# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_ecat
_database_code_depnum_ccdc_archive 'CCDC 2247944'
loop_
_audit_author_name
_audit_author_address
'Duane Choquesillo-Lazarte'
;Laboratorio de Estudios Cristalograficos,IACT,CSIC
Spain
;
_audit_update_record             
;
2023-03-11 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2023-03-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C9 H11 N O2), C6 H6 O2'
_chemical_formula_sum            'C24 H28 N2 O6'
_chemical_formula_weight         440.48
_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                   7.7814(12)
_cell_length_b                   10.0144(12)
_cell_length_c                   15.979(2)
_cell_angle_alpha                87.193(7)
_cell_angle_beta                 77.808(7)
_cell_angle_gamma                69.864(7)
_cell_volume                     1142.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2954
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      66.31
_cell_measurement_theta_min      21.81
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.928
_exptl_absorpt_coefficient_mu    0.761
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6845
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0698 before and 0.0445 after correction.
The Ratio of minimum to maximum transmission is 0.9093.
The λ/2 correction factor is 0.0000.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12456
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        66.709
_diffrn_reflns_theta_max         66.709
_diffrn_reflns_theta_min         2.830
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3241
_reflns_number_total             3966
_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       'Bruker Apex 4, 2022'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3966
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0593
_refine_ls_restrained_S_all      1.043
_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)+(0.1178P)²+0.4097P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1876
_refine_ls_wR_factor_ref         0.1971
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C22(H22), C23(H23), C24(H24), C25(H25)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A), O6(H6A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0626(3) 0.97530(17) 0.64141(11) 0.0612(5) Uani 1 1 d . . . . .
N1 N 0.0214(3) 1.2064(2) 0.63097(14) 0.0643(6) Uani 1 1 d . . . . .
H1A H -0.052353 1.224205 0.680514 0.077 Uiso 1 1 calc R U . . .
H1B H 0.046003 1.274417 0.601748 0.077 Uiso 1 1 calc R U . . .
C1 C 0.2202(3) 1.0447(2) 0.51244(14) 0.0457(5) Uani 1 1 d . . . . .
O2 O 0.2298(2) 1.27898(16) 0.49549(11) 0.0579(5) Uani 1 1 d . . . . .
C2 C 0.2824(3) 1.1445(2) 0.46143(14) 0.0470(5) Uani 1 1 d . . . . .
C3 C 0.3934(4) 1.1047(3) 0.38051(16) 0.0574(6) Uani 1 1 d . . . . .
H3 H 0.432789 1.171003 0.346487 0.069 Uiso 1 1 calc R U . . .
C4 C 0.4456(4) 0.9662(3) 0.35028(17) 0.0639(7) Uani 1 1 d . . . . .
H4 H 0.521415 0.939783 0.296176 0.077 Uiso 1 1 calc R U . . .
C5 C 0.3870(4) 0.8677(3) 0.39908(18) 0.0636(7) Uani 1 1 d . . . . .
H5 H 0.422674 0.774814 0.378336 0.076 Uiso 1 1 calc R U . . .
C6 C 0.2752(4) 0.9071(2) 0.47885(16) 0.0542(6) Uani 1 1 d . . . . .
H6 H 0.234858 0.839889 0.511483 0.065 Uiso 1 1 calc R U . . .
C7 C 0.0973(3) 1.0740(2) 0.59965(14) 0.0480(5) Uani 1 1 d . . . . .
C8 C 0.3094(4) 1.3787(3) 0.45042(17) 0.0613(7) Uani 1 1 d . . . . .
H8A H 0.262501 1.406703 0.398280 0.074 Uiso 1 1 calc R U . . .
H8B H 0.444606 1.336325 0.435311 0.074 Uiso 1 1 calc R U . . .
C9 C 0.2535(4) 1.5053(3) 0.5091(2) 0.0727(8) Uani 1 1 d . . . . .
H9A H 0.310249 1.572110 0.482360 0.109 Uiso 1 1 calc R U . . .
H9B H 0.294583 1.475354 0.561724 0.109 Uiso 1 1 calc R U . . .
H9C H 0.119856 1.549480 0.520895 0.109 Uiso 1 1 calc R U . . .
N2 N 0.8450(4) 0.0168(2) 0.81383(15) 0.0890(9) Uani 1 1 d . . . . .
H2A H 0.894804 0.006303 0.760053 0.107 Uiso 1 1 calc R U . . .
H2B H 0.856578 -0.056538 0.845425 0.107 Uiso 1 1 calc R U . . .
O3 O 0.7349(3) 0.25006(18) 0.80213(11) 0.0668(5) Uani 1 1 d . . . . .
O4 O 0.8363(3) -0.07597(19) 0.97048(11) 0.0706(6) Uani 1 1 d . . . . .
C11 C 0.6646(3) 0.1614(2) 0.94131(15) 0.0518(6) Uani 1 1 d . . . . .
C12 C 0.7088(4) 0.0534(3) 1.00090(16) 0.0588(6) Uani 1 1 d . . . . .
C13 C 0.6266(5) 0.0813(3) 1.08712(18) 0.0775(8) Uani 1 1 d . . . . .
H13 H 0.656561 0.010385 1.126768 0.093 Uiso 1 1 calc R U . . .
C14 C 0.5001(5) 0.2146(4) 1.1139(2) 0.0861(10) Uani 1 1 d . . . . .
H14 H 0.445999 0.232721 1.171821 0.103 Uiso 1 1 calc R U . . .
C15 C 0.4532(4) 0.3207(3) 1.0566(2) 0.0769(8) Uani 1 1 d . . . . .
H15 H 0.365524 0.409457 1.075017 0.092 Uiso 1 1 calc R U . . .
C16 C 0.5378(4) 0.2939(3) 0.97125(18) 0.0633(7) Uani 1 1 d . . . . .
H16 H 0.509043 0.366691 0.932616 0.076 Uiso 1 1 calc R U . . .
C17 C 0.7514(3) 0.1446(2) 0.84764(15) 0.0515(6) Uani 1 1 d . . . . .
C18 C 0.8891(4) -0.1901(3) 1.02793(17) 0.0652(7) Uani 1 1 d . . . . .
H18A H 0.780632 -0.213325 1.056913 0.078 Uiso 1 1 calc R U . . .
H18B H 0.944053 -0.163450 1.070713 0.078 Uiso 1 1 calc R U . . .
C19 C 1.0275(5) -0.3137(3) 0.9753(2) 0.0802(9) Uani 1 1 d . . . . .
H19A H 0.968691 -0.343474 0.936261 0.120 Uiso 1 1 calc R U . . .
H19B H 1.073931 -0.390575 1.012072 0.120 Uiso 1 1 calc R U . . .
H19C H 1.129595 -0.287004 0.943628 0.120 Uiso 1 1 calc R U . . .
