#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:02:01 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180056 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/02/7050240.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_7050240
loop_
_publ_author_name
'Mateo Alajarín'
'Angel Vidal'
'María-Mar Ortín'
'Delia Bautista'
_publ_section_title
;
 Persistent radical effect in the intramolecular addition of benzylic
 radicals onto ketenimines: selective cross-coupling of
 α-(indol-2-yl)benzyl radicals with the 1-cyano-1-methylethyl radical
;
_journal_issue                   5
_journal_name_full               'New J. Chem.'
_journal_page_first              570
_journal_page_last               577
_journal_paper_doi               10.1039/b312930f
_journal_volume                  28
_journal_year                    2004
_chemical_formula_sum            'C32 H28 N2'
_chemical_formula_weight         440.56
_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                97.4250(10)
_cell_angle_beta                 90.1360(10)
_cell_angle_gamma                110.4370(10)
_cell_formula_units_Z            2
_cell_length_a                   10.1741(8)
_cell_length_b                   10.6139(9)
_cell_length_c                   11.3542(9)
_cell_measurement_reflns_used    7642
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      18.05
_cell_measurement_theta_min      2.55
_cell_volume                     1137.81(16)
_computing_cell_refinement       'Bruker SAINT'
_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, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       Ω-scan
_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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12460
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.075
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    'NH free, rigid methyls, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4621
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0402
_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)+(0.0618P)²+0.2737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1065
_reflns_number_gt                4142
_reflns_number_total             4621
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b312930f.txt
_cod_data_source_block           17
_cod_database_code               7050240
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
N1 N 0.84549(9) 0.07981(9) 0.29163(8) 0.0163(2) Uani 1 1 d . . .
N2 N 0.93718(10) 0.22105(10) 0.48425(8) 0.0185(2) Uani 1 1 d . . .
H2 H 1.0190(17) 0.2071(15) 0.4890(13) 0.033(4) Uiso 1 1 d . . .
C1 C 0.84692(12) -0.02909(11) 0.10850(10) 0.0191(2) Uani 1 1 d . . .
H1 H 0.8565 -0.0466 0.0254 0.023 Uiso 1 1 calc R . .
C2 C 0.80718(11) -0.12673(11) 0.19035(10) 0.0179(2) Uani 1 1 d . . .
C3 C 0.76908(11) -0.26860(11) 0.17724(11) 0.0198(2) Uani 1 1 d . . .
H3 H 0.7675 -0.3187 0.1012 0.024 Uiso 1 1 calc R . .
C4 C 0.73411(11) -0.33420(11) 0.27581(11) 0.0210(2) Uani 1 1 d . . .
H4 H 0.7069 -0.4303 0.2669 0.025 Uiso 1 1 calc R . .
C5 C 0.73793(12) -0.26201(12) 0.38907(11) 0.0212(2) Uani 1 1 d . . .
H5 H 0.7147 -0.3101 0.4556 0.025 Uiso 1 1 calc R . .
C6 C 0.77492(11) -0.12199(11) 0.40604(10) 0.0191(2) Uani 1 1 d . . .
H6 H 0.7781 -0.0731 0.4829 0.023 Uiso 1 1 calc R . .
C7 C 0.80739(11) -0.05559(11) 0.30540(10) 0.0167(2) Uani 1 1 d . . .
C8 C 0.86815(11) 0.09393(11) 0.17422(10) 0.0176(2) Uani 1 1 d . . .
C9 C 0.90493(12) 0.23928(11) 0.15526(10) 0.0178(2) Uani 1 1 d . . .
C10 C 1.01897(12) 0.27952(12) 0.06458(10) 0.0211(2) Uani 1 1 d . . .
H10A H 1.0947 0.2469 0.0828 0.025 Uiso 1 1 calc R . .
H10B H 1.0568 0.3786 0.0687 0.025 Uiso 1 1 calc R . .
H10C H 0.9781 0.2387 -0.0156 0.025 Uiso 1 1 calc R . .
C11 C 0.95844(11) 0.31353(11) 0.28803(10) 0.0174(2) Uani 1 1 d . . .
C12 C 0.93927(12) 0.45043(11) 0.31310(10) 0.0202(2) Uani 1 1 d . . .
H12A H 0.9690 0.4897 0.3960 0.024 Uiso 1 1 calc R . .
H12B H 0.8401 0.4380 0.2993 0.024 Uiso 1 1 calc R . .
H12C H 0.9963 0.5117 0.2601 0.024 Uiso 1 1 calc R . .
