#------------------------------------------------------------------------------
#$Date: 2024-07-05 16:15:17 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/29/7132976.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_7132976
loop_
_publ_author_name
'Akbari, Alireza'
'Khosravi, Hormoz'
'Bauer, Felix'
'Rominger, Frank'
'Breit, Bernhard'
'Balalaie, Saeed'
_publ_section_title
;
 Metal- and solvent-free domino reaction of 2-isocyanophenol esters to
 benzoxazines: long-range 1,5-acyl migration on 1,4-diazabutatriene.
;
_journal_issue                   41
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5451
_journal_page_last               5454
_journal_paper_doi               10.1039/d4cc01214c
_journal_volume                  60
_journal_year                    2024
_chemical_formula_sum            'C28 H18 N2 O4'
_chemical_formula_weight         446.44
_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
;
2024-03-04 deposited with the CCDC.	2024-04-22 downloaded from the CCDC.
;
_cell_angle_alpha                92.2576(15)
_cell_angle_beta                 111.1719(14)
_cell_angle_gamma                93.0417(15)
_cell_formula_units_Z            2
_cell_length_a                   10.0719(6)
_cell_length_b                   10.5354(7)
_cell_length_c                   10.8948(7)
_cell_measurement_reflns_used    3255
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      23.33
_cell_measurement_theta_min      2.36
_cell_volume                     1074.38(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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14852
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.595
_diffrn_reflns_theta_min         1.940
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9590
_exptl_absorpt_correction_T_min  0.9267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       brick
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.146
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.111
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0525
_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)+(0.0372P)²+0.4526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1174
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2904
_reflns_number_total             4431
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc01214c2.cif
_cod_data_source_block           sba188
_cod_depositor_comments
'Adding full bibliography for 7132976--7132977.cif.'
_cod_database_code               7132976
_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   0.986
_shelx_estimated_absorpt_t_max   0.990
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
C11 C 0.6057(2) 0.10703(18) 0.9613(2) 0.0272(5) Uani 1 1 d . . . . .
O11 O 0.50939(14) 0.19164(13) 0.97388(13) 0.0296(3) Uani 1 1 d . . . . .
C12 C 0.7229(2) 0.0890(2) 1.0719(2) 0.0329(5) Uani 1 1 d . . . . .
H12 H 0.736427 0.132623 1.153934 0.039 Uiso 1 1 calc R U . . .
C13 C 0.8207(2) 0.0059(2) 1.0610(2) 0.0367(5) Uani 1 1 d . . . . .
H13 H 0.901675 -0.008245 1.136538 0.044 Uiso 1 1 calc R U . . .
C14 C 0.8014(2) -0.0568(2) 0.9411(2) 0.0381(6) Uani 1 1 d . . . . .
H14 H 0.870130 -0.112339 0.934486 0.046 Uiso 1 1 calc R U . . .
C15 C 0.6831(2) -0.0390(2) 0.8313(2) 0.0358(5) Uani 1 1 d . . . . .
H15 H 0.669548 -0.083158 0.749537 0.043 Uiso 1 1 calc R U . . .
C16 C 0.5836(2) 0.04370(19) 0.8404(2) 0.0285(5) Uani 1 1 d . . . . .
N16 N 0.46016(18) 0.05740(16) 0.72947(16) 0.0317(4) Uani 1 1 d . . . . .
C17 C 0.3700(2) 0.13260(19) 0.74485(19) 0.0275(5) Uani 1 1 d . . . . .
C18 C 0.3920(2) 0.21185(19) 0.86510(19) 0.0267(5) Uani 1 1 d . . . . .
C21 C 0.1994(2) 0.46448(19) 0.9316(2) 0.0280(5) Uani 1 1 d . . . . .
O21 O 0.08612(14) 0.44399(13) 0.81023(13) 0.0323(4) Uani 1 1 d . . . . .
C22 C 0.1968(2) 0.5657(2) 1.0145(2) 0.0339(5) Uani 1 1 d . . . . .
H22 H 0.117506 0.616797 0.991160 0.041 Uiso 1 1 calc R U . . .
