Crystal structure of 5-butylamino-3-methyl-1-(pyridin-2-yl)-1<i>H</i>-pyrazole-4-carbaldehyde obtained from a microwave-assisted reaction using caesium carbonate as catalyst
Macías, Mario A.; Orrego-Hernández, Jessica; Portilla, Jaime; Acta Crystallographica Section E 72 (2016) 1672–1674; doi:10.1107/S2056989016017187

data_2241911
_publ_section_title
;
 Crystal structure of
 5-butylamino-3-methyl-1-(pyridin-2-yl)-1<i>H</i>-pyrazole-4-carbaldehyde
 obtained from a microwave-assisted reaction using caesium carbonate as
 catalyst
;
_journal_coeditor_code           BG2597
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1672
_journal_page_last               1674
_journal_paper_doi               10.1107/S2056989016017187
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C14 H18 N4 O'
_chemical_formula_moiety         'C14 H18 N4 O'
_chemical_formula_sum            'C14 H18 N4 O'
_chemical_formula_weight         258.32
_chemical_name_systematic
;
5-Butylamino-3-methyl-1-(pyridin-2-yl)-1<i>H</i>-pyrazole-4-carbaldehyde
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 102.818(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2854(2)
_cell_length_b                   7.59144(18)
_cell_length_c                   19.4452(5)
_cell_measurement_reflns_used    5580
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.062
_cell_measurement_theta_min      2.148
_cell_volume                     1336.53(6)
_computing_cell_refinement
;
APEX2 (Bruker, 2011)
;
_computing_data_collection
;
APEX2 (Bruker, 2011)
;
_computing_data_reduction
;
SAINT (Bruker, 2011)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>,  2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR2011 (Burla <i>et al.</i>,  2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_device_type  'Rigaku MicroMax-007HF'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14709
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.062
_diffrn_reflns_theta_min         2.148
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[SADABS (Bruker, 2008) and Blessing (1995)]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.234
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         6368
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0645P)^2^+0.1608P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1102
_reflns_number_gt                5580
_reflns_number_total             6368
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            bg2597sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1336.52(6)
_cod_database_code               2241911
_cod_database_fobs_code          2241911
_shelx_estimated_absorpt_t_min   0.992
_shelx_estimated_absorpt_t_max   0.996
_shelx_hkl_checksum              51708
_shelx_res_checksum              29885
_shelxl_version_number           2.014