#------------------------------------------------------------------------------
#$Date: 2025-03-04 21:02:08 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298096 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/31/1573188.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_1573188
loop_
_publ_author_name
'Lückert, Paula L'
'Gilmer, Jannik'
'Virovets, Alexander'
'Lerner, Hans-Wolfram'
'Wagner, Matthias'
_publ_section_title
;
 Donor-free 9,10-dihydro-9,10-dialuminaanthracenes.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              147
_journal_page_last               155
_journal_paper_doi               10.1039/d4sc06940d
_journal_volume                  16
_journal_year                    2024
_chemical_formula_moiety         'C22 H18 Al2 Br2 N2, C6 H6'
_chemical_formula_sum            'C28 H24 Al2 Br2 N2'
_chemical_formula_weight         602.27
_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-2019/3
_audit_update_record
;
2024-09-22 deposited with the CCDC.	2024-11-18 downloaded from the CCDC.
;
_cell_angle_alpha                110.307(7)
_cell_angle_beta                 104.486(8)
_cell_angle_gamma                104.444(6)
_cell_formula_units_Z            1
_cell_length_a                   9.0374(7)
_cell_length_b                   9.3213(6)
_cell_length_c                   9.7274(9)
_cell_measurement_reflns_used    3581
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.8900
_cell_measurement_theta_min      3.8320
_cell_volume                     691.18(12)
_computing_cell_refinement       'CrysAlisPro 1.171.42.43a (Rigaku OD, 2022)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'CrysAlisPro 1.171.42.43a (Rigaku OD, 2022)'
_computing_publication_material  'IUCr PublCIF online service'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'image plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE image plate (34 cm diameter)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '2-circle goniometer'
_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  0.0534
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12141
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.035
_diffrn_reflns_theta_min         3.592
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    3.014
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.43a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       block
_exptl_crystal_F_000             302
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     92
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0366
_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)+(0.0176P)²+0.3795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0678
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2310
_reflns_number_total             2719
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc06940d3.cif
_cod_data_source_block           2py2_wa3239_av
_cod_depositor_comments
'Adding full bibliography for 1573178--1573190.cif.'
_cod_original_cell_volume        691.18(10)
_cod_database_code               1573188
_shelx_shelxl_version_number     2019/3
_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   0.475
_shelx_estimated_absorpt_t_max   0.508
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
Al1 Al 0.49265(9) 0.66661(9) 0.64586(9) 0.01699(18) Uani 1 1 d . . . . .
Br1 Br 0.66833(4) 0.88617(4) 0.88880(4) 0.03409(11) Uani 1 1 d . . . . .
C1 C 0.4457(3) 0.4524(3) 0.6529(3) 0.0171(5) Uani 1 1 d . . . . .
C2 C 0.4459(3) 0.3148(3) 0.5289(3) 0.0181(6) Uani 1 1 d . . . . .
C3 C 0.4032(3) 0.1625(3) 0.5356(4) 0.0260(6) Uani 1 1 d . . . . .
H3 H 0.402758 0.069569 0.453765 0.031 Uiso 1 1 calc R U . . .
C4 C 0.3617(4) 0.1434(4) 0.6572(4) 0.0307(7) Uani 1 1 d . . . . .
H4 H 0.333696 0.038637 0.658204 0.037 Uiso 1 1 calc R U . . .
C5 C 0.3608(3) 0.2763(4) 0.7775(4) 0.0296(7) Uani 1 1 d . . . . .
H5 H 0.332304 0.263451 0.861251 0.036 Uiso 1 1 calc R U . . .
C6 C 0.4020(3) 0.4288(3) 0.7749(3) 0.0231(6) Uani 1 1 d . . . . .
H6 H 0.400723 0.519795 0.857573 0.028 Uiso 1 1 calc R U . . .
N1 N 0.2838(3) 0.7065(2) 0.6155(3) 0.0180(5) Uani 1 1 d . . . . .
C12 C 0.1860(3) 0.6669(4) 0.4676(3) 0.0271(6) Uani 1 1 d . . . . .
H12 H 0.221349 0.623508 0.383384 0.033 Uiso 1 1 calc R U . . .
C13 C 0.0378(3) 0.6864(4) 0.4337(4) 0.0333(7) Uani 1 1 d . . . . .
H13 H -0.027782 0.657423 0.328091 0.040 Uiso 1 1 calc R U . . .
C14 C -0.0148(3) 0.7487(4) 0.5555(4) 0.0319(7) Uani 1 1 d . . . . .
H14 H -0.116315 0.764886 0.535291 0.038 Uiso 1 1 calc R U . . .
C15 C 0.0826(3) 0.7871(4) 0.7064(4) 0.0296(7) Uani 1 1 d . . . . .
H15 H 0.048273 0.828748 0.791834 0.035 Uiso 1 1 calc R U . . .
C16 C 0.2302(3) 0.7646(3) 0.7330(3) 0.0240(6) Uani 1 1 d . . . . .
H16 H 0.296346 0.790846 0.837585 0.029 Uiso 1 1 calc R U . . .