C23 C 0.3113(2) 0.5921(2) 1.1327(2) 0.0352(5) Uani 1 1 d . . . . .
H23 H 0.311361 0.662179 1.190332 0.042 Uiso 1 1 calc R U . . .
C24 C 0.4248(2) 0.5162(2) 1.1658(2) 0.0334(5) Uani 1 1 d . . . . .
H24 H 0.502534 0.533995 1.247031 0.040 Uiso 1 1 calc R U . . .
C25 C 0.4272(2) 0.41449(19) 1.0824(2) 0.0309(5) Uani 1 1 d . . . . .
H25 H 0.506017 0.362793 1.107460 0.037 Uiso 1 1 calc R U . . .
N26 N 0.30518(17) 0.29548(15) 0.86144(16) 0.0279(4) Uani 1 1 d . . . . .
C26 C 0.3144(2) 0.38704(19) 0.9615(2) 0.0274(5) Uani 1 1 d . . . . .
C30 C 0.2268(2) 0.1352(2) 0.6323(2) 0.0299(5) Uani 1 1 d . . . . .
O30 O 0.12456(16) 0.07822(16) 0.64377(15) 0.0434(4) Uani 1 1 d . . . . .
C31 C 0.2189(2) 0.20182(19) 0.5132(2) 0.0280(5) Uani 1 1 d . . . . .
C32 C 0.0890(2) 0.1979(2) 0.4085(2) 0.0378(6) Uani 1 1 d . . . . .
H32 H 0.007495 0.152637 0.414031 0.045 Uiso 1 1 calc R U . . .
C33 C 0.0782(2) 0.2597(2) 0.2966(2) 0.0427(6) Uani 1 1 d . . . . .
H33 H -0.010643 0.255934 0.224816 0.051 Uiso 1 1 calc R U . . .
C34 C 0.1950(3) 0.3266(2) 0.2880(2) 0.0418(6) Uani 1 1 d . . . . .
H34 H 0.186526 0.369738 0.210876 0.050 Uiso 1 1 calc R U . . .
C35 C 0.3250(2) 0.3313(2) 0.3916(2) 0.0403(6) Uani 1 1 d . . . . .
H35 H 0.405920 0.377222 0.385595 0.048 Uiso 1 1 calc R U . . .
C36 C 0.3369(2) 0.2689(2) 0.5041(2) 0.0340(5) Uani 1 1 d . . . . .
H36 H 0.426158 0.272062 0.575366 0.041 Uiso 1 1 calc R U . . .
C40 C 0.0006(2) 0.3343(2) 0.7932(2) 0.0310(5) Uani 1 1 d . . . . .
O40 O 0.01026(15) 0.26695(14) 0.88202(15) 0.0389(4) Uani 1 1 d . . . . .
C41 C -0.1040(2) 0.3123(2) 0.6568(2) 0.0328(5) Uani 1 1 d . . . . .
C42 C -0.1931(2) 0.2011(2) 0.6270(3) 0.0470(6) Uani 1 1 d . . . . .
H42 H -0.183674 0.141785 0.692545 0.056 Uiso 1 1 calc R U . . .
C43 C -0.2950(3) 0.1766(3) 0.5024(3) 0.0569(7) Uani 1 1 d . . . . .
H43 H -0.356342 0.100876 0.482251 0.068 Uiso 1 1 calc R U . . .
C44 C -0.3077(3) 0.2623(3) 0.4074(3) 0.0593(8) Uani 1 1 d . . . . .
H44 H -0.377887 0.245142 0.321577 0.071 Uiso 1 1 calc R U . . .
C45 C -0.2198(3) 0.3727(3) 0.4354(3) 0.0560(7) Uani 1 1 d . . . . .
H45 H -0.229304 0.431212 0.369113 0.067 Uiso 1 1 calc R U . . .
C46 C -0.1172(2) 0.3983(2) 0.5609(2) 0.0433(6) Uani 1 1 d . . . . .
H46 H -0.056454 0.474440 0.580822 0.052 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 C11 C16 121.62(19) . . ?
C12 C11 O11 117.78(18) . . ?
C16 C11 O11 120.60(17) . . ?
