# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_a
_audit_block_doi                 10.5517/ccdc.csd.cc270f8z
_database_code_depnum_ccdc_archive 'CCDC 2055990'
loop_
_audit_author_name
_audit_author_address
TPA-H
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2021-01-14 deposited with the CCDC.	2021-02-23 downloaded from the CCDC.
;
_audit_creation_date             2018-08-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H21 N O'
_chemical_formula_sum            'C26 H21 N O'
_chemical_formula_weight         363.44
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.928(4)
_cell_length_b                   10.831(2)
_cell_length_c                   8.5628(17)
_cell_angle_alpha                90
_cell_angle_beta                 93.09(3)
_cell_angle_gamma                90
_cell_volume                     1938.1(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5943
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4855
_cell_measurement_theta_min      2.1180
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12863
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         2.924
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3842
_reflns_number_total             4352
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0668
_refine_ls_restrained_S_all      1.144
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0303P)²+1.1144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1322
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C17(H17), C18(H18), C22(H22), C23(H23), C24(H24),
  C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.01925(7) 0.25138(16) 0.1340(2) 0.0511(4) Uani 1 1 d . . . . .
N1 N 0.31185(7) 0.37132(14) 0.33217(19) 0.0290(3) Uani 1 1 d . . . . .
C1 C 0.34077(8) 0.48865(17) 0.3628(2) 0.0276(4) Uani 1 1 d . . . . .
C2 C 0.32287(9) 0.59182(18) 0.2733(2) 0.0315(4) Uani 1 1 d . . . . .
H2 H 0.290319 0.584973 0.192087 0.038 Uiso 1 1 calc R . . . .
C3 C 0.35262(9) 0.70428(18) 0.3030(2) 0.0363(5) Uani 1 1 d . . . . .
H3 H 0.339761 0.774706 0.243113 0.044 Uiso 1 1 calc R . . . .
C4 C 0.40085(10) 0.71495(19) 0.4190(3) 0.0402(5) Uani 1 1 d . . . . .
H4 H 0.421633 0.791939 0.437689 0.048 Uiso 1 1 calc R . . . .
C5 C 0.41862(10) 0.61258(19) 0.5078(3) 0.0397(5) Uani 1 1 d . . . . .
H5 H 0.451928 0.619325 0.587171 0.048 Uiso 1 1 calc R . . . .
C6 C 0.38826(9) 0.50062(18) 0.4817(2) 0.0331(4) Uani 1 1 d . . . . .
H6 H 0.399893 0.431496 0.545367 0.040 Uiso 1 1 calc R . . . .
C7 C 0.35184(8) 0.26500(16) 0.3413(2) 0.0255(4) Uani 1 1 d . . . . .
C8 C 0.41349(8) 0.27118(18) 0.2864(2) 0.0294(4) Uani 1 1 d . . . . .
H8 H 0.427244 0.344188 0.236736 0.035 Uiso 1 1 calc R . . . .
C9 C 0.45465(8) 0.17113(18) 0.3043(2) 0.0323(4) Uani 1 1 d . . . . .
H9 H 0.496942 0.177072 0.269867 0.039 Uiso 1 1 calc R . . . .
C10 C 0.43463(9) 0.06314(18) 0.3716(2) 0.0324(4) Uani 1 1 d . . . . .
H10 H 0.462859 -0.005339 0.383130 0.039 Uiso 1 1 calc R . . . .
C11 C 0.37291(9) 0.05538(18) 0.4223(2) 0.0323(4) Uani 1 1 d . . . . .
H11 H 0.358658 -0.019423 0.466732 0.039 Uiso 1 1 calc R . . . .
C12 C 0.33192(9) 0.15541(17) 0.4087(2) 0.0299(4) Uani 1 1 d . . . . .
H12 H 0.290015 0.149387 0.445515 0.036 Uiso 1 1 calc R . . . .
C13 C 0.24484(8) 0.36174(17) 0.3067(2) 0.0261(4) Uani 1 1 d . . . . .
C14 C 0.20421(8) 0.44732(17) 0.3732(2) 0.0285(4) Uani 1 1 d . . . . .
H14 H 0.221855 0.511525 0.437606 0.034 Uiso 1 1 calc R . . . .
C15 C 0.13842(8) 0.43929(17) 0.3458(2) 0.0279(4) Uani 1 1 d . . . . .
H15 H 0.111534 0.498715 0.390744 0.033 Uiso 1 1 calc R . . . .
C16 C 0.11122(8) 0.34515(17) 0.2532(2) 0.0268(4) Uani 1 1 d . . . . .
C17 C 0.15196(8) 0.25966(18) 0.1880(2) 0.0289(4) Uani 1 1 d . . . . .
H17 H 0.134221 0.194876 0.124660 0.035 Uiso 1 1 calc R . . . .
C18 C 0.21758(8) 0.26732(17) 0.2137(2) 0.0287(4) Uani 1 1 d . . . . .
H18 H 0.244348 0.208091 0.167961 0.034 Uiso 1 1 calc R . . . .
C19 C 0.04090(8) 0.33247(18) 0.2207(2) 0.0302(4) Uani 1 1 d . . . . .
C20 C -0.00278(8) 0.42103(18) 0.3012(2) 0.0316(4) Uani 1 1 d . . . . .
H20A H 0.002603 0.408246 0.415601 0.038 Uiso 1 1 calc R . . . .
H20B H 0.010518 0.506674 0.278879 0.038 Uiso 1 1 calc R . . . .
C21 C -0.07254(8) 0.40637(18) 0.2513(2) 0.0292(4) Uani 1 1 d . . . . .
C22 C -0.09997(9) 0.47772(19) 0.1316(2) 0.0354(4) Uani 1 1 d . . . . .
H22 H -0.074639 0.537275 0.081898 0.042 Uiso 1 1 calc R . . . .
C23 C -0.16403(9) 0.4637(2) 0.0828(3) 0.0394(5) Uani 1 1 d . . . . .
H23 H -0.182102 0.512871 -0.000191 0.047 Uiso 1 1 calc R . . . .
C24 C -0.20110(9) 0.3784(2) 0.1550(3) 0.0437(5) Uani 1 1 d . . . . .
H24 H -0.244905 0.368478 0.122294 0.052 Uiso 1 1 calc R . . . .
C25 C -0.17439(10) 0.3072(2) 0.2751(3) 0.0493(6) Uani 1 1 d . . . . .
