Paired electrolysis enabled annulation for the quinolyl-modification of bioactive molecules
You, Shiqi; Ruan, Mengyao; Lu, Cuifen; Liu, Li; Weng, Yue; Yang, Guichun; Wang, Shengchun; Alhumade, Hesham; Lei, Aiwen; Gao, Meng; Chemical Science 13 (2022) 2310–2316; doi:10.1039/D1SC06757E

data_1566331
_publ_section_title
;
 Paired electrolysis enabled annulation for the quinolyl-modification of
 bioactive molecules
;
_journal_issue                   8
_journal_name_full               'Chemical Science'
_journal_page_first              2310
_journal_page_last               2316
_journal_paper_doi               10.1039/D1SC06757E
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C24 H29 N O6'
_chemical_formula_sum            'C24 H29 N O6'
_chemical_formula_weight         427.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc27t90d
_audit_creation_date             2021-01-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-25 deposited with the CCDC.	2022-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.6740(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.42220(10)
_cell_length_b                   8.60860(10)
_cell_length_c                   15.5730(2)
_cell_measurement_reflns_used    10704
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.8790
_cell_measurement_theta_min      2.8260
_cell_volume                     1126.77(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.960
_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    -82.00 -47.00   0.50    0.20    --  -98.50 111.00 -30.00   70
  2  \w    -41.00 -15.00   0.50    0.20    --  -98.50 111.00 -30.00   52
  3  \w      2.00  75.00   0.50    0.05    --   37.97  77.00-180.00  146
  4  \w     81.00 116.00   0.50    0.05    --   37.97  77.00-180.00   70
  5  \w     84.00 176.00   0.50    0.20    --  112.45  59.00-130.00  184
  6  \w     90.00 117.00   0.50    0.05    --   37.97  77.00 120.00   54
  7  \w     25.00  77.00   0.50    0.05    --   37.97  77.00 120.00  104
  8  \w     16.00  95.00   0.50    0.05    --   37.97  57.00   0.00  158
  9  \w      2.00  54.00   0.50    0.05    --   37.97  77.00 -60.00  104
 10  \w     15.00  66.00   0.50    0.05    --   37.97  59.00-130.00  102
 11  \w    -82.00 -10.00   0.50    0.05    --  -37.97 -57.00  30.00  144
 12  \w   -108.00 -82.00   0.50    0.05    --  -37.97 -59.00  89.00   52
 13  \w    -50.00  -9.00   0.50    0.05    --  -37.97 -57.00 120.00   82
 14  \w    -61.00  -3.00   0.50    0.05    --  -37.97 -77.00 -60.00  116
 15  \w   -114.00 -83.00   0.50    0.05    --  -37.97 -77.00 -60.00   62
 16  \w    -85.00 -60.00   0.50    0.20    --  -98.50 -77.00-120.00   50
 17  \w   -115.00 -62.00   0.50    0.20    --  -98.50 -72.00 -82.63  106
 18  \w   -172.00 -65.00   0.50    0.20    --  -98.50 -64.00 -63.00  214
 19  \w   -131.00 -65.00   0.50    0.20    --  -98.50 -67.00   6.15  132
 20  \w   -160.00 -60.00   0.50    0.20    --  -98.50 -77.00  30.00  200
 21  \w   -176.00-141.00   0.50    0.20    --  -98.50 -76.00  93.88   70
 22  \w   -172.00-101.00   0.50    0.20    --  -98.50 -59.00  89.00  142
 23  \w   -123.00 -61.00   0.50    0.20    --  -98.50 -76.00  93.88  124
 24  \w    -99.00 -60.00   0.50    0.20    --  -98.50 -77.00 -90.00   78
 25  \w   -129.00-103.00   0.50    0.20    --  -98.50 -77.00-120.00   52
 26  \w   -168.00-125.00   0.50    0.20    --  -98.50 -77.00-150.00   86
 27  \w   -174.00-116.00   0.50    0.20    --  -98.50 -77.00 -90.00  116
 28  \w   -174.00 -62.00   0.50    0.20    --  -98.50 -73.00 -17.89  224
 29  \w   -162.00-111.00   0.50    0.20    --  -98.50 -79.00 113.00  102
 30  \w   -160.00 -59.00   0.50    0.20    --  -98.50 -80.00 138.55  202
 31  \w    -93.00 -59.00   0.50    0.20    --  -98.50 -79.00 113.00   68
 32  \w   -143.00 -60.00   0.50    0.20    --  -98.50 -77.00   0.00  166
 33  \w    -89.00 -61.00   0.50    0.20    --  -98.50 -74.00-110.73   56
 34  \w   -152.00 -60.00   0.50    0.20    --  -98.50 -78.00-168.72  184
 35  \w   -173.00-123.00   0.50    0.20    --  -98.50 -74.00-110.73  100
 36  \w   -177.00-149.00   0.50    0.20    --  -98.50 -77.00   0.00   56
 37  \w   -174.00 -61.00   0.50    0.20    --  -98.50 -74.00  69.69  226
 38  \w   -108.00 -62.00   0.50    0.20    --  -98.50 -72.00  33.40   92
 39  \w   -146.00-115.00   0.50    0.20    --  -98.50 -72.00  33.40   62
 40  \w   -102.00 -60.00   0.50    0.20    --  -98.50 -77.00 -39.80   84
 41  \w    -85.00 -60.00   0.50    0.20    --  -98.50 -77.00 -60.00   50
