# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_181209f
_database_code_depnum_ccdc_archive 'CCDC 2036353'
loop_
_audit_author_name
_audit_author_address
'Bo Jiang'
;Jiangsu Normal University
China
;
_audit_update_record             
;
2020-10-09 deposited with the CCDC.	2020-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H24 N2 O2'
_chemical_formula_weight         456.52

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Cc

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   5.2240(5)
_cell_length_b                   16.3881(14)
_cell_length_c                   26.695(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.3710(10)
_cell_angle_gamma                90.00
_cell_volume                     2281.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1245
_cell_measurement_theta_min      2.486
_cell_measurement_theta_max      20.391

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9650
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5444
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0637
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2950
_reflns_number_gt                1860
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0129P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.2(16)
_refine_ls_number_reflns         2950
_refine_ls_number_parameters     316
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.0668
_refine_ls_wR_factor_gt          0.0590
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7135(6) 0.69698(16) 0.21463(10) 0.0546(8) Uani 1 1 d . . .
H1 H 0.5910 0.7309 0.2188 0.065 Uiso 1 1 calc R . .
N2 N 0.7537(6) 0.85477(18) 0.19277(11) 0.0561(9) Uani 1 1 d . . .
O1 O 0.3087(5) 0.37552(13) 0.43801(9) 0.0569(7) Uani 1 1 d . . .
O2 O 0.8628(5) 0.57275(15) 0.23896(10) 0.0747(9) Uani 1 1 d . . .
C1 C 0.2342(7) 0.4217(2) 0.39590(13) 0.0467(9) Uani 1 1 d . . .
C2 C 0.3661(6) 0.49350(19) 0.39522(12) 0.0433(9) Uani 1 1 d . . .
C3 C 0.5431(7) 0.4914(2) 0.43933(12) 0.0445(9) Uani 1 1 d . . .
C4 C 0.4974(8) 0.4197(2) 0.46318(14) 0.0503(10) Uani 1 1 d . . .
C5 C 0.6302(8) 0.3913(2) 0.50594(15) 0.0663(12) Uani 1 1 d . . .
H5 H 0.5903 0.3418 0.5206 0.080 Uiso 1 1 calc R . .
C6 C 0.8217(9) 0.4397(3) 0.52531(14) 0.0754(13) Uani 1 1 d . . .
H6 H 0.9160 0.4227 0.5541 0.091 Uiso 1 1 calc R . .
C7 C 0.8833(8) 0.5152(3) 0.50331(14) 0.0588(11) Uani 1 1 d . . .
C8 C 0.7372(7) 0.5442(2) 0.46040(13) 0.0501(10) Uani 1 1 d . . .
C9 C 0.7963(8) 0.6220(2) 0.44210(15) 0.0630(11) Uani 1 1 d . . .
H9 H 0.7014 0.6428 0.4144 0.076 Uiso 1 1 calc R . .
C10 C 0.9909(9) 0.6680(3) 0.46428(16) 0.0745(13) Uani 1 1 d . . .
H10 H 1.0241 0.7197 0.4518 0.089 Uiso 1 1 calc R . .
C11 C 1.1386(9) 0.6383(3) 0.50503(18) 0.0821(14) Uani 1 1 d . . .
H11 H 1.2728 0.6694 0.5193 0.099 Uiso 1 1 calc R . .
C12 C 1.0880(8) 0.5642(3) 0.52407(16) 0.0731(12) Uani 1 1 d . . .
H12 H 1.1890 0.5447 0.5513 0.088 Uiso 1 1 calc R . .
C13 C 0.0370(7) 0.3828(2) 0.36307(14) 0.0456(9) Uani 1 1 d . . .
C14 C 0.0120(7) 0.3999(2) 0.31235(14) 0.0553(11) Uani 1 1 d . . .
H14 H 0.1274 0.4352 0.2983 0.066 Uiso 1 1 calc R . .
C15 C -0.1827(8) 0.3651(2) 0.28227(15) 0.0585(11) Uani 1 1 d . . .
