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#$Date: 2016-03-22 12:37:16 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178956 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/85/4118581.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_4118581
loop_
_publ_author_name
'Fengtao Zhou'
'Jiajia Guo'
'Jianguang Liu'
'Ke Ding'
'Shouyun Yu'
'Qian Cai'
_publ_section_title
;
 Copper-Catalyzed Desymmetric Intramolecular Ullmann C-N Coupling: An
 Enantioselective Preparation of Indolines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14326
_journal_page_last               14329
_journal_paper_doi               10.1021/ja306631z
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C18 H16 Br2 I N O2'
_chemical_formula_weight         565.04
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.76968(13)
_cell_length_b                   12.3217(3)
_cell_length_c                   26.6953(6)
_cell_measurement_temperature    293(2)
_cell_volume                     1897.83(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            44901
_diffrn_reflns_theta_full        67.04
_diffrn_reflns_theta_max         67.04
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    18.276
_exptl_crystal_density_diffrn    1.978
_exptl_crystal_F_000             1080
_refine_diff_density_max         2.444
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.262
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.010(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0682
_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)+(0.1232P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1542
_refine_ls_wR_factor_ref         0.1567
_reflns_number_gt                3223
_reflns_number_total             3373
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja306631z_si_001.cif
_cod_data_source_block           d
_cod_original_cell_volume        1897.83(7)
_cod_database_code               4118581
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
I1 I 0.51188(10) 0.11860(4) 0.004566(17) 0.0906(2) Uani 1 1 d .
Br1 Br 0.58406(19) 0.81189(6) 0.04436(4) 0.1001(3) Uani 1 1 d .
Br2 Br -0.0168(2) -0.00501(8) 0.22174(4) 0.1054(3) Uani 1 1 d .
N1 N 0.8265(10) 0.3796(4) 0.1356(2) 0.0722(12) Uani 1 1 d .
H1B H 0.8805 0.3811 0.1672 0.08(2) Uiso 1 1 d R
O1 O 0.6041(9) 0.2915(4) 0.22159(17) 0.0790(11) Uani 1 1 d .
O2 O 0.2995(11) 0.3814(5) 0.1916(2) 0.0937(14) Uani 1 1 d .
C1 C 0.5216(13) 0.5887(5) 0.0695(2) 0.0716(13) Uani 1 1 d .
H1A H 0.3835 0.5941 0.0517 0.086 Uiso 1 1 calc R
C2 C 0.6685(14) 0.6761(5) 0.0737(3) 0.0762(15) Uani 1 1 d .
C3 C 0.8786(14) 0.6697(6) 0.0985(3) 0.0807(16) Uani 1 1 d .
H3A H 0.9764 0.7297 0.0998 0.097 Uiso 1 1 calc R
C4 C 0.9424(13) 0.5730(5) 0.1216(3) 0.0783(15) Uani 1 1 d .
H4A H 1.0822 0.5673 0.1388 0.094 Uiso 1 1 calc R
C5 C 0.7921(11) 0.4854(5) 0.1185(2) 0.0677(13) Uani 1 1 d .
C6 C 0.5839(12) 0.4931(5) 0.0924(2) 0.0681(12) Uani 1 1 d .
C7 C 0.4657(12) 0.3824(4) 0.0926(2) 0.0695(13) Uani 1 1 d .
H7A H 0.4800 0.3466 0.0604 0.083 Uiso 1 1 calc R
H7B H 0.3030 0.3886 0.1013 0.083 Uiso 1 1 calc R
C8 C 0.6042(11) 0.3210(5) 0.1341(2) 0.0678(12) Uani 1 1 d .
C9 C 0.6521(13) 0.2000(5) 0.1230(2) 0.0718(13) Uani 1 1 d .
H9A H 0.7391 0.1952 0.0920 0.086 Uiso 1 1 calc R
H9B H 0.7497 0.1713 0.1495 0.086 Uiso 1 1 calc R
C10 C 0.4415(12) 0.1291(4) 0.1185(2) 0.0702(13) Uani 1 1 d .
