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

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

data_gyy-20191114
_database_code_depnum_ccdc_archive 'CCDC 2193171'
loop_
_audit_author_name
_audit_author_address
'Yuan-Yang Guo'
;Henan Normal University
China
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2023-10-11 downloaded from the CCDC.
;
_audit_creation_date             2022-07-28
_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         'C23 H22 N2 O6'
_chemical_formula_sum            'C23 H23 N2 O6'
_chemical_formula_weight         423.43
_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 0.0181 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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.6195(3)
_cell_length_b                   5.88080(10)
_cell_length_c                   22.1130(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.446(2)
_cell_angle_gamma                90
_cell_volume                     1948.09(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4669
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71
_cell_measurement_theta_min      4
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.873
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             892
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11201
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.601
_diffrn_reflns_theta_min         4.066
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3174
_reflns_number_total             3731
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3731
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.055
_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)+(0.0577P)²+0.8725P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1250
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), N7(H7), C9(H9), C11(H11), C13(H13), C16(H16), C18(H18),
 C19(H19), C22(H22)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O23(H23)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
N1 N 0.47937(10) 0.8062(3) 0.09795(7) 0.0333(3) Uani 1 1 d . . . . .
H1 H 0.475751 0.940295 0.081923 0.040 Uiso 1 1 calc R . . . .
O2 O 0.60036(11) 0.4426(2) 0.45018(6) 0.0407(3) Uani 1 1 d . . . . .
H2 H 0.592009 0.312958 0.460912 0.061 Uiso 1 1 calc GR . . . .
O3 O 0.30194(11) 0.1374(3) 0.03645(7) 0.0490(4) Uani 1 1 d . . . . .
O4 O 0.43026(10) 0.7705(3) -0.03599(6) 0.0454(4) Uani 1 1 d . . . . .
O5 O 0.40655(15) 0.9919(3) 0.51469(7) 0.0604(5) Uani 1 1 d . . . . .
C6 C 0.58322(12) 0.5585(3) 0.17298(8) 0.0290(4) Uani 1 1 d . . . . .
H6 H 0.571723 0.442377 0.143206 0.035 Uiso 1 1 calc R . . . .
N7 N 0.38533(11) 0.3927(3) 0.14454(7) 0.0360(4) Uani 1 1 d . . . . .
H7 H 0.386074 0.249102 0.152090 0.043 Uiso 1 1 calc R . . . .
C8 C 0.64196(13) 0.4344(3) 0.40452(8) 0.0331(4) Uani 1 1 d . . . . .
C9 C 0.64239(12) 0.5221(3) 0.23238(8) 0.0296(4) Uani 1 1 d . . . . .
H9 H 0.669881 0.381119 0.241976 0.035 Uiso 1 1 calc R . . . .
C10 C 0.38418(13) 0.8330(4) 0.29524(8) 0.0361(4) Uani 1 1 d . . . . .
C11 C 0.33965(13) 0.8920(3) 0.23319(9) 0.0360(4) Uani 1 1 d . . . . .
H11 H 0.309078 1.029471 0.225199 0.043 Uiso 1 1 calc R . . . .
C12 C 0.38397(12) 0.5428(3) 0.19452(8) 0.0309(4) Uani 1 1 d . . . . .
C13 C 0.56097(13) 0.9399(3) 0.20247(8) 0.0336(4) Uani 1 1 d . . . . .
H13 H 0.534294 1.081742 0.192644 0.040 Uiso 1 1 calc R . . . .
C14 C 0.66092(11) 0.6926(3) 0.27738(7) 0.0295(4) Uani 1 1 d . . . . .
O15 O 0.64440(15) 0.2623(3) 0.37621(8) 0.0620(5) Uani 1 1 d . . . . .
C16 C 0.61993(13) 0.9020(3) 0.26121(8) 0.0351(4) Uani 1 1 d . . . . .
H16 H 0.632433 1.019491 0.290566 0.042 Uiso 1 1 calc R . . . .
C17 C 0.38554(12) 0.4589(3) 0.08524(8) 0.0300(4) Uani 1 1 d . . . . .
