# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2164016'
loop_
_audit_author_name
_audit_author_address
'He Jiang'
;Souther univercity of science and technology
China
;
_audit_update_record             
;
2022-04-02 deposited with the CCDC.	2022-10-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H15 N3 O2'
_chemical_formula_weight         353.37

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'

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

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

_cell_length_a                   10.2240(9)
_cell_length_b                   43.467(4)
_cell_length_c                   7.7850(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3459.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7018
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      28.21

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13118
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_k_max       57
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.812
_diffrn_reflns_theta_max         28.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             4160
_reflns_number_gt                3189
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_max     0.946
_reflns_Friedel_fraction_full    0.978

_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.1000P)²+0.4007P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1136 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4160
_refine_ls_number_parameters     245
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1783
_refine_ls_wR_factor_gt          0.1571
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_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
O2 O 0.3993(3) 0.69501(7) 0.2773(6) 0.0852(10) Uani 1 1 d . . . . .
O1 O 0.7567(3) 0.63757(7) 0.3388(6) 0.0898(11) Uani 1 1 d . . . . .
N003 N 0.5659(3) 0.66191(6) 0.3055(5) 0.0589(8) Uani 1 1 d . . . . .
N1 N 0.2945(3) 0.50388(8) 0.7988(6) 0.0731(10) Uani 1 1 d . . . . .
C1 C 0.2558(4) 0.52349(9) 0.7169(6) 0.0584(9) Uani 1 1 d . . . . .
C11 C 0.2299(3) 0.59935(8) 0.4641(5) 0.0506(8) Uani 1 1 d . . . . .
C5 C 0.5131(4) 0.55372(7) 0.6176(5) 0.0511(8) Uani 1 1 d . . . . .
H5 H 0.489301 0.535236 0.669049 0.061 Uiso 1 1 calc R U . . .
C6 C 0.5863(3) 0.60947(7) 0.4560(4) 0.0449(7) Uani 1 1 d . . . . .
C7 C 0.4561(3) 0.60188(6) 0.4785(4) 0.0421(7) Uani 1 1 d . . . . .
C3 C 0.2035(3) 0.54844(8) 0.6187(6) 0.0540(8) Uani 1 1 d . . . . .
C8 C 0.4193(3) 0.57394(7) 0.5579(4) 0.0436(7) Uani 1 1 d . . . . .
C12 C 0.3396(3) 0.61790(7) 0.4224(4) 0.0463(7) Uani 1 1 d . . . . .
C9 C 0.6439(3) 0.56172(8) 0.5987(5) 0.0546(9) Uani 1 1 d . . . . .
H9 H 0.708378 0.548643 0.640835 0.066 Uiso 1 1 calc R U . . .
C13 C 0.3259(3) 0.64640(8) 0.3471(5) 0.0508(8) Uani 1 1 d . . . . .
C10 C 0.6794(3) 0.58855(8) 0.5190(5) 0.0517(8) Uani 1 1 d . . . . .
H10 H 0.767823 0.593057 0.506307 0.062 Uiso 1 1 calc R U . . .
C4 C 0.2759(3) 0.57154(8) 0.5519(5) 0.0460(7) Uani 1 1 d . . . . .
C17 C 0.6398(4) 0.63682(8) 0.3653(5) 0.0555(9) Uani 1 1 d . . . . .
C18 C 0.4318(4) 0.66893(7) 0.3118(5) 0.0552(8) Uani 1 1 d . . . . .
C2 C 0.0640(4) 0.54695(11) 0.5974(8) 0.0798(14) Uani 1 1 d . . . . .
C14 C 0.1057(4) 0.60962(10) 0.4198(7) 0.0678(11) Uani 1 1 d . . . . .
H14 H 0.032341 0.597720 0.443461 0.081 Uiso 1 1 calc R U . . .
C15 C 0.1992(4) 0.65583(10) 0.3043(6) 0.0671(10) Uani 1 1 d . . . . .
H15 H 0.186990 0.674720 0.250606 0.081 Uiso 1 1 calc R U . . .
C19 C 0.6480(5) 0.68699(10) 0.2291(6) 0.0706(11) Uani 1 1 d . . . . .
H19A H 0.595542 0.698658 0.148304 0.085 Uiso 1 1 calc R U . . .
