# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_181008d
_database_code_depnum_ccdc_archive 'CCDC 2020983'
loop_
_audit_author_name
_audit_author_address
'Ruokun Feng'
;Shaoxing University
China
;
_audit_update_record             
;
2020-08-02 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H20 F2 N O'
_chemical_formula_weight         472.49

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0495(9)
_cell_length_b                   11.3463(11)
_cell_length_c                   13.2051(12)
_cell_angle_alpha                84.652(2)
_cell_angle_beta                 76.7280(10)
_cell_angle_gamma                75.7750(10)
_cell_volume                     1278.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1134
_cell_measurement_theta_min      2.560
_cell_measurement_theta_max      20.817

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             490
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9737
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13012
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4441
_reflns_number_gt                2352
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1103P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4441
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1926
_refine_ls_wR_factor_gt          0.1544
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.935
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1298(3) 0.04278(19) 0.18637(16) 0.0630(6) Uani 1 1 d . . .
H1 H 0.2155 0.0448 0.1423 0.076 Uiso 1 1 calc R . .
O1 O -0.1344(3) 0.1077(2) 0.20633(19) 0.1069(8) Uani 1 1 d . . .
F1 F -0.0733(4) 0.5518(2) 0.35520(17) 0.1837(14) Uani 1 1 d . . .
F2 F 0.4413(4) 0.6292(2) -0.38988(18) 0.1616(11) Uani 1 1 d . . .
C1 C 0.1464(3) -0.0147(2) 0.28476(19) 0.0613(7) Uani 1 1 d . . .
C2 C 0.0306(4) -0.0683(3) 0.3422(2) 0.0820(9) Uani 1 1 d . . .
H2A H -0.0625 -0.0582 0.3203 0.098 Uiso 1 1 calc R . .
C3 C 0.0521(5) -0.1377(3) 0.4333(3) 0.0925(10) Uani 1 1 d . . .
H3 H -0.0291 -0.1697 0.4730 0.111 Uiso 1 1 calc R . .
C4 C 0.1882(4) -0.1591(3) 0.4647(2) 0.0847(10) Uani 1 1 d . . .
H4 H 0.2020 -0.2088 0.5235 0.102 Uiso 1 1 calc R . .
C5 C 0.3106(4) -0.1057(2) 0.40805(19) 0.0658(8) Uani 1 1 d . . .
C6 C 0.2876(3) -0.0255(2) 0.31953(17) 0.0567(7) Uani 1 1 d . . .
C7 C 0.4086(3) 0.0365(2) 0.27174(18) 0.0578(7) Uani 1 1 d . . .
C8 C 0.5476(3) 0.0068(3) 0.3045(2) 0.0727(8) Uani 1 1 d . . .
H8 H 0.6265 0.0456 0.2722 0.087 Uiso 1 1 calc R . .
C9 C 0.5737(4) -0.0801(3) 0.3851(2) 0.0822(9) Uani 1 1 d . . .
H9 H 0.6709 -0.1021 0.4027 0.099 Uiso 1 1 calc R . .
C10 C 0.4560(4) -0.1321(3) 0.4373(2) 0.0801(9) Uani 1 1 d . . .
H10 H 0.4718 -0.1861 0.4933 0.096 Uiso 1 1 calc R . .
C11 C -0.0024(4) 0.0947(3) 0.1528(2) 0.0692(8) Uani 1 1 d . . .
C12 C 0.0255(4) 0.1418(2) 0.0411(2) 0.0654(7) Uani 1 1 d . . .
N2 N 0.1738(3) 0.1278(2) -0.01024(18) 0.0705(7) Uani 1 1 d . . .
C14 C 0.1990(4) 0.1735(3) -0.1080(2) 0.0811(9) Uani 1 1 d . . .
H14 H 0.3015 0.1655 -0.1448 0.097 Uiso 1 1 calc R . .
C15 C 0.0798(5) 0.2322(3) -0.1569(3) 0.0943(11) Uani 1 1 d . . .
H15 H 0.1020 0.2640 -0.2247 0.113 Uiso 1 1 calc R . .
C16 C -0.0704(6) 0.2425(3) -0.1043(3) 0.1066(12) Uani 1 1 d . . .
H16 H -0.1526 0.2798 -0.1361 0.128 Uiso 1 1 calc R . .
C17 C -0.0990(4) 0.1971(3) -0.0035(3) 0.0899(10) Uani 1 1 d . . .
H17 H -0.2008 0.2035 0.0342 0.108 Uiso 1 1 calc R . .
C18 C 0.3853(3) 0.1427(2) 0.19511(19) 0.0569(7) Uani 1 1 d . . .
C19 C 0.2657(3) 0.2529(2) 0.23475(19) 0.0594(7) Uani 1 1 d . . .
C20 C 0.1774(4) 0.3320(3) 0.1720(2) 0.0719(8) Uani 1 1 d . . .
H20 H 0.1950 0.3171 0.1017 0.086 Uiso 1 1 calc R . .
C21 C 0.0644(4) 0.4320(3) 0.2120(3) 0.0983(11) Uani 1 1 d . . .
H21 H 0.0063 0.4842 0.1694 0.118 Uiso 1 1 calc R . .
C22 C 0.0395(5) 0.4525(3) 0.3157(3) 0.1173(14) Uani 1 1 d . . .
