# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_4n_296k
_database_code_depnum_ccdc_archive 'CCDC 1994906'
loop_
_audit_author_name
_audit_author_address
'Hassan Allouchi'
;University
France
;


_audit_update_record             
;
2020-04-05 deposited with the CCDC.	2021-02-23 downloaded from the CCDC.
;
_publcif_datablock.id            {87fbad34-f439-41ca-bb78-cc5809cd79ab}

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            pyrazolo[3,4-c]pyrazole
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 N4 O2'
_chemical_formula_sum            'C19 H18 N4 O2'
_chemical_formula_weight         334.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.3904(8)
_cell_length_b                   19.8941(14)
_cell_length_c                   11.3675(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.409(9)
_cell_angle_gamma                90
_cell_volume                     1671.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1798
_cell_measurement_theta_min      4.094
_cell_measurement_theta_max      22.799

_exptl_crystal_description       'prism, axis [1 0 0]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_detector                 'CCD plate'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_type            'Sapphire2, large Be window'
_diffrn_detector_area_resol_mean 8.3622
_diffrn_reflns_number            11250
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.434
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_orient_matrix_UB_11      -0.0345233000
_diffrn_orient_matrix_UB_12      0.0332274000
_diffrn_orient_matrix_UB_13      0.0026410000
_diffrn_orient_matrix_UB_21      0.0080440000
_diffrn_orient_matrix_UB_22      0.0028450000
_diffrn_orient_matrix_UB_23      -0.0619488000
_diffrn_orient_matrix_UB_31      -0.0892085000
_diffrn_orient_matrix_UB_32      -0.0125855000
_diffrn_orient_matrix_UB_33      -0.0070503000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -36.00   48.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.8549   77.0000 -120.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega  -48.00    0.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.8549   77.0000 -150.0000 48

#__ type_ start__ end____ width___ exp.time_
  3 omega   -9.00   93.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -       17.7924   77.0000    0.0000 102

#__ type_ start__ end____ width___ exp.time_
  4 omega   -5.00   97.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -       17.7920   77.0000  120.0000 102
;
_reflns_number_total             3408
_reflns_number_gt                1635
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Wingx 2014.1 (L.J. Farrugia, 2012)'
_computing_publication_material  'Mercury 3.7'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0511P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3408
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1309
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1584
_refine_ls_wR_factor_gt          0.1233
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2563(3) 0.40542(12) 0.0658(2) 0.0505(7) Uani 1 1 d . . . . .
C2 C 0.2462(3) 0.51317(13) 0.1124(3) 0.0526(7) Uani 1 1 d . . . . .
C3 C 0.2516(4) 0.46333(14) 0.2842(3) 0.0652(8) Uani 1 1 d . . . . .
H3 H 0.2560 0.4301 0.3417 0.078 Uiso 1 1 calc R U . . .
C4 C 0.2459(3) 0.45045(12) 0.1618(2) 0.0542(7) Uani 1 1 d . . . . .
C5 C 0.2705(4) 0.55588(13) -0.0996(2) 0.0701(9) Uani 1 1 d . . . . .
H5A H 0.1509 0.5695 -0.1229 0.105 Uiso 1 1 calc R U . . .
H5B H 0.3311 0.5362 -0.1656 0.105 Uiso 1 1 calc R U . . .
H5C H 0.3373 0.5943 -0.0725 0.105 Uiso 1 1 calc R U . . .
C6 C 0.2624(3) 0.33194(12) 0.0645(2) 0.0503(7) Uani 1 1 d . . . . .
C7 C 0.1861(4) 0.29496(13) 0.1549(2) 0.0573(7) Uani 1 1 d . . . . .
H7 H 0.1329 0.3175 0.2175 0.069 Uiso 1 1 calc R U . . .
C8 C 0.1872(4) 0.22511(13) 0.1543(2) 0.0575(7) Uani 1 1 d . . . . .
H8 H 0.1351 0.2011 0.2156 0.069 Uiso 1 1 calc R U . . .
C9 C 0.2660(4) 0.19194(12) 0.0619(2) 0.0523(7) Uani 1 1 d . . . . .
C10 C 0.3425(4) 0.22771(13) -0.0291(2) 0.0553(7) Uani 1 1 d . . . . .
H10 H 0.3955 0.2050 -0.0915 0.066 Uiso 1 1 calc R U . . .
C11 C 0.3406(3) 0.29659(13) -0.0279(2) 0.0541(7) Uani 1 1 d . . . . .
H11 H 0.3924 0.3201 -0.0897 0.065 Uiso 1 1 calc R U . . .
C12 C 0.2092(5) 0.08317(14) 0.1456(3) 0.0957(12) Uani 1 1 d . . . . .
H12A H 0.2686 0.0950 0.2181 0.144 Uiso 1 1 calc R U . . .
H12B H 0.2307 0.0366 0.1285 0.144 Uiso 1 1 calc R U . . .
H12C H 0.0814 0.0907 0.1527 0.144 Uiso 1 1 calc R U . . .
C13 C 0.2422(4) 0.63218(12) 0.1933(2) 0.0524(7) Uani 1 1 d . . . . .
C14 C 0.1457(4) 0.66487(13) 0.1074(2) 0.0592(8) Uani 1 1 d . . . . .
H14 H 0.0793 0.6401 0.0528 0.071 Uiso 1 1 calc R U . . .
C15 C 0.1458(4) 0.73462(13) 0.1007(2) 0.0604(8) Uani 1 1 d . . . . .
H15 H 0.0831 0.7565 0.0407 0.073 Uiso 1 1 calc R U . . .
C16 C 0.2396(4) 0.77079(13) 0.1838(2) 0.0546(7) Uani 1 1 d . . . . .
C17 C 0.3307(4) 0.73787(14) 0.2738(2) 0.0604(7) Uani 1 1 d . . . . .
H17 H 0.3899 0.7626 0.3319 0.072 Uiso 1 1 calc R U . . .
C18 C 0.3340(4) 0.66912(13) 0.2776(2) 0.0569(7) Uani 1 1 d . . . . .
H18 H 0.3981 0.6472 0.3370 0.068 Uiso 1 1 calc R U . . .
C19 C 0.1816(5) 0.87590(14) 0.0895(3) 0.0969(12) Uani 1 1 d . . . . .
H19A H 0.2436 0.8620 0.0197 0.145 Uiso 1 1 calc R U . . .
H19B H 0.2013 0.9231 0.1021 0.145 Uiso 1 1 calc R U . . .
H19C H 0.0544 0.8675 0.0804 0.145 Uiso 1 1 calc R U . . .
N1 N 0.2629(3) 0.43960(10) -0.0346(2) 0.0595(6) Uani 1 1 d . . . . .
N2 N 0.2587(3) 0.50683(10) -0.0055(2) 0.0599(6) Uani 1 1 d . . . . .
N3 N 0.2470(3) 0.56088(10) 0.1980(2) 0.0573(6) Uani 1 1 d . . . . .
N4 N 0.2496(3) 0.52859(11) 0.3063(2) 0.0695(7) Uani 1 1 d . . . . .
O1 O 0.2786(3) 0.12357(9) 0.05269(16) 0.0692(6) Uani 1 1 d . . . . .
O2 O 0.2485(3) 0.83952(9) 0.18672(18) 0.0756(6) Uani 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
C1 N1 1.330(3) . ?
C1 C4 1.415(3) . ?
C1 C6 1.463(3) . ?
C2 N2 1.351(3) . ?
C2 N3 1.359(3) . ?
C2 C4 1.368(3) . ?
C3 N4 1.323(3) . ?
C3 C4 1.415(4) . ?
C3 H3 0.9300 . ?
C5 N2 1.451(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.387(3) . ?
C6 C11 1.393(3) . ?
C7 C8 1.390(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(3) . ?
C8 H8 0.9300 . ?
C9 O1 1.367(3) . ?
C9 C10 1.381(3) . ?
C10 C11 1.370(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 O1 1.426(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.369(3) . ?
C13 C18 1.382(3) . ?
C13 N3 1.420(3) . ?
C14 C15 1.390(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(3) . ?
C15 H15 0.9300 . ?
C16 O2 1.369(3) . ?
C16 C17 1.385(3) . ?
C17 C18 1.369(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O2 1.408(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N1 N2 1.378(3) . ?
N3 N4 1.389(3) . ?

