# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

####################################################################### 
# 
# 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_liyx0323
_database_code_depnum_ccdc_archive 'CCDC 1409382'
_audit_update_record             
;
2015-06-29 deposited with the CCDC.
2015-11-04 downloaded from the CCDC.
;
_audit_creation_date             2015-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H16 N2 O'
_chemical_formula_sum            'C22 H16 N2 O'
_chemical_formula_weight         324.37
_chemical_melting_point          ?
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 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'

_cell_length_a                   8.4582(5)
_cell_length_b                   11.1421(5)
_cell_length_c                   18.5214(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.439(5)
_cell_angle_gamma                90.00
_cell_volume                     1716.59(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1570
_cell_measurement_temperature    291.73(10)
_cell_measurement_theta_max      24.2740
_cell_measurement_theta_min      3.8140
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6540
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.52
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.73(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   84.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416   19.0000  150.0000 64

#__ type_ start__ end____ width___ exp.time_
  2 omega  -27.00    0.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3041   38.0000  -60.0000 18

#__ type_ start__ end____ width___ exp.time_
  3 omega  -32.00   40.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -57.0000  -60.0000 48

#__ type_ start__ end____ width___ exp.time_
  4 omega   46.00   73.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  178.0000  120.0000 18
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0742174000
_diffrn_orient_matrix_UB_12      -0.0252359000
_diffrn_orient_matrix_UB_13      -0.0173262000
_diffrn_orient_matrix_UB_21      0.0047710000
_diffrn_orient_matrix_UB_22      -0.0425630000
_diffrn_orient_matrix_UB_23      0.0287886000
_diffrn_orient_matrix_UB_31      -0.0416143000
_diffrn_orient_matrix_UB_32      0.0400645000
_diffrn_orient_matrix_UB_33      0.0197211000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2316
_reflns_number_total             3377
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.027(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3377
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0557
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0445P)²+0.5478P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1413
