1,3-Dipolar cycloadditions with meso-tetraarylchlorins ‒ site selectivity and mixed bisadducts
Almeida, José; Aguiar, António; Leite, Andreia; Silva, André M. N.; Cunha-Silva, Luís; de Castro, Baltazar; Rangel, Maria; Barone, Giampaolo; Tomé, Augusto C.; Silva, Ana M. G.; Organic Chemistry Frontiers 4 (2017) 534–; doi:10.1039/C6QO00771F

data_1553621
_publ_section_title
;
 1,3-Dipolar cycloadditions with meso-tetraarylchlorins -- site
 selectivity and mixed bisadducts
;
_journal_issue                   4
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              534
_journal_paper_doi               10.1039/C6QO00771F
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C60 H28 F20 N6 O2'
_chemical_formula_sum            'C60 H28 F20 N6 O2'
_chemical_formula_weight         1244.88
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             '28 June 2016'
_audit_creation_method           'SHELXL-2014/7 and enCIFer'
_audit_update_record
;
2016-11-29 deposited with the CCDC.
2017-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                102.651(5)
_cell_angle_beta                 95.439(6)
_cell_angle_gamma                92.290(6)
_cell_formula_units_Z            2
_cell_length_a                   12.4994(13)
_cell_length_b                   13.1859(14)
_cell_length_c                   16.0253(17)
_cell_measurement_reflns_used    7343
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      21.44
_cell_measurement_theta_min      2.21
_cell_volume                     2560.5(5)
_computing_cell_refinement       'SAINT (Bruker AXS Inc., 2012)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT (Bruker AXS Inc., 2012)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker X8 Kappa CCD APEX II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            51921
_diffrn_reflns_point_group_measured_fraction_full 0.989
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_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         3.660
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_correction_T_min  0.899
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_exptl_absorpt_process_details
; 
'SADABS V2012/1 (Bruker AXS Inc.)' 
;
_exptl_crystal_colour            black
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_exptl_crystal_description       prism
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_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_refine_diff_density_max         1.396
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_refine_ls_extinction_coef       0.050(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.614
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         8926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.614
_refine_ls_R_factor_all          0.1877
_refine_ls_R_factor_gt           0.1387
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4059
_refine_ls_wR_factor_ref         0.4340
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5527
_reflns_number_total             8926
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00771f2.cif
_cod_data_source_block           as0214
_cod_database_code               1553621
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              78958
_shelx_hkl_checksum              95446