Synthesis and Rotational Isomerism of 1-Substituted Methyl (S)-[5-(2-Nitrophenyl)-1H-pyrazole-4-carbonyl]alaninates.
Šenica, Luka; Stopar, Karmen; Friedrich, Miha; Grošelj, Uroš; Plavec, Janez; Počkaj, Marta; Podlipnik, Črtomir; Štefane, Bogdan; Svete, Jurij; The Journal of organic chemistry 81 (2016) 146–161; doi:10.1021/acs.joc.5b02467

data_4036522
_publ_section_title
;
 Synthesis and Rotational Isomerism of 1-Substituted Methyl
 (S)-[5-(2-Nitrophenyl)-1H-pyrazole-4-carbonyl]alaninates.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              146
_journal_page_last               161
_journal_paper_doi               10.1021/acs.joc.5b02467
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C20 H18 Cl N3 O3'
_chemical_formula_sum            'C20 H18 Cl N3 O3'
_chemical_formula_weight         383.82
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 111.754(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8681(3)
_cell_length_b                   19.3196(6)
_cell_length_c                   11.1852(4)
_cell_measurement_reflns_used    4479
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      .41
_cell_volume                     1980.57(11)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71072
_diffrn_reflns_av_unetI/netI     0.046
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_number            28934
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         27.119
_diffrn_reflns_theta_min         2.460
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO-SMN (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       platelet
_exptl_crystal_F_000             800
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .08
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.196
_refine_ls_abs_structure_details
;
 Flack x determined using 2074 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         8699
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.1419
_refine_ls_R_factor_gt           0.0760
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1461P)^2^+0.0001P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1983
_refine_ls_wR_factor_ref         0.2475
_reflns_Friedel_coverage         0.937
_reflns_Friedel_fraction_full    0.954
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                5300
_reflns_number_total             8699
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02467_si_001.cif
_cod_data_source_block           crystr25b
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4036522
_shelxl_version_number           2013-4
_shelx_res_checksum              47179
_shelx_hkl_checksum              50563