# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_baowen_0915_1
_database_code_depnum_ccdc_archive 'CCDC 1846237'
_audit_update_record             
;
2018-05-30 deposited with the CCDC.
2018-06-29 downloaded from the CCDC.
;
_audit_creation_date             2018-05-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H12 N2 O2'
_chemical_formula_sum            'C12 H12 N2 O2'
_chemical_formula_weight         216.24
_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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y, x-y, z'
3 '-x+y, -x, z'
4 'x+2/3, y+1/3, z+1/3'
5 '-y+2/3, x-y+1/3, z+1/3'
6 '-x+y+2/3, -x+1/3, z+1/3'
7 'x+1/3, y+2/3, z+2/3'
8 '-y+1/3, x-y+2/3, z+2/3'
9 '-x+y+1/3, -x+2/3, z+2/3'
10 '-x, -y, -z'
11 'y, -x+y, -z'
12 'x-y, x, -z'
13 '-x+2/3, -y+1/3, -z+1/3'
14 'y+2/3, -x+y+1/3, -z+1/3'
15 'x-y+2/3, x+1/3, -z+1/3'
16 '-x+1/3, -y+2/3, -z+2/3'
17 'y+1/3, -x+y+2/3, -z+2/3'
18 'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   28.7013(15)
_cell_length_b                   28.7013(15)
_cell_length_c                   6.9232(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     4939.0(5)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    701
_cell_measurement_temperature    295.26(10)
_cell_measurement_theta_max      23.4370
_cell_measurement_theta_min      3.6490
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78509
_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    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2052
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            3129
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.66
_diffrn_ambient_temperature      295.26(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  -41.00   69.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000   60.0000 110
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0121386000
_diffrn_orient_matrix_UB_12      0.0105130000
_diffrn_orient_matrix_UB_13      -0.0622574000
_diffrn_orient_matrix_UB_21      0.0257799000
_diffrn_orient_matrix_UB_22      0.0215673000
_diffrn_orient_matrix_UB_23      -0.0251286000
_diffrn_orient_matrix_UB_31      0.0013965000
_diffrn_orient_matrix_UB_32      -0.0154587000
_diffrn_orient_matrix_UB_33      -0.0773596000
_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                1185
_reflns_number_total             2171
_reflns_odcompleteness_completeness 99.78
_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         -0.186
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0570
_refine_ls_restrained_S_all      1.050
_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)+(0.0393P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1368
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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 0.78866(8) 0.55753(8) 0.4796(3) 0.0628(6) Uani 1 d . . .
O2 O 0.79642(8) 0.48552(7) 0.4146(3) 0.0556(6) Uani 1 d . . .
N1 N 0.83831(8) 0.60354(8) 0.1332(3) 0.0395(5) Uani 1 d . . .
N2 N 0.86346(12) 0.66950(10) -0.0934(4) 0.0547(7) Uani 1 d . . .
H2A H 0.8509(11) 0.6863(11) -0.011(4) 0.070(10) Uiso 1 d . . .
H2B H 0.8807(11) 0.6858(12) -0.192(4) 0.075(12) Uiso 1 d . . .
C1 C 0.86288(10) 0.62426(10) -0.0333(4) 0.0391(6) Uani 1 d . . .
C2 C 0.88758(10) 0.60038(10) -0.1481(3) 0.0385(6) Uani 1 d . . .
C3 C 0.91494(11) 0.62252(11) -0.3226(4) 0.0520(8) Uani 1 d . . .
H3 H 0.9185 0.6546 -0.3680 0.062 Uiso 1 calc . . R
C4 C 0.93630(12) 0.59706(12) -0.4257(4) 0.0607(8) Uani 1 d . . .
H4 H 0.9544 0.6121 -0.5406 0.073 Uiso 1 calc . . R
C5 C 0.93127(12) 0.54905(12) -0.3608(4) 0.0603(8) Uani 1 d . . .
H5 H 0.9453 0.5318 -0.4340 0.072 Uiso 1 calc . . R
C6 C 0.90602(10) 0.52701(11) -0.1909(4) 0.0487(7) Uani 1 d . . .
H6 H 0.9035 0.4952 -0.1476 0.058 Uiso 1 calc . . R
C7 C 0.88363(9) 0.55217(10) -0.0803(4) 0.0400(6) Uani 1 d . . .
C8 C 0.85631(10) 0.53045(10) 0.0954(4) 0.0427(7) Uani 1 d . . .
H8 H 0.8529 0.4987 0.1438 0.051 Uiso 1 calc . . R
C9 C 0.83506(9) 0.55641(10) 0.1927(3) 0.0374(6) Uani 1 d . . .
C10 C 0.80468(10) 0.53498(11) 0.3769(4) 0.0440(7) Uani 1 d . . .
C11 C 0.76672(12) 0.46035(12) 0.5886(4) 0.0616(8) Uani 1 d . . .
H11A H 0.7310 0.4559 0.5815 0.074 Uiso 1 calc . . R
H11B H 0.7850 0.4825 0.7000 0.074 Uiso 1 calc . . R
C12 C 0.76317(17) 0.40745(14) 0.6068(5) 0.1022(15) Uani 1 d . . .
H12A H 0.7446 0.3856 0.4969 0.153 Uiso 1 calc . . GR
H12B H 0.7439 0.3900 0.7225 0.153 Uiso 1 calc . . GR
H12C H 0.7987 0.4123 0.6130 0.153 Uiso 1 calc . . GR