C23 C 0.1250(5) 0.3782(3) 0.3800(3) 0.1165(14) Uani 1 1 d . . .
H23 H 0.1085 0.3953 0.4498 0.140 Uiso 1 1 calc R . .
C24 C 0.2357(4) 0.2780(3) 0.3394(2) 0.0818(9) Uani 1 1 d . . .
H24 H 0.2919 0.2258 0.3831 0.098 Uiso 1 1 calc R . .
C25 C 0.4812(3) 0.1355(3) 0.09940(19) 0.0649(7) Uani 1 1 d . . .
H25 H 0.5537 0.0621 0.0848 0.078 Uiso 1 1 calc R . .
C26 C 0.4830(3) 0.2285(3) 0.0183(2) 0.0648(8) Uani 1 1 d . . .
C27 C 0.4863(3) 0.3021(3) -0.0536(2) 0.0656(8) Uani 1 1 d . . .
C28 C 0.4781(3) 0.3892(3) -0.1397(2) 0.0643(7) Uani 1 1 d . . .
C29 C 0.5558(5) 0.3551(3) -0.2394(2) 0.1014(12) Uani 1 1 d . . .
H29 H 0.6171 0.2766 -0.2499 0.122 Uiso 1 1 calc R . .
C30 C 0.5436(5) 0.4356(4) -0.3233(3) 0.1204(15) Uani 1 1 d . . .
H30 H 0.5956 0.4122 -0.3902 0.145 Uiso 1 1 calc R . .
C31 C 0.4547(5) 0.5492(4) -0.3067(3) 0.1008(12) Uani 1 1 d . . .
C32 C 0.3795(5) 0.5883(3) -0.2108(3) 0.1054(12) Uani 1 1 d . . .
H32 H 0.3206 0.6677 -0.2016 0.127 Uiso 1 1 calc R . .
C33 C 0.3923(4) 0.5070(3) -0.1262(3) 0.0886(10) Uani 1 1 d . . .
H33 H 0.3421 0.5325 -0.0595 0.106 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C11 1.350(4) . ?
N1 C1 1.421(3) . ?
N1 H1 0.8600 . ?
O1 C11 1.222(3) . ?
F1 C22 1.372(4) . ?
F2 C31 1.366(3) . ?
C1 C2 1.381(4) . ?
C1 C6 1.428(4) . ?
C2 C3 1.401(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.347(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.421(4) . ?
C4 H4 0.9300 . ?
C5 C10 1.410(4) . ?
C5 C6 1.435(3) . ?
C6 C7 1.439(3) . ?
C7 C8 1.377(4) . ?
C7 C18 1.506(3) . ?
C8 C9 1.402(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.362(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.508(4) . ?
C12 N2 1.335(3) . ?
C12 C17 1.377(4) . ?
N2 C14 1.336(3) . ?
C14 C15 1.383(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.359(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C25 1.356(3) . ?
C18 C19 1.485(4) . ?
C19 C24 1.389(4) . ?
C19 C20 1.394(4) . ?
C20 C21 1.380(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.368(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.370(5) . ?
C23 C24 1.375(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.432(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.205(3) . ?
C27 C28 1.438(4) . ?
C28 C33 1.375(4) . ?
C28 C29 1.384(4) . ?
C29 C30 1.375(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.349(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.351(5) . ?
C32 C33 1.388(4) . ?
C32 H32 0.9300 . ?
C33 H33 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
C11 N1 C1 128.7(2) . . ?
C11 N1 H1 115.6 . . ?
C1 N1 H1 115.6 . . ?
C2 C1 N1 119.4(3) . . ?
C2 C1 C6 120.4(3) . . ?
N1 C1 C6 120.0(2) . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C10 C5 C4 120.5(3) . . ?
C10 C5 C6 119.4(2) . . ?
C4 C5 C6 120.1(3) . . ?
C1 C6 C5 117.1(2) . . ?
C1 C6 C7 125.0(2) . . ?
C5 C6 C7 117.9(3) . . ?
C8 C7 C6 119.3(2) . . ?
C8 C7 C18 117.3(2) . . ?
C6 C7 C18 123.1(2) . . ?
C7 C8 C9 122.0(3) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C5 121.3(3) . . ?
C9 C10 H10 119.3 . . ?
C5 C10 H10 119.3 . . ?
O1 C11 N1 125.0(3) . . ?
O1 C11 C12 121.1(3) . . ?
N1 C11 C12 113.8(3) . . ?
N2 C12 C17 122.9(3) . . ?
N2 C12 C11 117.0(3) . . ?
C17 C12 C11 120.1(3) . . ?
C12 N2 C14 117.2(3) . . ?
N2 C14 C15 123.0(3) . . ?
N2 C14 H14 118.5 . . ?
C15 C14 H14 118.5 . . ?
C16 C15 C14 118.9(3) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 119.0(3) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C16 C17 C12 119.0(3) . . ?
C16 C17 H17 120.5 . . ?
C12 C17 H17 120.5 . . ?
C25 C18 C19 124.8(2) . . ?
C25 C18 C7 118.8(3) . . ?
C19 C18 C7 116.2(2) . . ?
C24 C19 C20 117.6(3) . . ?
C24 C19 C18 119.4(3) . . ?
C20 C19 C18 123.0(2) . . ?
C21 C20 C19 121.4(3) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C22 C21 C20 118.6(3) . . ?
