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#$Date: 2020-07-22 04:03:49 +0300 (Wed, 22 Jul 2020) $
#$Revision: 254450 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/86/1558642.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_1558642
loop_
_publ_author_name
'Rekhroukh, Feriel'
'Chen, Wenyi'
'Brown, Ryan'
'White, Andrew J. P.'
'Crimmin, Mark Richard'
_publ_section_title
;
 Palladium-Catalysed C--F Alumination of Fluorobenzenes: Mechanistic
 Diversity and Origin of Selectivity
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC01915A
_journal_year                    2020
_chemical_formula_moiety         'C35 H45 Al F2 N2'
_chemical_formula_sum            'C35 H45 Al F2 N2'
_chemical_formula_weight         558.71
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-03-24 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6410(8)
_cell_length_b                   21.2084(7)
_cell_length_c                   8.9762(4)
_cell_measurement_reflns_used    1898
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.3720
_cell_measurement_theta_min      3.1150
_cell_volume                     3168.0(2)
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_collection       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0382
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.817
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.817
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6736
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.156
_diffrn_reflns_theta_min         2.630
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_description       'platy needles'
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.614
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.111
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3254
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0482
_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)+(0.0490P)²+1.1054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1179
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2577
_reflns_number_total             3254
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc01915a2.cif
_cod_data_source_block           2c
_cod_original_cell_volume        3167.9(2)
_cod_database_code               1558642
_shelx_shelxl_version_number     2017/1
_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. 
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Al1 Al 0.15385(4) 0.750000 0.56145(7) 0.02329(18) Uani 1 2 d S T P . .
F1 F 0.22510(8) 0.750000 0.43052(15) 0.0346(3) Uani 1 2 d S T P . .
N1 N 0.17797(8) 0.68334(6) 0.69286(14) 0.0245(3) Uani 1 1 d . . . . .
C1 C 0.23667(10) 0.69094(7) 0.79362(17) 0.0250(3) Uani 1 1 d . . . . .
C2 C 0.26784(14) 0.750000 0.8313(3) 0.0272(5) Uani 1 2 d S T P . .
H2A H 0.315645 0.750000 0.889187 0.033 Uiso 1 2 calc R U P . .
C3 C 0.26985(11) 0.63449(8) 0.8744(2) 0.0360(4) Uani 1 1 d . . . . .
H3A H 0.228263 0.616700 0.939237 0.054 Uiso 1 1 calc R U . . .
H3B H 0.316112 0.647340 0.934720 0.054 Uiso 1 1 calc R U . . .
H3C H 0.286800 0.602655 0.801731 0.054 Uiso 1 1 calc R U . . .
C4 C 0.14076(10) 0.62165(7) 0.67828(19) 0.0304(4) Uani 1 1 d . . . . .
C5 C 0.07355(11) 0.60773(9) 0.7659(2) 0.0412(5) Uani 1 1 d D . . . .
C6 C 0.03709(13) 0.54899(10) 0.7457(3) 0.0565(6) Uani 1 1 d . . . . .
H6A H -0.008564 0.538302 0.804027 0.068 Uiso 1 1 calc R U . . .
C7 C 0.06559(15) 0.50656(10) 0.6440(3) 0.0646(7) Uani 1 1 d . . . . .
H7A H 0.039727 0.466931 0.632279 0.078 Uiso 1 1 calc R U . . .
C8 C 0.13131(14) 0.52102(9) 0.5589(3) 0.0577(7) Uani 1 1 d . . . . .
H8A H 0.150421 0.491123 0.488472 0.069 Uiso 1 1 calc R U . . .
C9 C 0.17089(11) 0.57877(8) 0.5733(2) 0.0379(4) Uani 1 1 d . . . . .
