Chemoselective asymmetric dearomative [3 + 2] cycloaddition reactions of purines with aminocyclopropanes
Hao, Er-Jun; Fu, Dan-Dan; Wang, Dong-Chao; Zhang, Tao; Qu, Gui-Rong; Li, Gong-Xin; Lan, Yu; Guo, Hai-Ming; Organic Chemistry Frontiers 6 (2019) 863–; doi:10.1039/C9QO00039A

data_1554707
_publ_section_title
;
 Chemoselective asymmetric dearomative [3 + 2] cycloaddition reactions of
 purines with aminocyclopropanes
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              863
_journal_paper_doi               10.1039/C9QO00039A
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C22 H26 Cl N5 O9'
_chemical_formula_sum            'C22 H26 Cl N5 O9'
_chemical_formula_weight         539.93
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-02-05
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.01.22 svn.r3481 for OlexSys, GUI svn.r5465)
;
_audit_update_record
;
2018-04-18 deposited with the CCDC.
2019-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.1150(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6444(2)
_cell_length_b                   19.0270(3)
_cell_length_c                   9.29920(10)
_cell_measurement_reflns_used    10087
_cell_measurement_temperature    291.42(10)
_cell_measurement_theta_max      72.5720
_cell_measurement_theta_min      4.6390
_cell_volume                     2565.17(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.42(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_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     23.00  90.00   1.00    1.00    --   36.21-125.00  90.00   67
  2  \w    -31.00  53.00   1.00    1.00    --   36.21 -57.00  90.00   84
  3  \w     23.00  90.00   1.00    1.00    --   36.21-125.00 -60.00   67
  4  \w    -31.00  63.00   1.00    1.00    --   36.21 -77.00  60.00   94
  5  \w     17.00 105.00   1.00    1.00    --   36.21  38.00-120.00   88
  6  \w     19.00 103.00   1.00    1.00    --   36.21  57.00 -30.00   84
  7  \w     19.00 103.00   1.00    1.00    --   36.21  57.00  60.00   84
  8  \w     19.00 103.00   1.00    1.00    --   36.21  57.00-120.00   84
  9  \w     23.00  90.00   1.00    1.00    --   36.21-125.00 -90.00   67
 10  \w     42.00 127.00   1.00    1.86    --  109.31 -61.00-150.00   85
 11  \w     39.00 116.00   1.00    1.86    --  109.31-111.00  60.00   77
 12  \w     83.00 177.00   1.00    1.86    --  109.31  77.00-180.00   94
 13  \w    100.00 178.00   1.00    1.86    --  109.31 111.00 150.00   78
 14  \w     92.00 178.00   1.00    1.86    --  109.31  45.00 120.00   86
 15  \w     42.00 136.00   1.00    1.86    --  109.31 -77.00  90.00   94
 16  \w     42.00 127.00   1.00    1.86    --  109.31 -61.00  60.00   85
 17  \w     83.00 177.00   1.00    1.86    --  109.31  77.00-150.00   94
 18  \w     83.00 177.00   1.00    1.86    --  109.31  77.00 -90.00   94
 19  \w    -31.00  53.00   1.00    1.00    --   36.21 -57.00-180.00   84
 20  \w    -33.00  55.00   1.00    1.00    --   36.21 -38.00 -90.00   88
 21  \w      9.00 104.00   1.00    1.00    --   36.21  77.00 150.00   95
 22  \w      9.00  69.00   1.00    1.00    --   36.21  77.00   0.00   60
 23  \w     17.00 105.00   1.00    1.00    --   36.21  38.00 150.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0646719000
_diffrn_orient_matrix_UB_12      -0.0640654000
_diffrn_orient_matrix_UB_13      -0.0028380000
_diffrn_orient_matrix_UB_21      -0.0802044000
_diffrn_orient_matrix_UB_22      0.0444950000
_diffrn_orient_matrix_UB_23      -0.0771095000
_diffrn_orient_matrix_UB_31      0.0259941000
_diffrn_orient_matrix_UB_32      -0.0218548000
_diffrn_orient_matrix_UB_33      -0.1484089000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20088
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.482
_diffrn_reflns_theta_min         3.833
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.846
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       plate
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0664
_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^)+(0.1211P)^2^+0.9016P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1850
_refine_ls_wR_factor_ref         0.1976
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4205
_reflns_number_total             5015
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00039a2.cif
_cod_data_source_block           fdd-2-1-20180205
_cod_database_code               1554707
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C1 O1 N1'
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.581
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b), C11(H11a,H11b), C16(H16a,H16b), C33(H33a,H33b)
2.c Aromatic/amide H refined with riding coordinates:
 N13(H13), C29(H29), C30(H30), C5(H5)
2.d Idealised Me refined as rotating group:
 C23(H23a,H23b,H23c), C27(H27a,H27b,H27c), C34(H34a,H34b,H34c), C1(H1a,H1b,H1c)
;
_shelx_res_checksum              11987
_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 2.414
_oxdiff_exptl_absorpt_empirical_full_min 0.408