# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2299581'
loop_
_audit_author_name
_audit_author_address
'Zheng Luo'
;Huaiyin Normal University
China
;
_audit_update_record             
;
2023-10-06 deposited with the CCDC.	2023-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H22 N2 O8'
_chemical_formula_sum            'C30 H22 N2 O8'
_chemical_formula_weight         538.49

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.4827(4)
_cell_length_b                   11.1537(4)
_cell_length_c                   12.5636(5)
_cell_angle_alpha                77.9970(10)
_cell_angle_beta                 76.9340(10)
_cell_angle_gamma                62.4550(10)
_cell_volume                     1259.59(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    172(2)
_cell_measurement_reflns_used    3973
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      25.35

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6614
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      172(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9660
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.819
_diffrn_reflns_theta_max         25.380
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             4555
_reflns_number_gt                3552
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0437P)²+0.5260P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4555
_refine_ls_number_parameters     364
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1050
_refine_ls_wR_factor_gt          0.0932
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.74954(18) 0.54160(17) 0.40654(14) 0.0221(4) Uani 1 1 d . . . . .
C2 C 0.74382(18) 0.60359(17) 0.29994(14) 0.0232(4) Uani 1 1 d . . . . .
C3 C 0.63160(18) 0.73878(17) 0.30067(14) 0.0223(4) Uani 1 1 d . . . . .
C4 C 0.56870(18) 0.75696(16) 0.40941(14) 0.0207(4) Uani 1 1 d . . . . .
C5 C 0.45292(17) 0.86947(16) 0.46419(14) 0.0216(4) Uani 1 1 d . . . . .
C6 C 0.37003(18) 0.99421(17) 0.40513(16) 0.0260(4) Uani 1 1 d . . . . .
H6 H 0.3877 1.0050 0.3270 0.031 Uiso 1 1 calc R U . . .
C7 C 0.26352(19) 1.10058(18) 0.46017(16) 0.0291(4) Uani 1 1 d . . . . .
H7 H 0.2086 1.1843 0.4194 0.035 Uiso 1 1 calc R U . . .
C8 C 0.23532(19) 1.08697(18) 0.57471(17) 0.0297(4) Uani 1 1 d . . . . .
H8 H 0.1621 1.1612 0.6118 0.036 Uiso 1 1 calc R U . . .
C9 C 0.31428(19) 0.96517(18) 0.63396(16) 0.0275(4) Uani 1 1 d . . . . .
H9 H 0.2946 0.9559 0.7121 0.033 Uiso 1 1 calc R U . . .
C10 C 0.42339(18) 0.85467(17) 0.58032(14) 0.0225(4) Uani 1 1 d . . . . .
C11 C 0.50666(18) 0.72563(17) 0.64225(14) 0.0228(4) Uani 1 1 d . . . . .
C12 C 0.61222(18) 0.62005(17) 0.59083(14) 0.0211(4) Uani 1 1 d . . . . .
C13 C 0.85196(18) 0.39763(17) 0.44110(14) 0.0216(4) Uani 1 1 d . . . . .
C14 C 0.9010(2) 0.16858(18) 0.44535(19) 0.0364(5) Uani 1 1 d . . . . .
H14A H 0.9848 0.1439 0.3866 0.055 Uiso 1 1 calc R U . . .
H14B H 0.8491 0.1140 0.4475 0.055 Uiso 1 1 calc R U . . .
H14C H 0.9347 0.1510 0.5162 0.055 Uiso 1 1 calc R U . . .
C15 C 0.82986(19) 0.53617(18) 0.20071(15) 0.0258(4) Uani 1 1 d . . . . .
C16 C 1.0382(2) 0.3433(2) 0.13648(18) 0.0445(5) Uani 1 1 d . . . . .
H16A H 0.9758 0.3206 0.1050 0.067 Uiso 1 1 calc R U . . .
H16B H 1.1160 0.2594 0.1654 0.067 Uiso 1 1 calc R U . . .