C10 C 0.0434(2) 0.6475(2) 0.8839(4) 0.0465(10) Uani 0.715(6) 1 d D U P A 1
H10A H 0.075658 0.687297 0.884859 0.056 Uiso 0.715(6) 1 calc R U P A 1
C11 C -0.0453(3) 0.6650(3) 0.8515(6) 0.0587(13) Uani 0.715(6) 1 d D U P A 1
H11A H -0.065784 0.692000 0.931496 0.088 Uiso 0.715(6) 1 calc R U P A 1
H11B H -0.048587 0.687562 0.756397 0.088 Uiso 0.715(6) 1 calc R U P A 1
H11C H -0.077649 0.626442 0.846001 0.088 Uiso 0.715(6) 1 calc R U P A 1
C12 C 0.0504(2) 0.6167(2) 1.0367(3) 0.0788(16) Uani 0.715(6) 1 d D . P A 1
H12A H 0.029295 0.645316 1.112876 0.118 Uiso 0.715(6) 1 calc R U P A 1
H12B H 0.019561 0.577315 1.037735 0.118 Uiso 0.715(6) 1 calc R U P A 1
H12C H 0.107033 0.607496 1.057825 0.118 Uiso 0.715(6) 1 calc R U P A 1
C10' C 0.0326(6) 0.6682(5) 0.8661(11) 0.041(3) Uiso 0.285(6) 1 d D U P A 2
H10B H 0.046060 0.708522 0.814192 0.049 Uiso 0.285(6) 1 calc R U P A 2
C11' C -0.0590(7) 0.6661(9) 0.8885(16) 0.064(4) Uiso 0.285(6) 1 d D U P A 2
H11D H -0.085613 0.664188 0.791193 0.096 Uiso 0.285(6) 1 calc R U P A 2
H11E H -0.073283 0.628752 0.946929 0.096 Uiso 0.285(6) 1 calc R U P A 2
H11F H -0.076406 0.704134 0.941483 0.096 Uiso 0.285(6) 1 calc R U P A 2
C12' C 0.0690(5) 0.6712(4) 1.0258(9) 0.059(3) Uiso 0.285(6) 1 d D . P A 2
H12D H 0.127732 0.672581 1.019225 0.088 Uiso 0.285(6) 1 calc R U P A 2
H12E H 0.049487 0.709095 1.076680 0.088 Uiso 0.285(6) 1 calc R U P A 2
H12F H 0.052610 0.633713 1.082127 0.088 Uiso 0.285(6) 1 calc R U P A 2
C13 C 0.24285(12) 0.59264(8) 0.4756(2) 0.0408(5) Uani 1 1 d . . . . .
H13A H 0.267496 0.632882 0.511430 0.049 Uiso 1 1 calc R U . . .
C14 C 0.30741(13) 0.54102(9) 0.4848(3) 0.0615(7) Uani 1 1 d . . . . .
H14A H 0.322112 0.534064 0.589231 0.092 Uiso 1 1 calc R U . . .
H14B H 0.355004 0.554265 0.428640 0.092 Uiso 1 1 calc R U . . .
H14C H 0.286288 0.501797 0.442386 0.092 Uiso 1 1 calc R U . . .
C15 C 0.21677(15) 0.60255(11) 0.3137(2) 0.0615(6) Uani 1 1 d . . . . .
H15A H 0.190631 0.564219 0.276712 0.092 Uiso 1 1 calc R U . . .
H15B H 0.264031 0.611873 0.252370 0.092 Uiso 1 1 calc R U . . .
H15C H 0.178972 0.637913 0.308357 0.092 Uiso 1 1 calc R U . . .
C21 C 0.04497(15) 0.750000 0.4722(2) 0.0290(5) Uani 1 2 d S T P . .
C22 C 0.00628(11) 0.69409(8) 0.43089(19) 0.0328(4) Uani 1 1 d . . . . .
H22A H 0.029369 0.654754 0.457897 0.039 Uiso 1 1 calc R U . . .
C23 C -0.06500(11) 0.69501(9) 0.3515(2) 0.0380(4) Uani 1 1 d . . . . .
