#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:17:46 +0300 (Fri, 05 May 2023) $
#$Revision: 283453 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/92/7159238.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_7159238
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 H16 N4'
_chemical_formula_sum            'C18 H16 N4'
_chemical_formula_weight         288.35
_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
;
2022-10-31 deposited with the CCDC.	2023-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 122.24(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.637(1)
_cell_length_b                   14.143(1)
_cell_length_c                   9.403(1)
_cell_measurement_reflns_used    1458
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      0.988
_cell_measurement_theta_min      0.980
_cell_volume                     1421.4(3)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1023
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14639
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.386
_diffrn_reflns_theta_min         2.388
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       plate
_exptl_crystal_F_000             608.0
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1458
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0428
_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+0.2974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1441
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1119
_reflns_number_total             1458
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00121k2.cif
_cod_data_source_block           DATAM_a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7159236--7159238.cif.'
_cod_original_cell_volume        1421.5(1)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7159238
_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
N2 N 0.37221(12) 0.61378(9) 0.57610(15) 0.0383(4) Uani 1 1 d . . . . .
N1 N 0.29786(12) 0.62838(10) 0.40894(14) 0.0419(4) Uani 1 1 d . . . . .
C8 C 0.45558(13) 0.68441(10) 0.65986(17) 0.0367(4) Uani 1 1 d . . . . .
C9 C 0.43327(14) 0.75224(11) 0.53880(18) 0.0360(4) Uani 1 1 d . . . . .
C14 C 0.33464(14) 0.71379(11) 0.38544(18) 0.0382(4) Uani 1 1 d . . . . .
C15 C 0.35143(15) 0.52904(11) 0.64652(19) 0.0433(4) Uani 1 1 d . . . . .
H15A H 0.265024 0.509411 0.573428 0.052 Uiso 1 1 calc R U . . .
H15B H 0.364152 0.544701 0.755026 0.052 Uiso 1 1 calc R U . . .
C16 C 0.43595(15) 0.44650(11) 0.66880(19) 0.0447(4) Uani 1 1 d . . . . .
H16A H 0.393406 0.388288 0.663501 0.054 Uiso 1 1 calc R U . . .
H16B H 0.447736 0.446231 0.574968 0.054 Uiso 1 1 calc R U . . .
C13 C 0.28797(16) 0.76333(12) 0.23247(19) 0.0454(4) Uani 1 1 d . . . . .
H13 H 0.222658 0.739123 0.131362 0.054 Uiso 1 1 calc R U . . .
C10 C 0.48636(15) 0.84035(11) 0.54083(19) 0.0436(4) Uani 1 1 d . . . . .
H10 H 0.550678 0.866438 0.640780 0.052 Uiso 1 1 calc R U . . .
C11 C 0.44032(18) 0.88580(12) 0.3918(2) 0.0500(5) Uani 1 1 d . . . . .
H11 H 0.474316 0.943804 0.390140 0.060 Uiso 1 1 calc R U . . .
C12 C 0.34171(17) 0.84704(13) 0.2386(2) 0.0511(5) Uani 1 1 d . . . . .
H12 H 0.313169 0.880317 0.139225 0.061 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'
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
N1 N2 C8 113.94(13) . . ?
N1 N2 C15 118.18(12) . . ?
C8 N2 C15 127.81(13) . . ?
N2 N1 C14 103.90(12) . . ?
N2 C8 C9 106.01(13) . . ?
N2 C8 C8 123.73(11) . 2_656 ?
C9 C8 C8 130.24(11) . 2_656 ?
C8 C9 C10 135.05(14) . . ?
C8 C9 C14 104.53(13) . . ?
C10 C9 C14 120.41(14) . . ?
N1 C14 C13 127.91(14) . . ?
N1 C14 C9 111.61(13) . . ?
C13 C14 C9 120.48(15) . . ?
N2 C15 C16 114.21(13) . . ?
C16 C16 C15 115.57(11) 2_656 . ?
C12 C13 C14 117.60(15) . . ?
C11 C10 C9 117.73(15) . . ?
C10 C11 C12 121.68(17) . . ?
C13 C12 C11 122.09(15) . . ?
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
N2 N1 1.3491(17) . ?
N2 C8 1.3575(19) . ?
N2 C15 1.4593(19) . ?
N1 C14 1.354(2) . ?
C8 C9 1.398(2) . ?
C8 C8 1.450(3) 2_656 ?
C9 C10 1.411(2) . ?
C9 C14 1.418(2) . ?
C14 C13 1.415(2) . ?
C15 C16 1.519(2) . ?
C16 C16 1.521(3) 2_656 ?
C13 C12 1.351(2) . ?
C10 C11 1.359(2) . ?
C11 C12 1.419(2) . ?
