Synergistic promotion by intramolecular hydrogen bonding: a bi-functionally catalyzed cascade reaction for the synthesis of enantiopure chromenopyrrolidines
Cao, Jian; Liu, Jin-Yu; Zhang, Yi-Ming; Wang, Zhu-Yin; Xu, Peng-Fei; Organic Chemistry Frontiers 6 (2019) 674–; doi:10.1039/C8QO01208C

data_1554535
_publ_section_title
;
 Synergistic promotion by intramolecular hydrogen bonding: a
 bi-functionally catalyzed cascade reaction for the synthesis of
 enantiopure chromenopyrrolidines
;
_journal_issue                   5
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              674
_journal_paper_doi               10.1039/C8QO01208C
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C33 H32 Cl N O9'
_chemical_formula_sum            'C33 H32 Cl N O9'
_chemical_formula_weight         622.05
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-05-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-06-11 deposited with the CCDC.
2019-01-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0158(17)
_cell_length_b                   12.1300(16)
_cell_length_c                   23.587(3)
_cell_measurement_reflns_used    1003
_cell_measurement_temperature    295.19(10)
_cell_measurement_theta_max      19.5340
_cell_measurement_theta_min      3.8220
_cell_volume                     3151.7(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      295.19(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   -4.00   23.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -99.0000   60.0000 27

  2 omega  -45.00  -15.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273   77.0000 -180.0000 30

  3 omega  -51.00   52.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -38.0000  120.0000 103
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0548484000
_diffrn_orient_matrix_UB_12      -0.0286169000
_diffrn_orient_matrix_UB_13      0.0056244000
_diffrn_orient_matrix_UB_21      0.0311794000
_diffrn_orient_matrix_UB_22      0.0509674000
_diffrn_orient_matrix_UB_23      0.0024730000
_diffrn_orient_matrix_UB_31      -0.0131082000
_diffrn_orient_matrix_UB_32      0.0011516000
_diffrn_orient_matrix_UB_33      0.0294199000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.1189
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8253
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.36
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         5621
_refine_ls_number_restraints     69
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1754
_refine_ls_R_factor_gt           0.0917
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1185P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2117
_refine_ls_wR_factor_ref         0.2924
_reflns_number_gt                2366
_reflns_number_total             5621
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8qo01208c2.cif
_cod_data_source_block           caoj_0528
_cod_original_cell_volume        3151.8(8)
_cod_database_code               1554535
_reflns_odcompleteness_completeness 99.59
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H1A-N1
 0.82 with sigma of 0.01
 C20-C19
 1.45 with sigma of 0.01
 C22-C23
 1.45 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C19) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C20) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C23) \\sim Ueq, Uanis(C22) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C28) \\sim Ueq, Uanis(C29) \\sim Ueq, Uanis(C30) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(O9) \\sim Ueq, Uanis(O8) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O8) \\sim Ueq, Uanis(O9) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C1(H1), C9(H9), C10(H10)
4.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C22(H22A,H22B), C19(H19A,H19B)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C17(H17), C15(H15), C4(H4), C13(H13), C16(H16), C29(H29),
 C14(H14), C27(H27), C30(H30), C31(H31), C28(H28)
4.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C20(H20A,H20B,H20C), C23(H23A,H23B,H23C)
;
_olex2_date_sample_data_collection 2018-05-28
_olex2_submission_special_instructions 'No special instructions were received'