C22 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
C21 C22 C23 122.0(3) . . ?
C21 C22 F1 118.4(3) . . ?
C23 C22 F1 119.6(3) . . ?
C24 C23 C22 118.8(3) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C23 C24 C19 121.5(3) . . ?
C23 C24 H24 119.2 . . ?
C19 C24 H24 119.2 . . ?
C18 C25 C26 127.1(3) . . ?
C18 C25 H25 116.5 . . ?
C26 C25 H25 116.5 . . ?
C27 C26 C25 176.6(3) . . ?
C26 C27 C28 175.5(3) . . ?
C33 C28 C29 118.3(3) . . ?
C33 C28 C27 121.6(3) . . ?
C29 C28 C27 120.1(3) . . ?
C30 C29 C28 120.9(3) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C31 C30 C29 118.8(3) . . ?
C31 C30 H30 120.6 . . ?
C29 C30 H30 120.6 . . ?
C30 C31 C32 122.8(3) . . ?
C30 C31 F2 119.0(3) . . ?
C32 C31 F2 118.2(4) . . ?
C31 C32 C33 118.3(3) . . ?
C31 C32 H32 120.8 . . ?
C33 C32 H32 120.8 . . ?
C28 C33 C32 120.9(3) . . ?
C28 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?

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
C11 N1 C1 C2 27.4(4) . . . . ?
C11 N1 C1 C6 -157.8(3) . . . . ?
N1 C1 C2 C3 172.4(3) . . . . ?
C6 C1 C2 C3 -2.4(4) . . . . ?
C1 C2 C3 C4 -3.2(5) . . . . ?
C2 C3 C4 C5 3.2(5) . . . . ?
C3 C4 C5 C10 -176.9(3) . . . . ?
C3 C4 C5 C6 2.2(4) . . . . ?
C2 C1 C6 C5 7.5(4) . . . . ?
N1 C1 C6 C5 -167.3(2) . . . . ?
C2 C1 C6 C7 -173.4(2) . . . . ?
N1 C1 C6 C7 11.8(4) . . . . ?
C10 C5 C6 C1 171.7(2) . . . . ?
C4 C5 C6 C1 -7.4(4) . . . . ?
C10 C5 C6 C7 -7.5(4) . . . . ?
C4 C5 C6 C7 173.4(2) . . . . ?
C1 C6 C7 C8 -171.9(3) . . . . ?
C5 C6 C7 C8 7.3(4) . . . . ?
C1 C6 C7 C18 15.0(4) . . . . ?
C5 C6 C7 C18 -165.8(2) . . . . ?
C6 C7 C8 C9 -1.6(4) . . . . ?
C18 C7 C8 C9 171.9(3) . . . . ?
C7 C8 C9 C10 -4.0(5) . . . . ?
C8 C9 C10 C5 3.8(5) . . . . ?
C4 C5 C10 C9 -178.8(3) . . . . ?
C6 C5 C10 C9 2.1(4) . . . . ?
C1 N1 C11 O1 5.1(5) . . . . ?
C1 N1 C11 C12 -177.2(2) . . . . ?
O1 C11 C12 N2 177.4(3) . . . . ?
N1 C11 C12 N2 -0.4(4) . . . . ?
O1 C11 C12 C17 -2.2(4) . . . . ?
N1 C11 C12 C17 -180.0(3) . . . . ?
C17 C12 N2 C14 2.0(4) . . . . ?
C11 C12 N2 C14 -177.6(2) . . . . ?
C12 N2 C14 C15 -0.7(4) . . . . ?
N2 C14 C15 C16 -1.1(5) . . . . ?
C14 C15 C16 C17 1.6(5) . . . . ?
C15 C16 C17 C12 -0.3(5) . . . . ?
N2 C12 C17 C16 -1.5(5) . . . . ?
C11 C12 C17 C16 178.0(3) . . . . ?
C8 C7 C18 C25 63.6(3) . . . . ?
C6 C7 C18 C25 -123.1(3) . . . . ?
C8 C7 C18 C19 -111.1(3) . . . . ?
C6 C7 C18 C19 62.1(3) . . . . ?
C25 C18 C19 C24 -144.9(3) . . . . ?
C7 C18 C19 C24 29.5(3) . . . . ?
C25 C18 C19 C20 36.9(4) . . . . ?
C7 C18 C19 C20 -148.6(2) . . . . ?
C24 C19 C20 C21 0.2(4) . . . . ?
C18 C19 C20 C21 178.3(3) . . . . ?
C19 C20 C21 C22 -0.2(5) . . . . ?
C20 C21 C22 C23 1.1(6) . . . . ?
C20 C21 C22 F1 -179.8(3) . . . . ?
C21 C22 C23 C24 -2.0(7) . . . . ?
F1 C22 C23 C24 178.9(4) . . . . ?
C22 C23 C24 C19 2.0(6) . . . . ?
C20 C19 C24 C23 -1.1(4) . . . . ?
C18 C19 C24 C23 -179.3(3) . . . . ?
C19 C18 C25 C26 -2.2(4) . . . . ?
C7 C18 C25 C26 -176.5(2) . . . . ?
C18 C25 C26 C27 -144(4) . . . . ?
C25 C26 C27 C28 80(6) . . . . ?
C26 C27 C28 C33 76(4) . . . . ?
