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#$Date: 2023-05-05 06:17:46 +0300 (Fri, 05 May 2023) $
#$Revision: 283453 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/92/7159236.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_7159236
loop_
_publ_author_name
'Gugulothu, Kishan'
'Jatoth, Ramanna'
'Edukondalu, Peramalla'
'Vanga, Anusha'
'Matta, Raghavender'
'Shiva Kumar, K.'
_publ_section_title
;
 Synthesis of fused bis-indazoles/indazoles via a one-pot
 sequential strategy.
;
_journal_issue                   13
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2816
_journal_page_last               2821
_journal_paper_doi               10.1039/d3ob00121k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C18 H14 Cl2 N4'
_chemical_formula_sum            'C18 H14 Cl2 N4'
_chemical_formula_weight         357.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-12-10 deposited with the CCDC.	2023-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.12(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.586(1)
_cell_length_b                   9.123(1)
_cell_length_c                   15.330(1)
_cell_measurement_reflns_used    1941
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      0.941
_cell_measurement_theta_min      0.907
_cell_volume                     1620.1(2)
_computing_cell_refinement       'Bruker SHELXL'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker D8 Venture photon 100 CMOS detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.949
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11411
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.300
_diffrn_reflns_theta_min         4.662
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.407
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (G. Sheldrick, 2013)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.6243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1370
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1756
_reflns_number_total             1941
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00121k2.cif
_cod_data_source_block           datam_a
_cod_depositor_comments
'Adding full bibliography for 7159236--7159238.cif.'
_cod_original_cell_volume        1620.1(1)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7159236
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
Cl1 Cl 0.52304(3) 0.18398(4) 0.51199(2) 0.0436(2) Uani 1 1 d . . . . .
N2 N 0.62456(10) 0.75520(13) 0.71328(7) 0.0362(3) Uani 1 1 d . . . . .
N1 N 0.70072(10) 0.73782(14) 0.64880(7) 0.0386(3) Uani 1 1 d . . . . .
C5 C 0.57261(10) 0.54610(14) 0.65253(8) 0.0298(3) Uani 1 1 d . . . . .
C7 C 0.54568(11) 0.64541(15) 0.71847(8) 0.0331(3) Uani 1 1 d . . . . .
C4 C 0.66932(10) 0.61017(14) 0.61096(8) 0.0321(3) Uani 1 1 d . . . . .
C6 C 0.52524(11) 0.41207(14) 0.62296(8) 0.0320(3) Uani 1 1 d . . . . .
H6 H 0.462622 0.368842 0.649953 0.038 Uiso 1 1 calc R U . . .
C1 C 0.57621(11) 0.34917(15) 0.55261(9) 0.0324(3) Uani 1 1 d . . . . .
C3 C 0.71762(11) 0.54258(17) 0.53731(9) 0.0372(3) Uani 1 1 d . . . . .
H3 H 0.779435 0.584865 0.508818 0.045 Uiso 1 1 calc R U . . .
C2 C 0.67085(12) 0.41345(17) 0.50927(9) 0.0367(3) Uani 1 1 d . . . . .
H2 H 0.701394 0.366699 0.461003 0.044 Uiso 1 1 calc R U . . .
C18 C 0.63522(15) 0.88377(17) 0.77007(10) 0.0462(4) Uani 1 1 d . . . . .
H18A H 0.715699 0.912819 0.773843 0.055 Uiso 1 1 calc R U . . .
H18B H 0.611364 0.857156 0.828264 0.055 Uiso 1 1 calc R U . . .
C17 C 0.56356(18) 1.01379(18) 0.73852(12) 0.0567(5) Uani 1 1 d . . . . .
H17A H 0.598329 1.102353 0.762180 0.068 Uiso 1 1 calc R U . . .
H17B H 0.568832 1.019050 0.675534 0.068 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'
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 N2 C7 114.01(11) . . ?
N1 N2 C18 118.79(12) . . ?
C7 N2 C18 127.18(12) . . ?
N2 N1 C4 104.02(11) . . ?
C7 C5 C6 134.68(11) . . ?
C7 C5 C4 104.26(11) . . ?
C6 C5 C4 121.05(11) . . ?
N2 C7 C5 106.00(11) . . ?
N2 C7 C7 122.71(10) . 2_656 ?
C5 C7 C7 131.28(10) . 2_656 ?
N1 C4 C3 127.85(12) . . ?
N1 C4 C5 111.71(11) . . ?
C3 C4 C5 120.40(12) . . ?
C1 C6 C5 116.49(11) . . ?
C1 C6 H6 121.8 . . ?
C5 C6 H6 121.8 . . ?
C6 C1 C2 123.08(13) . . ?
C6 C1 Cl1 119.42(10) . . ?
C2 C1 Cl1 117.50(10) . . ?
C2 C3 C4 117.93(11) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C3 C2 C1 121.01(12) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
N2 C18 C17 113.35(13) . . ?
N2 C18 H18A 108.9 . . ?
C17 C18 H18A 108.9 . . ?
N2 C18 H18B 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C17 C17 C18 116.83(13) 2_656 . ?
C17 C17 H17A 108.1 2_656 . ?
C18 C17 H17A 108.1 . . ?
C17 C17 H17B 108.1 2_656 . ?
C18 C17 H17B 108.1 . . ?
H17A C17 H17B 107.3 . . ?
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
Cl1 C1 1.7388(14) . ?
N2 N1 1.3474(17) . ?
N2 C7 1.3593(17) . ?
N2 C18 1.4646(18) . ?
N1 C4 1.3479(17) . ?
C5 C7 1.3973(18) . ?
C5 C6 1.4115(18) . ?
C5 C4 1.4252(16) . ?
C7 C7 1.448(2) 2_656 ?
C4 C3 1.4118(18) . ?
C6 C1 1.3660(18) . ?
C6 H6 0.9300 . ?
C1 C2 1.4201(18) . ?
C3 C2 1.363(2) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C18 C17 1.521(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C17 C17 1.521(4) 2_656 ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
