Regio- and diastereoselective synthesis of cyclobutylated phenothiazines <i>via</i> [2 + 2] photocycloaddition: demonstrating wavelength-gated cycloreversion inside live cells.
Sharangi, Sanhati; Chakraborty, Barsha; Jha, Raushan Kumar; Mandal, Swarnadeep; Koner, Apurba Lal; Kumar, Sangit; Chemical science 16 (2025) 709–720; doi:10.1039/d4sc07817a

data_1573461
_publ_section_title
;
 Regio- and diastereoselective synthesis of cyclobutylated phenothiazines
 <i>via</i> [2 + 2] photocycloaddition: demonstrating wavelength-gated
 cycloreversion inside live cells.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              709
_journal_page_last               720
_journal_paper_doi               10.1039/d4sc07817a
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration S
_chemical_formula_moiety         'C30 H21 N O S'
_chemical_formula_sum            'C30 H21 N O S'
_chemical_formula_weight         443.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-11-18 deposited with the CCDC.	2024-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.368(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9514(19)
_cell_length_b                   16.600(5)
_cell_length_c                   22.163(7)
_cell_measurement_reflns_used    1524
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      21.84
_cell_measurement_theta_min      2.21
_cell_volume                     2189.5(12)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2866
_diffrn_reflns_av_unetI/netI     0.2275
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            75484
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_min         2.210
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.4814
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1291 before and 0.0849 after correction.
The Ratio of minimum to maximum transmission is 0.6453.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       needle
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.008
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.127
_refine_ls_abs_structure_details
;
 Flack x determined using 1542 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(10)
_refine_ls_extinction_coef       0.056(8)
_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   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     596
_refine_ls_number_reflns         12259
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.2350
_refine_ls_R_factor_gt           0.1177
_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^)+(0.1588P)^2^+0.9058P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2794
_refine_ls_wR_factor_ref         0.3453
_reflns_Friedel_coverage         0.936
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                5426
_reflns_number_total             12259
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07817a4.cif
_cod_data_source_block           2y
_cod_depositor_comments
;
Adding full bibliography for 1573456--1573463.cif.

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C60 H42 N2 O2 S2'
_cod_original_formula_weight         887.07
_cod_original_formula_moiety         '2(C30 H21 N O S)'
_cod_original_formula_units_Z            2
_cod_database_code               1573461
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C23(H23), C24A(H24A), C23A(H23A), C2(H2), C2A(H2A), C24(H24)
1.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C17A(H17A), C30A(H30A), C12(H12), C18(H18), C10(H10), C14(H14),
 C7(H7), C19(H19), C9(H9), C10A(H10A), C29A(H29A), C17(H17), C20A(H20A),
 C30(H30), C8(H8), C15(H15), C27A(H27A), C29(H29), C21(H21), C21A(H21A),
 C26(H26), C19A(H19A), C15A(H15A), C26A(H26A), C7A(H7A), C12A(H12A), C9A(H9A),
 C20(H20), C13A(H13A), C18A(H18A), C28(H28), C28A(H28A), C8A(H8A), C27(H27),
 C14A(H14A)
;
_shelx_res_checksum              21323
_shelx_hkl_checksum              88799
_olex2_submission_special_instructions 'No special instructions were received'