# Electronic Supplementary Material (ESI) for ChemComm.
# 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_202009199
_database_code_depnum_ccdc_archive 'CCDC 2060266'
loop_
_audit_author_name
_audit_author_address
'Yuan shupei'
;Chengdu Institute of Organic Chemistry, Chinese Academy of Science
China
;
_audit_update_record             
;
2021-02-01 deposited with the CCDC.	2021-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H22 Br N O2'
_chemical_formula_weight         472.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   9.5547(2)
_cell_length_b                   10.0105(3)
_cell_length_c                   24.6215(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2354.99(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.009
_exptl_absorpt_coefficient_mu    2.552
_shelx_estimated_absorpt_T_min   0.671
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8533
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.590
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_full        67.072
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4210
_reflns_number_gt                3469
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0373P)²+0.4003P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1197 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.029(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4210
_refine_ls_number_parameters     290
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.038
_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
Br1 Br 1.28046(13) 0.9783(2) 0.68460(5) 0.0971(5) Uani 0.858(4) 1 d . . P A 1
Br1A Br 1.3120(9) 0.9122(11) 0.6995(3) 0.0971(5) Uani 0.142(4) 1 d D . P A 2
O1 O 0.8819(3) 0.4841(4) 0.57579(12) 0.0637(9) Uani 1 1 d . . . . .
O2 O 0.9152(5) 0.2745(5) 0.54853(19) 0.0990(15) Uani 1 1 d . . . . .
N1 N 0.4550(5) 0.3654(5) 0.55324(17) 0.0670(11) Uani 1 1 d D . . . .
H1 H 0.432(6) 0.322(5) 0.5245(15) 0.069(16) Uiso 1 1 d D . . . .
C1 C 1.0796(6) 0.6521(7) 0.6175(3) 0.0845(19) Uani 1 1 d . . . . .
H1A H 1.1010 0.5873 0.5917 0.101 Uiso 1 1 calc R U . . .
C2 C 1.1783(6) 0.7472(7) 0.6311(2) 0.0878(19) Uani 1 1 d . . . . .
H2 H 1.2648 0.7483 0.6138 0.105 Uiso 1 1 calc R U . . .
C3 C 1.1478(6) 0.8390(6) 0.6698(2) 0.0713(14) Uani 1 1 d D . . . .
C4 C 1.0219(6) 0.8385(6) 0.6957(2) 0.0790(16) Uani 1 1 d . . . . .
H4 H 1.0023 0.9011 0.7225 0.095 Uiso 1 1 calc R U . . .
C5 C 0.9239(5) 0.7440(6) 0.6814(2) 0.0737(14) Uani 1 1 d . . . . .
H5 H 0.8381 0.7429 0.6992 0.088 Uiso 1 1 calc R U . . .
C6 C 0.9492(5) 0.6521(5) 0.64189(18) 0.0559(11) Uani 1 1 d . . . . .
C7 C 0.8374(5) 0.5518(5) 0.62525(18) 0.0576(12) Uani 1 1 d . . . . .
C8 C 0.8248(5) 0.4380(6) 0.6647(2) 0.0648(13) Uani 1 1 d . . . . .
H8 H 0.8018 0.4482 0.7011 0.078 Uiso 1 1 calc R U . . .
C9 C 0.8501(6) 0.3229(6) 0.6417(2) 0.0761(15) Uani 1 1 d . . . . .
C10 C 0.8858(6) 0.3511(6) 0.5843(2) 0.0745(15) Uani 1 1 d . . . . .
C11 C 0.8480(10) 0.1827(7) 0.6628(3) 0.118(3) Uani 1 1 d . . . . .
H11A H 0.7812 0.1312 0.6426 0.177 Uiso 1 1 calc R U . . .
H11B H 0.8222 0.1832 0.7005 0.177 Uiso 1 1 calc R U . . .
H11C H 0.9392 0.1438 0.6588 0.177 Uiso 1 1 calc R U . . .
C12 C 0.6921(4) 0.6175(5) 0.61497(17) 0.0548(11) Uani 1 1 d . . . . .
H12 H 0.6609 0.6472 0.6509 0.066 Uiso 1 1 calc R U . . .
C13 C 0.6930(5) 0.7431(5) 0.58081(19) 0.0593(11) Uani 1 1 d . . . . .
C14 C 0.7838(6) 0.7676(6) 0.5377(2) 0.0730(14) Uani 1 1 d . . . . .
H14 H 0.8519 0.7047 0.5291 0.088 Uiso 1 1 calc R U . . .
