Visible light-induced organo-photocatalyzed route to synthesize substituted pyrazoles.
Pal, Koustav; Srinivasu, Vinjamuri; Biswas, Sourabh; Sureshkumar, Devarajulu; Organic & biomolecular chemistry 22 (2024) 2384–2388; doi:10.1039/d4ob00248b

data_7159825
_publ_section_title
;
 Visible light-induced organo-photocatalyzed route to synthesize
 substituted pyrazoles.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2384
_journal_page_last               2388
_journal_paper_doi               10.1039/d4ob00248b
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         '0.154(C10 H9 N3)'
_chemical_formula_sum            'C1.54 H1.38 N0.46'
_chemical_formula_weight         26.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-14
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-07-20 deposited with the CCDC.	2024-02-29 downloaded from the CCDC.
;
_cell_angle_alpha                102.832(4)
_cell_angle_beta                 92.959(3)
_cell_angle_gamma                114.223(4)
_cell_formula_units_Z            13
_cell_length_a                   6.3402(3)
_cell_length_b                   7.4033(3)
_cell_length_c                   10.8259(4)
_cell_measurement_reflns_used    4020
_cell_measurement_temperature    107(4)
_cell_measurement_theta_max      67.6350
_cell_measurement_theta_min      4.2110
_cell_volume                     445.98(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      107(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     28.00 105.00   0.50    0.25    --   96.35 -77.00 150.00  154
  2  \w     28.00 105.00   0.50    0.25    --   96.35 -77.00  30.00  154
  3  \w    -29.00  31.00   0.50    0.20    --   40.58 -25.00   0.00  120
  4  \w    -26.00  57.00   0.50    0.20    --   40.58 -50.00  30.00  166
  5  \w    -35.00  24.00   0.50    0.20    --   40.58 -12.00 150.00  118
  6  \w     28.00  68.00   0.50    0.25    --   96.35 -59.00 150.00   80
  7  \w     29.00  83.00   0.50    0.25    --   96.35 -68.00  90.00  108
  8  \w     28.00  68.00   0.50    0.25    --   96.35 -59.00 -30.00   80
  9  \w     28.00  68.00   0.50    0.25    --   96.35 -59.00 -60.00   80
 10  \w     29.00  83.00   0.50    0.25    --   96.35 -68.00 -90.00  108
 11  \w     30.00  57.00   0.50    0.25    --   96.35 -50.00 -90.00   54
 12  \w     28.00  68.00   0.50    0.25    --   96.35 -59.00-180.00   80
 13  \w     26.00 127.00   0.50    0.25    --   96.35 -87.00 -90.00  202
 14  \w     44.00 127.00   0.50    0.25    --   96.35-145.00-120.00  166
 15  \w     39.00 119.00   0.50    0.25    --   96.35-135.00 -64.00  160
 16  \w     33.00 110.00   0.50    0.25    --   96.35-117.00 -90.00  154
 17  \w     33.00 110.00   0.50    0.25    --   96.35-117.00   0.00  154
 18  \w     39.00 119.00   0.50    0.25    --   96.35-134.00 114.00  160
 19  \w     39.00  96.00   0.50    0.20    --   40.58-134.00 114.00  114
 20  \w     81.00 167.00   0.50    0.25    --   96.35  25.00 -60.00  172
 21  \w     77.00 163.00   0.50    0.25    --   96.35  50.00   0.00  172
 22  \w     70.00 165.00   0.50    0.25    --   96.35  77.00-120.00  190
 23  \w     70.00 165.00   0.50    0.25    --   96.35  77.00 -60.00  190
 24  \w     83.00 164.00   0.50    0.25    --   96.35  33.00-120.00  162
 25  \w     72.00 164.00   0.50    0.25    --   96.35  68.00  60.00  184
 26  \w     70.00 165.00   0.50    0.25    --   96.35  77.00 150.00  190
 27  \w     83.00 164.00   0.50    0.25    --   96.35  33.00 120.00  162
 28  \w     81.00 167.00   0.50    0.25    --   96.35  25.00  60.00  172
 29  \w     81.00 167.00   0.50    0.25    --   96.35  25.00-180.00  172
 30  \w     99.00 160.00   0.50    0.25    --   96.35 117.00-150.00  122
 31  \w     81.00 165.00   0.50    0.25    --   96.35 145.00-120.00  168
 32  \w     89.00 162.00   0.50    0.25    --   96.35 134.00-179.00  146
 33  \w     88.00 164.00   0.50    0.25    --   96.35 135.00   0.00  152
 34  \w     18.00 108.00   0.50    0.20    --   40.58  64.00 -90.00  180
