#------------------------------------------------------------------------------
#$Date: 2023-04-04 11:37:24 +0200 (Tue 04 de Apr de 2023) $
#$Revision: 282257 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/13/7131314.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_7131314
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      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-2018/3
_audit_update_record
;
2021-01-29 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;
_cell_angle_alpha                80.396(2)
_cell_angle_beta                 88.581(2)
_cell_angle_gamma                72.582(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5695(13)
_cell_length_b                   9.9711(13)
_cell_length_c                   11.4136(17)
_cell_measurement_reflns_used    7159
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.195
_cell_measurement_theta_min      2.171
_cell_volume                     917.2(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0251
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8408
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_min         2.171
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3364
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0512
_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)+(0.0771P)²+0.4468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1403
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3032
_reflns_number_total             3364
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc06841a2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7131313--7131315.cif.'
_cod_database_code               7131314
_shelx_shelxl_version_number     2018/3
_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   0.983
_shelx_estimated_absorpt_t_max   0.987
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
N1 N 0.59119(16) 0.48358(14) 0.28633(12) 0.0337(3) Uani 1 1 d . . . . .
O1 O 0.44659(16) 0.39323(13) 0.43503(11) 0.0461(3) Uani 1 1 d . . . . .
O2 O 0.65265(16) 0.60233(13) 0.10952(12) 0.0469(3) Uani 1 1 d . . . . .
O3 O 0.28654(14) 0.70812(12) 0.10525(10) 0.0359(3) Uani 1 1 d . . . . .
O4 O 0.30281(17) 0.46838(13) 0.12457(12) 0.0466(3) Uani 1 1 d . . . . .
H4 H 0.311112 0.460419 0.054152 0.070 Uiso 1 1 calc R U . . .
C1 C 0.9081(3) 0.0217(2) 0.1783(2) 0.0624(6) Uani 1 1 d . . . . .
H1A H 1.009435 -0.051881 0.199821 0.094 Uiso 1 1 calc R U . . .
H1B H 0.907538 0.060363 0.095370 0.094 Uiso 1 1 calc R U . . .
H1C H 0.818664 -0.017531 0.193421 0.094 Uiso 1 1 calc R U . . .
C2 C 0.8906(2) 0.13799(19) 0.25075(17) 0.0434(4) Uani 1 1 d . . . . .
C3 C 1.0072(2) 0.1299(2) 0.33504(17) 0.0457(4) Uani 1 1 d . . . . .
H3 H 1.098795 0.049980 0.347142 0.055 Uiso 1 1 calc R U . . .
C4 C 0.9931(2) 0.2369(2) 0.40276(16) 0.0442(4) Uani 1 1 d . . . . .
C5 C 1.1255(3) 0.2248(3) 0.4925(2) 0.0657(6) Uani 1 1 d . . . . .
H5A H 1.094969 0.306790 0.531465 0.099 Uiso 1 1 calc R U . . .
H5B H 1.226546 0.219724 0.452692 0.099 Uiso 1 1 calc R U . . .
H5C H 1.138963 0.140189 0.550486 0.099 Uiso 1 1 calc R U . . .
C6 C 0.8546(2) 0.35510(19) 0.38491(16) 0.0399(4) Uani 1 1 d . . . . .
H6 H 0.841117 0.427965 0.429110 0.048 Uiso 1 1 calc R U . . .
C7 C 0.73716(19) 0.36341(17) 0.30101(15) 0.0351(4) Uani 1 1 d . . . . .
C8 C 0.7535(2) 0.25815(18) 0.23322(17) 0.0397(4) Uani 1 1 d . . . . .
H8 H 0.673665 0.267140 0.176215 0.048 Uiso 1 1 calc R U . . .
C9 C 0.4543(2) 0.48679(16) 0.35601(14) 0.0326(4) Uani 1 1 d . . . . .
C10 C 0.32239(19) 0.62458(15) 0.31406(14) 0.0310(3) Uani 1 1 d . . . . .
H10 H 0.296724 0.684310 0.376174 0.037 Uiso 1 1 calc R U . . .
C11 C 0.39073(18) 0.69849(15) 0.20392(13) 0.0294(3) Uani 1 1 d . . . . .
C12 C 0.5606(2) 0.59296(16) 0.18991(14) 0.0320(3) Uani 1 1 d . . . . .
C13 C 0.40592(18) 0.84464(15) 0.21183(14) 0.0299(3) Uani 1 1 d . . . . .
C14 C 0.4733(2) 0.86797(19) 0.31299(16) 0.0426(4) Uani 1 1 d . . . . .
H14 H 0.512762 0.792883 0.375419 0.051 Uiso 1 1 calc R U . . .
C15 C 0.4823(3) 1.0022(2) 0.32157(18) 0.0496(5) Uani 1 1 d . . . . .
H15 H 0.528977 1.016521 0.389306 0.060 Uiso 1 1 calc R U . . .
C16 C 0.4226(2) 1.11438(19) 0.2308(2) 0.0484(5) Uani 1 1 d . . . . .
