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#$Date: 2022-08-25 03:35:15 +0300 (Thu, 25 Aug 2022) $
#$Revision: 277399 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/88/7158840.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_7158840
loop_
_publ_author_name
'Pan, Liu-Na'
'Sun, Jing'
'Liu, Xue-Yan'
'Yan, Chaoguo'
_publ_section_title
;
 Efficient Construction of Diverse
 Spiro[indoline-3,4'-pyrrolo[3,4-b]pyridines] via [3+3] Cycloaddition of
 MBH Carbonates of Isatin with β-Enamino Maleimides
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01257J
_journal_year                    2022
_chemical_formula_moiety         'C31 H26 Cl N3 O5'
_chemical_formula_sum            'C31 H26 Cl N3 O5'
_chemical_formula_weight         556.00
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-07-12 deposited with the CCDC.	2022-08-23 downloaded from the CCDC.
;
_cell_angle_alpha                78.635(5)
_cell_angle_beta                 87.607(4)
_cell_angle_gamma                75.843(4)
_cell_formula_units_Z            2
_cell_length_a                   9.2939(12)
_cell_length_b                   11.4737(17)
_cell_length_c                   13.2237(18)
_cell_measurement_reflns_used    7610
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.56
_cell_volume                     1340.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19165
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.260
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       block
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5253
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0786
_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
'w=1/[σ²(Fo²)+(0.0514P)²+0.5560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1224
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3708
_reflns_number_total             5253
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01257j2.cif
_cod_data_source_block           3l
_cod_database_code               7158840
_shelx_shelxl_version_number     2014/7
_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   0.956
_shelx_estimated_absorpt_t_max   0.963
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
C1 C 1.1512(4) 0.4484(3) 0.7761(3) 0.0856(10) Uani 1 1 d . . . . .
H1 H 1.2148 0.3820 0.8168 0.103 Uiso 1 1 calc R U . . .
C2 C 1.1566(5) 0.5664(4) 0.7825(4) 0.1203(15) Uani 1 1 d . . . . .
H2 H 1.2231 0.5783 0.8278 0.144 Uiso 1 1 calc R U . . .
C3 C 1.0652(4) 0.6652(3) 0.7228(3) 0.0903(11) Uani 1 1 d . . . . .
H3 H 1.0688 0.7445 0.7265 0.108 Uiso 1 1 calc R U . . .
C4 C 0.9706(4) 0.6452(3) 0.6589(3) 0.0940(11) Uani 1 1 d . . . . .
H4 H 0.9071 0.7117 0.6182 0.113 Uiso 1 1 calc R U . . .
C5 C 0.9648(4) 0.5289(3) 0.6520(2) 0.0804(9) Uani 1 1 d . . . . .
H5 H 0.8986 0.5180 0.6058 0.096 Uiso 1 1 calc R U . . .
C6 C 1.0545(2) 0.4286(2) 0.71154(17) 0.0418(5) Uani 1 1 d . . . . .
C7 C 1.0500(2) 0.2999(2) 0.70639(18) 0.0449(5) Uani 1 1 d . . . . .
H7A H 1.0671 0.2884 0.6357 0.054 Uiso 1 1 calc R U . . .
H7B H 1.1303 0.2434 0.7484 0.054 Uiso 1 1 calc R U . . .
C8 C 0.8831(2) 0.22510(18) 0.84230(16) 0.0369(5) Uani 1 1 d . . . . .
C9 C 0.7249(2) 0.20249(17) 0.84904(14) 0.0312(4) Uani 1 1 d . . . . .
C10 C 0.6778(2) 0.23476(17) 0.73706(14) 0.0315(4) Uani 1 1 d . . . . .
C11 C 0.5472(2) 0.23383(18) 0.69256(15) 0.0366(5) Uani 1 1 d . . . . .
H11 H 0.4732 0.2049 0.7316 0.044 Uiso 1 1 calc R U . . .
C12 C 0.5301(2) 0.2775(2) 0.58759(16) 0.0444(5) Uani 1 1 d . . . . .
C13 C 0.6403(3) 0.3186(2) 0.52829(17) 0.0570(7) Uani 1 1 d . . . . .
H13 H 0.6255 0.3471 0.4577 0.068 Uiso 1 1 calc R U . . .
C14 C 0.7723(3) 0.3175(2) 0.57325(17) 0.0534(6) Uani 1 1 d . . . . .
H14 H 0.8475 0.3443 0.5339 0.064 Uiso 1 1 calc R U . . .
C15 C 0.7893(2) 0.27567(19) 0.67772(15) 0.0370(5) Uani 1 1 d . . . . .
C16 C 0.6626(3) 0.24674(18) 1.03087(15) 0.0389(5) Uani 1 1 d . . . . .
H16A H 0.7628 0.2534 1.0412 0.047 Uiso 1 1 calc R U . . .
H16B H 0.5960 0.3009 1.0695 0.047 Uiso 1 1 calc R U . . .
