#------------------------------------------------------------------------------
#$Date: 2025-06-02 21:20:34 +0300 (Mon, 02 Jun 2025) $
#$Revision: 299904 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/34/1573457.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1573457
loop_
_publ_author_name
'Sharangi, Sanhati'
'Chakraborty, Barsha'
'Jha, Raushan Kumar'
'Mandal, Swarnadeep'
'Koner, Apurba Lal'
'Kumar, Sangit'
_publ_section_title
;
 Regio- and diastereoselective synthesis of cyclobutylated phenothiazines
 via [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         'C25 N O S'
_chemical_formula_sum            'C25 N O S'
_chemical_formula_weight         362.32
_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_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                 117.294(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.545(2)
_cell_length_b                   7.4959(7)
_cell_length_c                   24.005(2)
_cell_measurement_reflns_used    2677
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      22.82
_cell_measurement_theta_min      2.66
_cell_volume                     3765.0(6)
_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      140.0
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1528
_diffrn_reflns_av_unetI/netI     0.1161
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            58260
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.089
_diffrn_reflns_theta_min         2.007
_exptl_absorpt_coefficient_mu    0.185
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       Block
_exptl_crystal_F_000             1448
_refine_diff_density_max         0.773
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         11018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1572
_refine_ls_R_factor_gt           0.0912
_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/[σ²(Fo²)+(0.1505P)²+1.3540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2367
_refine_ls_wR_factor_ref         0.2903
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6069
_reflns_number_total             11018
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc07817a4.cif
_cod_data_source_block           2x
_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            'C50 N2 O2 S2'
_cod_original_formula_weight         724.64
_cod_original_formula_moiety         '2(C25 N O S)'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        3764.9(6)
_cod_database_code               1573457
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S -0.39676(4) -0.53263(12) -0.77760(4) 0.0280(2) Uani 1 1 d . . . . .
S1 S -0.10960(4) -0.49837(12) -0.23858(5) 0.0280(2) Uani 1 1 d . . . . .
O003 O -0.30907(14) -0.3371(5) -0.55537(13) 0.0482(8) Uani 1 1 d . . . . .
N004 N -0.27743(13) -0.3393(4) -0.76692(13) 0.0248(6) Uani 1 1 d . . . . .
N1 N -0.23369(14) -0.6656(4) -0.25126(13) 0.0253(6) Uani 1 1 d . . . . .
O1 O -0.02625(16) -0.7439(6) -0.02160(14) 0.0621(11) Uani 1 1 d . . . . .
C007 C -0.24209(16) -0.2967(5) -0.60292(16) 0.0252(7) Uani 1 1 d . . . . .
C008 C -0.17414(17) -0.2719(4) -0.65326(17) 0.0264(7) Uani 1 1 d . . . . .
C009 C -0.23478(15) -0.3030(4) -0.65765(16) 0.0228(7) Uani 1 1 d . . . . .
C00A C -0.28859(16) -0.3378(4) -0.71956(16) 0.0237(7) Uani 1 1 d . . . . .
C00B C -0.12193(17) -0.2366(5) -0.59530(18) 0.0308(8) Uani 1 1 d . . . . .
C6 C -0.25229(18) -0.7060(5) -0.14672(18) 0.0282(8) Uani 1 1 d . . . . .
C00D C -0.43707(17) -0.1151(5) -0.79886(16) 0.0250(7) Uani 1 1 d . . . . .
C9 C -0.11631(16) -0.6789(5) -0.19276(16) 0.0236(7) Uani 1 1 d . . . . .
C11 C -0.09799(16) -0.9137(5) -0.26688(16) 0.0242(7) Uani 1 1 d . . . . .
C00G C -0.36053(17) -0.3856(5) -0.66325(17) 0.0276(7) Uani 1 1 d . . . . .
C7 C -0.19050(16) -0.7064(4) -0.14210(16) 0.0233(7) Uani 1 1 d . . . . .
C2 C -0.13794(18) -0.7287(5) -0.08267(17) 0.0285(8) Uani 1 1 d . . . . .
C00J C -0.30361(17) -0.3376(5) -0.60281(17) 0.0300(8) Uani 1 1 d . . . . .
