Acid-Mediated N-H/α,β-C(sp(3))-H Trifunctionalization of Pyrrolidine: Intermolecular [3 + 2] Cycloaddition for the Construction of 2,3-Dihydro-1H-Pyrrolizine Derivatives.
Zheng, Kai-Lu; Shu, Wen-Ming; Ma, Jun-Rui; Wu, Yan-Dong; Wu, An-Xin; Organic letters 18 (2016) 3526–3529; doi:10.1021/acs.orglett.6b01369

data_1543642
_publ_section_title
;
 Acid-Mediated N-H/\a,\b-C(sp(3))-H Trifunctionalization of Pyrrolidine:
 Intermolecular [3 + 2] Cycloaddition for the Construction of
 2,3-Dihydro-1H-Pyrrolizine Derivatives.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3526
_journal_page_last               3529
_journal_paper_doi               10.1021/acs.orglett.6b01369
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_sum            'C27 H26 N O6'
_chemical_formula_weight         460.49
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.491(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7825(11)
_cell_length_b                   33.713(5)
_cell_length_c                   9.4309(13)
_cell_measurement_reflns_used    5156
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.40
_cell_measurement_theta_min      2.36
_cell_volume                     2346.7(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            21467
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_correction_T_min  0.9800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             972
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.7(8)
_refine_ls_extinction_coef       0.0083(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     628
_refine_ls_number_reflns         11500
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0483
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0752P)^2^+0.0498P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1430
_reflns_number_gt                7659
_reflns_number_total             11500
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b01369_si_001.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1543642.cif.

2019-02-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C54 H52 N2 O12'
_cod_original_formula_weight         920.98
_cod_original_formula_units_Z            2
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1543642