# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_180419h
_database_code_depnum_ccdc_archive 'CCDC 1905891'
loop_
_audit_author_name
_audit_author_address
'Pengpeng Yang'
;Nanjing Tech University
China
;
_audit_update_record             
;
2019-08-30 deposited with the CCDC.	2019-09-26 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          185
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H20 N2 O4'
_chemical_formula_weight         220.27

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.6508(9)
_cell_length_b                   14.5943(13)
_cell_length_c                   7.9248(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.384(3)
_cell_angle_gamma                90
_cell_volume                     1175.57(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2094
_cell_measurement_theta_min      2.442
_cell_measurement_theta_max      28.414

_exptl_crystal_description       block
_exptl_crystal_colour            transparent
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9585
_exptl_absorpt_correction_T_max  0.9809
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5715
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.442
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        24.993
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2068
_reflns_number_gt                1507
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0793P)²+0.4744P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.197(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2068
_refine_ls_number_parameters     143
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1655
_refine_ls_wR_factor_gt          0.1493
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.05920(17) 0.65765(12) 0.6542(2) 0.0337(5) Uani 1 1 d . . . . .
H1A H 1.073044 0.711504 0.610141 0.051 Uiso 1 1 calc R U . . .
H1B H 1.118812 0.617454 0.642244 0.051 Uiso 1 1 calc R U . . .
H1C H 1.065929 0.664029 0.768237 0.051 Uiso 1 1 calc R U . . .
N2 N 0.33487(18) 0.69420(12) 0.4937(3) 0.0389(5) Uani 1 1 d . . . . .
H2A H 0.339810 0.685168 0.606549 0.058 Uiso 1 1 calc R U . . .
H2B H 0.259044 0.671997 0.424738 0.058 Uiso 1 1 calc R U . . .
H2C H 0.339197 0.753959 0.473699 0.058 Uiso 1 1 calc R U . . .
O1 O 0.38084(16) 0.64309(10) 0.8469(2) 0.0437(5) Uani 1 1 d . . . . .
O2 O 0.25649(17) 0.52712(11) 0.7177(2) 0.0500(5) Uani 1 1 d . . . . .
O3 O 0.10118(19) 0.67204(10) 0.0190(2) 0.0488(5) Uani 1 1 d . . . . .
O4 O 0.1184(2) 0.60906(12) 0.2779(2) 0.0589(6) Uani 1 1 d . . . . .
C1 C 0.9264(2) 0.62446(16) 0.5580(3) 0.0397(6) Uani 1 1 d . . . . .
H1D H 0.917020 0.561535 0.591781 0.048 Uiso 1 1 calc R U . . .
H1E H 0.915274 0.625504 0.431973 0.048 Uiso 1 1 calc R U . . .
C2 C 0.8209(2) 0.68237(17) 0.5965(3) 0.0437(6) Uani 1 1 d . . . . .
H2D H 0.823677 0.743797 0.551021 0.052 Uiso 1 1 calc R U . . .
H2E H 0.836756 0.686570 0.723320 0.052 Uiso 1 1 calc R U . . .
C3 C 0.6867(3) 0.6406(2) 0.5114(4) 0.0571(8) Uani 1 1 d . . . . .
H3A H 0.669310 0.641351 0.384037 0.068 Uiso 1 1 calc R U . . .
H3B H 0.688449 0.577062 0.547958 0.068 Uiso 1 1 calc R U . . .
C4 C 0.5755(2) 0.68861(18) 0.5561(4) 0.0477(7) Uani 1 1 d . . . . .
H4A H 0.576330 0.753183 0.527464 0.057 Uiso 1 1 calc R U . . .
H4B H 0.587492 0.683335 0.681989 0.057 Uiso 1 1 calc R U . . .
C5 C 0.4446(2) 0.64721(17) 0.4542(4) 0.0483(7) Uani 1 1 d . . . . .
H5A H 0.433699 0.651409 0.328488 0.058 Uiso 1 1 calc R U . . .
H5B H 0.443544 0.582873 0.484503 0.058 Uiso 1 1 calc R U . . .
C6 C 0.3486(2) 0.55921(15) 0.8365(3) 0.0354(6) Uani 1 1 d . . . . .
C7 C 0.4278(2) 0.49560(19) 0.9795(4) 0.0525(7) Uani 1 1 d . . . . .
H7A H 0.404134 0.507086 1.086738 0.063 Uiso 1 1 calc R U . . .
H7B H 0.403176 0.432949 0.943708 0.063 Uiso 1 1 calc R U . . .
C8 C 0.0923(3) 0.60608(16) 0.1145(3) 0.0512(7) Uani 1 1 d D . . . .
C9 C 0.0729(3) 0.5104(2) 0.0244(5) 0.0380(8) Uani 0.669(4) 1 d D . P A 1
H9A H 0.101957 0.511218 -0.080488 0.046 Uiso 0.669(4) 1 calc R U P A 1
H9B H 0.122907 0.464272 0.104966 0.046 Uiso 0.669(4) 1 calc R U P A 1
C9' C -0.0297(6) 0.5415(4) 0.0328(10) 0.0380(8) Uani 0.331(4) 1 d D . P A 2
H9'1 H -0.070971 0.523717 0.121560 0.046 Uiso 0.331(4) 1 calc R U P A 2
H9'2 H -0.094430 0.571544 -0.064066 0.046 Uiso 0.331(4) 1 calc R U P A 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
N1 C1 1.474(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 C5 1.467(3) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
O1 C6 1.267(3) . ?
O2 C6 1.232(3) . ?
O3 C8 1.246(3) . ?
O4 C8 1.241(3) . ?
C1 C2 1.508(3) . ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?
C2 C3 1.515(4) . ?
C2 H2D 0.9700 . ?
C2 H2E 0.9700 . ?
C3 C4 1.507(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.513(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.512(3) . ?
C7 C7 1.480(5) 3_667 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.554(4) . ?
C8 C9' 1.579(6) . ?
C9 C9 1.514(7) 3_565 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9' C9' 1.527(14) 3_565 ?
C9' H9'1 0.9700 . ?
C9' H9'2 0.9700 . ?

