# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_13nova_0m
_database_code_depnum_ccdc_archive 'CCDC 2122234'
_audit_update_record             
;
2021-11-15 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;
_audit_creation_date             2021-11-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C15 H15 N3 O)'
_chemical_formula_sum            'C30 H30 N6 O2'
_chemical_formula_weight         506.60
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.2949(2)
_cell_length_b                   11.9167(2)
_cell_length_c                   14.4321(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1254.60(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6983
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1470 before and 0.0646 after correction.
The Ratio of minimum to maximum transmission is 0.9364.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20258
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.298
_diffrn_reflns_theta_min         3.129
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2956
_reflns_number_total             3111
_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    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1190 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         3111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1183
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00B(H00I,H00J)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00K), C00D(H00L), C00G(H00M), C00H(H00N)
2.c Idealised Me refined as rotating group:
 C007(H00C,H00D,H00E), C009(H00F,H00G,H00H)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001), N002(H00A)
;
_atom_sites_solution_hydrogens   mixed
_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
O001 O 0.64279(19) 0.85412(10) 0.64473(8) 0.0167(3) Uani 1 1 d . . . . .
H001 H 0.605012 0.791141 0.657369 0.025 Uiso 1 1 calc R U . . .
N002 N 0.4596(2) 0.54297(12) 0.72979(10) 0.0184(3) Uani 1 1 d . . . . .
H00A H 0.465009 0.476527 0.744314 0.028 Uiso 1 1 calc R U . . .
N1 N 0.5067(2) 0.65860(12) 0.60524(10) 0.0139(3) Uani 1 1 d . . . . .
N2 N 0.5325(3) 0.26539(13) 0.65559(11) 0.0232(4) Uani 1 1 d . . . . .
C005 C 0.5004(2) 0.55422(14) 0.63897(11) 0.0136(3) Uani 1 1 d . . . . .
C006 C 0.5368(2) 0.35209(15) 0.62065(12) 0.0169(4) Uani 1 1 d . . . . .
C007 C 0.6571(3) 0.61210(15) 0.35475(12) 0.0170(4) Uani 1 1 d . . . . .
H00C H 0.741603 0.554831 0.335685 0.025 Uiso 1 1 calc R U . . .
H00D H 0.716093 0.684007 0.351694 0.025 Uiso 1 1 calc R U . . .
H00E H 0.552431 0.611684 0.314417 0.025 Uiso 1 1 calc R U . . .
C008 C 0.5415(2) 0.46175(14) 0.58090(12) 0.0140(3) Uani 1 1 d . . . . .
C009 C 0.4919(3) 0.33883(15) 0.36811(13) 0.0222(4) Uani 1 1 d . . . . .
H00F H 0.536834 0.281554 0.327214 0.033 Uiso 1 1 calc R U . . .
H00G H 0.445979 0.400612 0.332298 0.033 Uiso 1 1 calc R U . . .
H00H H 0.395065 0.308777 0.405693 0.033 Uiso 1 1 calc R U . . .
C00A C 0.5941(2) 0.47962(14) 0.48860(12) 0.0142(3) Uani 1 1 d . . . . .
C00B C 0.6481(3) 0.37959(14) 0.43057(13) 0.0178(4) Uani 1 1 d . . . . .
H00I H 0.685358 0.318856 0.471175 0.021 Uiso 1 1 calc R U . . .
H00J H 0.752550 0.399517 0.392351 0.021 Uiso 1 1 calc R U . . .
C00C C 0.4874(3) 0.94786(15) 0.37903(12) 0.0198(4) Uani 1 1 d . . . . .
H00K H 0.446894 0.970589 0.320889 0.024 Uiso 1 1 calc R U . . .
C00D C 0.4866(2) 0.83484(15) 0.40279(12) 0.0163(4) Uani 1 1 d . . . . .
H00L H 0.445670 0.782424 0.359770 0.020 Uiso 1 1 calc R U . . .
