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_7240371
_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 H10 Br2 N2 O2'
_chemical_formula_sum            'C11 H10 Br2 N2 O2'
_chemical_formula_weight         362.03
_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
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_audit_update_record
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2018-06-14 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.771(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0273(13)
_cell_length_b                   9.0598(6)
_cell_length_c                   16.3781(16)
_cell_measurement_reflns_used    2155
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.0590
_cell_measurement_theta_min      3.6150
_cell_volume                     1315.9(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
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
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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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -54.00   65.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -19.0000  -30.0000 119

  2 omega  -15.00   46.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -99.0000  -90.0000 61

  3 omega   55.00   81.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352 -178.0000  -90.0000 26

  4 omega   36.00   62.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -99.0000  150.0000 26

  5 omega   -1.00   86.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352   57.0000  150.0000 87

  6 omega  -49.00  -13.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -57.0000 -120.0000 36

  7 omega  -86.00  -13.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2884  -57.0000  -90.0000 73
;
_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      -0.0740785000
_diffrn_orient_matrix_UB_12      -0.0031426000
_diffrn_orient_matrix_UB_13      -0.0239756000
_diffrn_orient_matrix_UB_21      0.0253548000
_diffrn_orient_matrix_UB_22      0.0362058000
_diffrn_orient_matrix_UB_23      -0.0332381000
_diffrn_orient_matrix_UB_31      0.0165519000
_diffrn_orient_matrix_UB_32      -0.0692853000
_diffrn_orient_matrix_UB_33      -0.0162839000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8750
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.021
_diffrn_reflns_theta_max         25.021
_diffrn_reflns_theta_min         3.214
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    6.152
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24758
_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    1.827
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2311
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0262P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0786
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1600
_reflns_number_total             2311
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra02368j2.cif
_cod_data_source_block           shc_544_fldu
_cod_depositor_comments
'Adding full bibliography for 7240370--7240372.cif.'
_cod_database_code               7240371
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H20N4O2Cl1
_chemical_oxdiff_usercomment     I_191
_shelx_estimated_absorpt_t_max   0.345
_shelx_estimated_absorpt_t_min   0.222
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H8A,H8B,H8C} of C8
 At 1.5 times of:
  {H9A,H9B,H9C} of C9
2. Uiso/Uaniso restraints and constraints
Uanis(Br1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C10(H10)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_olex2_date_sample_data_collection 1518679427.4
_olex2_submission_special_instructions 'No special instructions were received'