# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_YJDP301
_database_code_depnum_ccdc_archive 'CCDC 2341570'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2024-03-19 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
_audit_creation_date             2023-07-17
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_chemical_formula_moiety         'C18 H15 N3 O'
_chemical_formula_sum            'C18 H15 N3 O'
_chemical_name_systematic        
;'6-benzyl-2-methylpyrazolo[1,5-c]quinazolin-5(6H)-one'
;
_chemical_formula_weight         289.339
_chemical_oxdiff_formula         C18H15N3O
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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                   15.8567(6)
_cell_length_b                   9.2722(4)
_cell_length_c                   9.8086(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.020(4)
_cell_angle_gamma                90
_cell_volume                     1434.17(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293.0
_cell_measurement_reflns_used    9458
_cell_measurement_theta_max      32.5260
_cell_measurement_theta_min      3.3470
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.639
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             608.0
_exptl_crystal_description       tab
_exptl_crystal_colour            colourless
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 5 0 0.1019
-4 -5 1 0.1104
0 0 -1 0.1929
0 0 1 0.2712
-1 0 0 0.0466
1 0 0 0.0448
-3 -5 0 0.0759

_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.09
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.9833 5.0047 0.0078 0.3625 0.1772 -0.1264
-3.9920 -5.0020 0.9933 -0.3400 -0.1665 0.1947
0.0086 -0.0027 -1.0011 -0.0225 -0.0107 -0.0683
-0.0086 0.0027 1.0011 0.0225 0.0107 0.0683
-0.9994 -0.0015 -0.0025 -0.0352 0.0279 0.0023
0.9994 0.0015 0.0025 0.0352 -0.0279 -0.0023
-2.9840 -5.0032 -0.0053 -0.3273 -0.2051 0.1241

_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.9988
_diffrn_reflns_Laue_measured_fraction_max 0.9984
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26314
_diffrn_reflns_point_group_measured_fraction_full 0.9988
_diffrn_reflns_point_group_measured_fraction_max 0.9984
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         3.03
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9984
_diffrn_ambient_temperature      293.0
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  99.00   0.50    6.00    --    9.20  57.00 -30.00  238
  2  ω    -20.00  99.00   0.50    6.00    --    9.20  57.00  60.00  238
  3  ω    -20.00  99.00   0.50    6.00    --    9.20  57.00 -90.00  238
  4  ω     23.00  99.00   0.50    6.00    --    9.20  57.00 -60.00  152
  5  ω      1.00  86.00   0.50    6.00    --    9.20  38.00 150.00  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0351014000
_diffrn_orient_matrix_UB_12      0.0444673000
_diffrn_orient_matrix_UB_13      0.0226875000
_diffrn_orient_matrix_UB_21      -0.0280287000
_diffrn_orient_matrix_UB_22      0.0576975000
_diffrn_orient_matrix_UB_23      0.0102486000
_diffrn_orient_matrix_UB_31      -0.0024129000
_diffrn_orient_matrix_UB_32      -0.0234466000
_diffrn_orient_matrix_UB_33      0.0682894000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              22
_reflns_limit_h_min              -22
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3366
_reflns_number_total             4365
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  
'olex2.refine 1.5-ac5-024 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.1209
_refine_diff_density_min         -0.1337
_refine_diff_density_rms         0.0320
_refine_ls_d_res_high            0.7001
_refine_ls_d_res_low             6.7205
_refine_ls_extinction_coef       0.0187(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0242
_refine_ls_restrained_S_all      1.0994
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0077P)²+0.0293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0441
_refine_ls_wR_factor_ref         0.0474
_refine_special_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:         PBE
   BASIS SET:      cc-pVTZ
   CHARGE:         0
   MULTIPLICITY:   1
   SOLVATION:      Acetone
   DATE:           2023-07-17_13-44-16
;
_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
;
_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 0.25858(2) 0.11177(4) 0.34076(4) 0.05003(11) Uani 1.000000 .
N1 N 0.26324(2) 0.35739(4) 0.32242(4) 0.03279(9) Uani 1.000000 .
N2 N 0.17268(2) 0.24721(4) 0.46193(4) 0.03427(10) Uani 1.000000 .
N3 N 0.13491(3) 0.13122(5) 0.51523(5) 0.04148(11) Uani 1.000000 .
C13 C 0.41455(3) 0.37075(5) 0.27352(5) 0.03391(11) Uani 1.000000 .
C8 C 0.23884(3) 0.49444(5) 0.36498(5) 0.03256(10) Uani 1.000000 .
C1 C 0.23418(3) 0.22991(5) 0.37131(5) 0.03429(11) Uani 1.000000 .
C2 C 0.14501(3) 0.37552(5) 0.51012(5) 0.03548(11) Uani 1.000000 .
C3 C 0.18018(3) 0.50629(5) 0.46197(5) 0.03573(11) Uani 1.000000 .
C12 C 0.32335(3) 0.34486(7) 0.21896(6) 0.03673(11) Uani 1.000000 .
