# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_dd18272_0m
_database_code_depnum_ccdc_archive 'CCDC 2245980'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2023-03-03 deposited with the CCDC.	2023-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H25 N3 O'
_chemical_formula_weight         371.47

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   6.8819(4)
_cell_length_b                   18.2382(10)
_cell_length_c                   8.3735(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.220(2)
_cell_angle_gamma                90
_cell_volume                     1030.90(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6077
_cell_measurement_theta_min      6.035
_cell_measurement_theta_max      54.847

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6356
_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            10712
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.480
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_point_group_measured_fraction_full 0.906
_reflns_number_total             3649
_reflns_number_gt                3304
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_max     0.804
_reflns_Friedel_fraction_full    0.821

_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)+(0.0364P)²+0.0906P] 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       0.084(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1282 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.1(5)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3649
_refine_ls_number_parameters     256
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0839
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.002
_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 0.5432(2) 0.46842(8) 0.74732(16) 0.0453(4) Uani 1 1 d . . . . .
N1 N 0.9242(3) 0.65527(10) 0.7287(2) 0.0513(5) Uani 1 1 d . . . . .
N2 N 0.1896(3) 0.41760(16) 0.9560(3) 0.0823(8) Uani 1 1 d . . . . .
N3 N 0.8118(2) 0.54687(10) 0.59834(19) 0.0442(4) Uani 1 1 d . . . . .
C1 C 0.9109(4) 0.71127(13) 0.8342(3) 0.0545(6) Uani 1 1 d . . . . .
C2 C 0.7682(4) 0.71369(13) 0.9251(3) 0.0563(6) Uani 1 1 d . . . . .
H2 H 0.7566 0.7547 0.9886 0.068 Uiso 1 1 calc R U . . .
C3 C 0.6371(3) 0.65388(12) 0.9235(3) 0.0482(5) Uani 1 1 d . . . . .
C4 C 0.4934(4) 0.65399(14) 1.0228(3) 0.0556(6) Uani 1 1 d . . . . .
H4 H 0.4824 0.6950 1.0864 0.067 Uiso 1 1 calc R U . . .
C5 C 0.3702(3) 0.59608(14) 1.0287(3) 0.0524(6) Uani 1 1 d . . . . .
C6 C 0.3967(3) 0.53361(13) 0.9351(2) 0.0463(5) Uani 1 1 d . . . . .
C7 C 0.5346(3) 0.53138(12) 0.8348(2) 0.0420(5) Uani 1 1 d . . . . .
C8 C 0.6549(3) 0.59324(12) 0.8207(2) 0.0417(5) Uani 1 1 d . . . . .
C9 C 0.7989(3) 0.59998(12) 0.7162(2) 0.0422(5) Uani 1 1 d . . . . .
C10 C 1.0593(5) 0.77190(16) 0.8368(4) 0.0780(8) Uani 1 1 d . . . . .
H10A H 1.1908 0.7519 0.8612 0.117 Uiso 1 1 calc R U . . .
H10B H 1.0437 0.8071 0.9187 0.117 Uiso 1 1 calc R U . . .
H10C H 1.0381 0.7954 0.7323 0.117 Uiso 1 1 calc R U . . .
C11 C 0.2124(4) 0.59711(18) 1.1302(3) 0.0705(7) Uani 1 1 d . . . . .
H11A H 0.2087 0.6446 1.1789 0.106 Uiso 1 1 calc R U . . .
H11B H 0.2417 0.5607 1.2142 0.106 Uiso 1 1 calc R U . . .
H11C H 0.0861 0.5867 1.0625 0.106 Uiso 1 1 calc R U . . .
C12 C 0.2802(3) 0.46904(16) 0.9447(3) 0.0556(6) Uani 1 1 d . . . . .
C13 C 0.6364(3) 0.54187(13) 0.4660(2) 0.0490(5) Uani 1 1 d . . . . .
H13A H 0.6324 0.5841 0.3951 0.059 Uiso 1 1 calc R U . . .
H13B H 0.5174 0.5423 0.5119 0.059 Uiso 1 1 calc R U . . .
C14 C 0.6413(4) 0.47274(14) 0.3680(3) 0.0580(6) Uani 1 1 d . . . . .
H14A H 0.5281 0.4718 0.2785 0.070 Uiso 1 1 calc R U . . .
H14B H 0.6331 0.4303 0.4363 0.070 Uiso 1 1 calc R U . . .
C15 C 0.8312(4) 0.46920(17) 0.3015(3) 0.0674(7) Uani 1 1 d . . . . .
H15A H 0.8384 0.4227 0.2469 0.081 Uiso 1 1 calc R U . . .
H15B H 0.8319 0.5081 0.2226 0.081 Uiso 1 1 calc R U . . .
C16 C 1.0076(4) 0.47726(15) 0.4382(3) 0.0633(7) Uani 1 1 d . . . . .
H16A H 1.1279 0.4776 0.3941 0.076 Uiso 1 1 calc R U . . .
H16B H 1.0137 0.4357 0.5113 0.076 Uiso 1 1 calc R U . . .
C17 C 0.9945(4) 0.54773(14) 0.5324(3) 0.0558(6) Uani 1 1 d . . . . .
H17A H 1.1085 0.5518 0.6206 0.067 Uiso 1 1 calc R U . . .
H17B H 0.9940 0.5896 0.4610 0.067 Uiso 1 1 calc R U . . .
C18 C 0.6764(3) 0.41328(13) 0.8283(3) 0.0568(6) Uani 1 1 d . . . . .
H18A H 0.6420 0.4006 0.9319 0.068 Uiso 1 1 calc R U . . .
H18B H 0.8113 0.4315 0.8487 0.068 Uiso 1 1 calc R U . . .
C19 C 0.6588(4) 0.34728(12) 0.7205(3) 0.0501(6) Uani 1 1 d . . . . .
C20 C 0.4749(4) 0.31972(15) 0.6490(3) 0.0704(7) Uani 1 1 d . . . . .
H20 H 0.3606 0.3409 0.6721 0.084 Uiso 1 1 calc R U . . .
C21 C 0.4609(6) 0.26125(18) 0.5441(4) 0.0906(11) Uani 1 1 d . . . . .
H21 H 0.3369 0.2433 0.4958 0.109 Uiso 1 1 calc R U . . .
C22 C 0.6277(7) 0.22919(18) 0.5101(4) 0.0943(11) Uani 1 1 d . . . . .
H22 H 0.6169 0.1900 0.4379 0.113 Uiso 1 1 calc R U . . .
C23 C 0.8089(6) 0.25460(16) 0.5819(4) 0.0803(9) Uani 1 1 d . . . . .
H23 H 0.9223 0.2320 0.5605 0.096 Uiso 1 1 calc R U . . .
C24 C 0.8261(4) 0.31376(13) 0.6865(3) 0.0599(6) Uani 1 1 d . . . . .
H24 H 0.9510 0.3311 0.7344 0.072 Uiso 1 1 calc R 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
O1 C7 1.370(2) . ?
O1 C18 1.439(3) . ?
N1 C9 1.317(3) . ?
N1 C1 1.364(3) . ?
N2 C12 1.141(3) . ?
N3 C9 1.398(3) . ?
N3 C17 1.468(3) . ?
N3 C13 1.474(3) . ?
C1 C2 1.356(3) . ?
C1 C10 1.502(3) . ?
C2 C3 1.414(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.410(3) . ?
C3 C8 1.422(3) . ?
C4 C5 1.361(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.415(3) . ?
C5 C11 1.504(3) . ?
C6 C7 1.384(3) . ?
C6 C12 1.436(3) . ?
C7 C8 1.418(3) . ?
C8 C9 1.449(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.508(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.519(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.505(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.520(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.496(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C24 1.381(4) . ?
C19 C20 1.385(3) . ?
C20 C21 1.373(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.366(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.356(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.380(4) . ?
C23 H23 0.9300 . ?
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
C7 O1 C18 115.07(15) . . ?
C9 N1 C1 119.97(18) . . ?
C9 N3 C17 115.76(18) . . ?
C9 N3 C13 114.75(16) . . ?
C17 N3 C13 110.71(16) . . ?
C2 C1 N1 122.3(2) . . ?
C2 C1 C10 122.1(2) . . ?
N1 C1 C10 115.5(2) . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 C8 120.7(2) . . ?
C2 C3 C8 118.43(19) . . ?
C5 C4 C3 122.2(2) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 C6 117.14(19) . . ?
C4 C5 C11 122.3(2) . . ?
C6 C5 C11 120.6(2) . . ?
C7 C6 C5 122.5(2) . . ?
C7 C6 C12 117.8(2) . . ?
C5 C6 C12 119.73(19) . . ?
O1 C7 C6 117.08(19) . . ?
O1 C7 C8 122.39(17) . . ?
C6 C7 C8 120.49(19) . . ?
C7 C8 C3 116.61(17) . . ?
C7 C8 C9 126.66(18) . . ?
C3 C8 C9 116.69(18) . . ?
N1 C9 N3 117.15(17) . . ?
N1 C9 C8 122.04(19) . . ?
N3 C9 C8 120.80(18) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C6 178.4(3) . . ?
N3 C13 C14 111.06(18) . . ?
N3 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
N3 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 110.3(2) . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 109.96(19) . . ?
C16 C15 H15A 109.7 . . ?
C14 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C15 C16 C17 110.9(2) . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.0 . . ?
N3 C17 C16 109.1(2) . . ?
N3 C17 H17A 109.9 . . ?
C16 C17 H17A 109.9 . . ?
N3 C17 H17B 109.9 . . ?
C16 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
O1 C18 C19 107.97(17) . . ?
O1 C18 H18A 110.1 . . ?
C19 C18 H18A 110.1 . . ?
O1 C18 H18B 110.1 . . ?
C19 C18 H18B 110.1 . . ?
H18A C18 H18B 108.4 . . ?
C24 C19 C20 118.6(2) . . ?
C24 C19 C18 120.5(2) . . ?
C20 C19 C18 120.8(2) . . ?
C21 C20 C19 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 120.6(3) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C21 119.9(3) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 120.4(3) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C19 120.3(3) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?

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
C9 N1 C1 C2 -2.0(3) . . . . ?
C9 N1 C1 C10 -179.2(2) . . . . ?
N1 C1 C2 C3 5.6(4) . . . . ?
C10 C1 C2 C3 -177.4(2) . . . . ?
C1 C2 C3 C4 177.2(2) . . . . ?
C1 C2 C3 C8 -2.1(3) . . . . ?
C2 C3 C4 C5 -177.4(2) . . . . ?
C8 C3 C4 C5 1.9(3) . . . . ?
C3 C4 C5 C6 2.4(3) . . . . ?
C3 C4 C5 C11 -177.9(2) . . . . ?
C4 C5 C6 C7 -3.0(3) . . . . ?
C11 C5 C6 C7 177.3(2) . . . . ?
C4 C5 C6 C12 175.9(2) . . . . ?
C11 C5 C6 C12 -3.8(3) . . . . ?
C18 O1 C7 C6 -89.3(2) . . . . ?
C18 O1 C7 C8 93.0(2) . . . . ?
C5 C6 C7 O1 -178.48(18) . . . . ?
C12 C6 C7 O1 2.6(3) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C12 C6 C7 C8 -179.70(19) . . . . ?
O1 C7 C8 C3 -177.44(18) . . . . ?
C6 C7 C8 C3 4.9(3) . . . . ?
O1 C7 C8 C9 0.3(3) . . . . ?
C6 C7 C8 C9 -177.33(19) . . . . ?
C4 C3 C8 C7 -5.5(3) . . . . ?
C2 C3 C8 C7 173.77(19) . . . . ?
C4 C3 C8 C9 176.50(19) . . . . ?
C2 C3 C8 C9 -4.2(3) . . . . ?
C1 N1 C9 N3 175.82(19) . . . . ?
C1 N1 C9 C8 -5.0(3) . . . . ?
C17 N3 C9 N1 15.8(3) . . . . ?
C13 N3 C9 N1 -115.2(2) . . . . ?
C17 N3 C9 C8 -163.47(19) . . . . ?
C13 N3 C9 C8 65.6(2) . . . . ?
C7 C8 C9 N1 -169.79(19) . . . . ?
C3 C8 C9 N1 7.9(3) . . . . ?
C7 C8 C9 N3 9.4(3) . . . . ?
C3 C8 C9 N3 -172.88(18) . . . . ?
C9 N3 C13 C14 -166.50(18) . . . . ?
C17 N3 C13 C14 60.2(2) . . . . ?
N3 C13 C14 C15 -56.5(2) . . . . ?
C13 C14 C15 C16 54.3(3) . . . . ?
C14 C15 C16 C17 -56.1(3) . . . . ?
C9 N3 C17 C16 166.76(18) . . . . ?
C13 N3 C17 C16 -60.4(2) . . . . ?
C15 C16 C17 N3 59.0(2) . . . . ?
C7 O1 C18 C19 176.83(18) . . . . ?
O1 C18 C19 C24 130.8(2) . . . . ?
O1 C18 C19 C20 -47.4(3) . . . . ?
C24 C19 C20 C21 -1.4(4) . . . . ?
C18 C19 C20 C21 176.9(3) . . . . ?
C19 C20 C21 C22 0.6(5) . . . . ?
C20 C21 C22 C23 0.8(5) . . . . ?
C21 C22 C23 C24 -1.4(5) . . . . ?
C22 C23 C24 C19 0.6(4) . . . . ?
C20 C19 C24 C23 0.8(4) . . . . ?
C18 C19 C24 C23 -177.5(2) . . . . ?

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
C18 H18B N2 0.97 2.60 3.486(3) 152.8 1_655
C13 H13B O1 0.97 2.37 2.889(3) 113.1 .
C13 H13B O1 0.97 2.37 2.889(3) 113.1 .
C18 H18B N2 0.97 2.60 3.486(3) 152.8 1_655
C13 H13B O1 0.97 2.37 2.889(3) 113.1 .
C18 H18B N2 0.97 2.60 3.486(3) 152.8 1_655

_refine_diff_density_max         0.113
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.020

_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_dd18273
_database_code_depnum_ccdc_archive 'CCDC 2245982'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2023-03-03 deposited with the CCDC.	2023-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 F N3 O'
_chemical_formula_weight         389.46

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   19.673(7)
_cell_length_b                   7.589(2)
_cell_length_c                   27.281(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4073(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1936
_cell_measurement_theta_min      5.102
_cell_measurement_theta_max      54.675

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             1648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4468
_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            16722
_diffrn_reflns_av_unetI/netI     0.1242
_diffrn_reflns_av_R_equivalents  0.1441
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.553
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             3565
_reflns_number_gt                1580
_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)+(0.0871P)²] 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       0.0116(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3565
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1827
_refine_ls_R_factor_gt           0.0749
_refine_ls_wR_factor_ref         0.2194
_refine_ls_wR_factor_gt          0.1566
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
F1 F 0.31965(17) -0.0568(4) -0.09821(10) 0.1094(12) Uani 1 1 d . . . . .
O1 O 0.46537(14) 0.2436(3) 0.08559(9) 0.0534(8) Uani 1 1 d . . . . .
N1 N 0.3578(2) 0.3337(4) 0.21781(12) 0.0662(11) Uani 1 1 d . . . . .
N2 N 0.6125(2) 0.3734(6) 0.03115(19) 0.0924(15) Uani 1 1 d . . . . .
N3 N 0.3805(2) 0.1091(4) 0.16307(12) 0.0565(10) Uani 1 1 d . . . . .
C1 C 0.3784(4) 0.4767(6) 0.24385(16) 0.0767(17) Uani 1 1 d . . . . .
C2 C 0.4419(4) 0.5430(6) 0.24007(17) 0.0780(17) Uani 1 1 d . . . . .
H2 H 0.4572 0.6253 0.2628 0.094 Uiso 1 1 calc R U . . .
C3 C 0.4856(3) 0.4869(5) 0.20136(17) 0.0676(15) Uani 1 1 d . . . . .
C4 C 0.5508(4) 0.5578(6) 0.1932(2) 0.0834(18) Uani 1 1 d . . . . .
H4 H 0.5692 0.6337 0.2164 0.100 Uiso 1 1 calc R U . . .
C5 C 0.5878(3) 0.5190(6) 0.1524(2) 0.0761(15) Uani 1 1 d . . . . .
C6 C 0.5559(3) 0.4139(5) 0.11560(17) 0.0642(13) Uani 1 1 d . . . . .
C7 C 0.4938(3) 0.3375(5) 0.12398(15) 0.0554(12) Uani 1 1 d . . . . .
C8 C 0.4590(3) 0.3578(5) 0.16893(14) 0.0558(12) Uani 1 1 d . . . . .
C9 C 0.3981(3) 0.2667(5) 0.18415(14) 0.0544(12) Uani 1 1 d . . . . .
C10 C 0.3265(3) 0.5530(7) 0.27845(17) 0.109(2) Uani 1 1 d . . . . .
H10A H 0.2919 0.6128 0.2600 0.163 Uiso 1 1 calc R U . . .
H10B H 0.3483 0.6350 0.3002 0.163 Uiso 1 1 calc R U . . .
H10C H 0.3062 0.4599 0.2972 0.163 Uiso 1 1 calc R U . . .
C11 C 0.6593(3) 0.5855(8) 0.1448(2) 0.116(2) Uani 1 1 d . . . . .
H11A H 0.6897 0.4872 0.1413 0.174 Uiso 1 1 calc R U . . .
H11B H 0.6728 0.6549 0.1726 0.174 Uiso 1 1 calc R U . . .
H11C H 0.6610 0.6567 0.1158 0.174 Uiso 1 1 calc R U . . .
C12 C 0.5880(3) 0.3907(6) 0.0683(2) 0.0725(15) Uani 1 1 d . . . . .
C13 C 0.4322(2) -0.0275(5) 0.15527(15) 0.0593(13) Uani 1 1 d . . . . .
H13A H 0.4377 -0.0954 0.1851 0.071 Uiso 1 1 calc R U . . .
H13B H 0.4754 0.0278 0.1478 0.071 Uiso 1 1 calc R U . . .
C14 C 0.4126(2) -0.1502(5) 0.11362(15) 0.0610(13) Uani 1 1 d . . . . .
H14A H 0.4134 -0.0855 0.0830 0.073 Uiso 1 1 calc R U . . .
H14B H 0.4457 -0.2447 0.1114 0.073 Uiso 1 1 calc R U . . .
C15 C 0.3426(3) -0.2277(6) 0.12139(17) 0.0727(15) Uani 1 1 d . . . . .
H15A H 0.3439 -0.3099 0.1486 0.087 Uiso 1 1 calc R U . . .
H15B H 0.3289 -0.2919 0.0923 0.087 Uiso 1 1 calc R U . . .
C16 C 0.2913(3) -0.0834(6) 0.13207(17) 0.0700(14) Uani 1 1 d . . . . .
H16A H 0.2855 -0.0111 0.1031 0.084 Uiso 1 1 calc R U . . .
H16B H 0.2478 -0.1363 0.1399 0.084 Uiso 1 1 calc R U . . .
C17 C 0.3138(2) 0.0316(6) 0.17432(16) 0.0663(14) Uani 1 1 d . . . . .
H17A H 0.2808 0.1246 0.1797 0.080 Uiso 1 1 calc R U . . .
H17B H 0.3168 -0.0383 0.2040 0.080 Uiso 1 1 calc R U . . .
C18 C 0.4122(3) 0.3401(5) 0.06095(15) 0.0686(14) Uani 1 1 d . . . . .
H18A H 0.4296 0.4520 0.0492 0.082 Uiso 1 1 calc R U . . .
H18B H 0.3752 0.3635 0.0835 0.082 Uiso 1 1 calc R U . . .
C19 C 0.3874(3) 0.2321(5) 0.01890(14) 0.0563(12) Uani 1 1 d . . . . .
C20 C 0.4321(3) 0.1643(5) -0.01502(16) 0.0649(13) Uani 1 1 d . . . . .
H20 H 0.4784 0.1848 -0.0113 0.078 Uiso 1 1 calc R U . . .
C21 C 0.4097(3) 0.0670(6) -0.05424(17) 0.0726(15) Uani 1 1 d . . . . .
H21 H 0.4403 0.0204 -0.0768 0.087 Uiso 1 1 calc R U . . .
C22 C 0.3418(4) 0.0405(6) -0.05926(16) 0.0734(16) Uani 1 1 d . . . . .
C23 C 0.2958(3) 0.1046(6) -0.02770(17) 0.0709(14) Uani 1 1 d . . . . .
H23 H 0.2496 0.0848 -0.0323 0.085 Uiso 1 1 calc R U . . .
C24 C 0.3190(3) 0.2005(6) 0.01171(15) 0.0674(14) Uani 1 1 d . . . . .
H24 H 0.2878 0.2451 0.0341 0.081 Uiso 1 1 calc R 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
F1 C22 1.366(5) . ?
O1 C7 1.385(4) . ?
O1 C18 1.443(4) . ?
N1 C9 1.316(5) . ?
N1 C1 1.359(6) . ?
N2 C12 1.130(6) . ?
N3 C9 1.371(5) . ?
N3 C13 1.467(5) . ?
N3 C17 1.471(5) . ?
C1 C2 1.352(7) . ?
C1 C10 1.506(7) . ?
C2 C3 1.426(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.409(7) . ?
C3 C8 1.420(5) . ?
C4 C5 1.362(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.427(6) . ?
C5 C11 1.509(7) . ?
C6 C7 1.372(6) . ?
C6 C12 1.448(7) . ?
C7 C8 1.413(6) . ?
C8 C9 1.444(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.518(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.512(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.517(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.512(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.492(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.375(6) . ?
C19 C24 1.382(6) . ?
C20 C21 1.372(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.358(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.341(6) . ?
C23 C24 1.376(6) . ?
C23 H23 0.9300 . ?
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
C7 O1 C18 112.6(3) . . ?
C9 N1 C1 119.6(5) . . ?
C9 N3 C13 120.2(4) . . ?
C9 N3 C17 119.1(4) . . ?
C13 N3 C17 111.4(3) . . ?
C2 C1 N1 122.2(5) . . ?
C2 C1 C10 122.1(5) . . ?
N1 C1 C10 115.6(6) . . ?
C1 C2 C3 120.2(5) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C8 120.0(5) . . ?
C4 C3 C2 123.5(5) . . ?
C8 C3 C2 116.5(5) . . ?
C5 C4 C3 122.3(5) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 C6 117.4(5) . . ?
C4 C5 C11 122.5(5) . . ?
C6 C5 C11 120.0(6) . . ?
C7 C6 C5 120.7(5) . . ?
C7 C6 C12 119.0(4) . . ?
C5 C6 C12 120.3(5) . . ?
C6 C7 O1 116.8(4) . . ?
C6 C7 C8 122.0(4) . . ?
O1 C7 C8 121.1(4) . . ?
C7 C8 C3 115.9(5) . . ?
C7 C8 C9 126.8(4) . . ?
C3 C8 C9 117.2(4) . . ?
N1 C9 N3 118.5(4) . . ?
N1 C9 C8 121.1(4) . . ?
N3 C9 C8 120.4(4) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C6 179.4(7) . . ?
N3 C13 C14 111.5(4) . . ?
N3 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N3 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 C13 111.4(4) . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C16 110.6(4) . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C15 111.6(4) . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
N3 C17 C16 109.4(4) . . ?
N3 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
N3 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
O1 C18 C19 108.4(3) . . ?
O1 C18 H18A 110.0 . . ?
C19 C18 H18A 110.0 . . ?
O1 C18 H18B 110.0 . . ?
C19 C18 H18B 110.0 . . ?
H18A C18 H18B 108.4 . . ?
C20 C19 C24 117.5(4) . . ?
C20 C19 C18 121.0(5) . . ?
C24 C19 C18 121.5(4) . . ?
C21 C20 C19 121.4(5) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C22 C21 C20 118.3(5) . . ?
C22 C21 H21 120.9 . . ?
C20 C21 H21 120.9 . . ?
C23 C22 C21 123.1(4) . . ?
C23 C22 F1 118.7(6) . . ?
C21 C22 F1 118.2(5) . . ?
C22 C23 C24 117.9(5) . . ?
C22 C23 H23 121.0 . . ?
C24 C23 H23 121.0 . . ?
C23 C24 C19 121.8(4) . . ?
C23 C24 H24 119.1 . . ?
C19 C24 H24 119.1 . . ?

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
C9 N1 C1 C2 -6.9(6) . . . . ?
C9 N1 C1 C10 175.0(4) . . . . ?
N1 C1 C2 C3 12.7(7) . . . . ?
C10 C1 C2 C3 -169.4(4) . . . . ?
C1 C2 C3 C4 175.9(4) . . . . ?
C1 C2 C3 C8 -1.5(6) . . . . ?
C8 C3 C4 C5 6.1(7) . . . . ?
C2 C3 C4 C5 -171.2(4) . . . . ?
C3 C4 C5 C6 5.0(7) . . . . ?
C3 C4 C5 C11 -176.2(4) . . . . ?
C4 C5 C6 C7 -7.9(6) . . . . ?
C11 C5 C6 C7 173.2(4) . . . . ?
C4 C5 C6 C12 170.3(4) . . . . ?
C11 C5 C6 C12 -8.6(7) . . . . ?
C5 C6 C7 O1 177.5(4) . . . . ?
C12 C6 C7 O1 -0.8(6) . . . . ?
C5 C6 C7 C8 -0.4(6) . . . . ?
C12 C6 C7 C8 -178.6(4) . . . . ?
C18 O1 C7 C6 -102.6(4) . . . . ?
C18 O1 C7 C8 75.3(4) . . . . ?
C6 C7 C8 C3 11.2(6) . . . . ?
O1 C7 C8 C3 -166.6(3) . . . . ?
C6 C7 C8 C9 -171.6(4) . . . . ?
O1 C7 C8 C9 10.6(6) . . . . ?
C4 C3 C8 C7 -13.9(6) . . . . ?
C2 C3 C8 C7 163.6(4) . . . . ?
C4 C3 C8 C9 168.6(4) . . . . ?
C2 C3 C8 C9 -13.9(5) . . . . ?
C1 N1 C9 N3 171.2(3) . . . . ?
C1 N1 C9 C8 -9.9(6) . . . . ?
C13 N3 C9 N1 -136.6(4) . . . . ?
C17 N3 C9 N1 7.2(5) . . . . ?
C13 N3 C9 C8 44.5(5) . . . . ?
C17 N3 C9 C8 -171.7(4) . . . . ?
C7 C8 C9 N1 -156.9(4) . . . . ?
C3 C8 C9 N1 20.3(6) . . . . ?
C7 C8 C9 N3 21.9(6) . . . . ?
C3 C8 C9 N3 -160.9(3) . . . . ?
C9 N3 C13 C14 -154.9(3) . . . . ?
C17 N3 C13 C14 58.8(4) . . . . ?
N3 C13 C14 C15 -54.0(4) . . . . ?
C13 C14 C15 C16 51.2(5) . . . . ?
C14 C15 C16 C17 -53.8(5) . . . . ?
C9 N3 C17 C16 153.2(3) . . . . ?
C13 N3 C17 C16 -60.1(4) . . . . ?
C15 C16 C17 N3 57.8(5) . . . . ?
C7 O1 C18 C19 177.2(4) . . . . ?
O1 C18 C19 C20 -51.9(5) . . . . ?
O1 C18 C19 C24 129.9(4) . . . . ?
C24 C19 C20 C21 -0.8(6) . . . . ?
C18 C19 C20 C21 -179.0(4) . . . . ?
C19 C20 C21 C22 0.8(7) . . . . ?
C20 C21 C22 C23 -0.2(7) . . . . ?
C20 C21 C22 F1 -179.8(4) . . . . ?
C21 C22 C23 C24 -0.5(7) . . . . ?
F1 C22 C23 C24 179.2(4) . . . . ?
C22 C23 C24 C19 0.5(7) . . . . ?
C20 C19 C24 C23 0.1(6) . . . . ?
C18 C19 C24 C23 178.4(4) . . . . ?

