# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_6a
_database_code_depnum_ccdc_archive 'CCDC 2193426'
loop_
_audit_author_name
_audit_author_address
'Israel Carreira-Barral'
;Universidad de Burgos
Spain
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        6a
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H25 N3 O5'
_chemical_formula_sum            'C24 H25 N3 O5'
_chemical_formula_weight         435.47

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.5652(2)
_cell_length_b                   14.3595(3)
_cell_length_c                   12.2203(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.2020(10)
_cell_angle_gamma                90
_cell_volume                     2170.05(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9923
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      72.19

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   0.7715
_exptl_transmission_factor_max   1
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.777
_shelx_estimated_absorpt_T_min   0.892
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5814
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37271
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.582
_diffrn_reflns_theta_max         72.162
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             4231
_reflns_number_gt                3564
_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       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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)+(0.0430P)²+0.7051P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4231
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.46743(11) 0.02171(10) 0.33045(11) 0.0413(3) Uani 1 1 d . . . . .
C2 C 0.38782(12) -0.00155(12) 0.39053(13) 0.0513(4) Uani 1 1 d . . . . .
H2 H 0.345277 0.044419 0.414717 0.062 Uiso 1 1 calc R U . . .
C3 C 0.37257(13) -0.09365(12) 0.41394(13) 0.0553(4) Uani 1 1 d . . . . .
H3 H 0.320282 -0.110630 0.455334 0.066 Uiso 1 1 calc R U . . .
C4 C 0.43513(13) -0.16046(12) 0.37574(14) 0.0556(4) Uani 1 1 d . . . . .
H4 H 0.425647 -0.222794 0.392290 0.067 Uiso 1 1 calc R U . . .
C5 C 0.51210(13) -0.13590(11) 0.31289(14) 0.0512(4) Uani 1 1 d . . . . .
H5 H 0.552121 -0.182496 0.286209 0.061 Uiso 1 1 calc R U . . .
C6 C 0.53126(11) -0.04385(9) 0.28857(11) 0.0402(3) Uani 1 1 d . . . . .
C7 C 0.61333(12) -0.01822(10) 0.21602(13) 0.0465(3) Uani 1 1 d . . . . .
H7A H 0.590894 0.039159 0.176726 0.056 Uiso 1 1 calc R U . . .
H7B H 0.682842 -0.007135 0.263059 0.056 Uiso 1 1 calc R U . . .
C8 C 0.55503(11) -0.12299(10) 0.04648(12) 0.0431(3) Uani 1 1 d . . . . .
C9 C 0.64177(11) -0.18064(10) 0.00576(12) 0.0429(3) Uani 1 1 d . . . . .
H9A H 0.654671 -0.163755 -0.067633 0.051 Uiso 1 1 calc R U . . .
H9B H 0.633317 -0.247407 0.012727 0.051 Uiso 1 1 calc R U . . .
C10 C 0.72155(10) -0.13494(9) 0.10365(10) 0.0367(3) Uani 1 1 d . . . . .
C11 C 0.78267(11) -0.19716(10) 0.19673(12) 0.0441(3) Uani 1 1 d . . . . .
C12 C 0.83488(11) -0.28595(10) 0.17274(12) 0.0430(3) Uani 1 1 d . . . . .
C13 C 0.84112(12) -0.31637(11) 0.06636(13) 0.0487(3) Uani 1 1 d . . . . .
H13 H 0.815128 -0.278787 0.005505 0.058 Uiso 1 1 calc R U . . .
C14 C 0.88574(14) -0.40220(12) 0.05018(17) 0.0630(4) Uani 1 1 d . . . . .
H14 H 0.888526 -0.422638 -0.021470 0.076 Uiso 1 1 calc R U . . .
C15 C 0.92609(16) -0.45748(12) 0.1402(2) 0.0716(5) Uani 1 1 d . . . . .
H15 H 0.955375 -0.515452 0.128974 0.086 Uiso 1 1 calc R U . . .
C16 C 0.92330(15) -0.42743(13) 0.24634(19) 0.0690(5) Uani 1 1 d . . . . .
H16 H 0.952534 -0.464204 0.306888 0.083 Uiso 1 1 calc R U . . .
C17 C 0.87708(13) -0.34262(12) 0.26308(14) 0.0563(4) Uani 1 1 d . . . . .
H17 H 0.873975 -0.323018 0.334978 0.068 Uiso 1 1 calc R U . . .
C18 C 0.80182(10) -0.06697(9) 0.06480(11) 0.0392(3) Uani 1 1 d . . . . .
C19 C 0.82533(11) 0.08715(9) -0.01681(12) 0.0415(3) Uani 1 1 d . . . . .
H19 H 0.898778 0.063620 -0.015368 0.050 Uiso 1 1 calc R U . . .
C20 C 0.83177(14) 0.17246(12) 0.05706(15) 0.0570(4) Uani 1 1 d . . . . .
H20A H 0.867309 0.156341 0.131713 0.068 Uiso 1 1 calc R U . . .
H20B H 0.759340 0.193980 0.060858 0.068 Uiso 1 1 calc R U . . .
C21 C 0.89456(16) 0.25013(13) 0.01173(18) 0.0709(5) Uani 1 1 d . . . . .
H21A H 0.894179 0.305218 0.057588 0.085 Uiso 1 1 calc R U . . .
H21B H 0.969115 0.230831 0.015600 0.085 Uiso 1 1 calc R U . . .
C22 C 0.84660(16) 0.27360(14) -0.1065(2) 0.0790(6) Uani 1 1 d . . . . .
H22A H 0.890779 0.320469 -0.134087 0.095 Uiso 1 1 calc R U . . .
H22B H 0.774738 0.299266 -0.109448 0.095 Uiso 1 1 calc R U . . .
C23 C 0.84002(16) 0.18861(15) -0.17914(16) 0.0706(5) Uani 1 1 d . . . . .
H23A H 0.912487 0.166733 -0.182131 0.085 Uiso 1 1 calc R U . . .
H23B H 0.805423 0.204813 -0.254090 0.085 Uiso 1 1 calc R U . . .
C24 C 0.77649(13) 0.11123(12) -0.13549(13) 0.0551(4) Uani 1 1 d . . . . .
H24A H 0.702107 0.130902 -0.139010 0.066 Uiso 1 1 calc R U . . .
H24B H 0.776486 0.056434 -0.181908 0.066 Uiso 1 1 calc R U . . .
N1 N 0.48266(11) 0.12099(9) 0.31309(11) 0.0536(3) Uani 1 1 d . . . . .
N2 N 0.62537(9) -0.09049(8) 0.13552(10) 0.0404(3) Uani 1 1 d . . . . .
N3 N 0.76183(9) 0.01424(8) 0.02530(10) 0.0452(3) Uani 1 1 d . . . . .
O1 O 0.57285(11) 0.14981(8) 0.30886(13) 0.0734(4) Uani 1 1 d . . . . .
O2 O 0.40411(13) 0.17167(10) 0.30459(17) 0.0992(6) Uani 1 1 d . . . . .
O3 O 0.45976(8) -0.10832(8) 0.01451(10) 0.0588(3) Uani 1 1 d . . . . .
O4 O 0.78389(12) -0.17113(9) 0.29136(9) 0.0737(4) Uani 1 1 d . . . . .
O5 O 0.89560(8) -0.09101(8) 0.06992(13) 0.0695(4) Uani 1 1 d . . . . .
H3N H 0.690001 0.026000 0.020000 0.083 Uiso 1 1 d . 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
C1 C2 1.383(2) . ?
C1 C6 1.3917(19) . ?
C1 N1 1.4589(19) . ?
C2 C3 1.374(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.5194(19) . ?
C7 N2 1.4562(18) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O3 1.2100(17) . ?
C8 N2 1.3573(18) . ?
C8 C9 1.5209(19) . ?
C9 C10 1.5626(18) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.4786(16) . ?
C10 C18 1.5378(18) . ?
C10 C11 1.5402(18) . ?
C11 O4 1.2128(18) . ?
C11 C12 1.487(2) . ?
C12 C13 1.387(2) . ?
C12 C17 1.398(2) . ?
C13 C14 1.383(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O5 1.2188(16) . ?
C18 N3 1.3265(18) . ?
C19 N3 1.4639(17) . ?
C19 C24 1.511(2) . ?
C19 C20 1.515(2) . ?
C19 H19 0.9800 . ?
C20 C21 1.526(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.502(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.503(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.519(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
N1 O2 1.2158(18) . ?
N1 O1 1.2162(18) . ?
N3 H3N 0.9092(11) . ?

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 C6 123.38(13) . . ?
C2 C1 N1 116.05(13) . . ?
C6 C1 N1 120.57(12) . . ?
C3 C2 C1 118.94(14) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 119.50(14) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.62(15) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 121.85(14) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 115.67(13) . . ?
C5 C6 C7 121.20(12) . . ?
C1 C6 C7 123.07(12) . . ?
N2 C7 C6 112.58(11) . . ?
N2 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
N2 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
O3 C8 N2 131.72(14) . . ?
O3 C8 C9 135.59(14) . . ?
N2 C8 C9 92.68(10) . . ?
C8 C9 C10 85.45(10) . . ?
C8 C9 H9A 114.4 . . ?
C10 C9 H9A 114.4 . . ?
C8 C9 H9B 114.4 . . ?
C10 C9 H9B 114.4 . . ?
H9A C9 H9B 111.5 . . ?
N2 C10 C18 114.75(10) . . ?
N2 C10 C11 112.31(10) . . ?
C18 C10 C11 109.13(10) . . ?
N2 C10 C9 86.53(9) . . ?
C18 C10 C9 113.40(11) . . ?
C11 C10 C9 119.35(11) . . ?
O4 C11 C12 121.39(13) . . ?
O4 C11 C10 116.48(13) . . ?
C12 C11 C10 122.11(12) . . ?
C13 C12 C17 118.71(14) . . ?
C13 C12 C11 123.72(13) . . ?
C17 C12 C11 117.54(14) . . ?
C14 C13 C12 120.43(15) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.03(18) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 120.36(16) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.94(17) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C12 120.49(17) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
O5 C18 N3 124.62(13) . . ?
O5 C18 C10 119.04(12) . . ?
N3 C18 C10 116.33(11) . . ?
N3 C19 C24 110.30(12) . . ?
N3 C19 C20 110.10(12) . . ?
C24 C19 C20 110.88(13) . . ?
N3 C19 H19 108.5 . . ?
C24 C19 H19 108.5 . . ?
C20 C19 H19 108.5 . . ?
C19 C20 C21 110.55(13) . . ?
C19 C20 H20A 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C22 C21 C20 111.60(15) . . ?
C22 C21 H21A 109.3 . . ?
C20 C21 H21A 109.3 . . ?
C22 C21 H21B 109.3 . . ?
C20 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 C23 110.89(15) . . ?
C21 C22 H22A 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 C24 111.34(16) . . ?
C22 C23 H23A 109.4 . . ?
C24 C23 H23A 109.4 . . ?
C22 C23 H23B 109.4 . . ?
C24 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C19 C24 C23 110.79(13) . . ?
C19 C24 H24A 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 108.1 . . ?
O2 N1 O1 122.76(15) . . ?
O2 N1 C1 118.16(14) . . ?
O1 N1 C1 119.07(13) . . ?
C8 N2 C7 130.97(12) . . ?
C8 N2 C10 94.99(10) . . ?
C7 N2 C10 132.31(11) . . ?
C18 N3 C19 124.18(11) . . ?
C18 N3 H3N 119.76(12) . . ?
C19 N3 H3N 115.99(11) . . ?

