# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_zhanzhzh_1214
_database_code_depnum_ccdc_archive 'CCDC 1910163'
_audit_update_record             
;
2019-04-15 deposited with the CCDC.	2019-04-24 downloaded from the CCDC.
;
_audit_creation_date             2018-12-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H10 N2 O'
_chemical_formula_sum            'C14 H10 N2 O'
_chemical_formula_weight         222.24
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   14.761(3)
_cell_length_b                   9.9736(8)
_cell_length_c                   15.8257(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2329.8(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    630
_cell_measurement_temperature    292.86(10)
_cell_measurement_theta_max      26.0770
_cell_measurement_theta_min      3.7640
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5227
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.43
_diffrn_ambient_temperature      292.86(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -9.00   36.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  -60.0000 45

#__ type_ start__ end____ width___ exp.time_
  2 omega  -33.00   66.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000  120.0000 99
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0055648000
_diffrn_orient_matrix_UB_12      -0.0244413000
_diffrn_orient_matrix_UB_13      0.0417698000
_diffrn_orient_matrix_UB_21      -0.0474746000
_diffrn_orient_matrix_UB_22      0.0104275000
_diffrn_orient_matrix_UB_23      -0.0033573000
_diffrn_orient_matrix_UB_31      -0.0053614000
_diffrn_orient_matrix_UB_32      -0.0658719000
_diffrn_orient_matrix_UB_33      -0.0160913000
_diffrn_radiation_monochromator  mirror
_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                1140
_reflns_number_total             2291
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1334
_refine_ls_R_factor_gt           0.0680
_refine_ls_restrained_S_all      1.063
_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)+(0.0511P)²+0.1442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1848
_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 N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2a), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14)
;
_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
O1 O 0.38337(16) -0.0112(2) 0.04168(16) 0.0683(8) Uani 1 d . . .
N1 N 0.22424(18) 0.20286(19) 0.14044(16) 0.0470(7) Uani 1 d . . .
N2 N 0.23279(17) -0.0204(2) 0.14851(16) 0.0490(7) Uani 1 d . . .
H2 H 0.2504 -0.1009 0.1379 0.059 Uiso 1 calc . . R
C1 C 0.1644(2) 0.1567(3) 0.20158(18) 0.0470(8) Uani 1 d . . .
C2 C 0.1053(3) 0.2288(3) 0.2529(2) 0.0668(11) Uani 1 d . . .
H2A H 0.1017 0.3218 0.2501 0.080 Uiso 1 calc . . R
C3 C 0.0528(3) 0.1569(4) 0.3077(2) 0.0802(12) Uani 1 d . . .
H3 H 0.0127 0.2027 0.3427 0.096 Uiso 1 calc . . R
C4 C 0.0570(3) 0.0179(4) 0.3132(2) 0.0750(11) Uani 1 d . . .
H4 H 0.0197 -0.0267 0.3513 0.090 Uiso 1 calc . . R
C5 C 0.1155(2) -0.0549(3) 0.2632(2) 0.0598(10) Uani 1 d . . .
H5 H 0.1188 -0.1478 0.2670 0.072 Uiso 1 calc . . R
C6 C 0.1695(2) 0.0168(3) 0.20670(19) 0.0466(8) Uani 1 d . . .
C7 C 0.2629(2) 0.0933(2) 0.11029(17) 0.0435(8) Uani 1 d . . .
C8 C 0.3366(2) 0.0899(3) 0.04738(19) 0.0463(8) Uani 1 d . . .
C9 C 0.3542(2) 0.2103(3) -0.0054(2) 0.0495(8) Uani 1 d . . .
C10 C 0.4433(3) 0.2423(3) -0.0250(2) 0.0666(10) Uani 1 d . . .
H10 H 0.4905 0.1885 -0.0057 0.080 Uiso 1 calc . . R
C11 C 0.4614(4) 0.3538(4) -0.0730(3) 0.0995(16) Uani 1 d . . .
H11 H 0.5211 0.3776 -0.0844 0.119 Uiso 1 calc . . R
C12 C 0.3919(4) 0.4303(5) -0.1043(3) 0.114(2) Uani 1 d . . .
H12 H 0.4050 0.5054 -0.1369 0.136 Uiso 1 calc . . R
C13 C 0.3030(4) 0.3977(4) -0.0882(2) 0.0955(16) Uani 1 d . . .
H13 H 0.2562 0.4481 -0.1114 0.115 Uiso 1 calc . . R
C14 C 0.2842(3) 0.2880(3) -0.0367(2) 0.0666(11) Uani 1 d . . .
H14 H 0.2245 0.2669 -0.0234 0.080 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
O1 C8 1.226(3) . ?
N1 C1 1.388(4) . ?
N1 C7 1.322(3) . ?
N2 H2 0.8600 . ?
N2 C6 1.363(4) . ?
N2 C7 1.360(3) . ?
C1 C2 1.392(4) . ?
C1 C6 1.399(4) . ?
C2 H2A 0.9300 . ?
C2 C3 1.366(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.396(4) . ?
C7 C8 1.475(4) . ?
C8 C9 1.487(4) . ?
C9 C10 1.389(5) . ?
C9 C14 1.383(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.373(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.371(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.375(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(4) . ?
C14 H14 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 C1 104.6(2) . . ?
C6 N2 H2 126.4 . . ?
C7 N2 H2 126.4 . . ?
C7 N2 C6 107.3(2) . . ?
N1 C1 C2 129.4(3) . . ?
N1 C1 C6 109.7(3) . . ?
C2 C1 C6 121.0(3) . . ?
C1 C2 H2A 121.5 . . ?
C3 C2 C1 117.1(3) . . ?
C3 C2 H2A 121.5 . . ?
C2 C3 H3 118.7 . . ?
C2 C3 C4 122.5(3) . . ?
C4 C3 H3 118.7 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 121.5 . . ?
C4 C5 C6 117.1(3) . . ?
C6 C5 H5 121.5 . . ?
N2 C6 C1 105.6(3) . . ?
N2 C6 C5 133.2(3) . . ?
C5 C6 C1 121.2(3) . . ?
N1 C7 N2 112.8(3) . . ?
N1 C7 C8 125.5(2) . . ?
N2 C7 C8 121.4(2) . . ?
O1 C8 C7 119.0(3) . . ?
O1 C8 C9 121.7(3) . . ?
C7 C8 C9 119.3(3) . . ?
C10 C9 C8 118.5(3) . . ?
C14 C9 C8 121.5(3) . . ?
C14 C9 C10 120.0(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(4) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.3(5) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 121.0(4) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.5 . . ?
C12 C13 C14 119.0(4) . . ?
C14 C13 H13 120.5 . . ?
C9 C14 C13 120.0(4) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?

