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_1573456
_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_formula_moiety         'C28 H19 N O S'
_chemical_formula_sum            'C28 H19 N O S'
_chemical_formula_weight         417.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-01-19
_audit_creation_method
;

Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-11-18 deposited with the CCDC.	2024-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.313(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.812(7)
_cell_length_b                   7.486(3)
_cell_length_c                   13.413(4)
_cell_measurement_reflns_used    500
_cell_measurement_temperature    110.00
_cell_measurement_theta_max      23.00
_cell_measurement_theta_min      3.14
_cell_volume                     2015.5(12)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      110.00
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.781
_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  0.1749
_diffrn_reflns_av_unetI/netI     0.2108
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 0.781
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13296
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.781
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.682
_diffrn_reflns_theta_min         3.144
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6987
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1470 before and 0.0591 after correction.
The Ratio of minimum to maximum transmission is 0.9366.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       rod
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       0.040(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4465
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1384
_refine_ls_R_factor_gt           0.0915
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2075
_refine_ls_wR_factor_ref         0.2539
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2697
_reflns_number_total             4465
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07817a4.cif
_cod_data_source_block           2ad
_cod_depositor_comments
'Adding full bibliography for 1573456--1573463.cif.'
_cod_original_cell_volume        2015.5(11)
_cod_database_code               1573456
_shelx_shelxl_version_number     2018/1
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C22(H22), C2(H2)
1.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
1.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C16(H16), C19(H19), C13(H13), C10(H10), C11(H11), C28(H28), C8(H8),
 C17(H17), C6(H6), C24(H24), C27(H27), C18(H18), C26(H26), C25(H25)
;
_shelx_res_checksum              16421
_shelx_hkl_checksum              69077
_olex2_submission_special_instructions 'No special instructions were received'