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
C18 H18A N2 0.97 2.69 3.358(6) 126.2 5_665
C13 H13B O1 0.97 2.37 2.876(5) 112.1 .
C18 H18A N2 0.97 2.69 3.358(6) 126.2 5_665
C13 H13B O1 0.97 2.37 2.876(5) 112.1 .
C13 H13B O1 0.97 2.37 2.876(5) 112.1 .
C18 H18A N2 0.97 2.69 3.358(6) 126.2 5_665

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.051

_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_dd18275_0m
_database_code_depnum_ccdc_archive 'CCDC 2245984'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2023-03-03 deposited with the CCDC.	2023-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 Br N3 O'
_chemical_formula_weight         450.37

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   21.3712(7)
_cell_length_b                   10.6818(3)
_cell_length_c                   19.0014(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.4240(10)
_cell_angle_gamma                90
_cell_volume                     4301.3(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5468
_cell_measurement_theta_min      4.897
_cell_measurement_theta_max      52.131

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             1856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.931
_shelx_estimated_absorpt_T_min   0.748
_shelx_estimated_absorpt_T_max   0.787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5593
_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            20532
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.336
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3993
_reflns_number_gt                2597
_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)+(0.0598P)²+6.0961P] 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       0.0036(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3993
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1504
_refine_ls_wR_factor_gt          0.1295
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.005
_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 0.76648(2) 0.48714(7) 0.81844(2) 0.1284(4) Uani 1 1 d . . . . .
O1 O 0.63412(10) 0.52128(19) 0.47902(11) 0.0590(6) Uani 1 1 d . . . . .
N1 N 0.58301(13) 0.2406(3) 0.32025(14) 0.0654(7) Uani 1 1 d . . . . .
N2 N 0.6563(2) 0.8326(3) 0.4880(2) 0.1065(13) Uani 1 1 d . . . . .
N3 N 0.58360(13) 0.2809(2) 0.43998(13) 0.0613(7) Uani 1 1 d . . . . .
C1 C 0.57987(16) 0.2787(4) 0.25147(18) 0.0707(10) Uani 1 1 d . . . . .
C2 C 0.57675(16) 0.4017(4) 0.23294(18) 0.0741(10) Uani 1 1 d . . . . .
H2 H 0.5691 0.4244 0.1854 0.089 Uiso 1 1 calc R U . . .
C3 C 0.58515(16) 0.4947(3) 0.28581(19) 0.0645(9) Uani 1 1 d . . . . .
C4 C 0.58568(17) 0.6238(4) 0.2691(2) 0.0754(10) Uani 1 1 d . . . . .
H4 H 0.5762 0.6479 0.2219 0.090 Uiso 1 1 calc R U . . .
C5 C 0.59947(17) 0.7140(4) 0.3190(2) 0.0735(10) Uani 1 1 d . . . . .
C6 C 0.61692(16) 0.6740(3) 0.38986(19) 0.0653(9) Uani 1 1 d . . . . .
C7 C 0.61553(15) 0.5493(3) 0.40892(17) 0.0571(8) Uani 1 1 d . . . . .
C8 C 0.59506(14) 0.4559(3) 0.35831(17) 0.0557(8) Uani 1 1 d . . . . .
C9 C 0.58698(14) 0.3241(3) 0.37157(16) 0.0577(8) Uani 1 1 d . . . . .
C10 C 0.5768(2) 0.1753(4) 0.1975(2) 0.0944(13) Uani 1 1 d . . . . .
H10A H 0.6073 0.1121 0.2134 0.142 Uiso 1 1 calc R U . . .
H10B H 0.5859 0.2086 0.1529 0.142 Uiso 1 1 calc R U . . .
H10C H 0.5353 0.1392 0.1915 0.142 Uiso 1 1 calc R U . . .
C11 C 0.5977(2) 0.8519(4) 0.3010(3) 0.1028(15) Uani 1 1 d . . . . .
H11A H 0.5650 0.8919 0.3229 0.154 Uiso 1 1 calc R U . . .
H11B H 0.5895 0.8622 0.2505 0.154 Uiso 1 1 calc R U . . .
H11C H 0.6376 0.8893 0.3182 0.154 Uiso 1 1 calc R U . . .
C12 C 0.63843(19) 0.7627(4) 0.4444(2) 0.0769(10) Uani 1 1 d . . . . .
C13 C 0.53495(16) 0.3376(3) 0.47804(17) 0.0638(9) Uani 1 1 d . . . . .
H13A H 0.4941 0.3024 0.4604 0.077 Uiso 1 1 calc R U . . .
H13B H 0.5332 0.4270 0.4692 0.077 Uiso 1 1 calc R U . . .
C14 C 0.54897(19) 0.3143(3) 0.55693(18) 0.0728(10) Uani 1 1 d . . . . .
H14A H 0.5886 0.3540 0.5752 0.087 Uiso 1 1 calc R U . . .
H14B H 0.5159 0.3509 0.5808 0.087 Uiso 1 1 calc R U . . .
C15 C 0.5531(3) 0.1756(4) 0.5719(2) 0.0951(13) Uani 1 1 d . . . . .
H15A H 0.5121 0.1373 0.5591 0.114 Uiso 1 1 calc R U . . .
H15B H 0.5658 0.1617 0.6222 0.114 Uiso 1 1 calc R U . . .
C16 C 0.6008(2) 0.1167(4) 0.5293(2) 0.0958(14) Uani 1 1 d . . . . .
H16A H 0.6426 0.1478 0.5468 0.115 Uiso 1 1 calc R U . . .
H16B H 0.6009 0.0267 0.5363 0.115 Uiso 1 1 calc R U . . .
C17 C 0.5865(2) 0.1448(3) 0.45069(19) 0.0779(11) Uani 1 1 d . . . . .
H17A H 0.6192 0.1094 0.4257 0.094 Uiso 1 1 calc R U . . .
H17B H 0.5466 0.1072 0.4318 0.094 Uiso 1 1 calc R U . . .
C18 C 0.69869(16) 0.4810(4) 0.49437(18) 0.0711(10) Uani 1 1 d . . . . .
H18A H 0.7261 0.5373 0.4725 0.085 Uiso 1 1 calc R U . . .
H18B H 0.7034 0.3975 0.4757 0.085 Uiso 1 1 calc R U . . .
C19 C 0.71570(16) 0.4812(3) 0.57254(18) 0.0622(9) Uani 1 1 d . . . . .
C20 C 0.7096(2) 0.5874(4) 0.6109(2) 0.0983(14) Uani 1 1 d . . . . .
H20 H 0.6953 0.6605 0.5876 0.118 Uiso 1 1 calc R U . . .
C21 C 0.7241(2) 0.5882(5) 0.6833(2) 0.1108(17) Uani 1 1 d . . . . .
H21 H 0.7185 0.6611 0.7085 0.133 Uiso 1 1 calc R U . . .
C22 C 0.74640(18) 0.4849(5) 0.71814(19) 0.0796(12) Uani 1 1 d . . . . .
C23 C 0.7548(3) 0.3796(5) 0.6817(2) 0.1047(15) Uani 1 1 d . . . . .
H23 H 0.7713 0.3083 0.7054 0.126 Uiso 1 1 calc R U . . .
C24 C 0.7387(2) 0.3782(4) 0.6085(2) 0.0949(13) Uani 1 1 d . . . . .
H24 H 0.7438 0.3047 0.5836 0.114 Uiso 1 1 calc R 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
Br1 C22 1.899(4) . ?
O1 C7 1.373(4) . ?
O1 C18 1.439(4) . ?
N1 C9 1.316(4) . ?
N1 C1 1.362(4) . ?
N2 C12 1.144(5) . ?
N3 C9 1.390(4) . ?
N3 C17 1.468(4) . ?
N3 C13 1.471(4) . ?
C1 C2 1.359(5) . ?
C1 C10 1.504(5) . ?
C2 C3 1.407(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.416(5) . ?
C3 C8 1.428(5) . ?
C4 C5 1.357(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.416(5) . ?
C5 C11 1.511(5) . ?
C6 C7 1.382(5) . ?
C6 C12 1.435(6) . ?
C7 C8 1.415(5) . ?
C8 C9 1.444(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.511(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.509(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.519(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.516(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.483(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C24 1.354(5) . ?
C19 C20 1.364(5) . ?
C20 C21 1.371(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.341(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.345(6) . ?
C23 C24 1.391(5) . ?
C23 H23 0.9300 . ?
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
C7 O1 C18 114.3(2) . . ?
C9 N1 C1 119.9(3) . . ?
C9 N3 C17 116.9(3) . . ?
C9 N3 C13 116.6(3) . . ?
C17 N3 C13 111.1(3) . . ?
C2 C1 N1 122.2(3) . . ?
C2 C1 C10 122.5(3) . . ?
N1 C1 C10 115.3(4) . . ?
C1 C2 C3 120.0(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 122.1(3) . . ?
C2 C3 C8 118.3(3) . . ?
C4 C3 C8 119.6(3) . . ?
C5 C4 C3 122.8(3) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C4 C5 C6 117.2(3) . . ?
C4 C5 C11 122.5(4) . . ?
C6 C5 C11 120.3(4) . . ?
C7 C6 C5 121.9(3) . . ?
C7 C6 C12 117.6(3) . . ?
C5 C6 C12 120.5(3) . . ?
O1 C7 C6 116.8(3) . . ?
O1 C7 C8 122.1(3) . . ?
C6 C7 C8 121.1(3) . . ?
C7 C8 C3 116.5(3) . . ?
C7 C8 C9 127.0(3) . . ?
C3 C8 C9 116.4(3) . . ?
N1 C9 N3 117.5(3) . . ?
N1 C9 C8 121.9(3) . . ?
N3 C9 C8 120.6(3) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C6 179.1(5) . . ?
N3 C13 C14 111.0(3) . . ?
N3 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
N3 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 C13 110.4(3) . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C16 109.5(3) . . ?
C14 C15 H15A 109.8 . . ?
C16 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
C17 C16 C15 112.3(4) . . ?
C17 C16 H16A 109.1 . . ?
C15 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
N3 C17 C16 109.4(3) . . ?
N3 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
N3 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
O1 C18 C19 107.9(3) . . ?
O1 C18 H18A 110.1 . . ?
C19 C18 H18A 110.1 . . ?
O1 C18 H18B 110.1 . . ?
C19 C18 H18B 110.1 . . ?
H18A C18 H18B 108.4 . . ?
C24 C19 C20 117.4(4) . . ?
C24 C19 C18 122.0(3) . . ?
C20 C19 C18 120.6(4) . . ?
C19 C20 C21 121.1(4) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C22 C21 C20 120.6(4) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 119.8(4) . . ?
C21 C22 Br1 120.3(3) . . ?
C23 C22 Br1 119.9(4) . . ?
C22 C23 C24 119.5(4) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C19 C24 C23 121.5(4) . . ?
C19 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?

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
C9 N1 C1 C2 -4.2(5) . . . . ?
C9 N1 C1 C10 178.8(3) . . . . ?
N1 C1 C2 C3 8.5(5) . . . . ?
C10 C1 C2 C3 -174.7(3) . . . . ?
C1 C2 C3 C4 176.6(3) . . . . ?
C1 C2 C3 C8 -1.7(5) . . . . ?
C2 C3 C4 C5 -173.7(4) . . . . ?
C8 C3 C4 C5 4.5(5) . . . . ?
C3 C4 C5 C6 3.2(5) . . . . ?
C3 C4 C5 C11 -177.8(4) . . . . ?
C4 C5 C6 C7 -4.8(5) . . . . ?
C11 C5 C6 C7 176.2(4) . . . . ?
C4 C5 C6 C12 173.6(3) . . . . ?
C11 C5 C6 C12 -5.5(6) . . . . ?
C18 O1 C7 C6 -97.3(3) . . . . ?
C18 O1 C7 C8 83.5(4) . . . . ?
C5 C6 C7 O1 179.3(3) . . . . ?
C12 C6 C7 O1 0.9(5) . . . . ?
C5 C6 C7 C8 -1.5(5) . . . . ?
C12 C6 C7 C8 -179.9(3) . . . . ?
O1 C7 C8 C3 -171.9(3) . . . . ?
C6 C7 C8 C3 9.0(5) . . . . ?
O1 C7 C8 C9 3.9(5) . . . . ?
C6 C7 C8 C9 -175.3(3) . . . . ?
C2 C3 C8 C7 167.9(3) . . . . ?
C4 C3 C8 C7 -10.4(5) . . . . ?
C2 C3 C8 C9 -8.3(5) . . . . ?
C4 C3 C8 C9 173.4(3) . . . . ?
C1 N1 C9 N3 173.6(3) . . . . ?
C1 N1 C9 C8 -6.9(5) . . . . ?
C17 N3 C9 N1 9.9(4) . . . . ?
C13 N3 C9 N1 -124.9(3) . . . . ?
C17 N3 C9 C8 -169.6(3) . . . . ?
C13 N3 C9 C8 55.6(4) . . . . ?
C7 C8 C9 N1 -162.8(3) . . . . ?
C3 C8 C9 N1 12.9(5) . . . . ?
C7 C8 C9 N3 16.7(5) . . . . ?
C3 C8 C9 N3 -167.6(3) . . . . ?
C9 N3 C13 C14 -162.1(3) . . . . ?
C17 N3 C13 C14 60.5(4) . . . . ?
N3 C13 C14 C15 -58.0(4) . . . . ?
C13 C14 C15 C16 54.3(5) . . . . ?
C14 C15 C16 C17 -54.5(5) . . . . ?
C9 N3 C17 C16 164.1(3) . . . . ?
C13 N3 C17 C16 -58.7(4) . . . . ?
C15 C16 C17 N3 56.4(5) . . . . ?
C7 O1 C18 C19 167.8(3) . . . . ?
O1 C18 C19 C24 124.6(4) . . . . ?
O1 C18 C19 C20 -56.5(5) . . . . ?
C24 C19 C20 C21 -2.2(7) . . . . ?
C18 C19 C20 C21 178.9(4) . . . . ?
C19 C20 C21 C22 1.7(8) . . . . ?
C20 C21 C22 C23 0.3(8) . . . . ?
C20 C21 C22 Br1 179.9(4) . . . . ?
C21 C22 C23 C24 -1.7(7) . . . . ?
Br1 C22 C23 C24 178.6(4) . . . . ?
C20 C19 C24 C23 0.7(7) . . . . ?
C18 C19 C24 C23 179.6(4) . . . . ?
C22 C23 C24 C19 1.2(8) . . . . ?

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
C16 H16B N2 0.97 2.61 3.387(5) 137.0 1_545
C13 H13B O1 0.97 2.36 2.887(4) 113.1 .
C10 H10A Br1 0.96 3.03 3.818(4) 140.2 7_656
C10 H10A Br1 0.96 3.03 3.818(4) 140.2 7_656
C13 H13B O1 0.97 2.36 2.887(4) 113.1 .
C16 H16B N2 0.97 2.61 3.387(5) 137.0 1_545

_refine_diff_density_max         0.485
_refine_diff_density_min         -0.806
_refine_diff_density_rms         0.042

_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_dd18274_0m
_database_code_depnum_ccdc_archive 'CCDC 2245983'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2023-03-03 deposited with the CCDC.	2023-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 Cl N3 O'
_chemical_formula_weight         405.91

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'
Cl Cl 0.1484 0.1585 '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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.7226(8)
_cell_length_b                   13.7126(11)
_cell_length_c                   14.8083(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.229(3)
_cell_angle_gamma                90
_cell_volume                     2173.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5883
_cell_measurement_theta_min      4.570
_cell_measurement_theta_max      46.136

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.195
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6492
_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            17855
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.411
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             7991
_reflns_number_gt                5353
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.979

_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)+(0.0501P)²+0.2669P] 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       0.027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1933 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.26(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         7991
_refine_ls_number_parameters     528
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1262
_refine_ls_wR_factor_gt          0.1063
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.003
_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
Cl1 Cl 0.3371(2) 0.37320(15) 0.66645(10) 0.1507(8) Uani 1 1 d . . . . .
O1 O 0.2408(2) 0.3353(2) 0.22097(19) 0.0655(7) Uani 1 1 d . . . . .
N1 N 0.5223(3) 0.3514(3) 0.0264(2) 0.0692(9) Uani 1 1 d . . . . .
N2 N -0.0706(5) 0.3703(5) 0.2259(4) 0.1249(19) Uani 1 1 d . . . . .
N3 N 0.4834(3) 0.2920(3) 0.1680(2) 0.0668(9) Uani 1 1 d . . . . .
C1 C 0.4833(5) 0.3801(4) -0.0589(3) 0.0761(13) Uani 1 1 d . . . . .
C2 C 0.3615(5) 0.3825(4) -0.0871(3) 0.0803(13) Uani 1 1 d . . . . .
H2 H 0.3390 0.3953 -0.1475 0.096 Uiso 1 1 calc R U . . .
C3 C 0.2685(4) 0.3658(3) -0.0257(3) 0.0716(12) Uani 1 1 d . . . . .
C4 C 0.1390(5) 0.3758(4) -0.0508(3) 0.0806(13) Uani 1 1 d . . . . .
H4 H 0.1146 0.3854 -0.1114 0.097 Uiso 1 1 calc R U . . .
C5 C 0.0500(4) 0.3717(3) 0.0104(4) 0.0776(13) Uani 1 1 d . . . . .
C6 C 0.0889(4) 0.3585(3) 0.1020(3) 0.0727(12) Uani 1 1 d . . . . .
C7 C 0.2132(4) 0.3450(3) 0.1295(3) 0.0654(11) Uani 1 1 d . . . . .
C8 C 0.3067(4) 0.3436(3) 0.0660(3) 0.0642(10) Uani 1 1 d . . . . .
C9 C 0.4393(4) 0.3291(3) 0.0849(3) 0.0630(11) Uani 1 1 d . . . . .
C10 C 0.5865(5) 0.4053(5) -0.1192(3) 0.0996(17) Uani 1 1 d . . . . .
H10A H 0.6365 0.4567 -0.0920 0.149 Uiso 1 1 calc R U . . .
H10B H 0.5512 0.4265 -0.1769 0.149 Uiso 1 1 calc R U . . .
H10C H 0.6377 0.3489 -0.1272 0.149 Uiso 1 1 calc R U . . .
C11 C -0.0876(4) 0.3832(4) -0.0186(4) 0.1041(18) Uani 1 1 d . . . . .
H11A H -0.1136 0.4488 -0.0068 0.156 Uiso 1 1 calc R U . . .
H11B H -0.1361 0.3385 0.0149 0.156 Uiso 1 1 calc R U . . .
H11C H -0.0998 0.3697 -0.0820 0.156 Uiso 1 1 calc R U . . .
C12 C -0.0004(5) 0.3642(4) 0.1717(4) 0.0914(16) Uani 1 1 d . . . . .
C13 C 0.4383(4) 0.1939(3) 0.1891(3) 0.0761(13) Uani 1 1 d . . . . .
H13A H 0.4795 0.1464 0.1525 0.091 Uiso 1 1 calc R U . . .
H13B H 0.3493 0.1902 0.1739 0.091 Uiso 1 1 calc R U . . .
C14 C 0.4631(5) 0.1695(4) 0.2876(3) 0.0918(15) Uani 1 1 d . . . . .
H14A H 0.4372 0.1029 0.2984 0.110 Uiso 1 1 calc R U . . .
H14B H 0.4145 0.2123 0.3241 0.110 Uiso 1 1 calc R U . . .
C15 C 0.6016(5) 0.1808(5) 0.3152(4) 0.1034(19) Uani 1 1 d . . . . .
H15A H 0.6149 0.1712 0.3799 0.124 Uiso 1 1 calc R U . . .
H15B H 0.6494 0.1318 0.2849 0.124 Uiso 1 1 calc R U . . .
C16 C 0.6455(4) 0.2809(5) 0.2902(3) 0.0931(17) Uani 1 1 d . . . . .
H16A H 0.7347 0.2861 0.3045 0.112 Uiso 1 1 calc R U . . .
H16B H 0.6040 0.3293 0.3257 0.112 Uiso 1 1 calc R U . . .
C17 C 0.6184(4) 0.3019(4) 0.1899(3) 0.0817(14) Uani 1 1 d . . . . .
H17A H 0.6454 0.3675 0.1760 0.098 Uiso 1 1 calc R U . . .
H17B H 0.6640 0.2565 0.1539 0.098 Uiso 1 1 calc R U . . .
C18 C 0.2775(5) 0.4252(3) 0.2653(3) 0.0755(13) Uani 1 1 d . . . . .
H18A H 0.2145 0.4747 0.2521 0.091 Uiso 1 1 calc R U . . .
H18B H 0.3558 0.4479 0.2430 0.091 Uiso 1 1 calc R U . . .
C19 C 0.2924(4) 0.4092(3) 0.3640(3) 0.0652(11) Uani 1 1 d . . . . .
C20 C 0.2098(4) 0.3517(4) 0.4099(3) 0.0778(12) Uani 1 1 d . . . . .
H20 H 0.1439 0.3209 0.3779 0.093 Uiso 1 1 calc R U . . .
C21 C 0.2244(5) 0.3400(4) 0.5021(3) 0.0920(15) Uani 1 1 d . . . . .
H21 H 0.1694 0.3007 0.5320 0.110 Uiso 1 1 calc R U . . .
C22 C 0.3198(6) 0.3862(4) 0.5497(3) 0.0879(15) Uani 1 1 d . . . . .
C23 C 0.4011(5) 0.4441(4) 0.5067(4) 0.0862(14) Uani 1 1 d . . . . .
H23 H 0.4651 0.4760 0.5398 0.103 Uiso 1 1 calc R U . . .
C24 C 0.3883(4) 0.4552(4) 0.4145(3) 0.0762(13) Uani 1 1 d . . . . .
H24 H 0.4448 0.4940 0.3854 0.091 Uiso 1 1 calc R U . . .
Cl2 Cl -0.0570(3) 0.59060(18) 0.79474(12) 0.1832(11) Uani 1 1 d . . . . .
O2 O -0.0751(2) 0.6523(2) 0.3512(2) 0.0653(7) Uani 1 1 d . . . . .
N4 N 0.2122(3) 0.6651(2) 0.1578(2) 0.0640(9) Uani 1 1 d . . . . .
N5 N -0.3848(4) 0.6063(5) 0.3488(4) 0.133(2) Uani 1 1 d . . . . .
N6 N 0.1659(3) 0.7168(2) 0.3011(2) 0.0583(8) Uani 1 1 d . . . . .
C25 C 0.1784(4) 0.6358(3) 0.0725(3) 0.0692(11) Uani 1 1 d . . . . .
C26 C 0.0559(5) 0.6277(3) 0.0437(3) 0.0759(13) Uani 1 1 d . . . . .
H26 H 0.0347 0.6167 -0.0172 0.091 Uiso 1 1 calc R U . . .
C27 C -0.0386(4) 0.6358(3) 0.1048(3) 0.0686(12) Uani 1 1 d . . . . .
C28 C -0.1656(5) 0.6234(3) 0.0767(4) 0.0833(14) Uani 1 1 d . . . . .
H28 H -0.1868 0.6169 0.0153 0.100 Uiso 1 1 calc R U . . .
C29 C -0.2579(5) 0.6205(3) 0.1354(4) 0.0824(14) Uani 1 1 d . . . . .
C30 C -0.2209(4) 0.6288(3) 0.2290(4) 0.0766(13) Uani 1 1 d . . . . .
C31 C -0.0978(4) 0.6455(3) 0.2592(3) 0.0639(11) Uani 1 1 d . . . . .
C32 C -0.0041(4) 0.6553(3) 0.1968(3) 0.0615(10) Uani 1 1 d . . . . .
C33 C 0.1254(4) 0.6789(3) 0.2175(3) 0.0574(10) Uani 1 1 d . . . . .
C34 C 0.2836(5) 0.6224(4) 0.0112(3) 0.0920(16) Uani 1 1 d . . . . .
H34A H 0.3287 0.6825 0.0069 0.138 Uiso 1 1 calc R U . . .
H34B H 0.2506 0.6034 -0.0478 0.138 Uiso 1 1 calc R U . . .
H34C H 0.3389 0.5725 0.0353 0.138 Uiso 1 1 calc R U . . .
C35 C -0.3939(4) 0.6078(5) 0.1066(4) 0.115(2) Uani 1 1 d . . . . .
H35A H -0.4323 0.6707 0.0982 0.172 Uiso 1 1 calc R U . . .
H35B H -0.4350 0.5725 0.1524 0.172 Uiso 1 1 calc R U . . .
H35C H -0.4012 0.5721 0.0508 0.172 Uiso 1 1 calc R U . . .
C36 C -0.3112(5) 0.6165(4) 0.2969(4) 0.0963(17) Uani 1 1 d . . . . .
C37 C 0.1053(4) 0.8076(3) 0.3289(3) 0.0667(11) Uani 1 1 d . . . . .
H37A H 0.0160 0.8035 0.3144 0.080 Uiso 1 1 calc R U . . .
H37B H 0.1377 0.8622 0.2957 0.080 Uiso 1 1 calc R U . . .
C38 C 0.1286(4) 0.8245(3) 0.4284(3) 0.0773(12) Uani 1 1 d . . . . .
H38A H 0.0917 0.7720 0.4617 0.093 Uiso 1 1 calc R U . . .
H38B H 0.0894 0.8851 0.4452 0.093 Uiso 1 1 calc R U . . .
C39 C 0.2678(5) 0.8294(4) 0.4531(3) 0.0876(15) Uani 1 1 d . . . . .
H39A H 0.3031 0.8868 0.4258 0.105 Uiso 1 1 calc R U . . .
H39B H 0.2818 0.8346 0.5182 0.105 Uiso 1 1 calc R U . . .
C40 C 0.3309(4) 0.7392(4) 0.4198(3) 0.0771(13) Uani 1 1 d . . . . .
H40A H 0.3038 0.6832 0.4536 0.093 Uiso 1 1 calc R U . . .
H40B H 0.4206 0.7456 0.4310 0.093 Uiso 1 1 calc R U . . .
C41 C 0.3018(4) 0.7219(4) 0.3200(3) 0.0721(12) Uani 1 1 d . . . . .
H41A H 0.3361 0.7746 0.2854 0.087 Uiso 1 1 calc R U . . .
H41B H 0.3401 0.6614 0.3019 0.087 Uiso 1 1 calc R U . . .
C42 C -0.0203(5) 0.5653(3) 0.3933(3) 0.0840(14) Uani 1 1 d . . . . .
H42A H 0.0662 0.5588 0.3783 0.101 Uiso 1 1 calc R U . . .
H42B H -0.0655 0.5078 0.3717 0.101 Uiso 1 1 calc R U . . .
C43 C -0.0284(4) 0.5753(3) 0.4941(3) 0.0711(12) Uani 1 1 d . . . . .
C44 C -0.1411(5) 0.5891(4) 0.5319(4) 0.0917(16) Uani 1 1 d . . . . .
H44 H -0.2134 0.5948 0.4945 0.110 Uiso 1 1 calc R U . . .
C45 C -0.1489(6) 0.5945(4) 0.6238(4) 0.108(2) Uani 1 1 d . . . . .
H45 H -0.2259 0.6040 0.6483 0.129 Uiso 1 1 calc R U . . .
C46 C -0.0444(7) 0.5861(4) 0.6789(4) 0.1012(17) Uani 1 1 d . . . . .
C47 C 0.0683(6) 0.5720(5) 0.6441(4) 0.1087(19) Uani 1 1 d . . . . .
H47 H 0.1396 0.5658 0.6824 0.130 Uiso 1 1 calc R U . . .
C48 C 0.0768(5) 0.5667(4) 0.5510(4) 0.0936(16) Uani 1 1 d . . . . .
H48 H 0.1542 0.5574 0.5270 0.112 Uiso 1 1 calc R 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
Cl1 C22 1.737(5) . ?
O1 C7 1.376(5) . ?
O1 C18 1.441(5) . ?
N1 C9 1.313(5) . ?
N1 C1 1.366(5) . ?
N2 C12 1.133(6) . ?
N3 C9 1.390(5) . ?
N3 C13 1.469(6) . ?
N3 C17 1.472(5) . ?
C1 C2 1.349(6) . ?
C1 C10 1.501(7) . ?
C2 C3 1.406(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.424(6) . ?
C3 C8 1.429(5) . ?
C4 C5 1.354(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.407(6) . ?
C5 C11 1.521(6) . ?
C6 C7 1.384(5) . ?
C6 C12 1.450(8) . ?
C7 C8 1.413(6) . ?
C8 C9 1.447(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.505(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.527(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.504(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.524(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.478(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C24 1.388(6) . ?
C19 C20 1.391(6) . ?
C20 C21 1.375(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.365(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.363(7) . ?
C23 C24 1.373(7) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
Cl2 C46 1.730(6) . ?
O2 C31 1.374(5) . ?
O2 C42 1.455(5) . ?
N4 C33 1.333(5) . ?
N4 C25 1.355(5) . ?
N5 C36 1.140(7) . ?
N6 C33 1.390(5) . ?
N6 C41 1.470(5) . ?
N6 C37 1.474(5) . ?
C25 C26 1.362(6) . ?
C25 C34 1.498(6) . ?
C26 C27 1.400(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.411(6) . ?
C27 C32 1.418(6) . ?
C28 C29 1.353(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.424(7) . ?
C29 C35 1.507(6) . ?
C30 C31 1.389(6) . ?
C30 C36 1.445(7) . ?
C31 C32 1.408(6) . ?
C32 C33 1.442(5) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C37 C38 1.499(6) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.518(6) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.507(7) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C41 1.512(6) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C43 1.506(6) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 C44 1.373(6) . ?
C43 C48 1.375(7) . ?
C44 C45 1.370(7) . ?
C44 H44 0.9300 . ?
C45 C46 1.353(8) . ?
C45 H45 0.9300 . ?
C46 C47 1.354(8) . ?
C47 C48 1.389(7) . ?
C47 H47 0.9300 . ?
C48 H48 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C18 113.8(3) . . ?
C9 N1 C1 119.5(4) . . ?
C9 N3 C13 115.1(3) . . ?
C9 N3 C17 116.3(3) . . ?
C13 N3 C17 111.7(3) . . ?
C2 C1 N1 122.3(4) . . ?
C2 C1 C10 122.9(4) . . ?
N1 C1 C10 114.8(4) . . ?
C1 C2 C3 120.4(4) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 122.2(4) . . ?
C2 C3 C8 118.3(4) . . ?
C4 C3 C8 119.4(4) . . ?
C5 C4 C3 122.3(4) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 C6 117.9(4) . . ?
C4 C5 C11 121.0(4) . . ?
C6 C5 C11 121.0(5) . . ?
C7 C6 C5 122.0(4) . . ?
C7 C6 C12 117.5(4) . . ?
C5 C6 C12 120.5(4) . . ?
O1 C7 C6 117.0(4) . . ?
O1 C7 C8 122.1(3) . . ?
C6 C7 C8 120.9(4) . . ?
C7 C8 C3 117.0(4) . . ?
C7 C8 C9 126.8(4) . . ?
C3 C8 C9 116.0(4) . . ?
N1 C9 N3 117.3(3) . . ?
N1 C9 C8 122.4(4) . . ?
N3 C9 C8 120.2(4) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C6 178.9(7) . . ?
N3 C13 C14 111.6(4) . . ?
N3 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N3 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 110.7(4) . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 109.9(4) . . ?
C16 C15 H15A 109.7 . . ?
C14 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C15 C16 C17 111.6(5) . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
N3 C17 C16 109.1(4) . . ?
N3 C17 H17A 109.9 . . ?
C16 C17 H17A 109.9 . . ?
N3 C17 H17B 109.9 . . ?
C16 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
O1 C18 C19 109.5(3) . . ?
O1 C18 H18A 109.8 . . ?
C19 C18 H18A 109.8 . . ?
O1 C18 H18B 109.8 . . ?
C19 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
C24 C19 C20 117.8(4) . . ?
C24 C19 C18 120.0(4) . . ?
C20 C19 C18 122.1(4) . . ?
C21 C20 C19 120.8(5) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C20 119.9(5) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 120.6(5) . . ?
C23 C22 Cl1 119.3(5) . . ?
C21 C22 Cl1 120.1(5) . . ?
C22 C23 C24 119.9(5) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C19 120.9(5) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
C31 O2 C42 114.4(3) . . ?
C33 N4 C25 120.0(4) . . ?
C33 N6 C41 116.4(3) . . ?
C33 N6 C37 116.3(3) . . ?
C41 N6 C37 110.8(3) . . ?
N4 C25 C26 121.2(4) . . ?
N4 C25 C34 115.4(4) . . ?
C26 C25 C34 123.1(4) . . ?
C25 C26 C27 120.8(4) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C26 C27 C28 121.5(4) . . ?
C26 C27 C32 118.5(4) . . ?
C28 C27 C32 120.1(4) . . ?
C29 C28 C27 122.9(5) . . ?
C29 C28 H28 118.6 . . ?
C27 C28 H28 118.6 . . ?
C28 C29 C30 116.7(4) . . ?
C28 C29 C35 123.6(5) . . ?
C30 C29 C35 119.8(5) . . ?
C31 C30 C29 122.3(4) . . ?
C31 C30 C36 117.2(5) . . ?
C29 C30 C36 120.5(4) . . ?
O2 C31 C30 116.3(4) . . ?
O2 C31 C32 123.4(4) . . ?
C30 C31 C32 120.3(4) . . ?
C31 C32 C27 117.0(4) . . ?
C31 C32 C33 126.6(4) . . ?
C27 C32 C33 116.3(4) . . ?
N4 C33 N6 116.7(3) . . ?
N4 C33 C32 121.8(4) . . ?
N6 C33 C32 121.5(3) . . ?
C25 C34 H34A 109.5 . . ?
C25 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C25 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C29 C35 H35A 109.5 . . ?
C29 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C29 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N5 C36 C30 178.2(6) . . ?
N6 C37 C38 110.6(3) . . ?
N6 C37 H37A 109.5 . . ?
C38 C37 H37A 109.5 . . ?
N6 C37 H37B 109.5 . . ?
C38 C37 H37B 109.5 . . ?
H37A C37 H37B 108.1 . . ?
C37 C38 C39 110.6(4) . . ?
C37 C38 H38A 109.5 . . ?
C39 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C39 C38 H38B 109.5 . . ?
H38A C38 H38B 108.1 . . ?
C40 C39 C38 109.8(4) . . ?
C40 C39 H39A 109.7 . . ?
C38 C39 H39A 109.7 . . ?
C40 C39 H39B 109.7 . . ?
C38 C39 H39B 109.7 . . ?
H39A C39 H39B 108.2 . . ?
C39 C40 C41 112.1(4) . . ?
C39 C40 H40A 109.2 . . ?
C41 C40 H40A 109.2 . . ?
C39 C40 H40B 109.2 . . ?
C41 C40 H40B 109.2 . . ?
H40A C40 H40B 107.9 . . ?
N6 C41 C40 109.9(3) . . ?
N6 C41 H41A 109.7 . . ?
C40 C41 H41A 109.7 . . ?
N6 C41 H41B 109.7 . . ?
C40 C41 H41B 109.7 . . ?
H41A C41 H41B 108.2 . . ?
O2 C42 C43 107.8(4) . . ?
O2 C42 H42A 110.2 . . ?
C43 C42 H42A 110.2 . . ?
O2 C42 H42B 110.2 . . ?
C43 C42 H42B 110.2 . . ?
H42A C42 H42B 108.5 . . ?
C44 C43 C48 118.2(5) . . ?
C44 C43 C42 121.2(5) . . ?
C48 C43 C42 120.6(4) . . ?
C45 C44 C43 121.1(5) . . ?
C45 C44 H44 119.5 . . ?
C43 C44 H44 119.5 . . ?
C46 C45 C44 120.0(5) . . ?
C46 C45 H45 120.0 . . ?
C44 C45 H45 120.0 . . ?
C45 C46 C47 120.6(5) . . ?
C45 C46 Cl2 119.2(5) . . ?
C47 C46 Cl2 120.2(6) . . ?
C46 C47 C48 119.7(6) . . ?
C46 C47 H47 120.2 . . ?
C48 C47 H47 120.2 . . ?
C43 C48 C47 120.4(5) . . ?
C43 C48 H48 119.8 . . ?
C47 C48 H48 119.8 . . ?

