Photoexcitation of (diarylmethylene)amino benziodoxolones for alkylamination of styrene derivatives with carboxylic acids.
Okumatsu, Daichi; Kiyokawa, Kensuke; Bao Nguyen, Linh Tran; Abe, Manabu; Minakata, Satoshi; Chemical science 15 (2024) 1068–1076; doi:10.1039/d3sc06090j

data_1570546
_publ_section_title
;
 Photoexcitation of (diarylmethylene)amino benziodoxolones for
 alkylamination of styrene derivatives with carboxylic acids.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              1068
_journal_page_last               1076
_journal_paper_doi               10.1039/d3sc06090j
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C32 H33 N3'
_chemical_formula_sum            'C32 H33 N3'
_chemical_formula_weight         459.61
_chemical_name_systematic
N-(2-(1-methylcyclohexyl)-1,1-di(pyridin-2-yl)ethyl)-1,1-diphenylmethanimine
_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             2023-07-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2023-08-04 deposited with the CCDC.	2023-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                107.1090(10)
_cell_angle_beta                 95.8940(10)
_cell_angle_gamma                102.6390(10)
_cell_formula_units_Z            4
_cell_length_a                   10.3382(2)
_cell_length_b                   15.2358(2)
_cell_length_c                   17.3918(2)
_cell_measurement_reflns_used    18485
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      77.5030
_cell_measurement_theta_min      3.4270
_cell_volume                     2513.40(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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_temperature      123.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1029869000
_diffrn_orient_matrix_UB_12      0.0352397000
_diffrn_orient_matrix_UB_13      0.0510285000
_diffrn_orient_matrix_UB_21      -0.1034278000
_diffrn_orient_matrix_UB_22      -0.0970302000
_diffrn_orient_matrix_UB_23      -0.0417682000
_diffrn_orient_matrix_UB_31      0.0528395000
_diffrn_orient_matrix_UB_32      -0.0368882000
_diffrn_orient_matrix_UB_33      0.0672767000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            33725
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.570
_diffrn_reflns_theta_min         3.145
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.544
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80920
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       prism
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.093
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.039
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     633
_refine_ls_number_reflns         10284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0447P)^2^+0.6308P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1058
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8723
_reflns_number_total             10284
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc06090j2.cif
_cod_data_source_block           OD_20230722
_cod_depositor_comments
'Adding full bibliography for 1570544--1570546.cif.'
_cod_database_code               1570546
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     OD_20230722
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.951
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C57(H57A,H57B), C25(H25A,H25B), C31(H31A,H31B), C27(H27A,H27B), C63(H63A,
 H63B), C30(H30A,H30B), C59(H59A,H59B), C62(H62A,H62B), C28(H28A,H28B),
 C29(H29A,H29B), C61(H61A,H61B), C60(H60A,H60B)
2.b Aromatic/amide H refined with riding coordinates:
 C35(H35), C9(H9), C41(H41), C39(H39), C7(H7), C36(H36), C45(H45), C48(H48),
 C53(H53), C21(H21), C13(H13), C38(H38), C3(H3), C51(H51), C22(H22), C16(H16),
 C37(H37), C19(H19), C12(H12), C6(H6), C56(H56), C44(H44), C49(H49), C18(H18),
 C17(H17), C4(H4), C42(H42), C10(H10), C5(H5), C50(H50), C24(H24), C23(H23),
 C11(H11), C43(H43), C54(H54), C55(H55)
2.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C64(H64A,H64B,H64C)
;
_shelx_res_checksum              76654
_shelx_hkl_checksum              30911
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_full_max 1.591
_oxdiff_exptl_absorpt_empirical_full_min 0.787