H25 H -0.199956 0.248107 0.324941 0.059 Uiso 1 1 calc R . . . .
C26 C -0.11036(9) 0.3212(2) 0.3237(3) 0.0398(5) Uani 1 1 d . . . . .
H26 H -0.092487 0.272043 0.407027 0.048 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
O1 C19 1.221(2) . ?
N1 C1 1.426(2) . ?
N1 C7 1.423(2) . ?
N1 C13 1.412(2) . ?
C1 C2 1.395(3) . ?
C1 C6 1.390(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.398(2) . ?
C7 C12 1.393(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.379(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.399(2) . ?
C13 C18 1.399(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.394(3) . ?
C16 C17 1.395(2) . ?
C16 C19 1.489(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.516(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.507(2) . ?
C21 C22 1.384(3) . ?
C21 C26 1.384(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.391(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.375(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.379(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.390(3) . ?
C26 H26 0.9500 . ?

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 N1 C1 117.94(14) . . ?
C13 N1 C1 120.15(15) . . ?
C13 N1 C7 121.70(15) . . ?
C2 C1 N1 120.94(17) . . ?
C6 C1 N1 119.85(17) . . ?
C6 C1 C2 119.20(18) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.93(19) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.59(19) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.46(19) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.31(19) . . ?
C5 C6 H6 119.8 . . ?
C8 C7 N1 119.55(16) . . ?
C12 C7 N1 121.59(15) . . ?
C12 C7 C8 118.82(16) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.28(18) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.50(17) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.42(17) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.67(18) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 H12 119.9 . . ?
C11 C12 C7 120.26(17) . . ?
C11 C12 H12 119.9 . . ?
C14 C13 N1 120.60(16) . . ?
C18 C13 N1 120.86(16) . . ?
C18 C13 C14 118.53(16) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.61(17) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.88(17) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C17 118.24(16) . . ?
C15 C16 C19 122.88(16) . . ?
C17 C16 C19 118.89(16) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.34(17) . . ?
C18 C17 H17 119.3 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.40(17) . . ?
C17 C18 H18 119.8 . . ?
O1 C19 C16 120.70(17) . . ?
O1 C19 C20 121.21(16) . . ?
C16 C19 C20 118.08(16) . . ?
C19 C20 H20A 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C21 C20 C19 113.78(16) . . ?
C21 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C22 C21 C20 120.51(17) . . ?
C22 C21 C26 118.69(17) . . ?
C26 C21 C20 120.80(18) . . ?
C21 C22 H22 119.5 . . ?
C21 C22 C23 121.08(19) . . ?
C23 C22 H22 119.5 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.8(2) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 120.2 . . ?
C23 C24 C25 119.68(19) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 H25 119.7 . . ?
C24 C25 C26 120.5(2) . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 120.2(2) . . ?
C21 C26 H26 119.9 . . ?
C25 C26 H26 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
O1 C19 C20 C21 -5.7(3) . . . . ?
N1 C1 C2 C3 -178.57(16) . . . . ?
N1 C1 C6 C5 177.05(17) . . . . ?
N1 C7 C8 C9 175.55(17) . . . . ?
N1 C7 C12 C11 -177.10(17) . . . . ?
N1 C13 C14 C15 178.80(17) . . . . ?
N1 C13 C18 C17 -179.21(17) . . . . ?
C1 N1 C7 C8 -38.4(2) . . . . ?
C1 N1 C7 C12 139.35(18) . . . . ?
C1 N1 C13 C14 -27.6(3) . . . . ?
C1 N1 C13 C18 151.92(17) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C2 C1 C6 C5 -1.9(3) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 1.9(3) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C7 N1 C1 C2 139.62(18) . . . . ?
C7 N1 C1 C6 -39.3(2) . . . . ?
C7 N1 C13 C14 147.04(18) . . . . ?
C7 N1 C13 C18 -33.5(3) . . . . ?
C7 C8 C9 C10 2.1(3) . . . . ?
C8 C7 C12 C11 0.7(3) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 -1.3(3) . . . . ?
C10 C11 C12 C7 1.1(3) . . . . ?
C12 C7 C8 C9 -2.3(3) . . . . ?
C13 N1 C1 C2 -45.6(2) . . . . ?
C13 N1 C1 C6 135.54(18) . . . . ?
C13 N1 C7 C8 146.83(17) . . . . ?
C13 N1 C7 C12 -35.4(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C13 C18 C17 0.3(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C14 C15 C16 C19 179.87(17) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C15 C16 C19 O1 177.19(19) . . . . ?
C15 C16 C19 C20 -4.2(3) . . . . ?
C16 C17 C18 C13 0.1(3) . . . . ?
C16 C19 C20 C21 175.77(16) . . . . ?
C17 C16 C19 O1 -2.6(3) . . . . ?
C17 C16 C19 C20 175.99(17) . . . . ?
C18 C13 C14 C15 -0.7(3) . . . . ?
C19 C16 C17 C18 179.72(17) . . . . ?
C19 C20 C21 C22 -93.5(2) . . . . ?
C19 C20 C21 C26 86.3(2) . . . . ?
C20 C21 C22 C23 178.94(19) . . . . ?
C20 C21 C26 C25 -179.0(2) . . . . ?
C21 C22 C23 C24 0.5(3) . . . . ?
C22 C21 C26 C25 0.8(3) . . . . ?
C22 C23 C24 C25 -0.1(4) . . . . ?
C23 C24 C25 C26 0.1(4) . . . . ?
C24 C25 C26 C21 -0.4(4) . . . . ?
C26 C21 C22 C23 -0.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dd20122
_audit_block_doi                 10.5517/ccdc.csd.cc270fb1
_database_code_depnum_ccdc_archive 'CCDC 2055992'
loop_
_audit_author_name
_audit_author_address
TPA-F
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2021-01-14 deposited with the CCDC.	2021-02-23 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 H20 F N O'
_chemical_formula_weight         381.43

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   21.548(2)
_cell_length_b                   10.8853(11)
_cell_length_c                   8.6636(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.981(4)
_cell_angle_gamma                90
_cell_volume                     2024.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1835
_cell_measurement_theta_min      5.330
_cell_measurement_theta_max      48.506

_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             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2403
_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            8516
_diffrn_reflns_av_unetI/netI     0.1163
_diffrn_reflns_av_R_equivalents  0.0821
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.012
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             3526
_reflns_number_gt                1821
_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)+(0.1560P)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       0.028(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3526
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1608
_refine_ls_R_factor_gt           0.0921
_refine_ls_wR_factor_ref         0.2919
_refine_ls_wR_factor_gt          0.2363
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.25715(14) 0.3674(4) 0.1194(5) 0.1498(16) Uani 1 1 d . . . . .