H16 H 0.424288 1.205418 0.238227 0.058 Uiso 1 1 calc R U . . .
C17 C 0.3604(3) 1.0910(2) 0.1288(2) 0.0545(5) Uani 1 1 d . . . . .
H17 H 0.323247 1.166124 0.066050 0.065 Uiso 1 1 calc R U . . .
C18 C 0.3526(2) 0.95697(19) 0.11857(16) 0.0436(4) Uani 1 1 d . . . . .
H18 H 0.311356 0.942201 0.048803 0.052 Uiso 1 1 calc R U . . .
C19 C 0.1676(2) 0.60307(18) 0.26666(16) 0.0385(4) Uani 1 1 d . . . . .
H19A H 0.153659 0.512934 0.304482 0.046 Uiso 1 1 calc R U . . .
H19B H 0.071222 0.679815 0.279203 0.046 Uiso 1 1 calc R U . . .
C20 C 0.1994(2) 0.60421(17) 0.13517(15) 0.0356(4) Uani 1 1 d . . . . .
C21 C 0.0488(2) 0.6515(2) 0.05439(19) 0.0508(5) Uani 1 1 d . . . . .
H21A H 0.081252 0.648401 -0.026460 0.076 Uiso 1 1 calc R U . . .
H21B H -0.013344 0.747182 0.061911 0.076 Uiso 1 1 calc R U . . .
H21C H -0.017090 0.589045 0.076444 0.076 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
C12 N1 C9 112.94(13) . . ?
C12 N1 C7 123.58(13) . . ?
C9 N1 C7 122.42(13) . . ?
C11 O3 C20 108.46(11) . . ?
C20 O4 H4 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C8 118.36(17) . . ?
C3 C2 C1 121.84(17) . . ?
C8 C2 C1 119.80(18) . . ?
C2 C3 C4 122.59(16) . . ?
C2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C6 C4 C3 118.17(17) . . ?
C6 C4 C5 121.05(18) . . ?
C3 C4 C5 120.78(17) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 119.46(17) . . ?
C7 C6 H6 120.3 . . ?
C4 C6 H6 120.3 . . ?
C8 C7 C6 121.92(15) . . ?
C8 C7 N1 118.99(15) . . ?
C6 C7 N1 119.07(15) . . ?
C7 C8 C2 119.48(16) . . ?
C7 C8 H8 120.3 . . ?
C2 C8 H8 120.3 . . ?
O1 C9 N1 124.34(15) . . ?
O1 C9 C10 127.16(15) . . ?
N1 C9 C10 108.49(13) . . ?
C9 C10 C19 113.36(13) . . ?
C9 C10 C11 105.59(12) . . ?
C19 C10 C11 104.04(13) . . ?
C9 C10 H10 111.2 . . ?
C19 C10 H10 111.2 . . ?
C11 C10 H10 111.2 . . ?
O3 C11 C13 110.01(12) . . ?
O3 C11 C12 109.62(12) . . ?
C13 C11 C12 110.40(12) . . ?
O3 C11 C10 106.80(12) . . ?
C13 C11 C10 115.91(13) . . ?
C12 C11 C10 103.81(12) . . ?
O2 C12 N1 124.97(15) . . ?
O2 C12 C11 126.71(14) . . ?
N1 C12 C11 108.32(12) . . ?
C18 C13 C14 118.78(15) . . ?
C18 C13 C11 120.74(15) . . ?
C14 C13 C11 120.48(14) . . ?
C15 C14 C13 120.40(16) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.44(18) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.41(17) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 120.65(17) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 120.22(17) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
C20 C19 C10 103.08(13) . . ?
C20 C19 H19A 111.1 . . ?
C10 C19 H19A 111.1 . . ?
C20 C19 H19B 111.1 . . ?
C10 C19 H19B 111.1 . . ?
H19A C19 H19B 109.1 . . ?
O4 C20 O3 109.68(13) . . ?
O4 C20 C21 113.36(14) . . ?
O3 C20 C21 107.26(14) . . ?
O4 C20 C19 106.53(13) . . ?
O3 C20 C19 103.85(13) . . ?
C21 C20 C19 115.68(15) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 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 C12 1.383(2) . ?
N1 C9 1.396(2) . ?
N1 C7 1.440(2) . ?
O1 C9 1.201(2) . ?
O2 C12 1.205(2) . ?
O3 C11 1.4273(19) . ?
O3 C20 1.4425(19) . ?
O4 C20 1.402(2) . ?
O4 H4 0.8200 . ?
C1 C2 1.503(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.380(3) . ?
C2 C8 1.395(2) . ?
C3 C4 1.394(3) . ?
C3 H3 0.9300 . ?
C4 C6 1.391(2) . ?
C4 C5 1.512(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.381(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.507(2) . ?
C10 C19 1.530(2) . ?
C10 C11 1.543(2) . ?
C10 H10 0.9800 . ?
C11 C13 1.519(2) . ?
C11 C12 1.542(2) . ?
C13 C18 1.384(2) . ?
C13 C14 1.387(2) . ?
C14 C15 1.383(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.517(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.512(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
