#------------------------------------------------------------------------------
#$Date: 2024-07-05 16:18:53 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292784 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/31/7133150.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_7133150
loop_
_publ_author_name
'Sakai, Dan'
'Kojima, Tatsuhiro'
'Kawasaki-Takasuka, Tomoko'
'Mori, Keiji'
_publ_section_title
;
 Stereoselective synthesis of 6/7/6-fused heterocycles with multiple
 stereocenters via an internal redox reaction/inverse
 electron-demand hetero-Diels-Alder reaction sequence.
;
_journal_issue                   53
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6797
_journal_page_last               6800
_journal_paper_doi               10.1039/d4cc02351j
_journal_volume                  60
_journal_year                    2024
_chemical_formula_sum            'C28 H30 N2 O4'
_chemical_formula_weight         458.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-04-25 deposited with the CCDC.	2024-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 129.444(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4111(4)
_cell_length_b                   20.2712(5)
_cell_length_c                   10.3678(3)
_cell_measurement_reflns_used    9826
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      30.2690
_cell_measurement_theta_min      2.0790
_cell_volume                     2338.94(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_molecular_graphics    Mercury
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.797
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.797
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11891
_diffrn_reflns_point_group_measured_fraction_full 0.930
_diffrn_reflns_point_group_measured_fraction_max 0.695
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.382
_diffrn_reflns_theta_min         2.088
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.75a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       plate
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1943 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4914
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0307
_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)+(0.0506P)²+0.3937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0807
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.862
_reflns_Friedel_fraction_max     0.593
_reflns_number_gt                4711
_reflns_number_total             4914
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc02351j2.cif
_cod_data_source_block           2aa
_cod_depositor_comments
'Adding full bibliography for 7133150--7133151.cif.'
_cod_original_cell_volume        2338.94(12)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7133150
_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   0.991
_shelx_estimated_absorpt_t_max   0.999
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
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 0.43385(15) 0.31409(8) 0.4427(2) 0.0158(3) Uani 1 1 d . . . . .
H1 H 0.347989 0.323040 0.389243 0.019 Uiso 1 1 calc R U . . .
C2 C 0.44130(15) 0.29601(8) 0.3067(2) 0.0155(3) Uani 1 1 d . . . . .
H2 H 0.524223 0.278902 0.363731 0.019 Uiso 1 1 calc R U . . .
C3 C 0.42007(15) 0.35391(8) 0.1930(2) 0.0155(3) Uani 1 1 d . . . . .
H3 H 0.379671 0.334878 0.079575 0.019 Uiso 1 1 calc R U . . .
C4 C 0.33943(15) 0.41029(8) 0.1704(2) 0.0168(3) Uani 1 1 d . . . . .
H4A H 0.308143 0.434970 0.067494 0.020 Uiso 1 1 calc R U . . .
H4B H 0.269802 0.391075 0.154939 0.020 Uiso 1 1 calc R U . . .
C5 C 0.40380(15) 0.45868(8) 0.3176(2) 0.0151(3) Uani 1 1 d . . . . .
C6 C 0.43544(15) 0.43008(8) 0.4788(2) 0.0174(3) Uani 1 1 d . . . . .
H6A H 0.480943 0.463701 0.568101 0.021 Uiso 1 1 calc R U . . .
H6B H 0.359909 0.421339 0.459572 0.021 Uiso 1 1 calc R U . . .
C7 C 0.53648(15) 0.38288(8) 0.2506(2) 0.0165(3) Uani 1 1 d . . . . .
C8 C 0.61111(17) 0.34680(9) 0.2279(2) 0.0192(3) Uani 1 1 d . . . . .
C9 C 0.75870(16) 0.43794(9) 0.3672(2) 0.0197(4) Uani 1 1 d . . . . .
C10 C 0.57533(15) 0.44201(8) 0.3291(2) 0.0157(3) Uani 1 1 d . . . . .
C11 C 0.8011(2) 0.34072(10) 0.2744(3) 0.0301(4) Uani 1 1 d . . . . .
H11A H 0.763608 0.298782 0.217056 0.045 Uiso 0.5 1 calc R U P . .
H11B H 0.816530 0.366900 0.210311 0.045 Uiso 0.5 1 calc R U P . .
H11C H 0.877194 0.332053 0.386126 0.045 Uiso 0.5 1 calc R U P . .
H11D H 0.874614 0.366375 0.325272 0.045 Uiso 0.5 1 calc R U P . .
H11E H 0.821691 0.298256 0.332017 0.045 Uiso 0.5 1 calc R U P . .
H11F H 0.761027 0.333104 0.156202 0.045 Uiso 0.5 1 calc R U P . .
C12 C 0.72289(17) 0.53259(9) 0.4781(2) 0.0232(4) Uani 1 1 d . . . . .
