# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_NSA_Cpd_1a
_database_code_depnum_ccdc_archive 'CCDC 2310781'
loop_
_audit_author_name
_audit_author_address
'Orde Munro'
;University of Leeds
United Kingdom
;
_audit_update_record             
;
2024-01-21 deposited with the CCDC.	2024-01-29 downloaded from the CCDC.
;
# mo_18OV_RR_Sample_1_0m
_audit_creation_date             2024-01-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C25 H17 N5 O2'
_chemical_formula_sum            'C25 H17 N5 O2'
_chemical_formula_weight         419.446
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.7392(4)
_cell_length_b                   14.6766(8)
_cell_length_c                   15.2758(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.656(2)
_cell_angle_gamma                90
_cell_volume                     1911.70(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      33.18
_cell_measurement_theta_min      2.39
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.7090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0554 before and 0.0367 after correction.
The Ratio of minimum to maximum transmission is 0.9498.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             872.568
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.9944
_diffrn_reflns_Laue_measured_fraction_max 0.9924
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            38141
_diffrn_reflns_point_group_measured_fraction_full 0.9944
_diffrn_reflns_point_group_measured_fraction_max 0.9924
_diffrn_reflns_theta_full        32.5000
_diffrn_reflns_theta_max         33.23
_diffrn_reflns_theta_min         3.07
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.9944
_diffrn_measured_fraction_theta_max 0.9924
_diffrn_measurement_device_type  'Bruker Venture D8 Photon I CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                6222
_reflns_number_total             7297
_reflns_threshold_expression     I>=2u(I)
_computing_data_collection       'APEX 3 (Bruker)'
_computing_cell_refinement       'APEX 3 (Bruker)'
_computing_data_reduction        'SAINT V8.38A (Bruker)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.1377
_refine_diff_density_min         -0.1293
_refine_diff_density_rms         0.0359
_refine_ls_d_res_high            0.6484
_refine_ls_d_res_low             6.6448
_refine_ls_goodness_of_fit_ref   1.0885
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     442
_refine_ls_number_reflns         7297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0187
_refine_ls_restrained_S_all      1.0885
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0153P)²+0.0490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0374
_refine_ls_wR_factor_ref         0.0410
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
;
_olex2_refine_details            
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA 5.0
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         R2SCAN
   BASIS SET:      cc-pVTZ
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2024-01-16_08-02-30
;
_atom_sites_solution_primary     dual
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
O1 O 0.45860(3) 0.520480(19) 0.649954(18) 0.02071(6) Uani 1.000000 .
O2 O 1.08697(3) 0.34861(2) 0.488849(18) 0.02352(6) Uani 1.000000 .
N2 N 0.76403(3) 0.456536(19) 0.546510(18) 0.01306(5) Uani 1.000000 .
N1 N 0.59016(4) 0.60899(2) 0.567079(19) 0.01450(5) Uani 1.000000 .
N3 N 0.88796(4) 0.42752(2) 0.396961(19) 0.01445(5) Uani 1.000000 .
N4 N 0.33241(4) 0.79019(2) 0.62427(2) 0.02446(7) Uani 1.000000 .
N5 N 1.11305(4) 0.35842(2) 0.22944(2) 0.02325(7) Uani 1.000000 .
C1 C 0.56631(4) 0.53199(2) 0.61132(2) 0.01386(6) Uani 1.000000 .
C6 C 0.86892(4) 0.38979(2) 0.54854(2) 0.01352(6) Uani 1.000000 .
C19 C 0.90290(4) 0.49823(2) 0.25308(2) 0.01309(6) Uani 1.000000 .
C2 C 0.68459(4) 0.45757(2) 0.61211(2) 0.01306(6) Uani 1.000000 .
C7 C 0.95920(4) 0.38678(2) 0.47532(2) 0.01486(6) Uani 1.000000 .
C10 C 0.50506(4) 0.75315(2) 0.49177(2) 0.01326(6) Uani 1.000000 .
C9 C 0.50167(4) 0.68998(2) 0.56250(2) 0.01334(6) Uani 1.000000 .
C11 C 0.58867(4) 0.73911(3) 0.42324(2) 0.01561(6) Uani 1.000000 .
H11 H 0.6512(6) 0.6770(4) 0.4209(3) 0.0339(13) Uani 1.000000 .
C3 C 0.70452(4) 0.39291(2) 0.68059(2) 0.01664(7) Uani 1.000000 .
H3a H 0.6362(7) 0.3966(4) 0.7311(3) 0.0362(14) Uani 1.000000 .
C18 C 0.94706(4) 0.42771(2) 0.31818(2) 0.01315(6) Uani 1.000000 .
C24 C 0.97252(4) 0.49593(2) 0.17738(2) 0.01633(6) Uani 1.000000 .
C20 C 0.79595(4) 0.56938(2) 0.25910(2) 0.01705(6) Uani 1.000000 .
H20 H 0.7417(6) 0.5730(4) 0.3156(4) 0.0381(14) Uani 1.000000 .
C17 C 1.04699(4) 0.35989(3) 0.30187(2) 0.01810(7) Uani 1.000000 .
H17 H 1.0763(7) 0.3042(4) 0.3476(4) 0.0383(14) Uani 1.000000 .
C5 C 0.89991(4) 0.32304(2) 0.61522(2) 0.01753(7) Uani 1.000000 .
H5 H 0.9886(6) 0.2719(4) 0.6143(4) 0.0352(14) Uani 1.000000 .
C22 C 0.83050(5) 0.63169(3) 0.11725(3) 0.02213(8) Uani 1.000000 .
H22 H 0.8021(7) 0.6836(4) 0.0657(4) 0.0408(15) Uani 1.000000 .
C15 C 0.42060(4) 0.83578(3) 0.49204(2) 0.01830(7) Uani 1.000000 .
C23 C 0.93588(5) 0.56425(3) 0.11048(2) 0.02102(7) Uani 1.000000 .
H23 H 0.9919(7) 0.5626(4) 0.0540(3) 0.0408(15) Uani 1.000000 .
C8 C 0.41547(4) 0.71165(3) 0.62553(2) 0.01813(7) Uani 1.000000 .
H8 H 0.4098(6) 0.6658(4) 0.6805(3) 0.0342(14) Uani 1.000000 .
C21 C 0.75997(5) 0.63372(3) 0.19213(3) 0.02132(7) Uani 1.000000 .
H21 H 0.6773(7) 0.6875(4) 0.1975(4) 0.0427(16) Uani 1.000000 .
C12 C 0.58995(5) 0.80550(3) 0.35991(3) 0.02053(7) Uani 1.000000 .
H12 H 0.6565(7) 0.7947(4) 0.3100(4) 0.0430(15) Uani 1.000000 .
C4 C 0.81510(4) 0.32455(3) 0.68224(2) 0.01888(7) Uani 1.000000 .
H4 H 0.8333(7) 0.2739(4) 0.7341(4) 0.0396(15) Uani 1.000000 .
C16 C 0.33620(5) 0.84939(3) 0.56011(3) 0.02471(8) Uani 1.000000 .
H16 H 0.2713(7) 0.9129(4) 0.5607(4) 0.0493(17) Uani 1.000000 .
C25 C 1.07841(5) 0.42468(3) 0.17058(3) 0.02235(8) Uani 1.000000 .
H25 H 1.1335(7) 0.4234(4) 0.1127(4) 0.0457(16) Uani 1.000000 .
C13 C 0.50691(5) 0.88819(3) 0.36087(3) 0.02508(8) Uani 1.000000 .
H13 H 0.5090(7) 0.9396(4) 0.3107(4) 0.0468(16) Uani 1.000000 .
C14 C 0.42273(5) 0.90282(3) 0.42551(3) 0.02441(8) Uani 1.000000 .
H14 H 0.3564(7) 0.9655(4) 0.4269(4) 0.0458(16) Uani 1.000000 .
H3 H 0.7832(7) 0.4553(4) 0.3958(4) 0.0314(14) Uani 1.000000 .
H1 H 0.6841(7) 0.6088(4) 0.5391(4) 0.0324(14) Uani 1.000000 .


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 1.2274(4) . ?
O2 C7 1.2257(4) . ?
N2 C6 1.3373(4) . ?
N2 C2 1.3384(4) . ?
N1 C1 1.3560(4) . ?
N1 C9 1.4114(4) . ?
N1 H1 1.005(5) . ?
N3 C7 1.3607(4) . ?
N3 C18 1.4097(4) . ?
N3 H3 0.999(5) . ?
N4 C8 1.3601(5) . ?
N4 C16 1.3155(5) . ?
N5 C17 1.3556(5) . ?
N5 C25 1.3140(5) . ?
C1 C2 1.5020(5) . ?
C6 C7 1.5041(5) . ?
C6 C5 1.3963(5) . ?
C19 C18 1.4287(5) . ?
C19 C24 1.4202(5) . ?
C19 C20 1.4178(5) . ?
C2 C3 1.3948(5) . ?
C10 C9 1.4289(5) . ?
C10 C11 1.4168(5) . ?
C10 C15 1.4201(5) . ?
C9 C8 1.3832(5) . ?
C11 H11 1.067(5) . ?
C11 C12 1.3748(5) . ?
C3 H3a 1.076(5) . ?
C3 C4 1.3894(5) . ?
C18 C17 1.3823(5) . ?
C24 C23 1.4174(5) . ?
C24 C25 1.4151(5) . ?
C20 H20 1.073(5) . ?
C20 C21 1.3770(5) . ?
C17 H17 1.070(5) . ?
C5 H5 1.081(5) . ?
C5 C4 1.3894(5) . ?
C22 H22 1.085(5) . ?
C22 C23 1.3712(6) . ?
C22 C21 1.4135(6) . ?
C15 C16 1.4148(5) . ?
C15 C14 1.4176(5) . ?
C23 H23 1.081(5) . ?
C8 H8 1.086(5) . ?
C21 H21 1.085(5) . ?
C12 H12 1.067(5) . ?
C12 C13 1.4158(6) . ?
C4 H4 1.072(5) . ?
C16 H16 1.092(6) . ?
C25 H25 1.095(5) . ?
C13 H13 1.078(5) . ?
C13 C14 1.3714(6) . ?
C14 H14 1.089(5) . ?