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
C9 N1 C1 C2 -3.0(7) . . . . ?
C9 N1 C1 C10 179.0(4) . . . . ?
N1 C1 C2 C3 7.3(8) . . . . ?
C10 C1 C2 C3 -174.8(5) . . . . ?
C1 C2 C3 C4 174.6(5) . . . . ?
C1 C2 C3 C8 -1.8(7) . . . . ?
C2 C3 C4 C5 -171.6(5) . . . . ?
C8 C3 C4 C5 4.8(7) . . . . ?
C3 C4 C5 C6 1.0(7) . . . . ?
C3 C4 C5 C11 179.6(5) . . . . ?
C4 C5 C6 C7 -3.3(7) . . . . ?
C11 C5 C6 C7 178.1(4) . . . . ?
C4 C5 C6 C12 173.2(5) . . . . ?
C11 C5 C6 C12 -5.5(7) . . . . ?
C18 O1 C7 C6 -94.9(5) . . . . ?
C18 O1 C7 C8 83.7(5) . . . . ?
C5 C6 C7 O1 178.4(4) . . . . ?
C12 C6 C7 O1 1.8(6) . . . . ?
C5 C6 C7 C8 -0.2(7) . . . . ?
C12 C6 C7 C8 -176.8(4) . . . . ?
O1 C7 C8 C3 -172.8(4) . . . . ?
C6 C7 C8 C3 5.8(6) . . . . ?
O1 C7 C8 C9 2.2(7) . . . . ?
C6 C7 C8 C9 -179.2(4) . . . . ?
C2 C3 C8 C7 168.6(4) . . . . ?
C4 C3 C8 C7 -7.9(6) . . . . ?
C2 C3 C8 C9 -6.9(6) . . . . ?
C4 C3 C8 C9 176.5(4) . . . . ?
C1 N1 C9 N3 174.4(4) . . . . ?
C1 N1 C9 C8 -6.7(6) . . . . ?
C13 N3 C9 N1 -120.0(4) . . . . ?
C17 N3 C9 N1 13.3(6) . . . . ?
C13 N3 C9 C8 61.1(5) . . . . ?
C17 N3 C9 C8 -165.6(4) . . . . ?
C7 C8 C9 N1 -163.5(4) . . . . ?
C3 C8 C9 N1 11.5(6) . . . . ?
C7 C8 C9 N3 15.3(6) . . . . ?
C3 C8 C9 N3 -169.6(4) . . . . ?
C9 N3 C13 C14 -165.7(4) . . . . ?
C17 N3 C13 C14 58.9(5) . . . . ?
N3 C13 C14 C15 -55.5(6) . . . . ?
C13 C14 C15 C16 53.6(6) . . . . ?
C14 C15 C16 C17 -55.5(6) . . . . ?
C9 N3 C17 C16 166.4(4) . . . . ?
C13 N3 C17 C16 -58.8(5) . . . . ?
C15 C16 C17 N3 57.8(6) . . . . ?
C7 O1 C18 C19 174.2(3) . . . . ?
O1 C18 C19 C24 141.8(4) . . . . ?
O1 C18 C19 C20 -40.8(6) . . . . ?
C24 C19 C20 C21 -1.0(7) . . . . ?
C18 C19 C20 C21 -178.5(4) . . . . ?
C19 C20 C21 C22 1.0(8) . . . . ?
C20 C21 C22 C23 0.0(8) . . . . ?
C20 C21 C22 Cl1 178.9(4) . . . . ?
C21 C22 C23 C24 -1.0(8) . . . . ?
Cl1 C22 C23 C24 -179.9(4) . . . . ?
C22 C23 C24 C19 0.9(7) . . . . ?
C20 C19 C24 C23 0.1(7) . . . . ?
C18 C19 C24 C23 177.6(4) . . . . ?
C33 N4 C25 C26 5.5(6) . . . . ?
C33 N4 C25 C34 -179.8(4) . . . . ?
N4 C25 C26 C27 -9.3(7) . . . . ?
C34 C25 C26 C27 176.5(4) . . . . ?
C25 C26 C27 C28 -177.2(4) . . . . ?
C25 C26 C27 C32 1.8(6) . . . . ?
C26 C27 C28 C29 172.9(5) . . . . ?
C32 C27 C28 C29 -6.1(7) . . . . ?
C27 C28 C29 C30 -1.2(7) . . . . ?
C27 C28 C29 C35 179.7(4) . . . . ?
C28 C29 C30 C31 4.2(7) . . . . ?
C35 C29 C30 C31 -176.7(4) . . . . ?
C28 C29 C30 C36 -173.7(5) . . . . ?
C35 C29 C30 C36 5.4(7) . . . . ?
C42 O2 C31 C30 102.2(4) . . . . ?
C42 O2 C31 C32 -78.3(5) . . . . ?
C29 C30 C31 O2 179.7(4) . . . . ?
C36 C30 C31 O2 -2.3(6) . . . . ?
C29 C30 C31 C32 0.2(6) . . . . ?
C36 C30 C31 C32 178.2(4) . . . . ?
O2 C31 C32 C27 173.2(3) . . . . ?
C30 C31 C32 C27 -7.4(6) . . . . ?
O2 C31 C32 C33 -3.8(6) . . . . ?
C30 C31 C32 C33 175.7(4) . . . . ?
C26 C27 C32 C31 -168.8(4) . . . . ?
C28 C27 C32 C31 10.3(6) . . . . ?
C26 C27 C32 C33 8.5(6) . . . . ?
C28 C27 C32 C33 -172.5(4) . . . . ?
C25 N4 C33 N6 -174.7(3) . . . . ?
C25 N4 C33 C32 5.6(6) . . . . ?
C41 N6 C33 N4 -10.0(5) . . . . ?
C37 N6 C33 N4 123.4(4) . . . . ?
C41 N6 C33 C32 169.7(4) . . . . ?
C37 N6 C33 C32 -56.9(5) . . . . ?
C31 C32 C33 N4 164.5(4) . . . . ?
C27 C32 C33 N4 -12.4(6) . . . . ?
C31 C32 C33 N6 -15.1(6) . . . . ?
C27 C32 C33 N6 167.9(3) . . . . ?
C33 N6 C37 C38 163.5(3) . . . . ?
C41 N6 C37 C38 -60.7(4) . . . . ?
N6 C37 C38 C39 58.1(5) . . . . ?
C37 C38 C39 C40 -54.3(5) . . . . ?
C38 C39 C40 C41 53.7(5) . . . . ?
C33 N6 C41 C40 -165.4(4) . . . . ?
C37 N6 C41 C40 58.8(5) . . . . ?
C39 C40 C41 N6 -56.1(5) . . . . ?
C31 O2 C42 C43 -167.3(4) . . . . ?
O2 C42 C43 C44 57.4(6) . . . . ?
O2 C42 C43 C48 -125.4(5) . . . . ?
C48 C43 C44 C45 0.2(8) . . . . ?
C42 C43 C44 C45 177.5(5) . . . . ?
C43 C44 C45 C46 -0.1(9) . . . . ?
C44 C45 C46 C47 -0.2(9) . . . . ?
C44 C45 C46 Cl2 -178.7(5) . . . . ?
C45 C46 C47 C48 0.4(10) . . . . ?
Cl2 C46 C47 C48 178.9(5) . . . . ?
C44 C43 C48 C47 0.0(8) . . . . ?
C42 C43 C48 C47 -177.3(5) . . . . ?
C46 C47 C48 C43 -0.3(9) . . . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.026

_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_dd18307
_database_code_depnum_ccdc_archive 'CCDC 2245981'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2023-03-03 deposited with the CCDC.	2023-04-26 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 H27 N3 O'
_chemical_formula_weight         385.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

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

_cell_length_a                   15.3952(10)
_cell_length_b                   31.5081(17)
_cell_length_c                   9.8531(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4779.5(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3467
_cell_measurement_theta_min      4.695
_cell_measurement_theta_max      49.020

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.071
_exptl_crystal_F_000             1648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.066
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6608
_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            21207
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.538
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4433
_reflns_number_gt                2513
_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)+(0.0952P)²] 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       0.0105(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4433
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.1887
_refine_ls_wR_factor_gt          0.1607
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.750 0.250 -0.024 299 22 ' '
2 0.250 0.750 -0.048 299 22 ' '
_platon_squeeze_details          
;
;


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 0.55264(10) 0.59657(5) 0.54989(14) 0.0554(5) Uani 1 1 d . . . . .
N1 N 0.81003(14) 0.63959(6) 0.4345(2) 0.0634(6) Uani 1 1 d . . . . .
N2 N 0.66530(13) 0.65896(6) 0.43577(19) 0.0579(5) Uani 1 1 d . . . . .
N3 N 0.46636(18) 0.52121(8) 0.7570(3) 0.0996(9) Uani 1 1 d . . . . .
C1 C 0.87780(16) 0.61559(9) 0.4779(3) 0.0649(7) Uani 1 1 d . . . . .
C2 C 0.86773(16) 0.58420(8) 0.5705(3) 0.0638(7) Uani 1 1 d . . . . .
H2 H 0.9161 0.5697 0.6029 0.077 Uiso 1 1 calc R U . . .
C3 C 0.78454(15) 0.57345(7) 0.6178(2) 0.0563(6) Uani 1 1 d . . . . .
C4 C 0.77208(17) 0.53970(7) 0.7116(2) 0.0634(7) Uani 1 1 d . . . . .
H4 H 0.8207 0.5257 0.7453 0.076 Uiso 1 1 calc R U . . .
C5 C 0.69240(17) 0.52700(7) 0.7543(2) 0.0603(7) Uani 1 1 d . . . . .
C6 C 0.61985(16) 0.54747(7) 0.6943(2) 0.0568(6) Uani 1 1 d . . . . .
C7 C 0.62884(15) 0.58046(7) 0.6020(2) 0.0504(6) Uani 1 1 d . . . . .
C8 C 0.71149(14) 0.59599(7) 0.5663(2) 0.0509(6) Uani 1 1 d . . . . .
C9 C 0.73108(16) 0.63157(7) 0.4784(2) 0.0539(6) Uani 1 1 d . . . . .
C10 C 0.96515(17) 0.62812(10) 0.4222(3) 0.0854(9) Uani 1 1 d . . . . .
H10A H 0.9638 0.6268 0.3249 0.128 Uiso 1 1 calc R U . . .
H10B H 1.0087 0.6090 0.4558 0.128 Uiso 1 1 calc R U . . .
H10C H 0.9787 0.6565 0.4504 0.128 Uiso 1 1 calc R U . . .
C11 C 0.6801(2) 0.49198(8) 0.8557(3) 0.0842(9) Uani 1 1 d . . . . .
H11A H 0.6472 0.5024 0.9314 0.126 Uiso 1 1 calc R U . . .
H11B H 0.7358 0.4823 0.8866 0.126 Uiso 1 1 calc R U . . .
H11C H 0.6495 0.4689 0.8138 0.126 Uiso 1 1 calc R U . . .
C12 C 0.5333(2) 0.53321(8) 0.7281(3) 0.0695(7) Uani 1 1 d . . . . .
C13 C 0.62318(17) 0.68289(8) 0.5452(3) 0.0685(7) Uani 1 1 d . . . . .
H13A H 0.6633 0.7039 0.5804 0.082 Uiso 1 1 calc R U . . .
H13B H 0.6083 0.6637 0.6186 0.082 Uiso 1 1 calc R U . . .
C14 C 0.54249(18) 0.70462(9) 0.4954(3) 0.0843(9) Uani 1 1 d . . . . .
H14A H 0.5179 0.7216 0.5681 0.101 Uiso 1 1 calc R U . . .
H14B H 0.4999 0.6835 0.4694 0.101 Uiso 1 1 calc R U . . .
C15 C 0.5625(2) 0.73320(9) 0.3737(4) 0.1041(11) Uani 1 1 d . . . . .
H15A H 0.5089 0.7445 0.3369 0.125 Uiso 1 1 calc R U . . .
H15B H 0.5983 0.7569 0.4027 0.125 Uiso 1 1 calc R U . . .
C16 C 0.6096(2) 0.70824(10) 0.2658(3) 0.0929(10) Uani 1 1 d . . . . .
H16A H 0.5708 0.6869 0.2286 0.111 Uiso 1 1 calc R U . . .
H16B H 0.6263 0.7272 0.1926 0.111 Uiso 1 1 calc R U . . .
C17 C 0.68904(19) 0.68693(8) 0.3216(3) 0.0774(8) Uani 1 1 d . . . . .
H17A H 0.7167 0.6704 0.2508 0.093 Uiso 1 1 calc R U . . .
H17B H 0.7300 0.7082 0.3524 0.093 Uiso 1 1 calc R U . . .
C18 C 0.53153(16) 0.57914(9) 0.4177(2) 0.0738(8) Uani 1 1 d . . . . .
H18A H 0.5359 0.5484 0.4201 0.089 Uiso 1 1 calc R U . . .
H18B H 0.5721 0.5897 0.3504 0.089 Uiso 1 1 calc R U . . .
C19 C 0.44108(15) 0.59198(8) 0.3805(2) 0.0602(6) Uani 1 1 d . . . . .
C20 C 0.3706(2) 0.57720(10) 0.4500(3) 0.0843(9) Uani 1 1 d . . . . .
H20 H 0.3791 0.5589 0.5228 0.101 Uiso 1 1 calc R U . . .
C21 C 0.28733(19) 0.58869(11) 0.4149(3) 0.0884(9) Uani 1 1 d . . . . .
H21 H 0.2408 0.5780 0.4643 0.106 Uiso 1 1 calc R U . . .
C22 C 0.27181(17) 0.61551(10) 0.3088(3) 0.0735(8) Uani 1 1 d . . . . .
C23 C 0.34295(19) 0.62984(9) 0.2378(3) 0.0798(8) Uani 1 1 d . . . . .
H23 H 0.3346 0.6478 0.1641 0.096 Uiso 1 1 calc R U . . .
C24 C 0.42605(17) 0.61822(9) 0.2730(3) 0.0712(7) Uani 1 1 d . . . . .
H24 H 0.4727 0.6284 0.2227 0.085 Uiso 1 1 calc R U . . .
C25 C 0.1797(2) 0.62903(13) 0.2719(4) 0.1150(12) Uani 1 1 d . . . . .
H25A H 0.1585 0.6487 0.3385 0.172 Uiso 1 1 calc R U . . .
H25B H 0.1426 0.6045 0.2697 0.172 Uiso 1 1 calc R U . . .
H25C H 0.1799 0.6424 0.1843 0.172 Uiso 1 1 calc R 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
O1 C7 1.378(3) . ?
O1 C18 1.451(3) . ?
N1 C9 1.315(3) . ?
N1 C1 1.358(3) . ?
N2 C9 1.395(3) . ?
N2 C13 1.467(3) . ?
N2 C17 1.475(3) . ?
N3 C12 1.134(3) . ?
C1 C2 1.355(4) . ?
C1 C10 1.505(3) . ?
C2 C3 1.404(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.422(3) . ?
C3 C8 1.424(3) . ?
C4 C5 1.357(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.419(3) . ?
C5 C11 1.500(3) . ?
C6 C7 1.388(3) . ?
C6 C12 1.445(4) . ?
C7 C8 1.408(3) . ?
C8 C9 1.448(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.501(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.531(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.508(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.500(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.496(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C24 1.364(3) . ?
C19 C20 1.365(4) . ?
C20 C21 1.376(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.365(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.376(4) . ?
C22 C25 1.525(4) . ?
C23 C24 1.375(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C18 112.72(17) . . ?
C9 N1 C1 120.0(2) . . ?
C9 N2 C13 114.69(18) . . ?
C9 N2 C17 114.8(2) . . ?
C13 N2 C17 111.29(19) . . ?
C2 C1 N1 122.1(2) . . ?
C2 C1 C10 122.6(3) . . ?
N1 C1 C10 115.2(2) . . ?
C1 C2 C3 120.3(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 C8 118.8(2) . . ?
C4 C3 C8 119.9(2) . . ?
C5 C4 C3 122.9(2) . . ?
C5 C4 H4 118.5 . . ?
C3 C4 H4 118.5 . . ?
C4 C5 C6 116.6(2) . . ?
C4 C5 C11 122.5(2) . . ?
C6 C5 C11 120.9(2) . . ?
C7 C6 C5 122.3(2) . . ?
C7 C6 C12 118.4(2) . . ?
C5 C6 C12 119.2(2) . . ?
O1 C7 C6 115.8(2) . . ?
O1 C7 C8 123.2(2) . . ?
C6 C7 C8 121.0(2) . . ?
C7 C8 C3 116.8(2) . . ?
C7 C8 C9 127.4(2) . . ?
C3 C8 C9 115.8(2) . . ?
N1 C9 N2 117.0(2) . . ?
N1 C9 C8 122.5(2) . . ?
N2 C9 C8 120.5(2) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C6 178.1(3) . . ?
N2 C13 C14 111.1(2) . . ?
N2 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
N2 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 110.9(3) . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 110.0(2) . . ?
C16 C15 H15A 109.7 . . ?
C14 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C17 C16 C15 111.5(3) . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
N2 C17 C16 110.2(2) . . ?
N2 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
N2 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
O1 C18 C19 109.0(2) . . ?
O1 C18 H18A 109.9 . . ?
C19 C18 H18A 109.9 . . ?
O1 C18 H18B 109.9 . . ?
C19 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
C24 C19 C20 117.5(2) . . ?
C24 C19 C18 120.8(2) . . ?
C20 C19 C18 121.7(3) . . ?
C19 C20 C21 121.7(3) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C22 C21 C20 121.2(3) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C23 116.9(3) . . ?
C21 C22 C25 121.2(3) . . ?
C23 C22 C25 121.8(3) . . ?
C24 C23 C22 121.7(3) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C19 C24 C23 121.0(2) . . ?
C19 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C2 -2.8(4) . . . . ?
C9 N1 C1 C10 -179.2(2) . . . . ?
N1 C1 C2 C3 4.6(4) . . . . ?
C10 C1 C2 C3 -179.2(2) . . . . ?
C1 C2 C3 C4 177.9(2) . . . . ?
C1 C2 C3 C8 0.3(4) . . . . ?
C2 C3 C4 C5 -176.6(2) . . . . ?
C8 C3 C4 C5 1.0(3) . . . . ?
C3 C4 C5 C6 3.7(3) . . . . ?
C3 C4 C5 C11 -178.6(2) . . . . ?
C4 C5 C6 C7 -3.5(3) . . . . ?
C11 C5 C6 C7 178.8(2) . . . . ?
C4 C5 C6 C12 175.5(2) . . . . ?
C11 C5 C6 C12 -2.2(3) . . . . ?
C18 O1 C7 C6 -97.9(2) . . . . ?
C18 O1 C7 C8 82.4(3) . . . . ?
C5 C6 C7 O1 178.57(19) . . . . ?
C12 C6 C7 O1 -0.4(3) . . . . ?
C5 C6 C7 C8 -1.7(3) . . . . ?
C12 C6 C7 C8 179.3(2) . . . . ?
O1 C7 C8 C3 -173.90(18) . . . . ?
C6 C7 C8 C3 6.4(3) . . . . ?
O1 C7 C8 C9 3.6(4) . . . . ?
C6 C7 C8 C9 -176.1(2) . . . . ?
C2 C3 C8 C7 171.57(19) . . . . ?
C4 C3 C8 C7 -6.1(3) . . . . ?
C2 C3 C8 C9 -6.2(3) . . . . ?
C4 C3 C8 C9 176.09(19) . . . . ?
C1 N1 C9 N2 176.4(2) . . . . ?
C1 N1 C9 C8 -4.0(3) . . . . ?
C13 N2 C9 N1 -116.6(2) . . . . ?
C17 N2 C9 N1 14.1(3) . . . . ?
C13 N2 C9 C8 63.8(3) . . . . ?
C17 N2 C9 C8 -165.5(2) . . . . ?
C7 C8 C9 N1 -169.2(2) . . . . ?
C3 C8 C9 N1 8.3(3) . . . . ?
C7 C8 C9 N2 10.4(3) . . . . ?
C3 C8 C9 N2 -172.07(19) . . . . ?
C9 N2 C13 C14 -168.6(2) . . . . ?
C17 N2 C13 C14 59.0(3) . . . . ?
N2 C13 C14 C15 -55.7(3) . . . . ?
C13 C14 C15 C16 53.1(3) . . . . ?
C14 C15 C16 C17 -54.2(3) . . . . ?
C9 N2 C17 C16 168.3(2) . . . . ?
C13 N2 C17 C16 -59.3(3) . . . . ?
C15 C16 C17 N2 57.3(3) . . . . ?
C7 O1 C18 C19 169.7(2) . . . . ?
O1 C18 C19 C24 114.7(3) . . . . ?
O1 C18 C19 C20 -67.0(3) . . . . ?
C24 C19 C20 C21 -1.0(4) . . . . ?
C18 C19 C20 C21 -179.3(3) . . . . ?
C19 C20 C21 C22 -0.1(5) . . . . ?
C20 C21 C22 C23 1.0(5) . . . . ?
C20 C21 C22 C25 -178.6(3) . . . . ?
C21 C22 C23 C24 -0.9(4) . . . . ?
C25 C22 C23 C24 178.7(3) . . . . ?
C20 C19 C24 C23 1.1(4) . . . . ?
C18 C19 C24 C23 179.5(2) . . . . ?
C22 C23 C24 C19 -0.2(4) . . . . ?

