# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2311771'
loop_
_audit_author_name
_audit_author_address
'Kai-kai Wang'
;xinxiang University
China
;
_audit_update_record             
;
2023-12-03 deposited with the CCDC.	2024-03-05 downloaded from the CCDC.
;
_audit_creation_date             2023-11-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H19 N O5'
_chemical_formula_sum            'C29 H19 N O5'
_chemical_formula_weight         461.45
_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                   9.9434(12)
_cell_length_b                   11.2111(13)
_cell_length_c                   11.3362(13)
_cell_angle_alpha                100.833(2)
_cell_angle_beta                 92.317(2)
_cell_angle_gamma                115.863(2)
_cell_volume                     1106.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2416
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.155
_cell_measurement_theta_min      2.742
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6563
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0603 before and 0.0263 after correction.
The Ratio of minimum to maximum transmission is 0.8802.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6746
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.636
_diffrn_reflns_theta_min         2.742
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3401
_reflns_number_total             4834
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4834
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0588P)²+0.2905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1305
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C20(H20), C4(H4), C19(H19), C25(H25), C17(H17), C29(H29), C18(H18),
 C3(H3), C1(H1), C28(H28), C27(H27), C2(H2), C26(H26)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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
O5 O 0.54033(13) 0.45222(12) 0.71891(11) 0.0397(3) Uani 1 1 d . . . . .
O4 O 0.63261(14) 0.23308(14) 0.75096(12) 0.0469(3) Uani 1 1 d . . . . .
O3 O 0.74445(15) 0.23709(15) 0.58399(13) 0.0547(4) Uani 1 1 d . . . . .
O2 O 0.46755(16) 0.08311(14) 0.33137(14) 0.0645(5) Uani 1 1 d . . . . .
O1 O 0.7487(2) 0.53756(15) 0.54710(16) 0.0814(6) Uani 1 1 d . . . . .
C11 C 0.64312(18) 0.23923(16) 0.63629(16) 0.0362(4) Uani 1 1 d . . . . .
C21 C 0.33344(19) 0.39417(17) 0.80671(16) 0.0343(4) Uani 1 1 d . . . . .
N1 N 0.1427(2) 0.3988(2) 0.95108(17) 0.0629(5) Uani 1 1 d . . . . .
C14 C 0.31611(18) 0.27601(17) 0.71733(15) 0.0336(4) Uani 1 1 d . . . . .
C15 C 0.18454(18) 0.14028(17) 0.68753(15) 0.0342(4) Uani 1 1 d . . . . .
C13 C 0.44562(18) 0.31812(17) 0.66746(16) 0.0363(4) Uani 1 1 d . . . . .
C23 C 0.47194(19) 0.49830(18) 0.80470(16) 0.0354(4) Uani 1 1 d . . . . .
C5 C 0.68807(19) 0.27236(18) 0.29972(16) 0.0371(4) Uani 1 1 d . . . . .
C24 C 0.5596(2) 0.63937(17) 0.87006(15) 0.0360(4) Uani 1 1 d . . . . .
C10 C 0.50863(18) 0.24901(17) 0.57695(16) 0.0365(4) Uani 1 1 d . . . . .
H10 H 0.4295 0.1552 0.5480 0.044 Uiso 1 1 calc R . . . .
C16 C 0.2006(2) 0.02134(18) 0.66839(16) 0.0401(4) Uani 1 1 d . . . . .
H16 H 0.2962 0.0263 0.6790 0.048 Uiso 1 1 calc R . . . .
C6 C 0.7765(2) 0.40259(18) 0.36925(16) 0.0391(4) Uani 1 1 d . . . . .
C20 C 0.03969(19) 0.12963(19) 0.67395(17) 0.0413(4) Uani 1 1 d . . . . .
H20 H 0.0267 0.2082 0.6875 0.050 Uiso 1 1 calc R . . . .
C22 C 0.2279(2) 0.39756(19) 0.88690(17) 0.0405(4) Uani 1 1 d . . . . .
C9 C 0.5547(2) 0.20279(19) 0.35777(17) 0.0410(4) Uani 1 1 d . . . . .
C8 C 0.5487(2) 0.30693(18) 0.46352(17) 0.0401(4) Uani 1 1 d . . . . .
H8 H 0.4692 0.3299 0.4383 0.048 Uiso 1 1 calc R . . . .
