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_1570545
_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         'C28 H31 N O2'
_chemical_formula_sum            'C28 H31 N O2'
_chemical_formula_weight         413.54
_chemical_name_systematic
'methyl 2-((diphenylmethylene)amino)-4,4-dimethyl-2-(p-tolyl)pentanoate'
_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             2022-06-30
_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                90
_cell_angle_beta                 96.5420(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.07670(10)
_cell_length_b                   10.2335(2)
_cell_length_c                   25.6684(3)
_cell_measurement_reflns_used    17520
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      77.1350
_cell_measurement_theta_min      3.4770
_cell_volume                     2368.72(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_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                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_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      -0.1588561000
_diffrn_orient_matrix_UB_12      -0.0519152000
_diffrn_orient_matrix_UB_13      -0.0142566000
_diffrn_orient_matrix_UB_21      -0.0377452000
_diffrn_orient_matrix_UB_22      0.0354782000
_diffrn_orient_matrix_UB_23      0.0552840000
_diffrn_orient_matrix_UB_31      -0.0503745000
_diffrn_orient_matrix_UB_32      0.1367484000
_diffrn_orient_matrix_UB_33      -0.0197372000
_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  0.0382
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            35672
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.467
_diffrn_reflns_theta_min         3.466
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82095
_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    1.160
_exptl_crystal_description       prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0495P)^2^+0.5727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1107
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4357
_reflns_number_total             4963
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc06090j2.cif
_cod_data_source_block           OD_416
_cod_depositor_comments
'Adding full bibliography for 1570544--1570546.cif.'
_cod_database_code               1570545
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C28 H31 N1 O2'
_chemical_oxdiff_usercomment     OD_416
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.923
_reflns_odcompleteness_completeness 99.98
_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. Others
 Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=1-FVAR(1)
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=
 Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C5(H5), C20(H20), C6(H6), C21(H21), C26(H26), C30(H30),
 C24(H24), C22(H22), C27(H27), C29(H29), C28(H28), C23(H23)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C31(H31A,H31B,H31C), C14(H14A,H14B,H14C), C13(H13A,H13B,
 H13C), C12(H12A,H12B,H12C), C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C16(H16A,
 H16B,H16C)
;
_shelx_res_checksum              11163
_shelx_hkl_checksum              6975
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_full_max 1.912
_oxdiff_exptl_absorpt_empirical_full_min 0.659