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 N2 C6 117.15(3) . . ?
C9 N1 C1 125.75(3) . . ?
H1 N1 C1 116.0(3) . . ?
H1 N1 C9 118.1(3) . . ?
C18 N3 C7 124.70(3) . . ?
H3 N3 C7 115.8(3) . . ?
H3 N3 C18 119.4(3) . . ?
C16 N4 C8 118.03(3) . . ?
C25 N5 C17 118.11(3) . . ?
N1 C1 O1 124.90(3) . . ?
C2 C1 O1 119.66(3) . . ?
C2 C1 N1 115.43(3) . . ?
C7 C6 N2 118.22(3) . . ?
C5 C6 N2 123.60(3) . . ?
C5 C6 C7 118.18(3) . . ?
C24 C19 C18 116.81(3) . . ?
C20 C19 C18 124.74(3) . . ?
C20 C19 C24 118.46(3) . . ?
C1 C2 N2 118.11(3) . . ?
C3 C2 N2 123.63(3) . . ?
C3 C2 C1 118.26(3) . . ?
N3 C7 O2 124.99(3) . . ?
C6 C7 O2 119.67(3) . . ?
C6 C7 N3 115.33(3) . . ?
C11 C10 C9 124.32(3) . . ?
C15 C10 C9 117.06(3) . . ?
C15 C10 C11 118.61(3) . . ?
C10 C9 N1 118.81(3) . . ?
C8 C9 N1 122.35(3) . . ?
C8 C9 C10 118.81(3) . . ?
H11 C11 C10 120.0(3) . . ?
C12 C11 C10 120.13(3) . . ?
C12 C11 H11 119.9(3) . . ?
H3a C3 C2 120.4(3) . . ?
C4 C3 C2 118.49(3) . . ?
C4 C3 H3a 121.1(3) . . ?
C19 C18 N3 120.14(3) . . ?
C17 C18 N3 121.10(3) . . ?
C17 C18 C19 118.76(3) . . ?
C23 C24 C19 120.05(3) . . ?
C25 C24 C19 118.75(3) . . ?
C25 C24 C23 121.20(3) . . ?
H20 C20 C19 120.2(3) . . ?
C21 C20 C19 120.22(3) . . ?
C21 C20 H20 119.6(3) . . ?
C18 C17 N5 123.88(3) . . ?
H17 C17 N5 115.9(3) . . ?
H17 C17 C18 120.2(3) . . ?
H5 C5 C6 120.2(3) . . ?
C4 C5 C6 118.47(3) . . ?
C4 C5 H5 121.4(3) . . ?
C23 C22 H22 120.2(3) . . ?
C21 C22 H22 120.1(3) . . ?
C21 C22 C23 119.69(3) . . ?
C16 C15 C10 118.54(3) . . ?
C14 C15 C10 120.14(3) . . ?
C14 C15 C16 121.32(3) . . ?
C22 C23 C24 120.38(3) . . ?
H23 C23 C24 119.3(3) . . ?
H23 C23 C22 120.3(3) . . ?
C9 C8 N4 123.73(3) . . ?
H8 C8 N4 114.9(3) . . ?
H8 C8 C9 121.3(3) . . ?
C22 C21 C20 121.17(4) . . ?
H21 C21 C20 119.4(3) . . ?
H21 C21 C22 119.5(3) . . ?
H12 C12 C11 119.2(3) . . ?
C13 C12 C11 121.13(4) . . ?
C13 C12 H12 119.7(3) . . ?
C5 C4 C3 118.65(3) . . ?
H4 C4 C3 120.3(3) . . ?
H4 C4 C5 121.1(3) . . ?
C15 C16 N4 123.82(4) . . ?
H16 C16 N4 117.4(3) . . ?
H16 C16 C15 118.8(3) . . ?
C24 C25 N5 123.57(3) . . ?
H25 C25 N5 117.6(3) . . ?
H25 C25 C24 118.9(3) . . ?
H13 C13 C12 120.3(3) . . ?
C14 C13 C12 119.91(4) . . ?
C14 C13 H13 119.8(3) . . ?
C13 C14 C15 120.06(4) . . ?
H14 C14 C15 118.8(3) . . ?
H14 C14 C13 121.2(3) . . ?

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 N1 C9 3.96(4) . . . . ?
O1 C1 C2 N2 156.64(3) . . . . ?
O1 C1 C2 C3 -22.76(4) . . . . ?
O2 C7 N3 C18 3.45(5) . . . . ?
O2 C7 C6 N2 155.95(3) . . . . ?
O2 C7 C6 C5 -23.68(4) . . . . ?
N2 C6 C7 N3 -24.66(3) . . . . ?
N2 C6 C5 C4 1.43(4) . . . . ?
N2 C2 C1 N1 -24.03(3) . . . . ?
N2 C2 C3 C4 1.38(4) . . . . ?
N1 C1 C2 C3 156.57(3) . . . . ?
N1 C9 C10 C11 1.86(4) . . . . ?
N1 C9 C10 C15 -177.03(3) . . . . ?
N1 C9 C8 N4 178.21(3) . . . . ?
N3 C7 C6 C5 155.72(3) . . . . ?
N3 C18 C19 C24 177.38(3) . . . . ?
N3 C18 C19 C20 -2.50(4) . . . . ?
N3 C18 C17 N5 -177.01(3) . . . . ?
N4 C8 C9 C10 0.15(4) . . . . ?
N4 C16 C15 C10 0.76(5) . . . . ?
N4 C16 C15 C14 -178.81(4) . . . . ?
N5 C17 C18 C19 3.58(5) . . . . ?
N5 C25 C24 C19 2.04(5) . . . . ?
N5 C25 C24 C23 -178.11(4) . . . . ?
C1 C2 C3 C4 -179.25(3) . . . . ?
C6 C5 C4 C3 -0.71(4) . . . . ?
C19 C24 C23 C22 -1.52(4) . . . . ?
C19 C20 C21 C22 -1.33(4) . . . . ?
C2 C3 C4 C5 -0.59(4) . . . . ?
C10 C11 C12 C13 -0.84(4) . . . . ?
C10 C15 C14 C13 -0.25(4) . . . . ?
C11 C12 C13 C14 -0.34(5) . . . . ?
C24 C23 C22 C21 0.96(4) . . . . ?
C20 C21 C22 C23 0.47(5) . . . . ?
C15 C14 C13 C12 0.87(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_NSA_Cpd_1d
_database_code_depnum_ccdc_archive 'CCDC 2310784'
loop_
_audit_author_name
_audit_author_address
'Orde Munro'
;University of Leeds
United Kingdom
;
_audit_update_record             
;
2024-01-21 deposited with the CCDC.	2024-01-29 downloaded from the CCDC.
;
# RRH84
_audit_creation_date             2024-01-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C23 H19 N7 O2'
_chemical_formula_sum            'C23 H19 N7 O2'
_chemical_formula_weight         425.453
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2

_symmetry_Int_Tables_number      13
_cell_length_a                   10.4220(2)
_cell_length_b                   11.8014(3)
_cell_length_c                   8.6298(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.076(1)
_cell_angle_gamma                90
_cell_volume                     983.60(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8103
_cell_measurement_temperature    153.15
_cell_measurement_theta_max      31.62
_cell_measurement_theta_min      2.72
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.7025
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0496 before and 0.0387 after correction.
The Ratio of minimum to maximum transmission is 0.9414.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       shard
_exptl_crystal_F_000             444.296
_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.296
_exptl_crystal_size_min          0.126
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.9979
_diffrn_reflns_Laue_measured_fraction_max 0.9973
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23461
_diffrn_reflns_point_group_measured_fraction_full 0.9979
_diffrn_reflns_point_group_measured_fraction_max 0.9973
_diffrn_reflns_theta_full        31.5000
_diffrn_reflns_theta_max         31.64
_diffrn_reflns_theta_min         2.11
_diffrn_ambient_temperature      153.15
_diffrn_measured_fraction_theta_full 0.9979
_diffrn_measured_fraction_theta_max 0.9973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -15
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2785
_reflns_number_total             3318
_reflns_threshold_expression     I>=2u(I)
_computing_data_collection       'APEX 2 (Bruker)'
_computing_cell_refinement       'APEX 2 (Bruker)'
_computing_data_reduction        'SAINT V8.34A (Bruker)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.2664
_refine_diff_density_min         -0.1915
_refine_diff_density_rms         0.0591
_refine_ls_d_res_high            0.6773
_refine_ls_d_res_low             9.6579
_refine_ls_goodness_of_fit_ref   1.0941
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0259
_refine_ls_restrained_S_all      1.0941
_refine_ls_shift/su_max          -0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0305P)²+0.0731P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0591
_refine_ls_wR_factor_ref         0.0639
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
;
_olex2_refine_details            
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA 5.0
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         R2SCAN
   BASIS SET:      cc-pVTZ
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2024-01-16_18-09-22
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O1 O 0.68064(5) 0.37829(4) 0.68148(5) 0.02258(10) Uani 1.000000 1 . . .
N1 N 0.5 0.41221(6) 0.25 0.01404(12) Uani 1.000000 2 S T P
N4 N 0.89258(5) 0.67676(4) 0.86602(6) 0.01887(10) Uani 1.000000 1 . . .
N2 N 0.69020(5) 0.52478(4) 0.51104(6) 0.01629(10) Uani 1.000000 1 . . .
N3 N 0.84421(5) 0.57718(4) 0.78602(6) 0.01710(10) Uani 1.000000 1 . . .
C3 C 0.57219(5) 0.35365(5) 0.38800(6) 0.01427(10) Uani 1.000000 1 . . .
C5 C 0.76269(5) 0.60421(5) 0.63143(6) 0.01464(10) Uani 1.000000 1 . . .
C11 C 0.84120(6) 0.76748(5) 0.76400(7) 0.01757(11) Uani 1.000000 1 . . .
C6 C 0.75653(6) 0.72398(5) 0.60615(7) 0.01591(10) Uani 1.000000 1 . . .
C4 C 0.65303(5) 0.42014(5) 0.54236(7) 0.01518(10) Uani 1.000000 1 . . .
C2 C 0.57389(6) 0.23562(5) 0.39481(7) 0.01845(11) Uani 1.000000 1 . . .
H2a H 0.6321(10) 0.1946(8) 0.5109(11) 0.042(2) Uani 1.000000 1 . . .
C7 C 0.68920(7) 0.79747(6) 0.47323(8) 0.02154(12) Uani 1.000000 1 . . .
H7 H 0.6271(10) 0.7655(7) 0.3569(11) 0.042(2) Uani 1.000000 1 . . .
C1 C 0.5 0.17594(7) 0.25 0.02051(16) Uani 1.000000 2 S T P
H1 H 0.5 0.0828(10) 0.25 0.046(4) Uani 1.000000 2 S T P
C10 C 0.85863(7) 0.88418(6) 0.79528(9) 0.02525(13) Uani 1.000000 1 . . .
H10 H 0.9262(10) 0.9117(9) 0.9200(11) 0.052(3) Uani 1.000000 1 . . .
C12 C 0.97415(7) 0.67728(7) 1.04310(8) 0.02413(13) Uani 1.000000 1 . . .
H12a H 0.9112(11) 0.6966(13) 1.1099(11) 0.087(4) Uani 1.000000 1 . . .
H12b H 1.0258(14) 0.6032(10) 1.0781(12) 0.084(4) Uani 1.000000 1 . . .
H12c H 1.0428(12) 0.7439(12) 1.0665(11) 0.084(5) Uani 1.000000 1 . . .
C8 C 0.70747(8) 0.91302(6) 0.50332(9) 0.02841(14) Uani 1.000000 1 . . .
H8 H 0.6599(11) 0.9729(8) 0.4038(13) 0.056(3) Uani 1.000000 1 . . .
C9 C 0.79042(8) 0.95538(6) 0.66269(9) 0.02998(15) Uani 1.000000 1 . . .
H9 H 0.7992(11) 1.0471(8) 0.6764(13) 0.056(3) Uani 1.000000 1 . . .
H2 H 0.6659(10) 0.5479(8) 0.3957(12) 0.040(2) Uani 1.000000 1 . . .