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
C6 C1 C2 C3 2.3(2) . . . . ?
N1 C1 C2 C3 -177.21(14) . . . . ?
C1 C2 C3 C4 -1.1(2) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 1.8(3) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
C4 C5 C6 C7 -177.82(15) . . . . ?
C2 C1 C6 C5 -1.4(2) . . . . ?
N1 C1 C6 C5 178.08(13) . . . . ?
C2 C1 C6 C7 175.72(14) . . . . ?
N1 C1 C6 C7 -4.8(2) . . . . ?
C5 C6 C7 N2 28.9(2) . . . . ?
C1 C6 C7 N2 -148.06(13) . . . . ?
O3 C8 C9 C10 174.68(18) . . . . ?
N2 C8 C9 C10 -4.45(10) . . . . ?
C8 C9 C10 N2 4.09(9) . . . . ?
C8 C9 C10 C18 -111.43(11) . . . . ?
C8 C9 C10 C11 117.81(12) . . . . ?
N2 C10 C11 O4 -34.73(18) . . . . ?
C18 C10 C11 O4 93.69(16) . . . . ?
C9 C10 C11 O4 -133.69(15) . . . . ?
N2 C10 C11 C12 143.53(12) . . . . ?
C18 C10 C11 C12 -88.06(15) . . . . ?
C9 C10 C11 C12 44.57(18) . . . . ?
O4 C11 C12 C13 -176.25(16) . . . . ?
C10 C11 C12 C13 5.6(2) . . . . ?
O4 C11 C12 C17 5.6(2) . . . . ?
C10 C11 C12 C17 -172.56(13) . . . . ?
C17 C12 C13 C14 1.7(2) . . . . ?
C11 C12 C13 C14 -176.46(14) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C14 C15 C16 C17 1.9(3) . . . . ?
C15 C16 C17 C12 -1.3(3) . . . . ?
C13 C12 C17 C16 -0.5(2) . . . . ?
C11 C12 C17 C16 177.78(15) . . . . ?
N2 C10 C18 O5 157.47(14) . . . . ?
C11 C10 C18 O5 30.43(18) . . . . ?
C9 C10 C18 O5 -105.24(16) . . . . ?
N2 C10 C18 N3 -23.95(17) . . . . ?
C11 C10 C18 N3 -150.99(12) . . . . ?
C9 C10 C18 N3 73.34(15) . . . . ?
N3 C19 C20 C21 -178.08(14) . . . . ?
C24 C19 C20 C21 -55.73(18) . . . . ?
C19 C20 C21 C22 55.7(2) . . . . ?
C20 C21 C22 C23 -55.8(2) . . . . ?
C21 C22 C23 C24 56.1(2) . . . . ?
N3 C19 C24 C23 178.53(14) . . . . ?
C20 C19 C24 C23 56.30(18) . . . . ?
C22 C23 C24 C19 -56.5(2) . . . . ?
C2 C1 N1 O2 -32.2(2) . . . . ?
C6 C1 N1 O2 148.24(16) . . . . ?
C2 C1 N1 O1 147.03(15) . . . . ?
C6 C1 N1 O1 -32.5(2) . . . . ?
O3 C8 N2 C7 -8.3(3) . . . . ?
C9 C8 N2 C7 170.86(13) . . . . ?
O3 C8 N2 C10 -174.48(16) . . . . ?
C9 C8 N2 C10 4.71(11) . . . . ?
C6 C7 N2 C8 66.30(19) . . . . ?
C6 C7 N2 C10 -132.52(14) . . . . ?
C18 C10 N2 C8 109.63(12) . . . . ?
C11 C10 N2 C8 -124.98(12) . . . . ?
C9 C10 N2 C8 -4.59(10) . . . . ?
C18 C10 N2 C7 -56.22(18) . . . . ?
C11 C10 N2 C7 69.17(18) . . . . ?
C9 C10 N2 C7 -170.44(14) . . . . ?
O5 C18 N3 C19 -0.7(2) . . . . ?
C10 C18 N3 C19 -179.18(12) . . . . ?
C24 C19 N3 C18 122.66(15) . . . . ?
C20 C19 N3 C18 -114.65(16) . . . . ?

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
C7 H7A O3 0.97 2.52 3.341(2) 143.0 3_655
C9 H9B O2 0.97 2.63 3.267(2) 123.3 2_645
N3 H3N O3 0.9092(11) 2.1989(10) 3.0553(15) 156.71(8) 3_655

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.029


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
####################################################################### 
# 
# 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_7d
_database_code_depnum_ccdc_archive 'CCDC 2193428'
loop_
_audit_author_name
_audit_author_address
'Israel Carreira-Barral'
;Universidad de Burgos
Spain
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        7d
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H27 N3 O5'
_chemical_formula_sum            'C25 H27 N3 O5'
_chemical_formula_weight         449.49

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                   10.1914(11)
_cell_length_b                   10.3790(11)
_cell_length_c                   11.8123(13)
_cell_angle_alpha                73.566(2)
_cell_angle_beta                 67.677(2)
_cell_angle_gamma                83.029(2)
_cell_volume                     1108.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2753
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      25.96

