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_1573462
_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         'C26 H19 N O S'
_chemical_formula_sum            'C26 H19 N O S'
_chemical_formula_weight         393.48
_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
_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                 95.524(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.2581(6)
_cell_length_b                   25.0852(11)
_cell_length_c                   12.7705(6)
_cell_measurement_reflns_used    9735
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.20
_cell_volume                     3908.7(3)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.993
_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  0.0575
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            93193
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.033
_diffrn_reflns_theta_min         2.200
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4996
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1493 before and 0.0715 after correction.
The Ratio of minimum to maximum transmission is 0.6696.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'Bright Yellow'
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.016
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         11369
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0617P)^2^+1.3178P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1088
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10005
_reflns_number_total             11369
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07817a4.cif
_cod_data_source_block           2af
_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            'C52 H38 N2 O2 S2'
_cod_original_formula_weight         786.96
_cod_original_formula_moiety         '2(C26 H19 N O S)'
_cod_original_formula_units_Z            4
_cod_database_code               1573462
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C00B(H00B), C00K(H00K), C00O(H00O), C00Y(H00Y)
1.b Secondary CH2 refined with riding coordinates:
 C017(H01G,H01H), C01F(H01O,H01P), C01G(H01C,H01D), C01H(H01E,H01F)
1.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00W(H00W),
 C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013), C014(H014),
 C015(H015), C016(H016), C018(H018), C019(H019), C01A(H01A), C01B(H01B),
 C01C(H01J), C01D(H01M), C01E(H01N), C01I(H01I), C01J(H01Q), C01K(H01K),
 C01L(H01L), C01M(H01R)
;
_shelx_res_checksum              92292
_shelx_hkl_checksum              88911
_olex2_submission_special_instructions 'No special instructions were received'