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#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/48/4034838.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_4034838
loop_
_publ_author_name
'Ausekle, Elina'
'Ehlers, Peter'
'Villinger, Alexander'
'Langer, Peter'
_publ_section_title
;
 One-Pot Synthesis of Dibenzo[ b, d]oxepines via Olefinic C-F Bond
 Functionalization and Intramolecular Pd-Catalyzed C-H Arylation.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14195
_journal_page_last               14202
_journal_paper_doi               10.1021/acs.joc.8b02374
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C20 H15 Br O2'
_chemical_formula_sum            'C20 H15 Br O2'
_chemical_formula_weight         367.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 110.894(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.3320(7)
_cell_length_b                   5.8285(3)
_cell_length_c                   18.1478(9)
_cell_measurement_reflns_used    9948
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.15
_cell_measurement_theta_min      2.40
_cell_volume                     1613.91(14)
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0997
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            49340
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.555
_diffrn_reflns_theta_min         2.295
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    2.554
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         5398
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0435
_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)+(0.0193P)²+1.5737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0665
_refine_ls_wR_factor_ref         0.0742
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3959
_reflns_number_total             5398
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b02374_si_002.cif
_cod_data_source_block           av_1e18
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034838
_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   0.701
_shelx_estimated_absorpt_t_max   0.883
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.29764(9) 0.9026(2) 0.40246(8) 0.0161(3) Uani 1 1 d . .
O2 O 0.21812(9) 0.6611(2) 0.30113(8) 0.0152(3) Uani 1 1 d . .
Br1 Br 0.49666(2) 0.20721(4) 0.42404(2) 0.01795(6) Uani 1 1 d . .
C1 C 0.43095(12) 0.2684(3) 0.31606(11) 0.0127(4) Uani 1 1 d . .
C2 C 0.37979(12) 0.4665(3) 0.29494(11) 0.0122(4) Uani 1 1 d . .
C3 C 0.33621(13) 0.5050(3) 0.21396(11) 0.0139(4) Uani 1 1 d . .
H3 H 0.3017 0.6396 0.1973 0.017 Uiso 1 1 calc R U
C4 C 0.34213(13) 0.3521(4) 0.15780(11) 0.0161(4) Uani 1 1 d . .
H4 H 0.3125 0.3831 0.1033 0.019 Uiso 1 1 calc R U
C5 C 0.39164(13) 0.1524(4) 0.18111(12) 0.0161(4) Uani 1 1 d . .
H5 H 0.3944 0.0449 0.1427 0.019 Uiso 1 1 calc R U
C6 C 0.43693(13) 0.1111(3) 0.26088(12) 0.0143(4) Uani 1 1 d . .
H6 H 0.4716 -0.0233 0.2773 0.017 Uiso 1 1 calc R U
C7 C 0.37302(13) 0.6315(3) 0.35408(11) 0.0140(4) Uani 1 1 d . .
H7 H 0.4252 0.6705 0.3965 0.017 Uiso 1 1 calc R U
C8 C 0.29914(13) 0.7285(3) 0.35201(11) 0.0148(4) Uani 1 1 d . .
C9 C 0.24141(13) 0.8714(4) 0.44435(11) 0.0145(4) Uani 1 1 d . .
C10 C 0.24516(15) 0.6730(4) 0.48754(12) 0.0212(5) Uani 1 1 d . .
H10 H 0.2836 0.5515 0.4867 0.025 Uiso 1 1 calc R U
C11 C 0.19167(16) 0.6554(4) 0.53199(13) 0.0258(5) Uani 1 1 d . .
H11 H 0.1933 0.5203 0.5618 0.031 Uiso 1 1 calc R U
C12 C 0.13587(15) 0.8333(4) 0.53330(12) 0.0256(5) Uani 1 1 d . .
H12 H 0.0995 0.8200 0.5639 0.031 Uiso 1 1 calc R U
C13 C 0.13314(14) 1.0307(4) 0.48985(13) 0.0235(5) Uani 1 1 d . .
H13 H 0.0951 1.1530 0.4909 0.028 Uiso 1 1 calc R U
C14 C 0.18622(13) 1.0500(4) 0.44451(12) 0.0184(4) Uani 1 1 d . .
H14 H 0.1843 1.1843 0.4142 0.022 Uiso 1 1 calc R U
C15 C 0.16351(13) 0.8270(3) 0.25240(11) 0.0140(4) Uani 1 1 d . .
C16 C 0.07558(13) 0.7677(4) 0.21891(12) 0.0192(4) Uani 1 1 d . .
H16 H 0.0553 0.6248 0.2309 0.023 Uiso 1 1 calc R U
C17 C 0.01801(14) 0.9205(4) 0.16775(13) 0.0256(5) Uani 1 1 d . .
H17 H -0.0422 0.8814 0.1442 0.031 Uiso 1 1 calc R U
C18 C 0.04732(15) 1.1303(4) 0.15049(13) 0.0238(5) Uani 1 1 d . .
H18 H 0.0074 1.2345 0.1154 0.029 Uiso 1 1 calc R U
C19 C 0.13503(14) 1.1858(4) 0.18479(12) 0.0202(4) Uani 1 1 d . .
H19 H 0.1552 1.3294 0.1732 0.024 Uiso 1 1 calc R U
C20 C 0.19402(13) 1.0349(4) 0.23584(12) 0.0157(4) Uani 1 1 d . .
