#------------------------------------------------------------------------------
#$Date: 2016-03-21 08:42:30 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178610 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/21/4072183.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_4072183
loop_
_publ_author_name
'Bouyahyi, Miloud'
'Grunova, Ekaterina'
'Marquet, Nicolas'
'Kirillov, Evgueni'
'Thomas, Christophe M.'
'Roisnel, Thierry'
'Carpentier, Jean-François'
_publ_section_title
;
 Aluminum Complexes of Fluorinated Dialkoxy-Diimino Salen-like Ligands:
 Syntheses, Structures, and Use in Ring-Opening Polymerization of Cyclic
 Esters
;
_journal_issue                   22
_journal_name_full               Organometallics
_journal_page_first              5815
_journal_paper_doi               10.1021/om800651z
_journal_volume                  27
_journal_year                    2008
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C22 H32 F12 N2 O2'
_chemical_formula_sum            'C22 H32 F12 N2 O2'
_chemical_formula_weight         584.5
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2007-09-20T16:47:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 91.228(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.3782(16)
_cell_length_b                   22.163(5)
_cell_length_c                   7.7542(14)
_cell_measurement_reflns_used    2123
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.03
_cell_measurement_theta_min      2.78
_cell_measurement_wavelength     0.71073
_cell_volume                     1267.7(5)
_computing_cell_refinement       'Bruker SMART, 2006'
_computing_data_collection       'Bruker SMART, 2006'
_computing_data_reduction        'Bruker SAINT, 2006'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.051
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8311
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.189
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0289P)²+0.9399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                2434
_reflns_number_total             2819
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om800651z_si_001.cif
_cod_data_source_block           job
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4072183
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_calc_flag
_atom_site_refinement_flags
C1 C 0.2648(3) 0.18915(11) 0.1341(3) 0.0206(5) Uani 1 d .
F1A F 0.11470(19) 0.17809(7) 0.0381(2) 0.0282(4) Uani 1 d .
F1B F 0.3170(2) 0.24570(6) 0.09960(18) 0.0260(3) Uani 1 d .
F1C F 0.2132(2) 0.18873(7) 0.29818(18) 0.0334(4) Uani 1 d .
C2 C 0.5950(3) 0.16633(11) 0.1818(3) 0.0207(5) Uani 1 d .
F2A F 0.5669(2) 0.19031(7) 0.33777(17) 0.0300(4) Uani 1 d .
F2B F 0.67452(19) 0.20940(7) 0.08912(18) 0.0262(3) Uani 1 d .
F2C F 0.7180(2) 0.12260(7) 0.20572(19) 0.0292(4) Uani 1 d .
C3 C 0.4154(3) 0.14114(10) 0.1016(3) 0.0134(4) Uani 1 d .
O4 O 0.3811(2) 0.09062(7) 0.20432(19) 0.0182(4) Uani 1 d .
H4 H 0.303(5) 0.0688(16) 0.138(4) 0.05 Uiso 1 d .
C5 C 0.4267(3) 0.12547(10) -0.0980(3) 0.0118(4) Uani 1 d .
C5A C 0.6005(3) 0.08909(12) -0.1316(3) 0.0212(5) Uani 1 d .
H5A1 H 0.5971 0.0739 -0.2504 0.032 Uiso 1 calc R
H5A2 H 0.6083 0.055 -0.0512 0.032 Uiso 1 calc R
H5A3 H 0.7066 0.1152 -0.1145 0.032 Uiso 1 calc R
C5B C 0.4279(3) 0.18380(11) -0.2081(3) 0.0216(5) Uani 1 d .
H5B1 H 0.5081 0.2137 -0.1528 0.032 Uiso 1 calc R
H5B2 H 0.3047 0.2001 -0.2176 0.032 Uiso 1 calc R
H5B3 H 0.4718 0.1745 -0.3235 0.032 Uiso 1 calc R
C6 C 0.2707(3) 0.08248(9) -0.1592(3) 0.0108(4) Uani 1 d .
