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#$Date: 2021-07-17 08:39:50 +0300 (Sat, 17 Jul 2021) $
#$Revision: 267615 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/32/7243240.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_7243240
loop_
_publ_author_name
'Ramle, Abdul Qaiyum'
'Fei, Chee Chin'
'Tiekink, Edward R. T.'
'Basirun, Wan Jefrey'
_publ_section_title
;
 Indoleninyl-substituted pyrimido[1,2-b]indazoles via a facile
 condensation reaction
;
_journal_issue                   40
_journal_name_full               'RSC Advances'
_journal_page_first              24647
_journal_page_last               24651
_journal_paper_doi               10.1039/D1RA04372B
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C20 H16 N4'
_chemical_formula_sum            'C20 H16 N4'
_chemical_formula_weight         312.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-05-10 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.4780(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.23710(10)
_cell_length_b                   6.86320(10)
_cell_length_c                   16.2164(3)
_cell_measurement_reflns_used    6410
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      76.1380
_cell_measurement_theta_min      5.5670
_cell_volume                     789.35(2)
_computing_cell_refinement
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_data_collection
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_data_reduction
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_molecular_graphics    'ORTEP-3 for Windows'
_computing_publication_material  SHELXL-2018/3
_computing_structure_refinement  SHELXL-2018/3
_computing_structure_solution    'SHELXT 2014/5'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10920
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.300
_diffrn_reflns_theta_min         5.568
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.448
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       prism
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.838
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         1774
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0687
_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)+(0.1078P)²+0.4133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1938
_refine_ls_wR_factor_ref         0.1978
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1622
_reflns_number_total             1774
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra04372b2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               7243240
_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   0.843
_shelx_estimated_absorpt_t_max   0.946
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
N1 N 0.6340(3) 0.750000 0.15165(15) 0.0459(6) Uani 1 2 d S T P . .
N2 N 0.6309(3) 0.750000 0.44951(16) 0.0513(6) Uani 1 2 d S T P . .
N3 N 0.9207(3) 0.750000 0.39999(14) 0.0417(5) Uani 1 2 d S T P . .
N4 N 1.1088(3) 0.750000 0.42513(15) 0.0473(6) Uani 1 2 d S T P . .
C1 C 0.5394(4) 0.750000 0.21144(17) 0.0392(6) Uani 1 2 d S T P . .
C2 C 0.3253(4) 0.750000 0.18087(18) 0.0430(6) Uani 1 2 d S T P . .
C3 C 0.3192(4) 0.750000 0.08756(18) 0.0459(7) Uani 1 2 d S T P . .
C4 C 0.1692(5) 0.750000 0.0191(2) 0.0673(10) Uani 1 2 d S T P . .
H4 H 0.045112 0.750000 0.026627 0.081 Uiso 1 2 calc R U P . .
C5 C 0.2104(6) 0.750000 -0.0610(2) 0.0711(10) Uani 1 2 d S T P . .
H5 H 0.112094 0.750000 -0.107710 0.085 Uiso 1 2 calc R U P . .
C6 C 0.3939(6) 0.750000 -0.0727(2) 0.0669(10) Uani 1 2 d S T P . .
H6 H 0.416611 0.750000 -0.127153 0.080 Uiso 1 2 calc R U P . .
C7 C 0.5438(5) 0.750000 -0.0059(2) 0.0569(8) Uani 1 2 d S T P . .
H7 H 0.667576 0.750000 -0.013808 0.068 Uiso 1 2 calc R U P . .
C8 C 0.5020(4) 0.750000 0.07444(17) 0.0439(6) Uani 1 2 d S T P . .
C9 C 0.2319(3) 0.5655(4) 0.20744(16) 0.0605(6) Uani 1 1 d . . . . .
H9A H 0.293532 0.452371 0.190925 0.091 Uiso 1 1 calc R U . . .
H9B H 0.101073 0.563565 0.180590 0.091 Uiso 1 1 calc R U . . .
H9C H 0.242613 0.565384 0.267409 0.091 Uiso 1 1 calc R U . . .
C10 C 0.6373(4) 0.750000 0.30042(17) 0.0423(6) Uani 1 2 d S T P . .
C11 C 0.5427(4) 0.750000 0.37006(18) 0.0498(7) Uani 1 2 d S T P . .
H11 H 0.411560 0.750000 0.358604 0.060 Uiso 1 2 calc R U P . .
C12 C 0.8158(4) 0.750000 0.46298(18) 0.0421(6) Uani 1 2 d S T P . .