C26 C27 C28 C29 -103(4) . . . . ?
C33 C28 C29 C30 -2.0(5) . . . . ?
C27 C28 C29 C30 177.0(3) . . . . ?
C28 C29 C30 C31 0.3(6) . . . . ?
C29 C30 C31 C32 1.4(7) . . . . ?
C29 C30 C31 F2 -179.5(4) . . . . ?
C30 C31 C32 C33 -1.3(6) . . . . ?
F2 C31 C32 C33 179.6(3) . . . . ?
C29 C28 C33 C32 2.1(5) . . . . ?
C27 C28 C33 C32 -176.9(3) . . . . ?
C31 C32 C33 C28 -0.6(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_180807b
_database_code_depnum_ccdc_archive 'CCDC 2020985'
loop_
_audit_author_name
_audit_author_address
'Ruokun Feng'
;Shaoxing University
China
;
_audit_update_record             
;
2020-08-02 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H21 Cl N2 O3'
_chemical_formula_weight         456.91

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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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

_cell_length_a                   13.5100(11)
_cell_length_b                   9.6529(8)
_cell_length_c                   17.2677(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.5150(10)
_cell_angle_gamma                90.00
_cell_volume                     2241.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3597
_cell_measurement_theta_min      2.369
_cell_measurement_theta_max      25.954

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9567
_exptl_absorpt_correction_T_max  0.9644
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10842
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3950
_reflns_number_gt                2734
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0476P)²+0.4530P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0115(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3950
_refine_ls_number_parameters     314
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1063
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.40229(4) 0.31930(6) 0.04091(4) 0.0754(2) Uani 1 1 d . A .
N1 N 0.88607(11) 0.22421(15) 0.09543(9) 0.0447(4) Uani 1 1 d . . .
H1 H 0.9036 0.1686 0.0603 0.054 Uiso 1 1 calc R . .
N2 N 0.92378(12) 0.27998(19) -0.04878(10) 0.0566(5) Uani 1 1 d . . .
O1 O 0.86985(19) -0.0520(3) -0.14905(13) 0.0618(8) Uani 0.734(4) 1 d PDU A 1
O2 O 0.7114(11) 0.001(2) -0.1321(6) 0.0656(13) Uani 0.734(4) 1 d PU A 1
O1' O 0.8418(6) -0.1199(10) -0.1512(4) 0.0618(8) Uani 0.266(4) 1 d PD A 2
O2' O 0.702(3) 0.003(6) -0.1461(18) 0.0656(13) Uani 0.266(4) 1 d P A 2
O3 O 0.83044(13) 0.44413(15) 0.11242(10) 0.0730(5) Uani 1 1 d . . .
C1 C 0.78935(17) -0.0344(2) -0.10706(12) 0.0557(5) Uani 1 1 d . . .
C2 C 0.82298(14) -0.0535(2) -0.02426(11) 0.0473(5) Uani 1 1 d . A .
H2 H 0.8830 -0.1000 -0.0136 0.057 Uiso 1 1 calc R . .
C3 C 0.77833(13) -0.01259(18) 0.03798(10) 0.0390(4) Uani 1 1 d . . .
C4 C 0.81794(12) -0.06361(18) 0.11683(10) 0.0380(4) Uani 1 1 d . A .
C5 C 0.80643(14) -0.20196(19) 0.13154(11) 0.0459(5) Uani 1 1 d . . .
H5 H 0.7847 -0.2602 0.0905 0.055 Uiso 1 1 calc R A .
C6 C 0.82619(14) -0.2590(2) 0.20606(12) 0.0513(5) Uani 1 1 d . A .
H6 H 0.8204 -0.3539 0.2136 0.062 Uiso 1 1 calc R . .
C7 C 0.85379(14) -0.1748(2) 0.26686(12) 0.0511(5) Uani 1 1 d . . .
H7 H 0.8621 -0.2114 0.3169 0.061 Uiso 1 1 calc R A .
C8 C 0.87018(13) -0.0318(2) 0.25561(11) 0.0434(5) Uani 1 1 d . A .
C9 C 0.85616(12) 0.02612(18) 0.17941(10) 0.0379(4) Uani 1 1 d . . .
C10 C 0.88313(13) 0.16787(19) 0.17070(11) 0.0413(4) Uani 1 1 d . A .
C11 C 0.91321(14) 0.2466(2) 0.23491(12) 0.0514(5) Uani 1 1 d . . .
H11 H 0.9284 0.3397 0.2288 0.062 Uiso 1 1 calc R A .
C12 C 0.92113(16) 0.1887(2) 0.30909(13) 0.0597(6) Uani 1 1 d . A .
H12 H 0.9401 0.2442 0.3520 0.072 Uiso 1 1 calc R . .
C13 C 0.90172(15) 0.0533(2) 0.31963(12) 0.0545(5) Uani 1 1 d . . .
H13 H 0.9092 0.0159 0.3695 0.065 Uiso 1 1 calc R A .
C14 C 0.68489(13) 0.07117(18) 0.03640(10) 0.0377(4) Uani 1 1 d . A .
C15 C 0.66775(14) 0.18886(19) -0.00929(11) 0.0457(5) Uani 1 1 d . . .
H15 H 0.7150 0.2163 -0.0420 0.055 Uiso 1 1 calc R A .
