# Electronic Supplementary Material (ESI) for Materials 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_1
_database_code_depnum_ccdc_archive 'CCDC 2010122'
loop_
_audit_author_name
_audit_author_address
' Kexin Zhang'
;South China University of Technology
China
;
_audit_update_record             
;
2020-06-16 deposited with the CCDC.	2020-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        CNP-DPAS
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H19 N3 O'
_chemical_formula_sum            'C27 H19 N3 O'
_chemical_formula_weight         401.45

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 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.9731(8)
_cell_length_b                   9.7283(10)
_cell_length_c                   21.672(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.362(3)
_cell_angle_gamma                90
_cell_volume                     2096.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2067
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      25.20

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6428
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12199
_diffrn_reflns_av_unetI/netI     0.0786
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.929
_diffrn_reflns_theta_max         25.337
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             3780
_reflns_number_gt                2225
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0293P)²+0.2685P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3780
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1175
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1009
_refine_ls_wR_factor_gt          0.0855
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1462(2) 0.0404(2) 0.40618(10) 0.0227(5) Uani 1 1 d . . . . .
C2 C 0.1501(2) 0.1014(2) 0.34402(11) 0.0233(5) Uani 1 1 d . . . . .
H2 H 0.1388 0.0387 0.3104 0.028 Uiso 1 1 calc R U . . .
C3 C -0.1501(2) 0.1536(2) 0.45222(11) 0.0228(6) Uani 1 1 d . . . . .
C4 C -0.1606(2) 0.1215(3) 0.51417(11) 0.0297(6) Uani 1 1 d . . . . .
H4 H -0.1660 0.0281 0.5265 0.036 Uiso 1 1 calc R U . . .
C5 C -0.1632(2) 0.2249(3) 0.55791(12) 0.0373(7) Uani 1 1 d . . . . .
H5 H -0.1676 0.2021 0.6003 0.045 Uiso 1 1 calc R U . . .
C6 C -0.1595(2) 0.3617(3) 0.54004(12) 0.0359(7) Uani 1 1 d . . . . .
H6 H -0.1631 0.4324 0.5701 0.043 Uiso 1 1 calc R U . . .
C7 C -0.1505(2) 0.3950(3) 0.47853(12) 0.0318(6) Uani 1 1 d . . . . .
H7 H -0.1487 0.4886 0.4662 0.038 Uiso 1 1 calc R U . . .
C8 C -0.1441(2) 0.2918(2) 0.43504(11) 0.0261(6) Uani 1 1 d . . . . .
H8 H -0.1354 0.3151 0.3929 0.031 Uiso 1 1 calc R U . . .
C9 C -0.2561(2) -0.0627(2) 0.40195(10) 0.0250(6) Uani 1 1 d . . . . .
C10 C -0.2361(2) -0.1922(3) 0.37595(12) 0.0355(7) Uani 1 1 d . . . . .
H10 H -0.1508 -0.2150 0.3620 0.043 Uiso 1 1 calc R U . . .
C11 C -0.3396(3) -0.2870(3) 0.37037(13) 0.0472(8) Uani 1 1 d . . . . .
H11 H -0.3251 -0.3746 0.3527 0.057 Uiso 1 1 calc R U . . .
C12 C -0.4646(3) -0.2545(3) 0.39051(14) 0.0484(8) Uani 1 1 d . . . . .
H12 H -0.5360 -0.3193 0.3862 0.058 Uiso 1 1 calc R U . . .
C13 C -0.4849(3) -0.1276(3) 0.41688(13) 0.0409(7) Uani 1 1 d . . . . .
H13 H -0.5701 -0.1058 0.4312 0.049 Uiso 1 1 calc R U . . .
C14 C -0.3818(2) -0.0322(3) 0.42259(11) 0.0308(6) Uani 1 1 d . . . . .
H14 H -0.3967 0.0548 0.4407 0.037 Uiso 1 1 calc R U . . .
C15 C 0.2955(2) 0.2742(2) 0.40253(11) 0.0258(6) Uani 1 1 d . . . . .
C16 C 0.2738(2) 0.1800(2) 0.35354(11) 0.0232(6) Uani 1 1 d . . . . .
C17 C 0.3762(2) 0.1576(2) 0.31407(11) 0.0248(6) Uani 1 1 d . . . . .
H17 H 0.3613 0.0942 0.2809 0.030 Uiso 1 1 calc R U . . .
C18 C 0.4995(2) 0.2252(2) 0.32189(11) 0.0236(6) Uani 1 1 d . . . . .
C19 C 0.5168(2) 0.3198(2) 0.37067(11) 0.0278(6) Uani 1 1 d . . . . .
H19 H 0.5993 0.3686 0.3766 0.033 Uiso 1 1 calc R U . . .
C20 C 0.4174(2) 0.3442(2) 0.41016(12) 0.0306(6) Uani 1 1 d . . . . .
H20 H 0.4322 0.4090 0.4428 0.037 Uiso 1 1 calc R U . . .
C21 C 0.8365(2) 0.1086(2) 0.22334(10) 0.0249(6) Uani 1 1 d . . . . .
C22 C 0.7350(2) 0.0143(2) 0.23155(11) 0.0286(6) Uani 1 1 d . . . . .
H22 H 0.7413 -0.0770 0.2165 0.034 Uiso 1 1 calc R U . . .
C23 C 0.6246(2) 0.0546(2) 0.26184(11) 0.0279(6) Uani 1 1 d . . . . .
H23 H 0.5556 -0.0103 0.2676 0.034 Uiso 1 1 calc R U . . .
C24 C 0.6118(2) 0.1882(2) 0.28418(11) 0.0240(6) Uani 1 1 d . . . . .
C25 C 0.7140(2) 0.2821(2) 0.27329(11) 0.0274(6) Uani 1 1 d . . . . .
H25 H 0.7061 0.3746 0.2867 0.033 Uiso 1 1 calc R U . . .
C26 C 0.8252(2) 0.2437(2) 0.24379(11) 0.0272(6) Uani 1 1 d . . . . .
H26 H 0.8939 0.3087 0.2374 0.033 Uiso 1 1 calc R U . . .
C27 C 0.9588(2) 0.0648(2) 0.19718(11) 0.0290(6) Uani 1 1 d . . . . .
N1 N -0.05175(18) 0.02329(19) 0.36889(9) 0.0257(5) Uani 1 1 d . . . . .
N2 N 0.05577(17) 0.11619(19) 0.38084(9) 0.0253(5) Uani 1 1 d . . . . .
N3 N 1.0580(2) 0.0299(2) 0.17846(10) 0.0388(6) Uani 1 1 d . . . . .
O1 O 0.20229(16) 0.30019(18) 0.44310(8) 0.0369(5) Uani 1 1 d . . . . .
H1A H 0.132(2) 0.244(3) 0.4345(12) 0.044 Uiso 1 1 d . U . . .