O5 O 0.5160(2) 0.50280(19) 0.75164(14) 0.0694(5) Uani 1 1 d . . . . .
H5A H 0.573794 0.423651 0.766971 0.104 Uiso 1 1 calc R U . . .
O6 O 0.2941(3) 0.74299(19) 0.70188(15) 0.0725(6) Uani 1 1 d . . . . .
H6A H 0.218145 0.809768 0.682911 0.109 Uiso 1 1 calc R U . . .
C20 C 0.3364(3) 0.5127(2) 0.75362(15) 0.0494(5) Uani 1 1 d . . . . .
C21 C 0.2186(3) 0.6395(2) 0.72650(15) 0.0509(6) Uani 1 1 d . . . . .
C22 C 0.0364(4) 0.6539(3) 0.72562(16) 0.0571(6) Uani 1 1 d . . . . .
H22 H -0.041585 0.737893 0.706949 0.069 Uiso 1 1 calc R U . . .
C23 C -0.0321(4) 0.5445(3) 0.75230(17) 0.0651(7) Uani 1 1 d . . . . .
H23 H -0.155369 0.555246 0.751615 0.078 Uiso 1 1 calc R U . . .
C24 C 0.0828(4) 0.4207(3) 0.77963(17) 0.0656(7) Uani 1 1 d . . . . .
H24 H 0.037407 0.347354 0.798076 0.079 Uiso 1 1 calc R U . . .
C25 C 0.2668(4) 0.4050(3) 0.77974(16) 0.0575(6) Uani 1 1 d . . . . .
H25 H 0.344479 0.320303 0.797762 0.069 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
O1 C7 1.241(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C7 1.325(3) . ?
C1 C2 1.408(3) . ?
C1 C6 1.393(3) . ?
C1 C7 1.492(3) . ?
O2 C2 1.370(3) . ?
O2 C8 1.438(3) . ?
C2 C3 1.385(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.369(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.372(4) . ?
C6 H6 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.496(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C17 1.312(3) . ?
O3 C17 1.237(3) . ?
O4 C12 1.368(3) . ?
O4 C18 1.432(3) . ?
C11 C12 1.406(3) . ?
C11 C16 1.387(3) . ?
C11 C17 1.498(3) . ?
C12 C13 1.389(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.371(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.379(4) . ?
C16 H16 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.483(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O5 H5A 0.8200 . ?
O5 C20 1.360(3) . ?
O6 H6A 0.8200 . ?
O6 C21 1.362(3) . ?
C20 C21 1.397(3) . ?
C20 C25 1.376(3) . ?
C21 C22 1.378(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.388(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.370(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.386(4) . ?
C25 H25 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
H1A N1 H1B 120.0 . . ?
C7 N1 H1A 120.0 . . ?
C7 N1 H1B 120.0 . . ?
C2 C1 C7 125.5(2) . . ?
C6 C1 C2 117.8(2) . . ?
C6 C1 C7 116.7(2) . . ?
C2 O2 C8 119.15(18) . . ?
O2 C2 C1 117.4(2) . . ?
O2 C2 C3 122.6(2) . . ?
C3 C2 C1 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(2) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 H6 119.0 . . ?
C5 C6 C1 122.0(2) . . ?
C5 C6 H6 119.0 . . ?
O1 C7 N1 120.4(2) . . ?
O1 C7 C1 119.9(2) . . ?
N1 C7 C1 119.6(2) . . ?
O2 C8 H8A 110.3 . . ?
O2 C8 H8B 110.3 . . ?
O2 C8 C9 107.1(2) . . ?
H8A C8 H8B 108.6 . . ?
C9 C8 H8A 110.3 . . ?
C9 C8 H8B 110.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H2A N2 H2B 120.0 . . ?
C17 N2 H2A 120.0 . . ?
C17 N2 H2B 120.0 . . ?
C12 O4 C18 120.3(2) . . ?
C12 C11 C17 124.2(2) . . ?
C16 C11 C12 118.2(2) . . ?
C16 C11 C17 117.5(2) . . ?
O4 C12 C11 117.4(2) . . ?
O4 C12 C13 122.7(2) . . ?
C13 C12 C11 119.8(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.1(3) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 119.0(3) . . ?
C16 C15 H15 120.5 . . ?
C11 C16 H16 119.0 . . ?
C15 C16 C11 121.9(3) . . ?
C15 C16 H16 119.0 . . ?
N2 C17 C11 119.5(2) . . ?
O3 C17 N2 120.0(2) . . ?
O3 C17 C11 120.6(2) . . ?
O4 C18 H18A 110.4 . . ?
O4 C18 H18B 110.4 . . ?
O4 C18 C19 106.8(2) . . ?
H18A C18 H18B 108.6 . . ?
C19 C18 H18A 110.4 . . ?
C19 C18 H18B 110.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 O5 H5A 109.5 . . ?
C21 O6 H6A 109.5 . . ?
O5 C20 C21 117.4(2) . . ?
O5 C20 C25 123.6(2) . . ?
C25 C20 C21 119.0(2) . . ?
O6 C21 C20 116.6(2) . . ?
O6 C21 C22 123.7(2) . . ?
C22 C21 C20 119.6(2) . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.8(2) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.6(3) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 120.1 . . ?
C23 C24 C25 119.9(2) . . ?
C25 C24 H24 120.1 . . ?
C20 C25 C24 121.1(2) . . ?
C20 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O3 0.86 2.23 3.084(3) 171.3 1_465 yes
N1 H1B O2 0.86 1.99 2.649(3) 133.2 . yes
N2 H2A O1 0.86 2.03 2.879(3) 168.1 1_645 yes
N2 H2B O4 0.86 1.98 2.622(3) 131.0 . yes
O5 H5A O3 0.82 1.90 2.715(2) 172.1 . yes
O6 H6A O1 0.82 1.87 2.687(2) 173.0 . yes

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
C1 C2 C3 C4 -1.0(4) . . . . ?
O2 C2 C3 C4 178.5(2) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
C2 C1 C7 O1 -174.6(2) . . . . ?
C2 C1 C7 N1 7.3(3) . . . . ?
C2 O2 C8 C9 -170.3(2) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C6 C1 C2 O2 -179.1(2) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C6 C1 C7 O1 6.3(3) . . . . ?
C6 C1 C7 N1 -171.7(2) . . . . ?
C7 C1 C2 O2 1.8(3) . . . . ?
C7 C1 C2 C3 -178.7(2) . . . . ?
C7 C1 C6 C5 179.5(2) . . . . ?
C8 O2 C2 C1 172.1(2) . . . . ?
C8 O2 C2 C3 -7.4(3) . . . . ?
O4 C12 C13 C14 179.3(3) . . . . ?
C11 C12 C13 C14 0.7(5) . . . . ?
C12 O4 C18 C19 180.0(2) . . . . ?
C12 C11 C16 C15 -1.1(4) . . . . ?
