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_7130095
_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 H71 N7 Ni O2, C6 H14'
_chemical_formula_sum            'C90 H85 N7 Ni O2'
_chemical_formula_weight         1355.35
_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                109.234(2)
_cell_angle_beta                 102.943(2)
_cell_angle_gamma                103.838(2)
_cell_formula_units_Z            1
_cell_length_a                   12.3458(2)
_cell_length_b                   12.9810(2)
_cell_length_c                   16.1260(3)
_cell_measurement_reflns_used    19648
_cell_measurement_temperature    169.99(16)
_cell_measurement_theta_max      75.0430
_cell_measurement_theta_min      3.8010
_cell_volume                     2236.35(9)
_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)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.956
_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    -82.00 -57.00   0.50    0.05    --  -46.95 132.00 -68.00   50
  2  \w   -118.00 -93.00   0.50    0.05    --  -46.95-132.00-138.00   50
  3  \w   -105.00 -80.00   0.50    0.05    --  -46.95-138.00  45.00   50
  4  \w    -85.00 -60.00   0.50    0.05    --  -46.95 138.00 107.00   50
  5  \w     72.00  97.00   0.50    0.05    --   46.95 138.00 107.00   50
  6  \w     49.00  99.00   0.50    0.05    --   46.95-138.00  45.00  100
  7  \w     24.00  95.00   0.50    0.05    --   46.95-132.00-138.00  142
  8  \w   -116.00 -28.00   0.50    0.10    --  -99.00 132.00 -68.00  176
  9  \w    -83.00 -29.00   0.50    0.10    --  -99.00 138.00 107.00  108
 10  \w   -121.00 -88.00   0.50    0.10    --  -99.00 138.00 107.00   66
 11  \w   -141.00-116.00   0.50    0.10    --  -99.00-138.00  45.00   50
 12  \w    116.00 144.00   0.50    0.10    --  103.25 138.00 107.00   56
 13  \w     96.00 121.00   0.50    0.10    --  103.25-138.00  45.00   50
 14  \w     50.00  75.00   0.50    0.10    --  103.25-132.00-138.00   50
 15  \w     81.00 123.00   0.50    0.10    --  103.25 132.00 -68.00   84
 16  \w   -110.00 -74.00   0.50    0.05    --  -46.95-125.00  60.00   72
 17  \w    -19.00  25.00   0.50    0.05    --  -46.95  19.00-180.00   88
 18  \w    -22.00  28.00   0.50    0.05    --  -46.95  19.00 -60.00  100
 19  \w    -11.00  27.00   0.50    0.05    --   46.95 -19.00   0.00   76
 20  \w    -26.00  18.00   0.50    0.05    --   46.95 -19.00 -30.00   88
 21  \w     25.00 119.00   0.50    0.05    --   46.95  77.00 -60.00  188
 22  \w   -110.00 -29.00   0.50    0.10    --  -99.00 125.00 -90.00  162
 23  \w    -54.00 -27.00   0.50    0.10    --  -99.00 125.00-180.00   54
 24  \w   -168.00 -85.00   0.50    0.10    --  -99.00 -15.00 -90.00  166
 25  \w   -161.00-111.00   0.50    0.10    --  -99.00 -94.00 -30.00  100
 26  \w    -79.00 -27.00   0.50    0.10    --  -99.00  77.00  60.00  104
 27  \w   -167.00 -93.00   0.50    0.10    --  -99.00 -69.00-145.04  148
 28  \w   -126.00-100.00   0.50    0.10    --  -99.00 147.00  42.84   52
 29  \w   -126.00 -63.00   0.50    0.10    --  -99.00 144.00 128.90  126
 30  \w   -143.00-118.00   0.50    0.10    --  -99.00-132.00-138.00   50
 31  \w   -168.00 -99.00   0.50    0.10    --  -99.00 -30.00  90.00  138
 32  \w   -111.00 -43.00   0.50    0.10    --  -99.00 125.00 -30.00  136
 33  \w   -164.00 -85.00   0.50    0.10    --  -99.00 -94.00-180.00  158
 34  \w    -56.00 -28.00   0.50    0.10    --  -99.00 147.00  42.84   56
 35  \w    -68.00 -40.00   0.50    0.10    --  -99.00  61.00 150.00   56