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 C4 1.2281(6) . ?
N1 C3 1.3373(6) . ?
N1 C3 1.3373(6) 2_655 ?
N4 N3 1.3602(7) . ?
N4 C11 1.3615(8) . ?
N4 C12 1.4428(8) . ?
N2 C5 1.3924(7) . ?
N2 C4 1.3516(7) . ?
N2 H2 0.970(9) . ?
N3 C5 1.3234(7) . ?
C3 C4 1.5022(8) . ?
C3 C2 1.3939(8) . ?
C5 C6 1.4280(8) . ?
C11 C6 1.4122(8) . ?
C11 C10 1.4020(9) . ?
C6 C7 1.3983(8) . ?
C2 H2a 1.072(8) . ?
C2 C1 1.3883(7) 2_655 ?
C7 H7 1.040(9) . ?
C7 C8 1.3878(10) . ?
C1 H1 1.100(12) . ?
C10 H10 1.091(8) . ?
C10 C9 1.3817(10) . ?
C12 H12a 1.049(10) . ?
C12 H12b 1.011(11) . ?
C12 H12c 1.031(10) . ?
C8 H8 1.078(9) . ?
C8 C9 1.4125(10) . ?
C9 H9 1.089(9) . ?

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
C3 N1 C3 117.77(7) . 2_655 ?
C11 N4 N3 111.75(5) . . ?
C12 N4 N3 119.98(5) . . ?
C12 N4 C11 127.84(5) . . ?
C4 N2 C5 125.57(5) . . ?
H2 N2 C5 115.8(5) . . ?
H2 N2 C4 118.6(5) . . ?
C5 N3 N4 106.17(5) . . ?
C4 C3 N1 117.39(5) . 2_655 ?
C2 C3 N1 123.22(5) . 2_655 ?
C2 C3 C4 119.38(5) . . ?
N3 C5 N2 123.55(5) . . ?
C6 C5 N2 124.87(5) . . ?
C6 C5 N3 111.56(5) . . ?
C6 C11 N4 106.81(5) . . ?
C10 C11 N4 131.07(6) . . ?
C10 C11 C6 122.11(6) . . ?
C11 C6 C5 103.68(5) . . ?
C7 C6 C5 135.98(6) . . ?
C7 C6 C11 120.32(5) . . ?
N2 C4 O1 125.69(5) . . ?
C3 C4 O1 120.27(5) . . ?
C3 C4 N2 114.04(5) . . ?
H2a C2 C3 119.0(5) . . ?
C1 C2 C3 118.36(6) 2_655 . ?
C1 C2 H2a 122.6(5) 2_655 . ?
H7 C7 C6 120.3(5) . . ?
C8 C7 C6 117.69(6) . . ?
C8 C7 H7 122.0(5) . . ?
C2 C1 C2 119.03(8) . 2_655 ?
H1 C1 C2 120.49(4) . 2_655 ?
H1 C1 C2 120.49(4) . . ?
H10 C10 C11 118.1(6) . . ?
C9 C10 C11 116.66(6) . . ?
C9 C10 H10 125.2(6) . . ?
H12a C12 N4 110.0(5) . . ?
H12b C12 N4 110.4(6) . . ?
H12b C12 H12a 113.3(11) . . ?
H12c C12 N4 107.4(5) . . ?
H12c C12 H12a 105.0(10) . . ?
H12c C12 H12b 110.4(11) . . ?
H8 C8 C7 120.3(5) . . ?
C9 C8 C7 121.38(6) . . ?
C9 C8 H8 118.3(5) . . ?
C8 C9 C10 121.82(6) . . ?
H9 C9 C10 121.2(6) . . ?
H9 C9 C8 117.0(6) . . ?

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 C4 N2 C5 -1.99(7) . . . . ?
O1 C4 C3 N1 154.67(5) . . . 2_655 ?
O1 C4 C3 C2 -24.49(6) . . . . ?
N1 C3 C4 N2 -25.80(5) 2_655 . . . ?
N1 C3 C4 N2 -25.80(5) . . . . ?
N1 C3 C2 C1 1.79(5) . . . 2_655 ?
N1 C3 C2 C1 1.79(5) . 2_655 2_655 . ?
N4 N3 C5 N2 -178.26(4) . . . . ?
N4 N3 C5 C6 0.38(5) . . . . ?
N4 C11 C6 C5 1.58(5) . . . . ?
N4 C11 C6 C7 -179.59(5) . . . . ?
N4 C11 C10 C9 -179.58(7) . . . . ?
N2 C5 C6 C11 177.38(6) . . . . ?
N2 C5 C6 C7 -1.17(7) . . . . ?
N2 C4 C3 C2 155.04(5) . . . . ?
N3 C5 C6 C11 -1.24(5) . . . . ?
N3 C5 C6 C7 -179.79(5) . . . . ?
C3 C2 C1 C2 -0.83(8) . . 2_655 2_655 ?
C5 C6 C11 C10 -177.25(4) . . . . ?
C5 C6 C7 C8 177.55(7) . . . . ?
C11 C6 C7 C8 -0.81(6) . . . . ?
C11 C10 C9 C8 -0.15(7) . . . . ?
C6 C7 C8 C9 -0.37(7) . . . . ?
C7 C8 C9 C10 0.88(8) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_NSA_Cpd_1c
_database_code_depnum_ccdc_archive 'CCDC 2310783'
loop_
_audit_author_name
_audit_author_address
'Orde Munro'
;University of Leeds
United Kingdom
;
_audit_update_record             
;
2024-01-21 deposited with the CCDC.	2024-01-29 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_STRVA01_NSA_Cpd_1c          
;
PROBLEM: Flack parameter is too small
RESPONSE: The absolute structure cannot be established from the Flack parameter and is unknown by other experimental methods.
;
# Added during the CSD deposition process: Sunday 21 January 2024 12:13 PM
# end Validation Reply Form

# mo_18OV_RRH8_Sample3_0m
_audit_creation_date             2024-01-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C25 H17 N5 O2'
_chemical_formula_sum            'C25 H17 N5 O2'
_chemical_formula_weight         419.446
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   4.4778(2)
_cell_length_b                   16.9420(7)
_cell_length_c                   25.8329(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1959.76(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9833
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.53
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0533 before and 0.0454 after correction.
The Ratio of minimum to maximum transmission is 0.9000.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       needle
_exptl_crystal_F_000             872.568
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.9964
_diffrn_reflns_Laue_measured_fraction_max 0.9965
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            30705
_diffrn_reflns_point_group_measured_fraction_full 0.9975
_diffrn_reflns_point_group_measured_fraction_max 0.9975
_diffrn_reflns_theta_full        28.0000
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.88
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.9965
_diffrn_measurement_device_type  'Bruker Venture D8 Photon I CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.999
_reflns_limit_h_max              5
_reflns_limit_h_min              -5
_reflns_limit_k_max              22
_reflns_limit_k_min              -22
_reflns_limit_l_max              34
_reflns_limit_l_min              -33
_reflns_number_gt                4418
_reflns_number_total             4830
_reflns_threshold_expression     I>=2u(I)
_computing_data_collection       'APEX 3 (Bruker)'
_computing_cell_refinement       'APEX 3 (Bruker)'
_computing_data_reduction        'SAINT V8.38A (Bruker)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.1037
_refine_diff_density_min         -0.1135
_refine_diff_density_rms         0.0289
_refine_ls_abs_structure_details 
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_d_res_high            0.7503
_refine_ls_d_res_low             7.0835
_refine_ls_goodness_of_fit_ref   1.1112
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     442
_refine_ls_number_reflns         4830
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0172
_refine_ls_restrained_S_all      1.1112
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0112P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0278
_refine_ls_wR_factor_ref         0.0292
_olex2_refinement_description    
;
;
_olex2_refine_details            
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA 5.0
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         R2SCAN
   BASIS SET:      cc-pVTZ
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2024-01-16_17-15-41
;
_atom_sites_solution_primary     dual
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
O1 O 1.19186(11) 0.70430(2) 0.752915(15) 0.02801(11) Uani 1.000000 .
O2 O 0.73915(11) 0.61077(3) 0.499885(15) 0.03244(12) Uani 1.000000 .
N4 N 0.44096(12) 0.49674(3) 0.730781(18) 0.01957(11) Uani 1.000000 .
N5 N 0.66442(12) 0.39488(3) 0.623536(17) 0.02038(12) Uani 1.000000 .
N1 N 0.84951(12) 0.60888(3) 0.732238(19) 0.01803(11) Uani 1.000000 .
N3 N 0.67580(14) 0.52875(3) 0.56960(2) 0.02260(13) Uani 1.000000 .
N2 N 0.93338(12) 0.63378(3) 0.631754(18) 0.01828(11) Uani 1.000000 .
C17 C 0.49691(13) 0.39693(3) 0.57963(2) 0.01648(12) Uani 1.000000 .
C18 C 0.50543(15) 0.46741(3) 0.54907(2) 0.01841(13) Uani 1.000000 .
C1 C 1.04842(15) 0.66624(3) 0.72138(2) 0.01842(13) Uani 1.000000 .
C8 C 0.56668(14) 0.51222(3) 0.77762(2) 0.01664(12) Uani 1.000000 .
C13 C 0.49400(14) 0.46986(3) 0.82324(2) 0.01853(13) Uani 1.000000 .
C23 C 0.31184(16) 0.26494(4) 0.59507(2) 0.02336(14) Uani 1.000000 .
C9 C 0.78327(14) 0.57429(3) 0.77981(2) 0.01613(12) Uani 1.000000 .
C2 C 1.07871(14) 0.68183(3) 0.66404(2) 0.01814(13) Uani 1.000000 .
C10 C 0.91441(15) 0.59353(4) 0.82641(2) 0.01968(14) Uani 1.000000 .
C16 C 0.24339(15) 0.43923(4) 0.72802(3) 0.02330(14) Uani 1.000000 .
C7 C 0.77776(15) 0.59415(3) 0.54555(2) 0.02183(14) Uani 1.000000 .
C20 C 0.17059(16) 0.40650(4) 0.48750(3) 0.02628(15) Uani 1.000000 .
C24 C 0.47945(16) 0.26337(4) 0.63938(3) 0.02475(15) Uani 1.000000 .
C22 C 0.31771(15) 0.33293(3) 0.56322(2) 0.01875(13) Uani 1.000000 .
C21 C 0.15442(16) 0.33886(4) 0.51647(2) 0.02480(15) Uani 1.000000 .
C19 C 0.34566(15) 0.47157(4) 0.50353(2) 0.02329(14) Uani 1.000000 .
C11 C 0.83625(16) 0.55129(4) 0.87168(2) 0.02233(14) Uani 1.000000 .
C12 C 0.63355(15) 0.49057(4) 0.87061(2) 0.02215(14) Uani 1.000000 .
C25 C 0.65468(16) 0.33008(4) 0.65178(2) 0.02312(14) Uani 1.000000 .
C3 C 1.24957(16) 0.74531(4) 0.64705(2) 0.02435(14) Uani 1.000000 .
C15 C 0.15828(16) 0.39267(4) 0.77094(3) 0.02496(14) Uani 1.000000 .
C14 C 0.28253(15) 0.40837(3) 0.81845(3) 0.02225(14) Uani 1.000000 .
C6 C 0.94977(15) 0.64836(3) 0.58091(2) 0.01989(13) Uani 1.000000 .
C4 C 1.26432(17) 0.76050(4) 0.59415(2) 0.02771(16) Uani 1.000000 .
C5 C 1.11014(16) 0.71129(4) 0.56035(3) 0.02577(16) Uani 1.000000 .
H10 H 1.0749(17) 0.6392(4) 0.8277(2) 0.0335(19) Uani 1.000000 .
H11 H 0.9474(18) 0.5677(4) 0.9077(3) 0.039(2) Uani 1.000000 .
H3 H 0.747(2) 0.5196(4) 0.6060(3) 0.042(3) Uani 1.000000 .
H19 H 0.3542(19) 0.5258(4) 0.4804(3) 0.043(2) Uani 1.000000 .
H3a H 1.3643(18) 0.7814(4) 0.6746(3) 0.045(2) Uani 1.000000 .
H16 H 0.1428(18) 0.4288(4) 0.6902(3) 0.045(2) Uani 1.000000 .
H4 H 1.392(2) 0.8093(4) 0.5790(3) 0.050(2) Uani 1.000000 .
H25 H 0.7959(18) 0.3285(4) 0.6864(2) 0.042(2) Uani 1.000000 .
H21 H 0.0126(19) 0.2903(4) 0.5045(3) 0.051(2) Uani 1.000000 .
H12 H 0.5760(19) 0.4583(4) 0.9054(3) 0.045(2) Uani 1.000000 .
H23 H 0.1714(19) 0.2158(4) 0.5839(3) 0.046(2) Uani 1.000000 .
H24 H 0.4789(19) 0.2136(4) 0.6651(3) 0.049(2) Uani 1.000000 .
H1 H 0.7404(19) 0.5830(4) 0.7027(3) 0.031(2) Uani 1.000000 .
H5 H 1.1160(19) 0.7199(4) 0.5189(3) 0.050(2) Uani 1.000000 .
H15 H -0.0057(19) 0.3460(4) 0.7661(3) 0.044(2) Uani 1.000000 .
H14 H 0.2180(19) 0.3756(4) 0.8529(3) 0.043(2) Uani 1.000000 .
H20 H 0.044(2) 0.4115(4) 0.4525(3) 0.050(2) Uani 1.000000 .


