#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:29:08 +0100 (Sun 04 de Feb de 2024) $
#$Revision: 289625 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/97/7159726.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7159726
loop_
_publ_author_name
'Sudarshana, K. A.'
'Sarma, Manas Jyoti'
'Radhakrishnan, Mydhili'
'Chakravarty, Sumana'
'Srihari, Pabbaraja'
'Mehta, Goverdhan'
_publ_section_title
;
 A protocol for directly accessing geminal C-4 diarylated
 pyrazol-5(4H)-ones via tandem C-H aryne insertion and their
 inceptive neurobiological evaluation.
;
_journal_issue                   4
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              714
_journal_page_last               719
_journal_paper_doi               10.1039/d3ob01932b
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C22 H18 N2 O'
_chemical_formula_sum            'C22 H18 N2 O'
_chemical_formula_weight         326.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-05-30 deposited with the CCDC.	2023-12-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.4620(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9291(3)
_cell_length_b                   8.5789(2)
_cell_length_c                   15.4251(3)
_cell_measurement_reflns_used    6890
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.92
_cell_measurement_theta_min      2.71
_cell_volume                     1748.38(7)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21077
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.697
_diffrn_reflns_theta_min         2.722
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         5395
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0598
_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)+(0.0579P)²+0.3634P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1561
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2877
_reflns_number_total             5395
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01932b2.cif
_cod_data_source_block           KA935_0m
_cod_depositor_comments
'Adding full bibliography for 7159724--7159726.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159726
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.988
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'
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 0.33736(13) 0.4538(2) 0.82126(11) 0.0496(4) Uani 1 1 d . . . . .
C2 C 0.35040(12) 0.61616(18) 0.81236(10) 0.0435(4) Uani 1 1 d . . . . .
C3 C 0.25548(12) 0.66695(18) 0.76443(10) 0.0428(4) Uani 1 1 d . . . . .
C4 C 0.41165(16) 0.3358(2) 0.87345(14) 0.0711(6) Uani 1 1 d . . . . .
H4A H 0.376278 0.244007 0.882092 0.107 Uiso 1 1 calc R U . . .
H4B H 0.449631 0.377966 0.931890 0.107 Uiso 1 1 calc R U . . .
H4C H 0.456931 0.309199 0.840025 0.107 Uiso 1 1 calc R U . . .
C5 C 0.44385(12) 0.70787(19) 0.84200(10) 0.0457(4) Uani 1 1 d . . . . .
C6 C 0.53306(13) 0.6462(2) 0.83437(13) 0.0589(5) Uani 1 1 d . . . . .
H6 H 0.533118 0.545828 0.811570 0.071 Uiso 1 1 calc R U . . .
C7 C 0.62101(15) 0.7310(3) 0.85992(15) 0.0712(6) Uani 1 1 d . . . . .
H7 H 0.680064 0.687641 0.854572 0.085 Uiso 1 1 calc R U . . .
C8 C 0.62239(16) 0.8788(3) 0.89320(15) 0.0712(6) Uani 1 1 d . . . . .
H8 H 0.682201 0.935942 0.910666 0.085 Uiso 1 1 calc R U . . .
C9 C 0.53516(16) 0.9424(2) 0.90070(14) 0.0687(5) Uani 1 1 d . . . . .
H9 H 0.535794 1.043228 0.922972 0.082 Uiso 1 1 calc R U . . .
C10 C 0.44648(14) 0.8579(2) 0.87547(12) 0.0575(5) Uani 1 1 d . . . . .
H10 H 0.387766 0.902190 0.881013 0.069 Uiso 1 1 calc R U . . .
C11 C 0.21341(11) 0.86234(17) 0.65108(10) 0.0399(3) Uani 1 1 d . . . . .
C12 C 0.27645(13) 0.8067(2) 0.60584(11) 0.0509(4) Uani 1 1 d . . . . .
H12 H 0.324616 0.730951 0.632171 0.061 Uiso 1 1 calc R U . . .
