Dirhodium(II)-Catalysed Cycloisomerization of Azaenyne: Rapid Assembly of Centrally and Axially Chiral Isoindazoles Frameworks
Qiu, Shaotong; Gao, Xiang; Zhu, Shifa; Chemical Science  (2021) –; doi:10.1039/D1SC04961E

data_1564787
_publ_section_title
;
 Dirhodium(II)-Catalysed Cycloisomerization of Azaenyne: Rapid Assembly of
 Centrally and Axially Chiral Isoindazoles Frameworks
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04961E
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C35 H25 Br N2 O5'
_chemical_formula_sum            'C35 H25 Br N2 O5'
_chemical_formula_weight         633.48
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-24
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-08-27 deposited with the CCDC.	2021-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.747(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.00919(18)
_cell_length_b                   14.8084(3)
_cell_length_c                   13.4349(3)
_cell_measurement_reflns_used    8213
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      73.7070
_cell_measurement_theta_min      2.9390
_cell_volume                     1392.87(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -61.00  30.00   1.00    1.00    --  -40.73  57.00-180.00   91
  2  \w    -94.00 -16.00   1.00    1.00    --  -40.73 -57.00 -60.00   78
  3  \w   -115.00  -8.00   1.00    1.00    --  -40.73 -77.00  60.00  107
  4  \w      1.00  70.00   1.00    1.00    --   40.73 -99.00 -90.00   69
  5  \w     23.00  50.00   1.00    1.00    --   40.73 -99.00-120.00   27
  6  \w     79.00 174.00   1.00    1.00    --  107.58  30.00  30.00   95
  7  \w     87.00 128.00   1.00    1.00    --  107.58 -45.00 150.00   41
  8  \w     85.00 140.00   1.00    1.00    --  107.58 -77.00 -90.00   55
  9  \w     36.00  84.00   1.00    1.00    --  107.58 -45.00 150.00   48
 10  \w     32.00 135.00   1.00    1.00    --  107.58 -77.00 120.00  103
 11  \w     81.00 178.00   1.00    1.00    --  107.58  61.00 -60.00   97
 12  \w     90.00 116.00   1.00    1.00    --  107.58  45.00 -90.00   26
 13  \w     43.00 108.00   1.00    1.00    --  107.58 -45.00   0.00   65
 14  \w     86.00 120.00   1.00    1.00    --  107.58-125.00 -90.00   34
 15  \w     25.00  77.00   1.00    1.00    --  107.58 -95.00 -30.00   52
 16  \w     67.00 120.00   1.00    1.00    --  107.58-125.00 120.00   53
 17  \w    135.00 161.00   1.00    1.00    --  107.58  45.00 -90.00   26
 18  \w     83.00 177.00   1.00    1.00    --  107.58  45.00-120.00   94
 19  \w     45.00  72.00   1.00    1.00    --  107.58 -77.00 -90.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0747038000
_diffrn_orient_matrix_UB_12      -0.0267783000
_diffrn_orient_matrix_UB_13      0.1056935000
_diffrn_orient_matrix_UB_21      -0.0539964000
_diffrn_orient_matrix_UB_22      0.0941071000
_diffrn_orient_matrix_UB_23      0.0387255000
_diffrn_orient_matrix_UB_31      -0.1997467000
_diffrn_orient_matrix_UB_32      -0.0353638000
_diffrn_orient_matrix_UB_33      0.0227495000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10046
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.789
_diffrn_reflns_theta_min         3.293
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.416
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 2442 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         5469
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0416P)^2^+0.1608P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0685
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                5340
_reflns_number_total             5469
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04961e2.cif
_cod_data_source_block           68-3
_cod_original_cell_volume        1392.88(6)
_cod_database_code               1564787
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C8(H8), C19(H19)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16),
 C17(H17), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C29(H29),
  C31(H31)
2.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C35(H35A,H35B,H35C)
;
_shelx_res_checksum              23257
_shelx_hkl_checksum              60486
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.483
_oxdiff_exptl_absorpt_empirical_full_min 0.713