# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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. 
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#######################################################################

data_3l
_database_code_depnum_ccdc_archive 'CCDC 2409299'
loop_
_audit_author_name
_audit_author_address
'Dikundwar A.G.'
;National Institute of Pharmaceutical Education and Research (NIPER) Hyderabad
India
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-05-21 downloaded from the CCDC.
;
_audit_creation_date             2025-03-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
amol.dikundwar@niperhyd.ac.in
subhajahnavi18@gmail.com
_chemical_name_common            3l
_chemical_name_systematic        
2-(4-methoxyphenyl)-5-phenyl-5,6-dihydropyrazolo[1,5-c]quinazoline
_chemical_formula_moiety         'C23 H19 N3 O'
_chemical_formula_sum            'C23 H19 N3 O'
_chemical_formula_weight         353.41
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.5160(10)
_cell_length_b                   13.0682(12)
_cell_length_c                   13.6833(14)
_cell_angle_alpha                71.107(3)
_cell_angle_beta                 77.855(3)
_cell_angle_gamma                71.037(3)
_cell_volume                     1829.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    298
_cell_measurement_theta_max      23.581
_cell_measurement_theta_min      2.236
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1311 before and 0.0630 after correction.
The Ratio of minimum to maximum transmission is 0.9529.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_preparation       
'Pre-heated ethanol is added to solubulize the solid compound and cooled down at room temperature'
_exptl_crystal_recrystallization_method 
'The saturated ethanol solution was subjected for slow solvent evaporation excpecting the formation of single crystal'
_exptl_crystal_size_max          0.694
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.095
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            74168
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.987
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker Photon III C14 CPAD detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.39
_diffrn_source_power             0.0695
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5043
_reflns_number_total             6439
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         6439
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0845P)²+0.2241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1563
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C8(H8), C8(H8)
1.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C5(H5), C4(H4), C3(H3), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C22(H22), C21(H21), C19(H19), C18(H18), C3(H3), C4(H4),
 C5(H5), C6(H6), N1(H1), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C21(H21), C22(H22)
1.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1_1 O 1.19934(16) 0.14633(13) 0.97137(13) 0.0892(5) Uani 1 1 d . . . . .
N2_1 N 0.70903(13) 0.66301(12) 0.71469(11) 0.0534(4) Uani 1 1 d . . . . .
N1_1 N 0.53186(14) 0.80493(14) 0.66061(13) 0.0646(4) Uani 1 1 d . . . . .
H1_1 H 0.452992 0.819562 0.663620 0.078 Uiso 1 1 calc R U . . .
N3_1 N 0.77135(13) 0.55396(12) 0.75021(11) 0.0551(4) Uani 1 1 d . . . . .
C2_1 C 0.69444(17) 0.85402(15) 0.70461(13) 0.0545(4) Uani 1 1 d . . . . .
C1_1 C 0.58065(16) 0.88678(16) 0.66494(14) 0.0565(4) Uani 1 1 d . . . . .
C6_1 C 0.51538(19) 1.00014(17) 0.63838(15) 0.0660(5) Uani 1 1 d . . . . .
H6_1 H 0.440768 1.022855 0.610957 0.079 Uiso 1 1 calc R U . . .
C5_1 C 0.5610(2) 1.07860(18) 0.65260(16) 0.0726(6) Uani 1 1 d . . . . .
H5_1 H 0.515409 1.153909 0.636677 0.087 Uiso 1 1 calc R U . . .
C4_1 C 0.6736(2) 1.04738(17) 0.69024(17) 0.0758(6) Uani 1 1 d . . . . .
H4_1 H 0.704123 1.101353 0.698591 0.091 Uiso 1 1 calc R U . . .
C3_1 C 0.7399(2) 0.93559(17) 0.71520(16) 0.0667(5) Uani 1 1 d . . . . .
H3_1 H 0.816229 0.914454 0.739489 0.080 Uiso 1 1 calc R U . . .
C7_1 C 0.75552(16) 0.73450(15) 0.73718(13) 0.0513(4) Uani 1 1 d . . . . .
C8_1 C 0.60895(15) 0.69507(15) 0.65116(14) 0.0546(4) Uani 1 1 d . . . . .
H8_1 H 0.559403 0.641531 0.682110 0.066 Uiso 1 1 calc R U . . .
C9_1 C 0.85312(16) 0.66749(15) 0.79267(13) 0.0537(4) Uani 1 1 d . . . . .
H9_1 H 0.903820 0.690982 0.820428 0.064 Uiso 1 1 calc R U . . .
C10_1 C 0.86026(15) 0.55637(15) 0.79867(12) 0.0508(4) Uani 1 1 d . . . . .
C11_1 C 0.65633(15) 0.68997(15) 0.54020(14) 0.0533(4) Uani 1 1 d . . . . .
C12_1 C 0.62452(18) 0.61757(15) 0.50312(15) 0.0611(5) Uani 1 1 d . . . . .
