Different molecular conformations co-exist in each of three 2-aryl-<i>N</i>-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1<i>H</i>-pyrazol-4-yl)acetamides: hydrogen bonding in zero, one and two dimensions
Narayana, Badiadka; Yathirajan, Hemmige S.; Rathore, Ravindranath S.; Glidewell, Christopher; Acta Crystallographica Section C 72 (2016) –; doi:10.1107/S2053229616012870

data_2020571
_publ_section_title
;
 Different molecular conformations co-exist in each of three
 2-aryl-<i>N</i>-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1<i>H</i>-pyrazol-4-yl)acetamides:
 hydrogen bonding in zero, one and two dimensions
;
_journal_coeditor_code           SK3634
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229616012870
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C19 H18 Cl N3 O2'
_chemical_formula_moiety         'C19 H18 Cl N3 O2'
_chemical_formula_sum            'C19 H18 Cl N3 O2'
_chemical_formula_weight         355.81
_chemical_name_systematic
2-(2-Chlorophenyl)-<i>N</i>-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1<i>H</i>-pyrazol-4-yl)acetamide
_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                 120.957(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.023(3)
_cell_length_b                   8.2976(10)
_cell_length_c                   21.602(3)
_cell_measurement_reflns_used    6192
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      32.213
_cell_measurement_theta_min      2.063
_cell_volume                     3538.9(10)
_computing_cell_refinement
;
APEX2 (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 2012)
;
_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      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII area-detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            33715
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.550
_diffrn_reflns_theta_min         2.063
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.405
_refine_ls_extinction_coef       0.0042(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4079
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0639P)^2^+3.3163P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1494
_reflns_number_gt                3038
_reflns_number_total             4079
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3634sup1.cif
_cod_data_source_block           II
_cod_original_cell_volume        3538.9(9)
_cod_database_code               2020571
_cod_database_fobs_code          2020571
_shelx_estimated_absorpt_t_min   0.913
_shelx_estimated_absorpt_t_max   0.955
_shelx_hkl_checksum              37498
_shelx_res_checksum              62519
_shelxl_version_number           2.014