C4 C 0.7345(2) 0.2227(2) 0.19626(17) 0.0463(5) Uani 1 1 d . . . . .
H4 H 0.6738 0.1364 0.1479 0.056 Uiso 1 1 calc R . . . .
C19 C -0.0851(2) 0.0036(2) 0.64057(18) 0.0493(5) Uani 1 1 d . . . . .
H19 H -0.1813 -0.0022 0.6321 0.059 Uiso 1 1 calc R . . . .
C25 C 0.6987(2) 0.71873(19) 0.83736(18) 0.0477(5) Uani 1 1 d . . . . .
H25 H 0.7336 0.6817 0.7725 0.057 Uiso 1 1 calc R . . . .
C17 C 0.0753(2) -0.10435(19) 0.63375(18) 0.0467(5) Uani 1 1 d . . . . .
H17 H 0.0873 -0.1833 0.6197 0.056 Uiso 1 1 calc R . . . .
C29 C 0.5094(2) 0.6977(2) 0.96691(17) 0.0449(5) Uani 1 1 d . . . . .
H29 H 0.4164 0.6467 0.9899 0.054 Uiso 1 1 calc R . . . .
C7 C 0.7009(2) 0.43231(18) 0.47236(18) 0.0454(5) Uani 1 1 d . . . . .
C18 C -0.0671(2) -0.1131(2) 0.61989(18) 0.0489(5) Uani 1 1 d . . . . .
H18 H -0.1511 -0.1978 0.5966 0.059 Uiso 1 1 calc R . . . .
C3 C 0.8730(3) 0.3049(2) 0.16721(19) 0.0545(5) Uani 1 1 d . . . . .
H3 H 0.9062 0.2735 0.0981 0.065 Uiso 1 1 calc R . . . .
C1 C 0.9166(2) 0.4847(2) 0.3401(2) 0.0530(5) Uani 1 1 d . . . . .
H1 H 0.9768 0.5717 0.3874 0.064 Uiso 1 1 calc R . . . .
C12 C 0.7504(2) 0.2206(2) 0.8178(2) 0.0546(5) Uani 1 1 d . . . . .
H12A H 0.7378 0.1291 0.7937 0.082 Uiso 1 1 calc GR . . . .
H12B H 0.7450 0.2415 0.9031 0.082 Uiso 1 1 calc GR . . . .
H12C H 0.8469 0.2827 0.8013 0.082 Uiso 1 1 calc GR . . . .
C28 C 0.5967(2) 0.8303(2) 1.02863(19) 0.0531(5) Uani 1 1 d . . . . .
H28 H 0.5623 0.8683 1.0932 0.064 Uiso 1 1 calc R . . . .
C27 C 0.7344(3) 0.9074(2) 0.9960(2) 0.0580(6) Uani 1 1 d . . . . .
H27 H 0.7931 0.9969 1.0385 0.070 Uiso 1 1 calc R . . . .
C2 C 0.9633(3) 0.4331(2) 0.2389(2) 0.0584(6) Uani 1 1 d . . . . .
H2 H 1.0575 0.4855 0.2185 0.070 Uiso 1 1 calc R . . . .
C26 C 0.7852(3) 0.8513(2) 0.8999(2) 0.0587(6) Uani 1 1 d . . . . .
H26 H 0.8782 0.9032 0.8773 0.070 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 C13 1.370(2) . ?
O5 C23 1.3587(19) . ?
O4 C11 1.321(2) . ?
O4 C12 1.442(2) . ?
O3 C11 1.1964(19) . ?
O2 C9 1.206(2) . ?
O1 C7 1.199(2) . ?
C11 C10 1.528(2) . ?
C21 C14 1.447(2) . ?
C21 C23 1.367(2) . ?
C21 C22 1.424(2) . ?
N1 C22 1.142(2) . ?
C14 C15 1.475(2) . ?
C14 C13 1.353(2) . ?
C15 C16 1.389(2) . ?
C15 C20 1.392(2) . ?
C13 C10 1.491(2) . ?
C23 C24 1.454(2) . ?
C5 C6 1.385(2) . ?
C5 C9 1.470(2) . ?
C5 C4 1.386(2) . ?
C24 C25 1.391(3) . ?
C24 C29 1.393(2) . ?
C10 H10 0.9800 . ?
C10 C8 1.537(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(3) . ?
C6 C7 1.478(3) . ?