O1 O 0.52849(14) 0.2615(3) 0.1351(4) 0.1042(13) Uani 1 1 d . . . . .
N1 N 0.81555(15) 0.3716(3) 0.3258(4) 0.0619(9) Uani 1 1 d . . . . .
C1 C 0.65791(18) 0.2654(4) 0.1872(5) 0.0602(11) Uani 1 1 d . . . . .
H1 H 0.6396 0.2032 0.1253 0.072 Uiso 1 1 calc R U . . .
C2 C 0.72121(19) 0.2718(3) 0.2089(4) 0.0596(11) Uani 1 1 d . . . . .
H2 H 0.7453 0.2149 0.1607 0.072 Uiso 1 1 calc R U . . .
C3 C 0.75026(17) 0.3635(3) 0.3033(4) 0.0547(10) Uani 1 1 d . . . . .
C4 C 0.71232(19) 0.4480(4) 0.3727(5) 0.0620(11) Uani 1 1 d . . . . .
H4 H 0.7303 0.5097 0.4361 0.074 Uiso 1 1 calc R U . . .
C5 C 0.64893(18) 0.4400(3) 0.3474(5) 0.0603(11) Uani 1 1 d . . . . .
H5 H 0.6246 0.4975 0.3938 0.072 Uiso 1 1 calc R U . . .
C6 C 0.61973(18) 0.3496(4) 0.2554(4) 0.0566(10) Uani 1 1 d . . . . .
C7 C 0.5512(2) 0.3379(4) 0.2251(5) 0.0655(11) Uani 1 1 d . . . . .
C8 C 0.51004(19) 0.4218(4) 0.3111(5) 0.0742(13) Uani 1 1 d . . . . .
H8A H 0.5172 0.4050 0.4212 0.089 Uiso 1 1 calc R U . . .
H8B H 0.5222 0.5062 0.2945 0.089 Uiso 1 1 calc R U . . .
C9 C 0.4421(2) 0.4086(4) 0.2635(5) 0.0652(11) Uani 1 1 d . . . . .
C10 C 0.4129(2) 0.4814(4) 0.1493(6) 0.0776(13) Uani 1 1 d . . . . .
H10 H 0.4360 0.5412 0.1031 0.093 Uiso 1 1 calc R U . . .
C11 C 0.3509(2) 0.4684(5) 0.1015(6) 0.0907(15) Uani 1 1 d . . . . .
H11 H 0.3319 0.5188 0.0247 0.109 Uiso 1 1 calc R U . . .
C12 C 0.3185(2) 0.3812(5) 0.1682(7) 0.0918(15) Uani 1 1 d . . . . .
C13 C 0.3441(3) 0.3074(5) 0.2825(7) 0.1035(18) Uani 1 1 d . . . . .
H13 H 0.3201 0.2489 0.3280 0.124 Uiso 1 1 calc R U . . .
C14 C 0.4061(2) 0.3209(5) 0.3298(6) 0.0879(15) Uani 1 1 d . . . . .
H14 H 0.4243 0.2704 0.4076 0.106 Uiso 1 1 calc R U . . .
C15 C 0.85416(18) 0.2663(3) 0.3351(4) 0.0532(10) Uani 1 1 d . . . . .
C16 C 0.83575(19) 0.1568(3) 0.4001(4) 0.0616(11) Uani 1 1 d . . . . .
H16 H 0.7964 0.1508 0.4357 0.074 Uiso 1 1 calc R U . . .
C17 C 0.8751(2) 0.0576(4) 0.4123(5) 0.0706(12) Uani 1 1 d . . . . .
H17 H 0.8613 -0.0160 0.4517 0.085 Uiso 1 1 calc R U . . .
C18 C 0.9349(2) 0.0652(4) 0.3669(5) 0.0704(12) Uani 1 1 d . . . . .
H18 H 0.9621 -0.0010 0.3805 0.084 Uiso 1 1 calc R U . . .
C19 C 0.95316(19) 0.1724(4) 0.3016(5) 0.0713(12) Uani 1 1 d . . . . .
H19 H 0.9931 0.1785 0.2691 0.086 Uiso 1 1 calc R U . . .
C20 C 0.91341(18) 0.2710(4) 0.2833(5) 0.0649(11) Uani 1 1 d . . . . .
H20 H 0.9263 0.3420 0.2356 0.078 Uiso 1 1 calc R U . . .
C21 C 0.84413(18) 0.4891(3) 0.3544(5) 0.0573(11) Uani 1 1 d . . . . .
C22 C 0.8906(2) 0.5024(4) 0.4743(5) 0.0708(12) Uani 1 1 d . . . . .
H22 H 0.9019 0.4356 0.5375 0.085 Uiso 1 1 calc R U . . .
C23 C 0.9197(3) 0.6120(4) 0.5004(6) 0.0891(15) Uani 1 1 d . . . . .
H23 H 0.9514 0.6192 0.5801 0.107 Uiso 1 1 calc R U . . .
C24 C 0.9032(3) 0.7108(5) 0.4115(7) 0.0899(16) Uani 1 1 d . . . . .
H24 H 0.9237 0.7852 0.4300 0.108 Uiso 1 1 calc R U . . .
C25 C 0.8563(3) 0.7021(4) 0.2944(7) 0.0835(15) Uani 1 1 d . . . . .
H25 H 0.8441 0.7709 0.2358 0.100 Uiso 1 1 calc R U . . .
C26 C 0.8272(2) 0.5891(4) 0.2641(5) 0.0700(13) Uani 1 1 d . . . . .
H26 H 0.7964 0.5816 0.1826 0.084 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 C12 1.361(5) . ?
O1 C7 1.214(5) . ?
N1 C3 1.406(5) . ?
N1 C15 1.415(4) . ?
N1 C21 1.432(5) . ?
C1 C2 1.362(5) . ?
C1 C6 1.396(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.403(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.401(5) . ?
C4 C5 1.367(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.482(5) . ?
C7 C8 1.513(5) . ?
