A Cascade Reaction of Cinnamyl Azides with Acrylates Directly Generates Tetrahydro-Pyrrolo-Pyrazole Heterocycles.
Carlson, Angela S.; Liu, En-Chih; Topczewski, Joseph J.; The Journal of organic chemistry 85 (2020) 6044–6059; doi:10.1021/acs.joc.0c00535

data_4038280
_publ_section_title
;
 A Cascade Reaction of Cinnamyl Azides with Acrylates Directly Generates
 Tetrahydro-Pyrrolo-Pyrazole Heterocycles.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6044
_journal_page_last               6059
_journal_paper_doi               10.1021/acs.joc.0c00535
_journal_volume                  85
_journal_year                    2020
_chemical_formula_sum            'C34 H45 Cl3 N6 O4'
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_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
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_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            8
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_cell_measurement_reflns_used    9879
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      27.60
_cell_measurement_theta_min      2.67
_cell_volume                     7101.4(16)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0715
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
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_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.058
_exptl_absorpt_coefficient_mu    0.304
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       prism
_exptl_crystal_F_000             2992
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     895
_refine_ls_number_reflns         14529
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_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0647
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_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0437P)^2^+5.3912P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1145
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10401
_reflns_number_total             14529
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00535_si_004.cif
_cod_data_source_block           20019a_a
_cod_depositor_comments
;
Adding full bibliography for 4038279--4038282.cif.

2025-07-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        7101.3(17)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C68 H90 Cl6 N12 O8'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1416.21
_cod_database_code               4038280
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.888
_shelx_estimated_absorpt_t_max   0.942
_shelx_res_checksum              76358
_shelx_hkl_checksum              21911