C21 C 0.127(3) 0.434(4) 0.036(3) 0.047(5) Uani 0.53 1 d D U P A 1
H21 H 0.210015 0.390988 0.060659 0.056 Uiso 0.53 1 calc R U P A 1
C22 C 0.158(2) 0.597(3) 0.068(2) 0.040(6) Uani 0.53 1 d D U P A 1
H22 H 0.269600 0.670781 0.116060 0.048 Uiso 0.53 1 calc R U P A 1
C23 C 0.038(4) 0.660(2) 0.036(4) 0.051(7) Uani 0.53 1 d D U P A 1
H23 H 0.071774 0.774977 0.065125 0.061 Uiso 0.53 1 calc R U P A 1
C21B C 0.018(4) 0.354(3) -0.010(5) 0.052(7) Uani 0.47 1 d D U P B 2
H21B H 0.036072 0.257614 -0.012032 0.062 Uiso 0.47 1 calc R U P B 2
C22B C 0.149(2) 0.500(4) 0.049(3) 0.035(5) Uani 0.47 1 d D U P B 2
H22B H 0.255797 0.497271 0.080176 0.042 Uiso 0.47 1 calc R U P B 2
C23B C 0.139(4) 0.649(3) 0.067(3) 0.042(6) Uani 0.47 1 d D U P B 2
H23B H 0.233582 0.747750 0.115835 0.050 Uiso 0.47 1 calc R U P B 2
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'
Al Al 0.0645 0.0514 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Al1 C1 117.40(11) 2_666 . ?
C2 Al1 N1 104.50(10) 2_666 . ?
C1 Al1 N1 106.03(10) . . ?
C2 Al1 Br1 112.07(8) 2_666 . ?
C1 Al1 Br1 112.84(8) . . ?
N1 Al1 Br1 102.23(7) . . ?
C6 C1 C2 118.6(2) . . ?
C6 C1 Al1 121.1(2) . . ?
C2 C1 Al1 120.21(19) . . ?
C3 C2 C1 117.9(2) . . ?
C3 C2 Al1 119.9(2) . 2_666 ?
C1 C2 Al1 122.24(19) . 2_666 ?
C4 C3 C2 122.2(3) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 121.8(3) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
C16 N1 C12 117.8(2) . . ?
C16 N1 Al1 123.89(18) . . ?
C12 N1 Al1 118.29(18) . . ?
N1 C12 C13 122.8(3) . . ?
N1 C12 H12 118.6 . . ?
C13 C12 H12 118.6 . . ?
C12 C13 C14 118.9(3) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 118.8(3) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 119.5(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
N1 C16 C15 122.1(3) . . ?
N1 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
C23 C21 C22 112.0(16) 2_565 . ?
C23 C21 H21 124.0 2_565 . ?
C22 C21 H21 124.0 . . ?
C23 C22 C21 124.3(16) . . ?
C23 C22 H22 117.8 . . ?
C21 C22 H22 117.8 . . ?
C21 C23 C22 123.7(18) 2_565 . ?
C21 C23 H23 118.2 2_565 . ?
C22 C23 H23 118.2 . . ?
C22B C21B H21B 120.6 . . ?
C23B C21B H21B 120.6 2_565 . ?
C23B C22B C21B 126.2(14) . . ?
C23B C22B H22B 116.9 . . ?
C21B C22B H22B 116.9 . . ?
C22B C23B H23B 122.5 . . ?
C21B C23B H23B 122.5 2_565 . ?
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
Al1 C2 1.964(3) 2_666 ?
Al1 C1 1.964(3) . ?
Al1 N1 1.984(2) . ?
Al1 Br1 2.3322(9) . ?
C1 C6 1.408(4) . ?
C1 C2 1.424(4) . ?
C2 C3 1.404(4) . ?
C3 C4 1.381(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N1 C16 1.347(3) . ?
N1 C12 1.348(3) . ?
C12 C13 1.371(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C23 1.373(10) 2_565 ?
C21 C22 1.382(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.376(9) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C21B C22B 1.375(10) . ?
C21B C23B 1.378(10) 2_565 ?
C21B H21B 0.9500 . ?
C22B C23B 1.364(11) . ?
C22B H22B 0.9500 . ?
C23B H23B 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C16 H16 Br1 0.95 3.12 3.582(3) 112.0 . yes
C16 H16 Br1 0.95 3.13 3.672(3) 118.1 2_677 yes
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
C6 C1 C2 C3 -0.4(4) . . . . ?
Al1 C1 C2 C3 -176.75(19) . . . . ?
C6 C1 C2 Al1 -179.19(19) . . . 2_666 ?
Al1 C1 C2 Al1 4.4(3) . . . 2_666 ?
C1 C2 C3 C4 0.0(4) . . . . ?
Al1 C2 C3 C4 178.9(2) 2_666 . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
Al1 C1 C6 C5 176.9(2) . . . . ?
C16 N1 C12 C13 1.4(4) . . . . ?
Al1 N1 C12 C13 178.6(2) . . . . ?
N1 C12 C13 C14 -0.2(5) . . . . ?
C12 C13 C14 C15 -0.9(5) . . . . ?
C13 C14 C15 C16 0.8(4) . . . . ?
C12 N1 C16 C15 -1.4(4) . . . . ?
Al1 N1 C16 C15 -178.5(2) . . . . ?
C14 C15 C16 N1 0.3(4) . . . . ?
C23 C21 C22 C23 1(5) 2_565 . . . ?
C21 C22 C23 C21 -2(5) . . . 2_565 ?
C23B C21B C22B C23B 5(6) 2_565 . . . ?
C21B C22B C23B C21B -4(6) . . . 2_565 ?