C8 C9 1.493(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.376(6) . ?
C9 C14 1.385(6) . ?
C10 C11 1.372(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.339(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.354(7) . ?
C13 C14 1.372(7) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.390(5) . ?
C15 C20 1.391(5) . ?
C16 C17 1.371(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.370(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.371(5) . ?
C21 C22 1.387(6) . ?
C22 C23 1.358(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.353(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.370(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.396(6) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C15 122.3(3) . . ?
C3 N1 C21 119.3(3) . . ?
C15 N1 C21 118.2(3) . . ?
C2 C1 C6 121.9(4) . . ?
C2 C1 H1 119.1 . . ?
C6 C1 H1 119.1 . . ?
C1 C2 C3 120.5(4) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 118.0(4) . . ?
C4 C3 N1 120.9(4) . . ?
C2 C3 N1 121.1(3) . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 122.4(4) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C1 117.1(4) . . ?
C5 C6 C7 124.0(4) . . ?
C1 C6 C7 118.9(4) . . ?
O1 C7 C6 120.8(4) . . ?
O1 C7 C8 120.5(4) . . ?
C6 C7 C8 118.6(4) . . ?
C9 C8 C7 114.2(4) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C14 117.2(4) . . ?
C10 C9 C8 121.3(4) . . ?
C14 C9 C8 121.5(4) . . ?
C11 C10 C9 122.0(4) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C12 C11 C10 118.3(5) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 C13 122.8(5) . . ?
C11 C12 F1 118.3(5) . . ?
C13 C12 F1 119.0(5) . . ?
C12 C13 C14 118.6(5) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C13 C14 C9 121.1(5) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
C16 C15 C20 117.7(4) . . ?
C16 C15 N1 122.0(4) . . ?
C20 C15 N1 120.2(3) . . ?
C17 C16 C15 120.6(4) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 121.2(4) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C19 C18 C17 118.4(4) . . ?
C19 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
C18 C19 C20 121.0(4) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C15 120.9(4) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
C26 C21 C22 118.9(4) . . ?
C26 C21 N1 121.4(4) . . ?
C22 C21 N1 119.6(3) . . ?
C23 C22 C21 120.7(4) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C22 120.5(5) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 120.5(5) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C26 119.4(4) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C21 C26 C25 119.9(4) . . ?
C21 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?

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
C6 C1 C2 C3 0.9(6) . . . . ?
C1 C2 C3 C4 -0.5(6) . . . . ?
C1 C2 C3 N1 -179.6(4) . . . . ?
C15 N1 C3 C4 145.2(4) . . . . ?
C21 N1 C3 C4 -29.0(5) . . . . ?
C15 N1 C3 C2 -35.7(5) . . . . ?
C21 N1 C3 C2 150.0(4) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
N1 C3 C4 C5 178.9(3) . . . . ?
C3 C4 C5 C6 0.6(6) . . . . ?
C4 C5 C6 C1 -0.3(6) . . . . ?
C4 C5 C6 C7 -180.0(4) . . . . ?
C2 C1 C6 C5 -0.4(6) . . . . ?
C2 C1 C6 C7 179.2(4) . . . . ?
C5 C6 C7 O1 175.1(4) . . . . ?
C1 C6 C7 O1 -4.6(6) . . . . ?
C5 C6 C7 C8 -6.0(6) . . . . ?
C1 C6 C7 C8 174.3(4) . . . . ?
O1 C7 C8 C9 -5.4(6) . . . . ?
C6 C7 C8 C9 175.7(4) . . . . ?
C7 C8 C9 C10 -92.3(5) . . . . ?
C7 C8 C9 C14 86.2(5) . . . . ?
C14 C9 C10 C11 -0.2(7) . . . . ?
C8 C9 C10 C11 178.3(4) . . . . ?
C9 C10 C11 C12 -0.5(8) . . . . ?
C10 C11 C12 C13 1.4(9) . . . . ?
C10 C11 C12 F1 -179.2(5) . . . . ?
C11 C12 C13 C14 -1.4(9) . . . . ?
F1 C12 C13 C14 179.2(5) . . . . ?
C12 C13 C14 C9 0.5(9) . . . . ?
C10 C9 C14 C13 0.2(7) . . . . ?
C8 C9 C14 C13 -178.3(4) . . . . ?
C3 N1 C15 C16 -33.5(5) . . . . ?
C21 N1 C15 C16 140.8(4) . . . . ?
C3 N1 C15 C20 148.7(4) . . . . ?
C21 N1 C15 C20 -37.0(5) . . . . ?
C20 C15 C16 C17 0.1(6) . . . . ?
N1 C15 C16 C17 -177.7(4) . . . . ?
C15 C16 C17 C18 2.9(6) . . . . ?
C16 C17 C18 C19 -3.4(6) . . . . ?
C17 C18 C19 C20 0.9(6) . . . . ?
C18 C19 C20 C15 2.1(7) . . . . ?
C16 C15 C20 C19 -2.6(6) . . . . ?
N1 C15 C20 C19 175.3(3) . . . . ?
C3 N1 C21 C26 -47.9(5) . . . . ?
C15 N1 C21 C26 137.6(4) . . . . ?
C3 N1 C21 C22 133.0(4) . . . . ?
C15 N1 C21 C22 -41.4(5) . . . . ?
C26 C21 C22 C23 -1.2(6) . . . . ?
N1 C21 C22 C23 177.9(4) . . . . ?
C21 C22 C23 C24 1.2(7) . . . . ?
C22 C23 C24 C25 0.5(7) . . . . ?
C23 C24 C25 C26 -2.2(7) . . . . ?
C22 C21 C26 C25 -0.5(6) . . . . ?
N1 C21 C26 C25 -179.5(4) . . . . ?
C24 C25 C26 C21 2.2(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8A O1 0.97 2.59 3.438(6) 146.4 4_566

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.064

_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_a_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc270fd3
_database_code_depnum_ccdc_archive 'CCDC 2055994'
loop_
_audit_author_name
_audit_author_address
TPA-Cl
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2021-01-14 deposited with the CCDC.	2021-02-23 downloaded from the CCDC.