H16C H 1.0809 0.3943 0.0793 0.067 Uiso 1 1 calc R U . . .
C17 C 0.60311(19) 0.83907(17) 0.20004(14) 0.0254(4) Uani 1 1 d . . . . .
C18 C 0.7168(2) 0.9303(2) 0.04303(16) 0.0426(5) Uani 1 1 d . . . . .
H18A H 0.6772 0.9009 -0.0047 0.064 Uiso 1 1 calc R U . . .
H18B H 0.8142 0.9209 0.0086 0.064 Uiso 1 1 calc R U . . .
H18C H 0.6530 1.0258 0.0538 0.064 Uiso 1 1 calc R U . . .
C19 C 0.47402(19) 0.70907(18) 0.76522(15) 0.0273(4) Uani 1 1 d . . . . .
C20 C 0.5607(2) 0.7198(2) 0.82820(16) 0.0362(5) Uani 1 1 d . . . . .
H20 H 0.6396 0.7405 0.7929 0.043 Uiso 1 1 calc R U . . .
C21 C 0.5331(3) 0.7005(2) 0.94196(17) 0.0451(5) Uani 1 1 d . . . . .
H21 H 0.5937 0.7068 0.9844 0.054 Uiso 1 1 calc R U . . .
C22 C 0.4176(3) 0.6722(2) 0.99362(17) 0.0497(6) Uani 1 1 d . . . . .
H22 H 0.3994 0.6578 1.0717 0.060 Uiso 1 1 calc R U . . .
C23 C 0.3290(3) 0.6646(3) 0.93259(18) 0.0532(6) Uani 1 1 d . . . . .
H23 H 0.2481 0.6472 0.9685 0.064 Uiso 1 1 calc R U . . .
C24 C 0.3572(2) 0.6822(2) 0.81849(17) 0.0422(5) Uani 1 1 d . . . . .
H24 H 0.2961 0.6759 0.7766 0.051 Uiso 1 1 calc R U . . .
C25 C 0.69459(18) 0.48323(17) 0.65041(14) 0.0222(4) Uani 1 1 d . . . . .
C26 C 0.81711(19) 0.45457(18) 0.69526(15) 0.0278(4) Uani 1 1 d . . . . .
H26 H 0.8494 0.5230 0.6884 0.033 Uiso 1 1 calc R U . . .
C27 C 0.8922(2) 0.32670(19) 0.74977(15) 0.0308(4) Uani 1 1 d . . . . .
H27 H 0.9748 0.3068 0.7817 0.037 Uiso 1 1 calc R U . . .
C28 C 0.8436(2) 0.22897(18) 0.75642(14) 0.0282(4) Uani 1 1 d . . . . .
C29 C 0.7220(2) 0.25429(19) 0.71459(15) 0.0305(4) Uani 1 1 d . . . . .
H29 H 0.6906 0.1852 0.7215 0.037 Uiso 1 1 calc R U . . .
C30 C 0.64602(19) 0.38362(18) 0.66199(15) 0.0272(4) Uani 1 1 d . . . . .
H30 H 0.5605 0.4042 0.6338 0.033 Uiso 1 1 calc R U . . .
N1 N 0.64405(14) 0.63449(13) 0.47452(11) 0.0203(3) Uani 1 1 d . . . . .
N2 N 0.92659(19) 0.09048(18) 0.80936(14) 0.0406(4) Uani 1 1 d . . . . .
O1 O 0.80379(13) 0.31199(12) 0.42433(11) 0.0281(3) Uani 1 1 d . . . . .
O2 O 0.96399(13) 0.36451(12) 0.47345(11) 0.0303(3) Uani 1 1 d . . . . .
O3 O 0.95212(14) 0.42585(13) 0.22484(10) 0.0344(3) Uani 1 1 d . . . . .
O4 O 0.79543(16) 0.57275(15) 0.11042(11) 0.0410(4) Uani 1 1 d . . . . .
O5 O 0.72566(14) 0.84630(13) 0.14898(10) 0.0333(3) Uani 1 1 d . . . . .