C00E C 0.5971(2) 0.87985(14) 0.55538(12) 0.0145(3) Uani 1 1 d . . . . .
C00F C 0.5955(2) 0.58958(14) 0.45359(11) 0.0135(3) Uani 1 1 d . . . . .
C00G C 0.5491(3) 1.02643(15) 0.44254(13) 0.0208(4) Uani 1 1 d . . . . .
H00M H 0.554248 1.101824 0.426114 0.025 Uiso 1 1 calc R U . . .
C00H C 0.6031(3) 0.99327(14) 0.53040(13) 0.0176(4) Uani 1 1 d . . . . .
H00N H 0.643350 1.046504 0.572884 0.021 Uiso 1 1 calc R U . . .
C00I C 0.5485(2) 0.67663(14) 0.51517(11) 0.0125(3) Uani 1 1 d . . . . .
C00J C 0.5460(2) 0.79792(14) 0.48991(11) 0.0128(3) Uani 1 1 d . . . . .
H00B H 0.440(3) 0.6029(19) 0.7629(16) 0.018(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 H001 0.8200 . ?
O001 C00E 1.367(2) . ?
N002 H00A 0.8200 . ?
N002 C005 1.351(2) . ?
N002 H00B 0.87(2) . ?
N1 C005 1.336(2) . ?
N1 C00I 1.353(2) . ?
N2 C006 1.150(2) . ?
C005 C008 1.417(2) . ?
C006 C008 1.428(2) . ?
C007 H00C 0.9600 . ?
C007 H00D 0.9600 . ?
C007 H00E 0.9600 . ?
C007 C00F 1.519(2) . ?
C008 C00A 1.403(2) . ?
C009 H00F 0.9600 . ?
C009 H00G 0.9600 . ?
C009 H00H 0.9600 . ?
C009 C00B 1.532(3) . ?
C00A C00B 1.509(2) . ?
C00A C00F 1.404(2) . ?
C00B H00I 0.9700 . ?
C00B H00J 0.9700 . ?
C00C H00K 0.9300 . ?
C00C C00D 1.390(2) . ?
C00C C00G 1.385(3) . ?
C00D H00L 0.9300 . ?
C00D C00J 1.401(2) . ?
C00E C00H 1.399(2) . ?
C00E C00J 1.409(2) . ?
C00F C00I 1.408(2) . ?
C00G H00M 0.9300 . ?
C00G C00H 1.385(3) . ?
C00H H00N 0.9300 . ?
C00I C00J 1.491(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00E O001 H001 109.5 . . ?
H00A N002 H00B 131.3 . . ?
C005 N002 H00A 109.5 . . ?
C005 N002 H00B 119.1(15) . . ?
C005 N1 C00I 120.38(14) . . ?
N002 C005 C008 122.92(15) . . ?
N1 C005 N002 116.96(14) . . ?
N1 C005 C008 120.08(15) . . ?
N2 C006 C008 177.68(18) . . ?
H00C C007 H00D 109.5 . . ?
H00C C007 H00E 109.5 . . ?
H00D C007 H00E 109.5 . . ?
C00F C007 H00C 109.5 . . ?
C00F C007 H00D 109.5 . . ?
C00F C007 H00E 109.5 . . ?
C005 C008 C006 117.98(15) . . ?
C00A C008 C005 120.12(15) . . ?
C00A C008 C006 121.82(15) . . ?
H00F C009 H00G 109.5 . . ?
H00F C009 H00H 109.5 . . ?
H00G C009 H00H 109.5 . . ?
C00B C009 H00F 109.5 . . ?
C00B C009 H00G 109.5 . . ?
C00B C009 H00H 109.5 . . ?
C008 C00A C00B 118.59(15) . . ?
C008 C00A C00F 119.04(15) . . ?
C00F C00A C00B 122.37(15) . . ?