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13009
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.929
_diffrn_reflns_theta_max         28.255
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5000
_reflns_number_gt                3058
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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)+(0.0648P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5000
_refine_ls_number_parameters     324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1274
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_restrained_S_all      0.914
_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 0.6291(2) 0.99588(19) 0.0963(2) 0.0415(5) Uani 1 1 d . . . . .
H1A H 0.724823 0.984650 0.036424 0.062 Uiso 1 1 calc R U . . .
H1B H 0.634017 1.043945 0.154973 0.062 Uiso 1 1 calc R U . . .
H1C H 0.569968 1.047486 0.049633 0.062 Uiso 1 1 calc R U . . .
C2 C 0.56524(19) 0.85993(18) 0.16975(18) 0.0309(4) Uani 1 1 d . . . . .
C3 C 0.5079(2) 0.82580(19) 0.30096(19) 0.0359(5) Uani 1 1 d . . . . .
H3 H 0.509445 0.888956 0.345008 0.043 Uiso 1 1 calc R U . . .
C4 C 0.4487(2) 0.70192(18) 0.36860(18) 0.0326(5) Uani 1 1 d . . . . .
H4 H 0.409518 0.681053 0.458489 0.039 Uiso 1 1 calc R U . . .
C5 C 0.44542(17) 0.60673(17) 0.30678(16) 0.0248(4) Uani 1 1 d . . . . .
C6 C 0.50592(17) 0.63965(17) 0.17446(16) 0.0256(4) Uani 1 1 d . . . . .
H6 H 0.507314 0.575679 0.130217 0.031 Uiso 1 1 calc R U . . .
C7 C 0.56356(18) 0.76466(17) 0.10796(17) 0.0286(4) Uani 1 1 d . . . . .
H7 H 0.602935 0.786084 0.018063 0.034 Uiso 1 1 calc R U . . .
C8 C 0.37456(18) 0.47737(18) 0.38619(17) 0.0265(4) Uani 1 1 d . . . . .
C9 C 0.37474(17) 0.36639(16) 0.32214(15) 0.0223(4) Uani 1 1 d . . . . .
C10 C 0.31537(18) 0.41571(17) 0.21483(16) 0.0247(4) Uani 1 1 d . . . . .
C11 C 0.12466(19) 0.5468(2) 0.15224(18) 0.0350(5) Uani 1 1 d . . . . .
H11 H 0.145236 0.485375 0.095657 0.042 Uiso 1 1 calc R U . . .
C12 C -0.0325(2) 0.5475(2) 0.2234(2) 0.0480(6) Uani 1 1 d . . . . .
H12A H -0.053713 0.596697 0.289085 0.058 Uiso 1 1 calc R U . . .
H12B H -0.064110 0.453836 0.266791 0.058 Uiso 1 1 calc R U . . .
C13 C -0.1155(2) 0.6121(2) 0.1383(2) 0.0548(7) Uani 1 1 d . . . . .
H13A H -0.108780 0.553912 0.082734 0.066 Uiso 1 1 calc R U . . .
H13B H -0.216758 0.619925 0.191159 0.066 Uiso 1 1 calc R U . . .
C14 C -0.0609(2) 0.7495(2) 0.0575(2) 0.0622(7) Uani 1 1 d . . . . .
H14A H -0.078290 0.811105 0.112409 0.075 Uiso 1 1 calc R U . . .
H14B H -0.112769 0.785557 -0.000955 0.075 Uiso 1 1 calc R U . . .
C15 C 0.0970(2) 0.7430(3) -0.0185(2) 0.0701(8) Uani 1 1 d . . . . .
H15A H 0.131591 0.834487 -0.068593 0.084 Uiso 1 1 calc R U . . .
H15B H 0.113913 0.686930 -0.078109 0.084 Uiso 1 1 calc R U . . .
C16 C 0.1787(2) 0.6832(2) 0.0703(2) 0.0552(7) Uani 1 1 d . . . . .
H16A H 0.280725 0.675978 0.019486 0.066 Uiso 1 1 calc R U . . .
H16B H 0.168532 0.743786 0.124654 0.066 Uiso 1 1 calc R U . . .
C17 C 0.52762(17) 0.31058(17) 0.27404(16) 0.0264(4) Uani 1 1 d . . . . .
H17A H 0.552746 0.298749 0.187947 0.032 Uiso 1 1 calc R U . . .
H17B H 0.595962 0.372576 0.271298 0.032 Uiso 1 1 calc R U . . .
C18 C 0.52996(18) 0.17743(17) 0.36658(17) 0.0249(4) Uani 1 1 d . . . . .
C19 C 0.28704(17) 0.24178(17) 0.42520(16) 0.0243(4) Uani 1 1 d . . . . .
H19 H 0.233803 0.268150 0.506075 0.029 Uiso 1 1 calc R U . . .
C20 C 0.18370(18) 0.18362(18) 0.38788(16) 0.0260(4) Uani 1 1 d . . . . .
C21 C 0.2333(2) 0.1082(2) 0.30040(17) 0.0355(5) Uani 1 1 d . . . . .
H21 H 0.332181 0.090193 0.265700 0.043 Uiso 1 1 calc R U . . .
C22 C 0.1411(2) 0.0582(2) 0.26209(19) 0.0475(6) Uani 1 1 d . . . . .
H22 H 0.177226 0.006527 0.201612 0.057 Uiso 1 1 calc R U . . .
C23 C -0.0034(2) 0.0835(2) 0.3119(2) 0.0497(6) Uani 1 1 d . . . . .
H23 H -0.065829 0.050904 0.283976 0.060 Uiso 1 1 calc R U . . .
C24 C -0.0559(2) 0.1546(2) 0.4002(2) 0.0448(6) Uani 1 1 d . . . . .
H24 H -0.155041 0.170449 0.436292 0.054 Uiso 1 1 calc R U . . .
C25 C 0.03719(19) 0.20330(19) 0.43672(19) 0.0347(5) Uani 1 1 d . . . . .
N1 N 0.19849(16) 0.49260(15) 0.24090(15) 0.0308(4) Uani 1 1 d . . . . .
N2 N 0.39652(15) 0.14355(15) 0.44319(14) 0.0262(4) Uani 1 1 d . . . . .
N3 N -0.0286(2) 0.2781(2) 0.5337(2) 0.0590(6) Uani 1 1 d . . . . .
O1 O 0.32093(17) 0.45646(14) 0.50020(12) 0.0500(4) Uani 1 1 d . . . . .
O2 O 0.37090(13) 0.38112(13) 0.11593(11) 0.0341(3) Uani 1 1 d . . . . .
O3 O 0.63677(12) 0.10972(12) 0.37072(12) 0.0320(3) Uani 1 1 d . . . . .
O4A O -0.1401(4) 0.2554(4) 0.6096(4) 0.0772(13) Uani 0.559(3) 1 d . . P A 1
O5A O 0.0288(3) 0.3934(3) 0.5077(2) 0.0498(10) Uani 0.559(3) 1 d . . P A 1
O4B O -0.1247(5) 0.3396(5) 0.5459(6) 0.0907(19) Uani 0.441(3) 1 d . . P A 2
O5B O 0.0149(4) 0.2238(4) 0.6391(4) 0.0613(14) Uani 0.441(3) 1 d . . P A 2
H1N H 0.160(3) 0.516(2) 0.315(2) 0.074 Uiso 1 1 d . U . . .
H2N H 0.377(2) 0.063(2) 0.503(2) 0.074 Uiso 1 1 d . 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
C1 C2 1.506(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.386(3) . ?
C2 C7 1.390(2) . ?
C3 C4 1.377(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(2) . ?
C5 C8 1.487(2) . ?
C6 C7 1.380(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 O1 1.210(2) . ?
C8 C9 1.546(2) . ?
C9 C10 1.541(2) . ?
C9 C17 1.543(2) . ?
C9 C19 1.586(2) . ?
C10 O2 1.225(2) . ?
C10 N1 1.334(2) . ?
C11 N1 1.464(2) . ?
C11 C12 1.500(3) . ?
C11 C16 1.501(3) . ?
C11 H11 1.0000 . ?
C12 C13 1.518(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.507(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.521(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.532(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.504(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 O3 1.2315(19) . ?
C18 N2 1.339(2) . ?
C19 N2 1.453(2) . ?
C19 C20 1.525(2) . ?
C19 H19 1.0000 . ?
C20 C21 1.378(2) . ?
C20 C25 1.394(2) . ?
C21 C22 1.390(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.355(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.375(3) . ?
C24 H24 0.9500 . ?
C25 N3 1.469(3) . ?
N1 H1N 0.91(2) . ?
N2 H2N 0.92(2) . ?
N3 O4B 1.087(4) . ?
N3 O4A 1.150(4) . ?
N3 O5A 1.301(3) . ?
N3 O5B 1.424(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 118.13(17) . . ?
C3 C2 C1 120.90(17) . . ?
C7 C2 C1 120.96(17) . . ?
C4 C3 C2 121.15(17) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.82(17) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 118.24(16) . . ?
C4 C5 C8 117.60(16) . . ?
C6 C5 C8 124.14(16) . . ?
C7 C6 C5 120.25(16) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 121.39(17) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
O1 C8 C5 120.91(17) . . ?
O1 C8 C9 119.73(16) . . ?
C5 C8 C9 119.32(15) . . ?
C10 C9 C17 111.56(14) . . ?
C10 C9 C8 112.95(13) . . ?
C17 C9 C8 108.15(14) . . ?
C10 C9 C19 109.95(13) . . ?
C17 C9 C19 104.07(13) . . ?
C8 C9 C19 109.77(13) . . ?
O2 C10 N1 124.01(17) . . ?
O2 C10 C9 120.99(15) . . ?
N1 C10 C9 114.96(15) . . ?
N1 C11 C12 109.92(15) . . ?
N1 C11 C16 111.04(15) . . ?
C12 C11 C16 112.48(17) . . ?
N1 C11 H11 107.7 . . ?
C12 C11 H11 107.7 . . ?
C16 C11 H11 107.7 . . ?
C11 C12 C13 112.82(17) . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 111.83(18) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 C15 110.8(2) . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C16 110.2(2) . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C11 C16 C15 111.19(18) . . ?
C11 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
C11 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C18 C17 C9 105.97(14) . . ?
C18 C17 H17A 110.5 . . ?
C9 C17 H17A 110.5 . . ?
C18 C17 H17B 110.5 . . ?
C9 C17 H17B 110.5 . . ?
H17A C17 H17B 108.7 . . ?
O3 C18 N2 125.40(16) . . ?
O3 C18 C17 125.74(16) . . ?
N2 C18 C17 108.86(15) . . ?
N2 C19 C20 110.77(14) . . ?
N2 C19 C9 103.30(13) . . ?
C20 C19 C9 115.26(13) . . ?
N2 C19 H19 109.1 . . ?
C20 C19 H19 109.1 . . ?
C9 C19 H19 109.1 . . ?
C21 C20 C25 116.16(17) . . ?
C21 C20 C19 120.32(15) . . ?
C25 C20 C19 123.52(17) . . ?
C20 C21 C22 121.12(19) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C23 C22 C21 120.2(2) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 118.7(2) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 H24 120.6 . . ?
C24 C25 C20 123.6(2) . . ?
C24 C25 N3 115.19(19) . . ?
C20 C25 N3 121.17(18) . . ?
C10 N1 C11 123.13(16) . . ?
C10 N1 H1N 121.8(15) . . ?
C11 N1 H1N 115.0(15) . . ?
C18 N2 C19 116.04(15) . . ?
C18 N2 H2N 121.0(15) . . ?
C19 N2 H2N 122.9(15) . . ?
O4A N3 O5A 120.0(3) . . ?
O4B N3 O5B 119.0(4) . . ?
O4B N3 C25 126.5(4) . . ?
O4A N3 C25 122.8(3) . . ?
O5A N3 C25 114.6(2) . . ?
O5B N3 C25 110.9(2) . . ?

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
C7 C2 C3 C4 -1.1(3) . . . . ?
C1 C2 C3 C4 179.64(17) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C3 C4 C5 C8 -177.63(16) . . . . ?
C4 C5 C6 C7 -1.7(2) . . . . ?
C8 C5 C6 C7 176.88(15) . . . . ?
C5 C6 C7 C2 1.0(3) . . . . ?
C3 C2 C7 C6 0.4(3) . . . . ?
C1 C2 C7 C6 179.69(16) . . . . ?
C4 C5 C8 O1 0.5(3) . . . . ?
C6 C5 C8 O1 -178.02(17) . . . . ?
C4 C5 C8 C9 -177.12(15) . . . . ?
C6 C5 C8 C9 4.3(2) . . . . ?
O1 C8 C9 C10 128.02(18) . . . . ?
C5 C8 C9 C10 -54.3(2) . . . . ?
O1 C8 C9 C17 -108.00(18) . . . . ?
C5 C8 C9 C17 69.67(18) . . . . ?
O1 C8 C9 C19 4.9(2) . . . . ?
C5 C8 C9 C19 -177.39(14) . . . . ?
C17 C9 C10 O2 17.2(2) . . . . ?
C8 C9 C10 O2 139.30(16) . . . . ?
C19 C9 C10 O2 -97.71(18) . . . . ?
C17 C9 C10 N1 -165.27(15) . . . . ?
C8 C9 C10 N1 -43.2(2) . . . . ?
C19 C9 C10 N1 79.80(18) . . . . ?
N1 C11 C12 C13 175.74(18) . . . . ?
C16 C11 C12 C13 51.5(3) . . . . ?
C11 C12 C13 C14 -52.0(3) . . . . ?
C12 C13 C14 C15 55.0(3) . . . . ?
C13 C14 C15 C16 -57.3(3) . . . . ?
N1 C11 C16 C15 -177.44(19) . . . . ?
C12 C11 C16 C15 -53.8(3) . . . . ?
C14 C15 C16 C11 56.7(3) . . . . ?
C10 C9 C17 C18 -131.71(14) . . . . ?
C8 C9 C17 C18 103.49(15) . . . . ?
C19 C9 C17 C18 -13.20(17) . . . . ?
C9 C17 C18 O3 -169.87(16) . . . . ?
C9 C17 C18 N2 10.79(19) . . . . ?
C10 C9 C19 N2 130.71(14) . . . . ?
C17 C9 C19 N2 11.10(16) . . . . ?
C8 C9 C19 N2 -104.45(15) . . . . ?
C10 C9 C19 C20 9.75(19) . . . . ?
C17 C9 C19 C20 -109.86(16) . . . . ?
C8 C9 C19 C20 134.59(15) . . . . ?
N2 C19 C20 C21 -42.8(2) . . . . ?
C9 C19 C20 C21 74.0(2) . . . . ?
N2 C19 C20 C25 137.99(17) . . . . ?
C9 C19 C20 C25 -105.20(19) . . . . ?
C25 C20 C21 C22 1.4(3) . . . . ?
C19 C20 C21 C22 -177.83(17) . . . . ?
C20 C21 C22 C23 -0.1(3) . . . . ?
C21 C22 C23 C24 -1.5(3) . . . . ?
C22 C23 C24 C25 1.5(3) . . . . ?
C23 C24 C25 C20 -0.1(3) . . . . ?
C23 C24 C25 N3 -179.46(19) . . . . ?
C21 C20 C25 C24 -1.4(3) . . . . ?
C19 C20 C25 C24 177.85(17) . . . . ?
C21 C20 C25 N3 177.95(18) . . . . ?
C19 C20 C25 N3 -2.8(3) . . . . ?
O2 C10 N1 C11 -1.3(3) . . . . ?
C9 C10 N1 C11 -178.72(15) . . . . ?
C12 C11 N1 C10 143.47(19) . . . . ?
C16 C11 N1 C10 -91.4(2) . . . . ?
O3 C18 N2 C19 177.18(17) . . . . ?
C17 C18 N2 C19 -3.5(2) . . . . ?
C20 C19 N2 C18 118.83(16) . . . . ?
C9 C19 N2 C18 -5.13(19) . . . . ?
C24 C25 N3 O4B -32.4(5) . . . . ?
C20 C25 N3 O4B 148.3(5) . . . . ?
C24 C25 N3 O4A 30.5(5) . . . . ?
C20 C25 N3 O4A -148.9(4) . . . . ?
C24 C25 N3 O5A -131.3(2) . . . . ?
C20 C25 N3 O5A 49.4(3) . . . . ?
C24 C25 N3 O5B 125.8(2) . . . . ?
C20 C25 N3 O5B -53.6(3) . . . . ?

