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_1554708
_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         'C25 H22 Cl N5 O8'
_chemical_formula_sum            'C25 H22 Cl N5 O8'
_chemical_formula_weight         555.92
_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
_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                103.938(3)
_cell_angle_beta                 101.104(4)
_cell_angle_gamma                102.417(4)
_cell_formula_units_Z            2
_cell_length_a                   8.9522(4)
_cell_length_b                   12.3288(5)
_cell_length_c                   12.6211(5)
_cell_measurement_reflns_used    6083
_cell_measurement_temperature    291.69(10)
_cell_measurement_theta_max      28.4420
_cell_measurement_theta_min      3.8950
_cell_volume                     1275.71(10)
_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      291.69(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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     -1.00  83.00   1.00    3.71    --   16.13  57.00 -90.00   84
  2  \w    -14.00  59.00   1.00    3.71    --   16.13-106.00  36.00   73
  3  \w    -11.00  84.00   1.00    3.71    --   16.13  77.00 150.00   95
  4  \w    -11.00  84.00   1.00    3.71    --   16.13  77.00 -60.00   95
  5  \w    -51.00  33.00   1.00    3.71    --   16.13 -57.00  60.00   84
  6  \w    -51.00  33.00   1.00    3.71    --   16.13 -57.00   0.00   84
  7  \w    -51.00  31.00   1.00    3.71    --   16.13 -57.00-180.00   82
;
_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      0.0791666000
_diffrn_orient_matrix_UB_12      0.0146285000
_diffrn_orient_matrix_UB_13      -0.0044337000
_diffrn_orient_matrix_UB_21      -0.0278834000
_diffrn_orient_matrix_UB_22      -0.0042502000
_diffrn_orient_matrix_UB_23      -0.0578036000
_diffrn_orient_matrix_UB_31      0.0024139000
_diffrn_orient_matrix_UB_32      0.0597328000
_diffrn_orient_matrix_UB_33      0.0151905000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14063
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.376
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84509
_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    1.447
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         4475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0665P)^2^+0.3673P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1314
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3674
_reflns_number_total             4475
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00039a2.cif
_cod_data_source_block           fdd-1-20180205
_cod_database_code               1554708
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C1 O1 N1'
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.912
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C10(H10), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C(Ha,Hb)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C16(H16), C19(H19), C24(H24), C25(H25), C18(H18), C17(H17)
2.d Idealised Me refined as rotating group:
 C31(H31a,H31b,H31c), C35(H35a,H35b,H35c), C0AA(H0Aa,H0Ab,H0Ac)
;
_shelx_res_checksum              98042
_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 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.716