C13 C 0.26691(16) 0.8654(2) 0.52062(12) 0.0654(5) Uani 1 1 d . . . . .
H13 H 0.309173 0.828969 0.488952 0.078 Uiso 1 1 calc R U . . .
C14 C 0.19616(17) 0.9764(3) 0.48190(12) 0.0701(6) Uani 1 1 d . . . . .
H14 H 0.190196 1.014765 0.424029 0.084 Uiso 1 1 calc R U . . .
C15 C 0.13418(15) 1.0312(2) 0.52804(13) 0.0648(5) Uani 1 1 d . . . . .
H15 H 0.086224 1.107232 0.501622 0.078 Uiso 1 1 calc R U . . .
C16 C 0.14243(13) 0.9742(2) 0.61381(12) 0.0529(4) Uani 1 1 d . . . . .
H16 H 0.100490 1.011245 0.645641 0.063 Uiso 1 1 calc R U . . .
C17 C 0.08718(12) 0.5361(2) 0.69405(11) 0.0480(4) Uani 1 1 d . . . . .
C18 C 0.02083(14) 0.6428(2) 0.70917(13) 0.0639(5) Uani 1 1 d . . . . .
H18 H 0.043952 0.722888 0.751265 0.077 Uiso 1 1 calc R U . . .
C19 C -0.08082(16) 0.6293(3) 0.66083(16) 0.0787(6) Uani 1 1 d . . . . .
H19 H -0.126634 0.700779 0.670368 0.094 Uiso 1 1 calc R U . . .
C20 C -0.11451(17) 0.5116(3) 0.59913(16) 0.0833(7) Uani 1 1 d . . . . .
H20 H -0.183154 0.502807 0.567060 0.100 Uiso 1 1 calc R U . . .
C21 C -0.04743(18) 0.4065(3) 0.58437(15) 0.0803(6) Uani 1 1 d . . . . .
H21 H -0.070624 0.326641 0.542103 0.096 Uiso 1 1 calc R U . . .
C22 C 0.05376(15) 0.4183(2) 0.63163(13) 0.0635(5) Uani 1 1 d . . . . .
H22 H 0.099379 0.347078 0.621456 0.076 Uiso 1 1 calc R U . . .
N1 N 0.19187(10) 0.54346(15) 0.74444(9) 0.0462(3) Uani 1 1 d . . . . .
N2 N 0.24267(11) 0.41003(16) 0.78011(10) 0.0521(4) Uani 1 1 d . . . . .
O1 O 0.22015(8) 0.81318(12) 0.73888(7) 0.0472(3) Uani 1 1 d . . . . .
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'
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
N2 C1 C2 111.77(14) . . ?
N2 C1 C4 118.87(16) . . ?
C2 C1 C4 129.23(16) . . ?
C3 C2 C1 103.55(14) . . ?
C3 C2 C5 127.58(15) . . ?
C1 C2 C5 128.77(14) . . ?
N1 C3 O1 120.38(14) . . ?
N1 C3 C2 109.00(14) . . ?
O1 C3 C2 130.60(15) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C5 C6 117.87(17) . . ?
C10 C5 C2 122.16(15) . . ?
C6 C5 C2 119.94(15) . . ?
C7 C6 C5 121.00(18) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C6 120.38(19) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 119.6(2) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C10 120.4(2) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C5 120.70(18) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
C16 C11 C12 121.71(15) . . ?
C16 C11 O1 116.01(13) . . ?
C12 C11 O1 122.24(14) . . ?
C11 C12 C13 118.47(17) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C14 C13 C12 120.80(17) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 120.04(17) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.21(18) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 118.77(17) . . ?
C11 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C22 C17 C18 120.91(17) . . ?
C22 C17 N1 118.59(15) . . ?
C18 C17 N1 120.48(16) . . ?
C17 C18 C19 118.9(2) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C20 C19 C18 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.1(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 120.3(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 119.4(2) . . ?