C15 C 0.7744(7) 0.8825(7) 0.5080(2) 0.0849(17) Uani 1 1 d . . . . .
H15 H 0.8358 0.8963 0.4792 0.102 Uiso 1 1 calc R U . . .
C16 C 0.6756(7) 0.9780(7) 0.5199(3) 0.098(2) Uani 1 1 d . . . . .
H16 H 0.6705 1.0562 0.4996 0.118 Uiso 1 1 calc R U . . .
C17 C 0.5846(7) 0.9564(7) 0.5621(3) 0.097(2) Uani 1 1 d . . . . .
H17 H 0.5164 1.0196 0.5703 0.116 Uiso 1 1 calc R U . . .
C18 C 0.5946(6) 0.8408(6) 0.5924(3) 0.0793(16) Uani 1 1 d . . . . .
H18 H 0.5337 0.8281 0.6214 0.095 Uiso 1 1 calc R U . . .
C19 C 0.4393(5) 0.4931(6) 0.6876(2) 0.0739(14) Uani 1 1 d . . . . .
H19 H 0.4907 0.5531 0.7085 0.089 Uiso 1 1 calc R U . . .
C20 C 0.3260(7) 0.4297(7) 0.7090(2) 0.092(2) Uani 1 1 d . . . . .
H20 H 0.3009 0.4470 0.7448 0.110 Uiso 1 1 calc R U . . .
C21 C 0.2466(7) 0.3398(7) 0.6789(3) 0.100(2) Uani 1 1 d . . . . .
H21 H 0.1685 0.2999 0.6945 0.120 Uiso 1 1 calc R U . . .
C22 C 0.2825(6) 0.3089(6) 0.6258(2) 0.0806(16) Uani 1 1 d . . . . .
H22 H 0.2306 0.2480 0.6057 0.097 Uiso 1 1 calc R U . . .
C23 C 0.3983(5) 0.3720(6) 0.6040(2) 0.0647(13) Uani 1 1 d . . . . .
C24 C 0.4778(5) 0.4666(5) 0.63334(18) 0.0597(11) Uani 1 1 d . . . . .
C25 C 0.5841(4) 0.5154(5) 0.59767(17) 0.0558(11) Uani 1 1 d . . . . .
C26 C 0.5662(5) 0.4539(6) 0.54905(18) 0.0604(12) Uani 1 1 d . . . . .
C27 C 0.6358(6) 0.4677(7) 0.49432(19) 0.0796(17) Uani 1 1 d . . . . .
H27A H 0.6862 0.5506 0.4929 0.119 Uiso 1 1 calc R U . . .
H27B H 0.5659 0.4664 0.4663 0.119 Uiso 1 1 calc R U . . .
H27C H 0.6996 0.3948 0.4890 0.119 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.919(5) . ?
Br1A C3 1.879(8) . ?
O1 C10 1.348(7) . ?
O1 C7 1.458(5) . ?
O2 C10 1.200(7) . ?
N1 C23 1.363(7) . ?
N1 C26 1.388(6) . ?
N1 H1 0.86(2) . ?
C1 C2 1.381(8) . ?
C1 C6 1.382(7) . ?
C1 H1A 0.9300 . ?
C2 C3 1.357(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.361(7) . ?
C4 C5 1.377(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.360(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.523(7) . ?
C7 C8 1.502(7) . ?
C7 C12 1.557(6) . ?
C8 C9 1.306(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.482(8) . ?
C9 C11 1.496(9) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.513(7) . ?
C12 C25 1.513(6) . ?
C12 H12 0.9800 . ?
C13 C18 1.386(8) . ?
C13 C14 1.392(7) . ?
C14 C15 1.367(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(9) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.361(8) . ?
C19 C24 1.412(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.392(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.383(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.414(7) . ?
C24 C25 1.428(6) . ?
C25 C26 1.357(6) . ?
C26 C27 1.509(6) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
C10 O1 C7 109.8(4) . . ?
C23 N1 C26 110.0(4) . . ?
C23 N1 H1 133(4) . . ?
C26 N1 H1 117(4) . . ?
C2 C1 C6 120.7(5) . . ?
C2 C1 H1A 119.6 . . ?
C6 C1 H1A 119.6 . . ?
C3 C2 C1 119.4(5) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 121.1(5) . . ?
C2 C3 Br1A 111.0(5) . . ?
C4 C3 Br1A 123.9(4) . . ?
C2 C3 Br1 118.9(4) . . ?
