# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_20191130-1
_database_code_depnum_ccdc_archive 'CCDC 2055637'
loop_
_audit_author_name
_audit_author_address
'Yu-Bo Fang'
;School of Chemistry and Chemical Engineering, Guangzhou University
China
;
_audit_update_record             
;
2021-01-13 deposited with the CCDC.	2021-05-14 downloaded from the CCDC.
;
_audit_creation_date             2020-01-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C H2 Cl2, C21 H14 N2 O3'
_chemical_formula_sum            'C22 H16 Cl2 N2 O3'
_chemical_formula_weight         427.29
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           ' P 61'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x-y,x,z+1/6
3 y,-x+y,z+5/6
4 -y,x-y,z+1/3
5 -x+y,-x,z+2/3
6 -x,-y,z+1/2

_symmetry_Int_Tables_number      169
_cell_length_a                   19.9112(5)
_cell_length_b                   19.9112(5)
_cell_length_c                   9.2146(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3163.73(15)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    2722
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.3810
_cell_measurement_theta_min      2.5260
_exptl_absorpt_coefficient_mu    2.983
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3455
_exptl_crystal_description       block
_exptl_crystal_F_000             1328.1516
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8009
_diffrn_reflns_theta_full        73.6262
_diffrn_reflns_theta_max         73.63
_diffrn_reflns_theta_min         2.56
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.8959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00   1.00   1.00    1.00    --  -40.98  57.00 120.00   67
  2  ω     35.00  96.00   1.00    1.00    --   40.98-125.00 -90.00   61
  3  ω     26.00 105.00   1.00    2.00    --  106.95 -95.00-120.00   79
  4  ω     84.00 177.00   1.00    2.00    --  106.95  30.00   0.00   93
  5  ω    148.00 173.00   1.00    2.00    --  106.95 111.00  74.00   25
  6  ω     83.00 172.00   1.00    2.00    --  106.95  62.00  37.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0552738000
_diffrn_orient_matrix_UB_12      -0.0222264000
_diffrn_orient_matrix_UB_13      -0.0752404000
_diffrn_orient_matrix_UB_21      -0.0339472000
_diffrn_orient_matrix_UB_22      -0.0747410000
_diffrn_orient_matrix_UB_23      0.0914204000
_diffrn_orient_matrix_UB_31      -0.0613085000
_diffrn_orient_matrix_UB_32      -0.0436094000
_diffrn_orient_matrix_UB_33      -0.1181728000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.805
_reflns_limit_h_max              20
_reflns_limit_h_min              -20
_reflns_limit_k_max              21
_reflns_limit_k_min              -21
_reflns_limit_l_max              11
_reflns_limit_l_min              -11
_reflns_number_gt                3412
_reflns_number_total             3821
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.2184
_refine_diff_density_min         -0.2991
_refine_diff_density_rms         0.0449
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_d_res_high            0.8035
_refine_ls_d_res_low             17.2436
_refine_ls_goodness_of_fit_ref   1.0334
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    29
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3821
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.0334
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0451P)²+0.2345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1027
_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 Ternary CH refined with riding coordinates:
 C10(H10), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C4ca(H4ca,H4cb)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C16(H16), C15(H15), C7(H7), C11(H11), C18(H18), C4(H4),
 C17(H17)
2.d Idealised Me refined as rotating group:
 C20(H20a,H20b,H20c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Cl Cl 0.29189(5) 0.23577(6) 0.99458(8) 0.0513(2) Uani 1.000000 .
Cl1 Cl 0.20352(7) 0.12214(6) 0.77062(12) 0.0760(4) Uani 1.000000 .
O3 O 0.34777(10) 0.30595(10) 0.3228(2) 0.0250(4) Uani 1.000000 .
O1 O 0.42282(10) 0.29596(10) 0.6310(2) 0.0258(4) Uani 1.000000 .
N1 N 0.54182(12) 0.38359(12) 0.7269(2) 0.0214(4) Uani 1.000000 .
O2 O 0.43418(12) 0.48018(12) 0.6267(2) 0.0323(4) Uani 1.000000 .
C5 C 0.71873(15) 0.58773(15) 0.5526(3) 0.0265(5) Uani 1.000000 .
H5 H 0.75676(15) 0.63346(15) 0.5103(3) 0.0319(7) Uiso 1.000000 R
C2 C 0.51922(14) 0.40619(13) 0.4859(3) 0.0203(5) Uani 1.000000 .
C1 C 0.48710(14) 0.35402(14) 0.6220(3) 0.0203(5) Uani 1.000000 .
C12 C 0.52717(15) 0.35956(14) 0.3642(3) 0.0232(5) Uani 1.000000 .
C8 C 0.60685(14) 0.45325(13) 0.6821(3) 0.0194(5) Uani 1.000000 .
C10 C 0.42207(15) 0.37289(14) 0.2894(3) 0.0235(5) Uani 1.000000 .
H10 H 0.41803(15) 0.40078(14) 0.2053(3) 0.0282(6) Uiso 1.000000 R
C3 C 0.59554(14) 0.47117(13) 0.5413(3) 0.0196(5) Uani 1.000000 .
N3 N 0.62712(17) 0.31371(18) 0.3943(3) 0.0436(7) Uani 1.000000 .
C6 C 0.72930(15) 0.56884(15) 0.6914(3) 0.0252(5) Uani 1.000000 .
H6 H 0.77467(15) 0.60220(15) 0.7409(3) 0.0302(6) Uiso 1.000000 R
C19 C 0.29890(16) 0.31707(16) 0.4101(3) 0.0268(5) Uani 1.000000 .
C16 C 0.19158(17) 0.33172(19) 0.5825(3) 0.0361(7) Uani 1.000000 .
H16 H 0.15541(17) 0.33697(19) 0.6378(3) 0.0433(8) Uiso 1.000000 R
C15 C 0.26940(16) 0.38513(17) 0.5933(3) 0.0305(6) Uani 1.000000 .
H15 H 0.28579(16) 0.42656(17) 0.6573(3) 0.0366(7) Uiso 1.000000 R
C7 C 0.67363(14) 0.50080(14) 0.7601(3) 0.0239(5) Uani 1.000000 .
H7 H 0.68111(14) 0.48813(14) 0.8536(3) 0.0287(6) Uiso 1.000000 R
C11 C 0.47555(15) 0.34203(14) 0.2579(3) 0.0237(5) Uani 1.000000 .
