# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_amide_H_sita3n2
_database_code_depnum_ccdc_archive 'CCDC 2055717'
loop_
_audit_author_name
_audit_author_address
'Tomoyuki Yoshimura'
;Kanazawa University
Japan
;
_audit_update_record             
;
2021-01-13 deposited with the CCDC.	2021-01-22 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C15 H22 N2 O4'
_chemical_formula_moiety         'C15 H22 N2 O4'
_chemical_formula_weight         294.35
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 -1/2-X,-1/2+Y,+Z
7 +X,-1/2-Y,-1/2+Z
8 -1/2+X,+Y,-1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.448(7)
_cell_length_b                   11.423(9)
_cell_length_c                   30.49(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     3291(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4603
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      25.14
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       unknown
_exptl_crystal_colour            unknown
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1264.00
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.384
_exptl_absorpt_correction_T_max  0.991

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            27508
_diffrn_reflns_av_unetI/netI     0.1006
_diffrn_reflns_av_R_equivalents  0.1799
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_min         2.536
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3737
_reflns_number_gt                1703
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.2338
_refine_ls_R_factor_gt           0.1122
_refine_ls_wR_factor_ref         0.2951
_refine_ls_wR_factor_gt          0.2330
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3737
_refine_ls_number_parameters     190
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1135P)²+1.0897P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8178(3) 0.2538(3) 0.18467(8) 0.0652(10) Uani 1 1 d . . . . .
H1 H 0.765453 0.197210 0.181415 0.078 Uiso 1 1 calc R U . . .
O2 O 0.8433(3) 0.5530(3) 0.19362(10) 0.0696(10) Uani 1 1 d . . . . .
O3 O 1.2165(5) 0.3835(4) 0.07641(15) 0.1164(17) Uani 1 1 d . . . . .
O4 O 1.3103(4) 0.4536(4) 0.13361(17) 0.1188(16) Uani 1 1 d . . . . .
N1 N 1.2221(5) 0.4550(4) 0.10471(16) 0.0702(12) Uani 1 1 d . . . . .
N2 N 1.0087(4) 0.4450(3) 0.22793(11) 0.0574(10) Uani 1 1 d . . . . .
C1 C 0.9299(4) 0.4734(4) 0.19242(13) 0.0455(10) Uani 1 1 d . . . . .
C2 C 0.8306(4) 0.2436(4) 0.10496(13) 0.0458(10) Uani 1 1 d . . . . .
C3 C 0.7493(5) 0.2672(4) 0.06799(14) 0.0643(13) Uani 1 1 d . . . . .
H3 H 0.686800 0.330027 0.068129 0.077 Uiso 1 1 calc R U . . .
C4 C 0.7609(7) 0.1976(6) 0.03094(16) 0.0809(17) Uani 1 1 d . . . . .
H4 H 0.705952 0.214000 0.006385 0.097 Uiso 1 1 calc R U . . .
C5 C 0.8519(6) 0.1056(6) 0.03029(18) 0.0856(18) Uani 1 1 d . . . . .
H5 H 0.859852 0.059504 0.005278 0.103 Uiso 1 1 calc R U . . .
C6 C 0.9324(6) 0.0809(5) 0.06686(18) 0.0783(16) Uani 1 1 d . . . . .
H6 H 0.994433 0.017697 0.066596 0.094 Uiso 1 1 calc R U . . .
C7 C 0.9211(4) 0.1495(4) 0.10363(15) 0.0591(12) Uani 1 1 d . . . . .
H7 H 0.975728 0.131926 0.128131 0.071 Uiso 1 1 calc R U . . .
C8 C 0.8205(4) 0.3210(4) 0.14525(13) 0.0486(11) Uani 1 1 d . . . . .
H8 H 0.734157 0.368264 0.143469 0.058 Uiso 1 1 calc R U . . .
C9 C 0.9494(4) 0.4030(3) 0.15019(12) 0.0428(10) Uani 1 1 d . . . . .
H9 H 1.035467 0.355598 0.152643 0.051 Uiso 1 1 calc R U . . .
C10 C 1.1087(6) 0.3468(5) 0.23090(16) 0.0839(16) Uani 1 1 d . . . . .
H10A H 1.151040 0.345700 0.259527 0.101 Uiso 1 1 calc R U . . .
H10B H 1.059263 0.274534 0.226002 0.101 Uiso 1 1 calc R U . . .
H10C H 1.181271 0.355884 0.209114 0.101 Uiso 1 1 calc R U . . .
C11 C 0.9866(6) 0.5129(5) 0.26814(16) 0.0966(19) Uani 1 1 d . . . . .
H11A H 1.048434 0.484304 0.290716 0.116 Uiso 1 1 calc R U . . .
H11B H 1.006832 0.593851 0.262558 0.116 Uiso 1 1 calc R U . . .
H11C H 0.890052 0.504864 0.277473 0.116 Uiso 1 1 calc R U . . .
C12 C 0.9643(4) 0.4867(4) 0.11086(13) 0.0508(11) Uani 1 1 d . . . . .
H12A H 0.948281 0.442054 0.084269 0.061 Uiso 1 1 calc R U . . .
H12B H 0.889546 0.544714 0.112810 0.061 Uiso 1 1 calc R U . . .
C13 C 1.1061(5) 0.5518(4) 0.10603(14) 0.0543(11) Uani 1 1 d . . . . .
C14 C 1.1417(6) 0.6350(5) 0.14278(19) 0.0895(18) Uani 1 1 d . . . . .