C16 C 0.58201(15) 0.2658(2) -0.00710(12) 0.0506(5) Uani 1 1 d . A .
H16 H 0.5724 0.3459 -0.0367 0.061 Uiso 1 1 calc R . .
C17 C 0.51128(14) 0.2225(2) 0.03929(12) 0.0471(5) Uani 1 1 d . . .
C18 C 0.52453(14) 0.1059(2) 0.08467(11) 0.0478(5) Uani 1 1 d . A .
H18 H 0.4753 0.0766 0.1151 0.057 Uiso 1 1 calc R . .
C19 C 0.61263(13) 0.03278(19) 0.08420(11) 0.0424(5) Uani 1 1 d . . .
H19 H 0.6236 -0.0437 0.1166 0.051 Uiso 1 1 calc R A .
C20 C 0.86449(14) 0.3554(2) 0.07216(12) 0.0491(5) Uani 1 1 d . . .
C21 C 0.88625(14) 0.3841(2) -0.00992(12) 0.0499(5) Uani 1 1 d . . .
C22 C 0.86902(17) 0.5137(2) -0.04168(15) 0.0687(7) Uani 1 1 d . . .
H22 H 0.8428 0.5841 -0.0131 0.082 Uiso 1 1 calc R . .
C23 C 0.8913(2) 0.5368(3) -0.11650(18) 0.0857(8) Uani 1 1 d . . .
H23 H 0.8805 0.6234 -0.1393 0.103 Uiso 1 1 calc R . .
C24 C 0.9294(2) 0.4317(3) -0.15711(16) 0.0814(8) Uani 1 1 d . . .
H24 H 0.9448 0.4451 -0.2079 0.098 Uiso 1 1 calc R . .
C25 C 0.94459(17) 0.3051(3) -0.12121(14) 0.0685(7) Uani 1 1 d . . .
H25 H 0.9707 0.2335 -0.1490 0.082 Uiso 1 1 calc R . .
C26 C 0.8526(3) -0.0308(4) -0.2325(2) 0.0704(10) Uani 0.734(4) 1 d PDU A 1
H26A H 0.9138 -0.0002 -0.2524 0.085 Uiso 0.734(4) 1 calc PR A 1
H26B H 0.8031 0.0413 -0.2433 0.085 Uiso 0.734(4) 1 calc PR A 1
C27 C 0.8180(3) -0.1594(4) -0.2726(3) 0.0825(11) Uani 0.734(4) 1 d PDU A 1
H27A H 0.8682 -0.2296 -0.2638 0.124 Uiso 0.734(4) 1 calc PR A 1
H27B H 0.8055 -0.1421 -0.3274 0.124 Uiso 0.734(4) 1 calc PR A 1
H27C H 0.7579 -0.1902 -0.2526 0.124 Uiso 0.734(4) 1 calc PR A 1
C26' C 0.8165(9) -0.1248(13) -0.2335(5) 0.0704(10) Uani 0.266(4) 1 d PD A 2
H26C H 0.7455 -0.1408 -0.2437 0.085 Uiso 0.266(4) 1 calc PR A 2
H26D H 0.8506 -0.2022 -0.2548 0.085 Uiso 0.266(4) 1 calc PR A 2
C27' C 0.8436(8) 0.0078(11) -0.2745(7) 0.0825(11) Uani 0.266(4) 1 d PD A 2
H27D H 0.7987 0.0805 -0.2631 0.124 Uiso 0.266(4) 1 calc PR A 2
H27E H 0.8386 -0.0077 -0.3297 0.124 Uiso 0.266(4) 1 calc PR A 2
H27F H 0.9104 0.0341 -0.2567 0.124 Uiso 0.266(4) 1 calc PR A 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
Cl1 C17 1.7462(19) . ?
N1 C20 1.352(2) . ?
N1 C10 1.413(2) . ?
N1 H1 0.8600 . ?
N2 C25 1.330(3) . ?
N2 C21 1.336(3) . ?
O1 C1 1.374(3) . ?
O1 C26 1.453(4) . ?
O2 C1 1.152(14) . ?
O1' C1 1.367(8) . ?
O1' C26' 1.430(8) . ?
O2' C1 1.35(4) . ?
O3 C20 1.221(2) . ?
C1 C2 1.470(3) . ?
C2 C3 1.341(2) . ?
C2 H2 0.9300 . ?
C3 C14 1.497(2) . ?
C3 C4 1.498(2) . ?
C4 C5 1.371(2) . ?
C4 C9 1.441(2) . ?
C5 C6 1.402(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.352(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.414(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.410(3) . ?
C8 C9 1.426(2) . ?
C9 C10 1.428(3) . ?
C10 C11 1.373(3) . ?
C11 C12 1.392(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.348(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.388(2) . ?
C14 C15 1.390(2) . ?
C15 C16 1.379(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.370(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.374(3) . ?
C18 C19 1.384(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.501(3) . ?
C21 C22 1.376(3) . ?
C22 C23 1.373(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.362(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.377(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.475(5) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C26' C27' 1.525(9) . ?
C26' H26C 0.9700 . ?
C26' H26D 0.9700 . ?
C27' H27D 0.9600 . ?
C27' H27E 0.9600 . ?
C27' H27F 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
C20 N1 C10 127.57(17) . . ?
C20 N1 H1 116.2 . . ?
C10 N1 H1 116.2 . . ?
C25 N2 C21 117.4(2) . . ?