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.048

_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_dd18276_0m
_database_code_depnum_ccdc_archive 'CCDC 2245985'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2023-03-03 deposited with the CCDC.	2023-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H27 N3 O3'
_chemical_formula_weight         429.50

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           2
_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'
'-x, -y, -z'

_cell_length_a                   11.0228(14)
_cell_length_b                   11.0661(13)
_cell_length_c                   19.024(3)
_cell_angle_alpha                80.438(4)
_cell_angle_beta                 87.096(4)
_cell_angle_gamma                85.625(4)
_cell_volume                     2279.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      4.346
_cell_measurement_theta_max      54.933

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6940
_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            33903
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.854
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             8916
_reflns_number_gt                6701
_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)+(0.0580P)²+0.4587P] 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       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8916
_refine_ls_number_parameters     584
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1338
_refine_ls_wR_factor_gt          0.1174
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.017
_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 0.47935(10) 0.29875(9) 0.12465(6) 0.0490(3) Uani 1 1 d . . . . .
O2 O 0.66467(12) 0.81094(13) 0.27740(9) 0.0838(5) Uani 1 1 d . . . . .
O3 O 0.46504(11) 0.83886(10) 0.26619(7) 0.0626(3) Uani 1 1 d . . . . .
N1 N 0.74456(13) 0.01379(13) 0.07878(8) 0.0564(4) Uani 1 1 d . . . . .
N2 N 0.17202(17) 0.33126(18) 0.15358(11) 0.0869(6) Uani 1 1 d . . . . .
N3 N 0.71250(12) 0.22546(13) 0.06558(8) 0.0541(4) Uani 1 1 d . . . . .
C1 C 0.70266(19) -0.10055(16) 0.08437(9) 0.0575(5) Uani 1 1 d . . . . .
C2 C 0.58284(18) -0.11898(15) 0.08453(9) 0.0562(5) Uani 1 1 d . . . . .
H2 H 0.5583 -0.1965 0.0816 0.067 Uiso 1 1 calc R U . . .
C3 C 0.49531(16) -0.02098(14) 0.08914(8) 0.0475(4) Uani 1 1 d . . . . .
C4 C 0.36944(17) -0.03789(15) 0.09330(9) 0.0536(4) Uani 1 1 d . . . . .
H4 H 0.3440 -0.1147 0.0896 0.064 Uiso 1 1 calc R U . . .
C5 C 0.28375(16) 0.05390(16) 0.10256(9) 0.0518(4) Uani 1 1 d . . . . .
C6 C 0.32670(15) 0.16672(15) 0.11441(9) 0.0488(4) Uani 1 1 d . . . . .
C7 C 0.44894(15) 0.18733(13) 0.11009(8) 0.0441(4) Uani 1 1 d . . . . .
C8 C 0.53707(15) 0.09682(13) 0.09163(8) 0.0442(4) Uani 1 1 d . . . . .
C9 C 0.66613(15) 0.10992(15) 0.07829(8) 0.0478(4) Uani 1 1 d . . . . .
C10 C 0.7994(2) -0.20508(19) 0.08756(12) 0.0837(7) Uani 1 1 d . . . . .
H10A H 0.8738 -0.1750 0.0654 0.126 Uiso 1 1 calc R U . . .
H10B H 0.7732 -0.2669 0.0629 0.126 Uiso 1 1 calc R U . . .
H10C H 0.8126 -0.2399 0.1365 0.126 Uiso 1 1 calc R U . . .
C11 C 0.14978(18) 0.0374(2) 0.10094(11) 0.0715(6) Uani 1 1 d . . . . .
H11A H 0.1081 0.0681 0.1406 0.107 Uiso 1 1 calc R U . . .
H11B H 0.1373 -0.0483 0.1040 0.107 Uiso 1 1 calc R U . . .
H11C H 0.1184 0.0818 0.0572 0.107 Uiso 1 1 calc R U . . .
C12 C 0.24164(17) 0.25994(17) 0.13552(10) 0.0591(5) Uani 1 1 d . . . . .
C13 C 0.66083(17) 0.31681(15) 0.00777(10) 0.0564(4) Uani 1 1 d . . . . .
H13A H 0.5733 0.3119 0.0084 0.068 Uiso 1 1 calc R U . . .
H13B H 0.6941 0.2987 -0.0378 0.068 Uiso 1 1 calc R U . . .
C14 C 0.68915(19) 0.44571(17) 0.01571(12) 0.0693(5) Uani 1 1 d . . . . .
H14A H 0.6575 0.5038 -0.0242 0.083 Uiso 1 1 calc R U . . .
H14B H 0.6497 0.4668 0.0592 0.083 Uiso 1 1 calc R U . . .
C15 C 0.8254(2) 0.4541(2) 0.01810(15) 0.0891(7) Uani 1 1 d . . . . .
H15A H 0.8421 0.5342 0.0281 0.107 Uiso 1 1 calc R U . . .
H15B H 0.8637 0.4444 -0.0279 0.107 Uiso 1 1 calc R U . . .
C16 C 0.8779(2) 0.3547(2) 0.07553(15) 0.0924(8) Uani 1 1 d . . . . .
H16A H 0.9658 0.3568 0.0740 0.111 Uiso 1 1 calc R U . . .
H16B H 0.8473 0.3711 0.1220 0.111 Uiso 1 1 calc R U . . .
C17 C 0.84516(17) 0.2281(2) 0.06612(13) 0.0769(6) Uani 1 1 d . . . . .
H17A H 0.8815 0.2081 0.0216 0.092 Uiso 1 1 calc R U . . .
H17B H 0.8768 0.1674 0.1048 0.092 Uiso 1 1 calc R U . . .
C18 C 0.53160(18) 0.29183(15) 0.19326(9) 0.0556(4) Uani 1 1 d . . . . .
H18A H 0.6114 0.2482 0.1935 0.067 Uiso 1 1 calc R U . . .
H18B H 0.4802 0.2475 0.2301 0.067 Uiso 1 1 calc R U . . .
C19 C 0.54238(15) 0.41938(15) 0.20771(8) 0.0481(4) Uani 1 1 d . . . . .
C20 C 0.44848(15) 0.50972(15) 0.19348(9) 0.0497(4) Uani 1 1 d . . . . .
H20 H 0.3791 0.4923 0.1722 0.060 Uiso 1 1 calc R U . . .
C21 C 0.45691(15) 0.62493(14) 0.21052(9) 0.0475(4) Uani 1 1 d . . . . .
H21 H 0.3932 0.6846 0.2009 0.057 Uiso 1 1 calc R U . . .
C22 C 0.55991(14) 0.65235(14) 0.24197(8) 0.0447(4) Uani 1 1 d . . . . .
C23 C 0.65448(16) 0.56369(17) 0.25527(10) 0.0590(5) Uani 1 1 d . . . . .
H23 H 0.7244 0.5817 0.2757 0.071 Uiso 1 1 calc R U . . .
C24 C 0.64544(17) 0.44833(17) 0.23831(10) 0.0604(5) Uani 1 1 d . . . . .
H24 H 0.7096 0.3891 0.2476 0.073 Uiso 1 1 calc R U . . .
C25 C 0.57121(15) 0.77415(15) 0.26307(9) 0.0506(4) Uani 1 1 d . . . . .
C26 C 0.4693(2) 0.95831(17) 0.28626(13) 0.0817(7) Uani 1 1 d . . . . .
H26A H 0.5408 0.9958 0.2648 0.123 Uiso 1 1 calc R U . . .
H26B H 0.4717 0.9499 0.3372 0.123 Uiso 1 1 calc R U . . .
H26C H 0.3981 1.0088 0.2702 0.123 Uiso 1 1 calc R U . . .
O4 O 1.02452(10) 0.21646(9) 0.37954(6) 0.0466(3) Uani 1 1 d . . . . .
O5 O 1.17338(13) -0.30397(14) 0.21383(11) 0.0975(6) Uani 1 1 d . . . . .
O6 O 0.97685(11) -0.33187(10) 0.22902(7) 0.0606(3) Uani 1 1 d . . . . .
N4 N 0.71698(13) 0.45088(13) 0.43945(8) 0.0551(4) Uani 1 1 d . . . . .
N5 N 1.32754(16) 0.23580(18) 0.34542(11) 0.0810(5) Uani 1 1 d . . . . .
N6 N 0.78269(12) 0.24808(12) 0.43810(8) 0.0506(3) Uani 1 1 d . . . . .
C27 C 0.73541(18) 0.57244(16) 0.43530(10) 0.0595(5) Uani 1 1 d . . . . .
C28 C 0.84786(19) 0.61453(15) 0.42508(9) 0.0591(5) Uani 1 1 d . . . . .
H28 H 0.8581 0.6970 0.4258 0.071 Uiso 1 1 calc R U . . .
C29 C 0.94987(16) 0.53445(14) 0.41329(8) 0.0498(4) Uani 1 1 d . . . . .
C30 C 1.06801(18) 0.57689(16) 0.40149(9) 0.0564(5) Uani 1 1 d . . . . .
H30 H 1.0782 0.6588 0.4036 0.068 Uiso 1 1 calc R U . . .
C31 C 1.16752(17) 0.50326(16) 0.38713(9) 0.0544(4) Uani 1 1 d . . . . .
C32 C 1.14753(15) 0.38002(15) 0.38043(8) 0.0488(4) Uani 1 1 d . . . . .
C33 C 1.03339(14) 0.33494(13) 0.39090(8) 0.0438(4) Uani 1 1 d . . . . .
C34 C 0.93101(15) 0.40897(14) 0.41191(8) 0.0448(4) Uani 1 1 d . . . . .
C35 C 0.80901(15) 0.37158(14) 0.43037(8) 0.0461(4) Uani 1 1 d . . . . .
C36 C 0.6221(2) 0.65308(19) 0.44601(13) 0.0818(6) Uani 1 1 d . . . . .
H36A H 0.5590 0.6340 0.4174 0.123 Uiso 1 1 calc R U . . .
H36B H 0.6391 0.7377 0.4320 0.123 Uiso 1 1 calc R U . . .
H36C H 0.5957 0.6390 0.4954 0.123 Uiso 1 1 calc R U . . .
C37 C 1.29300(19) 0.54895(19) 0.37598(11) 0.0721(6) Uani 1 1 d . . . . .
H37A H 1.3419 0.5117 0.4152 0.108 Uiso 1 1 calc R U . . .
H37B H 1.2878 0.6366 0.3733 0.108 Uiso 1 1 calc R U . . .
H37C H 1.3295 0.5277 0.3324 0.108 Uiso 1 1 calc R U . . .
C38 C 1.24734(17) 0.29923(18) 0.36079(10) 0.0584(5) Uani 1 1 d . . . . .
C39 C 0.84436(16) 0.16436(14) 0.49588(9) 0.0537(4) Uani 1 1 d . . . . .
H39A H 0.8079 0.1785 0.5416 0.064 Uiso 1 1 calc R U . . .
H39B H 0.9296 0.1812 0.4948 0.064 Uiso 1 1 calc R U . . .
C40 C 0.83412(19) 0.03164(16) 0.48793(12) 0.0690(5) Uani 1 1 d . . . . .
H40A H 0.8770 0.0155 0.4443 0.083 Uiso 1 1 calc R U . . .
H40B H 0.8719 -0.0219 0.5277 0.083 Uiso 1 1 calc R U . . .
C41 C 0.7021(2) 0.0041(2) 0.48589(15) 0.0898(7) Uani 1 1 d . . . . .
H41A H 0.6620 0.0082 0.5321 0.108 Uiso 1 1 calc R U . . .
H41B H 0.6975 -0.0783 0.4756 0.108 Uiso 1 1 calc R U . . .
C42 C 0.63783(19) 0.0959(2) 0.42919(14) 0.0842(7) Uani 1 1 d . . . . .
H42A H 0.6709 0.0838 0.3824 0.101 Uiso 1 1 calc R U . . .
H42B H 0.5519 0.0816 0.4314 0.101 Uiso 1 1 calc R U . . .
C43 C 0.65259(16) 0.22690(18) 0.43910(12) 0.0683(5) Uani 1 1 d . . . . .
H43A H 0.6133 0.2835 0.4011 0.082 Uiso 1 1 calc R U . . .
H43B H 0.6141 0.2415 0.4842 0.082 Uiso 1 1 calc R U . . .
C44 C 0.97641(17) 0.20919(15) 0.31145(9) 0.0546(4) Uani 1 1 d . . . . .
H44A H 1.0155 0.2657 0.2743 0.066 Uiso 1 1 calc R U . . .
H44B H 0.8896 0.2318 0.3121 0.066 Uiso 1 1 calc R U . . .
C45 C 0.99931(15) 0.08054(14) 0.29660(9) 0.0478(4) Uani 1 1 d . . . . .
C46 C 1.11531(16) 0.02273(16) 0.29992(10) 0.0590(5) Uani 1 1 d . . . . .
H46 H 1.1786 0.0615 0.3153 0.071 Uiso 1 1 calc R U . . .
C47 C 1.13788(16) -0.09184(16) 0.28062(10) 0.0595(5) Uani 1 1 d . . . . .
H47 H 1.2164 -0.1293 0.2824 0.071 Uiso 1 1 calc R U . . .
C48 C 1.04411(14) -0.15125(14) 0.25856(9) 0.0472(4) Uani 1 1 d . . . . .
C49 C 0.92803(15) -0.09612(16) 0.25726(10) 0.0584(5) Uani 1 1 d . . . . .
H49 H 0.8640 -0.1365 0.2440 0.070 Uiso 1 1 calc R U . . .
C50 C 0.90661(16) 0.01962(16) 0.27575(11) 0.0598(5) Uani 1 1 d . . . . .
H50 H 0.8281 0.0569 0.2740 0.072 Uiso 1 1 calc R U . . .
C51 C 1.07381(16) -0.26916(15) 0.23184(10) 0.0535(4) Uani 1 1 d . . . . .
C52 C 0.9993(2) -0.44595(17) 0.20196(13) 0.0780(6) Uani 1 1 d . . . . .
H52A H 1.0210 -0.4292 0.1520 0.117 Uiso 1 1 calc R U . . .
H52B H 0.9271 -0.4905 0.2090 0.117 Uiso 1 1 calc R U . . .
H52C H 1.0647 -0.4941 0.2269 0.117 Uiso 1 1 calc R 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
O1 C7 1.3766(17) . ?
O1 C18 1.4415(19) . ?
O2 C25 1.196(2) . ?
O3 C25 1.329(2) . ?
O3 C26 1.440(2) . ?
N1 C9 1.318(2) . ?
N1 C1 1.366(2) . ?
N2 C12 1.141(2) . ?
N3 C9 1.393(2) . ?
N3 C17 1.465(2) . ?
N3 C13 1.470(2) . ?
C1 C2 1.351(3) . ?
C1 C10 1.508(2) . ?
C2 C3 1.406(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.411(2) . ?
C3 C8 1.424(2) . ?
C4 C5 1.361(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.424(2) . ?
C5 C11 1.504(3) . ?
C6 C7 1.380(2) . ?
C6 C12 1.434(2) . ?
C7 C8 1.416(2) . ?
C8 C9 1.446(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.516(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.515(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.519(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.514(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.496(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C24 1.384(2) . ?
C19 C20 1.387(2) . ?
C20 C21 1.377(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.386(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.379(2) . ?
C22 C25 1.484(2) . ?
C23 C24 1.379(2) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
O4 C33 1.3752(17) . ?
O4 C44 1.4409(19) . ?
O5 C51 1.188(2) . ?
O6 C51 1.326(2) . ?
O6 C52 1.4406(19) . ?
N4 C35 1.314(2) . ?
N4 C27 1.365(2) . ?
N5 C38 1.143(2) . ?
N6 C35 1.401(2) . ?
N6 C43 1.469(2) . ?
N6 C39 1.473(2) . ?
C27 C28 1.351(3) . ?
C27 C36 1.504(3) . ?
C28 C29 1.410(2) . ?
C28 H28 0.9300 . ?
C29 C30 1.413(2) . ?
C29 C34 1.424(2) . ?
C30 C31 1.360(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.425(2) . ?
C31 C37 1.502(2) . ?
C32 C33 1.382(2) . ?
C32 C38 1.438(3) . ?
C33 C34 1.424(2) . ?
C34 C35 1.446(2) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C39 C40 1.514(2) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C41 1.513(3) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 C42 1.517(3) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C43 1.515(3) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 C45 1.497(2) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C45 C50 1.375(2) . ?
C45 C46 1.385(2) . ?
C46 C47 1.379(2) . ?
C46 H46 0.9300 . ?
C47 C48 1.384(2) . ?
C47 H47 0.9300 . ?
C48 C49 1.374(2) . ?
C48 C51 1.485(2) . ?
C49 C50 1.384(2) . ?
C49 H49 0.9300 . ?
C50 H50 0.9300 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C18 113.97(12) . . ?
C25 O3 C26 115.89(14) . . ?
C9 N1 C1 119.47(16) . . ?
C9 N3 C17 116.47(14) . . ?
C9 N3 C13 117.82(13) . . ?
C17 N3 C13 111.46(15) . . ?
C2 C1 N1 122.50(15) . . ?
C2 C1 C10 121.95(18) . . ?
N1 C1 C10 115.52(19) . . ?
C1 C2 C3 120.01(16) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 121.72(15) . . ?
C2 C3 C8 118.09(16) . . ?
C4 C3 C8 120.16(14) . . ?
C5 C4 C3 122.53(15) . . ?
C5 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
C4 C5 C6 116.86(16) . . ?
C4 C5 C11 121.86(16) . . ?
C6 C5 C11 121.28(16) . . ?
C7 C6 C5 122.15(15) . . ?
C7 C6 C12 118.32(15) . . ?
C5 C6 C12 119.43(16) . . ?
O1 C7 C6 116.71(13) . . ?
O1 C7 C8 122.64(14) . . ?
C6 C7 C8 120.64(14) . . ?
C7 C8 C3 116.63(15) . . ?
C7 C8 C9 126.71(14) . . ?
C3 C8 C9 116.60(14) . . ?
N1 C9 N3 117.36(15) . . ?
N1 C9 C8 121.72(15) . . ?
N3 C9 C8 120.91(14) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C6 177.8(2) . . ?
N3 C13 C14 111.11(15) . . ?
N3 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
N3 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 C13 110.35(17) . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C16 110.03(18) . . ?
C14 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C17 C16 C15 111.9(2) . . ?
C17 C16 H16A 109.2 . . ?
C15 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N3 C17 C16 109.61(17) . . ?
N3 C17 H17A 109.7 . . ?
C16 C17 H17A 109.7 . . ?
N3 C17 H17B 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
O1 C18 C19 108.90(13) . . ?
O1 C18 H18A 109.9 . . ?
C19 C18 H18A 109.9 . . ?
O1 C18 H18B 109.9 . . ?
C19 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
C24 C19 C20 118.47(15) . . ?
C24 C19 C18 120.22(15) . . ?
C20 C19 C18 121.27(15) . . ?
C21 C20 C19 120.69(15) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 120.31(15) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 119.38(15) . . ?
C23 C22 C25 118.58(15) . . ?
C21 C22 C25 122.04(15) . . ?
C22 C23 C24 120.09(16) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C19 121.06(16) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
O2 C25 O3 122.53(16) . . ?
O2 C25 C22 124.56(17) . . ?
O3 C25 C22 112.90(14) . . ?
O3 C26 H26A 109.5 . . ?
O3 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O3 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C33 O4 C44 113.44(12) . . ?
C51 O6 C52 115.66(15) . . ?
C35 N4 C27 120.25(16) . . ?
C35 N6 C43 115.09(13) . . ?
C35 N6 C39 115.76(13) . . ?
C43 N6 C39 110.91(14) . . ?
C28 C27 N4 121.81(16) . . ?
C28 C27 C36 123.46(17) . . ?
N4 C27 C36 114.68(18) . . ?
C27 C28 C29 120.51(16) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C28 C29 C30 121.43(15) . . ?
C28 C29 C34 118.36(16) . . ?
C30 C29 C34 120.19(15) . . ?
C31 C30 C29 122.93(15) . . ?
C31 C30 H30 118.5 . . ?
C29 C30 H30 118.5 . . ?
C30 C31 C32 116.97(16) . . ?
C30 C31 C37 122.41(16) . . ?
C32 C31 C37 120.58(17) . . ?
C33 C32 C31 121.97(15) . . ?
C33 C32 C38 117.99(15) . . ?
C31 C32 C38 120.03(15) . . ?
O4 C33 C32 116.61(14) . . ?
O4 C33 C34 122.41(14) . . ?
C32 C33 C34 120.98(14) . . ?
C33 C34 C29 116.52(15) . . ?
C33 C34 C35 127.16(14) . . ?
C29 C34 C35 116.30(14) . . ?
N4 C35 N6 116.49(15) . . ?
N4 C35 C34 122.23(14) . . ?
N6 C35 C34 121.26(13) . . ?
C27 C36 H36A 109.5 . . ?
C27 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C27 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C31 C37 H37A 109.5 . . ?
C31 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C31 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N5 C38 C32 179.3(2) . . ?
N6 C39 C40 110.83(15) . . ?
N6 C39 H39A 109.5 . . ?
C40 C39 H39A 109.5 . . ?
N6 C39 H39B 109.5 . . ?
C40 C39 H39B 109.5 . . ?
H39A C39 H39B 108.1 . . ?
C41 C40 C39 110.74(16) . . ?
C41 C40 H40A 109.5 . . ?
C39 C40 H40A 109.5 . . ?
C41 C40 H40B 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 108.1 . . ?
C40 C41 C42 110.32(18) . . ?
C40 C41 H41A 109.6 . . ?
C42 C41 H41A 109.6 . . ?
C40 C41 H41B 109.6 . . ?
C42 C41 H41B 109.6 . . ?
H41A C41 H41B 108.1 . . ?
C43 C42 C41 111.55(19) . . ?
C43 C42 H42A 109.3 . . ?
C41 C42 H42A 109.3 . . ?
C43 C42 H42B 109.3 . . ?
C41 C42 H42B 109.3 . . ?
H42A C42 H42B 108.0 . . ?
N6 C43 C42 109.62(15) . . ?
N6 C43 H43A 109.7 . . ?
C42 C43 H43A 109.7 . . ?
N6 C43 H43B 109.7 . . ?
C42 C43 H43B 109.7 . . ?
H43A C43 H43B 108.2 . . ?
O4 C44 C45 109.04(13) . . ?
O4 C44 H44A 109.9 . . ?
C45 C44 H44A 109.9 . . ?
O4 C44 H44B 109.9 . . ?
C45 C44 H44B 109.9 . . ?
H44A C44 H44B 108.3 . . ?
C50 C45 C46 118.54(15) . . ?
C50 C45 C44 120.56(15) . . ?
C46 C45 C44 120.81(15) . . ?
C47 C46 C45 120.63(16) . . ?
C47 C46 H46 119.7 . . ?
C45 C46 H46 119.7 . . ?
C46 C47 C48 120.21(16) . . ?
C46 C47 H47 119.9 . . ?
C48 C47 H47 119.9 . . ?
C49 C48 C47 119.49(15) . . ?
C49 C48 C51 121.72(15) . . ?
C47 C48 C51 118.64(15) . . ?
C48 C49 C50 119.85(16) . . ?
C48 C49 H49 120.1 . . ?
C50 C49 H49 120.1 . . ?
C45 C50 C49 121.23(16) . . ?
C45 C50 H50 119.4 . . ?
C49 C50 H50 119.4 . . ?
O5 C51 O6 122.89(16) . . ?
O5 C51 C48 124.13(16) . . ?
O6 C51 C48 112.98(14) . . ?
O6 C52 H52A 109.5 . . ?
O6 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
O6 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C2 4.7(2) . . . . ?
C9 N1 C1 C10 -177.55(16) . . . . ?
N1 C1 C2 C3 -9.1(3) . . . . ?
C10 C1 C2 C3 173.25(16) . . . . ?
C1 C2 C3 C4 -176.57(16) . . . . ?
C1 C2 C3 C8 1.6(2) . . . . ?
C2 C3 C4 C5 175.51(16) . . . . ?
C8 C3 C4 C5 -2.7(2) . . . . ?
C3 C4 C5 C6 -5.5(2) . . . . ?
C3 C4 C5 C11 174.95(16) . . . . ?
C4 C5 C6 C7 6.0(2) . . . . ?
C11 C5 C6 C7 -174.38(16) . . . . ?
C4 C5 C6 C12 -170.32(16) . . . . ?
C11 C5 C6 C12 9.3(2) . . . . ?
C18 O1 C7 C6 105.27(16) . . . . ?
C18 O1 C7 C8 -74.61(19) . . . . ?
C5 C6 C7 O1 -178.21(14) . . . . ?
C12 C6 C7 O1 -1.8(2) . . . . ?
C5 C6 C7 C8 1.7(2) . . . . ?
C12 C6 C7 C8 178.07(15) . . . . ?
O1 C7 C8 C3 170.26(13) . . . . ?
C6 C7 C8 C3 -9.6(2) . . . . ?
O1 C7 C8 C9 -6.6(2) . . . . ?
C6 C7 C8 C9 173.49(15) . . . . ?
C2 C3 C8 C7 -168.08(14) . . . . ?
C4 C3 C8 C7 10.1(2) . . . . ?
C2 C3 C8 C9 9.1(2) . . . . ?
C4 C3 C8 C9 -172.65(14) . . . . ?
C1 N1 C9 N3 -173.92(14) . . . . ?
C1 N1 C9 C8 7.2(2) . . . . ?
C17 N3 C9 N1 -10.1(2) . . . . ?
C13 N3 C9 N1 126.35(16) . . . . ?
C17 N3 C9 C8 168.82(16) . . . . ?
C13 N3 C9 C8 -54.7(2) . . . . ?
C7 C8 C9 N1 162.99(15) . . . . ?
C3 C8 C9 N1 -13.9(2) . . . . ?
C7 C8 C9 N3 -15.9(2) . . . . ?
C3 C8 C9 N3 167.22(14) . . . . ?
C9 N3 C13 C14 161.58(15) . . . . ?
C17 N3 C13 C14 -59.9(2) . . . . ?
N3 C13 C14 C15 56.6(2) . . . . ?
C13 C14 C15 C16 -53.5(2) . . . . ?
C14 C15 C16 C17 54.4(3) . . . . ?
C9 N3 C17 C16 -161.81(18) . . . . ?
C13 N3 C17 C16 59.1(2) . . . . ?
C15 C16 C17 N3 -56.7(3) . . . . ?
C7 O1 C18 C19 -171.17(13) . . . . ?
O1 C18 C19 C24 -138.72(17) . . . . ?
O1 C18 C19 C20 43.7(2) . . . . ?
C24 C19 C20 C21 -1.0(3) . . . . ?
C18 C19 C20 C21 176.53(15) . . . . ?
C19 C20 C21 C22 0.2(3) . . . . ?
C20 C21 C22 C23 0.8(3) . . . . ?
C20 C21 C22 C25 -178.21(15) . . . . ?
C21 C22 C23 C24 -1.0(3) . . . . ?
C25 C22 C23 C24 178.05(16) . . . . ?
C22 C23 C24 C19 0.2(3) . . . . ?
C20 C19 C24 C23 0.8(3) . . . . ?
C18 C19 C24 C23 -176.76(17) . . . . ?
C26 O3 C25 O2 1.5(3) . . . . ?
C26 O3 C25 C22 -179.90(16) . . . . ?
C23 C22 C25 O2 16.0(3) . . . . ?
C21 C22 C25 O2 -164.96(19) . . . . ?
C23 C22 C25 O3 -162.50(16) . . . . ?
C21 C22 C25 O3 16.5(2) . . . . ?
C35 N4 C27 C28 -3.0(3) . . . . ?
C35 N4 C27 C36 179.40(16) . . . . ?
N4 C27 C28 C29 4.5(3) . . . . ?
C36 C27 C28 C29 -178.14(18) . . . . ?
C27 C28 C29 C30 179.09(17) . . . . ?
C27 C28 C29 C34 0.5(3) . . . . ?
C28 C29 C30 C31 -177.29(16) . . . . ?
C34 C29 C30 C31 1.3(3) . . . . ?
C29 C30 C31 C32 3.3(3) . . . . ?
C29 C30 C31 C37 -178.88(16) . . . . ?
C30 C31 C32 C33 -2.7(2) . . . . ?
C37 C31 C32 C33 179.48(16) . . . . ?
C30 C31 C32 C38 176.03(16) . . . . ?
C37 C31 C32 C38 -1.8(3) . . . . ?
C44 O4 C33 C32 -100.74(17) . . . . ?
C44 O4 C33 C34 78.84(18) . . . . ?
C31 C32 C33 O4 176.93(14) . . . . ?
C38 C32 C33 O4 -1.8(2) . . . . ?
C31 C32 C33 C34 -2.7(2) . . . . ?
C38 C32 C33 C34 178.63(15) . . . . ?
O4 C33 C34 C29 -172.50(13) . . . . ?
C32 C33 C34 C29 7.1(2) . . . . ?
O4 C33 C34 C35 5.9(3) . . . . ?
C32 C33 C34 C35 -174.57(15) . . . . ?
C28 C29 C34 C33 172.22(15) . . . . ?
C30 C29 C34 C33 -6.4(2) . . . . ?
C28 C29 C34 C35 -6.3(2) . . . . ?
C30 C29 C34 C35 175.04(15) . . . . ?
C27 N4 C35 N6 177.75(15) . . . . ?
C27 N4 C35 C34 -3.5(2) . . . . ?
C43 N6 C35 N4 13.4(2) . . . . ?
C39 N6 C35 N4 -118.21(16) . . . . ?
C43 N6 C35 C34 -165.42(16) . . . . ?
C39 N6 C35 C34 63.0(2) . . . . ?
C33 C34 C35 N4 -170.30(16) . . . . ?
C29 C34 C35 N4 8.1(2) . . . . ?
C33 C34 C35 N6 8.4(3) . . . . ?
C29 C34 C35 N6 -173.23(14) . . . . ?
C35 N6 C39 C40 -166.13(14) . . . . ?
C43 N6 C39 C40 60.38(18) . . . . ?
N6 C39 C40 C41 -56.5(2) . . . . ?
C39 C40 C41 C42 53.1(3) . . . . ?
C40 C41 C42 C43 -54.0(3) . . . . ?
C35 N6 C43 C42 166.05(17) . . . . ?
C39 N6 C43 C42 -60.1(2) . . . . ?
C41 C42 C43 N6 57.2(2) . . . . ?
C33 O4 C44 C45 165.95(13) . . . . ?
O4 C44 C45 C50 130.28(17) . . . . ?
O4 C44 C45 C46 -53.1(2) . . . . ?
C50 C45 C46 C47 2.0(3) . . . . ?
C44 C45 C46 C47 -174.71(17) . . . . ?
C45 C46 C47 C48 -0.9(3) . . . . ?
C46 C47 C48 C49 -1.1(3) . . . . ?
C46 C47 C48 C51 174.43(17) . . . . ?
C47 C48 C49 C50 2.1(3) . . . . ?
C51 C48 C49 C50 -173.36(18) . . . . ?
C46 C45 C50 C49 -1.0(3) . . . . ?
C44 C45 C50 C49 175.65(18) . . . . ?
C48 C49 C50 C45 -1.0(3) . . . . ?
C52 O6 C51 O5 -0.4(3) . . . . ?
C52 O6 C51 C48 178.63(16) . . . . ?
C49 C48 C51 O5 158.9(2) . . . . ?
C47 C48 C51 O5 -16.6(3) . . . . ?
C49 C48 C51 O6 -20.2(2) . . . . ?
C47 C48 C51 O6 164.37(16) . . . . ?

