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_1573463
_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 unk
_chemical_formula_moiety         'C24 H17 N O2 S'
_chemical_formula_sum            'C24 H17 N O2 S'
_chemical_formula_weight         383.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_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
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3105(8)
_cell_length_b                   9.5818(10)
_cell_length_c                   26.479(3)
_cell_measurement_reflns_used    1046
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      18.63
_cell_measurement_theta_min      2.26
_cell_volume                     1854.8(4)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      140.0
_diffrn_measured_fraction_theta_full 0.9947
_diffrn_measured_fraction_theta_max 0.9947
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1912
_diffrn_reflns_av_unetI/netI     0.1939
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            28021
_diffrn_reflns_theta_full        30.1650
_diffrn_reflns_theta_max         30.17
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6615
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0775 before and 0.0684 after correction.
The Ratio of minimum to maximum transmission is 0.8867.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.3732
_exptl_crystal_description       block
_exptl_crystal_F_000             800.8416
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.6772
_refine_diff_density_min         -0.7383
_refine_diff_density_rms         0.1495
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_d_res_high            0.7072
_refine_ls_d_res_low             9.0100
_refine_ls_goodness_of_fit_ref   0.9935
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    33
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9935
_refine_ls_R_factor_all          0.1755
_refine_ls_R_factor_gt           0.0689
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0141P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1729
_reflns_Friedel_coverage         0.993
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              37
_reflns_limit_l_min              -37
_reflns_number_gt                2602
_reflns_number_total             5461
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4sc07817a4.cif
_cod_data_source_block           2al
_cod_depositor_comments
'Adding full bibliography for 1573456--1573463.cif.'
_cod_original_cell_volume        1854.8(3)
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               1573463
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C18(H18), C2(H2)
1.b Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b)
1.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C14(H14), C20(H20), C10(H10), C7(H7), C13(H13), C8(H8),
 C24(H24), C23(H23), C9(H9), C21(H21), C22(H22)
;
_olex2_submission_special_instructions 'No special instructions were received'