C00K C -0.18961(19) -0.2553(5) -0.54507(18) 0.0323(8) Uani 1 1 d . . . . .
C00L C -0.35405(15) -0.3562(5) -0.72391(16) 0.0228(7) Uani 1 1 d . . . . .
C8 C -0.18294(16) -0.6806(4) -0.19893(16) 0.0236(7) Uani 1 1 d . . . . .
C5 C -0.2604(2) -0.7214(5) -0.09324(19) 0.0341(9) Uani 1 1 d . . . . .
C00O C -0.38226(17) -0.4678(5) -0.83972(18) 0.0278(8) Uani 1 1 d . . . . .
C23 C -0.05815(17) -0.6725(5) -0.12667(17) 0.0271(7) Uani 1 1 d . . . . .
C00Q C -0.31539(18) -0.3203(5) -0.87748(18) 0.0314(8) Uani 1 1 d . . . . .
C10 C -0.09081(16) -0.8642(5) -0.20311(17) 0.0253(7) Uani 1 1 d . . . . .
C00S C -0.32629(17) -0.3746(5) -0.82773(17) 0.0272(7) Uani 1 1 d . . . . .
C00T C -0.13056(18) -0.2247(5) -0.54181(18) 0.0324(8) Uani 1 1 d . . . . .
C16 C -0.15312(18) -1.0021(5) -0.30874(17) 0.0289(8) Uani 1 1 d . . . . .
C21 C -0.28370(19) -0.6690(5) -0.36315(18) 0.0326(8) Uani 1 1 d . . . . .
C15 C -0.1635(2) -1.0379(5) -0.36905(19) 0.0358(9) Uani 1 1 d . . . . .
C00X C -0.42553(19) -0.5112(6) -0.90091(19) 0.0358(9) Uani 1 1 d . . . . .
C4 C -0.2077(2) -0.7433(5) -0.0347(2) 0.0387(10) Uani 1 1 d . . . . .
C00Z C -0.50095(18) -0.1597(5) -0.82765(18) 0.0319(8) Uani 1 1 d . . . . .
C010 C -0.39250(16) -0.1754(5) -0.73340(16) 0.0250(7) Uani 1 1 d . . . . .
C011 C -0.41193(19) -0.0210(5) -0.83247(18) 0.0318(8) Uani 1 1 d . . . . .
C22 C -0.23015(17) -0.6293(5) -0.30687(17) 0.0263(7) Uani 1 1 d . . . . .
C3 C -0.1475(2) -0.7489(5) -0.03003(19) 0.0362(9) Uani 1 1 d . . . . .
C1 C -0.07074(19) -0.7219(6) -0.07263(18) 0.0355(9) Uani 1 1 d . . . . .
C015 C -0.41608(17) -0.2453(5) -0.68744(17) 0.0294(8) Uani 1 1 d . . . . .
C24 C -0.02472(17) -0.8163(5) -0.14854(18) 0.0312(8) Uani 1 1 d . . . . .
C17 C -0.17802(18) -0.5447(5) -0.30833(17) 0.0266(7) Uani 1 1 d . . . . .
C018 C -0.5144(2) -0.0223(6) -0.92387(18) 0.0378(9) Uani 1 1 d . . . . .
C019 C -0.54046(19) -0.1140(6) -0.89076(18) 0.0388(10) Uani 1 1 d . . . . .
C14 C -0.1184(2) -0.9881(5) -0.38843(19) 0.0345(9) Uani 1 1 d . . . . .
C18 C -0.1810(2) -0.4938(5) -0.36537(19) 0.0340(9) Uani 1 1 d . . . . .
C13 C -0.0632(2) -0.9041(5) -0.3464(2) 0.0361(9) Uani 1 1 d . . . . .
C12 C -0.05293(18) -0.8648(5) -0.28608(19) 0.0319(8) Uani 1 1 d . . . . .
C20 C -0.2865(2) -0.6189(6) -0.41971(19) 0.0411(10) Uani 1 1 d . . . . .
C01F C -0.3582(2) -0.3629(6) -0.93849(19) 0.0396(10) Uani 1 1 d . . . . .
C01G C -0.4506(2) 0.0249(6) -0.8949(2) 0.0379(9) Uani 1 1 d . . . . .
