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#$Date: 2024-04-05 01:48:11 +0300 (Fri, 05 Apr 2024) $
#$Revision: 290845 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/10/1571074.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1571074
loop_
_publ_author_name
'Zhan, Tangyu'
'Zhou, Liang'
'Zhou, Yuqiao'
'Yang, Bingqian'
'Feng, Xiaoming'
'Liu, Xiaohua'
_publ_section_title
;
 IronIII-catalyzed asymmetric inverse-electron-demand
 hetero-Diels-Alder reaction of dioxopyrrolidines with simple olefins.
;
_journal_issue                   13
_journal_name_full               'Chemical science'
_journal_page_first              4797
_journal_page_last               4803
_journal_paper_doi               10.1039/d4sc00078a
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H23 N O4'
_chemical_formula_sum            'C26 H23 N O4'
_chemical_formula_weight         413.45
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-12-23 deposited with the CCDC.	2024-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7506(2)
_cell_length_b                   9.9990(2)
_cell_length_c                   25.0270(6)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      79.14
_cell_measurement_theta_min      3.53
_cell_volume                     2189.79(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            37727
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.473
_diffrn_reflns_theta_min         3.532
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  0.9356
_exptl_absorpt_correction_T_min  0.6124
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       rod
_exptl_crystal_F_000             872
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, Hexane'
_exptl_crystal_size_max          0.866
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.167
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
; 
 Flack x determined using 1929 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0530P)²+0.5015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0958
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                4580
_reflns_number_total             4660
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc00078a2.cif
_cod_data_source_block           lii028
_cod_depositor_comments
'Adding full bibliography for 1571072--1571074.cif.'
_cod_database_code               1571074
_shelx_shelxl_version_number     2019/1
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.589
_shelx_estimated_absorpt_t_max   0.894
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.83062(18) 0.43394(16) 0.34752(6) 0.0406(4) Uani 1 1 d . . . . .
O2 O 0.92921(16) 0.19050(12) 0.40634(5) 0.0269(3) Uani 1 1 d . . . . .
O3 O 1.00958(17) 0.09403(14) 0.48317(6) 0.0338(3) Uani 1 1 d . . . . .
O4 O 1.18789(17) 0.33433(15) 0.48655(6) 0.0345(3) Uani 1 1 d . . . . .
N N 0.97419(18) 0.43383(15) 0.45310(6) 0.0266(3) Uani 1 1 d . . . . .
C1 C 0.8090(2) 0.42189(19) 0.44298(8) 0.0287(4) Uani 1 1 d . . . . .
H1A H 0.759549 0.508303 0.451607 0.034 Uiso 1 1 calc R U . . .
H1B H 0.766237 0.353580 0.467413 0.034 Uiso 1 1 calc R U . . .
C2 C 0.7681(2) 0.38371(19) 0.38543(8) 0.0293(4) Uani 1 1 d . . . . .
C3 C 0.6413(2) 0.2773(2) 0.37907(7) 0.0287(4) Uani 1 1 d . . . . .
H3 H 0.601077 0.254444 0.415339 0.034 Uiso 1 1 calc R U . . .
C4 C 0.7117(2) 0.1499(2) 0.35430(8) 0.0326(4) Uani 1 1 d . . . . .
H4A H 0.628494 0.085792 0.346447 0.039 Uiso 1 1 calc R U . . .
H4B H 0.760518 0.174010 0.319935 0.039 Uiso 1 1 calc R U . . .
C5 C 0.8300(2) 0.08077(18) 0.38957(7) 0.0282(4) Uani 1 1 d . . . . .
H5 H 0.779855 0.038181 0.421190 0.034 Uiso 1 1 calc R U . . .
C6 C 0.9955(2) 0.18831(17) 0.45450(7) 0.0242(3) Uani 1 1 d . . . . .
C7 C 1.0605(2) 0.32771(18) 0.46670(7) 0.0253(3) Uani 1 1 d . . . . .
C11 C 1.0384(2) 0.56741(18) 0.46083(8) 0.0308(4) Uani 1 1 d . . . . .
H11A H 1.006142 0.625153 0.430738 0.037 Uiso 1 1 calc R U . . .
H11B H 1.151289 0.561143 0.459905 0.037 Uiso 1 1 calc R U . . .
C12 C 0.9906(2) 0.63285(18) 0.51281(8) 0.0294(4) Uani 1 1 d . . . . .
C13 C 0.9375(3) 0.5603(2) 0.55622(9) 0.0414(5) Uani 1 1 d . . . . .
H13 H 0.928540 0.465830 0.553734 0.050 Uiso 1 1 calc R U . . .
C14 C 0.8971(4) 0.6249(3) 0.60335(10) 0.0530(6) Uani 1 1 d . . . . .
H14 H 0.860494 0.574478 0.632871 0.064 Uiso 1 1 calc R U . . .
C15 C 0.9104(3) 0.7629(3) 0.60734(11) 0.0539(6) Uani 1 1 d . . . . .
H15 H 0.883302 0.807126 0.639569 0.065 Uiso 1 1 calc R U . . .
