#------------------------------------------------------------------------------
#$Date: 2024-04-05 03:13:37 +0300 (Fri, 05 Apr 2024) $
#$Revision: 291062 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/98/7159825.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_7159825
loop_
_publ_author_name
'Pal, Koustav'
'Srinivasu, Vinjamuri'
'Biswas, Sourabh'
'Sureshkumar, Devarajulu'
_publ_section_title
;
 Visible light-induced organo-photocatalyzed route to synthesize
 substituted pyrazoles.
;
_journal_issue                   12
_journal_name_full               'Organic & 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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     28.00 105.00   0.50    0.25    --   96.35 -77.00 150.00  154
  2  ω     28.00 105.00   0.50    0.25    --   96.35 -77.00  30.00  154
  3  ω    -29.00  31.00   0.50    0.20    --   40.58 -25.00   0.00  120
  4  ω    -26.00  57.00   0.50    0.20    --   40.58 -50.00  30.00  166
  5  ω    -35.00  24.00   0.50    0.20    --   40.58 -12.00 150.00  118
  6  ω     28.00  68.00   0.50    0.25    --   96.35 -59.00 150.00   80
  7  ω     29.00  83.00   0.50    0.25    --   96.35 -68.00  90.00  108
  8  ω     28.00  68.00   0.50    0.25    --   96.35 -59.00 -30.00   80
  9  ω     28.00  68.00   0.50    0.25    --   96.35 -59.00 -60.00   80
 10  ω     29.00  83.00   0.50    0.25    --   96.35 -68.00 -90.00  108
 11  ω     30.00  57.00   0.50    0.25    --   96.35 -50.00 -90.00   54
 12  ω     28.00  68.00   0.50    0.25    --   96.35 -59.00-180.00   80
 13  ω     26.00 127.00   0.50    0.25    --   96.35 -87.00 -90.00  202
 14  ω     44.00 127.00   0.50    0.25    --   96.35-145.00-120.00  166
 15  ω     39.00 119.00   0.50    0.25    --   96.35-135.00 -64.00  160
 16  ω     33.00 110.00   0.50    0.25    --   96.35-117.00 -90.00  154
 17  ω     33.00 110.00   0.50    0.25    --   96.35-117.00   0.00  154
 18  ω     39.00 119.00   0.50    0.25    --   96.35-134.00 114.00  160
 19  ω     39.00  96.00   0.50    0.20    --   40.58-134.00 114.00  114
 20  ω     81.00 167.00   0.50    0.25    --   96.35  25.00 -60.00  172
 21  ω     77.00 163.00   0.50    0.25    --   96.35  50.00   0.00  172
 22  ω     70.00 165.00   0.50    0.25    --   96.35  77.00-120.00  190
 23  ω     70.00 165.00   0.50    0.25    --   96.35  77.00 -60.00  190
 24  ω     83.00 164.00   0.50    0.25    --   96.35  33.00-120.00  162
 25  ω     72.00 164.00   0.50    0.25    --   96.35  68.00  60.00  184
 26  ω     70.00 165.00   0.50    0.25    --   96.35  77.00 150.00  190
 27  ω     83.00 164.00   0.50    0.25    --   96.35  33.00 120.00  162
 28  ω     81.00 167.00   0.50    0.25    --   96.35  25.00  60.00  172
 29  ω     81.00 167.00   0.50    0.25    --   96.35  25.00-180.00  172
 30  ω     99.00 160.00   0.50    0.25    --   96.35 117.00-150.00  122
 31  ω     81.00 165.00   0.50    0.25    --   96.35 145.00-120.00  168
 32  ω     89.00 162.00   0.50    0.25    --   96.35 134.00-179.00  146
 33  ω     88.00 164.00   0.50    0.25    --   96.35 135.00   0.00  152
 34  ω     18.00 108.00   0.50    0.20    --   40.58  64.00 -90.00  180
 35  ω     14.00 109.00   0.50    0.20    --   40.58  77.00-180.00  190
 36  ω     14.00 109.00   0.50    0.20    --   40.58  77.00 120.00  190
 37  ω    -94.00 -18.00   0.50    0.20    --  -40.58 135.00   0.00  152
 38  ω    -93.00 -17.00   0.50    0.20    --  -40.58 134.00-179.00  152
