Installation of cationic phosphorus on dimethyldihydropyrene photoswitches: expanding the atomic repertoire towards far-red photoswitching in water.
Maity, Manik Lal; Chandra, Sayan; Mahato, Samyadeb; Bandyopadhyay, Subhajit; Chemical science 16 (2025) 21991–22001; doi:10.1039/d5sc06168g

data_1576321
_publ_section_title
;
 Installation of cationic phosphorus on dimethyldihydropyrene
 photoswitches: expanding the atomic repertoire towards far-red
 photoswitching in water.
;
_journal_issue                   46
_journal_name_full               'Chemical science'
_journal_page_first              21991
_journal_page_last               22001
_journal_paper_doi               10.1039/d5sc06168g
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         C39H44F6P2
_chemical_formula_sum            'C39 H44 F6 P2'
_chemical_formula_weight         688.68
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'Intrinsic Phasing'
_audit_creation_method
;FinalCif 2024.9-RC113 by Daniel Kratzert, Freiburg 2025, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2025-04-10 deposited with the CCDC.	2025-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   38.743(13)
_cell_length_b                   18.182(6)
_cell_length_c                   9.838(3)
_cell_measurement_reflns_used    9872
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.6388
_cell_measurement_theta_min      2.2368
_cell_measurement_wavelength     0.71073
_cell_volume                     6930(4)
_computing_cell_refinement       'SAINT V8.41 (Bruker AXS LLC)'
_computing_data_reduction        'SAINT V8.41 (Bruker AXS LLC)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1503)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.391
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;<Phi   scan: start=   0.0; len= 180.0; end= 180.0 at [Counterclockwise Eulerian 
angles: dx= 60.00 mm theta=   0.000 deg omega=   0.000 deg chi=  54.740 deg] 
measure for 1.0 seconds; frame angle 1.00 degrees, wavelength=0.71073>
<Phi   scan: start= 180.0; len= 180.0; end= 360.0 at [Counterclockwise Eulerian 
angles: dx= 60.00 mm theta=   0.000 deg omega=   0.000 deg chi=  54.740 deg] 
measure for 1.0 seconds; frame angle 1.00 degrees, wavelength=0.71073>
<Phi   scan: start= 360.0; len=   0.5; end= 360.5 at [Counterclockwise Eulerian 
angles: dx= 60.00 mm theta=   6.481 deg omega= 272.722 deg chi=  22.000 deg] 
measure for 5.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Omega scan: start= 324.6; len=  75.0; end= 399.6 at [Counterclockwise Eulerian 
angles: dx= 60.00 mm theta=   9.721 deg phi= 360.000 deg chi=  68.500 deg] 
measure for 5.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Omega scan: start= 324.6; len=  68.5; end= 393.1 at [Counterclockwise Eulerian 
angles: dx= 60.00 mm theta=   6.481 deg phi= 180.000 deg chi=  68.500 deg] 
measure for 5.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Omega scan: start= 358.9; len= 134.5; end= 493.4 at [Counterclockwise Eulerian 
angles: dx= 60.00 mm theta=   6.481 deg phi= 153.000 deg chi= -44.500 deg] 
measure for 5.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Phi   scan: start=   0.0; len= 360.0; end= 360.0 at [Counterclockwise Eulerian 
angles: dx= 60.00 mm theta=   6.481 deg omega= 344.575 deg chi= -22.000 deg] 
measure for 5.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Omega scan: start= 358.9; len= 134.5; end= 493.4 at [Counterclockwise Eulerian 
angles: dx= 60.00 mm theta=   6.481 deg phi=   0.000 deg chi= -44.500 deg] 
measure for 5.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Omega scan: start= 324.6; len=  68.5; end= 393.1 at [Counterclockwise Eulerian 
angles: dx= 60.00 mm theta=   6.481 deg phi= 108.000 deg chi=  68.500 deg] 
measure for 5.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Omega scan: start= 324.6; len=  68.5; end= 393.1 at [Counterclockwise Eulerian 
angles: dx= 60.00 mm theta=   6.481 deg phi=  36.000 deg chi=  68.500 deg] 
measure for 5.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Omega scan: start= 358.9; len= 134.5; end= 493.4 at [Counterclockwise Eulerian 
angles: dx= 60.00 mm theta=   6.481 deg phi= 306.000 deg chi= -44.500 deg] 
measure for 5.0 seconds; frame angle 0.50 degrees, wavelength=0.71073>
<Phi   scan: start=   0.0; len=-180.0; end=-180.0 at [Counterclockwise Eulerian 
angles: dx= 50.00 mm theta=   2.500 deg omega=   0.000 deg chi=  57.540 deg] 
measure for 1.0 seconds; frame angle 1.00 degrees, wavelength=0.71073>
;
_diffrn_measurement_device       'Four Circle Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1461
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            259288
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_reduction_process narrow-frame
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.351
_diffrn_reflns_theta_min         1.934
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           1.4
_diffrn_source_target            Mo
_diffrn_source_type              'INCOATEC I\mS 3.0'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for single-crystal
 structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.32
_exptl_crystal_description       block
_exptl_crystal_F_000             2896
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.068
_refine_diff_density_min         -0.887
_refine_diff_density_rms         0.133
_refine_ls_abs_structure_details
;
 Flack x determined using 4053 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.48(5)
_refine_ls_extinction_coef       0.0014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     770
_refine_ls_number_reflns         17261
_refine_ls_number_restraints     4743
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1721
_refine_ls_R_factor_gt           0.1356
_refine_ls_shift/su_max          0.049
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0522P)^2^+63.2962P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2914
_refine_ls_wR_factor_ref         0.3140
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                12507
_reflns_number_total             17261
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06168g2.cif
_cod_data_source_block           sb_mlm_419_a_sq
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               1576321
_shelx_shelxl_version_number     2019/3
_exptl_bruker_absorpt_correction_t_ratio 0.8786
_shelx_estimated_absorpt_t_min   0.962
_shelx_estimated_absorpt_t_max   0.980
_bruker_diffrn_measurement_temperature_device 'Oxford Cryostream 1000'
_diffrn_measurement_bruker_total_exposure_time 14580.0
_diffrn_reflns_bruker_av_norm_i  130.85
_diffrn_reflns_bruker_number_gt  94616
_computing_bruker_data_scaling
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction'
_geom_details
; All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
_shelx_res_checksum              5756
_shelx_fab_checksum              431