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
C12 H12A O5A 0.99 2.54 3.417(4) 147.6 2_566
C12 H12A O5B 0.99 2.38 3.289(4) 151.8 2_566
C19 H19 O5A 1.00 2.32 2.875(3) 114.0 .
C19 H19 O5B 1.00 2.20 2.940(4) 129.7 .
N1 H1N O5A 0.91(2) 2.24(2) 2.905(3) 129(2) .
N1 H1N O5A 0.91(2) 2.56(2) 3.418(3) 157(2) 2_566
N1 H1N O4B 0.91(2) 2.42(3) 3.266(6) 155(2) 2_566
N2 H2N O3 0.92(2) 1.96(2) 2.8701(19) 172(2) 2_656

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.044


# start Validation Reply Form
_vrf_PLAT430_7d                  
;
PROBLEM: Short Inter D...A Contact O1..O4B. 2.82 Ang.
RESPONSE: The nitro group of the molecule has been found to be disordered in two different orientations. Therefore, the atoms of this group have been included in the model in two sets of positions, with complementary occupancy factors. Although the positions of O(1) and O(4B) are too close, since O(4B) is badly disordered in the channels of the framework, the distance between them is reasonable. In addition to single-crystal X-ray diffraction, this compound has been properly characterised by other techniques (NMR spectroscopy and mass spectrometry).
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_7jdiast2
_database_code_depnum_ccdc_archive 'CCDC 2193429'
loop_
_audit_author_name
_audit_author_address
'Israel Carreira-Barral'
;Universidad de Burgos
Spain
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;
_audit_creation_date             2022-05-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        7jdiast2
_chemical_formula_moiety         'C H Cl3, C30 H28 F N3 O5'
_chemical_formula_sum            'C31 H29 Cl3 F N3 O5'
_chemical_formula_weight         648.92
_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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   9.940(16)
_cell_length_b                   10.793(10)
_cell_length_c                   16.25(2)
_cell_angle_alpha                108.53(4)
_cell_angle_beta                 96.84(7)
_cell_angle_gamma                106.91(5)
_cell_volume                     1538(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6451
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      66.076
_cell_measurement_theta_min      2.953
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.745
_exptl_absorpt_coefficient_mu    3.129
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1243 before and 0.0889 after correction.
The Ratio of minimum to maximum transmission is 0.6647.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29480
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.666
_diffrn_reflns_theta_max         66.666
_diffrn_reflns_theta_min         2.949
_diffrn_ambient_temperature      230(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     1.54184
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3218
_reflns_number_total             5392
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0025(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         5392
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0657
_refine_ls_restrained_S_all      1.023
_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)+(0.0915P)²+1.9055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1647
_refine_ls_wR_factor_ref         0.2160
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C7(H7), C19(H19), C31(H31)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C23(H23A,H23B), C24(H24A,H24B), C22(H22A,H22B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C13(H13), C30(H30), C26(H26), C17(H17), C5(H5), C4(H4),
 C2(H2A), C14(H14), C29(H29), C27(H27), C3(H3A), C28(H28), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl -0.15516(17) 0.75651(16) 0.66092(9) 0.0931(5) Uani 1 1 d . . . . .
Cl1 Cl -0.36288(18) 0.64986(16) 0.49427(9) 0.0932(5) Uani 1 1 d . . . . .
Cl3 Cl -0.0782(2) 0.6312(2) 0.49665(15) 0.1286(8) Uani 1 1 d . . . . .
O5 O 0.4803(3) 0.6583(3) 0.08060(18) 0.0543(7) Uani 1 1 d . . . . .
O4 O 0.3900(3) 0.5053(3) 0.30591(18) 0.0561(7) Uani 1 1 d . . . . .
O3 O 0.0956(3) 0.3874(3) -0.04408(18) 0.0618(8) Uani 1 1 d . . . . .
N2 N 0.1391(3) 0.5325(3) 0.1014(2) 0.0493(8) Uani 1 1 d . . . . .
H2 H 0.072236 0.567445 0.093446 0.059 Uiso 1 1 calc R U . . .
N3 N 0.5802(4) 0.7345(3) 0.2284(2) 0.0555(9) Uani 1 1 d . . . . .
H3 H 0.574409 0.717316 0.276923 0.067 Uiso 1 1 calc R U . . .
O2 O 0.1335(4) 0.5920(4) 0.3591(2) 0.0787(10) Uani 1 1 d . . . . .
F1 F 0.8607(4) 0.2439(4) 0.2018(2) 0.1137(13) Uani 1 1 d . . . . .
O1 O 0.3314(5) 0.7208(4) 0.4604(2) 0.0916(12) Uani 1 1 d . . . . .
N1 N 0.2489(5) 0.6899(5) 0.3887(2) 0.0659(11) Uani 1 1 d . . . . .
C18 C 0.4820(4) 0.6454(4) 0.1529(3) 0.0456(9) Uani 1 1 d . . . . .
C11 C 0.4266(4) 0.4797(4) 0.2347(2) 0.0430(9) Uani 1 1 d . . . . .
C8 C 0.3629(4) 0.5237(4) 0.1630(2) 0.0410(8) Uani 1 1 d . . . . .
C25 C 0.2427(4) 0.2550(4) 0.0687(2) 0.0453(9) Uani 1 1 d . . . . .
C12 C 0.5393(4) 0.4127(4) 0.2209(3) 0.0447(9) Uani 1 1 d . . . . .
C9 C 0.2935(4) 0.4038(3) 0.0689(2) 0.0409(8) Uani 1 1 d . . . . .
H9 H 0.362682 0.411401 0.030117 0.049 Uiso 1 1 calc R U . . .
C7 C 0.2311(4) 0.5716(4) 0.1886(2) 0.0432(9) Uani 1 1 d . . . . .
H7 H 0.179903 0.515360 0.220501 0.052 Uiso 1 1 calc R U . . .
C10 C 0.1648(4) 0.4387(4) 0.0342(3) 0.0480(9) Uani 1 1 d . . . . .
C6 C 0.2712(4) 0.7263(4) 0.2446(3) 0.0500(10) Uani 1 1 d . . . . .
C13 C 0.6114(5) 0.4097(4) 0.1524(3) 0.0537(10) Uani 1 1 d . . . . .
H13 H 0.586176 0.446657 0.110155 0.064 Uiso 1 1 calc R U . . .
C30 C 0.1389(5) 0.2129(4) 0.1138(3) 0.0569(11) Uani 1 1 d . . . . .
H30 H 0.098193 0.276436 0.145405 0.068 Uiso 1 1 calc R U . . .
C26 C 0.3025(5) 0.1608(4) 0.0220(3) 0.0563(11) Uani 1 1 d . . . . .
H26 H 0.372113 0.187988 -0.009323 0.068 Uiso 1 1 calc R U . . .
C1 C 0.2894(5) 0.7799(4) 0.3368(3) 0.0557(11) Uani 1 1 d . . . . .
C17 C 0.5779(5) 0.3597(5) 0.2838(3) 0.0581(11) Uani 1 1 d . . . . .
H17 H 0.530905 0.363044 0.330945 0.070 Uiso 1 1 calc R U . . .
C5 C 0.3008(5) 0.8240(4) 0.2033(3) 0.0573(11) Uani 1 1 d . . . . .
H5 H 0.288079 0.792248 0.140956 0.069 Uiso 1 1 calc R U . . .
C4 C 0.3484(5) 0.9667(5) 0.2522(3) 0.0703(14) Uani 1 1 d . . . . .
H4 H 0.366133 1.029896 0.222726 0.084 Uiso 1 1 calc R U . . .
C2 C 0.3407(5) 0.9223(5) 0.3863(3) 0.0693(14) Uani 1 1 d . . . . .
H2A H 0.355752 0.955206 0.448757 0.083 Uiso 1 1 calc R U . . .
C19 C 0.6978(5) 0.8603(5) 0.2340(3) 0.0727(14) Uani 1 1 d . . . . .
H19 H 0.662373 0.898899 0.191711 0.087 Uiso 1 1 calc R U . . .
C14 C 0.7206(5) 0.3527(5) 0.1455(3) 0.0645(12) Uani 1 1 d . . . . .
H14 H 0.769255 0.350192 0.099203 0.077 Uiso 1 1 calc R U . . .
C29 C 0.0942(5) 0.0766(5) 0.1128(3) 0.0694(13) Uani 1 1 d . . . . .
H29 H 0.024242 0.048859 0.143660 0.083 Uiso 1 1 calc R U . . .
C27 C 0.2584(6) 0.0246(5) 0.0218(3) 0.0721(14) Uani 1 1 d . . . . .
H27 H 0.300277 -0.038723 -0.008542 0.086 Uiso 1 1 calc R U . . .
C3 C 0.3695(6) 1.0151(5) 0.3433(4) 0.0767(15) Uani 1 1 d . . . . .
H3A H 0.403588 1.111595 0.376425 0.092 Uiso 1 1 calc R U . . .
C28 C 0.1536(6) -0.0168(5) 0.0661(4) 0.0757(16) Uani 1 1 d . . . . .
H28 H 0.122797 -0.108741 0.064402 0.091 Uiso 1 1 calc R U . . .
C16 C 0.6859(6) 0.3014(6) 0.2772(4) 0.0773(15) Uani 1 1 d . . . . .
H16 H 0.711566 0.263543 0.318774 0.093 Uiso 1 1 calc R U . . .
C15 C 0.7545(6) 0.3007(6) 0.2082(4) 0.0750(15) Uani 1 1 d . . . . .
C20 C 0.7404(5) 0.9718(5) 0.3304(4) 0.091(2) Uani 1 1 d . . . . .
H20A H 0.801835 1.061628 0.331121 0.110 Uiso 1 1 calc R U . . .
H20B H 0.652971 0.983170 0.348792 0.110 Uiso 1 1 calc R U . . .
C31 C -0.2172(6) 0.6272(5) 0.5529(3) 0.0735(14) Uani 1 1 d . . . . .
H31 H -0.252373 0.535006 0.558277 0.088 Uiso 1 1 calc R U . . .
C23 C 0.8922(6) 0.7801(6) 0.2709(5) 0.100(2) Uani 1 1 d . . . . .
H23A H 0.978053 0.765367 0.251826 0.120 Uiso 1 1 calc R U . . .
H23B H 0.827608 0.690694 0.269046 0.120 Uiso 1 1 calc R U . . .
C24 C 0.8203(7) 0.8233(7) 0.2097(4) 0.0941(19) Uani 1 1 d . . . . .
H24A H 0.787072 0.747742 0.150882 0.113 Uiso 1 1 calc R U . . .
H24B H 0.890347 0.903928 0.204294 0.113 Uiso 1 1 calc R U . . .
C22 C 0.9376(7) 0.8840(8) 0.3656(4) 0.103(2) Uani 1 1 d . . . . .
H22A H 0.972216 0.842078 0.405263 0.124 Uiso 1 1 calc R U . . .
H22B H 1.018196 0.965894 0.370289 0.124 Uiso 1 1 calc R U . . .
C21 C 0.8207(8) 0.9287(7) 0.3956(4) 0.104(2) Uani 1 1 d . . . . .
H21A H 0.861022 1.007537 0.452856 0.125 Uiso 1 1 calc R U . . .
H21B H 0.751668 0.852239 0.405563 0.125 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
Cl2 C31 1.759(6) . ?
Cl1 C31 1.758(6) . ?
Cl3 C31 1.744(6) . ?
O5 C18 1.226(5) . ?
O4 C11 1.226(5) . ?
O3 C10 1.233(5) . ?
N2 H2 0.8700 . ?
N2 C7 1.452(5) . ?
N2 C10 1.341(5) . ?
N3 H3 0.8700 . ?
N3 C18 1.342(5) . ?
N3 C19 1.480(6) . ?
O2 N1 1.226(6) . ?
F1 C15 1.365(5) . ?
O1 N1 1.229(5) . ?
N1 C1 1.480(6) . ?
C18 C8 1.558(6) . ?
C11 C8 1.529(5) . ?
C11 C12 1.502(5) . ?
C8 C9 1.569(5) . ?
C8 C7 1.595(5) . ?
C25 C9 1.536(5) . ?
C25 C30 1.390(6) . ?
C25 C26 1.390(6) . ?
C12 C13 1.392(6) . ?
C12 C17 1.388(6) . ?
C9 H9 0.9900 . ?
C9 C10 1.529(5) . ?
C7 H7 0.9900 . ?
C7 C6 1.528(5) . ?
C6 C1 1.392(6) . ?
C6 C5 1.402(6) . ?
C13 H13 0.9400 . ?
C13 C14 1.394(6) . ?
C30 H30 0.9400 . ?
C30 C29 1.401(6) . ?
C26 H26 0.9400 . ?
C26 C27 1.405(7) . ?
C1 C2 1.389(6) . ?
C17 H17 0.9400 . ?
C17 C16 1.392(6) . ?
C5 H5 0.9400 . ?
C5 C4 1.391(6) . ?
C4 H4 0.9400 . ?
C4 C3 1.372(7) . ?
C2 H2A 0.9400 . ?
C2 C3 1.378(8) . ?
C19 H19 0.9900 . ?
C19 C20 1.557(8) . ?
C19 C24 1.448(8) . ?
C14 H14 0.9400 . ?
C14 C15 1.363(7) . ?
C29 H29 0.9400 . ?
C29 C28 1.381(8) . ?
C27 H27 0.9400 . ?
C27 C28 1.384(8) . ?
C3 H3A 0.9400 . ?
C28 H28 0.9400 . ?
C16 H16 0.9400 . ?
C16 C15 1.379(8) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 C21 1.518(9) . ?
C31 H31 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 C24 1.428(9) . ?
C23 C22 1.508(9) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 C21 1.460(9) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?

