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_7130102
_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, 1.5(C6 H14)'
_chemical_formula_sum            'C93 H92 N7 Ni O2'
_chemical_formula_weight         1398.44
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-29
_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                75.1920(10)
_cell_angle_beta                 78.6760(10)
_cell_angle_gamma                86.7300(10)
_cell_formula_units_Z            4
_cell_length_a                   13.9400(3)
_cell_length_b                   22.0062(3)
_cell_length_c                   28.7167(4)
_cell_measurement_reflns_used    23749
_cell_measurement_temperature    170.00(16)
_cell_measurement_theta_max      73.9000
_cell_measurement_theta_min      3.2310
_cell_volume                     8350.7(2)
_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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(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     30.00 114.00   0.50    1.00    --   46.45  65.00  28.00  168
  2  \w     94.00 167.00   0.50    3.00    --  103.25  65.00  28.00  146
  3  \w     87.00 163.00   0.50    3.00    --  103.25  61.00 -30.00  152
  4  \w     94.00 168.00   0.50    3.00    --  103.25  30.00-180.00  148
  5  \w     90.00 165.00   0.50    3.00    --  103.25  15.00 -90.00  150
  6  \w     88.00 168.00   0.50    3.00    --  103.25  61.00 -60.00  160
  7  \w     81.00 107.00   0.50    3.00    --  103.25 -77.00  90.00   52
  8  \w     80.00 107.00   0.50    3.00    --  103.25-125.00  60.00   54
  9  \w     78.00 110.00   0.50    3.00    --  103.25-125.00  30.00   64
 10  \w     65.00  92.00   0.50    3.00    --  103.25 -94.00  30.00   54
 11  \w     36.00  65.00   0.50    3.00    --  103.25-125.00  60.00   58
 12  \w     43.00  70.00   0.50    3.00    --  103.25-125.00 120.00   54
 13  \w     44.00 104.00   0.50    3.00    --  103.25 -94.00 120.00  120
 14  \w     34.00  84.00   0.50    3.00    --  103.25 -77.00 150.00  100
 15  \w     33.00  60.00   0.50    3.00    --  103.25 -77.00  90.00   54
 16  \w     31.00 107.00   0.50    3.00    --  103.25-106.00  34.13  152
 17  \w     45.00  72.00   0.50    3.00    --  103.25 -61.00  30.00   54
 18  \w     47.00  98.00   0.50    3.00    --  103.25-125.00 -60.00  102
 19  \w     32.00  57.00   0.50    3.00    --  103.25 -65.00-106.00   50
 20  \w     34.00  61.00   0.50    3.00    --  103.25 -94.00-120.00   54
 21  \w     32.00  93.00   0.50    3.00    --  103.25 -94.00 -60.00  122
 22  \w     23.00  93.00   0.50    1.00    --   46.45-125.00 -90.00  140
 23  \w     34.00  60.00   0.50    3.00    --  103.25-125.00  30.00   52
 24  \w      6.00  64.00   0.50    1.00    --   46.45 -65.00-106.00  116
 25  \w    -22.00   4.00   0.50    1.00    --   46.45 -65.00-106.00   52
 26  \w    -39.00  27.00   0.50    1.00    --  -46.45  38.00  30.00  132
 27  \w    -17.00  11.00   0.50    1.00    --  -46.45  65.00  28.00   56
 28  \w    -54.00 -27.00   0.50    1.00    --  -46.45  65.00  28.00   54
 29  \w    -74.00 -49.00   0.50    3.00    --  -99.00  65.00  28.00   50
 30  \w    -67.00 -33.00   0.50    3.00    --  -99.00  61.00  90.00   68
 31  \w    -23.00   2.00   0.50    1.00    --  -46.45  19.00 150.00   50
 32  \w   -106.00 -33.00   0.50    1.00    --  -46.45 -57.00 150.00  146
 33  \w   -116.00 -29.00   0.50    1.00    --  -46.45 -65.00-106.00  174
 34  \w    -66.00 -35.00   0.50    3.00    --  -99.00  61.00-150.00   62
 35  \w   -108.00 -26.00   0.50    3.00    --  -99.00 110.00-178.41  164
 36  \w   -111.00 -55.00   0.50    3.00    --  -99.00 125.00 -60.00  112
 37  \w   -120.00 -27.00   0.50    3.00    --  -99.00 136.00  37.95  186
 38  \w   -124.00 -72.00   0.50    3.00    --  -99.00 143.00-130.06  104
 39  \w   -125.00 -70.00   0.50    3.00    --  -99.00 143.00  74.97  110
 40  \w   -127.00 -47.00   0.50    3.00    --  -99.00 146.00 166.78  160
 41  \w   -167.00 -86.00   0.50    3.00    --  -99.00 -49.00 130.39  162
 42  \w   -157.00-117.00   0.50    3.00    --  -99.00 -55.00 143.76   80
 43  \w   -167.00 -89.00   0.50    3.00    --  -99.00 -65.00-106.00  156
;
_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      -0.0843858000
_diffrn_orient_matrix_UB_12      -0.0422720000
_diffrn_orient_matrix_UB_13      0.0326223000
