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_7240370
_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         'C11 H12 Br2 N2 O3'
_chemical_formula_sum            'C11 H12 Br2 N2 O3'
_chemical_formula_weight         380.05
_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             2018-06-13
_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                 99.867(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6989(11)
_cell_length_b                   10.7694(15)
_cell_length_c                   15.0669(17)
_cell_measurement_reflns_used    1935
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.6210
_cell_measurement_theta_min      3.4930
_cell_volume                     1390.6(3)
_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  -36.00  -10.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2884  -57.0000   60.0000 26

  2 omega   -6.00   56.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -99.0000   90.0000 62

  3 omega  -49.00   41.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -57.0000  -30.0000 90

  4 omega  -49.00   36.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -57.0000 -150.0000 85

  5 omega   -8.00   25.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352   77.0000  -30.0000 33

  6 omega  -12.00   26.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352   77.0000 -150.0000 38

  7 omega   37.00   63.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  178.0000   90.0000 26

  8 omega  -49.00   29.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -57.0000   90.0000 78
;
_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      -0.0707858000
_diffrn_orient_matrix_UB_12      0.0254834000
_diffrn_orient_matrix_UB_13      -0.0231914000
_diffrn_orient_matrix_UB_21      0.0408293000
_diffrn_orient_matrix_UB_22      0.0271026000
_diffrn_orient_matrix_UB_23      -0.0320975000
_diffrn_orient_matrix_UB_31      -0.0128116000
_diffrn_orient_matrix_UB_32      -0.0543758000
_diffrn_orient_matrix_UB_33      -0.0267522000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1378
_diffrn_reflns_av_unetI/netI     0.1145
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9371
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         3.161
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.831
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09078
_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    1.815
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.995
_refine_diff_density_rms         0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1174
_refine_ls_R_factor_gt           0.0750
_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^)+(0.0704P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1788
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1526
_reflns_number_total             2447
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra02368j2.cif
_cod_data_source_block           shc_547_fldu
_cod_depositor_comments
'Adding full bibliography for 7240370--7240372.cif.'
_cod_database_code               7240370
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H20N4O1Br1
_chemical_oxdiff_usercomment     I_485
_shelx_estimated_absorpt_t_max   0.292
_shelx_estimated_absorpt_t_min   0.235
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'