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_7130097
_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 H51 N5 Ni'
_chemical_formula_sum            'C60 H51 N5 Ni'
_chemical_formula_weight         900.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_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                90
_cell_angle_beta                 105.144(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9639(3)
_cell_length_b                   27.0997(6)
_cell_length_c                   16.6678(5)
_cell_measurement_reflns_used    20173
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      74.9900
_cell_measurement_theta_min      3.1460
_cell_volume                     4780.3(2)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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     10.00  35.00   0.50   34.00    --   59.64 -30.00  30.00   50
  2  \w     12.00  37.00   0.50   34.00    --   59.64 -30.00-150.00   50
  3  \w     62.00  97.00   0.50   34.00    --   59.64  30.00  90.00   70
  4  \w     10.00  35.00   0.50   34.00    --   59.64 -30.00 -30.00   50
  5  \w     10.00  35.00   0.50   34.00    --   59.64 -30.00-120.00   50
  6  \w     63.00 109.00   0.50   34.00    --   59.64  30.00-180.00   92
  7  \w     45.00  80.00   0.50   34.00    --   74.25 -95.00-180.00   70
  8  \w     47.00  81.00   0.50   34.00    --   74.25 -95.00 -90.00   68
  9  \w   -121.00 -94.00   0.50   34.00    --  -75.31-125.00  60.00   54
 10  \w   -112.00 -77.00   0.50   34.00    --  -75.31-125.00   0.00   70
 11  \w   -121.00 -96.00   0.50   34.00    --  -75.31-125.00-120.00   50
 12  \w     79.00 105.00   0.50   34.00    --   79.20 125.00 -60.00   52
 13  \w     40.00  74.00   0.50   34.00    --   79.20 -95.00  30.00   68
 14  \w     40.00  66.00   0.50   34.00    --   79.20 -95.00   0.00   52
 15  \w     41.00  71.00   0.50   34.00    --   79.20 -95.00-120.00   60
 16  \w     33.00  68.00   0.50   34.00    --   79.20-125.00-180.00   70
 17  \w     79.00 104.00   0.50   34.00    --   79.20 125.00-180.00   50
 18  \w     95.00 120.00   0.50   34.00    --   79.20  30.00-180.00   50
 19  \w     89.00 115.00   0.50   34.00    --   79.20  30.00-120.00   52
 20  \w     80.00 115.00   0.50   34.00    --   79.20  30.00-150.00   70
 21  \w     79.00 104.00   0.50   34.00    --   79.20 125.00 -30.00   50
 22  \w     85.00 110.00   0.50   34.00    --   79.20-125.00-180.00   50
 23  \w     67.00 108.00   0.50   34.00    --   82.00-118.00 108.61   82
 24  \w     77.00 122.00   0.50   34.00    --   83.00   1.00-108.21   90
 25  \w     44.00  70.00   0.50   34.00    --   83.00   1.00-108.21   52
 26  \w     99.00 126.00   0.50   34.00    --   83.00  22.00  38.06   54
 27  \w     64.00  92.00   0.50   34.00    --   83.00  22.00  38.06   56
 28  \w     72.00  98.00   0.50   34.00    --   83.00-170.00 -21.80   52
 29  \w     72.00 127.00   0.50   34.00    --   83.00  22.00 154.18  110
 30  \w     99.00 125.00   0.50   34.00    --   83.00   7.00 -46.88   52
 31  \w     55.00  86.00   0.50   34.00    --   83.00   7.00 -46.88   62
 32  \w     39.00  65.00   0.50   34.00    --   83.00 -55.00 138.65   52
 33  \w     85.00 118.00   0.50   34.00    --   83.00  15.00-143.33   66
 34  \w     79.00 114.00   0.50   34.00    --   83.00  20.00  97.49   70
 35  \w     97.00 126.00   0.50   34.00    --   83.00  44.00  84.89   58
 36  \w     87.00 128.00   0.50   34.00    --   83.00 111.00-155.00   82
 37  \w     52.00  76.50   0.50   34.00    --   83.00 -83.00 134.50   49
;
_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      -0.0861614000
_diffrn_orient_matrix_UB_12      0.0458140000
_diffrn_orient_matrix_UB_13      -0.0122193000
_diffrn_orient_matrix_UB_21      0.0397245000
_diffrn_orient_matrix_UB_22      0.0095511000
_diffrn_orient_matrix_UB_23      0.0943568000
_diffrn_orient_matrix_UB_31      0.1103493000
_diffrn_orient_matrix_UB_32      0.0323419000
_diffrn_orient_matrix_UB_33      -0.0104853000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0919
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            38217
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        62.493
_diffrn_reflns_theta_max         62.493
_diffrn_reflns_theta_min         3.194
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.925
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_correction_T_min  0.831
_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            brown
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       block
_exptl_crystal_F_000             1896
_exptl_crystal_size_max          0.284
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.118
_refine_diff_density_max         1.311
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     607
_refine_ls_number_reflns         7595
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0834
_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^)+(0.0722P)^2^+15.5526P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1930
_refine_ls_wR_factor_ref         0.2029
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6373
_reflns_number_total             7595
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02071h3.cif
_cod_data_source_block           1abs_sq
_cod_original_cell_volume        4780.4(2)
_cod_database_code               7130097
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N Ni'
_reflns_odcompleteness_completeness 98.05
_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 Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C21(H21), C44(H44)
2.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C7(H7), C8(H8), C11(H11), C12(H12), C17(H17), C24(H24), C25(H25),
 C26(H26), C31(H31), C33(H33), C39(H39), C40(H40), C41(H41), C42(H42), C53(H53),
  C55(H55), C143(H143), C145(H145)
2.c Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C57(H57A,H57B,
 H57C), C58(H58A,H58B,H58C), C59(H59A,H59B,H59C), C147(H14A,H14B,H14C),
 C148(H14D,H14E,H14F), C149(H14G,H14H,H14I)
;
_shelx_res_checksum              5616
_shelx_fab_checksum              16412
_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 2.059
_oxdiff_exptl_absorpt_empirical_full_min 0.320