# Electronic Supplementary Material (ESI) for ChemComm.
# 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_p170511a
_database_code_depnum_ccdc_archive 'CCDC 1839497'
loop_
_audit_author_name
_audit_author_address
'xia li'
;Nankai University, China
China
;
_audit_update_record             
;
2018-04-25 deposited with the CCDC.	2019-04-01 downloaded from the CCDC.
;
_audit_creation_date             2018-04-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H14 N4 O2'
_chemical_formula_sum            'C16 H14 N4 O2'
_chemical_formula_weight         294.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C 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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.7783(13)
_cell_length_b                   9.7768(7)
_cell_length_c                   10.5658(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.828(10)
_cell_angle_gamma                90.00
_cell_volume                     1330.28(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    820
_cell_measurement_temperature    117.4(5)
_cell_measurement_theta_max      28.5190
_cell_measurement_theta_min      3.6550
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2386
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.96
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      117.4(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2116
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  61.00   1.00   15.00    --   18.78 -19.00  30.00  105
  2  ω      9.00  39.00   1.00   15.00    --   18.78 -57.00  90.00   30
  3  ω    -83.00 -35.00   1.00   15.00    --  -19.10-178.00  90.00   48
  4  ω     51.00  87.00   1.00   15.00    --   18.78 178.00   0.00   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0287101000
_diffrn_orient_matrix_UB_12      -0.0318573000
_diffrn_orient_matrix_UB_13      0.0626164000
_diffrn_orient_matrix_UB_21      -0.0436404000
_diffrn_orient_matrix_UB_22      -0.0410842000
_diffrn_orient_matrix_UB_23      -0.0052849000
_diffrn_orient_matrix_UB_31      0.0174641000
_diffrn_orient_matrix_UB_32      -0.0505612000
_diffrn_orient_matrix_UB_33      -0.0349812000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                816
_reflns_number_total             1174
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.847
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1174
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0523
_refine_ls_restrained_S_all      0.847
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0860P)²+1.6460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1551
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 N2-H2B = N2-H2A
 0.85 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C1(H1A), C2(H2), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N 0.07837(15) 0.1213(2) 0.90160(18) 0.0233(6) Uani 1 d . . .
H1 H 0.0490 0.1999 0.8808 0.028 Uiso 1 calc . . R
N2 N 0.43873(17) 0.1236(2) 1.3679(2) 0.0274(6) Uani 1 d . . D
O1 O 0.08089(14) -0.22107(18) 0.90423(15) 0.0285(5) Uani 1 d . . .
C4 C 0.33080(19) 0.0147(3) 1.1576(2) 0.0233(6) Uani 1 d . . .
H4 H 0.3806 -0.0532 1.1698 0.028 Uiso 1 calc . . R
C8 C 0.03779(19) -0.1312(3) 0.8216(2) 0.0233(6) Uani 1 d . . .
C7 C 0.03636(19) 0.0184(3) 0.8170(2) 0.0210(6) Uani 1 d . . .
C6 C 0.16665(19) 0.1138(3) 1.0224(2) 0.0214(6) Uani 1 d . . .
C1 C 0.1807(2) 0.2129(3) 1.1225(2) 0.0227(6) Uani 1 d . . .
H1A H 0.1298 0.2789 1.1117 0.027 Uiso 1 calc . . R
C2 C 0.2691(2) 0.2143(3) 1.2372(2) 0.0263(7) Uani 1 d . . .
H2 H 0.2777 0.2819 1.3022 0.032 Uiso 1 calc . . R
C5 C 0.2426(2) 0.0148(3) 1.0412(2) 0.0242(6) Uani 1 d . . .
H5 H 0.2344 -0.0519 0.9754 0.029 Uiso 1 calc . . R
C3 C 0.34576(19) 0.1152(3) 1.2565(2) 0.0228(6) Uani 1 d . . .
H2A H 0.429(2) 0.159(2) 1.4358(18) 0.027 Uiso 1 d . . DR
H2B H 0.4744(18) 0.0498(18) 1.382(2) 0.027 Uiso 1 d . . DR

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0250(12) 0.0201(12) 0.0207(10) 0.0008(9) 0.0032(9) 0.0015(10)
N2 0.0277(13) 0.0305(15) 0.0211(10) -0.0020(10) 0.0050(10) 0.0038(11)
O1 0.0332(11) 0.0261(11) 0.0242(9) 0.0054(8) 0.0079(8) 0.0042(9)
C4 0.0234(14) 0.0210(14) 0.0241(12) 0.0015(11) 0.0066(11) -0.0001(12)
C8 0.0251(14) 0.0233(14) 0.0222(12) 0.0001(11) 0.0092(11) -0.0025(13)
C7 0.0232(14) 0.0219(14) 0.0174(11) -0.0013(10) 0.0066(11) -0.0004(12)
C6 0.0217(13) 0.0224(15) 0.0180(11) 0.0005(10) 0.0046(10) -0.0019(12)
C1 0.0231(14) 0.0225(14) 0.0215(11) -0.0026(10) 0.0069(10) 0.0024(12)
C2 0.0320(15) 0.0275(16) 0.0210(12) -0.0051(11) 0.0111(11) 0.0012(13)
C5 0.0307(15) 0.0207(14) 0.0222(11) -0.0040(10) 0.0106(11) -0.0025(12)
C3 0.0266(14) 0.0237(15) 0.0197(11) 0.0002(10) 0.0101(11) -0.0063(13)

_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 C7 1.333(3) . ?
N1 C6 1.418(3) . ?
N2 C3 1.400(3) . ?
O1 C8 1.232(3) . ?
C4 C5 1.388(3) . ?
C4 C3 1.395(3) . ?
C8 C8 1.501(5) 2_556 ?
C8 C7 1.464(4) . ?
C7 C7 1.415(4) 2_556 ?
C6 C1 1.396(3) . ?
C6 C5 1.387(4) . ?
C1 C2 1.380(3) . ?
C2 C3 1.393(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C6 126.4(2) . . ?
C5 C4 C3 120.9(2) . . ?
O1 C8 C8 134.53(14) . 2_556 ?
O1 C8 C7 137.2(2) . . ?
C7 C8 C8 88.31(13) . 2_556 ?
N1 C7 C8 137.3(2) . . ?
N1 C7 C7 130.94(14) . 2_556 ?
C7 C7 C8 91.68(13) 2_556 . ?
C1 C6 N1 119.3(2) . . ?
C5 C6 N1 121.8(2) . . ?
C5 C6 C1 118.8(2) . . ?
C2 C1 C6 120.9(2) . . ?
C1 C2 C3 120.6(2) . . ?
C6 C5 C4 120.4(2) . . ?
C4 C3 N2 121.2(2) . . ?
C2 C3 N2 120.1(2) . . ?
C2 C3 C4 118.5(2) . . ?

_olex2_date_sample_data_collection 2017-05-11
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.331
_oxdiff_exptl_absorpt_empirical_full_min 0.257