H15 H -0.1977 0.3777 0.2482 0.070 Uiso 1 1 calc R . .
C16 C -0.3536(7) 0.3125(2) 0.30189(15) 0.0597(11) Uani 1 1 d . . .
H16 H -0.4863 0.2900 0.2816 0.072 Uiso 1 1 calc R . .
C17 C -0.3257(8) 0.2935(2) 0.35218(16) 0.0639(12) Uani 1 1 d . . .
H17 H -0.4391 0.2570 0.3658 0.077 Uiso 1 1 calc R . .
C18 C -0.1331(7) 0.3275(2) 0.38259(13) 0.0547(11) Uani 1 1 d . . .
H18 H -0.1163 0.3135 0.4164 0.066 Uiso 1 1 calc R . .
C19 C 0.7158(7) 0.6287(2) 0.24348(12) 0.0478(9) Uani 1 1 d . . .
C20 C 0.5166(7) 0.6296(2) 0.28236(14) 0.0538(10) Uani 1 1 d . . .
H20A H 0.5297 0.6808 0.3006 0.065 Uiso 1 1 calc R . .
H20B H 0.3475 0.6274 0.2653 0.065 Uiso 1 1 calc R . .
C21 C 0.5426(6) 0.5602(2) 0.31933(12) 0.0483(10) Uani 1 1 d . . .
H21A H 0.7085 0.5638 0.3375 0.058 Uiso 1 1 calc R . .
H21B H 0.5368 0.5090 0.3010 0.058 Uiso 1 1 calc R . .
C22 C 0.3330(6) 0.55975(19) 0.35697(12) 0.0480(9) Uani 1 1 d . . .
H22A H 0.3329 0.6120 0.3740 0.058 Uiso 1 1 calc R . .
H22B H 0.1677 0.5533 0.3389 0.058 Uiso 1 1 calc R . .
C23 C 0.8876(7) 0.7189(2) 0.17865(13) 0.0492(10) Uani 1 1 d . . .
C24 C 1.0363(7) 0.6649(2) 0.15460(13) 0.0578(11) Uani 1 1 d . . .
H24 H 1.0241 0.6094 0.1613 0.069 Uiso 1 1 calc R . .
C25 C 1.2074(8) 0.6927(3) 0.11988(14) 0.0688(12) Uani 1 1 d . . .
H25 H 1.3061 0.6552 0.1034 0.083 Uiso 1 1 calc R . .
C26 C 1.2313(7) 0.7726(3) 0.11005(13) 0.0630(12) Uani 1 1 d . . .
H26 H 1.3460 0.7897 0.0868 0.076 Uiso 1 1 calc R . .
C27 C 1.0849(7) 0.8305(2) 0.13442(13) 0.0501(9) Uani 1 1 d . . .
C28 C 0.9059(7) 0.8038(2) 0.16847(13) 0.0458(9) Uani 1 1 d . . .
C29 C 0.7785(8) 0.9329(3) 0.18508(14) 0.0661(12) Uani 1 1 d . . .
H29 H 0.6735 0.9684 0.2017 0.079 Uiso 1 1 calc R . .
C30 C 0.9538(8) 0.9664(2) 0.15323(15) 0.0687(12) Uani 1 1 d . . .
H30 H 0.9686 1.0226 0.1497 0.082 Uiso 1 1 calc R . .
C31 C 1.1015(8) 0.9150(2) 0.12770(15) 0.0647(12) Uani 1 1 d . . .
H31 H 1.2151 0.9360 0.1055 0.078 Uiso 1 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 C19 1.358(4) . ?
N1 C23 1.408(4) . ?
N2 C29 1.305(4) . ?
N2 C28 1.345(4) . ?
O1 C4 1.367(4) . ?
O1 C1 1.391(4) . ?
O2 C19 1.207(4) . ?
C1 C2 1.364(4) . ?
C1 C13 1.459(5) . ?
C2 C3 1.454(4) . ?
C2 C22 1.494(4) . ?
