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#$Date: 2024-07-05 16:15:17 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/29/7132977.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_7132977
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            'C16 H13 N O3'
_chemical_formula_weight         267.27
_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
;
2024-03-05 deposited with the CCDC.	2024-04-22 downloaded from the CCDC.
;
_cell_angle_alpha                100.298(2)
_cell_angle_beta                 96.3058(19)
_cell_angle_gamma                111.3892(18)
_cell_formula_units_Z            2
_cell_length_a                   6.7066(7)
_cell_length_b                   8.7863(9)
_cell_length_c                   12.6844(13)
_cell_measurement_reflns_used    3607
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.56
_cell_volume                     672.14(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 0.995
_diffrn_measured_fraction_theta_max 0.913
_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  0.0383
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12848
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.291
_diffrn_reflns_theta_min         1.662
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9598
_exptl_absorpt_correction_T_min  0.9169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       brick
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0493
_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)+(0.0441P)²+0.2865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1299
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2185
_reflns_number_total             3342
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc01214c2.cif
_cod_data_source_block           sba200
_cod_depositor_comments
'Adding full bibliography for 7132976--7132977.cif.'
_cod_database_code               7132977
_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   0.989
_shelx_estimated_absorpt_t_max   0.994
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 0.5701(3) 0.3912(2) 0.28482(14) 0.0345(4) Uani 1 1 d . . . . .
O2 O 0.7225(2) 0.32163(15) 0.29774(9) 0.0385(3) Uani 1 1 d . . . . .
O1 O 0.4185(2) 0.33183(17) 0.20985(11) 0.0504(4) Uani 1 1 d . . . . .
C11 C 0.6203(3) 0.5423(2) 0.37191(13) 0.0314(4) Uani 1 1 d . . . . .
C12 C 0.8129(3) 0.6159(2) 0.44754(14) 0.0361(4) Uani 1 1 d . . . . .
H12 H 0.918615 0.567771 0.444260 0.043 Uiso 1 1 calc R U . . .
C13 C 0.8547(3) 0.7584(2) 0.52806(14) 0.0369(4) Uani 1 1 d . . . . .
H13 H 0.987774 0.807545 0.579819 0.044 Uiso 1 1 calc R U . . .
C14 C 0.7002(3) 0.8289(2) 0.53245(14) 0.0340(4) Uani 1 1 d . . . . .
C15 C 0.5069(3) 0.7577(2) 0.45530(14) 0.0378(4) Uani 1 1 d . . . . .
H15 H 0.402611 0.807355 0.457299 0.045 Uiso 1 1 calc R U . . .
C16 C 0.4673(3) 0.6153(2) 0.37619(14) 0.0360(4) Uani 1 1 d . . . . .
H16 H 0.334777 0.566252 0.324074 0.043 Uiso 1 1 calc R U . . .
O18 O 0.7222(2) 0.96721(16) 0.60859(11) 0.0454(4) Uani 1 1 d . . . . .
C18 C 0.9084(4) 1.0348(3) 0.69564(17) 0.0505(5) Uani 1 1 d . . . . .
H18A H 0.903282 1.131396 0.745920 0.076 Uiso 1 1 calc R U . . .
H18B H 1.041934 1.071045 0.665500 0.076 Uiso 1 1 calc R U . . .
H18C H 0.907297 0.948290 0.735028 0.076 Uiso 1 1 calc R U . . .
C21 C 0.7195(3) 0.2017(2) 0.20811(13) 0.0321(4) Uani 1 1 d . . . . .
C22 C 0.8236(3) 0.2593(2) 0.12513(14) 0.0320(4) Uani 1 1 d . . . . .
C23 C 0.8329(3) 0.1428(2) 0.03770(14) 0.0342(4) Uani 1 1 d . . . . .
H23 H 0.901741 0.179775 -0.019914 0.041 Uiso 1 1 calc R U . . .
C24 C 0.7418(3) -0.0265(2) 0.03502(14) 0.0330(4) Uani 1 1 d . . . . .
H24 H 0.747914 -0.105382 -0.025088 0.040 Uiso 1 1 calc R U . . .
C25 C 0.6414(3) -0.0837(2) 0.11831(14) 0.0329(4) Uani 1 1 d . . . . .
C26 C 0.6301(3) 0.0329(2) 0.20558(14) 0.0341(4) Uani 1 1 d . . . . .
H26 H 0.560883 -0.004359 0.263032 0.041 Uiso 1 1 calc R U . . .
N28 N 0.9887(3) 0.5781(2) 0.13809(16) 0.0558(5) Uani 1 1 d . . . . .
C28 C 0.9166(3) 0.4366(2) 0.13141(15) 0.0385(4) Uani 1 1 d . . . . .
