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#$Date: 2022-08-23 01:52:10 +0300 (Tue, 23 Aug 2022) $
#$Revision: 277349 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/10/7711044.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_7711044
loop_
_publ_author_name
'Ouadoudi, Omar'
'Kaehler, Tanja'
'Çevik, Enes Görkem'
'Bolte, Michael'
'Stöger, Berthold'
'Virovets, Alexander'
'Lerner, Hans-Wolfram'
'Wagner, Matthias'
_publ_section_title
;
 Late-stage derivatization of a (B,O)2-doped perylene
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT02364D
_journal_year                    2022
_chemical_formula_moiety         'C18 H12 B2 Br2 O2 (C4 H8 O)0.33'
_chemical_formula_sum            'C19.33 H14.67 B2 Br2 O2.33'
_chemical_formula_weight         465.75
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-08-11 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   33.594(3)
_cell_length_b                   33.594(3)
_cell_length_c                   3.9159(5)
_cell_measurement_reflns_used    3567
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      3.64
_cell_volume                     3827.2(7)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            3567
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.587
_diffrn_reflns_theta_min         4.203
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    4.779
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_description       needle
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0508P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0978
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1260
_reflns_number_total             1584
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt02364d2.cif
_cod_data_source_block           wa2947_AV
_cod_original_cell_volume        3827.2(8)
_cod_database_code               7711044
_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   0.434
_shelx_estimated_absorpt_t_max   0.701
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
Br1 Br 0.34155(2) 0.48802(2) 0.15591(11) 0.02571(18) Uani 1 1 d . . . . .
O1 O 0.20837(11) 0.42816(11) 0.5016(8) 0.0205(7) Uani 1 1 d . . . . .
B1 B 0.18748(19) 0.38170(19) 0.4232(13) 0.0195(11) Uani 1 1 d . . . . .
C1 C 0.21621(16) 0.36460(16) 0.2367(10) 0.0184(9) Uani 1 1 d . . . . .
C2 C 0.19720(16) 0.31764(16) 0.1440(10) 0.0190(10) Uani 1 1 d . . . . .
C3 C 0.22462(16) 0.30341(16) -0.0185(11) 0.0198(10) Uani 1 1 d . . . . .
H3 H 0.212330 0.272040 -0.079329 0.024 Uiso 1 1 calc R U . . .
C4 C 0.27081(17) 0.33568(17) -0.0928(11) 0.0238(10) Uani 1 1 d . . . . .
H4 H 0.289206 0.325739 -0.207813 0.029 Uiso 1 1 calc R U . . .
C5 C 0.28988(17) 0.38106(18) -0.0034(11) 0.0231(10) Uani 1 1 d . . . . .
H5 H 0.321263 0.402130 -0.052086 0.028 Uiso 1 1 calc R U . . .
C6 C 0.26236(16) 0.39620(16) 0.1621(10) 0.0180(9) Uani 1 1 d . . . . .
C7 C 0.27956(15) 0.44393(16) 0.2622(11) 0.0200(10) Uani 1 1 d . . . . .
C8 C 0.25362(17) 0.45859(16) 0.4223(11) 0.0226(10) Uani 1 1 d . . . . .
C9 C 0.26756(18) 0.50613(17) 0.5334(12) 0.0246(10) Uani 1 1 d . . . . .
H9A H 0.298922 0.520955 0.624439 0.037 Uiso 1 1 calc R U . . .
H9B H 0.246495 0.505022 0.711184 0.037 Uiso 1 1 calc R U . . .
H9C H 0.266448 0.523748 0.337813 0.037 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'
B B 0.0013 0.0007 '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'
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
C8 O1 B1 122.3(4) . . ?
O1 B1 C1 117.9(4) . . ?
O1 B1 C2 119.7(4) . 16 ?
C1 B1 C2 122.5(4) . 16 ?
C6 C1 C2 120.0(4) . . ?
C6 C1 B1 118.7(4) . . ?
C2 C1 B1 121.3(4) . . ?
C3 C2 C1 119.5(4) . . ?
C3 C2 B1 124.2(4) . 16 ?
C1 C2 B1 116.2(4) . 16 ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 121.7(5) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 119.4(4) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 119.8(4) . . ?
C1 C6 C7 117.1(4) . . ?
C5 C6 C7 123.1(4) . . ?
C8 C7 C6 123.5(4) . . ?
C8 C7 Br1 118.2(4) . . ?
C6 C7 Br1 118.3(4) . . ?
C7 C8 O1 120.5(4) . . ?
C7 C8 C9 127.8(5) . . ?
O1 C8 C9 111.7(4) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
Br1 C7 1.902(5) . ?
O1 C8 1.378(6) . ?
O1 B1 1.388(6) . ?
B1 C1 1.532(7) . ?
B1 C2 1.562(7) 16 ?
C1 C6 1.404(6) . ?
C1 C2 1.422(7) . ?
C2 C3 1.387(6) . ?
C3 C4 1.409(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.416(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.460(7) . ?
C7 C8 1.350(7) . ?
C8 C9 1.487(7) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
C8 O1 B1 C1 -1.0(6) . . . . ?
C8 O1 B1 C2 179.6(4) . . . 16 ?
O1 B1 C1 C6 1.7(6) . . . . ?
C2 B1 C1 C6 -178.9(4) 16 . . . ?
O1 B1 C1 C2 -179.3(4) . . . . ?
C2 B1 C1 C2 0.1(7) 16 . . . ?
C6 C1 C2 C3 0.3(6) . . . . ?
B1 C1 C2 C3 -178.7(4) . . . . ?
C6 C1 C2 B1 178.9(4) . . . 16 ?
B1 C1 C2 B1 -0.1(6) . . . 16 ?
C1 C2 C3 C4 -0.6(6) . . . . ?
B1 C2 C3 C4 -179.1(4) 16 . . . ?
C2 C3 C4 C5 1.1(7) . . . . ?
C3 C4 C5 C6 -1.2(7) . . . . ?
C2 C1 C6 C5 -0.4(6) . . . . ?
B1 C1 C6 C5 178.6(4) . . . . ?
C2 C1 C6 C7 179.6(4) . . . . ?
B1 C1 C6 C7 -1.4(6) . . . . ?
C4 C5 C6 C1 0.9(6) . . . . ?
C4 C5 C6 C7 -179.1(4) . . . . ?
C1 C6 C7 C8 0.5(6) . . . . ?
C5 C6 C7 C8 -179.5(4) . . . . ?
C1 C6 C7 Br1 -178.6(3) . . . . ?
C5 C6 C7 Br1 1.4(6) . . . . ?
C6 C7 C8 O1 0.2(6) . . . . ?
Br1 C7 C8 O1 179.3(3) . . . . ?
C6 C7 C8 C9 -179.7(4) . . . . ?
Br1 C7 C8 C9 -0.6(6) . . . . ?
B1 O1 C8 C7 0.1(6) . . . . ?
B1 O1 C8 C9 180.0(4) . . . . ?
