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#$Date: 2023-07-10 10:20:06 +0300 (Mon, 10 Jul 2023) $
#$Revision: 285107 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/74/8107441.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_8107441
loop_
_publ_author_name
'Cui, Beibei'
'Mi, Xia'
'Zhang, Jingyu'
_publ_section_title
;
 Crystal structure of 2-(2-(4-methoxyphenyl)-2H-indazol-3-yl)acetonitrile,
 C16H13N3O
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              361
_journal_page_last               362
_journal_paper_doi               10.1515/ncrs-2023-0025
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C16 H13 N3 O1'
_chemical_formula_sum            'C16 H13 N3 O'
_chemical_formula_weight         263.29
_chemical_name_systematic
;
 2-(2-(4-methoxyphenyl)-2H-indazol-3-yl)acetonitrile, C16H13N3O1? 
C₁₆H₁₃N₃O₁  
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6087(4)
_cell_length_b                   9.6681(4)
_cell_length_c                   18.6600(9)
_cell_measurement_reflns_used    1547
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0850
_cell_measurement_theta_min      4.7230
_cell_volume                     1372.66(11)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'[2]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'[2]'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'[3]'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'[4]'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5203
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.074
_diffrn_reflns_theta_min         4.740
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_min  0.94709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0024(5)
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2594
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0420
_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)+(0.0442P)²+0.0440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1093
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                2212
_reflns_number_total             2594
_cod_data_source_file            suppl_j_ncrs-2023-0025_suppl.cif
_cod_data_source_block           exp_1115
_cod_original_formula_sum        'C16 H13 N3 O1'
_cod_database_code               8107441
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
O1 O 0.4133(3) 0.9572(3) 0.73803(13) 0.0715(8) Uani 1 1 d . . . . .
N1 N 0.3250(3) 0.7969(2) 0.41251(13) 0.0450(6) Uani 1 1 d . . . . .
N2 N 0.3875(3) 0.7178(2) 0.46781(12) 0.0407(5) Uani 1 1 d . . . . .
N3 N 0.3008(5) 0.3044(3) 0.5388(2) 0.0913(12) Uani 1 1 d . . . . .
C1 C 0.4543(4) 0.4859(3) 0.31992(16) 0.0491(7) Uani 1 1 d . . . . .
H1 H 0.5034 0.4007 0.3315 0.059 Uiso 1 1 calc R . . . .
C2 C 0.4142(4) 0.5192(4) 0.25077(18) 0.0583(8) Uani 1 1 d . . . . .
H2 H 0.4393 0.4561 0.2146 0.070 Uiso 1 1 calc R . . . .
C3 C 0.3357(4) 0.6471(4) 0.23256(17) 0.0574(8) Uani 1 1 d . . . . .
H3 H 0.3082 0.6650 0.1849 0.069 Uiso 1 1 calc R . . . .
C4 C 0.2996(4) 0.7444(3) 0.28302(16) 0.0521(7) Uani 1 1 d . . . . .
H4 H 0.2470 0.8278 0.2705 0.063 Uiso 1 1 calc R . . . .
C5 C 0.3442(4) 0.7153(3) 0.35493(15) 0.0420(6) Uani 1 1 d . . . . .
C6 C 0.4184(4) 0.5855(3) 0.37325(15) 0.0404(6) Uani 1 1 d . . . . .
C7 C 0.4457(3) 0.5914(3) 0.44621(15) 0.0399(6) Uani 1 1 d . . . . .
C8 C 0.5274(4) 0.4855(3) 0.49453(15) 0.0457(7) Uani 1 1 d . . . . .
H8A H 0.6208 0.4385 0.4689 0.055 Uiso 1 1 calc R . . . .
H8B H 0.5794 0.5318 0.5355 0.055 Uiso 1 1 calc R . . . .
C9 C 0.4003(5) 0.3830(3) 0.51996(18) 0.0580(8) Uani 1 1 d . . . . .
C10 C 0.3909(3) 0.7765(3) 0.53805(15) 0.0414(6) Uani 1 1 d . . . . .
C11 C 0.3338(4) 0.7024(3) 0.59619(16) 0.0501(7) Uani 1 1 d . . . . .
H11 H 0.2897 0.6135 0.5898 0.060 Uiso 1 1 calc R . . . .
C12 C 0.3412(4) 0.7588(3) 0.66444(16) 0.0539(8) Uani 1 1 d . . . . .
H12 H 0.3049 0.7073 0.7038 0.065 Uiso 1 1 calc R . . . .
C13 C 0.4027(4) 0.8920(3) 0.67353(17) 0.0536(8) Uani 1 1 d . . . . .
C14 C 0.4563(4) 0.9676(3) 0.61448(18) 0.0562(8) Uani 1 1 d . . . . .
H14 H 0.4954 1.0580 0.6205 0.067 Uiso 1 1 calc R . . . .
C15 C 0.4523(4) 0.9102(3) 0.54704(17) 0.0487(7) Uani 1 1 d . . . . .
H15 H 0.4905 0.9610 0.5077 0.058 Uiso 1 1 calc R . . . .
C16 C 0.3641(6) 0.8822(5) 0.80045(19) 0.0874(14) Uani 1 1 d . . . . .
H16A H 0.3774 0.9402 0.8419 0.131 Uiso 1 1 calc GR . . . .
H16B H 0.4379 0.8022 0.8053 0.131 Uiso 1 1 calc GR . . . .
H16C H 0.2437 0.8536 0.7964 0.131 Uiso 1 1 calc GR . . . .
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_absorpt_correction_T_max
1.00000
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
C13 O1 C16 118.2(3) . .
C5 N1 N2 103.7(2) . .
N1 N2 C10 118.4(2) . .