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
C44 H44B N6 0.97 2.64 3.199(2) 116.6 .
C39 H39B O4 0.97 2.37 2.912(2) 114.9 .
C18 H18B N5 0.97 2.69 3.575(3) 152.2 1_455
C18 H18A N3 0.97 2.67 3.208(2) 115.7 .
C13 H13A O1 0.97 2.38 2.907(2) 113.5 .
C10 H10C O6 0.96 2.62 3.450(2) 145.0 .
C44 H44B N6 0.97 2.64 3.199(2) 116.6 .
C39 H39B O4 0.97 2.37 2.912(2) 114.9 .
C18 H18B N5 0.97 2.69 3.575(3) 152.2 1_455
C18 H18A N3 0.97 2.67 3.208(2) 115.7 .
C13 H13A O1 0.97 2.38 2.907(2) 113.5 .
C10 H10C O6 0.96 2.62 3.450(2) 145.0 .
C10 H10C O6 0.96 2.62 3.450(2) 145.0 .
C13 H13A O1 0.97 2.38 2.907(2) 113.5 .
C18 H18A N3 0.97 2.67 3.208(2) 115.7 .
C18 H18B N5 0.97 2.69 3.575(3) 152.2 1_455
C39 H39B O4 0.97 2.37 2.912(2) 114.9 .
C44 H44B N6 0.97 2.64 3.199(2) 116.6 .

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.029

_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_dd18249_0m
_database_code_depnum_ccdc_archive 'CCDC 2245989'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2023-03-03 deposited with the CCDC.	2023-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H23 F6 N3 O'
_chemical_formula_weight         507.47

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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'
'-x, -y, -z'

_cell_length_a                   9.4961(3)
_cell_length_b                   16.3124(5)
_cell_length_c                   17.0312(6)
_cell_angle_alpha                75.8520(10)
_cell_angle_beta                 84.4340(10)
_cell_angle_gamma                78.9830(10)
_cell_volume                     2507.53(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      4.376
_cell_measurement_theta_max      53.710

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5755
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            36842
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.449
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             9300
_reflns_number_gt                6128
_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)+(0.0558P)²+0.4454P] 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       0.039(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9300
_refine_ls_number_parameters     762
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1418
_refine_ls_wR_factor_gt          0.1192
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.001

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
N1 N 0.92336(17) 0.68221(10) 0.29018(10) 0.0631(4) Uani 1 1 d . . . . .
N2 N 0.88739(15) 0.75321(9) 0.15641(9) 0.0550(4) Uani 1 1 d . . . . .
N3 N 0.6947(2) 0.50315(14) -0.01228(16) 0.0988(7) Uani 1 1 d . . . . .
N4 N 0.40605(17) 0.80832(11) 0.09258(11) 0.0685(4) Uani 1 1 d . . . . .
N5 N 0.36849(17) 0.87974(10) 0.19617(10) 0.0666(4) Uani 1 1 d . . . . .
N6 N 0.3702(3) 0.60111(16) 0.51475(15) 0.1157(8) Uani 1 1 d . . . . .
O1 O 0.83577(13) 0.64443(8) 0.05784(8) 0.0623(4) Uani 1 1 d . . . . .
O2 O 0.41257(13) 0.76133(8) 0.35154(8) 0.0628(3) Uani 1 1 d . . . . .
C1 C 0.9065(2) 0.61684(13) 0.35616(13) 0.0703(6) Uani 1 1 d . . . . .
C2 C 0.8354(2) 0.55336(13) 0.35251(14) 0.0764(6) Uani 1 1 d . . . . .
H2 H 0.8156 0.5136 0.3997 0.092 Uiso 1 1 calc R U . . .
C3 C 0.7913(2) 0.54712(12) 0.27800(14) 0.0680(6) Uani 1 1 d . . . . .
C4 C 0.7219(2) 0.47977(13) 0.27144(16) 0.0805(7) Uani 1 1 d . . . . .
H4 H 0.6977 0.4415 0.3187 0.097 Uiso 1 1 calc R U . . .
C5 C 0.6892(2) 0.46848(12) 0.19982(17) 0.0756(6) Uani 1 1 d . . . . .
C6 C 0.7324(2) 0.52614(12) 0.12835(14) 0.0682(6) Uani 1 1 d . . . . .
C7 C 0.79868(19) 0.59369(11) 0.13192(13) 0.0607(5) Uani 1 1 d . . . . .
C8 C 0.82242(19) 0.60956(11) 0.20681(12) 0.0582(5) Uani 1 1 d . . . . .
C9 C 0.87889(18) 0.68112(11) 0.21991(12) 0.0553(5) Uani 1 1 d . . . . .
C10 C 0.9631(3) 0.62411(16) 0.43284(14) 0.0931(7) Uani 1 1 d . . . . .
H10A H 0.8937 0.6620 0.4582 0.140 Uiso 1 1 calc R U . . .
H10B H 1.0511 0.6466 0.4205 0.140 Uiso 1 1 calc R U . . .
H10C H 0.9808 0.5684 0.4690 0.140 Uiso 1 1 calc R U . . .
C11 C 0.6133(3) 0.39726(15) 0.19318(18) 0.1025(9) Uani 1 1 d . . . . .
H11A H 0.5829 0.3681 0.2464 0.154 Uiso 1 1 calc R U . . .
H11B H 0.6779 0.3573 0.1677 0.154 Uiso 1 1 calc R U . . .
H11C H 0.5310 0.4211 0.1612 0.154 Uiso 1 1 calc R U . . .
C12 C 0.7107(2) 0.51405(14) 0.05026(18) 0.0764(6) Uani 1 1 d . . . . .
C13 C 0.75045(18) 0.79703(11) 0.11997(11) 0.0548(4) Uani 1 1 d . . . . .
H13A H 0.6937 0.8298 0.1561 0.066 Uiso 1 1 calc R U . . .
H13B H 0.6966 0.7546 0.1130 0.066 Uiso 1 1 calc R U . . .
C14 C 0.7760(2) 0.85623(12) 0.03912(12) 0.0629(5) Uani 1 1 d . . . . .
H14A H 0.6846 0.8862 0.0174 0.075 Uiso 1 1 calc R U . . .
H14B H 0.8257 0.8230 0.0015 0.075 Uiso 1 1 calc R U . . .
C15 C 0.8652(3) 0.92082(13) 0.04815(13) 0.0770(6) Uani 1 1 d . . . . .
H15A H 0.8910 0.9539 -0.0051 0.092 Uiso 1 1 calc R U . . .
H15B H 0.8089 0.9602 0.0784 0.092 Uiso 1 1 calc R U . . .
C16 C 1.0001(2) 0.87637(13) 0.09166(12) 0.0727(6) Uani 1 1 d . . . . .
H16A H 1.0494 0.9192 0.1021 0.087 Uiso 1 1 calc R U . . .
H16B H 1.0637 0.8447 0.0570 0.087 Uiso 1 1 calc R U . . .
C17 C 0.9686(2) 0.81530(12) 0.17107(12) 0.0651(5) Uani 1 1 d . . . . .
H17A H 1.0579 0.7854 0.1954 0.078 Uiso 1 1 calc R U . . .
H17B H 0.9133 0.8472 0.2083 0.078 Uiso 1 1 calc R U . . .
C18 C 0.9860(2) 0.62931(14) 0.03286(13) 0.0750(6) Uani 1 1 d . . . . .
H18A H 1.0214 0.5683 0.0399 0.090 Uiso 1 1 calc R U . . .
H18B H 1.0414 0.6520 0.0649 0.090 Uiso 1 1 calc R U . . .
C19 C 0.9986(2) 0.67401(13) -0.05452(13) 0.0670(5) Uani 1 1 d . . . . .
C20 C 0.9351(3) 0.64858(14) -0.11217(15) 0.0801(6) Uani 1 1 d . . . . .
H20 H 0.8870 0.6021 -0.0964 0.096 Uiso 1 1 calc R U . . .
C21 C 0.9417(3) 0.69080(16) -0.19237(16) 0.0858(7) Uani 1 1 d . . . . .
C22 C 1.0102(3) 0.76131(15) -0.21741(15) 0.0814(6) Uani 1 1 d . . . . .
H22 H 1.0141 0.7900 -0.2717 0.098 Uiso 1 1 calc R U . . .
C23 C 1.0722(2) 0.78808(13) -0.16055(14) 0.0720(6) Uani 1 1 d . . . . .
C24 C 1.0681(2) 0.74404(13) -0.07995(13) 0.0696(6) Uani 1 1 d . . . . .
H24 H 1.1127 0.7618 -0.0423 0.084 Uiso 1 1 calc R U . . .
C25 C 0.8720(6) 0.6621(4) -0.2534(3) 0.1330(14) Uani 1 1 d . . . . .
C26 C 1.1408(4) 0.8658(2) -0.1859(2) 0.0943(8) Uani 1 1 d . . . . .
C27 C 0.4106(2) 0.73737(16) 0.06253(13) 0.0738(6) Uani 1 1 d . . . . .
C28 C 0.3720(2) 0.66447(15) 0.10876(14) 0.0731(6) Uani 1 1 d . . . . .
H28 H 0.3590 0.6211 0.0849 0.088 Uiso 1 1 calc R U . . .
C29 C 0.3513(2) 0.65441(13) 0.19331(13) 0.0644(5) Uani 1 1 d . . . . .
C30 C 0.3266(2) 0.57596(14) 0.24424(15) 0.0745(6) Uani 1 1 d . . . . .
H30 H 0.3091 0.5334 0.2206 0.089 Uiso 1 1 calc R U . . .
C31 C 0.3270(2) 0.55968(14) 0.32616(15) 0.0765(6) Uani 1 1 d . . . . .
C32 C 0.3567(2) 0.62559(14) 0.36005(13) 0.0687(5) Uani 1 1 d . . . . .
C33 C 0.37808(19) 0.70434(12) 0.31195(12) 0.0589(5) Uani 1 1 d . . . . .
C34 C 0.36706(18) 0.72336(12) 0.22757(12) 0.0574(5) Uani 1 1 d . . . . .
C35 C 0.37895(19) 0.80391(12) 0.17060(13) 0.0602(5) Uani 1 1 d . . . . .
C36 C 0.4622(3) 0.7458(2) -0.02480(15) 0.1058(9) Uani 1 1 d . . . . .
H36A H 0.5639 0.7453 -0.0298 0.159 Uiso 1 1 calc R U . . .
H36B H 0.4139 0.7988 -0.0568 0.159 Uiso 1 1 calc R U . . .
H36C H 0.4418 0.6986 -0.0436 0.159 Uiso 1 1 calc R U . . .
C37 C 0.3043(3) 0.47434(16) 0.38010(17) 0.1088(9) Uani 1 1 d . . . . .
H37A H 0.3250 0.4311 0.3493 0.163 Uiso 1 1 calc R U . . .
H37B H 0.2063 0.4785 0.4011 0.163 Uiso 1 1 calc R U . . .
H37C H 0.3670 0.4592 0.4243 0.163 Uiso 1 1 calc R U . . .
C38 C 0.3658(3) 0.61203(15) 0.44618(17) 0.0843(7) Uani 1 1 d . . . . .
C39 C 0.2439(2) 0.90505(14) 0.24938(14) 0.0735(6) Uani 1 1 d . . . . .
H39A H 0.2215 0.8546 0.2887 0.088 Uiso 1 1 calc R U . . .
H39B H 0.1610 0.9301 0.2171 0.088 Uiso 1 1 calc R U . . .
C40 C 0.2750(3) 0.96933(16) 0.29339(17) 0.0921(7) Uani 1 1 d . . . . .
H40A H 0.1905 0.9869 0.3262 0.111 Uiso 1 1 calc R U . . .
H40B H 0.3526 0.9427 0.3293 0.111 Uiso 1 1 calc R U . . .
C41 C 0.3163(3) 1.04724(17) 0.2335(2) 0.1095(9) Uani 1 1 d . . . . .
H41A H 0.2345 1.0782 0.2022 0.131 Uiso 1 1 calc R U . . .
H41B H 0.3444 1.0854 0.2624 0.131 Uiso 1 1 calc R U . . .
C42 C 0.4396(3) 1.01963(16) 0.17714(19) 0.1027(9) Uani 1 1 d . . . . .
H42A H 0.5245 0.9950 0.2079 0.123 Uiso 1 1 calc R U . . .
H42B H 0.4606 1.0695 0.1365 0.123 Uiso 1 1 calc R U . . .
C43 C 0.4054(3) 0.95420(14) 0.13531(15) 0.0835(7) Uani 1 1 d . . . . .
H43A H 0.3255 0.9799 0.1008 0.100 Uiso 1 1 calc R U . . .
H43B H 0.4880 0.9360 0.1015 0.100 Uiso 1 1 calc R U . . .
C44 C 0.5623(2) 0.76414(16) 0.34693(13) 0.0747(6) Uani 1 1 d . . . . .
H44A H 0.5894 0.7978 0.2943 0.090 Uiso 1 1 calc R U . . .
H44B H 0.6171 0.7065 0.3533 0.090 Uiso 1 1 calc R U . . .
C45 C 0.5955(2) 0.80330(13) 0.41198(12) 0.0638(5) Uani 1 1 d . . . . .
C46 C 0.4999(2) 0.81334(15) 0.47674(13) 0.0756(6) Uani 1 1 d . . . . .
H46 H 0.4108 0.7966 0.4799 0.091 Uiso 1 1 calc R U . . .
C47 C 0.5352(3) 0.84798(17) 0.53678(14) 0.0871(7) Uani 1 1 d . . . . .
C48 C 0.6674(3) 0.87208(18) 0.53349(17) 0.0991(8) Uani 1 1 d . . . . .
H48 H 0.6912 0.8953 0.5741 0.119 Uiso 1 1 calc R U . . .
C49 C 0.7637(3) 0.86157(16) 0.46971(16) 0.0885(7) Uani 1 1 d . . . . .
C50 C 0.7277(2) 0.82806(14) 0.40901(14) 0.0749(6) Uani 1 1 d . . . . .
H50 H 0.7930 0.8220 0.3656 0.090 Uiso 1 1 calc R U . . .
C51 C 0.4343(5) 0.8552(4) 0.6092(3) 0.1256(13) Uani 1 1 d . . . . .
C52 C 0.9088(5) 0.8846(4) 0.4672(4) 0.1324(14) Uani 1 1 d . . . . .
F1 F 0.9015(5) 0.5745(2) -0.2411(3) 0.1410(12) Uani 0.7 1 d . . P A 1
F2 F 0.7261(6) 0.6738(7) -0.2393(5) 0.179(2) Uani 0.6 1 d . . P A 1
F3 F 0.8928(15) 0.6953(8) -0.3267(4) 0.233(6) Uani 0.6 1 d . . P A 1
F4 F 1.1132(12) 0.9088(6) -0.2631(4) 0.124(3) Uani 0.5 1 d . . P B 1
F5 F 1.2768(8) 0.8490(5) -0.1884(5) 0.143(3) Uani 0.6 1 d . . P B 1
F6 F 1.0809(8) 0.9236(4) -0.1457(5) 0.128(2) Uani 0.5 1 d . . P B 1
F7 F 0.3120(9) 0.8316(9) 0.6079(6) 0.162(4) Uani 0.5 1 d . . P C 1
F8 F 0.4927(7) 0.8102(6) 0.6790(4) 0.147(3) Uani 0.5 1 d . . P C 1
F9 F 0.4085(13) 0.9337(6) 0.6187(7) 0.212(6) Uani 0.5 1 d . . P C 1
F10 F 0.9448(11) 0.8921(11) 0.5395(5) 0.179(4) Uani 0.5 1 d . . P D 1
F11 F 0.9283(9) 0.9559(7) 0.4132(11) 0.191(5) Uani 0.5 1 d . . P D 1
F12 F 1.0172(7) 0.8285(8) 0.4405(11) 0.186(4) Uani 0.5 1 d . . P D 1
F1' F 0.790(2) 0.6129(11) -0.2251(7) 0.178(3) Uani 0.3 1 d . U P A 2
F2' F 0.7835(15) 0.7215(9) -0.2932(8) 0.179(3) Uani 0.4 1 d . U P A 2
F3' F 0.9676(13) 0.6523(9) -0.3173(8) 0.171(3) Uani 0.4 1 d . U P A 2
F4' F 1.0852(12) 0.9244(6) -0.2369(8) 0.220(6) Uani 0.5 1 d . . P B 2
F5' F 1.2803(12) 0.8451(9) -0.2056(7) 0.128(5) Uani 0.4 1 d . . P B 2
F6' F 1.1674(8) 0.8945(4) -0.1167(5) 0.139(2) Uani 0.5 1 d . . P B 2
F7' F 0.3060(11) 0.8972(7) 0.5755(5) 0.187(3) Uani 0.5 1 d . U P C 2
F8' F 0.410(2) 0.7870(7) 0.6520(7) 0.264(8) Uani 0.5 1 d . . P C 2
F9' F 0.4403(10) 0.9181(8) 0.6409(6) 0.172(3) Uani 0.5 1 d . U P C 2
F10' F 0.9012(11) 0.9525(11) 0.4935(12) 0.222(3) Uani 0.5 1 d . U P D 2
F11' F 0.9600(19) 0.9038(15) 0.3980(9) 0.220(4) Uani 0.5 1 d . U P D 2
F12' F 0.9938(10) 0.8224(10) 0.5076(11) 0.220(5) Uani 0.5 1 d . . P D 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9 1.312(2) . ?
N1 C1 1.368(2) . ?
N2 C9 1.399(2) . ?
N2 C17 1.463(2) . ?
N2 C13 1.474(2) . ?
N3 C12 1.150(3) . ?
N4 C35 1.316(2) . ?
N4 C27 1.367(3) . ?
N5 C35 1.392(2) . ?
N5 C43 1.466(3) . ?
N5 C39 1.476(3) . ?
N6 C38 1.141(3) . ?
O1 C7 1.384(2) . ?
O1 C18 1.440(2) . ?
O2 C33 1.375(2) . ?
O2 C44 1.426(2) . ?
C1 C2 1.356(3) . ?
C1 C10 1.498(3) . ?
C2 C3 1.407(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.416(3) . ?
C3 C8 1.427(3) . ?
C4 C5 1.350(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.423(3) . ?
C5 C11 1.510(3) . ?
C6 C7 1.386(3) . ?
C6 C12 1.431(4) . ?
C7 C8 1.409(3) . ?
C8 C9 1.446(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.504(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.516(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.511(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.513(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.493(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.382(3) . ?
C19 C24 1.385(3) . ?
C20 C21 1.373(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(3) . ?
C21 C25 1.492(4) . ?
C22 C23 1.375(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.386(3) . ?
C23 C26 1.488(3) . ?
C24 H24 0.9300 . ?
C25 F1' 1.205(13) . ?
C25 F3 1.247(8) . ?
C25 F2' 1.259(11) . ?
C25 F3' 1.369(13) . ?
C25 F2 1.368(9) . ?
C25 F1 1.370(7) . ?
C26 F4' 1.199(9) . ?
C26 F5 1.267(8) . ?
C26 F6 1.309(7) . ?
C26 F5' 1.335(11) . ?
C26 F4 1.354(9) . ?
C26 F6' 1.430(8) . ?
C27 C28 1.350(3) . ?
C27 C36 1.502(3) . ?
C28 C29 1.407(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.406(3) . ?
C29 C34 1.425(3) . ?
C30 C31 1.355(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.421(3) . ?
C31 C37 1.510(3) . ?
C32 C33 1.384(3) . ?
C32 C38 1.438(3) . ?
C33 C34 1.404(3) . ?
C34 C35 1.447(3) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C39 C40 1.514(3) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C41 1.513(4) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 C42 1.512(4) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C43 1.517(3) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 C45 1.492(3) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C45 C46 1.381(3) . ?
C45 C50 1.383(3) . ?
C46 C47 1.378(3) . ?
C46 H46 0.9300 . ?
C47 C48 1.377(3) . ?
C47 C51 1.501(4) . ?
C48 C49 1.373(3) . ?
C48 H48 0.9300 . ?
C49 C50 1.379(3) . ?
C49 C52 1.490(4) . ?
C50 H50 0.9300 . ?
C51 F8' 1.220(9) . ?
C51 F9' 1.282(9) . ?
C51 F7 1.295(8) . ?
C51 F9 1.304(11) . ?
C51 F8 1.344(9) . ?
C51 F7' 1.381(11) . ?
C52 F11' 1.222(12) . ?
C52 F12' 1.269(11) . ?
C52 F10' 1.278(9) . ?
C52 F11 1.326(11) . ?
C52 F10 1.349(10) . ?
C52 F12 1.363(9) . ?