H12_1 H 0.574903 0.572988 0.546099 0.073 Uiso 1 1 calc R U . . .
C13_1 C 0.6661(2) 0.61096(19) 0.40237(18) 0.0792(6) Uani 1 1 d . . . . .
H13_1 H 0.644805 0.561664 0.377816 0.095 Uiso 1 1 calc R U . . .
C14_1 C 0.7383(2) 0.6768(2) 0.33889(18) 0.0859(7) Uani 1 1 d . . . . .
H14_1 H 0.766704 0.671630 0.271335 0.103 Uiso 1 1 calc R U . . .
C15_1 C 0.7692(2) 0.7504(2) 0.37397(17) 0.0839(7) Uani 1 1 d . . . . .
H15_1 H 0.817360 0.795890 0.330026 0.101 Uiso 1 1 calc R U . . .
C16_1 C 0.72871(18) 0.75688(18) 0.47462(16) 0.0672(5) Uani 1 1 d . . . . .
H16_1 H 0.750159 0.806494 0.498580 0.081 Uiso 1 1 calc R U . . .
C17_1 C 0.94831(16) 0.45085(15) 0.84684(13) 0.0530(4) Uani 1 1 d . . . . .
C22_1 C 1.05130(17) 0.45009(16) 0.88503(14) 0.0589(5) Uani 1 1 d . . . . .
H22_1 H 1.063188 0.518237 0.881794 0.071 Uiso 1 1 calc R U . . .
C21_1 C 1.13654(18) 0.35093(16) 0.92766(14) 0.0614(5) Uani 1 1 d . . . . .
H21_1 H 1.204452 0.352740 0.953079 0.074 Uiso 1 1 calc R U . . .
C20_1 C 1.12064(19) 0.24959(16) 0.93239(15) 0.0639(5) Uani 1 1 d . . . . .
C19_1 C 1.0175(2) 0.24818(18) 0.89591(17) 0.0736(6) Uani 1 1 d . . . . .
H19_1 H 1.005663 0.179861 0.899603 0.088 Uiso 1 1 calc R U . . .
C18_1 C 0.9332(2) 0.34694(17) 0.85458(15) 0.0659(5) Uani 1 1 d . . . . .
H18_1 H 0.864165 0.344605 0.831109 0.079 Uiso 1 1 calc R U . . .
C23_1 C 1.3136(2) 0.1422(2) 0.9978(2) 0.0993(8) Uani 1 1 d . . . . .
H23A_1 H 1.360255 0.178187 0.937149 0.149 Uiso 1 1 calc R U . . .
H23B_1 H 1.359565 0.065138 1.023795 0.149 Uiso 1 1 calc R U . . .
H23C_1 H 1.298562 0.180517 1.050330 0.149 Uiso 1 1 calc R U . . .
O1_2 O 1.67276(17) 0.13878(14) 1.01740(13) 0.0995(6) Uani 1 1 d . . . . .
N2_2 N 1.29699(14) 0.68873(13) 0.68893(11) 0.0552(4) Uani 1 1 d . . . . .
N3_2 N 1.37466(14) 0.58467(13) 0.71625(11) 0.0562(4) Uani 1 1 d . . . . .
C2_2 C 1.14212(18) 0.83657(16) 0.75092(16) 0.0617(5) Uani 1 1 d . . . . .
C3_2 C 1.05721(19) 0.87803(18) 0.82715(18) 0.0732(6) Uani 1 1 d . . . . .
H3_2 H 1.050185 0.831158 0.894422 0.088 Uiso 1 1 calc R U . . .
C4_2 C 0.9831(2) 0.9877(2) 0.8047(2) 0.0869(7) Uani 1 1 d . . . . .
H4_2 H 0.927224 1.015067 0.856391 0.104 Uiso 1 1 calc R U . . .
C5_2 C 0.9931(2) 1.0558(2) 0.7047(2) 0.0892(7) Uani 1 1 d . . . . .
H5_2 H 0.943671 1.129876 0.689051 0.107 Uiso 1 1 calc R U . . .
C6_2 C 1.0755(2) 1.01611(18) 0.6267(2) 0.0812(6) Uani 1 1 d . . . . .
H6_2 H 1.080171 1.063093 0.559293 0.097 Uiso 1 1 calc R U . . .
C1_2 C 1.15114(19) 0.90639(17) 0.64912(17) 0.0657(5) Uani 1 1 d . . . . .
N1_2 N 1.24310(17) 0.86728(14) 0.57475(13) 0.0719(5) Uani 1 1 d . . . . .
H1_2 H 1.274369 0.914397 0.525183 0.086 Uiso 1 1 calc R U . . .
C8_2 C 1.28688(17) 0.74830(15) 0.57966(14) 0.0570(4) Uani 1 1 d . . . . .
H8_2 H 1.370666 0.734640 0.542631 0.068 Uiso 1 1 calc R U . . .
C7_2 C 1.22718(17) 0.72382(16) 0.77138(14) 0.0565(4) Uani 1 1 d . . . . .
