#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/61/4106183.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_4106183
loop_
_publ_author_name
'Ester Böeß'
'Devarajulu Sureshkumar'
'Abhishek Sud'
'Cornelia Wirtz'
'Christophe Farès'
'Martin Klußmann'
_publ_section_title
;
 Mechanistic Studies on a Cu-Catalyzed Aerobic Oxidative Coupling Reaction
 with N-Phenyl Tetrahydroisoquinoline: Structure of Intermediates and the
 Role of Methanol As a Solvent
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8106
_journal_page_last               8109
_journal_paper_doi               10.1021/ja201610c
_journal_volume                  133
_journal_year                    2011
_chemical_compound_source        methanole
_chemical_formula_moiety         'C15 H14 N, 0.5(Br4 Cu2)'
_chemical_formula_sum            'C15 H14 Br2 Cu N'
_chemical_formula_weight         431.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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_block_code                BSR-BD-061-02
_audit_creation_date             2011-02-04
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.01.21 svn.r1625, GUI svn.r3464)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.803(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0417(12)
_cell_length_b                   10.888(2)
_cell_length_c                   13.8614(17)
_cell_measurement_reflns_used    28322
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.798
_cell_measurement_theta_min      2.6042
_cell_volume                     1510.2(4)
_computing_cell_refinement       'DENZO (Bruker AXS, 2006)'
_computing_data_collection       'DATCOL (Bruker AXS, 2006)'
_computing_data_reduction        'DENZO (Bruker AXS, 2006)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 18.02
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0973
_diffrn_reflns_av_unetI/netI     0.0894
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26070
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         32.90
_diffrn_reflns_theta_min         2.61
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.723
_exptl_absorpt_correction_T_max  0.99793
_exptl_absorpt_correction_T_min  0.99270
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.131
_refine_diff_density_min         -1.402
_refine_diff_density_rms         0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         5631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1294
_refine_ls_R_factor_gt           0.0631
_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)+(0.0341P)²+3.7452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1284
_reflns_number_gt                3310
_reflns_number_total             5631
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja201610c_si_003_2.cif
_cod_data_source_block           7239sadabs
_cod_original_cell_volume        1510.1(4)
_cod_original_sg_symbol_Hall     '-p 2yn)'
_cod_database_code               4106183
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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
Br1 Br 0.10589(5) 0.31135(4) 0.41793(4) 0.02882(13) Uani 1 1 d .
Br2 Br -0.09292(5) 0.07724(5) 0.60236(3) 0.02914(13) Uani 1 1 d .
Cu1 Cu 0.04195(6) 0.11883(5) 0.46770(4) 0.02620(14) Uani 1 1 d .
N1 N 0.8465(4) 0.3868(4) 0.6719(3) 0.0281(9) Uani 1 1 d .
C1 C 0.7247(6) 0.3846(6) 0.7220(4) 0.0404(14) Uani 1 1 d .
H1A H 0.6940 0.4681 0.7304 0.048 Uiso 1 1 calc R
H1B H 0.7440 0.3489 0.7858 0.048 Uiso 1 1 calc R
C2 C 0.6150(6) 0.3113(6) 0.6672(4) 0.0434(14) Uani 1 1 d .
H2A H 0.6330 0.2245 0.6771 0.052 Uiso 1 1 calc R
H2B H 0.5308 0.3296 0.6937 0.052 Uiso 1 1 calc R
C3 C 0.6014(5) 0.3368(5) 0.5621(4) 0.0284(11) Uani 1 1 d .
C4 C 0.4829(5) 0.3247(5) 0.5024(4) 0.0322(11) Uani 1 1 d .
H4 H 0.4044 0.3009 0.5282 0.039 Uiso 1 1 calc R
C5 C 0.4838(5) 0.3485(5) 0.4044(4) 0.0321(11) Uani 1 1 d .
H5 H 0.4046 0.3414 0.3649 0.038 Uiso 1 1 calc R
C6 C 0.6002(6) 0.3831(5) 0.3632(4) 0.0349(12) Uani 1 1 d .
H6 H 0.5981 0.3988 0.2972 0.042 Uiso 1 1 calc R
C7 C 0.7178(5) 0.3937(5) 0.4206(4) 0.0329(12) Uani 1 1 d .