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
O1 C8 C9 C10 -35.1(4) . . . . ?
O1 C8 C9 C14 143.2(3) . . . . ?
N1 C1 C2 C3 179.3(3) . . . . ?
N1 C1 C6 N2 0.2(3) . . . . ?
N1 C1 C6 C5 -179.6(3) . . . . ?
N1 C7 C8 O1 159.9(3) . . . . ?
N1 C7 C8 C9 -18.1(4) . . . . ?
N2 C7 C8 O1 -14.6(4) . . . . ?
N2 C7 C8 C9 167.4(3) . . . . ?
C1 N1 C7 N2 -0.7(3) . . . . ?
C1 N1 C7 C8 -175.6(3) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C2 C1 C6 N2 179.8(3) . . . . ?
C2 C1 C6 C5 0.1(5) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 N2 -179.4(3) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
C6 N2 C7 N1 0.8(3) . . . . ?
C6 N2 C7 C8 176.0(3) . . . . ?
C6 C1 C2 C3 -0.3(5) . . . . ?
C7 N1 C1 C2 -179.3(3) . . . . ?
C7 N1 C1 C6 0.3(3) . . . . ?
C7 N2 C6 C1 -0.6(3) . . . . ?
C7 N2 C6 C5 179.1(3) . . . . ?
C7 C8 C9 C10 142.8(3) . . . . ?
C7 C8 C9 C14 -38.9(4) . . . . ?
C8 C9 C10 C11 -179.4(3) . . . . ?
C8 C9 C14 C13 -178.0(3) . . . . ?
C9 C10 C11 C12 -2.6(6) . . . . ?
C10 C9 C14 C13 0.3(5) . . . . ?
C10 C11 C12 C13 0.3(7) . . . . ?
C11 C12 C13 C14 2.4(7) . . . . ?
C12 C13 C14 C9 -2.6(6) . . . . ?
C14 C9 C10 C11 2.3(5) . . . . ?


_olex2_date_sample_data_collection 2018-12-14
_olex2_submission_special_instructions 'No special instructions were received'