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 1.2215(7) . ?
O2 C7 1.2250(7) . ?
N4 C8 1.3600(7) . ?
N4 C16 1.3180(8) . ?
N5 C17 1.3602(7) . ?
N5 C25 1.3189(8) . ?
N1 C1 1.3477(8) . ?
N1 C9 1.3936(7) . ?
N1 H1 1.006(7) . ?
N3 C18 1.3940(8) . ?
N3 C7 1.3500(7) . ?
N3 H3 1.006(8) . ?
N2 C2 1.3348(7) . ?
N2 C6 1.3385(7) . ?
C17 C18 1.4319(8) . ?
C17 C22 1.4140(8) . ?
C18 C19 1.3788(8) . ?
C1 C2 1.5105(8) . ?
C8 C13 1.4177(8) . ?
C8 C9 1.4317(8) . ?
C13 C12 1.4181(9) . ?
C13 C14 1.4133(9) . ?
C23 C24 1.3690(9) . ?
C23 C22 1.4158(8) . ?
C23 H23 1.083(7) . ?
C9 C10 1.3784(8) . ?
C2 C3 1.3910(8) . ?
C10 C11 1.4150(9) . ?
C10 H10 1.056(7) . ?
C16 C15 1.4130(9) . ?
C16 H16 1.090(6) . ?
C7 C6 1.5070(8) . ?
C20 C21 1.3705(9) . ?
C20 C19 1.4148(9) . ?
C20 H20 1.071(7) . ?
C24 C25 1.4128(9) . ?
C24 H24 1.073(7) . ?
C22 C21 1.4154(9) . ?
C21 H21 1.084(7) . ?
C19 H19 1.097(6) . ?
C11 C12 1.3723(10) . ?
C11 H11 1.091(7) . ?
C12 H12 1.083(7) . ?
C25 H25 1.096(7) . ?
C3 C4 1.3922(9) . ?
C3 H3a 1.070(7) . ?
C15 C14 1.3734(9) . ?
C15 H15 1.086(8) . ?
C14 H14 1.087(6) . ?
C6 C5 1.3908(8) . ?
C4 C5 1.3907(9) . ?
C4 H4 1.079(7) . ?
C5 H5 1.081(7) . ?

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
C16 N4 C8 117.93(5) . . ?
C25 N5 C17 117.67(5) . . ?
C9 N1 C1 128.87(5) . . ?
H1 N1 C1 118.5(4) . . ?
H1 N1 C9 112.5(4) . . ?
C7 N3 C18 128.45(5) . . ?
H3 N3 C18 114.5(4) . . ?
H3 N3 C7 116.8(5) . . ?
C6 N2 C2 118.29(5) . . ?
C18 C17 N5 117.80(5) . . ?
C22 C17 N5 122.91(5) . . ?
C22 C17 C18 119.29(5) . . ?
C17 C18 N3 115.24(5) . . ?
C19 C18 N3 124.78(5) . . ?
C19 C18 C17 119.95(6) . . ?
N1 C1 O1 126.10(6) . . ?
C2 C1 O1 120.96(5) . . ?
C2 C1 N1 112.93(5) . . ?
C13 C8 N4 123.16(5) . . ?
C9 C8 N4 117.21(5) . . ?
C9 C8 C13 119.63(5) . . ?
C12 C13 C8 119.41(5) . . ?
C14 C13 C8 117.00(6) . . ?
C14 C13 C12 123.59(5) . . ?
C22 C23 C24 119.44(6) . . ?
H23 C23 C24 121.7(4) . . ?
H23 C23 C22 118.8(4) . . ?
C8 C9 N1 114.72(5) . . ?
C10 C9 N1 125.45(6) . . ?
C10 C9 C8 119.80(5) . . ?
C1 C2 N2 117.54(5) . . ?
C3 C2 N2 122.85(5) . . ?
C3 C2 C1 119.60(5) . . ?
C11 C10 C9 119.78(6) . . ?
H10 C10 C9 119.4(3) . . ?
H10 C10 C11 120.9(4) . . ?
C15 C16 N4 123.45(6) . . ?
H16 C16 N4 116.5(4) . . ?
H16 C16 C15 120.1(4) . . ?
N3 C7 O2 125.74(6) . . ?
C6 C7 O2 121.05(5) . . ?
C6 C7 N3 113.21(5) . . ?
C19 C20 C21 121.40(6) . . ?
H20 C20 C21 120.0(4) . . ?
H20 C20 C19 118.6(4) . . ?
C25 C24 C23 118.59(6) . . ?
H24 C24 C23 122.1(4) . . ?
H24 C24 C25 119.3(4) . . ?
C23 C22 C17 117.40(5) . . ?
C21 C22 C17 119.64(5) . . ?
C21 C22 C23 122.96(6) . . ?
C22 C21 C20 119.87(6) . . ?
H21 C21 C20 120.7(4) . . ?
H21 C21 C22 119.4(4) . . ?
C20 C19 C18 119.83(6) . . ?
H19 C19 C18 119.3(4) . . ?
H19 C19 C20 120.9(4) . . ?
C12 C11 C10 121.75(6) . . ?
H11 C11 C10 117.6(4) . . ?
H11 C11 C12 120.7(4) . . ?
C11 C12 C13 119.62(6) . . ?
H12 C12 C13 119.1(4) . . ?
H12 C12 C11 121.3(4) . . ?
C24 C25 N5 123.97(6) . . ?
H25 C25 N5 116.9(3) . . ?
H25 C25 C24 119.1(3) . . ?
C4 C3 C2 118.61(6) . . ?
H3a C3 C2 119.7(4) . . ?
H3a C3 C4 121.7(4) . . ?
C14 C15 C16 118.94(6) . . ?
H15 C15 C16 119.8(4) . . ?
H15 C15 C14 121.2(4) . . ?
C15 C14 C13 119.50(6) . . ?
H14 C14 C13 118.9(4) . . ?
H14 C14 C15 121.6(4) . . ?
C7 C6 N2 117.02(5) . . ?
C5 C6 N2 122.99(6) . . ?
C5 C6 C7 119.97(5) . . ?
C5 C4 C3 118.81(6) . . ?
H4 C4 C3 121.5(4) . . ?
H4 C4 C5 119.7(4) . . ?
C4 C5 C6 118.43(6) . . ?
H5 C5 C6 119.7(4) . . ?
H5 C5 C4 121.9(4) . . ?