H19B H 0.720091 0.677848 0.166209 0.085 Uiso 1 1 calc R U . . .
C16 C 0.0933(4) 0.63786(10) 0.3398(7) 0.0740(12) Uani 1 1 d . . . . .
H16 H 0.010416 0.644791 0.309325 0.089 Uiso 1 1 calc R U . . .
C20 C 0.7016(6) 0.70843(11) 0.3632(7) 0.0889(15) Uani 1 1 d . . . . .
H20A H 0.752374 0.696768 0.445882 0.107 Uiso 1 1 calc R U . . .
H20B H 0.629727 0.718128 0.423923 0.107 Uiso 1 1 calc R U . . .
N2 N -0.0449(4) 0.54512(12) 0.5831(12) 0.133(3) Uani 1 1 d . . . . .
C21 C 0.7875(6) 0.73306(11) 0.2828(9) 0.0977(18) Uani 1 1 d . . . . .
H21A H 0.737059 0.743438 0.194598 0.117 Uiso 1 1 calc R U . . .
H21B H 0.807978 0.748167 0.370489 0.117 Uiso 1 1 calc R U . . .
C22 C 0.9095(6) 0.72262(17) 0.2067(16) 0.135(3) Uani 1 1 d . . . . .
H22A H 0.959105 0.711448 0.290799 0.202 Uiso 1 1 calc R U . . .
H22B H 0.959056 0.740074 0.168305 0.202 Uiso 1 1 calc R U . . .
H22C H 0.890918 0.709452 0.110780 0.202 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
O2 C18 1.211(4) . ?
O1 C17 1.213(4) . ?
N003 C18 1.405(5) . ?
N003 C17 1.406(5) . ?
N003 C19 1.499(5) . ?
N1 C1 1.136(6) . ?
C1 C3 1.430(6) . ?
C11 C14 1.389(5) . ?
C11 C12 1.419(5) . ?
C11 C4 1.466(5) . ?
C5 C8 1.381(5) . ?
C5 C9 1.390(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.382(4) . ?
C6 C10 1.405(5) . ?
C6 C17 1.487(5) . ?
C7 C8 1.413(5) . ?
C7 C12 1.447(4) . ?
C3 C4 1.352(5) . ?
C3 C2 1.437(5) . ?
C8 C4 1.471(4) . ?
C12 C13 1.377(5) . ?
C9 C10 1.370(5) . ?
C9 H9 0.9300 . ?
C13 C15 1.399(5) . ?
C13 C18 1.486(5) . ?
C10 H10 0.9300 . ?
C2 N2 1.122(5) . ?
C14 C16 1.382(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.363(6) . ?
C15 H15 0.9300 . ?
C19 C20 1.503(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C16 H16 0.9300 . ?
C20 C21 1.519(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.454(10) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C18 N003 C17 132.9(3) . . ?
C18 N003 C19 113.7(3) . . ?
C17 N003 C19 113.2(3) . . ?
N1 C1 C3 177.9(5) . . ?
C14 C11 C12 118.9(3) . . ?
C14 C11 C4 132.4(4) . . ?
C12 C11 C4 108.7(3) . . ?
C8 C5 C9 118.2(3) . . ?
C8 C5 H5 120.9 . . ?
C9 C5 H5 120.9 . . ?
C7 C6 C10 117.0(3) . . ?
C7 C6 C17 127.2(3) . . ?
C10 C6 C17 115.7(3) . . ?
C6 C7 C8 121.1(3) . . ?
C6 C7 C12 129.8(3) . . ?
C8 C7 C12 109.0(3) . . ?
C4 C3 C1 124.4(3) . . ?
C4 C3 C2 122.2(3) . . ?
C1 C3 C2 113.5(3) . . ?
C5 C8 C7 120.6(3) . . ?
C5 C8 C4 131.1(3) . . ?
C7 C8 C4 108.2(3) . . ?
C13 C12 C11 121.8(3) . . ?
C13 C12 C7 130.1(3) . . ?
C11 C12 C7 108.0(3) . . ?
C10 C9 C5 121.1(3) . . ?
C10 C9 H9 119.5 . . ?
C5 C9 H9 119.5 . . ?
C12 C13 C15 117.3(4) . . ?
C12 C13 C18 126.7(3) . . ?
C15 C13 C18 116.0(3) . . ?