C17 C 0.6227(2) 0.28735(17) 0.91650(14) 0.0342(5) Uani 1 1 d . . . . .
H17 H 0.5207 0.2811 0.9085 0.041 Uiso 1 1 calc R U . . .
C18 C 0.6248(3) 0.4209(2) 0.88374(17) 0.0487(6) Uani 1 1 d . U . . .
C19 C 0.5730(4) 0.5920(2) 0.7484(2) 0.0873(10) Uani 1 1 d . U . . .
H19A H 0.4820 0.6461 0.7638 0.131 Uiso 1 1 calc R U . . .
H19B H 0.5836 0.6002 0.6749 0.131 Uiso 1 1 calc R U . . .
H19C H 0.6550 0.6126 0.7764 0.131 Uiso 1 1 calc R U . . .
C20 C 0.5731(2) 0.0879(2) 1.25036(16) 0.0427(5) Uani 1 1 d . . . . .
H20 H 0.4746 0.1141 1.2286 0.051 Uiso 1 1 calc R U . . .
C21 C 0.6077(3) 0.0574(2) 1.35452(16) 0.0504(6) Uani 1 1 d . . . . .
H21 H 0.5312 0.0637 1.4022 0.061 Uiso 1 1 calc R U . . .
C22 C 0.7529(3) 0.01796(19) 1.38962(15) 0.0419(5) Uani 1 1 d . . . . .
C23 C 0.7889(3) -0.0134(3) 1.50339(17) 0.0646(7) Uani 1 1 d . . . . .
H23A H 0.7906 0.0599 1.5275 0.097 Uiso 1 1 calc R U . . .
H23B H 0.8843 -0.0700 1.5149 0.097 Uiso 1 1 calc R U . . .
H23C H 0.7147 -0.0500 1.5402 0.097 Uiso 1 1 calc R U . . .
C24 C 0.8641(2) 0.0089(2) 1.31666(16) 0.0438(5) Uani 1 1 d . . . . .
H24 H 0.9627 -0.0185 1.3381 0.053 Uiso 1 1 calc R U . . .
C25 C 0.8309(2) 0.0398(2) 1.21255(16) 0.0419(5) Uani 1 1 d . . . . .
H25 H 0.9071 0.0339 1.1646 0.050 Uiso 1 1 calc R U . . .
C26 C 0.6859(2) 0.07906(17) 1.17942(14) 0.0316(4) Uani 1 1 d . . . . .
C27 C 0.7028(2) -0.09227(18) 1.02803(15) 0.0320(4) Uani 1 1 d . . . . .
C28 C 0.6968(2) 0.04288(17) 1.00339(14) 0.0297(4) Uani 1 1 d . . . . .
C29 C 0.7280(2) 0.07394(17) 0.90294(14) 0.0306(4) Uani 1 1 d . . . . .
C30 C 0.7673(2) -0.03769(18) 0.85975(15) 0.0337(4) Uani 1 1 d . . . . .
C31 C 0.7870(3) -0.2627(2) 0.93145(19) 0.0531(6) Uani 1 1 d . . . . .
H31A H 0.8744 -0.3048 0.9718 0.080 Uiso 1 1 calc R U . . .
H31B H 0.8052 -0.2695 0.8606 0.080 Uiso 1 1 calc R U . . .
H31C H 0.7062 -0.2986 0.9567 0.080 Uiso 1 1 calc R U . . .
Cl1 Cl 0.36398(7) 0.28203(7) 0.52849(5) 0.0682(2) Uani 1 1 d . . . . .
N1 N 0.90984(18) 0.26906(16) 0.74136(13) 0.0390(4) Uani 1 1 d . . . . .
N2 N 0.65263(18) 0.11990(14) 1.07054(12) 0.0346(4) Uani 1 1 d . . . . .
N3 N 0.74933(18) -0.13437(15) 0.93939(12) 0.0363(4) Uani 1 1 d . . . . .
O1 O 0.96902(17) 0.20622(15) 0.91347(12) 0.0537(4) Uani 1 1 d . . . . .
O2 O 0.7063(14) 0.4685(7) 0.9231(7) 0.081(2) Uani 0.553(18) 1 d . U P A 1
O2' O 0.6263(18) 0.4875(7) 0.9447(6) 0.074(2) Uani 0.447(18) 1 d . U P A 2
O3 O 0.5706(3) 0.46811(15) 0.79304(13) 0.0755(6) Uani 1 1 d . U . . .
O4 O 0.66864(16) -0.15170(13) 1.10746(11) 0.0420(4) Uani 1 1 d . . . . .
O5 O 0.80871(17) -0.05141(14) 0.77412(11) 0.0475(4) 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
C6 C1 C2 120.9(3) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 118.4(3) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 121.5(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 117.5(2) . . ?
C1 C6 C7 119.9(2) . . ?
C5 C6 C7 122.5(2) . . ?