O6 O 0.48737(15) 0.90439(15) 0.16779(11) 0.0406(4) Uani 1 1 d . . . . .
O7 O 1.0170(2) 0.07378(18) 0.86389(17) 0.0711(6) Uani 1 1 d . . . . .
O8 O 0.9018(2) -0.00143(15) 0.79464(15) 0.0587(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.374(2) . ?
C1 N1 1.381(2) . ?
C1 C13 1.499(2) . ?
C2 C3 1.421(2) . ?
C2 C15 1.479(2) . ?
C3 C4 1.388(2) . ?
C3 C17 1.487(2) . ?
C4 N1 1.410(2) . ?
C4 C5 1.447(2) . ?
C5 C6 1.409(2) . ?
C5 C10 1.412(2) . ?
C6 C7 1.378(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.393(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.405(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.455(2) . ?
C11 C12 1.348(2) . ?
C11 C19 1.496(2) . ?
C12 N1 1.416(2) . ?
C12 C25 1.494(2) . ?
C13 O2 1.197(2) . ?
C13 O1 1.338(2) . ?
C14 O1 1.451(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 O4 1.200(2) . ?
C15 O3 1.346(2) . ?
C16 O3 1.448(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 O6 1.204(2) . ?
C17 O5 1.331(2) . ?
C18 O5 1.454(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.389(3) . ?
C19 C24 1.386(3) . ?
C20 C21 1.384(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.378(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.371(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C30 1.392(2) . ?
C25 C26 1.393(2) . ?
C26 C27 1.386(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.382(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.375(3) . ?
C28 N2 1.475(2) . ?
C29 C30 1.389(2) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
N2 O7 1.217(2) . ?
N2 O8 1.225(2) . ?

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
C2 C1 N1 107.99(14) . . ?
C2 C1 C13 125.29(15) . . ?
N1 C1 C13 126.72(15) . . ?
C1 C2 C3 108.53(15) . . ?
C1 C2 C15 125.46(15) . . ?
C3 C2 C15 125.74(15) . . ?
C4 C3 C2 107.35(14) . . ?
C4 C3 C17 129.45(15) . . ?
C2 C3 C17 123.01(16) . . ?
C3 C4 N1 107.20(14) . . ?
C3 C4 C5 134.45(15) . . ?
N1 C4 C5 118.33(15) . . ?
C6 C5 C10 118.94(16) . . ?
C6 C5 C4 121.94(16) . . ?
C10 C5 C4 119.11(15) . . ?
C7 C6 C5 120.35(17) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.88(17) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 119.63(17) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 120.89(17) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C5 119.30(16) . . ?
C9 C10 C11 121.20(16) . . ?
C5 C10 C11 119.49(15) . . ?
C12 C11 C10 121.20(16) . . ?
C12 C11 C19 119.22(15) . . ?
C10 C11 C19 119.58(15) . . ?
C11 C12 N1 119.73(15) . . ?
C11 C12 C25 123.13(15) . . ?
N1 C12 C25 117.06(14) . . ?
O2 C13 O1 125.29(15) . . ?
O2 C13 C1 124.64(15) . . ?
O1 C13 C1 109.96(14) . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 O3 123.82(17) . . ?
O4 C15 C2 125.07(16) . . ?
O3 C15 C2 111.10(15) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O6 C17 O5 124.11(16) . . ?
O6 C17 C3 125.89(16) . . ?
O5 C17 C3 109.99(14) . . ?
O5 C18 H18A 109.5 . . ?
O5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 118.74(18) . . ?
C20 C19 C11 120.57(17) . . ?
C24 C19 C11 120.69(17) . . ?
C21 C20 C19 120.6(2) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 119.9(2) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 120.2(2) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.2(2) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C19 C24 C23 120.4(2) . . ?
C19 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C30 C25 C26 119.80(15) . . ?
C30 C25 C12 118.85(15) . . ?
C26 C25 C12 121.34(15) . . ?
