#------------------------------------------------------------------------------
#$Date: 2020-07-22 04:03:49 +0300 (Wed, 22 Jul 2020) $
#$Revision: 254450 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/86/1558641.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_1558641
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 H46 Al F N2'
_chemical_formula_sum            'C35 H46 Al F N2'
_chemical_formula_weight         540.72
_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
;
2019-05-21 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                   16.6384(4)
_cell_length_b                   21.0131(6)
_cell_length_c                   9.0227(2)
_cell_measurement_reflns_used    1922
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.5680
_cell_measurement_theta_min      4.1830
_cell_volume                     3154.56(14)
_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 10.4115
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Agilent Xcalibur PX Ultra A'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6501
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.389
_diffrn_reflns_theta_min         4.208
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.854
_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    1.139
_exptl_crystal_description       needles
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.073
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3135
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0458
_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)+(0.0478P)²+0.8441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1248
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2310
_reflns_number_total             3135
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc01915a2.cif
_cod_data_source_block           2a
_cod_original_cell_volume        3154.55(14)
_cod_database_code               1558641
_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 0.15287(4) 0.750000 0.55938(8) 0.02575(19) Uani 1 2 d S T P . .
F1 F 0.22445(10) 0.750000 0.42904(18) 0.0381(4) Uani 1 2 d S T P . .
N1 N 0.17801(9) 0.68257(7) 0.69017(17) 0.0261(3) Uani 1 1 d . . . . .
C1 C 0.23602(10) 0.69039(9) 0.7918(2) 0.0268(4) Uani 1 1 d . . . . .
C2 C 0.26714(15) 0.750000 0.8298(3) 0.0311(6) Uani 1 2 d S T P . .
H2A H 0.314719 0.750000 0.888042 0.037 Uiso 1 2 calc R U P . .
C3 C 0.26876(12) 0.63365(10) 0.8729(2) 0.0376(5) Uani 1 1 d . . . . .
H3A H 0.228228 0.617746 0.942443 0.056 Uiso 1 1 calc R U . . .
H3B H 0.317179 0.646010 0.927595 0.056 Uiso 1 1 calc R U . . .
H3C H 0.282233 0.600142 0.801516 0.056 Uiso 1 1 calc R U . . .
C4 C 0.14205(11) 0.61997(9) 0.6738(2) 0.0302(4) Uani 1 1 d . . . . .
C5 C 0.07505(12) 0.60455(10) 0.7612(2) 0.0380(5) Uani 1 1 d D . . . .
C6 C 0.03929(13) 0.54520(12) 0.7384(3) 0.0486(6) Uani 1 1 d . . . . .
H6A H -0.006315 0.533707 0.795820 0.058 Uiso 1 1 calc R U . . .
C7 C 0.06837(15) 0.50301(12) 0.6351(3) 0.0537(7) Uani 1 1 d . . . . .
H7A H 0.043106 0.462849 0.622088 0.064 Uiso 1 1 calc R U . . .
C8 C 0.13432(14) 0.51911(10) 0.5504(3) 0.0477(6) Uani 1 1 d . . . . .
H8A H 0.153898 0.489758 0.478939 0.057 Uiso 1 1 calc R U . . .
C9 C 0.17285(12) 0.57756(9) 0.5676(2) 0.0356(4) Uani 1 1 d . . . . .
C10 C 0.0427(3) 0.6484(3) 0.8785(6) 0.0496(14) Uani 0.800(10) 1 d D U P A 1
H10A H 0.075036 0.688489 0.879847 0.059 Uiso 0.800(10) 1 calc R U P A 1
C11 C -0.0452(3) 0.6642(3) 0.8444(6) 0.0570(11) Uani 0.800(10) 1 d D U P A 1
H11A H -0.066319 0.692799 0.920922 0.085 Uiso 0.800(10) 1 calc R U P A 1
H11B H -0.048729 0.685098 0.747470 0.085 Uiso 0.800(10) 1 calc R U P A 1
H11C H -0.076933 0.624918 0.842922 0.085 Uiso 0.800(10) 1 calc R U P A 1
C12 C 0.0481(2) 0.6154(3) 1.0333(4) 0.0693(16) Uani 0.800(10) 1 d D . P A 1
H12A H 0.026988 0.644147 1.109425 0.104 Uiso 0.800(10) 1 calc R U P A 1
H12B H 0.016414 0.576119 1.032106 0.104 Uiso 0.800(10) 1 calc R U P A 1
H12C H 0.104355 0.605302 1.055381 0.104 Uiso 0.800(10) 1 calc R U P A 1
C10' C 0.0327(14) 0.6497(18) 0.866(3) 0.070(8) Uiso 0.200(10) 1 d D U P A 2
H10B H 0.050342 0.690579 0.819552 0.084 Uiso 0.200(10) 1 calc R U P A 2
C11' C -0.0586(11) 0.6651(16) 0.879(3) 0.069(7) Uiso 0.200(10) 1 d D U P A 2
H11D H -0.067126 0.696383 0.957591 0.104 Uiso 0.200(10) 1 calc R U P A 2
H11E H -0.077879 0.682484 0.784333 0.104 Uiso 0.200(10) 1 calc R U P A 2
H11F H -0.088276 0.626046 0.901870 0.104 Uiso 0.200(10) 1 calc R U P A 2
C12' C 0.0686(11) 0.6610(12) 1.024(2) 0.082(6) Uiso 0.200(10) 1 d D . P A 2
H12D H 0.034745 0.691184 1.078150 0.122 Uiso 0.200(10) 1 calc R U P A 2
H12E H 0.070683 0.620541 1.077721 0.122 Uiso 0.200(10) 1 calc R U P A 2
H12F H 0.123082 0.678377 1.014639 0.122 Uiso 0.200(10) 1 calc R U P A 2
C13 C 0.24524(13) 0.59328(10) 0.4719(3) 0.0410(5) Uani 1 1 d . . . . .
