Photoinduced [4+2] cycloaddition of dienes and quinonemethides.
Jose, Jobsy; Yadav, Arun; Tripathi, Chandra Bhushan; Chemical communications (Cambridge, England) 60 (2024) 11315–11318; doi:10.1039/d4cc03778b

data_7133714
_publ_section_title
;
 Photoinduced [4+2] cycloaddition of dienes and quinonemethides.
;
_journal_issue                   80
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11315
_journal_page_last               11318
_journal_paper_doi               10.1039/d4cc03778b
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C27 H37 O4 P'
_chemical_formula_sum            'C27 H37 O4 P'
_chemical_formula_weight         456.53
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-27
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2024-07-11 deposited with the CCDC.	2024-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.0870(10)
_cell_angle_beta                 103.6160(10)
_cell_angle_gamma                118.610(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8921(2)
_cell_length_b                   10.1200(2)
_cell_length_c                   14.8901(2)
_cell_measurement_reflns_used    8984
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.4640
_cell_measurement_theta_min      3.0800
_cell_volume                     1260.38(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -70.00  25.00   0.50    0.05    --  -47.50  83.00-121.00  190
  2  \w    -17.00  73.00   0.50    0.05    --   47.50 -83.00 117.00  180
  3  \w    -68.00 -43.00   0.50    0.15    --  -91.75  83.00-121.00   50
  4  \w   -144.00-110.00   0.50    0.15    --  -91.75 -83.00 117.00   68
  5  \w     37.00  70.00   0.50    0.15    --  109.69 -83.00 117.00   66
  6  \w    102.00 157.00   0.50    0.15    --  109.69  83.00-121.00  110
  7  \w    -62.00  -8.00   0.50    0.05    --  -47.50  57.00-180.00  108
  8  \w    -13.00  24.00   0.50    0.05    --  -47.50  19.00-120.00   74
  9  \w     -9.00  26.00   0.50    0.05    --  -47.50  19.00 150.00   70
 10  \w    -23.00  27.00   0.50    0.05    --  -47.50  19.00 -60.00  100
 11  \w    -19.00  23.00   0.50    0.05    --  -47.50  19.00-150.00   84
 12  \w    -20.00   6.00   0.50    0.05    --  -47.50  19.00 -90.00   52
 13  \w   -111.00 -86.00   0.50    0.15    --  -91.75 -99.00-120.00   50
 14  \w   -166.00-107.00   0.50    0.15    --  -91.75 -19.00 -60.00  118
 15  \w   -142.00 -86.00   0.50    0.15    --  -91.75 -99.00-150.00  112
 16  \w   -162.00-116.00   0.50    0.15    --  -91.75 -57.00  60.00   92
 17  \w   -157.00 -87.00   0.50    0.15    --  -91.75 -99.00  90.00  140
 18  \w   -159.00-116.00   0.50    0.15    --  -91.75 -99.00-120.00   86
 19  \w   -105.00 -77.00   0.50    0.15    --  -91.75 -57.00  60.00   56
 20  \w     39.00  96.00   0.50    0.15    --  109.69 -99.00 -90.00  114
 21  \w     39.00 104.00   0.50    0.15    --  109.69 -99.00  30.00  130
 22  \w     40.00  75.00   0.50    0.15    --  109.69 -77.00 -90.00   70
 23  \w     65.00 105.00   0.50    0.15    --  109.69 -99.00 120.00   80
 24  \w     37.00  68.00   0.50    0.15    --  109.69 -57.00  60.00   62
 25  \w     45.00  87.00   0.50    0.15    --  109.69-125.00  90.00   84
 26  \w     43.00 102.00   0.50    0.15    --  109.69 -99.00-150.00  118
 27  \w     38.00  68.00   0.50    0.15    --  109.69 -57.00-150.00   60
 28  \w     40.00  68.00   0.50    0.15    --  109.69 -57.00 120.00   56
 29  \w     68.00  94.00   0.50    0.15    --  109.69 -77.00 -30.00   52
 30  \w     98.00 170.00   0.50    0.15    --  109.69  19.00 150.00  144
 31  \w    138.00 176.00   0.50    0.15    --  109.69  57.00-180.00   76
 32  \w     95.00 132.00   0.50    0.15    --  109.69  57.00-180.00   74
 33  \w     64.00 106.00   0.50    0.15    --  109.69 -99.00  90.00   84
 34  \w     78.00 106.00   0.50    0.15    --  109.69 -99.00 -60.00   56
 35  \w     38.00  63.00   0.50    0.15    --  109.69 -57.00 -60.00   50
 36  \w     58.00  84.00   0.50    0.15    --  109.69 -99.00-180.00   52
 37  \w     82.00 107.00   0.50    0.15    --  109.69 -77.00 -90.00   50
 38  \w     37.00  68.00   0.50    0.15    --  109.69 -57.00 -90.00   62
 39  \w     77.00 105.00   0.50    0.15    --  109.69 -83.00 117.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1224838000
_diffrn_orient_matrix_UB_12      -0.0857358000
_diffrn_orient_matrix_UB_13      -0.0940703000
_diffrn_orient_matrix_UB_21      -0.0757503000
_diffrn_orient_matrix_UB_22      0.1014747000
_diffrn_orient_matrix_UB_23      0.0034034000
_diffrn_orient_matrix_UB_31      0.1148201000
_diffrn_orient_matrix_UB_32      0.1138826000
_diffrn_orient_matrix_UB_33      -0.0517541000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15215
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.965
_diffrn_reflns_theta_min         3.081
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.198
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.627
_exptl_crystal_size_mid          0.269
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         5127
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0624P)^2^+0.2343P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1235
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4512
_reflns_number_total             5127
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03778b2.cif
_cod_data_source_block           xrf03052024b_auto
_cod_depositor_comments
'Adding full bibliography for 7133713--7133714.cif.'
_cod_database_code               7133714
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'c27 h37 O4 P'
_chemical_oxdiff_usercomment     'crystallized from 1-PrOH'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00B), C00G(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C00D(H00C,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 C006(H006), C00A(H00A), C00F(H00F), C00J(H00J), C00K(H00K), C00L(H00L),
 C00N(H00N), C00S(H00Z), C00U(H1)
2.d Idealised Me refined as rotating group:
 C00M(H00E,H00H,H00I), C00O(H00M,H00O,H00P), C00P(H00Q,H00R,H00S), C00Q(H00T,
 H00U,H00V), C00R(H00W,H00X,H00Y), C00T(H00,H,HA), C00V(H2,HB,HC), C00W(H3,HD,
 HE)
;
_shelx_res_checksum              54555
_shelx_hkl_checksum              79189
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.491
_oxdiff_exptl_absorpt_empirical_full_min 0.606