 39  ω    -93.00 -17.00   0.50    0.25    --  -82.50 134.00-179.00  152
 40  ω    -57.00 -16.00   0.50    0.25    --  -82.50  50.00-120.00   82
 41  ω    -47.00 -15.00   0.50    0.25    --  -82.50  42.00-180.00   64
 42  ω    -47.00 -15.00   0.50    0.25    --  -82.50  42.00 -30.00   64
 43  ω    -47.00 -15.00   0.50    0.25    --  -82.50  42.00   0.00   64
 44  ω    -47.00 -15.00   0.50    0.25    --  -82.50  42.00  60.00   64
 45  ω    -43.00  26.00   0.50    0.20    --  -40.58  38.00   0.00  138
 46  ω    -43.00  26.00   0.50    0.20    --  -40.58  38.00  30.00  138
 47  ω    -24.00  35.00   0.50    0.20    --  -40.58  12.00 -60.00  118
 48  ω    -24.00  35.00   0.50    0.20    --  -40.58  12.00-150.00  118
 49  ω    -24.00  35.00   0.50    0.20    --  -40.58  12.00-120.00  118
 50  ω   -108.00 -17.00   0.50    0.20    --  -40.58 -64.00 -30.00  182
 51  ω   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00  30.00  190
 52  ω   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00  60.00  190
 53  ω   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00  90.00  190
 54  ω   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00-180.00  190
 55  ω   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00-120.00  190
 56  ω   -108.00 -17.00   0.50    0.20    --  -40.58 -64.00 -90.00  182
 57  ω   -151.00 -55.00   0.50    0.25    --  -82.50 -77.00  30.00  192
 58  ω   -151.00 -55.00   0.50    0.25    --  -82.50 -77.00  90.00  192
 59  ω   -151.00 -61.00   0.50    0.25    --  -82.50 -59.00 120.00  180
 60  ω   -150.00 -69.00   0.50    0.25    --  -82.50 -33.00 150.00  162
 61  ω   -151.00 -55.00   0.50    0.25    --  -82.50 -77.00   0.00  192
 62  ω   -151.00 -55.00   0.50    0.25    --  -82.50 -77.00-150.00  192
 63  ω   -151.00 -55.00   0.50    0.25    --  -82.50 -77.00 -90.00  192
 64  ω   -150.00 -66.00   0.50    0.25    --  -82.50-135.00 -64.00  168
 65  ω   -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       'ω 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/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/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 > 2σ(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
_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.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
N001 N 0.63153(16) 0.25212(13) 0.44402(9) 0.0253(3) Uani 1 1 d . . . . .
N002 N 0.43443(15) 0.23640(13) 0.47188(9) 0.0249(3) Uani 1 1 d . . . . .
N003 N 0.93695(16) 0.22814(14) 0.04899(8) 0.0347(3) Uani 1 1 d . . . . .
C004 C 0.41890(18) 0.25345(15) 0.60448(10) 0.0235(3) Uani 1 1 d . . . . .
C005 C 0.60199(19) 0.28482(15) 0.69707(10) 0.0255(3) Uani 1 1 d . . . . .
H005 H 0.747662 0.295407 0.672870 0.031 Uiso 1 1 calc R U . . .
C006 C 0.17484(19) 0.25288(16) 0.76738(11) 0.0273(3) Uani 1 1 d . . . . .
H006 H 0.029500 0.242674 0.791917 0.033 Uiso 1 1 calc R U . . .
C007 C 0.85366(19) 0.25061(15) 0.28110(10) 0.0270(3) Uani 1 1 d . . . . .
H007 H 0.973551 0.271814 0.346624 0.032 Uiso 1 1 calc R U . . .
C008 C 0.64396(19) 0.23391(15) 0.31167(10) 0.0241(3) Uani 1 1 d . . . . .
C009 C 0.57035(18) 0.30035(15) 0.82380(10) 0.0267(3) Uani 1 1 d . . . . .
H009 H 0.694616 0.322463 0.886855 0.032 Uiso 1 1 calc R U . . .
C00A C 0.89917(18) 0.23707(16) 0.15229(10) 0.0278(3) Uani 1 1 d . . . . .
C00B C 0.35566(19) 0.28352(15) 0.85899(10) 0.0267(3) Uani 1 1 d . . . . .