N1 C7 C6 113.89(18) . . ?
N1 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
N1 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
O1 C8 N1 125.70(19) . . ?
O1 C8 C9 126.35(18) . . ?
N1 C8 C9 107.95(16) . . ?
C29 C9 C10 115.79(15) . . ?
C29 C9 C8 110.84(15) . . ?
C10 C9 C8 101.87(15) . . ?
C29 C9 C17 105.44(15) . . ?
C10 C9 C17 112.61(15) . . ?
C8 C9 C17 110.36(15) . . ?
C11 C10 C15 120.89(18) . . ?
C11 C10 C9 130.08(17) . . ?
C15 C10 C9 108.95(16) . . ?
C10 C11 C12 117.46(18) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
C13 C12 C11 121.9(2) . . ?
C13 C12 Cl1 119.09(16) . . ?
C11 C12 Cl1 119.01(16) . . ?
C12 C13 C14 120.4(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 118.0(2) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C14 C15 C10 121.34(19) . . ?
C14 C15 N1 128.83(18) . . ?
C10 C15 N1 109.80(17) . . ?
N2 C16 C17 111.89(16) . . ?
N2 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
N2 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C18 C17 C16 108.56(16) . . ?
C18 C17 C9 113.32(17) . . ?
C16 C17 C9 112.13(16) . . ?
C18 C17 H17 107.5 . . ?
C16 C17 H17 107.5 . . ?
C9 C17 H17 107.5 . . ?
O2' C18 O3 119.3(4) . . ?
O2 C18 O3 120.7(4) . . ?
O2' C18 C17 123.2(4) . . ?
O2 C18 C17 123.1(4) . . ?
O3 C18 C17 112.83(19) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C26 C20 C21 119.32(19) . . ?
C26 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C22 C21 C20 121.9(2) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C21 C22 C24 117.63(19) . . ?
C21 C22 C23 121.2(2) . . ?
C24 C22 C23 121.1(2) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C22 121.0(2) . . ?
C25 C24 H24 119.5 . . ?
C22 C24 H24 119.5 . . ?
C26 C25 C24 120.37(19) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C20 119.81(18) . . ?
C25 C26 N2 119.86(17) . . ?
C20 C26 N2 120.16(17) . . ?
O4 C27 N3 126.35(18) . . ?
O4 C27 C28 128.11(18) . . ?
N3 C27 C28 105.48(16) . . ?
C29 C28 N2 126.80(17) . . ?
C29 C28 C27 108.54(17) . . ?
N2 C28 C27 124.36(16) . . ?
C28 C29 C30 108.28(16) . . ?
C28 C29 C9 123.84(17) . . ?
C30 C29 C9 127.86(16) . . ?
O5 C30 N3 123.56(18) . . ?
O5 C30 C29 129.79(18) . . ?
N3 C30 C29 106.65(16) . . ?
N3 C31 H31A 109.5 . . ?
N3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C8 N1 C15 111.33(16) . . ?
C8 N1 C7 122.83(17) . . ?
C15 N1 C7 125.79(17) . . ?
C28 N2 C26 120.93(16) . . ?
C28 N2 C16 114.65(15) . . ?
C26 N2 C16 113.55(15) . . ?
C27 N3 C30 110.84(16) . . ?
C27 N3 C31 124.30(17) . . ?
C30 N3 C31 124.67(17) . . ?
C18 O3 C19 119.6(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
C1 C6 1.352(3) . ?
C1 C2 1.386(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.364(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.332(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.503(3) . ?
C7 N1 1.465(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.212(2) . ?
C8 N1 1.366(3) . ?
C8 C9 1.550(3) . ?
C9 C29 1.500(3) . ?
C9 C10 1.510(3) . ?
C9 C17 1.570(3) . ?
C10 C11 1.374(3) . ?
C10 C15 1.391(3) . ?
C11 C12 1.382(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(3) . ?
C12 Cl1 1.744(2) . ?
C13 C14 1.382(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 N1 1.408(3) . ?
C16 N2 1.471(2) . ?
C16 C17 1.525(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.513(3) . ?
C17 H17 0.9800 . ?
C18 O2' 1.218(7) . ?
C18 O2 1.221(6) . ?
C18 O3 1.283(3) . ?
C19 O3 1.433(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C26 1.376(3) . ?
C20 C21 1.384(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.382(3) . ?
C21 H21 0.9300 . ?
C22 C24 1.383(3) . ?
C22 C23 1.508(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.381(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.373(3) . ?
C25 H25 0.9300 . ?
C26 N2 1.445(2) . ?
C27 O4 1.210(2) . ?
C27 N3 1.369(3) . ?
C27 C28 1.508(3) . ?
C28 C29 1.344(3) . ?
C28 N2 1.356(2) . ?
C29 C30 1.464(3) . ?
C30 O5 1.208(2) . ?
C30 N3 1.408(2) . ?
C31 N3 1.451(3) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