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
N1 C1 C4 109.9(2) . . ?
N1 C1 C6 120.1(2) . . ?
C4 C1 C6 130.0(2) . . ?
N2 C2 N3 140.9(2) . . ?
N2 C2 C4 108.8(2) . . ?
N3 C2 C4 110.1(2) . . ?
N4 C3 C4 111.4(2) . . ?
N4 C3 H3 124.3 . . ?
C4 C3 H3 124.3 . . ?
C2 C4 C1 105.1(2) . . ?
C2 C4 C3 103.8(2) . . ?
C1 C4 C3 150.7(3) . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C11 117.6(2) . . ?
C7 C6 C1 120.7(2) . . ?
C11 C6 C1 121.7(2) . . ?
C6 C7 C8 121.6(2) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C9 C8 C7 119.1(2) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
O1 C9 C8 124.5(2) . . ?
O1 C9 C10 115.3(2) . . ?
C8 C9 C10 120.3(2) . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C6 121.2(2) . . ?
C10 C11 H11 119.4 . . ?
C6 C11 H11 119.4 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 119.5(2) . . ?
C14 C13 N3 120.9(2) . . ?
C18 C13 N3 119.5(2) . . ?
C13 C14 C15 120.8(2) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 119.1(3) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
O2 C16 C15 124.3(3) . . ?
O2 C16 C17 115.6(3) . . ?
C15 C16 C17 120.1(2) . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C13 120.0(3) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 N1 N2 106.8(2) . . ?
C2 N2 N1 109.3(2) . . ?
C2 N2 C5 132.4(2) . . ?
N1 N2 C5 118.3(2) . . ?
C2 N3 N4 108.2(2) . . ?
C2 N3 C13 132.1(2) . . ?
N4 N3 C13 119.7(2) . . ?
C3 N4 N3 106.6(2) . . ?
C9 O1 C12 118.6(2) . . ?
C16 O2 C19 118.6(2) . . ?

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.050


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