C6 C1 1.389(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.382(3) . ?
C9 C8 1.531(2) . ?
C8 H8 0.9800 . ?
C8 C7 1.535(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.378(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.375(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.375(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(3) . ?
C29 H29 0.9300 . ?
C29 C28 1.373(3) . ?
C18 H18 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.382(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.376(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C28 H28 0.9300 . ?
C28 C27 1.374(3) . ?
C27 H27 0.9300 . ?
C27 C26 1.379(3) . ?
C2 H2 0.9300 . ?
C26 H26 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C23 O5 C13 108.30(13) . . ?
C11 O4 C12 117.78(15) . . ?
O4 C11 C10 111.68(14) . . ?
O3 C11 O4 124.83(17) . . ?
O3 C11 C10 123.49(17) . . ?
C23 C21 C14 107.78(14) . . ?
C23 C21 C22 126.59(16) . . ?
C22 C21 C14 125.53(16) . . ?
C21 C14 C15 126.97(15) . . ?
C13 C14 C21 104.90(15) . . ?
C13 C14 C15 128.13(15) . . ?
C16 C15 C14 121.90(15) . . ?
C16 C15 C20 118.45(16) . . ?
C20 C15 C14 119.61(15) . . ?
O5 C13 C10 115.10(14) . . ?
C14 C13 O5 110.64(14) . . ?
C14 C13 C10 134.12(15) . . ?
O5 C23 C21 108.37(14) . . ?
O5 C23 C24 115.24(14) . . ?
C21 C23 C24 136.38(15) . . ?
C6 C5 C9 109.78(15) . . ?
C6 C5 C4 120.72(17) . . ?
C4 C5 C9 129.37(17) . . ?
C25 C24 C23 119.75(15) . . ?
C25 C24 C29 118.45(17) . . ?
C29 C24 C23 121.79(16) . . ?
C11 C10 H10 106.1 . . ?
C11 C10 C8 110.23(14) . . ?
C13 C10 C11 111.36(15) . . ?
C13 C10 H10 106.1 . . ?
C13 C10 C8 116.16(15) . . ?
C8 C10 H10 106.1 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.49(17) . . ?
C17 C16 H16 119.8 . . ?
C5 C6 C7 110.28(16) . . ?
C5 C6 C1 120.98(18) . . ?
C1 C6 C7 128.72(17) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.73(18) . . ?
C19 C20 H20 119.6 . . ?
N1 C22 C21 179.2(2) . . ?
O2 C9 C5 126.61(16) . . ?
O2 C9 C8 124.94(17) . . ?
C5 C9 C8 108.38(15) . . ?
C10 C8 H8 107.7 . . ?
C9 C8 C10 111.95(15) . . ?
C9 C8 H8 107.7 . . ?
C9 C8 C7 102.90(14) . . ?
C7 C8 C10 118.31(15) . . ?
C7 C8 H8 107.7 . . ?
C5 C4 H4 121.0 . . ?
C3 C4 C5 118.05(19) . . ?
C3 C4 H4 121.0 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 C20 120.08(18) . . ?
C18 C19 H19 120.0 . . ?
C24 C25 H25 119.6 . . ?
C26 C25 C24 120.74(18) . . ?
C26 C25 H25 119.6 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.31(18) . . ?
C18 C17 H17 119.8 . . ?
C24 C29 H29 119.8 . . ?
C28 C29 C24 120.32(18) . . ?
C28 C29 H29 119.8 . . ?
O1 C7 C6 125.71(18) . . ?
O1 C7 C8 126.42(18) . . ?
C6 C7 C8 107.84(15) . . ?
C19 C18 C17 119.92(18) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C4 C3 H3 119.4 . . ?
C4 C3 C2 121.12(19) . . ?
C2 C3 H3 119.4 . . ?
C6 C1 H1 121.1 . . ?
C2 C1 C6 117.80(19) . . ?
C2 C1 H1 121.1 . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C29 C28 H28 119.7 . . ?
C29 C28 C27 120.67(18) . . ?
C27 C28 H28 119.7 . . ?
C28 C27 H27 120.2 . . ?
C28 C27 C26 119.68(19) . . ?
C26 C27 H27 120.2 . . ?
C3 C2 H2 119.4 . . ?
C1 C2 C3 121.26(19) . . ?
C1 C2 H2 119.4 . . ?
