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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/63/7106376.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_7106376
loop_
_publ_author_name
'Huai-Long Teng'
'He Huang'
'Hai-Yan Tao'
'Chun-Jiang Wang'
_publ_section_title
;
 Morita-Baylis-Hillman adducts as effective dipolarophiles in
 Copper(I)-catalyzed 1,3-dipolar cycloaddition with azomethine ylides:
 asymmetric construction of pyrrolidine derivatives containing quaternary
 stereogenic center
;
_journal_name_full               Chem.Commun.
_journal_page_first              5494
_journal_paper_doi               10.1039/c1cc11138h
_journal_volume                  47
_journal_year                    2011
_chemical_absolute_configuration 7R,8S,10R
_chemical_formula_sum            'C32 H32 Cl N O7'
_chemical_formula_weight         578.04
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.401(3)
_cell_length_b                   24.000(3)
_cell_length_c                   6.6143(9)
_cell_measurement_reflns_used    5228
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.61
_cell_measurement_theta_min      2.26
_cell_volume                     3079.8(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            17928
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.9538
_exptl_absorpt_correction_T_min  0.9474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_coef       0.0049(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         6359
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0231P)²+0.7880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0844
_reflns_number_gt                4817
_reflns_number_total             6359
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc11138h.txt
_cod_data_source_block           9
_cod_original_sg_symbol_H-M      P2(1)2(1)2
_cod_database_code               7106376
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.07478(14) 0.64911(11) 0.6625(5) 0.0808(8) Uani 1 1 d . . .
C2 C 1.01317(13) 0.65238(11) 0.7594(4) 0.0785(8) Uani 1 1 d . . .
H2 H 1.0096 0.6420 0.8944 0.094 Uiso 1 1 calc R . .
C3 C 0.95609(12) 0.67120(10) 0.6566(4) 0.0638(6) Uani 1 1 d . . .
H3 H 0.9141 0.6738 0.7236 0.077 Uiso 1 1 calc R . .
C4 C 0.96016(10) 0.68616(8) 0.4561(3) 0.0476(5) Uani 1 1 d . . .
C5 C 1.02327(11) 0.68110(9) 0.3598(4) 0.0662(6) Uani 1 1 d . . .
H5 H 1.0269 0.6901 0.2235 0.079 Uiso 1 1 calc R . .
C6 C 1.08095(12) 0.66280(10) 0.4632(6) 0.0808(8) Uani 1 1 d . . .
H6 H 1.1233 0.6599 0.3980 0.097 Uiso 1 1 calc R . .
C7 C 0.89882(9) 0.70739(7) 0.3376(3) 0.0442(4) Uani 1 1 d . . .
H7 H 0.9039 0.6960 0.1961 0.053 Uiso 1 1 calc R . .
C8 C 0.88823(9) 0.77222(7) 0.3459(3) 0.0426(4) Uani 1 1 d . . .
C9 C 0.83852(10) 0.77995(7) 0.5214(3) 0.0452(5) Uani 1 1 d . . .
H9A H 0.8142 0.8151 0.5103 0.054 Uiso 1 1 calc R . .
H9B H 0.8628 0.7789 0.6496 0.054 Uiso 1 1 calc R . .
C10 C 0.78865(9) 0.73092(7) 0.5030(3) 0.0435(5) Uani 1 1 d . . .
H10 H 0.7506 0.7404 0.4118 0.052 Uiso 1 1 calc R . .
C11 C 0.76122(10) 0.71512(8) 0.7086(3) 0.0472(5) Uani 1 1 d . . .
C12 C 0.66563(12) 0.72418(12) 0.9262(4) 0.0792(7) Uani 1 1 d . . .
H12A H 0.6783 0.6880 0.9759 0.119 Uiso 1 1 calc R . .
H12B H 0.6164 0.7263 0.9130 0.119 Uiso 1 1 calc R . .
H12C H 0.6811 0.7522 1.0193 0.119 Uiso 1 1 calc R . .
C13 C 0.80511(11) 0.63575(8) 0.3969(3) 0.0508(5) Uani 1 1 d . . .
C14 C 0.84780(11) 0.58923(8) 0.3134(4) 0.0524(5) Uani 1 1 d . . .
C15 C 0.85880(15) 0.54440(10) 0.4392(5) 0.0840(8) Uani 1 1 d . . .
H15 H 0.8439 0.5455 0.5727 0.101 Uiso 1 1 calc R . .
C16 C 0.89198(19) 0.49798(12) 0.3661(7) 0.1161(13) Uani 1 1 d . . .
H16 H 0.9003 0.4680 0.4519 0.139 Uiso 1 1 calc R . .
C17 C 0.91269(18) 0.49525(13) 0.1704(8) 0.1154(13) Uani 1 1 d . . .
H17 H 0.9345 0.4634 0.1222 0.138 Uiso 1 1 calc R . .
