Visible light-mediated C(sp3)-H bond functionalization inside an all-organic nanocavity
Roy, Debojyoti; Paul, Sunandita; Dasgupta, Jyotishman; Chemical Communications  (2023) –; doi:10.1039/D3CC03987K

data_7132200
_publ_section_title
;
 Visible light-mediated C(sp3)-H bond functionalization inside an
 all-organic nanocavity
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03987K
_journal_year                    2023
_chemical_formula_moiety         '4(F6 P), C48 H40 N4, 2(C15 H12), 2(C2 H3 N)'
_chemical_formula_sum            'C82 H70 F24 N6 P4'
_chemical_formula_weight         1719.32
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-08-03 deposited with the CCDC.	2023-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                66.889(3)
_cell_angle_beta                 79.115(3)
_cell_angle_gamma                85.113(3)
_cell_formula_units_Z            2
_cell_length_a                   12.3744(5)
_cell_length_b                   16.8795(5)
_cell_length_c                   19.4847(8)
_cell_measurement_reflns_used    6933
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      22.1740
_cell_measurement_theta_min      1.9860
_cell_volume                     3675.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f   -349.73   9.27   1.00    4.00   6.61  -9.84 -31.50    --   359
  2  \w    -60.89   0.11   1.00    4.00    --  -14.77  94.56 -34.84   61
  3  \w    -65.46  -0.46   1.00    4.00    --  -19.34  94.56 145.16   65
  4  \w   -100.81  15.19   1.00    4.00    --   -9.84 -59.25 -51.92  116
  5  \w    -65.46  -0.46   1.00    4.00    --  -19.34  94.56  73.16   65
  6  \f    -10.27 348.73   1.00    4.00  81.02  -9.84  31.50    --   359
  7  \w    -65.46  -0.46   1.00    4.00    --  -19.34  94.56   1.16   65
  8  \w   -100.81  15.19   1.00    4.00    --   -9.84 -59.25 164.08  116
  9  \f   -339.82  19.18   1.00    4.00  15.81  -9.84 -59.25    --   359
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0020736000
_diffrn_orient_matrix_UB_12      -0.0089003000
_diffrn_orient_matrix_UB_13      0.0384630000
_diffrn_orient_matrix_UB_21      -0.0545266000
_diffrn_orient_matrix_UB_22      -0.0157041000
_diffrn_orient_matrix_UB_23      0.0105474000
_diffrn_orient_matrix_UB_31      0.0207393000
_diffrn_orient_matrix_UB_32      -0.0419747000
_diffrn_orient_matrix_UB_33      0.0047169000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1403
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            159688
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.676
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       plate
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.246
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.864
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1049
_refine_ls_number_reflns         12931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1144
_refine_ls_R_factor_gt           0.0622
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0984P)^2^+0.6235P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1606
_refine_ls_wR_factor_ref         0.1917
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7727
_reflns_number_total             12931
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03987k2.cif
_cod_data_source_block           x_box_autored
_cod_database_code               7132200
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C41 H32 F12 N3 P2'
_reflns_odcompleteness_completeness 80.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     36.87
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C13(H13A,H13B), C41(H41A,H41B), C48(H48A,H48B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14),
 C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C26(H26),
  C27(H27), C29(H29), C30(H30), C32(H32), C33(H33), C34(H34), C35(H35),
 C37(H37), C38(H38), C39(H39), C40(H40), C43(H43), C44(H44), C46(H46), C47(H47),
  C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13),
 C14(H14), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C11(H11), C12(H12), C13(H13),
  C14(H14)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C15(H15A,H15B,H15C), C1(H1A,H1B,H1C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              20710
_shelx_hkl_checksum              79305
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.682
_oxdiff_exptl_absorpt_empirical_full_min 0.673