# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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_mo_dd19294_0m
_database_code_depnum_ccdc_archive 'CCDC 2018725'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2020-07-24 deposited with the CCDC.	2020-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H18 Br N O2'
_chemical_formula_weight         444.31

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'
Br Br -0.2901 2.4595 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.0234(3)
_cell_length_b                   17.1521(6)
_cell_length_c                   14.4245(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.059(2)
_cell_angle_gamma                90
_cell_volume                     1982.24(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6545
_cell_measurement_theta_min      5.528
_cell_measurement_theta_max      62.992

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.095
_shelx_estimated_absorpt_T_min   0.704
_shelx_estimated_absorpt_T_max   0.787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4439
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19746
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.375
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3887
_reflns_number_gt                2843
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0573P)²+2.0227P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3887
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1346
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.004
_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
Br1 Br -0.02897(6) 0.17412(2) 0.31982(3) 0.0774(2) Uani 1 1 d . . . . .
O1 O 0.0911(4) 0.29426(14) 0.46058(17) 0.0598(7) Uani 1 1 d . . . . .
O2 O 0.1596(3) 0.36900(15) 0.20063(15) 0.0573(7) Uani 1 1 d . . . . .
N1 N 0.3056(4) 0.58937(15) 0.68120(17) 0.0433(6) Uani 1 1 d . . . . .
C1 C 0.1091(4) 0.31885(19) 0.3824(2) 0.0472(8) Uani 1 1 d . . . . .
C2 C 0.0641(5) 0.27336(19) 0.2999(3) 0.0530(9) Uani 1 1 d . . . . .
C3 C 0.0886(5) 0.2979(2) 0.2154(3) 0.0582(10) Uani 1 1 d . . . . .
C4 C 0.2028(4) 0.4169(2) 0.2739(2) 0.0480(8) Uani 1 1 d . . . . .
C5 C 0.1773(4) 0.39663(18) 0.3625(2) 0.0415(7) Uani 1 1 d . . . . .
C6 C 0.2191(4) 0.44938(17) 0.4425(2) 0.0393(7) Uani 1 1 d . . . . .
C7 C 0.1697(4) 0.52697(18) 0.4430(2) 0.0424(7) Uani 1 1 d . . . . .
H7 H 0.1149 0.5479 0.3903 0.051 Uiso 1 1 calc R U . . .
C8 C 0.2001(4) 0.57384(18) 0.5201(2) 0.0416(7) Uani 1 1 d . . . . .
H8 H 0.1661 0.6257 0.5188 0.050 Uiso 1 1 calc R U . . .
C9 C 0.2810(4) 0.54363(17) 0.5989(2) 0.0405(7) Uani 1 1 d . . . . .
C10 C 0.3339(4) 0.46671(19) 0.5985(2) 0.0449(8) Uani 1 1 d . . . . .
H10 H 0.3908 0.4461 0.6507 0.054 Uiso 1 1 calc R U . . .
C11 C 0.3032(4) 0.42072(18) 0.5217(2) 0.0447(8) Uani 1 1 d . . . . .
H11 H 0.3396 0.3692 0.5228 0.054 Uiso 1 1 calc R U . . .
C12 C 0.0543(7) 0.2571(3) 0.1247(3) 0.0896(16) Uani 1 1 d . . . . .
H12A H -0.0641 0.2543 0.1113 0.134 Uiso 1 1 calc R U . . .
H12B H 0.0998 0.2053 0.1282 0.134 Uiso 1 1 calc R U . . .
H12C H 0.1051 0.2855 0.0763 0.134 Uiso 1 1 calc R U . . .
C13 C 0.2822(5) 0.4883(2) 0.2386(3) 0.0589(10) Uani 1 1 d . . . . .
H13A H 0.3694 0.4739 0.1989 0.088 Uiso 1 1 calc R U . . .
H13B H 0.3286 0.5182 0.2900 0.088 Uiso 1 1 calc R U . . .
H13C H 0.2001 0.5189 0.2042 0.088 Uiso 1 1 calc R U . . .
C14 C 0.3792(4) 0.66305(17) 0.6880(2) 0.0411(7) Uani 1 1 d . . . . .
C15 C 0.4406(5) 0.70964(19) 0.6185(2) 0.0498(8) Uani 1 1 d . . . . .
H15 H 0.4315 0.6944 0.5565 0.060 Uiso 1 1 calc R U . . .
C16 C 0.5152(5) 0.7790(2) 0.6446(3) 0.0602(10) Uani 1 1 d . . . . .
H16 H 0.5586 0.8107 0.5995 0.072 Uiso 1 1 calc R U . . .
C17 C 0.5272(5) 0.8027(2) 0.7367(3) 0.0626(10) Uani 1 1 d . . . . .
H17 H 0.5769 0.8503 0.7519 0.075 Uiso 1 1 calc R U . . .
C18 C 0.4676(5) 0.7575(2) 0.8055(3) 0.0576(10) Uani 1 1 d . . . . .
H18 H 0.4764 0.7740 0.8670 0.069 Uiso 1 1 calc R U . . .
C19 C 0.3931(4) 0.68587(19) 0.7816(2) 0.0468(8) Uani 1 1 d . . . . .
C20 C 0.3251(5) 0.6233(2) 0.8342(2) 0.0480(8) Uani 1 1 d . . . . .
C21 C 0.3068(6) 0.6119(3) 0.9293(2) 0.0674(11) Uani 1 1 d . . . . .
H21 H 0.3419 0.6496 0.9724 0.081 Uiso 1 1 calc R U . . .
C22 C 0.2366(7) 0.5443(3) 0.9570(3) 0.0796(14) Uani 1 1 d . . . . .
H22 H 0.2245 0.5360 1.0200 0.096 Uiso 1 1 calc R U . . .
C23 C 0.1826(6) 0.4878(3) 0.8945(3) 0.0731(12) Uani 1 1 d . . . . .
H23 H 0.1330 0.4428 0.9163 0.088 Uiso 1 1 calc R U . . .
C24 C 0.2005(5) 0.4963(2) 0.8000(3) 0.0572(9) Uani 1 1 d . . . . .
H24 H 0.1656 0.4579 0.7579 0.069 Uiso 1 1 calc R U . . .
C25 C 0.2731(4) 0.56495(19) 0.7711(2) 0.0453(8) Uani 1 1 d . . . . .