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
C7 N2 H2 122.5 . . ?
C10 N2 H2 122.5 . . ?
C10 N2 C7 115.0(3) . . ?
C18 N3 H3 118.0 . . ?
C18 N3 C19 123.9(4) . . ?
C19 N3 H3 118.0 . . ?
O2 N1 O1 123.9(5) . . ?
O2 N1 C1 118.4(4) . . ?
O1 N1 C1 117.6(5) . . ?
O5 C18 N3 123.8(4) . . ?
O5 C18 C8 120.8(3) . . ?
N3 C18 C8 115.4(3) . . ?
O4 C11 C8 119.5(3) . . ?
O4 C11 C12 119.6(3) . . ?
C12 C11 C8 120.8(3) . . ?
C18 C8 C9 108.7(3) . . ?
C18 C8 C7 110.0(3) . . ?
C11 C8 C18 109.8(3) . . ?
C11 C8 C9 114.7(3) . . ?
C11 C8 C7 110.3(3) . . ?
C9 C8 C7 103.2(3) . . ?
C30 C25 C9 121.6(4) . . ?
C30 C25 C26 119.6(4) . . ?
C26 C25 C9 118.9(4) . . ?
C13 C12 C11 123.2(3) . . ?
C17 C12 C11 117.1(4) . . ?
C17 C12 C13 119.5(4) . . ?
C8 C9 H9 109.3 . . ?
C25 C9 C8 115.7(3) . . ?
C25 C9 H9 109.3 . . ?
C10 C9 C8 102.6(3) . . ?
C10 C9 C25 110.5(3) . . ?
C10 C9 H9 109.3 . . ?
N2 C7 C8 102.0(3) . . ?
N2 C7 H7 109.1 . . ?
N2 C7 C6 111.8(3) . . ?
C8 C7 H7 109.1 . . ?
C6 C7 C8 115.4(3) . . ?
C6 C7 H7 109.1 . . ?
O3 C10 N2 125.5(4) . . ?
O3 C10 C9 124.6(4) . . ?
N2 C10 C9 109.9(3) . . ?
C1 C6 C7 124.2(4) . . ?
C1 C6 C5 116.3(4) . . ?
C5 C6 C7 119.4(4) . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.8(4) . . ?
C14 C13 H13 119.6 . . ?
C25 C30 H30 119.7 . . ?
C25 C30 C29 120.6(4) . . ?
C29 C30 H30 119.7 . . ?
C25 C26 H26 120.2 . . ?
C25 C26 C27 119.6(5) . . ?
C27 C26 H26 120.2 . . ?
C6 C1 N1 122.6(4) . . ?
C2 C1 N1 115.1(4) . . ?
C2 C1 C6 122.2(4) . . ?
C12 C17 H17 119.9 . . ?
C12 C17 C16 120.1(4) . . ?
C16 C17 H17 119.9 . . ?
C6 C5 H5 119.1 . . ?
C4 C5 C6 121.7(4) . . ?
C4 C5 H5 119.1 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.0(5) . . ?
C3 C4 H4 120.0 . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 C1 119.7(5) . . ?
C3 C2 H2A 120.2 . . ?
N3 C19 H19 108.8 . . ?
N3 C19 C20 109.3(4) . . ?
C20 C19 H19 108.8 . . ?
C24 C19 N3 109.7(5) . . ?
C24 C19 H19 108.8 . . ?
C24 C19 C20 111.3(4) . . ?
C13 C14 H14 121.1 . . ?
C15 C14 C13 117.9(5) . . ?
C15 C14 H14 121.1 . . ?
C30 C29 H29 120.2 . . ?
C28 C29 C30 119.7(5) . . ?
C28 C29 H29 120.2 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.3(5) . . ?
C28 C27 H27 119.8 . . ?
C4 C3 C2 120.0(5) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C29 C28 C27 120.2(5) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C17 C16 H16 120.8 . . ?
C15 C16 C17 118.3(4) . . ?
C15 C16 H16 120.8 . . ?
F1 C15 C16 118.4(5) . . ?
C14 C15 F1 118.3(5) . . ?
C14 C15 C16 123.3(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C21 C20 C19 110.8(4) . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
Cl2 C31 H31 108.3 . . ?
Cl1 C31 Cl2 109.3(3) . . ?
Cl1 C31 H31 108.3 . . ?
Cl3 C31 Cl2 111.1(3) . . ?
Cl3 C31 Cl1 111.3(3) . . ?
Cl3 C31 H31 108.3 . . ?
H23A C23 H23B 107.7 . . ?
C24 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C24 C23 C22 113.2(5) . . ?
C22 C23 H23A 108.9 . . ?
C22 C23 H23B 108.9 . . ?
C19 C24 H24A 108.6 . . ?
C19 C24 H24B 108.6 . . ?
C23 C24 C19 114.8(5) . . ?
C23 C24 H24A 108.6 . . ?
C23 C24 H24B 108.6 . . ?
H24A C24 H24B 107.5 . . ?
C23 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C21 C22 C23 113.0(5) . . ?
C21 C22 H22A 109.0 . . ?
C21 C22 H22B 109.0 . . ?
C20 C21 H21A 108.8 . . ?
C20 C21 H21B 108.8 . . ?
C22 C21 C20 113.8(5) . . ?
C22 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?