C9 C10 C6 122.0(3) . . ?
C9 C10 H10 119.0 . . ?
C6 C10 H10 119.0 . . ?
C3 C4 C11 128.1(3) . . ?
C3 C4 C8 125.9(3) . . ?
C11 C4 C8 106.0(3) . . ?
O1 C17 N003 116.9(3) . . ?
O1 C17 C6 117.7(3) . . ?
N003 C17 C6 125.4(3) . . ?
O2 C18 N003 117.6(4) . . ?
O2 C18 C13 117.3(4) . . ?
N003 C18 C13 125.0(3) . . ?
N2 C2 C3 178.3(6) . . ?
C16 C14 C11 118.8(4) . . ?
C16 C14 H14 120.6 . . ?
C11 C14 H14 120.6 . . ?
C16 C15 C13 121.3(4) . . ?
C16 C15 H15 119.4 . . ?
C13 C15 H15 119.4 . . ?
N003 C19 C20 112.3(4) . . ?
N003 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
N003 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
C15 C16 C14 121.8(4) . . ?
C15 C16 H16 119.1 . . ?
C14 C16 H16 119.1 . . ?
C19 C20 C21 111.2(5) . . ?
C19 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C22 C21 C20 116.4(5) . . ?
C22 C21 H21A 108.2 . . ?
C20 C21 H21A 108.2 . . ?
C22 C21 H21B 108.2 . . ?
C20 C21 H21B 108.2 . . ?
H21A C21 H21B 107.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.039



####################################################################### 
# 
# 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_tx10669_auto
_database_code_depnum_ccdc_archive 'CCDC 2165586'
loop_
_audit_author_name
_audit_author_address
'Pu Wang'
;Souther univercity of science and thenology
China
;
_audit_update_record             
;
2022-04-10 deposited with the CCDC.	2022-10-11 downloaded from the CCDC.
;
_audit_creation_date             2022-04-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H19 N3 O2'
_chemical_formula_sum            'C24 H19 N3 O2'
_chemical_formula_weight         381.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N F'
_chemical_oxdiff_usercomment     CHONS
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                   4.96443(14)
_cell_length_b                   9.1287(2)
_cell_length_c                   21.2708(6)
_cell_angle_alpha                80.708(2)
_cell_angle_beta                 88.385(2)
_cell_angle_gamma                88.576(2)
_cell_volume                     950.74(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5009
_cell_measurement_temperature    169.98(10)
_cell_measurement_theta_max      75.2990
_cell_measurement_theta_min      2.1460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10550
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.986
_diffrn_reflns_theta_min         2.105
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     95.00 178.00   0.50    0.29    --  107.36  57.00  30.00  166
  2  ω     87.00 178.00   0.50    0.29    --  107.36  92.00-112.00  182
  3  ω    147.00 175.00   0.50    0.29    --  107.36  38.00 150.00   56
  4  ω     94.00 144.00   0.50    0.29    --  107.36  38.00 150.00  100
  5  ω     -5.00  21.00   0.50    0.07    --  -47.45  19.00 150.00   52
  6  ω    -62.00 -37.00   0.50    0.29    -- -104.50  57.00  90.00   50
  7  ω    -61.00 -32.00   0.50    0.29    -- -104.50  57.00   0.00   58
  8  ω    -61.00 -34.00   0.50    0.29    -- -104.50  57.00  30.00   54
  9  ω    -95.00 -68.00   0.50    0.29    -- -104.50  77.00 -60.00   54
 10  ω    -60.00 -32.00   0.50    0.29    -- -104.50  57.00-120.00   56
 11  ω    -61.00 -32.00   0.50    0.29    -- -104.50  57.00-150.00   58
 12  ω    -20.00  26.00   0.50    0.07    --  -47.45  38.00-120.00   92
 13  ω     38.00 110.00   0.50    0.29    --  107.36-125.00 150.00  144
 14  ω     75.00 109.00   0.50    0.29    --  107.36-125.00 120.00   68
 15  ω     35.00  62.00   0.50    0.29    --  107.36-125.00 120.00   54