C27 C26 C25 120.32(16) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C28 C27 C26 118.24(17) . . ?
C28 C27 H27 120.9 . . ?
C26 C27 H27 120.9 . . ?
C29 C28 C27 122.97(16) . . ?
C29 C28 N2 118.18(17) . . ?
C27 C28 N2 118.84(17) . . ?
C28 C29 C30 118.23(16) . . ?
C28 C29 H29 120.9 . . ?
C30 C29 H29 120.9 . . ?
C29 C30 C25 120.38(16) . . ?
C29 C30 H30 119.8 . . ?
C25 C30 H30 119.8 . . ?
C1 N1 C4 108.92(13) . . ?
C1 N1 C12 128.96(14) . . ?
C4 N1 C12 122.09(14) . . ?
O7 N2 O8 123.77(18) . . ?
O7 N2 C28 118.18(18) . . ?
O8 N2 C28 118.04(17) . . ?
C13 O1 C14 115.00(13) . . ?
C15 O3 C16 116.16(15) . . ?
C17 O5 C18 115.81(15) . . ?

_refine_diff_density_max         0.670
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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 2299583'
loop_
_audit_author_name
_audit_author_address
'Zheng Luo'
;Huaiyin Normal University
China
;
_audit_update_record             
;
2023-10-06 deposited with the CCDC.	2023-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H23 N O6'
_chemical_formula_sum            'C26 H23 N O6'
_chemical_formula_weight         445.45

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   11.3722(4)
_cell_length_b                   10.3911(4)
_cell_length_c                   18.8309(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.105(2)
_cell_angle_gamma                90
_cell_volume                     2212.62(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3927
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      25.33

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.290
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6375
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12879
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.802
_diffrn_reflns_theta_max         25.357
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4045
_reflns_number_gt                3034
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0504P)²+1.1565P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4045
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.21876(16) 0.55662(18) 1.03514(10) 0.0226(4) Uani 1 1 d . . . . .
C2 C 0.26528(17) 0.45888(18) 1.07918(10) 0.0231(4) Uani 1 1 d . . . . .
C3 C 0.34250(16) 0.38453(18) 1.04131(10) 0.0222(4) Uani 1 1 d . . . . .
C4 C 0.34263(16) 0.43874(18) 0.97434(10) 0.0212(4) Uani 1 1 d . . . . .
C5 C 0.40280(16) 0.40693(18) 0.91295(10) 0.0221(4) Uani 1 1 d . . . . .
C6 C 0.49458(17) 0.31615(19) 0.91718(11) 0.0269(4) Uani 1 1 d . . . . .
H6 H 0.5173 0.2731 0.9610 0.032 Uiso 1 1 calc R U . . .
C7 C 0.55195(17) 0.2891(2) 0.85811(11) 0.0293(5) Uani 1 1 d . . . . .
H7 H 0.6144 0.2279 0.8615 0.035 Uiso 1 1 calc R U . . .
C8 C 0.51903(18) 0.3510(2) 0.79358(12) 0.0318(5) Uani 1 1 d . . . . .
H8 H 0.5582 0.3311 0.7528 0.038 Uiso 1 1 calc R U . . .
C9 C 0.43015(18) 0.4405(2) 0.78874(11) 0.0294(5) Uani 1 1 d . . . . .
H9 H 0.4083 0.4820 0.7443 0.035 Uiso 1 1 calc R U . . .
C10 C 0.37043(17) 0.47252(19) 0.84827(10) 0.0244(4) Uani 1 1 d . . . . .
C11 C 0.28242(17) 0.57439(19) 0.84562(10) 0.0254(4) Uani 1 1 d . . . . .
C12 C 0.23520(17) 0.61172(18) 0.90551(10) 0.0235(4) Uani 1 1 d . . . . .
C13 C 0.13762(17) 0.65947(19) 1.05658(10) 0.0230(4) Uani 1 1 d . . . . .