_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
C1 N1 1.298(3) . ?
C1 C9 1.484(3) . ?
C1 C3 1.488(3) . ?
C2 N2 1.287(3) . ?
C2 C16 1.453(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(3) . ?
C3 C8 1.397(3) . ?
C4 C5 1.384(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C14 1.394(3) . ?
C9 C10 1.400(3) . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 O1 1.351(3) . ?
C15 C20 1.392(3) . ?
C15 C16 1.407(3) . ?
C16 C17 1.398(3) . ?
C17 C18 1.393(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.403(3) . ?
C18 C24 1.480(3) . ?
C19 C20 1.378(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.388(3) . ?
C21 C26 1.394(3) . ?
C21 C27 1.447(3) . ?
C22 C23 1.380(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.396(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.402(3) . ?
C25 C26 1.374(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 N3 1.149(3) . ?
N1 N2 1.411(2) . ?
O1 H1A 0.89(2) . ?

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
N1 C1 C9 116.3(2) . . ?
N1 C1 C3 124.7(2) . . ?
C9 C1 C3 119.01(19) . . ?
N2 C2 C16 120.4(2) . . ?
N2 C2 H2 119.8 . . ?
C16 C2 H2 119.8 . . ?
C4 C3 C8 118.8(2) . . ?
C4 C3 C1 119.3(2) . . ?
C8 C3 C1 122.0(2) . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 120.0(2) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 119.9(2) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C8 C3 120.8(2) . . ?
C7 C8 H8 119.6 . . ?
C3 C8 H8 119.6 . . ?
C14 C9 C10 118.7(2) . . ?
C14 C9 C1 120.9(2) . . ?
C10 C9 C1 120.4(2) . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 119.8(2) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 120.6(2) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
O1 C15 C20 118.0(2) . . ?
O1 C15 C16 122.6(2) . . ?
C20 C15 C16 119.4(2) . . ?
C17 C16 C15 119.1(2) . . ?
C17 C16 C2 118.9(2) . . ?
C15 C16 C2 122.0(2) . . ?
C18 C17 C16 122.0(2) . . ?
C18 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C17 C18 C19 117.3(2) . . ?
C17 C18 C24 121.1(2) . . ?
C19 C18 C24 121.4(2) . . ?
C20 C19 C18 121.8(2) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C19 C20 C15 120.3(2) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
C22 C21 C26 120.3(2) . . ?
C22 C21 C27 120.0(2) . . ?
C26 C21 C27 119.6(2) . . ?
C23 C22 C21 119.3(2) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C24 121.8(2) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C23 C24 C25 117.4(2) . . ?
C23 C24 C18 120.7(2) . . ?
C25 C24 C18 121.7(2) . . ?
C26 C25 C24 121.6(2) . . ?
C26 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C25 C26 C21 119.5(2) . . ?
C25 C26 H26 120.3 . . ?
C21 C26 H26 120.3 . . ?
N3 C27 C21 177.6(3) . . ?
C1 N1 N2 112.40(19) . . ?
C2 N2 N1 113.31(19) . . ?
C15 O1 H1A 108.5(16) . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.052



####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2010125'
loop_
_audit_author_name
_audit_author_address
' Kexin Zhang'
;South China University of Technology
China
;
_audit_update_record             
;
2020-06-16 deposited with the CCDC.	2020-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-DPAN
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 N2 O'
_chemical_formula_sum            'C24 H18 N2 O'
_chemical_formula_weight         350.40

