Protonation Dependent Topological Dichotomy of Core Modified Hexaphyrins: Synthesis, Characterization, and Excited State Dynamics.
Mallick, Abhijit; Oh, Juwon; Majewski, Marcin A.; Stępień, Marcin; Kim, Dongho; Rath, Harapriya; The Journal of organic chemistry 82 (2017) 556–566; doi:10.1021/acs.joc.6b02576

data_4032108
_publ_section_title
;
 Protonation Dependent Topological Dichotomy of Core Modified Hexaphyrins:
 Synthesis, Characterization, and Excited State Dynamics.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              556
_journal_page_last               566
_journal_paper_doi               10.1021/acs.joc.6b02576
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C82 H58 F10 N4 S4, 2(C H2 Cl2)'
_chemical_formula_sum            'C84 H62 Cl4 F10 N4 S4'
_chemical_formula_weight         1587.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-09-19
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 126.247(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   33.509(4)
_cell_length_b                   13.9343(14)
_cell_length_c                   20.097(3)
_cell_measurement_reflns_used    1743
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      18.50
_cell_measurement_theta_min      2.60
_cell_volume                     7567.8(17)
_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_temperature      100.15
_diffrn_measured_fraction_theta_full 0.697
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1714
_diffrn_reflns_av_unetI/netI     0.0966
_diffrn_reflns_Laue_measured_fraction_full 0.697
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            33764
_diffrn_reflns_point_group_measured_fraction_full 0.697
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         22.231
_diffrn_reflns_theta_min         1.507
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_T_max  0.7447
_exptl_absorpt_correction_T_min  0.5987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0769 before and 0.0603 after correction.
The Ratio of minimum to maximum transmission is 0.8039.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       irregular
_exptl_crystal_F_000             3264
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.813
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         4774
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1640
_refine_ls_R_factor_gt           0.0856
_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^)+(0.1468P)^2^+61.3335P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2279
_refine_ls_wR_factor_ref         0.2921
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2665
_reflns_number_total             4774
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02576_si_002.cif
_cod_data_source_block           HR_91
_cod_depositor_comments          'Adding full bibliography for 4032108.cif.'
_cod_original_cell_volume        7567.7(15)
_cod_database_code               4032108
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N3-H3
 0.88 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(C2) = Uanis(C3) = Uanis(C4) = Uanis(C5) = Uanis(C6)
4.a Secondary CH2 refined with riding coordinates:
 C43(H43A,H43B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C9(H9), C10(H10), C14(H14), C15(H15), C26(H26), C29(H29),
 C36(H36), C39(H39)
4.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C28(H28A,H28B,H28C), C31(H31A,H31B,H31C), C35(H35A,H35B,
 H35C), C38(H38A,H38B,H38C), C41(H41A,H41B,H41C)
;
_shelx_res_checksum              23241
_shelx_hkl_checksum              90603