 16  ω     62.00 102.00   0.50    0.29    --  107.36 -92.00 134.00   80
 17  ω     54.00 106.00   0.50    0.29    --  107.36 -99.00  30.00  104
 18  ω     70.00 101.00   0.50    0.29    --  107.36 -99.00 -30.00   62
 19  ω     40.00  91.00   0.50    0.29    --  107.36 -99.00 -60.00  102
 20  ω     39.00  68.00   0.50    0.29    --  107.36 -99.00 -30.00   58
 21  ω    -24.00  77.00   0.50    0.07    --   47.45 -92.00 134.00  202
 22  ω     35.00  68.00   0.50    0.29    --  107.36 -57.00 -30.00   66
 23  ω     37.00  67.00   0.50    0.29    --  107.36 -57.00-150.00   60
 24  ω     41.00 109.00   0.50    0.29    --  107.36 -77.00-150.00  136
 25  ω     39.00  66.00   0.50    0.29    --  107.36 -57.00 120.00   54
 26  ω    -26.00  30.00   0.50    0.07    --   47.45 -19.00  60.00  112
 27  ω    -12.00  13.00   0.50    0.07    --   47.45 -19.00 -60.00   50
 28  ω     10.00  46.00   0.50    0.07    --   47.45 -38.00-180.00   72
 29  ω   -112.00 -75.00   0.50    0.07    --  -47.45-125.00-120.00   74
 30  ω   -113.00 -74.00   0.50    0.07    --  -47.45-125.00 -90.00   78
 31  ω   -174.00 -80.00   0.50    0.29    -- -104.50 -92.00 134.00  188
 32  ω   -147.00-120.00   0.50    0.29    -- -104.50 -62.00 177.90   54
 33  ω   -173.00-126.00   0.50    0.29    -- -104.50 -38.00  60.00   94
 34  ω   -124.00 -97.00   0.50    0.29    -- -104.50 -38.00  60.00   54
 35  ω   -131.00 -97.00   0.50    0.29    -- -104.50 -38.00 -60.00   68
 36  ω   -174.00-142.00   0.50    0.29    -- -104.50 -38.00 -60.00   64
 37  ω   -158.00-109.00   0.50    0.29    -- -104.50 -53.00-162.37   98
 38  ω    -93.00 -68.00   0.50    0.29    -- -104.50  92.00-112.00   50
 39  ω    -78.00 -48.00   0.50    0.29    -- -104.50 148.00 -35.96   60
 40  ω   -128.00 -93.00   0.50    0.29    -- -104.50 148.00 -35.96   70
 41  ω    -77.00  25.00   0.50    0.07    --  -47.45  92.00-112.00  204
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0966475000
_diffrn_orient_matrix_UB_12      -0.0190025000
_diffrn_orient_matrix_UB_13      -0.0663476000
_diffrn_orient_matrix_UB_21      -0.0839212000
_diffrn_orient_matrix_UB_22      0.1655070000
_diffrn_orient_matrix_UB_23      -0.0131422000
_diffrn_orient_matrix_UB_31      0.2828998000
_diffrn_orient_matrix_UB_32      0.0387414000
_diffrn_orient_matrix_UB_33      -0.0285388000
_diffrn_oxdiff_digest_frames     
;
01f79092db6192077c01da9585326c3d9900037f473
;
_diffrn_oxdiff_digest_hkl        
;
0188160c9a500e2355883a69a9fe53bf4545ea
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2905
_reflns_number_total             3433
_reflns_odcompleteness_completeness 100.00
_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 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.0017(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.050
_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)+(0.0905P)²+0.2988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1521
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C5(H5A,H5B), C4(H4A,H4B), C3(H3A,H3B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C22(H22), C24(H24), C17(H17), C16(H16), C23(H23)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
O14 O 0.5127(3) 0.03302(16) 0.25508(7) 0.0447(4) Uani 1 1 d . . . . .
O15 O -0.1613(3) 0.32205(17) 0.16730(8) 0.0505(4) Uani 1 1 d . . . . .
N7 N 0.1762(3) 0.19113(17) 0.21970(8) 0.0317(4) Uani 1 1 d . . . . .
N29 N 0.8038(4) 0.6558(2) 0.48854(9) 0.0444(5) Uani 1 1 d . . . . .
N25 N 0.1820(4) 0.9408(2) 0.40148(10) 0.0506(5) Uani 1 1 d . . . . .
C10 C 0.1953(3) 0.47305(19) 0.28720(8) 0.0272(4) Uani 1 1 d . . . . .