C25 C26 C27 120.1(2) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?

_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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2311772'
loop_
_audit_author_name
_audit_author_address
'Kai-kai Wang'
;xinxiang University
China
;
_audit_update_record             
;
2023-12-03 deposited with the CCDC.	2024-03-05 downloaded from the CCDC.
;
_audit_creation_date             2023-11-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H18 O6'
_chemical_formula_sum            'C29 H18 O6'
_chemical_formula_weight         462.43
_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 0.0033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.5559(17)
_cell_length_b                   26.500(5)
_cell_length_c                   9.988(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.097(4)
_cell_angle_gamma                90
_cell_volume                     2236.1(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2371
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.36
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6706
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0576 before and 0.0319 after correction.
The Ratio of minimum to maximum transmission is 0.8994.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13401
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.547
_diffrn_reflns_theta_min         2.530
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2832
_reflns_number_total             5050
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5050
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0514P)²+0.0162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1197
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C27(H27), C25(H25), C17(H17), C26(H26), C4(H4), C12(H12), C16(H16),
 C14(H14), C1(H1), C13(H13), C15(H15), C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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
O6 O 0.54989(16) 0.70031(5) 0.30240(13) 0.0500(4) Uani 1 1 d . . . . .
O2 O 0.31946(17) 0.69832(5) 0.02425(14) 0.0532(4) Uani 1 1 d . . . . .
O4 O 0.68777(16) 0.57782(5) 0.35117(14) 0.0531(4) Uani 1 1 d . . . . .
O5 O 0.34102(18) 0.54268(5) 0.37793(14) 0.0582(4) Uani 1 1 d . . . . .
O3 O 0.62701(19) 0.51685(6) 0.19737(16) 0.0684(5) Uani 1 1 d . . . . .
O1 O 0.05451(19) 0.61371(7) 0.33794(17) 0.0796(5) Uani 1 1 d . . . . .
C23 C 0.4595(2) 0.66251(7) 0.49505(18) 0.0361(4) Uani 1 1 d . . . . .
C22 C 0.4797(2) 0.66751(7) 0.35159(19) 0.0371(4) Uani 1 1 d . . . . .
C9 C 0.2417(2) 0.68921(7) 0.11200(19) 0.0401(5) Uani 1 1 d . . . . .
C21 C 0.3954(2) 0.62274(6) 0.27298(18) 0.0365(4) Uani 1 1 d . . . . .
C29 C 0.3666(2) 0.58714(7) 0.38906(19) 0.0412(5) Uani 1 1 d . . . . .
C8 C 0.2346(2) 0.63727(7) 0.18208(18) 0.0384(5) Uani 1 1 d . . . . .
C18 C 0.4867(2) 0.59563(7) 0.17355(18) 0.0399(5) Uani 1 1 d . . . . .
H18 H 0.5428 0.6211 0.1283 0.048 Uiso 1 1 calc R . . . .
C28 C 0.3903(2) 0.61664(7) 0.51590(18) 0.0390(5) Uani 1 1 d . . . . .
C24 C 0.5020(2) 0.69605(7) 0.6010(2) 0.0434(5) Uani 1 1 d . . . . .
H24 H 0.5517 0.7265 0.5879 0.052 Uiso 1 1 calc R . . . .
C19 C 0.6055(2) 0.55818(8) 0.2393(2) 0.0471(5) Uani 1 1 d . . . . .
C11 C 0.0673(2) 0.58389(7) -0.01347(19) 0.0460(5) Uani 1 1 d . . . . .
C27 C 0.3589(2) 0.60315(8) 0.64298(19) 0.0494(5) Uani 1 1 d . . . . .
H27 H 0.3139 0.5721 0.6575 0.059 Uiso 1 1 calc R . . . .
C5 C 0.1322(2) 0.72365(8) 0.1658(2) 0.0468(5) Uani 1 1 d . . . . .
C25 C 0.4681(3) 0.68267(8) 0.7264(2) 0.0510(5) Uani 1 1 d . . . . .
H25 H 0.4940 0.7047 0.7990 0.061 Uiso 1 1 calc R . . . .
C10 C 0.2177(2) 0.59512(7) 0.07598(18) 0.0423(5) Uani 1 1 d . . . . .
C17 C 0.3574(3) 0.57434(7) 0.07178(19) 0.0457(5) Uani 1 1 d . . . . .
