#------------------------------------------------------------------------------
#$Date: 2016-03-25 08:47:12 +0100 (vie 25 de mar de 2016) $
#$Revision: 179733 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/29/7002925.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_7002925
loop_
_publ_author_name
'Uhl, Werner'
'Claesener, Michael'
'Hepp, Alexander'
'Jasper, Beate'
'Vinogradov, Andrej'
'van Wüllen, Leo'
'Köster, Thomas K.-J.'
_publ_section_title
;
 The influence of halogen substituents on the course of hydrogallation
 and hydroalumination reactions
;
_journal_issue                   47
_journal_name_full               'Dalton Transactions'
_journal_page_first              10550
_journal_page_last               10562
_journal_paper_doi               10.1039/b913568e
_journal_year                    2009
_chemical_formula_sum            'C15 H20 Cl2 F5 Ga O Si'
_chemical_formula_weight         480.02
_chemical_name_systematic
;
?
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 126.747(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.403(4)
_cell_length_b                   7.6345(15)
_cell_length_c                   15.866(3)
_cell_measurement_reflns_used    913
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      29.710
_cell_measurement_theta_min      3.775
_cell_volume                     2077.4(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11465
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    1.683
_exptl_absorpt_correction_T_max  0.7295
_exptl_absorpt_correction_T_min  0.5525
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod-like
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.002(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         5758
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0242
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0357P)²+0.0306P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0588
_refine_ls_wR_factor_ref         0.0594
_reflns_number_gt                5536
_reflns_number_total             5758
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b913568e.txt
_cod_data_source_block           sad7
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               7002925
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ga1 Ga 0.501285(8) 0.97336(2) 0.699543(9) 0.02146(5) Uani 1 1 d . . .
Cl1 Cl 0.37608(3) 1.00107(8) 0.58434(4) 0.03899(12) Uani 1 1 d . . .
Cl2 Cl 0.55602(3) 1.14334(6) 0.65033(4) 0.03351(10) Uani 1 1 d . . .
Si1 Si 0.66918(3) 0.95228(9) 0.93617(4) 0.03429(13) Uani 1 1 d . . .
C11 C 0.69856(15) 1.1866(4) 0.9521(2) 0.0517(6) Uani 1 1 d . . .
H11A H 0.7543 1.1944 0.9930 0.062 Uiso 1 1 calc R . .
H11B H 0.6812 1.2483 0.9873 0.062 Uiso 1 1 calc R . .
H11C H 0.6753 1.2379 0.8841 0.062 Uiso 1 1 calc R . .
C12 C 0.70634(13) 0.8257(3) 0.87379(19) 0.0426(5) Uani 1 1 d . . .
H12A H 0.6874 0.8777 0.8074 0.051 Uiso 1 1 calc R . .
H12B H 0.6884 0.7068 0.8630 0.051 Uiso 1 1 calc R . .
H12C H 0.7623 0.8275 0.9190 0.051 Uiso 1 1 calc R . .
C13 C 0.70980(15) 0.8534(5) 1.06728(19) 0.0662(9) Uani 1 1 d . . .
H13A H 0.6901 0.7365 1.0578 0.079 Uiso 1 1 calc R . .
H13B H 0.6945 0.9228 1.1026 0.079 Uiso 1 1 calc R . .
H13C H 0.7657 0.8501 1.1088 0.079 Uiso 1 1 calc R . .
C1 C 0.55908(10) 0.9440(2) 0.85115(13) 0.0241(3) Uani 1 1 d . . .
C2 C 0.52537(11) 0.9131(3) 0.89874(14) 0.0273(3) Uani 1 1 d . . .
H2 H 0.5604 0.8869 0.9725 0.033 Uiso 1 1 calc R . .
C3 C 0.44144(10) 0.9138(3) 0.85316(13) 0.0243(3) Uani 1 1 d . . .
C4 C 0.39387(11) 1.0600(3) 0.80728(15) 0.0279(4) Uani 1 1 d . . .
C5 C 0.31842(12) 1.0636(3) 0.77551(16) 0.0334(4) Uani 1 1 d . . .
C6 C 0.28783(12) 0.9184(3) 0.78939(16) 0.0364(4) Uani 1 1 d . . .
C7 C 0.33261(12) 0.7707(3) 0.83451(16) 0.0357(4) Uani 1 1 d . . .
C8 C 0.40786(11) 0.7710(3) 0.86570(15) 0.0291(4) Uani 1 1 d . . .
F4 F 0.42300(8) 1.20793(16) 0.79709(10) 0.0386(3) Uani 1 1 d . . .
F5 F 0.27497(8) 1.2078(2) 0.73116(12) 0.0512(4) Uani 1 1 d . . .
F6 F 0.21422(8) 0.9196(2) 0.75839(13) 0.0554(4) Uani 1 1 d . . .
F7 F 0.30318(9) 0.6277(2) 0.84745(13) 0.0551(4) Uani 1 1 d . . .
F8 F 0.45064(8) 0.62481(16) 0.90954(11) 0.0434(3) Uani 1 1 d . . .