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
C9 N1 C1 119.81(17) . . ?
C9 N2 C17 115.99(15) . . ?
C9 N2 C13 115.57(13) . . ?
C17 N2 C13 110.86(14) . . ?
C35 N4 C27 120.03(18) . . ?
C35 N5 C43 116.69(18) . . ?
C35 N5 C39 118.96(16) . . ?
C43 N5 C39 111.28(17) . . ?
C7 O1 C18 115.08(14) . . ?
C33 O2 C44 113.80(14) . . ?
C2 C1 N1 121.6(2) . . ?
C2 C1 C10 123.1(2) . . ?
N1 C1 C10 115.20(19) . . ?
C1 C2 C3 120.62(19) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 122.1(2) . . ?
C2 C3 C8 118.27(19) . . ?
C4 C3 C8 119.6(2) . . ?
C5 C4 C3 123.2(2) . . ?
C5 C4 H4 118.4 . . ?
C3 C4 H4 118.4 . . ?
C4 C5 C6 117.12(19) . . ?
C4 C5 C11 123.0(2) . . ?
C6 C5 C11 119.9(2) . . ?
C7 C6 C5 121.6(2) . . ?
C7 C6 C12 118.26(19) . . ?
C5 C6 C12 120.08(19) . . ?
O1 C7 C6 115.59(19) . . ?
O1 C7 C8 123.23(15) . . ?
C6 C7 C8 121.16(18) . . ?
C7 C8 C3 116.81(17) . . ?
C7 C8 C9 127.29(16) . . ?
C3 C8 C9 115.87(19) . . ?
N1 C9 N2 117.22(16) . . ?
N1 C9 C8 122.67(16) . . ?
N2 C9 C8 120.11(17) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C6 179.0(3) . . ?
N2 C13 C14 111.00(14) . . ?
N2 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
N2 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 110.24(16) . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 110.96(16) . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 C17 112.24(17) . . ?
C15 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N2 C17 C16 109.50(16) . . ?
N2 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
N2 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
O1 C18 C19 106.79(17) . . ?
O1 C18 H18A 110.4 . . ?
C19 C18 H18A 110.4 . . ?
O1 C18 H18B 110.4 . . ?
C19 C18 H18B 110.4 . . ?
H18A C18 H18B 108.6 . . ?
C20 C19 C24 118.0(2) . . ?
C20 C19 C18 120.39(19) . . ?
C24 C19 C18 121.6(2) . . ?
C21 C20 C19 121.1(2) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 120.7(2) . . ?
C20 C21 C25 120.0(3) . . ?
C22 C21 C25 119.3(3) . . ?
C23 C22 C21 118.8(2) . . ?
C23 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
C22 C23 C24 120.3(2) . . ?
C22 C23 C26 119.5(2) . . ?
C24 C23 C26 120.2(2) . . ?
C19 C24 C23 121.1(2) . . ?
C19 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
F1' C25 F2' 97.9(11) . . ?
F1' C25 F3' 122.9(11) . . ?
F2' C25 F3' 96.3(9) . . ?
F3 C25 F2 105.6(8) . . ?
F3 C25 F1 109.6(8) . . ?
F2 C25 F1 99.8(6) . . ?
F1' C25 C21 114.9(6) . . ?
F3 C25 C21 118.6(5) . . ?
F2' C25 C21 112.5(6) . . ?
F3' C25 C21 109.7(6) . . ?
F2 C25 C21 110.9(5) . . ?
F1 C25 C21 110.6(4) . . ?
F5 C26 F6 116.0(6) . . ?
F4' C26 F5' 110.3(8) . . ?
F5 C26 F4 102.4(6) . . ?
F6 C26 F4 101.2(6) . . ?
F4' C26 F6' 111.1(8) . . ?
F5' C26 F6' 93.3(6) . . ?
F4' C26 C23 117.7(6) . . ?
F5 C26 C23 113.5(4) . . ?
F6 C26 C23 110.7(4) . . ?
F5' C26 C23 111.0(6) . . ?
F4 C26 C23 112.0(5) . . ?
F6' C26 C23 110.6(3) . . ?
C28 C27 N4 121.9(2) . . ?
C28 C27 C36 122.4(2) . . ?
N4 C27 C36 115.7(2) . . ?
C27 C28 C29 119.7(2) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 H28 120.2 . . ?
C30 C29 C28 121.2(2) . . ?
C30 C29 C34 119.9(2) . . ?
C28 C29 C34 118.67(19) . . ?
C31 C30 C29 122.9(2) . . ?
C31 C30 H30 118.5 . . ?
C29 C30 H30 118.5 . . ?
C30 C31 C32 117.0(2) . . ?
C30 C31 C37 122.4(2) . . ?
C32 C31 C37 120.5(2) . . ?
C33 C32 C31 121.6(2) . . ?
C33 C32 C38 117.81(19) . . ?
C31 C32 C38 120.5(2) . . ?
O2 C33 C32 116.12(18) . . ?
O2 C33 C34 122.66(17) . . ?
C32 C33 C34 121.22(18) . . ?
C33 C34 C29 116.63(18) . . ?
C33 C34 C35 127.25(17) . . ?
C29 C34 C35 116.00(18) . . ?
N4 C35 N5 116.82(18) . . ?
N4 C35 C34 121.56(18) . . ?
N5 C35 C34 121.55(18) . . ?
C27 C36 H36A 109.5 . . ?
C27 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C27 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C31 C37 H37A 109.5 . . ?
C31 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C31 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N6 C38 C32 178.6(3) . . ?
N5 C39 C40 110.91(18) . . ?
N5 C39 H39A 109.5 . . ?
C40 C39 H39A 109.5 . . ?
N5 C39 H39B 109.5 . . ?
C40 C39 H39B 109.5 . . ?
H39A C39 H39B 108.0 . . ?
C41 C40 C39 110.6(2) . . ?
C41 C40 H40A 109.5 . . ?
C39 C40 H40A 109.5 . . ?
C41 C40 H40B 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 108.1 . . ?
C42 C41 C40 109.9(2) . . ?
C42 C41 H41A 109.7 . . ?
C40 C41 H41A 109.7 . . ?
C42 C41 H41B 109.7 . . ?
C40 C41 H41B 109.7 . . ?
H41A C41 H41B 108.2 . . ?
C41 C42 C43 111.8(2) . . ?
C41 C42 H42A 109.3 . . ?
C43 C42 H42A 109.3 . . ?
C41 C42 H42B 109.3 . . ?
C43 C42 H42B 109.3 . . ?
H42A C42 H42B 107.9 . . ?
N5 C43 C42 109.7(2) . . ?
N5 C43 H43A 109.7 . . ?
C42 C43 H43A 109.7 . . ?
N5 C43 H43B 109.7 . . ?
C42 C43 H43B 109.7 . . ?
H43A C43 H43B 108.2 . . ?
O2 C44 C45 109.72(16) . . ?
O2 C44 H44A 109.7 . . ?
C45 C44 H44A 109.7 . . ?
O2 C44 H44B 109.7 . . ?
C45 C44 H44B 109.7 . . ?
H44A C44 H44B 108.2 . . ?
C46 C45 C50 118.64(19) . . ?
C46 C45 C44 122.01(18) . . ?
C50 C45 C44 119.31(19) . . ?
C47 C46 C45 120.5(2) . . ?
C47 C46 H46 119.7 . . ?
C45 C46 H46 119.7 . . ?
C48 C47 C46 120.4(2) . . ?
C48 C47 C51 118.8(3) . . ?
C46 C47 C51 120.7(3) . . ?
C49 C48 C47 119.4(2) . . ?
C49 C48 H48 120.3 . . ?
C47 C48 H48 120.3 . . ?
C48 C49 C50 120.2(2) . . ?
C48 C49 C52 119.7(3) . . ?
C50 C49 C52 120.0(3) . . ?
C49 C50 C45 120.7(2) . . ?
C49 C50 H50 119.6 . . ?
C45 C50 H50 119.6 . . ?
F8' C51 F9' 120.4(8) . . ?
F7 C51 F9 107.9(8) . . ?
F7 C51 F8 107.0(8) . . ?
F9 C51 F8 102.9(6) . . ?
F8' C51 F7' 106.1(9) . . ?
F9' C51 F7' 90.9(8) . . ?
F8' C51 C47 115.1(6) . . ?
F9' C51 C47 115.4(5) . . ?
F7 C51 C47 115.3(4) . . ?
F9 C51 C47 110.7(7) . . ?
F8 C51 C47 112.3(5) . . ?
F7' C51 C47 103.5(5) . . ?
F11' C52 F12' 108.6(11) . . ?
F11' C52 F10' 103.9(9) . . ?
F12' C52 F10' 111.2(9) . . ?
F11 C52 F10 107.4(7) . . ?
F11 C52 F12 98.9(9) . . ?
F10 C52 F12 107.0(9) . . ?
F11' C52 C49 112.0(7) . . ?
F12' C52 C49 110.2(6) . . ?
F10' C52 C49 110.7(6) . . ?
F11 C52 C49 114.9(6) . . ?
F10 C52 C49 113.4(5) . . ?
F12 C52 C49 114.1(4) . . ?

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
C9 N1 C1 C2 -4.8(3) . . . . ?
C9 N1 C1 C10 179.15(19) . . . . ?
N1 C1 C2 C3 7.6(3) . . . . ?
C10 C1 C2 C3 -176.6(2) . . . . ?
C1 C2 C3 C4 177.4(2) . . . . ?
C1 C2 C3 C8 -0.5(3) . . . . ?
C2 C3 C4 C5 -174.4(2) . . . . ?
C8 C3 C4 C5 3.4(3) . . . . ?
C3 C4 C5 C6 2.3(3) . . . . ?
C3 C4 C5 C11 -179.1(2) . . . . ?
C4 C5 C6 C7 -3.2(3) . . . . ?
C11 C5 C6 C7 178.23(19) . . . . ?
C4 C5 C6 C12 175.4(2) . . . . ?
C11 C5 C6 C12 -3.2(3) . . . . ?
C18 O1 C7 C6 -103.1(2) . . . . ?
C18 O1 C7 C8 78.4(2) . . . . ?
C5 C6 C7 O1 179.62(17) . . . . ?
C12 C6 C7 O1 1.0(3) . . . . ?
C5 C6 C7 C8 -1.8(3) . . . . ?
C12 C6 C7 C8 179.57(18) . . . . ?
O1 C7 C8 C3 -174.15(16) . . . . ?
C6 C7 C8 C3 7.4(3) . . . . ?
O1 C7 C8 C9 4.0(3) . . . . ?
C6 C7 C8 C9 -174.45(18) . . . . ?
C2 C3 C8 C7 169.78(18) . . . . ?
C4 C3 C8 C7 -8.2(3) . . . . ?
C2 C3 C8 C9 -8.6(3) . . . . ?
C4 C3 C8 C9 173.48(17) . . . . ?
C1 N1 C9 N2 174.53(16) . . . . ?
C1 N1 C9 C8 -5.2(3) . . . . ?
C17 N2 C9 N1 10.6(2) . . . . ?
C13 N2 C9 N1 -121.65(18) . . . . ?
C17 N2 C9 C8 -169.62(16) . . . . ?
C13 N2 C9 C8 58.1(2) . . . . ?
C7 C8 C9 N1 -166.35(18) . . . . ?
C3 C8 C9 N1 11.8(3) . . . . ?
C7 C8 C9 N2 13.9(3) . . . . ?
C3 C8 C9 N2 -167.98(16) . . . . ?
C9 N2 C13 C14 -163.76(16) . . . . ?
C17 N2 C13 C14 61.6(2) . . . . ?
N2 C13 C14 C15 -56.8(2) . . . . ?
C13 C14 C15 C16 52.1(2) . . . . ?
C14 C15 C16 C17 -52.4(3) . . . . ?
C9 N2 C17 C16 165.72(16) . . . . ?
C13 N2 C17 C16 -59.9(2) . . . . ?
C15 C16 C17 N2 55.8(2) . . . . ?
C7 O1 C18 C19 167.17(16) . . . . ?
O1 C18 C19 C20 -63.8(2) . . . . ?
O1 C18 C19 C24 113.2(2) . . . . ?
C24 C19 C20 C21 0.7(3) . . . . ?
C18 C19 C20 C21 177.8(2) . . . . ?
C19 C20 C21 C22 -1.3(4) . . . . ?
C19 C20 C21 C25 -179.9(3) . . . . ?
C20 C21 C22 C23 0.4(4) . . . . ?
C25 C21 C22 C23 179.0(3) . . . . ?
C21 C22 C23 C24 1.1(3) . . . . ?
C21 C22 C23 C26 -177.5(2) . . . . ?
C20 C19 C24 C23 0.8(3) . . . . ?
C18 C19 C24 C23 -176.28(18) . . . . ?
C22 C23 C24 C19 -1.8(3) . . . . ?
C26 C23 C24 C19 176.8(2) . . . . ?
C20 C21 C25 F1' 13.5(14) . . . . ?
C22 C21 C25 F1' -165.1(13) . . . . ?
C20 C21 C25 F3 -172.3(10) . . . . ?
C22 C21 C25 F3 9.0(12) . . . . ?
C20 C21 C25 F2' 124.4(11) . . . . ?
C22 C21 C25 F2' -54.3(12) . . . . ?
C20 C21 C25 F3' -129.7(7) . . . . ?
C22 C21 C25 F3' 51.6(8) . . . . ?
C20 C21 C25 F2 65.3(8) . . . . ?
C22 C21 C25 F2 -113.4(7) . . . . ?
C20 C21 C25 F1 -44.5(6) . . . . ?
C22 C21 C25 F1 136.9(4) . . . . ?
C22 C23 C26 F4' 36.8(10) . . . . ?
C24 C23 C26 F4' -141.8(9) . . . . ?
C22 C23 C26 F5 -106.0(5) . . . . ?
C24 C23 C26 F5 75.4(5) . . . . ?
C22 C23 C26 F6 121.5(5) . . . . ?
C24 C23 C26 F6 -57.1(6) . . . . ?
C22 C23 C26 F5' -91.7(6) . . . . ?
C24 C23 C26 F5' 89.7(6) . . . . ?
C22 C23 C26 F4 9.4(6) . . . . ?
C24 C23 C26 F4 -169.2(5) . . . . ?
C22 C23 C26 F6' 166.1(4) . . . . ?
C24 C23 C26 F6' -12.5(5) . . . . ?
C35 N4 C27 C28 7.8(3) . . . . ?
C35 N4 C27 C36 -171.9(2) . . . . ?
N4 C27 C28 C29 -11.8(3) . . . . ?
C36 C27 C28 C29 167.8(2) . . . . ?
C27 C28 C29 C30 -172.9(2) . . . . ?
C27 C28 C29 C34 2.2(3) . . . . ?
C28 C29 C30 C31 170.1(2) . . . . ?
C34 C29 C30 C31 -5.0(3) . . . . ?
C29 C30 C31 C32 -1.1(3) . . . . ?
C29 C30 C31 C37 -178.3(2) . . . . ?
C30 C31 C32 C33 2.7(3) . . . . ?
C37 C31 C32 C33 179.9(2) . . . . ?
C30 C31 C32 C38 -177.1(2) . . . . ?
C37 C31 C32 C38 0.2(3) . . . . ?
C44 O2 C33 C32 99.4(2) . . . . ?
C44 O2 C33 C34 -79.6(2) . . . . ?
C31 C32 C33 O2 -177.05(18) . . . . ?
C38 C32 C33 O2 2.7(3) . . . . ?
C31 C32 C33 C34 2.0(3) . . . . ?
C38 C32 C33 C34 -178.23(18) . . . . ?
O2 C33 C34 C29 171.15(16) . . . . ?
C32 C33 C34 C29 -7.8(3) . . . . ?
O2 C33 C34 C35 -4.6(3) . . . . ?
C32 C33 C34 C35 176.43(18) . . . . ?
C30 C29 C34 C33 9.2(3) . . . . ?
C28 C29 C34 C33 -165.96(17) . . . . ?
C30 C29 C34 C35 -174.52(17) . . . . ?
C28 C29 C34 C35 10.3(3) . . . . ?
C27 N4 C35 N5 -176.71(17) . . . . ?
C27 N4 C35 C34 6.0(3) . . . . ?
C43 N5 C35 N4 -7.0(2) . . . . ?
C39 N5 C35 N4 130.94(19) . . . . ?
C43 N5 C35 C34 170.29(17) . . . . ?
C39 N5 C35 C34 -51.8(2) . . . . ?
C33 C34 C35 N4 161.06(18) . . . . ?
C29 C34 C35 N4 -14.7(3) . . . . ?
C33 C34 C35 N5 -16.1(3) . . . . ?
C29 C34 C35 N5 168.13(16) . . . . ?
C35 N5 C39 C40 160.41(19) . . . . ?
C43 N5 C39 C40 -59.6(2) . . . . ?
N5 C39 C40 C41 56.8(3) . . . . ?
C39 C40 C41 C42 -54.1(3) . . . . ?
C40 C41 C42 C43 54.8(3) . . . . ?
C35 N5 C43 C42 -160.15(19) . . . . ?
C39 N5 C43 C42 58.8(2) . . . . ?
C41 C42 C43 N5 -56.9(3) . . . . ?
C33 O2 C44 C45 -161.26(17) . . . . ?
O2 C44 C45 C46 14.9(3) . . . . ?
O2 C44 C45 C50 -167.15(19) . . . . ?
C50 C45 C46 C47 0.5(3) . . . . ?
C44 C45 C46 C47 178.5(2) . . . . ?
C45 C46 C47 C48 -0.8(4) . . . . ?
C45 C46 C47 C51 -177.1(3) . . . . ?
C46 C47 C48 C49 0.2(4) . . . . ?
C51 C47 C48 C49 176.6(4) . . . . ?
C47 C48 C49 C50 0.7(4) . . . . ?
C47 C48 C49 C52 -177.9(4) . . . . ?
C48 C49 C50 C45 -1.0(4) . . . . ?
C52 C49 C50 C45 177.5(4) . . . . ?
C46 C45 C50 C49 0.4(3) . . . . ?
C44 C45 C50 C49 -177.6(2) . . . . ?
C48 C47 C51 F8' -113.5(12) . . . . ?
C46 C47 C51 F8' 62.9(13) . . . . ?
C48 C47 C51 F9' 33.6(9) . . . . ?
C46 C47 C51 F9' -150.0(7) . . . . ?
C48 C47 C51 F7 179.8(9) . . . . ?
C46 C47 C51 F7 -3.8(11) . . . . ?
C48 C47 C51 F9 57.1(8) . . . . ?
C46 C47 C51 F9 -126.6(7) . . . . ?
C48 C47 C51 F8 -57.3(7) . . . . ?
C46 C47 C51 F8 119.1(5) . . . . ?
C48 C47 C51 F7' 131.2(6) . . . . ?
C46 C47 C51 F7' -52.4(7) . . . . ?
C48 C49 C52 F11' -153.7(14) . . . . ?
C50 C49 C52 F11' 27.7(15) . . . . ?
C48 C49 C52 F12' 85.2(12) . . . . ?
C50 C49 C52 F12' -93.4(12) . . . . ?
C48 C49 C52 F10' -38.3(14) . . . . ?
C50 C49 C52 F10' 143.1(12) . . . . ?
C48 C49 C52 F11 -106.9(12) . . . . ?
C50 C49 C52 F11 74.5(11) . . . . ?
C48 C49 C52 F10 17.1(11) . . . . ?
C50 C49 C52 F10 -161.5(9) . . . . ?
C48 C49 C52 F12 139.9(10) . . . . ?
C50 C49 C52 F12 -38.7(12) . . . . ?

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
C39 H39A O2 0.97 2.30 2.864(3) 116.4 .
C36 H36B F5 0.96 2.58 3.350(8) 137.5 1_455
C18 H18B N2 0.97 2.68 3.219(3) 115.4 .
C13 H13B O1 0.97 2.35 2.885(2) 113.8 .
C39 H39A O2 0.97 2.30 2.864(3) 116.4 .
C36 H36B F5 0.96 2.58 3.350(8) 137.5 1_455
C18 H18B N2 0.97 2.68 3.219(3) 115.4 .
C13 H13B O1 0.97 2.35 2.885(2) 113.8 .
C13 H13B O1 0.97 2.35 2.885(2) 113.8 .
C18 H18B N2 0.97 2.68 3.219(3) 115.4 .
C36 H36B F5 0.96 2.58 3.350(8) 137.5 1_455
C39 H39A O2 0.97 2.30 2.864(3) 116.4 .

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.030

_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_dd18305_0m
_database_code_depnum_ccdc_archive 'CCDC 2245988'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2023-03-03 deposited with the CCDC.	2023-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H29 N3 O'
_chemical_formula_weight         399.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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'
'-x, -y, -z'

_cell_length_a                   10.8627(3)
_cell_length_b                   10.9176(3)
_cell_length_c                   10.9887(4)
_cell_angle_alpha                80.5480(10)
_cell_angle_beta                 87.9690(10)
_cell_angle_gamma                61.5120(10)
_cell_volume                     1128.47(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4843
_cell_measurement_theta_min      5.434
_cell_measurement_theta_max      54.937