 42  \w    -85.00 -60.00   0.50    0.20    --  -98.50 -77.00 -24.58   50
 43  \w   -136.00-111.00   0.50    0.20    --  -98.50 -77.00 -60.00   50
 44  \w   -170.00-145.00   0.50    0.20    --  -98.50 -77.00 -60.00   50
 45  \w   -116.00 -60.00   0.50    0.20    --  -98.50 -77.00-150.00  112
 46  \w    -83.00 -58.00   0.50    0.20    --  -98.50 -82.00-127.83   50
 47  \w   -177.00-114.00   0.50    0.20    --  -98.50 -82.00-127.83  126
 48  \w   -129.00-103.00   0.50    0.20    --  -98.50 -83.00  59.93   52
 49  \w   -154.00-128.00   0.50    0.20    --  -98.50 -81.00 164.36   52
 50  \w   -166.00-141.00   0.50    0.20    --  -98.50 -81.00 175.87   50
 51  \w   -157.00 -90.00   0.50    0.20    --  -98.50 -83.00 155.70  134
 52  \w   -103.00 -58.00   0.50    0.20    --  -98.50 -81.00 175.87   90
 53  \w    -83.00 -58.00   0.50    0.20    --  -98.50 -81.00 164.36   50
 54  \w    -87.00 -59.00   0.50    0.20    --  -98.50 -83.00 155.70   56
 55  \w    -83.00 -58.00   0.50    0.20    --  -98.50 -83.00  59.93   50
 56  \w    -73.00 -16.00   0.50    0.05    --  -37.97 -77.00  30.00  114
 57  \w    -76.00 -42.00   0.50    0.20    --  -98.50  59.00-130.00   68
 58  \w    -68.00  32.00   0.50    0.05    --  -37.97  59.00-130.00  200
 59  \w     71.00 103.00   0.50    0.05    --   37.97  59.00-130.00   64
 60  \w     44.00  70.00   0.50    0.20    --  112.45 -77.00-180.00   52
 61  \w     76.00 135.00   0.50    0.20    --  112.45 -77.00-180.00  118
 62  \w     41.00  89.00   0.50    0.20    --  112.45 -59.00  89.00   96
 63  \w      8.00  34.00   0.50    0.05    --   37.97 -59.00  89.00   52
 64  \w    -18.00   7.00   0.50   10.00    --    0.00 -59.00  89.00   50
 65  \w   -115.00 -60.00   0.50    0.05    --  -37.97 -57.00 120.00  110
 66  \w    -38.00   0.00   0.50    0.05    --   37.97 -59.00  89.00   76
 67  \w     33.00 110.00   0.50    0.20    --  112.45-111.00   0.00  154
 68  \w     61.00 108.00   0.50    0.20    --  112.45 -94.00  90.00   94
 69  \w     37.00 107.00   0.50    0.20    --  112.45-111.00  90.00  140
 70  \w     43.00  90.00   0.50    0.20    --  112.45-111.00 -60.00   94
 71  \w     28.00 105.00   0.50    0.20    --  112.45 -94.00-180.00  154
 72  \w    -11.00  14.00   0.50    0.05    --   37.97  99.00 -73.88   50
 73  \w     70.00 124.00   0.50    0.05    --   37.97 178.00-120.00  108
 74  \w     60.00 126.00   0.50    0.05    --   37.97 178.00   0.00  132
 75  \w     74.00 112.00   0.50    0.05    --   37.97 178.00 120.00   76
 76  \w     70.00 110.00   0.50    0.05    --   37.97 178.00 150.00   80
;
_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      -0.1174106000
_diffrn_orient_matrix_UB_12      -0.0822094000
_diffrn_orient_matrix_UB_13      -0.0649411000
_diffrn_orient_matrix_UB_21      -0.1335719000
_diffrn_orient_matrix_UB_22      0.1104061000
_diffrn_orient_matrix_UB_23      0.0248175000
_diffrn_orient_matrix_UB_31      0.0444645000
_diffrn_orient_matrix_UB_32      0.1143146000
_diffrn_orient_matrix_UB_33      -0.0706705000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21426
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.984
_diffrn_reflns_theta_min         2.843
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1859 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4277
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0278
_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^)+(0.0446P)^2^+0.0983P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0723
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.906
_reflns_number_gt                4190
_reflns_number_total             4277
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc06757e3.cif
_cod_data_source_block           ganshaol
_cod_depositor_comments          'Adding full bibliography for 1566331.cif.'
_cod_database_code               1566331
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.930
_shelx_estimated_absorpt_t_min   0.808
_reflns_odcompleteness_completeness 100.00
_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:
 C22(H22), C26(H26), C23(H23), C28(H28)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C25(H25A,H25B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1), C3(H3), C2(H2)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C31(H31A,H31B,H31C), C29(H29A,H29B,
 H29C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              65632
_shelx_hkl_checksum              91127
_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 1.216
_oxdiff_exptl_absorpt_empirical_full_min 0.808