C21 C22 H22 120.3 . . ?
C17 C22 H22 120.3 . . ?
C3 N1 N2 110.24(13) . . ?
C3 N1 C17 130.14(13) . . ?
N2 N1 C17 119.61(13) . . ?
C1 N2 N1 105.42(13) . . ?
C3 O1 C11 117.91(11) . . ?
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 N2 1.324(2) . ?
C1 C2 1.417(2) . ?
C1 C4 1.489(2) . ?
C2 C3 1.366(2) . ?
C2 C5 1.465(2) . ?
C3 N1 1.353(2) . ?
C3 O1 1.3595(18) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C10 1.383(2) . ?
C5 C6 1.390(2) . ?
C6 C7 1.371(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.366(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.370(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C16 1.367(2) . ?
C11 C12 1.369(2) . ?
C11 O1 1.3929(17) . ?
C12 C13 1.374(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.365(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.365(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.371(3) . ?
C17 C18 1.372(2) . ?
C17 N1 1.420(2) . ?
C18 C19 1.380(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.365(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.368(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.370(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
N1 N2 1.3664(18) . ?
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
N2 C1 C2 C3 1.36(17) . . . . ?
C4 C1 C2 C3 -174.40(17) . . . . ?
N2 C1 C2 C5 -175.19(14) . . . . ?
C4 C1 C2 C5 9.0(3) . . . . ?
C1 C2 C3 N1 -1.51(16) . . . . ?
C5 C2 C3 N1 175.09(14) . . . . ?
C1 C2 C3 O1 176.75(15) . . . . ?
C5 C2 C3 O1 -6.6(2) . . . . ?
C3 C2 C5 C10 40.2(2) . . . . ?
C1 C2 C5 C10 -144.07(17) . . . . ?
C3 C2 C5 C6 -137.91(17) . . . . ?
C1 C2 C5 C6 37.9(2) . . . . ?
C10 C5 C6 C7 0.5(3) . . . . ?
C2 C5 C6 C7 178.67(16) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C8 C9 C10 C5 -0.2(3) . . . . ?
C6 C5 C10 C9 -0.3(2) . . . . ?
C2 C5 C10 C9 -178.41(16) . . . . ?
C16 C11 C12 C13 -0.3(3) . . . . ?
O1 C11 C12 C13 -177.81(15) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C12 C11 C16 C15 0.4(3) . . . . ?
O1 C11 C16 C15 178.05(15) . . . . ?
C14 C15 C16 C11 -0.1(3) . . . . ?
C22 C17 C18 C19 0.5(3) . . . . ?
N1 C17 C18 C19 -178.11(16) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C22 0.3(4) . . . . ?
C20 C21 C22 C17 0.2(3) . . . . ?
C18 C17 C22 C21 -0.6(3) . . . . ?
N1 C17 C22 C21 178.01(17) . . . . ?
O1 C3 N1 N2 -177.24(12) . . . . ?
C2 C3 N1 N2 1.23(16) . . . . ?
O1 C3 N1 C17 3.4(2) . . . . ?
C2 C3 N1 C17 -178.09(14) . . . . ?
C22 C17 N1 C3 135.75(17) . . . . ?
C18 C17 N1 C3 -45.7(2) . . . . ?
C22 C17 N1 N2 -43.5(2) . . . . ?
C18 C17 N1 N2 135.08(17) . . . . ?
C2 C1 N2 N1 -0.65(17) . . . . ?
C4 C1 N2 N1 175.60(15) . . . . ?
C3 N1 N2 C1 -0.34(16) . . . . ?
C17 N1 N2 C1 179.06(13) . . . . ?
N1 C3 O1 C11 -85.58(17) . . . . ?
C2 C3 O1 C11 96.32(18) . . . . ?
C16 C11 O1 C3 153.64(14) . . . . ?
C12 C11 O1 C3 -28.7(2) . . . . ?