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6683
_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            11024
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.881
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4161
_reflns_number_gt                3187
_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)+(0.0887P)²+0.2877P] 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       0.048(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4161
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1747
_refine_ls_wR_factor_gt          0.1564
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.020
_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 0.49631(13) 0.79736(12) 0.35423(11) 0.0480(4) Uani 1 1 d . . . . .
N1 N 0.84091(19) 0.73138(18) 0.11450(15) 0.0583(5) Uani 1 1 d . . . . .
N2 N 0.76657(16) 0.78000(17) 0.30859(14) 0.0496(4) Uani 1 1 d . . . . .
N3 N 0.1459(2) 0.8974(3) 0.3164(3) 0.0993(8) Uani 1 1 d . . . . .
C1 C 0.8164(3) 0.7316(2) -0.00683(19) 0.0629(6) Uani 1 1 d . . . . .
C2 C 0.6865(3) 0.7782(2) -0.05535(18) 0.0619(6) Uani 1 1 d . . . . .
H2 H 0.6722 0.7874 -0.1400 0.074 Uiso 1 1 calc R U . . .
C3 C 0.5724(2) 0.8132(2) 0.02153(17) 0.0534(5) Uani 1 1 d . . . . .
C4 C 0.4366(2) 0.8566(2) -0.0259(2) 0.0610(6) Uani 1 1 d . . . . .
H4 H 0.4222 0.8660 -0.1106 0.073 Uiso 1 1 calc R U . . .
C5 C 0.3260(2) 0.8852(2) 0.0465(2) 0.0616(6) Uani 1 1 d . . . . .
C6 C 0.3520(2) 0.8627(2) 0.1763(2) 0.0561(5) Uani 1 1 d . . . . .
C7 C 0.4835(2) 0.82057(18) 0.22741(17) 0.0468(5) Uani 1 1 d . . . . .
C8 C 0.5966(2) 0.80312(19) 0.15071(16) 0.0465(5) Uani 1 1 d . . . . .
C9 C 0.7357(2) 0.77163(19) 0.18948(16) 0.0467(5) Uani 1 1 d . . . . .
C10 C 0.9434(3) 0.6850(3) -0.0837(2) 0.0922(9) Uani 1 1 d . . . . .
H10A H 0.9603 0.7634 -0.1115 0.138 Uiso 1 1 calc R U . . .
H10B H 0.9274 0.6514 -0.1538 0.138 Uiso 1 1 calc R U . . .
H10C H 1.0234 0.6104 -0.0348 0.138 Uiso 1 1 calc R U . . .
C11 C 0.1800(3) 0.9366(3) -0.0053(3) 0.0864(8) Uani 1 1 d . . . . .
H11A H 0.1799 0.9489 -0.0939 0.130 Uiso 1 1 calc R U . . .
H11B H 0.1175 1.0253 0.0198 0.130 Uiso 1 1 calc R U . . .
H11C H 0.1494 0.8685 0.0250 0.130 Uiso 1 1 calc R U . . .
C12 C 0.2392(2) 0.8820(3) 0.2562(2) 0.0681(6) Uani 1 1 d . . . . .
C13 C 0.6837(2) 0.9183(2) 0.35022(18) 0.0522(5) Uani 1 1 d . . . . .
H13A H 0.5859 0.9575 0.3245 0.063 Uiso 1 1 calc R U . . .
H13B H 0.7164 0.9834 0.3117 0.063 Uiso 1 1 calc R U . . .
C14 C 0.6972(2) 0.9027(2) 0.4883(2) 0.0630(6) Uani 1 1 d . . . . .
H14A H 0.6578 0.8435 0.5270 0.076 Uiso 1 1 calc R U . . .
H14B H 0.6450 0.9947 0.5130 0.076 Uiso 1 1 calc R U . . .
C15 C 0.8507(3) 0.8365(3) 0.5312(2) 0.0792(7) Uani 1 1 d . . . . .
H15A H 0.8872 0.9008 0.5007 0.095 Uiso 1 1 calc R U . . .
H15B H 0.8590 0.8195 0.6208 0.095 Uiso 1 1 calc R U . . .
C16 C 0.9344(3) 0.6987(3) 0.4837(2) 0.0794(7) Uani 1 1 d . . . . .
H16A H 1.0329 0.6605 0.5062 0.095 Uiso 1 1 calc R U . . .
H16B H 0.9048 0.6312 0.5223 0.095 Uiso 1 1 calc R U . . .
C17 C 0.9154(2) 0.7182(3) 0.3451(2) 0.0657(6) Uani 1 1 d . . . . .
H17A H 0.9518 0.7798 0.3058 0.079 Uiso 1 1 calc R U . . .
H17B H 0.9676 0.6276 0.3178 0.079 Uiso 1 1 calc R U . . .
C18 C 0.5655(2) 0.6497(2) 0.40807(18) 0.0568(5) Uani 1 1 d . . . . .
H18A H 0.6660 0.6099 0.4008 0.068 Uiso 1 1 calc R U . . .
H18B H 0.5333 0.5986 0.3651 0.068 Uiso 1 1 calc R U . . .
C19 C 0.5317(2) 0.6364(2) 0.54214(18) 0.0533(5) Uani 1 1 d . . . . .
C20 C 0.3927(2) 0.6939(2) 0.5753(2) 0.0594(5) Uani 1 1 d . . . . .
H20 H 0.3209 0.7472 0.5148 0.071 Uiso 1 1 calc R U . . .
C21 C 0.3598(3) 0.6726(3) 0.6976(2) 0.0675(6) Uani 1 1 d . . . . .
C22 C 0.4690(3) 0.5950(3) 0.7854(2) 0.0718(7) Uani 1 1 d . . . . .
H22 H 0.4478 0.5808 0.8675 0.086 Uiso 1 1 calc R U . . .
C23 C 0.6075(3) 0.5379(2) 0.75681(19) 0.0635(6) Uani 1 1 d . . . . .
C24 C 0.6380(2) 0.5590(2) 0.63272(19) 0.0604(6) Uani 1 1 d . . . . .
H24 H 0.7310 0.5205 0.6109 0.072 Uiso 1 1 calc R U . . .
C25 C 0.2086(3) 0.7283(4) 0.7303(3) 0.1095(11) Uani 1 1 d . . . . .
H25A H 0.1502 0.8095 0.6706 0.164 Uiso 1 1 calc R U . . .
H25B H 0.1975 0.7546 0.8108 0.164 Uiso 1 1 calc R U . . .
H25C H 0.1817 0.6563 0.7305 0.164 Uiso 1 1 calc R U . . .
C26 C 0.7241(3) 0.4527(3) 0.8535(2) 0.0902(8) Uani 1 1 d . . . . .
H26A H 0.7351 0.3590 0.8746 0.135 Uiso 1 1 calc R U . . .
H26B H 0.7021 0.4968 0.9258 0.135 Uiso 1 1 calc R U . . .
H26C H 0.8097 0.4477 0.8221 0.135 Uiso 1 1 calc R 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
O1 C7 1.375(2) . ?
O1 C18 1.441(2) . ?
N1 C9 1.323(2) . ?
N1 C1 1.368(3) . ?
N2 C9 1.390(2) . ?
N2 C17 1.465(3) . ?
N2 C13 1.483(2) . ?
N3 C12 1.148(3) . ?
C1 C2 1.347(3) . ?
C1 C10 1.504(3) . ?
C2 C3 1.406(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.407(3) . ?
C3 C8 1.430(3) . ?
C4 C5 1.352(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.422(3) . ?
C5 C11 1.505(3) . ?
C6 C7 1.383(3) . ?
C6 C12 1.434(3) . ?
C7 C8 1.419(3) . ?
C8 C9 1.444(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.503(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.523(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.511(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.510(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.506(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C24 1.383(3) . ?
C19 C20 1.392(3) . ?
C20 C21 1.389(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.382(4) . ?
C21 C25 1.508(4) . ?
C22 C23 1.373(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.400(3) . ?
C23 C26 1.499(4) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C18 113.39(13) . . ?
C9 N1 C1 119.83(19) . . ?
C9 N2 C17 116.47(16) . . ?
C9 N2 C13 116.88(15) . . ?
C17 N2 C13 110.86(16) . . ?
C2 C1 N1 122.17(19) . . ?
C2 C1 C10 122.5(2) . . ?
N1 C1 C10 115.3(2) . . ?
C1 C2 C3 120.24(19) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 121.45(19) . . ?
C2 C3 C8 118.64(19) . . ?
C4 C3 C8 119.90(19) . . ?
C5 C4 C3 122.8(2) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C4 C5 C6 117.55(19) . . ?
C4 C5 C11 122.5(2) . . ?
C6 C5 C11 120.0(2) . . ?
C7 C6 C5 121.8(2) . . ?
C7 C6 C12 119.2(2) . . ?
C5 C6 C12 118.93(19) . . ?
O1 C7 C6 116.23(17) . . ?
O1 C7 C8 123.21(16) . . ?
C6 C7 C8 120.56(18) . . ?
C7 C8 C3 116.83(17) . . ?
C7 C8 C9 126.98(17) . . ?
C3 C8 C9 116.16(17) . . ?
N1 C9 N2 116.46(17) . . ?
N1 C9 C8 121.96(17) . . ?
N2 C9 C8 121.56(16) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C6 177.3(3) . . ?
N2 C13 C14 111.06(16) . . ?
N2 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
N2 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 110.35(19) . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 109.66(19) . . ?
C16 C15 H15A 109.7 . . ?
C14 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C17 C16 C15 111.6(2) . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
N2 C17 C16 110.20(18) . . ?
N2 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
N2 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
O1 C18 C19 108.49(15) . . ?
O1 C18 H18A 110.0 . . ?
C19 C18 H18A 110.0 . . ?
O1 C18 H18B 110.0 . . ?
C19 C18 H18B 110.0 . . ?
H18A C18 H18B 108.4 . . ?
C24 C19 C20 119.35(19) . . ?
C24 C19 C18 120.35(19) . . ?
C20 C19 C18 120.2(2) . . ?
C21 C20 C19 120.8(2) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C20 118.0(2) . . ?
C22 C21 C25 122.0(2) . . ?
C20 C21 C25 119.9(3) . . ?
C23 C22 C21 123.0(2) . . ?
C23 C22 H22 118.5 . . ?
C21 C22 H22 118.5 . . ?
C22 C23 C24 118.0(2) . . ?
C22 C23 C26 122.0(2) . . ?
C24 C23 C26 120.1(2) . . ?
C19 C24 C23 120.8(2) . . ?
C19 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C21 C25 H25A 109.5 . . ?
C21 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C21 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C2 3.3(3) . . . . ?
C9 N1 C1 C10 179.5(2) . . . . ?
N1 C1 C2 C3 -7.5(3) . . . . ?
C10 C1 C2 C3 176.5(2) . . . . ?
C1 C2 C3 C4 -177.32(19) . . . . ?
C1 C2 C3 C8 2.3(3) . . . . ?
C2 C3 C4 C5 177.15(19) . . . . ?
C8 C3 C4 C5 -2.4(3) . . . . ?
C3 C4 C5 C6 -3.3(3) . . . . ?
C3 C4 C5 C11 177.71(19) . . . . ?
C4 C5 C6 C7 3.4(3) . . . . ?
C11 C5 C6 C7 -177.58(19) . . . . ?
C4 C5 C6 C12 -175.44(19) . . . . ?
C11 C5 C6 C12 3.6(3) . . . . ?
C18 O1 C7 C6 103.62(19) . . . . ?
C18 O1 C7 C8 -76.3(2) . . . . ?
C5 C6 C7 O1 -177.64(16) . . . . ?
C12 C6 C7 O1 1.2(3) . . . . ?
C5 C6 C7 C8 2.3(3) . . . . ?
C12 C6 C7 C8 -178.84(17) . . . . ?
O1 C7 C8 C3 172.14(15) . . . . ?
C6 C7 C8 C3 -7.8(3) . . . . ?
O1 C7 C8 C9 -5.7(3) . . . . ?
C6 C7 C8 C9 174.34(17) . . . . ?
C2 C3 C8 C7 -171.69(17) . . . . ?
C4 C3 C8 C7 7.9(3) . . . . ?
C2 C3 C8 C9 6.4(3) . . . . ?
C4 C3 C8 C9 -174.02(16) . . . . ?
C1 N1 C9 N2 -174.75(17) . . . . ?
C1 N1 C9 C8 6.2(3) . . . . ?
C17 N2 C9 N1 -11.3(2) . . . . ?
C13 N2 C9 N1 123.03(18) . . . . ?
C17 N2 C9 C8 167.78(17) . . . . ?
C13 N2 C9 C8 -57.9(2) . . . . ?
C7 C8 C9 N1 167.01(18) . . . . ?
C3 C8 C9 N1 -10.8(3) . . . . ?
C7 C8 C9 N2 -12.0(3) . . . . ?
C3 C8 C9 N2 170.17(16) . . . . ?
C9 N2 C13 C14 163.71(16) . . . . ?
C17 N2 C13 C14 -59.6(2) . . . . ?
N2 C13 C14 C15 57.2(2) . . . . ?
C13 C14 C15 C16 -54.6(3) . . . . ?
C14 C15 C16 C17 54.9(3) . . . . ?
C9 N2 C17 C16 -164.42(19) . . . . ?
C13 N2 C17 C16 58.7(2) . . . . ?
C15 C16 C17 N2 -57.2(3) . . . . ?
C7 O1 C18 C19 -161.33(16) . . . . ?
O1 C18 C19 C24 -128.41(19) . . . . ?
O1 C18 C19 C20 55.9(2) . . . . ?
C24 C19 C20 C21 -1.0(3) . . . . ?
C18 C19 C20 C21 174.72(19) . . . . ?
C19 C20 C21 C22 1.2(3) . . . . ?
C19 C20 C21 C25 -176.3(2) . . . . ?
C20 C21 C22 C23 -0.4(3) . . . . ?
C25 C21 C22 C23 177.0(2) . . . . ?
C21 C22 C23 C24 -0.5(3) . . . . ?
C21 C22 C23 C26 -179.3(2) . . . . ?
C20 C19 C24 C23 0.0(3) . . . . ?
C18 C19 C24 C23 -175.67(18) . . . . ?
C22 C23 C24 C19 0.7(3) . . . . ?
C26 C23 C24 C19 179.5(2) . . . . ?

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
C18 H18A N2 0.97 2.63 3.205(3) 118.4 .
C13 H13A O1 0.97 2.35 2.903(2) 115.5 .

_refine_diff_density_max         0.369
_refine_diff_density_min         -0.142
_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_mo_dd18246_0m
_database_code_depnum_ccdc_archive 'CCDC 2245986'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2023-03-03 deposited with the CCDC.	2023-04-26 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 H24 N4 O'
_chemical_formula_weight         396.48

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           2
_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'
'-x, -y, -z'

_cell_length_a                   7.8031(3)
_cell_length_b                   10.8097(4)
_cell_length_c                   13.6803(5)
_cell_angle_alpha                104.0820(10)
_cell_angle_beta                 92.9470(10)
_cell_angle_gamma                108.1090(10)
_cell_volume                     1053.66(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5549
_cell_measurement_theta_min      5.546
_cell_measurement_theta_max      53.755

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4683
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            14730
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.897
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3919
_reflns_number_gt                3009
_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)+(0.0709P)²+0.2593P] 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       0.102(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3919
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1689
_refine_ls_wR_factor_gt          0.1540
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_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 0.65912(17) 0.79869(13) 0.35318(9) 0.0503(4) Uani 1 1 d . . . . .
N1 N 0.4517(2) 0.40806(17) 0.13673(13) 0.0554(5) Uani 1 1 d . . . . .
N2 N 0.6997(2) 0.54599(16) 0.25661(12) 0.0509(4) Uani 1 1 d . . . . .
N3 N 0.6387(3) 1.1111(2) 0.38206(17) 0.0792(6) Uani 1 1 d . . . . .
N4 N 1.1472(3) 0.9065(3) 0.86314(17) 0.0985(8) Uani 1 1 d . . . . .
C1 C 0.3108(3) 0.3898(2) 0.06535(15) 0.0577(6) Uani 1 1 d . . . . .
C2 C 0.2697(3) 0.4956(2) 0.04567(15) 0.0603(6) Uani 1 1 d . . . . .
H2 H 0.1825 0.4804 -0.0089 0.072 Uiso 1 1 calc R U . . .
C3 C 0.3590(3) 0.6285(2) 0.10783(15) 0.0536(5) Uani 1 1 d . . . . .
C4 C 0.3193(3) 0.7414(2) 0.09141(16) 0.0607(6) Uani 1 1 d . . . . .
H4 H 0.2375 0.7283 0.0349 0.073 Uiso 1 1 calc R U . . .
C5 C 0.3957(3) 0.8685(2) 0.15470(16) 0.0594(6) Uani 1 1 d . . . . .
C6 C 0.5090(3) 0.8828(2) 0.24512(15) 0.0533(5) Uani 1 1 d . . . . .
C7 C 0.5535(3) 0.7754(2) 0.26273(14) 0.0487(5) Uani 1 1 d . . . . .
C8 C 0.4917(3) 0.6468(2) 0.19053(14) 0.0482(5) Uani 1 1 d . . . . .
C9 C 0.5451(3) 0.5308(2) 0.19314(14) 0.0477(5) Uani 1 1 d . . . . .
C10 C 0.2127(3) 0.2455(2) 0.00595(18) 0.0749(7) Uani 1 1 d . . . . .
H10A H 0.2951 0.2102 -0.0322 0.112 Uiso 1 1 calc R U . . .
H10B H 0.1126 0.2416 -0.0399 0.112 Uiso 1 1 calc R U . . .
H10C H 0.1676 0.1924 0.0520 0.112 Uiso 1 1 calc R U . . .
C11 C 0.3632(4) 0.9899(3) 0.1335(2) 0.0830(8) Uani 1 1 d . . . . .
H11A H 0.4756 1.0508 0.1230 0.124 Uiso 1 1 calc R U . . .
H11B H 0.3176 1.0351 0.1903 0.124 Uiso 1 1 calc R U . . .
H11C H 0.2758 0.9614 0.0735 0.124 Uiso 1 1 calc R U . . .
C12 C 0.5796(3) 1.0100(2) 0.32142(17) 0.0601(6) Uani 1 1 d . . . . .
C13 C 0.8714(3) 0.6453(2) 0.24653(15) 0.0524(5) Uani 1 1 d . . . . .
H13A H 0.8485 0.7256 0.2383 0.063 Uiso 1 1 calc R U . . .
H13B H 0.9179 0.6074 0.1861 0.063 Uiso 1 1 calc R U . . .
C14 C 1.0124(3) 0.6840(2) 0.33838(17) 0.0604(6) Uani 1 1 d . . . . .
H14A H 0.9709 0.7289 0.3981 0.072 Uiso 1 1 calc R U . . .
H14B H 1.1255 0.7465 0.3283 0.072 Uiso 1 1 calc R U . . .
C15 C 1.0449(3) 0.5587(3) 0.3548(2) 0.0721(7) Uani 1 1 d . . . . .
H15A H 1.1025 0.5210 0.2994 0.086 Uiso 1 1 calc R U . . .
H15B H 1.1258 0.5830 0.4177 0.086 Uiso 1 1 calc R U . . .
C16 C 0.8659(3) 0.4540(2) 0.35961(19) 0.0693(7) Uani 1 1 d . . . . .
H16A H 0.8875 0.3720 0.3647 0.083 Uiso 1 1 calc R U . . .
H16B H 0.8165 0.4878 0.4201 0.083 Uiso 1 1 calc R U . . .
C17 C 0.7284(3) 0.4212(2) 0.26668(18) 0.0618(6) Uani 1 1 d . . . . .
H17A H 0.7726 0.3805 0.2063 0.074 Uiso 1 1 calc R U . . .
H17B H 0.6141 0.3569 0.2734 0.074 Uiso 1 1 calc R U . . .
C18 C 0.5569(3) 0.7487(2) 0.42830(15) 0.0610(6) Uani 1 1 d . . . . .
H18A H 0.5005 0.6512 0.4042 0.073 Uiso 1 1 calc R U . . .
H18B H 0.4618 0.7884 0.4408 0.073 Uiso 1 1 calc R U . . .
C19 C 0.6847(3) 0.7857(2) 0.52436(14) 0.0498(5) Uani 1 1 d . . . . .
C20 C 0.8185(3) 0.9112(2) 0.55790(16) 0.0590(6) Uani 1 1 d . . . . .
H20 H 0.8287 0.9742 0.5209 0.071 Uiso 1 1 calc R U . . .
C21 C 0.9370(3) 0.9438(2) 0.64561(16) 0.0628(6) Uani 1 1 d . . . . .
H21 H 1.0278 1.0281 0.6670 0.075 Uiso 1 1 calc R U . . .
C22 C 0.9214(3) 0.8518(2) 0.70167(14) 0.0537(5) Uani 1 1 d . . . . .
C23 C 0.7837(3) 0.7285(2) 0.67103(16) 0.0605(6) Uani 1 1 d . . . . .
H23 H 0.7693 0.6674 0.7100 0.073 Uiso 1 1 calc R U . . .
C24 C 0.6676(3) 0.6961(2) 0.58241(16) 0.0589(6) Uani 1 1 d . . . . .
H24 H 0.5761 0.6122 0.5614 0.071 Uiso 1 1 calc R U . . .
C25 C 1.0470(3) 0.8833(3) 0.79243(17) 0.0696(7) 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 C7 1.374(2) . ?
O1 C18 1.439(2) . ?
N1 C9 1.316(2) . ?
N1 C1 1.365(3) . ?
N2 C9 1.391(2) . ?
N2 C13 1.471(2) . ?
N2 C17 1.472(3) . ?
N3 C12 1.141(3) . ?
N4 C25 1.137(3) . ?
C1 C2 1.362(3) . ?
C1 C10 1.502(3) . ?
C2 C3 1.412(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.414(3) . ?
C3 C8 1.426(3) . ?
C4 C5 1.361(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.430(3) . ?
C5 C11 1.502(3) . ?
C6 C7 1.381(3) . ?
C6 C12 1.433(3) . ?
C7 C8 1.417(3) . ?
C8 C9 1.446(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.510(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.518(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.516(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.515(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.497(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C24 1.375(3) . ?
C19 C20 1.381(3) . ?
C20 C21 1.377(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.378(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(3) . ?
C22 C25 1.442(3) . ?
C23 C24 1.377(3) . ?
C23 H23 0.9300 . ?
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
C7 O1 C18 113.42(14) . . ?
C9 N1 C1 119.56(19) . . ?
C9 N2 C13 117.00(15) . . ?
C9 N2 C17 116.86(16) . . ?
C13 N2 C17 110.79(17) . . ?
C2 C1 N1 122.14(19) . . ?
C2 C1 C10 122.7(2) . . ?
N1 C1 C10 115.1(2) . . ?
C1 C2 C3 120.18(19) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 122.33(19) . . ?
C2 C3 C8 117.9(2) . . ?
C4 C3 C8 119.80(19) . . ?
C5 C4 C3 122.84(19) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C4 C5 C6 116.9(2) . . ?
C4 C5 C11 122.8(2) . . ?
C6 C5 C11 120.3(2) . . ?
C7 C6 C5 121.61(19) . . ?
C7 C6 C12 117.53(18) . . ?
C5 C6 C12 120.85(19) . . ?
O1 C7 C6 117.11(17) . . ?
O1 C7 C8 121.75(17) . . ?
C6 C7 C8 121.14(17) . . ?
C7 C8 C3 116.58(18) . . ?
C7 C8 C9 126.95(17) . . ?
C3 C8 C9 116.45(18) . . ?
N1 C9 N2 117.31(18) . . ?
N1 C9 C8 122.24(18) . . ?
N2 C9 C8 120.45(17) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C6 178.8(2) . . ?
N2 C13 C14 111.56(16) . . ?
N2 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N2 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 110.05(18) . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.2 . . ?
C16 C15 C14 110.19(19) . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C15 111.78(19) . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
N2 C17 C16 109.52(18) . . ?
N2 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
N2 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
O1 C18 C19 108.40(16) . . ?
O1 C18 H18A 110.0 . . ?
C19 C18 H18A 110.0 . . ?
O1 C18 H18B 110.0 . . ?
C19 C18 H18B 110.0 . . ?
H18A C18 H18B 108.4 . . ?
C24 C19 C20 118.65(18) . . ?
C24 C19 C18 120.34(18) . . ?
C20 C19 C18 120.99(19) . . ?
C21 C20 C19 120.63(19) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 120.1(2) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C23 119.68(19) . . ?
C21 C22 C25 120.7(2) . . ?
C23 C22 C25 119.6(2) . . ?
C24 C23 C22 119.71(19) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C19 C24 C23 121.15(19) . . ?
C19 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
N4 C25 C22 178.8(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
C9 N1 C1 C2 4.2(3) . . . . ?
C9 N1 C1 C10 -179.49(19) . . . . ?
N1 C1 C2 C3 -7.7(3) . . . . ?
C10 C1 C2 C3 176.2(2) . . . . ?
C1 C2 C3 C4 -179.1(2) . . . . ?
C1 C2 C3 C8 0.0(3) . . . . ?
C2 C3 C4 C5 175.5(2) . . . . ?
C8 C3 C4 C5 -3.6(3) . . . . ?
C3 C4 C5 C6 -5.0(3) . . . . ?
C3 C4 C5 C11 175.8(2) . . . . ?
C4 C5 C6 C7 6.2(3) . . . . ?
C11 C5 C6 C7 -174.6(2) . . . . ?
C4 C5 C6 C12 -173.4(2) . . . . ?
C11 C5 C6 C12 5.9(3) . . . . ?
C18 O1 C7 C6 101.5(2) . . . . ?
C18 O1 C7 C8 -78.2(2) . . . . ?
C5 C6 C7 O1 -178.28(17) . . . . ?
C12 C6 C7 O1 1.3(3) . . . . ?
C5 C6 C7 C8 1.4(3) . . . . ?
C12 C6 C7 C8 -179.02(19) . . . . ?
O1 C7 C8 C3 169.85(17) . . . . ?
C6 C7 C8 C3 -9.9(3) . . . . ?
O1 C7 C8 C9 -8.3(3) . . . . ?
C6 C7 C8 C9 171.96(19) . . . . ?
C2 C3 C8 C7 -168.26(19) . . . . ?
C4 C3 C8 C7 10.9(3) . . . . ?
C2 C3 C8 C9 10.1(3) . . . . ?
C4 C3 C8 C9 -170.74(18) . . . . ?
C1 N1 C9 N2 -172.95(17) . . . . ?
C1 N1 C9 C8 7.1(3) . . . . ?
C13 N2 C9 N1 125.53(19) . . . . ?
C17 N2 C9 N1 -9.3(3) . . . . ?
C13 N2 C9 C8 -54.5(2) . . . . ?
C17 N2 C9 C8 170.73(18) . . . . ?
C7 C8 C9 N1 164.06(19) . . . . ?
C3 C8 C9 N1 -14.1(3) . . . . ?
C7 C8 C9 N2 -15.9(3) . . . . ?
C3 C8 C9 N2 165.89(17) . . . . ?
C9 N2 C13 C14 162.20(18) . . . . ?
C17 N2 C13 C14 -60.4(2) . . . . ?
N2 C13 C14 C15 56.9(2) . . . . ?
C13 C14 C15 C16 -53.4(3) . . . . ?
C14 C15 C16 C17 54.5(3) . . . . ?
C9 N2 C17 C16 -163.23(18) . . . . ?
C13 N2 C17 C16 59.3(2) . . . . ?
C15 C16 C17 N2 -57.1(3) . . . . ?
C7 O1 C18 C19 -177.33(17) . . . . ?
O1 C18 C19 C24 -140.7(2) . . . . ?
O1 C18 C19 C20 41.0(3) . . . . ?
C24 C19 C20 C21 2.5(3) . . . . ?
C18 C19 C20 C21 -179.1(2) . . . . ?
C19 C20 C21 C22 -0.9(4) . . . . ?
C20 C21 C22 C23 -1.7(3) . . . . ?
C20 C21 C22 C25 178.6(2) . . . . ?
C21 C22 C23 C24 2.7(3) . . . . ?
C25 C22 C23 C24 -177.6(2) . . . . ?
C20 C19 C24 C23 -1.6(3) . . . . ?
C18 C19 C24 C23 -179.9(2) . . . . ?
C22 C23 C24 C19 -1.0(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
C18 H18B N3 0.97 2.67 3.360(3) 128.7 2_676
C13 H13A O1 0.97 2.37 2.898(3) 113.3 .