_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
Br1 C2 1.887(4) . ?
O1 C1 1.220(4) . ?
O2 C3 1.368(5) . ?
O2 C4 1.369(4) . ?
N1 C14 1.396(4) . ?
N1 C25 1.401(4) . ?
N1 C9 1.428(4) . ?
C1 C2 1.452(5) . ?
C1 C5 1.476(5) . ?
C2 C3 1.313(5) . ?
C3 C12 1.497(5) . ?
C4 C5 1.351(4) . ?
C4 C13 1.482(5) . ?
C5 C6 1.489(4) . ?
C6 C11 1.386(4) . ?
C6 C7 1.389(4) . ?
C7 C8 1.383(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.386(4) . ?
C10 C11 1.371(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.393(5) . ?
C14 C19 1.404(4) . ?
C15 C16 1.375(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.388(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.366(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.402(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.438(5) . ?
C20 C25 1.401(4) . ?
C20 C21 1.402(5) . ?
C21 C22 1.358(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.379(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.387(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.387(5) . ?
C24 H24 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
C3 O2 C4 120.4(3) . . ?
C14 N1 C25 107.7(2) . . ?
C14 N1 C9 126.5(3) . . ?
C25 N1 C9 125.5(3) . . ?
O1 C1 C2 122.4(3) . . ?
O1 C1 C5 123.7(3) . . ?
C2 C1 C5 113.9(3) . . ?
C3 C2 C1 123.0(3) . . ?
C3 C2 Br1 120.7(3) . . ?
C1 C2 Br1 116.3(3) . . ?
C2 C3 O2 120.9(3) . . ?
C2 C3 C12 129.2(4) . . ?
O2 C3 C12 109.8(4) . . ?
C5 C4 O2 122.1(3) . . ?
C5 C4 C13 128.8(3) . . ?
O2 C4 C13 109.1(3) . . ?
C4 C5 C1 119.5(3) . . ?
C4 C5 C6 122.5(3) . . ?
C1 C5 C6 118.0(3) . . ?
C11 C6 C7 117.5(3) . . ?
C11 C6 C5 120.1(3) . . ?
C7 C6 C5 122.3(3) . . ?
C8 C7 C6 121.6(3) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 119.0(3) . . ?
C8 C9 N1 121.1(3) . . ?
C10 C9 N1 119.9(3) . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C6 121.4(3) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N1 129.3(3) . . ?
C15 C14 C19 121.3(3) . . ?
N1 C14 C19 109.4(3) . . ?
C16 C15 C14 117.7(3) . . ?
C16 C15 H15 121.2 . . ?
C14 C15 H15 121.2 . . ?
C15 C16 C17 121.5(4) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 121.4(3) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 118.7(3) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C18 C19 C14 119.4(3) . . ?
C18 C19 C20 133.9(3) . . ?
C14 C19 C20 106.6(3) . . ?
C25 C20 C21 119.5(3) . . ?
C25 C20 C19 107.4(3) . . ?
C21 C20 C19 133.0(3) . . ?
C22 C21 C20 118.3(4) . . ?
C22 C21 H21 120.9 . . ?
C20 C21 H21 120.9 . . ?
C21 C22 C23 121.9(4) . . ?
C21 C22 H22 119.0 . . ?
C23 C22 H22 119.0 . . ?
C22 C23 C24 121.5(4) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C23 C24 C25 116.9(4) . . ?
C23 C24 H24 121.5 . . ?
C25 C24 H24 121.5 . . ?
C24 C25 C20 121.8(3) . . ?
C24 C25 N1 129.3(3) . . ?
C20 C25 N1 108.9(3) . . ?

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 C1 C2 C3 -177.3(4) . . . . ?
C5 C1 C2 C3 2.8(5) . . . . ?
O1 C1 C2 Br1 1.3(5) . . . . ?
C5 C1 C2 Br1 -178.6(2) . . . . ?
C1 C2 C3 O2 0.1(6) . . . . ?
Br1 C2 C3 O2 -178.5(3) . . . . ?
C1 C2 C3 C12 177.8(4) . . . . ?
Br1 C2 C3 C12 -0.7(6) . . . . ?
C4 O2 C3 C2 -1.6(5) . . . . ?
C4 O2 C3 C12 -179.7(3) . . . . ?
C3 O2 C4 C5 -0.2(5) . . . . ?
C3 O2 C4 C13 177.9(3) . . . . ?
O2 C4 C5 C1 3.3(5) . . . . ?
C13 C4 C5 C1 -174.4(3) . . . . ?
O2 C4 C5 C6 -178.0(3) . . . . ?
C13 C4 C5 C6 4.3(6) . . . . ?
O1 C1 C5 C4 175.7(3) . . . . ?
C2 C1 C5 C4 -4.4(5) . . . . ?
O1 C1 C5 C6 -3.0(5) . . . . ?
C2 C1 C5 C6 176.9(3) . . . . ?
C4 C5 C6 C11 -134.4(4) . . . . ?
C1 C5 C6 C11 44.3(4) . . . . ?
C4 C5 C6 C7 48.7(5) . . . . ?
C1 C5 C6 C7 -132.6(3) . . . . ?
C11 C6 C7 C8 -1.2(5) . . . . ?
C5 C6 C7 C8 175.8(3) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
C7 C8 C9 C10 1.5(5) . . . . ?
C7 C8 C9 N1 -176.4(3) . . . . ?
C14 N1 C9 C8 -53.3(5) . . . . ?
C25 N1 C9 C8 132.7(3) . . . . ?
C14 N1 C9 C10 128.8(4) . . . . ?
C25 N1 C9 C10 -45.2(5) . . . . ?
C8 C9 C10 C11 -1.4(5) . . . . ?
N1 C9 C10 C11 176.5(3) . . . . ?
C9 C10 C11 C6 0.1(5) . . . . ?
C7 C6 C11 C10 1.2(5) . . . . ?
C5 C6 C11 C10 -175.8(3) . . . . ?
C25 N1 C14 C15 176.8(3) . . . . ?
C9 N1 C14 C15 1.9(6) . . . . ?
C25 N1 C14 C19 -0.3(4) . . . . ?
C9 N1 C14 C19 -175.2(3) . . . . ?
N1 C14 C15 C16 -176.9(3) . . . . ?
C19 C14 C15 C16 -0.1(5) . . . . ?
C14 C15 C16 C17 -0.9(6) . . . . ?
C15 C16 C17 C18 1.0(7) . . . . ?
C16 C17 C18 C19 0.0(6) . . . . ?
C17 C18 C19 C14 -1.0(6) . . . . ?
C17 C18 C19 C20 176.8(4) . . . . ?
C15 C14 C19 C18 1.1(5) . . . . ?
N1 C14 C19 C18 178.4(3) . . . . ?
C15 C14 C19 C20 -177.3(3) . . . . ?
N1 C14 C19 C20 0.1(4) . . . . ?
C18 C19 C20 C25 -177.8(4) . . . . ?
C14 C19 C20 C25 0.1(4) . . . . ?
C18 C19 C20 C21 1.1(8) . . . . ?
C14 C19 C20 C21 179.0(4) . . . . ?
C25 C20 C21 C22 -0.8(6) . . . . ?
C19 C20 C21 C22 -179.6(4) . . . . ?
C20 C21 C22 C23 -0.4(8) . . . . ?
C21 C22 C23 C24 1.4(8) . . . . ?
C22 C23 C24 C25 -0.9(7) . . . . ?
C23 C24 C25 C20 -0.4(6) . . . . ?
C23 C24 C25 N1 -179.6(4) . . . . ?
C21 C20 C25 C24 1.2(6) . . . . ?
C19 C20 C25 C24 -179.7(3) . . . . ?
C21 C20 C25 N1 -179.4(3) . . . . ?
C19 C20 C25 N1 -0.3(4) . . . . ?
C14 N1 C25 C24 179.7(4) . . . . ?
C9 N1 C25 C24 -5.4(6) . . . . ?
C14 N1 C25 C20 0.4(4) . . . . ?
C9 N1 C25 C20 175.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 O1 0.93 2.51 3.275(4) 139.7 3_566
C8 H8 O1 0.93 2.51 3.275(4) 139.7 3_566

