# 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_r20201010a
_database_code_depnum_ccdc_archive 'CCDC 2036666'
loop_
_audit_author_name
_audit_author_address
'Kaikai Niu'
;Nankai University
China
;
_audit_update_record             
;
2020-10-12 deposited with the CCDC.	2021-04-13 downloaded from the CCDC.
;
_audit_creation_date             2020-10-11
_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 H10 N4 O, 0.5(H2 O)'
_chemical_formula_sum            'C12 H11 N4 O1.50'
_chemical_formula_weight         235.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.0472(7)
_cell_length_b                   7.0440(3)
_cell_length_c                   16.9293(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.096(4)
_cell_angle_gamma                90
_cell_volume                     2139.96(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9309
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.5340
_cell_measurement_theta_min      2.2660
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9092
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.362
_diffrn_reflns_theta_min         2.270
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  35.00   1.00    1.00    --  -25.00  45.00  90.00  150
  3  ω   -115.00   5.00   1.00    1.00    --  -25.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0011321000
_diffrn_orient_matrix_UB_12      -0.0466918000
_diffrn_orient_matrix_UB_13      -0.0347007000
_diffrn_orient_matrix_UB_21      -0.0105687000
_diffrn_orient_matrix_UB_22      0.0860081000
_diffrn_orient_matrix_UB_23      -0.0189438000
_diffrn_orient_matrix_UB_31      0.0407782000
_diffrn_orient_matrix_UB_32      0.0235498000
_diffrn_orient_matrix_UB_33      0.0003944000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1828
_reflns_number_total             2181
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       CrystalClear(Rigaku,2008)
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.240
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0092(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.053
_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)+(0.0526P)²+1.9817P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1226
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Rigid bond restraints
 C3, C4
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Others
 Fixed Sof: O2(0.5) H2A(0.5) H2B(0.5)
4.a Free rotating group:
 O2(H2A,H2B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12)
4.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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
O1 O 0.16094(6) 0.61848(16) -0.02998(7) 0.0290(3) Uani 1 1 d . . . . .
N1 N 0.03896(7) 0.69308(18) -0.06495(7) 0.0233(3) Uani 1 1 d . . . . .
N2 N 0.02387(7) 0.76453(19) 0.09400(8) 0.0282(3) Uani 1 1 d . . . . .
N3 N 0.14455(7) 0.6707(2) 0.13195(8) 0.0297(4) Uani 1 1 d . . . . .
N4 N 0.12626(9) 0.6266(3) 0.20664(8) 0.0458(5) Uani 1 1 d . . . . .
C1 C -0.02988(8) 0.7534(2) -0.04358(10) 0.0260(4) Uani 1 1 d . . . . .
C2 C -0.09199(10) 0.7788(2) -0.09947(12) 0.0394(5) Uani 1 1 d . . . . .
H2 H -0.088268 0.756231 -0.154226 0.047 Uiso 1 1 calc R . . . .
C3 C -0.15821(10) 0.8366(3) -0.07460(16) 0.0530(6) Uani 1 1 d . U . . .
H3 H -0.200503 0.851280 -0.112577 0.064 Uiso 1 1 calc R . . . .
C4 C -0.16488(10) 0.8740(3) 0.00463(17) 0.0554(6) Uani 1 1 d . U . . .
H4 H -0.211145 0.915640 0.020473 0.066 Uiso 1 1 calc R . . . .
C5 C -0.10422(10) 0.8507(2) 0.06040(14) 0.0431(5) Uani 1 1 d . . . . .
H5 H -0.108547 0.876401 0.114809 0.052 Uiso 1 1 calc R . . . .
C6 C -0.03599(8) 0.7889(2) 0.03675(10) 0.0281(4) Uani 1 1 d . . . . .
C7 C 0.08604(8) 0.7076(2) 0.07206(9) 0.0227(3) Uani 1 1 d . . . . .
C8 C 0.10029(8) 0.66895(19) -0.01100(9) 0.0209(3) Uani 1 1 d . . . . .
C9 C 0.04753(10) 0.6556(3) -0.14886(10) 0.0400(5) Uani 1 1 d . . . . .
H9A H 0.039160 0.773089 -0.179479 0.060 Uiso 1 1 calc GR . . . .
H9B H 0.011123 0.559746 -0.169503 0.060 Uiso 1 1 calc GR . . . .
H9C H 0.098010 0.608783 -0.153564 0.060 Uiso 1 1 calc GR . . . .
C10 C 0.21972(9) 0.6707(3) 0.12904(11) 0.0364(4) Uani 1 1 d . . . . .
H10 H 0.245207 0.698431 0.084115 0.044 Uiso 1 1 calc R . . . .
C11 C 0.25103(11) 0.6234(3) 0.20273(12) 0.0532(6) Uani 1 1 d . . . . .
H11 H 0.302607 0.610234 0.219995 0.064 Uiso 1 1 calc R . . . .
C12 C 0.19147(12) 0.5980(4) 0.24782(12) 0.0599(7) Uani 1 1 d . . . . .