H12A H 0.800019 0.545386 0.508083 0.035 Uiso 1 1 calc R U . . .
H12B H 0.663144 0.567030 0.408386 0.035 Uiso 1 1 calc R U . . .
H12C H 0.732497 0.527016 0.579917 0.035 Uiso 1 1 calc R U . . .
C13 C 0.33136(16) 0.52122(8) 0.2761(2) 0.0169(3) Uani 1 1 d . . . . .
C14 C 0.38125(17) 0.58400(9) 0.3075(2) 0.0208(3) Uani 1 1 d . . . . .
H14 H 0.462108 0.588649 0.350970 0.025 Uiso 1 1 calc R U . . .
C15 C 0.31353(19) 0.63981(9) 0.2757(3) 0.0244(4) Uani 1 1 d . . . . .
H15 H 0.348204 0.682324 0.296215 0.029 Uiso 1 1 calc R U . . .
C16 C 0.19630(19) 0.63405(10) 0.2145(2) 0.0241(4) Uani 1 1 d . . . . .
H16 H 0.150992 0.672306 0.195280 0.029 Uiso 1 1 calc R U . . .
C17 C 0.14541(17) 0.57197(10) 0.1813(3) 0.0265(4) Uani 1 1 d . . . . .
H17 H 0.064326 0.567710 0.137099 0.032 Uiso 1 1 calc R U . . .
C18 C 0.21233(17) 0.51591(9) 0.2123(2) 0.0233(4) Uani 1 1 d . . . . .
H18 H 0.176756 0.473555 0.189831 0.028 Uiso 1 1 calc R U . . .
C19 C 0.35467(16) 0.23835(8) 0.2119(2) 0.0177(3) Uani 1 1 d . . . . .
H19A H 0.344460 0.229672 0.109530 0.021 Uiso 1 1 calc R U . . .
H19B H 0.275153 0.250318 0.177511 0.021 Uiso 1 1 calc R U . . .
C20 C 0.40054(15) 0.17515(8) 0.3193(2) 0.0166(3) Uani 1 1 d . . . . .
C21 C 0.46133(15) 0.19109(8) 0.5017(2) 0.0161(3) Uani 1 1 d . . . . .
C22 C 0.50398(16) 0.13895(9) 0.6160(2) 0.0200(4) Uani 1 1 d . . . . .
H22 H 0.493235 0.094844 0.577741 0.024 Uiso 1 1 calc R U . . .
C23 C 0.56142(19) 0.15032(10) 0.7834(2) 0.0267(4) Uani 1 1 d . . . . .
H23 H 0.590699 0.114370 0.858882 0.032 Uiso 1 1 calc R U . . .
C24 C 0.5759(2) 0.21473(10) 0.8399(2) 0.0293(4) Uani 1 1 d . . . . .
H24 H 0.614352 0.222931 0.954124 0.035 Uiso 1 1 calc R U . . .
C25 C 0.53394(18) 0.26690(9) 0.7290(2) 0.0247(4) Uani 1 1 d . . . . .
H25 H 0.543678 0.310815 0.767820 0.030 Uiso 1 1 calc R U . . .
C26 C 0.47777(15) 0.25576(8) 0.5614(2) 0.0170(3) Uani 1 1 d . . . . .
C27 C 0.49161(19) 0.14070(9) 0.3106(3) 0.0252(4) Uani 1 1 d . . . . .
H27A H 0.453105 0.130389 0.194059 0.038 Uiso 1 1 calc R U . . .
H27B H 0.560324 0.169972 0.356497 0.038 Uiso 1 1 calc R U . . .
H27C H 0.519402 0.099810 0.375841 0.038 Uiso 1 1 calc R U . . .
C28 C 0.29303(18) 0.12895(10) 0.2458(2) 0.0254(4) Uani 1 1 d . . . . .
H28A H 0.254993 0.119159 0.129101 0.038 Uiso 1 1 calc R U . . .
H28B H 0.320849 0.087818 0.310032 0.038 Uiso 1 1 calc R U . . .
H28C H 0.234631 0.150377 0.251200 0.038 Uiso 1 1 calc R U . . .
N1 N 0.72012(15) 0.37742(8) 0.2892(2) 0.0216(3) Uani 1 1 d . . . . .
N2 N 0.68243(13) 0.47014(7) 0.38508(19) 0.0176(3) Uani 1 1 d . . . . .
O1 O 0.50384(11) 0.37122(6) 0.53550(15) 0.0175(3) Uani 1 1 d . . . . .
O2 O 0.51737(11) 0.48092(6) 0.36102(15) 0.0170(2) Uani 1 1 d . . . . .
O3 O 0.58539(13) 0.29234(6) 0.16102(18) 0.0266(3) Uani 1 1 d . . . . .