C4 C3 Br1 119.9(4) . . ?
C3 C4 C5 119.0(5) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 121.8(5) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 118.1(5) . . ?
C5 C6 C7 120.9(4) . . ?
C1 C6 C7 121.1(4) . . ?
O1 C7 C8 102.2(4) . . ?
O1 C7 C6 109.0(4) . . ?
C8 C7 C6 112.5(4) . . ?
O1 C7 C12 108.7(4) . . ?
C8 C7 C12 110.7(4) . . ?
C6 C7 C12 113.1(4) . . ?
C9 C8 C7 112.0(5) . . ?
C9 C8 H8 124.0 . . ?
C7 C8 H8 124.0 . . ?
C8 C9 C10 106.7(6) . . ?
C8 C9 C11 132.5(6) . . ?
C10 C9 C11 120.8(6) . . ?
O2 C10 O1 121.6(6) . . ?
O2 C10 C9 129.2(6) . . ?
O1 C10 C9 109.3(5) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C25 114.1(4) . . ?
C13 C12 C7 115.8(4) . . ?
C25 C12 C7 111.6(4) . . ?
C13 C12 H12 104.6 . . ?
C25 C12 H12 104.6 . . ?
C7 C12 H12 104.6 . . ?
C18 C13 C14 117.1(5) . . ?
C18 C13 C12 117.9(5) . . ?
C14 C13 C12 125.0(5) . . ?
C15 C14 C13 121.1(6) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 121.0(6) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 119.1(6) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 119.9(6) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C13 121.8(6) . . ?
C17 C18 H18 119.1 . . ?
C13 C18 H18 119.1 . . ?
C20 C19 C24 119.1(5) . . ?
C20 C19 H19 120.5 . . ?
C24 C19 H19 120.5 . . ?
C19 C20 C21 121.9(5) . . ?
C19 C20 H20 119.0 . . ?
C21 C20 H20 119.0 . . ?
C22 C21 C20 120.8(5) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 117.6(5) . . ?
C23 C22 H22 121.2 . . ?
C21 C22 H22 121.2 . . ?
N1 C23 C22 130.8(5) . . ?
N1 C23 C24 106.7(4) . . ?
C22 C23 C24 122.5(5) . . ?
C19 C24 C23 118.0(4) . . ?
C19 C24 C25 134.7(5) . . ?
C23 C24 C25 107.3(4) . . ?
C26 C25 C24 107.3(4) . . ?
C26 C25 C12 129.8(4) . . ?
C24 C25 C12 122.8(4) . . ?
C25 C26 N1 108.7(4) . . ?
C25 C26 C27 133.7(5) . . ?
N1 C26 C27 117.5(4) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.9(11) . . . . ?
C1 C2 C3 C4 0.3(11) . . . . ?
C1 C2 C3 Br1A 158.5(7) . . . . ?
C1 C2 C3 Br1 -175.6(6) . . . . ?
C2 C3 C4 C5 -0.9(10) . . . . ?
Br1A C3 C4 C5 -156.2(7) . . . . ?
Br1 C3 C4 C5 174.9(5) . . . . ?
C3 C4 C5 C6 -0.6(10) . . . . ?
C4 C5 C6 C1 2.7(10) . . . . ?
C4 C5 C6 C7 -177.6(5) . . . . ?
C2 C1 C6 C5 -3.3(10) . . . . ?
C2 C1 C6 C7 177.0(6) . . . . ?
C10 O1 C7 C8 3.4(5) . . . . ?
C10 O1 C7 C6 122.6(4) . . . . ?
C10 O1 C7 C12 -113.7(4) . . . . ?
C5 C6 C7 O1 169.0(5) . . . . ?
C1 C6 C7 O1 -11.3(7) . . . . ?
C5 C6 C7 C8 -78.4(6) . . . . ?
C1 C6 C7 C8 101.3(6) . . . . ?
C5 C6 C7 C12 47.9(6) . . . . ?
C1 C6 C7 C12 -132.3(6) . . . . ?
O1 C7 C8 C9 -3.0(5) . . . . ?
C6 C7 C8 C9 -119.7(5) . . . . ?
C12 C7 C8 C9 112.7(5) . . . . ?
C7 C8 C9 C10 1.4(6) . . . . ?
C7 C8 C9 C11 -178.4(7) . . . . ?
C7 O1 C10 O2 177.4(5) . . . . ?
C7 O1 C10 C9 -2.8(6) . . . . ?
