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#$Date: 2022-11-12 03:50:58 +0200 (Sat, 12 Nov 2022) $
#$Revision: 279242 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/89/7158984.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_7158984
loop_
_publ_author_name
'Sobhani, Maryam'
'Figueira de Abreu, Rúben Manuel'
'Villinger, Alexander'
'Ehlers, Peter'
'Langer, Peter'
_publ_section_title
;
 Synthesis of imidazo[1,2-a]benzoazepines by alkyne-carbonyl-metathesis
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01320G
_journal_year                    2022
_chemical_formula_moiety         'C24 H16 F2 N2 O2'
_chemical_formula_sum            'C24 H16 F2 N2 O2'
_chemical_formula_weight         402.39
_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-2014/7
_audit_update_record
;
2022-04-06 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                109.827(7)
_cell_angle_beta                 97.404(7)
_cell_angle_gamma                104.970(7)
_cell_formula_units_Z            2
_cell_length_a                   6.6890(13)
_cell_length_b                   11.222(2)
_cell_length_c                   13.775(3)
_cell_measurement_reflns_used    9879
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      34.13
_cell_measurement_theta_min      3.06
_cell_volume                     912.6(3)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Apex Kappa-II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0913
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_number            4376
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.996
_diffrn_reflns_theta_min         3.237
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.746926
_exptl_absorpt_correction_T_min  0.452788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(TWINABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.990
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0667
_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)+(0.1478P)²+0.0021P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1897
_refine_ls_wR_factor_ref         0.2042
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3432
_reflns_number_total             4376
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01320g2.cif
_cod_data_source_block           is_rfmyda501
_cod_database_code               7158984
_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.
;
_shelx_estimated_absorpt_t_min   0.901
_shelx_estimated_absorpt_t_max   0.989
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
F1 F 0.11406(17) 0.69527(11) 0.00068(9) 0.0259(3) Uani 1 1 d . . . . .
F2 F 0.49596(19) 0.78308(12) -0.03226(9) 0.0306(3) Uani 1 1 d . . . . .
O1 O 0.9501(2) 0.34188(15) 0.42148(12) 0.0310(4) Uani 1 1 d . . . . .
O2 O 0.3904(2) 0.08347(14) 0.67831(11) 0.0273(3) Uani 1 1 d . . . . .
N1 N 0.7629(2) 0.58632(14) 0.20106(12) 0.0208(3) Uani 1 1 d . . . . .
N2 N 0.4340(2) 0.50496(14) 0.22402(12) 0.0178(3) Uani 1 1 d . . . . .
C1 C 0.6465(3) 0.51708(17) 0.24762(14) 0.0190(4) Uani 1 1 d . . . . .
C2 C 0.7301(3) 0.46322(18) 0.31957(14) 0.0204(4) Uani 1 1 d . . . . .
H2 H 0.8699 0.5129 0.3630 0.024 Uiso 1 1 calc R U . . .
C3 C 0.6306(3) 0.35031(17) 0.33132(14) 0.0198(4) Uani 1 1 d . . . . .
C4 C 0.4201(3) 0.25232(17) 0.26475(13) 0.0189(4) Uani 1 1 d . . . . .
C5 C 0.3945(3) 0.11508(18) 0.23060(15) 0.0244(4) Uani 1 1 d . . . . .
H5 H 0.5086 0.0872 0.2527 0.029 Uiso 1 1 calc R U . . .
C6 C 0.2040(3) 0.01980(19) 0.16488(15) 0.0284(4) Uani 1 1 d . . . . .
H6 H 0.1895 -0.0726 0.1412 0.034 Uiso 1 1 calc R U . . .
C7 C 0.0354(3) 0.0591(2) 0.13379(15) 0.0290(5) Uani 1 1 d . . . . .
H7 H -0.0953 -0.0063 0.0895 0.035 Uiso 1 1 calc R U . . .
C8 C 0.0575(3) 0.19459(18) 0.16746(14) 0.0232(4) Uani 1 1 d . . . . .
H8 H -0.0589 0.2214 0.1463 0.028 Uiso 1 1 calc R U . . .
C9 C 0.2495(3) 0.29151(16) 0.23211(13) 0.0185(4) Uani 1 1 d . . . . .
C10 C 0.2722(3) 0.43849(17) 0.26736(14) 0.0190(4) Uani 1 1 d . . . . .
H10A H 0.1339 0.4482 0.2427 0.023 Uiso 1 1 calc R U . . .
H10B H 0.3130 0.4813 0.3459 0.023 Uiso 1 1 calc R U . . .
C11 C 0.4115(3) 0.57175(16) 0.15761(14) 0.0174(4) Uani 1 1 d . . . . .
C12 C 0.2350(3) 0.59627(16) 0.11248(14) 0.0190(4) Uani 1 1 d . . . . .
H12 H 0.0977 0.5660 0.1245 0.023 Uiso 1 1 calc R U . . .
C13 C 0.2753(3) 0.66729(17) 0.04960(14) 0.0201(4) Uani 1 1 d . . . . .