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 N1 C9 -7.22(8) . . . . ?
O1 C1 C2 N2 174.75(6) . . . . ?
O1 C1 C2 C3 -6.32(7) . . . . ?
O2 C7 N3 C18 -0.88(9) . . . . ?
O2 C7 C6 N2 167.55(6) . . . . ?
O2 C7 C6 C5 -10.95(8) . . . . ?
N4 C8 C13 C12 -179.28(6) . . . . ?
N4 C8 C13 C14 0.74(7) . . . . ?
N4 C8 C9 N1 -3.11(6) . . . . ?
N4 C8 C9 C10 178.89(5) . . . . ?
N4 C16 C15 C14 1.11(8) . . . . ?
N5 C17 C18 N3 -3.27(6) . . . . ?
N5 C17 C18 C19 178.29(5) . . . . ?
N5 C17 C22 C23 1.21(7) . . . . ?
N5 C17 C22 C21 -178.66(6) . . . . ?
N5 C25 C24 C23 0.95(8) . . . . ?
N1 C1 C2 N2 -6.23(6) . . . . ?
N1 C1 C2 C3 172.70(5) . . . . ?
N1 C9 C8 C13 176.57(5) . . . . ?
N1 C9 C10 C11 -177.15(6) . . . . ?
N3 C18 C17 C22 176.86(5) . . . . ?
N3 C18 C19 C20 -177.45(6) . . . . ?
N3 C7 C6 N2 -12.04(7) . . . . ?
N3 C7 C6 C5 169.45(6) . . . . ?
N2 C2 C3 C4 1.49(7) . . . . ?
N2 C6 C5 C4 1.07(7) . . . . ?
C17 C18 C19 C20 0.83(7) . . . . ?
C17 C22 C23 C24 -0.78(7) . . . . ?
C17 C22 C21 C20 -0.10(7) . . . . ?
C18 C19 C20 C21 0.30(7) . . . . ?
C1 C2 C3 C4 -177.38(6) . . . . ?
C8 C13 C12 C11 0.12(7) . . . . ?
C8 C13 C14 C15 -0.20(7) . . . . ?
C8 C9 C10 C11 0.61(7) . . . . ?
C13 C12 C11 C10 -0.97(7) . . . . ?
C13 C14 C15 C16 -0.65(7) . . . . ?
C23 C22 C21 C20 -179.96(6) . . . . ?
C9 C10 C11 C12 0.60(7) . . . . ?
C2 C3 C4 C5 -0.58(8) . . . . ?
C7 C6 C5 C4 179.48(6) . . . . ?
C3 C4 C5 C6 -0.62(8) . . . . ?


_olex2_exptl_crystal_mounting_method 
'mounted on a MiTeGen 300 um needle loop with Paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_NSA_Cpd_1e
_database_code_depnum_ccdc_archive 'CCDC 2310785'
loop_
_audit_author_name
_audit_author_address
'Orde Munro'
;University of Leeds
United Kingdom
;
_audit_update_record             
;
2024-01-21 deposited with the CCDC.	2024-01-29 downloaded from the CCDC.
;
_audit_creation_date             2024-01-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C33 H23 N3 O4'
_chemical_formula_sum            'C33 H23 N3 O4'
_chemical_formula_weight         525.568
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.4952(2)
_cell_length_b                   18.3345(4)
_cell_length_c                   16.2123(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.689(1)
_cell_angle_gamma                90
_cell_volume                     2524.97(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4838
_cell_measurement_temperature    153.15
_cell_measurement_theta_max      23.59
_cell_measurement_theta_min      2.55
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0558 before and 0.0525 after correction.
The Ratio of minimum to maximum transmission is 0.9599.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1096.719
_exptl_crystal_preparation       'grown from methanol'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9978
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            38759
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.9978
_diffrn_reflns_theta_full        28.0000
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         1.68
_diffrn_ambient_temperature      153.15
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              24
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              -9
_reflns_number_gt                4263
_reflns_number_total             6322
_reflns_threshold_expression     I>=2u(I)
_computing_data_collection       'APEX 2 (Bruker)'
_computing_cell_refinement       'APEX 2 (Bruker)'
_computing_data_reduction        'SAINT V8.34A (Bruker)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.3434
_refine_diff_density_min         -0.3559
_refine_diff_density_rms         0.0778
_refine_ls_d_res_high            0.7476
_refine_ls_d_res_low             12.1447
_refine_ls_goodness_of_fit_ref   1.0553
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     568
_refine_ls_number_reflns         6322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.0553
_refine_ls_shift/su_max          -0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0145P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0461
_refine_ls_wR_factor_ref         0.0550
_refine_special_details          ?
_olex2_refinement_description    
;
;
_olex2_refine_details            
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing
cluster charges or modelled using implicit solvation models, depending on 
the software used.
The following options were used:
   SOFTWARE:       ORCA 5.0
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         R2SCAN
   BASIS SET:      cc-pVTZ
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2024-01-17_08-00-43
;
_atom_sites_solution_primary     dual
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
O1 O -0.20562(9) 0.74238(4) 0.20871(4) 0.0374(2) Uani 1.000000 .
O2 O 0.26327(9) 0.86637(4) -0.11481(4) 0.02799(19) Uani 1.000000 .
O3 O 0.05563(9) 0.97059(4) 0.19581(4) 0.0316(2) Uani 1.000000 .
O4 O 0.36380(9) 0.87120(4) 0.18650(4) 0.0312(2) Uani 1.000000 .
N1 N -0.02015(12) 0.83277(5) 0.21989(6) 0.0211(2) Uani 1.000000 .
N2 N 0.05383(10) 0.81712(4) 0.06347(5) 0.01676(19) Uani 1.000000 .
N3 N 0.33346(12) 0.87114(5) 0.02275(6) 0.0200(2) Uani 1.000000 .
C1 C -0.10868(12) 0.78306(5) 0.17880(6) 0.0206(2) Uani 1.000000 .
C2 C -0.07559(12) 0.78232(5) 0.08779(6) 0.0186(2) Uani 1.000000 .
C3 C -0.17720(15) 0.74670(6) 0.03339(7) 0.0249(3) Uani 1.000000 .
H3a H -0.2762(14) 0.7187(6) 0.0567(7) 0.047(4) Uani 1.000000 .
C4 C -0.14273(15) 0.74795(6) -0.05020(7) 0.0288(3) Uani 1.000000 .
H4 H -0.2190(14) 0.7206(7) -0.0935(7) 0.055(4) Uani 1.000000 .
C5 C -0.00843(15) 0.78408(6) -0.07587(7) 0.0256(3) Uani 1.000000 .
H5 H 0.0271(14) 0.7865(6) -0.1382(7) 0.052(4) Uani 1.000000 .
C6 C 0.08692(12) 0.81773(5) -0.01671(6) 0.0183(2) Uani 1.000000 .
C7 C 0.23667(13) 0.85514(5) -0.04208(6) 0.0193(2) Uani 1.000000 .
C8 C -0.01750(12) 0.84894(5) 0.30374(6) 0.0179(2) Uani 1.000000 .
C9 C -0.06241(13) 0.79691(6) 0.36178(7) 0.0220(3) Uani 1.000000 .
H9 H -0.1045(13) 0.7450(6) 0.3421(6) 0.042(3) Uani 1.000000 .
C10 C -0.05259(13) 0.81280(6) 0.44532(7) 0.0235(3) Uani 1.000000 .
H10 H -0.0843(13) 0.7728(5) 0.4889(6) 0.042(3) Uani 1.000000 .
C11 C 0.00178(14) 0.88034(6) 0.47254(7) 0.0221(3) Uani 1.000000 .
H11 H 0.0103(13) 0.8930(6) 0.5361(6) 0.043(3) Uani 1.000000 .
C12 C 0.04402(13) 0.93268(6) 0.41522(6) 0.0202(2) Uani 1.000000 .
H12 H 0.0831(13) 0.9858(6) 0.4361(6) 0.036(3) Uani 1.000000 .
C13 C 0.03568(12) 0.91854(5) 0.33016(6) 0.0177(2) Uani 1.000000 .
C14 C 0.07105(12) 0.97827(5) 0.27065(6) 0.0205(2) Uani 1.000000 .
C15 C 0.11893(12) 1.05254(5) 0.30081(6) 0.0192(2) Uani 1.000000 .
C16 C 0.02836(14) 1.11199(6) 0.27537(7) 0.0225(3) Uani 1.000000 .
H16 H -0.0741(14) 1.1031(6) 0.2377(7) 0.050(4) Uani 1.000000 .
C17 C 0.07265(15) 1.18201(6) 0.29830(7) 0.0247(3) Uani 1.000000 .
H17 H 0.0018(14) 1.2277(6) 0.2827(7) 0.050(4) Uani 1.000000 .
C18 C 0.21157(14) 1.19351(6) 0.34266(7) 0.0256(3) Uani 1.000000 .
H18 H 0.2475(14) 1.2487(6) 0.3583(7) 0.053(4) Uani 1.000000 .
C19 C 0.30365(15) 1.13425(6) 0.36656(7) 0.0257(3) Uani 1.000000 .
H19 H 0.4191(14) 1.1434(6) 0.3999(7) 0.052(4) Uani 1.000000 .
C20 C 0.25599(14) 1.06346(6) 0.34706(7) 0.0229(3) Uani 1.000000 .
H20 H 0.3289(13) 1.0167(6) 0.3663(7) 0.044(3) Uani 1.000000 .
C21 C 0.48689(12) 0.89872(5) 0.02213(6) 0.0191(2) Uani 1.000000 .
C22 C 0.56912(15) 0.90697(6) -0.05143(7) 0.0255(3) Uani 1.000000 .
H22 H 0.5142(12) 0.8910(6) -0.1087(6) 0.035(3) Uani 1.000000 .
C23 C 0.72303(16) 0.93306(6) -0.05045(8) 0.0305(3) Uani 1.000000 .
H23 H 0.7810(14) 0.9390(6) -0.1077(7) 0.056(4) Uani 1.000000 .
C24 C 0.79751(16) 0.95038(6) 0.02374(8) 0.0296(3) Uani 1.000000 .
H24 H 0.9167(15) 0.9703(6) 0.0253(7) 0.054(4) Uani 1.000000 .
C25 C 0.71734(14) 0.94205(6) 0.09691(8) 0.0246(3) Uani 1.000000 .
H25 H 0.7786(13) 0.9535(6) 0.1536(6) 0.041(3) Uani 1.000000 .
C26 C 0.56162(12) 0.91722(5) 0.09823(6) 0.0195(2) Uani 1.000000 .
C27 C 0.48373(13) 0.90787(5) 0.17917(6) 0.0210(2) Uani 1.000000 .
C28 C 0.55186(12) 0.94214(6) 0.25570(6) 0.0214(2) Uani 1.000000 .
C29 C 0.54574(15) 0.90131(7) 0.32814(7) 0.0293(3) Uani 1.000000 .
H29 H 0.4990(15) 0.8465(6) 0.3233(7) 0.056(4) Uani 1.000000 .
C30 C 0.59839(16) 0.93092(8) 0.40211(8) 0.0369(3) Uani 1.000000 .
H30 H 0.5945(15) 0.8980(7) 0.4552(7) 0.065(4) Uani 1.000000 .
C31 C 0.65379(15) 1.00236(8) 0.40506(8) 0.0363(3) Uani 1.000000 .
H31 H 0.6937(15) 1.0262(7) 0.4637(7) 0.069(4) Uani 1.000000 .
C32 C 0.65851(15) 1.04364(7) 0.33319(8) 0.0316(3) Uani 1.000000 .
H32 H 0.6999(14) 1.0985(7) 0.3351(7) 0.054(4) Uani 1.000000 .
C33 C 0.60931(14) 1.01341(6) 0.25844(7) 0.0244(3) Uani 1.000000 .
H33 H 0.6089(14) 1.0456(6) 0.2033(7) 0.050(4) Uani 1.000000 .
H1 H 0.0394(15) 0.8642(7) 0.1852(8) 0.043(4) Uani 1.000000 .
H3 H 0.2909(15) 0.8627(6) 0.0781(8) 0.034(4) Uani 1.000000 .