C11 C 0.3525(13) 0.0888(5) 0.0732(3) 0.0746(15) Uani 1 1 d .
C12 C 0.1579(15) 0.0225(6) 0.0722(3) 0.0855(18) Uani 1 1 d .
H12A H 0.1027 -0.0035 0.0418 0.103 Uiso 1 1 calc R
C13 C 0.0449(15) -0.0055(6) 0.1164(4) 0.092(2) Uani 1 1 d .
H13A H -0.0874 -0.0486 0.1159 0.111 Uiso 1 1 calc R
C14 C 0.1346(14) 0.0324(5) 0.1607(3) 0.0781(16) Uani 1 1 d .
C15 C 0.3302(13) 0.0969(5) 0.1623(3) 0.0776(15) Uani 1 1 d .
H15A H 0.3884 0.1192 0.1931 0.093 Uiso 1 1 calc R
C16 C 0.4791(13) 0.3345(4) 0.1848(2) 0.0703(13) Uani 1 1 d .
C17 C 0.5088(17) 0.2989(7) 0.2721(3) 0.0926(19) Uani 1 1 d .
H17A H 0.3471 0.2775 0.2722 0.111 Uiso 1 1 calc R
H17B H 0.5199 0.3728 0.2844 0.111 Uiso 1 1 calc R
C18 C 0.647(3) 0.2247(12) 0.3042(4) 0.129(4) Uani 1 1 d .
H18A H 0.5912 0.2286 0.3380 0.194 Uiso 1 1 calc R
H18B H 0.8069 0.2459 0.3032 0.194 Uiso 1 1 calc R
H18C H 0.6317 0.1517 0.2920 0.194 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 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C5 N1 C8 109.0(5)
C5 N1 H1B 109.7
C8 N1 H1B 109.7
C16 O1 C17 117.0(6)
C6 C1 C2 118.3(7)
C6 C1 H1A 120.8
C2 C1 H1A 120.8
C1 C2 C3 122.3(6)
C1 C2 Br1 119.7(6)
C3 C2 Br1 118.0(5)
C2 C3 C4 119.5(6)
C2 C3 H3A 120.2
C4 C3 H3A 120.2
C5 C4 C3 118.3(7)
C5 C4 H4A 120.9
C3 C4 H4A 120.9
C4 C5 C6 121.1(6)
C4 C5 N1 128.1(6)
C6 C5 N1 110.5(5)
C1 C6 C5 120.4(6)
C1 C6 C7 130.7(6)
C5 C6 C7 108.8(5)
C6 C7 C8 102.0(5)
C6 C7 H7A 111.4
C8 C7 H7A 111.4
C6 C7 H7B 111.4
C8 C7 H7B 111.4
H7A C7 H7B 109.2
N1 C8 C16 109.3(5)
N1 C8 C9 108.8(5)
C16 C8 C9 110.9(5)
N1 C8 C7 103.1(5)
C16 C8 C7 109.2(5)
C9 C8 C7 115.1(5)
C10 C9 C8 115.6(6)
C10 C9 H9A 108.4
C8 C9 H9A 108.4
C10 C9 H9B 108.4
C8 C9 H9B 108.4
H9A C9 H9B 107.4
C15 C10 C11 117.0(6)
C15 C10 C9 118.2(6)
C11 C10 C9 124.7(6)
C12 C11 C10 121.2(7)
C12 C11 I1 116.4(5)
C10 C11 I1 122.3(5)
C11 C12 C13 120.7(7)
C11 C12 H12A 119.7
C13 C12 H12A 119.7
C14 C13 C12 118.0(7)
C14 C13 H13A 121.0
C12 C13 H13A 121.0
C13 C14 C15 122.0(7)
C13 C14 Br2 118.8(6)
C15 C14 Br2 119.1(6)
C14 C15 C10 121.0(7)
C14 C15 H15A 119.5
C10 C15 H15A 119.5
O2 C16 O1 123.2(6)
O2 C16 C8 126.1(6)
