Two different reaction products from the reaction of 1-aryl-5-chloro-3-methyl-1<i>H</i>-pyrazole-4-carbaldehyde with cyclohexylamine when the aryl substituent is phenyl or pyridin-2-yl: hydrogen-bonded sheets <i>versus</i> dimers
Orrego Hernandez, Jessica; Portilla, Jaime; Cobo, Justo; Glidewell, Christopher; Acta Crystallographica Section C 71 (2015) –; doi:10.1107/S2053229615006403

data_2019924
_publ_section_title
;
 Two different reaction products from the reaction of
 1-aryl-5-chloro-3-methyl-1<i>H</i>-pyrazole-4-carbaldehyde with
 cyclohexylamine when the aryl substituent is phenyl or pyridin-2-yl:
 hydrogen-bonded sheets <i>versus</i> dimers
;
_journal_coeditor_code           QS3046
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229615006403
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C16 H20 N4 O'
_chemical_formula_moiety         'C16 H20 N4 O'
_chemical_formula_sum            'C16 H20 N4 O'
_chemical_formula_weight         284.36
_chemical_name_systematic
;
5-Cyclohexylamino-3-methyl-1-(pyridin-2-yl)-1<i>H</i>-pyrazole-4-carbaldehyde
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 95.978(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.369(2)
_cell_length_b                   20.489(3)
_cell_length_c                   6.7444(10)
_cell_measurement_reflns_used    3370
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      2.762
_cell_measurement_theta_min      27.50
_cell_volume                     2936.8(7)
_computing_cell_refinement
;
DIRAX/LSQ (Duisenberg <i>et al.</i>,  2000)
;
_computing_data_collection
;
COLLECT (Nonius, 1999)
;
_computing_data_reduction
;
EVALCCD (Duisenberg <i>et al.</i>,  2003)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10192
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         3.956
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.296
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3367
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0561P)^2^+0.4348P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1150
_reflns_number_gt                2149
_reflns_number_total             3367
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            qs3046sup1.cif
_cod_data_source_block           I
_cod_database_code               2019924
_cod_database_fobs_code          2019924
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.983
_shelx_hkl_checksum              87781
_shelx_res_checksum              28173
_shelxl_version_number           2.014