# 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_exp_6638
_database_code_depnum_ccdc_archive 'CCDC 1913836'
loop_
_audit_author_name
_audit_author_address
'Xingxing Ma'
;Huaqiao university
China
;
_audit_update_record             
;
2019-05-03 deposited with the CCDC.	2019-06-10 downloaded from the CCDC.
;
_audit_creation_date             2019-05-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_formula_moiety         '0.67(C17 H14 N3 O2)'
_chemical_formula_sum            'C11.333 H9.333 N2 O1.333'
_chemical_formula_weight         194.88
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   15.409(2)
_cell_length_b                   8.2878(8)
_cell_length_c                   12.3822(16)
_cell_angle_alpha                90
_cell_angle_beta                 111.992(16)
_cell_angle_gamma                90
_exptl_crystal_description       block
_cell_measurement_temperature    298
_diffrn_ambient_temperature      298
_cell_volume                     1466.3(4)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    1426
_cell_measurement_theta_max      26.7630
_cell_measurement_theta_min      3.6570
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.3241
_exptl_crystal_F_000             612.2802
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6918
_diffrn_reflns_theta_full        24.9994
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.55
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.9977
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0466291000
_diffrn_orient_matrix_UB_12      -0.0274201000
_diffrn_orient_matrix_UB_13      -0.0156414000
_diffrn_orient_matrix_UB_21      0.0045869000
_diffrn_orient_matrix_UB_22      0.0052717000
_diffrn_orient_matrix_UB_23      0.0591251000
_diffrn_orient_matrix_UB_31      -0.0161116000
_diffrn_orient_matrix_UB_32      0.0809956000
_diffrn_orient_matrix_UB_33      -0.0091227000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -18
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1717
_reflns_number_total             2576
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.5335
_refine_diff_density_min         -0.4955
_refine_diff_density_rms         0.1196
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             5.7406
_refine_ls_goodness_of_fit_ref   1.0767
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0630
_refine_ls_restrained_S_all      1.0767
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.1828
_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
2.a Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00E(H00E), C00B(H00B), C00D(H00D), C00I(H00I), C00K(H00K),
 C00F(H00F), C00C(H00C)
2.b Idealised Me refined as rotating group:
 C00L(H00a,H00g,H00h), C00M(H00l,H00m,H00n)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
O001 O 0.97775(12) 0.5027(2) 0.65742(15) 0.0672(6) Uani 1.000000 .
N002 N 0.57073(13) 0.1979(2) 0.41752(14) 0.0431(5) Uani 1.000000 .
O003 O 0.17263(12) 0.1411(2) 0.45768(16) 0.0714(6) Uani 1.000000 .
N004 N 0.64441(15) 0.1105(2) 0.29032(15) 0.0521(5) Uani 1.000000 .
N005 N 0.48674(14) 0.0391(2) 0.25186(15) 0.0536(6) Uani 1.000000 .
C006 C 0.41149(16) 0.1265(2) 0.38022(17) 0.0414(6) Uani 1.000000 .
C007 C 0.73088(16) 0.2732(2) 0.45822(17) 0.0422(6) Uani 1.000000 .
C008 C 0.49395(16) 0.1206(2) 0.34938(17) 0.0421(6) Uani 1.000000 .
C009 C 0.64418(17) 0.1899(2) 0.38522(17) 0.0431(6) Uani 1.000000 .
C00A C 0.89383(16) 0.4303(3) 0.59605(19) 0.0477(6) Uani 1.000000 .
C00B C 0.73742(16) 0.3520(3) 0.55971(18) 0.0473(6) Uani 1.000000 .
C00C C 0.41360(17) 0.2051(3) 0.48051(19) 0.0474(6) Uani 1.000000 .
C00D C 0.81784(17) 0.4300(3) 0.62812(19) 0.0490(6) Uani 1.000000 .
C00E C 0.80845(17) 0.2750(3) 0.42693(19) 0.0497(6) Uani 1.000000 .
C00F C 0.33619(17) 0.2128(3) 0.50978(19) 0.0499(6) Uani 1.000000 .
C00G C 0.25360(17) 0.1409(3) 0.4379(2) 0.0509(6) Uani 1.000000 .
C00H C 0.56358(18) 0.0390(3) 0.22840(19) 0.0528(6) Uani 1.000000 .
C00I C 0.32801(18) 0.0556(3) 0.3096(2) 0.0549(7) Uani 1.000000 .
C00J C 0.88915(17) 0.3520(3) 0.4943(2) 0.0528(7) Uani 1.000000 .
C00K C 0.25058(18) 0.0631(3) 0.3377(2) 0.0618(7) Uani 1.000000 .
C00L C 0.1747(2) 0.2043(4) 0.5653(2) 0.0762(9) Uani 1.000000 .
C00M C 0.9863(2) 0.5860(4) 0.7619(3) 0.0804(9) Uani 1.000000 .