C18 C 0.42574(14) 0.6213(4) 0.30536(8) 0.0392(4) Uani 1 1 d . . . . .
H18 H 0.454057 0.575531 0.346415 0.047 Uiso 1 1 calc R . . . .
C19 C 0.34001(13) 0.7499(3) 0.18309(8) 0.0352(4) Uani 1 1 d . . . . .
H19 H 0.310828 0.793575 0.142001 0.042 Uiso 1 1 calc R . . . .
C20 C 0.54151(11) 0.7667(3) 0.15814(7) 0.0272(4) Uani 1 1 d . . . . .
C21 C 0.40419(12) 0.6315(3) -0.00432(8) 0.0328(4) Uani 1 1 d . . . . .
C22 C 0.42603(14) 0.4774(3) 0.25606(8) 0.0361(4) Uani 1 1 d . . . . .
H22 H 0.454374 0.337014 0.264096 0.043 Uiso 1 1 calc R . . . .
O23 O 0.36947(16) 1.2708(3) 0.44563(7) 0.0655(6) Uani 1 1 d . . . . .
H23 H 0.375440 1.346320 0.477736 0.098 Uiso 1 1 calc GR . . . .
C24 C 0.42556(11) 0.6392(3) 0.06495(8) 0.0299(4) Uani 1 1 d . . . . .
C25 C 0.39182(17) 1.0006(4) 0.34863(9) 0.0452(5) Uani 1 1 d . . . . .
H25A H 0.451701 1.063349 0.360910 0.054 Uiso 1 1 calc R . . . .
H25B H 0.350546 1.124980 0.333440 0.054 Uiso 1 1 calc R . . . .
C26 C 0.34062(12) 0.3132(3) 0.03171(8) 0.0331(4) Uani 1 1 d . . . . .
C27 C 0.35063(14) 0.4198(4) -0.02775(8) 0.0374(4) Uani 1 1 d . . . . .
C28 C 0.72647(13) 0.6558(4) 0.34189(8) 0.0387(5) Uani 1 1 d . . . . .
H28A H 0.771040 0.775343 0.349452 0.046 Uiso 1 1 calc R . . . .
H28B H 0.756956 0.512305 0.341572 0.046 Uiso 1 1 calc R . . . .
C29 C 0.68432(14) 0.6533(4) 0.39646(8) 0.0365(4) Uani 1 1 d . . . . .
H29A H 0.730101 0.688280 0.435213 0.044 Uiso 1 1 calc R . . . .
H29B H 0.639654 0.772457 0.389596 0.044 Uiso 1 1 calc R . . . .
C30 C 0.37277(19) 0.8985(4) 0.40550(11) 0.0532(6) Uani 1 1 d . . . . .
H30A H 0.411424 0.767823 0.418758 0.064 Uiso 1 1 calc R . . . .
H30B H 0.311667 0.843945 0.393494 0.064 Uiso 1 1 calc R . . . .
C31 C 0.38514(16) 1.0558(4) 0.46076(9) 0.0438(5) Uani 1 1 d . . . . .
H27A H 0.3833(16) 0.317(4) -0.0452(10) 0.042(6) Uiso 1 1 d . . . . .
H27B H 0.2952(19) 0.448(4) -0.0568(12) 0.056(7) Uiso 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
N1 C20 1.427(2) . ?
N1 C24 1.362(2) . ?
O2 C8 1.347(2) . ?
O3 C26 1.217(3) . ?
O4 C21 1.219(2) . ?
O5 C31 1.204(3) . ?
C6 C9 1.392(2) . ?
C6 C20 1.382(2) . ?
N7 C12 1.419(2) . ?
N7 C17 1.369(2) . ?
C8 O15 1.196(2) . ?
C8 C29 1.481(3) . ?
C9 C14 1.384(3) . ?
C10 C11 1.395(3) . ?
C10 C18 1.393(3) . ?
C10 C25 1.516(3) . ?
C11 C19 1.389(3) . ?
C12 C19 1.386(3) . ?
C12 C22 1.387(3) . ?
C13 C16 1.381(3) . ?
C13 C20 1.387(2) . ?
C14 C16 1.388(3) . ?
C14 C28 1.518(2) . ?