C01H C -0.4122(2) -0.4602(6) -0.9501(2) 0.0415(10) Uani 1 1 d . . . . .
C19 C -0.2352(2) -0.5274(6) -0.4206(2) 0.0402(10) Uani 1 1 d . . . . .
C01J C -0.4211(2) -0.1152(6) -0.6416(2) 0.0385(9) Uani 1 1 d . . . . .
C25 C 0.0136(2) -0.9680(6) -0.1058(2) 0.0503(13) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00O S001 C00L 98.24(17) . . ?
C17 S1 C9 97.81(17) . . ?
C00A N004 C00S 121.3(3) . . ?
C8 N1 C22 121.0(3) . . ?
C009 C007 C00J 122.3(3) . . ?
C009 C007 C00K 120.2(3) . . ?
C00K C007 C00J 117.4(3) . . ?
C00B C008 C009 120.5(3) . . ?
C007 C009 C008 118.8(3) . . ?
C007 C009 C00A 122.3(3) . . ?
C008 C009 C00A 118.8(3) . . ?
N004 C00A C009 117.9(3) . . ?
N004 C00A C00L 124.0(3) . . ?
C009 C00A C00L 117.9(3) . . ?
C00T C00B C008 119.8(3) . . ?
C5 C6 C7 120.2(4) . . ?
C00Z C00D C010 122.0(3) . . ?
C00Z C00D C011 119.3(3) . . ?
C011 C00D C010 118.6(3) . . ?
C8 C9 S1 109.0(2) . . ?
C8 C9 C23 119.5(3) . . ?
C8 C9 C10 115.6(3) . . ?
C23 C9 S1 108.6(2) . . ?
C23 C9 C10 88.1(2) . . ?
C10 C9 S1 114.9(2) . . ?
C16 C11 C10 118.9(3) . . ?
C12 C11 C10 121.8(3) . . ?
C12 C11 C16 119.2(3) . . ?
C00J C00G C00L 116.5(3) . . ?
C00J C00G C015 114.9(3) . . ?
C00L C00G C015 88.9(3) . . ?
C6 C7 C8 119.2(3) . . ?
C2 C7 C6 118.5(3) . . ?
C2 C7 C8 122.3(3) . . ?
C7 C2 C1 122.4(3) . . ?
C3 C2 C7 120.1(4) . . ?
C3 C2 C1 117.4(3) . . ?
O003 C00J C007 122.0(3) . . ?
O003 C00J C00G 118.7(3) . . ?
C007 C00J C00G 119.2(3) . . ?
C00T C00K C007 120.0(4) . . ?
C00A C00L S001 109.6(2) . . ?
C00A C00L C00G 119.2(3) . . ?
C00A C00L C010 115.5(3) . . ?
C00G C00L S001 107.8(2) . . ?
C00G C00L C010 87.8(3) . . ?
C010 C00L S001 115.5(2) . . ?
N1 C8 C9 123.8(3) . . ?
N1 C8 C7 117.8(3) . . ?
C7 C8 C9 118.3(3) . . ?
C6 C5 C4 120.4(4) . . ?
C00S C00O S001 119.9(3) . . ?
C00X C00O S001 120.2(3) . . ?
C00X C00O C00S 119.9(4) . . ?
C9 C23 C24 88.8(3) . . ?
C1 C23 C9 116.4(3) . . ?
C1 C23 C24 116.7(3) . . ?
C01F C00Q C00S 120.6(4) . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 C24 121.2(3) . . ?
C24 C10 C9 88.3(3) . . ?
C00O C00S N004 123.5(3) . . ?
C00Q C00S N004 116.7(3) . . ?
C00Q C00S C00O 119.7(3) . . ?
C00K C00T C00B 120.5(4) . . ?
C15 C16 C11 120.5(4) . . ?
C20 C21 C22 120.6(4) . . ?
C16 C15 C14 120.2(4) . . ?
C00O C00X C01H 119.1(4) . . ?
C3 C4 C5 119.7(4) . . ?
C00D C00Z C019 120.7(4) . . ?
C00D C010 C00L 119.1(3) . . ?
C00D C010 C015 122.9(3) . . ?