H00B H 0.333532 0.293102 0.945919 0.032 Uiso 1 1 calc R U . . .
C00C C 0.20472(18) 0.23700(15) 0.64004(10) 0.0258(3) Uani 1 1 d . . . . .
H00C H 0.079987 0.215046 0.577354 0.031 Uiso 1 1 calc R U . . .
C00D C 0.44150(18) 0.20136(16) 0.21870(10) 0.0277(3) Uani 1 1 d . . . . .
H00A H 0.301055 0.084635 0.227189 0.041 Uiso 1 1 calc R U . . .
H00D H 0.475717 0.172778 0.131125 0.041 Uiso 1 1 calc R U . . .
H00E H 0.414674 0.325263 0.236675 0.041 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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
N002 N001 C008 113.02(10) . . ?
N001 N002 C004 113.67(10) . . ?
C005 C004 N002 124.14(10) . . ?
C00C C004 N002 115.85(10) . . ?
C00C C004 C005 120.00(10) . . ?
C004 C005 H005 120.1 . . ?
C009 C005 C004 119.89(10) . . ?
C009 C005 H005 120.1 . . ?
C00B C006 H006 119.8 . . ?
C00B C006 C00C 120.39(10) . . ?
C00C C006 H006 119.8 . . ?
C008 C007 H007 119.3 . . ?
C008 C007 C00A 121.39(10) . . ?
C00A C007 H007 119.3 . . ?
N001 C008 C00D 121.74(9) . . ?
C007 C008 N001 113.42(10) . . ?
C007 C008 C00D 124.84(10) . . ?
C005 C009 H009 120.0 . . ?
C005 C009 C00B 119.95(10) . . ?
C00B C009 H009 120.0 . . ?
N003 C00A C007 179.36(11) . . ?
C006 C00B C009 120.12(10) . . ?
C006 C00B H00B 119.9 . . ?
C009 C00B H00B 119.9 . . ?
C004 C00C H00C 120.2 . . ?
C006 C00C C004 119.65(10) . . ?
C006 C00C H00C 120.2 . . ?
C008 C00D H00A 109.5 . . ?
C008 C00D H00D 109.5 . . ?
C008 C00D H00E 109.5 . . ?
H00A C00D H00D 109.5 . . ?
H00A C00D H00E 109.5 . . ?
H00D C00D H00E 109.5 . . ?
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
N001 N002 1.2654(13) . ?
N001 C008 1.4185(13) . ?
N002 C004 1.4251(15) . ?
N003 C00A 1.1489(13) . ?
C004 C005 1.4005(16) . ?
C004 C00C 1.3951(14) . ?
C005 H005 0.9500 . ?
C005 C009 1.3832(14) . ?
C006 H006 0.9500 . ?
C006 C00B 1.3851(16) . ?
C006 C00C 1.3868(14) . ?
C007 H007 0.9500 . ?
C007 C008 1.3495(15) . ?
C007 C00A 1.4287(14) . ?
C008 C00D 1.4913(16) . ?
C009 H009 0.9500 . ?
C009 C00B 1.3960(15) . ?
C00B H00B 0.9500 . ?
C00C H00C 0.9500 . ?
C00D H00A 0.9800 . ?
C00D H00D 0.9800 . ?
C00D H00E 0.9800 . ?
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
N001 N002 C004 C005 0.05(17) . . . . ?
N001 N002 C004 C00C -179.97(8) . . . . ?
N002 N001 C008 C007 179.97(8) . . . . ?
N002 N001 C008 C00D 0.46(15) . . . . ?
N002 C004 C005 C009 179.69(8) . . . . ?
N002 C004 C00C C006 -179.67(8) . . . . ?
C004 C005 C009 C00B 0.38(16) . . . . ?
C005 C004 C00C C006 0.31(16) . . . . ?
C005 C009 C00B C006 -0.50(16) . . . . ?
C008 N001 N002 C004 179.73(7) . . . . ?
C00A C007 C008 N001 -179.74(8) . . . . ?
C00A C007 C008 C00D -0.25(17) . . . . ?
C00B C006 C00C C004 -0.43(16) . . . . ?
C00C C004 C005 C009 -0.29(16) . . . . ?
C00C C006 C00B C009 0.53(16) . . . . ?
