Synthesis of Locked meso-β-Substituted Chlorins via 1,3-Dipolar Cycloaddition
Michał Gałȩzowski; Daniel T. Gryko; Journal of Organic Chemistry 71 (2006) 5942–5950; doi:10.1021/jo060545x

data_4021834
_publ_section_title
;
 Synthesis of Locked meso-\b-Substituted Chlorins via
 1,3-Dipolar Cycloaddition
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5942
_journal_page_last               5950
_journal_paper_doi               10.1021/jo060545x
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C45 H36 F3 N7 O6'
_chemical_formula_weight         827.81
_chemical_name_common            chlorin45
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 93.011(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   33.411(4)
_cell_length_b                   7.6918(6)
_cell_length_c                   32.527(5)
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.99
_cell_measurement_theta_min      2.72
_cell_volume                     8347.8(16)
_computing_cell_refinement       'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction        'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  184 frames, \w rotation 1.4\% per frame (728s per frame)
   29 frames, \w rotation 1.4\% per frame (728s per frame)
;
_diffrn_measurement_device       '\k-geometry diffractometr'
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'area detector \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_av_sigmaI/netI    0.1090
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            9617
_diffrn_reflns_theta_full        21.99
_diffrn_reflns_theta_max         21.99
_diffrn_reflns_theta_min         2.72
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             3440
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.00157(19)
_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_ref   0.935
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     589
_refine_ls_number_reflns         5071
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.935
_refine_ls_R_factor_all          0.1187
_refine_ls_R_factor_gt           0.0653
_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^)+(0.0847P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1517
_refine_ls_wR_factor_ref         0.1737
_reflns_number_gt                2785
_reflns_number_total             5071
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo060545xsi20060524_061725.cif
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4021834