C14 C -0.05561(19) 0.6958(2) 1.08701(14) 0.0386(6) Uani 1 1 d . . . . .
H14A H -0.0186 0.7403 1.1295 0.058 Uiso 1 1 calc R U . . .
H14B H -0.1235 0.6459 1.0996 0.058 Uiso 1 1 calc R U . . .
H14C H -0.0824 0.7593 1.0503 0.058 Uiso 1 1 calc R U . . .
C15 C 0.24650(17) 0.44855(19) 1.15504(10) 0.0258(4) Uani 1 1 d . . . . .
C16 C 0.3032(2) 0.3351(2) 1.26192(12) 0.0453(6) Uani 1 1 d . . . . .
H16A H 0.3566 0.3987 1.2865 0.068 Uiso 1 1 calc R U . . .
H16B H 0.3290 0.2483 1.2768 0.068 Uiso 1 1 calc R U . . .
H16C H 0.2226 0.3496 1.2741 0.068 Uiso 1 1 calc R U . . .
C17 C 0.40303(17) 0.26373(19) 1.06782(11) 0.0255(4) Uani 1 1 d . . . . .
C18 C 0.3722(3) 0.0427(2) 1.08901(17) 0.0594(8) Uani 1 1 d . . . . .
H18A H 0.4433 0.0191 1.0668 0.089 Uiso 1 1 calc R U . . .
H18B H 0.3118 -0.0239 1.0789 0.089 Uiso 1 1 calc R U . . .
H18C H 0.3920 0.0505 1.1408 0.089 Uiso 1 1 calc R U . . .
C19 C 0.2440(2) 0.6397(2) 0.77517(11) 0.0387(6) Uani 1 1 d . . . . .
H19A H 0.3144 0.6578 0.7501 0.046 Uiso 1 1 calc R U . . .
H19B H 0.2058 0.7229 0.7843 0.046 Uiso 1 1 calc R U . . .
C20 C 0.1575(3) 0.5562(3) 0.72768(14) 0.0604(8) Uani 1 1 d . . . . .
H20A H 0.1938 0.4724 0.7203 0.091 Uiso 1 1 calc R U . . .
H20B H 0.1381 0.5987 0.6815 0.091 Uiso 1 1 calc R U . . .
H20C H 0.0851 0.5438 0.7508 0.091 Uiso 1 1 calc R U . . .
C21 C 0.15585(17) 0.72496(18) 0.90826(10) 0.0234(4) Uani 1 1 d . . . . .
C22 C 0.20551(18) 0.84725(19) 0.91638(11) 0.0288(5) Uani 1 1 d . . . . .
H22 H 0.2890 0.8571 0.9201 0.035 Uiso 1 1 calc R U . . .
C23 C 0.1342(2) 0.9544(2) 0.91910(12) 0.0333(5) Uani 1 1 d . . . . .
H23 H 0.1687 1.0375 0.9250 0.040 Uiso 1 1 calc R U . . .
C24 C 0.01200(19) 0.9409(2) 0.91319(11) 0.0326(5) Uani 1 1 d . . . . .
H24 H -0.0371 1.0145 0.9153 0.039 Uiso 1 1 calc R U . . .
C25 C -0.03773(19) 0.8198(2) 0.90416(12) 0.0332(5) Uani 1 1 d . . . . .
H25 H -0.1213 0.8104 0.8995 0.040 Uiso 1 1 calc R U . . .
C26 C 0.03352(17) 0.7120(2) 0.90189(11) 0.0280(5) Uani 1 1 d . . . . .
H26 H -0.0013 0.6291 0.8960 0.034 Uiso 1 1 calc R U . . .
N1 N 0.26523(13) 0.54446(14) 0.97047(8) 0.0210(4) Uani 1 1 d . . . . .
O1 O 0.02956(11) 0.61021(13) 1.05984(8) 0.0285(3) Uani 1 1 d . . . . .
O2 O 0.16637(12) 0.76823(13) 1.07228(7) 0.0282(3) Uani 1 1 d . . . . .