O1 O 0.51675(8) 0.74462(16) 0.65493(10) 0.0272(3) Uani 1 1 d . . .
C01 C 0.49795(12) 0.7241(3) 0.55038(15) 0.0311(4) Uani 1 1 d . . .
H01A H 0.4777 0.8325 0.5126 0.037 Uiso 1 1 calc R . .
H01B H 0.4583 0.6364 0.5121 0.037 Uiso 1 1 calc R . .
C02 C 0.56802(14) 0.6724(4) 0.55698(19) 0.0450(5) Uani 1 1 d . . .
H02A H 0.6074 0.7610 0.5941 0.054 Uiso 1 1 calc R . .
H02B H 0.5538 0.6599 0.4873 0.054 Uiso 1 1 calc R . .
H02C H 0.5878 0.5630 0.5937 0.054 Uiso 1 1 calc R . .
C03 C 0.51643(15) 0.5814(3) 0.7026(2) 0.0412(5) Uani 1 1 d . . .
H03A H 0.5453 0.5976 0.7771 0.049 Uiso 1 1 calc R . .
H03B H 0.5419 0.4917 0.6909 0.049 Uiso 1 1 calc R . .
C04 C 0.4353(2) 0.5232(4) 0.6581(4) 0.0677(9) Uani 1 1 d . . .
H04A H 0.4093 0.6134 0.6685 0.081 Uiso 1 1 calc R . .
H04B H 0.4375 0.4181 0.6930 0.081 Uiso 1 1 calc R . .
H04C H 0.4072 0.5007 0.5842 0.081 Uiso 1 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 0.0000 0.0000 '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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C1 Ga1 O1 102.75(7) . . ?
C1 Ga1 Cl1 127.05(6) . . ?
O1 Ga1 Cl1 99.83(4) . . ?
C1 Ga1 Cl2 115.43(6) . . ?
O1 Ga1 Cl2 98.96(4) . . ?
Cl1 Ga1 Cl2 107.31(3) . . ?
C11 Si1 C12 110.63(11) . . ?
C11 Si1 C13 110.04(15) . . ?
C12 Si1 C13 108.61(14) . . ?
C11 Si1 C1 107.72(11) . . ?
C12 Si1 C1 110.42(10) . . ?
C13 Si1 C1 109.41(10) . . ?
Si1 C11 H11A 109.5 . . ?
Si1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Si1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Si1 C12 H12A 109.5 . . ?
Si1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Si1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Si1 C13 H13A 109.5 . . ?
Si1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Si1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C1 Si1 117.71(13) . . ?
C2 C1 Ga1 123.82(14) . . ?
Si1 C1 Ga1 118.44(9) . . ?
C1 C2 C3 128.92(16) . . ?
C1 C2 H2 115.5 . . ?
C3 C2 H2 115.5 . . ?
C8 C3 C4 115.34(17) . . ?
C8 C3 C2 120.61(17) . . ?
C4 C3 C2 123.61(18) . . ?
F4 C4 C5 117.78(18) . . ?
F4 C4 C3 119.41(17) . . ?
C5 C4 C3 122.75(18) . . ?
F5 C5 C6 120.11(19) . . ?
F5 C5 C4 120.3(2) . . ?
C6 C5 C4 119.6(2) . . ?
F6 C6 C5 120.4(2) . . ?
F6 C6 C7 119.8(2) . . ?
C5 C6 C7 119.80(18) . . ?
F7 C7 C6 120.36(19) . . ?
F7 C7 C8 120.3(2) . . ?
C6 C7 C8 119.31(19) . . ?
F8 C8 C7 118.33(18) . . ?
F8 C8 C3 118.49(17) . . ?
C7 C8 C3 123.18(18) . . ?
C03 O1 C01 114.38(15) . . ?
C03 O1 Ga1 120.85(12) . . ?
C01 O1 Ga1 120.48(11) . . ?
O1 C01 C02 111.45(17) . . ?
O1 C01 H01A 109.3 . . ?
C02 C01 H01A 109.3 . . ?
O1 C01 H01B 109.3 . . ?
C02 C01 H01B 109.3 . . ?
H01A C01 H01B 108.0 . . ?
C01 C02 H02A 109.5 . . ?
C01 C02 H02B 109.5 . . ?
H02A C02 H02B 109.5 . . ?
C01 C02 H02C 109.5 . . ?
H02A C02 H02C 109.5 . . ?
H02B C02 H02C 109.5 . . ?
O1 C03 C04 111.9(2) . . ?
O1 C03 H03A 109.2 . . ?
C04 C03 H03A 109.2 . . ?
O1 C03 H03B 109.2 . . ?
C04 C03 H03B 109.2 . . ?
H03A C03 H03B 107.9 . . ?
C03 C04 H04A 109.5 . . ?
C03 C04 H04B 109.5 . . ?
H04A C04 H04B 109.5 . . ?
C03 C04 H04C 109.5 . . ?
H04A C04 H04C 109.5 . . ?