C12 C11 C17 N2 14.7(4) . . . . ?
C12 C11 C17 O3 -165.6(3) . . . . ?
C12 C13 C14 C15 0.3(6) . . . . ?
C13 C14 C15 C16 -1.6(6) . . . . ?
C14 C15 C16 C11 2.1(5) . . . . ?
C16 C11 C12 O4 -179.0(2) . . . . ?
C16 C11 C12 C13 -0.3(4) . . . . ?
C16 C11 C17 N2 -167.8(3) . . . . ?
C16 C11 C17 O3 11.9(4) . . . . ?
C17 C11 C12 O4 -1.6(4) . . . . ?
C17 C11 C12 C13 177.2(3) . . . . ?
C17 C11 C16 C15 -178.7(3) . . . . ?
C18 O4 C12 C11 179.3(2) . . . . ?
C18 O4 C12 C13 0.6(4) . . . . ?
O5 C20 C21 O6 -1.1(3) . . . . ?
O5 C20 C21 C22 178.7(2) . . . . ?
O5 C20 C25 C24 -179.4(2) . . . . ?
O6 C21 C22 C23 -179.4(2) . . . . ?
C20 C21 C22 C23 0.7(4) . . . . ?
C21 C20 C25 C24 -0.1(4) . . . . ?
C21 C22 C23 C24 -0.1(4) . . . . ?
C22 C23 C24 C25 -0.6(4) . . . . ?
C23 C24 C25 C20 0.7(4) . . . . ?
C25 C20 C21 O6 179.6(2) . . . . ?
C25 C20 C21 C22 -0.6(4) . . . . ?


_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_ehq
_database_code_depnum_ccdc_archive 'CCDC 2247946'
loop_
_audit_author_name
_audit_author_address
'Duane Choquesillo-Lazarte'
;Laboratorio de Estudios Cristalograficos,IACT,CSIC
Spain
;
_audit_update_record             
;
2023-03-11 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2023-03-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H11 N O2, C3 H3 O'
_chemical_formula_sum            'C12 H14 N O3'
_chemical_formula_weight         220.24
_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                   7.2548(5)
_cell_length_b                   9.0844(6)
_cell_length_c                   9.5457(5)
_cell_angle_alpha                99.864(3)
_cell_angle_beta                 99.082(3)
_cell_angle_gamma                107.888(3)
_cell_volume                     574.80(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3416
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      66.35
_cell_measurement_theta_min      6.57
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.928
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5177
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1140 before and 0.0802 after correction.
The Ratio of minimum to maximum transmission is 0.6877.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             234
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9342
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        66.467
_diffrn_reflns_theta_max         66.467
_diffrn_reflns_theta_min         5.262
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1790
_reflns_number_total             1958
_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       'Bruker Apex 4, 2022'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.070(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1958
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.065
_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)+(0.0726P)²+0.0506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1264
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.15112(18) 0.79946(12) 0.17966(11) 0.0781(4) Uani 1 1 d . . . . .
N1 N 0.19059(18) 0.80486(13) -0.04633(12) 0.0635(4) Uani 1 1 d . . . . .
H1A H 0.163357 0.703559 -0.069468 0.076 Uiso 1 1 calc R U . . .
H1B H 0.218181 0.860210 -0.109716 0.076 Uiso 1 1 calc R U . . .
C1 C 0.23964(17) 1.05258(15) 0.12506(13) 0.0501(3) Uani 1 1 d . . . . .
O2 O 0.30166(15) 1.08970(11) -0.10497(10) 0.0629(3) Uani 1 1 d . . . . .
C2 C 0.29384(18) 1.15533(15) 0.03285(14) 0.0523(4) Uani 1 1 d . . . . .
C3 C 0.3345(2) 1.31767(17) 0.08268(17) 0.0661(4) Uani 1 1 d . . . . .
H3 H 0.370933 1.385942 0.021696 0.079 Uiso 1 1 calc R U . . .
C4 C 0.3211(2) 1.37783(17) 0.22197(18) 0.0710(4) Uani 1 1 d . . . . .
H4 H 0.349040 1.486589 0.254135 0.085 Uiso 1 1 calc R U . . .
C5 C 0.2672(2) 1.27952(18) 0.31369(16) 0.0681(4) Uani 1 1 d . . . . .
H5 H 0.257619 1.320599 0.407376 0.082 Uiso 1 1 calc R U . . .
C6 C 0.2273(2) 1.11853(17) 0.26463(14) 0.0599(4) Uani 1 1 d . . . . .
H6 H 0.190858 1.051809 0.326884 0.072 Uiso 1 1 calc R U . . .
C7 C 0.19002(18) 0.87525(15) 0.08619(14) 0.0536(3) Uani 1 1 d . . . . .
C8 C 0.3534(2) 1.18944(19) -0.20390(16) 0.0688(4) Uani 1 1 d . . . . .
H8A H 0.487228 1.265341 -0.166528 0.083 Uiso 1 1 calc R U . . .
H8B H 0.262433 1.247694 -0.216571 0.083 Uiso 1 1 calc R U . . .
C9 C 0.3399(3) 1.0831(2) -0.34593(17) 0.0874(5) Uani 1 1 d . . . . .
H9A H 0.378804 1.146308 -0.414236 0.131 Uiso 1 1 calc R U . . .
H9B H 0.205635 1.011454 -0.383621 0.131 Uiso 1 1 calc R U . . .
H9C H 0.426685 1.023123 -0.331168 0.131 Uiso 1 1 calc R U . . .
O3 O -0.09200(15) 0.52848(11) 0.21541(10) 0.0651(3) Uani 1 1 d . . . . .
H3A H -0.015210 0.610811 0.204055 0.098 Uiso 1 1 calc R U . . .
C10 C -0.04387(19) 0.51832(14) 0.35810(13) 0.0522(4) Uani 1 1 d . . . . .
C11 C -0.16779(19) 0.39349(15) 0.40123(14) 0.0557(4) Uani 1 1 d . . . . .
H11 H -0.281111 0.321687 0.335186 0.067 Uiso 1 1 calc R U . . .
C12 C -0.12392(19) 0.37497(14) 0.54219(14) 0.0559(4) Uani 1 1 d . . . . .
H12 H -0.207546 0.290390 0.570172 0.067 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
O1 C7 1.2330(16) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C7 1.3173(16) . ?
C1 C2 1.4021(17) . ?
C1 C6 1.3926(18) . ?
C1 C7 1.5030(18) . ?
O2 C2 1.3656(15) . ?
O2 C8 1.4317(15) . ?
C2 C3 1.3915(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.371(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(2) . ?
C6 H6 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.494(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
O3 H3A 0.8200 . ?
O3 C10 1.3778(15) . ?
C10 C11 1.3835(18) . ?
C10 C12 1.3859(19) 2_566 ?
C11 H11 0.9300 . ?
C11 C12 1.3840(18) . ?
