#------------------------------------------------------------------------------
#$Date: 2015-12-06 10:03:19 +0200 (Sun, 06 Dec 2015) $
#$Revision: 170824 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/63/4086337.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_4086337
loop_
_publ_author_name
'Chu, Terry'
'Boyko, Yaroslav'
'Korobkov, Ilia'
'Nikonov, Georgii I.'
_publ_section_title
;
 Transition Metal-like Oxidative Addition of C--F and C--O Bonds to an
 Aluminum(I) Center
;
_journal_issue                   22
_journal_name_full               Organometallics
_journal_page_first              5363
_journal_paper_doi               10.1021/acs.organomet.5b00793
_journal_volume                  34
_journal_year                    2015
_chemical_formula_sum            'C35 H52 Al F N2'
_chemical_formula_weight         546.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 114.2542(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.9145(6)
_cell_length_b                   19.8791(12)
_cell_length_c                   10.0955(6)
_cell_measurement_reflns_used    8024
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.21
_cell_volume                     1631.13(18)
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_collection       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_laue_measured_fraction_full 0.996
_diffrn_reflns_laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14090
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.354
_diffrn_reflns_theta_min         2.049
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         4169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0398
_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)+(0.0634P)²+0.3312P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1164
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3626
_reflns_number_total             4169
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om5b00793_si_002.cif
_cod_data_source_block           gn052
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/a' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4086334--4086337.cif.
;
_cod_database_code               4086337
_shelx_shelxl_version_number     2014/7
_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   0.968
_shelx_estimated_absorpt_t_max   0.979
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
Al1 Al 0.00634(5) 0.2500 0.78102(4) 0.02512(12) Uani 1 2 d S T P
F1 F 0.20306(12) 0.2500 0.89968(11) 0.0438(3) Uani 1 2 d S T P
N1 N -0.02047(9) 0.32057(4) 0.64645(9) 0.02430(18) Uani 1 1 d . . .
C1 C 0.02934(14) 0.37308(6) 0.44723(12) 0.0344(2) Uani 1 1 d . . .
H1A H -0.0701 0.4004 0.4218 0.052 Uiso 1 1 calc R U .
H1B H 0.0381 0.3581 0.3582 0.052 Uiso 1 1 calc R U .
H1C H 0.1262 0.4000 0.5053 0.052 Uiso 1 1 calc R U .
C2 C 0.01991(11) 0.31282(5) 0.53363(10) 0.0259(2) Uani 1 1 d . . .
C3 C 0.05104(17) 0.2500 0.48877(15) 0.0283(3) Uani 1 2 d S T P
H3A H 0.0987 0.2500 0.4201 0.034 Uiso 1 2 calc R U P
C4 C -0.06934(12) 0.38624(5) 0.67541(11) 0.0263(2) Uani 1 1 d . . .
C5 C -0.23863(13) 0.40105(6) 0.62105(11) 0.0304(2) Uani 1 1 d . . .
C6 C -0.28419(15) 0.46361(6) 0.65518(14) 0.0387(3) Uani 1 1 d . . .
H6A H -0.3975 0.4751 0.6187 0.046 Uiso 1 1 calc R U .
C7 C -0.16821(17) 0.50900(6) 0.74073(14) 0.0419(3) Uani 1 1 d . . .
H7A H -0.2021 0.5513 0.7628 0.050 Uiso 1 1 calc R U .
C8 C -0.00272(15) 0.49333(6) 0.79461(13) 0.0382(3) Uani 1 1 d . . .
H8A H 0.0761 0.5249 0.8544 0.046 Uiso 1 1 calc R U .
C9 C 0.05021(13) 0.43189(5) 0.76238(11) 0.0301(2) Uani 1 1 d . . .
C10 C 0.23323(13) 0.41641(6) 0.82357(12) 0.0346(2) Uani 1 1 d . . .
H10A H 0.2481 0.3731 0.7799 0.041 Uiso 1 1 calc R U .
C11 C 0.32827(17) 0.47137(8) 0.78379(17) 0.0503(3) Uani 1 1 d . . .