C17 C24 1.369(3) . ?
C17 C26 1.469(2) . ?
C18 C22 1.381(3) . ?
C21 C24 1.473(2) . ?
C21 C27 1.507(3) . ?
O23 C31 1.313(3) . ?
C25 C30 1.498(3) . ?
C26 C27 1.504(3) . ?
C28 C29 1.530(2) . ?
C30 C31 1.501(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
C24 N1 C20 122.41(15) . . ?
C20 C6 C9 120.17(15) . . ?
C17 N7 C12 125.01(16) . . ?
O2 C8 C29 112.67(16) . . ?
O15 C8 O2 121.07(19) . . ?
O15 C8 C29 126.23(18) . . ?
C14 C9 C6 120.98(17) . . ?
C11 C10 C25 120.77(19) . . ?
C18 C10 C11 117.39(17) . . ?
C18 C10 C25 121.71(17) . . ?
C19 C11 C10 121.42(18) . . ?
C19 C12 N7 121.37(16) . . ?
C19 C12 C22 119.66(17) . . ?
C22 C12 N7 118.96(17) . . ?
C16 C13 C20 120.04(17) . . ?
C9 C14 C16 118.07(16) . . ?
C9 C14 C28 121.37(18) . . ?
C16 C14 C28 120.53(17) . . ?
C13 C16 C14 121.45(16) . . ?
N7 C17 C24 131.25(16) . . ?
N7 C17 C26 118.43(17) . . ?
C24 C17 C26 110.23(16) . . ?
C22 C18 C10 121.77(17) . . ?
C12 C19 C11 119.81(17) . . ?
C6 C20 N1 121.07(15) . . ?
C6 C20 C13 119.27(15) . . ?
C13 C20 N1 119.66(16) . . ?
O4 C21 C24 124.23(18) . . ?
O4 C21 C27 126.83(16) . . ?
C24 C21 C27 108.86(16) . . ?
C18 C22 C12 119.88(18) . . ?
N1 C24 C17 130.71(16) . . ?
N1 C24 C21 120.20(17) . . ?
C17 C24 C21 109.07(16) . . ?
C30 C25 C10 113.75(19) . . ?
O3 C26 C17 124.17(18) . . ?
O3 C26 C27 127.32(17) . . ?
C17 C26 C27 108.51(17) . . ?
C26 C27 C21 103.21(15) . . ?
C14 C28 C29 114.61(16) . . ?
C8 C29 C28 114.20(17) . . ?
C25 C30 C31 115.23(19) . . ?
O5 C31 O23 122.18(19) . . ?
O5 C31 C30 123.3(2) . . ?
O23 C31 C30 114.48(19) . . ?

_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_gyy-20191220
_database_code_depnum_ccdc_archive 'CCDC 2209966'
loop_
_audit_author_name
_audit_author_address
'Yuan-Yang Guo'
;School of chemistry and chemical engineering, Henan Normal University
China
;
_audit_update_record             
;
2022-09-28 deposited with the CCDC.	2023-10-11 downloaded from the CCDC.
