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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/7/15/89/7158985.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_7158985
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_absolute_configuration unk
_chemical_formula_moiety         'C24 H16 F2 N2 O'
_chemical_formula_sum            'C24 H16 F2 N2 O'
_chemical_formula_weight         386.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 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                90
_cell_angle_beta                 124.943(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.3551(19)
_cell_length_b                   6.4154(5)
_cell_length_c                   14.5468(12)
_cell_measurement_reflns_used    9633
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.69
_cell_measurement_theta_min      2.81
_cell_volume                     1786.7(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      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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  0.0573
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            35432
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         2.806
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         5188
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0395
_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)+(0.0511P)²+0.5869P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0998
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4600
_reflns_number_total             5188
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01320g2.cif
_cod_data_source_block           is_rfmydc501
_cod_original_cell_volume        1786.6(3)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7158985
_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   0.950
_shelx_estimated_absorpt_t_max   0.998
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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 1.02015(7) 0.4559(3) 0.87391(14) 0.0469(4) Uani 1 1 d . . . . .
F2 F 0.97865(7) 0.0820(2) 0.88590(13) 0.0396(3) Uani 1 1 d . . . . .
O1 O 0.55646(9) 0.9212(3) 0.65053(16) 0.0408(4) Uani 1 1 d . . . . .
N1 N 0.79039(9) 0.7164(3) 0.74724(15) 0.0265(4) Uani 1 1 d . . . . .
N2 N 0.75685(8) 0.3994(3) 0.76588(13) 0.0217(3) Uani 1 1 d . . . . .
C1 C 0.73914(10) 0.6042(3) 0.73669(16) 0.0233(4) Uani 1 1 d . . . . .
C2 C 0.67073(10) 0.6852(3) 0.69627(17) 0.0243(4) Uani 1 1 d . . . . .
H2 H 0.6539 0.7960 0.6436 0.029 Uiso 1 1 calc R U . . .
C3 C 0.62827(10) 0.6200(3) 0.72547(16) 0.0225(4) Uani 1 1 d . . . . .
C4 C 0.64403(9) 0.4601(3) 0.80973(15) 0.0218(4) Uani 1 1 d . . . . .
C5 C 0.61822(10) 0.4874(4) 0.87558(16) 0.0268(4) Uani 1 1 d . . . . .
H5 H 0.5924 0.6095 0.8664 0.032 Uiso 1 1 calc R U . . .
C6 C 0.62973(11) 0.3397(4) 0.95350(17) 0.0301(5) Uani 1 1 d . . . . .
H6 H 0.6113 0.3599 0.9965 0.036 Uiso 1 1 calc R U . . .
C7 C 0.66804(11) 0.1622(4) 0.96919(18) 0.0301(5) Uani 1 1 d . . . . .
H7 H 0.6756 0.0601 1.0224 0.036 Uiso 1 1 calc R U . . .
C8 C 0.69548(10) 0.1340(3) 0.90670(17) 0.0266(4) Uani 1 1 d . . . . .
H8 H 0.7227 0.0137 0.9187 0.032 Uiso 1 1 calc R U . . .
C9 C 0.68348(9) 0.2799(3) 0.82691(16) 0.0206(4) Uani 1 1 d . . . . .
C10 C 0.70895(10) 0.2374(3) 0.75429(17) 0.0230(4) Uani 1 1 d . . . . .
H10A H 0.7331 0.1009 0.7752 0.028 Uiso 1 1 calc R U . . .
H10B H 0.6684 0.2293 0.6749 0.028 Uiso 1 1 calc R U . . .
C11 C 0.82465(10) 0.3764(3) 0.79773(16) 0.0225(4) Uani 1 1 d . . . . .
C12 C 0.86760(11) 0.2022(3) 0.83014(17) 0.0262(4) Uani 1 1 d . . . . .
H12 H 0.8529 0.0668 0.8345 0.031 Uiso 1 1 calc R U . . .
C13 C 0.93300(11) 0.2411(4) 0.85529(19) 0.0292(4) Uani 1 1 d . . . . .
C14 C 0.95485(11) 0.4382(4) 0.8478(2) 0.0326(5) Uani 1 1 d . . . . .
C15 C 0.91202(12) 0.6083(4) 0.81273(19) 0.0317(4) Uani 1 1 d . . . . .
H15 H 0.9271 0.7418 0.8064 0.038 Uiso 1 1 calc R U . . .
C16 C 0.84473(11) 0.5765(3) 0.78650(17) 0.0258(4) Uani 1 1 d . . . . .
C17 C 0.55927(11) 0.7351(3) 0.66826(17) 0.0261(4) Uani 1 1 d . . . . .