H11A H 0.4456 0.4600 0.8247 0.076 Uiso 1 1 calc R U .
H11B H 0.2869 0.4747 0.6778 0.076 Uiso 1 1 calc R U .
H11C H 0.3131 0.5146 0.8234 0.076 Uiso 1 1 calc R U .
C12 C 0.30347(16) 0.40741(8) 0.98829(14) 0.0477(3) Uani 1 1 d . . .
H12A H 0.4214 0.3975 1.0252 0.072 Uiso 1 1 calc R U .
H12B H 0.2871 0.4489 1.0333 0.072 Uiso 1 1 calc R U .
H12C H 0.2470 0.3701 1.0121 0.072 Uiso 1 1 calc R U .
C13 C -0.36801(13) 0.35114(6) 0.52915(13) 0.0366(3) Uani 1 1 d . . .
H13A H -0.3179 0.3053 0.5515 0.044 Uiso 1 1 calc R U .
C14 C -0.51986(16) 0.35089(9) 0.56312(17) 0.0545(4) Uani 1 1 d . . .
H14A H -0.5994 0.3179 0.5010 0.082 Uiso 1 1 calc R U .
H14B H -0.4876 0.3389 0.6653 0.082 Uiso 1 1 calc R U .
H14C H -0.5701 0.3957 0.5448 0.082 Uiso 1 1 calc R U .
C15 C -0.42055(18) 0.36365(9) 0.36700(15) 0.0537(4) Uani 1 1 d . . .
H15A H -0.5040 0.3305 0.3112 0.081 Uiso 1 1 calc R U .
H15B H -0.4665 0.4090 0.3425 0.081 Uiso 1 1 calc R U .
H15C H -0.3248 0.3594 0.3433 0.081 Uiso 1 1 calc R U .
C16 C -0.1511(2) 0.2500 0.87274(16) 0.0330(3) Uani 1 2 d S T P
H16A H -0.2633 0.2500 0.7913 0.040 Uiso 1 2 calc R U P
C17 C -0.14353(18) 0.31270(7) 0.96493(14) 0.0442(3) Uani 1 1 d . . .
H17A H -0.0362 0.3138 1.0501 0.053 Uiso 1 1 calc R U .
H17B H -0.1516 0.3536 0.9064 0.053 Uiso 1 1 calc R U .
C18 C -0.2823(2) 0.31317(8) 1.01730(15) 0.0528(4) Uani 1 1 d . . .
H18A H -0.2696 0.3530 1.0800 0.063 Uiso 1 1 calc R U .
H18B H -0.3893 0.3171 0.9323 0.063 Uiso 1 1 calc R U .
C19 C -0.2826(3) 0.2500 1.1017(2) 0.0515(5) Uani 1 2 d S T P
H19A H -0.1843 0.2500 1.1953 0.062 Uiso 1 2 calc R U P
H19B H -0.3814 0.2500 1.1233 0.062 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'
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'
F F 0.0171 0.0103 '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
F1 Al1 N1 107.46(4) . 4_565
F1 Al1 N1 107.46(4) . .
N1 Al1 N1 95.28(5) 4_565 .
F1 Al1 C16 113.80(6) . .
N1 Al1 C16 115.53(4) 4_565 .
N1 Al1 C16 115.53(4) . .
C2 N1 C4 119.07(8) . .
C2 N1 Al1 121.72(7) . .
C4 N1 Al1 118.88(6) . .
N1 C2 C3 122.61(10) . .
N1 C2 C1 120.07(10) . .
C3 C2 C1 117.31(9) . .
C2 C3 C2 127.13(13) 4_565 .
C9 C4 C5 121.76(10) . .
C9 C4 N1 119.85(9) . .
C5 C4 N1 118.30(9) . .
C6 C5 C4 117.65(10) . .
C6 C5 C13 120.63(10) . .
C4 C5 C13 121.72(10) . .
C7 C6 C5 121.30(11) . .
C6 C7 C8 120.29(11) . .
C7 C8 C9 120.93(11) . .
C8 C9 C4 118.05(10) . .