C7 N2 N1 113.0(2) . .
C7 N2 C10 128.5(2) . .
C2 C1 H1 121.2 . .
C2 C1 C6 117.6(3) . .
C6 C1 H1 121.2 . .
C1 C2 H2 119.1 . .
C1 C2 C3 121.8(3) . .
C3 C2 H2 119.1 . .
C2 C3 H3 119.2 . .
C4 C3 C2 121.6(3) . .
C4 C3 H3 119.2 . .
C3 C4 H4 120.9 . .
C3 C4 C5 118.1(3) . .
C5 C4 H4 120.9 . .
N1 C5 C4 128.2(3) . .
N1 C5 C6 111.8(2) . .
C4 C5 C6 120.1(3) . .
C1 C6 C5 120.7(3) . .
C7 C6 C1 134.1(3) . .
C7 C6 C5 105.2(2) . .
N2 C7 C6 106.3(2) . .
N2 C7 C8 124.8(2) . .
C6 C7 C8 128.9(2) . .
C7 C8 H8A 109.1 . .
C7 C8 H8B 109.1 . .
H8A C8 H8B 107.8 . .
C9 C8 C7 112.5(3) . .
C9 C8 H8A 109.1 . .
C9 C8 H8B 109.1 . .
N3 C9 C8 179.1(4) . .
C11 C10 N2 120.8(3) . .
C11 C10 C15 119.9(3) . .
C15 C10 N2 119.2(3) . .
C10 C11 H11 119.7 . .
C10 C11 C12 120.6(3) . .
C12 C11 H11 119.7 . .
C11 C12 H12 120.2 . .
C13 C12 C11 119.6(3) . .
C13 C12 H12 120.2 . .
O1 C13 C12 124.1(3) . .
O1 C13 C14 116.2(3) . .
C12 C13 C14 119.7(3) . .
C13 C14 H14 119.7 . .
C15 C14 C13 120.6(3) . .
C15 C14 H14 119.7 . .
C10 C15 H15 120.2 . .
C14 C15 C10 119.6(3) . .
C14 C15 H15 120.2 . .
O1 C16 H16A 109.5 . .
O1 C16 H16B 109.5 . .
O1 C16 H16C 109.5 . .
H16A C16 H16B 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C13 1.361(4) .
O1 C16 1.422(5) .
N1 N2 1.369(3) .
N1 C5 1.341(4) .
N2 C7 1.361(3) .
N2 C10 1.429(3) .
N3 C9 1.129(4) .
C1 H1 0.9300 .
C1 C2 1.364(4) .
C1 C6 1.412(4) .
C2 H2 0.9300 .
C2 C3 1.415(5) .
C3 H3 0.9300 .
C3 C4 1.359(5) .
C4 H4 0.9300 .
C4 C5 1.413(4) .
C5 C6 1.417(4) .
C6 C7 1.378(4) .
C7 C8 1.500(4) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C8 C9 1.463(4) .
C10 C11 1.371(4) .
C10 C15 1.385(4) .
C11 H11 0.9300 .
C11 C12 1.387(4) .
C12 H12 0.9300 .
C12 C13 1.380(5) .
C13 C14 1.384(5) .
C14 H14 0.9300 .
C14 C15 1.376(4) .
C15 H15 0.9300 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
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
O1 C13 C14 C15 179.3(3) . . . .
N1 N2 C7 C6 -0.8(3) . . . .
N1 N2 C7 C8 177.5(2) . . . .
N1 N2 C10 C11 135.0(3) . . . .
N1 N2 C10 C15 -44.8(4) . . . .
N1 C5 C6 C1 -178.2(2) . . . .
N1 C5 C6 C7 -0.4(3) . . . .
N2 N1 C5 C4 179.6(3) . . . .
N2 N1 C5 C6 -0.1(3) . . . .
N2 C7 C8 C9 96.0(3) . . . .
N2 C10 C11 C12 178.5(3) . . . .
N2 C10 C15 C14 -179.9(3) . . . .
C1 C2 C3 C4 1.4(5) . . . .
C1 C6 C7 N2 178.0(3) . . . .
C1 C6 C7 C8 -0.2(5) . . . .
C2 C1 C6 C5 -0.3(4) . . . .
C2 C1 C6 C7 -177.2(3) . . . .
C2 C3 C4 C5 0.6(5) . . . .
C3 C4 C5 N1 178.1(3) . . . .
C3 C4 C5 C6 -2.3(4) . . . .
C4 C5 C6 C1 2.2(4) . . . .
C4 C5 C6 C7 180.0(3) . . . .
C5 N1 N2 C7 0.5(3) . . . .
C5 N1 N2 C10 178.1(2) . . . .
C5 C6 C7 N2 0.7(3) . . . .
C5 C6 C7 C8 -177.5(3) . . . .
C6 C1 C2 C3 -1.5(5) . . . .
C6 C7 C8 C9 -86.2(4) . . . .
C7 N2 C10 C11 -47.8(4) . . . .
C7 N2 C10 C15 132.4(3) . . . .
C10 N2 C7 C6 -178.1(2) . . . .
C10 N2 C7 C8 0.2(4) . . . .
C10 C11 C12 C13 1.6(5) . . . .
C11 C10 C15 C14 0.4(4) . . . .
C11 C12 C13 O1 179.2(3) . . . .
C11 C12 C13 C14 0.0(5) . . . .
C12 C13 C14 C15 -1.4(5) . . . .
C13 C14 C15 C10 1.2(5) . . . .
C15 C10 C11 C12 -1.7(5) . . . .
C16 O1 C13 C12 2.4(5) . . . .
C16 O1 C13 C14 -178.3(3) . . . .