C10_2 C 1.35567(16) 0.55321(15) 0.82085(14) 0.0545(4) Uani 1 1 d . . . . .
C9_2 C 1.26439(17) 0.63757(16) 0.85821(14) 0.0600(5) Uani 1 1 d . . . . .
H9_2 H 1.235048 0.635684 0.927314 0.072 Uiso 1 1 calc R U . . .
C11_2 C 1.21175(16) 0.70475(14) 0.53229(13) 0.0520(4) Uani 1 1 d . . . . .
C12_2 C 1.09868(18) 0.68812(18) 0.58015(16) 0.0678(5) Uani 1 1 d . . . . .
H12_2 H 1.065817 0.705534 0.642844 0.081 Uiso 1 1 calc R U . . .
C13_2 C 1.0343(2) 0.64611(19) 0.53601(17) 0.0749(6) Uani 1 1 d . . . . .
H13_2 H 0.958217 0.635237 0.568913 0.090 Uiso 1 1 calc R U . . .
C14_2 C 1.0820(2) 0.61996(17) 0.44317(17) 0.0691(5) Uani 1 1 d . . . . .
H14_2 H 1.038097 0.591774 0.413271 0.083 Uiso 1 1 calc R U . . .
C15_2 C 1.19421(19) 0.63559(15) 0.39515(15) 0.0625(5) Uani 1 1 d . . . . .
H15_2 H 1.226759 0.617893 0.332533 0.075 Uiso 1 1 calc R U . . .
C16_2 C 1.25918(17) 0.67765(14) 0.43960(14) 0.0566(4) Uani 1 1 d . . . . .
H16_2 H 1.335603 0.687811 0.406793 0.068 Uiso 1 1 calc R U . . .
C17_2 C 1.43356(17) 0.44502(16) 0.87661(14) 0.0570(5) Uani 1 1 d . . . . .
C18_2 C 1.5241(2) 0.37773(19) 0.82103(16) 0.0785(6) Uani 1 1 d . . . . .
H18_2 H 1.532545 0.401432 0.748725 0.094 Uiso 1 1 calc R U . . .
C19_2 C 1.6007(2) 0.2780(2) 0.86998(18) 0.0871(7) Uani 1 1 d . . . . .
H19_2 H 1.660650 0.235281 0.830665 0.105 Uiso 1 1 calc R U . . .
C20_2 C 1.5903(2) 0.23974(18) 0.97704(16) 0.0707(5) Uani 1 1 d . . . . .
C21_2 C 1.50197(19) 0.30462(18) 1.03428(15) 0.0681(5) Uani 1 1 d . . . . .
H21_2 H 1.494054 0.280229 1.106565 0.082 Uiso 1 1 calc R U . . .
C22_2 C 1.42504(19) 0.40612(17) 0.98411(15) 0.0638(5) Uani 1 1 d . . . . .
H22_2 H 1.366141 0.449290 1.023605 0.077 Uiso 1 1 calc R U . . .
C23_2 C 1.6538(3) 0.0857(2) 1.12465(19) 0.0951(8) Uani 1 1 d . . . . .
H23A_2 H 1.575963 0.068263 1.140786 0.143 Uiso 1 1 calc R U . . .
H23B_2 H 1.653416 0.135166 1.163574 0.143 Uiso 1 1 calc R U . . .
H23C_2 H 1.719214 0.017495 1.142635 0.143 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1_1 C20_1 1.367(2) . ?
O1_1 C23_1 1.417(3) . ?
N2_1 N3_1 1.348(2) . ?
N2_1 C7_1 1.354(2) . ?
N2_1 C8_1 1.460(2) . ?
N1_1 H1_1 0.8600 . ?
N1_1 C1_1 1.382(2) . ?
N1_1 C8_1 1.453(2) . ?
N3_1 C10_1 1.345(2) . ?
C2_1 C1_1 1.407(3) . ?
C2_1 C3_1 1.388(3) . ?
C2_1 C7_1 1.449(2) . ?
C1_1 C6_1 1.391(3) . ?
C6_1 H6_1 0.9300 . ?
C6_1 C5_1 1.374(3) . ?
C5_1 H5_1 0.9300 . ?
C5_1 C4_1 1.384(3) . ?
C4_1 H4_1 0.9300 . ?
C4_1 C3_1 1.377(3) . ?
C3_1 H3_1 0.9300 . ?
C7_1 C9_1 1.377(2) . ?
C8_1 H8_1 0.9800 . ?
C8_1 C11_1 1.517(2) . ?
C9_1 H9_1 0.9300 . ?
C9_1 C10_1 1.404(2) . ?
C10_1 C17_1 1.466(2) . ?
C11_1 C12_1 1.379(2) . ?
C11_1 C16_1 1.384(3) . ?
C12_1 H12_1 0.9300 . ?
C12_1 C13_1 1.382(3) . ?
C13_1 H13_1 0.9300 . ?