O4 O 0.85405(13) 0.46241(7) 0.41792(19) 0.0270(3) 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'
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
O1 C1 C26 109.30(13) . . ?
O1 C1 C2 112.49(13) . . ?
C26 C1 C2 108.87(13) . . ?
C1 C2 C19 105.68(13) . . ?
C1 C2 C3 115.18(13) . . ?
C19 C2 C3 113.84(13) . . ?
C7 C3 C4 108.41(14) . . ?
C7 C3 C2 111.33(14) . . ?
C4 C3 C2 116.31(14) . . ?
C5 C4 C3 113.76(14) . . ?
O2 C5 C13 105.21(13) . . ?
O2 C5 C4 110.71(13) . . ?
C13 C5 C4 112.28(14) . . ?
O2 C5 C6 106.24(13) . . ?
C13 C5 C6 107.33(13) . . ?
C4 C5 C6 114.47(14) . . ?
O1 C6 C5 114.58(13) . . ?
C10 C7 C8 118.80(16) . . ?
C10 C7 C3 121.17(15) . . ?
C8 C7 C3 119.99(15) . . ?
O3 C8 N1 119.99(16) . . ?
O3 C8 C7 124.08(17) . . ?
N1 C8 C7 115.93(15) . . ?
O4 C9 N1 122.59(17) . . ?
O4 C9 N2 121.39(17) . . ?
N1 C9 N2 116.02(16) . . ?
O2 C10 C7 125.97(16) . . ?
O2 C10 N2 111.12(14) . . ?
C7 C10 N2 122.90(15) . . ?
C14 C13 C18 118.49(16) . . ?
C14 C13 C5 122.37(16) . . ?
C18 C13 C5 119.06(16) . . ?
C15 C14 C13 120.48(18) . . ?
C16 C15 C14 120.63(19) . . ?
C15 C16 C17 119.41(17) . . ?
C16 C17 C18 120.35(18) . . ?
C17 C18 C13 120.64(18) . . ?
C2 C19 C20 111.74(13) . . ?
C21 C20 C28 110.33(14) . . ?
C21 C20 C27 109.16(14) . . ?
C28 C20 C27 108.84(15) . . ?
C21 C20 C19 111.29(13) . . ?
C28 C20 C19 108.26(14) . . ?
C27 C20 C19 108.92(14) . . ?
C26 C21 C22 118.04(16) . . ?
C26 C21 C20 123.05(15) . . ?
C22 C21 C20 118.90(15) . . ?
C23 C22 C21 121.56(17) . . ?
C22 C23 C24 119.59(17) . . ?
C25 C24 C23 119.73(18) . . ?
C24 C25 C26 120.86(17) . . ?
C25 C26 C21 120.20(16) . . ?
C25 C26 C1 119.74(15) . . ?
C21 C26 C1 120.06(15) . . ?
C9 N1 C8 125.12(15) . . ?
C9 N1 C11 117.40(17) . . ?
C8 N1 C11 117.44(16) . . ?
C10 N2 C9 121.20(15) . . ?
C10 N2 C12 120.22(14) . . ?
C9 N2 C12 118.37(15) . . ?
C6 O1 C1 113.28(12) . . ?
C10 O2 C5 119.66(13) . . ?
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 O1 1.432(2) . ?
C1 C26 1.525(2) . ?
C1 C2 1.525(2) . ?
C2 C19 1.527(2) . ?
C2 C3 1.550(2) . ?
C3 C7 1.497(2) . ?
C3 C4 1.538(2) . ?
C4 C5 1.534(2) . ?
C5 O2 1.466(2) . ?
C5 C13 1.520(2) . ?
C5 C6 1.539(2) . ?
C6 O1 1.416(2) . ?
C7 C10 1.354(2) . ?
C7 C8 1.438(2) . ?
C8 O3 1.229(2) . ?
C8 N1 1.410(2) . ?
C9 O4 1.222(2) . ?
C9 N1 1.377(2) . ?
C9 N2 1.388(2) . ?
C10 O2 1.334(2) . ?
C10 N2 1.381(2) . ?
C11 N1 1.472(2) . ?
C12 N2 1.469(2) . ?
C13 C14 1.395(2) . ?
C13 C18 1.396(3) . ?
C14 C15 1.390(3) . ?
C15 C16 1.381(3) . ?
C16 C17 1.385(3) . ?
C17 C18 1.390(3) . ?
C19 C20 1.544(2) . ?
C20 C21 1.531(2) . ?
C20 C28 1.535(2) . ?
C20 C27 1.539(2) . ?
C21 C26 1.404(2) . ?
C21 C22 1.405(2) . ?
C22 C23 1.387(3) . ?
C23 C24 1.392(3) . ?
C24 C25 1.387(3) . ?
C25 C26 1.392(3) . ?
