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_4036518
_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_formula_moiety         'C15 H10 Br N3 O2'
_chemical_formula_sum            'C15 H10 Br N3 O2'
_chemical_formula_weight         344.17
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 107.814(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5293(2)
_cell_length_b                   15.6705(4)
_cell_length_c                   7.8287(2)
_cell_measurement_reflns_used    3440
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1463.39(6)
_computing_cell_refinement       'DENZO-SMN (Otwinovski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction        'DENZO-SMN (Otwinovski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR-97 Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6469
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_min         2.146
_exptl_absorpt_coefficient_mu    2.816
_exptl_absorpt_correction_T_max  .655
_exptl_absorpt_correction_T_min  .575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO-SMN (Otwinovski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          .2
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .15
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3332
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0601P)^2^+0.2316P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.1108
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2521
_reflns_number_total             3332
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02467_si_001.cif
_cod_data_source_block           crystr4
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4036518
_shelxl_version_number           2013-4
_shelx_res_checksum              79546
_shelx_hkl_checksum              82149