C13_1 C14_1 1.365(3) . ?
C14_1 H14_1 0.9300 . ?
C14_1 C15_1 1.370(3) . ?
C15_1 H15_1 0.9300 . ?
C15_1 C16_1 1.379(3) . ?
C16_1 H16_1 0.9300 . ?
C17_1 C22_1 1.389(2) . ?
C17_1 C18_1 1.392(3) . ?
C22_1 H22_1 0.9300 . ?
C22_1 C21_1 1.381(3) . ?
C21_1 H21_1 0.9300 . ?
C21_1 C20_1 1.374(3) . ?
C20_1 C19_1 1.390(3) . ?
C19_1 H19_1 0.9300 . ?
C19_1 C18_1 1.368(3) . ?
C18_1 H18_1 0.9300 . ?
C23_1 H23A_1 0.9600 . ?
C23_1 H23B_1 0.9600 . ?
C23_1 H23C_1 0.9600 . ?
O1_2 C20_2 1.372(3) . ?
O1_2 C23_2 1.410(3) . ?
N2_2 N3_2 1.345(2) . ?
N2_2 C8_2 1.455(2) . ?
N2_2 C7_2 1.358(2) . ?
N3_2 C10_2 1.346(2) . ?
C2_2 C3_2 1.389(3) . ?
C2_2 C1_2 1.400(3) . ?
C2_2 C7_2 1.456(3) . ?
C3_2 H3_2 0.9300 . ?
C3_2 C4_2 1.381(3) . ?
C4_2 H4_2 0.9300 . ?
C4_2 C5_2 1.375(4) . ?
C5_2 H5_2 0.9300 . ?
C5_2 C6_2 1.386(3) . ?
C6_2 H6_2 0.9300 . ?
C6_2 C1_2 1.387(3) . ?
C1_2 N1_2 1.396(3) . ?
N1_2 H1_2 0.8600 . ?
N1_2 C8_2 1.454(2) . ?
C8_2 H8_2 0.9800 . ?
C8_2 C11_2 1.513(2) . ?
C7_2 C9_2 1.378(3) . ?
C10_2 C9_2 1.403(3) . ?
C10_2 C17_2 1.467(3) . ?
C9_2 H9_2 0.9300 . ?
C11_2 C12_2 1.380(3) . ?
C11_2 C16_2 1.381(2) . ?
C12_2 H12_2 0.9300 . ?
C12_2 C13_2 1.372(3) . ?
C13_2 H13_2 0.9300 . ?
C13_2 C14_2 1.378(3) . ?
C14_2 H14_2 0.9300 . ?
C14_2 C15_2 1.367(3) . ?
C15_2 H15_2 0.9300 . ?
C15_2 C16_2 1.381(3) . ?
C16_2 H16_2 0.9300 . ?
C17_2 C18_2 1.394(3) . ?
C17_2 C22_2 1.385(3) . ?
C18_2 H18_2 0.9300 . ?
C18_2 C19_2 1.365(3) . ?
C19_2 H19_2 0.9300 . ?
C19_2 C20_2 1.379(3) . ?
C20_2 C21_2 1.379(3) . ?
C21_2 H21_2 0.9300 . ?
C21_2 C22_2 1.385(3) . ?
C22_2 H22_2 0.9300 . ?
C23_2 H23A_2 0.9600 . ?
C23_2 H23B_2 0.9600 . ?
C23_2 H23C_2 0.9600 . ?

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
C20_1 O1_1 C23_1 118.17(18) . . ?
N3_1 N2_1 C7_1 113.28(14) . . ?
N3_1 N2_1 C8_1 120.46(14) . . ?
C7_1 N2_1 C8_1 126.06(15) . . ?
C1_1 N1_1 H1_1 118.8 . . ?
C1_1 N1_1 C8_1 122.38(15) . . ?
C8_1 N1_1 H1_1 118.8 . . ?
C10_1 N3_1 N2_1 104.34(14) . . ?
C1_1 C2_1 C7_1 117.33(16) . . ?
C3_1 C2_1 C1_1 119.33(18) . . ?
C3_1 C2_1 C7_1 123.27(17) . . ?
N1_1 C1_1 C2_1 119.19(17) . . ?
N1_1 C1_1 C6_1 121.36(17) . . ?
C6_1 C1_1 C2_1 119.26(17) . . ?
C1_1 C6_1 H6_1 120.0 . . ?
C5_1 C6_1 C1_1 120.09(19) . . ?
C5_1 C6_1 H6_1 120.0 . . ?
C6_1 C5_1 H5_1 119.5 . . ?
C6_1 C5_1 C4_1 121.1(2) . . ?
C4_1 C5_1 H5_1 119.5 . . ?
C5_1 C4_1 H4_1 120.3 . . ?
C3_1 C4_1 C5_1 119.3(2) . . ?
C3_1 C4_1 H4_1 120.3 . . ?
C2_1 C3_1 H3_1 119.6 . . ?
C4_1 C3_1 C2_1 120.9(2) . . ?