C8 C9 C10 O2 -179.4(6) . . . . ?
C11 C9 C10 O2 0.5(10) . . . . ?
C8 C9 C10 O1 0.8(6) . . . . ?
C11 C9 C10 O1 -179.3(6) . . . . ?
O1 C7 C12 C13 -75.1(5) . . . . ?
C8 C7 C12 C13 173.5(4) . . . . ?
C6 C7 C12 C13 46.2(5) . . . . ?
O1 C7 C12 C25 57.8(5) . . . . ?
C8 C7 C12 C25 -53.7(5) . . . . ?
C6 C7 C12 C25 179.1(4) . . . . ?
C25 C12 C13 C18 81.5(5) . . . . ?
C7 C12 C13 C18 -146.8(4) . . . . ?
C25 C12 C13 C14 -97.3(5) . . . . ?
C7 C12 C13 C14 34.5(7) . . . . ?
C18 C13 C14 C15 -0.8(8) . . . . ?
C12 C13 C14 C15 178.0(5) . . . . ?
C13 C14 C15 C16 0.4(9) . . . . ?
C14 C15 C16 C17 -0.5(10) . . . . ?
C15 C16 C17 C18 0.9(11) . . . . ?
C16 C17 C18 C13 -1.3(10) . . . . ?
C14 C13 C18 C17 1.2(8) . . . . ?
C12 C13 C18 C17 -177.6(6) . . . . ?
C24 C19 C20 C21 -0.2(11) . . . . ?
C19 C20 C21 C22 1.6(12) . . . . ?
C20 C21 C22 C23 -0.9(11) . . . . ?
C26 N1 C23 C22 175.9(6) . . . . ?
C26 N1 C23 C24 -0.9(6) . . . . ?
C21 C22 C23 N1 -177.5(6) . . . . ?
C21 C22 C23 C24 -1.0(9) . . . . ?
C20 C19 C24 C23 -1.6(9) . . . . ?
C20 C19 C24 C25 177.8(6) . . . . ?
N1 C23 C24 C19 179.5(5) . . . . ?
C22 C23 C24 C19 2.3(8) . . . . ?
N1 C23 C24 C25 -0.1(6) . . . . ?
C22 C23 C24 C25 -177.3(5) . . . . ?
C19 C24 C25 C26 -178.4(6) . . . . ?
C23 C24 C25 C26 1.1(6) . . . . ?
C19 C24 C25 C12 1.5(9) . . . . ?
C23 C24 C25 C12 -179.0(4) . . . . ?
C13 C12 C25 C26 57.7(7) . . . . ?
C7 C12 C25 C26 -76.1(6) . . . . ?
C13 C12 C25 C24 -122.2(5) . . . . ?
C7 C12 C25 C24 104.1(5) . . . . ?
C24 C25 C26 N1 -1.7(6) . . . . ?
C12 C25 C26 N1 178.5(5) . . . . ?
C24 C25 C26 C27 175.2(6) . . . . ?
C12 C25 C26 C27 -4.7(10) . . . . ?
C23 N1 C26 C25 1.7(6) . . . . ?
C23 N1 C26 C27 -175.8(5) . . . . ?

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_202010214
_database_code_depnum_ccdc_archive 'CCDC 2060270'
loop_
_audit_author_name
_audit_author_address
'Yuan shupei'
;Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2021-02-01 deposited with the CCDC.	2021-04-13 downloaded from the CCDC.