H00J H 0.94065(17) 0.3521(3) 0.4724(2) 0.0633(8) Uiso 1.000000 R
H00E H 0.80555(17) 0.2231(3) 0.35909(19) 0.0597(8) Uiso 1.000000 R
H00B H 0.68611(16) 0.3520(3) 0.58201(18) 0.0568(7) Uiso 1.000000 R
H00D H 0.82071(17) 0.4824(3) 0.69581(19) 0.0588(7) Uiso 1.000000 R
H00I H 0.32478(18) 0.0023(3) 0.2421(2) 0.0659(8) Uiso 1.000000 R
H00K H 0.19513(18) 0.0153(3) 0.2889(2) 0.0742(9) Uiso 1.000000 R
H00F H 0.33915(17) 0.2658(3) 0.57728(19) 0.0599(7) Uiso 1.000000 R
H00C H 0.46889(17) 0.2538(3) 0.52890(19) 0.0569(7) Uiso 1.000000 R
H00a H 0.1141(4) 0.192(2) 0.5697(8) 0.1143(13) Uiso 1.000000 GR
H00g H 0.2204(11) 0.1469(17) 0.6285(2) 0.1143(13) Uiso 1.000000 GR
H00h H 0.1909(15) 0.3167(7) 0.5705(8) 0.1143(13) Uiso 1.000000 GR
H00l H 0.9404(10) 0.6704(17) 0.7440(4) 0.1205(14) Uiso 1.000000 GR
H00m H 0.9764(16) 0.5117(6) 0.8157(8) 0.1205(14) Uiso 1.000000 GR
H00n H 1.0478(5) 0.632(2) 0.7962(11) 0.1205(14) Uiso 1.000000 GR


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
O001 C00A 1.369(3) . ?
O001 C00M 1.428(3) . ?
N002 C008 1.332(3) . ?
N002 C009 1.336(3) . ?
O003 C00G 1.358(3) . ?
O003 C00L 1.421(3) . ?
N004 C009 1.348(3) . ?
N004 C00H 1.332(3) . ?
N005 C008 1.351(3) . ?
N005 C00H 1.321(3) . ?
C006 C008 1.458(3) . ?
C006 C00C 1.392(3) . ?
C006 C00I 1.386(3) . ?
C007 C009 1.474(3) . ?
C007 C00B 1.386(3) . ?
C007 C00E 1.388(3) . ?
C00A C00D 1.370(3) . ?
C00A C00J 1.394(3) . ?
C00B C00D 1.373(3) . ?
C00B H00B 0.9300 . ?
C00C C00F 1.372(3) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00E C00J 1.369(3) . ?
C00E H00E 0.9300 . ?
C00F C00G 1.385(3) . ?
C00F H00F 0.9300 . ?
C00G C00K 1.384(3) . ?
C00I C00K 1.363(3) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00L H00a 0.9600 . ?
C00L H00g 0.9600 . ?
C00L H00h 0.9600 . ?
C00M H00l 0.9600 . ?
C00M H00m 0.9600 . ?
C00M H00n 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
C00M O001 C00A 117.52(19) . . ?
C009 N002 C008 115.96(17) . . ?
C00L O003 C00G 118.0(2) . . ?
C00H N004 C009 114.3(2) . . ?
C00H N005 C008 114.62(19) . . ?
C00C C006 C008 121.2(2) . . ?
C00I C006 C008 121.0(2) . . ?
C00I C006 C00C 117.8(2) . . ?
C00B C007 C009 121.2(2) . . ?
C00E C007 C009 120.75(19) . . ?
C00E C007 C00B 118.1(2) . . ?
N005 C008 N002 124.2(2) . . ?
C006 C008 N002 118.19(18) . . ?
C006 C008 N005 117.56(19) . . ?
N004 C009 N002 124.4(2) . . ?
C007 C009 N002 117.91(18) . . ?
C007 C009 N004 117.7(2) . . ?
C00D C00A O001 124.9(2) . . ?
C00J C00A O001 115.1(2) . . ?
C00J C00A C00D 120.0(2) . . ?
C00D C00B C007 121.6(2) . . ?
H00B C00B C007 119.21(13) . . ?
H00B C00B C00D 119.21(13) . . ?
C00F C00C C006 121.7(2) . . ?
H00C C00C C006 119.16(14) . . ?
H00C C00C C00F 119.16(13) . . ?
C00B C00D C00A 119.6(2) . . ?
H00D C00D C00A 120.20(13) . . ?
H00D C00D C00B 120.20(13) . . ?
C00J C00E C007 121.0(2) . . ?
H00E C00E C007 119.48(13) . . ?
H00E C00E C00J 119.48(13) . . ?
C00G C00F C00C 119.4(2) . . ?
H00F C00F C00C 120.29(13) . . ?
H00F C00F C00G 120.29(14) . . ?
C00F C00G O003 124.7(2) . . ?
C00K C00G O003 116.0(2) . . ?
C00K C00G C00F 119.4(2) . . ?
N005 C00H N004 126.5(2) . . ?
C00K C00I C006 121.0(2) . . ?
H00I C00I C006 119.52(14) . . ?
H00I C00I C00K 119.52(14) . . ?
C00E C00J C00A 119.7(2) . . ?
H00J C00J C00A 120.14(14) . . ?
H00J C00J C00E 120.14(13) . . ?
C00I C00K C00G 120.7(2) . . ?
H00K C00K C00G 119.64(14) . . ?
H00K C00K C00I 119.64(14) . . ?
H00a C00L O003 109.5 . . ?
H00g C00L O003 109.5 . . ?
H00g C00L H00a 109.5 . . ?
H00h C00L O003 109.5 . . ?
H00h C00L H00a 109.5 . . ?
H00h C00L H00g 109.5 . . ?
H00l C00M O001 109.5 . . ?
H00m C00M O001 109.5 . . ?
H00m C00M H00l 109.5 . . ?
H00n C00M O001 109.5 . . ?
H00n C00M H00l 109.5 . . ?
H00n C00M H00m 109.5 . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.590
_oxdiff_exptl_absorpt_empirical_full_min 0.661