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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.9845(6)
_cell_length_b                   10.7831(11)
_cell_length_c                   14.7402(15)
_cell_angle_alpha                71.289(3)
_cell_angle_beta                 83.476(3)
_cell_angle_gamma                86.979(3)
_cell_volume                     894.97(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4092
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      25.18

_exptl_crystal_description       sheet
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6956
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18286
_diffrn_reflns_av_unetI/netI     0.1325
_diffrn_reflns_av_R_equivalents  0.0756
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.933
_diffrn_reflns_theta_max         26.395
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             6977
_reflns_number_gt                4055
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.909
_reflns_Friedel_fraction_max     0.902
_reflns_Friedel_fraction_full    0.934

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0306P)²+0.2624P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1383 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6977
_refine_ls_number_parameters     493
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1547
_refine_ls_R_factor_gt           0.0700
_refine_ls_wR_factor_ref         0.1165
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.6633(10) -0.1435(5) 0.8139(4) 0.0263(15) Uani 1 1 d . . . . .
C2A C 0.8112(9) -0.1541(5) 0.8812(4) 0.0285(15) Uani 1 1 d . . . . .
C3A C 0.8056(11) -0.2693(6) 0.9631(4) 0.0361(16) Uani 1 1 d . . . . .
H3A H 0.9070 -0.2782 1.0100 0.043 Uiso 1 1 calc R U . . .
C4A C 0.6592(10) -0.3660(6) 0.9753(4) 0.0368(16) Uani 1 1 d . . . . .
H4A H 0.6611 -0.4424 1.0299 0.044 Uiso 1 1 calc R U . . .
C5A C 0.5031(9) -0.3546(5) 0.9077(4) 0.0279(14) Uani 1 1 d . . . . .
C6A C 0.5036(9) -0.2415(5) 0.8261(4) 0.0238(14) Uani 1 1 d . . . . .
C7A C 0.3494(11) -0.2293(6) 0.7594(5) 0.0353(17) Uani 1 1 d . . . . .
H7A H 0.3486 -0.1534 0.7043 0.042 Uiso 1 1 calc R U . . .
C8A C 0.1986(12) -0.3273(7) 0.7734(5) 0.0458(19) Uani 1 1 d . . . . .
H8A H 0.0931 -0.3184 0.7281 0.055 Uiso 1 1 calc R U . . .
C9A C 0.1994(11) -0.4390(6) 0.8533(5) 0.0436(18) Uani 1 1 d . . . . .
H9A H 0.0948 -0.5062 0.8621 0.052 Uiso 1 1 calc R U . . .
C10A C 0.3487(10) -0.4531(6) 0.9189(4) 0.0371(17) Uani 1 1 d . . . . .
H10A H 0.3485 -0.5304 0.9729 0.044 Uiso 1 1 calc R U . . .
C11A C 0.9740(9) -0.0556(6) 0.8708(4) 0.0299(15) Uani 1 1 d . . . . .
H11A H 1.0706 -0.0661 0.9198 0.036 Uiso 1 1 calc R U . . .
C12A C 1.2206(9) 0.2138(5) 0.7166(4) 0.0231(14) Uani 1 1 d . . . . .
C13A C 1.1561(9) 0.2077(5) 0.6235(4) 0.0212(14) Uani 1 1 d . . . . .
C14A C 1.3027(10) 0.1446(5) 0.5716(4) 0.0261(15) Uani 1 1 d . . . . .
H14A H 1.4414 0.1086 0.5948 0.031 Uiso 1 1 calc R U . . .
C15A C 1.2450(10) 0.1344(6) 0.4856(4) 0.0316(16) Uani 1 1 d . . . . .
H15A H 1.3450 0.0907 0.4505 0.038 Uiso 1 1 calc R U . . .
C16A C 1.0456(11) 0.1864(6) 0.4504(4) 0.0317(16) Uani 1 1 d . . . . .
H16A H 1.0080 0.1796 0.3913 0.038 Uiso 1 1 calc R U . . .
C17A C 0.9021(10) 0.2482(6) 0.5021(4) 0.0372(17) Uani 1 1 d . . . . .
H17A H 0.7632 0.2838 0.4789 0.045 Uiso 1 1 calc R U . . .
C18A C 0.9574(10) 0.2595(6) 0.5881(4) 0.0330(16) Uani 1 1 d . . . . .
H18A H 0.8568 0.3035 0.6227 0.040 Uiso 1 1 calc R U . . .
C19A C 1.3864(9) 0.3114(6) 0.7148(4) 0.0240(15) Uani 1 1 d . . . . .
C20A C 1.5241(9) 0.2883(6) 0.7889(4) 0.0291(15) Uani 1 1 d . . . . .
H20A H 1.5107 0.2085 0.8408 0.035 Uiso 1 1 calc R U . . .
C21A C 1.6785(11) 0.3780(6) 0.7885(5) 0.0394(18) Uani 1 1 d . . . . .