C13 C 0.86681(11) 0.20942(11) 0.36968(10) 0.0166(2) Uani 1 1 d . . .
C14 C 0.72193(12) 0.21737(12) 0.40630(10) 0.0201(2) Uani 1 1 d . . .
H14A H 0.7202 0.3097 0.4043 0.024 Uiso 1 1 calc R . .
H14B H 0.6447 0.1514 0.3528 0.024 Uiso 1 1 calc R . .
C15 C 0.70937(12) 0.18256(11) 0.53074(10) 0.0190(2) Uani 1 1 d . . .
C16 C 0.59707(12) 0.15502(12) 0.60363(11) 0.0238(3) Uani 1 1 d . . .
H16 H 0.5074 0.1503 0.5749 0.029 Uiso 1 1 calc R . .
C17 C 0.61749(13) 0.13434(13) 0.72001(11) 0.0283(3) Uani 1 1 d . . .
H17 H 0.5414 0.1157 0.7713 0.034 Uiso 1 1 calc R . .
C18 C 0.74883(14) 0.14093(13) 0.76122(11) 0.0272(3) Uani 1 1 d . . .
H18 H 0.7612 0.1270 0.8409 0.033 Uiso 1 1 calc R . .
C19 C 0.86277(12) 0.16744(12) 0.68846(10) 0.0221(2) Uani 1 1 d . . .
H19 H 0.9521 0.1710 0.7168 0.026 Uiso 1 1 calc R . .
C20 C 0.84066(12) 0.18855(11) 0.57277(10) 0.0176(2) Uani 1 1 d . . .
C21 C 0.77290(12) 0.26162(11) 0.10864(10) 0.0191(2) Uani 1 1 d D . .
C22 C 0.63902(12) 0.16384(12) 0.10945(10) 0.0218(2) Uani 1 1 d D . .
H22 H 0.6277 0.0840 0.1440 0.026 Uiso 1 1 calc R . .
C23 C 0.52196(13) 0.18090(13) 0.06075(11) 0.0268(3) Uani 1 1 d D . .
H23 H 0.4316 0.1136 0.0633 0.032 Uiso 1 1 calc R . .
C24 C 0.53642(14) 0.29545(13) 0.00866(12) 0.0299(3) Uani 1 1 d D . .
H24 H 0.4565 0.3069 -0.0252 0.036 Uiso 1 1 calc R . .
C25 C 0.66828(14) 0.39324(13) 0.00627(11) 0.0284(3) Uani 1 1 d D . .
H25 H 0.6790 0.4718 -0.0299 0.034 Uiso 1 1 calc R . .
C26 C 0.78507(13) 0.37733(12) 0.05640(10) 0.0240(3) Uani 1 1 d D . .
H26 H 0.8747 0.4461 0.0552 0.029 Uiso 1 1 calc R . .
C31 C 1.11530(11) 0.33034(11) 0.30632(10) 0.0185(2) Uani 1 1 d D . .
C32 C 1.16089(12) 0.21853(12) 0.29687(10) 0.0205(2) Uani 1 1 d D . .
H32 H 1.0930 0.1293 0.2853 0.025 Uiso 1 1 calc R . .
C33 C 1.30236(13) 0.23551(13) 0.30403(11) 0.0243(3) Uani 1 1 d D . .
H33 H 1.3300 0.1582 0.2967 0.029 Uiso 1 1 calc R . .
C34 C 1.40357(13) 0.36464(14) 0.32177(12) 0.0299(3) Uani 1 1 d D . .
H34 H 1.5005 0.3765 0.3254 0.036 Uiso 1 1 calc R . .
C35 C 1.36149(13) 0.47583(13) 0.33403(13) 0.0322(3) Uani 1 1 d D . .
H35 H 1.4300 0.5647 0.3476 0.039 Uiso 1 1 calc R . .
C36 C 1.21966(13) 0.45891(12) 0.32673(11) 0.0252(3) Uani 1 1 d D . .
H36 H 1.1931 0.5369 0.3359 0.030 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'
N N 0.0061 0.0033 '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
C8 N1 C7 109.39(9) . . ?
C8 N1 C13 113.99(9) . . ?
C7 N1 C13 136.62(9) . . ?
C20 N2 C13 111.19(9) . . ?
C8 C1 C2 106.06(10) . . ?
C3 C2 C7 118.70(10) . . ?
C3 C2 C1 133.50(11) . . ?
C7 C2 C1 107.80(10) . . ?
