1 calc R . . . .
H2B H 0.5250 0.5766 0.8382 0.068 Uiso 1 1 calc R . . . .
C3 C 0.4835(2) 0.44251(18) 0.6955(2) 0.0458(4) Uani 1 1 d . . . . .
H3A H 0.3658 0.4819 0.7135 0.055 Uiso 1 1 calc R . . . .
H3B H 0.5357 0.4198 0.5902 0.055 Uiso 1 1 calc R . . . .
C4 C 0.5964(2) 0.19522(19) 0.7245(2) 0.0502(4) Uani 1 1 d . . . . .
H4 H 0.6690 0.1991 0.6259 0.060 Uiso 1 1 calc R . . . .
C5 C 0.6041(2) 0.07312(18) 0.80668(19) 0.0501(4) Uani 1 1 d . . . . .
H5 H 0.6822 -0.0050 0.7636 0.060 Uiso 1 1 calc R . . . .
C6 C 0.49614(19) 0.06528(15) 0.95377(16) 0.0337(3) Uani 1 1 d . . . . .
C7 C 0.3795(2) 0.18379(17) 1.01091(17) 0.0421(4) Uani 1 1 d . . . . .
H7 H 0.3022 0.1814 1.1079 0.051 Uiso 1 1 calc R . . . .
C8 C 0.3776(2) 0.30409(18) 0.92528(18) 0.0430(4) Uani 1 1 d . . . . .
H8 H 0.3003 0.3835 0.9654 0.052 Uiso 1 1 calc R . . . .
C9 C 0.1151(2) 0.06337(17) 0.68258(17) 0.0415(4) Uani 1 1 d . . . . .
C10 C 0.05937(19) 0.03675(15) 0.84840(16) 0.0344(3) Uani 1 1 d . . . . .
C11 C 0.1014(2) -0.09983(15) 0.89578(17) 0.0361(3) Uani 1 1 d . . . . .
H11 H 0.1706 -0.1670 0.8259 0.043 Uiso 1 1 calc R . . . .
C12 C -0.04161(19) 0.13791(15) 0.95392(17) 0.0341(3) Uani 1 1 d . . . . .
C13 C -0.0831(2) 0.29152(15) 0.91659(17) 0.0384(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 O5 1.208(2) . ?
N1 O6 1.2469(17) . ?
N1 O7 1.2533(18) . ?
N2 C3 1.486(2) . ?
N2 C4 1.337(2) . ?
N2 C8 1.339(2) . ?
O1 C9 1.195(2) . ?
O2 H2 0.8200 . ?
O2 C9 1.313(2) . ?
O3 C13 1.201(2) . ?
O4 H4A 0.8200 . ?
O4 C13 1.316(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.516(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.502(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C5 1.369(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(2) . ?
C6 C6 1.488(3) 2_657 ?
C6 C7 1.387(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.368(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.507(2) . ?
C10 C11 1.389(2) . ?
C10 C12 1.395(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.392(2) 2_557 ?
C12 C11 1.392(2) 2_557 ?
C12 C13 1.5023(19) . ?

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
O5 N1 O6 120.72(15) . . ?
O5 N1 O7 120.93(14) . . ?
O6 N1 O7 118.27(14) . . ?
C4 N2 C3 120.00(14) . . ?
C4 N2 C8 120.36(14) . . ?
C8 N2 C3 119.64(14) . . ?
C9 O2 H2 109.5 . . ?
C13 O4 H4A 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 C1 110.77(16) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
N2 C3 C2 112.31(14) . . ?
N2 C3 H3A 109.1 . . ?
N2 C3 H3B 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
N2 C4 H4 119.6 . . ?
N2 C4 C5 120.74(16) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.39(15) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C6 121.46(16) . 2_657 ?
C7 C6 C5 117.27(14) . . ?
C7 C6 C6 121.27(16) . 2_657 ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.31(15) . . ?
C8 C7 H7 119.8 . . ?
N2 C8 C7 120.88(14) . . ?
N2 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
O1 C9 O2 124.57(15) . . ?
O1 C9 C10 123.77(15) . . ?
O2 C9 C10 111.54(14) . . ?
C11 C10 C9 117.17(14) . . ?
C11 C10 C12 119.21(14) . . ?
C12 C10 C9 123.44(13) . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.11(14) . 2_557 ?
C12 C11 H11 119.4 2_557 . ?
C10 C12 C13 123.65(13) . . ?
C11 C12 C10 119.66(13) 2_557 . ?
C11 C12 C13 116.59(14) 2_557 . ?
O3 C13 O4 124.86(14) . . ?
O3 C13 C12 122.52(15) . . ?
O4 C13 C12 112.56(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