_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
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C5(H5), C13(H13), C1(H1), C22(H22), C16(H16), C10(H10), C18(H18),
 C3(H3), C11(H11), C12(H12), C21(H21), C2(H2), C4(H4), C20(H20), C19(H19)
;
_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 0.2681(2) 0.43647(15) 0.04699(9) 0.0424(4) Uani 1 d . . .
N2 N 0.1941(2) 0.44762(15) -0.07441(9) 0.0461(5) Uani 1 d . . .
C7 C 0.2501(2) 0.50853(19) -0.01357(11) 0.0422(5) Uani 1 d . . .
C15 C 0.2200(3) 0.32170(18) 0.02209(11) 0.0427(5) Uani 1 d . . .
C8 C 0.1741(2) 0.33221(18) -0.05309(11) 0.0426(5) Uani 1 d . . .
C9 C 0.1101(3) 0.24116(18) -0.10841(11) 0.0443(5) Uani 1 d . . .
C17 C 0.3216(2) 0.47449(19) 0.12210(11) 0.0433(5) Uani 1 d . . .
C14 C -0.0032(3) 0.1569(2) -0.09692(13) 0.0531(6) Uani 1 d . . .
H14 H -0.0379 0.1548 -0.0521 0.064 Uiso 1 calc . . R
O1 O 0.2530(3) 0.20716(16) 0.13189(10) 0.0816(6) Uani 1 d . . .
C6 C 0.2814(3) 0.63836(19) -0.01507(12) 0.0451(5) Uani 1 d . . .
C5 C 0.3991(3) 0.6970(2) 0.03476(14) 0.0573(6) Uani 1 d . . .
H5 H 0.4627 0.6538 0.0721 0.069 Uiso 1 calc . . R
C13 C -0.0653(3) 0.0758(2) -0.15141(14) 0.0607(7) Uani 1 d . . .
H13 H -0.1410 0.0195 -0.1429 0.073 Uiso 1 calc . . R
C1 C 0.1903(3) 0.7039(2) -0.07130(13) 0.0554(6) Uani 1 d . . .
H1 H 0.1123 0.6654 -0.1053 0.066 Uiso 1 calc . . R
C22 C 0.2292(3) 0.5554(2) 0.15200(13) 0.0533(6) Uani 1 d . . .
H22 H 0.1295 0.5788 0.1259 0.064 Uiso 1 calc . . R
C16 C 0.2244(3) 0.2138(2) 0.06614(13) 0.0563(6) Uani 1 d . . .
H16 H 0.2026 0.1420 0.0407 0.068 Uiso 1 calc . . R
C10 C 0.1586(3) 0.2432(2) -0.17615(12) 0.0559(6) Uani 1 d . . .
H10 H 0.2336 0.2998 -0.1851 0.067 Uiso 1 calc . . R
C18 C 0.4664(3) 0.4356(3) 0.16052(13) 0.0696(8) Uani 1 d . . .
H18 H 0.5275 0.3796 0.1404 0.084 Uiso 1 calc . . R
C3 C 0.3292(4) 0.8834(2) -0.02667(19) 0.0781(9) Uani 1 d . . .
H3 H 0.3443 0.9658 -0.0301 0.094 Uiso 1 calc . . R
C11 C 0.0969(3) 0.1625(2) -0.23010(14) 0.0666(7) Uani 1 d . . .
H11 H 0.1311 0.1644 -0.2751 0.080 Uiso 1 calc . . R
C12 C -0.0152(3) 0.0786(2) -0.21797(15) 0.0657(7) Uani 1 d . . .
H12 H -0.0568 0.0242 -0.2546 0.079 Uiso 1 calc . . R
C21 C 0.2853(4) 0.6015(3) 0.22082(15) 0.0748(8) Uani 1 d . . .
H21 H 0.2249 0.6580 0.2409 0.090 Uiso 1 calc . . R
C2 C 0.2145(4) 0.8262(2) -0.07721(16) 0.0707(8) Uani 1 d . . .
H2 H 0.1534 0.8695 -0.1152 0.085 Uiso 1 calc . . R
C4 C 0.4215(4) 0.8193(2) 0.02884(17) 0.0751(8) Uani 1 d . . .
H4 H 0.4995 0.8582 0.0626 0.090 Uiso 1 calc . . R
C20 C 0.4290(4) 0.5642(3) 0.25948(16) 0.0947(11) Uani 1 d . . .
H20 H 0.4662 0.5950 0.3061 0.114 Uiso 1 calc . . R
C19 C 0.5192(4) 0.4819(4) 0.23020(16) 0.0988(12) Uani 1 d . . .
H19 H 0.6170 0.4567 0.2573 0.119 Uiso 1 calc . . R