C12 H12 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
H1A N1 H1B 120.0 . . ?
C7 N1 H1A 120.0 . . ?
C7 N1 H1B 120.0 . . ?
C2 C1 C7 125.76(11) . . ?
C6 C1 C2 117.88(12) . . ?
C6 C1 C7 116.35(11) . . ?
C2 O2 C8 119.76(11) . . ?
O2 C2 C1 117.68(11) . . ?
O2 C2 C3 122.53(12) . . ?
C3 C2 C1 119.78(12) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.34(13) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.89(13) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.86(13) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 H6 118.9 . . ?
C5 C6 C1 122.24(13) . . ?
C5 C6 H6 118.9 . . ?
O1 C7 N1 121.66(12) . . ?
O1 C7 C1 119.07(12) . . ?
N1 C7 C1 119.26(11) . . ?
O2 C8 H8A 110.3 . . ?
O2 C8 H8B 110.3 . . ?
O2 C8 C9 107.03(13) . . ?
H8A C8 H8B 108.6 . . ?
C9 C8 H8A 110.3 . . ?
C9 C8 H8B 110.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 O3 H3A 109.5 . . ?
O3 C10 C11 117.81(12) . . ?
O3 C10 C12 122.90(11) . 2_566 ?
C11 C10 C12 119.27(12) . 2_566 ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.32(12) . . ?
C12 C11 H11 119.8 . . ?
C10 C12 H12 119.8 2_566 . ?
C11 C12 C10 120.41(12) . 2_566 ?
C11 C12 H12 119.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O3 0.86 2.18 2.9861(15) 156.2 2_565 yes
N1 H1B O2 0.86 1.97 2.6488(14) 134.4 . yes
O3 H3A O1 0.82 1.84 2.6642(13) 178.0 . yes

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
C1 C2 C3 C4 -0.2(2) . . . . ?
O2 C2 C3 C4 178.82(12) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
C2 C1 C7 O1 177.56(12) . . . . ?
C2 C1 C7 N1 -1.95(19) . . . . ?
C2 O2 C8 C9 -177.43(12) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
C6 C1 C2 O2 -178.63(10) . . . . ?
C6 C1 C2 C3 0.47(19) . . . . ?
C6 C1 C7 O1 -3.41(18) . . . . ?
C6 C1 C7 N1 177.08(11) . . . . ?
C7 C1 C2 O2 0.39(19) . . . . ?
C7 C1 C2 C3 179.48(12) . . . . ?
C7 C1 C6 C5 -179.42(12) . . . . ?
C8 O2 C2 C1 179.07(11) . . . . ?
C8 O2 C2 C3 0.0(2) . . . . ?
O3 C10 C11 C12 178.30(11) . . . . ?
C10 C11 C12 C10 0.4(2) . . . 2_566 ?
C12 C10 C11 C12 -0.4(2) 2_566 . . . ?


_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_ephl
_database_code_depnum_ccdc_archive 'CCDC 2247947'
loop_
_audit_author_name
_audit_author_address
'Duane Choquesillo-Lazarte'
;Laboratorio de Estudios Cristalograficos,IACT,CSIC
Spain
;
_audit_update_record             
;
2023-03-11 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2023-03-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C9 H11 N O2), C6 H6 O3'
_chemical_formula_sum            'C24 H28 N2 O7'
_chemical_formula_weight         456.48
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   9.9310(7)
_cell_length_b                   10.0681(6)
_cell_length_c                   12.1027(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.780(4)
_cell_angle_gamma                90
_cell_volume                     1192.52(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    574
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      65.77
_cell_measurement_theta_min      27.25
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.926
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6372
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0880 before and 0.0768 after correction.
The Ratio of minimum to maximum transmission is 0.8464.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16420
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        66.498
_diffrn_reflns_theta_max         66.498
_diffrn_reflns_theta_min         4.391
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    0.820
_reflns_Friedel_fraction_max     0.820
_reflns_number_gt                3301
_reflns_number_total             3793
_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       'Bruker Apex 4, 2022'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1309 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.16(13)
_refine_ls_extinction_coef       0.0096(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3793
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0404
_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)+(0.0635P)²+0.0422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1108
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C21(H21), C23(H23), C25(H25)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A), O6(H6A), O7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7317(3) 0.7116(2) 0.1651(3) 0.0751(7) Uani 1 1 d . . . . .
N1 N 0.7168(3) 0.4912(3) 0.1689(3) 0.0783(9) Uani 1 1 d . . . . .
H1A H 0.788176 0.483872 0.137786 0.094 Uiso 1 1 calc R U . . .
H1B H 0.675277 0.421245 0.186074 0.094 Uiso 1 1 calc R U . . .
C1 C 0.5469(3) 0.6228(3) 0.2426(3) 0.0552(7) Uani 1 1 d . . . . .
O2 O 0.5117(2) 0.3902(2) 0.2496(2) 0.0673(6) Uani 1 1 d . . . . .
C2 C 0.4684(3) 0.5144(3) 0.2704(3) 0.0557(8) Uani 1 1 d . . . . .
C3 C 0.3526(4) 0.5382(4) 0.3179(3) 0.0649(9) Uani 1 1 d . . . . .
H3 H 0.300146 0.467090 0.335089 0.078 Uiso 1 1 calc R U . . .
C4 C 0.3148(4) 0.6654(4) 0.3397(3) 0.0752(10) Uani 1 1 d . . . . .
H4 H 0.237327 0.679689 0.371697 0.090 Uiso 1 1 calc R U . . .
C5 C 0.3914(4) 0.7726(4) 0.3143(4) 0.0795(11) Uani 1 1 d . . . . .
H5 H 0.366185 0.858841 0.329344 0.095 Uiso 1 1 calc R U . . .
C6 C 0.5051(4) 0.7497(3) 0.2665(3) 0.0701(10) Uani 1 1 d . . . . .
H6 H 0.556188 0.821991 0.249423 0.084 Uiso 1 1 calc R U . . .
C7 C 0.6711(3) 0.6100(3) 0.1902(3) 0.0573(8) Uani 1 1 d . . . . .
C8 C 0.4356(4) 0.2761(3) 0.2730(3) 0.0671(9) Uani 1 1 d . . . . .
H8A H 0.343735 0.279280 0.230155 0.080 Uiso 1 1 calc R U . . .
H8B H 0.429519 0.272612 0.352124 0.080 Uiso 1 1 calc R U . . .
C9 C 0.5101(5) 0.1576(4) 0.2404(4) 0.0869(12) Uani 1 1 d . . . . .
H9A H 0.510967 0.159905 0.161270 0.130 Uiso 1 1 calc R U . . .
H9B H 0.464947 0.078202 0.258653 0.130 Uiso 1 1 calc R U . . .
H9C H 0.602234 0.158363 0.280434 0.130 Uiso 1 1 calc R U . . .