 36  \w   -112.00 -59.00   0.50    0.10    --  -99.00 125.00-180.00  106
 37  \w     33.00  59.00   0.50    0.10    --  103.25-125.00  90.00   52
 38  \w     50.00  76.00   0.50    0.10    --  103.25-125.00 120.00   52
 39  \w     34.00  73.00   0.50    0.10    --  103.25 -94.00  60.00   78
 40  \w     31.00  75.00   0.50    0.10    --  103.25 -61.00-180.00   88
 41  \w     36.00  75.00   0.50    0.10    --  103.25 -61.00-120.00   78
 42  \w     34.00 109.00   0.50    0.10    --  103.25 -77.00  60.00  150
 43  \w     77.00 110.00   0.50    0.10    --  103.25-125.00 120.00   66
 44  \w     71.00  97.00   0.50    0.10    --  103.25 -94.00-120.00   52
 45  \w     35.00  87.00   0.50    0.10    --  103.25 -77.00-120.00  104
 46  \w     32.00  70.00   0.50    0.10    --  103.25 -61.00  90.00   76
 47  \w     35.00  74.00   0.50    0.10    --  103.25 -61.00 120.00   78
 48  \w     66.00 100.00   0.50    0.10    --  103.25-125.00  90.00   68
 49  \w     82.00 169.00   0.50    0.10    --  103.25  77.00   0.00  174
;
_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      0.0261995000
_diffrn_orient_matrix_UB_12      -0.0975409000
_diffrn_orient_matrix_UB_13      0.0261943000
_diffrn_orient_matrix_UB_21      0.0428431000
_diffrn_orient_matrix_UB_22      0.0813970000
_diffrn_orient_matrix_UB_23      0.1039150000
_diffrn_orient_matrix_UB_31      -0.1265538000
_diffrn_orient_matrix_UB_32      -0.0415441000
_diffrn_orient_matrix_UB_33      0.0025139000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33345
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.441
_diffrn_reflns_theta_min         3.824
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76741
_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    1.006
_exptl_crystal_description       rod
_exptl_crystal_F_000             718
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.846
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     504
_refine_ls_number_reflns         8863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0666
_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^)+(0.1233P)^2^+0.7657P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1933
_refine_ls_wR_factor_ref         0.1966
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8055
_reflns_number_total             8863
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02071h3.cif
_cod_data_source_block           tx2499_sq
_cod_original_cell_volume        2236.35(7)
_cod_database_code               7130095
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C31A)=Sof(H31D)=Sof(H31E)=Sof(H31F)=Sof(C32A)=Sof(H32D)=Sof(H32E)=
 Sof(H32F)=Sof(C30A)=Sof(H30D)=Sof(H30E)=Sof(H30F)=1-FVAR(1)
 Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=
 Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(H32C)=FVAR(1)
 Fixed Sof: O1(0.5) O2(0.5) N3(0.5) H2(0.5)
3.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C27(H27)
3.b Secondary CH2 refined with riding coordinates:
 C44(H44A,H44B), C45(H45A,H45B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C11(H11), C12(H12), C13(H13), C14(H14), C17(H17), C19(H19),
 C22(H22), C23(H23), C24(H24), C25(H25), C36(H36), C38(H38)
3.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C40(H40A,H40B,
 H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C),
 C31A(H31D,H31E,H31F), C32A(H32D,H32E,H32F), C30A(H30D,H30E,H30F)
;
_shelx_res_checksum              53616
_shelx_fab_checksum              14280
_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 1.539
_oxdiff_exptl_absorpt_empirical_full_min 0.678