C14 C 0.4778(3) 0.71390(17) 0.03191(14) 0.0209(4) Uani 1 1 d . . . . .
C15 C 0.6505(3) 0.69172(17) 0.07699(15) 0.0219(4) Uani 1 1 d . . . . .
H15 H 0.7871 0.7235 0.0647 0.026 Uiso 1 1 calc R U . . .
C16 C 0.6171(3) 0.61950(16) 0.14258(14) 0.0185(4) Uani 1 1 d . . . . .
C17 C 0.7585(3) 0.31819(18) 0.41307(14) 0.0215(4) Uani 1 1 d . . . . .
C18 C 0.6511(3) 0.26172(17) 0.48307(14) 0.0192(4) Uani 1 1 d . . . . .
C19 C 0.7698(3) 0.22038(19) 0.54908(15) 0.0244(4) Uani 1 1 d . . . . .
H19 H 0.9153 0.2316 0.5485 0.029 Uiso 1 1 calc R U . . .
C20 C 0.6821(3) 0.1640(2) 0.61466(15) 0.0261(4) Uani 1 1 d . . . . .
H20 H 0.7666 0.1372 0.6588 0.031 Uiso 1 1 calc R U . . .
C21 C 0.4682(3) 0.14649(18) 0.61593(14) 0.0213(4) Uani 1 1 d . . . . .
C22 C 0.3505(3) 0.19349(18) 0.55548(14) 0.0221(4) Uani 1 1 d . . . . .
H22 H 0.2074 0.1867 0.5593 0.027 Uiso 1 1 calc R U . . .
C23 C 0.4405(3) 0.25026(18) 0.48956(14) 0.0212(4) Uani 1 1 d . . . . .
H23 H 0.3582 0.2816 0.4485 0.025 Uiso 1 1 calc R U . . .
C24 C 0.1668(3) 0.0489(2) 0.67165(17) 0.0312(5) Uani 1 1 d . . . . .
H24A H 0.0888 -0.0001 0.5971 0.047 Uiso 1 1 calc R U . . .
H24B H 0.1297 0.1307 0.7017 0.047 Uiso 1 1 calc R U . . .
H24C H 0.1282 -0.0075 0.7117 0.047 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'
F F 0.0171 0.0103 '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
C21 O2 C24 117.61(15) . . ?
C1 N1 C16 104.42(14) . . ?
C1 N2 C11 106.68(14) . . ?
C1 N2 C10 124.63(15) . . ?
C11 N2 C10 128.63(14) . . ?
N1 C1 N2 113.11(16) . . ?
N1 C1 C2 124.96(16) . . ?
N2 C1 C2 121.88(16) . . ?
C3 C2 C1 126.78(16) . . ?
C3 C2 H2 116.6 . . ?
C1 C2 H2 116.6 . . ?
C2 C3 C4 125.06(16) . . ?
C2 C3 C17 115.19(15) . . ?
C4 C3 C17 119.50(15) . . ?
C9 C4 C5 118.84(16) . . ?
C9 C4 C3 122.65(15) . . ?
C5 C4 C3 118.48(16) . . ?
C6 C5 C4 120.70(17) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C6 C5 120.18(18) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 119.91(17) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 120.46(18) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C4 119.90(16) . . ?
C8 C9 C10 119.97(15) . . ?
C4 C9 C10 120.12(14) . . ?
N2 C10 C9 110.35(14) . . ?
N2 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
N2 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N2 C11 C12 131.72(15) . . ?
N2 C11 C16 105.33(15) . . ?
C12 C11 C16 122.93(16) . . ?
C13 C12 C11 114.81(16) . . ?
C13 C12 H12 122.6 . . ?
C11 C12 H12 122.6 . . ?
F1 C13 C12 119.67(16) . . ?
F1 C13 C14 117.02(16) . . ?
C12 C13 C14 123.31(17) . . ?
F2 C14 C15 120.65(16) . . ?
F2 C14 C13 117.38(16) . . ?
C15 C14 C13 121.96(17) . . ?
C14 C15 C16 116.80(16) . . ?
C14 C15 H15 121.6 . . ?
C16 C15 H15 121.6 . . ?
N1 C16 C15 129.42(16) . . ?
N1 C16 C11 110.41(15) . . ?
C15 C16 C11 120.15(16) . . ?
O1 C17 C18 120.82(16) . . ?
O1 C17 C3 119.14(17) . . ?
C18 C17 C3 120.02(15) . . ?
C23 C18 C19 117.69(17) . . ?
C23 C18 C17 124.30(16) . . ?
C19 C18 C17 118.00(16) . . ?
C20 C19 C18 122.02(17) . . ?
C20 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C19 C20 C21 119.57(17) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
O2 C21 C22 124.60(16) . . ?
O2 C21 C20 116.01(16) . . ?
C22 C21 C20 119.39(17) . . ?
C23 C22 C21 120.48(16) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C18 120.68(16) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
F1 C13 1.359(2) . ?
F2 C14 1.358(2) . ?
O1 C17 1.221(2) . ?
