#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/47/7104767.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_7104767
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         'C15 H20 N O, Br'
_chemical_formula_sum            'C15 H20 Br N O'
_chemical_formula_weight         310.23
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.960(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6662(18)
_cell_length_b                   13.109(2)
_cell_length_c                   11.3363(18)
_cell_measurement_reflns_used    4440
_cell_measurement_temperature    383(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.53
_cell_volume                     1425.2(4)
_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      383(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13289
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    2.873
_exptl_absorpt_correction_T_max  0.772
_exptl_absorpt_correction_T_min  0.593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.03; (Sheldrick)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.998
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3504
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0357
_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)+(0.0550P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                2800
_reflns_number_total             3504
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b906823f.txt
_cod_data_source_block           jms0805m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      P2(1)/n
_cod_database_code               7104767
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.04747(3) 0.234211(18) 0.05305(2) 0.02821(10) Uani 1 1 d . . .
C1 C 0.7692(2) 0.01646(19) -0.2116(2) 0.0255(5) Uani 1 1 d . . .
H1A H 0.8406 -0.0359 -0.1861 0.031 Uiso 1 1 calc R . .
H1B H 0.8095 0.0810 -0.2194 0.031 Uiso 1 1 calc R . .
C2 C 0.6453(2) -0.01144(18) -0.3408(2) 0.0239(5) Uani 1 1 d . . .
H2A H 0.6711 -0.0639 -0.3865 0.029 Uiso 1 1 calc R . .
H2B H 0.6122 0.0479 -0.3972 0.029 Uiso 1 1 calc R . .
C3 C 0.5327(2) -0.05087(19) -0.3022(2) 0.0269(5) Uani 1 1 d . . .
H3A H 0.4561 -0.0028 -0.3280 0.032 Uiso 1 1 calc R . .
H3B H 0.4965 -0.1161 -0.3434 0.032 Uiso 1 1 calc R . .
C4 C 0.6069(2) -0.06171(18) -0.1534(2) 0.0239(5) Uani 1 1 d . . .
H4A H 0.5420 -0.0546 -0.1150 0.029 Uiso 1 1 calc R . .
H4B H 0.6536 -0.1271 -0.1281 0.029 Uiso 1 1 calc R . .
C5 C 0.6399(3) 0.12631(18) -0.1263(2) 0.0309(5) Uani 1 1 d . . .
H5A H 0.5814 0.1247 -0.0817 0.046 Uiso 1 1 calc R . .
H5B H 0.5841 0.1408 -0.2176 0.046 Uiso 1 1 calc R . .
H5C H 0.7094 0.1784 -0.0885 0.046 Uiso 1 1 calc R . .
C6 C 0.8257(2) 0.01453(18) 0.02221(19) 0.0200(4) Uani 1 1 d . . .
H6A H 0.8975 0.0638 0.0321 0.024 Uiso 1 1 calc R . .
H6B H 0.8663 -0.0529 0.0314 0.024 Uiso 1 1 calc R . .
C7 C 0.7832(2) 0.03053(17) 0.1321(2) 0.0208(4) Uani 1 1 d . . .
C8 C 0.8933(2) 0.06998(17) 0.2539(2) 0.0207(4) Uani 1 1 d . . .
H8 H 0.9813 0.0823 0.2588 0.025 Uiso 1 1 calc R . .
C9 C 0.8699(2) 0.08859(16) 0.3580(2) 0.0195(4) Uani 1 1 d . . .
H9 H 0.7807 0.0740 0.3486 0.023 Uiso 1 1 calc R . .
C10 C 0.9673(2) 0.12901(16) 0.4848(2) 0.0197(4) Uani 1 1 d . . .
C11 C 0.9184(2) 0.15130(17) 0.5779(2) 0.0228(5) Uani 1 1 d . . .
H11 H 0.8246 0.1420 0.5570 0.027 Uiso 1 1 calc R . .
C12 C 1.0080(3) 0.18696(17) 0.7003(2) 0.0264(5) Uani 1 1 d . . .
H12 H 0.9746 0.2008 0.7619 0.032 Uiso 1 1 calc R . .
C13 C 1.1469(3) 0.20224(18) 0.7318(2) 0.0296(5) Uani 1 1 d . . .
H13 H 1.2070 0.2262 0.8147 0.035 Uiso 1 1 calc R . .
C14 C 1.1969(3) 0.18207(18) 0.6406(2) 0.0284(5) Uani 1 1 d . . .