_refine_diff_density_max         0.699
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_dd19318_0m
_database_code_depnum_ccdc_archive 'CCDC 2018727'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2020-07-24 deposited with the CCDC.	2020-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C43 H30 N2 O2'
_chemical_formula_weight         606.69

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                   9.8491(8)
_cell_length_b                   21.1814(12)
_cell_length_c                   15.1737(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.426(2)
_cell_angle_gamma                90
_cell_volume                     3131.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3874
_cell_measurement_theta_min      5.022
_cell_measurement_theta_max      52.829

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             1272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6873
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15032
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.823
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5792
_reflns_number_gt                3779
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0528P)²+0.6548P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0207(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5792
_refine_ls_number_parameters     427
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1368
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
O1 O 0.71955(19) 0.49266(7) 0.62032(10) 0.0615(5) Uani 1 1 d . . . . .
O2 O 0.97194(15) 0.61394(6) 0.76707(9) 0.0448(4) Uani 1 1 d . . . . .
N1 N 0.7687(2) 0.58088(8) 0.24402(11) 0.0488(5) Uani 1 1 d . . . . .
N2 N 0.68230(19) 0.28118(8) 0.88510(11) 0.0456(5) Uani 1 1 d . . . . .
C1 C 0.9541(2) 0.61862(10) 0.67597(14) 0.0439(5) Uani 1 1 d . . . . .
C2 C 0.8713(2) 0.57920(9) 0.62392(13) 0.0413(5) Uani 1 1 d . . . . .
C3 C 0.8026(2) 0.52799(9) 0.66409(13) 0.0407(5) Uani 1 1 d . . . . .
C4 C 0.8419(2) 0.51955(9) 0.76039(13) 0.0362(5) Uani 1 1 d . . . . .
C5 C 0.9193(2) 0.56356(9) 0.80734(13) 0.0386(5) Uani 1 1 d . . . . .
C6 C 0.9584(2) 0.56707(11) 0.90562(13) 0.0506(6) Uani 1 1 d . . . . .
H6A H 1.0554 0.5603 0.9207 0.076 Uiso 1 1 calc R U . . .
H6B H 0.9098 0.5352 0.9334 0.076 Uiso 1 1 calc R U . . .
H6C H 0.9352 0.6080 0.9263 0.076 Uiso 1 1 calc R U . . .
C7 C 1.0380(3) 0.67190(11) 0.64884(16) 0.0615(7) Uani 1 1 d . . . . .
H7A H 1.0238 0.7087 0.6833 0.092 Uiso 1 1 calc R U . . .
H7B H 1.0109 0.6808 0.5867 0.092 Uiso 1 1 calc R U . . .
H7C H 1.1334 0.6605 0.6591 0.092 Uiso 1 1 calc R U . . .
C8 C 0.8481(2) 0.58403(10) 0.52452(14) 0.0443(6) Uani 1 1 d . . . . .
C9 C 0.9536(3) 0.57743(11) 0.47456(15) 0.0535(6) Uani 1 1 d . . . . .
H9 H 1.0432 0.5727 0.5031 0.064 Uiso 1 1 calc R U . . .
C10 C 0.9276(3) 0.57772(11) 0.38257(15) 0.0550(6) Uani 1 1 d . . . . .
H10 H 0.9999 0.5737 0.3498 0.066 Uiso 1 1 calc R U . . .
C11 C 0.7967(3) 0.58384(10) 0.33946(14) 0.0472(6) Uani 1 1 d . . . . .
C12 C 0.6906(3) 0.59163(15) 0.38795(16) 0.0775(9) Uani 1 1 d . . . . .
H12 H 0.6014 0.5970 0.3590 0.093 Uiso 1 1 calc R U . . .
C13 C 0.7171(3) 0.59138(14) 0.47987(16) 0.0746(9) Uani 1 1 d . . . . .
H13 H 0.6447 0.5963 0.5123 0.090 Uiso 1 1 calc R U . . .