H7 H 0.7965 0.4149 0.3938 0.039 Uiso 1 1 calc R
C8 C 0.7175(5) 0.3723(4) 0.5193(4) 0.0280(10) Uani 1 1 d .
C9 C 0.8425(5) 0.3866(4) 0.5792(4) 0.0282(10) Uani 1 1 d .
H9 H 0.9216 0.3958 0.5495 0.034 Uiso 1 1 calc R
C10 C 0.9732(5) 0.4056(5) 0.7313(4) 0.0296(11) Uani 1 1 d .
C11 C 0.9705(6) 0.4676(5) 0.8172(4) 0.0374(13) Uani 1 1 d .
H11 H 0.8905 0.4969 0.8375 0.045 Uiso 1 1 calc R
C12 C 1.0903(7) 0.4855(6) 0.8733(4) 0.0477(16) Uani 1 1 d .
H12 H 1.0901 0.5273 0.9319 0.057 Uiso 1 1 calc R
C13 C 1.2105(7) 0.4422(7) 0.8434(5) 0.0545(19) Uani 1 1 d .
H13 H 1.2901 0.4550 0.8813 0.065 Uiso 1 1 calc R
C14 C 1.2099(6) 0.3798(6) 0.7564(5) 0.0489(16) Uani 1 1 d .
H14 H 1.2895 0.3505 0.7355 0.059 Uiso 1 1 calc R
C15 C 1.0895(6) 0.3607(5) 0.6998(4) 0.0391(14) Uani 1 1 d .
H15 H 1.0884 0.3182 0.6415 0.047 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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 -1.00 0.0150
1.00 0.00 1.00 0.0150
1.00 2.00 -2.00 0.0500
-1.00 -2.00 2.00 0.0400
1.00 -2.00 -2.00 0.0600
-1.00 2.00 2.00 0.0600
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
Cu1 Br2 Cu1 72.94(3) 3_556 .
Br1 Cu1 Br2 125.60(3) . .
Br1 Cu1 Br2 127.35(3) . 3_556
Br1 Cu1 Cu1 178.75(4) . 3_556
Br2 Cu1 Br2 107.06(3) 3_556 .
Br2 Cu1 Cu1 53.20(2) . 3_556
Br2 Cu1 Cu1 53.86(2) 3_556 3_556
C1 N1 C10 117.2(4) . .
C9 N1 C1 121.4(5) . .
C9 N1 C10 121.0(4) . .
N1 C1 C2 112.0(5) . .
C3 C2 C1 113.6(5) . .
C4 C3 C2 124.7(5) . .
C4 C3 C8 118.1(5) . .
C8 C3 C2 117.2(5) . .
C5 C4 C3 119.2(5) . .
C4 C5 C6 121.8(5) . .
C7 C6 C5 119.7(5) . .
C6 C7 C8 118.9(5) . .
C3 C8 C9 119.7(5) . .
C7 C8 C3 122.2(5) . .
C7 C8 C9 118.1(5) . .
N1 C9 C8 121.7(5) . .
C11 C10 N1 118.4(5) . .
C15 C10 N1 119.5(5) . .
C15 C10 C11 122.1(5) . .
C10 C11 C12 118.4(6) . .
C11 C12 C13 121.1(6) . .
C14 C13 C12 119.1(6) . .
C13 C14 C15 120.1(6) . .
C10 C15 C14 119.1(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 Cu1 2.3142(8) .
Br2 Cu1 2.4386(8) .
Br2 Cu1 2.4177(9) 3_556
Cu1 Br2 2.4177(9) 3_556
Cu1 Cu1 2.8867(13) 3_556
N1 C1 1.457(6) .
N1 C9 1.282(6) .
N1 C10 1.471(7) .
C1 C2 1.512(8) .
C2 C3 1.478(7) .
C3 C4 1.398(7) .
C3 C8 1.405(7) .
C4 C5 1.383(8) .
C5 C6 1.394(8) .
C6 C7 1.373(7) .
C7 C8 1.388(7) .
C8 C9 1.454(7) .
C10 C11 1.371(7) .
C10 C15 1.370(8) .
C11 C12 1.391(8) .
C12 C13 1.391(10) .
C13 C14 1.384(9) .
C14 C15 1.400(8) .