H11 H 0.47303(15) 0.31426(14) 0.1749(3) 0.0285(6) Uiso 1.000000 R
C18 C 0.22069(16) 0.26255(17) 0.3997(3) 0.0321(6) Uani 1.000000 .
H18 H 0.20375(16) 0.22154(17) 0.3346(3) 0.0386(7) Uiso 1.000000 R
C9 C 0.46158(15) 0.42862(14) 0.4175(3) 0.0218(5) Uani 1.000000 .
H9 H 0.49281(15) 0.48068(14) 0.3763(3) 0.0261(6) Uiso 1.000000 R
C20 C 0.53241(16) 0.34992(15) 0.8700(3) 0.0281(6) Uani 1.000000 .
H20a H 0.5405(12) 0.3880(4) 0.9422(3) 0.0421(8) Uiso 1.000000 GR
H20b H 0.4810(4) 0.3063(8) 0.8794(9) 0.0421(8) Uiso 1.000000 GR
H20c H 0.5696(8) 0.3331(11) 0.8833(9) 0.0421(8) Uiso 1.000000 GR
C14 C 0.32442(15) 0.37809(15) 0.5095(3) 0.0238(5) Uani 1.000000 .
C4 C 0.65110(15) 0.53860(14) 0.4746(3) 0.0254(5) Uani 1.000000 .
H4 H 0.64380(15) 0.55095(14) 0.3808(3) 0.0304(6) Uiso 1.000000 R
C17 C 0.16799(18) 0.26965(19) 0.4871(4) 0.0412(7) Uani 1.000000 .
H17 H 0.11574(18) 0.23218(19) 0.4820(4) 0.0495(9) Uiso 1.000000 R
C13 C 0.40760(15) 0.43304(15) 0.5270(3) 0.0246(5) Uani 1.000000 .
C21 C 0.58278(17) 0.33392(16) 0.3762(3) 0.0300(6) Uani 1.000000 .
C4ca C 0.2626(2) 0.2201(2) 0.8101(4) 0.0439(8) Uani 1.000000 .
H4ca H 0.2348(2) 0.2473(2) 0.7884(4) 0.0527(9) Uiso 1.000000 R
H4cb H 0.3082(2) 0.2414(2) 0.7486(4) 0.0527(9) Uiso 1.000000 R


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
Cl C4ca 1.774(4) . ?
Cl1 C4ca 1.740(4) . ?
O3 C10 1.445(3) . ?
O3 C19 1.363(3) . ?
O1 C1 1.225(3) . ?
N1 C1 1.351(3) . ?
N1 C8 1.405(3) . ?
N1 C20 1.449(3) . ?
O2 C13 1.228(3) . ?
C5 C6 1.379(4) . ?
C5 C4 1.404(4) . ?
C2 C1 1.549(3) . ?
C2 C12 1.514(3) . ?
C2 C3 1.509(3) . ?
C2 C9 1.558(3) . ?
C12 C11 1.334(4) . ?
C12 C21 1.437(4) . ?
C8 C3 1.393(3) . ?
C8 C7 1.386(3) . ?
C10 C11 1.500(3) . ?
C10 C9 1.539(3) . ?
C3 C4 1.385(3) . ?
N3 C21 1.151(4) . ?
C6 C7 1.401(4) . ?
C19 C18 1.386(4) . ?
C19 C14 1.399(4) . ?
C16 C15 1.376(4) . ?
C16 C17 1.393(5) . ?
C15 C14 1.404(4) . ?
C18 C17 1.385(4) . ?
C9 C13 1.508(4) . ?
C14 C13 1.468(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
C19 O3 C10 117.4(2) . . ?
C8 N1 C1 111.4(2) . . ?
C20 N1 C1 124.0(2) . . ?
C20 N1 C8 124.5(2) . . ?
C4 C5 C6 120.6(2) . . ?
C12 C2 C1 108.88(18) . . ?
C3 C2 C1 101.65(19) . . ?
C3 C2 C12 114.0(2) . . ?
C9 C2 C1 113.81(19) . . ?
C9 C2 C12 101.19(19) . . ?
C9 C2 C3 117.49(19) . . ?
N1 C1 O1 126.7(2) . . ?
C2 C1 O1 125.0(2) . . ?
C2 C1 N1 108.32(19) . . ?
C11 C12 C2 113.7(2) . . ?
C21 C12 C2 119.8(2) . . ?
C21 C12 C11 126.4(2) . . ?
C3 C8 N1 109.8(2) . . ?
C7 C8 N1 128.1(2) . . ?
C7 C8 C3 122.0(2) . . ?
C11 C10 O3 105.81(19) . . ?
C9 C10 O3 114.8(2) . . ?
C9 C10 C11 103.4(2) . . ?
C8 C3 C2 108.5(2) . . ?
C4 C3 C2 130.9(2) . . ?
C4 C3 C8 120.6(2) . . ?
C7 C6 C5 121.9(2) . . ?
C18 C19 O3 116.5(2) . . ?
C14 C19 O3 123.3(2) . . ?
C14 C19 C18 120.2(3) . . ?
C17 C16 C15 118.8(3) . . ?
C14 C15 C16 121.1(3) . . ?
C6 C7 C8 116.8(2) . . ?
C10 C11 C12 111.3(2) . . ?
C17 C18 C19 119.5(3) . . ?
C10 C9 C2 106.73(19) . . ?
C13 C9 C2 113.25(19) . . ?
C13 C9 C10 115.6(2) . . ?
C15 C14 C19 119.0(2) . . ?
C13 C14 C19 120.2(2) . . ?
C13 C14 C15 120.8(2) . . ?
C3 C4 C5 118.1(2) . . ?
C18 C17 C16 121.4(3) . . ?
C9 C13 O2 119.8(2) . . ?
C14 C13 O2 123.1(2) . . ?
C14 C13 C9 117.0(2) . . ?
N3 C21 C12 176.1(3) . . ?
Cl1 C4ca Cl 112.1(2) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.585 258.3 66.3 ?


_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 1.392
_oxdiff_exptl_absorpt_empirical_full_min 0.757
####################################################################### 
# 
# 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_20191113
_database_code_depnum_ccdc_archive 'CCDC 2055644'
loop_
_audit_author_name
_audit_author_address
'Yu-Bo Fang'
;School of Chemistry and Chemical Engineering, Guangzhou University
China
;
_audit_update_record             
;
2021-01-13 deposited with the CCDC.	2021-05-14 downloaded from the CCDC.