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
O5 C18 C8 C11 148.3(3) . . . . ?
O5 C18 C8 C9 22.1(5) . . . . ?
O5 C18 C8 C7 -90.2(4) . . . . ?
O4 C11 C8 C18 109.9(4) . . . . ?
O4 C11 C8 C9 -127.4(4) . . . . ?
O4 C11 C8 C7 -11.4(5) . . . . ?
O4 C11 C12 C13 -164.4(4) . . . . ?
O4 C11 C12 C17 11.5(5) . . . . ?
N2 C7 C6 C1 145.5(4) . . . . ?
N2 C7 C6 C5 -38.6(5) . . . . ?
N3 C18 C8 C11 -33.9(4) . . . . ?
N3 C18 C8 C9 -160.1(3) . . . . ?
N3 C18 C8 C7 87.6(4) . . . . ?
N3 C19 C20 C21 71.7(6) . . . . ?
N3 C19 C24 C23 -67.4(6) . . . . ?
O2 N1 C1 C6 -43.4(6) . . . . ?
O2 N1 C1 C2 133.7(4) . . . . ?
O1 N1 C1 C6 138.8(4) . . . . ?
O1 N1 C1 C2 -44.1(5) . . . . ?
N1 C1 C2 C3 -174.4(4) . . . . ?
C18 N3 C19 C20 152.6(4) . . . . ?
C18 N3 C19 C24 -85.1(5) . . . . ?
C18 C8 C9 C25 147.2(3) . . . . ?
C18 C8 C9 C10 -92.4(3) . . . . ?
C18 C8 C7 N2 90.0(3) . . . . ?
C18 C8 C7 C6 -31.5(4) . . . . ?
C11 C8 C9 C25 23.9(5) . . . . ?
C11 C8 C9 C10 144.3(3) . . . . ?
C11 C8 C7 N2 -148.8(3) . . . . ?
C11 C8 C7 C6 89.7(4) . . . . ?
C11 C12 C13 C14 176.6(4) . . . . ?
C11 C12 C17 C16 -177.3(4) . . . . ?
C8 C11 C12 C13 12.2(5) . . . . ?
C8 C11 C12 C17 -171.9(4) . . . . ?
C8 C9 C10 O3 165.6(4) . . . . ?
C8 C9 C10 N2 -14.5(4) . . . . ?
C8 C7 C6 C1 -98.5(5) . . . . ?
C8 C7 C6 C5 77.4(4) . . . . ?
C25 C9 C10 O3 -70.5(5) . . . . ?
C25 C9 C10 N2 109.4(4) . . . . ?
C25 C30 C29 C28 -0.3(6) . . . . ?
C25 C26 C27 C28 1.5(6) . . . . ?
C12 C11 C8 C18 -66.7(4) . . . . ?
C12 C11 C8 C9 56.1(5) . . . . ?
C12 C11 C8 C7 172.0(3) . . . . ?
C12 C13 C14 C15 -0.3(7) . . . . ?
C12 C17 C16 C15 1.3(7) . . . . ?
C9 C8 C7 N2 -25.9(4) . . . . ?
C9 C8 C7 C6 -147.3(3) . . . . ?
C9 C25 C30 C29 -180.0(4) . . . . ?
C9 C25 C26 C27 179.4(4) . . . . ?
C7 N2 C10 O3 176.9(4) . . . . ?
C7 N2 C10 C9 -3.0(5) . . . . ?
C7 C8 C9 C25 -96.1(4) . . . . ?
C7 C8 C9 C10 24.3(4) . . . . ?
C7 C6 C1 N1 -10.1(6) . . . . ?
C7 C6 C1 C2 173.0(4) . . . . ?
C7 C6 C5 C4 -175.0(4) . . . . ?
C10 N2 C7 C8 18.8(4) . . . . ?
C10 N2 C7 C6 142.7(4) . . . . ?
C6 C1 C2 C3 2.8(7) . . . . ?
C6 C5 C4 C3 0.9(7) . . . . ?
C13 C12 C17 C16 -1.3(6) . . . . ?
C13 C14 C15 F1 179.6(4) . . . . ?
C13 C14 C15 C16 0.3(8) . . . . ?
C30 C25 C9 C8 59.8(5) . . . . ?
C30 C25 C9 C10 -56.3(5) . . . . ?
C30 C25 C26 C27 -0.7(6) . . . . ?
C30 C29 C28 C27 1.1(7) . . . . ?
C26 C25 C9 C8 -120.3(4) . . . . ?
C26 C25 C9 C10 123.7(4) . . . . ?
C26 C25 C30 C29 0.1(6) . . . . ?
C26 C27 C28 C29 -1.7(7) . . . . ?
C1 C6 C5 C4 1.3(6) . . . . ?
C1 C2 C3 C4 -0.5(8) . . . . ?
C17 C12 C13 C14 0.7(6) . . . . ?
C17 C16 C15 F1 179.9(5) . . . . ?
C17 C16 C15 C14 -0.8(8) . . . . ?
C5 C6 C1 N1 173.8(4) . . . . ?
C5 C6 C1 C2 -3.1(6) . . . . ?
C5 C4 C3 C2 -1.3(8) . . . . ?
C19 N3 C18 O5 0.7(6) . . . . ?
C19 N3 C18 C8 -177.1(4) . . . . ?
C19 C20 C21 C22 48.4(7) . . . . ?
C20 C19 C24 C23 53.7(7) . . . . ?
C23 C22 C21 C20 -48.4(8) . . . . ?
C24 C19 C20 C21 -49.6(7) . . . . ?
C24 C23 C22 C21 50.0(8) . . . . ?
C22 C23 C24 C19 -53.6(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform, hexane'
####################################################################### 
# 
# 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_8m
_database_code_depnum_ccdc_archive 'CCDC 2193430'
loop_
_audit_author_name
_audit_author_address
'Israel Carreira-Barral'
;Universidad de Burgos
Spain
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;
_audit_creation_date             2019-07-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        8m
_chemical_formula_moiety         'C25 H24 N2 O4'
_chemical_formula_sum            'C25 H24 N2 O4'
_chemical_formula_weight         416.46
_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                   8.9559(3)
_cell_length_b                   11.0368(4)
_cell_length_c                   12.1951(5)
_cell_angle_alpha                90.7300(10)
_cell_angle_beta                 106.0010(10)
_cell_angle_gamma                100.4010(10)
_cell_volume                     1137.18(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9688
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.65
_cell_measurement_theta_min      4.08
_shelx_estimated_absorpt_T_max   0.877
_shelx_estimated_absorpt_T_min   0.824
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1411 before and 0.0846 after correction. The Ratio of minimum to maximum transmission is 0.6080. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   1
_exptl_transmission_factor_min   0.6080
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            48611
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        66.793
_diffrn_reflns_theta_max         66.793
_diffrn_reflns_theta_min         5.379
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3736
_reflns_number_total             3983
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       0.057(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3983
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0605
_refine_ls_restrained_S_all      1.136
_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)+(0.0902P)²+0.9454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1691
_refine_ls_wR_factor_ref         0.1716
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.04987(17) 0.63788(14) 0.46605(13) 0.0265(3) Uani 1 1 d . . . . .
O2 O 0.45953(18) 0.84846(14) 0.59779(14) 0.0300(4) Uani 1 1 d . . . . .
O3 O 0.0789(2) 1.10580(15) 0.39825(15) 0.0327(4) Uani 1 1 d . . . . .
O4 O -0.0234(2) 0.73598(17) 0.16648(15) 0.0415(5) Uani 1 1 d . . . . .
N1 N 0.2604(2) 0.98075(16) 0.41669(16) 0.0248(4) Uani 1 1 d . . . . .
H1 H 0.344319 1.040443 0.436082 0.030 Uiso 1 1 calc R . . . .
N2 N 0.2072(2) 0.73316(16) 0.55716(16) 0.0244(4) Uani 1 1 d . . . . .
C1 C 0.2169(3) 0.6808(2) 0.66986(19) 0.0280(5) Uani 1 1 d . . . . .
H1A H 0.112501 0.626280 0.663941 0.034 Uiso 1 1 calc R . . . .
C2 C 0.2441(3) 0.7815(2) 0.7634(2) 0.0341(5) Uani 1 1 d . . . . .
H2A H 0.156915 0.828397 0.744022 0.041 Uiso 1 1 calc R . . . .
H2B H 0.344537 0.839579 0.769329 0.041 Uiso 1 1 calc R . . . .
C3 C 0.2512(3) 0.7239(3) 0.8774(2) 0.0400(6) Uani 1 1 d . . . . .
H3A H 0.272379 0.790112 0.938329 0.048 Uiso 1 1 calc R . . . .
H3B H 0.147652 0.670936 0.872843 0.048 Uiso 1 1 calc R . . . .
C4 C 0.3803(3) 0.6470(2) 0.9077(2) 0.0338(5) Uani 1 1 d . . . . .
H4A H 0.380871 0.609219 0.980978 0.041 Uiso 1 1 calc R . . . .
H4B H 0.484747 0.700891 0.917357 0.041 Uiso 1 1 calc R . . . .
C5 C 0.3523(3) 0.5458(2) 0.8140(2) 0.0342(5) Uani 1 1 d . . . . .
H5A H 0.252406 0.487629 0.809466 0.041 Uiso 1 1 calc R . . . .
H5B H 0.439675 0.499213 0.833527 0.041 Uiso 1 1 calc R . . . .
C6 C 0.3426(3) 0.5999(2) 0.6975(2) 0.0300(5) Uani 1 1 d . . . . .
H6A H 0.446782 0.649909 0.698786 0.036 Uiso 1 1 calc R . . . .
H6B H 0.315693 0.532056 0.637369 0.036 Uiso 1 1 calc R . . . .
C7 C 0.3288(2) 0.81228(19) 0.53219(19) 0.0238(5) Uani 1 1 d . . . . .
C8 C 0.2738(2) 0.85197(19) 0.40956(18) 0.0233(5) Uani 1 1 d . . . . .
C9 C 0.0961(2) 0.78182(19) 0.36601(19) 0.0241(5) Uani 1 1 d . . . . .
C10 C -0.0041(3) 0.8837(2) 0.3532(2) 0.0271(5) Uani 1 1 d . . . . .
H10A H -0.066614 0.885100 0.272636 0.032 Uiso 1 1 calc R . . . .
H10B H -0.077608 0.869247 0.401299 0.032 Uiso 1 1 calc R . . . .
C11 C 0.1122(3) 1.0041(2) 0.39200(19) 0.0264(5) Uani 1 1 d . . . . .
C12 C 0.0709(2) 0.70679(19) 0.46553(18) 0.0228(4) Uani 1 1 d . . . . .
C13 C 0.0593(3) 0.7020(2) 0.25260(19) 0.0263(5) Uani 1 1 d . . . . .
C14 C 0.1266(2) 0.5888(2) 0.24543(19) 0.0262(5) Uani 1 1 d . . . . .
C15 C 0.1421(3) 0.5555(2) 0.1389(2) 0.0333(5) Uani 1 1 d . . . . .
H15 H 0.115552 0.606635 0.077148 0.040 Uiso 1 1 calc R . . . .
C16 C 0.1957(3) 0.4488(3) 0.1223(2) 0.0398(6) Uani 1 1 d . . . . .
H16 H 0.207479 0.427408 0.049865 0.048 Uiso 1 1 calc R . . . .
C17 C 0.2324(3) 0.3727(2) 0.2121(2) 0.0373(6) Uani 1 1 d . . . . .
H17 H 0.268040 0.298838 0.200623 0.045 Uiso 1 1 calc R . . . .
C18 C 0.2172(3) 0.4042(2) 0.3177(2) 0.0329(5) Uani 1 1 d . . . . .
H18 H 0.241474 0.351644 0.378554 0.039 Uiso 1 1 calc R . . . .
C19 C 0.1665(3) 0.5124(2) 0.3353(2) 0.0271(5) Uani 1 1 d . . . . .
H19 H 0.158859 0.534711 0.408726 0.033 Uiso 1 1 calc R . . . .
C20 C 0.3848(3) 0.8308(2) 0.33946(19) 0.0256(5) Uani 1 1 d . . . . .
C21 C 0.4900(3) 0.7496(2) 0.3716(2) 0.0309(5) Uani 1 1 d . . . . .
H21 H 0.493711 0.706521 0.438953 0.037 Uiso 1 1 calc R . . . .
C22 C 0.5887(3) 0.7318(2) 0.3059(2) 0.0373(6) Uani 1 1 d . . . . .
H22 H 0.660810 0.677272 0.328865 0.045 Uiso 1 1 calc R . . . .
C23 C 0.5831(3) 0.7926(3) 0.2076(2) 0.0401(6) Uani 1 1 d . . . . .
H23 H 0.649925 0.779112 0.162072 0.048 Uiso 1 1 calc R . . . .
C24 C 0.4794(3) 0.8738(3) 0.1751(2) 0.0389(6) Uani 1 1 d . . . . .
H24 H 0.475977 0.916269 0.107486 0.047 Uiso 1 1 calc R . . . .
C25 C 0.3810(3) 0.8932(2) 0.2409(2) 0.0310(5) Uani 1 1 d . . . . .
H25 H 0.310898 0.949274 0.218537 0.037 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.206(3) . ?
O2 C7 1.215(3) . ?
O3 C11 1.219(3) . ?
O4 C13 1.214(3) . ?
N1 H1 0.8800 . ?
N1 C8 1.451(3) . ?
N1 C11 1.350(3) . ?
N2 C1 1.484(3) . ?
N2 C7 1.374(3) . ?
N2 C12 1.391(3) . ?
C1 H1A 1.0000 . ?
C1 C2 1.521(3) . ?
C1 C6 1.529(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.526(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.524(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.524(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.535(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.536(3) . ?
C8 C9 1.579(3) . ?
C8 C20 1.523(3) . ?
C9 C10 1.545(3) . ?
C9 C12 1.523(3) . ?
C9 C13 1.552(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.512(3) . ?
C13 C14 1.493(3) . ?
C14 C15 1.396(3) . ?
C14 C19 1.399(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.378(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.398(3) . ?
C20 C25 1.388(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.382(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.374(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.389(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.385(4) . ?
C25 H25 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
C8 N1 H1 121.8 . . ?
C11 N1 H1 121.8 . . ?
C11 N1 C8 116.46(18) . . ?
C7 N2 C1 124.36(17) . . ?
C7 N2 C12 113.08(18) . . ?
C12 N2 C1 122.56(17) . . ?
N2 C1 H1A 107.4 . . ?
N2 C1 C2 111.37(18) . . ?
N2 C1 C6 110.43(19) . . ?
C2 C1 H1A 107.4 . . ?
C2 C1 C6 112.48(18) . . ?
C6 C1 H1A 107.4 . . ?
C1 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
C1 C2 C3 109.8(2) . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.1(2) . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 C5 110.5(2) . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C4 C5 C6 111.35(19) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C1 C6 C5 110.3(2) . . ?
C1 C6 H6A 109.6 . . ?
C1 C6 H6B 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
O2 C7 N2 125.4(2) . . ?
O2 C7 C8 124.63(19) . . ?
N2 C7 C8 109.92(17) . . ?
N1 C8 C7 107.67(17) . . ?
N1 C8 C9 103.43(16) . . ?
N1 C8 C20 111.85(17) . . ?
C7 C8 C9 103.25(16) . . ?
C20 C8 C7 112.14(17) . . ?
C20 C8 C9 117.60(18) . . ?
C10 C9 C8 105.31(16) . . ?
C10 C9 C13 111.86(17) . . ?
C12 C9 C8 104.26(16) . . ?
C12 C9 C10 108.19(18) . . ?
C12 C9 C13 113.33(17) . . ?
C13 C9 C8 113.27(18) . . ?
C9 C10 H10A 110.5 . . ?
C9 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
C11 C10 C9 106.08(17) . . ?
C11 C10 H10A 110.5 . . ?
C11 C10 H10B 110.5 . . ?
O3 C11 N1 125.4(2) . . ?
O3 C11 C10 126.1(2) . . ?
N1 C11 C10 108.55(18) . . ?
O1 C12 N2 125.2(2) . . ?
O1 C12 C9 125.36(19) . . ?
N2 C12 C9 109.38(17) . . ?
O4 C13 C9 118.1(2) . . ?
O4 C13 C14 119.4(2) . . ?
C14 C13 C9 122.41(18) . . ?
C15 C14 C13 116.4(2) . . ?
C15 C14 C19 118.8(2) . . ?
C19 C14 C13 124.7(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.8(2) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.4(2) . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C8 121.6(2) . . ?
C25 C20 C8 119.3(2) . . ?
C25 C20 C21 119.1(2) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.3(2) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.8(2) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.3(3) . . ?
C25 C24 H24 119.8 . . ?
C20 C25 H25 119.9 . . ?
C24 C25 C20 120.1(2) . . ?
C24 C25 H25 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C7 C8 N1 -69.2(3) . . . . ?
O2 C7 C8 C9 -178.2(2) . . . . ?
O2 C7 C8 C20 54.3(3) . . . . ?
O4 C13 C14 C15 23.6(3) . . . . ?
O4 C13 C14 C19 -153.0(2) . . . . ?
N1 C8 C9 C10 -0.4(2) . . . . ?
N1 C8 C9 C12 -114.17(18) . . . . ?
N1 C8 C9 C13 122.18(18) . . . . ?
N1 C8 C20 C21 140.3(2) . . . . ?
N1 C8 C20 C25 -40.0(3) . . . . ?
N2 C1 C2 C3 179.24(19) . . . . ?
N2 C1 C6 C5 -179.95(18) . . . . ?
N2 C7 C8 N1 109.10(19) . . . . ?
N2 C7 C8 C9 0.1(2) . . . . ?
N2 C7 C8 C20 -127.44(19) . . . . ?
C1 N2 C7 O2 0.8(3) . . . . ?
C1 N2 C7 C8 -177.43(19) . . . . ?
C1 N2 C12 O1 -2.0(3) . . . . ?
C1 N2 C12 C9 176.01(18) . . . . ?
C1 C2 C3 C4 57.2(3) . . . . ?
C2 C1 C6 C5 54.9(3) . . . . ?
C2 C3 C4 C5 -58.0(3) . . . . ?
C3 C4 C5 C6 56.6(3) . . . . ?
C4 C5 C6 C1 -54.6(3) . . . . ?
C6 C1 C2 C3 -56.2(3) . . . . ?
C7 N2 C1 C2 62.9(3) . . . . ?
C7 N2 C1 C6 -62.8(3) . . . . ?
C7 N2 C12 O1 178.4(2) . . . . ?
C7 N2 C12 C9 -3.6(2) . . . . ?
C7 C8 C9 C10 111.76(18) . . . . ?
C7 C8 C9 C12 -2.0(2) . . . . ?
C7 C8 C9 C13 -125.69(18) . . . . ?
C7 C8 C20 C21 19.2(3) . . . . ?
C7 C8 C20 C25 -161.03(19) . . . . ?
C8 N1 C11 O3 176.7(2) . . . . ?
C8 N1 C11 C10 -4.4(3) . . . . ?
C8 C9 C10 C11 -1.9(2) . . . . ?
C8 C9 C12 O1 -178.6(2) . . . . ?
C8 C9 C12 N2 3.4(2) . . . . ?
C8 C9 C13 O4 -109.4(2) . . . . ?
C8 C9 C13 C14 68.2(3) . . . . ?
C8 C20 C21 C22 179.7(2) . . . . ?
C8 C20 C25 C24 -179.1(2) . . . . ?
C9 C8 C20 C21 -100.2(2) . . . . ?
C9 C8 C20 C25 79.5(3) . . . . ?
C9 C10 C11 O3 -177.4(2) . . . . ?
C9 C10 C11 N1 3.8(2) . . . . ?
C9 C13 C14 C15 -154.0(2) . . . . ?
C9 C13 C14 C19 29.4(3) . . . . ?
C10 C9 C12 O1 69.7(3) . . . . ?
C10 C9 C12 N2 -108.35(19) . . . . ?
C10 C9 C13 O4 9.4(3) . . . . ?
C10 C9 C13 C14 -172.98(19) . . . . ?
C11 N1 C8 C7 -105.8(2) . . . . ?
C11 N1 C8 C9 3.0(2) . . . . ?
C11 N1 C8 C20 130.5(2) . . . . ?
C12 N2 C1 C2 -116.6(2) . . . . ?
C12 N2 C1 C6 117.7(2) . . . . ?
C12 N2 C7 O2 -179.6(2) . . . . ?
C12 N2 C7 C8 2.2(2) . . . . ?
C12 C9 C10 C11 109.08(19) . . . . ?
C12 C9 C13 O4 132.1(2) . . . . ?
C12 C9 C13 C14 -50.3(3) . . . . ?
C13 C9 C10 C11 -125.39(19) . . . . ?
C13 C9 C12 O1 -55.0(3) . . . . ?
C13 C9 C12 N2 126.99(19) . . . . ?
C13 C14 C15 C16 -176.7(2) . . . . ?
C13 C14 C19 C18 175.1(2) . . . . ?
C14 C15 C16 C17 1.0(4) . . . . ?
C15 C14 C19 C18 -1.4(3) . . . . ?
C15 C16 C17 C18 -0.8(4) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
C17 C18 C19 C14 1.6(3) . . . . ?
C19 C14 C15 C16 0.1(3) . . . . ?
C20 C8 C9 C10 -124.2(2) . . . . ?
C20 C8 C9 C12 122.01(19) . . . . ?
C20 C8 C9 C13 -1.6(3) . . . . ?
C20 C21 C22 C23 -0.8(4) . . . . ?
C21 C20 C25 C24 0.7(3) . . . . ?
C21 C22 C23 C24 1.0(4) . . . . ?
C22 C23 C24 C25 -0.4(4) . . . . ?
C23 C24 C25 C20 -0.4(4) . . . . ?
C25 C20 C21 C22 -0.1(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 143.2 48.1 'water 1/2diisopropyl ether'