C4_1 C3_1 H3_1 119.6 . . ?
N2_1 C7_1 C2_1 118.24(15) . . ?
N2_1 C7_1 C9_1 105.77(15) . . ?
C9_1 C7_1 C2_1 135.93(16) . . ?
N2_1 C8_1 H8_1 107.8 . . ?
N2_1 C8_1 C11_1 112.40(14) . . ?
N1_1 C8_1 N2_1 106.38(14) . . ?
N1_1 C8_1 H8_1 107.8 . . ?
N1_1 C8_1 C11_1 114.48(15) . . ?
C11_1 C8_1 H8_1 107.8 . . ?
C7_1 C9_1 H9_1 127.1 . . ?
C7_1 C9_1 C10_1 105.77(16) . . ?
C10_1 C9_1 H9_1 127.1 . . ?
N3_1 C10_1 C9_1 110.82(16) . . ?
N3_1 C10_1 C17_1 119.72(16) . . ?
C9_1 C10_1 C17_1 129.45(16) . . ?
C12_1 C11_1 C8_1 118.83(16) . . ?
C12_1 C11_1 C16_1 119.03(18) . . ?
C16_1 C11_1 C8_1 122.12(16) . . ?
C11_1 C12_1 H12_1 119.9 . . ?
C11_1 C12_1 C13_1 120.3(2) . . ?
C13_1 C12_1 H12_1 119.9 . . ?
C12_1 C13_1 H13_1 120.0 . . ?
C14_1 C13_1 C12_1 120.0(2) . . ?
C14_1 C13_1 H13_1 120.0 . . ?
C13_1 C14_1 H14_1 119.8 . . ?
C13_1 C14_1 C15_1 120.5(2) . . ?
C15_1 C14_1 H14_1 119.8 . . ?
C14_1 C15_1 H15_1 120.1 . . ?
C14_1 C15_1 C16_1 119.8(2) . . ?
C16_1 C15_1 H15_1 120.1 . . ?
C11_1 C16_1 H16_1 119.8 . . ?
C15_1 C16_1 C11_1 120.4(2) . . ?
C15_1 C16_1 H16_1 119.8 . . ?
C22_1 C17_1 C10_1 121.59(16) . . ?
C22_1 C17_1 C18_1 117.19(17) . . ?
C18_1 C17_1 C10_1 121.21(17) . . ?
C17_1 C22_1 H22_1 119.1 . . ?
C21_1 C22_1 C17_1 121.82(18) . . ?
C21_1 C22_1 H22_1 119.1 . . ?
C22_1 C21_1 H21_1 120.1 . . ?
C20_1 C21_1 C22_1 119.76(18) . . ?
C20_1 C21_1 H21_1 120.1 . . ?
O1_1 C20_1 C21_1 125.11(19) . . ?
O1_1 C20_1 C19_1 115.44(18) . . ?
C21_1 C20_1 C19_1 119.44(19) . . ?
C20_1 C19_1 H19_1 119.9 . . ?
C18_1 C19_1 C20_1 120.25(19) . . ?
C18_1 C19_1 H19_1 119.9 . . ?
C17_1 C18_1 H18_1 119.2 . . ?
C19_1 C18_1 C17_1 121.52(19) . . ?
C19_1 C18_1 H18_1 119.2 . . ?
O1_1 C23_1 H23A_1 109.5 . . ?
O1_1 C23_1 H23B_1 109.5 . . ?
O1_1 C23_1 H23C_1 109.5 . . ?
H23A_1 C23_1 H23B_1 109.5 . . ?
H23A_1 C23_1 H23C_1 109.5 . . ?
H23B_1 C23_1 H23C_1 109.5 . . ?
C20_2 O1_2 C23_2 118.24(18) . . ?
N3_2 N2_2 C8_2 120.12(14) . . ?
N3_2 N2_2 C7_2 113.37(15) . . ?
C7_2 N2_2 C8_2 126.31(16) . . ?
N2_2 N3_2 C10_2 104.32(14) . . ?
C3_2 C2_2 C1_2 119.5(2) . . ?
C3_2 C2_2 C7_2 123.44(19) . . ?
C1_2 C2_2 C7_2 117.00(18) . . ?
C2_2 C3_2 H3_2 119.5 . . ?
C4_2 C3_2 C2_2 121.1(2) . . ?
C4_2 C3_2 H3_2 119.5 . . ?
C3_2 C4_2 H4_2 120.5 . . ?
C5_2 C4_2 C3_2 119.0(2) . . ?
C5_2 C4_2 H4_2 120.5 . . ?
C4_2 C5_2 H5_2 119.4 . . ?
C4_2 C5_2 C6_2 121.1(2) . . ?
C6_2 C5_2 H5_2 119.4 . . ?
C5_2 C6_2 H6_2 119.9 . . ?
C5_2 C6_2 C1_2 120.1(2) . . ?
C1_2 C6_2 H6_2 119.9 . . ?