;
_audit_creation_date             2018-12-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H20 Cl N O'
_chemical_formula_sum            'C26 H20 Cl N O'
_chemical_formula_weight         397.88
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   22.361(5)
_cell_length_b                   10.757(2)
_cell_length_c                   8.4111(17)
_cell_angle_alpha                90
_cell_angle_beta                 92.09(3)
_cell_angle_gamma                90
_cell_volume                     2021.9(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6268
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      2.1012
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13279
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         2.734
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4091
_reflns_number_total             4564
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4564
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0666
_refine_ls_restrained_S_all      1.175
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0338P)²+1.1809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1340
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C17(H17), C18(H18), C22(H22), C23(H23), C25(H25),
  C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 1.23223(3) 0.64327(9) 0.35250(10) 0.0754(3) Uani 1 1 d . . . . .
O1 O 0.95159(6) 0.72401(16) 0.3702(2) 0.0462(4) Uani 1 1 d . . . . .
N1 N 0.67797(7) 0.62559(15) 0.1619(2) 0.0292(4) Uani 1 1 d . . . . .
C1 C 0.64119(8) 0.73407(18) 0.1558(2) 0.0262(4) Uani 1 1 d . . . . .
C2 C 0.66068(8) 0.84482(19) 0.0905(2) 0.0291(4) Uani 1 1 d . . . . .
H2 H 0.700468 0.851249 0.055457 0.035 Uiso 1 1 calc R . . . .
C3 C 0.62264(9) 0.94572(19) 0.0761(2) 0.0313(4) Uani 1 1 d . . . . .
H3 H 0.636686 1.021540 0.033206 0.038 Uiso 1 1 calc R . . . .
C4 C 0.56407(9) 0.9371(2) 0.1239(2) 0.0327(5) Uani 1 1 d . . . . .
H4 H 0.537564 1.005577 0.110390 0.039 Uiso 1 1 calc R . . . .
C5 C 0.54461(8) 0.8278(2) 0.1915(3) 0.0325(5) Uani 1 1 d . . . . .
H5 H 0.504619 0.821438 0.225066 0.039 Uiso 1 1 calc R . . . .
C6 C 0.58312(8) 0.72724(19) 0.2106(2) 0.0293(4) Uani 1 1 d . . . . .
H6 H 0.569934 0.653676 0.261071 0.035 Uiso 1 1 calc R . . . .
C7 C 0.64991(8) 0.50816(18) 0.1311(2) 0.0274(4) Uani 1 1 d . . . . .
C8 C 0.60471(9) 0.4997(2) 0.0129(3) 0.0324(5) Uani 1 1 d . . . . .
H8 H 0.594630 0.570500 -0.050058 0.039 Uiso 1 1 calc R . . . .
C9 C 0.57445(10) 0.3890(2) -0.0132(3) 0.0382(5) Uani 1 1 d . . . . .
H9 H 0.542831 0.384686 -0.091551 0.046 Uiso 1 1 calc R . . . .
C10 C 0.59018(9) 0.2851(2) 0.0745(3) 0.0386(5) Uani 1 1 d . . . . .
H10 H 0.569426 0.209006 0.056593 0.046 Uiso 1 1 calc R . . . .
C11 C 0.63615(9) 0.2916(2) 0.1884(3) 0.0353(5) Uani 1 1 d . . . . .
H11 H 0.647518 0.219264 0.246814 0.042 Uiso 1 1 calc R . . . .
C12 C 0.66599(9) 0.40328(19) 0.2183(3) 0.0315(5) Uani 1 1 d . . . . .
H12 H 0.697151 0.407539 0.297909 0.038 Uiso 1 1 calc R . . . .
C13 C 0.74064(8) 0.63275(18) 0.1854(2) 0.0268(4) Uani 1 1 d . . . . .
C14 C 0.77785(8) 0.54601(19) 0.1143(2) 0.0295(4) Uani 1 1 d . . . . .
H14 H 0.760794 0.482951 0.047821 0.035 Uiso 1 1 calc R . . . .
C15 C 0.83927(8) 0.55127(19) 0.1399(2) 0.0292(4) Uani 1 1 d . . . . .
H15 H 0.863941 0.491623 0.090847 0.035 Uiso 1 1 calc R . . . .
C16 C 0.86543(8) 0.64313(19) 0.2368(2) 0.0278(4) Uani 1 1 d . . . . .
C17 C 0.82801(8) 0.7300(2) 0.3067(2) 0.0296(4) Uani 1 1 d . . . . .
H17 H 0.845115 0.793376 0.372579 0.036 Uiso 1 1 calc R . . . .
C18 C 0.76678(8) 0.72543(19) 0.2819(2) 0.0292(4) Uani 1 1 d . . . . .
H18 H 0.742202 0.785471 0.330466 0.035 Uiso 1 1 calc R . . . .
C19 C 0.93113(9) 0.6520(2) 0.2703(2) 0.0315(5) Uani 1 1 d . . . . .
C20 C 0.97165(9) 0.5698(2) 0.1750(3) 0.0358(5) Uani 1 1 d . . . . .
H20A H 0.960845 0.481765 0.192767 0.043 Uiso 1 1 calc R . . . .
H20B H 0.964723 0.587912 0.060415 0.043 Uiso 1 1 calc R . . . .
C21 C 1.03710(8) 0.5874(2) 0.2178(2) 0.0313(4) Uani 1 1 d . . . . .
C22 C 1.06609(9) 0.5091(2) 0.3265(3) 0.0376(5) Uani 1 1 d . . . . .
H22 H 1.044491 0.443088 0.372816 0.045 Uiso 1 1 calc R . . . .
C23 C 1.12622(10) 0.5255(2) 0.3690(3) 0.0429(6) Uani 1 1 d . . . . .
H23 H 1.145822 0.471641 0.443672 0.051 Uiso 1 1 calc R . . . .
C24 C 1.15676(9) 0.6216(2) 0.3004(3) 0.0420(6) Uani 1 1 d . . . . .
C25 C 1.12943(10) 0.7005(2) 0.1919(3) 0.0435(6) Uani 1 1 d . . . . .
H25 H 1.151253 0.766240 0.145865 0.052 Uiso 1 1 calc R . . . .
C26 C 1.06933(9) 0.6825(2) 0.1507(3) 0.0380(5) Uani 1 1 d . . . . .
H26 H 1.050065 0.736293 0.075391 0.046 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
Cl1 C24 1.744(2) . ?
O1 C19 1.220(2) . ?
N1 C1 1.428(2) . ?
N1 C7 1.430(2) . ?
N1 C13 1.410(2) . ?
C1 C2 1.389(3) . ?