H20 H 0.2543 1.0737 0.2590 0.019 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C8 O1 C9 116.00(15)
C8 O2 C15 118.17(15)
C6 C1 C2 122.52(17)
C6 C1 Br1 117.46(15)
C2 C1 Br1 120.02(14)
C1 C2 C3 116.72(18)
C1 C2 C7 122.16(17)
C3 C2 C7 121.11(18)
C4 C3 C2 121.75(19)
C4 C3 H3 119.1
C2 C3 H3 119.1
C3 C4 C5 119.98(18)
C3 C4 H4 120.0
C5 C4 H4 120.0
C6 C5 C4 119.70(18)
C6 C5 H5 120.1
C4 C5 H5 120.1
C1 C6 C5 119.28(18)
C1 C6 H6 120.4
C5 C6 H6 120.4
C8 C7 C2 124.29(18)
C8 C7 H7 117.9
C2 C7 H7 117.9
C7 C8 O1 122.06(18)
C7 C8 O2 123.21(18)
O1 C8 O2 114.71(17)
C14 C9 C10 121.8(2)
C14 C9 O1 117.40(18)
C10 C9 O1 120.74(19)
C9 C10 C11 118.7(2)
C9 C10 H10 120.6
C11 C10 H10 120.6
C12 C11 C10 120.5(2)
C12 C11 H11 119.7
C10 C11 H11 119.7
C11 C12 C13 119.9(2)
C11 C12 H12 120.0
C13 C12 H12 120.0
C12 C13 C14 120.1(2)
C12 C13 H13 120.0
C14 C13 H13 120.0
C9 C14 C13 119.0(2)
C9 C14 H14 120.5
C13 C14 H14 120.5
C20 C15 C16 121.27(19)
C20 C15 O2 123.09(18)
C16 C15 O2 115.60(18)
C17 C16 C15 118.9(2)
C17 C16 H16 120.6
C15 C16 H16 120.6
C16 C17 C18 120.7(2)
C16 C17 H17 119.6
C18 C17 H17 119.6
C19 C18 C17 119.3(2)
C19 C18 H18 120.3
C17 C18 H18 120.3
C18 C19 C20 120.9(2)
C18 C19 H19 119.5
C20 C19 H19 119.5
C15 C20 C19 118.84(19)
C15 C20 H20 120.6
C19 C20 H20 120.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.372(2)
O1 C9 1.397(2)
O2 C8 1.373(2)
O2 C15 1.396(2)
Br1 C1 1.9023(18)
C1 C6 1.386(3)
C1 C2 1.397(3)
C2 C3 1.404(3)
C2 C7 1.474(3)
C3 C4 1.383(3)
C3 H3 0.9500
C4 C5 1.394(3)
C4 H4 0.9500
C5 C6 1.392(3)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.321(3)
C7 H7 0.9500
C9 C14 1.378(3)
C9 C10 1.386(3)
C10 C11 1.388(3)
C10 H10 0.9500
C11 C12 1.387(3)
C11 H11 0.9500
C12 C13 1.387(3)
C12 H12 0.9500
C13 C14 1.396(3)
C13 H13 0.9500
C14 H14 0.9500
C15 C20 1.384(3)
C15 C16 1.389(3)
C16 C17 1.384(3)
C16 H16 0.9500
C17 C18 1.389(4)
C17 H17 0.9500
C18 C19 1.381(3)
C18 H18 0.9500
C19 C20 1.387(3)
C19 H19 0.9500
C20 H20 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
C6 C1 C2 C3 -2.2(3)
Br1 C1 C2 C3 177.31(14)
C6 C1 C2 C7 179.28(19)
Br1 C1 C2 C7 -1.2(3)
C1 C2 C3 C4 1.3(3)
C7 C2 C3 C4 179.84(19)
C2 C3 C4 C5 0.7(3)
C3 C4 C5 C6 -1.8(3)
C2 C1 C6 C5 1.1(3)
Br1 C1 C6 C5 -178.40(15)
C4 C5 C6 C1 1.0(3)
C1 C2 C7 C8 -137.2(2)
C3 C2 C7 C8 44.3(3)
C2 C7 C8 O1 -171.46(18)
C2 C7 C8 O2 10.1(3)
C9 O1 C8 C7 -127.8(2)
C9 O1 C8 O2 50.7(2)
C15 O2 C8 C7 -125.3(2)
C15 O2 C8 O1 56.2(2)
C8 O1 C9 C14 -131.19(19)
C8 O1 C9 C10 52.4(2)
C14 C9 C10 C11 0.0(3)
O1 C9 C10 C11 176.22(18)
C9 C10 C11 C12 -0.2(3)
C10 C11 C12 C13 0.1(3)
C11 C12 C13 C14 0.3(3)
C10 C9 C14 C13 0.4(3)
O1 C9 C14 C13 -175.94(18)
C12 C13 C14 C9 -0.5(3)
C8 O2 C15 C20 19.2(3)
C8 O2 C15 C16 -162.77(17)
C20 C15 C16 C17 0.3(3)
O2 C15 C16 C17 -177.78(18)
C15 C16 C17 C18 -0.5(3)
C16 C17 C18 C19 0.2(3)
C17 C18 C19 C20 0.2(3)
C16 C15 C20 C19 0.1(3)
O2 C15 C20 C19 178.03(18)
C18 C19 C20 C15 -0.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 138966515
