#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/47/7104766.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_7104766
loop_
_publ_author_name
'Bäuerlein, Patrick S'
'Fairlamb, Ian J S'
'Jarvis, Amanda G'
'Lee, Adam F'
'Müller, Christian'
'Slattery, John M'
'Thatcher, Robert J'
'Vogt, Dieter'
'Whitwood, Adrian C'
_publ_section_title
;
 Ion-tagged pi-acidic alkene ligands promote Pd-catalysed allyl-aryl
 couplings in an ionic liquid.
;
_journal_issue                   38
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5734
_journal_page_last               5736
_journal_paper_doi               10.1039/b906823f
_journal_volume                  34
_journal_year                    2009
_chemical_formula_moiety         'C22 H26 N O2 Br'
_chemical_formula_sum            'C22 H26 Br N O2'
_chemical_formula_weight         416.35
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.0820(10)
_cell_angle_beta                 94.3980(10)
_cell_angle_gamma                112.7110(10)
_cell_formula_units_Z            2
_cell_length_a                   8.2923(5)
_cell_length_b                   10.5937(6)
_cell_length_c                   13.0176(8)
_cell_measurement_reflns_used    5304
_cell_measurement_temperature    383(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.68
_cell_volume                     1015.67(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10520
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    2.039
_exptl_absorpt_correction_T_max  0.849
_exptl_absorpt_correction_T_min  0.765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v1.03 (Sheldrick)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.006
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0576P)²+1.1647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1203
_reflns_number_gt                4480
_reflns_number_total             4982
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b906823f.txt
_cod_data_source_block           jms0803m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C22 H26 N O2 Br'
_cod_database_code               7104766
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.4356(4) 1.2484(3) -0.1887(2) 0.0354(6) Uani 1 1 d . . .
H1 H 1.5325 1.2857 -0.1335 0.042 Uiso 1 1 calc R . .
C2 C 1.4427(4) 1.3108(3) -0.2736(3) 0.0380(7) Uani 1 1 d . . .
H2 H 1.5452 1.3875 -0.2760 0.046 Uiso 1 1 calc R . .
C3 C 1.2977(5) 1.2587(3) -0.3536(3) 0.0394(7) Uani 1 1 d . . .
H3 H 1.3015 1.3015 -0.4094 0.047 Uiso 1 1 calc R . .
C4 C 1.1458(4) 1.1424(4) -0.3514(3) 0.0406(7) Uani 1 1 d . . .
H4 H 1.0476 1.1080 -0.4054 0.049 Uiso 1 1 calc R . .
C5 C 1.1402(4) 1.0773(3) -0.2688(2) 0.0362(6) Uani 1 1 d . . .
H5 H 1.0393 0.9977 -0.2689 0.043 Uiso 1 1 calc R . .
C6 C 1.2840(4) 1.1301(3) -0.1857(2) 0.0292(5) Uani 1 1 d . . .
C7 C 1.2873(4) 1.0675(3) -0.0961(2) 0.0298(5) Uani 1 1 d . . .
H7 H 1.3850 1.1172 -0.0414 0.036 Uiso 1 1 calc R . .
C8 C 1.1657(4) 0.9466(3) -0.0835(2) 0.0299(5) Uani 1 1 d . . .
H8 H 1.0632 0.8936 -0.1343 0.036 Uiso 1 1 calc R . .
C9 C 1.1965(3) 0.8983(3) 0.0121(2) 0.0277(5) Uani 1 1 d . . .
C10 C 1.0577(3) 0.7701(3) 0.0311(2) 0.0268(5) Uani 1 1 d . . .
C11 C 0.8885(3) 0.6980(3) -0.0309(2) 0.0275(5) Uani 1 1 d . . .
H11 H 0.8610 0.7260 -0.0906 0.033 Uiso 1 1 calc R . .
C12 C 0.7611(4) 0.5853(3) -0.0046(2) 0.0285(5) Uani 1 1 d . . .
H12 H 0.6479 0.5390 -0.0456 0.034 Uiso 1 1 calc R . .
C13 C 0.8029(3) 0.5416(3) 0.0834(2) 0.0262(5) Uani 1 1 d . . .
C14 C 0.9720(4) 0.6086(3) 0.1441(2) 0.0322(6) Uani 1 1 d . . .
H14 H 1.0012 0.5770 0.2013 0.039 Uiso 1 1 calc R . .
C15 C 1.0967(4) 0.7233(3) 0.1180(2) 0.0323(6) Uani 1 1 d . . .
H15 H 1.2094 0.7702 0.1597 0.039 Uiso 1 1 calc R . .