C1 C6 1.395(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(3) . ?
C7 C12 1.386(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.393(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.399(3) . ?
C13 C18 1.400(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.396(3) . ?
C16 C17 1.398(3) . ?
C16 C19 1.489(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.378(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.516(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.506(3) . ?
C21 C22 1.387(3) . ?
C21 C26 1.384(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.390(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.377(3) . ?
C24 C25 1.373(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.389(3) . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C7 117.85(15) . . ?
C13 N1 C1 121.92(16) . . ?
C13 N1 C7 120.06(16) . . ?
C2 C1 N1 121.79(17) . . ?
C2 C1 C6 119.02(18) . . ?
C6 C1 N1 119.14(18) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.50(18) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.44(19) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.39(19) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.45(18) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.10(19) . . ?
C5 C6 H6 119.9 . . ?
C8 C7 N1 119.25(17) . . ?
C12 C7 N1 121.31(18) . . ?
C12 C7 C8 119.43(19) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 119.9(2) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C11 119.6(2) . . ?
C7 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 N1 120.46(18) . . ?
C14 C13 C18 118.72(17) . . ?
C18 C13 N1 120.81(17) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.58(19) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.81(18) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C17 118.32(17) . . ?
C15 C16 C19 123.06(18) . . ?
C17 C16 C19 118.62(18) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.25(19) . . ?
C18 C17 H17 119.4 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.32(18) . . ?
C17 C18 H18 119.8 . . ?
O1 C19 C16 120.91(18) . . ?
O1 C19 C20 121.23(18) . . ?
C16 C19 C20 117.86(17) . . ?
C19 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C21 C20 C19 113.25(18) . . ?
C21 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
C22 C21 C20 120.6(2) . . ?
C26 C21 C20 120.8(2) . . ?
C26 C21 C22 118.69(19) . . ?
C21 C22 H22 119.4 . . ?
C21 C22 C23 121.1(2) . . ?
C23 C22 H22 119.4 . . ?
C22 C23 H23 120.7 . . ?
C24 C23 C22 118.5(2) . . ?
C24 C23 H23 120.7 . . ?
C23 C24 Cl1 119.03(18) . . ?
C25 C24 Cl1 119.18(19) . . ?
C25 C24 C23 121.8(2) . . ?
C24 C25 H25 120.6 . . ?
C24 C25 C26 118.9(2) . . ?
C26 C25 H25 120.6 . . ?
C21 C26 C25 121.0(2) . . ?
C21 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?

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
Cl1 C24 C25 C26 179.86(19) . . . . ?
O1 C19 C20 C21 0.1(3) . . . . ?
N1 C1 C2 C3 175.47(18) . . . . ?
N1 C1 C6 C5 -173.66(18) . . . . ?
N1 C7 C8 C9 -176.27(19) . . . . ?
N1 C7 C12 C11 177.76(18) . . . . ?
N1 C13 C14 C15 -178.65(18) . . . . ?
N1 C13 C18 C17 178.66(19) . . . . ?
C1 N1 C7 C8 38.7(3) . . . . ?
C1 N1 C7 C12 -140.12(19) . . . . ?
C1 N1 C13 C14 -146.86(19) . . . . ?
C1 N1 C13 C18 34.0(3) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C1 C6 C5 3.6(3) . . . . ?
C2 C3 C4 C5 2.3(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 -2.6(3) . . . . ?
C6 C1 C2 C3 -1.7(3) . . . . ?
C7 N1 C1 C2 -140.76(19) . . . . ?
C7 N1 C1 C6 36.4(3) . . . . ?
C7 N1 C13 C14 28.3(3) . . . . ?
C7 N1 C13 C18 -150.81(19) . . . . ?
C7 C8 C9 C10 -2.0(3) . . . . ?
C8 C7 C12 C11 -1.0(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C10 C11 C12 1.5(3) . . . . ?
C10 C11 C12 C7 -1.0(3) . . . . ?
C12 C7 C8 C9 2.5(3) . . . . ?
C13 N1 C1 C2 34.5(3) . . . . ?
C13 N1 C1 C6 -148.30(19) . . . . ?
C13 N1 C7 C8 -136.72(19) . . . . ?
C13 N1 C7 C12 44.5(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C13 C18 C17 -0.5(3) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C14 C15 C16 C19 179.07(19) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C15 C16 C19 O1 -171.1(2) . . . . ?
C15 C16 C19 C20 9.5(3) . . . . ?
C16 C17 C18 C13 0.1(3) . . . . ?
C16 C19 C20 C21 179.50(18) . . . . ?
C17 C16 C19 O1 8.3(3) . . . . ?
C17 C16 C19 C20 -171.11(19) . . . . ?
C18 C13 C14 C15 0.5(3) . . . . ?
C19 C16 C17 C18 -179.09(19) . . . . ?
C19 C20 C21 C22 95.7(2) . . . . ?
C19 C20 C21 C26 -83.6(3) . . . . ?
C20 C21 C22 C23 -179.0(2) . . . . ?
C20 C21 C26 C25 178.8(2) . . . . ?
C21 C22 C23 C24 -0.1(4) . . . . ?
C22 C21 C26 C25 -0.6(3) . . . . ?
C22 C23 C24 Cl1 -179.98(18) . . . . ?
C22 C23 C24 C25 -0.1(4) . . . . ?
C23 C24 C25 C26 0.0(4) . . . . ?
C24 C25 C26 C21 0.3(4) . . . . ?
C26 C21 C22 C23 0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a_CCDC2
_audit_block_doi                 10.5517/ccdc.csd.cc270fmb
_database_code_depnum_ccdc_archive 'CCDC 2056001'
loop_
_audit_author_name
_audit_author_address
TPA-Br
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2021-01-14 deposited with the CCDC.	2021-02-23 downloaded from the CCDC.