C14 C 0.7565(2) 0.63200(10) 0.18595(14) 0.0449(6) Uani 1 1 d . . . . .
C15 C 0.7732(3) 0.69568(11) 0.20477(16) 0.0586(7) Uani 1 1 d . . . . .
H15 H 0.8000 0.7100 0.2626 0.070 Uiso 1 1 calc R U . . .
C16 C 0.7483(3) 0.73693(13) 0.13405(19) 0.0729(8) Uani 1 1 d . . . . .
H16 H 0.7570 0.7801 0.1446 0.087 Uiso 1 1 calc R U . . .
C17 C 0.7107(3) 0.71568(14) 0.04767(19) 0.0833(9) Uani 1 1 d . . . . .
H17 H 0.6954 0.7448 0.0014 0.100 Uiso 1 1 calc R U . . .
C18 C 0.6956(3) 0.65278(13) 0.02930(17) 0.0686(8) Uani 1 1 d . . . . .
H18 H 0.6706 0.6390 -0.0290 0.082 Uiso 1 1 calc R U . . .
C19 C 0.7181(2) 0.60961(11) 0.09903(14) 0.0478(6) Uani 1 1 d . . . . .
C20 C 0.7057(2) 0.54230(11) 0.10446(14) 0.0453(6) Uani 1 1 d . . . . .
C21 C 0.6685(2) 0.49391(13) 0.04291(16) 0.0583(7) Uani 1 1 d . . . . .
H21 H 0.6475 0.5031 -0.0175 0.070 Uiso 1 1 calc R U . . .
C22 C 0.6631(3) 0.43271(13) 0.07205(19) 0.0663(7) Uani 1 1 d . . . . .
H22 H 0.6375 0.4006 0.0312 0.080 Uiso 1 1 calc R U . . .
C23 C 0.6955(3) 0.41832(12) 0.1619(2) 0.0676(7) Uani 1 1 d . . . . .
H23 H 0.6923 0.3765 0.1800 0.081 Uiso 1 1 calc R U . . .
C24 C 0.7320(3) 0.46424(11) 0.22457(17) 0.0595(7) Uani 1 1 d . . . . .
H24 H 0.7529 0.4543 0.2847 0.071 Uiso 1 1 calc R U . . .
C25 C 0.7368(2) 0.52610(11) 0.19498(14) 0.0462(6) Uani 1 1 d . . . . .
C26 C 0.7984(2) 0.46039(9) 0.80140(12) 0.0346(5) Uani 1 1 d . . . . .
C27 C 0.6607(2) 0.44395(10) 0.79609(13) 0.0411(5) Uani 1 1 d . . . . .
H27 H 0.5933 0.4722 0.7716 0.049 Uiso 1 1 calc R U . . .
C28 C 0.6233(2) 0.38596(10) 0.82700(13) 0.0424(5) Uani 1 1 d . . . . .
H28 H 0.5309 0.3761 0.8251 0.051 Uiso 1 1 calc R U . . .
C29 C 0.7225(2) 0.34251(9) 0.86077(12) 0.0383(5) Uani 1 1 d . . . . .
C30 C 0.8596(2) 0.35911(9) 0.86860(13) 0.0421(5) Uani 1 1 d . . . . .
H30 H 0.9269 0.3308 0.8932 0.051 Uiso 1 1 calc R U . . .
C31 C 0.8962(2) 0.41763(9) 0.83993(13) 0.0397(5) Uani 1 1 d . . . . .
H31 H 0.9885 0.4287 0.8466 0.048 Uiso 1 1 calc R U . . .
C32 C 0.5959(2) 0.24084(10) 0.82966(14) 0.0456(6) Uani 1 1 d . . . . .
C33 C 0.5353(3) 0.24981(11) 0.74243(15) 0.0563(6) Uani 1 1 d . . . . .
H33 H 0.5498 0.2866 0.7117 0.068 Uiso 1 1 calc R U . . .
C34 C 0.4528(3) 0.20218(13) 0.70272(18) 0.0708(8) Uani 1 1 d . . . . .
H34 H 0.4089 0.2077 0.6447 0.085 Uiso 1 1 calc R U . . .
C35 C 0.4333(3) 0.14641(13) 0.74669(19) 0.0715(8) Uani 1 1 d . . . . .
H35 H 0.3769 0.1152 0.7179 0.086 Uiso 1 1 calc R U . . .
C36 C 0.4964(3) 0.13676(11) 0.83217(18) 0.0613(7) Uani 1 1 d . . . . .
H36 H 0.4843 0.0990 0.8613 0.074 Uiso 1 1 calc R U . . .
C37 C 0.5790(2) 0.18440(10) 0.87517(15) 0.0492(6) Uani 1 1 d . . . . .
C38 C 0.6593(2) 0.19026(10) 0.96214(15) 0.0473(6) Uani 1 1 d . . . . .
C39 C 0.6846(3) 0.15039(12) 1.03606(17) 0.0598(7) Uani 1 1 d . . . . .
H39 H 0.6449 0.1105 1.0347 0.072 Uiso 1 1 calc R U . . .
C40 C 0.7680(3) 0.17064(13) 1.10999(18) 0.0688(8) Uani 1 1 d . . . . .
H40 H 0.7852 0.1442 1.1593 0.083 Uiso 1 1 calc R U . . .
C41 C 0.8281(3) 0.23019(13) 1.11322(16) 0.0689(8) Uani 1 1 d . . . . .
H41 H 0.8839 0.2429 1.1649 0.083 Uiso 1 1 calc R U . . .
C42 C 0.8066(3) 0.27091(11) 1.04121(15) 0.0569(7) Uani 1 1 d . . . . .
H42 H 0.8474 0.3106 1.0433 0.068 Uiso 1 1 calc R U . . .
C43 C 0.7220(2) 0.25017(10) 0.96622(13) 0.0441(5) Uani 1 1 d . . . . .