C20 C 0.3837(3) 0.58979(19) 0.36519(9) 0.0274(4) Uani 1 1 d . . . . .
C27 C 0.4366(4) 0.6908(2) 0.40390(9) 0.0296(4) Uani 1 1 d . . . . .
C11 C 0.4005(3) 0.37395(19) 0.31926(9) 0.0271(4) Uani 1 1 d . . . . .
C21 C 0.5163(4) 0.44363(19) 0.36627(9) 0.0282(4) Uani 1 1 d . . . . .
C19 C 0.1840(4) 0.60511(19) 0.31465(9) 0.0279(4) Uani 1 1 d . . . . .
C9 C 0.0266(4) 0.4541(2) 0.23896(9) 0.0303(4) Uani 1 1 d . . . . .
C18 C 0.0047(4) 0.7193(2) 0.29222(9) 0.0318(4) Uani 1 1 d . . . . .
H18 H -0.002751 0.808373 0.309972 0.038 Uiso 1 1 calc R . . . .
C28 C 0.6408(4) 0.6684(2) 0.45081(9) 0.0324(4) Uani 1 1 d . . . . .
C12 C 0.4886(4) 0.23418(19) 0.30909(9) 0.0290(4) Uani 1 1 d . . . . .
C22 C 0.7188(4) 0.3734(2) 0.40428(9) 0.0315(4) Uani 1 1 d . . . . .
H22 H 0.796894 0.420180 0.435941 0.038 Uiso 1 1 calc R . . . .
C13 C 0.3942(4) 0.1489(2) 0.25986(9) 0.0315(4) Uani 1 1 d . . . . .
C24 C 0.6932(4) 0.1653(2) 0.34826(9) 0.0332(4) Uani 1 1 d . . . . .
H24 H 0.757046 0.069216 0.342542 0.040 Uiso 1 1 calc R . . . .
C17 C -0.1639(4) 0.7005(2) 0.24316(10) 0.0341(4) Uani 1 1 d . . . . .
H17 H -0.287502 0.777847 0.227262 0.041 Uiso 1 1 calc R . . . .
C8 C 0.0093(4) 0.3197(2) 0.20703(10) 0.0342(4) Uani 1 1 d . . . . .
C26 C 0.2936(4) 0.8293(2) 0.40146(10) 0.0341(4) Uani 1 1 d . . . . .
C16 C -0.1548(4) 0.5710(2) 0.21712(10) 0.0338(4) Uani 1 1 d . . . . .
H16 H -0.273223 0.560838 0.183851 0.041 Uiso 1 1 calc R . . . .
C6 C 0.1185(4) 0.0790(2) 0.17831(10) 0.0354(5) Uani 1 1 d . . . . .
H6A H -0.077134 0.080944 0.170290 0.043 Uiso 1 1 calc R . . . .
H6B H 0.167695 -0.021238 0.200854 0.043 Uiso 1 1 calc R . . . .
C5 C 0.2726(4) 0.1076(2) 0.11515(10) 0.0401(5) Uani 1 1 d . . . . .
H5A H 0.468303 0.103947 0.123135 0.048 Uiso 1 1 calc R . . . .
H5B H 0.225708 0.208480 0.092920 0.048 Uiso 1 1 calc R . . . .
C23 C 0.8042(4) 0.2319(2) 0.39463(10) 0.0342(4) Uani 1 1 d . . . . .
H23 H 0.941112 0.180956 0.420440 0.041 Uiso 1 1 calc R . . . .
C4 C 0.2099(5) -0.0056(3) 0.07243(11) 0.0448(5) Uani 1 1 d . . . . .
H4A H 0.011692 -0.011067 0.069829 0.054 Uiso 1 1 calc R . . . .
H4B H 0.281369 0.031109 0.028965 0.054 Uiso 1 1 calc R . . . .
C3 C 0.3223(5) -0.1608(3) 0.09349(11) 0.0479(6) Uani 1 1 d . . . . .
H3A H 0.257090 -0.197542 0.137491 0.057 Uiso 1 1 calc R . . . .
H3B H 0.521407 -0.157696 0.093816 0.057 Uiso 1 1 calc R . . . .
C2 C 0.2386(7) -0.2686(3) 0.04948(14) 0.0654(7) Uani 1 1 d . . . . .
H2A H 0.039399 -0.270139 0.048904 0.079 Uiso 1 1 calc R . . . .