H21A H 1.7716 0.3603 0.8395 0.047 Uiso 1 1 calc R U . . .
C22A C 1.6974(11) 0.4932(7) 0.7143(5) 0.0401(18) Uani 1 1 d . . . . .
H22A H 1.8043 0.5554 0.7140 0.048 Uiso 1 1 calc R U . . .
C23A C 1.5644(11) 0.5205(6) 0.6400(5) 0.0344(16) Uani 1 1 d . . . . .
H23A H 1.5781 0.6012 0.5890 0.041 Uiso 1 1 calc R U . . .
C24A C 1.4096(10) 0.4288(6) 0.6402(4) 0.0301(16) Uani 1 1 d . . . . .
H24A H 1.3184 0.4468 0.5886 0.036 Uiso 1 1 calc R U . . .
C1B C 0.4258(10) 1.0920(5) 0.1824(4) 0.0253(14) Uani 1 1 d . . . . .
C2B C 0.4061(9) 1.0276(5) 0.1165(4) 0.0244(14) Uani 1 1 d . . . . .
C3B C 0.5710(10) 1.0472(5) 0.0359(4) 0.0310(15) Uani 1 1 d . . . . .
H3B H 0.5571 1.0036 -0.0099 0.037 Uiso 1 1 calc R U . . .
C4B C 0.7475(10) 1.1267(5) 0.0232(4) 0.0302(15) Uani 1 1 d . . . . .
H4B H 0.8574 1.1366 -0.0304 0.036 Uiso 1 1 calc R U . . .
C5B C 0.7702(9) 1.1956(5) 0.0892(4) 0.0253(14) Uani 1 1 d . . . . .
C6B C 0.6055(9) 1.1788(5) 0.1687(4) 0.0240(14) Uani 1 1 d . . . . .
C7B C 0.6254(10) 1.2514(6) 0.2324(4) 0.0300(16) Uani 1 1 d . . . . .
H7B H 0.5167 1.2420 0.2863 0.036 Uiso 1 1 calc R U . . .
C8B C 0.7989(11) 1.3340(6) 0.2166(5) 0.0345(17) Uani 1 1 d . . . . .
H8B H 0.8073 1.3839 0.2587 0.041 Uiso 1 1 calc R U . . .
C9B C 0.9658(10) 1.3478(6) 0.1399(4) 0.0342(16) Uani 1 1 d . . . . .
H9B H 1.0888 1.4040 0.1313 0.041 Uiso 1 1 calc R U . . .
C10B C 0.9500(10) 1.2793(5) 0.0772(4) 0.0322(15) Uani 1 1 d . . . . .
H10B H 1.0627 1.2887 0.0247 0.039 Uiso 1 1 calc R U . . .
C11B C 0.2252(9) 0.9377(5) 0.1292(4) 0.0261(14) Uani 1 1 d . . . . .
H11B H 0.2148 0.8970 0.0814 0.031 Uiso 1 1 calc R U . . .
C12B C -0.1877(9) 0.7644(5) 0.2853(4) 0.0224(14) Uani 1 1 d . . . . .
C13B C -0.1533(9) 0.7917(5) 0.3750(4) 0.0204(14) Uani 1 1 d . . . . .
C14B C -0.3201(10) 0.8554(6) 0.4170(5) 0.0336(16) Uani 1 1 d . . . . .
H14B H -0.4558 0.8822 0.3878 0.040 Uiso 1 1 calc R U . . .
C15B C -0.2908(11) 0.8802(6) 0.5008(5) 0.0375(17) Uani 1 1 d . . . . .
H15B H -0.4068 0.9235 0.5293 0.045 Uiso 1 1 calc R U . . .
C16B C -0.0955(11) 0.8428(6) 0.5434(4) 0.0348(16) Uani 1 1 d . . . . .
H16B H -0.0753 0.8612 0.6008 0.042 Uiso 1 1 calc R U . . .
C17B C 0.0709(11) 0.7786(7) 0.5028(5) 0.0415(18) Uani 1 1 d . . . . .
H17B H 0.2054 0.7510 0.5327 0.050 Uiso 1 1 calc R U . . .
C18B C 0.0425(10) 0.7542(6) 0.4183(5) 0.0344(16) Uani 1 1 d . . . . .
H18B H 0.1591 0.7112 0.3899 0.041 Uiso 1 1 calc R U . . .
C19B C -0.3618(9) 0.6714(5) 0.2873(4) 0.0235(15) Uani 1 1 d . . . . .
C20B C -0.4642(9) 0.6809(6) 0.2065(4) 0.0297(16) Uani 1 1 d . . . . .
H20B H -0.4187 0.7465 0.1475 0.036 Uiso 1 1 calc R U . . .
C21B C -0.6334(10) 0.5958(6) 0.2100(5) 0.0349(17) Uani 1 1 d . . . . .
H21B H -0.7051 0.6048 0.1539 0.042 Uiso 1 1 calc R U . . .
C22B C -0.6980(10) 0.4984(6) 0.2946(5) 0.0335(17) Uani 1 1 d . . . . .
H22B H -0.8154 0.4409 0.2972 0.040 Uiso 1 1 calc R U . . .
C23B C -0.5906(10) 0.4850(6) 0.3751(5) 0.0322(16) Uani 1 1 d . . . . .
H23B H -0.6304 0.4161 0.4330 0.039 Uiso 1 1 calc R U . . .
C24B C -0.4262(10) 0.5711(6) 0.3721(5) 0.0281(15) Uani 1 1 d . . . . .
H24B H -0.3555 0.5621 0.4285 0.034 Uiso 1 1 calc R U . . .
N1A N 0.9896(8) 0.0466(5) 0.7957(3) 0.0288(13) Uani 1 1 d . . . . .
N2A N 1.1486(8) 0.1364(5) 0.7996(4) 0.0297(12) Uani 1 1 d . . . . .
N1B N 0.0790(8) 0.9113(5) 0.2027(3) 0.0267(12) Uani 1 1 d . . . . .
N2B N -0.0762(8) 0.8176(4) 0.2023(3) 0.0251(12) Uani 1 1 d . . . . .
O1A O 0.6645(7) -0.0384(4) 0.7334(3) 0.0343(11) Uani 1 1 d D . . . .
H1AA H 0.756(8) 0.015(5) 0.733(5) 0.041 Uiso 1 1 d D U . . .
O1B O 0.2813(6) 1.0748(4) 0.2621(3) 0.0297(10) Uani 1 1 d D . . . .
H1BA H 0.188(8) 1.024(5) 0.259(4) 0.036 Uiso 1 1 d D U . . .