;
_audit_creation_date             2021-01-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H26 N4 O5'
_chemical_formula_sum            'C29 H26 N4 O5'
_chemical_formula_weight         510.54
_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      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                   11.538(3)
_cell_length_b                   12.0654(11)
_cell_length_c                   12.568(2)
_cell_angle_alpha                94.880(10)
_cell_angle_beta                 104.196(17)
_cell_angle_gamma                91.692(12)
_cell_volume                     1687.7(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1532
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.4930
_cell_measurement_theta_min      3.5800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.005
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_av_unetI/netI     0.1102
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11284
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.869
_diffrn_reflns_theta_min         3.644
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  33.00   1.00    2.00    --  -40.48  57.00-120.00   92
  2  ω    -92.00 -19.00   1.00    2.00    --  -40.48 125.00 -90.00   73
  3  ω   -112.00 -16.00   1.00    2.00    --  -40.48 -38.00 -30.00   96
  4  ω    -65.00 -38.00   1.00    2.00    --  -40.48  38.00 150.00   27
  5  ω   -114.00 -10.00   1.00    2.00    --  -40.48 -77.00 120.00  104
  6  ω     37.00 117.00   1.00    3.00    --  106.95 -61.00 -30.00   80
  7  ω     76.00 109.00   1.00    3.00    --  106.95 -94.00 -60.00   33
  8  ω     56.00 120.00   1.00    3.00    --  106.95-125.00 -90.00   64
  9  ω     38.00 133.00   1.00    3.00    --  106.95 -30.00  60.00   95
 10  ω     83.00 147.00   1.00    3.00    --  106.95  30.00 -60.00   64
 11  ω    150.00 177.00   1.00    3.00    --  106.95  45.00-120.00   27
 12  ω     82.00 132.00   1.00    3.00    --  106.95  45.00-120.00   50
 13  ω     40.00 130.00   1.00    3.00    --  106.95 -61.00-150.00   90
 14  ω     25.00 159.00   1.00    3.00    --  106.95 -15.00 -90.00  134
 15  ω     79.00 120.00   1.00    3.00    --  106.95-125.00 120.00   41
 16  ω     48.00  75.00   1.00    3.00    --  106.95-125.00 120.00   27
 17  ω     42.00 140.00   1.00    3.00    --  106.95 -77.00  90.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1338832000
_diffrn_orient_matrix_UB_12      -0.0303003000
_diffrn_orient_matrix_UB_13      -0.0512321000
_diffrn_orient_matrix_UB_21      0.0323560000
_diffrn_orient_matrix_UB_22      -0.0756912000
_diffrn_orient_matrix_UB_23      -0.0923696000
_diffrn_orient_matrix_UB_31      0.0069062000
_diffrn_orient_matrix_UB_32      -0.0990944000
_diffrn_orient_matrix_UB_33      0.0705502000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3721
_reflns_number_total             6558
_reflns_odcompleteness_completeness 99.40
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         6558
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1456
_refine_ls_R_factor_gt           0.1012
_refine_ls_restrained_S_all      1.039
_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)+(0.1786P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2791
_refine_ls_wR_factor_ref         0.3345
_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:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C24(H24), C4(H4), C15(H15), C6(H6), C7(H7), C18(H18), C16(H16),
 C17(H17)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C1(H1A,H1B,H1C), C27(H27A,H27B,H27C), C29(H29A,H29B,
 H29C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O2 O 0.6281(3) 0.5120(2) 0.4310(2) 0.0462(7) Uani 1 1 d . . . . .
O3 O 0.6445(3) 0.6371(2) 0.8000(2) 0.0442(7) Uani 1 1 d . . . . .
O4 O 0.4811(3) 0.5791(2) 0.8550(2) 0.0493(8) Uani 1 1 d . . . . .
O5 O 0.5937(3) 0.7369(2) 0.9295(2) 0.0510(8) Uani 1 1 d . . . . .
O1 O 0.6650(3) 0.1802(2) 0.7694(2) 0.0511(8) Uani 1 1 d . . . . .
N3 N 0.8052(3) 0.4232(3) 0.4455(3) 0.0448(9) Uani 1 1 d . . . . .
N1 N 0.6774(4) -0.0010(3) 0.7011(3) 0.0460(9) Uani 1 1 d . . . . .
N2 N 0.5792(4) 0.2315(3) 0.3171(3) 0.0502(10) Uani 1 1 d . . . . .
N4 N 0.9072(4) 0.6539(3) 0.7183(4) 0.0609(11) Uani 1 1 d . . . . .
C9 C 0.6486(4) 0.0149(3) 0.5162(3) 0.0376(9) Uani 1 1 d . . . . .
C14 C 0.8380(4) 0.3660(3) 0.6182(4) 0.0410(10) Uani 1 1 d . . . . .
C11 C 0.5985(4) 0.2274(3) 0.4103(4) 0.0411(10) Uani 1 1 d . . . . .
C21 C 0.7084(4) 0.4587(3) 0.4817(4) 0.0417(10) Uani 1 1 d . . . . .
C10 C 0.6211(4) 0.2250(3) 0.5280(3) 0.0373(9) Uani 1 1 d . . . . .
C13 C 0.7181(4) 0.4199(3) 0.5963(3) 0.0388(9) Uani 1 1 d . . . . .
C23 C 0.8245(4) 0.5949(3) 0.7040(4) 0.0450(10) Uani 1 1 d . . . . .
C22 C 0.7198(4) 0.5201(3) 0.6793(3) 0.0392(9) Uani 1 1 d . . . . .
C12 C 0.6130(4) 0.3361(3) 0.5924(3) 0.0400(9) Uani 1 1 d . . . . .
H12A H 0.611588 0.322993 0.667188 0.048 Uiso 1 1 calc R U . . .
H12B H 0.538415 0.368431 0.558902 0.048 Uiso 1 1 calc R U . . .
C19 C 0.8819(4) 0.3685(3) 0.5247(4) 0.0453(10) Uani 1 1 d . . . . .
C5 C 0.6484(4) -0.1390(3) 0.3840(4) 0.0470(11) Uani 1 1 d . . . . .
