Introducing chirality in halogenated 3-arylsydnones and their corresponding 1-arylpyrazoles obtained by 1,3-dipolar cycloaddition
Popa, Marcel Mirel; Shova, Sergiu; Hrubaru, Madalina; Barbu, Loredana; Draghici, Constantin; Dumitrascu, Florea; Dumitrescu, Denisa E.; RSC Advances 10 (2020) 15656–15664; doi:10.1039/D0RA02368J

data_7240372
_publ_section_title
;
 Introducing chirality in halogenated 3-arylsydnones and their
 corresponding 1-arylpyrazoles obtained by 1,3-dipolar cycloaddition
;
_journal_issue                   27
_journal_name_full               'RSC Advances'
_journal_page_first              15656
_journal_page_last               15664
_journal_paper_doi               10.1039/D0RA02368J
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C16 H17 Br N2 O4'
_chemical_formula_sum            'C16 H17 Br N2 O4'
_chemical_formula_weight         381.22
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2018-06-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-06-14 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.285(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1295(6)
_cell_length_b                   12.3462(8)
_cell_length_c                   16.9591(7)
_cell_measurement_reflns_used    3108
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.3450
_cell_measurement_theta_min      3.7350
_cell_volume                     1684.39(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0851
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega    6.00   35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352   57.0000   30.0000 29

  2 omega  -37.00    2.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2884  -57.0000  150.0000 39

  3 omega  -52.00   93.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352    0.0000    0.0000 145

  4 omega   48.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352 -178.0000  -90.0000 41

  5 omega   70.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352 -178.0000  -30.0000 26

  6 omega  -48.00   37.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -37.0000  -60.0000 85

  7 omega  -87.00  -11.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2884  -57.0000 -120.0000 76

  8 omega   59.00   84.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  178.0000 -180.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0375702000
_diffrn_orient_matrix_UB_12      -0.0313457000
_diffrn_orient_matrix_UB_13      -0.0275636000
_diffrn_orient_matrix_UB_21      0.0795473000
_diffrn_orient_matrix_UB_22      0.0182494000
_diffrn_orient_matrix_UB_23      0.0177274000
_diffrn_orient_matrix_UB_31      0.0061273000
_diffrn_orient_matrix_UB_32      -0.0445521000
_diffrn_orient_matrix_UB_33      0.0266809000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12209
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         3.118
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.461
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2969
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0387
_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^)+(0.0436P)^2^+0.4160P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2287
_reflns_number_total             2969
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra02368j2.cif
_cod_data_source_block           shc_545_fldu
_cod_depositor_comments
'Adding full bibliography for 7240370--7240372.cif.'
_cod_original_cell_volume        1684.41(17)
_cod_database_code               7240372
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H20N4O2Cl1
_chemical_oxdiff_usercomment     I_479
_shelx_estimated_absorpt_t_max   0.709
_shelx_estimated_absorpt_t_min   0.639
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C12(H12)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'