Highly Strained, Radially π-Conjugated Porphyrinylene Nanohoops.
Xu, Youzhi; Gsänger, Sebastian; Minameyer, Martin B.; Imaz, Inhar; Maspoch, Daniel; Shyshov, Oleksandr; Schwer, Fabian; Ribas, Xavi; Drewello, Thomas; Meyer, Bernd; von Delius, Max; Journal of the American Chemical Society 141 (2019) 18500–18507; doi:10.1021/jacs.9b08584

data_4129084
_publ_section_title
;
 Highly Strained, Radially \p-Conjugated Porphyrinylene Nanohoops.
;
_journal_issue                   46
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18500
_journal_page_last               18507
_journal_paper_doi               10.1021/jacs.9b08584
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C66 H64 N4 Ni O2, C2 H3 N'
_chemical_formula_sum            'C68 H67 N5 Ni O2'
_chemical_formula_weight         1044.97
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-11-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                94.574(3)
_cell_angle_beta                 103.809(3)
_cell_angle_gamma                110.373(3)
_cell_formula_units_Z            2
_cell_length_a                   14.9071(5)
_cell_length_b                   15.8745(5)
_cell_length_c                   18.8299(6)
_cell_measurement_reflns_used    9765
_cell_measurement_temperature    150.00(14)
_cell_measurement_theta_max      73.4570
_cell_measurement_theta_min      3.2610
_cell_volume                     3991.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_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    -72.00 -32.00   1.00    1.00    --  -43.06 125.00-180.00   40
  2  \w   -112.00 -20.00   1.00    1.00    --  -43.06 -57.00   0.00   92
  3  \w   -124.00 -80.00   1.00    1.00    --  -43.06 -99.00  90.00   44
  4  \w   -117.00 -90.00   1.00    1.00    --  -43.06 -99.00 150.00   27
  5  \w    -70.00  30.00   1.00    1.00    --  -43.06  57.00 150.00  100
  6  \w      8.00  77.00   1.00    1.00    --   43.06 -99.00 -90.00   69
  7  \w    107.00 178.00   1.00    4.00    --  107.13  45.00 -60.00   71
  8  \w     89.00 115.00   1.00    4.00    --  107.13 -61.00 -30.00   26
  9  \w     33.00 120.00   1.00    4.00    --  107.13 -77.00 120.00   87
 10  \w    149.00 175.00   1.00    4.00    --  107.13  77.00 -30.00   26
 11  \w     40.00 113.00   1.00    4.00    --  107.13-125.00 120.00   73
 12  \w     79.00 142.00   1.00    4.00    --  107.13  61.00-180.00   63
 13  \w    150.00 178.00   1.00    4.00    --  107.13  61.00-180.00   28
 14  \w     79.00 127.00   1.00    4.00    --  107.13  77.00 -30.00   48
 15  \w     35.00  93.00   1.00    4.00    --  107.13-125.00  60.00   58
 16  \w     35.00  60.00   1.00    4.00    --  107.13-125.00 150.00   25
 17  \w     44.00 117.00   1.00    4.00    --  107.13 -45.00-180.00   73
 18  \w     70.00 117.00   1.00    4.00    --  107.13-125.00 -60.00   47
 19  \w     28.00 109.00   1.00    4.00    --  107.13 -95.00 -30.00   81
 20  \w     88.00 176.00   1.00    4.00    --  107.13   0.00  90.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0198742000
_diffrn_orient_matrix_UB_12      0.0257289000
_diffrn_orient_matrix_UB_13      0.0844999000
_diffrn_orient_matrix_UB_21      -0.1123078000
_diffrn_orient_matrix_UB_22      -0.0482007000
_diffrn_orient_matrix_UB_23      -0.0086148000
_diffrn_orient_matrix_UB_31      0.0148409000
_diffrn_orient_matrix_UB_32      -0.0899209000
_diffrn_orient_matrix_UB_33      0.0108728000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0716
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            28109
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.486
_diffrn_reflns_theta_min         3.018
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.683
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    0.870
_exptl_crystal_description       block
_exptl_crystal_F_000             1108
_exptl_crystal_preparation       'Vapour diffusion'
_exptl_crystal_recrystallization_method acetonitril/chloroform/THF
_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.115
_refine_diff_density_max         1.119
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     728
_refine_ls_number_reflns         15606
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0764
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1293P)^2^+5.2736P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2374
_refine_ls_wR_factor_ref         0.2569
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11333
_reflns_number_total             15606
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b08584_si_002.cif
_cod_data_source_block           yol18052
_cod_depositor_comments
'Adding full bibliography for 4129084--4129086.cif.'
_cod_original_cell_volume        3991.1(2)
_cod_database_code               4129084
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C132 H128 N8 Ni O4'
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2. Restrained distances
 C13-C12 \\sim C12-N1
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 N1, C12, C13
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: N1(0.5) C12(0.5) C13(0.5) H13A(0.5) H13B(0.5) H13C(0.5) N2(0.5)
 C3(0.5) C4(0.5) H4A(0.5) H4B(0.5) H4C(0.5)
5.a Free rotating group:
 N1(C12,C13), N2(C3,C4,H4A,H4B,H4C)
5.b Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00P(H00P), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z),
 C014(H014), C015(H015), C016(H016), C017(H017), C(H), C01A(H01A), C01B(H01B),
 C01E(H01E), C01F(H01F), C01G(H01G), C01H(H01H), C01I(H01I), C01J(H01J),
 C01K(H01K), C01L(H01L), C01M(H01M), C01O(H01O), C1(H1), C2AA(H2AA)
5.c Idealised Me refined as rotating group:
 C01U(H01C,H01D,H01N), C01V(H01P,H01Q,H01R), C01W(H01S,H01T,H01U), C01X(H01V,
 H01W,H01X), C01Y(H01Y,HA,HB), C01Z(H01Z,HC,HD), C13(H13A,H13B,H13C), C4AA(H4AA,
 H4AB,H4AC), C5AA(H5AA,H5AB,H5AC), C6AA(H6AA,H6AB,H6AC), C9AA(H9AA,H9AB,H9AC),
 C8AA(H8AA,H8AB,H8AC), C0BA(H0BA,H0BB,H0BC)
5.d Idealised tetrahedral OH refined as rotating group:
 O003(H003), O2BA(H2BA)
;
_shelx_res_checksum              98297
_shelx_hkl_checksum              65622
_shelx_fab_checksum              49080
_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 1.767
_oxdiff_exptl_absorpt_empirical_full_min 0.389