C6_2 C1_2 C2_2 119.1(2) . . ?
C6_2 C1_2 N1_2 121.4(2) . . ?
N1_2 C1_2 C2_2 119.24(19) . . ?
C1_2 N1_2 H1_2 119.4 . . ?
C1_2 N1_2 C8_2 121.13(15) . . ?
C8_2 N1_2 H1_2 119.4 . . ?
N2_2 C8_2 H8_2 107.3 . . ?
N2_2 C8_2 C11_2 112.16(14) . . ?
N1_2 C8_2 N2_2 105.74(14) . . ?
N1_2 C8_2 H8_2 107.3 . . ?
N1_2 C8_2 C11_2 116.52(16) . . ?
C11_2 C8_2 H8_2 107.3 . . ?
N2_2 C7_2 C2_2 118.00(17) . . ?
N2_2 C7_2 C9_2 105.59(16) . . ?
C9_2 C7_2 C2_2 136.30(17) . . ?
N3_2 C10_2 C9_2 110.90(17) . . ?
N3_2 C10_2 C17_2 118.31(16) . . ?
C9_2 C10_2 C17_2 130.69(17) . . ?
C7_2 C9_2 C10_2 105.80(16) . . ?
C7_2 C9_2 H9_2 127.1 . . ?
C10_2 C9_2 H9_2 127.1 . . ?
C12_2 C11_2 C8_2 122.16(16) . . ?
C12_2 C11_2 C16_2 118.76(17) . . ?
C16_2 C11_2 C8_2 119.05(16) . . ?
C11_2 C12_2 H12_2 119.7 . . ?
C13_2 C12_2 C11_2 120.56(19) . . ?
C13_2 C12_2 H12_2 119.7 . . ?
C12_2 C13_2 H13_2 119.9 . . ?
C12_2 C13_2 C14_2 120.28(19) . . ?
C14_2 C13_2 H13_2 119.9 . . ?
C13_2 C14_2 H14_2 120.1 . . ?
C15_2 C14_2 C13_2 119.76(19) . . ?
C15_2 C14_2 H14_2 120.1 . . ?
C14_2 C15_2 H15_2 120.0 . . ?
C14_2 C15_2 C16_2 120.02(18) . . ?
C16_2 C15_2 H15_2 120.0 . . ?
C11_2 C16_2 C15_2 120.62(17) . . ?
C11_2 C16_2 H16_2 119.7 . . ?
C15_2 C16_2 H16_2 119.7 . . ?
C18_2 C17_2 C10_2 119.87(17) . . ?
C22_2 C17_2 C10_2 123.21(17) . . ?
C22_2 C17_2 C18_2 116.89(19) . . ?
C17_2 C18_2 H18_2 119.2 . . ?
C19_2 C18_2 C17_2 121.7(2) . . ?
C19_2 C18_2 H18_2 119.2 . . ?
C18_2 C19_2 H19_2 119.6 . . ?
C18_2 C19_2 C20_2 120.8(2) . . ?
C20_2 C19_2 H19_2 119.6 . . ?
O1_2 C20_2 C19_2 115.53(19) . . ?
O1_2 C20_2 C21_2 125.52(19) . . ?
C19_2 C20_2 C21_2 118.9(2) . . ?
C20_2 C21_2 H21_2 120.0 . . ?
C20_2 C21_2 C22_2 119.98(19) . . ?
C22_2 C21_2 H21_2 120.0 . . ?
C17_2 C22_2 H22_2 119.1 . . ?
C21_2 C22_2 C17_2 121.71(19) . . ?
C21_2 C22_2 H22_2 119.1 . . ?
O1_2 C23_2 H23A_2 109.5 . . ?
O1_2 C23_2 H23B_2 109.5 . . ?
O1_2 C23_2 H23C_2 109.5 . . ?
H23A_2 C23_2 H23B_2 109.5 . . ?
H23A_2 C23_2 H23C_2 109.5 . . ?
H23B_2 C23_2 H23C_2 109.5 . . ?

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_1 C20_1 C19_1 C18_1 -179.52(19) . . . . ?
N2_1 N3_1 C10_1 C9_1 -0.25(18) . . . . ?
N2_1 N3_1 C10_1 C17_1 -179.38(14) . . . . ?
N2_1 C7_1 C9_1 C10_1 0.92(18) . . . . ?
N2_1 C8_1 C11_1 C12_1 118.94(17) . . . . ?
N2_1 C8_1 C11_1 C16_1 -62.1(2) . . . . ?
N1_1 C1_1 C6_1 C5_1 173.93(18) . . . . ?
N1_1 C8_1 C11_1 C12_1 -119.54(18) . . . . ?
N1_1 C8_1 C11_1 C16_1 59.4(2) . . . . ?
N3_1 N2_1 C7_1 C2_1 -178.80(14) . . . . ?
N3_1 N2_1 C7_1 C9_1 -1.16(19) . . . . ?
N3_1 N2_1 C8_1 N1_1 157.88(14) . . . . ?