 35  \w     14.00 109.00   0.50    0.20    --   40.58  77.00-180.00  190
 36  \w     14.00 109.00   0.50    0.20    --   40.58  77.00 120.00  190
 37  \w    -94.00 -18.00   0.50    0.20    --  -40.58 135.00   0.00  152
 38  \w    -93.00 -17.00   0.50    0.20    --  -40.58 134.00-179.00  152
 39  \w    -93.00 -17.00   0.50    0.25    --  -82.50 134.00-179.00  152
 40  \w    -57.00 -16.00   0.50    0.25    --  -82.50  50.00-120.00   82
 41  \w    -47.00 -15.00   0.50    0.25    --  -82.50  42.00-180.00   64
 42  \w    -47.00 -15.00   0.50    0.25    --  -82.50  42.00 -30.00   64
 43  \w    -47.00 -15.00   0.50    0.25    --  -82.50  42.00   0.00   64
 44  \w    -47.00 -15.00   0.50    0.25    --  -82.50  42.00  60.00   64
 45  \w    -43.00  26.00   0.50    0.20    --  -40.58  38.00   0.00  138
 46  \w    -43.00  26.00   0.50    0.20    --  -40.58  38.00  30.00  138
 47  \w    -24.00  35.00   0.50    0.20    --  -40.58  12.00 -60.00  118
 48  \w    -24.00  35.00   0.50    0.20    --  -40.58  12.00-150.00  118
 49  \w    -24.00  35.00   0.50    0.20    --  -40.58  12.00-120.00  118
 50  \w   -108.00 -17.00   0.50    0.20    --  -40.58 -64.00 -30.00  182
 51  \w   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00  30.00  190
 52  \w   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00  60.00  190
 53  \w   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00  90.00  190
 54  \w   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00-180.00  190
 55  \w   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00-120.00  190
 56  \w   -108.00 -17.00   0.50    0.20    --  -40.58 -64.00 -90.00  182
 57  \w   -151.00 -55.00   0.50    0.25    --  -82.50 -77.00  30.00  192
 58  \w   -151.00 -55.00   0.50    0.25    --  -82.50 -77.00  90.00  192
 59  \w   -151.00 -61.00   0.50    0.25    --  -82.50 -59.00 120.00  180
 60  \w   -150.00 -69.00   0.50    0.25    --  -82.50 -33.00 150.00  162
 61  \w   -151.00 -55.00   0.50    0.25    --  -82.50 -77.00   0.00  192
 62  \w   -151.00 -55.00   0.50    0.25    --  -82.50 -77.00-150.00  192
 63  \w   -151.00 -55.00   0.50    0.25    --  -82.50 -77.00 -90.00  192
 64  \w   -150.00 -66.00   0.50    0.25    --  -82.50-135.00 -64.00  168
 65  \w   -148.00 -67.00   0.50    0.25    --  -82.50-134.00 114.00  162
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0922119000
_diffrn_orient_matrix_UB_12      -0.0327659000
_diffrn_orient_matrix_UB_13      0.1259702000
_diffrn_orient_matrix_UB_21      -0.2311253000
_diffrn_orient_matrix_UB_22      -0.1765738000
_diffrn_orient_matrix_UB_23      -0.0774229000
_diffrn_orient_matrix_UB_31      0.1046298000
_diffrn_orient_matrix_UB_32      -0.1543211000
_diffrn_orient_matrix_UB_33      0.0012358000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7820
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.100
_diffrn_reflns_theta_min         4.243
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             180
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1604
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0432
_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/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1339
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1430
_reflns_number_total             1604
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00248b2.cif
_cod_data_source_block           skd-f-kp-137smiso-r_auto
_cod_depositor_comments          'Adding full bibliography for 7159825.cif.'
_cod_database_code               7159825
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N'
_chemical_oxdiff_usercomment     100K
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C005(H005), C006(H006), C007(H007), C009(H009), C00B(H00B), C00C(H00C)
2.b Idealised Me refined as rotating group:
 C00D(H00A,H00D,H00E)
;
_shelx_res_checksum              23264
_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 1.966
_oxdiff_exptl_absorpt_empirical_full_min 0.837