;
_audit_creation_date             2020-10-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H23 N O4'
_chemical_formula_sum            'C27 H23 N O4'
_chemical_formula_weight         425.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N4
_chemical_oxdiff_usercomment     r
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2533(10)
_cell_length_b                   10.7469(10)
_cell_length_c                   11.7360(9)
_cell_angle_alpha                93.016(7)
_cell_angle_beta                 99.314(7)
_cell_angle_gamma                116.142(10)
_cell_volume                     1134.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1324
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3740
_cell_measurement_theta_min      3.8310
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.905
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.15
_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  0.0358
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7932
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.061
_diffrn_reflns_theta_max         67.061
_diffrn_reflns_theta_min         3.855
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -15.00   1.00    1.50    --  -33.50 -57.00 -60.00   87
  2  ω   -108.00 -32.00   1.00    1.50    --  -33.50 178.00  90.00   76
  3  ω   -108.00 -32.00   1.00    1.50    --  -33.50 178.00 -30.00   76
  4  ω    -71.00  39.00   1.00    1.50    --  -33.50  19.00 120.00  110
  5  ω     59.00  97.00   1.00    1.50    --   36.47 178.00 -30.00   38
  6  ω     27.00  54.00   1.00    1.50    --   36.47  77.00   0.00   27
  7  ω     -3.00  25.00   1.00    1.50    --   36.47 -99.00   0.00   28
  8  ω     27.00  75.00   1.00    1.50    --   36.47 -99.00   0.00   48
  9  ω     41.00  74.00   1.00    1.50    --   36.47 -99.00-180.00   33
 10  ω     52.00 104.00   1.00    1.50    --   36.47  19.00 150.00   52
 11  ω     32.00  70.00   1.00    1.50    --   36.47  37.00-150.00   38
 12  ω     74.00 105.00   1.00    1.50    --   36.47  77.00   0.00   31
 13  ω     36.00  75.00   1.00    1.50    --   36.47 -99.00 -90.00   39
 14  ω      0.00  44.00   1.00    1.50    --   36.47  19.00 150.00   44
 15  ω     -3.00  30.00   1.00    1.50    --   36.47 -99.00 -90.00   33
 16  ω     66.00  91.00   1.00    1.50    --   36.47 178.00  60.00   25
 17  ω     67.00 108.00   1.00    1.50    --   36.47 178.00-150.00   41
 18  ω     70.00 112.00   1.00    7.00    --  108.00-111.00 -90.00   42
 19  ω    126.00 173.00   1.00    7.00    --  108.00 111.00 120.00   47
 20  ω     53.00 134.00   1.00    7.00    --  108.00 -77.00  90.00   81
 21  ω     85.00 110.00   1.00    7.00    --  108.00-111.00 120.00   25
 22  ω    115.00 147.00   1.00    7.00    --  108.00 178.00 120.00   32
 23  ω     43.00 125.00   1.00    7.00    --  108.00 -61.00-150.00   82
 24  ω     39.00  65.00   1.00    7.00    --  108.00-111.00 120.00   26
 25  ω     80.00 112.00   1.00    7.00    --  108.00 178.00 120.00   32
 26  ω    125.00 176.00   1.00    7.00    --  108.00  61.00-180.00   51
 27  ω     51.00 149.00   1.00    7.00    --  108.00 -15.00-150.00   98
 28  ω     70.00 122.00   1.00    7.00    --  108.00 -30.00 150.00   52
 29  ω     38.00  64.00   1.00    7.00    --  108.00 -30.00 150.00   26
 30  ω     46.00  91.00   1.00    7.00    --  108.00 -94.00-180.00   45
 31  ω     88.00 175.00   1.00    7.00    --  108.00  45.00-120.00   87
 32  ω     38.00 126.00   1.00    7.00    --  108.00 -30.00  60.00   88
 33  ω    114.00 169.00   1.00    7.00    --  108.00 131.00-174.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1133619000
_diffrn_orient_matrix_UB_12      -0.0535379000
_diffrn_orient_matrix_UB_13      -0.1168162000
_diffrn_orient_matrix_UB_21      -0.1277820000
_diffrn_orient_matrix_UB_22      -0.0405771000
_diffrn_orient_matrix_UB_23      0.0662547000
_diffrn_orient_matrix_UB_31      0.0089931000
_diffrn_orient_matrix_UB_32      0.1466108000
_diffrn_orient_matrix_UB_33      -0.0036513000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2581
_reflns_number_total             4034
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.181
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4034
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0525
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0554P)²+0.0907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1505
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C -0.1909(3) 0.5852(3) 0.5658(2) 0.0515(6) Uani 1 1 d . . . . .
C2 C -0.2268(3) 0.6985(3) 0.5338(2) 0.0512(6) Uani 1 1 d . . . . .
C3 C -0.1160(3) 0.7887(2) 0.4913(2) 0.0473(5) Uani 1 1 d . . . . .
H3 H -0.1108 0.8714 0.4668 0.057 Uiso 1 1 calc R . . . .
C4 C 0.0004(3) 0.7406(2) 0.4875(2) 0.0458(5) Uani 1 1 d . . . . .
C5 C 0.0083(3) 0.6976(2) 0.3606(2) 0.0475(5) Uani 1 1 d . . . . .
H5 H 0.0655 0.6446 0.3649 0.057 Uiso 1 1 calc R . . . .
C6 C 0.0876(3) 0.8257(3) 0.3024(2) 0.0488(6) Uani 1 1 d . . . . .
C7 C 0.1507(3) 0.8117(3) 0.1997(2) 0.0521(6) Uani 1 1 d . . . . .