C8 C9 C10 119.46(10) . .
C4 C9 C10 122.48(10) . .
C9 C10 C12 110.96(9) . .
C9 C10 C11 111.44(11) . .
C12 C10 C11 110.18(10) . .
C5 C13 C15 111.78(10) . .
C5 C13 C14 112.74(11) . .
C15 C13 C14 109.36(11) . .
C17 C16 C17 108.04(13) 4_565 .
C17 C16 Al1 114.84(8) 4_565 .
C17 C16 Al1 114.84(8) . .
C18 C17 C16 111.84(12) . .
C19 C18 C17 112.12(12) . .
C18 C19 C18 111.62(15) 4_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Al1 F1 1.6687(10) .
Al1 N1 1.8984(9) 4_565
Al1 N1 1.8984(9) .
Al1 C16 1.9739(16) .
N1 C2 1.3369(13) .
N1 C4 1.4438(13) .
C1 C2 1.5044(14) .
C2 C3 1.3946(12) .
C3 C2 1.3946(12) 4_565
C4 C9 1.4004(15) .
C4 C5 1.4089(14) .
C5 C6 1.3946(16) .
C5 C13 1.5153(16) .
C6 C7 1.3768(19) .
C7 C8 1.3820(18) .
C8 C9 1.3953(16) .
C9 C10 1.5199(15) .
C10 C12 1.5278(17) .
C10 C11 1.5337(17) .
C13 C15 1.5267(19) .
C13 C14 1.5269(17) .
C16 C17 1.5403(15) 4_565
C16 C17 1.5403(15) .
C17 C18 1.5321(19) .
C18 C19 1.5181(18) .
C19 C18 1.5180(18) 4_565
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_4
F1 Al1 N1 C2 81.67(8) . .
N1 Al1 N1 C2 -28.50(9) 4_565 .
C16 Al1 N1 C2 -150.09(8) . .
F1 Al1 N1 C4 -91.73(8) . .
N1 Al1 N1 C4 158.09(5) 4_565 .
C16 Al1 N1 C4 36.51(9) . .
C4 N1 C2 C3 -172.85(10) . .
Al1 N1 C2 C3 13.75(14) . .
C4 N1 C2 C1 5.67(13) . .
Al1 N1 C2 C1 -167.73(7) . .
N1 C2 C3 C2 11.5(2) . 4_565
C1 C2 C3 C2 -167.05(10) . 4_565
C2 N1 C4 C9 -87.36(11) . .
Al1 N1 C4 C9 86.22(10) . .
C2 N1 C4 C5 96.13(11) . .
Al1 N1 C4 C5 -90.29(10) . .
C9 C4 C5 C6 0.85(15) . .
N1 C4 C5 C6 177.29(9) . .
C9 C4 C5 C13 -178.90(10) . .
N1 C4 C5 C13 -2.46(14) . .
C4 C5 C6 C7 -0.94(16) . .
C13 C5 C6 C7 178.81(11) . .
C5 C6 C7 C8 0.18(18) . .
C6 C7 C8 C9 0.72(18) . .
C7 C8 C9 C4 -0.80(16) . .
C7 C8 C9 C10 179.99(11) . .
C5 C4 C9 C8 0.00(15) . .
N1 C4 C9 C8 -176.39(9) . .
C5 C4 C9 C10 179.19(10) . .
N1 C4 C9 C10 2.80(15) . .
C8 C9 C10 C12 68.30(14) . .
C4 C9 C10 C12 -110.87(12) . .
C8 C9 C10 C11 -54.88(14) . .
C4 C9 C10 C11 125.95(11) . .
C6 C5 C13 C15 85.58(14) . .
C4 C5 C13 C15 -94.67(13) . .
C6 C5 C13 C14 -38.10(15) . .
C4 C5 C13 C14 141.65(11) . .
C17 C16 C17 C18 -57.25(18) 4_565 .
Al1 C16 C17 C18 173.13(10) . .
C16 C17 C18 C19 56.06(17) . .
C17 C18 C19 C18 -52.4(2) . 4_565