C13 C 0.8289(4) 0.750000 0.31794(17) 0.0448(6) Uani 1 2 d S T P . .
H13 H 0.896240 0.750000 0.274718 0.054 Uiso 1 2 calc R U P . .
C14 C 0.9548(4) 0.750000 0.53902(18) 0.0452(7) Uani 1 2 d S T P . .
C15 C 0.9510(5) 0.750000 0.62640(19) 0.0520(7) Uani 1 2 d S T P . .
H15 H 0.837709 0.750000 0.645196 0.062 Uiso 1 2 calc R U P . .
C16 C 1.1202(5) 0.750000 0.68156(19) 0.0566(8) Uani 1 2 d S T P . .
H16 H 1.122740 0.750000 0.739125 0.068 Uiso 1 2 calc R U P . .
C17 C 1.2913(5) 0.750000 0.65228(19) 0.0523(7) Uani 1 2 d S T P . .
H17 H 1.404087 0.750000 0.691546 0.063 Uiso 1 2 calc R U P . .
C18 C 1.2981(4) 0.750000 0.56932(19) 0.0506(7) Uani 1 2 d S T P . .
H18 H 1.412752 0.750000 0.551670 0.061 Uiso 1 2 calc R U P . .
C19 C 1.1268(4) 0.750000 0.51105(17) 0.0437(6) Uani 1 2 d S T P . .
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
C1 N1 C8 107.4(2) . . ?
C12 N2 C11 116.2(2) . . ?
N4 N3 C13 124.4(2) . . ?
N4 N3 C12 116.6(2) . . ?
C13 N3 C12 119.1(2) . . ?
N3 N4 C19 101.2(2) . . ?
N1 C1 C10 120.7(2) . . ?
N1 C1 C2 114.2(2) . . ?
C10 C1 C2 125.1(2) . . ?
C3 C2 C1 98.7(2) . . ?
C3 C2 C9 110.82(16) . . ?
C1 C2 C9 112.51(15) . . ?
C3 C2 C9 110.82(16) . 4_575 ?
C1 C2 C9 112.51(15) . 4_575 ?
C9 C2 C9 110.9(3) . 4_575 ?
C8 C3 C4 119.8(3) . . ?
C8 C3 C2 108.5(2) . . ?
C4 C3 C2 131.7(3) . . ?
C5 C4 C3 117.9(3) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C7 C6 C5 121.6(3) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 116.9(3) . . ?
C6 C7 H7 121.5 . . ?
C8 C7 H7 121.5 . . ?
C3 C8 C7 122.4(3) . . ?
C3 C8 N1 111.2(2) . . ?
C7 C8 N1 126.3(3) . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C13 C10 C11 117.6(3) . . ?
C13 C10 C1 118.4(3) . . ?
C11 C10 C1 124.0(3) . . ?
N2 C11 C10 123.8(3) . . ?
N2 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
N2 C12 N3 124.5(3) . . ?
N2 C12 C14 131.6(2) . . ?
N3 C12 C14 103.9(2) . . ?
C10 C13 N3 118.9(3) . . ?
C10 C13 H13 120.6 . . ?
N3 C13 H13 120.6 . . ?
C19 C14 C15 121.0(3) . . ?
C19 C14 C12 103.8(2) . . ?
C15 C14 C12 135.2(3) . . ?
C16 C15 C14 117.4(3) . . ?
C16 C15 H15 121.3 . . ?
C14 C15 H15 121.3 . . ?
C15 C16 C17 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 122.8(3) . . ?
C18 C17 H17 118.6 . . ?
C16 C17 H17 118.6 . . ?
C17 C18 C19 117.8(3) . . ?
C17 C18 H18 121.1 . . ?
C19 C18 H18 121.1 . . ?
N4 C19 C18 125.2(3) . . ?
N4 C19 C14 114.6(3) . . ?
C18 C19 C14 120.2(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
N1 C1 1.294(4) . ?
N1 C8 1.416(3) . ?
N2 C12 1.312(4) . ?
N2 C11 1.319(4) . ?
N3 N4 1.341(3) . ?
N3 C13 1.364(4) . ?
N3 C12 1.389(3) . ?
N4 C19 1.373(3) . ?
C1 C10 1.475(4) . ?
C1 C2 1.530(3) . ?
C2 C3 1.505(4) . ?
C2 C9 1.537(3) . ?
C2 C9 1.537(3) 4_575 ?
C3 C8 1.381(4) . ?