C18 C 0.90131(16) 0.53950(12) 0.0441(6) 0.0961(10) Uani 1 1 d . . .
H18 H 0.9151 0.5378 -0.0904 0.115 Uiso 1 1 calc R . .
C19 C 0.86921(13) 0.58674(10) 0.1174(4) 0.0674(7) Uani 1 1 d . . .
H19 H 0.8622 0.6171 0.0324 0.081 Uiso 1 1 calc R . .
C20 C 0.85593(11) 0.79078(8) 0.1471(3) 0.0518(5) Uani 1 1 d . . .
H20A H 0.8865 0.7828 0.0347 0.062 Uiso 1 1 calc R . .
H20B H 0.8124 0.7719 0.1247 0.062 Uiso 1 1 calc R . .
C21 C 0.81332(11) 0.87606(9) 0.0181(3) 0.0557(5) Uani 1 1 d . . .
C22 C 0.80956(11) 0.93678(9) 0.0538(4) 0.0572(6) Uani 1 1 d . . .
C23 C 0.81529(13) 0.95898(10) 0.2448(4) 0.0725(7) Uani 1 1 d . . .
H23 H 0.8231 0.9356 0.3546 0.087 Uiso 1 1 calc R . .
C24 C 0.80947(15) 1.01573(11) 0.2748(6) 0.0940(9) Uani 1 1 d . . .
H24 H 0.8119 1.0305 0.4047 0.113 Uiso 1 1 calc R . .
C25 C 0.80023(17) 1.04979(12) 0.1134(7) 0.1043(11) Uani 1 1 d . . .
H25 H 0.7965 1.0880 0.1340 0.125 Uiso 1 1 calc R . .
C26 C 0.79631(17) 1.02922(13) -0.0777(6) 0.1047(11) Uani 1 1 d . . .
H26 H 0.7919 1.0533 -0.1870 0.126 Uiso 1 1 calc R . .
C27 C 0.79895(14) 0.97164(12) -0.1094(5) 0.0881(9) Uani 1 1 d . . .
H27 H 0.7936 0.9570 -0.2386 0.106 Uiso 1 1 calc R . .
C28 C 0.95587(11) 0.80367(8) 0.3654(3) 0.0481(5) Uani 1 1 d . . .
C29 C 1.01751(12) 0.86864(11) 0.5877(4) 0.0731(7) Uani 1 1 d . . .
C30 C 1.08047(14) 0.83336(16) 0.6152(6) 0.1220(13) Uani 1 1 d . . .
H30A H 1.0705 0.8037 0.7081 0.183 Uiso 1 1 calc R . .
H30B H 1.1173 0.8558 0.6678 0.183 Uiso 1 1 calc R . .
H30C H 1.0939 0.8179 0.4872 0.183 Uiso 1 1 calc R . .
C31 C 0.99493(17) 0.89416(15) 0.7854(5) 0.1169(13) Uani 1 1 d . . .
H31A H 0.9518 0.9130 0.7668 0.175 Uiso 1 1 calc R . .
H31B H 1.0291 0.9203 0.8303 0.175 Uiso 1 1 calc R . .
H31C H 0.9896 0.8654 0.8849 0.175 Uiso 1 1 calc R . .
C32 C 1.02521(19) 0.91288(13) 0.4274(6) 0.1234(13) Uani 1 1 d . . .
H32A H 1.0413 0.8961 0.3044 0.185 Uiso 1 1 calc R . .
H32B H 1.0578 0.9404 0.4719 0.185 Uiso 1 1 calc R . .
H32C H 0.9814 0.9303 0.4038 0.185 Uiso 1 1 calc R . .
Cl1 Cl 1.14719(4) 0.62573(4) 0.79315(19) 0.1359(4) Uani 1 1 d . . .
N1 N 0.83186(8) 0.68736(6) 0.4135(2) 0.0439(4) Uani 1 1 d . . .
O1 O 0.79392(7) 0.69215(6) 0.8384(2) 0.0608(4) Uani 1 1 d . . .
O2 O 0.69729(7) 0.73328(6) 0.7311(2) 0.0600(4) Uani 1 1 d . . .
O3 O 0.99948(8) 0.80264(7) 0.2361(2) 0.0670(4) Uani 1 1 d . . .
O4 O 0.95849(7) 0.83235(6) 0.5363(2) 0.0543(4) Uani 1 1 d . . .
O5 O 0.84548(8) 0.84983(5) 0.1676(2) 0.0573(4) Uani 1 1 d . . .
O6 O 0.79037(11) 0.85174(8) -0.1254(3) 0.0917(6) Uani 1 1 d . . .
O7 O 0.74660(8) 0.62672(6) 0.4568(3) 0.0708(5) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 121.3(2) . . ?
C2 C1 Cl1 119.6(3) . . ?