H5 H 0.640578 -0.167718 0.311378 0.056 Uiso 1 1 calc R U . . .
C3 C 0.6429(4) 0.1266(3) 0.5719(4) 0.0397(9) Uani 1 1 d . . . . .
C8 C 0.6698(4) -0.0566(3) 0.5978(4) 0.0420(10) Uani 1 1 d . . . . .
C24 C 0.6311(4) 0.5435(3) 0.7285(4) 0.0431(10) Uani 1 1 d . . . . .
H24 H 0.562230 0.496959 0.714103 0.052 Uiso 1 1 calc R U . . .
C4 C 0.6386(4) -0.0248(3) 0.4069(4) 0.0439(10) Uani 1 1 d . . . . .
H4 H 0.625781 0.022849 0.351164 0.053 Uiso 1 1 calc R U . . .
C15 C 0.8998(4) 0.3176(3) 0.7079(4) 0.0494(11) Uani 1 1 d . . . . .
H15 H 0.869671 0.314766 0.769864 0.059 Uiso 1 1 calc R U . . .
C25 C 0.5620(4) 0.6456(3) 0.8636(4) 0.0444(11) Uani 1 1 d . . . . .
C6 C 0.6695(4) -0.2104(3) 0.4658(4) 0.0507(12) Uani 1 1 d . . . . .
H6 H 0.676213 -0.285852 0.447517 0.061 Uiso 1 1 calc R U . . .
C7 C 0.6808(4) -0.1711(3) 0.5757(4) 0.0497(11) Uani 1 1 d . . . . .
H7 H 0.694951 -0.218598 0.631528 0.060 Uiso 1 1 calc R U . . .
C2 C 0.6628(4) 0.1105(3) 0.6919(4) 0.0433(10) Uani 1 1 d . . . . .
C20 C 0.8181(5) 0.4340(4) 0.3334(4) 0.0577(13) Uani 1 1 d . . . . .
H20A H 0.748999 0.467435 0.291786 0.087 Uiso 1 1 calc R U . . .
H20B H 0.825087 0.361577 0.298137 0.087 Uiso 1 1 calc R U . . .
H20C H 0.888473 0.479966 0.336880 0.087 Uiso 1 1 calc R U . . .
C18 C 0.9915(5) 0.3221(4) 0.5208(5) 0.0571(13) Uani 1 1 d . . . . .
H18 H 1.021197 0.323736 0.458461 0.068 Uiso 1 1 calc R U . . .
C1 C 0.6939(5) -0.0508(4) 0.8018(4) 0.0618(14) Uani 1 1 d . . . . .
H1A H 0.627627 -0.102567 0.797359 0.093 Uiso 1 1 calc R U . . .
H1B H 0.698223 0.005882 0.861230 0.093 Uiso 1 1 calc R U . . .
H1C H 0.766788 -0.089531 0.814795 0.093 Uiso 1 1 calc R U . . .
C26 C 0.5244(5) 0.7698(3) 1.0115(4) 0.0559(13) Uani 1 1 d . . . . .
C16 C 1.0095(5) 0.2721(4) 0.7048(5) 0.0608(13) Uani 1 1 d . . . . .
H16 H 1.053460 0.239883 0.765637 0.073 Uiso 1 1 calc R U . . .
C17 C 1.0527(5) 0.2749(4) 0.6113(5) 0.0637(14) Uani 1 1 d . . . . .
H17 H 1.125241 0.243739 0.610339 0.076 Uiso 1 1 calc R U . . .
C27 C 0.5925(6) 0.8759(3) 1.0700(4) 0.0660(16) Uani 1 1 d . . . . .
H27A H 0.673479 0.859825 1.103945 0.099 Uiso 1 1 calc R U . . .
H27B H 0.554764 0.905687 1.125534 0.099 Uiso 1 1 calc R U . . .
H27C H 0.592479 0.929351 1.017637 0.099 Uiso 1 1 calc R U . . .
C29 C 0.3965(6) 0.7902(4) 0.9541(5) 0.0674(16) Uani 1 1 d . . . . .
H29A H 0.396003 0.843464 0.901434 0.101 Uiso 1 1 calc R U . . .
H29B H 0.355322 0.818566 1.007593 0.101 Uiso 1 1 calc R U . . .
H29C H 0.356885 0.721518 0.916792 0.101 Uiso 1 1 calc R U . . .
C28 C 0.5327(6) 0.6788(4) 1.0909(4) 0.0642(15) Uani 1 1 d . . . . .
H28A H 0.492718 0.611219 1.051422 0.096 Uiso 1 1 calc R U . . .
H28B H 0.495364 0.702315 1.148803 0.096 Uiso 1 1 calc R U . . .
H28C H 0.615330 0.666095 1.122140 0.096 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 C21 1.223(5) . ?
O3 C24 1.362(5) . ?
O3 C25 1.387(5) . ?
O4 C25 1.191(5) . ?
O5 C25 1.306(5) . ?
O5 C26 1.488(5) . ?
O1 C2 1.226(5) . ?
N3 C21 1.373(5) . ?
N3 C19 1.388(6) . ?
N3 C20 1.468(6) . ?
N1 C8 1.391(6) . ?
N1 C2 1.371(5) . ?
N1 C1 1.421(6) . ?
N2 C11 1.142(5) . ?
N4 C23 1.142(6) . ?
C9 C3 1.476(5) . ?
C9 C8 1.377(6) . ?
C9 C4 1.392(6) . ?
C14 C13 1.520(6) . ?
C14 C19 1.391(6) . ?
C14 C15 1.365(6) . ?
C11 C10 1.441(6) . ?
C21 C13 1.531(6) . ?
C10 C12 1.523(5) . ?
C10 C3 1.356(5) . ?
C13 C22 1.524(5) . ?
C13 C12 1.544(6) . ?
C23 C22 1.440(6) . ?
C22 C24 1.346(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C19 C18 1.407(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.397(5) . ?
C5 C6 1.378(6) . ?
C3 C2 1.500(6) . ?
C8 C7 1.402(5) . ?
C24 H24 0.9300 . ?
C4 H4 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.403(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.394(7) . ?
C7 H7 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C18 H18 0.9300 . ?
C18 C17 1.363(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C26 C27 1.514(7) . ?
C26 C29 1.513(8) . ?