C29 C 0.5473(3) -0.2691(2) 0.11417(17) 0.0458(5) Uani 1 1 d . . . . .
H29A H 0.403519 -0.300355 0.134687 0.069 Uiso 1 1 calc R U . . .
H29B H 0.644456 -0.294779 0.165151 0.069 Uiso 1 1 calc R U . . .
H29C H 0.532611 -0.332903 0.039969 0.069 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
O1 C1 O2 121.90(15) . . ?
O1 C1 C11 126.25(16) . . ?
O2 C1 C11 111.84(14) . . ?
C1 O2 C21 116.49(13) . . ?
C12 C11 C16 119.06(15) . . ?
C12 C11 C1 122.82(15) . . ?
C16 C11 C1 118.11(15) . . ?
C11 C12 C13 121.20(16) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C14 119.29(16) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
O18 C14 C13 124.48(16) . . ?
O18 C14 C15 115.46(15) . . ?
C13 C14 C15 120.06(16) . . ?
C16 C15 C14 119.85(16) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 120.52(16) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C14 O18 C18 117.33(14) . . ?
O18 C18 H18A 109.5 . . ?
O18 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O18 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C26 C21 C22 121.08(15) . . ?
C26 C21 O2 120.93(15) . . ?
C22 C21 O2 117.83(15) . . ?
C23 C22 C21 119.00(16) . . ?
C23 C22 C28 121.66(16) . . ?
C21 C22 C28 119.34(15) . . ?
C24 C23 C22 119.77(17) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 121.29(16) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C24 C25 C26 119.03(16) . . ?
C24 C25 C29 120.07(16) . . ?
C26 C25 C29 120.90(17) . . ?
C21 C26 C25 119.82(16) . . ?
C21 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
N28 C28 C22 178.7(2) . . ?
C25 C29 H29A 109.5 . . ?
C25 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C25 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
C1 O1 1.197(2) . ?
C1 O2 1.378(2) . ?
C1 C11 1.472(2) . ?
O2 C21 1.3979(19) . ?
C11 C12 1.380(2) . ?
C11 C16 1.395(2) . ?
C12 C13 1.383(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(2) . ?
C13 H13 0.9500 . ?
C14 O18 1.3601(19) . ?
C14 C15 1.393(2) . ?
C15 C16 1.376(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
O18 C18 1.433(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C21 C26 1.375(2) . ?
C21 C22 1.395(2) . ?
C22 C23 1.392(2) . ?
C22 C28 1.435(2) . ?
C23 C24 1.379(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.396(2) . ?
C25 C29 1.506(2) . ?
C26 H26 0.9500 . ?
N28 C28 1.141(2) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
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
O1 C1 O2 C21 13.3(3) . . . . ?
C11 C1 O2 C21 -166.13(14) . . . . ?
O1 C1 C11 C12 -171.22(19) . . . . ?
O2 C1 C11 C12 8.2(2) . . . . ?
O1 C1 C11 C16 7.5(3) . . . . ?
O2 C1 C11 C16 -173.04(15) . . . . ?
C16 C11 C12 C13 1.0(3) . . . . ?
C1 C11 C12 C13 179.76(17) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 O18 179.10(17) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
O18 C14 C15 C16 -178.66(17) . . . . ?
C13 C14 C15 C16 1.4(3) . . . . ?
C14 C15 C16 C11 -0.6(3) . . . . ?
C12 C11 C16 C15 -0.6(3) . . . . ?
C1 C11 C16 C15 -179.38(17) . . . . ?
C13 C14 O18 C18 -6.0(3) . . . . ?
C15 C14 O18 C18 174.10(17) . . . . ?
C1 O2 C21 C26 -103.01(18) . . . . ?
C1 O2 C21 C22 81.46(19) . . . . ?
C26 C21 C22 C23 1.2(2) . . . . ?
O2 C21 C22 C23 176.67(14) . . . . ?
C26 C21 C22 C28 -179.38(16) . . . . ?
O2 C21 C22 C28 -3.9(2) . . . . ?
C21 C22 C23 C24 -0.7(2) . . . . ?
C28 C22 C23 C24 179.86(16) . . . . ?
C22 C23 C24 C25 -0.4(2) . . . . ?
C23 C24 C25 C26 1.0(2) . . . . ?
C23 C24 C25 C29 -178.81(16) . . . . ?
C22 C21 C26 C25 -0.6(2) . . . . ?
O2 C21 C26 C25 -175.94(14) . . . . ?
C24 C25 C26 C21 -0.5(2) . . . . ?
C29 C25 C26 C21 179.28(16) . . . . ?