H17 H 0.3733 0.5489 0.0112 0.055 Uiso 1 1 calc R . . . .
C7 C 0.1024(2) 0.64530(9) 0.2670(2) 0.0501(5) Uani 1 1 d . . . . .
C26 C 0.3965(3) 0.63722(8) 0.7468(2) 0.0531(6) Uani 1 1 d . . . . .
H26 H 0.3733 0.6295 0.8324 0.064 Uiso 1 1 calc R . . . .
C6 C 0.0494(2) 0.69765(9) 0.2523(2) 0.0525(6) Uani 1 1 d . . . . .
C4 C 0.1013(3) 0.77400(9) 0.1358(2) 0.0638(7) Uani 1 1 d . . . . .
H4 H 0.1558 0.7915 0.0770 0.077 Uiso 1 1 calc R . . . .
C12 C 0.0587(3) 0.54401(9) -0.1045(2) 0.0633(6) Uani 1 1 d . . . . .
H12 H 0.1494 0.5253 -0.1103 0.076 Uiso 1 1 calc R . . . .
C16 C -0.0691(3) 0.61071(9) -0.0106(2) 0.0666(7) Uani 1 1 d . . . . .
H16 H -0.0673 0.6381 0.0477 0.080 Uiso 1 1 calc R . . . .
C14 C -0.2148(3) 0.55821(10) -0.1805(2) 0.0695(7) Uani 1 1 d . . . . .
H14 H -0.3090 0.5495 -0.2357 0.083 Uiso 1 1 calc R . . . .
C1 C -0.0691(3) 0.72112(13) 0.3097(3) 0.0758(8) Uani 1 1 d . . . . .
H1 H -0.1263 0.7035 0.3663 0.091 Uiso 1 1 calc R . . . .
C20 C 0.8016(3) 0.54537(8) 0.4308(3) 0.0695(7) Uani 1 1 d . . . . .
H20A H 0.8694 0.5306 0.3735 0.104 Uiso 1 1 calc GR . . . .
H20B H 0.7472 0.5191 0.4710 0.104 Uiso 1 1 calc GR . . . .
H20C H 0.8641 0.5647 0.5009 0.104 Uiso 1 1 calc GR . . . .
C13 C -0.0800(3) 0.53155(10) -0.1860(2) 0.0737(7) Uani 1 1 d . . . . .
H13 H -0.0821 0.5046 -0.2458 0.088 Uiso 1 1 calc R . . . .
C15 C -0.2097(3) 0.59788(10) -0.0926(3) 0.0778(8) Uani 1 1 d . . . . .
H15 H -0.3010 0.6164 -0.0878 0.093 Uiso 1 1 calc R . . . .
C3 C -0.0139(4) 0.79719(12) 0.1968(3) 0.0942(10) Uani 1 1 d . . . . .
H3 H -0.0349 0.8313 0.1814 0.113 Uiso 1 1 calc R . . . .
C2 C -0.0988(3) 0.77044(15) 0.2807(3) 0.0962(11) Uani 1 1 d . . . . .
H2 H -0.1780 0.7868 0.3179 0.115 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O6 C22 1.204(2) . ?
O2 C9 1.205(2) . ?
O4 C19 1.329(2) . ?
O4 C20 1.441(2) . ?
O5 C29 1.200(2) . ?
O3 C19 1.197(2) . ?
O1 C7 1.209(2) . ?
C23 C22 1.476(3) . ?
C23 C28 1.382(2) . ?
C23 C24 1.386(2) . ?
C22 C21 1.538(2) . ?
C9 C8 1.550(3) . ?
C9 C5 1.469(3) . ?
C21 C29 1.545(3) . ?
C21 C8 1.572(3) . ?
C21 C18 1.535(3) . ?
C29 C28 1.475(3) . ?
C8 C10 1.531(2) . ?
C8 C7 1.532(3) . ?
C18 H18 0.9800 . ?
C18 C19 1.496(3) . ?
C18 C17 1.490(2) . ?
C28 C27 1.385(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.376(3) . ?
C11 C10 1.476(3) . ?
C11 C12 1.389(3) . ?
C11 C16 1.371(3) . ?
C27 H27 0.9300 . ?
C27 C26 1.374(3) . ?
C5 C6 1.385(3) . ?
C5 C4 1.384(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.381(3) . ?