_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 C3 1.229(2) . ?
O2 C5 1.369(2) . ?
O2 C1 1.371(2) . ?
N1 C14 1.390(3) . ?
N1 C25 1.389(3) . ?
N1 C11 1.435(3) . ?
N2 C32 1.397(3) . ?
N2 C43 1.400(2) . ?
N2 C29 1.422(2) . ?
C1 C2 1.341(3) . ?
C1 C7 1.492(3) . ?
C2 C3 1.458(3) . ?
C2 C8 1.495(3) . ?
C3 C4 1.467(3) . ?
C4 C5 1.341(3) . ?
C4 C26 1.490(3) . ?
C5 C6 1.486(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.375(3) . ?
C8 C9 1.380(3) . ?
C9 C10 1.382(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.364(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(3) . ?
C12 C13 1.381(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.384(3) . ?
C14 C19 1.401(3) . ?
C15 C16 1.378(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.365(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.391(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.434(3) . ?
C20 C21 1.399(3) . ?
C20 C25 1.405(3) . ?
C21 C22 1.373(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.388(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.371(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.388(3) . ?
C24 H24 0.9300 . ?
C26 C31 1.387(3) . ?
C26 C27 1.390(3) . ?
C27 C28 1.384(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.385(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.383(3) . ?
C30 C31 1.379(3) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 C33 1.383(3) . ?
C32 C37 1.402(3) . ?
C33 C34 1.378(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.384(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.369(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.397(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.441(3) . ?
C38 C39 1.397(3) . ?
C38 C43 1.409(3) . ?
C39 C40 1.359(4) . ?
C39 H39 0.9300 . ?
C40 C41 1.391(4) . ?
C40 H40 0.9300 . ?
C41 C42 1.384(3) . ?
C41 H41 0.9300 . ?
C42 C43 1.380(3) . ?
C42 H42 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
C5 O2 C1 120.36(16) . . ?
C14 N1 C25 108.63(17) . . ?
C14 N1 C11 126.25(18) . . ?
C25 N1 C11 124.89(18) . . ?
C32 N2 C43 108.04(17) . . ?
C32 N2 C29 124.77(17) . . ?
C43 N2 C29 127.18(17) . . ?
C2 C1 O2 121.74(18) . . ?
C2 C1 C7 128.5(2) . . ?
O2 C1 C7 109.79(18) . . ?
C1 C2 C3 119.76(18) . . ?
C1 C2 C8 122.79(19) . . ?
C3 C2 C8 117.43(18) . . ?
O1 C3 C2 122.66(19) . . ?
O1 C3 C4 121.44(19) . . ?
C2 C3 C4 115.87(18) . . ?
C5 C4 C3 119.40(18) . . ?
C5 C4 C26 122.60(18) . . ?
C3 C4 C26 117.94(17) . . ?
C4 C5 O2 121.85(18) . . ?
C4 C5 C6 127.66(19) . . ?
O2 C5 C6 110.47(17) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 117.9(2) . . ?
C13 C8 C2 119.9(2) . . ?
C9 C8 C2 122.1(2) . . ?
C8 C9 C10 120.8(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.7(2) . . ?
C10 C11 N1 120.6(2) . . ?
C12 C11 N1 119.8(2) . . ?
C11 C12 C13 119.6(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C8 C13 C12 121.5(2) . . ?
C8 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C15 C14 N1 129.2(2) . . ?
C15 C14 C19 122.1(2) . . ?
N1 C14 C19 108.63(19) . . ?
C16 C15 C14 117.1(2) . . ?
C16 C15 H15 121.5 . . ?
C14 C15 H15 121.5 . . ?
C15 C16 C17 121.6(3) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C16 121.1(3) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 119.1(2) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C18 C19 C14 119.0(2) . . ?
C18 C19 C20 133.8(2) . . ?
C14 C19 C20 107.22(18) . . ?
C21 C20 C25 118.2(2) . . ?
C21 C20 C19 134.9(2) . . ?
C25 C20 C19 106.89(19) . . ?
C22 C21 C20 119.7(2) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 120.6(2) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 121.7(2) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C23 C24 C25 117.6(2) . . ?
C23 C24 H24 121.2 . . ?
C25 C24 H24 121.2 . . ?
C24 C25 N1 129.1(2) . . ?
C24 C25 C20 122.2(2) . . ?
N1 C25 C20 108.63(19) . . ?
C31 C26 C27 118.14(18) . . ?
C31 C26 C4 120.05(19) . . ?
C27 C26 C4 121.61(18) . . ?
C28 C27 C26 120.6(2) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C29 C28 C27 120.5(2) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 C30 119.31(19) . . ?
C28 C29 N2 119.7(2) . . ?
C30 C29 N2 121.01(19) . . ?
C31 C30 C29 119.89(19) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C30 C31 C26 121.5(2) . . ?
C30 C31 H31 119.3 . . ?
C26 C31 H31 119.3 . . ?
C33 C32 N2 129.1(2) . . ?
C33 C32 C37 121.5(2) . . ?
N2 C32 C37 109.29(19) . . ?
C34 C33 C32 117.5(2) . . ?
C34 C33 H33 121.2 . . ?
C32 C33 H33 121.2 . . ?
C33 C34 C35 121.9(3) . . ?
C33 C34 H34 119.0 . . ?
C35 C34 H34 119.0 . . ?
C36 C35 C34 120.6(2) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C35 C36 C37 119.2(2) . . ?
C35 C36 H36 120.4 . . ?
C37 C36 H36 120.4 . . ?
C36 C37 C32 119.3(2) . . ?
C36 C37 C38 133.9(2) . . ?
C32 C37 C38 106.80(19) . . ?
C39 C38 C43 118.9(2) . . ?
C39 C38 C37 133.9(2) . . ?
C43 C38 C37 107.22(18) . . ?
C40 C39 C38 119.2(2) . . ?
C40 C39 H39 120.4 . . ?
C38 C39 H39 120.4 . . ?
C39 C40 C41 121.2(2) . . ?
C39 C40 H40 119.4 . . ?
C41 C40 H40 119.4 . . ?
C42 C41 C40 121.5(2) . . ?
C42 C41 H41 119.3 . . ?
C40 C41 H41 119.3 . . ?
C43 C42 C41 117.2(2) . . ?
C43 C42 H42 121.4 . . ?
C41 C42 H42 121.4 . . ?
C42 C43 N2 129.3(2) . . ?
C42 C43 C38 122.1(2) . . ?
N2 C43 C38 108.64(19) . . ?