C26 C28 1.535(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(7) . ?
C17 H17 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 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
C24 O3 C25 115.4(3) . . ?
C25 O5 C26 119.8(4) . . ?
C21 N3 C19 111.1(4) . . ?
C21 N3 C20 123.3(4) . . ?
C19 N3 C20 125.4(4) . . ?
C8 N1 C1 125.9(3) . . ?
C2 N1 C8 110.0(3) . . ?
C2 N1 C1 124.0(4) . . ?
C8 C9 C3 106.1(3) . . ?
C8 C9 C4 120.5(3) . . ?
C4 C9 C3 133.5(4) . . ?
C19 C14 C13 108.4(4) . . ?
C15 C14 C13 131.0(4) . . ?
C15 C14 C19 120.6(4) . . ?
N2 C11 C10 178.4(4) . . ?
O2 C21 N3 125.8(4) . . ?
O2 C21 C13 125.9(4) . . ?
N3 C21 C13 108.4(4) . . ?
C11 C10 C12 115.4(3) . . ?
C3 C10 C11 119.1(3) . . ?
C3 C10 C12 125.5(4) . . ?
C14 C13 C21 101.7(3) . . ?
C14 C13 C22 111.4(3) . . ?
C14 C13 C12 112.4(3) . . ?
C21 C13 C12 110.0(3) . . ?
C22 C13 C21 109.8(3) . . ?
C22 C13 C12 111.2(3) . . ?
N4 C23 C22 176.7(5) . . ?
C23 C22 C13 116.4(3) . . ?
C24 C22 C13 124.9(4) . . ?
C24 C22 C23 118.7(4) . . ?
C10 C12 C13 113.0(3) . . ?
C10 C12 H12A 109.0 . . ?
C10 C12 H12B 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
N3 C19 C14 110.3(4) . . ?
N3 C19 C18 128.8(4) . . ?
C14 C19 C18 120.9(5) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C6 C5 C4 122.0(4) . . ?
C9 C3 C2 105.5(3) . . ?
C10 C3 C9 129.4(4) . . ?
C10 C3 C2 125.1(3) . . ?
N1 C8 C7 125.9(4) . . ?
C9 C8 N1 111.7(3) . . ?
C9 C8 C7 122.5(4) . . ?
O3 C24 H24 120.8 . . ?
C22 C24 O3 118.3(4) . . ?
C22 C24 H24 120.8 . . ?
C9 C4 C5 117.4(4) . . ?
C9 C4 H4 121.3 . . ?
C5 C4 H4 121.3 . . ?
C14 C15 H15 120.6 . . ?
C14 C15 C16 118.7(5) . . ?
C16 C15 H15 120.6 . . ?
O4 C25 O3 123.6(3) . . ?
O4 C25 O5 130.5(4) . . ?
O5 C25 O3 105.9(4) . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 120.9(4) . . ?
C7 C6 H6 119.5 . . ?
C8 C7 H7 121.6 . . ?
C6 C7 C8 116.7(4) . . ?
C6 C7 H7 121.6 . . ?
O1 C2 N1 124.6(4) . . ?
O1 C2 C3 128.7(4) . . ?
N1 C2 C3 106.7(3) . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C18 H18 121.1 . . ?
C17 C18 C19 117.8(5) . . ?
C17 C18 H18 121.1 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O5 C26 C27 101.9(4) . . ?
O5 C26 C29 110.6(4) . . ?
O5 C26 C28 108.4(3) . . ?
C27 C26 C28 110.7(4) . . ?
C29 C26 C27 112.0(4) . . ?
C29 C26 C28 112.6(5) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(5) . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 121.7(5) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
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 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
O2 C21 C13 C14 -176.4(4) . . . . ?
O2 C21 C13 C22 -58.4(5) . . . . ?
O2 C21 C13 C12 64.2(5) . . . . ?
N3 C21 C13 C14 3.8(4) . . . . ?
N3 C21 C13 C22 121.8(4) . . . . ?
N3 C21 C13 C12 -115.5(3) . . . . ?
N3 C19 C18 C17 178.2(4) . . . . ?
N1 C8 C7 C6 179.6(4) . . . . ?
C9 C3 C2 O1 -179.6(4) . . . . ?
C9 C3 C2 N1 -0.4(5) . . . . ?
C9 C8 C7 C6 0.1(7) . . . . ?
C14 C13 C22 C23 43.8(5) . . . . ?
C14 C13 C22 C24 -137.3(4) . . . . ?
C14 C13 C12 C10 -43.2(5) . . . . ?
C14 C19 C18 C17 0.1(7) . . . . ?
C14 C15 C16 C17 -1.1(7) . . . . ?
C11 C10 C12 C13 -71.4(5) . . . . ?
C11 C10 C3 C9 0.7(7) . . . . ?
C11 C10 C3 C2 -177.3(4) . . . . ?
C21 N3 C19 C14 -0.1(5) . . . . ?
C21 N3 C19 C18 -178.4(4) . . . . ?
C21 C13 C22 C23 -68.1(5) . . . . ?
C21 C13 C22 C24 110.8(5) . . . . ?
C21 C13 C12 C10 69.3(4) . . . . ?
C10 C3 C2 O1 -1.2(8) . . . . ?
C10 C3 C2 N1 178.0(4) . . . . ?
C13 C14 C19 N3 2.7(5) . . . . ?
C13 C14 C19 C18 -178.9(4) . . . . ?
C13 C14 C15 C16 178.9(4) . . . . ?
C13 C22 C24 O3 -179.1(3) . . . . ?
C23 C22 C24 O3 -0.2(6) . . . . ?
C22 C13 C12 C10 -168.9(3) . . . . ?
C12 C10 C3 C9 177.9(4) . . . . ?
C12 C10 C3 C2 -0.1(7) . . . . ?
C12 C13 C22 C23 170.0(3) . . . . ?
C12 C13 C22 C24 -11.1(6) . . . . ?
C19 N3 C21 O2 177.8(4) . . . . ?
C19 N3 C21 C13 -2.5(4) . . . . ?
C19 C14 C13 C21 -3.9(4) . . . . ?
C19 C14 C13 C22 -120.8(4) . . . . ?
C19 C14 C13 C12 113.7(4) . . . . ?
C19 C14 C15 C16 1.1(6) . . . . ?
C19 C18 C17 C16 -0.1(7) . . . . ?