N2 N 0.4958(3) 0.3174(3) 0.5899(3) 0.0806(10) Uani 1 1 d . . . . .
H2A H 0.419738 0.309348 0.614201 0.097 Uiso 1 1 calc R U . . .
H2B H 0.538443 0.247922 0.573104 0.097 Uiso 1 1 calc R U . . .
O3 O 0.4848(2) 0.5377(2) 0.6031(2) 0.0669(6) Uani 1 1 d . . . . .
O4 O 0.7133(3) 0.2186(2) 0.5240(2) 0.0720(7) Uani 1 1 d . . . . .
C11 C 0.6772(3) 0.4508(3) 0.5330(2) 0.0537(7) Uani 1 1 d . . . . .
C12 C 0.7578(3) 0.3445(3) 0.5067(3) 0.0582(8) Uani 1 1 d . . . . .
C13 C 0.8779(4) 0.3694(4) 0.4663(3) 0.0706(10) Uani 1 1 d . . . . .
H13 H 0.932064 0.299025 0.450266 0.085 Uiso 1 1 calc R U . . .
C14 C 0.9170(4) 0.4978(5) 0.4500(3) 0.0767(11) Uani 1 1 d . . . . .
H14 H 0.997217 0.513656 0.422102 0.092 Uiso 1 1 calc R U . . .
C15 C 0.8388(5) 0.6030(4) 0.4744(3) 0.0755(10) Uani 1 1 d . . . . .
H15 H 0.866416 0.689611 0.463595 0.091 Uiso 1 1 calc R U . . .
C16 C 0.7197(4) 0.5796(3) 0.5149(3) 0.0628(8) Uani 1 1 d . . . . .
H16 H 0.666582 0.651116 0.530397 0.075 Uiso 1 1 calc R U . . .
C17 C 0.5474(3) 0.4370(3) 0.5784(3) 0.0561(8) Uani 1 1 d . . . . .
C18 C 0.7948(4) 0.1071(4) 0.5051(4) 0.0739(10) Uani 1 1 d . . . . .
H18A H 0.882830 0.110668 0.554143 0.089 Uiso 1 1 calc R U . . .
H18B H 0.809811 0.105713 0.427962 0.089 Uiso 1 1 calc R U . . .
C19 C 0.7165(6) -0.0140(4) 0.5300(6) 0.1015(15) Uani 1 1 d . . . . .
H19A H 0.628799 -0.014773 0.482215 0.152 Uiso 1 1 calc R U . . .
H19B H 0.704205 -0.012025 0.606984 0.152 Uiso 1 1 calc R U . . .
H19C H 0.766381 -0.092357 0.516733 0.152 Uiso 1 1 calc R U . . .
O5 O 0.7861(3) -0.0352(2) 0.1309(2) 0.0707(7) Uani 1 1 d . . . . .
H5A H 0.762800 -0.109300 0.148458 0.106 Uiso 1 1 calc R U . . .
O6 O 1.0981(2) 0.3083(2) 0.2727(2) 0.0671(6) Uani 1 1 d . . . . .
H6A H 1.054182 0.348479 0.219562 0.101 Uiso 1 1 calc R U . . .
O7 O 1.1127(3) -0.1063(2) 0.4609(2) 0.0674(7) Uani 1 1 d . . . . .
H7 H 1.170501 -0.065935 0.504753 0.101 Uiso 1 1 calc R U . . .
C20 C 0.8941(3) 0.0084(3) 0.2092(2) 0.0506(7) Uani 1 1 d . . . . .
C21 C 0.9531(3) -0.0733(3) 0.2968(2) 0.0506(7) Uani 1 1 d . . . . .
H21 H 0.921508 -0.159409 0.303293 0.061 Uiso 1 1 calc R U . . .
C22 C 1.0595(3) -0.0238(3) 0.3736(3) 0.0493(7) Uani 1 1 d . . . . .
C23 C 1.1091(3) 0.1031(3) 0.3648(3) 0.0519(7) Uani 1 1 d . . . . .
H23 H 1.181885 0.134648 0.416841 0.062 Uiso 1 1 calc R U . . .
C24 C 1.0479(3) 0.1831(3) 0.2763(3) 0.0497(7) Uani 1 1 d . . . . .
C25 C 0.9406(3) 0.1360(3) 0.1983(3) 0.0508(7) Uani 1 1 d . . . . .
H25 H 0.900340 0.189645 0.139295 0.061 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
O1 C7 1.250(4) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C7 1.319(4) . ?
C1 C2 1.415(4) . ?
C1 C6 1.389(5) . ?
C1 C7 1.486(5) . ?
O2 C2 1.360(4) . ?
O2 C8 1.430(4) . ?
C2 C3 1.391(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(6) . ?
C6 H6 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.492(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C17 1.325(4) . ?
O3 C17 1.252(4) . ?
O4 C12 1.369(4) . ?
O4 C18 1.425(4) . ?
C11 C12 1.406(5) . ?
C11 C16 1.393(5) . ?
C11 C17 1.491(5) . ?
C12 C13 1.386(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.375(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.376(6) . ?
C16 H16 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.504(7) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O5 H5A 0.8200 . ?
O5 C20 1.377(3) . ?
O6 H6A 0.8200 . ?
O6 C24 1.359(4) . ?
O7 H7 0.8200 . ?
O7 C22 1.376(4) . ?
C20 C21 1.390(4) . ?
C20 C25 1.379(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.377(4) . ?
C22 C23 1.380(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.395(4) . ?
C24 C25 1.381(4) . ?
C25 H25 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
H1A N1 H1B 120.0 . . ?
C7 N1 H1A 120.0 . . ?
C7 N1 H1B 120.0 . . ?
C2 C1 C7 124.4(3) . . ?
C6 C1 C2 117.7(3) . . ?
C6 C1 C7 117.9(3) . . ?
C2 O2 C8 120.5(3) . . ?
O2 C2 C1 117.5(3) . . ?
O2 C2 C3 123.0(3) . . ?
C3 C2 C1 119.5(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(4) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 119.0(4) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 H6 118.7 . . ?
C5 C6 C1 122.6(3) . . ?
C5 C6 H6 118.7 . . ?
O1 C7 N1 119.9(3) . . ?
O1 C7 C1 120.1(3) . . ?
N1 C7 C1 120.0(3) . . ?
O2 C8 H8A 110.4 . . ?
O2 C8 H8B 110.4 . . ?
O2 C8 C9 106.7(3) . . ?
H8A C8 H8B 108.6 . . ?
C9 C8 H8A 110.4 . . ?
C9 C8 H8B 110.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H2A N2 H2B 120.0 . . ?
C17 N2 H2A 120.0 . . ?
C17 N2 H2B 120.0 . . ?
C12 O4 C18 119.8(3) . . ?
C12 C11 C17 125.0(3) . . ?
C16 C11 C12 118.3(3) . . ?
