#------------------------------------------------------------------------------
#$Date: 2020-07-22 04:03:49 +0300 (Wed, 22 Jul 2020) $
#$Revision: 254450 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/86/1558645.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_1558645
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
'0.75(C29 H33 Al F2 N2), 0.25(C29 H34 Al F N2)'
_chemical_formula_sum            'C29 H33.25 Al F1.75 N2'
_chemical_formula_weight         470.05
_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                   14.5388(5)
_cell_length_b                   20.1047(6)
_cell_length_c                   8.9393(3)
_cell_measurement_reflns_used    1655
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      73.7470
_cell_measurement_theta_min      4.3740
_cell_volume                     2612.94(15)
_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 0.985
_diffrn_measured_fraction_theta_max 0.961
_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  0.0381
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5296
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.856
_diffrn_reflns_theta_min         4.398
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.929
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_correction_T_min  0.831
_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    1.195
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.149
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2615
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0549
_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)+(0.0912P)²+0.4098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1609
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2027
_reflns_number_total             2615
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc01915a2.cif
_cod_data_source_block           2c-prime
_cod_database_code               1558645
_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 0.64350(5) 0.250000 0.63368(9) 0.0342(2) Uani 1 2 d S T P . .
F1 F 0.57651(14) 0.250000 0.7845(2) 0.0422(5) Uani 0.75 2 d S T P A 1
N1 N 0.72865(11) 0.17947(8) 0.64957(18) 0.0370(4) Uani 1 1 d . . . . .
C1 C 0.81929(14) 0.18756(11) 0.6573(2) 0.0403(5) Uani 1 1 d . . . . .
C2 C 0.86210(18) 0.250000 0.6545(3) 0.0405(6) Uani 1 2 d S T P . .
H2A H 0.927387 0.250000 0.650162 0.049 Uiso 1 2 calc R U P . .
C3 C 0.88150(17) 0.12793(14) 0.6738(3) 0.0565(6) Uani 1 1 d . . . . .
H3A H 0.872429 0.107942 0.772691 0.085 Uiso 1 1 calc R U . . .
H3B H 0.945734 0.141939 0.663199 0.085 Uiso 1 1 calc R U . . .
H3C H 0.866750 0.095174 0.596229 0.085 Uiso 1 1 calc R U . . .
C4 C 0.68898(14) 0.11385(10) 0.6675(2) 0.0407(5) Uani 1 1 d . . . . .
C5 C 0.66391(16) 0.09200(11) 0.8106(3) 0.0465(5) Uani 1 1 d . . . . .
C6 C 0.61857(19) 0.03151(12) 0.8246(3) 0.0591(6) Uani 1 1 d . . . . .
H6A H 0.600711 0.016664 0.921233 0.071 Uiso 1 1 calc R U . . .
C7 C 0.5986(2) -0.00788(12) 0.7010(4) 0.0684(8) Uani 1 1 d . . . . .
C8 C 0.6269(2) 0.01392(12) 0.5617(4) 0.0661(8) Uani 1 1 d . . . . .
H8A H 0.615058 -0.013384 0.477128 0.079 Uiso 1 1 calc R U . . .
C9 C 0.67224(17) 0.07457(11) 0.5402(3) 0.0508(6) Uani 1 1 d . . . . .
C10 C 0.6874(2) 0.13132(12) 0.9484(3) 0.0565(6) Uani 1 1 d . . . . .
H10A H 0.753478 0.127618 0.968535 0.085 Uiso 1 1 calc R U . . .
H10B H 0.652774 0.113846 1.033840 0.085 Uiso 1 1 calc R U . . .
H10C H 0.671319 0.178137 0.932684 0.085 Uiso 1 1 calc R U . . .
C11 C 0.5498(3) -0.07358(15) 0.7193(6) 0.1024(15) Uani 1 1 d . . . . .
H11A H 0.591736 -0.105878 0.765117 0.154 Uiso 1 1 calc R U . . .
H11B H 0.530251 -0.089919 0.621030 0.154 Uiso 1 1 calc R U . . .
H11C H 0.495860 -0.067642 0.783542 0.154 Uiso 1 1 calc R U . . .
C12 C 0.7021(2) 0.09565(14) 0.3879(3) 0.0621(7) Uani 1 1 d . . . . .
H12A H 0.657671 0.127469 0.347041 0.093 Uiso 1 1 calc R U . . .