;
_audit_creation_date             2022-09-28
_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         'C17 H14 N2 O2'
_chemical_formula_sum            'C17 H11 N2 O2'
_chemical_formula_weight         278.28
_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 0.0181 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      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                   13.9490(3)
_cell_length_b                   7.20400(10)
_cell_length_c                   13.9933(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.396(2)
_cell_angle_gamma                90
_cell_volume                     1403.70(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4214
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.4810
_cell_measurement_theta_min      6.3090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80376
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             572
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7841
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.579
_diffrn_reflns_theta_min         6.337
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00  28.00   1.00    1.35    --  -35.62  92.00  63.00   99
  2  ω     -7.00  71.00   1.00    1.35    --   35.62 -92.00 -49.00   78
  3  ω    100.00 176.00   1.00    5.42    --  107.12  92.00  63.00   76
  4  ω     38.00 109.00   1.00    5.42    --  107.12 -92.00 -49.00   71
  5  ω   -105.00 -17.00   1.00    1.35    --  -35.62 -38.00  90.00   88
  6  ω     57.00 108.00   1.00    1.35    --   35.62 178.00 120.00   51
  7  ω     57.00 108.00   1.00    1.35    --   35.62 178.00 -60.00   51
  8  ω      1.00  75.00   1.00    1.35    --   35.62 -99.00 120.00   74
  9  ω     57.00 108.00   1.00    1.35    --   35.62 178.00-150.00   51
 10  ω     55.00 108.00   1.00    1.35    --   35.62-178.00 -30.00   53
 11  ω     40.00 125.00   1.00    5.42    --  107.12 -61.00 -30.00   85
 12  ω     38.00 110.00   1.00    5.42    --  107.12 -95.00 -30.00   72
 13  ω     90.00 176.00   1.00    5.42    --  107.12  45.00  90.00   86
 14  ω     38.00 110.00   1.00    5.42    --  107.12 -95.00 120.00   72
 15  ω     37.00 129.00   1.00    5.42    --  107.12 -30.00  60.00   92
 16  ω     38.00 110.00   1.00    5.42    --  107.12 -95.00-120.00   72
 17  ω     69.00 178.00   1.00    5.42    --  107.12  15.00  30.00  109
 18  ω   -103.00 -21.00   1.00    1.35    --  -35.62 -57.00   0.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2289
_reflns_number_total             2688
_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         0.373
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2688
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0716
_refine_ls_restrained_S_all      1.097
_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)+(0.1408P)²+0.5328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2156
_refine_ls_wR_factor_ref         0.2230
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 0.56624(14) 0.2075(3) 0.51357(14) 0.0455(5) Uani 1 1 d . . . . .
O2 O 0.44280(14) 0.0562(3) 0.20295(12) 0.0440(5) Uani 1 1 d . . . . .
N3 N 0.29310(14) 0.2468(3) 0.28979(14) 0.0304(5) Uani 1 1 d . . . . .
H3 H 0.284(3) 0.193(5) 0.234(3) 0.056(10) Uiso 1 1 d . . . . .
N6 N 0.37371(15) 0.3289(3) 0.50291(14) 0.0323(5) Uani 1 1 d . . . . .
H6 H 0.413(2) 0.368(5) 0.555(2) 0.049(9) Uiso 1 1 d . . . . .
C4 C 0.38073(15) 0.2103(3) 0.33592(14) 0.0238(5) Uani 1 1 d . . . . .
C5 C 0.51621(16) 0.1887(3) 0.44033(16) 0.0289(5) Uani 1 1 d . . . . .
C7 C 0.24441(16) 0.4182(3) 0.29437(14) 0.0267(5) Uani 1 1 d . . . . .
C8 C 0.27441(17) 0.3220(4) 0.51792(15) 0.0325(5) Uani 1 1 d . . . . .
C9 C 0.45421(17) 0.1125(3) 0.28516(15) 0.0279(5) Uani 1 1 d . . . . .
C10 C 0.41517(16) 0.2483(3) 0.42752(15) 0.0250(5) Uani 1 1 d . . . . .
C11 C 0.2304(2) 0.4726(4) 0.55929(18) 0.0446(7) Uani 1 1 d . . . . .
H11 H 0.271(3) 0.586(5) 0.579(3) 0.060(10) Uiso 1 1 d . . . . .
C12 C 0.29065(18) 0.5767(3) 0.32957(16) 0.0318(5) Uani 1 1 d . . . . .
H12 H 0.364(3) 0.571(5) 0.359(2) 0.055(9) Uiso 1 1 d . . . . .
C13 C 0.1490(2) 0.4273(4) 0.2610(2) 0.0486(7) Uani 1 1 d . . . . .
H13 H 0.115(3) 0.311(6) 0.238(3) 0.074(12) Uiso 1 1 d . . . . .
C14 C 0.54439(18) 0.0975(4) 0.34916(17) 0.0347(6) Uani 1 1 d . . . . .
H14A H 0.600(3) 0.162(5) 0.323(3) 0.064(10) Uiso 1 1 d . . . . .
H14B H 0.562(3) -0.034(5) 0.361(2) 0.057(9) Uiso 1 1 d . . . . .