;
_audit_creation_date             2018-12-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H20 Br N O'
_chemical_formula_sum            'C26 H20 Br N O'
_chemical_formula_weight         442.34
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   22.628(5)
_cell_length_b                   10.750(2)
_cell_length_c                   8.3962(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.56(3)
_cell_angle_gamma                90
_cell_volume                     2041.7(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6189
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4662
_cell_measurement_theta_min      1.8943
_shelx_estimated_absorpt_T_max   0.854
_shelx_estimated_absorpt_T_min   0.750
_exptl_absorpt_coefficient_mu    2.030
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13536
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.460
_diffrn_reflns_theta_min         2.701
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3858
_reflns_number_total             4644
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.793
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4644
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0618
_refine_ls_restrained_S_all      1.155
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0227P)²+2.2753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1139
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C6(H6), C22(H22), C2(H2), C15(H15), C18(H18), C3(H3), C5(H5),
 C4(H4), C10(H10), C11(H11), C26(H26), C8(H8), C17(H17), C23(H23), C12(H12),
 C25(H25), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 1.23117(2) 0.64386(5) 0.34976(5) 0.06121(16) Uani 1 1 d . . . . .
C24 C 1.14989(13) 0.6204(3) 0.2967(4) 0.0341(7) Uani 1 1 d . . . . .
N1 N 0.67620(10) 0.6260(2) 0.1591(3) 0.0253(5) Uani 1 1 d . . . . .
C16 C 0.86158(12) 0.6418(3) 0.2360(3) 0.0242(6) Uani 1 1 d . . . . .
C14 C 0.77505(12) 0.5458(3) 0.1121(3) 0.0252(6) Uani 1 1 d . . . . .
H14 H 0.758422 0.483059 0.045002 0.030 Uiso 1 1 calc R . . . .
C1 C 0.63965(12) 0.7341(3) 0.1539(3) 0.0227(6) Uani 1 1 d . . . . .
O1 O 0.94622(9) 0.7209(2) 0.3716(3) 0.0398(6) Uani 1 1 d . . . . .
C6 C 0.65967(13) 0.8452(3) 0.0880(3) 0.0257(6) Uani 1 1 d . . . . .
H6 H 0.699111 0.851711 0.052954 0.031 Uiso 1 1 calc R . . . .
C19 C 0.92605(12) 0.6501(3) 0.2703(3) 0.0256(6) Uani 1 1 d . . . . .
C22 C 1.06007(14) 0.5075(3) 0.3235(4) 0.0335(7) Uani 1 1 d . . . . .
H22 H 1.038751 0.441439 0.370334 0.040 Uiso 1 1 calc R . . . .
C2 C 0.58194(12) 0.7274(3) 0.2093(3) 0.0256(6) Uani 1 1 d . . . . .
H2 H 0.568728 0.653939 0.260237 0.031 Uiso 1 1 calc R . . . .
C7 C 0.64851(12) 0.5082(2) 0.1278(3) 0.0227(6) Uani 1 1 d . . . . .
C13 C 0.73795(12) 0.6325(3) 0.1829(3) 0.0244(6) Uani 1 1 d . . . . .
C15 C 0.83563(13) 0.5501(3) 0.1382(3) 0.0267(6) Uani 1 1 d . . . . .
H15 H 0.860002 0.490041 0.089216 0.032 Uiso 1 1 calc R . . . .
C18 C 0.76374(12) 0.7254(3) 0.2801(3) 0.0252(6) Uani 1 1 d . . . . .
H18 H 0.739441 0.785911 0.328439 0.030 Uiso 1 1 calc R . . . .
C3 C 0.54422(13) 0.8276(3) 0.1900(3) 0.0284(6) Uani 1 1 d . . . . .
H3 H 0.504554 0.821164 0.223333 0.034 Uiso 1 1 calc R . . . .
C5 C 0.62146(13) 0.9460(3) 0.0742(3) 0.0283(6) Uani 1 1 d . . . . .
H5 H 0.635264 1.021964 0.031025 0.034 Uiso 1 1 calc R . . . .
C4 C 0.56358(13) 0.9374(3) 0.1224(3) 0.0284(6) Uani 1 1 d . . . . .
H4 H 0.537425 1.005995 0.109350 0.034 Uiso 1 1 calc R . . . .
C20 C 0.96680(13) 0.5691(3) 0.1736(4) 0.0310(7) Uani 1 1 d . . . . .
H20A H 0.956160 0.480753 0.189874 0.037 Uiso 1 1 calc R . . . .
H20B H 0.960251 0.588273 0.059123 0.037 Uiso 1 1 calc R . . . .
C10 C 0.58901(14) 0.2851(3) 0.0719(4) 0.0322(7) Uani 1 1 d . . . . .
H10 H 0.568367 0.209182 0.054046 0.039 Uiso 1 1 calc R . . . .
C11 C 0.63428(14) 0.2913(3) 0.1850(4) 0.0320(7) Uani 1 1 d . . . . .
H11 H 0.645264 0.218795 0.243303 0.038 Uiso 1 1 calc R . . . .
C26 C 1.06331(14) 0.6823(3) 0.1489(4) 0.0332(7) Uani 1 1 d . . . . .
H26 H 1.044237 0.736549 0.074530 0.040 Uiso 1 1 calc R . . . .
C8 C 0.60396(13) 0.5006(3) 0.0103(3) 0.0284(6) Uani 1 1 d . . . . .
H8 H 0.594147 0.571460 -0.052577 0.034 Uiso 1 1 calc R . . . .
C17 C 0.82417(13) 0.7289(3) 0.3053(3) 0.0262(6) Uani 1 1 d . . . . .
H17 H 0.840857 0.792177 0.371540 0.031 Uiso 1 1 calc R . . . .
C23 C 1.11958(14) 0.5237(3) 0.3641(4) 0.0371(7) Uani 1 1 d . . . . .
H23 H 1.138978 0.468802 0.437121 0.045 Uiso 1 1 calc R . . . .
C12 C 0.66399(13) 0.4023(3) 0.2146(3) 0.0269(6) Uani 1 1 d . . . . .
H12 H 0.694739 0.405985 0.293742 0.032 Uiso 1 1 calc R . . . .
C25 C 1.12261(14) 0.7005(3) 0.1886(4) 0.0366(7) Uani 1 1 d . . . . .
H25 H 1.144065 0.766747 0.142562 0.044 Uiso 1 1 calc R . . . .
C21 C 1.03129(13) 0.5861(3) 0.2158(3) 0.0283(6) Uani 1 1 d . . . . .
C9 C 0.57394(14) 0.3894(3) -0.0149(4) 0.0331(7) Uani 1 1 d . . . . .
H9 H 0.542726 0.385391 -0.092755 0.040 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
Br1 C24 1.897(3) . ?
C24 C23 1.376(4) . ?
C24 C25 1.384(4) . ?
N1 C1 1.427(3) . ?