C10 C17 1.323(3) . ?
C17 H17 0.9300 . ?
C7 C6 1.460(3) . ?
C26 H26 0.9300 . ?
C6 C1 1.388(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.382(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.387(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.361(4) . ?
C14 C15 1.366(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.354(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C13 H13 0.9300 . ?
C15 H15 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.387(4) . ?
C2 H2 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O4 C20 116.88(17) . . ?
C28 C23 C22 110.11(16) . . ?
C28 C23 C24 121.07(18) . . ?
C24 C23 C22 128.80(17) . . ?
O6 C22 C23 127.11(17) . . ?
O6 C22 C21 124.91(17) . . ?
C23 C22 C21 107.98(15) . . ?
O2 C9 C8 124.89(17) . . ?
O2 C9 C5 126.75(19) . . ?
C5 C9 C8 108.28(17) . . ?
C22 C21 C29 101.87(14) . . ?
C22 C21 C8 113.76(14) . . ?
C29 C21 C8 110.72(14) . . ?
C18 C21 C22 116.47(15) . . ?
C18 C21 C29 110.97(15) . . ?
C18 C21 C8 103.26(13) . . ?
O5 C29 C21 125.34(18) . . ?
O5 C29 C28 126.74(18) . . ?
C28 C29 C21 107.72(15) . . ?
C9 C8 C21 112.64(14) . . ?
C10 C8 C9 109.97(14) . . ?
C10 C8 C21 101.49(15) . . ?
C10 C8 C7 119.18(16) . . ?
C7 C8 C9 102.24(16) . . ?
C7 C8 C21 111.70(15) . . ?
C21 C18 H18 108.2 . . ?
C19 C18 C21 113.97(15) . . ?
C19 C18 H18 108.2 . . ?
C17 C18 C21 102.69(15) . . ?
C17 C18 H18 108.2 . . ?
C17 C18 C19 115.33(17) . . ?
C23 C28 C29 109.94(16) . . ?
C23 C28 C27 120.99(17) . . ?
C27 C28 C29 129.02(17) . . ?
C23 C24 H24 121.2 . . ?
C25 C24 C23 117.53(18) . . ?
C25 C24 H24 121.2 . . ?
O4 C19 C18 109.99(18) . . ?
O3 C19 O4 124.2(2) . . ?
O3 C19 C18 125.79(19) . . ?
C12 C11 C10 120.04(19) . . ?
C16 C11 C10 123.12(19) . . ?
C16 C11 C12 116.83(19) . . ?
C28 C27 H27 121.1 . . ?
C26 C27 C28 117.73(18) . . ?
C26 C27 H27 121.1 . . ?
C6 C5 C9 109.74(19) . . ?
C4 C5 C9 129.1(2) . . ?
C4 C5 C6 121.0(2) . . ?
C24 C25 H25 119.3 . . ?
C24 C25 C26 121.39(18) . . ?
C26 C25 H25 119.3 . . ?
C11 C10 C8 122.95(18) . . ?
C17 C10 C8 109.81(16) . . ?
C17 C10 C11 127.05(18) . . ?
C18 C17 H17 123.3 . . ?
C10 C17 C18 113.46(17) . . ?
C10 C17 H17 123.3 . . ?
O1 C7 C8 125.2(2) . . ?
O1 C7 C6 126.0(2) . . ?
C6 C7 C8 108.72(18) . . ?
C27 C26 C25 121.24(19) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C5 C6 C7 110.76(19) . . ?
C5 C6 C1 120.9(2) . . ?
C1 C6 C7 128.3(2) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 C5 117.3(3) . . ?
C3 C4 H4 121.3 . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.6(2) . . ?
C13 C12 H12 119.2 . . ?
C11 C16 H16 119.3 . . ?
C11 C16 C15 121.5(2) . . ?
C15 C16 H16 119.3 . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 119.0(2) . . ?
C15 C14 H14 120.5 . . ?
C6 C1 H1 121.0 . . ?
C2 C1 C6 118.0(3) . . ?
C2 C1 H1 121.0 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C16 C15 H15 119.8 . . ?
C14 C15 C16 120.4(2) . . ?
C14 C15 H15 119.8 . . ?
C4 C3 H3 119.4 . . ?
C4 C3 C2 121.1(3) . . ?
C2 C3 H3 119.4 . . ?
C1 C2 C3 121.6(3) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