C18 O11 C11 118.99(16) . . ?
C11 C12 C13 118.6(2) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C14 C13 C12 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.9(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 118.92(19) . . ?
C15 C16 N16 119.62(19) . . ?
C11 C16 N16 121.40(18) . . ?
C17 N16 C16 116.80(18) . . ?
N16 C17 C18 124.95(19) . . ?
N16 C17 C30 117.74(18) . . ?
C18 C17 C30 117.25(17) . . ?
N26 C18 O11 124.51(19) . . ?
N26 C18 C17 118.69(18) . . ?
O11 C18 C17 116.77(17) . . ?
C22 C21 O21 118.07(18) . . ?
C22 C21 C26 122.36(19) . . ?
O21 C21 C26 119.47(18) . . ?
C40 O21 C21 116.27(15) . . ?
C21 C22 C23 119.3(2) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C24 C23 C22 119.6(2) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 121.0(2) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C24 C25 C26 120.6(2) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C18 N26 C26 127.32(18) . . ?
C21 C26 N26 114.84(18) . . ?
C21 C26 C25 117.09(19) . . ?
N26 C26 C25 127.96(19) . . ?
O30 C30 C31 123.14(19) . . ?
O30 C30 C17 117.44(19) . . ?
C31 C30 C17 119.38(18) . . ?
C36 C31 C32 119.4(2) . . ?
C36 C31 C30 121.86(19) . . ?
C32 C31 C30 118.77(19) . . ?
C33 C32 C31 120.1(2) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C34 C33 C32 120.5(2) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C33 C34 C35 120.0(2) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C34 C35 C36 119.9(2) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
C35 C36 C31 120.2(2) . . ?
C35 C36 H36 119.9 . . ?
C31 C36 H36 119.9 . . ?
O40 C40 O21 122.2(2) . . ?
O40 C40 C41 125.3(2) . . ?
O21 C40 C41 112.44(18) . . ?
C46 C41 C42 119.9(2) . . ?
C46 C41 C40 122.7(2) . . ?
C42 C41 C40 117.4(2) . . ?
C43 C42 C41 120.1(3) . . ?
C43 C42 H42 119.9 . . ?
C41 C42 H42 119.9 . . ?
C44 C43 C42 119.8(3) . . ?
C44 C43 H43 120.1 . . ?
C42 C43 H43 120.1 . . ?
C43 C44 C45 120.7(2) . . ?
C43 C44 H44 119.6 . . ?
C45 C44 H44 119.6 . . ?
C44 C45 C46 119.9(3) . . ?
C44 C45 H45 120.1 . . ?
C46 C45 H45 120.1 . . ?
C41 C46 C45 119.6(2) . . ?
C41 C46 H46 120.2 . . ?
C45 C46 H46 120.2 . . ?
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
C11 C12 1.377(3) . ?
C11 C16 1.390(3) . ?
C11 O11 1.390(2) . ?
O11 C18 1.372(2) . ?
C12 C13 1.385(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(3) . ?
C15 H15 0.9500 . ?
C16 N16 1.405(2) . ?
N16 C17 1.287(3) . ?
C17 C18 1.465(3) . ?
C17 C30 1.521(3) . ?
C18 N26 1.266(2) . ?
C21 C22 1.377(3) . ?
C21 O21 1.400(2) . ?
C21 C26 1.400(3) . ?
O21 C40 1.369(2) . ?
C22 C23 1.389(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.377(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.401(3) . ?
C25 H25 0.9500 . ?
N26 C26 1.401(3) . ?
C30 O30 1.212(2) . ?
C30 C31 1.478(3) . ?
C31 C36 1.387(3) . ?
C31 C32 1.388(3) . ?
C32 C33 1.376(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.374(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.382(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.383(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C40 O40 1.201(2) . ?
C40 C41 1.479(3) . ?
C41 C46 1.384(3) . ?
C41 C42 1.390(3) . ?
C42 C43 1.378(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.376(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.378(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.389(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C11 O11 C18 179.70(17) . . . . ?
C16 C11 O11 C18 -0.1(3) . . . . ?
C16 C11 C12 C13 0.3(3) . . . . ?