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 1.2161(11) . ?
O2 C7 1.2208(11) . ?
O3 C14 1.2269(11) . ?
O4 C27 1.2276(11) . ?
N1 C1 1.3521(13) . ?
N1 C8 1.3912(13) . ?
N1 H1 0.954(12) . ?
N2 C2 1.3348(12) . ?
N2 C6 1.3333(12) . ?
N3 C7 1.3588(13) . ?
N3 C21 1.3981(13) . ?
N3 H3 0.984(12) . ?
C1 C2 1.5055(13) . ?
C2 C3 1.3897(15) . ?
C3 H3a 1.060(12) . ?
C3 C4 1.3900(16) . ?
C4 H4 1.074(11) . ?
C4 C5 1.3875(17) . ?
C5 H5 1.059(11) . ?
C5 C6 1.3922(15) . ?
C6 C7 1.5067(14) . ?
C8 C9 1.3962(13) . ?
C8 C13 1.4181(13) . ?
C9 H9 1.064(10) . ?
C9 C10 1.3868(14) . ?
C10 H10 1.056(9) . ?
C10 C11 1.3916(15) . ?
C11 H11 1.057(10) . ?
C11 C12 1.3861(14) . ?
C12 H12 1.082(10) . ?
C12 C13 1.4042(13) . ?
C13 C14 1.4924(13) . ?
C14 C15 1.5014(13) . ?
C15 C16 1.3936(14) . ?
C15 C20 1.3918(14) . ?
C16 H16 1.070(10) . ?
C16 C17 1.3873(15) . ?
C17 H17 1.061(11) . ?
C17 C18 1.3907(16) . ?
C18 H18 1.087(10) . ?
C18 C19 1.3911(16) . ?
C19 H19 1.127(11) . ?
C19 C20 1.3948(15) . ?
C20 H20 1.101(11) . ?
C21 C22 1.3976(14) . ?
C21 C26 1.4218(13) . ?
C22 H22 1.074(10) . ?
C22 C23 1.3921(17) . ?
C23 H23 1.061(11) . ?
C23 C24 1.3892(18) . ?
C24 H24 1.076(12) . ?
C24 C25 1.3834(16) . ?
C25 H25 1.072(10) . ?
C25 C26 1.3994(15) . ?
C26 C27 1.4866(14) . ?
C27 C28 1.5007(14) . ?
C28 C29 1.3942(14) . ?
C28 C33 1.3954(14) . ?
C29 H29 1.083(11) . ?
C29 C30 1.3857(17) . ?
C30 H30 1.052(12) . ?
C30 C31 1.3924(18) . ?
C31 H31 1.096(12) . ?
C31 C32 1.3903(17) . ?
C32 H32 1.066(11) . ?
C32 C33 1.3922(16) . ?
C33 H33 1.071(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
C8 N1 C1 128.86(9) . . ?
H1 N1 C1 114.4(8) . . ?
H1 N1 C8 116.4(8) . . ?
C6 N2 C2 118.43(8) . . ?
C21 N3 C7 128.90(9) . . ?
H3 N3 C7 116.5(8) . . ?
H3 N3 C21 114.6(8) . . ?
N1 C1 O1 126.32(10) . . ?
C2 C1 O1 121.37(9) . . ?
C2 C1 N1 112.31(9) . . ?
C1 C2 N2 116.71(9) . . ?
C3 C2 N2 123.01(10) . . ?
C3 C2 C1 120.29(10) . . ?
H3a C3 C2 119.4(6) . . ?
C4 C3 C2 118.32(12) . . ?
C4 C3 H3a 122.2(6) . . ?
H4 C4 C3 119.8(6) . . ?
C5 C4 C3 118.95(12) . . ?
C5 C4 H4 121.2(6) . . ?
H5 C5 C4 123.5(7) . . ?
C6 C5 C4 118.60(11) . . ?
C6 C5 H5 117.9(7) . . ?
C5 C6 N2 122.69(10) . . ?
C7 C6 N2 117.29(9) . . ?
C7 C6 C5 119.99(9) . . ?
N3 C7 O2 126.40(10) . . ?
C6 C7 O2 120.47(9) . . ?
C6 C7 N3 113.10(9) . . ?
C9 C8 N1 120.77(9) . . ?
C13 C8 N1 119.22(9) . . ?
C13 C8 C9 119.99(9) . . ?
H9 C9 C8 120.1(6) . . ?
C10 C9 C8 120.06(10) . . ?
C10 C9 H9 119.8(6) . . ?
H10 C10 C9 119.7(6) . . ?
C11 C10 C9 120.83(11) . . ?
C11 C10 H10 119.5(6) . . ?
H11 C11 C10 121.5(6) . . ?
C12 C11 C10 119.41(11) . . ?
C12 C11 H11 119.1(6) . . ?
H12 C12 C11 119.6(5) . . ?
C13 C12 C11 121.35(10) . . ?
C13 C12 H12 119.1(5) . . ?
C12 C13 C8 118.35(9) . . ?
C14 C13 C8 122.07(9) . . ?
C14 C13 C12 119.42(9) . . ?
C13 C14 O3 122.35(9) . . ?
C15 C14 O3 116.83(9) . . ?
C15 C14 C13 120.73(9) . . ?
C16 C15 C14 117.81(9) . . ?
C20 C15 C14 121.84(9) . . ?
C20 C15 C16 120.15(10) . . ?
H16 C16 C15 119.5(6) . . ?
C17 C16 C15 119.83(11) . . ?
C17 C16 H16 120.6(6) . . ?
H17 C17 C16 121.1(6) . . ?
C18 C17 C16 120.30(11) . . ?
C18 C17 H17 118.6(6) . . ?
H18 C18 C17 119.7(6) . . ?
C19 C18 C17 119.77(11) . . ?
C19 C18 H18 120.5(6) . . ?
H19 C19 C18 120.1(6) . . ?
C20 C19 C18 120.19(12) . . ?
C20 C19 H19 119.7(6) . . ?
C19 C20 C15 119.64(11) . . ?
H20 C20 C15 120.3(6) . . ?
H20 C20 C19 120.0(6) . . ?
C22 C21 N3 121.40(10) . . ?
C26 C21 N3 119.11(9) . . ?
C26 C21 C22 119.48(10) . . ?
H22 C22 C21 119.4(6) . . ?
C23 C22 C21 120.43(12) . . ?
C23 C22 H22 120.1(6) . . ?
H23 C23 C22 118.1(7) . . ?
C24 C23 C22 120.42(12) . . ?
C24 C23 H23 121.5(7) . . ?
H24 C24 C23 121.1(6) . . ?
C25 C24 C23 119.56(13) . . ?
C25 C24 H24 119.4(6) . . ?
H25 C25 C24 118.4(6) . . ?
C26 C25 C24 121.62(12) . . ?
C26 C25 H25 120.0(6) . . ?
C25 C26 C21 118.47(10) . . ?
C27 C26 C21 122.66(9) . . ?
C27 C26 C25 118.81(10) . . ?
C26 C27 O4 121.82(9) . . ?
C28 C27 O4 117.49(9) . . ?
C28 C27 C26 120.68(9) . . ?
C29 C28 C27 116.98(10) . . ?
C33 C28 C27 123.34(9) . . ?
C33 C28 C29 119.51(10) . . ?
H29 C29 C28 117.0(6) . . ?
C30 C29 C28 120.24(12) . . ?
C30 C29 H29 122.7(6) . . ?
H30 C30 C29 118.0(7) . . ?
C31 C30 C29 120.25(12) . . ?
C31 C30 H30 121.7(7) . . ?
H31 C31 C30 120.4(7) . . ?
C32 C31 C30 119.76(13) . . ?
C32 C31 H31 119.8(7) . . ?
H32 C32 C31 120.1(6) . . ?
C33 C32 C31 120.10(13) . . ?
C33 C32 H32 119.8(6) . . ?
C32 C33 C28 120.11(11) . . ?
H33 C33 C28 119.4(6) . . ?
H33 C33 C32 120.3(6) . . ?

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
C22 H22 O2 1.074(10) 2.180(10) 2.8804(15) 120.7(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
O1 C1 N1 C8 0.34(15) . . . . ?
O1 C1 C2 N2 -166.30(10) . . . . ?
O1 C1 C2 C3 13.73(13) . . . . ?
O2 C7 N3 C21 -4.89(13) . . . . ?
O2 C7 C6 N2 -169.98(9) . . . . ?
O2 C7 C6 C5 11.60(12) . . . . ?
O3 C14 C13 C8 0.24(12) . . . . ?
O3 C14 C13 C12 -175.05(10) . . . . ?
O3 C14 C15 C16 53.87(11) . . . . ?
O3 C14 C15 C20 -120.95(10) . . . . ?
O4 C27 C26 C21 14.15(12) . . . . ?
O4 C27 C26 C25 -162.83(10) . . . . ?
O4 C27 C28 C29 37.83(11) . . . . ?
O4 C27 C28 C33 -137.51(10) . . . . ?
N1 C1 C2 N2 13.82(10) . . . . ?
N1 C1 C2 C3 -166.15(9) . . . . ?
N1 C8 C9 C10 177.19(10) . . . . ?
N1 C8 C13 C12 -177.25(10) . . . . ?
N1 C8 C13 C14 7.41(12) . . . . ?
N2 C2 C3 C4 -0.50(12) . . . . ?
N2 C6 C5 C4 -0.52(12) . . . . ?
N2 C6 C7 N3 12.04(10) . . . . ?
N3 C7 C6 C5 -166.38(9) . . . . ?
N3 C21 C22 C23 -178.61(10) . . . . ?
N3 C21 C26 C25 177.53(9) . . . . ?
N3 C21 C26 C27 0.54(11) . . . . ?
C1 C2 C3 C4 179.47(10) . . . . ?
C2 C3 C4 C5 0.43(13) . . . . ?
C3 C4 C5 C6 0.05(13) . . . . ?
C4 C5 C6 C7 177.81(10) . . . . ?
C8 C9 C10 C11 -0.01(13) . . . . ?
C8 C13 C12 C11 0.06(12) . . . . ?
C8 C13 C14 C15 176.74(10) . . . . ?
C9 C10 C11 C12 1.10(13) . . . . ?
C10 C11 C12 C13 -1.12(13) . . . . ?
C11 C12 C13 C14 175.53(10) . . . . ?
C12 C13 C14 C15 1.44(11) . . . . ?
C13 C14 C15 C16 -122.81(10) . . . . ?
C13 C14 C15 C20 62.37(11) . . . . ?
C14 C15 C16 C17 -176.78(10) . . . . ?
C14 C15 C20 C19 173.56(10) . . . . ?
C15 C16 C17 C18 3.56(13) . . . . ?
C15 C20 C19 C18 2.48(13) . . . . ?
C16 C17 C18 C19 -2.22(14) . . . . ?
C17 C18 C19 C20 -0.81(13) . . . . ?
C21 C22 C23 C24 0.80(13) . . . . ?
C21 C26 C25 C24 1.48(11) . . . . ?
C21 C26 C27 C28 -167.09(9) . . . . ?
C22 C23 C24 C25 -0.47(13) . . . . ?
C23 C24 C25 C26 -0.70(13) . . . . ?
C24 C25 C26 C27 178.59(10) . . . . ?
C25 C26 C27 C28 15.93(11) . . . . ?
C26 C27 C28 C29 -140.97(10) . . . . ?
C26 C27 C28 C33 43.69(12) . . . . ?
C27 C28 C29 C30 -176.43(10) . . . . ?
C27 C28 C33 C32 174.55(11) . . . . ?
C28 C29 C30 C31 1.76(14) . . . . ?
C28 C33 C32 C31 1.41(13) . . . . ?
C29 C30 C31 C32 -1.02(15) . . . . ?
C30 C31 C32 C33 -0.56(15) . . . . ?