O2 C21 1.359(2) . ?
O2 C24 1.428(3) . ?
N1 C1 1.333(2) . ?
N1 C16 1.388(2) . ?
N2 C1 1.377(2) . ?
N2 C11 1.382(2) . ?
N2 C10 1.462(2) . ?
C1 C2 1.449(2) . ?
C2 C3 1.344(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.489(2) . ?
C3 C17 1.522(2) . ?
C4 C9 1.400(2) . ?
C4 C5 1.405(3) . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.397(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.513(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.397(2) . ?
C11 C16 1.410(2) . ?
C12 C13 1.369(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.405(3) . ?
C14 C15 1.360(3) . ?
C15 C16 1.407(3) . ?
C15 H15 0.9500 . ?
C17 C18 1.485(3) . ?
C18 C23 1.398(3) . ?
C18 C19 1.401(2) . ?
C19 C20 1.376(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.396(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(2) . ?
C22 C23 1.389(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C16 N1 C1 N2 -0.9(2) . . . . ?
C16 N1 C1 C2 -178.46(16) . . . . ?
C11 N2 C1 N1 -0.2(2) . . . . ?
C10 N2 C1 N1 -177.63(14) . . . . ?
C11 N2 C1 C2 177.43(15) . . . . ?
C10 N2 C1 C2 0.0(3) . . . . ?
N1 C1 C2 C3 -147.7(2) . . . . ?
N2 C1 C2 C3 34.9(3) . . . . ?
C1 C2 C3 C4 5.7(3) . . . . ?
C1 C2 C3 C17 179.77(16) . . . . ?
C2 C3 C4 C9 -40.6(3) . . . . ?
C17 C3 C4 C9 145.49(17) . . . . ?
C2 C3 C4 C5 137.22(19) . . . . ?
C17 C3 C4 C5 -36.7(2) . . . . ?
C9 C4 C5 C6 0.5(3) . . . . ?
C3 C4 C5 C6 -177.42(16) . . . . ?
C4 C5 C6 C7 -1.2(3) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C7 C8 C9 C4 -1.0(3) . . . . ?
C7 C8 C9 C10 179.44(17) . . . . ?
C5 C4 C9 C8 0.6(3) . . . . ?
C3 C4 C9 C8 178.42(16) . . . . ?
C5 C4 C9 C10 -179.90(15) . . . . ?
C3 C4 C9 C10 -2.0(3) . . . . ?
C1 N2 C10 C9 -63.2(2) . . . . ?
C11 N2 C10 C9 120.02(17) . . . . ?
C8 C9 C10 N2 -116.24(17) . . . . ?
C4 C9 C10 N2 64.2(2) . . . . ?
C1 N2 C11 C12 -177.24(18) . . . . ?
C10 N2 C11 C12 0.0(3) . . . . ?
C1 N2 C11 C16 1.24(18) . . . . ?
C10 N2 C11 C16 178.48(16) . . . . ?
N2 C11 C12 C13 -179.94(16) . . . . ?
C16 C11 C12 C13 1.8(2) . . . . ?
C11 C12 C13 F1 179.18(14) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
F1 C13 C14 F2 0.1(2) . . . . ?
C12 C13 C14 F2 179.97(15) . . . . ?
F1 C13 C14 C15 179.93(16) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
F2 C14 C15 C16 179.81(14) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C1 N1 C16 C15 -179.54(17) . . . . ?
C1 N1 C16 C11 1.67(19) . . . . ?
C14 C15 C16 N1 -177.59(17) . . . . ?
C14 C15 C16 C11 1.1(3) . . . . ?
N2 C11 C16 N1 -1.84(18) . . . . ?
C12 C11 C16 N1 176.81(15) . . . . ?
N2 C11 C16 C15 179.24(15) . . . . ?
C12 C11 C16 C15 -2.1(3) . . . . ?
C2 C3 C17 O1 -37.6(2) . . . . ?
C4 C3 C17 O1 136.85(18) . . . . ?
C2 C3 C17 C18 140.99(17) . . . . ?
C4 C3 C17 C18 -44.6(2) . . . . ?
O1 C17 C18 C23 170.11(17) . . . . ?
C3 C17 C18 C23 -8.5(3) . . . . ?
O1 C17 C18 C19 -8.1(3) . . . . ?
C3 C17 C18 C19 173.29(16) . . . . ?
C23 C18 C19 C20 3.2(3) . . . . ?
C17 C18 C19 C20 -178.44(17) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C24 O2 C21 C22 7.8(3) . . . . ?
C24 O2 C21 C20 -172.42(17) . . . . ?
C19 C20 C21 O2 176.48(16) . . . . ?
C19 C20 C21 C22 -3.8(3) . . . . ?
O2 C21 C22 C23 -176.48(16) . . . . ?
C20 C21 C22 C23 3.8(3) . . . . ?
C21 C22 C23 C18 -0.3(3) . . . . ?
C19 C18 C23 C22 -3.2(3) . . . . ?
C17 C18 C23 C22 178.59(16) . . . . ?