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
O1 0.0734(14) 0.0595(14) 0.0668(14) 0.0059(11) 0.0257(11) 0.0418(12)
O2 0.0695(13) 0.0540(13) 0.0508(12) 0.0120(10) 0.0187(10) 0.0366(11)
N1 0.0407(13) 0.0393(13) 0.0428(13) -0.0023(10) -0.0013(10) 0.0232(11)
N2 0.083(2) 0.0483(16) 0.0474(16) 0.0029(14) 0.0069(15) 0.0443(16)
C1 0.0421(15) 0.0366(15) 0.0412(15) -0.0049(12) -0.0066(12) 0.0216(13)
C2 0.0401(15) 0.0381(15) 0.0379(15) -0.0061(12) -0.0015(12) 0.0199(13)
C3 0.0625(19) 0.0445(17) 0.0484(17) 0.0021(14) 0.0059(14) 0.0263(15)
C4 0.068(2) 0.064(2) 0.0492(18) 0.0035(16) 0.0199(16) 0.0328(18)
C5 0.069(2) 0.065(2) 0.060(2) -0.0065(17) 0.0113(17) 0.0430(18)
C6 0.0540(17) 0.0470(17) 0.0531(18) -0.0032(14) 0.0081(14) 0.0312(15)
C7 0.0366(14) 0.0421(16) 0.0440(16) -0.0041(13) -0.0003(12) 0.0217(13)
C8 0.0447(16) 0.0390(15) 0.0495(16) 0.0009(13) 0.0036(13) 0.0248(13)
C9 0.0340(14) 0.0402(15) 0.0405(15) -0.0030(12) -0.0012(12) 0.0204(12)
C10 0.0398(15) 0.0447(17) 0.0488(17) -0.0027(14) -0.0024(13) 0.0222(14)
C11 0.070(2) 0.067(2) 0.0500(18) 0.0173(16) 0.0204(16) 0.0364(18)
C12 0.154(4) 0.086(3) 0.092(3) 0.045(2) 0.055(3) 0.079(3)

_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 C10 1.197(3) . ?
O2 C10 1.343(3) . ?
O2 C11 1.444(3) . ?
N1 C1 1.327(3) . ?
N1 C9 1.372(3) . ?
N2 H2A 0.93(3) . ?
N2 H2B 0.84(3) . ?
N2 C1 1.356(3) . ?
C1 C2 1.446(3) . ?
C2 C3 1.407(3) . ?
C2 C7 1.411(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.366(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.360(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.409(3) . ?
C7 C8 1.413(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.355(3) . ?
C9 C10 1.493(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.475(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C10 O2 C11 116.1(2) . . ?
C1 N1 C9 117.5(2) . . ?
H2A N2 H2B 119(3) . . ?
C1 N2 H2A 119.3(17) . . ?
C1 N2 H2B 120(2) . . ?
N1 C1 N2 116.4(2) . . ?
N1 C1 C2 122.8(2) . . ?
N2 C1 C2 120.8(2) . . ?
C3 C2 C1 123.6(2) . . ?
C3 C2 C7 118.8(2) . . ?
C7 C2 C1 117.7(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.7(3) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.3(3) . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C8 118.3(2) . . ?
C6 C7 C2 119.2(2) . . ?
C6 C7 C8 122.5(2) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.3(2) . . ?
C9 C8 H8 120.4 . . ?
N1 C9 C10 113.6(2) . . ?
C8 C9 N1 124.4(2) . . ?
C8 C9 C10 121.9(2) . . ?
O1 C10 O2 122.9(3) . . ?
O1 C10 C9 126.0(2) . . ?
O2 C10 C9 111.1(2) . . ?
O2 C11 H11A 110.1 . . ?
O2 C11 H11B 110.1 . . ?
O2 C11 C12 107.8(2) . . ?
H11A C11 H11B 108.5 . . ?
C12 C11 H11A 110.1 . . ?
C12 C11 H11B 110.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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 -178.4(2) . . . . ?
N1 C1 C2 C7 1.8(4) . . . . ?
N1 C9 C10 O1 -7.6(4) . . . . ?
N1 C9 C10 O2 171.6(2) . . . . ?
N2 C1 C2 C3 2.2(4) . . . . ?
N2 C1 C2 C7 -177.6(2) . . . . ?
C1 N1 C9 C8 1.6(4) . . . . ?
C1 N1 C9 C10 -177.5(2) . . . . ?
C1 C2 C3 C4 -178.6(2) . . . . ?
C1 C2 C7 C6 178.4(2) . . . . ?
C1 C2 C7 C8 -0.5(3) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C2 C7 C8 C9 -0.2(4) . . . . ?
C3 C2 C7 C6 -1.4(4) . . . . ?
C3 C2 C7 C8 179.7(2) . . . . ?
C3 C4 C5 C6 -1.5(5) . . . . ?
C4 C5 C6 C7 1.3(4) . . . . ?
C5 C6 C7 C2 0.2(4) . . . . ?
C5 C6 C7 C8 179.0(3) . . . . ?
C6 C7 C8 C9 -179.0(2) . . . . ?
C7 C2 C3 C4 1.2(4) . . . . ?
C7 C8 C9 N1 -0.4(4) . . . . ?
C7 C8 C9 C10 178.6(2) . . . . ?
C8 C9 C10 O1 173.3(3) . . . . ?
C8 C9 C10 O2 -7.5(3) . . . . ?
C9 N1 C1 N2 177.1(2) . . . . ?
C9 N1 C1 C2 -2.3(3) . . . . ?
C10 O2 C11 C12 -178.6(3) . . . . ?
C11 O2 C10 O1 0.0(4) . . . . ?
C11 O2 C10 C9 -179.3(2) . . . . ?

_olex2_date_sample_data_collection 2017-09-15
_olex2_submission_special_instructions 'No special instructions were received'