C15 C 0.2410(2) 0.7427(4) 0.3306(2) 0.0459(7) Uani 1 1 d . . . . .
H15 H 0.278(3) 0.857(5) 0.357(3) 0.064(10) Uiso 1 1 d . . . . .
C16 C 0.1324(3) 0.4645(6) 0.5716(2) 0.0650(10) Uani 1 1 d . . . . .
H16 H 0.103(4) 0.568(7) 0.603(4) 0.095(15) Uiso 1 1 d . . . . .
C17 C 0.1005(3) 0.5953(6) 0.2625(3) 0.0687(10) Uani 1 1 d . . . . .
H17 H 0.035(4) 0.603(7) 0.234(4) 0.104(16) Uiso 1 1 d . . . . .
C18 C 0.1237(3) 0.1612(7) 0.5041(3) 0.0729(12) Uani 1 1 d . . . . .
H18 H 0.082(4) 0.039(8) 0.488(4) 0.123(19) Uiso 1 1 d . . . . .
C19 C 0.2216(2) 0.1654(5) 0.4925(2) 0.0512(8) Uani 1 1 d . . . . .
H19 H 0.252(3) 0.055(6) 0.465(3) 0.073(12) Uiso 1 1 d . . . . .
C20 C 0.0794(3) 0.3114(8) 0.5435(3) 0.0757(13) Uani 1 1 d . . . . .
H20 H 0.009(4) 0.299(7) 0.548(4) 0.100(15) Uiso 1 1 d . . . . .
C21 C 0.1465(3) 0.7532(5) 0.2974(3) 0.0606(9) Uani 1 1 d . . . . .
H21 H 0.107(3) 0.876(6) 0.296(3) 0.082(12) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.213(3) . ?
O2 C9 1.221(3) . ?
N3 C4 1.374(3) . ?
N3 C7 1.413(3) . ?
N6 C8 1.414(3) . ?
N6 C10 1.363(3) . ?
C4 C9 1.462(3) . ?
C4 C10 1.370(3) . ?
C5 C10 1.474(3) . ?
C5 C14 1.508(3) . ?
C7 C12 1.387(3) . ?
C7 C13 1.386(3) . ?
C8 C11 1.390(4) . ?
C8 C19 1.383(4) . ?
C9 C14 1.504(3) . ?
C11 C16 1.388(5) . ?
C12 C15 1.382(3) . ?
C13 C17 1.387(4) . ?
C15 C21 1.373(5) . ?
C16 C20 1.372(7) . ?
C17 C21 1.381(6) . ?
C18 C19 1.385(5) . ?
C18 C20 1.377(7) . ?

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
C4 N3 C7 124.26(18) . . ?
C10 N6 C8 124.37(19) . . ?
N3 C4 C9 119.61(18) . . ?
C10 C4 N3 130.9(2) . . ?
C10 C4 C9 109.51(18) . . ?
O1 C5 C10 124.6(2) . . ?
O1 C5 C14 126.7(2) . . ?
C10 C5 C14 108.63(18) . . ?
C12 C7 N3 121.4(2) . . ?
C13 C7 N3 118.7(2) . . ?
C13 C7 C12 119.9(2) . . ?
C11 C8 N6 119.7(2) . . ?
C19 C8 N6 120.1(2) . . ?
C19 C8 C11 120.1(3) . . ?
O2 C9 C4 124.2(2) . . ?
O2 C9 C14 126.5(2) . . ?
C4 C9 C14 109.35(18) . . ?
N6 C10 C4 131.9(2) . . ?
N6 C10 C5 118.46(19) . . ?
C4 C10 C5 109.59(19) . . ?
C16 C11 C8 118.8(3) . . ?
C15 C12 C7 119.5(2) . . ?
C7 C13 C17 119.7(3) . . ?
C9 C14 C5 102.79(18) . . ?
C21 C15 C12 121.1(3) . . ?
C20 C16 C11 121.1(3) . . ?
C21 C17 C13 120.5(3) . . ?
C20 C18 C19 119.9(4) . . ?
C8 C19 C18 120.1(3) . . ?
C16 C20 C18 120.0(3) . . ?
C15 C21 C17 119.4(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
;