C7 C 0.2350(3) 0.07952(10) -0.3543(3) 0.0150(5) Uani 1 d .
H7 H 0.3336 0.1034 -0.4087 0.018 Uiso 1 calc R
C7A C 0.2483(3) 0.01529(11) -0.4271(3) 0.0180(5) Uani 1 d .
H7A1 H 0.3543 -0.0051 -0.3755 0.027 Uiso 1 calc R
H7A2 H 0.2609 0.0172 -0.5526 0.027 Uiso 1 calc R
H7A3 H 0.1384 -0.0073 -0.3997 0.027 Uiso 1 calc R
C7B C 0.0552(3) 0.11113(11) -0.4047(3) 0.0204(5) Uani 1 d .
H7B1 H -0.0456 0.0904 -0.3495 0.031 Uiso 1 calc R
H7B2 H 0.0375 0.1098 -0.5303 0.031 Uiso 1 calc R
H7B3 H 0.0595 0.1532 -0.3663 0.031 Uiso 1 calc R
N8 N 0.1935(2) 0.05009(8) -0.0466(2) 0.0123(4) Uani 1 d .
C9 C 0.0508(3) 0.00557(10) -0.0827(3) 0.0130(4) Uani 1 d .
H9A H 0.105 -0.0325 -0.1237 0.016 Uiso 1 calc R
H9B H -0.0334 0.0209 -0.1736 0.016 Uiso 1 calc R
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 0 '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'
O O 0.0106 0.006 '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
F1C C1 F1B 106.59(18) . .
F1C C1 F1A 106.12(19) . .
F1B C1 F1A 107.29(19) . .
F1C C1 C3 111.54(19) . .
F1B C1 C3 113.35(18) . .
F1A C1 C3 111.54(18) . .
F2C C2 F2B 106.7(2) . .
F2C C2 F2A 106.23(19) . .
F2B C2 F2A 106.23(19) . .
F2C C2 C3 111.41(19) . .
F2B C2 C3 114.88(19) . .
F2A C2 C3 110.89(19) . .
O4 C3 C2 102.84(18) . .
O4 C3 C1 108.33(17) . .
C2 C3 C1 107.07(18) . .
O4 C3 C5 113.13(17) . .
C2 C3 C5 113.97(17) . .
C1 C3 C5 110.97(17) . .
C3 O4 H4 103(2) . .
C5A C5 C5B 109.18(18) . .
C5A C5 C6 103.88(17) . .
C5B C5 C6 110.81(17) . .
C5A C5 C3 109.85(17) . .
C5B C5 C3 110.78(17) . .
C6 C5 C3 112.09(16) . .
C5 C5A H5A1 109.5 . .
C5 C5A H5A2 109.5 . .
H5A1 C5A H5A2 109.5 . .
C5 C5A H5A3 109.5 . .
H5A1 C5A H5A3 109.5 . .
H5A2 C5A H5A3 109.5 . .
C5 C5B H5B1 109.5 . .
C5 C5B H5B2 109.5 . .
H5B1 C5B H5B2 109.5 . .
C5 C5B H5B3 109.5 . .
H5B1 C5B H5B3 109.5 . .
H5B2 C5B H5B3 109.5 . .
N8 C6 C7 125.64(19) . .
N8 C6 C5 118.25(18) . .
C7 C6 C5 115.91(16) . .
C6 C7 C7A 113.06(17) . .
C6 C7 C7B 111.07(17) . .
C7A C7 C7B 112.92(19) . .
C6 C7 H7 106.4 . .
C7A C7 H7 106.4 . .
C7B C7 H7 106.4 . .
C7 C7A H7A1 109.5 . .
C7 C7A H7A2 109.5 . .
H7A1 C7A H7A2 109.5 . .
C7 C7A H7A3 109.5 . .
H7A1 C7A H7A3 109.5 . .
H7A2 C7A H7A3 109.5 . .