C5 C6 C7 C8 0.0(7) . . . . ?
C3 C9 C8 N1 0.3(5) . . . . ?
C3 C9 C8 C7 179.9(4) . . . . ?
C3 C9 C4 C5 -179.7(4) . . . . ?
C3 C10 C12 C13 111.3(5) . . . . ?
C8 N1 C2 O1 179.8(4) . . . . ?
C8 N1 C2 C3 0.6(5) . . . . ?
C8 C9 C3 C10 -178.3(4) . . . . ?
C8 C9 C3 C2 0.0(4) . . . . ?
C8 C9 C4 C5 1.2(6) . . . . ?
C24 O3 C25 O4 -3.0(6) . . . . ?
C24 O3 C25 O5 176.9(3) . . . . ?
C4 C9 C3 C10 2.5(8) . . . . ?
C4 C9 C3 C2 -179.2(5) . . . . ?
C4 C9 C8 N1 179.7(4) . . . . ?
C4 C9 C8 C7 -0.7(7) . . . . ?
C4 C5 C6 C7 0.6(7) . . . . ?
C15 C14 C13 C21 178.2(4) . . . . ?
C15 C14 C13 C22 61.2(5) . . . . ?
C15 C14 C13 C12 -64.3(6) . . . . ?
C15 C14 C19 N3 -179.1(4) . . . . ?
C15 C14 C19 C18 -0.6(6) . . . . ?
C15 C16 C17 C18 0.6(8) . . . . ?
C25 O3 C24 C22 -168.0(4) . . . . ?
C25 O5 C26 C27 178.7(4) . . . . ?
C25 O5 C26 C29 -62.0(5) . . . . ?
C25 O5 C26 C28 61.8(6) . . . . ?
C6 C5 C4 C9 -1.1(7) . . . . ?
C2 N1 C8 C9 -0.6(5) . . . . ?
C2 N1 C8 C7 179.8(4) . . . . ?
C20 N3 C21 O2 -7.3(7) . . . . ?
C20 N3 C21 C13 172.5(4) . . . . ?
C20 N3 C19 C14 -175.0(4) . . . . ?
C20 N3 C19 C18 6.8(7) . . . . ?
C1 N1 C8 C9 177.4(4) . . . . ?
C1 N1 C8 C7 -2.2(8) . . . . ?
C1 N1 C2 O1 1.8(8) . . . . ?
C1 N1 C2 C3 -177.4(4) . . . . ?
C26 O5 C25 O3 -178.7(3) . . . . ?
C26 O5 C25 O4 1.1(7) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.522 -0.153 584.4 127.9 ?

_smtbx_masks_void_probe_radius   1.0
_smtbx_masks_void_truncation_radius 1.0
_olex2_date_sample_data_collection 2019-11-15
_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 2.470
_oxdiff_exptl_absorpt_empirical_full_min 0.156
####################################################################### 
# 
# 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_lyl-10-19-01
_database_code_depnum_ccdc_archive 'CCDC 2055640'
loop_
_audit_author_name
_audit_author_address
'Yu-Bo Fang'
;School of Chemistry and Chemical Engineering, Guangzhou University
China
;
_audit_update_record             
;
2021-01-13 deposited with the CCDC.	2021-05-14 downloaded from the CCDC.
;
_audit_creation_date             2020-12-31
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H13 N3 O5'
_chemical_formula_sum            'C21 H13 N3 O5'
_chemical_formula_weight         387.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   7.6966(5)
_cell_length_b                   8.9106(5)
_cell_length_c                   13.8343(9)
_cell_angle_alpha                74.371(5)
_cell_angle_beta                 81.939(5)
_cell_angle_gamma                71.066(5)
_cell_volume                     862.80(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2884
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      28.5600
_cell_measurement_theta_min      2.8080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6640
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.403
_diffrn_reflns_theta_min         2.489
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  37.00   1.00    2.00    --   11.90 -57.00   0.00   91
  2  ω    -13.00  78.00   1.00    2.00    --   11.90  77.00 -90.00   91
  3  ω    -13.00  85.00   1.00    2.00    --   11.90  57.00 150.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0185004000
_diffrn_orient_matrix_UB_12      -0.0022744000
_diffrn_orient_matrix_UB_13      0.0492657000
_diffrn_orient_matrix_UB_21      -0.0754556000
_diffrn_orient_matrix_UB_22      -0.0303687000
_diffrn_orient_matrix_UB_23      0.0198432000
_diffrn_orient_matrix_UB_31      0.0590656000
_diffrn_orient_matrix_UB_32      -0.0811423000
_diffrn_orient_matrix_UB_33      0.0048109000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3181
_reflns_number_total             3985
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.014(3)
_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   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3985
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.048
_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)+(0.0525P)²+0.2847P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1255
_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 Aromatic/amide H refined with riding coordinates:
 C17(H17), C13(H13), C6(H6), C12(H12), C3(H3a), C19(H19), C20(H20), C4(H4),
 C5(H5)
2.b Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.59780(16) 0.61300(14) 0.68448(9) 0.0252(3) Uani 1 1 d . . . . .
O3 O 1.12755(16) 0.31727(16) 0.46139(10) 0.0283(3) Uani 1 1 d . . . . .
O2 O 0.92636(15) 0.27360(16) 0.63992(9) 0.0260(3) Uani 1 1 d . . . . .
O5 O 0.56228(17) 0.00398(16) 0.38020(10) 0.0314(3) Uani 1 1 d . . . . .
N1 N 0.66755(18) 0.43903(17) 0.83984(10) 0.0211(3) Uani 1 1 d . . . . .
N3 N 0.68746(19) 0.04082(19) 0.32403(11) 0.0249(3) Uani 1 1 d . . . . .
O4 O 0.7145(2) 0.0289(2) 0.23683(11) 0.0505(4) Uani 1 1 d . . . . .
C14 C 0.6188(2) 0.30563(19) 0.62379(12) 0.0175(3) Uani 1 1 d . . . . .
C7 C 0.6386(2) 0.2014(2) 0.81932(12) 0.0181(3) Uani 1 1 d . . . . .
C17 C 0.7666(2) 0.13855(19) 0.45574(12) 0.0174(3) Uani 1 1 d . . . . .
H17 H 0.669210 0.110112 0.495854 0.021 Uiso 1 1 calc R U . . .
