1,3-Dipolar cycloaddition of polycyclic azomethine ylide to norcorroles: towards dibenzoullazine-fused derivatives
Li, Sha; Sun, Yahan; Li, Xiaofang; Smaga, Oskar; Koniarz, Sebastian; Stępień, Marcin; Chmielewski, Piotr J.; Chemical Communications  (2022) –; doi:10.1039/D2CC02071H

data_7130096
_publ_section_title
;
 1,3-Dipolar cycloaddition of polycyclic azomethine ylide to norcorroles:
 towards dibenzoullazine-fused derivatives
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02071H
_journal_year                    2022
_chemical_formula_moiety         'C84 H64 N6 Ni, 2(C6 H6)'
_chemical_formula_sum            'C96 H76 N6 Ni'
_chemical_formula_weight         1372.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-05-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-10-20 deposited with the CCDC.	2022-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                104.320(4)
_cell_angle_beta                 108.420(5)
_cell_angle_gamma                98.286(4)
_cell_formula_units_Z            1
_cell_length_a                   11.8776(7)
_cell_length_b                   12.4674(5)
_cell_length_c                   13.0460(7)
_cell_measurement_reflns_used    7147
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      74.6960
_cell_measurement_theta_min      3.7420
_cell_volume                     1723.27(17)
_computing_cell_refinement       'CrysAlisPro 1.171.41.75a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.75a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.75a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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     66.00 109.00   0.50    5.00    --   59.37  30.00  60.00   86
  2  \w     20.00  66.00   0.50    5.00    --   59.37-126.00  30.00   92
  3  \w     28.00  61.00   0.50    5.00    --   59.37 -95.00-150.00   66
  4  \w     11.00  37.00   0.50    5.00    --   59.37 -30.00  60.00   52
  5  \w     10.00  36.00   0.50    5.00    --   59.37 -30.00 -90.00   52
  6  \w     11.00  37.00   0.50    5.00    --   59.37 -30.00  30.00   52
  7  \w     61.00  97.00   0.50    5.00    --   59.37  30.00-150.00   72
  8  \w     64.00 109.00   0.50    5.00    --   59.37  30.00 -90.00   90
  9  \w     10.00  35.00   0.50    5.00    --   59.37 -30.00-120.00   50
 10  \w    -96.00 -62.00   0.50    5.00    --  -61.12 -30.00  90.00   68
 11  \w     34.00  69.00   0.50    5.00    --   73.92 -95.00-120.00   70
 12  \w     68.00 107.00   0.50    5.00    --   73.92   0.00-120.00   78
 13  \w     42.00  82.00   0.50    5.00    --   73.92 -95.00  60.00   80
 14  \w     38.00  64.00   0.50    5.00    --   73.92 -95.00 120.00   52
 15  \w     38.00  66.00   0.50    5.00    --   73.92 -95.00 -60.00   56
 16  \w     37.00  63.00   0.50    5.00    --   73.92 -95.00  30.00   52
 17  \w     40.00  66.00   0.50    5.00    --   73.92   0.00-120.00   52
 18  \w   -117.00 -77.00   0.50    5.00    --  -74.77-126.00 -60.00   80
 19  \w   -120.00 -95.00   0.50    5.00    --  -74.77-126.00 120.00   50
 20  \w   -121.00 -85.00   0.50    5.00    --  -74.77 -30.00   0.00   72
 21  \w   -119.00 -93.00   0.50    5.00    --  -74.77 -30.00 -90.00   52
 22  \w   -121.00 -88.00   0.50    5.00    --  -75.16 -30.00 -30.00   66
 23  \w   -105.00 -67.00   0.50    5.00    --  -75.16 126.00 -90.00   76
 24  \w   -106.00 -34.00   0.50    5.00    --  -75.16 126.00 120.00  144
 25  \w    -62.00 -34.00   0.50    5.00    --  -75.16 126.00 -90.00   56
 26  \w     46.00  73.00   0.50    5.00    --   79.25 -95.00-120.00   54
 27  \w     39.00  64.00   0.50    5.00    --   79.25 -95.00 150.00   50
 28  \w     46.00 123.00   0.50    5.00    --   79.25  15.00-180.00  154
 29  \w     80.00 123.00   0.50    5.00    --   79.25  30.00 -60.00   86
 30  \w     54.00 126.00   0.50    5.00    --   79.25  15.00 -90.00  144
 31  \w     84.00 111.00   0.50    5.00    --   79.25-126.00  60.00   54
 32  \w     46.00 111.00   0.50    5.00    --   79.25-126.00-120.00  130
 33  \w     84.00 111.00   0.50    5.00    --   79.25-126.00 -90.00   54
 34  \w     92.00 120.00   0.50    5.00    --   79.25  15.00 120.00   56
 35  \w     62.00  89.00   0.50    5.00    --   79.25  15.00 120.00   54
 36  \w     41.00 111.00   0.50    5.00    --   79.25-126.00  30.00  140
 37  \w     42.00  67.00   0.50    5.00    --   79.25 -95.00 -30.00   50
 38  \w     94.00 121.00   0.50    5.00    --   83.00-138.00 117.33   54
 39  \w     41.00 103.00   0.50    5.00    --   83.00-109.00 127.40  124
 40  \w     39.00  87.00   0.50    5.00    --   83.00-138.00 117.33   96
 41  \w     44.00 104.00   0.50    5.00    --   83.00-108.00 -66.18  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1088383000
_diffrn_orient_matrix_UB_12      -0.0294639000
_diffrn_orient_matrix_UB_13      0.0802153000
_diffrn_orient_matrix_UB_21      -0.0724485000
_diffrn_orient_matrix_UB_22      -0.0138086000
_diffrn_orient_matrix_UB_23      0.0771448000
_diffrn_orient_matrix_UB_31      -0.0524861000
_diffrn_orient_matrix_UB_32      -0.1273371000
_diffrn_orient_matrix_UB_33      -0.0691038000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19555
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        65.000
_diffrn_reflns_theta_max         65.000
_diffrn_reflns_theta_min         3.759
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.840
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.75a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark orange'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       needle
_exptl_crystal_F_000             722
_exptl_crystal_size_max          0.142
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.881
_refine_diff_density_min         -0.741
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     472
_refine_ls_number_reflns         5833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0705
_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^)+(0.0739P)^2^+3.3640P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1790
_refine_ls_wR_factor_ref         0.1966
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4069
_reflns_number_total             5833
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02071h3.cif
_cod_data_source_block           ov_osylid_auto
_cod_original_cell_volume        1723.27(16)
_cod_database_code               7130096
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 95.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 Aromatic/amide H refined with riding coordinates:
 C8(H8), C55(H55), C43(H43), C42(H42), C40(H40), C7(H7), C24(H24), C32(H32),
 C41(H41), C53(H53), C34(H34), C27(H27), C25(H25), C26(H26), C104(H104),
 C103(H103), C102(H102), C101(H101), C105(H105), C100(H100)
2.b Idealised Me refined as rotating group:
 C59(H59A,H59B,H59C), C57(H57A,H57B,H57C), C58(H58A,H58B,H58C), C36(H36A,H36B,
 H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              84166
_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 1.436
_oxdiff_exptl_absorpt_empirical_full_min 0.719