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_7130098
_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         'C60 H47 N5 Ni'
_chemical_formula_sum            'C60 H47 N5 Ni'
_chemical_formula_weight         896.73
_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             2021-09-28
_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                73.327(2)
_cell_angle_beta                 74.156(2)
_cell_angle_gamma                82.126(2)
_cell_formula_units_Z            2
_cell_length_a                   10.9575(2)
_cell_length_b                   13.4987(3)
_cell_length_c                   18.8848(4)
_cell_measurement_reflns_used    25285
_cell_measurement_temperature    169.98(11)
_cell_measurement_theta_max      75.1970
_cell_measurement_theta_min      2.5190
_cell_volume                     2568.97(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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      169.98(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.964
_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    -79.00 -42.00   0.50    0.05    --  -47.20 108.00 -57.00   74
  2  \w     18.00  86.00   0.50    0.05    --   47.20-108.00-154.00  136
  3  \w   -140.00 -85.00   0.50    0.08    --  -99.00-108.00-154.00  110
  4  \w    -91.00 -66.00   0.50    0.08    --  -99.00 108.00 -57.00   50
  5  \w     46.00 102.00   0.50    0.08    --  103.25-108.00-154.00  112
  6  \w     90.00 115.00   0.50    0.08    --  103.25 108.00 -57.00   50
  7  \w    -61.00  14.00   0.50    0.05    --  -47.20  57.00   0.00  150
  8  \w   -110.00 -34.00   0.50    0.05    --  -47.20 -38.00-180.00  152
  9  \w    -39.00  26.00   0.50    0.05    --  -47.20  38.00 -60.00  130
 10  \w   -107.00 -74.00   0.50    0.05    --  -47.20-125.00 120.00   66
 11  \w   -120.00 -95.00   0.50    0.05    --  -47.20-125.00 -90.00   50
 12  \w     28.00 120.00   0.50    0.05    --   47.20  77.00 -60.00  184
 13  \w   -112.00 -86.00   0.50    0.08    --  -99.00 125.00 -60.00   52
 14  \w    -75.00 -49.00   0.50    0.08    --  -99.00 142.00-159.12   52
 15  \w   -124.00 -77.00   0.50    0.08    --  -99.00 142.00-159.12   94
 16  \w    -76.00 -31.00   0.50    0.08    --  -99.00 125.00 150.00   90
 17  \w   -124.00 -74.00   0.50    0.08    --  -99.00 142.00-121.51  100
 18  \w   -124.00 -59.00   0.50    0.08    --  -99.00 144.00 100.00  130
 19  \w   -127.00 -82.00   0.50    0.08    --  -99.00 147.00  57.70   90
 20  \w   -167.00-104.00   0.50    0.08    --  -99.00 -60.00 -40.47  126
 21  \w    -61.00 -35.00   0.50    0.08    --  -99.00 125.00 -60.00   52
 22  \w   -167.00 -87.00   0.50    0.08    --  -99.00 -39.00-122.19  160
 23  \w    -75.00 -49.00   0.50    0.08    --  -99.00 125.00  90.00   52
 24  \w    -55.00 -27.00   0.50    0.08    --  -99.00 142.00-121.51   56
 25  \w   -168.00 -89.00   0.50    0.08    --  -99.00 -56.00 -69.51  158
 26  \w   -112.00 -57.00   0.50    0.08    --  -99.00 125.00  30.00  110
 27  \w     31.00  84.00   0.50    0.08    --  103.25-125.00 -30.00  106
 28  \w     31.00 111.00   0.50    0.08    --  103.25-125.00   0.00  160
 29  \w     31.00  56.00   0.50    0.08    --  103.25 -61.00-180.00   50
 30  \w     46.00  72.00   0.50    0.08    --  103.25-125.00  90.00   52
 31  \w    137.00 169.00   0.50    0.08    --  103.25   0.00-180.00   64
 32  \w    102.00 168.00   0.50    0.08    --  103.25  30.00  30.00  132
 33  \w     74.00 111.00   0.50    0.08    --  103.25-125.00  90.00   74
 34  \w     74.00 133.00   0.50    0.08    --  103.25   0.00-180.00  118
 35  \w     37.00  65.00   0.50    0.08    --  103.25   0.00-180.00   56
 36  \w     32.00  75.00   0.50    0.08    --  103.25 -61.00 120.00   86
 37  \w     31.00  74.00   0.50    0.08    --  103.25 -61.00  90.00   86
 38  \w     40.00  99.00   0.50    0.08    --  103.25-125.00  30.00  118
 39  \w     42.00  74.00   0.50    0.08    --  103.25 -61.00-150.00   64
 40  \w     33.00  70.00   0.50    0.08    --  103.25 -77.00-150.00   74
 41  \w     31.00  74.00   0.50    0.08    --  103.25 -61.00  60.00   86
 42  \w     32.00  77.00   0.50    0.08    --  103.25 -94.00  90.00   90
 43  \w     71.00  96.00   0.50    0.08    --  103.25 -94.00-150.00   50
 44  \w     31.00  89.00   0.50    0.08    --  103.25-125.00  60.00  116
 45  \w     38.00  75.00   0.50    0.08    --  103.25 -61.00   0.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1374398000
_diffrn_orient_matrix_UB_12      -0.0333737000
_diffrn_orient_matrix_UB_13      0.0237262000
_diffrn_orient_matrix_UB_21      0.0133307000
_diffrn_orient_matrix_UB_22      -0.0496816000
_diffrn_orient_matrix_UB_23      0.0820655000
_diffrn_orient_matrix_UB_31      -0.0487682000
_diffrn_orient_matrix_UB_32      0.1032903000
_diffrn_orient_matrix_UB_33      0.0205506000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            37849
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.562
_diffrn_reflns_theta_min         2.520
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.860
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_description       plate
_exptl_crystal_F_000             940
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     604
_refine_ls_number_reflns         10270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0517P)^2^+1.3651P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1141
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9403
_reflns_number_total             10270
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02071h3.cif
_cod_data_source_block           tx2443_sq
_cod_database_code               7130098
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNNi
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.801
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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:
 C2(H2), C3(H3), C6(H6), C7(H7), C11(H11), C12(H12), C21(H21), C23(H23),
 C30(H30), C31(H31), C32(H32), C33(H33), C36(H36), C38(H38), C42(H42), C43(H43),
  C44(H44), C45(H45), C54(H54), C56(H56)
2.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C49(H49A,H49B,
 H49C), C50(H50A,H50B,H50C), C51(H51A,H51B,H51C), C58(H58A,H58B,H58C), C59(H59A,
 H59B,H59C), C60(H60A,H60B,H60C)
;
_shelx_res_checksum              19336
_shelx_fab_checksum              94404
_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 1.839
_oxdiff_exptl_absorpt_empirical_full_min 0.621