C18 C 0.49523(10) 0.6130(4) 0.63109(16) 0.0259(4) Uani 1 1 d . . . . .
C19 C 0.43842(12) 0.7157(4) 0.61965(19) 0.0340(5) Uani 1 1 d . . . . .
H19 H 0.4417 0.8595 0.6378 0.041 Uiso 1 1 calc R U . . .
C20 C 0.37748(12) 0.6067(5) 0.58183(19) 0.0384(6) Uani 1 1 d . . . . .
H20 H 0.3397 0.6762 0.5763 0.046 Uiso 1 1 calc R U . . .
C21 C 0.37053(11) 0.3985(5) 0.55188(18) 0.0363(5) Uani 1 1 d . . . . .
C22 C 0.42685(11) 0.2980(4) 0.56210(19) 0.0332(5) Uani 1 1 d . . . . .
H22 H 0.4226 0.1561 0.5404 0.040 Uiso 1 1 calc R U . . .
C23 C 0.48922(10) 0.4036(4) 0.60381(17) 0.0273(4) Uani 1 1 d . . . . .
H23 H 0.5279 0.3317 0.6136 0.033 Uiso 1 1 calc R U . . .
C24 C 0.30373(13) 0.2825(6) 0.5102(2) 0.0508(8) Uani 1 1 d . . . . .
H24A H 0.2646 0.3542 0.4446 0.076 Uiso 1 1 calc R U . . .
H24B H 0.2960 0.2776 0.5696 0.076 Uiso 1 1 calc R U . . .
H24C H 0.3073 0.1402 0.4894 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'
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
C1 N1 C16 104.44(17) . . ?
C1 N2 C11 106.93(16) . . ?
C1 N2 C10 124.76(16) . . ?
C11 N2 C10 128.10(17) . . ?
N1 C1 N2 113.07(17) . . ?
N1 C1 C2 124.40(19) . . ?
N2 C1 C2 122.51(18) . . ?
C3 C2 C1 126.90(19) . . ?
C3 C2 H2 116.6 . . ?
C1 C2 H2 116.6 . . ?
C2 C3 C4 126.78(17) . . ?
C2 C3 C17 114.69(18) . . ?
C4 C3 C17 118.44(17) . . ?
C5 C4 C9 118.29(17) . . ?
C5 C4 C3 118.67(18) . . ?
C9 C4 C3 123.04(16) . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 120.24(19) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C8 119.7(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C4 119.98(17) . . ?
C8 C9 C10 119.54(18) . . ?
C4 C9 C10 120.37(17) . . ?
N2 C10 C9 111.94(16) . . ?
N2 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
N2 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N2 C11 C12 131.73(19) . . ?
N2 C11 C16 104.95(18) . . ?
C12 C11 C16 123.26(17) . . ?
C13 C12 C11 114.8(2) . . ?
C13 C12 H12 122.6 . . ?
C11 C12 H12 122.6 . . ?
F2 C13 C12 119.8(2) . . ?
F2 C13 C14 117.15(18) . . ?
C12 C13 C14 123.1(2) . . ?
F1 C14 C15 120.3(2) . . ?
F1 C14 C13 117.5(2) . . ?
C15 C14 C13 122.20(19) . . ?
C14 C15 C16 116.8(2) . . ?
C14 C15 H15 121.6 . . ?
C16 C15 H15 121.6 . . ?
N1 C16 C15 129.6(2) . . ?
N1 C16 C11 110.60(17) . . ?
C15 C16 C11 119.8(2) . . ?
O1 C17 C18 121.27(19) . . ?
O1 C17 C3 120.4(2) . . ?
C18 C17 C3 118.27(18) . . ?
C23 C18 C19 119.2(2) . . ?
C23 C18 C17 122.04(19) . . ?
C19 C18 C17 118.7(2) . . ?
C20 C19 C18 119.7(2) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C21 C20 C19 121.3(2) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C22 118.6(2) . . ?
C20 C21 C24 120.7(3) . . ?
C22 C21 C24 120.7(3) . . ?
C23 C22 C21 120.6(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C18 C23 C22 120.4(2) . . ?
C18 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 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 C14 1.349(2) . ?
F2 C13 1.354(3) . ?
O1 C17 1.215(3) . ?
N1 C1 1.328(3) . ?
N1 C16 1.383(3) . ?
N2 C1 1.370(3) . ?
N2 C11 1.380(2) . ?
N2 C10 1.464(2) . ?
C1 C2 1.447(3) . ?
C2 C3 1.350(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.474(3) . ?
C3 C17 1.516(3) . ?
C4 C5 1.405(3) . ?
