Rhodium(II)-catalyzed annulation of N-sulfonyl-1,2,3-triazoles with 1,3,5-triazinanes to produce octahydro-1H-purine derivatives: A combined experimental and computational study
Ge, Jiemin; Wu, Xueli; Bao, Xiaoguang; Chemical Communications  (2019) –; doi:10.1039/C9CC02294E

data_7123347
_publ_section_title
;
 Rhodium(II)-catalyzed annulation of N-sulfonyl-1,2,3-triazoles with
 1,3,5-triazinanes to produce octahydro-1H-purine derivatives: A combined
 experimental and computational study
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC02294E
_journal_year                    2019
_chemical_formula_moiety         'C37 H36 N4 O3 S'
_chemical_formula_sum            'C37 H36 N4 O3 S'
_chemical_formula_weight         616.76
_chemical_name_systematic
5-(4-methoxyphenyl)-1,7,9-triphenyl-3-tosyloctahydro-1H-purine
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-15 deposited with the CCDC.    2019-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                74.55(2)
_cell_angle_beta                 87.703(15)
_cell_angle_gamma                79.93(2)
_cell_formula_units_Z            2
_cell_length_a                   9.503(6)
_cell_length_b                   10.244(7)
_cell_length_c                   17.165(11)
_cell_measurement_reflns_used    8527
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.45
_cell_volume                     1585.8(18)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26413
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.612
_diffrn_reflns_theta_min         2.508
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1703 before and 0.0678 after correction.
The Ratio of minimum to maximum transmission is 0.8920.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       block
_exptl_crystal_F_000             652
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate'
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         7341
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0583
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0805P)^2^+0.4221P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.1646
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4840
_reflns_number_total             7341
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc02294e2.cif
_cod_data_source_block           cc_a
_cod_database_code               7123347
_shelx_shelxl_version_number     2018/3
_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. Rigid bond restraints
 C00U, C00D
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Ternary CH refined with riding coordinates:
 C00G(H00G)
3.b Secondary CH2 refined with riding coordinates:
 C00J(H00A,H00B), C00L(H00C,H00D), C00R(H00H,H00J)
3.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00I(H00I), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V),
 C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012),
 C013(H013), C014(H014), C015(H015), C017(H017), C019(H019)
3.d Idealised Me refined as rotating group:
 C016(H01A,H01B,H01C), C018(H01D,H01E,H01F)
;
_shelx_res_checksum              3017
_olex2_submission_special_instructions 'No special instructions were received'