_olex2_submission_original_sample_id mg28-30
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_9n
_database_code_depnum_ccdc_archive 'CCDC 2193435'
loop_
_audit_author_name
_audit_author_address
'Israel Carreira-Barral'
;Universidad de Burgos
Spain
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;
_audit_creation_date             2022-05-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        9n
_chemical_formula_moiety         'C13 H18 N2 O3'
_chemical_formula_sum            'C13 H18 N2 O3'
_chemical_formula_weight         250.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.9497(11)
_cell_length_b                   10.1546(11)
_cell_length_c                   12.5474(19)
_cell_angle_alpha                90
_cell_angle_beta                 111.425(8)
_cell_angle_gamma                90
_cell_volume                     1298.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9198
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      72.39
_cell_measurement_theta_min      5.78
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.929
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1223 before and 0.0799 after correction.
The Ratio of minimum to maximum transmission is 0.7967.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_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  0.0687
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            38343
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.473
_diffrn_reflns_theta_min         5.774
_diffrn_ambient_temperature      230(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2194
_reflns_number_total             2560
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2560
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.065
_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)+(0.0395P)²+0.5942P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1093
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C2(H2A,H2B), C9(H9A,H9B), C12(H12A,H12B), C11(H11A,H11B),
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.04157(10) 0.35929(11) 0.60374(9) 0.0419(3) Uani 1 1 d . . . . .
O2 O 0.60304(10) 0.44771(11) 0.25820(9) 0.0412(3) Uani 1 1 d . . . . .
N1 N 0.88115(11) 0.37867(11) 0.42591(9) 0.0320(3) Uani 1 1 d . . . . .
H1 H 0.887132 0.463609 0.420114 0.038 Uiso 1 1 calc R U . . .
O3 O 0.63760(13) 0.07273(12) 0.46680(13) 0.0609(4) Uani 1 1 d . . . . .
N2 N 0.58790(11) 0.26134(12) 0.35733(10) 0.0349(3) Uani 1 1 d . . . . .
C1 C 0.95435(13) 0.31189(14) 0.51953(12) 0.0323(3) Uani 1 1 d . . . . .
C6 C 0.65076(13) 0.34791(14) 0.30910(11) 0.0315(3) Uani 1 1 d . . . . .
C4 C 0.79059(13) 0.29865(14) 0.33425(11) 0.0311(3) Uani 1 1 d . . . . .
C3 C 0.79547(14) 0.16460(14) 0.39282(13) 0.0347(3) Uani 1 1 d . . . . .
H3 H 0.802811 0.091858 0.342969 0.042 Uiso 1 1 calc R U . . .
C13 C 0.44886(15) 0.31715(16) 0.46928(13) 0.0413(4) Uani 1 1 d . . . . .
H13A H 0.510448 0.388622 0.504769 0.050 Uiso 1 1 calc R U . . .
H13B H 0.474896 0.239655 0.519038 0.050 Uiso 1 1 calc R U . . .
C8 C 0.45293(13) 0.28509(16) 0.35211(13) 0.0384(3) Uani 1 1 d . . . . .
H8 H 0.419783 0.363507 0.303173 0.046 Uiso 1 1 calc R U . . .
C2 C 0.91541(15) 0.16860(15) 0.50382(14) 0.0410(4) Uani 1 1 d . . . . .
H2A H 0.893428 0.136545 0.568290 0.049 Uiso 1 1 calc R U . . .
H2B H 0.986581 0.114560 0.497460 0.049 Uiso 1 1 calc R U . . .
C7 C 0.66723(15) 0.15623(14) 0.41244(13) 0.0386(3) Uani 1 1 d . . . . .
C5 C 0.82519(15) 0.29908(17) 0.22729(13) 0.0422(4) Uani 1 1 d . . . . .
H5A H 0.832101 0.389224 0.204551 0.063 Uiso 1 1 calc R U . . .
H5B H 0.757183 0.253790 0.165855 0.063 Uiso 1 1 calc R U . . .
H5C H 0.908351 0.254480 0.243300 0.063 Uiso 1 1 calc R U . . .
C9 C 0.36037(16) 0.1715(2) 0.29671(15) 0.0548(5) Uani 1 1 d . . . . .
H9A H 0.387322 0.092400 0.344292 0.066 Uiso 1 1 calc R U . . .
H9B H 0.363600 0.152071 0.221284 0.066 Uiso 1 1 calc R U . . .
C12 C 0.31023(17) 0.35849(19) 0.45559(16) 0.0513(4) Uani 1 1 d . . . . .
H12A H 0.306859 0.378459 0.530878 0.062 Uiso 1 1 calc R U . . .
H12B H 0.286038 0.438331 0.408647 0.062 Uiso 1 1 calc R U . . .
C11 C 0.21343(17) 0.2490(2) 0.39909(16) 0.0597(5) Uani 1 1 d . . . . .
H11A H 0.124301 0.278483 0.387624 0.072 Uiso 1 1 calc R U . . .
H11B H 0.232944 0.171944 0.449606 0.072 Uiso 1 1 calc R U . . .
C10 C 0.22046(17) 0.2103(3) 0.28421(17) 0.0672(6) Uani 1 1 d . . . . .
H10A H 0.191265 0.284424 0.230872 0.081 Uiso 1 1 calc R U . . .
H10B H 0.161199 0.136055 0.252190 0.081 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 C1 1.2341(17) . ?
O2 C6 1.2100(17) . ?
N1 H1 0.8700 . ?
N1 C1 1.3395(18) . ?
N1 C4 1.4605(17) . ?
O3 C7 1.2046(19) . ?
N2 C6 1.3846(18) . ?
N2 C8 1.4750(18) . ?
N2 C7 1.3904(19) . ?
C1 C2 1.509(2) . ?
C6 C4 1.5301(19) . ?
C4 C3 1.5386(19) . ?
C4 C5 1.5219(19) . ?
C3 H3 0.9900 . ?
C3 C2 1.526(2) . ?
C3 C7 1.514(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 C8 1.522(2) . ?
C13 C12 1.523(2) . ?
C8 H8 0.9900 . ?
C8 C9 1.525(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 C10 1.533(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 C11 1.521(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 C10 1.523(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?