C6 C1 Cl1 119.1(2) . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 118.1(2) . . ?
C3 C4 C7 122.82(19) . . ?
C5 C4 C7 119.1(2) . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.9(3) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
N1 C7 C4 114.00(16) . . ?
N1 C7 C8 101.30(14) . . ?
C4 C7 C8 114.74(15) . . ?
N1 C7 H7 108.8 . . ?
C4 C7 H7 108.8 . . ?
C8 C7 H7 108.8 . . ?
C9 C8 C28 114.99(16) . . ?
C9 C8 C20 111.25(15) . . ?
C28 C8 C20 106.45(16) . . ?
C9 C8 C7 103.34(15) . . ?
C28 C8 C7 112.46(15) . . ?
C20 C8 C7 108.26(15) . . ?
C8 C9 C10 104.29(15) . . ?
C8 C9 H9A 110.9 . . ?
C10 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
C10 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
N1 C10 C11 112.75(15) . . ?
N1 C10 C9 102.67(14) . . ?
C11 C10 C9 110.19(16) . . ?
N1 C10 H10 110.3 . . ?
C11 C10 H10 110.3 . . ?
C9 C10 H10 110.3 . . ?
O1 C11 O2 124.5(2) . . ?
O1 C11 C10 124.97(18) . . ?
O2 C11 C10 110.44(18) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O7 C13 N1 119.64(18) . . ?
O7 C13 C14 120.12(18) . . ?
N1 C13 C14 120.20(18) . . ?
C19 C14 C15 119.6(2) . . ?
C19 C14 C13 123.58(19) . . ?
C15 C14 C13 116.5(2) . . ?
C14 C15 C16 119.6(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 119.8(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 119.7(3) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C14 C19 C18 120.5(3) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
O5 C20 C8 105.36(15) . . ?
O5 C20 H20A 110.7 . . ?
C8 C20 H20A 110.7 . . ?
O5 C20 H20B 110.7 . . ?
C8 C20 H20B 110.7 . . ?
H20A C20 H20B 108.8 . . ?
O6 C21 O5 122.2(2) . . ?
O6 C21 C22 126.0(2) . . ?
O5 C21 C22 111.8(2) . . ?
C23 C22 C27 119.7(2) . . ?
C23 C22 C21 121.6(2) . . ?
C27 C22 C21 118.7(2) . . ?
C22 C23 C24 120.5(3) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C25 C24 C23 119.5(3) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C26 C25 C24 121.4(3) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C25 C26 C27 119.8(3) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C22 C27 C26 119.1(3) . . ?
C22 C27 H27 120.4 . . ?
C26 C27 H27 120.4 . . ?
O3 C28 O4 126.17(18) . . ?
O3 C28 C8 122.48(19) . . ?
O4 C28 C8 111.33(17) . . ?
O4 C29 C30 109.1(2) . . ?
O4 C29 C31 102.3(2) . . ?
C30 C29 C31 111.2(3) . . ?
O4 C29 C32 109.2(2) . . ?
C30 C29 C32 113.7(3) . . ?
C31 C29 C32 110.6(3) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C13 N1 C10 117.94(16) . . ?
C13 N1 C7 127.72(16) . . ?
C10 N1 C7 114.16(14) . . ?
C11 O2 C12 116.67(18) . . ?
C28 O4 C29 122.17(17) . . ?
C21 O5 C20 117.60(17) . . ?
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
C1 C2 1.359(4) . ?
C1 C6 1.363(4) . ?
C1 Cl1 1.742(3) . ?
C2 C3 1.376(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(3) . ?
C4 C7 1.513(3) . ?
C5 C6 1.383(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.474(2) . ?
C7 C8 1.570(2) . ?
C7 H7 0.9800 . ?
C8 C9 1.520(3) . ?
C8 C28 1.519(3) . ?
C8 C20 1.523(3) . ?
C9 C10 1.528(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N1 1.465(2) . ?
C10 C11 1.509(3) . ?
C10 H10 0.9800 . ?
C11 O1 1.201(2) . ?
C11 O2 1.323(2) . ?
C12 O2 1.446(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O7 1.222(2) . ?
C13 N1 1.347(2) . ?
C13 C14 1.496(3) . ?
C14 C19 1.362(3) . ?
C14 C15 1.377(3) . ?
C15 C16 1.374(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.357(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.369(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.381(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 O5 1.438(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 O6 1.200(3) . ?
C21 O5 1.328(2) . ?
C21 C22 1.478(3) . ?
C22 C23 1.376(3) . ?
C22 C27 1.381(3) . ?
C23 C24 1.381(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.357(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.359(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.399(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 O3 1.203(2) . ?
C28 O4 1.324(2) . ?
C29 O4 1.478(2) . ?
C29 C30 1.497(4) . ?
C29 C31 1.509(4) . ?
C29 C32 1.508(4) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653290
2 PubChem 139181879