C16 C 0.9631(3) 0.8354(2) 0.56421(11) 0.0485(6) Uani 1 1 d . . . . .
H16 H 0.972158 0.929882 0.566793 0.058 Uiso 1 1 calc R U . . .
C17 C 1.0028(3) 0.7714(2) 0.51725(9) 0.0389(5) Uani 1 1 d . . . . .
H17 H 1.038685 0.822296 0.487757 0.047 Uiso 1 1 calc R U . . .
C21 C 0.5094(2) 0.3277(2) 0.34514(7) 0.0319(4) Uani 1 1 d . . . . .
C22 C 0.5239(3) 0.3452(4) 0.29036(10) 0.0627(8) Uani 1 1 d . . . . .
H22 H 0.618728 0.326755 0.273389 0.075 Uiso 1 1 calc R U . . .
C23 C 0.4007(4) 0.3895(4) 0.26025(11) 0.0688(10) Uani 1 1 d . . . . .
H23 H 0.411974 0.401458 0.222804 0.083 Uiso 1 1 calc R U . . .
C24 C 0.2630(3) 0.4160(3) 0.28400(10) 0.0496(6) Uani 1 1 d . . . . .
H24 H 0.180349 0.450043 0.263497 0.060 Uiso 1 1 calc R U . . .
C25 C 0.2457(3) 0.3930(3) 0.33734(10) 0.0436(5) Uani 1 1 d . . . . .
H25 H 0.149129 0.407113 0.353763 0.052 Uiso 1 1 calc R U . . .
C26 C 0.3691(2) 0.3490(2) 0.36791(9) 0.0347(4) Uani 1 1 d . . . . .
H26 H 0.355686 0.333532 0.405066 0.042 Uiso 1 1 calc R U . . .
C31 C 0.9203(2) -0.0212(2) 0.35822(7) 0.0318(4) Uani 1 1 d . . . . .
C32 C 1.0360(3) 0.0206(2) 0.32314(9) 0.0400(5) Uani 1 1 d . . . . .
H32 H 1.062786 0.112592 0.321415 0.048 Uiso 1 1 calc R U . . .
C33 C 1.1115(3) -0.0710(3) 0.29094(10) 0.0510(6) Uani 1 1 d . . . . .
H33 H 1.189219 -0.041932 0.267135 0.061 Uiso 1 1 calc R U . . .
C34 C 1.0729(4) -0.2043(3) 0.29373(11) 0.0566(7) Uani 1 1 d . . . . .
H34 H 1.125342 -0.267140 0.271965 0.068 Uiso 1 1 calc R U . . .
C35 C 0.9602(4) -0.2473(2) 0.32741(10) 0.0568(8) Uani 1 1 d . . . . .
H35 H 0.934245 -0.339484 0.328718 0.068 Uiso 1 1 calc R U . . .
C36 C 0.8825(3) -0.1551(2) 0.36020(9) 0.0441(5) Uani 1 1 d . . . . .
H36 H 0.804185 -0.185100 0.383613 0.053 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O2 C5 120.27(14) . . ?
C7 N C11 118.11(16) . . ?
C7 N C1 122.02(15) . . ?
C11 N C1 118.31(15) . . ?
N C1 C2 114.27(15) . . ?
O1 C2 C1 122.02(18) . . ?
O1 C2 C3 122.13(18) . . ?
C1 C2 C3 115.85(15) . . ?
C21 C3 C4 110.65(16) . . ?
C21 C3 C2 112.00(16) . . ?
C4 C3 C2 108.81(15) . . ?
C5 C4 C3 114.34(15) . . ?
O2 C5 C31 110.20(16) . . ?
O2 C5 C4 103.23(14) . . ?
C31 C5 C4 111.14(15) . . ?
O3 C6 O2 126.93(17) . . ?
O3 C6 C7 124.04(16) . . ?
O2 C6 C7 108.95(14) . . ?
O4 C7 N 124.87(17) . . ?
O4 C7 C6 117.90(16) . . ?
N C7 C6 117.20(15) . . ?
N C11 C12 113.71(15) . . ?
C13 C12 C17 118.88(19) . . ?
C13 C12 C11 122.65(17) . . ?
C17 C12 C11 118.46(17) . . ?
C12 C13 C14 120.5(2) . . ?
C15 C14 C13 120.1(2) . . ?
C16 C15 C14 119.6(2) . . ?
C15 C16 C17 120.4(2) . . ?
C16 C17 C12 120.6(2) . . ?
C26 C21 C22 118.3(2) . . ?
C26 C21 C3 119.98(17) . . ?
C22 C21 C3 121.61(19) . . ?
C21 C22 C23 120.3(2) . . ?
C24 C23 C22 120.6(2) . . ?
C25 C24 C23 119.4(2) . . ?
C24 C25 C26 120.3(2) . . ?
C21 C26 C25 121.0(2) . . ?
C36 C31 C32 119.0(2) . . ?
C36 C31 C5 120.7(2) . . ?
C32 C31 C5 120.07(18) . . ?
C33 C32 C31 120.6(2) . . ?
