#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/76/7217636.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_7217636
loop_
_publ_author_name
'Vidyacharan, Shinde'
'Sagar, A.'
'Chaitra, N. C.'
'Sharada, Duddu S.'
_publ_section_title
;
 A facile synthesis of 2H-indazoles under neat conditions and further
 transformation into aza-γ-carboline alkaloid analogues in a tandem
 one-pot fashion
;
_journal_issue                   65
_journal_name_full               'RSC Advances'
_journal_page_first              34232
_journal_paper_doi               10.1039/C4RA06838F
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C15 H14 N2 O'
_chemical_formula_sum            'C15 H14 N2 O'
_chemical_formula_weight         238.28
_chemical_melting_point          117.0(10)
_chemical_name_systematic
;
 2-(4-methoxybenzyl)-2H-indazole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 110.273(18)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4150(16)
_cell_length_b                   5.6395(9)
_cell_length_c                   12.3566(18)
_cell_measurement_temperature    293(2)
_cell_volume                     615.44(18)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.974
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2239
_diffrn_reflns_point_group_measured_fraction_full 0.722
_diffrn_reflns_point_group_measured_fraction_max 0.701
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.672
_diffrn_reflns_theta_min         3.814
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
_exptl_special_details
;
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 335 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1654
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0386
_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)+(0.0545P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1079
_reflns_Friedel_coverage         0.298
_reflns_Friedel_fraction_full    0.380
_reflns_Friedel_fraction_max     0.362
_reflns_number_gt                1425
_reflns_number_total             1654
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ra06838f2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '116-118' was changed to '117.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_database_code               7217636
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'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
N1 N 0.7382(3) 0.1090(5) 0.53885(19) 0.0579(7) Uani 1 1 d . .
O1 O 0.7611(2) 0.7341(5) 0.98013(18) 0.0750(7) Uani 1 1 d . .
C2 C 0.8430(3) 0.0865(6) 0.4063(2) 0.0549(7) Uani 1 1 d . .
C7 C 0.7583(3) 0.2981(6) 0.3967(2) 0.0527(7) Uani 1 1 d . .
C14 C 0.5851(3) 0.3933(7) 0.7130(2) 0.0664(9) Uani 1 1 d . .
H14 H 0.4958 0.3882 0.6496 0.080 Uiso 1 1 calc R U
N2 N 0.6935(3) 0.3115(5) 0.4780(2) 0.0593(6) Uani 1 1 d . .
C9 C 0.6970(3) 0.2329(6) 0.7194(2) 0.0588(8) Uani 1 1 d . .
C1 C 0.8258(3) -0.0286(6) 0.5005(2) 0.0601(7) Uani 1 1 d . .
H1 H 0.8674 -0.1740 0.5310 0.072 Uiso 1 1 calc R U
C13 C 0.5997(3) 0.5625(7) 0.7972(2) 0.0657(9) Uani 1 1 d . .
H13 H 0.5213 0.6684 0.7904 0.079 Uiso 1 1 calc R U
C6 C 0.7471(3) 0.4609(6) 0.3069(2) 0.0625(8) Uani 1 1 d . .
H6 H 0.6918 0.6004 0.2994 0.075 Uiso 1 1 calc R U
C4 C 0.9047(4) 0.1984(7) 0.2416(3) 0.0687(9) Uani 1 1 d . .
H4 H 0.9526 0.1686 0.1886 0.082 Uiso 1 1 calc R U
C3 C 0.9178(3) 0.0386(6) 0.3280(3) 0.0652(9) Uani 1 1 d . .
H3 H 0.9750 -0.0987 0.3348 0.078 Uiso 1 1 calc R U
C10 C 0.8305(3) 0.2457(7) 0.8158(3) 0.0665(9) Uani 1 1 d . .
H10 H 0.9085 0.1389 0.8229 0.080 Uiso 1 1 calc R U
C11 C 0.8478(3) 0.4139(7) 0.9001(2) 0.0670(9) Uani 1 1 d . .
H11 H 0.9377 0.4207 0.9628 0.080 Uiso 1 1 calc R U
C12 C 0.7332(3) 0.5723(7) 0.8924(2) 0.0595(8) Uani 1 1 d . .
C5 C 0.8191(4) 0.4082(7) 0.2323(3) 0.0687(9) Uani 1 1 d . .
H5 H 0.8120 0.5136 0.1728 0.082 Uiso 1 1 calc R U
C8 C 0.6760(4) 0.0446(8) 0.6288(3) 0.0713(10) Uani 1 1 d . .
H8A H 0.7243 -0.1003 0.6660 0.086 Uiso 1 1 calc R U
H8B H 0.5686 0.0124 0.5926 0.086 Uiso 1 1 calc R U
C15 C 0.6422(4) 0.8907(8) 0.9796(3) 0.0859(11) Uani 1 1 d . .
H15A H 0.6147 0.9882 0.9118 0.129 Uiso 1 1 calc R U
H15B H 0.6759 0.9895 1.0471 0.129 Uiso 1 1 calc R U
H15C H 0.5560 0.8000 0.9797 0.129 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'
O O 0.0492 0.0322 '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
C1 N1 N2 113.9(2)
C1 N1 C8 125.6(3)
N2 N1 C8 120.0(3)
C12 O1 C15 118.3(3)
C1 C2 C3 135.9(3)
C1 C2 C7 103.7(2)
C3 C2 C7 120.4(3)
N2 C7 C6 128.2(3)
N2 C7 C2 111.9(3)
C6 C7 C2 119.9(3)
C9 C14 C13 122.6(3)
C7 N2 N1 103.5(3)
C14 C9 C10 117.4(3)
C14 C9 C8 121.5(3)
C10 C9 C8 121.1(3)
N1 C1 C2 107.0(3)
C14 C13 C12 119.2(3)
C5 C6 C7 118.2(3)
C3 C4 C5 120.6(3)
C4 C3 C2 118.6(3)
C11 C10 C9 121.0(3)
C10 C11 C12 120.7(3)
O1 C12 C11 116.5(3)
O1 C12 C13 124.3(3)
C11 C12 C13 119.2(3)
C6 C5 C4 122.3(3)
N1 C8 C9 113.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.333(4)
N1 N2 1.352(4)
N1 C8 1.470(4)
O1 C12 1.371(4)
O1 C15 1.424(4)
C2 C1 1.391(4)
C2 C3 1.405(4)
C2 C7 1.417(4)
C7 N2 1.346(3)
C7 C6 1.415(4)
C14 C9 1.370(5)
C14 C13 1.383(5)
C9 C10 1.403(4)
C9 C8 1.506(5)
C13 C12 1.394(4)
C6 C5 1.353(4)
C4 C3 1.370(5)
C4 C5 1.414(5)
C10 C11 1.375(5)
C11 C12 1.379(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 44238330
