Ligand electronic fine-tuning and its repercussion on the photocatalytic activity and mechanistic pathways of the copper-photocatalysed aza-Henry reaction
Li, Chenfei; Dickson, Robert; Rockstroh, Nils; Rabeah, Jabor; Cordes, David B.; Slawin, Alexandra M. Z.; Hünemörder, Paul; Spannenberg, Anke; Bühl, Michael; Mejía, Esteban; Zysman-Colman, Eli; Kamer, Paul C. J.; Catalysis Science & Technology 10 (2020) 7745–7756; doi:10.1039/D0CY01221A

data_1559280
_publ_section_title
;
 Ligand electronic fine-tuning and its repercussion on the photocatalytic
 activity and mechanistic pathways of the copper-photocatalysed aza-Henry
 reaction
;
_journal_issue                   22
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              7745
_journal_page_last               7756
_journal_paper_doi               10.1039/D0CY01221A
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C57 H40 Cu F12 N2 O P2, F6 P'
_chemical_formula_sum            'C57 H40 Cu F18 N2 O P3'
_chemical_formula_weight         1267.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-24 deposited with the CCDC.	2020-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.8050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.44340(10)
_cell_length_b                   20.2661(2)
_cell_length_c                   27.9804(4)
_cell_measurement_reflns_used    57137
_cell_measurement_temperature    150
_cell_measurement_theta_max      69.3300
_cell_measurement_theta_min      2.2140
_cell_volume                     6394.24(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.40a (Rigaku OD, 2019)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'CrysAlisPro 1.171.40.40a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 CCD
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    156.17 290.17   0.50    5.00    -- -109.22 -76.83-130.24  268
  2  \w    158.38 291.88   0.50    5.00    -- -107.17 -76.14 -37.39  267
  3  \w    -47.98  86.52   0.50    1.00    --   46.61 -77.00 105.93  269
  4  \w    -36.32  97.68   0.50    1.00    --   58.37 -74.61 -97.61  268
  5  \w    160.56 293.56   0.50    5.00    -- -104.95 -74.21 170.60  266
  6  \w   -108.54 -30.54   0.50    5.00    -- -102.69 100.06  71.77  156
  7  \w    157.01 288.51   0.50    5.00    -- -108.51 -66.45 -90.98  263
  8  \w    -18.98 112.52   0.50    3.00    --   75.67 -35.94  60.50  263
  9  \f   -103.62  80.38   0.50    5.00 -14.25-108.94  35.48    --   368
 10  \w    -38.78  94.72   0.50    1.00    --   55.75 -74.01  -3.11  267
 11  \f    -96.62 113.38   0.50    1.00 -34.53   2.55  35.48    --   420
 12  \w   -138.73  -2.23   0.50    4.00    --  -96.77  83.33  16.96  273
 13  \w    157.40 286.90   0.50    5.00    -- -107.98 -50.05  64.08  259
 14  \w   -108.76 -29.76   0.50    5.00    -- -105.43  99.10  76.58  158
 15  \w   -140.11 -10.61   0.50    5.00    -- -105.22  50.66  49.23  259
 16  \w    167.69 258.19   0.50    5.00    -- -106.20-126.04  91.94  181
 17  \w    157.67 289.17   0.50    5.00    -- -108.77 -73.76  25.75  263
 18  \f   -333.16  26.84   0.50    1.00 -45.76  48.94 -76.41    --   720
 19  \w   -151.60 -15.09   0.50    5.00    -- -108.77  88.11 168.12  273
 20  \f   -333.16  26.84   0.50    3.00 -39.07 -78.94 -76.41    --   720
 21  \w   -151.60 -15.09   0.50    5.00    -- -108.77  88.11  -6.88  273
 22  \w    157.68 288.68   0.50    5.00    -- -108.77 -73.76  -9.25  262
 23  \w   -151.60 -15.09   0.50    5.00    -- -108.77  88.11  43.12  273
 24  \w    157.67 289.17   0.50    5.00    -- -108.77 -73.76 125.75  263
 25  \w    157.67 289.17   0.50    5.00    -- -108.77 -73.76 175.75  263
 26  \w    157.67 289.17   0.50    5.00    -- -108.77 -73.76 100.75  263
 27  \f      6.84 246.34   0.50    5.00 -69.07-108.94 -76.41    --   479
 28  \f   -142.84  57.16   0.50    1.00   3.29  43.14  76.41    --   400
 29  \w    157.67 289.17   0.50    5.00    -- -108.77 -73.76 150.75  263
 30  \w    -20.70  91.80   0.50    1.00    --   49.16 -88.11-148.12  225
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0362849000
_diffrn_orient_matrix_UB_12      0.0725471000
_diffrn_orient_matrix_UB_13      -0.0098242000
_diffrn_orient_matrix_UB_21      0.0348527000
_diffrn_orient_matrix_UB_22      -0.0047763000
_diffrn_orient_matrix_UB_23      -0.0507126000
_diffrn_orient_matrix_UB_31      -0.1270306000
_diffrn_orient_matrix_UB_32      -0.0220567000
_diffrn_orient_matrix_UB_33      -0.0213790000
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            99275
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.509
_diffrn_reflns_theta_min         2.706
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'I\mS (Cu) microfocus X-ray tube'
_exptl_absorpt_coefficient_mu    1.994
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.40a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       prism
_exptl_crystal_F_000             2560
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.252
_exptl_crystal_size_min          0.196
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     743
_refine_ls_number_reflns         11910
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0786
_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^)+(0.0018P)^2^+29.1314P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1611
_refine_ls_wR_factor_ref         0.1615
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11501
_reflns_number_total             11910
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cy01221a2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 1559279--1559280.cif.'
_cod_original_cell_volume        6394.23(13)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1559280
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C17(H17), C18(H18), C19(H19),
 C23(H23), C24(H24), C25(H25), C31(H31), C32(H32), C34(H34), C35(H35), C38(H38),
  C39(H39), C41(H41), C42(H42), C45(H45), C46(H46), C48(H48), C49(H49),
 C52(H52), C53(H53), C55(H55), C56(H56)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C)
;
_shelx_res_checksum              84200
_shelx_fab_checksum              67527