_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
C1A O1A 1.353(7) . ?
C1A C2A 1.378(7) . ?
C1A C6A 1.417(7) . ?
C2A C3A 1.425(8) . ?
C2A C11A 1.439(7) . ?
C3A C4A 1.352(8) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.415(8) . ?
C4A H4A 0.9500 . ?
C5A C10A 1.402(8) . ?
C5A C6A 1.412(7) . ?
C6A C7A 1.395(8) . ?
C7A C8A 1.375(9) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.389(9) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.358(8) . ?
C9A H9A 0.9500 . ?
C10A H10A 0.9500 . ?
C11A N1A 1.285(7) . ?
C11A H11A 0.9500 . ?
C12A N2A 1.282(7) . ?
C12A C19A 1.476(8) . ?
C12A C13A 1.490(8) . ?
C13A C18A 1.372(8) . ?
C13A C14A 1.391(8) . ?
C14A C15A 1.390(8) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.375(8) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.371(8) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.389(8) . ?
C17A H17A 0.9500 . ?
C18A H18A 0.9500 . ?
C19A C24A 1.386(8) . ?
C19A C20A 1.394(8) . ?
C20A C21A 1.371(8) . ?
C20A H20A 0.9500 . ?
C21A C22A 1.367(9) . ?
C21A H21A 0.9500 . ?
C22A C23A 1.373(8) . ?
C22A H22A 0.9500 . ?
C23A C24A 1.389(8) . ?
C23A H23A 0.9500 . ?
C24A H24A 0.9500 . ?
C1B O1B 1.344(7) . ?
C1B C2B 1.381(7) . ?
C1B C6B 1.418(7) . ?
C2B C3B 1.423(7) . ?
C2B C11B 1.448(7) . ?
C3B C4B 1.355(7) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.422(7) . ?
C4B H4B 0.9500 . ?
C5B C10B 1.400(7) . ?
C5B C6B 1.414(7) . ?
C6B C7B 1.420(8) . ?
C7B C8B 1.355(9) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.396(8) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.368(7) . ?
C9B H9B 0.9500 . ?
C10B H10B 0.9500 . ?
C11B N1B 1.278(7) . ?
C11B H11B 0.9500 . ?
C12B N2B 1.295(7) . ?
C12B C19B 1.476(8) . ?
C12B C13B 1.482(8) . ?
C13B C18B 1.378(8) . ?
C13B C14B 1.382(8) . ?
C14B C15B 1.377(9) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.370(9) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.374(8) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.383(8) . ?
C17B H17B 0.9500 . ?
C18B H18B 0.9500 . ?
C19B C20B 1.373(8) . ?
C19B C24B 1.396(8) . ?
C20B C21B 1.388(8) . ?
C20B H20B 0.9500 . ?
C21B C22B 1.378(9) . ?
C21B H21B 0.9500 . ?
C22B C23B 1.378(8) . ?
C22B H22B 0.9500 . ?
C23B C24B 1.375(8) . ?
C23B H23B 0.9500 . ?
C24B H24B 0.9500 . ?
N1A N2A 1.411(6) . ?
N1B N2B 1.410(6) . ?
O1A H1AA 0.81(3) . ?
O1B H1BA 0.82(3) . ?