H04B C04 H04C 109.5 . . ?
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
Ga1 C1 1.9509(18) . ?
Ga1 O1 1.9851(13) . ?
Ga1 Cl1 2.1692(7) . ?
Ga1 Cl2 2.1820(5) . ?
Si1 C11 1.863(3) . ?
Si1 C12 1.868(2) . ?
Si1 C13 1.868(3) . ?
Si1 C1 1.8902(19) . ?
C11 H11A 0.9599 . ?
C11 H11B 0.9599 . ?
C11 H11C 0.9599 . ?
C12 H12A 0.9599 . ?
C12 H12B 0.9599 . ?
C12 H12C 0.9599 . ?
C13 H13A 0.9599 . ?
C13 H13B 0.9599 . ?
C13 H13C 0.9599 . ?
C1 C2 1.341(2) . ?
C2 C3 1.482(3) . ?
C2 H2 0.9600 . ?
C3 C8 1.384(3) . ?
C3 C4 1.388(3) . ?
C4 F4 1.346(2) . ?
C4 C5 1.374(3) . ?
C5 F5 1.338(2) . ?
C5 C6 1.371(3) . ?
C6 F6 1.340(2) . ?
C6 C7 1.372(3) . ?
C7 F7 1.336(2) . ?
C7 C8 1.373(3) . ?
C8 F8 1.344(2) . ?
O1 C03 1.460(2) . ?
O1 C01 1.463(2) . ?
C01 C02 1.493(3) . ?
C01 H01A 0.9600 . ?
C01 H01B 0.9600 . ?
C02 H02A 0.9599 . ?
C02 H02B 0.9599 . ?
C02 H02C 0.9599 . ?
C03 C04 1.497(4) . ?
C03 H03A 0.9600 . ?
C03 H03B 0.9600 . ?
C04 H04A 0.9599 . ?
C04 H04B 0.9599 . ?
C04 H04C 0.9599 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 Si1 C1 C2 -103.93(18) . . . . ?
C12 Si1 C1 C2 135.16(17) . . . . ?
C13 Si1 C1 C2 15.7(2) . . . . ?
C11 Si1 C1 Ga1 77.97(13) . . . . ?
C12 Si1 C1 Ga1 -42.94(14) . . . . ?
C13 Si1 C1 Ga1 -162.42(15) . . . . ?
O1 Ga1 C1 C2 -103.11(17) . . . . ?
Cl1 Ga1 C1 C2 9.9(2) . . . . ?
Cl2 Ga1 C1 C2 150.37(15) . . . . ?
O1 Ga1 C1 Si1 74.86(11) . . . . ?
Cl1 Ga1 C1 Si1 -172.17(6) . . . . ?
Cl2 Ga1 C1 Si1 -31.67(12) . . . . ?
Si1 C1 C2 C3 174.63(16) . . . . ?
Ga1 C1 C2 C3 -7.4(3) . . . . ?
C1 C2 C3 C8 126.7(2) . . . . ?
C1 C2 C3 C4 -61.3(3) . . . . ?
C8 C3 C4 F4 176.52(16) . . . . ?
C2 C3 C4 F4 4.1(3) . . . . ?
C8 C3 C4 C5 -0.5(3) . . . . ?
C2 C3 C4 C5 -172.90(17) . . . . ?
F4 C4 C5 F5 3.3(3) . . . . ?
C3 C4 C5 F5 -179.63(19) . . . . ?
F4 C4 C5 C6 -176.76(18) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
F5 C5 C6 F6 0.2(3) . . . . ?
C4 C5 C6 F6 -179.70(19) . . . . ?
F5 C5 C6 C7 179.7(2) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
F6 C6 C7 F7 0.2(3) . . . . ?
C5 C6 C7 F7 -179.29(19) . . . . ?
F6 C6 C7 C8 179.84(19) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
F7 C7 C8 F8 -0.2(3) . . . . ?
C6 C7 C8 F8 -179.89(18) . . . . ?
F7 C7 C8 C3 179.06(18) . . . . ?
C6 C7 C8 C3 -0.6(3) . . . . ?
C4 C3 C8 F8 179.93(16) . . . . ?
C2 C3 C8 F8 -7.4(3) . . . . ?
C4 C3 C8 C7 0.6(3) . . . . ?
C2 C3 C8 C7 173.30(18) . . . . ?
C1 Ga1 O1 C03 38.66(16) . . . . ?
Cl1 Ga1 O1 C03 -93.11(15) . . . . ?
Cl2 Ga1 O1 C03 157.44(14) . . . . ?
C1 Ga1 O1 C01 -165.93(14) . . . . ?
Cl1 Ga1 O1 C01 62.30(13) . . . . ?
Cl2 Ga1 O1 C01 -47.16(14) . . . . ?
C03 O1 C01 C02 -83.4(2) . . . . ?
Ga1 O1 C01 C02 119.69(17) . . . . ?
C01 O1 C03 C04 -78.0(2) . . . . ?
Ga1 O1 C03 C04 78.8(2) . . . . ?