C1 O1 C26 116.5(2) . . ?
C1 O1' C26' 119.1(8) . . ?
O2 C1 O2' 8(2) . . ?
O2 C1 O1' 118.3(8) . . ?
O2' C1 O1' 111(2) . . ?
O2 C1 O1 125.5(7) . . ?
O2' C1 O1 117.7(18) . . ?
O1' C1 O1 32.0(3) . . ?
O2 C1 C2 126.1(7) . . ?
O2' C1 C2 134.0(18) . . ?
O1' C1 C2 109.8(4) . . ?
O1 C1 C2 108.1(2) . . ?
C3 C2 C1 128.44(18) . . ?
C3 C2 H2 115.8 . . ?
C1 C2 H2 115.8 . . ?
C2 C3 C14 126.00(17) . . ?
C2 C3 C4 118.86(16) . . ?
C14 C3 C4 114.90(15) . . ?
C5 C4 C9 119.04(17) . . ?
C5 C4 C3 116.85(16) . . ?
C9 C4 C3 123.71(16) . . ?
C4 C5 C6 122.53(19) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C7 C6 C5 119.39(19) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 121.03(19) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C13 C8 C7 120.05(18) . . ?
C13 C8 C9 119.86(18) . . ?
C7 C8 C9 120.08(18) . . ?
C8 C9 C10 117.43(16) . . ?
C8 C9 C4 117.54(16) . . ?
C10 C9 C4 125.01(16) . . ?
C11 C10 N1 119.82(17) . . ?
C11 C10 C9 120.29(18) . . ?
N1 C10 C9 119.72(16) . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 121.0(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C8 120.48(19) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
C19 C14 C15 117.87(17) . . ?
C19 C14 C3 119.01(16) . . ?
C15 C14 C3 123.09(16) . . ?
C16 C15 C14 121.26(18) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 119.14(19) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 121.56(18) . . ?
C16 C17 Cl1 118.89(16) . . ?
C18 C17 Cl1 119.55(16) . . ?
C17 C18 C19 118.64(18) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C18 C19 C14 121.45(17) . . ?
C18 C19 H19 119.3 . . ?
C14 C19 H19 119.3 . . ?
O3 C20 N1 124.8(2) . . ?
O3 C20 C21 121.79(18) . . ?
N1 C20 C21 113.44(18) . . ?
N2 C21 C22 122.8(2) . . ?
N2 C21 C20 116.97(17) . . ?
C22 C21 C20 120.2(2) . . ?
C23 C22 C21 118.6(3) . . ?
C23 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
C24 C23 C22 119.5(2) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 118.5(3) . . ?
C23 C24 H24 120.8 . . ?
C25 C24 H24 120.8 . . ?
N2 C25 C24 123.3(3) . . ?
N2 C25 H25 118.3 . . ?
C24 C25 H25 118.3 . . ?
O1 C26 C27 111.1(4) . . ?
O1 C26 H26A 109.4 . . ?
C27 C26 H26A 109.4 . . ?
O1 C26 H26B 109.4 . . ?
C27 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
O1' C26' C27' 112.9(11) . . ?
O1' C26' H26C 109.0 . . ?
C27' C26' H26C 109.0 . . ?
O1' C26' H26D 109.0 . . ?
C27' C26' H26D 109.0 . . ?
H26C C26' H26D 107.8 . . ?
C26' C27' H27D 109.5 . . ?
C26' C27' H27E 109.5 . . ?
H27D C27' H27E 109.5 . . ?
C26' C27' H27F 109.5 . . ?
H27D C27' H27F 109.5 . . ?
H27E C27' H27F 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_190426c
_database_code_depnum_ccdc_archive 'CCDC 2021029'
loop_
_audit_author_name
_audit_author_address
'Ruokun Feng'
;Shaoxing University
China
;
_audit_update_record             
;
2020-08-02 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H23 N2 O'
_chemical_formula_weight         451.52

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   10.6041(11)
_cell_length_b                   18.1154(19)
_cell_length_c                   13.0961(16)
_cell_angle_alpha                90
_cell_angle_beta                 104.601(3)
_cell_angle_gamma                90
_cell_volume                     2434.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1849
_cell_measurement_theta_min      2.484
_cell_measurement_theta_max      21.069

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_F_000             948
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11947
_diffrn_reflns_av_unetI/netI     0.1297
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.486
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_full        25.019
_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             4289
_reflns_number_gt                2022
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+1.0177P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4289
_refine_ls_number_parameters     316
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1572
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.1926
_refine_ls_wR_factor_gt          0.1523
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.050
_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 0.3952(3) 0.09602(14) 0.8321(2) 0.0489(7) Uani 1 1 d . . . . .
N2 N 0.3188(3) -0.01487(15) 0.9353(2) 0.0538(8) Uani 1 1 d . . . . .
O1 O 0.3070(3) 0.03832(16) 0.6743(2) 0.0999(11) Uani 1 1 d . . . . .
C1 C 0.4592(3) 0.15763(18) 0.7987(3) 0.0488(9) Uani 1 1 d . . . . .
C2 C 0.4828(4) 0.1596(2) 0.7000(3) 0.0674(11) Uani 1 1 d . . . . .
H2 H 0.447021 0.123592 0.650482 0.081 Uiso 1 1 calc R U . . .
