#------------------------------------------------------------------------------
#$Date: 2023-04-04 12:37:24 +0300 (Tue, 04 Apr 2023) $
#$Revision: 282257 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/13/7131313.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_7131313
loop_
_publ_author_name
'Song, Yimei'
'Wu, Chaofei'
'Zhang, Jinhai'
'Zhang, Wenhai'
'Qin, Xin'
'Yang, Yixiao'
'Kang, Guowei'
'Jiang, Jun'
'Liu, Hongxin'
_publ_section_title
;
 Switchable multipath cascade cyclization to synthesize bicyclic lactams
 and succinimides via chemodivergent reaction.
;
_journal_issue                   22
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3313
_journal_page_last               3316
_journal_paper_doi               10.1039/d2cc06841a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_sum            'C21 H21 N O4'
_chemical_formula_weight         351.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-01-29 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.569(2)
_cell_length_b                   14.570(3)
_cell_length_c                   20.867(4)
_cell_measurement_reflns_used    7500
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.45
_cell_volume                     3517.3(12)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0203
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14890
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         1.952
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   saadabs
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       noodle
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3265
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0447
_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)+(0.1700P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1787
_refine_ls_wR_factor_ref         0.1941
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2813
_reflns_number_total             3265
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc06841a2.cif
_cod_data_source_block           mo_20200522c_0m_a
_cod_depositor_comments
'Adding full bibliography for 7131313--7131315.cif.'
_cod_original_cell_volume        3517.4(10)
_cod_database_code               7131313
_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.
;
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'
'-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
N1 N 0.69506(11) 0.57891(8) 0.36689(6) 0.0265(4) Uani 1 1 d . . . . .
O1 O 0.63976(10) 0.43970(7) 0.32449(6) 0.0355(3) Uani 1 1 d . . . . .
O2 O 0.83420(11) 0.47151(8) 0.23924(5) 0.0353(3) Uani 1 1 d . . . . .
H2 H 0.8260 0.4156 0.2388 0.053 Uiso 1 1 calc R U . . .
O3 O 0.80342(11) 0.64958(8) 0.24976(5) 0.0340(3) Uani 1 1 d . . . . .
O4 O 0.70205(11) 0.77627(8) 0.23059(6) 0.0438(4) Uani 1 1 d . . . . .
C1 C 0.70876(13) 0.50132(10) 0.33114(7) 0.0259(4) Uani 1 1 d . . . . .
C2 C 0.83121(13) 0.50284(10) 0.30251(7) 0.0270(4) Uani 1 1 d . . . . .
C3 C 0.86149(14) 0.60581(10) 0.30421(7) 0.0285(4) Uani 1 1 d . . . . .
C4 C 0.79307(13) 0.64272(10) 0.36222(7) 0.0276(4) Uani 1 1 d . . . . .
H4 H 0.8394 0.6450 0.4015 0.033 Uiso 1 1 calc R U . . .
C5 C 0.75358(15) 0.73615(11) 0.34044(8) 0.0342(4) Uani 1 1 d . . . . .
H5A H 0.6785 0.7512 0.3583 0.041 Uiso 1 1 calc R U . . .
H5B H 0.8086 0.7832 0.3527 0.041 Uiso 1 1 calc R U . . .
C6 C 0.74731(14) 0.72650(11) 0.26876(8) 0.0327(4) Uani 1 1 d . . . . .
C7 C 0.60192(14) 0.59416(10) 0.41098(7) 0.0278(4) Uani 1 1 d . . . . .
C8 C 0.62765(15) 0.62583(11) 0.47191(8) 0.0350(4) Uani 1 1 d . . . . .
H8 H 0.7039 0.6383 0.4830 0.042 Uiso 1 1 calc R U . . .
C9 C 0.54012(17) 0.63905(12) 0.51664(8) 0.0398(5) Uani 1 1 d . . . . .
C10 C 0.42719(15) 0.62072(12) 0.49805(9) 0.0404(5) Uani 1 1 d . . . . .
H10 H 0.3679 0.6288 0.5276 0.048 Uiso 1 1 calc R U . . .
C11 C 0.39980(15) 0.59063(13) 0.43654(8) 0.0386(4) Uani 1 1 d . . . . .
C12 C 0.48908(15) 0.57724(12) 0.39282(7) 0.0331(4) Uani 1 1 d . . . . .
H12 H 0.4728 0.5570 0.3515 0.040 Uiso 1 1 calc R U . . .
C13 C 0.5684(2) 0.67227(18) 0.58300(10) 0.0617(7) Uani 1 1 d . . . . .
H13A H 0.5649 0.7381 0.5840 0.093 Uiso 1 1 calc R U . . .
H13B H 0.6448 0.6525 0.5945 0.093 Uiso 1 1 calc R U . . .
H13C H 0.5135 0.6475 0.6129 0.093 Uiso 1 1 calc R U . . .
C14 C 0.27682(18) 0.57292(19) 0.41677(11) 0.0610(6) Uani 1 1 d . . . . .
H14A H 0.2730 0.5662 0.3711 0.092 Uiso 1 1 calc R U . . .
H14B H 0.2292 0.6236 0.4298 0.092 Uiso 1 1 calc R U . . .
H14C H 0.2497 0.5177 0.4369 0.092 Uiso 1 1 calc R U . . .
C15 C 0.91091(13) 0.44808(10) 0.34717(8) 0.0300(4) Uani 1 1 d . . . . .