C34 C33 C32 119.6(3) . . ?
C35 C34 C33 120.8(2) . . ?
C34 C35 C36 120.1(2) . . ?
C31 C36 C35 119.9(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.205(2) . ?
O2 C6 1.338(2) . ?
O2 C5 1.461(2) . ?
O3 C6 1.191(2) . ?
O4 C7 1.222(2) . ?
N C7 1.346(2) . ?
N C11 1.462(2) . ?
N C1 1.473(2) . ?
C1 C2 1.532(3) . ?
C2 C3 1.546(3) . ?
C3 C21 1.519(3) . ?
C3 C4 1.545(3) . ?
C4 C5 1.526(3) . ?
C5 C31 1.510(3) . ?
C6 C7 1.536(2) . ?
C11 C12 1.515(3) . ?
C12 C13 1.387(3) . ?
C12 C17 1.394(3) . ?
C13 C14 1.390(3) . ?
C14 C15 1.389(4) . ?
C15 C16 1.380(4) . ?
C16 C17 1.383(3) . ?
C21 C26 1.370(3) . ?
C21 C22 1.388(3) . ?
C22 C23 1.388(4) . ?
C23 C24 1.369(4) . ?
C24 C25 1.363(4) . ?
C25 C26 1.395(3) . ?
C31 C36 1.380(3) . ?
C31 C32 1.404(3) . ?
C32 C33 1.387(3) . ?
C33 C34 1.376(4) . ?
C34 C35 1.367(5) . ?
C35 C36 1.409(4) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N C1 C2 -86.6(2) . . . . ?
C11 N C1 C2 107.91(18) . . . . ?
N C1 C2 O1 -43.3(3) . . . . ?
N C1 C2 C3 136.92(17) . . . . ?
O1 C2 C3 C21 -56.6(2) . . . . ?
C1 C2 C3 C21 123.18(17) . . . . ?
O1 C2 C3 C4 66.1(2) . . . . ?
C1 C2 C3 C4 -114.17(17) . . . . ?
C21 C3 C4 C5 -171.77(17) . . . . ?
C2 C3 C4 C5 64.8(2) . . . . ?
C6 O2 C5 C31 -93.97(18) . . . . ?
C6 O2 C5 C4 147.27(16) . . . . ?
C3 C4 C5 O2 -48.2(2) . . . . ?
C3 C4 C5 C31 -166.27(17) . . . . ?
C5 O2 C6 O3 16.3(3) . . . . ?
C5 O2 C6 C7 -166.75(15) . . . . ?
C11 N C7 O4 2.1(3) . . . . ?
C1 N C7 O4 -163.39(17) . . . . ?
C11 N C7 C6 -175.70(15) . . . . ?
C1 N C7 C6 18.8(2) . . . . ?
O3 C6 C7 O4 40.3(3) . . . . ?
O2 C6 C7 O4 -136.73(16) . . . . ?
O3 C6 C7 N -141.71(19) . . . . ?
O2 C6 C7 N 41.3(2) . . . . ?
C7 N C11 C12 -96.3(2) . . . . ?
C1 N C11 C12 69.8(2) . . . . ?
N C11 C12 C13 20.9(3) . . . . ?
N C11 C12 C17 -159.99(19) . . . . ?
C17 C12 C13 C14 0.0(4) . . . . ?
C11 C12 C13 C14 179.0(2) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C15 C16 C17 C12 -0.2(4) . . . . ?
C13 C12 C17 C16 0.2(4) . . . . ?
C11 C12 C17 C16 -178.9(2) . . . . ?
C4 C3 C21 C26 126.0(2) . . . . ?
C2 C3 C21 C26 -112.4(2) . . . . ?
C4 C3 C21 C22 -49.8(3) . . . . ?
C2 C3 C21 C22 71.8(3) . . . . ?
C26 C21 C22 C23 3.1(5) . . . . ?
C3 C21 C22 C23 179.0(3) . . . . ?
C21 C22 C23 C24 -0.3(6) . . . . ?
C22 C23 C24 C25 -2.8(6) . . . . ?
C23 C24 C25 C26 3.0(5) . . . . ?
C22 C21 C26 C25 -2.9(4) . . . . ?
C3 C21 C26 C25 -178.9(2) . . . . ?
C24 C25 C26 C21 -0.1(4) . . . . ?
O2 C5 C31 C36 148.05(18) . . . . ?
C4 C5 C31 C36 -98.1(2) . . . . ?
O2 C5 C31 C32 -37.3(2) . . . . ?
C4 C5 C31 C32 76.5(2) . . . . ?
C36 C31 C32 C33 -0.1(3) . . . . ?
C5 C31 C32 C33 -174.8(2) . . . . ?
C31 C32 C33 C34 -0.4(4) . . . . ?
C32 C33 C34 C35 0.7(4) . . . . ?
C33 C34 C35 C36 -0.5(4) . . . . ?
C32 C31 C36 C35 0.3(3) . . . . ?
C5 C31 C36 C35 174.9(2) . . . . ?
C34 C35 C36 C31 0.0(4) . . . . ?