C3 C4 1.363(4) . ?
C3 C8 1.424(5) . ?
C4 C5 1.381(5) . ?
C5 C6 1.355(5) . ?
C6 C7 1.415(5) . ?
C7 C8 1.420(5) . ?
C7 C12 1.423(5) . ?
C8 C9 1.407(4) . ?
C9 C10 1.372(5) . ?
C10 C11 1.385(6) . ?
C11 C12 1.348(5) . ?
C13 C14 1.381(5) . ?
C13 C18 1.392(4) . ?
C14 C15 1.381(5) . ?
C15 C16 1.367(5) . ?
C16 C17 1.378(5) . ?
C17 C18 1.373(5) . ?
C19 C20 1.513(4) . ?
C20 C21 1.508(4) . ?
C21 C22 1.529(4) . ?
C23 C24 1.362(4) . ?
C23 C28 1.423(4) . ?
C24 C25 1.401(4) . ?
C25 C26 1.342(4) . ?
C26 C27 1.403(5) . ?
C27 C31 1.399(4) . ?
C27 C28 1.411(5) . ?
C29 C30 1.398(5) . ?
C30 C31 1.353(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
C19 N1 C23 127.8(3) . . ?
C29 N2 C28 117.8(3) . . ?
C4 O1 C1 105.6(3) . . ?
C2 C1 O1 111.2(3) . . ?
C2 C1 C13 135.1(3) . . ?
O1 C1 C13 113.7(3) . . ?
C1 C2 C3 105.4(3) . . ?
C1 C2 C22 126.7(3) . . ?
C3 C2 C22 127.9(3) . . ?
C4 C3 C8 118.7(4) . . ?
C4 C3 C2 106.2(4) . . ?
C8 C3 C2 135.2(3) . . ?
C3 C4 O1 111.6(3) . . ?
C3 C4 C5 125.6(4) . . ?
O1 C4 C5 122.7(4) . . ?
C6 C5 C4 116.2(4) . . ?
C5 C6 C7 122.3(4) . . ?
C6 C7 C8 120.2(4) . . ?
C6 C7 C12 121.0(4) . . ?
C8 C7 C12 118.8(4) . . ?
C9 C8 C7 117.7(4) . . ?
C9 C8 C3 125.5(4) . . ?
C7 C8 C3 116.9(3) . . ?
C10 C9 C8 121.4(4) . . ?
C9 C10 C11 120.7(4) . . ?
C12 C11 C10 120.0(5) . . ?
C11 C12 C7 121.4(4) . . ?
C14 C13 C18 118.3(4) . . ?
C14 C13 C1 121.5(3) . . ?
C18 C13 C1 120.2(3) . . ?
C15 C14 C13 120.7(4) . . ?
C16 C15 C14 120.8(4) . . ?
C15 C16 C17 118.8(4) . . ?
C18 C17 C16 121.1(3) . . ?
C17 C18 C13 120.3(3) . . ?
O2 C19 N1 123.6(3) . . ?
O2 C19 C20 122.9(3) . . ?
N1 C19 C20 113.4(3) . . ?
C21 C20 C19 113.7(3) . . ?
C20 C21 C22 113.1(2) . . ?
C2 C22 C21 113.2(3) . . ?
C24 C23 N1 124.4(3) . . ?
C24 C23 C28 119.9(3) . . ?
N1 C23 C28 115.7(3) . . ?
C23 C24 C25 120.3(3) . . ?
C26 C25 C24 121.1(4) . . ?
C25 C26 C27 120.6(4) . . ?
C31 C27 C26 124.8(4) . . ?
C31 C27 C28 115.9(3) . . ?
C26 C27 C28 119.3(3) . . ?
N2 C28 C27 123.4(3) . . ?
N2 C28 C23 117.8(3) . . ?
C27 C28 C23 118.7(3) . . ?
N2 C29 C30 123.7(4) . . ?
C31 C30 C29 118.4(4) . . ?
C30 C31 C27 120.7(4) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.033