N3_1 N2_1 C8_1 C11_1 -76.08(19) . . . . ?
N3_1 C10_1 C17_1 C22_1 171.05(16) . . . . ?
N3_1 C10_1 C17_1 C18_1 -7.8(2) . . . . ?
C2_1 C1_1 C6_1 C5_1 -1.1(3) . . . . ?
C2_1 C7_1 C9_1 C10_1 177.93(18) . . . . ?
C1_1 N1_1 C8_1 N2_1 37.9(2) . . . . ?
C1_1 N1_1 C8_1 C11_1 -86.9(2) . . . . ?
C1_1 C2_1 C3_1 C4_1 1.9(3) . . . . ?
C1_1 C2_1 C7_1 N2_1 8.9(2) . . . . ?
C1_1 C2_1 C7_1 C9_1 -167.88(19) . . . . ?
C1_1 C6_1 C5_1 C4_1 2.0(3) . . . . ?
C6_1 C5_1 C4_1 C3_1 -1.0(3) . . . . ?
C5_1 C4_1 C3_1 C2_1 -1.0(3) . . . . ?
C3_1 C2_1 C1_1 N1_1 -175.95(17) . . . . ?
C3_1 C2_1 C1_1 C6_1 -0.8(3) . . . . ?
C3_1 C2_1 C7_1 N2_1 -174.16(17) . . . . ?
C3_1 C2_1 C7_1 C9_1 9.1(3) . . . . ?
C7_1 N2_1 N3_1 C10_1 0.88(18) . . . . ?
C7_1 N2_1 C8_1 N1_1 -27.6(2) . . . . ?
C7_1 N2_1 C8_1 C11_1 98.40(19) . . . . ?
C7_1 C2_1 C1_1 N1_1 1.2(2) . . . . ?
C7_1 C2_1 C1_1 C6_1 176.31(16) . . . . ?
C7_1 C2_1 C3_1 C4_1 -175.06(18) . . . . ?
C7_1 C9_1 C10_1 N3_1 -0.43(19) . . . . ?
C7_1 C9_1 C10_1 C17_1 178.60(16) . . . . ?
C8_1 N2_1 N3_1 C10_1 176.02(14) . . . . ?
C8_1 N2_1 C7_1 C2_1 6.4(2) . . . . ?
C8_1 N2_1 C7_1 C9_1 -175.98(15) . . . . ?
C8_1 N1_1 C1_1 C2_1 -27.4(3) . . . . ?
C8_1 N1_1 C1_1 C6_1 157.58(17) . . . . ?
C8_1 C11_1 C12_1 C13_1 179.95(17) . . . . ?
C8_1 C11_1 C16_1 C15_1 -179.50(18) . . . . ?
C9_1 C10_1 C17_1 C22_1 -7.9(3) . . . . ?
C9_1 C10_1 C17_1 C18_1 173.21(18) . . . . ?
C10_1 C17_1 C22_1 C21_1 -178.02(16) . . . . ?
C10_1 C17_1 C18_1 C19_1 177.52(18) . . . . ?
C11_1 C12_1 C13_1 C14_1 -0.4(3) . . . . ?
C12_1 C11_1 C16_1 C15_1 -0.5(3) . . . . ?
C12_1 C13_1 C14_1 C15_1 -0.6(4) . . . . ?
C13_1 C14_1 C15_1 C16_1 1.0(4) . . . . ?
C14_1 C15_1 C16_1 C11_1 -0.4(3) . . . . ?
C16_1 C11_1 C12_1 C13_1 1.0(3) . . . . ?
C17_1 C22_1 C21_1 C20_1 0.4(3) . . . . ?
C22_1 C17_1 C18_1 C19_1 -1.4(3) . . . . ?
C22_1 C21_1 C20_1 O1_1 179.05(18) . . . . ?
C22_1 C21_1 C20_1 C19_1 -1.2(3) . . . . ?
C21_1 C20_1 C19_1 C18_1 0.7(3) . . . . ?
C20_1 C19_1 C18_1 C17_1 0.6(3) . . . . ?
C18_1 C17_1 C22_1 C21_1 0.9(3) . . . . ?
C23_1 O1_1 C20_1 C21_1 -8.0(3) . . . . ?
C23_1 O1_1 C20_1 C19_1 172.3(2) . . . . ?
O1_2 C20_2 C21_2 C22_2 179.1(2) . . . . ?
N2_2 N3_2 C10_2 C9_2 0.95(18) . . . . ?
N2_2 N3_2 C10_2 C17_2 -175.73(14) . . . . ?
N2_2 C8_2 C11_2 C12_2 47.8(2) . . . . ?
N2_2 C8_2 C11_2 C16_2 -130.31(17) . . . . ?
N2_2 C7_2 C9_2 C10_2 -0.83(19) . . . . ?
N3_2 N2_2 C8_2 N1_2 -155.70(14) . . . . ?
N3_2 N2_2 C8_2 C11_2 76.3(2) . . . . ?