C009 C00B H00I 109.1 . . ?
C009 C00B H00J 109.1 . . ?
C00A C00B C009 112.51(15) . . ?
C00A C00B H00I 109.1 . . ?
C00A C00B H00J 109.1 . . ?
H00I C00B H00J 107.8 . . ?
C00D C00C H00K 120.2 . . ?
C00G C00C H00K 120.2 . . ?
C00G C00C C00D 119.54(17) . . ?
C00C C00D H00L 119.2 . . ?
C00C C00D C00J 121.64(17) . . ?
C00J C00D H00L 119.2 . . ?
O001 C00E C00H 116.88(15) . . ?
O001 C00E C00J 122.80(15) . . ?
C00H C00E C00J 120.31(16) . . ?
C00A C00F C007 120.32(15) . . ?
C00A C00F C00I 117.28(15) . . ?
C00I C00F C007 122.30(15) . . ?
C00C C00G H00M 119.8 . . ?
C00C C00G C00H 120.34(17) . . ?
C00H C00G H00M 119.8 . . ?
C00E C00H H00N 119.9 . . ?
C00G C00H C00E 120.16(17) . . ?
C00G C00H H00N 119.9 . . ?
N1 C00I C00F 122.99(15) . . ?
N1 C00I C00J 112.71(14) . . ?
C00F C00I C00J 124.26(15) . . ?
C00D C00J C00E 117.78(15) . . ?
C00D C00J C00I 121.86(15) . . ?
C00E C00J C00I 120.31(15) . . ?

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
O001 C00E C00H C00G -176.52(16) . . . . ?
O001 C00E C00J C00D 174.56(15) . . . . ?
O001 C00E C00J C00I -3.0(3) . . . . ?
N002 C005 C008 C006 0.8(3) . . . . ?
N002 C005 C008 C00A -175.93(17) . . . . ?
N1 C005 C008 C006 178.65(16) . . . . ?
N1 C005 C008 C00A 1.9(2) . . . . ?
N1 C00I C00J C00D -144.66(18) . . . . ?
N1 C00I C00J C00E 32.8(2) . . . . ?
C005 N1 C00I C00F -3.0(3) . . . . ?
C005 N1 C00I C00J 179.08(15) . . . . ?
C005 C008 C00A C00B 176.27(15) . . . . ?
C005 C008 C00A C00F -3.5(2) . . . . ?
C006 C008 C00A C00B -0.4(2) . . . . ?
C006 C008 C00A C00F 179.88(16) . . . . ?
C007 C00F C00I N1 -174.94(16) . . . . ?
C007 C00F C00I C00J 2.7(3) . . . . ?
C008 C00A C00B C009 98.77(19) . . . . ?
C008 C00A C00F C007 178.25(15) . . . . ?
C008 C00A C00F C00I 1.9(2) . . . . ?
C00A C00F C00I N1 1.3(3) . . . . ?
C00A C00F C00I C00J 178.99(15) . . . . ?
C00B C00A C00F C007 -1.5(3) . . . . ?
C00B C00A C00F C00I -177.84(15) . . . . ?
C00C C00D C00J C00E 3.6(3) . . . . ?
C00C C00D C00J C00I -178.88(16) . . . . ?
C00C C00G C00H C00E 0.5(3) . . . . ?
C00D C00C C00G C00H -2.4(3) . . . . ?
C00F C00A C00B C009 -81.5(2) . . . . ?
C00F C00I C00J C00D 37.5(2) . . . . ?
C00F C00I C00J C00E -145.08(18) . . . . ?
C00G C00C C00D C00J 0.3(3) . . . . ?
C00H C00E C00J C00D -5.5(3) . . . . ?
C00H C00E C00J C00I 176.96(15) . . . . ?
C00I N1 C005 N002 179.30(16) . . . . ?
C00I N1 C005 C008 1.3(2) . . . . ?
C00J C00E C00H C00G 3.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