H2B H 0.304454 -0.231271 0.005590 0.079 Uiso 1 1 calc R . . . .
C1 C 0.3436(8) -0.4235(3) 0.06876(16) 0.0817(10) Uani 1 1 d . . . . .
H1A H 0.272739 -0.487534 0.040584 0.122 Uiso 1 1 calc GR . . . .
H1B H 0.286083 -0.460005 0.112840 0.122 Uiso 1 1 calc GR . . . .
H1C H 0.540928 -0.424577 0.065539 0.122 Uiso 1 1 calc GR . . . .


_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
O14 C13 1.214(2) . ?
O15 C8 1.210(2) . ?
N7 C13 1.405(3) . ?
N7 C8 1.414(2) . ?
N7 C6 1.492(2) . ?
N29 C28 1.146(3) . ?
N25 C26 1.146(3) . ?
C10 C11 1.454(2) . ?
C10 C19 1.421(3) . ?
C10 C9 1.377(3) . ?
C20 C27 1.366(3) . ?
C20 C21 1.470(2) . ?
C20 C19 1.471(3) . ?
C27 C28 1.431(3) . ?
C27 C26 1.429(3) . ?
C11 C21 1.411(3) . ?
C11 C12 1.386(2) . ?
C21 C22 1.386(3) . ?
C19 C18 1.387(3) . ?
C9 C8 1.501(3) . ?
C9 C16 1.408(3) . ?
C18 C17 1.390(3) . ?
C12 C13 1.494(3) . ?
C12 C24 1.403(3) . ?
C22 C23 1.394(3) . ?
C24 C23 1.374(3) . ?
C17 C16 1.383(3) . ?
C6 C5 1.515(3) . ?
C5 C4 1.525(3) . ?
C4 C3 1.513(3) . ?
C3 C2 1.536(3) . ?
C2 C1 1.492(4) . ?

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
C13 N7 C8 134.39(16) . . ?
C13 N7 C6 112.79(15) . . ?
C8 N7 C6 112.70(15) . . ?
C19 C10 C11 108.47(16) . . ?
C9 C10 C11 130.34(17) . . ?
C9 C10 C19 121.18(16) . . ?
C27 C20 C21 126.37(17) . . ?
C27 C20 C19 127.04(16) . . ?
C21 C20 C19 106.59(15) . . ?
C20 C27 C28 123.31(16) . . ?
C20 C27 C26 123.33(17) . . ?
C26 C27 C28 113.35(16) . . ?
C21 C11 C10 108.73(15) . . ?
C12 C11 C10 130.28(17) . . ?
C12 C11 C21 120.98(17) . . ?
C11 C21 C20 108.27(15) . . ?
C22 C21 C20 130.78(17) . . ?
C22 C21 C11 120.94(16) . . ?
C10 C19 C20 107.95(15) . . ?
C18 C19 C10 120.19(18) . . ?
C18 C19 C20 131.87(17) . . ?
C10 C9 C8 127.13(17) . . ?
C10 C9 C16 117.69(17) . . ?
C16 C9 C8 115.17(17) . . ?
C19 C18 C17 118.54(17) . . ?
N29 C28 C27 177.6(2) . . ?
C11 C12 C13 127.27(17) . . ?
C11 C12 C24 116.98(17) . . ?
C24 C12 C13 115.73(16) . . ?
C21 C22 C23 117.97(18) . . ?
O14 C13 N7 117.77(17) . . ?
O14 C13 C12 117.26(17) . . ?
N7 C13 C12 124.96(16) . . ?
C23 C24 C12 122.24(17) . . ?
C16 C17 C18 121.11(17) . . ?
O15 C8 N7 117.66(17) . . ?
O15 C8 C9 117.17(17) . . ?
N7 C8 C9 125.17(17) . . ?
N25 C26 C27 177.7(2) . . ?
C17 C16 C9 121.27(19) . . ?
N7 C6 C5 112.11(16) . . ?
C6 C5 C4 112.07(17) . . ?
C24 C23 C22 120.87(17) . . ?
C3 C4 C5 115.54(19) . . ?
C4 C3 C2 111.9(2) . . ?
C1 C2 C3 113.8(3) . . ?


_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 1.424
_oxdiff_exptl_absorpt_empirical_full_min 0.764