H12A H 0.3034(3) 0.4183(7) 0.1347(6) 0.0568(16) Uani 1.000000 .
H12B H 0.3167(4) 0.2348(7) 0.1785(6) 0.0543(16) Uani 1.000000 .
C18 C 0.44788(3) 0.31515(6) 0.39913(6) 0.04339(13) Uani 1.000000 .
H18 H 0.4067(4) 0.2583(8) 0.4623(7) 0.075(2) Uani 1.000000 .
C14 C 0.46784(3) 0.44436(7) 0.19436(6) 0.04486(13) Uani 1.000000 .
H14 H 0.4414(4) 0.4916(8) 0.0982(7) 0.073(2) Uani 1.000000 .
C9 C 0.08214(3) 0.18824(6) 0.59654(5) 0.04386(13) Uani 1.000000 .
C7 C 0.27258(4) 0.62008(6) 0.31299(6) 0.04307(12) Uani 1.000000 .
H7 H 0.3196(4) 0.6146(7) 0.2389(7) 0.0676(19) Uani 1.000000 .
C17 C 0.53341(4) 0.33040(7) 0.44373(7) 0.05121(15) Uani 1.000000 .
H17 H 0.5584(4) 0.2867(9) 0.5425(8) 0.091(2) Uani 1.000000 .
C10 C 0.08582(3) 0.34044(7) 0.59737(6) 0.04629(13) Uani 1.000000 .
H10 H 0.0511(4) 0.4137(8) 0.6556(7) 0.078(2) Uani 1.000000 .
C15 C 0.55371(4) 0.45916(7) 0.23848(7) 0.05246(15) Uani 1.000000 .
H15 H 0.5944(4) 0.5162(9) 0.1758(7) 0.086(2) Uani 1.000000 .
C16 C 0.58663(4) 0.40116(7) 0.36249(7) 0.05100(15) Uani 1.000000 .
H16 H 0.6540(4) 0.4131(8) 0.3963(7) 0.083(2) Uani 1.000000 .
C6 C 0.24804(4) 0.75363(6) 0.35796(7) 0.05182(15) Uani 1.000000 .
H6 H 0.2733(5) 0.8497(7) 0.3171(8) 0.082(2) Uani 1.000000 .
C4 C 0.15718(4) 0.64236(6) 0.50703(7) 0.04917(14) Uani 1.000000 .
H4 H 0.1131(4) 0.6479(7) 0.5823(7) 0.0708(19) Uani 1.000000 .
C11 C 0.02819(5) 0.09349(11) 0.67394(9) 0.06079(19) Uani 1.000000 .
H11A H -0.0301(6) 0.0744(13) 0.6265(9) 0.136(4) Uani 1.000000 .
H11B H 0.0219(8) 0.1349(14) 0.7692(11) 0.142(5) Uani 1.000000 .
H11C H 0.0553(6) -0.0113(13) 0.6917(13) 0.140(5) Uani 1.000000 .
C5 C 0.19089(4) 0.76602(7) 0.45572(7) 0.05522(16) Uani 1.000000 .
H5 H 0.1742(5) 0.8707(7) 0.4899(8) 0.085(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 1.2099(6) . ?
N1 C8 1.4045(6) . ?
N1 C1 1.3732(6) . ?
N1 C12 1.4678(6) . ?
N2 N3 1.3618(5) . ?
N2 C1 1.3959(6) . ?
N2 C2 1.3692(6) . ?
N3 C9 1.3250(7) . ?
C13 C12 1.5077(7) . ?
C13 C18 1.3880(7) . ?
C13 C14 1.3857(7) . ?
C8 C3 1.4029(7) . ?
C8 C7 1.4003(7) . ?
C2 C3 1.4350(7) . ?
C2 C10 1.3739(7) . ?
C3 C4 1.3978(7) . ?
C12 H12A 1.091(6) . ?
C12 H12B 1.096(6) . ?
C18 H18 1.084(6) . ?
C18 C17 1.3878(8) . ?
C14 H14 1.083(7) . ?
C14 C15 1.3917(8) . ?
C9 C10 1.4123(9) . ?
C9 C11 1.4888(8) . ?
C7 H7 1.096(6) . ?
C7 C6 1.3839(8) . ?
C17 H17 1.086(7) . ?
C17 C16 1.3852(9) . ?
C10 H10 1.076(7) . ?
C15 H15 1.075(6) . ?
C15 C16 1.3813(9) . ?
C16 H16 1.090(6) . ?
C6 H6 1.071(6) . ?
C6 C5 1.3915(9) . ?
C4 H4 1.070(7) . ?
C4 C5 1.3820(9) . ?
C11 H11A 1.005(8) . ?
C11 H11B 1.025(10) . ?
C11 H11C 1.070(11) . ?
C5 H5 1.069(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 124.19(4) . . ?
C12 N1 C8 119.74(4) . . ?
C12 N1 C1 116.06(4) . . ?
C1 N2 N3 121.23(4) . . ?