N1 C7 1.434(3) . ?
N1 C13 1.408(3) . ?
C16 C19 1.482(4) . ?
C16 C15 1.402(4) . ?
C16 C17 1.399(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.398(4) . ?
C14 C15 1.383(4) . ?
C1 C6 1.396(4) . ?
C1 C2 1.400(4) . ?
O1 C19 1.221(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.389(4) . ?
C19 C20 1.519(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.391(4) . ?
C22 C21 1.387(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(4) . ?
C7 C8 1.393(4) . ?
C7 C12 1.391(4) . ?
C13 C18 1.406(4) . ?
C15 H15 0.9500 . ?
C18 H18 0.9500 . ?
C18 C17 1.378(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.384(4) . ?
C4 H4 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.503(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(4) . ?
C10 C9 1.376(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(4) . ?
C26 H26 0.9500 . ?
C26 C25 1.388(4) . ?
C26 C21 1.390(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(4) . ?
C17 H17 0.9500 . ?
C23 H23 0.9500 . ?
C12 H12 0.9500 . ?
C25 H25 0.9500 . ?
C9 H9 0.9500 . ?

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
C23 C24 Br1 119.6(2) . . ?
C23 C24 C25 121.4(3) . . ?
C25 C24 Br1 118.9(2) . . ?
C1 N1 C7 117.6(2) . . ?
C13 N1 C1 122.4(2) . . ?
C13 N1 C7 119.8(2) . . ?
C15 C16 C19 123.4(3) . . ?
C17 C16 C19 118.9(2) . . ?
C17 C16 C15 117.8(3) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C15 C14 C13 121.0(3) . . ?
C6 C1 N1 121.0(3) . . ?
C6 C1 C2 119.4(3) . . ?
C2 C1 N1 119.5(2) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 H6 120.3 . . ?
C16 C19 C20 118.1(2) . . ?
O1 C19 C16 121.3(3) . . ?
O1 C19 C20 120.6(3) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C21 C22 C23 121.2(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C8 C7 N1 119.1(2) . . ?
C12 C7 N1 121.6(2) . . ?
C12 C7 C8 119.3(3) . . ?
C14 C13 N1 120.8(2) . . ?
C14 C13 C18 118.4(3) . . ?
C18 C13 N1 120.8(2) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 C16 120.9(3) . . ?
C14 C15 H15 119.5 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
C19 C20 H20A 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C21 C20 C19 113.8(2) . . ?
C21 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(3) . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C25 C26 H26 119.4 . . ?
C25 C26 C21 121.3(3) . . ?
C21 C26 H26 119.3 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.0(3) . . ?
C9 C8 H8 120.0 . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.8(3) . . ?
C18 C17 H17 119.1 . . ?
C24 C23 C22 118.9(3) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C7 C12 H12 120.2 . . ?
C11 C12 C7 119.7(3) . . ?
C11 C12 H12 120.2 . . ?
C24 C25 C26 118.7(3) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
C22 C21 C20 121.0(3) . . ?
C22 C21 C26 118.4(3) . . ?
C26 C21 C20 120.6(3) . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?

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
Br1 C24 C23 C22 -179.8(2) . . . . ?
Br1 C24 C25 C26 179.3(2) . . . . ?
N1 C1 C6 C5 175.3(2) . . . . ?
N1 C1 C2 C3 -173.4(2) . . . . ?
N1 C7 C8 C9 -175.8(3) . . . . ?
N1 C7 C12 C11 177.2(3) . . . . ?
N1 C13 C18 C17 178.5(3) . . . . ?
C16 C19 C20 C21 179.0(2) . . . . ?
C14 C13 C18 C17 -0.8(4) . . . . ?
C1 N1 C7 C8 38.4(4) . . . . ?
C1 N1 C7 C12 -139.9(3) . . . . ?
C1 N1 C13 C14 -147.3(3) . . . . ?
C1 N1 C13 C18 33.5(4) . . . . ?
C1 C6 C5 C4 -1.0(4) . . . . ?
C1 C2 C3 C4 -2.9(4) . . . . ?
O1 C19 C20 C21 0.0(4) . . . . ?
C6 C1 C2 C3 3.9(4) . . . . ?
C6 C5 C4 C3 2.0(4) . . . . ?
C19 C16 C15 C14 179.1(3) . . . . ?
C19 C16 C17 C18 -179.1(3) . . . . ?
C19 C20 C21 C22 95.4(3) . . . . ?
C19 C20 C21 C26 -83.8(3) . . . . ?
C2 C1 C6 C5 -1.9(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C7 N1 C1 C6 -140.8(3) . . . . ?
C7 N1 C1 C2 36.4(4) . . . . ?
C7 N1 C13 C14 28.3(4) . . . . ?
C7 N1 C13 C18 -150.9(3) . . . . ?
C7 C8 C9 C10 -2.1(5) . . . . ?
C13 N1 C1 C6 34.9(4) . . . . ?
C13 N1 C1 C2 -147.9(3) . . . . ?
C13 N1 C7 C8 -137.4(3) . . . . ?
C13 N1 C7 C12 44.3(4) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
C13 C18 C17 C16 0.2(4) . . . . ?
C15 C16 C19 O1 -170.5(3) . . . . ?
C15 C16 C19 C20 10.5(4) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C15 C14 C13 N1 -178.5(3) . . . . ?
C15 C14 C13 C18 0.8(4) . . . . ?
C10 C11 C12 C7 -0.9(4) . . . . ?
C11 C10 C9 C8 0.1(5) . . . . ?
C8 C7 C12 C11 -1.1(4) . . . . ?
C17 C16 C19 O1 8.9(4) . . . . ?
C17 C16 C19 C20 -170.1(3) . . . . ?
C17 C16 C15 C14 -0.3(4) . . . . ?
C23 C24 C25 C26 0.3(5) . . . . ?
C23 C22 C21 C20 -179.4(3) . . . . ?
C23 C22 C21 C26 -0.1(5) . . . . ?
C12 C7 C8 C9 2.5(4) . . . . ?
C25 C24 C23 C22 -0.7(5) . . . . ?
C25 C26 C21 C22 -0.3(5) . . . . ?
C25 C26 C21 C20 178.9(3) . . . . ?
C21 C22 C23 C24 0.6(5) . . . . ?
C21 C26 C25 C24 0.3(5) . . . . ?
C9 C10 C11 C12 1.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