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
O1A C1A C2A 121.1(5) . . ?
O1A C1A C6A 117.3(5) . . ?
C2A C1A C6A 121.6(5) . . ?
C1A C2A C3A 118.2(5) . . ?
C1A C2A C11A 122.7(5) . . ?
C3A C2A C11A 119.1(5) . . ?
C4A C3A C2A 121.4(6) . . ?
C4A C3A H3A 119.3 . . ?
C2A C3A H3A 119.3 . . ?
C3A C4A C5A 120.7(6) . . ?
C3A C4A H4A 119.6 . . ?
C5A C4A H4A 119.6 . . ?
C10A C5A C6A 118.9(5) . . ?
C10A C5A C4A 121.8(5) . . ?
C6A C5A C4A 119.3(5) . . ?
C7A C6A C5A 119.6(5) . . ?
C7A C6A C1A 121.7(5) . . ?
C5A C6A C1A 118.7(5) . . ?
C8A C7A C6A 119.9(6) . . ?
C8A C7A H7A 120.1 . . ?
C6A C7A H7A 120.1 . . ?
C7A C8A C9A 120.5(6) . . ?
C7A C8A H8A 119.7 . . ?
C9A C8A H8A 119.7 . . ?
C10A C9A C8A 120.5(6) . . ?
C10A C9A H9A 119.7 . . ?
C8A C9A H9A 119.7 . . ?
C9A C10A C5A 120.6(6) . . ?
C9A C10A H10A 119.7 . . ?
C5A C10A H10A 119.7 . . ?
N1A C11A C2A 120.5(5) . . ?
N1A C11A H11A 119.8 . . ?
C2A C11A H11A 119.8 . . ?
N2A C12A C19A 116.6(5) . . ?
N2A C12A C13A 124.6(5) . . ?
C19A C12A C13A 118.7(5) . . ?
C18A C13A C14A 119.1(6) . . ?
C18A C13A C12A 122.7(5) . . ?
C14A C13A C12A 118.2(5) . . ?
C15A C14A C13A 119.7(5) . . ?
C15A C14A H14A 120.2 . . ?
C13A C14A H14A 120.2 . . ?
C16A C15A C14A 121.1(6) . . ?
C16A C15A H15A 119.5 . . ?
C14A C15A H15A 119.5 . . ?
C17A C16A C15A 118.9(6) . . ?
C17A C16A H16A 120.6 . . ?
C15A C16A H16A 120.6 . . ?
C16A C17A C18A 120.8(6) . . ?
C16A C17A H17A 119.6 . . ?
C18A C17A H17A 119.6 . . ?
C13A C18A C17A 120.5(6) . . ?
C13A C18A H18A 119.8 . . ?
C17A C18A H18A 119.8 . . ?
C24A C19A C20A 117.9(5) . . ?
C24A C19A C12A 121.4(5) . . ?
C20A C19A C12A 120.7(6) . . ?
C21A C20A C19A 121.4(6) . . ?
C21A C20A H20A 119.3 . . ?
C19A C20A H20A 119.3 . . ?
C22A C21A C20A 119.5(6) . . ?
C22A C21A H21A 120.3 . . ?
C20A C21A H21A 120.3 . . ?
C21A C22A C23A 121.1(6) . . ?
C21A C22A H22A 119.5 . . ?
C23A C22A H22A 119.5 . . ?
C22A C23A C24A 119.2(6) . . ?
C22A C23A H23A 120.4 . . ?
C24A C23A H23A 120.4 . . ?
C19A C24A C23A 120.9(6) . . ?
C19A C24A H24A 119.6 . . ?
C23A C24A H24A 119.6 . . ?
O1B C1B C2B 122.7(5) . . ?
O1B C1B C6B 117.0(5) . . ?
C2B C1B C6B 120.3(5) . . ?
C1B C2B C3B 119.3(5) . . ?
C1B C2B C11B 121.4(5) . . ?
C3B C2B C11B 119.3(5) . . ?
C4B C3B C2B 121.2(5) . . ?
C4B C3B H3B 119.4 . . ?
C2B C3B H3B 119.4 . . ?
C3B C4B C5B 120.7(5) . . ?
C3B C4B H4B 119.6 . . ?
C5B C4B H4B 119.6 . . ?
C10B C5B C6B 119.6(5) . . ?
C10B C5B C4B 121.8(5) . . ?
C6B C5B C4B 118.6(5) . . ?
C5B C6B C1B 119.8(5) . . ?
C5B C6B C7B 118.2(5) . . ?
C1B C6B C7B 121.9(5) . . ?
C8B C7B C6B 120.2(6) . . ?
C8B C7B H7B 119.9 . . ?
C6B C7B H7B 119.9 . . ?
C7B C8B C9B 121.7(6) . . ?
C7B C8B H8B 119.1 . . ?
C9B C8B H8B 119.1 . . ?
C10B C9B C8B 119.2(6) . . ?
C10B C9B H9B 120.4 . . ?
C8B C9B H9B 120.4 . . ?
C9B C10B C5B 121.0(5) . . ?
C9B C10B H10B 119.5 . . ?
C5B C10B H10B 119.5 . . ?
N1B C11B C2B 122.0(5) . . ?
N1B C11B H11B 119.0 . . ?
C2B C11B H11B 119.0 . . ?
N2B C12B C19B 115.6(5) . . ?
N2B C12B C13B 124.8(5) . . ?
C19B C12B C13B 119.5(5) . . ?
C18B C13B C14B 118.8(6) . . ?
C18B C13B C12B 121.3(5) . . ?
C14B C13B C12B 119.9(5) . . ?
C15B C14B C13B 120.4(6) . . ?
C15B C14B H14B 119.8 . . ?
C13B C14B H14B 119.8 . . ?
C16B C15B C14B 120.5(6) . . ?
C16B C15B H15B 119.8 . . ?
C14B C15B H15B 119.8 . . ?
C17B C16B C15B 119.7(6) . . ?
C17B C16B H16B 120.2 . . ?
C15B C16B H16B 120.2 . . ?
C16B C17B C18B 120.0(6) . . ?
C16B C17B H17B 120.0 . . ?
C18B C17B H17B 120.0 . . ?
C13B C18B C17B 120.6(6) . . ?
C13B C18B H18B 119.7 . . ?
C17B C18B H18B 119.7 . . ?
C20B C19B C24B 118.4(6) . . ?
C20B C19B C12B 121.2(5) . . ?
C24B C19B C12B 120.3(6) . . ?
C19B C20B C21B 120.7(6) . . ?
C19B C20B H20B 119.6 . . ?
C21B C20B H20B 119.6 . . ?
C22B C21B C20B 120.3(6) . . ?
C22B C21B H21B 119.8 . . ?
C20B C21B H21B 119.8 . . ?
C23B C22B C21B 119.3(6) . . ?
C23B C22B H22B 120.3 . . ?
C21B C22B H22B 120.3 . . ?
C24B C23B C22B 120.3(6) . . ?
C24B C23B H23B 119.8 . . ?
C22B C23B H23B 119.8 . . ?
C23B C24B C19B 120.8(6) . . ?
C23B C24B H24B 119.6 . . ?
C19B C24B H24B 119.6 . . ?
C11A N1A N2A 113.0(5) . . ?
C12A N2A N1A 113.4(5) . . ?
C11B N1B N2B 112.5(5) . . ?
C12B N2B N1B 113.6(5) . . ?
C1A O1A H1AA 112(4) . . ?
C1B O1B H1BA 105(4) . . ?