_diffrn_orient_matrix_UB_21      -0.0738210000
_diffrn_orient_matrix_UB_22      0.0428226000
_diffrn_orient_matrix_UB_23      -0.0269030000
_diffrn_orient_matrix_UB_31      0.0115418000
_diffrn_orient_matrix_UB_32      -0.0402851000
_diffrn_orient_matrix_UB_33      -0.0374751000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            123013
_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         75.837
_diffrn_reflns_theta_min         2.936
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69142
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.112
_exptl_crystal_description       plate
_exptl_crystal_F_000             2972
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.152
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.407
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1885
_refine_ls_number_reflns         33267
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.407
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0773
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2076
_refine_ls_wR_factor_ref         0.2231
_reflns_Friedel_coverage         0.000
_reflns_number_gt                22710
_reflns_number_total             33267
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02071h3.cif
_cod_data_source_block           tx2444_sq
_cod_depositor_comments
;

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C186 H184 N14 Ni2 O4'
_cod_original_formula_weight         2796.88
_cod_original_formula_moiety         '2(C84 H71 N7 Ni O2), 3(C6 H14)'
_cod_original_formula_units_Z            2
_cod_database_code               7130102
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNONi
_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, {H82A,H82B,H82C} of C82, All C(H,H) groups
 At 1.5 times of:
  {H26D,H26E,H26F} of C26A, {H27D,H27E,H27F} of C27A, {H25D,H25E,H25F} of
  C25A, {H51D,H51E,H51F} of C51A, {H49D,H49E,H49F} of C49A, {H58D,H58E,H58F} of
  C58A, {H59D,H59E,H59F} of C59A, {H60D,H60E,H60F} of C60A, {H50D,H50E,H50F} of
  C50A, {H10E,H10F,H10G} of C102, {H91A,H91B,H91C} of C91, {H85A,H85B,H85C} of
  C85, {H82D,H82E,H82F} of C82A, {H90A,H90B,H90C} of C90, {H83D,H83E,H83F} of
  C83A, {H84D,H84E,H84F} of C84A, {H97A,H97B,H97C} of C97, {H96A,H96B,H96C} of
  C96, {H49A,H49B,H49C} of C49, {H25A,H25B,H25C} of C25, {H27A,H27B,H27C} of
  C27, {H26A,H26B,H26C} of C26, {H59A,H59B,H59C} of C59, {H50A,H50B,H50C} of
  C50, {H51A,H51B,H51C} of C51, {H58A,H58B,H58C} of C58, {H60A,H60B,H60C} of
  C60, {H83A,H83B,H83C} of C83, {H84A,H84B,H84C} of C84
2. Rigid bond restraints
 C23, C22
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C16(H16), C17(H17), C28(H28), C47(H47), C61(H61), C80(H80),
 C7A(H7A), C8A(H8A), C16A(H16A), C17A(H17A), C28A(H28A), C47A(H47A), C61A(H61A),
  C80A(H80A)
3.b Secondary CH2 refined with riding coordinates:
 C86(H86A,H86B), C87(H87A,H87B), C88(H88A,H88B), C89(H89A,H89B), C92(H92A,
 H92B), C93(H93A,H93B), C94(H94A,H94B), C95(H95A,H95B), C98(H98A,H98B),
 C99(H99A,H99B), C100(H10A,H10B), C101(H10C,H10D)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), 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), C63(H63), C64(H64), C65(H65), C66(H66), C69(H69), C71(H71),
 C75(H75), C76(H76), C77(H77), C78(H78), C2A(H2A), C11A(H11A), C12A(H12A),
 C21A(H21A), C23A(H23A), C30A(H30A), C31A(H31A), C32A(H32A), C33A(H33A),
 C36A(H36A), C38A(H38A), C42A(H42A), C43A(H43A), C44A(H44A), C45A(H45A),
 C54A(H54A), C56A(H56A), C63A(H63A), C64A(H64A), C65A(H65A), C66A(H66A),
 C69A(H69A), C71A(H71A), C75A(H75A), C76A(H76A), C77A(H77A), C78A(H78A)
3.d 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), C82(H82A,H82B,H82C), C83(H83A,H83B,H83C),
 C84(H84A,H84B,H84C), C25A(H25D,H25E,H25F), C26A(H26D,H26E,H26F), C27A(H27D,
 H27E,H27F), C49A(H49D,H49E,H49F), C50A(H50D,H50E,H50F), C51A(H51D,H51E,H51F),
 C58A(H58D,H58E,H58F), C59A(H59D,H59E,H59F), C60A(H60D,H60E,H60F), C82A(H82D,
 H82E,H82F), C83A(H83D,H83E,H83F), C84A(H84D,H84E,H84F), C85(H85A,H85B,H85C),
 C90(H90A,H90B,H90C), C91(H91A,H91B,H91C), C96(H96A,H96B,H96C), C97(H97A,H97B,
 H97C), C102(H10E,H10F,H10G)
;
_shelx_res_checksum              37482
_shelx_fab_checksum              60948
_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 1.936
_oxdiff_exptl_absorpt_empirical_full_min 0.537