N2 N 0.1618(2) 0.4489(2) 0.88713(13) 0.0446(5) Uani 1 1 d . . . . .
C2 C 0.6912(2) 0.2713(2) 0.88486(12) 0.0198(3) Uani 1 1 d . . . . .
C13 C 0.4651(2) 0.33869(19) 0.57476(12) 0.0200(4) Uani 1 1 d . . . . .
H13 H 0.464402 0.333751 0.508531 0.024 Uiso 1 1 calc R U . . .
C18 C 0.8084(2) 0.1060(2) 0.36184(12) 0.0193(3) Uani 1 1 d . . . . .
C9 C 0.6142(2) 0.4801(2) 0.74472(12) 0.0199(4) Uani 1 1 d . . . . .
C8 C 0.5645(2) 0.33421(19) 0.72808(12) 0.0175(3) Uani 1 1 d . . . . .
C16 C 0.8699(2) 0.21404(19) 0.49100(12) 0.0176(3) Uani 1 1 d . . . . .
C21 C 1.0239(2) 0.2448(2) 0.43025(13) 0.0201(4) Uani 1 1 d . . . . .
C11 C 0.3553(2) 0.3825(2) 0.72890(12) 0.0203(4) Uani 1 1 d . . . . .
C15 C 0.8147(2) 0.26382(19) 0.58856(12) 0.0185(3) Uani 1 1 d . . . . .
C6 C 0.6493(2) 0.0385(2) 0.84609(12) 0.0213(4) Uani 1 1 d . . . . .
H6 H 0.611697 -0.008422 0.803475 0.026 Uiso 1 1 calc R U . . .
C12 C 0.3021(2) 0.3828(2) 0.64015(13) 0.0213(4) Uani 1 1 d . . . . .
H12 H 0.181368 0.407208 0.623636 0.026 Uiso 1 1 calc R U . . .
C3 C 0.7561(2) 0.1819(2) 0.97767(13) 0.0258(4) Uani 1 1 d . . . . .
H3A H 0.789860 0.229944 1.021027 0.031 Uiso 1 1 calc R U . . .
C19 C 0.9574(2) 0.1389(2) 0.30123(12) 0.0234(4) Uani 1 1 d . . . . .
H19 H 0.982916 0.117228 0.237786 0.028 Uiso 1 1 calc R U . . .
C10 C 0.2441(2) 0.4189(2) 0.81560(13) 0.0274(4) Uani 1 1 d . . . . .
C20 C 1.0666(2) 0.2045(2) 0.33731(13) 0.0237(4) Uani 1 1 d . . . . .
H20 H 1.170716 0.222232 0.299099 0.028 Uiso 1 1 calc R U . . .
C4 C 0.7690(2) 0.0166(2) 1.00365(13) 0.0273(4) Uani 1 1 d . . . . .
H4 H 0.812562 -0.047264 1.065612 0.033 Uiso 1 1 calc R U . . .
C5 C 0.7182(2) -0.0548(2) 0.93898(13) 0.0257(4) Uani 1 1 d . . . . .
H5 H 0.730159 -0.165853 0.957632 0.031 Uiso 1 1 calc R U . . .
C1 C 0.6977(2) 0.5533(2) 0.88886(14) 0.0283(4) Uani 1 1 d . . . . .
H1A H 0.645944 0.535915 0.956759 0.043 Uiso 1 1 calc R U . . .
H1B H 0.639530 0.663182 0.852929 0.043 Uiso 1 1 calc R U . . .
H1C H 0.827331 0.536183 0.889198 0.043 Uiso 1 1 calc R U . . .
H3 H 1.218(4) 0.335(3) 0.409(2) 0.068(8) 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 C9 1.230(2) . ?
O3 C21 1.349(2) . ?
O3 H3 0.95(3) . ?
O2 C15 1.227(2) . ?
O5 N3 1.2237(18) . ?
N1 C2 1.417(2) . ?
N1 C9 1.352(2) . ?
N1 C1 1.456(2) . ?
N3 O4 1.2224(19) . ?
N3 C18 1.459(2) . ?
C14 C13 1.355(2) . ?
C14 C8 1.510(2) . ?
C14 C15 1.475(2) . ?
C7 C2 1.395(2) . ?
C7 C8 1.510(2) . ?
C7 C6 1.376(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(2) . ?
C17 C16 1.398(2) . ?
N2 C10 1.144(2) . ?
C2 C3 1.380(2) . ?
C13 H13 0.9300 . ?
C13 C12 1.449(2) . ?
C18 C19 1.386(2) . ?
C9 C8 1.549(2) . ?
C8 C11 1.525(2) . ?
C16 C21 1.412(2) . ?
C16 C15 1.496(2) . ?
C21 C20 1.394(2) . ?
C11 C12 1.347(2) . ?
C11 C10 1.421(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.397(2) . ?
C12 H12 0.9300 . ?
C3 H3A 0.9300 . ?
C3 C4 1.392(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.375(2) . ?
C20 H20 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.387(3) . ?
C5 H5 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
C21 O3 H3 107.5(17) . . ?
C2 N1 C1 124.68(14) . . ?
C9 N1 C2 111.39(14) . . ?
C9 N1 C1 123.93(15) . . ?
O5 N3 C18 118.64(14) . . ?
O4 N3 O5 123.32(16) . . ?
O4 N3 C18 118.02(14) . . ?
C13 C14 C8 109.35(14) . . ?
C13 C14 C15 130.87(15) . . ?
C15 C14 C8 119.52(13) . . ?
C2 C7 C8 108.39(14) . . ?
C6 C7 C2 120.39(15) . . ?
C6 C7 C8 131.09(15) . . ?
C18 C17 H17 119.8 . . ?
C18 C17 C16 120.36(14) . . ?
C16 C17 H17 119.8 . . ?
C7 C2 N1 109.33(14) . . ?
C3 C2 N1 128.55(16) . . ?
C3 C2 C7 122.12(16) . . ?
C14 C13 H13 124.8 . . ?
C14 C13 C12 110.40(15) . . ?
C12 C13 H13 124.8 . . ?
C17 C18 N3 118.70(14) . . ?
C17 C18 C19 121.98(16) . . ?
C19 C18 N3 119.28(15) . . ?
O1 C9 N1 126.01(16) . . ?
O1 C9 C8 126.24(15) . . ?