N3_2 N2_2 C7_2 C2_2 178.40(14) . . . . ?
N3_2 N2_2 C7_2 C9_2 1.53(19) . . . . ?
N3_2 C10_2 C9_2 C7_2 -0.1(2) . . . . ?
N3_2 C10_2 C17_2 C18_2 -0.2(3) . . . . ?
N3_2 C10_2 C17_2 C22_2 177.67(16) . . . . ?
C2_2 C3_2 C4_2 C5_2 0.8(3) . . . . ?
C2_2 C1_2 N1_2 C8_2 31.1(3) . . . . ?
C2_2 C7_2 C9_2 C10_2 -176.84(19) . . . . ?
C3_2 C2_2 C1_2 C6_2 0.5(3) . . . . ?
C3_2 C2_2 C1_2 N1_2 175.02(17) . . . . ?
C3_2 C2_2 C7_2 N2_2 173.37(17) . . . . ?
C3_2 C2_2 C7_2 C9_2 -11.0(3) . . . . ?
C3_2 C4_2 C5_2 C6_2 0.3(4) . . . . ?
C4_2 C5_2 C6_2 C1_2 -0.9(3) . . . . ?
C5_2 C6_2 C1_2 C2_2 0.5(3) . . . . ?
C5_2 C6_2 C1_2 N1_2 -173.84(19) . . . . ?
C6_2 C1_2 N1_2 C8_2 -154.54(18) . . . . ?
C1_2 C2_2 C3_2 C4_2 -1.2(3) . . . . ?
C1_2 C2_2 C7_2 N2_2 -8.8(2) . . . . ?
C1_2 C2_2 C7_2 C9_2 166.8(2) . . . . ?
C1_2 N1_2 C8_2 N2_2 -41.4(2) . . . . ?
C1_2 N1_2 C8_2 C11_2 84.0(2) . . . . ?
N1_2 C8_2 C11_2 C12_2 -74.2(2) . . . . ?
N1_2 C8_2 C11_2 C16_2 107.64(19) . . . . ?
C8_2 N2_2 N3_2 C10_2 -176.70(14) . . . . ?
C8_2 N2_2 C7_2 C2_2 -6.8(2) . . . . ?
C8_2 N2_2 C7_2 C9_2 176.32(15) . . . . ?
C8_2 C11_2 C12_2 C13_2 -178.54(19) . . . . ?
C8_2 C11_2 C16_2 C15_2 178.73(16) . . . . ?
C7_2 N2_2 N3_2 C10_2 -1.55(18) . . . . ?
C7_2 N2_2 C8_2 N1_2 29.8(2) . . . . ?
C7_2 N2_2 C8_2 C11_2 -98.2(2) . . . . ?
C7_2 C2_2 C3_2 C4_2 176.55(18) . . . . ?
C7_2 C2_2 C1_2 C6_2 -177.39(17) . . . . ?
C7_2 C2_2 C1_2 N1_2 -2.9(3) . . . . ?
C10_2 C17_2 C18_2 C19_2 178.2(2) . . . . ?
C10_2 C17_2 C22_2 C21_2 -178.53(18) . . . . ?
C9_2 C10_2 C17_2 C18_2 -176.10(19) . . . . ?
C9_2 C10_2 C17_2 C22_2 1.8(3) . . . . ?
C11_2 C12_2 C13_2 C14_2 0.0(3) . . . . ?
C12_2 C11_2 C16_2 C15_2 0.6(3) . . . . ?
C12_2 C13_2 C14_2 C15_2 0.3(3) . . . . ?
C13_2 C14_2 C15_2 C16_2 -0.1(3) . . . . ?
C14_2 C15_2 C16_2 C11_2 -0.3(3) . . . . ?
C16_2 C11_2 C12_2 C13_2 -0.4(3) . . . . ?
C17_2 C10_2 C9_2 C7_2 176.07(17) . . . . ?
C17_2 C18_2 C19_2 C20_2 0.5(4) . . . . ?
C18_2 C17_2 C22_2 C21_2 -0.6(3) . . . . ?
C18_2 C19_2 C20_2 O1_2 -179.6(2) . . . . ?
C18_2 C19_2 C20_2 C21_2 -0.8(4) . . . . ?
C19_2 C20_2 C21_2 C22_2 0.3(3) . . . . ?
C20_2 C21_2 C22_2 C17_2 0.3(3) . . . . ?
C22_2 C17_2 C18_2 C19_2 0.2(3) . . . . ?
C23_2 O1_2 C20_2 C19_2 -169.3(2) . . . . ?
C23_2 O1_2 C20_2 C21_2 11.9(4) . . . . ?


_olex2_exptl_crystal_mounting_method 
'A fine quality crystal was isolated and loaded on 0.3 mm nylon cryloop using paratone oil and the data was collected at room temperature'
_olex2_submission_original_sample_id 3l
_olex2_submission_special_instructions 'No special instructions were received'