C16 C 0.7007(3) 0.3970(3) 0.2026(2) 0.0278(5) Uani 1 1 d . . .
H16A H 0.7509 0.4813 0.2618 0.033 Uiso 1 1 calc R . .
H16B H 0.7811 0.3503 0.1980 0.033 Uiso 1 1 calc R . .
C17 C 0.5177(3) 0.2974(3) 0.2153(2) 0.0264(5) Uani 1 1 d . . .
H17A H 0.4409 0.3473 0.2200 0.032 Uiso 1 1 calc R . .
H17B H 0.4674 0.2180 0.1524 0.032 Uiso 1 1 calc R . .
C18 C 0.5894(4) 0.3611(3) 0.4123(2) 0.0301(5) Uani 1 1 d . . .
H18A H 0.7115 0.4206 0.4138 0.045 Uiso 1 1 calc R . .
H18B H 0.5799 0.3228 0.4734 0.045 Uiso 1 1 calc R . .
H18C H 0.5203 0.4160 0.4138 0.045 Uiso 1 1 calc R . .
C19 C 0.6252(4) 0.1514(3) 0.3072(2) 0.0281(5) Uani 1 1 d . . .
H19A H 0.7516 0.2098 0.3279 0.034 Uiso 1 1 calc R . .
H19B H 0.6024 0.0906 0.2359 0.034 Uiso 1 1 calc R . .
C20 C 0.5568(4) 0.0640(3) 0.3867(2) 0.0331(6) Uani 1 1 d . . .
H20A H 0.6287 0.1120 0.4571 0.040 Uiso 1 1 calc R . .
H20B H 0.5593 -0.0284 0.3640 0.040 Uiso 1 1 calc R . .
C21 C 0.3645(4) 0.0492(3) 0.3878(2) 0.0335(6) Uani 1 1 d . . .
H21A H 0.2811 -0.0492 0.3607 0.040 Uiso 1 1 calc R . .
H21B H 0.3489 0.0843 0.4596 0.040 Uiso 1 1 calc R . .
C22 C 0.3362(3) 0.1377(3) 0.3156(2) 0.0291(5) Uani 1 1 d . . .
H22A H 0.2758 0.0784 0.2447 0.035 Uiso 1 1 calc R . .
H22B H 0.2662 0.1872 0.3447 0.035 Uiso 1 1 calc R . .
O1 O 1.3362(3) 0.9654(2) 0.07711(16) 0.0377(5) Uani 1 1 d . . .
O2 O 0.6674(2) 0.4315(2) 0.10468(15) 0.0305(4) Uani 1 1 d . . .
N1 N 0.5214(3) 0.2420(2) 0.31214(17) 0.0248(4) Uani 1 1 d . . .
Br1 Br 0.13366(4) 0.39257(3) 0.34067(2) 0.02610(10) Uani 0.8561(13) 1 d P A 1
Br1A Br 0.9457(4) 0.3234(3) 0.5574(2) 0.0575(9) Uani 0.1439(13) 1 d P A 2
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C2 C1 C6 120.7(3) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 118.5(3) . . ?
C5 C6 C7 123.7(2) . . ?
C1 C6 C7 117.8(3) . . ?
C8 C7 C6 127.5(3) . . ?
C8 C7 H7 116.3 . . ?
C6 C7 H7 116.3 . . ?
C7 C8 C9 119.3(2) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
O1 C9 C8 120.3(2) . . ?
O1 C9 C10 119.7(2) . . ?
C8 C9 C10 120.0(2) . . ?
C15 C10 C11 118.4(2) . . ?
C15 C10 C9 118.0(2) . . ?
C11 C10 C9 123.5(2) . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 119.8(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
O2 C13 C14 123.8(2) . . ?
O2 C13 C12 115.6(2) . . ?
C14 C13 C12 120.6(2) . . ?
C15 C14 C13 118.9(2) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C10 121.6(2) . . ?
C14 C15 H15 119.2 . . ?
C10 C15 H15 119.2 . . ?
O2 C16 C17 103.6(2) . . ?
O2 C16 H16A 111.0 . . ?
C17 C16 H16A 111.0 . . ?
O2 C16 H16B 111.0 . . ?
C17 C16 H16B 111.0 . . ?
H16A C16 H16B 109.0 . . ?
N1 C17 C16 113.1(2) . . ?
N1 C17 H17A 109.0 . . ?
C16 C17 H17A 109.0 . . ?
N1 C17 H17B 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C20 103.9(2) . . ?
N1 C19 H19A 111.0 . . ?
C20 C19 H19A 111.0 . . ?
N1 C19 H19B 111.0 . . ?