H23A H -0.089182 0.656023 0.324866 0.046 Uiso 0.5 1 calc R U P B 2
F23 F -0.09918(14) 0.64349(10) 0.3113(3) 0.0528(6) Uani 0.5 1 d . . P C 1
C24 C -0.10212(15) 0.750000 0.3096(3) 0.0357(6) Uani 1 2 d S T P C .
H24A H -0.150892 0.749999 0.254571 0.043 Uiso 1 2 calc R U P . .
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'
Al Al 0.0645 0.0514 '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'
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
F1 Al1 N1 106.82(6) . 7_575 ?
F1 Al1 N1 106.82(6) . . ?
N1 Al1 N1 97.22(8) 7_575 . ?
F1 Al1 C21 111.39(9) . . ?
N1 Al1 C21 116.62(6) 7_575 . ?
N1 Al1 C21 116.62(6) . . ?
C1 N1 C4 118.64(12) . . ?
C1 N1 Al1 119.16(10) . . ?
C4 N1 Al1 121.88(10) . . ?
N1 C1 C2 122.79(15) . . ?
N1 C1 C3 119.78(14) . . ?
C2 C1 C3 117.41(15) . . ?
C1 C2 C1 127.4(2) . 7_575 ?
C5 C4 C9 121.79(16) . . ?
C5 C4 N1 118.69(15) . . ?
C9 C4 N1 119.46(15) . . ?
C6 C5 C4 117.5(2) . . ?
C6 C5 C10 117.7(2) . . ?
C4 C5 C10 124.5(2) . . ?
C6 C5 C10' 124.3(4) . . ?
C4 C5 C10' 117.2(4) . . ?
C7 C6 C5 121.5(2) . . ?
C6 C7 C8 120.16(19) . . ?
C7 C8 C9 121.4(2) . . ?
C8 C9 C4 117.53(19) . . ?
C8 C9 C13 119.35(18) . . ?
C4 C9 C13 123.11(15) . . ?
C5 C10 C12 112.4(3) . . ?
C5 C10 C11 109.5(3) . . ?
C12 C10 C11 110.2(3) . . ?
C11' C10' C12' 105.5(8) . . ?
C11' C10' C5 116.3(9) . . ?
C12' C10' C5 111.1(6) . . ?
C9 C13 C15 110.62(17) . . ?
C9 C13 C14 112.58(17) . . ?
C15 C13 C14 110.31(18) . . ?
C22 C21 C22 115.9(2) 7_575 . ?
C22 C21 Al1 121.87(11) 7_575 . ?
C22 C21 Al1 121.87(11) . . ?
C23 C22 C21 121.26(17) . . ?
F23 C23 C24 116.56(19) . . ?
F23 C23 C22 120.83(19) . . ?
C24 C23 C22 122.60(17) . . ?
C23 C24 C23 116.4(2) . 7_575 ?
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 F1 1.6694(15) . ?
Al1 N1 1.8844(13) 7_575 ?
Al1 N1 1.8845(13) . ?
Al1 C21 1.981(2) . ?
N1 C1 1.341(2) . ?
N1 C4 1.4534(19) . ?
C1 C2 1.3975(18) . ?
C1 C3 1.504(2) . ?
C4 C5 1.399(3) . ?
C4 C9 1.403(3) . ?
C5 C6 1.397(3) . ?
C5 C10 1.445(4) . ?
C5 C10' 1.708(9) . ?
C6 C7 1.367(4) . ?
C7 C8 1.369(3) . ?
C8 C9 1.397(2) . ?
C9 C13 1.513(3) . ?
C10 C12 1.525(5) . ?
C10 C11 1.549(5) . ?
C10' C11' 1.537(12) . ?
C10' C12' 1.557(10) . ?
C13 C15 1.531(3) . ?
C13 C14 1.536(3) . ?
C21 C22 1.399(2) 7_575 ?
C21 C22 1.399(2) . ?
C22 C23 1.384(2) . ?
C23 F23 1.283(3) . ?
C23 C24 1.372(2) . ?