O3 O 0.30519(14) 0.34789(14) 1.18560(8) 0.0353(4) Uani 1 1 d . . . . .
O4 O 0.18797(14) 0.52192(15) 1.18637(8) 0.0371(4) Uani 1 1 d . . . . .
O5 O 0.32715(13) 0.16493(13) 1.06022(9) 0.0380(4) Uani 1 1 d . . . . .
O6 O 0.50448(13) 0.25235(15) 1.09104(9) 0.0437(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.380(3) . ?
C1 N1 1.384(2) . ?
C1 C13 1.495(3) . ?
C2 C3 1.418(3) . ?
C2 C15 1.471(3) . ?
C3 C4 1.381(3) . ?
C3 C17 1.492(3) . ?
C4 N1 1.405(2) . ?
C4 C5 1.443(3) . ?
C5 C6 1.403(3) . ?
C5 C10 1.410(3) . ?
C6 C7 1.377(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.370(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.411(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.454(3) . ?
C11 C12 1.356(3) . ?
C11 C19 1.513(3) . ?
C12 N1 1.419(2) . ?
C12 C21 1.487(3) . ?
C13 O2 1.205(2) . ?
C13 O1 1.339(2) . ?
C14 O1 1.448(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 O4 1.207(2) . ?
C15 O3 1.338(2) . ?
C16 O3 1.446(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 O6 1.195(2) . ?
C17 O5 1.339(2) . ?
C18 O5 1.453(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.527(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C26 1.390(3) . ?
C21 C22 1.392(3) . ?
C22 C23 1.382(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.389(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.383(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.386(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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
C2 C1 N1 107.67(16) . . ?
C2 C1 C13 124.87(17) . . ?
N1 C1 C13 127.39(16) . . ?
C1 C2 C3 108.49(17) . . ?
C1 C2 C15 123.45(17) . . ?
C3 C2 C15 127.63(17) . . ?
C4 C3 C2 107.33(16) . . ?
C4 C3 C17 127.11(18) . . ?
C2 C3 C17 125.36(17) . . ?
C3 C4 N1 107.74(16) . . ?
C3 C4 C5 133.21(18) . . ?
N1 C4 C5 119.05(16) . . ?
C6 C5 C10 119.90(18) . . ?
C6 C5 C4 121.46(18) . . ?
C10 C5 C4 118.60(17) . . ?
C7 C6 C5 120.32(19) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.34(19) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.02(19) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 121.43(19) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C5 C10 C9 117.96(18) . . ?
C5 C10 C11 119.82(17) . . ?
C9 C10 C11 122.14(18) . . ?
C12 C11 C10 120.77(18) . . ?
C12 C11 C19 119.85(18) . . ?
C10 C11 C19 119.38(17) . . ?
C11 C12 N1 119.72(17) . . ?
C11 C12 C21 123.41(18) . . ?
N1 C12 C21 116.82(16) . . ?
O2 C13 O1 125.03(18) . . ?
O2 C13 C1 125.29(17) . . ?
O1 C13 C1 109.57(16) . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 O3 124.03(19) . . ?
O4 C15 C2 125.00(18) . . ?
O3 C15 C2 110.96(17) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O6 C17 O5 123.31(18) . . ?
O6 C17 C3 126.77(18) . . ?
O5 C17 C3 109.89(16) . . ?
O5 C18 H18A 109.5 . . ?
O5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C19 C20 111.5(2) . . ?
C11 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
C11 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 119.24(18) . . ?
C26 C21 C12 121.72(17) . . ?
C22 C21 C12 119.03(17) . . ?
C23 C22 C21 120.44(19) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 120.1(2) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 119.63(19) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.44(19) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.14(19) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?
C1 N1 C4 108.76(15) . . ?
C1 N1 C12 129.37(16) . . ?
C4 N1 C12 121.47(16) . . ?
C13 O1 C14 115.66(16) . . ?
C15 O3 C16 116.08(17) . . ?
C17 O5 C18 115.64(17) . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.049