C8 C 0.1974(3) 0.9179(3) 0.1281(2) 0.0579(7) Uani 1 1 d . . . . .
C9 C 0.2607(4) 0.8999(4) 0.0350(3) 0.0795(9) Uani 1 1 d . . . . .
H9 H 0.2950 0.9706 -0.0112 0.095 Uiso 1 1 calc R . . . .
C10 C 0.2727(5) 0.7803(4) 0.0113(3) 0.0984(12) Uani 1 1 d . . . . .
H10 H 0.3134 0.7698 -0.0516 0.118 Uiso 1 1 calc R . . . .
C11 C 0.2258(5) 0.6754(4) 0.0788(3) 0.0949(12) Uani 1 1 d . . . . .
H11 H 0.2343 0.5941 0.0618 0.114 Uiso 1 1 calc R . . . .
C12 C 0.1658(4) 0.6910(3) 0.1721(3) 0.0730(8) Uani 1 1 d . . . . .
H12 H 0.1344 0.6195 0.2179 0.088 Uiso 1 1 calc R . . . .
C13 C -0.3677(3) 0.7017(3) 0.5493(3) 0.0762(9) Uani 1 1 d . . . . .
H13A H -0.4461 0.6454 0.4841 0.114 Uiso 1 1 calc GR . . . .
H13B H -0.3536 0.7964 0.5539 0.114 Uiso 1 1 calc GR . . . .
H13C H -0.3937 0.6655 0.6198 0.114 Uiso 1 1 calc GR . . . .
C14 C 0.1526(3) 0.8385(2) 0.5633(2) 0.0456(5) Uani 1 1 d . . . . .
C15 C 0.1628(3) 0.9291(3) 0.6561(2) 0.0562(6) Uani 1 1 d . . . . .
H15 H 0.0771 0.9307 0.6707 0.067 Uiso 1 1 calc R . . . .
C16 C 0.2993(3) 1.0183(3) 0.7283(3) 0.0671(8) Uani 1 1 d . . . . .
H16 H 0.3042 1.0779 0.7910 0.081 Uiso 1 1 calc R . . . .
C17 C 0.4262(3) 1.0175(3) 0.7063(3) 0.0697(8) Uani 1 1 d . . . . .
H17 H 0.5179 1.0784 0.7528 0.084 Uiso 1 1 calc R . . . .
C18 C 0.4177(3) 0.9268(3) 0.6154(3) 0.0712(8) Uani 1 1 d . . . . .
H18 H 0.5039 0.9258 0.6013 0.085 Uiso 1 1 calc R . . . .
C19 C 0.2815(3) 0.8362(3) 0.5442(3) 0.0614(7) Uani 1 1 d . . . . .
H19 H 0.2769 0.7741 0.4837 0.074 Uiso 1 1 calc R . . . .
C20 C -0.1462(3) 0.6038(3) 0.2863(2) 0.0516(6) Uani 1 1 d . . . . .
C21 C -0.2237(3) 0.6595(3) 0.2173(3) 0.0676(8) Uani 1 1 d . . . . .
H21 H -0.1801 0.7550 0.2129 0.081 Uiso 1 1 calc R . . . .
C22 C -0.3658(4) 0.5738(4) 0.1548(3) 0.0858(10) Uani 1 1 d . . . . .
H22 H -0.4172 0.6121 0.1084 0.103 Uiso 1 1 calc R . . . .
C23 C -0.4314(4) 0.4329(4) 0.1606(3) 0.0836(10) Uani 1 1 d . . . . .
H23 H -0.5270 0.3758 0.1181 0.100 Uiso 1 1 calc R . . . .
C24 C -0.3564(4) 0.3767(3) 0.2286(3) 0.0745(9) Uani 1 1 d . . . . .
H24 H -0.4017 0.2814 0.2338 0.089 Uiso 1 1 calc R . . . .
C25 C -0.2127(3) 0.4612(3) 0.2903(2) 0.0613(7) Uani 1 1 d . . . . .
H25 H -0.1609 0.4217 0.3345 0.074 Uiso 1 1 calc R . . . .
C26 C 0.1735(3) 1.1287(3) 0.0750(3) 0.0699(8) Uani 1 1 d . . . . .
C27 C 0.1348(4) 1.2374(3) 0.1222(3) 0.0823(10) Uani 1 1 d . . . . .
H27A H 0.2136 1.2996 0.1849 0.123 Uiso 1 1 calc GR . . . .