O1 C16 C8 110.6(6)
O1 C17 C18 107.0(7)
O1 C17 H17A 110.3
C18 C17 H17A 110.3
O1 C17 H17B 110.3
C18 C17 H17B 110.3
H17A C17 H17B 108.6
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C11 2.082(7)
Br1 C2 1.910(6)
Br2 C14 1.906(7)
N1 C5 1.396(8)
N1 C8 1.473(9)
N1 H1B 0.8999
O1 C16 1.329(8)
O1 C17 1.458(9)
O2 C16 1.200(9)
C1 C6 1.374(9)
C1 C2 1.375(10)
C1 H1A 0.9300
C2 C3 1.385(12)
C3 C4 1.391(10)
C3 H3A 0.9300
C4 C5 1.388(9)
C4 H4A 0.9300
C5 C6 1.392(10)
C6 C7 1.524(8)
C7 C8 1.561(8)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C16 1.542(9)
C8 C9 1.545(8)
C9 C10 1.501(10)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C15 1.391(10)
C10 C11 1.406(9)
C11 C12 1.389(11)
C12 C13 1.390(12)
C12 H12A 0.9300
C13 C14 1.373(12)
C13 H13A 0.9300
C14 C15 1.381(11)
C15 H15A 0.9300
C17 C18 1.484(13)
C17 H17A 0.9700
C17 H17B 0.9700
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B O2 0.90 2.50 3.112(9) 125.3 1_655
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
C6 C1 C2 C3 2.1(10)
C6 C1 C2 Br1 -178.0(5)
C1 C2 C3 C4 -2.0(11)
Br1 C2 C3 C4 178.0(6)
C2 C3 C4 C5 0.5(11)
C3 C4 C5 C6 0.8(10)
C3 C4 C5 N1 175.3(6)
C8 N1 C5 C4 167.8(6)
C8 N1 C5 C6 -17.2(7)
C2 C1 C6 C5 -0.7(9)
C2 C1 C6 C7 -176.9(6)
C4 C5 C6 C1 -0.7(9)
N1 C5 C6 C1 -176.1(6)
C4 C5 C6 C7 176.3(6)
N1 C5 C6 C7 0.9(7)
C1 C6 C7 C8 -169.1(6)
C5 C6 C7 C8 14.3(6)
C5 N1 C8 C16 -90.8(6)
C5 N1 C8 C9 148.0(5)
C5 N1 C8 C7 25.3(6)
C6 C7 C8 N1 -23.2(6)
C6 C7 C8 C16 93.0(6)
C6 C7 C8 C9 -141.5(6)
N1 C8 C9 C10 -178.1(5)
C16 C8 C9 C10 61.6(7)
C7 C8 C9 C10 -63.0(7)
C8 C9 C10 C15 -77.4(7)
C8 C9 C10 C11 105.3(7)
C15 C10 C11 C12 1.9(9)
C9 C10 C11 C12 179.2(6)
C15 C10 C11 I1 -175.2(5)
C9 C10 C11 I1 2.1(8)
C10 C11 C12 C13 0.3(11)
I1 C11 C12 C13 177.5(6)
C11 C12 C13 C14 -1.4(11)
C12 C13 C14 C15 0.3(11)
C12 C13 C14 Br2 -179.9(6)
C13 C14 C15 C10 1.9(11)
Br2 C14 C15 C10 -177.8(5)
C11 C10 C15 C14 -3.0(9)
C9 C10 C15 C14 179.5(6)
C17 O1 C16 O2 2.7(10)
C17 O1 C16 C8 179.5(6)
N1 C8 C16 O2 114.5(7)
C9 C8 C16 O2 -125.5(7)
C7 C8 C16 O2 2.4(9)
N1 C8 C16 O1 -62.1(6)
C9 C8 C16 O1 57.9(7)
C7 C8 C16 O1 -174.3(5)
C16 O1 C17 C18 167.1(9)