H12B H 0.705581 0.056651 0.322341 0.093 Uiso 1 1 calc R U . . .
H12C H 0.762824 0.116692 0.394089 0.093 Uiso 1 1 calc R U . . .
C21 C 0.56345(19) 0.250000 0.4549(3) 0.0365(6) Uani 1 2 d S T P A .
C22 C 0.46814(19) 0.250000 0.4790(3) 0.0383(6) Uani 1 2 d S T P . .
H22A H 0.444590 0.250000 0.578140 0.046 Uiso 1 2 calc R U P A .
C23 C 0.4082(2) 0.250000 0.3582(4) 0.0446(7) Uani 1 2 d S T P A .
F23 F 0.31610(14) 0.250000 0.3856(3) 0.0711(6) Uani 1 2 d S T P . .
C24 C 0.4373(2) 0.250000 0.2132(3) 0.0466(7) Uani 1 2 d S T P . .
H24A H 0.394388 0.250000 0.133098 0.056 Uiso 1 2 calc R U P A .
C25 C 0.5302(3) 0.250000 0.1861(3) 0.0499(7) Uani 1 2 d S T P A .
H25A H 0.552369 0.250000 0.086082 0.060 Uiso 1 2 calc R U P . .
C26 C 0.5920(2) 0.250000 0.3051(4) 0.0453(6) Uani 1 2 d S T P . .
H26A H 0.656043 0.250000 0.283976 0.054 Uiso 1 2 calc R U P A .
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 108.85(7) . . ?
F1 Al1 N1 108.84(7) . 7_565 ?
N1 Al1 N1 97.38(11) . 7_565 ?
F1 Al1 C21 108.09(12) . . ?
N1 Al1 C21 116.55(7) . . ?
N1 Al1 C21 116.55(7) 7_565 . ?
C1 N1 C4 120.02(17) . . ?
C1 N1 Al1 124.20(15) . . ?
C4 N1 Al1 115.55(12) . . ?
N1 C1 C2 123.3(2) . . ?
N1 C1 C3 120.1(2) . . ?
C2 C1 C3 116.57(19) . . ?
C1 C2 C1 127.2(2) . 7_565 ?
C5 C4 C9 121.2(2) . . ?
C5 C4 N1 119.36(18) . . ?
C9 C4 N1 119.4(2) . . ?
C6 C5 C4 118.7(2) . . ?
C6 C5 C10 119.6(2) . . ?
C4 C5 C10 121.6(2) . . ?
C5 C6 C7 121.7(3) . . ?
C8 C7 C6 118.3(2) . . ?
C8 C7 C11 121.0(3) . . ?
C6 C7 C11 120.7(3) . . ?
C7 C8 C9 122.7(2) . . ?
C8 C9 C4 117.4(2) . . ?
C8 C9 C12 120.7(2) . . ?
C4 C9 C12 121.9(2) . . ?
C26 C21 C22 116.1(3) . . ?
C26 C21 Al1 126.7(2) . . ?
C22 C21 Al1 117.2(2) . . ?
C23 C22 C21 120.1(3) . . ?
F23 C23 C24 118.5(3) . . ?
F23 C23 C22 118.5(3) . . ?
C24 C23 C22 123.0(3) . . ?
C23 C24 C25 118.3(3) . . ?
C24 C25 C26 120.0(3) . . ?
C25 C26 C21 122.6(3) . . ?
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 1.663(2) . ?
Al1 N1 1.8878(17) . ?
Al1 N1 1.8878(17) 7_565 ?
Al1 C21 1.977(3) . ?
N1 C1 1.330(3) . ?
N1 C4 1.449(3) . ?
C1 C2 1.401(3) . ?
C1 C3 1.509(3) . ?
C4 C5 1.401(3) . ?
C4 C9 1.406(3) . ?
C5 C6 1.389(3) . ?
C5 C10 1.503(3) . ?
C6 C7 1.390(4) . ?
C7 C8 1.383(5) . ?
C7 C11 1.508(4) . ?
C8 C9 1.399(4) . ?
C9 C12 1.491(4) . ?
C21 C26 1.402(4) . ?
C21 C22 1.402(4) . ?
C22 C23 1.388(4) . ?
C23 F23 1.361(4) . ?
C23 C24 1.363(5) . ?
C24 C25 1.373(5) . ?
C25 C26 1.393(5) . ?