_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 1.365(2) . ?
N1 C15 1.395(2) . ?
N1 C17 1.446(2) . ?
N2 C7 1.327(2) . ?
N2 C8 1.365(3) . ?
C7 C6 1.472(3) . ?
C15 C8 1.381(3) . ?
C15 C16 1.450(3) . ?
C8 C9 1.474(3) . ?
C9 C14 1.385(3) . ?
C9 C10 1.389(3) . ?
C17 C22 1.374(3) . ?
C17 C18 1.370(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.386(3) . ?
O1 C16 1.200(3) . ?
C6 C5 1.391(3) . ?
C6 C1 1.386(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.383(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.374(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.385(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.376(3) . ?
C16 H16 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.376(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.387(4) . ?
C3 H3 0.9300 . ?
C3 C2 1.377(4) . ?
C3 C4 1.374(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(4) . ?
C12 H12 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.359(4) . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
C20 H20 0.9300 . ?
C20 C19 1.366(5) . ?
C19 H19 0.9300 . ?

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 C15 106.57(16) . . ?
C7 N1 C17 125.93(17) . . ?
C15 N1 C17 127.47(17) . . ?
C7 N2 C8 106.26(17) . . ?
N1 C7 C6 126.86(19) . . ?
N2 C7 N1 111.48(18) . . ?
N2 C7 C6 121.63(18) . . ?
N1 C15 C16 126.73(19) . . ?
C8 C15 N1 105.51(17) . . ?
C8 C15 C16 127.7(2) . . ?
N2 C8 C15 110.17(18) . . ?
N2 C8 C9 119.78(18) . . ?
C15 C8 C9 130.04(19) . . ?
C14 C9 C8 122.5(2) . . ?
C14 C9 C10 118.4(2) . . ?
C10 C9 C8 119.0(2) . . ?
C22 C17 N1 118.55(18) . . ?
C18 C17 N1 120.1(2) . . ?
C18 C17 C22 121.2(2) . . ?
C9 C14 H14 119.6 . . ?
C9 C14 C13 120.8(2) . . ?
C13 C14 H14 119.6 . . ?
C5 C6 C7 123.9(2) . . ?
C1 C6 C7 117.0(2) . . ?
C1 C6 C5 119.0(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 119.9 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 120.0 . . ?
C6 C1 H1 119.8 . . ?
C2 C1 C6 120.5(2) . . ?
C2 C1 H1 119.8 . . ?
C17 C22 H22 120.3 . . ?
C17 C22 C21 119.5(2) . . ?
C21 C22 H22 120.3 . . ?
C15 C16 H16 116.5 . . ?
O1 C16 C15 127.0(2) . . ?
O1 C16 H16 116.5 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C17 C18 H18 120.9 . . ?
C17 C18 C19 118.2(3) . . ?
C19 C18 H18 120.9 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C4 C3 C2 120.2(2) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.5(2) . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 119.6(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 C22 120.0(3) . . ?
C20 C21 H21 120.0 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.1 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.8 . . ?
C21 C20 H20 119.8 . . ?
C21 C20 C19 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.7(3) . . ?
C20 C19 H19 119.7 . . ?

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 C7 C6 C5 31.9(3) . . . . ?
N1 C7 C6 C1 -150.2(2) . . . . ?
N1 C15 C8 N2 0.6(2) . . . . ?
N1 C15 C8 C9 -178.8(2) . . . . ?
N1 C15 C16 O1 8.8(4) . . . . ?
N1 C17 C22 C21 -173.8(2) . . . . ?
N1 C17 C18 C19 174.8(2) . . . . ?
N2 C7 C6 C5 -150.2(2) . . . . ?
N2 C7 C6 C1 27.7(3) . . . . ?
N2 C8 C9 C14 -137.7(2) . . . . ?
N2 C8 C9 C10 39.0(3) . . . . ?
C7 N1 C15 C8 -0.5(2) . . . . ?
C7 N1 C15 C16 177.2(2) . . . . ?
C7 N1 C17 C22 63.1(3) . . . . ?
C7 N1 C17 C18 -113.0(3) . . . . ?
C7 N2 C8 C15 -0.5(2) . . . . ?
C7 N2 C8 C9 178.98(18) . . . . ?
C7 C6 C5 C4 179.3(2) . . . . ?
C7 C6 C1 C2 -178.9(2) . . . . ?
C15 N1 C7 N2 0.2(2) . . . . ?
C15 N1 C7 C6 178.3(2) . . . . ?
C15 N1 C17 C22 -114.7(2) . . . . ?
C15 N1 C17 C18 69.2(3) . . . . ?
C15 C8 C9 C14 41.7(3) . . . . ?
C15 C8 C9 C10 -141.7(2) . . . . ?
C8 N2 C7 N1 0.2(2) . . . . ?
C8 N2 C7 C6 -177.99(19) . . . . ?
C8 C15 C16 O1 -174.0(2) . . . . ?
C8 C9 C14 C13 177.4(2) . . . . ?
C8 C9 C10 C11 -177.6(2) . . . . ?
C9 C14 C13 C12 -0.3(4) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C17 N1 C7 N2 -177.99(17) . . . . ?
C17 N1 C7 C6 0.1(3) . . . . ?
C17 N1 C15 C8 177.65(18) . . . . ?
C17 N1 C15 C16 -4.7(3) . . . . ?
C17 C22 C21 C20 -1.9(4) . . . . ?
C17 C18 C19 C20 -0.1(5) . . . . ?
C14 C9 C10 C11 -0.8(3) . . . . ?
C14 C13 C12 C11 0.0(4) . . . . ?
C6 C5 C4 C3 -0.7(4) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C5 C6 C1 C2 -0.9(3) . . . . ?
C1 C6 C5 C4 1.4(3) . . . . ?
C22 C17 C18 C19 -1.3(4) . . . . ?
C22 C21 C20 C19 0.6(5) . . . . ?
C16 C15 C8 N2 -177.0(2) . . . . ?
C16 C15 C8 C9 3.6(4) . . . . ?
C10 C9 C14 C13 0.7(3) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C18 C17 C22 C21 2.3(4) . . . . ?
C21 C20 C19 C18 0.4(5) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C4 C3 C2 C1 1.1(4) . . . . ?

_olex2_date_sample_data_collection 2015-03-23
_olex2_submission_special_instructions 'No special instructions were received'