H27B H 0.0445 1.1926 0.1505 0.123 Uiso 1 1 calc GR . . . .
H27C H 0.1213 1.2896 0.0614 0.123 Uiso 1 1 calc GR . . . .
N1 N 0.1813(3) 1.0393(3) 0.1504(2) 0.0627(6) Uani 1 1 d . . . . .
H1 H 0.153(3) 1.043(3) 0.217(3) 0.071(9) Uiso 1 1 d . . . . .
O1 O -0.05761(18) 0.61080(16) 0.53862(15) 0.0487(4) Uani 1 1 d . . . . .
O2 O -0.2577(2) 0.4840(2) 0.61052(19) 0.0710(6) Uani 1 1 d . . . . .
O3 O 0.0925(2) 0.93711(18) 0.33846(16) 0.0621(5) Uani 1 1 d . . . . .
O4 O 0.1939(4) 1.1217(3) -0.0229(2) 0.1169(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.468(3) . ?
C1 O1 1.366(3) . ?
C1 O2 1.203(3) . ?
C2 C3 1.320(3) . ?
C2 C13 1.500(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.501(3) . ?
C4 C5 1.562(3) . ?
C4 C14 1.530(3) . ?
C4 O1 1.460(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.522(3) . ?
C5 C20 1.529(3) . ?
C6 C7 1.487(3) . ?
C6 O3 1.225(3) . ?
C7 C8 1.410(4) . ?
C7 C12 1.400(4) . ?
C8 C9 1.404(4) . ?
C8 N1 1.402(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.363(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.367(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(4) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.381(3) . ?
C14 C19 1.386(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.394(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.370(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.371(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.391(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.382(4) . ?
C20 C25 1.383(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.382(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.371(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.363(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.387(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.496(4) . ?
C26 N1 1.359(4) . ?
C26 O4 1.205(4) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
N1 H1 0.89(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 108.8(2) . . ?
O2 C1 C2 130.4(2) . . ?
O2 C1 O1 120.8(2) . . ?
C1 C2 C13 123.0(2) . . ?
C3 C2 C1 107.6(2) . . ?
C3 C2 C13 129.4(2) . . ?
C2 C3 H3 124.4 . . ?
C2 C3 C4 111.3(2) . . ?
C4 C3 H3 124.4 . . ?
C3 C4 C5 112.8(2) . . ?
C3 C4 C14 114.4(2) . . ?
C14 C4 C5 113.1(2) . . ?
O1 C4 C3 102.55(18) . . ?
O1 C4 C5 105.66(18) . . ?
O1 C4 C14 107.25(18) . . ?
C4 C5 H5 108.0 . . ?
C6 C5 C4 111.26(19) . . ?
C6 C5 H5 108.0 . . ?
C6 C5 C20 109.9(2) . . ?
C20 C5 C4 111.6(2) . . ?
C20 C5 H5 108.0 . . ?
C7 C6 C5 119.5(2) . . ?
O3 C6 C5 118.9(2) . . ?
O3 C6 C7 121.5(2) . . ?
C8 C7 C6 121.8(2) . . ?
C12 C7 C6 120.1(2) . . ?
C12 C7 C8 118.1(3) . . ?
C9 C8 C7 118.8(3) . . ?
N1 C8 C7 120.3(2) . . ?
N1 C8 C9 120.9(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(3) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 120.9(3) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.5(3) . . ?
C12 C11 H11 120.2 . . ?
C7 C12 H12 119.1 . . ?
C11 C12 C7 121.7(3) . . ?
C11 C12 H12 119.1 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C4 119.6(2) . . ?
C15 C14 C19 118.5(2) . . ?
C19 C14 C4 121.9(2) . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.2(3) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.9(3) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.7(3) . . ?
C19 C18 H18 119.6 . . ?
C14 C19 C18 120.1(3) . . ?
C14 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C5 121.1(2) . . ?
C21 C20 C25 118.7(3) . . ?
C25 C20 C5 120.1(2) . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.3(3) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.4(3) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.9(3) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.2(3) . . ?
C25 C24 H24 119.9 . . ?
C20 C25 C24 120.4(3) . . ?
C20 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
N1 C26 C27 114.7(3) . . ?
O4 C26 C27 121.7(3) . . ?
O4 C26 N1 123.6(3) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C8 N1 H1 111.7(19) . . ?
C26 N1 C8 128.2(3) . . ?
C26 N1 H1 118.4(19) . . ?
C1 O1 C4 109.67(17) . . ?