H13A H 0.269053 0.633906 0.509358 0.049 Uiso 1 1 calc R U . . .
C14 C 0.30997(15) 0.54144(12) 0.4819(3) 0.0580(7) Uani 1 1 d . . . . .
H14A H 0.324180 0.534374 0.586037 0.087 Uiso 1 1 calc R U . . .
H14B H 0.357782 0.555015 0.426949 0.087 Uiso 1 1 calc R U . . .
H14C H 0.289272 0.501818 0.439180 0.087 Uiso 1 1 calc R U . . .
C15 C 0.22004(18) 0.60368(15) 0.3105(3) 0.0586(7) Uani 1 1 d . . . . .
H15A H 0.195713 0.564605 0.271712 0.088 Uiso 1 1 calc R U . . .
H15B H 0.267382 0.614623 0.251140 0.088 Uiso 1 1 calc R U . . .
H15C H 0.180893 0.638452 0.305382 0.088 Uiso 1 1 calc R U . . .
C21 C 0.04441(16) 0.750000 0.4703(3) 0.0321(6) Uani 1 2 d S T P . .
C22 C 0.00549(12) 0.69353(10) 0.4295(2) 0.0366(5) Uani 1 1 d . . . . .
H22A H 0.029264 0.654041 0.456132 0.044 Uiso 1 1 calc R U . . .
C23 C -0.06692(12) 0.69307(11) 0.3513(2) 0.0414(5) Uani 1 1 d . . . . .
H23A H -0.091360 0.653722 0.325697 0.050 Uiso 1 1 calc R U . . .
C24 C -0.10336(16) 0.750000 0.3108(3) 0.0395(7) Uani 1 2 d S T P . .
H24A H -0.152270 0.749999 0.256491 0.047 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 0.0181 0.0091 '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 0.2130 0.2455 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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 106.33(6) . 7_575 ?
F1 Al1 N1 106.33(6) . . ?
N1 Al1 N1 97.07(10) 7_575 . ?
F1 Al1 C21 111.35(11) . . ?
N1 Al1 C21 117.13(7) 7_575 . ?
N1 Al1 C21 117.13(7) . . ?
C1 N1 C4 118.48(15) . . ?
C1 N1 Al1 119.60(12) . . ?
C4 N1 Al1 121.60(12) . . ?
N1 C1 C2 122.97(17) . . ?
N1 C1 C3 119.80(16) . . ?
C2 C1 C3 117.22(17) . . ?
C1 C2 C1 127.2(2) 7_575 . ?
C5 C4 C9 121.76(19) . . ?
C5 C4 N1 118.64(18) . . ?
C9 C4 N1 119.55(17) . . ?
C6 C5 C4 117.5(2) . . ?
C6 C5 C10 119.9(3) . . ?
C4 C5 C10 122.6(3) . . ?
C6 C5 C10' 116.9(15) . . ?
C4 C5 C10' 125.2(15) . . ?
C7 C6 C5 121.7(2) . . ?
C6 C7 C8 119.8(2) . . ?
C7 C8 C9 121.4(2) . . ?
C8 C9 C4 117.8(2) . . ?
C8 C9 C13 119.6(2) . . ?
C4 C9 C13 122.62(18) . . ?
C5 C10 C11 109.5(4) . . ?
C5 C10 C12 109.7(4) . . ?
C11 C10 C12 109.3(4) . . ?
C5 C10' C11' 129(2) . . ?
C5 C10' C12' 119.1(17) . . ?
C11' C10' C12' 106.0(13) . . ?
C9 C13 C15 110.76(19) . . ?
C9 C13 C14 111.7(2) . . ?
C15 C13 C14 110.5(2) . . ?
C22 C21 C22 115.8(2) 7_575 . ?
C22 C21 Al1 121.94(12) 7_575 . ?
C22 C21 Al1 121.94(12) . . ?
C23 C22 C21 122.5(2) . . ?
C24 C23 C22 120.2(2) . . ?
C23 C24 C23 118.8(3) . 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 1.6737(17) . ?
Al1 N1 1.8908(16) 7_575 ?
Al1 N1 1.8909(16) . ?
Al1 C21 1.976(3) . ?
N1 C1 1.341(2) . ?
N1 C4 1.453(2) . ?
C1 C2 1.398(2) . ?
C1 C3 1.501(3) . ?
C4 C5 1.403(3) . ?
C4 C9 1.406(3) . ?
C5 C6 1.397(3) . ?
C5 C10 1.503(4) . ?
C5 C10' 1.514(16) . ?
C6 C7 1.374(4) . ?
C7 C8 1.379(4) . ?
C8 C9 1.394(3) . ?
C9 C13 1.518(3) . ?
C10 C11 1.532(5) . ?
C10 C12 1.561(7) . ?
C10' C11' 1.557(14) . ?
C10' C12' 1.563(15) . ?
C13 C15 1.531(3) . ?
C13 C14 1.534(3) . ?
C21 C22 1.401(2) 7_575 ?
C21 C22 1.401(2) . ?
C22 C23 1.396(3) . ?
C23 C24 1.390(3) . ?