C3 C 0.5604(4) 0.2155(3) 0.6740(4) 0.0825(14) Uani 1 1 d . . . . .
H3 H 0.573591 0.217046 0.606460 0.099 Uiso 1 1 calc R U . . .
C4 C 0.6160(4) 0.2669(2) 0.7449(4) 0.0722(12) Uani 1 1 d . . . . .
H4 H 0.671321 0.301847 0.727376 0.087 Uiso 1 1 calc R U . . .
C5 C 0.5915(3) 0.2684(2) 0.8447(3) 0.0582(10) Uani 1 1 d . . . . .
C6 C 0.5056(3) 0.21558(17) 0.8729(3) 0.0447(9) Uani 1 1 d . . . . .
C7 C 0.4772(3) 0.22371(18) 0.9735(3) 0.0484(9) Uani 1 1 d . . . . .
C8 C 0.5410(4) 0.2770(2) 1.0420(3) 0.0647(11) Uani 1 1 d . . . . .
H8 H 0.523523 0.280889 1.107880 0.078 Uiso 1 1 calc R U . . .
C9 C 0.6311(4) 0.3257(2) 1.0168(4) 0.0768(13) Uani 1 1 d . . . . .
H9 H 0.675305 0.359927 1.065807 0.092 Uiso 1 1 calc R U . . .
C10 C 0.6522(4) 0.3215(2) 0.9196(4) 0.0755(13) Uani 1 1 d . . . . .
H10 H 0.709120 0.355140 0.901243 0.091 Uiso 1 1 calc R U . . .
C11 C 0.3765(3) 0.18018(17) 1.0100(3) 0.0452(8) Uani 1 1 d . . . . .
C12 C 0.2386(3) 0.19386(19) 0.9562(3) 0.0466(9) Uani 1 1 d . . . . .
C13 C 0.2021(4) 0.2615(2) 0.9083(3) 0.0626(11) Uani 1 1 d . . . . .
H13 H 0.265505 0.297250 0.909887 0.075 Uiso 1 1 calc R U . . .
C14 C 0.0740(5) 0.2772(3) 0.8583(4) 0.0860(14) Uani 1 1 d . . . . .
H14 H 0.051376 0.323561 0.828731 0.103 Uiso 1 1 calc R U . . .
C15 C -0.0191(4) 0.2244(3) 0.8526(4) 0.0898(15) Uani 1 1 d . . . . .
H15 H -0.105279 0.234297 0.817834 0.108 Uiso 1 1 calc R U . . .
C16 C 0.0144(4) 0.1569(3) 0.8979(4) 0.0835(14) Uani 1 1 d . . . . .
H16 H -0.049480 0.121092 0.893552 0.100 Uiso 1 1 calc R U . . .
C17 C 0.1417(4) 0.1412(2) 0.9501(3) 0.0662(11) Uani 1 1 d . . . . .
H17 H 0.162677 0.095190 0.981318 0.079 Uiso 1 1 calc R U . . .
C18 C 0.4198(3) 0.13615(18) 1.0945(3) 0.0516(9) Uani 1 1 d . . . . .
H18 H 0.509920 0.132379 1.117972 0.062 Uiso 1 1 calc R U . . .
C19 C 0.3490(4) 0.09478(19) 1.1530(3) 0.0559(10) Uani 1 1 d D . . . .
C20 C 0.3023(4) 0.05830(19) 1.2108(3) 0.0611(11) Uani 1 1 d D . . . .
C21 C 0.2476(4) 0.01754(19) 1.2824(3) 0.0561(10) Uani 1 1 d . . . . .
C22 C 0.1149(5) 0.0078(2) 1.2653(4) 0.0789(13) Uani 1 1 d . . . . .
H22 H 0.058909 0.025596 1.203788 0.095 Uiso 1 1 calc R U . . .
C23 C 0.0648(5) -0.0284(3) 1.3393(4) 0.0924(15) Uani 1 1 d . . . . .
H23 H -0.024702 -0.035270 1.326648 0.111 Uiso 1 1 calc R U . . .
C24 C 0.1438(5) -0.0539(2) 1.4292(4) 0.0879(14) Uani 1 1 d . . . . .
H24 H 0.108927 -0.077704 1.478739 0.105 Uiso 1 1 calc R U . . .
C25 C 0.2761(5) -0.0446(3) 1.4479(4) 0.0908(14) Uani 1 1 d . . . . .
H25 H 0.331116 -0.062541 1.509791 0.109 Uiso 1 1 calc R U . . .
C26 C 0.3274(4) -0.0086(2) 1.3747(4) 0.0762(12) Uani 1 1 d . . . . .
H26 H 0.417047 -0.001880 1.388117 0.091 Uiso 1 1 calc R U . . .
C27 C 0.3321(4) 0.04112(19) 0.7705(3) 0.0555(10) Uani 1 1 d . . . . .
C28 C 0.2913(3) -0.02092(18) 0.8305(3) 0.0488(9) Uani 1 1 d . . . . .
C29 C 0.2303(4) -0.0821(2) 0.7769(3) 0.0686(11) Uani 1 1 d . . . . .
H29 H 0.212341 -0.084641 0.703745 0.082 Uiso 1 1 calc R U . . .
C30 C 0.1967(4) -0.1395(2) 0.8343(4) 0.0733(12) Uani 1 1 d . . . . .
