Cyclo[m]pyridine[n]pyrroles: Hybrid Macrocycles That Display Expanded π-Conjugation upon Protonation
Zhan Zhang; Jong Min Lim; Masatoshi Ishida; Vladimir V. Roznyatovskiy; Vincent M. Lynch; Han-Yuan Gong; Xiaoping Yang; Dongho Kim; Jonathan L. Sessler; Journal of the American Chemical Society 134 (2012) 4076–4079; doi:10.1021/ja211985k

data_4117609
_publ_contact_author_address
;Department of Chemistry and Biochemistry,
University of Texas at Austin,
1 University Station A5300, Austin
TX 78712 USA
;
_publ_contact_author_email       sessler@mail.utexas.edu
_publ_contact_author_fax         1-512-471-6835
_publ_contact_author_name        'Jonathan L. Sessler'
_publ_section_title
;
 Cyclo[m]pyridine[n]pyrroles: Hybrid Macrocycles That Display Expanded
 \p-Conjugation upon Protonation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4076
_journal_page_last               4079
_journal_paper_doi               10.1021/ja211985k
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C23 H30 Cl3 N3 O3 S'
_chemical_formula_weight         534.91
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.000(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.6300(15)
_cell_length_b                   16.2000(19)
_cell_length_c                   12.8300(15)
_cell_measurement_reflns_used    41438
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.00
_cell_volume                     2535.6(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku SCX-Mini with Mercury CCD'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            41438
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.474
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Abscor.  T. Higashi (2001).  The Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         5774
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0440P)^2^+1.1233P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0974
_reflns_number_gt                4708
_reflns_number_total             5774
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja211985k_si_007.cif
_cod_data_source_block           5-2MSA
_cod_database_code               4117609