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
C1 N1 H1 122.4 . . ?
C1 N1 C4 115.18(12) . . ?
C4 N1 H1 122.4 . . ?
C6 N2 C8 121.79(12) . . ?
C6 N2 C7 112.63(12) . . ?
C7 N2 C8 125.55(12) . . ?
O1 C1 N1 125.55(13) . . ?
O1 C1 C2 125.54(13) . . ?
N1 C1 C2 108.89(12) . . ?
O2 C6 N2 125.08(13) . . ?
O2 C6 C4 126.10(12) . . ?
N2 C6 C4 108.79(12) . . ?
N1 C4 C6 108.72(11) . . ?
N1 C4 C3 102.77(11) . . ?
N1 C4 C5 112.13(11) . . ?
C6 C4 C3 104.20(11) . . ?
C5 C4 C6 111.71(11) . . ?
C5 C4 C3 116.57(12) . . ?
C4 C3 H3 110.8 . . ?
C2 C3 C4 106.29(11) . . ?
C2 C3 H3 110.8 . . ?
C7 C3 C4 104.77(11) . . ?
C7 C3 H3 110.8 . . ?
C7 C3 C2 113.14(13) . . ?
H13A C13 H13B 108.3 . . ?
C8 C13 H13A 109.8 . . ?
C8 C13 H13B 109.8 . . ?
C8 C13 C12 109.25(13) . . ?
C12 C13 H13A 109.8 . . ?
C12 C13 H13B 109.8 . . ?
N2 C8 C13 111.99(12) . . ?
N2 C8 H8 107.1 . . ?
N2 C8 C9 112.64(13) . . ?
C13 C8 H8 107.1 . . ?
C13 C8 C9 110.66(13) . . ?
C9 C8 H8 107.1 . . ?
C1 C2 C3 104.64(11) . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
O3 C7 N2 124.99(14) . . ?
O3 C7 C3 126.10(14) . . ?
N2 C7 C3 108.91(12) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C8 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
C8 C9 C10 108.98(16) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
C13 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C11 C12 C13 110.31(15) . . ?
C11 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C12 C11 C10 111.23(15) . . ?
H11A C11 H11B 108.0 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C11 C10 C9 111.32(15) . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 174.41(14) . . . . ?
O2 C6 C4 N1 74.73(17) . . . . ?
O2 C6 C4 C3 -176.21(13) . . . . ?
O2 C6 C4 C5 -49.53(19) . . . . ?
N1 C1 C2 C3 -7.18(16) . . . . ?
N1 C4 C3 C2 -14.65(14) . . . . ?
N1 C4 C3 C7 105.38(12) . . . . ?
N2 C6 C4 N1 -103.45(13) . . . . ?
N2 C6 C4 C3 5.60(14) . . . . ?
N2 C6 C4 C5 132.28(13) . . . . ?
N2 C8 C9 C10 -174.47(14) . . . . ?
C1 N1 C4 C6 121.11(13) . . . . ?
C1 N1 C4 C3 11.09(15) . . . . ?
C1 N1 C4 C5 -114.87(14) . . . . ?
C6 N2 C8 C13 -111.10(15) . . . . ?
C6 N2 C8 C9 123.40(15) . . . . ?
C6 N2 C7 O3 175.12(16) . . . . ?
C6 N2 C7 C3 -4.84(17) . . . . ?
C6 C4 C3 C2 -128.03(12) . . . . ?
C6 C4 C3 C7 -8.00(14) . . . . ?
C4 N1 C1 O1 175.77(13) . . . . ?
C4 N1 C1 C2 -2.64(16) . . . . ?
C4 C3 C2 C1 13.54(15) . . . . ?
C4 C3 C7 O3 -171.89(16) . . . . ?
C4 C3 C7 N2 8.07(15) . . . . ?
C13 C8 C9 C10 59.31(19) . . . . ?
C13 C12 C11 C10 -56.5(2) . . . . ?
C8 N2 C6 O2 -0.9(2) . . . . ?
C8 N2 C6 C4 177.29(12) . . . . ?
C8 N2 C7 O3 -2.7(3) . . . . ?
C8 N2 C7 C3 177.35(12) . . . . ?
C8 C13 C12 C11 58.72(18) . . . . ?
C8 C9 C10 C11 -56.2(2) . . . . ?
C2 C3 C7 O3 -56.5(2) . . . . ?
C2 C3 C7 N2 123.41(13) . . . . ?
C7 N2 C6 O2 -178.83(14) . . . . ?
C7 N2 C6 C4 -0.62(16) . . . . ?
C7 N2 C8 C13 66.53(19) . . . . ?
C7 N2 C8 C9 -58.97(19) . . . . ?
C7 C3 C2 C1 -100.90(14) . . . . ?
C5 C4 C3 C2 108.39(14) . . . . ?
C5 C4 C3 C7 -131.58(13) . . . . ?
C12 C13 C8 N2 172.43(13) . . . . ?
C12 C13 C8 C9 -60.99(18) . . . . ?
C12 C11 C10 C9 55.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform, hexane'