C4 C9 1.409(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.505(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.392(3) . ?
C11 C16 1.408(3) . ?
C12 C13 1.375(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C14 C15 1.367(3) . ?
C15 C16 1.404(3) . ?
C15 H15 0.9500 . ?
C17 C18 1.489(3) . ?
C18 C23 1.385(3) . ?
C18 C19 1.404(3) . ?
C19 C20 1.386(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.394(3) . ?
C21 C24 1.507(3) . ?
C22 C23 1.392(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 -0.5(2) . . . . ?
C16 N1 C1 C2 -179.16(18) . . . . ?
C11 N2 C1 N1 0.0(2) . . . . ?
C10 N2 C1 N1 -175.09(17) . . . . ?
C11 N2 C1 C2 178.61(18) . . . . ?
C10 N2 C1 C2 3.6(3) . . . . ?
N1 C1 C2 C3 -149.5(2) . . . . ?
N2 C1 C2 C3 32.0(3) . . . . ?
C1 C2 C3 C4 3.7(3) . . . . ?
C1 C2 C3 C17 -179.7(2) . . . . ?
C2 C3 C4 C5 144.0(2) . . . . ?
C17 C3 C4 C5 -32.4(3) . . . . ?
C2 C3 C4 C9 -36.4(3) . . . . ?
C17 C3 C4 C9 147.14(18) . . . . ?
C9 C4 C5 C6 -1.4(3) . . . . ?
C3 C4 C5 C6 178.15(18) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C5 C6 C7 C8 0.5(3) . . . . ?
C6 C7 C8 C9 -1.4(3) . . . . ?
C7 C8 C9 C4 0.9(3) . . . . ?
C7 C8 C9 C10 -175.22(18) . . . . ?
C5 C4 C9 C8 0.5(3) . . . . ?
C3 C4 C9 C8 -179.04(18) . . . . ?
C5 C4 C9 C10 176.62(18) . . . . ?
C3 C4 C9 C10 -2.9(3) . . . . ?
C1 N2 C10 C9 -63.5(2) . . . . ?
C11 N2 C10 C9 122.5(2) . . . . ?
C8 C9 C10 N2 -121.60(19) . . . . ?
C4 C9 C10 N2 62.3(2) . . . . ?
C1 N2 C11 C12 -176.7(2) . . . . ?
C10 N2 C11 C12 -1.8(3) . . . . ?
C1 N2 C11 C16 0.6(2) . . . . ?
C10 N2 C11 C16 175.42(18) . . . . ?
N2 C11 C12 C13 179.4(2) . . . . ?
C16 C11 C12 C13 2.6(3) . . . . ?
C11 C12 C13 F2 -178.85(18) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
F2 C13 C14 F1 -1.4(3) . . . . ?
C12 C13 C14 F1 -179.5(2) . . . . ?
F2 C13 C14 C15 176.9(2) . . . . ?
C12 C13 C14 C15 -1.2(4) . . . . ?
F1 C14 C15 C16 179.58(19) . . . . ?
C13 C14 C15 C16 1.4(3) . . . . ?
C1 N1 C16 C15 179.9(2) . . . . ?
C1 N1 C16 C11 0.9(2) . . . . ?
C14 C15 C16 N1 -178.5(2) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?
N2 C11 C16 N1 -1.0(2) . . . . ?
C12 C11 C16 N1 176.61(18) . . . . ?
N2 C11 C16 C15 179.96(18) . . . . ?
C12 C11 C16 C15 -2.5(3) . . . . ?
C2 C3 C17 O1 -37.4(3) . . . . ?
C4 C3 C17 O1 139.5(2) . . . . ?
C2 C3 C17 C18 140.5(2) . . . . ?
C4 C3 C17 C18 -42.7(3) . . . . ?
O1 C17 C18 C23 150.8(2) . . . . ?
C3 C17 C18 C23 -27.0(3) . . . . ?
O1 C17 C18 C19 -26.9(3) . . . . ?
C3 C17 C18 C19 155.30(19) . . . . ?
C23 C18 C19 C20 0.3(3) . . . . ?
C17 C18 C19 C20 178.0(2) . . . . ?
C18 C19 C20 C21 -1.8(3) . . . . ?
C19 C20 C21 C22 1.0(3) . . . . ?
C19 C20 C21 C24 -179.6(2) . . . . ?
C20 C21 C22 C23 1.4(3) . . . . ?
C24 C21 C22 C23 -178.0(2) . . . . ?
C19 C18 C23 C22 2.1(3) . . . . ?
C17 C18 C23 C22 -175.61(19) . . . . ?
C21 C22 C23 C18 -2.9(3) . . . . ?