H12 H 0.197275 0.563844 0.302413 0.072 Uiso 1 1 calc R . . . .
O2 O -0.02227(14) 0.9423(3) 0.2420(2) 0.0385(8) Uani 0.5 1 d . . P A -1
H2A H -0.032425 0.862535 0.278612 0.058 Uiso 0.5 1 d G . P A -1
H2B H -0.002717 0.881633 0.204552 0.058 Uiso 0.5 1 d G . P A -1


_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 1.2257(17) . ?
N1 C1 1.397(2) . ?
N1 C8 1.3688(19) . ?
N1 C9 1.469(2) . ?
N2 C6 1.383(2) . ?
N2 C7 1.283(2) . ?
N3 N4 1.3759(19) . ?
N3 C7 1.408(2) . ?
N3 C10 1.363(2) . ?
N4 C12 1.318(3) . ?
C1 C2 1.399(2) . ?
C1 C6 1.398(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.370(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.404(2) . ?
C7 C8 1.481(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 0.9500 . ?
C10 C11 1.355(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.394(3) . ?
C12 H12 0.9500 . ?
O2 H2A 0.8700 . ?
O2 H2B 0.8705 . ?

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 C9 119.55(13) . . ?
C8 N1 C1 122.92(13) . . ?
C8 N1 C9 117.53(13) . . ?
C7 N2 C6 118.53(14) . . ?
N4 N3 C7 117.94(13) . . ?
C10 N3 N4 111.72(14) . . ?
C10 N3 C7 130.34(14) . . ?
C12 N4 N3 103.46(15) . . ?
N1 C1 C2 122.30(16) . . ?
N1 C1 C6 118.06(14) . . ?
C6 C1 C2 119.63(16) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.50(19) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.78(18) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.9(2) . . ?
C6 C5 H5 120.0 . . ?
N2 C6 C1 121.53(14) . . ?
N2 C6 C5 118.81(16) . . ?
C1 C6 C5 119.66(17) . . ?
N2 C7 N3 117.46(14) . . ?
N2 C7 C8 125.28(14) . . ?
N3 C7 C8 117.19(13) . . ?
O1 C8 N1 122.85(14) . . ?
O1 C8 C7 123.50(14) . . ?
N1 C8 C7 113.64(13) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10 126.7 . . ?
C11 C10 N3 106.63(17) . . ?
C11 C10 H10 126.7 . . ?
C10 C11 H11 127.3 . . ?
C10 C11 C12 105.37(18) . . ?
C12 C11 H11 127.3 . . ?
N4 C12 C11 112.82(17) . . ?
N4 C12 H12 123.6 . . ?
C11 C12 H12 123.6 . . ?
H2A O2 H2B 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
N1 C1 C2 C3 179.37(15) . . . . ?
N1 C1 C6 N2 -0.3(2) . . . . ?
N1 C1 C6 C5 179.66(14) . . . . ?
N2 C7 C8 O1 178.40(14) . . . . ?
N2 C7 C8 N1 -2.2(2) . . . . ?
N3 N4 C12 C11 0.4(3) . . . . ?
N3 C7 C8 O1 -4.6(2) . . . . ?
N3 C7 C8 N1 174.82(12) . . . . ?
N3 C10 C11 C12 -0.5(2) . . . . ?
N4 N3 C7 N2 24.4(2) . . . . ?
N4 N3 C7 C8 -152.89(14) . . . . ?
N4 N3 C10 C11 0.8(2) . . . . ?
C1 N1 C8 O1 -178.97(13) . . . . ?
C1 N1 C8 C7 1.64(19) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C2 C1 C6 N2 179.63(14) . . . . ?
C2 C1 C6 C5 -0.4(2) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 N2 -179.29(15) . . . . ?
C4 C5 C6 C1 0.7(2) . . . . ?
C6 N2 C7 N3 -175.52(13) . . . . ?
C6 N2 C7 C8 1.5(2) . . . . ?
C6 C1 C2 C3 -0.6(2) . . . . ?
C7 N2 C6 C1 -0.2(2) . . . . ?
C7 N2 C6 C5 179.85(14) . . . . ?
C7 N3 N4 C12 179.18(17) . . . . ?
C7 N3 C10 C11 -179.12(17) . . . . ?
C8 N1 C1 C2 179.51(14) . . . . ?
C8 N1 C1 C6 -0.6(2) . . . . ?
C9 N1 C1 C2 0.4(2) . . . . ?
C9 N1 C1 C6 -179.66(14) . . . . ?
C9 N1 C8 O1 0.2(2) . . . . ?
C9 N1 C8 C7 -179.24(13) . . . . ?
C10 N3 N4 C12 -0.7(2) . . . . ?
C10 N3 C7 N2 -155.73(17) . . . . ?
C10 N3 C7 C8 27.0(2) . . . . ?
C10 C11 C12 N4 0.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.363
_oxdiff_exptl_absorpt_empirical_full_min 0.815
