Diversifying chemical space of DNA-encoded libraries: synthesis of 2-oxa-1-azaspiro(bicyclo[3.2.0])heptanes on-DNA <i>via</i> visible light-mediated energy transfer catalysis.
Matsuo, Bianca; Kim, Saegun; Shreiber, Scott T.; Levitre, Guillaume; Li, Longbo; Crane, Erika A.; McClain, Edward J.; Voight, Eric A.; Molander, Gary A.; Chemical communications (Cambridge, England)  (2023) –; doi:10.1039/d3cc03421f

data_7132045
_publ_section_title
;
 Diversifying chemical space of DNA-encoded libraries: synthesis of
 2-oxa-1-azaspiro(bicyclo[3.2.0])heptanes on-DNA <i>via</i> visible
 light-mediated energy transfer catalysis.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d3cc03421f
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H21 N O3'
_chemical_formula_sum            'C17 H21 N O3'
_chemical_formula_weight         287.35
_chemical_name_common            'chemical 1''
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-05
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-05-08 deposited with the CCDC.	2023-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.78560(10)
_cell_length_b                   32.0930(3)
_cell_length_c                   5.26760(10)
_cell_measurement_reflns_used    15994
_cell_measurement_temperature    100
_cell_measurement_theta_max      74.2610
_cell_measurement_theta_min      2.7300
_cell_volume                     1485.23(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2018)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -119.00 -34.00   0.50    1.00    --  -47.31 -50.00  20.00  170
  2  \w    -60.00  25.00   0.50    1.00    --  -47.31  50.00 167.00  170
  3  \w     34.00 120.00   0.50    1.00    --   47.31  50.00 167.00  172
  4  \w    -24.00  54.00   0.50    1.00    --   47.31 -50.00  20.00  156
  5  \w   -161.00 -76.00   0.50    1.00    --  -90.00 -50.00  20.00  170
  6  \w    -60.00 -17.00   0.50    1.00    --  -90.00  50.00 167.00   86
  7  \w    100.00 178.00   0.50    1.00    --  113.25  50.00 167.00  156
  8  \w     25.00 120.00   0.50    1.00    --   47.31  77.00 -90.00  190
  9  \w     35.00 121.00   0.50    1.00    --   47.31  37.00 -90.00  172
 10  \w    -27.00  23.00   0.50    1.00    --   47.31 -19.00-150.00  100
 11  \w   -162.00 -73.00   0.50    1.00    --  -90.00 -63.00 -92.11  178
 12  \w   -162.00 -68.00   0.50    1.00    --  -90.00 -75.00-117.94  188
 13  \w    -54.00 -18.00   0.50    1.00    --  -90.00  45.00   0.00   72
 14  \w    -54.00 -18.00   0.50    1.00    --  -90.00  45.00 -30.00   72
 15  \w   -141.00 -76.00   0.50    1.00    --  -90.00 -52.00 -69.21  130
 16  \w    -99.00 -69.00   0.50    1.00    --  -90.00 -77.00 -90.00   60
 17  \w    -93.00 -67.00   0.50    1.00    --  -90.00 -77.00 -60.00   52
 18  \w    -98.00 -72.00   0.50    1.00    --  -90.00 -64.00 -39.17   52
 19  \w    136.00 178.00   0.50    1.00    --  113.25  77.00 -90.00   84
 20  \w    119.00 177.00   0.50    1.00    --  113.25  30.00  60.00  116
 21  \w     42.00  68.00   0.50    1.00    --  113.25 -61.00-180.00   52
 22  \w     42.00  67.00   0.50    1.00    --  113.25 -61.00 -60.00   50
 23  \w     62.00  98.00   0.50    1.00    --  113.25 -77.00 -30.00   72
 24  \w     64.00 101.00   0.50    1.00    --  113.25 -77.00 120.00   74
 25  \w     42.00  68.00   0.50    1.00    --  113.25 -61.00 150.00   52
 26  \w    151.00 177.00   0.50    1.00    --  113.25  77.00-150.00   52
 27  \w     91.00 129.00   0.50    1.00    --  113.25  77.00-150.00   76
 28  \w     42.00  67.00   0.50    1.00    --  113.25 -61.00 -30.00   50
 29  \w     42.00  67.00   0.50    1.00    --  113.25 -61.00  90.00   50
 30  \w    103.00 129.00   0.50    1.00    --  113.25  47.00-104.00   52
 31  \w     45.00  98.00   0.50    1.00    --  113.25 -77.00  90.00  106
 32  \w    101.00 127.00   0.50    1.00    --  113.25  45.00 -90.00   52
 33  \w    130.00 155.00   0.50    1.00    --  113.25  45.00 -90.00   50
 34  \w     94.00 119.00   0.50    1.00    --  113.25  77.00 -90.00   50
 35  \w    151.00 176.00   0.50    1.00    --  113.25  61.00 -30.00   50
 36  \w     98.00 151.00   0.50    1.00    --  113.25  61.00 -60.00  106
 37  \w    110.00 136.00   0.50    1.00    --  113.25  61.00 -30.00   52
 38  \w     63.00  89.00   0.50    1.00    --  113.25 -77.00 -90.00   52
 39  \w     42.00  67.00   0.50    1.00    --  113.25 -61.00-120.00   50
 40  \w    122.00 175.00   0.50    1.00    --  113.25  77.00-180.00  106
 41  \w    103.00 121.00   0.50    1.00    --  113.25  61.00 -90.00   36
;
_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      0.0284994000
_diffrn_orient_matrix_UB_12      0.0473129000
_diffrn_orient_matrix_UB_13      -0.0132923000
_diffrn_orient_matrix_UB_21      0.1383492000
_diffrn_orient_matrix_UB_22      -0.0048976000
_diffrn_orient_matrix_UB_23      0.1772612000
_diffrn_orient_matrix_UB_31      0.1039257000
_diffrn_orient_matrix_UB_32      -0.0064465000
_diffrn_orient_matrix_UB_33      -0.2322263000
_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  0.0349
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            19650
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.438
_diffrn_reflns_theta_min         2.754
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALE3 ABSPACK'
_exptl_crystal_colour            colorless
_exptl_crystal_colour_primary    colorless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1269 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3023
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0425P)^2^+0.3159P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0771
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2942
_reflns_number_total             3023
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03421f2.cif
_cod_data_source_block           9262
_cod_database_code               7132045
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.732
_shelx_res_checksum              28414
_shelx_hkl_checksum              205
_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 1.490
_oxdiff_exptl_absorpt_empirical_full_min 0.366