C16 C 0.89201(16) 0.44229(12) 0.41260(9) 0.0386(4) Uani 1 1 d . . . . .
H16 H 0.8293 0.4727 0.4306 0.046 Uiso 1 1 calc R U . . .
C17 C 0.96533(18) 0.39182(15) 0.45158(9) 0.0501(5) Uani 1 1 d . . . . .
H17 H 0.9526 0.3897 0.4956 0.060 Uiso 1 1 calc R U . . .
C18 C 1.05656(18) 0.34500(15) 0.42539(11) 0.0521(5) Uani 1 1 d . . . . .
H18 H 1.1050 0.3103 0.4514 0.062 Uiso 1 1 calc R U . . .
C19 C 1.07600(18) 0.34962(16) 0.36071(11) 0.0559(6) Uani 1 1 d . . . . .
H19 H 1.1380 0.3178 0.3430 0.067 Uiso 1 1 calc R U . . .
C20 C 1.00443(16) 0.40118(14) 0.32114(9) 0.0438(5) Uani 1 1 d . . . . .
H20 H 1.0191 0.4043 0.2774 0.053 Uiso 1 1 calc R U . . .
C21 C 0.98769(15) 0.63052(13) 0.30112(9) 0.0411(5) Uiso 1 1 d . . . . .
H21A H 1.0211 0.6051 0.2629 0.062 Uiso 1 1 calc R U . . .
H21B H 1.0267 0.6061 0.3380 0.062 Uiso 1 1 calc R U . . .
H21C H 0.9958 0.6961 0.3005 0.062 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 0.0033 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'
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
C1 N1 C7 124.52(12) . . ?
C1 N1 C4 113.48(12) . . ?
C7 N1 C4 121.63(12) . . ?
C2 O2 H2 109.5 . . ?
C6 O3 C3 110.65(12) . . ?
O1 C1 N1 126.98(14) . . ?
O1 C1 C2 125.04(13) . . ?
N1 C1 C2 107.92(12) . . ?
O2 C2 C15 112.89(12) . . ?
O2 C2 C1 112.66(12) . . ?
C15 C2 C1 108.07(11) . . ?
O2 C2 C3 109.52(12) . . ?
C15 C2 C3 110.83(12) . . ?
C1 C2 C3 102.39(11) . . ?
O3 C3 C21 107.90(12) . . ?
O3 C3 C2 107.55(12) . . ?
C21 C3 C2 116.89(14) . . ?
O3 C3 C4 102.79(12) . . ?
C21 C3 C4 116.60(13) . . ?
C2 C3 C4 103.93(12) . . ?
N1 C4 C5 110.96(13) . . ?
N1 C4 C3 103.15(12) . . ?
C5 C4 C3 103.53(12) . . ?
N1 C4 H4 112.8 . . ?
C5 C4 H4 112.8 . . ?
C3 C4 H4 112.8 . . ?
C6 C5 C4 103.31(13) . . ?
C6 C5 H5A 111.1 . . ?
C4 C5 H5A 111.1 . . ?
C6 C5 H5B 111.1 . . ?
C4 C5 H5B 111.1 . . ?
H5A C5 H5B 109.1 . . ?
O4 C6 O3 121.05(15) . . ?
O4 C6 C5 128.74(16) . . ?
O3 C6 C5 110.20(13) . . ?
C12 C7 C8 120.95(14) . . ?
C12 C7 N1 120.43(13) . . ?
C8 C7 N1 118.62(14) . . ?
C7 C8 C9 120.38(16) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 118.10(16) . . ?
C10 C9 C13 121.60(16) . . ?
C8 C9 C13 120.30(17) . . ?
C9 C10 C11 122.13(15) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C12 C11 C10 118.64(16) . . ?
C12 C11 C14 119.89(17) . . ?
C10 C11 C14 121.47(16) . . ?
C7 C12 C11 119.77(15) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 118.55(15) . . ?
C16 C15 C2 122.37(14) . . ?
C20 C15 C2 119.07(15) . . ?
C15 C16 C17 120.93(16) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 120.08(18) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 119.66(18) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.94(19) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C15 119.82(18) . . ?
C19 C20 H20 120.1 . . ?
C15 C20 H20 120.1 . . ?
C3 C21 H21A 109.5 . . ?
C3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
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
N1 C1 1.364(2) . ?
N1 C7 1.4341(19) . ?
N1 C4 1.4695(19) . ?
O1 C1 1.2094(18) . ?
O2 C2 1.3973(17) . ?
O2 H2 0.8200 . ?
O3 C6 1.355(2) . ?
O3 C3 1.4658(19) . ?
O4 C6 1.198(2) . ?
C1 C2 1.538(2) . ?
C2 C15 1.535(2) . ?
C2 C3 1.541(2) . ?
C3 C21 1.505(2) . ?
C3 C4 1.543(2) . ?
C4 C5 1.506(2) . ?
C4 H4 0.9800 . ?
C5 C6 1.504(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C7 C12 1.381(2) . ?
C7 C8 1.385(2) . ?
C8 C9 1.391(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(3) . ?
C9 C13 1.503(3) . ?
C10 C11 1.393(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(2) . ?
C11 C14 1.504(3) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.385(2) . ?
C15 C20 1.390(2) . ?
C16 C17 1.386(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.370(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.370(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.390(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