C2 N2 N3 112.58(4) . . ?
C2 N2 C1 126.17(4) . . ?
C9 N3 N2 104.29(4) . . ?
C18 C13 C12 121.18(4) . . ?
C14 C13 C12 119.88(5) . . ?
C14 C13 C18 118.85(5) . . ?
C3 C8 N1 119.69(4) . . ?
C7 C8 N1 121.12(4) . . ?
C7 C8 C3 119.18(5) . . ?
N1 C1 O1 124.41(4) . . ?
N2 C1 O1 121.65(4) . . ?
N2 C1 N1 113.94(4) . . ?
C3 C2 N2 118.10(4) . . ?
C10 C2 N2 105.89(5) . . ?
C10 C2 C3 136.01(5) . . ?
C2 C3 C8 117.72(4) . . ?
C4 C3 C8 119.91(5) . . ?
C4 C3 C2 122.37(5) . . ?
C13 C12 N1 114.22(4) . . ?
H12A C12 N1 108.5(3) . . ?
H12A C12 C13 111.1(3) . . ?
H12B C12 N1 106.2(3) . . ?
H12B C12 C13 109.2(3) . . ?
H12B C12 H12A 107.3(5) . . ?
H18 C18 C13 119.5(3) . . ?
C17 C18 C13 120.70(5) . . ?
C17 C18 H18 119.8(3) . . ?
H14 C14 C13 118.9(3) . . ?
C15 C14 C13 120.57(6) . . ?
C15 C14 H14 120.5(3) . . ?
C10 C9 N3 111.96(5) . . ?
C11 C9 N3 120.29(6) . . ?
C11 C9 C10 127.76(6) . . ?
H7 C7 C8 121.0(3) . . ?
C6 C7 C8 119.83(6) . . ?
C6 C7 H7 119.1(3) . . ?
H17 C17 C18 119.8(4) . . ?
C16 C17 C18 120.07(6) . . ?
C16 C17 H17 120.1(4) . . ?
C9 C10 C2 105.28(5) . . ?
H10 C10 C2 127.0(4) . . ?
H10 C10 C9 127.7(4) . . ?
H15 C15 C14 119.8(4) . . ?
C16 C15 C14 120.17(6) . . ?
C16 C15 H15 120.1(4) . . ?
C15 C16 C17 119.61(6) . . ?
H16 C16 C17 120.7(4) . . ?
H16 C16 C15 119.7(4) . . ?
H6 C6 C7 119.7(4) . . ?
C5 C6 C7 121.25(6) . . ?
C5 C6 H6 119.0(4) . . ?
H4 C4 C3 118.2(3) . . ?
C5 C4 C3 120.67(6) . . ?
C5 C4 H4 121.1(3) . . ?
H11A C11 C9 114.7(5) . . ?
H11B C11 C9 111.1(5) . . ?
H11B C11 H11A 108.3(8) . . ?
H11C C11 C9 112.1(5) . . ?
H11C C11 H11A 104.5(8) . . ?
H11C C11 H11B 105.5(9) . . ?
C4 C5 C6 119.15(6) . . ?
H5 C5 C6 119.5(4) . . ?
H5 C5 C4 121.4(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 C8 -175.64(5) . . . . ?
O1 C1 N1 C12 4.53(6) . . . . ?
O1 C1 N2 N3 -2.86(6) . . . . ?
O1 C1 N2 C2 175.30(5) . . . . ?
N1 C8 C3 C2 -2.24(5) . . . . ?
N1 C8 C3 C4 178.52(5) . . . . ?
N1 C8 C7 C6 -179.30(5) . . . . ?
N1 C1 N2 N3 177.30(4) . . . . ?
N1 C1 N2 C2 -4.54(5) . . . . ?
N1 C12 C13 C18 41.73(6) . . . . ?
N1 C12 C13 C14 -141.91(5) . . . . ?
N2 N3 C9 C10 -0.48(4) . . . . ?
N2 N3 C9 C11 179.71(5) . . . . ?
N2 C2 C3 C8 1.99(5) . . . . ?
N2 C2 C3 C4 -178.79(5) . . . . ?
N2 C2 C10 C9 0.40(4) . . . . ?
N3 C9 C10 C2 0.05(5) . . . . ?
C13 C18 C17 C16 -0.27(7) . . . . ?
C13 C14 C15 C16 -0.41(7) . . . . ?
C8 C3 C2 C10 -177.19(5) . . . . ?
C8 C3 C4 C5 0.81(6) . . . . ?
C8 C7 C6 C5 0.79(6) . . . . ?
C2 C3 C4 C5 -178.39(5) . . . . ?
C2 C10 C9 C11 179.84(5) . . . . ?
C3 C4 C5 C6 0.19(7) . . . . ?
C18 C17 C16 C15 1.46(7) . . . . ?
C14 C15 C16 C17 -1.12(7) . . . . ?
C7 C6 C5 C4 -0.99(7) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.318
_oxdiff_exptl_absorpt_empirical_full_min 0.752

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
