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_1576322
_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_formula_moiety         '1(C37.96 H35 O P)'
_chemical_formula_sum            'C37.96 H35 O P'
_chemical_formula_weight         538.15
_chemical_name_systematic        SB-MLM-DHPP2
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-03-03
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-04-16 deposited with the CCDC.	2025-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                101.427(2)
_cell_angle_beta                 90.026(2)
_cell_angle_gamma                115.072(2)
_cell_formula_units_Z            4
_cell_length_a                   10.8852(5)
_cell_length_b                   12.4834(6)
_cell_length_c                   25.1186(12)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.277
_cell_measurement_theta_min      2.494
_cell_volume                     3016.6(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_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 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 microsource'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            68550
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.308
_diffrn_reflns_theta_min         2.098
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1038 before and 0.0636 after correction.
The Ratio of minimum to maximum transmission is 0.8722.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic dark green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       block
_exptl_crystal_F_000             1143
_exptl_crystal_preparation       'dissolve in acetonitrile'
_exptl_crystal_recrystallization_method 'slow evaporation in acetonitrile'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.578
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     805
_refine_ls_number_reflns         14930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0841
_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^)+(0.1031P)^2^+6.0166P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2276
_refine_ls_wR_factor_ref         0.2374
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12488
_reflns_number_total             14930
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06168g2.cif
_cod_data_source_block           sbmlmdhpp2
_cod_database_code               1576322
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C01X(0.66) C01Y(0.66) C01Z(0.66) C023(0.66) C025(0.66) C026(0.66)
 C027(0.66) C028(0.66) C5(0.33) C9(0.33) C6(0.33) C8(0.33) C7(0.33) C4(0.33)
 C10(0.33) C11(0.33)
3.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00F(H00F), C00G(H00G), C00H(H00H), C00J(H00J),
 C00L(H00L), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U), C00W(H00W), C00Y(H00Y), C00Z(H00Z), C010(H010),
 C011(H011), C014(H014), C016(H016), C017(H017), C018(H018), C019(H019),
 C01A(H01J), C01B(H01K), C01D(H01O), C01E(H01P), C01L(H01L), C01M(H01M),
 C01N(H01N), C01R(H01Z), C01S(H01), C01T(H1)
3.b Idealised Me refined as rotating group:
 C01J(H01A,H01B,H01C), C01K(H01Q,H01R,H01S), C01O(H01T,H01U,H01V), C01P(H01W,
 H01X,H01Y), C01Q(H01D,H01E,H01F), C01U(H2,H,HA), C01V(H01G,H01H,H01I),
 C020(H02A,H02B,H02C), C022(H02D,H02E,H02F), C1(H1A,H1B,H1C), C2(H2A,H2B,H2C),
 C3(H3A,H3B,H3C)
;
_shelx_res_checksum              46018
_olex2_submission_special_instructions 'No special instructions were received'