H30 H 0.156755 -0.181634 0.800414 0.088 Uiso 1 1 calc R U . . .
C31 C 0.2231(4) -0.1335(2) 0.9419(4) 0.0677(12) Uani 1 1 d . . . . .
H31 H 0.200400 -0.171163 0.982085 0.081 Uiso 1 1 calc R U . . .
C32 C 0.2836(4) -0.0707(2) 0.9894(3) 0.0646(11) Uani 1 1 d . . . . .
H32 H 0.300875 -0.066791 1.062381 0.078 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 C27 1.348(4) . ?
N1 C1 1.431(4) . ?
N2 C28 1.334(4) . ?
N2 C32 1.340(4) . ?
O1 C27 1.221(4) . ?
C1 C2 1.378(5) . ?
C1 C6 1.431(4) . ?
C2 C3 1.401(5) . ?
C3 C4 1.342(6) . ?
C4 C5 1.396(5) . ?
C5 C10 1.408(6) . ?
C5 C6 1.432(4) . ?
C6 C7 1.431(5) . ?
C7 C8 1.374(5) . ?
C7 C11 1.500(4) . ?
C8 C9 1.399(5) . ?
C9 C10 1.350(6) . ?
C11 C18 1.347(4) . ?
C11 C12 1.475(5) . ?
C12 C13 1.387(5) . ?
C12 C17 1.390(5) . ?
C13 C14 1.380(5) . ?
C14 C15 1.363(6) . ?
C15 C16 1.366(6) . ?
C16 C17 1.380(5) . ?
C18 C19 1.414(5) . ?
C19 C20 1.202(4) . ?
C20 C21 1.426(5) . ?
C21 C26 1.374(5) . ?
C21 C22 1.380(5) . ?
C22 C23 1.382(6) . ?
C23 C24 1.343(6) . ?
C24 C25 1.372(6) . ?
C25 C26 1.379(6) . ?
C27 C28 1.496(5) . ?
C28 C29 1.382(5) . ?
C29 C30 1.381(5) . ?
C30 C31 1.369(6) . ?
C31 C32 1.375(5) . ?

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
C27 N1 C1 126.5(3) . . ?
C28 N2 C32 117.6(3) . . ?
C2 C1 N1 121.2(3) . . ?
C2 C1 C6 120.4(3) . . ?
N1 C1 C6 118.3(3) . . ?
C1 C2 C3 120.2(4) . . ?
C4 C3 C2 121.1(4) . . ?
C3 C4 C5 120.6(4) . . ?
C4 C5 C10 120.3(4) . . ?
C4 C5 C6 120.6(4) . . ?
C10 C5 C6 119.1(4) . . ?
C1 C6 C7 125.7(3) . . ?
C1 C6 C5 116.6(3) . . ?
C7 C6 C5 117.6(3) . . ?
C8 C7 C6 119.3(3) . . ?
C8 C7 C11 115.8(3) . . ?
C6 C7 C11 124.8(3) . . ?
C7 C8 C9 122.8(4) . . ?
C10 C9 C8 118.2(4) . . ?
C9 C10 C5 122.6(4) . . ?
C18 C11 C12 125.7(3) . . ?
C18 C11 C7 116.8(3) . . ?
C12 C11 C7 117.3(3) . . ?
C13 C12 C17 117.5(3) . . ?
C13 C12 C11 119.7(3) . . ?
C17 C12 C11 122.8(3) . . ?
C14 C13 C12 121.8(4) . . ?
C15 C14 C13 119.6(4) . . ?
C14 C15 C16 119.9(4) . . ?
C15 C16 C17 121.0(4) . . ?
C16 C17 C12 120.2(4) . . ?
C11 C18 C19 129.8(3) . . ?
C20 C19 C18 172.5(4) . . ?
C19 C20 C21 177.6(4) . . ?
C26 C21 C22 118.4(4) . . ?
C26 C21 C20 119.7(4) . . ?
C22 C21 C20 121.8(4) . . ?
C21 C22 C23 120.3(4) . . ?
C24 C23 C22 120.8(4) . . ?
C23 C24 C25 119.9(4) . . ?
C24 C25 C26 119.9(5) . . ?
C21 C26 C25 120.8(4) . . ?
O1 C27 N1 126.5(4) . . ?
O1 C27 C28 119.6(3) . . ?
N1 C27 C28 113.9(3) . . ?
N2 C28 C29 122.8(3) . . ?
N2 C28 C27 117.5(3) . . ?
C29 C28 C27 119.7(4) . . ?
C30 C29 C28 118.6(4) . . ?
C31 C30 C29 119.1(4) . . ?
C30 C31 C32 118.8(4) . . ?
N2 C32 C31 123.1(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
_geom_hbond_publ_flag
C2 H2 O1 0.93 2.22 2.845(5) 124.0 . yes
C2 H2 O1 0.93 2.22 2.845(5) 124.0 . yes
C2 H2 O1 0.93 2.22 2.845(5) 124.0 . yes
C2 H2 O1 0.93 2.22 2.845(5) 124.0 . yes
C2 H2 O1 0.93 2.22 2.845(5) 124.0 . yes
C2 H2 O1 0.93 2.22 2.845(5) 124.0 . yes
C2 H2 O1 0.93 2.22 2.845(5) 124.0 . yes

_refine_diff_density_max         0.487
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.044