C4 C3 C2 119.21(11) . . ?
C3 C4 C5 121.30(10) . . ?
C6 C5 C4 121.40(11) . . ?
C5 C6 C7 117.31(11) . . ?
N1 C7 C6 131.68(10) . . ?
N1 C7 C2 106.25(9) . . ?
C6 C7 C2 122.06(10) . . ?
C1 C8 N1 110.50(10) . . ?
C1 C8 C9 138.63(10) . . ?
N1 C8 C9 110.84(9) . . ?
C8 C9 C10 111.70(9) . . ?
C8 C9 C21 109.69(9) . . ?
C10 C9 C21 108.37(9) . . ?
C8 C9 C11 100.02(8) . . ?
C10 C9 C11 113.02(9) . . ?
C21 C9 C11 113.86(9) . . ?
C12 C11 C31 110.71(9) . . ?
C12 C11 C13 111.80(9) . . ?
C31 C11 C13 109.35(9) . . ?
C12 C11 C9 112.43(9) . . ?
C31 C11 C9 108.41(9) . . ?
C13 C11 C9 103.87(8) . . ?
N2 C13 N1 114.01(9) . . ?
N2 C13 C14 102.18(9) . . ?
N1 C13 C14 109.85(8) . . ?
N2 C13 C11 112.81(9) . . ?
N1 C13 C11 99.97(8) . . ?
C14 C13 C11 118.55(9) . . ?
C15 C14 C13 104.04(9) . . ?
C16 C15 C20 120.50(11) . . ?
C16 C15 C14 130.98(11) . . ?
C20 C15 C14 108.44(10) . . ?
C15 C16 C17 118.89(11) . . ?
C18 C17 C16 120.20(11) . . ?
C17 C18 C19 121.57(11) . . ?
C20 C19 C18 117.44(11) . . ?
C19 C20 C15 121.40(11) . . ?
C19 C20 N2 128.77(10) . . ?
C15 C20 N2 109.81(10) . . ?
C22 C21 C26 117.53(11) . . ?
C22 C21 C9 121.62(10) . . ?
C26 C21 C9 120.71(10) . . ?
C23 C22 C21 121.31(11) . . ?
C24 C23 C22 120.25(11) . . ?
C23 C24 C25 119.38(11) . . ?
C24 C25 C26 120.46(12) . . ?
C25 C26 C21 121.06(11) . . ?
C36 C31 C32 116.51(11) . . ?
C36 C31 C11 120.99(10) . . ?
C32 C31 C11 122.40(10) . . ?
C33 C32 C31 121.69(11) . . ?
C34 C33 C32 120.35(11) . . ?
C35 C34 C33 119.07(11) . . ?
C34 C35 C36 120.62(11) . . ?
C35 C36 C31 121.72(11) . . ?
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
N1 C8 1.3717(14) . ?
N1 C7 1.3819(14) . ?
N1 C13 1.4834(14) . ?
N2 C20 1.3969(14) . ?
N2 C13 1.4534(14) . ?
C1 C8 1.3634(16) . ?
C1 C2 1.4350(16) . ?
C2 C3 1.4050(15) . ?
C2 C7 1.4215(16) . ?
C3 C4 1.3763(17) . ?
C4 C5 1.4024(17) . ?
C5 C6 1.3865(16) . ?
C6 C7 1.3996(16) . ?
C8 C9 1.4998(15) . ?
C9 C10 1.5369(15) . ?
C9 C21 1.5467(15) . ?
C9 C11 1.6060(15) . ?
C11 C12 1.5238(15) . ?
C11 C31 1.5529(15) . ?
C11 C13 1.5808(15) . ?
C13 C14 1.5600(15) . ?
C14 C15 1.5006(16) . ?
C15 C16 1.3820(16) . ?
C15 C20 1.3950(16) . ?
C16 C17 1.3938(18) . ?
C17 C18 1.3902(19) . ?
C18 C19 1.3937(17) . ?
C19 C20 1.3914(16) . ?
C21 C22 1.3956(16) . ?
C21 C26 1.3993(16) . ?
C22 C23 1.3894(17) . ?
C23 C24 1.3824(19) . ?
C24 C25 1.3831(19) . ?
C25 C26 1.3878(17) . ?
C31 C36 1.3959(16) . ?
C31 C32 1.4096(16) . ?
C32 C33 1.3876(16) . ?
C33 C34 1.3861(18) . ?
C34 C35 1.3807(19) . ?
C35 C36 1.3914(18) . ?