H14 H 1.2904 0.1932 0.6615 0.034 Uiso 1 1 calc R . .
C15 C 1.1076(2) 0.14519(17) 0.5179(2) 0.0236(5) Uani 1 1 d . . .
H15 H 1.1418 0.1311 0.4569 0.028 Uiso 1 1 calc R . .
N1 N 0.71023(18) 0.02429(14) -0.11242(16) 0.0196(4) Uani 1 1 d . . .
O1 O 0.66669(15) 0.00997(14) 0.11834(14) 0.0301(4) Uani 1 1 d . . .
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
N1 C1 C2 105.21(17) . . ?
N1 C1 H1A 110.7 . . ?
C2 C1 H1A 110.7 . . ?
N1 C1 H1B 110.7 . . ?
C2 C1 H1B 110.7 . . ?
H1A C1 H1B 108.8 . . ?
C1 C2 C3 105.30(17) . . ?
C1 C2 H2A 110.7 . . ?
C3 C2 H2A 110.7 . . ?
C1 C2 H2B 110.7 . . ?
C3 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
C4 C3 C2 104.73(17) . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
N1 C4 C3 103.16(18) . . ?
N1 C4 H4A 111.1 . . ?
C3 C4 H4A 111.1 . . ?
N1 C4 H4B 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 C7 114.84(17) . . ?
N1 C6 H6A 108.6 . . ?
C7 C6 H6A 108.6 . . ?
N1 C6 H6B 108.6 . . ?
C7 C6 H6B 108.6 . . ?
H6A C6 H6B 107.5 . . ?
O1 C7 C8 123.7(2) . . ?
O1 C7 C6 121.5(2) . . ?
C8 C7 C6 114.85(18) . . ?
C9 C8 C7 121.2(2) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 127.8(2) . . ?
C8 C9 H9 116.1 . . ?
C10 C9 H9 116.1 . . ?
C15 C10 C11 118.5(2) . . ?
C15 C10 C9 122.71(19) . . ?
C11 C10 C9 118.75(19) . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 119.9(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C10 120.7(2) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C6 N1 C4 114.73(17) . . ?
C6 N1 C5 109.50(17) . . ?
C4 N1 C5 111.70(17) . . ?
C6 N1 C1 109.24(16) . . ?
C4 N1 C1 101.94(17) . . ?
C5 N1 C1 109.40(18) . . ?
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 N1 1.513(3) . ?
C1 C2 1.527(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.536(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.525(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.501(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N1 1.508(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 N1 1.489(2) . ?
C6 C7 1.515(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O1 1.213(3) . ?
C7 C8 1.460(3) . ?
C8 C9 1.331(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.456(3) . ?
C9 H9 0.9300 . ?
C10 C15 1.391(3) . ?
C10 C11 1.397(3) . ?
C11 C12 1.377(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
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
N1 C1 C2 C3 -17.3(3) . . . . ?
C1 C2 C3 C4 -10.0(3) . . . . ?
C2 C3 C4 N1 33.9(2) . . . . ?
N1 C6 C7 O1 29.6(3) . . . . ?
N1 C6 C7 C8 -151.55(19) . . . . ?
O1 C7 C8 C9 -1.9(3) . . . . ?
C6 C7 C8 C9 179.3(2) . . . . ?
C7 C8 C9 C10 -179.0(2) . . . . ?
C8 C9 C10 C15 -6.3(4) . . . . ?
C8 C9 C10 C11 174.5(2) . . . . ?
C15 C10 C11 C12 -1.0(3) . . . . ?
C9 C10 C11 C12 178.2(2) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C13 C14 C15 C10 0.6(3) . . . . ?
C11 C10 C15 C14 0.3(3) . . . . ?
C9 C10 C15 C14 -178.8(2) . . . . ?
C7 C6 N1 C4 -71.6(2) . . . . ?
C7 C6 N1 C5 54.9(2) . . . . ?
C7 C6 N1 C1 174.73(18) . . . . ?
C3 C4 N1 C6 -162.40(17) . . . . ?
C3 C4 N1 C5 72.2(2) . . . . ?
C3 C4 N1 C1 -44.5(2) . . . . ?
C2 C1 N1 C6 160.08(19) . . . . ?
C2 C1 N1 C4 38.3(2) . . . . ?
C2 C1 N1 C5 -80.1(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653149
