A facile synthesis of 2H-indazoles under neat conditions and further transformation into aza-γ-carboline alkaloid analogues in a tandem one-pot fashion
Vidyacharan, Shinde; Sagar, A.; Chaitra, N. C.; Sharada, Duddu S.; RSC Advances 4 (2014) 34232–; doi:10.1039/C4RA06838F

data_7217636
_publ_section_title
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 A facile synthesis of 2H-indazoles under neat conditions and further
 transformation into aza-\g-carboline alkaloid analogues in a tandem
 one-pot fashion
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_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
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 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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0545P)^2^] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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 
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_cod_database_code               7217636
_shelxl_version_number           2013-4
_shelx_res_checksum              66336