C16 C11 C17 116.7(3) . . ?
O4 C12 C11 117.3(3) . . ?
O4 C12 C13 122.7(3) . . ?
C13 C12 C11 119.9(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.7(4) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(4) . . ?
C16 C15 H15 120.1 . . ?
C11 C16 H16 119.4 . . ?
C15 C16 C11 121.1(3) . . ?
C15 C16 H16 119.4 . . ?
N2 C17 C11 119.8(3) . . ?
O3 C17 N2 119.6(3) . . ?
O3 C17 C11 120.5(3) . . ?
O4 C18 H18A 110.5 . . ?
O4 C18 H18B 110.5 . . ?
O4 C18 C19 106.2(3) . . ?
H18A C18 H18B 108.7 . . ?
C19 C18 H18A 110.5 . . ?
C19 C18 H18B 110.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 O5 H5A 109.5 . . ?
C24 O6 H6A 109.5 . . ?
C22 O7 H7 109.5 . . ?
O5 C20 C21 121.0(3) . . ?
O5 C20 C25 117.8(3) . . ?
C25 C20 C21 121.3(3) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 C20 118.5(3) . . ?
C22 C21 H21 120.8 . . ?
O7 C22 C21 116.8(3) . . ?
O7 C22 C23 121.5(3) . . ?
C21 C22 C23 121.7(3) . . ?
C22 C23 H23 120.7 . . ?
C22 C23 C24 118.6(3) . . ?
C24 C23 H23 120.7 . . ?
O6 C24 C23 116.5(3) . . ?
O6 C24 C25 122.8(3) . . ?
C25 C24 C23 120.8(3) . . ?
C20 C25 C24 119.1(3) . . ?
C20 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O3 0.86 2.08 2.919(4) 165.9 2_564 yes
N1 H1B O2 0.86 1.94 2.611(4) 134.2 . yes
N2 H2A O1 0.86 2.07 2.933(4) 177.3 2_465 yes
N2 H2B O4 0.86 1.95 2.623(4) 134.0 . yes
O5 H5A O1 0.82 1.85 2.653(3) 167.7 1_545 yes
O6 H6A O3 0.82 1.86 2.664(3) 168.5 2_564 yes
O7 H7 O5 0.82 2.02 2.833(3) 169.4 2 yes

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
C1 C2 C3 C4 -1.0(5) . . . . ?
O2 C2 C3 C4 178.5(3) . . . . ?
C2 C1 C6 C5 -0.7(5) . . . . ?
C2 C1 C7 O1 177.7(3) . . . . ?
C2 C1 C7 N1 -1.6(5) . . . . ?
C2 O2 C8 C9 179.8(3) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C4 C5 C6 C1 -0.1(6) . . . . ?
C6 C1 C2 O2 -178.3(3) . . . . ?
C6 C1 C2 C3 1.2(5) . . . . ?
C6 C1 C7 O1 -2.7(5) . . . . ?
C6 C1 C7 N1 178.1(3) . . . . ?
C7 C1 C2 O2 1.4(5) . . . . ?
C7 C1 C2 C3 -179.1(3) . . . . ?
C7 C1 C6 C5 179.6(4) . . . . ?
C8 O2 C2 C1 -178.5(3) . . . . ?
C8 O2 C2 C3 2.0(5) . . . . ?
O4 C12 C13 C14 179.6(3) . . . . ?
C11 C12 C13 C14 -1.3(5) . . . . ?
C12 O4 C18 C19 -179.2(4) . . . . ?
C12 C11 C16 C15 -1.4(5) . . . . ?
C12 C11 C17 N2 -4.3(5) . . . . ?
C12 C11 C17 O3 177.6(3) . . . . ?
C12 C13 C14 C15 0.7(6) . . . . ?
C13 C14 C15 C16 -0.5(6) . . . . ?
C14 C15 C16 C11 0.8(6) . . . . ?
C16 C11 C12 O4 -179.3(3) . . . . ?
C16 C11 C12 C13 1.6(5) . . . . ?
C16 C11 C17 N2 175.0(3) . . . . ?
C16 C11 C17 O3 -3.1(4) . . . . ?
C17 C11 C12 O4 0.0(5) . . . . ?
C17 C11 C12 C13 -179.1(3) . . . . ?
C17 C11 C16 C15 179.3(3) . . . . ?
C18 O4 C12 C11 -176.3(3) . . . . ?
C18 O4 C12 C13 2.8(5) . . . . ?
O5 C20 C21 C22 -179.0(3) . . . . ?
O5 C20 C25 C24 179.3(3) . . . . ?
O6 C24 C25 C20 -178.8(3) . . . . ?
O7 C22 C23 C24 -178.0(3) . . . . ?
C20 C21 C22 O7 178.2(3) . . . . ?
C20 C21 C22 C23 -0.8(5) . . . . ?
C21 C20 C25 C24 -0.1(5) . . . . ?
C21 C22 C23 C24 0.9(5) . . . . ?
C22 C23 C24 O6 178.5(3) . . . . ?
C22 C23 C24 C25 -0.6(4) . . . . ?
C23 C24 C25 C20 0.3(5) . . . . ?
C25 C20 C21 C22 0.4(4) . . . . ?


_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_eres
_database_code_depnum_ccdc_archive 'CCDC 2247945'
loop_
_audit_author_name
_audit_author_address
'Duane Choquesillo-Lazarte'
;Laboratorio de Estudios Cristalograficos,IACT,CSIC
Spain
;
_audit_update_record             
;
2023-03-11 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_audit_creation_date             2023-03-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C9 H11 N O2), C6 H6 O2'
_chemical_formula_sum            'C24 H28 N2 O6'
_chemical_formula_weight         440.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.2189(6)
_cell_length_b                   13.8655(10)
_cell_length_c                   16.3778(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.473(3)
_cell_angle_gamma                90
_cell_volume                     2316.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2423
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      66.62
_cell_measurement_theta_min      4.18
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6222
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1073 before and 0.0731 after correction.
The Ratio of minimum to maximum transmission is 0.8265.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_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  0.0538
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31842
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.590
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_min         4.181
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3483
_reflns_number_total             4058
_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       'Bruker Apex 4, 2022'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0081(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4058
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.064
_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)+(0.0643P)²+0.2566P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1208
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C20(H20), C22(H22), C23(H23), C24(H24)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A), O6(H6A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.89762(9) 0.57322(8) 0.38376(6) 0.0696(3) Uani 1 1 d . . . . .
N1 N 0.68070(12) 0.58719(10) 0.38162(7) 0.0703(4) Uani 1 1 d . . . . .
H1A H 0.673890 0.573192 0.330388 0.084 Uiso 1 1 calc R U . . .
H1B H 0.611527 0.599087 0.407295 0.084 Uiso 1 1 calc R U . . .
C1 C 0.80893(13) 0.61469(9) 0.51017(8) 0.0545(3) Uani 1 1 d . . . . .