C7 C7B H7B1 109.5 . .
C7 C7B H7B2 109.5 . .
H7B1 C7B H7B2 109.5 . .
C7 C7B H7B3 109.5 . .
H7B1 C7B H7B3 109.5 . .
H7B2 C7B H7B3 109.5 . .
C6 N8 C9 125.35(18) . .
N8 C9 C9 108.3(2) . 3
N8 C9 H9A 110 . .
C9 C9 H9A 110 3 .
N8 C9 H9B 110 . .
C9 C9 H9B 110 3 .
H9A C9 H9B 108.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 F1C 1.336(3) .
C1 F1B 1.340(3) .
C1 F1A 1.344(3) .
C1 C3 1.563(3) .
C2 F2C 1.338(3) .
C2 F2B 1.338(3) .
C2 F2A 1.341(3) .
C2 C3 1.555(3) .
C3 O4 1.401(2) .
C3 C5 1.590(3) .
O4 H4 0.90(3) .
C5 C5A 1.542(3) .
C5 C5B 1.549(3) .
C5 C6 1.560(3) .
C5A H5A1 0.98 .
C5A H5A2 0.98 .
C5A H5A3 0.98 .
C5B H5B1 0.98 .
C5B H5B2 0.98 .
C5B H5B3 0.98 .
C6 N8 1.274(3) .
C6 C7 1.531(3) .
C7 C7A 1.535(3) .
C7 C7B 1.543(3) .
C7 H7 1 .
C7A H7A1 0.98 .
C7A H7A2 0.98 .
C7A H7A3 0.98 .
C7B H7B1 0.98 .
C7B H7B2 0.98 .
C7B H7B3 0.98 .
N8 C9 1.465(3) .
C9 C9 1.519(4) 3
C9 H9A 0.99 .
C9 H9B 0.99 .
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_4
F2C C2 C3 O4 47.9(2) .
F2B C2 C3 O4 169.35(18) .
F2A C2 C3 O4 -70.2(2) .
F2C C2 C3 C1 161.96(17) .
F2B C2 C3 C1 -76.6(2) .
F2A C2 C3 C1 43.9(2) .
F2C C2 C3 C5 -74.9(2) .
F2B C2 C3 C5 46.5(3) .
F2A C2 C3 C5 166.96(18) .
F1C C1 C3 O4 35.2(2) .
F1B C1 C3 O4 155.50(18) .
F1A C1 C3 O4 -83.3(2) .
F1C C1 C3 C2 -75.1(2) .
F1B C1 C3 C2 45.2(2) .
F1A C1 C3 C2 166.44(18) .
F1C C1 C3 C5 159.96(18) .
F1B C1 C3 C5 -79.7(2) .
F1A C1 C3 C5 41.5(2) .
O4 C3 C5 C5A -70.1(2) .
C2 C3 C5 C5A 46.9(2) .
C1 C3 C5 C5A 167.87(18) .
O4 C3 C5 C5B 169.17(18) .
C2 C3 C5 C5B -73.8(2) .
C1 C3 C5 C5B 47.2(2) .
O4 C3 C5 C6 44.8(2) .
C2 C3 C5 C6 161.85(18) .
C1 C3 C5 C6 -77.2(2) .
C5A C5 C6 N8 96.3(2) .
C5B C5 C6 N8 -146.62(19) .
C3 C5 C6 N8 -22.3(3) .
C5A C5 C6 C7 -78.9(2) .
C5B C5 C6 C7 38.2(2) .
C3 C5 C6 C7 162.54(17) .
N8 C6 C7 C7A -51.5(3) .
C5 C6 C7 C7A 123.3(2) .
N8 C6 C7 C7B 76.7(3) .
C5 C6 C7 C7B -108.6(2) .
C7 C6 N8 C9 -2.5(3) .
C5 C6 N8 C9 -177.20(18) .
C6 N8 C9 C9 -159.2(2) 3