C3 C4 1.390(4) . ?
C4 C5 1.389(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.372(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.394(4) . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C13 1.359(4) . ?
C10 C11 1.432(4) . ?
C11 H11 0.9300 . ?
C12 C14 1.428(4) . ?
C13 H13 0.9300 . ?
C14 C19 1.407(4) . ?
C14 C15 1.423(4) . ?
C15 C16 1.365(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.412(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.356(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.401(4) . ?
C18 H18 0.9300 . ?
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
C13 N3 N4 C19 180.000(1) . . . . ?
C12 N3 N4 C19 0.000(1) . . . . ?
C8 N1 C1 C10 180.000(0) . . . . ?
C8 N1 C1 C2 0.000(0) . . . . ?
N1 C1 C2 C3 0.000(0) . . . . ?
C10 C1 C2 C3 180.000(0) . . . . ?
N1 C1 C2 C9 116.90(18) . . . . ?
C10 C1 C2 C9 -63.10(18) . . . . ?
N1 C1 C2 C9 -116.90(18) . . . 4_575 ?
C10 C1 C2 C9 63.10(18) . . . 4_575 ?
C1 C2 C3 C8 0.000(0) . . . . ?
C9 C2 C3 C8 -118.18(16) . . . . ?
C9 C2 C3 C8 118.18(16) 4_575 . . . ?
C1 C2 C3 C4 180.000(0) . . . . ?
C9 C2 C3 C4 61.82(16) . . . . ?
C9 C2 C3 C4 -61.82(16) 4_575 . . . ?
C8 C3 C4 C5 0.000(0) . . . . ?
C2 C3 C4 C5 180.000(0) . . . . ?
C3 C4 C5 C6 0.000(0) . . . . ?
C4 C5 C6 C7 0.000(0) . . . . ?
C5 C6 C7 C8 0.000(0) . . . . ?
C4 C3 C8 C7 0.000(0) . . . . ?
C2 C3 C8 C7 180.000(0) . . . . ?
C4 C3 C8 N1 180.000(0) . . . . ?
C2 C3 C8 N1 0.000(0) . . . . ?
C6 C7 C8 C3 0.000(0) . . . . ?
C6 C7 C8 N1 180.000(0) . . . . ?
C1 N1 C8 C3 0.000(0) . . . . ?
C1 N1 C8 C7 180.000(0) . . . . ?
N1 C1 C10 C13 0.000(1) . . . . ?
C2 C1 C10 C13 180.000(0) . . . . ?
N1 C1 C10 C11 180.000(1) . . . . ?
C2 C1 C10 C11 0.000(1) . . . . ?
C12 N2 C11 C10 0.000(1) . . . . ?
C13 C10 C11 N2 0.000(1) . . . . ?
C1 C10 C11 N2 180.000(1) . . . . ?
C11 N2 C12 N3 0.000(1) . . . . ?
C11 N2 C12 C14 180.000(1) . . . . ?
N4 N3 C12 N2 180.000(1) . . . . ?
C13 N3 C12 N2 0.000(1) . . . . ?
N4 N3 C12 C14 0.000(1) . . . . ?
C13 N3 C12 C14 180.000(1) . . . . ?
C11 C10 C13 N3 0.000(1) . . . . ?
C1 C10 C13 N3 180.000(1) . . . . ?
N4 N3 C13 C10 180.000(1) . . . . ?
C12 N3 C13 C10 0.000(1) . . . . ?
N2 C12 C14 C19 180.000(1) . . . . ?
N3 C12 C14 C19 0.000(1) . . . . ?
N2 C12 C14 C15 0.000(2) . . . . ?
N3 C12 C14 C15 180.000(1) . . . . ?
C19 C14 C15 C16 0.000(2) . . . . ?
C12 C14 C15 C16 180.000(2) . . . . ?
C14 C15 C16 C17 0.000(2) . . . . ?
C15 C16 C17 C18 0.000(2) . . . . ?
C16 C17 C18 C19 0.000(2) . . . . ?
N3 N4 C19 C18 180.000(1) . . . . ?
N3 N4 C19 C14 0.000(1) . . . . ?
C17 C18 C19 N4 180.000(1) . . . . ?
C17 C18 C19 C14 0.000(2) . . . . ?
C15 C14 C19 N4 180.000(1) . . . . ?
C12 C14 C19 N4 0.000(1) . . . . ?
C15 C14 C19 C18 0.000(2) . . . . ?
C12 C14 C19 C18 180.000(1) . . . . ?