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
N1 H1 O3 0.89(3) 1.88(3) 2.633(3) 141(3) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 1.9(3) . . . . ?
C2 C1 O1 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 111.2(2) . . . . ?
C2 C3 C4 C14 -117.8(2) . . . . ?
C2 C3 C4 O1 -2.0(3) . . . . ?
C3 C4 C5 C6 76.8(2) . . . . ?
C3 C4 C5 C20 -46.4(3) . . . . ?
C3 C4 C14 C15 22.7(3) . . . . ?
C3 C4 C14 C19 -159.5(2) . . . . ?
C3 C4 O1 C1 1.2(2) . . . . ?
C4 C5 C6 C7 160.0(2) . . . . ?
C4 C5 C6 O3 -23.0(3) . . . . ?
C4 C5 C20 C21 94.0(3) . . . . ?
C4 C5 C20 C25 -83.9(3) . . . . ?
C4 C14 C15 C16 178.9(2) . . . . ?
C4 C14 C19 C18 -179.8(2) . . . . ?
C5 C4 C14 C15 153.6(2) . . . . ?
C5 C4 C14 C19 -28.6(3) . . . . ?
C5 C4 O1 C1 -117.1(2) . . . . ?
C5 C6 C7 C8 166.7(2) . . . . ?
C5 C6 C7 C12 -13.7(4) . . . . ?
C5 C20 C21 C22 -177.1(3) . . . . ?
C5 C20 C25 C24 176.0(3) . . . . ?
C6 C5 C20 C21 -29.9(3) . . . . ?
C6 C5 C20 C25 152.2(2) . . . . ?
C6 C7 C8 C9 177.8(3) . . . . ?
C6 C7 C8 N1 -1.9(4) . . . . ?
C6 C7 C12 C11 -179.0(3) . . . . ?
C7 C8 C9 C10 2.2(5) . . . . ?
C7 C8 N1 C26 -156.8(3) . . . . ?
C8 C7 C12 C11 0.7(5) . . . . ?
C8 C9 C10 C11 -1.1(6) . . . . ?
C9 C8 N1 C26 23.6(5) . . . . ?
C9 C10 C11 C12 -0.1(7) . . . . ?
C10 C11 C12 C7 0.3(6) . . . . ?
C12 C7 C8 C9 -1.9(4) . . . . ?
C12 C7 C8 N1 178.5(3) . . . . ?
C13 C2 C3 C4 -177.7(3) . . . . ?
C14 C4 C5 C6 -55.0(2) . . . . ?
C14 C4 C5 C20 -178.10(18) . . . . ?
C14 C4 O1 C1 122.0(2) . . . . ?
C14 C15 C16 C17 0.8(4) . . . . ?
C15 C14 C19 C18 -1.9(4) . . . . ?
C15 C16 C17 C18 -1.7(5) . . . . ?
C16 C17 C18 C19 0.7(5) . . . . ?
C17 C18 C19 C14 1.1(5) . . . . ?
C19 C14 C15 C16 1.0(4) . . . . ?
C20 C5 C6 C7 -75.9(3) . . . . ?
C20 C5 C6 O3 101.1(3) . . . . ?
C20 C21 C22 C23 0.1(6) . . . . ?
C21 C20 C25 C24 -1.9(4) . . . . ?
C21 C22 C23 C24 0.2(6) . . . . ?
C22 C23 C24 C25 -1.3(6) . . . . ?
C23 C24 C25 C20 2.2(5) . . . . ?
C25 C20 C21 C22 0.8(5) . . . . ?
C27 C26 N1 C8 171.7(3) . . . . ?
N1 C8 C9 C10 -178.2(3) . . . . ?
O1 C1 C2 C3 -1.1(3) . . . . ?
O1 C1 C2 C13 178.5(3) . . . . ?
O1 C4 C5 C6 -171.96(18) . . . . ?
O1 C4 C5 C20 64.9(2) . . . . ?
O1 C4 C14 C15 -90.3(2) . . . . ?
O1 C4 C14 C19 87.5(3) . . . . ?
O2 C1 C2 C3 177.6(3) . . . . ?
O2 C1 C2 C13 -2.8(5) . . . . ?
O2 C1 O1 C4 -179.0(2) . . . . ?
O3 C6 C7 C8 -10.3(4) . . . . ?
O3 C6 C7 C12 169.4(3) . . . . ?
O4 C26 N1 C8 -7.4(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.360
_oxdiff_exptl_absorpt_empirical_full_min 0.878