H14A H 1.134469 0.594821 0.170343 0.107 Uiso 1 1 calc R U . . .
H14B H 1.236463 0.663582 0.139022 0.107 Uiso 1 1 calc R U . . .
H14C H 1.076750 0.699657 0.142397 0.107 Uiso 1 1 calc R U . . .
C15 C 1.1162(5) 0.6119(5) 0.06153(17) 0.0805(16) Uani 1 1 d . . . . .
H15A H 1.093032 0.556967 0.038820 0.097 Uiso 1 1 calc R U . . .
H15B H 1.051062 0.676393 0.060556 0.097 Uiso 1 1 calc R U . . .
H15C H 1.210776 0.640318 0.057182 0.097 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.427(5) . ?
O1 H1 0.8200 . ?
O2 C1 1.224(5) . ?
O3 N1 1.189(5) . ?
O4 N1 1.213(5) . ?
N1 C13 1.557(6) . ?
N2 C1 1.354(5) . ?
N2 C11 1.466(5) . ?
N2 C10 1.470(6) . ?
C1 C9 1.529(5) . ?
C2 C7 1.375(6) . ?
C2 C3 1.390(6) . ?
C2 C8 1.516(6) . ?
C3 C4 1.385(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.358(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.372(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.543(5) . ?
C8 H8 0.9800 . ?
C9 C12 1.540(5) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.540(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.507(6) . ?
C13 C15 1.523(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
C8 O1 H1 109.5 . . ?
O3 N1 O4 123.3(6) . . ?
O3 N1 C13 118.4(5) . . ?
O4 N1 C13 118.3(5) . . ?
C1 N2 C11 117.6(4) . . ?
C1 N2 C10 125.9(4) . . ?
C11 N2 C10 116.4(4) . . ?
O2 C1 N2 121.5(4) . . ?
O2 C1 C9 119.8(4) . . ?
N2 C1 C9 118.7(4) . . ?
C7 C2 C3 118.1(4) . . ?
C7 C2 C8 121.3(4) . . ?
C3 C2 C8 120.6(4) . . ?
C4 C3 C2 120.5(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 120.4(5) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.7(5) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 120.0(5) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 121.3(5) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
O1 C8 C2 111.7(3) . . ?
O1 C8 C9 105.0(3) . . ?
C2 C8 C9 112.6(3) . . ?
O1 C8 H8 109.2 . . ?
C2 C8 H8 109.2 . . ?
C9 C8 H8 109.2 . . ?
C1 C9 C12 109.9(3) . . ?
C1 C9 C8 107.8(3) . . ?
C12 C9 C8 111.9(3) . . ?
C1 C9 H9 109.1 . . ?
C12 C9 H9 109.1 . . ?
C8 C9 H9 109.1 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C9 117.0(3) . . ?
C13 C12 H12A 108.0 . . ?
C9 C12 H12A 108.0 . . ?
C13 C12 H12B 108.0 . . ?
C9 C12 H12B 108.0 . . ?
H12A C12 H12B 107.3 . . ?
C14 C13 C15 111.3(4) . . ?
C14 C13 C12 115.3(4) . . ?
C15 C13 C12 110.9(4) . . ?
C14 C13 N1 108.1(4) . . ?
C15 C13 N1 104.7(4) . . ?
C12 C13 N1 105.8(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N2 C1 O2 0.2(6) . . . . ?
C10 N2 C1 O2 175.9(4) . . . . ?
C11 N2 C1 C9 -179.2(4) . . . . ?
C10 N2 C1 C9 -3.5(6) . . . . ?
C7 C2 C3 C4 -0.4(6) . . . . ?
C8 C2 C3 C4 178.7(4) . . . . ?
C2 C3 C4 C5 -0.1(8) . . . . ?
C3 C4 C5 C6 0.5(8) . . . . ?
C4 C5 C6 C7 -0.4(8) . . . . ?
C5 C6 C7 C2 -0.1(7) . . . . ?
C3 C2 C7 C6 0.6(6) . . . . ?
C8 C2 C7 C6 -178.6(4) . . . . ?
C7 C2 C8 O1 -43.4(5) . . . . ?
C3 C2 C8 O1 137.5(4) . . . . ?
C7 C2 C8 C9 74.4(5) . . . . ?
C3 C2 C8 C9 -104.7(4) . . . . ?
O2 C1 C9 C12 48.0(5) . . . . ?
N2 C1 C9 C12 -132.6(4) . . . . ?
O2 C1 C9 C8 -74.2(4) . . . . ?
N2 C1 C9 C8 105.3(4) . . . . ?
O1 C8 C9 C1 -56.5(4) . . . . ?
C2 C8 C9 C1 -178.2(3) . . . . ?
O1 C8 C9 C12 -177.4(3) . . . . ?
C2 C8 C9 C12 60.8(4) . . . . ?
C1 C9 C12 C13 74.6(4) . . . . ?
C8 C9 C12 C13 -165.7(3) . . . . ?
C9 C12 C13 C14 -63.4(5) . . . . ?
C9 C12 C13 C15 168.9(4) . . . . ?
C9 C12 C13 N1 56.0(5) . . . . ?
O3 N1 C13 C14 -176.5(4) . . . . ?
O4 N1 C13 C14 6.4(5) . . . . ?
O3 N1 C13 C15 -57.8(5) . . . . ?
O4 N1 C13 C15 125.1(5) . . . . ?
O3 N1 C13 C12 59.5(5) . . . . ?
O4 N1 C13 C12 -117.6(4) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


