Synthesis, Photophysical and Electrochemistry of Near-IR Absorbing Bacteriochlorins Related to Bacteriochlorophylla
Andrei Kozyrev; Manivannan Ethirajan; Ping Chen; Kei Ohkubo; Byron C. Robinson; Kathleen M. Barkigia; Shunichi Fukuzumi; Karl M. Kadish; Ravindra K. Pandey; Journal of Organic Chemistry 77 (2012) 10260–10271; doi:10.1021/jo301895p

data_4027727
_publ_contact_author
;
 K.M. Barkigia (regarding the crystallographic data and cif)
 Materials Science Dept.
 Molecular Materials Division
 Bldg. 555
 Brookhaven National Laboratory
 Upton, NY 11973 USA
;
_publ_contact_author_email       barkigia@bnl.gov
_publ_contact_author_fax         631-344-5815
_publ_contact_author_phone       631-344-7661
_publ_section_title
;
 Synthesis, Photophysical and Electrochemistry of Near-IR Absorbing
 Bacteriochlorins Related to Bacteriochlorophylla
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10260
_journal_page_last               10271
_journal_paper_doi               10.1021/jo301895p
_journal_volume                  77
_journal_year                    2012
_chemical_compound_source        'methylene chloride/methanol'
_chemical_formula_moiety         'C36 H40 N4 O5'
_chemical_formula_sum            'C36 H40 N4 O5'
_chemical_formula_weight         608.72
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                77.55(1)
_cell_angle_beta                 82.90(1)
_cell_angle_gamma                76.99(1)
_cell_formula_units_Z            3
_cell_length_a                   7.326(1)
_cell_length_b                   15.248(1)
_cell_length_c                   22.073(1)
_cell_measurement_reflns_used    62294
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.98
_cell_measurement_theta_min      2.4
_cell_volume                     2338.6(4)
_computing_cell_refinement
'Denzo/Scalepack (Otwinowski and Minor, 1997)'
_computing_data_collection
'  Software developed by Skinner et al. (1993) was used to run the beamline.'
_computing_data_reduction
'Denzo/Scalepack (Otwinowski and Minor, 1997)'
_computing_molecular_graphics
'SHELXTL Version 5.0 and other inhouse programs'
_computing_publication_material  'SHELXTL Version 5.0'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SnB (Weeks et al., 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_device       'Quantum 315 detector'
_diffrn_measurement_method       rotation
_diffrn_radiation_monochromator  Si(III)
_diffrn_radiation_source         'x-rays from beamline X25 at the NSLS'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.90000
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            62294
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_min         2.40
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       'miniscule plate'
_exptl_crystal_F_000             972
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.007
_refine_diff_density_max         1.258
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(81)
_refine_ls_extinction_coef       0.0931(62)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.060
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1243
_refine_ls_number_reflns         9691
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.060
_refine_ls_restrained_S_obs      1.051
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0782
_refine_ls_shift/esd_mean        0.007
_refine_ls_shift/su_max          0.040
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
' w=1/[\s^2^(Fo^2^)+(0.1620P)^2^+1.8112P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2091
_refine_ls_wR_factor_ref         0.2037
_reflns_number_gt                9379
_reflns_number_total             9691
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301895p_si_002.cif
_cod_data_source_block           14fin
_cod_database_code               4027727