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
C5 O2 C1 C2 8.5(3) . . . . ?
C5 O2 C1 C7 -171.55(19) . . . . ?
O2 C1 C2 C3 -2.8(3) . . . . ?
C7 C1 C2 C3 177.2(2) . . . . ?
O2 C1 C2 C8 178.85(19) . . . . ?
C7 C1 C2 C8 -1.1(4) . . . . ?
C1 C2 C3 O1 175.7(2) . . . . ?
C8 C2 C3 O1 -5.9(3) . . . . ?
C1 C2 C3 C4 -6.2(3) . . . . ?
C8 C2 C3 C4 172.17(18) . . . . ?
O1 C3 C4 C5 -171.7(2) . . . . ?
C2 C3 C4 C5 10.1(3) . . . . ?
O1 C3 C4 C26 10.9(3) . . . . ?
C2 C3 C4 C26 -167.24(18) . . . . ?
C3 C4 C5 O2 -5.1(3) . . . . ?
C26 C4 C5 O2 172.13(18) . . . . ?
C3 C4 C5 C6 173.5(2) . . . . ?
C26 C4 C5 C6 -9.2(3) . . . . ?
C1 O2 C5 C4 -4.3(3) . . . . ?
C1 O2 C5 C6 176.82(19) . . . . ?
C1 C2 C8 C13 -122.9(3) . . . . ?
C3 C2 C8 C13 58.8(3) . . . . ?
C1 C2 C8 C9 61.3(3) . . . . ?
C3 C2 C8 C9 -117.1(2) . . . . ?
C13 C8 C9 C10 -0.5(4) . . . . ?
C2 C8 C9 C10 175.4(2) . . . . ?
C8 C9 C10 C11 -0.7(4) . . . . ?
C9 C10 C11 C12 1.9(4) . . . . ?
C9 C10 C11 N1 -176.8(2) . . . . ?
C14 N1 C11 C10 -95.4(3) . . . . ?
C25 N1 C11 C10 90.8(3) . . . . ?
C14 N1 C11 C12 86.0(3) . . . . ?
C25 N1 C11 C12 -87.9(3) . . . . ?
C10 C11 C12 C13 -1.8(4) . . . . ?
N1 C11 C12 C13 176.8(3) . . . . ?
C9 C8 C13 C12 0.6(4) . . . . ?
C2 C8 C13 C12 -175.5(3) . . . . ?
C11 C12 C13 C8 0.6(5) . . . . ?
C25 N1 C14 C15 177.4(2) . . . . ?
C11 N1 C14 C15 2.8(4) . . . . ?
C25 N1 C14 C19 -0.6(3) . . . . ?
C11 N1 C14 C19 -175.3(2) . . . . ?
N1 C14 C15 C16 -176.9(2) . . . . ?
C19 C14 C15 C16 0.9(4) . . . . ?
C14 C15 C16 C17 -1.1(4) . . . . ?
C15 C16 C17 C18 0.6(5) . . . . ?
C16 C17 C18 C19 0.3(5) . . . . ?
C17 C18 C19 C14 -0.5(4) . . . . ?
C17 C18 C19 C20 176.6(3) . . . . ?
C15 C14 C19 C18 -0.1(4) . . . . ?
N1 C14 C19 C18 178.1(2) . . . . ?
C15 C14 C19 C20 -177.9(2) . . . . ?
N1 C14 C19 C20 0.3(3) . . . . ?
C18 C19 C20 C21 1.0(5) . . . . ?
C14 C19 C20 C21 178.3(3) . . . . ?
C18 C19 C20 C25 -177.2(3) . . . . ?
C14 C19 C20 C25 0.2(3) . . . . ?
C25 C20 C21 C22 0.2(3) . . . . ?
C19 C20 C21 C22 -177.9(3) . . . . ?
C20 C21 C22 C23 -0.6(4) . . . . ?
C21 C22 C23 C24 0.8(4) . . . . ?
C22 C23 C24 C25 -0.6(4) . . . . ?
C23 C24 C25 N1 179.1(2) . . . . ?
C23 C24 C25 C20 0.1(4) . . . . ?
C14 N1 C25 C24 -178.4(2) . . . . ?
C11 N1 C25 C24 -3.6(4) . . . . ?
C14 N1 C25 C20 0.7(3) . . . . ?
C11 N1 C25 C20 175.5(2) . . . . ?
C21 C20 C25 C24 0.1(3) . . . . ?
C19 C20 C25 C24 178.6(2) . . . . ?
C21 C20 C25 N1 -179.1(2) . . . . ?
C19 C20 C25 N1 -0.5(3) . . . . ?
C5 C4 C26 C31 -61.7(3) . . . . ?
C3 C4 C26 C31 115.6(2) . . . . ?
C5 C4 C26 C27 123.5(2) . . . . ?
C3 C4 C26 C27 -59.2(3) . . . . ?
C31 C26 C27 C28 -1.2(3) . . . . ?
C4 C26 C27 C28 173.65(19) . . . . ?
C26 C27 C28 C29 -2.3(3) . . . . ?
C27 C28 C29 C30 4.1(3) . . . . ?
C27 C28 C29 N2 -174.62(18) . . . . ?
C32 N2 C29 C28 52.6(3) . . . . ?
C43 N2 C29 C28 -128.4(2) . . . . ?
C32 N2 C29 C30 -126.0(2) . . . . ?
C43 N2 C29 C30 53.0(3) . . . . ?
C28 C29 C30 C31 -2.3(3) . . . . ?
N2 C29 C30 C31 176.39(18) . . . . ?
C29 C30 C31 C26 -1.3(3) . . . . ?
C27 C26 C31 C30 3.0(3) . . . . ?
C4 C26 C31 C30 -171.92(18) . . . . ?
C43 N2 C32 C33 -177.4(2) . . . . ?
C29 N2 C32 C33 1.7(4) . . . . ?
C43 N2 C32 C37 0.6(3) . . . . ?
C29 N2 C32 C37 179.7(2) . . . . ?
N2 C32 C33 C34 -179.6(2) . . . . ?
C37 C32 C33 C34 2.6(4) . . . . ?
C32 C33 C34 C35 -1.8(4) . . . . ?
C33 C34 C35 C36 0.0(4) . . . . ?
C34 C35 C36 C37 1.1(4) . . . . ?
C35 C36 C37 C32 -0.2(4) . . . . ?
C35 C36 C37 C38 -179.6(3) . . . . ?
C33 C32 C37 C36 -1.7(4) . . . . ?
N2 C32 C37 C36 -179.8(2) . . . . ?
C33 C32 C37 C38 177.8(2) . . . . ?
N2 C32 C37 C38 -0.3(3) . . . . ?
C36 C37 C38 C39 0.1(5) . . . . ?
C32 C37 C38 C39 -179.3(2) . . . . ?
C36 C37 C38 C43 179.4(3) . . . . ?
C32 C37 C38 C43 0.0(3) . . . . ?
C43 C38 C39 C40 0.5(3) . . . . ?
C37 C38 C39 C40 179.8(3) . . . . ?
C38 C39 C40 C41 0.1(4) . . . . ?
C39 C40 C41 C42 -0.7(4) . . . . ?
C40 C41 C42 C43 0.5(4) . . . . ?
C41 C42 C43 N2 179.6(2) . . . . ?
C41 C42 C43 C38 0.1(4) . . . . ?
C32 N2 C43 C42 179.9(2) . . . . ?
C29 N2 C43 C42 0.8(4) . . . . ?
C32 N2 C43 C38 -0.6(2) . . . . ?
C29 N2 C43 C38 -179.7(2) . . . . ?
C39 C38 C43 C42 -0.6(3) . . . . ?
C37 C38 C43 C42 179.9(2) . . . . ?
C39 C38 C43 N2 179.8(2) . . . . ?
C37 C38 C43 N2 0.4(2) . . . . ?