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.050



####################################################################### 
# 
# 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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2010123'
loop_
_audit_author_name
_audit_author_address
' Kexin Zhang'
;South China University of Technology
China
;
_audit_update_record             
;
2020-06-16 deposited with the CCDC.	2020-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        1-DPAN
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 N2 O'
_chemical_formula_sum            'C24 H18 N2 O'
_chemical_formula_weight         350.40

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 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   16.6827(16)
_cell_length_b                   6.1420(7)
_cell_length_c                   18.096(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.896(5)
_cell_angle_gamma                90
_cell_volume                     1847.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1376
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      25.11

_exptl_crystal_description       sheet
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6112
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10502
_diffrn_reflns_av_unetI/netI     0.1140
_diffrn_reflns_av_R_equivalents  0.1090
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.189
_diffrn_reflns_theta_max         25.388
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3379
_reflns_number_gt                1806
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0235P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3379
_refine_ls_number_parameters     247
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1393
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.0995
_refine_ls_wR_factor_gt          0.0830
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.32466(14) 0.6907(4) 0.24532(14) 0.0173(6) Uani 1 1 d . . . . .
C2 C 0.26450(14) 0.5338(4) 0.24295(14) 0.0200(6) Uani 1 1 d . . . . .
C3 C 0.26818(15) 0.3457(4) 0.19904(14) 0.0230(7) Uani 1 1 d . . . . .
H3 H 0.2275 0.2378 0.1998 0.028 Uiso 1 1 calc R U . . .
C4 C 0.32988(15) 0.3178(5) 0.15542(15) 0.0269(7) Uani 1 1 d . . . . .
H4 H 0.3317 0.1898 0.1261 0.032 Uiso 1 1 calc R U . . .
C5 C 0.39146(14) 0.4759(5) 0.15282(14) 0.0223(7) Uani 1 1 d . . . . .
C6 C 0.39022(14) 0.6637(4) 0.19846(14) 0.0193(6) Uani 1 1 d . . . . .
C7 C 0.45236(14) 0.8189(4) 0.19421(15) 0.0253(7) Uani 1 1 d . . . . .
H7 H 0.4530 0.9457 0.2243 0.030 Uiso 1 1 calc R U . . .
C8 C 0.51171(15) 0.7889(5) 0.14723(16) 0.0313(8) Uani 1 1 d . . . . .
H8 H 0.5528 0.8953 0.1454 0.038 Uiso 1 1 calc R U . . .
C9 C 0.51269(16) 0.6033(5) 0.10177(15) 0.0349(8) Uani 1 1 d . . . . .
H9 H 0.5538 0.5850 0.0691 0.042 Uiso 1 1 calc R U . . .
C10 C 0.45388(15) 0.4498(5) 0.10519(15) 0.0299(7) Uani 1 1 d . . . . .
H10 H 0.4549 0.3233 0.0751 0.036 Uiso 1 1 calc R U . . .
C11 C 0.32226(14) 0.8768(4) 0.29433(13) 0.0187(6) Uani 1 1 d . . . . .
H11 H 0.3665 0.9744 0.2995 0.022 Uiso 1 1 calc R U . . .
C12 C 0.20631(14) 1.1576(4) 0.40573(14) 0.0183(6) Uani 1 1 d . . . . .
C13 C 0.21522(14) 1.3387(4) 0.46003(14) 0.0183(6) Uani 1 1 d . . . . .
C14 C 0.15815(15) 1.3703(4) 0.51105(15) 0.0243(7) Uani 1 1 d . . . . .
H14 H 0.1128 1.2767 0.5105 0.029 Uiso 1 1 calc R U . . .
C15 C 0.16728(16) 1.5379(5) 0.56275(15) 0.0296(7) Uani 1 1 d . . . . .
H15 H 0.1285 1.5568 0.5977 0.036 Uiso 1 1 calc R U . . .
C16 C 0.23223(16) 1.6766(5) 0.56350(15) 0.0297(7) Uani 1 1 d . . . . .
H16 H 0.2378 1.7924 0.5984 0.036 Uiso 1 1 calc R U . . .
C17 C 0.28966(16) 1.6467(5) 0.51294(15) 0.0273(7) Uani 1 1 d . . . . .
H17 H 0.3347 1.7415 0.5134 0.033 Uiso 1 1 calc R U . . .
C18 C 0.28108(14) 1.4785(4) 0.46200(15) 0.0234(7) Uani 1 1 d . . . . .
H18 H 0.3207 1.4582 0.4279 0.028 Uiso 1 1 calc R U . . .
C19 C 0.12335(14) 1.0719(4) 0.38429(13) 0.0175(6) Uani 1 1 d . . . . .
C20 C 0.10049(15) 0.8662(5) 0.40643(15) 0.0268(7) Uani 1 1 d . . . . .
H20 H 0.1384 0.7756 0.4339 0.032 Uiso 1 1 calc R U . . .
C21 C 0.02248(16) 0.7920(5) 0.38858(16) 0.0322(8) Uani 1 1 d . . . . .
H21 H 0.0069 0.6521 0.4046 0.039 Uiso 1 1 calc R U . . .
C22 C -0.03235(16) 0.9222(5) 0.34752(16) 0.0337(8) Uani 1 1 d . . . . .
H22 H -0.0857 0.8721 0.3355 0.040 Uiso 1 1 calc R U . . .
C23 C -0.00940(15) 1.1254(5) 0.32404(15) 0.0323(8) Uani 1 1 d . . . . .
H23 H -0.0468 1.2134 0.2950 0.039 Uiso 1 1 calc R U . . .
C24 C 0.06785(14) 1.2008(4) 0.34275(15) 0.0263(7) Uani 1 1 d . . . . .
H24 H 0.0830 1.3415 0.3271 0.032 Uiso 1 1 calc R U . . .
N1 N 0.26035(12) 0.9109(4) 0.33115(11) 0.0201(5) Uani 1 1 d . . . . .
N2 N 0.27160(11) 1.0880(4) 0.38052(11) 0.0211(5) Uani 1 1 d . . . . .
O1 O 0.19925(11) 0.5528(3) 0.28181(11) 0.0271(5) Uani 1 1 d D . . . .
H1A H 0.2008(16) 0.672(3) 0.3054(14) 0.033 Uiso 1 1 d D U . . .