C20 C19 H19B 111.0 . . ?
H19A C19 H19B 109.0 . . ?
C19 C20 C21 105.3(2) . . ?
C19 C20 H20A 110.7 . . ?
C21 C20 H20A 110.7 . . ?
C19 C20 H20B 110.7 . . ?
C21 C20 H20B 110.7 . . ?
H20A C20 H20B 108.8 . . ?
C22 C21 C20 105.5(2) . . ?
C22 C21 H21A 110.6 . . ?
C20 C21 H21A 110.6 . . ?
C22 C21 H21B 110.6 . . ?
C20 C21 H21B 110.6 . . ?
H21A C21 H21B 108.8 . . ?
N1 C22 C21 105.0(2) . . ?
N1 C22 H22A 110.8 . . ?
C21 C22 H22A 110.8 . . ?
N1 C22 H22B 110.8 . . ?
C21 C22 H22B 110.8 . . ?
H22A C22 H22B 108.8 . . ?
C13 O2 C16 116.4(2) . . ?
C17 N1 C18 110.89(19) . . ?
C17 N1 C19 112.72(19) . . ?
C18 N1 C19 111.3(2) . . ?
C17 N1 C22 109.71(19) . . ?
C18 N1 C22 109.8(2) . . ?
C19 N1 C22 102.14(19) . . ?
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
C1 C2 1.396(4) . ?
C1 C6 1.402(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.461(4) . ?
C7 C8 1.342(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.481(4) . ?
C8 H8 0.9300 . ?
C9 O1 1.235(3) . ?
C9 C10 1.486(4) . ?
C10 C15 1.392(4) . ?
C10 C11 1.394(4) . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9300 . ?
C13 O2 1.368(3) . ?
C13 C14 1.386(4) . ?
C14 C15 1.384(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 O2 1.433(3) . ?
C16 C17 1.522(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N1 1.500(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 N1 1.503(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 N1 1.512(3) . ?
C19 C20 1.529(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.542(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.525(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 N1 1.517(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
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
C6 C1 C2 C3 2.0(4) . . . . ?
C1 C2 C3 C4 -1.4(4) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C3 C4 C5 C6 1.9(5) . . . . ?
C4 C5 C6 C1 -1.3(4) . . . . ?
C4 C5 C6 C7 179.8(3) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
C2 C1 C6 C7 178.3(3) . . . . ?
C5 C6 C7 C8 6.5(4) . . . . ?
C1 C6 C7 C8 -172.4(3) . . . . ?
C6 C7 C8 C9 178.0(2) . . . . ?
C7 C8 C9 O1 -3.2(4) . . . . ?
C7 C8 C9 C10 175.8(2) . . . . ?
O1 C9 C10 C15 -5.2(4) . . . . ?
C8 C9 C10 C15 175.9(2) . . . . ?
O1 C9 C10 C11 172.1(3) . . . . ?
C8 C9 C10 C11 -6.9(4) . . . . ?
C15 C10 C11 C12 1.9(4) . . . . ?
C9 C10 C11 C12 -175.4(2) . . . . ?
C10 C11 C12 C13 -1.2(4) . . . . ?
C11 C12 C13 O2 178.5(2) . . . . ?
C11 C12 C13 C14 -1.0(4) . . . . ?
O2 C13 C14 C15 -177.0(3) . . . . ?
C12 C13 C14 C15 2.4(4) . . . . ?
C13 C14 C15 C10 -1.8(4) . . . . ?
C11 C10 C15 C14 -0.4(4) . . . . ?
C9 C10 C15 C14 177.0(3) . . . . ?
O2 C16 C17 N1 177.7(2) . . . . ?
N1 C19 C20 C21 28.5(3) . . . . ?
C19 C20 C21 C22 -4.1(3) . . . . ?
C20 C21 C22 N1 -21.7(3) . . . . ?
C14 C13 O2 C16 7.4(4) . . . . ?
C12 C13 O2 C16 -172.1(2) . . . . ?
C17 C16 O2 C13 167.5(2) . . . . ?
C16 C17 N1 C18 61.7(3) . . . . ?
C16 C17 N1 C19 -63.8(3) . . . . ?
C16 C17 N1 C22 -176.9(2) . . . . ?
C20 C19 N1 C17 -159.5(2) . . . . ?
C20 C19 N1 C18 75.2(3) . . . . ?
C20 C19 N1 C22 -41.9(2) . . . . ?
C21 C22 N1 C17 159.2(2) . . . . ?
C21 C22 N1 C18 -78.7(2) . . . . ?
C21 C22 N1 C19 39.4(2) . . . . ?
