meso-Triaryl-Substituted Smaragdyrins: Facile Aromaticity Switching.
Xie, Daguan; Liu, Yang; Rao, Yutao; Kim, Gakhyun; Zhou, Mingbo; Yu, Donghai; Xu, Ling; Yin, Bangshao; Liu, Shubin; Tanaka, Takayuki; Aratani, Naoki; Osuka, Atsuhiro; Liu, Qingyun; Kim, Dongho; Song, Jianxin; Journal of the American Chemical Society 140 (2018) 16553–16559; doi:10.1021/jacs.8b07973

data_4133020
_publ_section_title
;
 meso-Triaryl-Substituted Smaragdyrins: Facile Aromaticity Switching.
;
_journal_issue                   48
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16553
_journal_page_last               16559
_journal_paper_doi               10.1021/jacs.8b07973
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C H Cl3, C50 H46 B F2 N5'
_chemical_formula_sum            'C51 H47 B Cl3 F2 N5'
_chemical_formula_weight         885.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;
_cell_angle_alpha                90
_cell_angle_beta                 117.612(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.1823(4)
_cell_length_b                   15.6106(2)
_cell_length_c                   17.7090(4)
_cell_measurement_reflns_used    11486
_cell_measurement_temperature    291.80(10)
_cell_measurement_theta_max      72.4170
_cell_measurement_theta_min      3.9840
_cell_volume                     4453.98(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.80(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
  1 omega   23.00   88.00   1.0000    2.4300
omega____ theta____ kappa____ phi______ frames
    -       34.4807 -125.0000   90.0000 65

  2 omega   10.00   79.00   1.0000    2.4300
omega____ theta____ kappa____ phi______ frames
    -       34.4807 -109.0000  142.0000 69

  3 omega  -35.00   53.00   1.0000    2.4300
omega____ theta____ kappa____ phi______ frames
    -       34.4807  -38.0000    0.0000 88

  4 omega    1.00   73.00   1.0000    2.4300
omega____ theta____ kappa____ phi______ frames
    -       34.4807  -99.0000  -90.0000 72

  5 omega    1.00   73.00   1.0000    2.4300
omega____ theta____ kappa____ phi______ frames
    -       34.4807  -99.0000  -60.0000 72

  6 omega   18.00  102.00   1.0000    2.4300
omega____ theta____ kappa____ phi______ frames
    -       34.4807   57.0000 -120.0000 84

  7 omega  -33.00   51.00   1.0000    2.4300
omega____ theta____ kappa____ phi______ frames
    -       34.4807  -57.0000    0.0000 84

  8 omega    1.00   73.00   1.0000    2.4300
omega____ theta____ kappa____ phi______ frames
    -       34.4807  -99.0000 -120.0000 72

  9 omega   18.00  102.00   1.0000    2.4300
omega____ theta____ kappa____ phi______ frames
    -       34.4807   57.0000  -60.0000 84

 10 omega   90.00  176.00   1.0000    9.7300
omega____ theta____ kappa____ phi______ frames
    -      107.4557   45.0000  -30.0000 86

 11 omega   39.00   98.00   1.0000    9.7300
omega____ theta____ kappa____ phi______ frames
    -      107.4557  -45.0000  -90.0000 59

 12 omega   81.00  175.00   1.0000    9.7300
omega____ theta____ kappa____ phi______ frames
    -      107.4557   77.0000  -90.0000 94

 13 omega   38.00  109.00   1.0000    9.7300
omega____ theta____ kappa____ phi______ frames
    -      107.4557  -94.0000   30.0000 71

 14 omega   38.00   91.00   1.0000    9.7300
omega____ theta____ kappa____ phi______ frames
    -      107.4557  -30.0000 -150.0000 53

 15 omega   49.00  115.00   1.0000    9.7300
omega____ theta____ kappa____ phi______ frames
    -      107.4557 -111.0000 -150.0000 66

 16 omega   38.00   96.00   1.0000    9.7300
omega____ theta____ kappa____ phi______ frames
    -      107.4557 -111.0000 -120.0000 58

 17 omega   46.00  126.00   1.0000    9.7300
omega____ theta____ kappa____ phi______ frames
    -      107.4557  -61.0000    0.0000 80

 18 omega  104.00  176.00   1.0000    9.7300
omega____ theta____ kappa____ phi______ frames
    -      107.4557   45.0000  150.0000 72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0913617000
_diffrn_orient_matrix_UB_12      -0.0176396000
_diffrn_orient_matrix_UB_13      0.0229681000
_diffrn_orient_matrix_UB_21      0.0182238000
_diffrn_orient_matrix_UB_22      0.0967946000
_diffrn_orient_matrix_UB_23      0.0112978000
_diffrn_orient_matrix_UB_31      0.0215745000
_diffrn_orient_matrix_UB_32      -0.0073286000
_diffrn_orient_matrix_UB_33      0.0947827000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25185
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.574
_diffrn_reflns_theta_min         4.997
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.267
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1848
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.740
_refine_diff_density_min         -1.784
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     568
_refine_ls_number_reflns         8660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0732
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0996P)^2^+9.9184P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1980
_refine_ls_wR_factor_ref         0.2100
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7068
_reflns_number_total             8660
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b07973_si_002.cif
_cod_data_source_block           3
_cod_original_cell_volume        4454.00(17)
_cod_database_code               4133020
_chemical_oxdiff_formula         'C50 H46 N5 B F2'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 N20(H20), N16(H16), N12(H12), C61(H61), C39(H39), C9(H9), C38(H38), C54(H54),
 C23(H23), C24(H24), C42(H42), C62(H62), C27(H27), C52(H52), C8(H8), C33(H33),
 C31(H31), C28(H28), C44(H44)
2.c Idealised Me refined as rotating group:
 C48(H48A,H48B,H48C), C36(H36A,H36B,H36C), C58(H58A,H58B,H58C), C37(H37A,H37B,
 H37C), C56(H56A,H56B,H56C), C35(H35A,H35B,H35C), C46(H46A,H46B,H46C), C57(H57A,
 H57B,H57C), C47(H47A,H47B,H47C)
;
_shelx_res_checksum              5061
_shelx_hkl_checksum              84113
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'