_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
C1 C2 1.390(3) . ?
C1 C6 1.449(3) . ?
C1 C11 1.449(4) . ?
C2 O1 1.351(3) . ?
C2 C3 1.406(4) . ?
C3 C4 1.360(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.417(4) . ?
C4 H4 0.9500 . ?
C5 C10 1.416(3) . ?
C5 C6 1.420(4) . ?
C6 C7 1.415(3) . ?
C7 C8 1.371(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.407(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.366(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 N1 1.293(3) . ?
C11 H11 0.9500 . ?
C12 N2 1.289(3) . ?
C12 C13 1.483(4) . ?
C12 C19 1.500(3) . ?
C13 C18 1.392(3) . ?
C13 C14 1.395(3) . ?
C14 C15 1.391(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.389(4) . ?
C19 C24 1.389(3) . ?
C20 C21 1.391(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.383(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
N1 N2 1.410(3) . ?
O1 H1A 0.847(17) . ?

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
C2 C1 C6 118.8(2) . . ?
C2 C1 C11 120.6(2) . . ?
C6 C1 C11 120.7(2) . . ?
O1 C2 C1 122.4(2) . . ?
O1 C2 C3 116.2(2) . . ?
C1 C2 C3 121.4(2) . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 121.3(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C10 C5 C4 121.0(3) . . ?
C10 C5 C6 119.6(3) . . ?
C4 C5 C6 119.4(3) . . ?
C7 C6 C5 117.9(2) . . ?
C7 C6 C1 123.2(2) . . ?
C5 C6 C1 118.8(2) . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 121.1(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C5 121.2(3) . . ?
C9 C10 H10 119.4 . . ?
C5 C10 H10 119.4 . . ?
N1 C11 C1 120.6(2) . . ?
N1 C11 H11 119.7 . . ?
C1 C11 H11 119.7 . . ?
N2 C12 C13 116.3(2) . . ?
N2 C12 C19 125.5(2) . . ?
C13 C12 C19 118.2(2) . . ?
C18 C13 C14 118.6(3) . . ?
C18 C13 C12 120.9(2) . . ?
C14 C13 C12 120.5(2) . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.8(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 119.9(3) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C13 120.9(3) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
C20 C19 C24 119.2(2) . . ?
C20 C19 C12 121.0(2) . . ?
C24 C19 C12 119.8(2) . . ?
C21 C20 C19 120.4(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 119.9(3) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C23 C22 C21 119.9(3) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 120.2(3) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 120.3(3) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
C11 N1 N2 112.5(2) . . ?
C12 N2 N1 114.2(2) . . ?
C2 O1 H1A 110.2(19) . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.054