_olex2_exptl_crystal_mounting_method 
'mounted on a nylon cryoloop with Paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_NSA_Cpd_1b
_database_code_depnum_ccdc_archive 'CCDC 2310782'
loop_
_audit_author_name
_audit_author_address
'Orde Munro'
;University of Leeds
United Kingdom
;
_audit_update_record             
;
2024-01-21 deposited with the CCDC.	2024-01-29 downloaded from the CCDC.
;
# mo_21ov_RRH_3AmQuin_Pin_0m
_audit_creation_date             2024-01-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C25 H17 N5 O2, 2(C H4 O)'
_chemical_formula_sum            'C27 H25 N5 O4'
_chemical_formula_weight         483.531
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.2743(3)
_cell_length_b                   11.3528(5)
_cell_length_c                   14.9566(5)
_cell_angle_alpha                76.605(1)
_cell_angle_beta                 78.871(1)
_cell_angle_gamma                78.901(2)
_cell_volume                     1164.76(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9827
_cell_measurement_temperature    153.00
_cell_measurement_theta_max      33.06
_cell_measurement_theta_min      2.56
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.7102
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0601 before and 0.0534 after correction.
The Ratio of minimum to maximum transmission is 0.9514.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       plate
_exptl_crystal_F_000             508.344
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.096
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.9964
_diffrn_reflns_Laue_measured_fraction_max 0.9945
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            85728
_diffrn_reflns_point_group_measured_fraction_full 0.9964
_diffrn_reflns_point_group_measured_fraction_max 0.9945
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         33.21
_diffrn_reflns_theta_min         2.89
_diffrn_ambient_temperature      153.00
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.9945
_diffrn_measurement_device_type  'Bruker Venture D8 Photon I CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -10
_reflns_limit_k_max              17
_reflns_limit_k_min              -16
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                7062
_reflns_number_total             8894
_reflns_threshold_expression     I>=2u(I)
_computing_data_collection       'APEX 3 (Bruker)'
_computing_cell_refinement       'APEX 3 (Bruker)'
_computing_data_reduction        'SAINT V8.38A (Bruker)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.2373
_refine_diff_density_min         -0.2323
_refine_diff_density_rms         0.0576
_refine_ls_d_res_high            0.6488
_refine_ls_d_res_low             7.0514
_refine_ls_goodness_of_fit_ref   1.3006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     550
_refine_ls_number_reflns         8894
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0290
_refine_ls_restrained_S_all      1.3003
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0114P)²+0.0074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0419
_refine_ls_wR_factor_ref         0.0453
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Ueq(H2Sb), Ueq(H2Sa), Ueq(H2Sc): fixed at 0.07 with sigma of 0.1
;
_olex2_refine_details            
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA 5.0
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         R2SCAN
   BASIS SET:      cc-pVTZ
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2024-01-16_13-11-16
;
_atom_sites_solution_primary     dual
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
O2 O 0.75800(6) 1.15571(3) 0.43396(2) 0.02369(8) Uani 1.000000 .
O1 O 0.33993(6) 0.88111(4) 0.87885(2) 0.03176(10) Uani 1.000000 .
O2S O 0.26790(6) 0.29790(4) 0.38076(3) 0.02376(9) Uani 1.000000 .
O1S O 0.28538(7) 0.50765(4) 0.43200(3) 0.02941(10) Uani 1.000000 .
N3 N 0.79264(6) 0.94780(4) 0.48548(3) 0.01584(8) Uani 1.000000 .
N2 N 0.56573(6) 0.97802(4) 0.64784(3) 0.01502(8) Uani 1.000000 .
N1 N 0.43159(7) 0.77989(4) 0.75820(3) 0.01855(9) Uani 1.000000 .
N5 N 1.07758(6) 0.72740(4) 0.35275(3) 0.02020(9) Uani 1.000000 .
N4 N 0.27295(6) 0.49376(4) 0.76252(3) 0.02021(9) Uani 1.000000 .
C16 C 1.29922(9) 0.81154(6) 0.11055(4) 0.02925(13) Uani 1.000000 .
H16 H 1.3862(11) 0.7679(7) 0.0579(4) 0.052(2) Uani 1.000000 .
C17 C 1.24182(10) 0.93996(6) 0.09270(4) 0.03319(14) Uani 1.000000 .
H17 H 1.2841(11) 0.9925(7) 0.0249(4) 0.063(2) Uani 1.000000 .
C18 C 1.13255(9) 0.99667(6) 0.16118(4) 0.02900(13) Uani 1.000000 .
H18 H 1.0885(11) 1.0947(7) 0.1478(4) 0.053(2) Uani 1.000000 .
C13 C 1.07434(7) 0.92737(5) 0.25068(3) 0.01856(10) Uani 1.000000 .
C12 C 0.96228(8) 0.98282(5) 0.32327(3) 0.01792(10) Uani 1.000000 .
H12 H 0.9198(10) 1.0806(6) 0.3109(4) 0.0390(18) Uani 1.000000 .
C11 C 0.90730(7) 0.90898(4) 0.40754(3) 0.01480(9) Uani 1.000000 .
C25 C 0.72505(7) 1.06545(4) 0.49407(3) 0.01563(9) Uani 1.000000 .
C24 C 0.60428(7) 1.07941(4) 0.58614(3) 0.01474(9) Uani 1.000000 .
C20 C 0.46459(7) 0.99161(4) 0.73053(3) 0.01585(9) Uani 1.000000 .
C19 C 0.40789(7) 0.87858(5) 0.79797(3) 0.01797(10) Uani 1.000000 .
C2 C 0.37030(7) 0.66718(4) 0.79895(3) 0.01626(10) Uani 1.000000 .
C3 C 0.34038(7) 0.61907(5) 0.89295(3) 0.01843(10) Uani 1.000000 .
H3a H 0.3653(10) 0.6680(6) 0.9429(4) 0.0359(17) Uani 1.000000 .
C4 C 0.27422(7) 0.50477(5) 0.92331(3) 0.01761(10) Uani 1.000000 .
C5 C 0.23714(7) 0.44629(5) 0.85587(3) 0.01711(10) Uani 1.000000 .
C6 C 0.15680(8) 0.33679(5) 0.88514(4) 0.02145(11) Uani 1.000000 .
H6 H 0.1206(10) 0.2973(6) 0.8327(4) 0.0377(18) Uani 1.000000 .
C7 C 0.12103(9) 0.28486(5) 0.97805(4) 0.02632(12) Uani 1.000000 .
H7 H 0.0564(11) 0.2021(6) 0.9998(4) 0.047(2) Uani 1.000000 .
C14 C 1.12999(7) 0.79848(5) 0.26767(3) 0.01800(10) Uani 1.000000 .
C15 C 1.24430(8) 0.74193(6) 0.19658(4) 0.02446(12) Uani 1.000000 .
H15 H 1.2878(10) 0.6439(6) 0.2109(4) 0.0434(19) Uani 1.000000 .
C10 C 0.97110(7) 0.78079(5) 0.41821(3) 0.01851(10) Uani 1.000000 .
H10 H 0.9324(10) 0.7223(6) 0.4839(4) 0.0423(18) Uani 1.000000 .
C23 C 0.53828(8) 1.19703(5) 0.60294(4) 0.01851(10) Uani 1.000000 .
H23 H 0.5695(10) 1.2741(6) 0.5485(4) 0.0370(17) Uani 1.000000 .
C22 C 0.43561(8) 1.21013(5) 0.68971(4) 0.02065(11) Uani 1.000000 .
H22 H 0.3836(10) 1.2987(6) 0.7054(4) 0.0408(18) Uani 1.000000 .
C21 C 0.40048(8) 1.10522(5) 0.75559(3) 0.01905(10) Uani 1.000000 .
H21 H 0.3235(10) 1.1082(6) 0.8247(4) 0.0371(18) Uani 1.000000 .
C1 C 0.33759(8) 0.59862(5) 0.73639(3) 0.01919(10) Uani 1.000000 .
H1a H 0.3630(10) 0.6348(6) 0.6631(4) 0.0397(18) Uani 1.000000 .
C8 C 0.16523(9) 0.34025(5) 1.04520(4) 0.02871(13) Uani 1.000000 .
H8 H 0.1330(12) 0.2991(7) 1.1186(4) 0.057(2) Uani 1.000000 .
C9 C 0.23850(8) 0.44824(5) 1.01876(4) 0.02441(12) Uani 1.000000 .
H9 H 0.2658(11) 0.4920(6) 1.0708(4) 0.046(2) Uani 1.000000 .
C2S C 0.14255(12) 0.32850(9) 0.31480(6) 0.03973(17) Uani 1.000000 .
H2Sa H 0.0391(17) 0.3959(15) 0.3254(9) 0.165(7) Uani 1.000000 .
H2Sb H 0.2020(15) 0.3660(15) 0.2528(6) 0.135(5) Uani 1.000000 .
H2Sc H 0.093(3) 0.2595(11) 0.3100(12) 0.206(9) Uani 1.000000 .
C1S C 0.24483(11) 0.51015(7) 0.52844(4) 0.02766(12) Uani 1.000000 .
H1Sa H 0.3599(13) 0.4618(9) 0.5612(5) 0.086(3) Uani 1.000000 .
H1Sb H 0.2242(13) 0.6001(7) 0.5408(5) 0.070(3) Uani 1.000000 .
H1Sc H 0.1187(14) 0.4741(9) 0.5627(5) 0.086(3) Uani 1.000000 .
H3 H 0.7549(9) 0.8827(6) 0.5391(4) 0.0287(17) Uani 1.000000 .
H1 H 0.4895(10) 0.7901(6) 0.6910(4) 0.0340(18) Uani 1.000000 .
H2S H 0.2816(11) 0.3698(7) 0.4002(5) 0.0307(19) Uani 1.000000 .
H1S H 0.2076(11) 0.5795(8) 0.3983(5) 0.045(2) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C25 1.2248(6) . ?
O1 C19 1.2199(6) . ?
O2S C2S 1.4114(8) . ?
O2S H2S 0.956(7) . ?
O1S C1S 1.4212(7) . ?
O1S H1S 0.990(8) . ?
N3 C11 1.4036(6) . ?
N3 C25 1.3581(6) . ?
N3 H3 0.992(6) . ?
N2 C24 1.3369(6) . ?
N2 C20 1.3372(6) . ?
N1 C19 1.3541(6) . ?
N1 C2 1.4003(6) . ?
N1 H1 1.001(6) . ?
N5 C14 1.3680(6) . ?
N5 C10 1.3144(6) . ?
N4 C5 1.3685(6) . ?
N4 C1 1.3115(7) . ?
C16 H16 1.065(6) . ?
C16 C17 1.4140(9) . ?
C16 C15 1.3754(8) . ?
C17 H17 1.071(6) . ?
C17 C18 1.3746(8) . ?
C18 H18 1.080(7) . ?
C18 C13 1.4183(7) . ?
C13 C12 1.4201(7) . ?
C13 C14 1.4174(7) . ?
C12 H12 1.076(6) . ?
C12 C11 1.3770(7) . ?
C11 C10 1.4212(7) . ?
C25 C24 1.5079(6) . ?
C24 C23 1.3924(7) . ?
C20 C19 1.5092(7) . ?
C20 C21 1.3951(7) . ?
C2 C3 1.3763(6) . ?
C2 C1 1.4256(7) . ?
C3 H3a 1.088(6) . ?
C3 C4 1.4158(7) . ?
C4 C5 1.4195(7) . ?
C4 C9 1.4191(7) . ?
C5 C6 1.4168(7) . ?
C6 H6 1.083(6) . ?
C6 C7 1.3734(7) . ?
C7 H7 1.086(6) . ?
C7 C8 1.4150(8) . ?
C14 C15 1.4155(7) . ?
C15 H15 1.079(7) . ?
C10 H10 1.072(6) . ?
C23 H23 1.074(6) . ?
C23 C22 1.3917(7) . ?
C22 H22 1.067(6) . ?
C22 C21 1.3896(7) . ?
C21 H21 1.082(6) . ?
C1 H1a 1.071(5) . ?
C8 H8 1.088(6) . ?
C8 C9 1.3745(8) . ?
C9 H9 1.081(6) . ?
C2S H2Sa 0.982(10) . ?
C2S H2Sb 0.980(10) . ?
C2S H2Sc 0.944(9) . ?
C1S H1Sa 1.049(8) . ?
C1S H1Sb 1.057(8) . ?
C1S H1Sc 1.067(8) . ?