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
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C5 N2 H2A 109.5 . . ?
C5 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C5 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
N1 C1 C2 111.65(19) . . ?
N1 C1 H1D 109.3 . . ?
C2 C1 H1D 109.3 . . ?
N1 C1 H1E 109.3 . . ?
C2 C1 H1E 109.3 . . ?
H1D C1 H1E 108.0 . . ?
C1 C2 C3 110.2(2) . . ?
C1 C2 H2D 109.6 . . ?
C3 C2 H2D 109.6 . . ?
C1 C2 H2E 109.6 . . ?
C3 C2 H2E 109.6 . . ?
H2D C2 H2E 108.1 . . ?
C4 C3 C2 114.3(2) . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 C5 110.6(2) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N2 C5 C4 111.4(2) . . ?
N2 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
N2 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
O2 C6 O1 123.8(2) . . ?
O2 C6 C7 118.6(2) . . ?
O1 C6 C7 117.7(2) . . ?
C7 C7 C6 114.9(3) 3_667 . ?
C7 C7 H7A 108.5 3_667 . ?
C6 C7 H7A 108.5 . . ?
C7 C7 H7B 108.5 3_667 . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
O4 C8 O3 125.0(2) . . ?
O4 C8 C9 117.9(2) . . ?
O3 C8 C9 116.1(2) . . ?
O4 C8 C9' 110.4(3) . . ?
O3 C8 C9' 114.5(3) . . ?
C9 C9 C8 106.4(3) 3_565 . ?
C9 C9 H9A 110.4 3_565 . ?
C8 C9 H9A 110.4 . . ?
C9 C9 H9B 110.4 3_565 . ?
C8 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
C9' C9' C8 103.9(6) 3_565 . ?
C9' C9' H9'1 111.0 3_565 . ?
C8 C9' H9'1 111.0 . . ?
C9' C9' H9'2 111.0 3_565 . ?
C8 C9' H9'2 111.0 . . ?
H9'1 C9' H9'2 109.0 . . ?

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
N1 C1 C2 C3 -174.0(2) . . . . ?
C1 C2 C3 C4 174.6(2) . . . . ?
C2 C3 C4 C5 175.4(2) . . . . ?
C3 C4 C5 N2 -179.0(2) . . . . ?
O2 C6 C7 C7 132.4(3) . . . 3_667 ?
O1 C6 C7 C7 -48.0(4) . . . 3_667 ?
O4 C8 C9 C9 92.3(4) . . . 3_565 ?
O3 C8 C9 C9 -98.9(4) . . . 3_565 ?
O4 C8 C9' C9' -110.1(7) . . . 3_565 ?
O3 C8 C9' C9' 102.6(6) . . . 3_565 ?

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
C9^a H9A^a O2 0.97 2.63 3.554(4) 160.4 1_554 yes
C4 H4A O1 0.97 2.63 3.321(3) 128.8 4_575 yes
N2 H2C O1 0.89 1.93 2.752(2) 152.5 4_575 yes
N2 H2B O4 0.89 1.84 2.725(3) 170.4 . yes
N2 H2A O1 0.89 1.92 2.795(3) 166.0 . yes
N1 H1C O3 0.89 1.91 2.798(2) 173.2 1_656 yes
N1 H1B O2 0.89 1.93 2.769(2) 156.6 1_655 yes
N1 H1A O3 0.89 1.91 2.795(2) 178.9 4_676 yes

_refine_diff_density_max         0.373
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.056


_chemical_properties_physical    Moisture-sensitive,Hygroscopic