N1 C9 C8 107.62(14) . . ?
C14 C8 C9 113.79(13) . . ?
C14 C8 C11 101.24(12) . . ?
C7 C8 C14 120.48(13) . . ?
C7 C8 C9 101.89(13) . . ?
C7 C8 C11 111.87(13) . . ?
C11 C8 C9 107.25(12) . . ?
C17 C16 C21 117.69(14) . . ?
C17 C16 C15 120.61(14) . . ?
C21 C16 C15 121.68(15) . . ?
O3 C21 C16 119.70(15) . . ?
O3 C21 C20 119.87(15) . . ?
C20 C21 C16 120.41(15) . . ?
C12 C11 C8 110.59(14) . . ?
C12 C11 C10 128.59(15) . . ?
C10 C11 C8 120.82(14) . . ?
O2 C15 C14 118.55(14) . . ?
O2 C15 C16 122.32(14) . . ?
C14 C15 C16 119.13(14) . . ?
C7 C6 H6 120.9 . . ?
C7 C6 C5 118.26(17) . . ?
C5 C6 H6 120.9 . . ?
C13 C12 H12 125.8 . . ?
C11 C12 C13 108.35(14) . . ?
C11 C12 H12 125.8 . . ?
C2 C3 H3A 121.4 . . ?
C2 C3 C4 117.16(17) . . ?
C4 C3 H3A 121.4 . . ?
C18 C19 H19 120.9 . . ?
C20 C19 C18 118.29(15) . . ?
C20 C19 H19 120.9 . . ?
N2 C10 C11 176.7(2) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 C21 121.10(15) . . ?
C19 C20 H20 119.4 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.32(16) . . ?
C5 C4 H4 119.3 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.72(17) . . ?
C4 C5 H5 119.6 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
O1 C9 C8 C14 41.0(2) . . . . ?
O1 C9 C8 C7 172.20(15) . . . . ?
O1 C9 C8 C11 -70.15(19) . . . . ?
O3 C21 C20 C19 -176.36(15) . . . . ?
O5 N3 C18 C17 -6.2(2) . . . . ?
O5 N3 C18 C19 176.09(15) . . . . ?
N1 C2 C3 C4 -178.94(15) . . . . ?
N1 C9 C8 C14 -142.96(13) . . . . ?
N1 C9 C8 C7 -11.70(15) . . . . ?
N1 C9 C8 C11 105.94(14) . . . . ?
N3 C18 C19 C20 178.25(15) . . . . ?
O4 N3 C18 C17 172.35(16) . . . . ?
O4 N3 C18 C19 -5.3(2) . . . . ?
C14 C13 C12 C11 2.1(2) . . . . ?
C14 C8 C11 C12 -0.67(18) . . . . ?
C14 C8 C11 C10 179.00(15) . . . . ?
C7 C2 C3 C4 0.6(2) . . . . ?
C7 C8 C11 C12 -130.24(15) . . . . ?
C7 C8 C11 C10 49.4(2) . . . . ?
C7 C6 C5 C4 2.0(2) . . . . ?
C17 C18 C19 C20 0.6(3) . . . . ?
C17 C16 C21 O3 -179.91(14) . . . . ?
C17 C16 C21 C20 1.7(2) . . . . ?
C17 C16 C15 O2 152.85(16) . . . . ?
C17 C16 C15 C14 -28.3(2) . . . . ?
C2 N1 C9 O1 -173.59(14) . . . . ?
C2 N1 C9 C8 10.31(16) . . . . ?
C2 C7 C8 C14 136.16(15) . . . . ?
C2 C7 C8 C9 9.12(15) . . . . ?
C2 C7 C8 C11 -105.15(15) . . . . ?
C2 C7 C6 C5 -1.6(2) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C13 C14 C8 C7 125.85(16) . . . . ?
C13 C14 C8 C9 -112.77(15) . . . . ?
C13 C14 C8 C11 1.95(17) . . . . ?
C13 C14 C15 O2 164.38(17) . . . . ?
C13 C14 C15 C16 -14.5(3) . . . . ?
C18 C17 C16 C21 -4.2(2) . . . . ?
C18 C17 C16 C15 174.25(14) . . . . ?
C18 C19 C20 C21 -3.2(3) . . . . ?
C9 N1 C2 C7 -4.39(17) . . . . ?
C9 N1 C2 C3 175.16(15) . . . . ?
C9 C8 C11 C12 118.83(15) . . . . ?
C9 C8 C11 C10 -61.50(19) . . . . ?
C8 C14 C13 C12 -2.55(19) . . . . ?
C8 C14 C15 O2 -9.1(2) . . . . ?
C8 C14 C15 C16 171.94(14) . . . . ?
C8 C7 C2 N1 -3.72(16) . . . . ?
C8 C7 C2 C3 176.69(14) . . . . ?
C8 C7 C6 C5 -176.99(15) . . . . ?
C8 C11 C12 C13 -0.76(19) . . . . ?
C16 C17 C18 N3 -174.50(14) . . . . ?
C16 C17 C18 C19 3.1(2) . . . . ?
C16 C21 C20 C19 2.1(3) . . . . ?
C21 C16 C15 O2 -28.8(2) . . . . ?
C21 C16 C15 C14 150.09(15) . . . . ?
C15 C14 C13 C12 -176.58(16) . . . . ?
C15 C14 C8 C7 -59.3(2) . . . . ?
C15 C14 C8 C9 62.05(18) . . . . ?
C15 C14 C8 C11 176.76(14) . . . . ?
C15 C16 C21 O3 1.7(2) . . . . ?
C15 C16 C21 C20 -176.76(15) . . . . ?
C6 C7 C2 N1 179.92(13) . . . . ?
C6 C7 C2 C3 0.3(2) . . . . ?
C6 C7 C8 C14 -48.0(2) . . . . ?
C6 C7 C8 C9 -175.04(15) . . . . ?
C6 C7 C8 C11 70.7(2) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C10 C11 C12 C13 179.60(17) . . . . ?
C1 N1 C2 C7 175.99(14) . . . . ?
C1 N1 C2 C3 -4.5(3) . . . . ?
C1 N1 C9 O1 6.0(2) . . . . ?
C1 N1 C9 C8 -170.06(13) . . . . ?

_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 1.168
_oxdiff_exptl_absorpt_empirical_full_min 0.730