O11 C11 C12 C13 -179.47(18) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C15 -1.2(3) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C14 C15 C16 C11 -0.1(3) . . . . ?
C14 C15 C16 N16 -177.36(19) . . . . ?
C12 C11 C16 C15 -0.5(3) . . . . ?
O11 C11 C16 C15 179.25(18) . . . . ?
C12 C11 C16 N16 176.67(19) . . . . ?
O11 C11 C16 N16 -3.6(3) . . . . ?
C15 C16 N16 C17 178.11(19) . . . . ?
C11 C16 N16 C17 0.9(3) . . . . ?
C16 N16 C17 C18 5.2(3) . . . . ?
C16 N16 C17 C30 -171.82(17) . . . . ?
C11 O11 C18 N26 -172.63(18) . . . . ?
C11 O11 C18 C17 5.5(2) . . . . ?
N16 C17 C18 N26 169.6(2) . . . . ?
C30 C17 C18 N26 -13.3(3) . . . . ?
N16 C17 C18 O11 -8.7(3) . . . . ?
C30 C17 C18 O11 168.39(17) . . . . ?
C22 C21 O21 C40 -114.1(2) . . . . ?
C26 C21 O21 C40 69.5(2) . . . . ?
O21 C21 C22 C23 -176.77(18) . . . . ?
C26 C21 C22 C23 -0.4(3) . . . . ?
C21 C22 C23 C24 -0.7(3) . . . . ?
C22 C23 C24 C25 0.6(3) . . . . ?
C23 C24 C25 C26 0.6(3) . . . . ?
O11 C18 N26 C26 4.0(3) . . . . ?
C17 C18 N26 C26 -174.18(18) . . . . ?
C22 C21 C26 N26 -174.75(18) . . . . ?
O21 C21 C26 N26 1.5(3) . . . . ?
C22 C21 C26 C25 1.6(3) . . . . ?
O21 C21 C26 C25 177.88(17) . . . . ?
C18 N26 C26 C21 -177.62(19) . . . . ?
C18 N26 C26 C25 6.5(3) . . . . ?
C24 C25 C26 C21 -1.7(3) . . . . ?
C24 C25 C26 N26 174.14(19) . . . . ?
N16 C17 C30 O30 102.4(2) . . . . ?
C18 C17 C30 O30 -74.9(2) . . . . ?
N16 C17 C30 C31 -75.3(2) . . . . ?
C18 C17 C30 C31 107.4(2) . . . . ?
O30 C30 C31 C36 178.4(2) . . . . ?
C17 C30 C31 C36 -4.0(3) . . . . ?
O30 C30 C31 C32 -0.8(3) . . . . ?
C17 C30 C31 C32 176.74(19) . . . . ?
C36 C31 C32 C33 0.4(3) . . . . ?
C30 C31 C32 C33 179.6(2) . . . . ?
C31 C32 C33 C34 -0.7(4) . . . . ?
C32 C33 C34 C35 0.7(4) . . . . ?
C33 C34 C35 C36 -0.3(4) . . . . ?
C34 C35 C36 C31 0.0(3) . . . . ?
C32 C31 C36 C35 0.0(3) . . . . ?
C30 C31 C36 C35 -179.25(19) . . . . ?
C21 O21 C40 O40 9.0(3) . . . . ?
C21 O21 C40 C41 -172.47(16) . . . . ?
O40 C40 C41 C46 175.0(2) . . . . ?
O21 C40 C41 C46 -3.5(3) . . . . ?
O40 C40 C41 C42 -3.8(3) . . . . ?
O21 C40 C41 C42 177.73(19) . . . . ?
C46 C41 C42 C43 -0.4(3) . . . . ?
C40 C41 C42 C43 178.5(2) . . . . ?
C41 C42 C43 C44 0.4(4) . . . . ?
C42 C43 C44 C45 -0.2(4) . . . . ?
C43 C44 C45 C46 -0.1(4) . . . . ?
C42 C41 C46 C45 0.1(3) . . . . ?
C40 C41 C46 C45 -178.7(2) . . . . ?
C44 C45 C46 C41 0.2(4) . . . . ?