C015 C010 C00L 88.6(3) . . ?
C00D C011 C01G 120.5(4) . . ?
C21 C22 N1 117.3(3) . . ?
C21 C22 C17 119.2(3) . . ?
C17 C22 N1 123.3(3) . . ?
C4 C3 C2 121.0(4) . . ?
O1 C1 C2 121.6(4) . . ?
O1 C1 C23 119.2(4) . . ?
C2 C1 C23 119.0(3) . . ?
C010 C015 C00G 88.8(3) . . ?
C01J C015 C00G 119.5(3) . . ?
C01J C015 C010 118.5(3) . . ?
C10 C24 C23 88.8(3) . . ?
C25 C24 C23 121.6(4) . . ?
C25 C24 C10 116.9(3) . . ?
C22 C17 S1 120.1(3) . . ?
C18 C17 S1 119.8(3) . . ?
C18 C17 C22 120.0(4) . . ?
C01G C018 C019 120.2(4) . . ?
C018 C019 C00Z 119.2(4) . . ?
C13 C14 C15 119.1(4) . . ?
C19 C18 C17 120.2(4) . . ?
C14 C13 C12 120.9(4) . . ?
C11 C12 C13 119.9(4) . . ?
C21 C20 C19 119.8(4) . . ?
C01H C01F C00Q 119.6(4) . . ?
C018 C01G C011 120.0(4) . . ?
C01F C01H C00X 120.9(4) . . ?
C18 C19 C20 120.0(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 C00L 1.798(4) . ?
S001 C00O 1.744(4) . ?
S1 C9 1.796(3) . ?
S1 C17 1.745(4) . ?
O003 C00J 1.203(4) . ?
N004 C00A 1.279(4) . ?
N004 C00S 1.409(4) . ?
N1 C8 1.281(4) . ?
N1 C22 1.402(4) . ?
O1 C1 1.203(5) . ?
C007 C009 1.402(5) . ?
C007 C00J 1.482(5) . ?
C007 C00K 1.406(5) . ?
C008 C009 1.402(5) . ?
C008 C00B 1.396(5) . ?
C009 C00A 1.468(5) . ?
C00A C00L 1.503(5) . ?
C00B C00T 1.392(6) . ?
C6 C7 1.407(5) . ?
C6 C5 1.387(5) . ?
C00D C00Z 1.378(5) . ?
C00D C010 1.504(5) . ?
C00D C011 1.392(5) . ?
C9 C8 1.507(5) . ?
C9 C23 1.550(5) . ?
C9 C10 1.578(5) . ?
C11 C10 1.507(5) . ?
C11 C16 1.392(5) . ?
C11 C12 1.386(5) . ?
C00G C00J 1.499(5) . ?
C00G C00L 1.548(5) . ?
C00G C015 1.568(5) . ?
C7 C2 1.405(5) . ?
C7 C8 1.467(5) . ?
C2 C3 1.389(5) . ?
C2 C1 1.488(5) . ?
C00K C00T 1.376(6) . ?
C00L C010 1.587(5) . ?
C5 C4 1.394(6) . ?
C00O C00S 1.400(5) . ?
C00O C00X 1.389(5) . ?
C23 C1 1.504(5) . ?
C23 C24 1.560(5) . ?
C00Q C00S 1.392(5) . ?
C00Q C01F 1.382(5) . ?
C10 C24 1.548(5) . ?
C16 C15 1.379(5) . ?
C21 C22 1.393(5) . ?
C21 C20 1.381(6) . ?
C15 C14 1.392(6) . ?
C00X C01H 1.406(6) . ?
C4 C3 1.370(6) . ?
C00Z C019 1.409(5) . ?
C010 C015 1.537(5) . ?
C011 C01G 1.394(5) . ?
C22 C17 1.396(5) . ?
C015 C01J 1.515(6) . ?
C24 C25 1.520(6) . ?
C17 C18 1.391(5) . ?
C018 C019 1.389(6) . ?
C018 C01G 1.381(6) . ?
C14 C13 1.379(6) . ?
C18 C19 1.377(6) . ?
C13 C12 1.387(6) . ?
C20 C19 1.397(7) . ?
C01F C01H 1.379(6) . ?