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_dd19315
_database_code_depnum_ccdc_archive 'CCDC 2018726'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2020-07-24 deposited with the CCDC.	2020-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H19 N O2'
_chemical_formula_weight         365.41

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           161
_space_group_name_H-M_alt        'R 3 c :H'
_space_group_name_Hall           'R 3 -2"c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   33.0425(9)
_cell_length_b                   33.0425(9)
_cell_length_c                   8.7370(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     8261.1(13)
_cell_formula_units_Z            18
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9983
_cell_measurement_theta_min      4.931
_cell_measurement_theta_max      50.886

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             3456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7033
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40683
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.466
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3611
_reflns_number_gt                3145
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.990
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0316P)²+3.1692P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00179(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1387 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.0(5)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3611
_refine_ls_number_parameters     256
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0794
_refine_ls_wR_factor_gt          0.0734
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
O1 O 0.65372(8) 0.61712(8) 0.7459(2) 0.0582(6) Uani 1 1 d . . . . .
O2 O 0.75688(7) 0.61167(7) 0.9746(2) 0.0497(5) Uani 1 1 d . . . . .
N1 N 0.64645(8) 0.49736(8) 0.1776(3) 0.0428(5) Uani 1 1 d . . . . .
C1 C 0.73927(10) 0.63858(10) 1.0267(3) 0.0422(7) Uani 1 1 d . . . . .
C2 C 0.70427(10) 0.63951(10) 0.9576(3) 0.0442(7) Uani 1 1 d . . . . .
H2 H 0.6917 0.6564 1.0014 0.053 Uiso 1 1 calc R U . . .
C3 C 0.68486(10) 0.61481(10) 0.8151(3) 0.0404(6) Uani 1 1 d . . . . .
C4 C 0.70585(9) 0.58733(9) 0.7592(3) 0.0386(6) Uani 1 1 d . . . . .
C5 C 0.73961(10) 0.58637(10) 0.8411(3) 0.0447(7) Uani 1 1 d . . . . .
C6 C 0.76512(14) 0.56092(14) 0.8081(4) 0.0698(10) Uani 1 1 d . . . . .
H6A H 0.7977 0.5808 0.8306 0.105 Uiso 1 1 calc R U . . .
H6B H 0.7614 0.5522 0.7020 0.105 Uiso 1 1 calc R U . . .
H6C H 0.7527 0.5333 0.8705 0.105 Uiso 1 1 calc R U . . .
C7 C 0.76572(11) 0.66597(12) 1.1640(3) 0.0536(8) Uani 1 1 d . . . . .
H7A H 0.7691 0.6457 1.2350 0.080 Uiso 1 1 calc R U . . .
H7B H 0.7490 0.6794 1.2121 0.080 Uiso 1 1 calc R U . . .
H7C H 0.7961 0.6905 1.1331 0.080 Uiso 1 1 calc R U . . .
C8 C 0.69002(9) 0.56293(9) 0.6092(3) 0.0396(6) Uani 1 1 d . . . . .
C9 C 0.69115(10) 0.58806(9) 0.4804(3) 0.0428(7) Uani 1 1 d . . . . .
H9 H 0.7013 0.6198 0.4893 0.051 Uiso 1 1 calc R U . . .
C10 C 0.67742(11) 0.56661(10) 0.3393(3) 0.0441(7) Uani 1 1 d . . . . .
H10 H 0.6791 0.5841 0.2537 0.053 Uiso 1 1 calc R U . . .
C11 C 0.66111(10) 0.51921(9) 0.3243(3) 0.0396(6) Uani 1 1 d . . . . .
C12 C 0.65901(10) 0.49361(10) 0.4519(3) 0.0454(7) Uani 1 1 d . . . . .
H12 H 0.6477 0.4617 0.4435 0.054 Uiso 1 1 calc R U . . .
C13 C 0.67366(10) 0.51540(9) 0.5917(3) 0.0442(7) Uani 1 1 d . . . . .
H13 H 0.6726 0.4979 0.6766 0.053 Uiso 1 1 calc R U . . .
C14 C 0.61598(10) 0.50215(10) 0.0771(3) 0.0394(6) Uani 1 1 d . . . . .
C15 C 0.59462(11) 0.52882(11) 0.0903(3) 0.0493(7) Uani 1 1 d . . . . .
H15 H 0.5998 0.5478 0.1753 0.059 Uiso 1 1 calc R U . . .
C16 C 0.56547(12) 0.52653(12) -0.0256(4) 0.0559(8) Uani 1 1 d . . . . .
H16 H 0.5509 0.5443 -0.0190 0.067 Uiso 1 1 calc R U . . .
C17 C 0.55726(11) 0.49801(11) -0.1533(4) 0.0556(8) Uani 1 1 d . . . . .
H17 H 0.5374 0.4971 -0.2304 0.067 Uiso 1 1 calc R U . . .
C18 C 0.57824(11) 0.47134(11) -0.1655(3) 0.0485(7) Uani 1 1 d . . . . .
H18 H 0.5728 0.4524 -0.2506 0.058 Uiso 1 1 calc R U . . .
C19 C 0.60771(10) 0.47290(9) -0.0497(3) 0.0400(6) Uani 1 1 d . . . . .
C20 C 0.63417(9) 0.44966(9) -0.0263(3) 0.0395(6) Uani 1 1 d . . . . .
C21 C 0.64020(10) 0.41761(10) -0.1124(3) 0.0466(7) Uani 1 1 d . . . . .
H21 H 0.6244 0.4064 -0.2045 0.056 Uiso 1 1 calc R U . . .
C22 C 0.66975(11) 0.40269(11) -0.0599(4) 0.0531(8) Uani 1 1 d . . . . .
H22 H 0.6737 0.3811 -0.1165 0.064 Uiso 1 1 calc R U . . .
C23 C 0.69378(12) 0.41963(11) 0.0773(4) 0.0552(8) Uani 1 1 d . . . . .
H23 H 0.7140 0.4095 0.1098 0.066 Uiso 1 1 calc R U . . .
C24 C 0.68837(11) 0.45101(11) 0.1661(3) 0.0490(7) Uani 1 1 d . . . . .
H24 H 0.7044 0.4620 0.2580 0.059 Uiso 1 1 calc R U . . .
C25 C 0.65800(9) 0.46587(9) 0.1140(3) 0.0391(6) Uani 1 1 d . . . . .