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.040

_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_dd18245_0m
_database_code_depnum_ccdc_archive 'CCDC 2245987'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2023-03-03 deposited with the CCDC.	2023-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 N4 O3'
_chemical_formula_weight         416.47

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.7300(9)
_cell_length_b                   13.6341(10)
_cell_length_c                   14.8150(14)
_cell_angle_alpha                90
_cell_angle_beta                 90.254(3)
_cell_angle_gamma                90
_cell_volume                     2167.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3638
_cell_measurement_theta_min      4.831
_cell_measurement_theta_max      48.498

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6576
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            10438
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.349
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.932
_reflns_number_total             7518
_reflns_number_gt                5255
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_max     0.865
_reflns_Friedel_fraction_full    0.867

_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)+(0.0474P)²+0.1028P] 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       0.039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1862 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.8(8)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         7518
_refine_ls_number_parameters     564
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1224
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
N1 N 1.0425(3) 0.0865(3) 0.0320(2) 0.0634(9) Uani 1 1 d . . . . .
N2 N 0.9942(3) 0.0239(3) 0.1731(2) 0.0636(10) Uani 1 1 d . . . . .
N3 N 0.4419(4) 0.0994(5) 0.2338(4) 0.1200(19) Uani 1 1 d . . . . .
N4 N 0.8352(5) 0.1214(3) 0.6469(3) 0.0794(12) Uani 1 1 d . . . . .
N5 N 0.7183(3) 0.3987(2) 0.1627(2) 0.0578(9) Uani 1 1 d . . . . .
N6 N 0.6669(3) 0.4551(2) 0.3049(2) 0.0525(8) Uani 1 1 d . . . . .
N7 N 0.1176(4) 0.3589(4) 0.3672(4) 0.1156(19) Uani 1 1 d . . . . .
N8 N 0.4680(6) 0.3272(4) 0.7845(4) 0.1031(16) Uani 1 1 d . . . . .
O1 O 0.7490(2) 0.06872(19) 0.22568(19) 0.0613(7) Uani 1 1 d . . . . .
O2 O 0.9339(4) 0.1465(4) 0.6810(3) 0.1244(16) Uani 1 1 d . . . . .
O3 O 0.7460(4) 0.0921(3) 0.6900(2) 0.1045(12) Uani 1 1 d . . . . .
O4 O 0.4250(2) 0.39308(18) 0.36036(19) 0.0552(7) Uani 1 1 d . . . . .
O5 O 0.5657(6) 0.3156(5) 0.8237(3) 0.171(3) Uani 1 1 d . . . . .
O6 O 0.3689(5) 0.3375(4) 0.8218(3) 0.1426(19) Uani 1 1 d . . . . .
C1 C 1.0097(4) 0.1150(3) -0.0522(3) 0.0658(12) Uani 1 1 d . . . . .
C2 C 0.8894(5) 0.1128(3) -0.0818(3) 0.0712(13) Uani 1 1 d . . . . .
H2 H 0.8711 0.1232 -0.1425 0.085 Uiso 1 1 calc R U . . .
C3 C 0.7923(4) 0.0947(3) -0.0197(3) 0.0630(11) Uani 1 1 d . . . . .
C4 C 0.6653(5) 0.1034(3) -0.0455(3) 0.0742(13) Uani 1 1 d . . . . .
H4 H 0.6454 0.1121 -0.1062 0.089 Uiso 1 1 calc R U . . .
C5 C 0.5720(4) 0.0993(3) 0.0159(4) 0.0700(13) Uani 1 1 d . . . . .
C6 C 0.6043(4) 0.0880(3) 0.1079(3) 0.0654(11) Uani 1 1 d . . . . .
C7 C 0.7268(4) 0.0766(3) 0.1348(3) 0.0589(11) Uani 1 1 d . . . . .
C8 C 0.8245(4) 0.0747(3) 0.0711(3) 0.0565(10) Uani 1 1 d . . . . .
C9 C 0.9559(4) 0.0619(3) 0.0902(3) 0.0595(11) Uani 1 1 d . . . . .
C10 C 1.1149(5) 0.1449(4) -0.1120(4) 0.0886(16) Uani 1 1 d . . . . .
H10A H 1.1581 0.1995 -0.0856 0.133 Uiso 1 1 calc R U . . .
H10B H 1.0827 0.1634 -0.1701 0.133 Uiso 1 1 calc R U . . .
H10C H 1.1716 0.0909 -0.1188 0.133 Uiso 1 1 calc R U . . .
C11 C 0.4370(4) 0.1106(4) -0.0119(4) 0.0945(18) Uani 1 1 d . . . . .
H11A H 0.4110 0.1771 -0.0021 0.142 Uiso 1 1 calc R U . . .
H11B H 0.3864 0.0672 0.0235 0.142 Uiso 1 1 calc R U . . .
H11C H 0.4280 0.0945 -0.0747 0.142 Uiso 1 1 calc R U . . .
C12 C 0.5132(5) 0.0924(4) 0.1773(4) 0.0829(15) Uani 1 1 d . . . . .
C13 C 0.9470(4) -0.0743(3) 0.1945(3) 0.0722(13) Uani 1 1 d . . . . .
H13A H 0.9903 -0.1226 0.1582 0.087 Uiso 1 1 calc R U . . .
H13B H 0.8590 -0.0778 0.1796 0.087 Uiso 1 1 calc R U . . .
C14 C 0.9653(4) -0.0979(4) 0.2933(3) 0.0814(14) Uani 1 1 d . . . . .
H14A H 0.9372 -0.1642 0.3052 0.098 Uiso 1 1 calc R U . . .
H14B H 0.9159 -0.0534 0.3297 0.098 Uiso 1 1 calc R U . . .
C15 C 1.1015(4) -0.0882(5) 0.3188(4) 0.0996(19) Uani 1 1 d . . . . .
H15A H 1.1115 -0.0981 0.3833 0.120 Uiso 1 1 calc R U . . .
H15B H 1.1496 -0.1381 0.2879 0.120 Uiso 1 1 calc R U . . .
C16 C 1.1487(4) 0.0114(5) 0.2935(3) 0.0867(16) Uani 1 1 d . . . . .
H16A H 1.2371 0.0154 0.3071 0.104 Uiso 1 1 calc R U . . .
H16B H 1.1063 0.0606 0.3294 0.104 Uiso 1 1 calc R U . . .
C17 C 1.1278(4) 0.0332(4) 0.1937(3) 0.0775(14) Uani 1 1 d . . . . .
H17A H 1.1559 0.0992 0.1800 0.093 Uiso 1 1 calc R U . . .
H17B H 1.1750 -0.0125 0.1572 0.093 Uiso 1 1 calc R U . . .
C18 C 0.7853(5) 0.1598(3) 0.2654(3) 0.0701(13) Uani 1 1 d . . . . .
H18A H 0.7232 0.2095 0.2522 0.084 Uiso 1 1 calc R U . . .
H18B H 0.8641 0.1811 0.2402 0.084 Uiso 1 1 calc R U . . .
C19 C 0.7981(4) 0.1473(3) 0.3656(3) 0.0582(11) Uani 1 1 d . . . . .
C20 C 0.8956(4) 0.1926(3) 0.4106(3) 0.0685(12) Uani 1 1 d . . . . .
H20 H 0.9531 0.2294 0.3782 0.082 Uiso 1 1 calc R U . . .
C21 C 0.9084(4) 0.1838(3) 0.5018(3) 0.0702(12) Uani 1 1 d . . . . .
H21 H 0.9739 0.2148 0.5317 0.084 Uiso 1 1 calc R U . . .
C22 C 0.8240(4) 0.1290(3) 0.5488(3) 0.0616(11) Uani 1 1 d . . . . .
C23 C 0.7266(4) 0.0827(3) 0.5068(3) 0.0662(11) Uani 1 1 d . . . . .
H23 H 0.6700 0.0457 0.5399 0.079 Uiso 1 1 calc R U . . .
C24 C 0.7138(4) 0.0920(3) 0.4149(3) 0.0642(11) Uani 1 1 d . . . . .
H24 H 0.6481 0.0609 0.3854 0.077 Uiso 1 1 calc R U . . .
C25 C 0.6877(4) 0.3666(3) 0.0786(3) 0.0615(11) Uani 1 1 d . . . . .
C26 C 0.5672(4) 0.3564(3) 0.0523(3) 0.0663(12) Uani 1 1 d . . . . .
H26 H 0.5487 0.3421 -0.0077 0.080 Uiso 1 1 calc R U . . .
C27 C 0.4705(4) 0.3673(3) 0.1146(3) 0.0594(11) Uani 1 1 d . . . . .
C28 C 0.3452(4) 0.3541(3) 0.0894(3) 0.0729(13) Uani 1 1 d . . . . .
H28 H 0.3263 0.3440 0.0288 0.087 Uiso 1 1 calc R U . . .
C29 C 0.2509(4) 0.3555(3) 0.1496(4) 0.0736(13) Uani 1 1 d . . . . .
C30 C 0.2841(4) 0.3677(3) 0.2417(3) 0.0644(12) Uani 1 1 d . . . . .
C31 C 0.4044(4) 0.3843(3) 0.2687(3) 0.0540(10) Uani 1 1 d . . . . .
C32 C 0.5014(4) 0.3903(3) 0.2049(3) 0.0515(10) Uani 1 1 d . . . . .
C33 C 0.6305(4) 0.4145(3) 0.2224(3) 0.0503(10) Uani 1 1 d . . . . .
C34 C 0.7955(4) 0.3508(4) 0.0166(3) 0.0823(15) Uani 1 1 d . . . . .
H34A H 0.8376 0.4120 0.0068 0.123 Uiso 1 1 calc R U . . .
H34B H 0.7658 0.3255 -0.0400 0.123 Uiso 1 1 calc R U . . .
H34C H 0.8524 0.3047 0.0433 0.123 Uiso 1 1 calc R U . . .
C35 C 0.1166(4) 0.3432(5) 0.1218(4) 0.107(2) Uani 1 1 d . . . . .
H35A H 0.0787 0.2929 0.1578 0.161 Uiso 1 1 calc R U . . .
H35B H 0.1124 0.3250 0.0593 0.161 Uiso 1 1 calc R U . . .
H35C H 0.0730 0.4039 0.1306 0.161 Uiso 1 1 calc R U . . .
C36 C 0.1913(5) 0.3628(4) 0.3122(4) 0.0824(16) Uani 1 1 d . . . . .
C37 C 0.6058(4) 0.5476(3) 0.3298(3) 0.0589(11) Uani 1 1 d . . . . .
H37A H 0.5174 0.5434 0.3165 0.071 Uiso 1 1 calc R U . . .
H37B H 0.6404 0.6009 0.2945 0.071 Uiso 1 1 calc R U . . .
C38 C 0.6249(4) 0.5679(3) 0.4289(3) 0.0699(12) Uani 1 1 d . . . . .
H38A H 0.5867 0.5160 0.4640 0.084 Uiso 1 1 calc R U . . .
H38B H 0.5846 0.6292 0.4446 0.084 Uiso 1 1 calc R U . . .
C39 C 0.7618(4) 0.5740(4) 0.4518(3) 0.0799(14) Uani 1 1 d . . . . .
H39A H 0.7725 0.5811 0.5166 0.096 Uiso 1 1 calc R U . . .
H39B H 0.7983 0.6309 0.4228 0.096 Uiso 1 1 calc R U . . .
C40 C 0.8268(4) 0.4817(4) 0.4200(3) 0.0719(13) Uani 1 1 d . . . . .
H40A H 0.9159 0.4888 0.4293 0.086 Uiso 1 1 calc R U . . .
H40B H 0.7987 0.4266 0.4560 0.086 Uiso 1 1 calc R U . . .
C41 C 0.8016(3) 0.4606(3) 0.3214(3) 0.0634(11) Uani 1 1 d . . . . .
H41A H 0.8375 0.5121 0.2846 0.076 Uiso 1 1 calc R U . . .
H41B H 0.8404 0.3990 0.3048 0.076 Uiso 1 1 calc R U . . .
C42 C 0.4778(5) 0.3063(3) 0.4006(3) 0.0740(13) Uani 1 1 d . . . . .
H42A H 0.5630 0.2977 0.3805 0.089 Uiso 1 1 calc R U . . .
H42B H 0.4302 0.2490 0.3826 0.089 Uiso 1 1 calc R U . . .
C43 C 0.4748(4) 0.3175(3) 0.5008(3) 0.0583(11) Uani 1 1 d . . . . .
C44 C 0.3650(4) 0.3354(3) 0.5460(3) 0.0695(12) Uani 1 1 d . . . . .
H44 H 0.2918 0.3448 0.5133 0.083 Uiso 1 1 calc R U . . .
C45 C 0.3624(4) 0.3397(4) 0.6387(3) 0.0766(14) Uani 1 1 d . . . . .
H45 H 0.2880 0.3514 0.6689 0.092 Uiso 1 1 calc R U . . .
C46 C 0.4706(5) 0.3267(3) 0.6855(3) 0.0695(12) Uani 1 1 d . . . . .
C47 C 0.5808(4) 0.3107(4) 0.6431(4) 0.0773(14) Uani 1 1 d . . . . .
H47 H 0.6540 0.3024 0.6761 0.093 Uiso 1 1 calc R U . . .
C48 C 0.5819(4) 0.3070(3) 0.5502(4) 0.0705(13) Uani 1 1 d . . . . .
H48 H 0.6570 0.2972 0.5205 0.085 Uiso 1 1 calc R 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
N1 C9 1.314(5) . ?
N1 C1 1.352(5) . ?
N2 C9 1.393(5) . ?
N2 C13 1.467(5) . ?
N2 C17 1.469(5) . ?
N3 C12 1.140(7) . ?
N4 O2 1.220(5) . ?
N4 O3 1.221(5) . ?
N4 C22 1.460(6) . ?
N5 C33 1.312(5) . ?
N5 C25 1.360(5) . ?
N6 C33 1.395(5) . ?
N6 C41 1.466(5) . ?
N6 C37 1.469(5) . ?
N7 C36 1.139(6) . ?
N8 O5 1.206(6) . ?
N8 O6 1.210(6) . ?
N8 C46 1.467(6) . ?
O1 C7 1.370(5) . ?
O1 C18 1.428(5) . ?
O4 C31 1.381(5) . ?
O4 C42 1.440(5) . ?
C1 C2 1.362(6) . ?
C1 C10 1.495(6) . ?
C2 C3 1.414(6) . ?
C2 H2 0.9300 . ?
C3 C8 1.414(5) . ?
C3 C4 1.419(6) . ?
C4 C5 1.357(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.414(6) . ?
C5 C11 1.511(5) . ?
C6 C7 1.381(5) . ?
C6 C12 1.422(7) . ?
C7 C8 1.414(6) . ?
C8 C9 1.448(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.510(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.514(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.498(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.523(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.500(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.383(6) . ?
C19 C24 1.388(5) . ?
C20 C21 1.363(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.368(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.368(6) . ?
C23 C24 1.374(6) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.356(6) . ?
C25 C34 1.496(6) . ?
C26 C27 1.400(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.405(6) . ?
C27 C32 1.413(5) . ?
C28 C29 1.352(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.418(6) . ?
C29 C35 1.507(6) . ?
C30 C31 1.368(5) . ?
C30 C36 1.449(7) . ?
C31 C32 1.411(5) . ?
C32 C33 1.446(5) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C37 C38 1.507(6) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.509(6) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.515(7) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C41 1.512(6) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C43 1.493(6) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 C48 1.367(6) . ?
C43 C44 1.379(5) . ?
C44 C45 1.375(6) . ?
C44 H44 0.9300 . ?
C45 C46 1.361(6) . ?
C45 H45 0.9300 . ?
C46 C47 1.359(6) . ?
C47 C48 1.377(6) . ?
C47 H47 0.9300 . ?
C48 H48 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
C9 N1 C1 119.8(4) . . ?
C9 N2 C13 115.4(3) . . ?
C9 N2 C17 115.8(3) . . ?
C13 N2 C17 111.8(3) . . ?
O2 N4 O3 123.8(5) . . ?
O2 N4 C22 117.4(5) . . ?
O3 N4 C22 118.8(4) . . ?
C33 N5 C25 119.9(3) . . ?
C33 N6 C41 116.0(3) . . ?
C33 N6 C37 115.9(3) . . ?
C41 N6 C37 110.8(3) . . ?
O5 N8 O6 124.0(6) . . ?
O5 N8 C46 117.4(6) . . ?
O6 N8 C46 118.6(6) . . ?
C7 O1 C18 112.5(3) . . ?
C31 O4 C42 113.4(3) . . ?
N1 C1 C2 122.2(4) . . ?
N1 C1 C10 115.5(4) . . ?
C2 C1 C10 122.2(4) . . ?
C1 C2 C3 119.6(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C8 C3 C2 118.4(4) . . ?
C8 C3 C4 120.2(4) . . ?
C2 C3 C4 121.3(4) . . ?
C5 C4 C3 121.8(4) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 118.2(4) . . ?
C4 C5 C11 121.5(5) . . ?
C6 C5 C11 120.3(5) . . ?
C7 C6 C5 121.3(4) . . ?
C7 C6 C12 116.9(5) . . ?
C5 C6 C12 121.7(4) . . ?
O1 C7 C6 117.0(4) . . ?
O1 C7 C8 121.9(4) . . ?
C6 C7 C8 121.1(4) . . ?
C3 C8 C7 116.9(4) . . ?
C3 C8 C9 116.3(4) . . ?
C7 C8 C9 126.6(4) . . ?
N1 C9 N2 117.8(4) . . ?
N1 C9 C8 122.1(4) . . ?
N2 C9 C8 120.1(4) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C6 177.4(6) . . ?
N2 C13 C14 111.1(4) . . ?
N2 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
N2 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 110.1(4) . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 110.1(4) . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.2 . . ?
C15 C16 C17 111.8(5) . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
N2 C17 C16 108.9(4) . . ?
N2 C17 H17A 109.9 . . ?
C16 C17 H17A 109.9 . . ?
N2 C17 H17B 109.9 . . ?
C16 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
O1 C18 C19 109.4(3) . . ?
O1 C18 H18A 109.8 . . ?
C19 C18 H18A 109.8 . . ?
O1 C18 H18B 109.8 . . ?
C19 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
C20 C19 C24 118.9(4) . . ?
C20 C19 C18 119.4(4) . . ?
C24 C19 C18 121.7(4) . . ?
C21 C20 C19 120.8(4) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 119.2(4) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C21 C22 C23 121.8(4) . . ?
C21 C22 N4 119.5(4) . . ?
C23 C22 N4 118.7(4) . . ?
C22 C23 C24 118.7(4) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C23 C24 C19 120.6(4) . . ?
C23 C24 H24 119.7 . . ?
C19 C24 H24 119.7 . . ?
C26 C25 N5 121.5(4) . . ?
C26 C25 C34 123.2(4) . . ?
N5 C25 C34 115.1(4) . . ?
C25 C26 C27 120.6(4) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C26 C27 C28 121.5(4) . . ?
C26 C27 C32 118.5(4) . . ?
C28 C27 C32 120.0(4) . . ?
C29 C28 C27 122.7(5) . . ?
C29 C28 H28 118.6 . . ?
C27 C28 H28 118.6 . . ?
C28 C29 C30 116.8(4) . . ?
C28 C29 C35 122.4(5) . . ?
C30 C29 C35 120.8(5) . . ?
C31 C30 C29 122.2(4) . . ?
C31 C30 C36 116.6(4) . . ?
C29 C30 C36 121.2(4) . . ?
C30 C31 O4 116.6(4) . . ?
C30 C31 C32 120.8(4) . . ?
O4 C31 C32 122.6(3) . . ?
C31 C32 C27 116.8(4) . . ?
C31 C32 C33 127.0(4) . . ?
C27 C32 C33 116.2(4) . . ?
N5 C33 N6 117.1(3) . . ?
N5 C33 C32 122.1(4) . . ?
N6 C33 C32 120.8(4) . . ?
C25 C34 H34A 109.5 . . ?
C25 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C25 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C29 C35 H35A 109.5 . . ?
C29 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C29 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N7 C36 C30 179.4(6) . . ?
N6 C37 C38 110.1(3) . . ?
N6 C37 H37A 109.6 . . ?
C38 C37 H37A 109.6 . . ?
N6 C37 H37B 109.6 . . ?
C38 C37 H37B 109.6 . . ?
H37A C37 H37B 108.2 . . ?
C37 C38 C39 110.9(4) . . ?
C37 C38 H38A 109.4 . . ?
C39 C38 H38A 109.4 . . ?
C37 C38 H38B 109.4 . . ?
C39 C38 H38B 109.4 . . ?
H38A C38 H38B 108.0 . . ?
C38 C39 C40 109.4(4) . . ?
C38 C39 H39A 109.8 . . ?
C40 C39 H39A 109.8 . . ?
C38 C39 H39B 109.8 . . ?
C40 C39 H39B 109.8 . . ?
H39A C39 H39B 108.2 . . ?
C41 C40 C39 112.2(4) . . ?
C41 C40 H40A 109.2 . . ?
C39 C40 H40A 109.2 . . ?
C41 C40 H40B 109.2 . . ?
C39 C40 H40B 109.2 . . ?
H40A C40 H40B 107.9 . . ?
N6 C41 C40 110.1(3) . . ?
N6 C41 H41A 109.6 . . ?
C40 C41 H41A 109.6 . . ?
N6 C41 H41B 109.6 . . ?
C40 C41 H41B 109.6 . . ?
H41A C41 H41B 108.2 . . ?
O4 C42 C43 108.5(3) . . ?
O4 C42 H42A 110.0 . . ?
C43 C42 H42A 110.0 . . ?
O4 C42 H42B 110.0 . . ?
C43 C42 H42B 110.0 . . ?
H42A C42 H42B 108.4 . . ?
C48 C43 C44 118.5(4) . . ?
C48 C43 C42 120.0(4) . . ?
C44 C43 C42 121.6(4) . . ?
C45 C44 C43 121.0(4) . . ?
C45 C44 H44 119.5 . . ?
C43 C44 H44 119.5 . . ?
C46 C45 C44 118.7(4) . . ?
C46 C45 H45 120.6 . . ?
C44 C45 H45 120.6 . . ?
C47 C46 C45 121.9(5) . . ?
C47 C46 N8 118.9(5) . . ?
C45 C46 N8 119.2(5) . . ?
C46 C47 C48 118.6(5) . . ?
C46 C47 H47 120.7 . . ?
C48 C47 H47 120.7 . . ?
C43 C48 C47 121.3(4) . . ?
C43 C48 H48 119.3 . . ?
C47 C48 H48 119.3 . . ?

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
C9 N1 C1 C2 -4.6(7) . . . . ?
C9 N1 C1 C10 177.9(4) . . . . ?
N1 C1 C2 C3 9.8(7) . . . . ?
C10 C1 C2 C3 -172.9(4) . . . . ?
C1 C2 C3 C8 -2.9(6) . . . . ?
C1 C2 C3 C4 172.4(4) . . . . ?
C8 C3 C4 C5 4.3(7) . . . . ?
C2 C3 C4 C5 -170.9(4) . . . . ?
C3 C4 C5 C6 1.3(7) . . . . ?
C3 C4 C5 C11 178.9(4) . . . . ?
C4 C5 C6 C7 -3.1(6) . . . . ?
C11 C5 C6 C7 179.3(4) . . . . ?
C4 C5 C6 C12 174.0(5) . . . . ?
C11 C5 C6 C12 -3.6(7) . . . . ?
C18 O1 C7 C6 -97.3(4) . . . . ?
C18 O1 C7 C8 81.8(5) . . . . ?
C5 C6 C7 O1 178.4(4) . . . . ?
C12 C6 C7 O1 1.2(6) . . . . ?
C5 C6 C7 C8 -0.7(6) . . . . ?
C12 C6 C7 C8 -177.9(4) . . . . ?
C2 C3 C8 C7 167.5(4) . . . . ?
C4 C3 C8 C7 -7.9(6) . . . . ?
C2 C3 C8 C9 -7.8(6) . . . . ?
C4 C3 C8 C9 176.8(4) . . . . ?
O1 C7 C8 C3 -172.9(4) . . . . ?
C6 C7 C8 C3 6.2(6) . . . . ?
O1 C7 C8 C9 1.8(6) . . . . ?
C6 C7 C8 C9 -179.1(4) . . . . ?
C1 N1 C9 N2 173.8(4) . . . . ?
C1 N1 C9 C8 -7.2(6) . . . . ?
C13 N2 C9 N1 -121.8(4) . . . . ?
C17 N2 C9 N1 11.5(6) . . . . ?
C13 N2 C9 C8 59.2(5) . . . . ?
C17 N2 C9 C8 -167.4(4) . . . . ?
C3 C8 C9 N1 13.3(6) . . . . ?
C7 C8 C9 N1 -161.5(4) . . . . ?
C3 C8 C9 N2 -167.8(4) . . . . ?
C7 C8 C9 N2 17.5(6) . . . . ?
C9 N2 C13 C14 -165.4(4) . . . . ?
C17 N2 C13 C14 59.5(5) . . . . ?
N2 C13 C14 C15 -56.5(5) . . . . ?
C13 C14 C15 C16 54.5(6) . . . . ?
C14 C15 C16 C17 -55.8(6) . . . . ?
C9 N2 C17 C16 166.6(4) . . . . ?
C13 N2 C17 C16 -58.5(5) . . . . ?
C15 C16 C17 N2 57.1(6) . . . . ?
C7 O1 C18 C19 175.5(3) . . . . ?
O1 C18 C19 C20 139.8(4) . . . . ?
O1 C18 C19 C24 -40.7(5) . . . . ?
C24 C19 C20 C21 -0.6(6) . . . . ?
C18 C19 C20 C21 178.9(4) . . . . ?
C19 C20 C21 C22 0.5(7) . . . . ?
C20 C21 C22 C23 -0.2(6) . . . . ?
C20 C21 C22 N4 -178.4(4) . . . . ?
O2 N4 C22 C21 -15.5(6) . . . . ?
O3 N4 C22 C21 163.5(4) . . . . ?
O2 N4 C22 C23 166.2(4) . . . . ?
O3 N4 C22 C23 -14.8(6) . . . . ?
C21 C22 C23 C24 0.0(6) . . . . ?
N4 C22 C23 C24 178.2(4) . . . . ?
C22 C23 C24 C19 -0.1(6) . . . . ?
C20 C19 C24 C23 0.4(6) . . . . ?
C18 C19 C24 C23 -179.1(4) . . . . ?
C33 N5 C25 C26 4.5(6) . . . . ?
C33 N5 C25 C34 -179.7(4) . . . . ?
N5 C25 C26 C27 -7.9(6) . . . . ?
C34 C25 C26 C27 176.7(4) . . . . ?
C25 C26 C27 C28 -178.0(4) . . . . ?
C25 C26 C27 C32 0.9(6) . . . . ?
C26 C27 C28 C29 174.0(4) . . . . ?
C32 C27 C28 C29 -4.9(6) . . . . ?
C27 C28 C29 C30 -2.1(7) . . . . ?
C27 C28 C29 C35 178.8(4) . . . . ?
C28 C29 C30 C31 4.5(6) . . . . ?
C35 C29 C30 C31 -176.4(4) . . . . ?
C28 C29 C30 C36 -175.3(4) . . . . ?
C35 C29 C30 C36 3.8(7) . . . . ?
C29 C30 C31 O4 -178.8(3) . . . . ?
C36 C30 C31 O4 1.0(5) . . . . ?
C29 C30 C31 C32 0.3(6) . . . . ?
C36 C30 C31 C32 -179.9(4) . . . . ?
C42 O4 C31 C30 102.4(4) . . . . ?
C42 O4 C31 C32 -76.6(4) . . . . ?
C30 C31 C32 C27 -7.2(5) . . . . ?
O4 C31 C32 C27 171.9(3) . . . . ?
C30 C31 C32 C33 175.1(4) . . . . ?
O4 C31 C32 C33 -5.9(6) . . . . ?
C26 C27 C32 C31 -169.5(4) . . . . ?
C28 C27 C32 C31 9.4(5) . . . . ?
C26 C27 C32 C33 8.5(5) . . . . ?
C28 C27 C32 C33 -172.6(4) . . . . ?
C25 N5 C33 N6 -174.8(3) . . . . ?
C25 N5 C33 C32 5.8(6) . . . . ?
C41 N6 C33 N5 -9.8(5) . . . . ?
C37 N6 C33 N5 122.8(4) . . . . ?
C41 N6 C33 C32 169.7(3) . . . . ?
C37 N6 C33 C32 -57.8(5) . . . . ?
C31 C32 C33 N5 165.6(4) . . . . ?
C27 C32 C33 N5 -12.2(5) . . . . ?
C31 C32 C33 N6 -13.8(6) . . . . ?
C27 C32 C33 N6 168.4(3) . . . . ?
C33 N6 C37 C38 163.9(3) . . . . ?
C41 N6 C37 C38 -61.1(4) . . . . ?
N6 C37 C38 C39 58.8(5) . . . . ?
C37 C38 C39 C40 -54.3(5) . . . . ?
C38 C39 C40 C41 53.1(5) . . . . ?
C33 N6 C41 C40 -166.0(3) . . . . ?
C37 N6 C41 C40 59.2(4) . . . . ?
C39 C40 C41 N6 -55.7(5) . . . . ?
C31 O4 C42 C43 -170.1(3) . . . . ?
O4 C42 C43 C48 -125.5(4) . . . . ?
O4 C42 C43 C44 56.5(5) . . . . ?
C48 C43 C44 C45 -2.0(6) . . . . ?
C42 C43 C44 C45 176.0(4) . . . . ?
C43 C44 C45 C46 0.5(7) . . . . ?
C44 C45 C46 C47 0.8(7) . . . . ?
C44 C45 C46 N8 -177.6(4) . . . . ?
O5 N8 C46 C47 1.7(8) . . . . ?
O6 N8 C46 C47 -177.1(5) . . . . ?
O5 N8 C46 C45 -179.9(6) . . . . ?
O6 N8 C46 C45 1.3(8) . . . . ?
C45 C46 C47 C48 -0.5(7) . . . . ?
N8 C46 C47 C48 177.9(4) . . . . ?
C44 C43 C48 C47 2.2(6) . . . . ?
C42 C43 C48 C47 -175.8(4) . . . . ?
C46 C47 C48 C43 -1.1(7) . . . . ?

_refine_diff_density_max         0.145
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.028

_shelxl_version_number           2013-4