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
H2S O2S C2S 110.1(4) . . ?
H1S O1S C1S 108.4(5) . . ?
C25 N3 C11 126.53(4) . . ?
H3 N3 C11 116.7(4) . . ?
H3 N3 C25 116.8(4) . . ?
C20 N2 C24 117.66(4) . . ?
C2 N1 C19 126.87(4) . . ?
H1 N1 C19 117.1(4) . . ?
H1 N1 C2 115.9(4) . . ?
C10 N5 C14 118.62(4) . . ?
C1 N4 C5 117.83(4) . . ?
C17 C16 H16 120.5(4) . . ?
C15 C16 H16 119.4(4) . . ?
C15 C16 C17 120.17(6) . . ?
H17 C17 C16 119.1(4) . . ?
C18 C17 C16 120.51(5) . . ?
C18 C17 H17 120.4(4) . . ?
H18 C18 C17 120.7(3) . . ?
C13 C18 C17 120.62(6) . . ?
C13 C18 H18 118.7(3) . . ?
C12 C13 C18 122.20(5) . . ?
C14 C13 C18 118.57(5) . . ?
C14 C13 C12 119.22(4) . . ?
H12 C12 C13 119.6(3) . . ?
C11 C12 C13 118.75(5) . . ?
C11 C12 H12 121.6(3) . . ?
C12 C11 N3 126.28(5) . . ?
C10 C11 N3 115.77(4) . . ?
C10 C11 C12 117.95(5) . . ?
N3 C25 O2 124.56(5) . . ?
C24 C25 O2 120.67(4) . . ?
C24 C25 N3 114.77(4) . . ?
C25 C24 N2 118.32(4) . . ?
C23 C24 N2 123.11(4) . . ?
C23 C24 C25 118.56(4) . . ?
C19 C20 N2 118.05(4) . . ?
C21 C20 N2 123.42(5) . . ?
C21 C20 C19 118.43(4) . . ?
N1 C19 O1 125.11(5) . . ?
C20 C19 O1 121.48(4) . . ?
C20 C19 N1 113.32(4) . . ?
C3 C2 N1 125.26(4) . . ?
C1 C2 N1 116.07(4) . . ?
C1 C2 C3 118.67(5) . . ?
H3a C3 C2 120.9(3) . . ?
C4 C3 C2 118.41(5) . . ?
C4 C3 H3a 120.7(3) . . ?
C5 C4 C3 118.71(4) . . ?
C9 C4 C3 122.46(5) . . ?
C9 C4 C5 118.80(5) . . ?
C4 C5 N4 122.01(4) . . ?
C6 C5 N4 118.33(4) . . ?
C6 C5 C4 119.64(4) . . ?
H6 C6 C5 118.3(3) . . ?
C7 C6 C5 120.35(5) . . ?
C7 C6 H6 121.3(3) . . ?
H7 C7 C6 119.7(3) . . ?
C8 C7 C6 120.09(5) . . ?
C8 C7 H7 120.2(3) . . ?
C13 C14 N5 120.92(4) . . ?
C15 C14 N5 119.11(5) . . ?
C15 C14 C13 119.97(5) . . ?
C14 C15 C16 120.16(6) . . ?
H15 C15 C16 120.7(3) . . ?
H15 C15 C14 119.2(3) . . ?
C11 C10 N5 124.50(5) . . ?
H10 C10 N5 116.6(3) . . ?
H10 C10 C11 118.8(3) . . ?
H23 C23 C24 118.7(3) . . ?
C22 C23 C24 118.72(5) . . ?
C22 C23 H23 122.6(3) . . ?
H22 C22 C23 120.9(3) . . ?
C21 C22 C23 118.62(5) . . ?
C21 C22 H22 120.4(3) . . ?
C22 C21 C20 118.34(5) . . ?
H21 C21 C20 118.9(3) . . ?
H21 C21 C22 122.8(3) . . ?
C2 C1 N4 124.25(5) . . ?
H1a C1 N4 116.7(3) . . ?
H1a C1 C2 119.0(3) . . ?
H8 C8 C7 119.2(4) . . ?
C9 C8 C7 120.66(5) . . ?
C9 C8 H8 120.0(4) . . ?
C8 C9 C4 120.37(5) . . ?
H9 C9 C4 119.5(3) . . ?
H9 C9 C8 120.1(3) . . ?
H2Sa C2S O2S 114.0(6) . . ?
H2Sb C2S O2S 112.6(6) . . ?
H2Sb C2S H2Sa 98.6(10) . . ?
H2Sc C2S O2S 111.8(6) . . ?
H2Sc C2S H2Sa 110.3(12) . . ?
H2Sc C2S H2Sb 108.7(11) . . ?
H1Sa C1S O1S 109.8(4) . . ?
H1Sb C1S O1S 112.3(4) . . ?
H1Sb C1S H1Sa 106.1(7) . . ?
H1Sc C1S O1S 113.3(4) . . ?
H1Sc C1S H1Sa 109.7(7) . . ?
H1Sc C1S H1Sb 105.3(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
O2 C25 N3 C11 -1.07(6) . . . . ?
O2 C25 C24 N2 177.13(5) . . . . ?
O2 C25 C24 C23 -2.88(6) . . . . ?
O1 C19 N1 C2 5.46(7) . . . . ?
O1 C19 C20 N2 169.32(5) . . . . ?
O1 C19 C20 C21 -14.05(6) . . . . ?
N3 C11 C12 C13 -178.07(5) . . . . ?
N3 C11 C10 N5 179.21(4) . . . . ?
N3 C25 C24 N2 -3.68(5) . . . . ?
N3 C25 C24 C23 176.31(4) . . . . ?
N2 C24 C23 C22 3.48(6) . . . . ?
N2 C20 C19 N1 -13.76(5) . . . . ?
N2 C20 C21 C22 3.19(6) . . . . ?
N1 C19 C20 C21 162.87(4) . . . . ?
N1 C2 C3 C4 178.66(5) . . . . ?
N1 C2 C1 N4 -177.22(4) . . . . ?
N5 C14 C13 C18 -179.97(5) . . . . ?
N5 C14 C13 C12 -0.14(6) . . . . ?
N5 C14 C15 C16 -179.82(5) . . . . ?
N5 C10 C11 C12 -0.78(6) . . . . ?
N4 C5 C4 C3 3.56(6) . . . . ?
N4 C5 C4 C9 -178.21(5) . . . . ?
N4 C5 C6 C7 179.04(5) . . . . ?
N4 C1 C2 C3 2.86(7) . . . . ?
C16 C17 C18 C13 -0.45(7) . . . . ?
C16 C15 C14 C13 -0.98(7) . . . . ?
C17 C18 C13 C12 179.67(6) . . . . ?
C17 C18 C13 C14 -0.50(7) . . . . ?
C18 C13 C12 C11 178.33(5) . . . . ?
C18 C13 C14 C15 1.21(6) . . . . ?
C13 C12 C11 C10 1.92(6) . . . . ?
C25 C24 C23 C22 -176.51(4) . . . . ?
C24 C23 C22 C21 -1.03(6) . . . . ?
C20 C21 C22 C23 -2.07(6) . . . . ?
C2 C3 C4 C5 -1.55(6) . . . . ?
C2 C3 C4 C9 -179.72(5) . . . . ?
C3 C4 C5 C6 -175.05(5) . . . . ?
C3 C4 C9 C8 176.69(6) . . . . ?
C4 C5 C6 C7 -2.30(6) . . . . ?
C4 C9 C8 C7 -1.15(7) . . . . ?
C5 C6 C7 C8 -0.33(7) . . . . ?
C6 C7 C8 C9 2.09(7) . . . . ?


_olex2_exptl_crystal_mounting_method 
'mounted on a nylon cryoloop with Paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_U_Ueq_atom_site_label_1
_restr_U_Ueq_weight_param
_restr_U_Ueq_target
_restr_U_Ueq_diff
H2Sa 0.1000 0.0700 0.0946
H2Sb 0.1000 0.0700 0.0652
H2Sc 0.1000 0.0700 0.1357