O2 O 0.57962(9) 0.62905(8) 0.52169(5) 0.0661(3) Uani 1 1 d . . . . .
C2 C 0.70256(13) 0.63405(9) 0.55859(8) 0.0569(3) Uani 1 1 d . . . . .
C3 C 0.72538(16) 0.65726(11) 0.64109(9) 0.0687(4) Uani 1 1 d . . . . .
H3 H 0.655190 0.669394 0.673199 0.082 Uiso 1 1 calc R U . . .
C4 C 0.85188(18) 0.66219(12) 0.67501(10) 0.0769(4) Uani 1 1 d . . . . .
H4 H 0.866530 0.679000 0.729774 0.092 Uiso 1 1 calc R U . . .
C5 C 0.95745(17) 0.64246(12) 0.62862(10) 0.0768(4) Uani 1 1 d . . . . .
H5 H 1.042536 0.645398 0.652094 0.092 Uiso 1 1 calc R U . . .
C6 C 0.93524(15) 0.61835(10) 0.54709(9) 0.0657(4) Uani 1 1 d . . . . .
H6 H 1.006208 0.604250 0.516179 0.079 Uiso 1 1 calc R U . . .
C7 C 0.79709(13) 0.59042(9) 0.42079(8) 0.0547(3) Uani 1 1 d . . . . .
C8 C 0.46817(14) 0.64911(12) 0.56773(9) 0.0675(4) Uani 1 1 d . . . . .
H8A H 0.473863 0.713838 0.590121 0.081 Uiso 1 1 calc R U . . .
H8B H 0.463751 0.603720 0.612547 0.081 Uiso 1 1 calc R U . . .
C9 C 0.34956(15) 0.63962(13) 0.51002(10) 0.0772(4) Uani 1 1 d . . . . .
H9A H 0.352698 0.687407 0.467771 0.116 Uiso 1 1 calc R U . . .
H9B H 0.272026 0.648876 0.539379 0.116 Uiso 1 1 calc R U . . .
H9C H 0.347898 0.576491 0.485909 0.116 Uiso 1 1 calc R U . . .
N2 N 0.88519(12) 0.93796(11) 0.70296(7) 0.0759(4) Uani 1 1 d . . . . .
H2A H 0.895864 0.954934 0.753425 0.091 Uiso 1 1 calc R U . . .
H2B H 0.951719 0.921167 0.676513 0.091 Uiso 1 1 calc R U . . .
O3 O 0.66962(9) 0.96200(7) 0.70417(6) 0.0670(3) Uani 1 1 d . . . . .
O4 O 0.97665(9) 0.88937(7) 0.56121(6) 0.0632(3) Uani 1 1 d . . . . .
C11 C 0.74878(13) 0.90891(9) 0.57817(8) 0.0536(3) Uani 1 1 d . . . . .
C12 C 0.85105(13) 0.88405(9) 0.52793(8) 0.0547(3) Uani 1 1 d . . . . .
C13 C 0.82161(15) 0.85626(10) 0.44716(9) 0.0643(4) Uani 1 1 d . . . . .
H13 H 0.888728 0.839711 0.413905 0.077 Uiso 1 1 calc R U . . .
C14 C 0.69299(16) 0.85330(12) 0.41650(9) 0.0719(4) Uani 1 1 d . . . . .
H14 H 0.674188 0.834678 0.362505 0.086 Uiso 1 1 calc R U . . .
C15 C 0.59177(16) 0.87751(12) 0.46461(10) 0.0734(4) Uani 1 1 d . . . . .
H15 H 0.505342 0.875388 0.443358 0.088 Uiso 1 1 calc R U . . .
C16 C 0.62041(14) 0.90493(10) 0.54472(9) 0.0640(4) Uani 1 1 d . . . . .
H16 H 0.552154 0.921159 0.577184 0.077 Uiso 1 1 calc R U . . .
C17 C 0.76672(13) 0.93768(9) 0.66608(8) 0.0560(3) Uani 1 1 d . . . . .
C18 C 1.08362(14) 0.86320(11) 0.51283(9) 0.0626(4) Uani 1 1 d . . . . .
H18A H 1.086697 0.905598 0.465874 0.075 Uiso 1 1 calc R U . . .
H18B H 1.073198 0.797400 0.493395 0.075 Uiso 1 1 calc R U . . .
C19 C 1.20673(15) 0.87263(12) 0.56657(11) 0.0777(4) Uani 1 1 d . . . . .
H19A H 1.281045 0.858840 0.535363 0.117 Uiso 1 1 calc R U . . .
H19B H 1.204459 0.827926 0.611222 0.117 Uiso 1 1 calc R U . . .
H19C H 1.213635 0.937178 0.587598 0.117 Uiso 1 1 calc R U . . .
O5 O 1.04171(10) 0.77426(8) 0.84205(7) 0.0771(3) Uani 1 1 d . . . . .
H5A H 1.009601 0.825964 0.854656 0.116 Uiso 1 1 calc R U . . .
O6 O 1.44389(9) 0.63818(8) 0.76770(6) 0.0691(3) Uani 1 1 d . . . . .
H6A H 1.404013 0.588741 0.777926 0.104 Uiso 1 1 calc R U . . .
C20 C 1.23957(13) 0.70763(10) 0.80440(8) 0.0569(3) Uani 1 1 d . . . . .
H20 H 1.204619 0.646805 0.813026 0.068 Uiso 1 1 calc R U . . .
C21 C 1.16519(13) 0.78932(10) 0.81677(8) 0.0589(3) Uani 1 1 d . . . . .
C22 C 1.21610(15) 0.88032(11) 0.80397(9) 0.0669(4) Uani 1 1 d . . . . .
H22 H 1.166526 0.935217 0.812631 0.080 Uiso 1 1 calc R U . . .
C23 C 1.34180(16) 0.88797(12) 0.77813(10) 0.0727(4) Uani 1 1 d . . . . .
H23 H 1.376419 0.948827 0.769183 0.087 Uiso 1 1 calc R U . . .
C24 C 1.41754(14) 0.80724(12) 0.76523(9) 0.0676(4) Uani 1 1 d . . . . .
H24 H 1.501830 0.813614 0.747445 0.081 Uiso 1 1 calc R U . . .
C25 C 1.36561(13) 0.71653(10) 0.77926(7) 0.0575(3) 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
O1 C7 1.2472(15) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C7 1.3174(18) . ?
C1 C2 1.4095(18) . ?
C1 C6 1.393(2) . ?
C1 C7 1.4998(18) . ?
O2 C2 1.3625(16) . ?
O2 C8 1.4306(15) . ?
C2 C3 1.3948(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(2) . ?
C6 H6 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.497(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C17 1.3197(18) . ?
O3 C17 1.2500(15) . ?
O4 C12 1.3656(16) . ?
O4 C18 1.4351(15) . ?