_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 C3 1.228(3) . ?
O2 C1 1.362(3) . ?
O2 C5 1.381(3) . ?
N1 C25 1.391(3) . ?
N1 C14 1.403(4) . ?
N1 C11 1.431(3) . ?
C1 C2 1.319(4) . ?
C1 C7 1.494(4) . ?
C2 C3 1.451(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.474(4) . ?
C4 C5 1.339(4) . ?
C4 C8 1.490(4) . ?
C5 C6 1.487(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.388(4) . ?
C8 C13 1.390(4) . ?
C9 C10 1.381(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(4) . ?
C12 C13 1.377(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.382(4) . ?
C14 C19 1.404(4) . ?
C15 C16 1.373(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.396(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.371(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.387(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.438(4) . ?
C20 C21 1.392(4) . ?
C20 C25 1.410(4) . ?
C21 C22 1.374(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.391(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.377(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.396(4) . ?
C24 H24 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
C1 O2 C5 119.7(2) . . ?
C25 N1 C14 108.4(2) . . ?
C25 N1 C11 125.8(2) . . ?
C14 N1 C11 125.8(2) . . ?
C2 C1 O2 121.9(3) . . ?
C2 C1 C7 127.4(3) . . ?
O2 C1 C7 110.6(2) . . ?
C1 C2 C3 121.7(3) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
O1 C3 C2 122.4(3) . . ?
O1 C3 C4 122.8(3) . . ?
C2 C3 C4 114.8(2) . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 C8 121.9(3) . . ?
C3 C4 C8 118.6(2) . . ?
C4 C5 O2 122.3(3) . . ?
C4 C5 C6 128.7(3) . . ?
O2 C5 C6 109.0(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 117.8(3) . . ?
C9 C8 C4 119.5(2) . . ?
C13 C8 C4 122.8(2) . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.5(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 119.2(2) . . ?
C12 C11 N1 120.9(2) . . ?
C10 C11 N1 119.8(2) . . ?
C13 C12 C11 120.0(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C8 121.6(3) . . ?
C12 C13 H13 119.2 . . ?
C8 C13 H13 119.2 . . ?
C15 C14 N1 130.0(2) . . ?
C15 C14 C19 121.3(3) . . ?
N1 C14 C19 108.6(2) . . ?
C16 C15 C14 118.1(3) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
C15 C16 C17 121.4(3) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 119.4(3) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C18 C19 C14 119.5(3) . . ?
C18 C19 C20 133.4(3) . . ?
C14 C19 C20 107.2(2) . . ?
C21 C20 C25 119.6(3) . . ?
C21 C20 C19 133.3(3) . . ?
C25 C20 C19 107.1(2) . . ?
C22 C21 C20 119.4(3) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C23 120.5(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 121.7(3) . . ?
C24 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
C23 C24 C25 117.9(3) . . ?
C23 C24 H24 121.1 . . ?
C25 C24 H24 121.1 . . ?
N1 C25 C24 130.4(2) . . ?
N1 C25 C20 108.7(2) . . ?
C24 C25 C20 120.9(2) . . ?

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
C5 O2 C1 C2 3.5(4) . . . . ?
C5 O2 C1 C7 -175.0(3) . . . . ?
O2 C1 C2 C3 -5.0(4) . . . . ?
C7 C1 C2 C3 173.3(3) . . . . ?
C1 C2 C3 O1 -176.6(3) . . . . ?
C1 C2 C3 C4 2.7(4) . . . . ?
O1 C3 C4 C5 -179.8(3) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
O1 C3 C4 C8 2.6(4) . . . . ?
C2 C3 C4 C8 -176.6(2) . . . . ?
C3 C4 C5 O2 -2.3(4) . . . . ?
C8 C4 C5 O2 175.1(2) . . . . ?
C3 C4 C5 C6 179.3(3) . . . . ?
C8 C4 C5 C6 -3.3(5) . . . . ?
C1 O2 C5 C4 0.2(4) . . . . ?
C1 O2 C5 C6 178.9(3) . . . . ?
C5 C4 C8 C9 -124.1(3) . . . . ?
C3 C4 C8 C9 53.4(4) . . . . ?
C5 C4 C8 C13 56.3(4) . . . . ?
C3 C4 C8 C13 -126.2(3) . . . . ?
C13 C8 C9 C10 -1.4(4) . . . . ?
C4 C8 C9 C10 179.0(3) . . . . ?
C8 C9 C10 C11 1.6(5) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C9 C10 C11 N1 179.2(3) . . . . ?
C25 N1 C11 C12 -45.5(4) . . . . ?
C14 N1 C11 C12 130.9(3) . . . . ?
C25 N1 C11 C10 134.8(3) . . . . ?
C14 N1 C11 C10 -48.8(4) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
N1 C11 C12 C13 179.4(3) . . . . ?
C11 C12 C13 C8 1.1(4) . . . . ?
C9 C8 C13 C12 0.1(4) . . . . ?
C4 C8 C13 C12 179.7(3) . . . . ?
C25 N1 C14 C15 179.2(3) . . . . ?
C11 N1 C14 C15 2.3(5) . . . . ?
C25 N1 C14 C19 0.9(3) . . . . ?
C11 N1 C14 C19 -176.0(2) . . . . ?
N1 C14 C15 C16 -179.1(3) . . . . ?
C19 C14 C15 C16 -1.0(4) . . . . ?
C14 C15 C16 C17 0.3(5) . . . . ?
C15 C16 C17 C18 0.2(5) . . . . ?
C16 C17 C18 C19 0.1(5) . . . . ?
C17 C18 C19 C14 -0.8(4) . . . . ?
C17 C18 C19 C20 179.2(3) . . . . ?
C15 C14 C19 C18 1.2(4) . . . . ?
N1 C14 C19 C18 179.7(2) . . . . ?
C15 C14 C19 C20 -178.7(3) . . . . ?
N1 C14 C19 C20 -0.3(3) . . . . ?
C18 C19 C20 C21 0.9(5) . . . . ?
C14 C19 C20 C21 -179.1(3) . . . . ?
C18 C19 C20 C25 179.6(3) . . . . ?
C14 C19 C20 C25 -0.4(3) . . . . ?
C25 C20 C21 C22 -0.7(4) . . . . ?
C19 C20 C21 C22 177.8(3) . . . . ?
C20 C21 C22 C23 -0.5(4) . . . . ?
C21 C22 C23 C24 1.1(5) . . . . ?
C22 C23 C24 C25 -0.4(5) . . . . ?
C14 N1 C25 C24 177.1(3) . . . . ?
C11 N1 C25 C24 -6.0(4) . . . . ?
C14 N1 C25 C20 -1.2(3) . . . . ?
C11 N1 C25 C20 175.7(2) . . . . ?
C23 C24 C25 N1 -178.9(3) . . . . ?
C23 C24 C25 C20 -0.8(4) . . . . ?
C21 C20 C25 N1 179.9(2) . . . . ?
C19 C20 C25 N1 1.0(3) . . . . ?
C21 C20 C25 C24 1.4(4) . . . . ?
C19 C20 C25 C24 -177.5(2) . . . . ?

_refine_diff_density_max         0.109
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.027

_shelxl_version_number           2013-4

