Dearomative intermolecular [2 + 2] photocycloaddition for construction of C(sp<sup>3</sup>)-rich heterospirocycles on-DNA.
Li, Longbo; Matsuo, Bianca; Levitre, Guillaume; McClain, Edward J.; Voight, Eric A.; Crane, Erika A.; Molander, Gary A.; Chemical science 14 (2023) 2713–2720; doi:10.1039/d3sc00144j

data_1568486
_publ_section_title
;
 Dearomative intermolecular [2 + 2] photocycloaddition for construction of
 C(sp<sup>3</sup>)-rich heterospirocycles on-DNA.
;
_journal_issue                   10
_journal_name_full               'Chemical science'
_journal_page_first              2713
_journal_page_last               2720
_journal_paper_doi               10.1039/d3sc00144j
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C24 H31 N O6'
_chemical_formula_sum            'C24 H31 N O6'
_chemical_formula_weight         429.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-27
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2022-10-26 deposited with the CCDC.	2023-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 137.586(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.0386(15)
_cell_length_b                   13.2446(3)
_cell_length_c                   11.5475(8)
_cell_measurement_reflns_used    11718
_cell_measurement_temperature    100
_cell_measurement_theta_max      74.3750
_cell_measurement_theta_min      4.4450
_cell_volume                     2273.4(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'HPC area detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix-6000HE
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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   -120.00 -35.00   0.50    2.00    --  -47.04 -37.00  41.00  170
  2  \w    -26.00  39.00   0.50    2.00    --   47.04 -37.00  41.00  130
  3  \w     35.00 120.00   0.50    2.00    --   47.04  37.00-162.00  170
  4  \w    -45.00 -17.00   0.50    2.00    --  -90.00  37.00-162.00   56
  5  \w   -163.00 -77.00   0.50    2.00    --  -90.00 -37.00  41.00  172
  6  \w    101.00 178.00   0.50    2.00    --  113.25  37.00-162.00  154
  7  \w    -30.00  28.00   0.50    2.00    --  -47.04  19.00  30.00  116
  8  \w    -30.00  28.00   0.50    2.00    --  -47.04  19.00 -30.00  116
  9  \w    -45.00  26.00   0.50    2.00    --  -47.04  37.00-162.00  142
 10  \w     35.00 120.00   0.50    2.00    --   47.04  37.00 -90.00  170
 11  \w    -26.00  39.00   0.50    2.00    --   47.04 -37.00 -60.00  130
 12  \w    -25.00  70.00   0.50    2.00    --   47.04 -77.00-180.00  190
 13  \w    -54.00 -18.00   0.50    2.00    --  -90.00  45.00 -60.00   72
 14  \w   -109.00 -17.00   0.50    2.00    --  -90.00  77.00  60.00  184
 15  \w    -74.00 -17.00   0.50    2.00    --  -90.00  61.00   0.00  114
 16  \w   -109.00 -17.00   0.50    2.00    --  -90.00  77.00 -60.00  184
 17  \w   -109.00 -17.00   0.50    2.00    --  -90.00  77.00-180.00  184
 18  \w     48.00 102.00   0.50    2.00    --  113.25 -77.00  60.00  108
 19  \w    102.00 133.00   0.50    2.00    --  113.25  15.00-180.00   62
 20  \w    141.00 174.00   0.50    2.00    --  113.25  45.00 -90.00   66
 21  \w     42.00  68.00   0.50    2.00    --  113.25 -61.00-180.00   52
 22  \w    103.00 178.00   0.50    2.00    --  113.25  45.00   0.00  150
 23  \w    137.00 163.00   0.50    2.00    --  113.25  77.00 120.00   52
 24  \w    109.00 138.00   0.50    2.00    --  113.25  45.00 -90.00   58
 25  \w     74.00 102.00   0.50    2.00    --  113.25 -77.00 -60.00   56
 26  \w    144.00 170.00   0.50    2.00    --  113.25  45.00  60.00   52
 27  \w     91.00 135.00   0.50    2.00    --  113.25  77.00 120.00   88
 28  \w    101.00 133.00   0.50    2.00    --  113.25  45.00  60.00   64
 29  \w     54.00 102.00   0.50    2.00    --  113.25 -80.00 127.41   96
 30  \w     71.00  97.00   0.50    2.00    --  113.25 -77.00  30.00   52
 31  \w     67.00 119.00   0.50    2.00    --  113.25 -80.00  -5.36  104
 32  \w     42.00  67.00   0.50    2.00    --  113.25 -61.00  90.00   50
 33  \w     50.00 102.00   0.50    2.00    --  113.25 -77.00 150.00  104
 34  \w    141.00 172.00   0.50    2.00    --  113.25  15.00-180.00   62
 35  \w     48.00  86.00   0.50    2.00    --  113.25 -77.00-120.00   76
 36  \w    153.00 178.00   0.50    2.00    --  113.25  61.00  90.00   50
 37  \w     54.00 100.00   0.50    2.00    --  113.25 -77.00-180.00   92
 38  \w     99.00 139.00   0.50    2.00    --  113.25  61.00  90.00   80
 39  \w     44.00  97.00   0.50    2.00    --  113.25 -77.00 -90.00  106
 40  \w     67.00 129.00   0.50    2.00    --  113.25 -80.00-129.80  124
 41  \w     43.00  68.00   0.50    2.00    --  113.25 -61.00   0.00   50
 42  \w     45.00  72.00   0.50    2.00    --  113.25 -66.00 -33.61   54
 43  \w    106.00 154.00   0.50    2.00    --  113.25  45.00 -60.00   96
 44  \w     79.00 118.00   0.50    2.00    --  113.25 -80.00  72.07   78
 45  \w     94.00 177.00   0.50    2.00    --  113.25  77.00-150.00  166
 46  \w     48.00 101.00   0.50    2.00    --  113.25 -77.00   0.00  106
 47  \w     42.00  67.00   0.50    2.00    --  113.25 -61.00-150.00   50
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0880665000
_diffrn_orient_matrix_UB_12      0.0592076000
_diffrn_orient_matrix_UB_13      -0.1427395000
_diffrn_orient_matrix_UB_21      -0.0343072000
_diffrn_orient_matrix_UB_22      -0.0839281000
_diffrn_orient_matrix_UB_23      -0.1296242000
_diffrn_orient_matrix_UB_31      -0.0425407000
_diffrn_orient_matrix_UB_32      -0.0546234000
_diffrn_orient_matrix_UB_33      0.0441615000
_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  0.0430
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17402
_diffrn_reflns_point_group_measured_fraction_full 0.873
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.670
_diffrn_reflns_theta_min         4.471
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALE3 ABSPACK'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       needle
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1453 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3997
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0719P)^2^+0.2868P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    0.745
_reflns_Friedel_fraction_max     0.713
_reflns_number_gt                3771
_reflns_number_total             3997
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00144j2.cif
_cod_data_source_block           9259
_cod_depositor_comments          'Adding full bibliography for 1568486.cif.'
_cod_original_cell_volume        2273.4(4)
_cod_database_code               1568486
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              11502
_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 1.997
_oxdiff_exptl_absorpt_empirical_full_min 0.679