C11 C12 1.4115(18) . ?
C11 C16 1.392(2) . ?
C11 C17 1.4946(18) . ?
C12 C13 1.3931(19) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.380(2) . ?
C16 H16 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.497(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O5 H5A 0.8200 . ?
O5 C21 1.3678(16) . ?
O6 H6A 0.8200 . ?
O6 C25 1.3691(17) . ?
C20 H20 0.9300 . ?
C20 C21 1.3858(19) . ?
C20 C25 1.3812(19) . ?
C21 C22 1.385(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.381(2) . ?
C23 H23 0.9300 . ?
C23 C24 1.384(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.390(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
H1A N1 H1B 120.0 . . ?
C7 N1 H1A 120.0 . . ?
C7 N1 H1B 120.0 . . ?
C2 C1 C7 124.92(12) . . ?
C6 C1 C2 118.35(12) . . ?
C6 C1 C7 116.73(12) . . ?
C2 O2 C8 119.90(10) . . ?
O2 C2 C1 117.55(11) . . ?
O2 C2 C3 122.47(13) . . ?
C3 C2 C1 119.97(13) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.99(15) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.84(14) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.37(15) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 H6 119.3 . . ?
C5 C6 C1 121.47(15) . . ?
C5 C6 H6 119.3 . . ?
O1 C7 N1 120.18(12) . . ?
O1 C7 C1 119.82(12) . . ?
N1 C7 C1 119.99(11) . . ?
O2 C8 H8A 110.3 . . ?
O2 C8 H8B 110.3 . . ?
O2 C8 C9 106.87(12) . . ?
H8A C8 H8B 108.6 . . ?
C9 C8 H8A 110.3 . . ?
C9 C8 H8B 110.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H2A N2 H2B 120.0 . . ?
C17 N2 H2A 120.0 . . ?
C17 N2 H2B 120.0 . . ?
C12 O4 C18 119.66(10) . . ?
C12 C11 C17 125.09(12) . . ?
C16 C11 C12 118.32(12) . . ?
C16 C11 C17 116.59(12) . . ?
O4 C12 C11 117.73(11) . . ?
O4 C12 C13 122.52(12) . . ?
C13 C12 C11 119.75(13) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.02(14) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.5 . . ?
C13 C14 C15 121.06(14) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.14(14) . . ?
C16 C15 H15 120.4 . . ?
C11 C16 H16 119.1 . . ?
C15 C16 C11 121.72(14) . . ?
C15 C16 H16 119.1 . . ?
N2 C17 C11 119.81(11) . . ?
O3 C17 N2 120.31(12) . . ?
O3 C17 C11 119.87(12) . . ?
O4 C18 H18A 110.3 . . ?
O4 C18 H18B 110.3 . . ?
O4 C18 C19 107.12(12) . . ?
H18A C18 H18B 108.5 . . ?
C19 C18 H18A 110.3 . . ?
C19 C18 H18B 110.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 O5 H5A 109.5 . . ?
C25 O6 H6A 109.5 . . ?
C21 C20 H20 120.0 . . ?
C25 C20 H20 120.0 . . ?
C25 C20 C21 120.01(12) . . ?
O5 C21 C20 116.34(12) . . ?
O5 C21 C22 123.13(13) . . ?
C22 C21 C20 120.53(13) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 C21 118.76(14) . . ?
C23 C22 H22 120.6 . . ?
C22 C23 H23 119.2 . . ?
C22 C23 C24 121.59(14) . . ?
C24 C23 H23 119.2 . . ?
C23 C24 H24 120.5 . . ?
C23 C24 C25 118.94(13) . . ?
C25 C24 H24 120.5 . . ?
O6 C25 C20 122.25(12) . . ?
O6 C25 C24 117.58(12) . . ?
C20 C25 C24 120.17(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O3 0.86 2.12 2.9807(15) 176.5 4_575 yes
N1 H1B O2 0.86 1.97 2.6369(14) 134.0 . yes
N2 H2A O1 0.86 2.17 2.9603(16) 152.8 4_576 yes
N2 H2B O4 0.86 1.97 2.6418(14) 134.0 . yes
O5 H5A O1 0.82 1.89 2.6886(15) 165.9 4_576 yes
O6 H6A O3 0.82 1.94 2.7550(14) 171.8 2_746 yes

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
C1 C2 C3 C4 0.7(2) . . . . ?
O2 C2 C3 C4 -179.37(13) . . . . ?
C2 C1 C6 C5 -1.5(2) . . . . ?
C2 C1 C7 O1 -179.04(12) . . . . ?
C2 C1 C7 N1 0.86(19) . . . . ?
C2 O2 C8 C9 178.83(12) . . . . ?
C2 C3 C4 C5 -1.3(2) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 C1 0.9(2) . . . . ?
C6 C1 C2 O2 -179.25(11) . . . . ?
C6 C1 C2 C3 0.73(19) . . . . ?
C6 C1 C7 O1 1.16(18) . . . . ?
C6 C1 C7 N1 -178.93(12) . . . . ?
C7 C1 C2 O2 0.95(19) . . . . ?
C7 C1 C2 C3 -179.06(13) . . . . ?
C7 C1 C6 C5 178.31(13) . . . . ?
C8 O2 C2 C1 -179.28(12) . . . . ?
C8 O2 C2 C3 0.7(2) . . . . ?
O4 C12 C13 C14 -179.21(13) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 O4 C18 C19 -177.77(12) . . . . ?
C12 C11 C16 C15 0.0(2) . . . . ?
C12 C11 C17 N2 -2.3(2) . . . . ?
C12 C11 C17 O3 177.19(12) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C14 C15 C16 C11 0.1(2) . . . . ?
C16 C11 C12 O4 179.23(11) . . . . ?
C16 C11 C12 C13 -0.13(19) . . . . ?
C16 C11 C17 N2 176.38(13) . . . . ?
C16 C11 C17 O3 -4.13(18) . . . . ?
C17 C11 C12 O4 -2.10(19) . . . . ?
C17 C11 C12 C13 178.54(12) . . . . ?
C17 C11 C16 C15 -178.76(13) . . . . ?
C18 O4 C12 C11 178.95(11) . . . . ?
C18 O4 C12 C13 -1.71(19) . . . . ?
O5 C21 C22 C23 -179.77(14) . . . . ?
C20 C21 C22 C23 0.5(2) . . . . ?
C21 C20 C25 O6 178.74(12) . . . . ?
C21 C20 C25 C24 -0.9(2) . . . . ?
C21 C22 C23 C24 -0.3(2) . . . . ?
C22 C23 C24 C25 -0.5(2) . . . . ?
C23 C24 C25 O6 -178.60(13) . . . . ?
C23 C24 C25 C20 1.0(2) . . . . ?
C25 C20 C21 O5 -179.66(12) . . . . ?
C25 C20 C21 C22 0.1(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
