#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:47:24 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178444 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/65/4026573.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_4026573
loop_
_publ_author_name
'Yao-Zong Liu'
'Jie Zhang'
'Peng-Fei Xu'
'Yong-Chun Luo'
_publ_section_title
;
 Organocatalytic Asymmetric Michael Addition of 1-Acetylindolin-3-ones to
 α,β-Unsaturated Aldehydes: Synthesis of 2-Substituted Indolin-3-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7551
_journal_page_last               7555
_journal_paper_doi               10.1021/jo201123p
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C19 H16 Br N O3'
_chemical_formula_weight         386.24
_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                82.408(12)
_cell_angle_beta                 80.410(13)
_cell_angle_gamma                77.913(14)
_cell_formula_units_Z            2
_cell_length_a                   8.663(11)
_cell_length_b                   9.218(11)
_cell_length_c                   12.471(15)
_cell_measurement_reflns_used    1560
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.36
_cell_measurement_theta_min      2.27
_cell_volume                     955(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0798
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6870
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    2.166
_exptl_absorpt_correction_T_max  0.6472
_exptl_absorpt_correction_T_min  0.6135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0538
_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)+(0.0543P)²+0.5917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1368
_reflns_number_gt                1980
_reflns_number_total             3499
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201123p_si_002.cif
_cod_data_source_block           p-1
_cod_database_code               4026573
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
Br1 Br 0.42968(10) 0.23839(7) 1.12135(4) 0.0860(3) Uani 1 1 d .
C1 C 0.6484(5) 0.1576(4) 0.5657(3) 0.0290(10) Uani 1 1 d .
H1 H 0.6289 0.0622 0.6047 0.035 Uiso 1 1 calc R
C2 C 0.6186(5) 0.1739(5) 0.4463(3) 0.0315(10) Uani 1 1 d .
C3 C 0.7379(5) 0.2692(5) 0.3918(3) 0.0324(10) Uani 1 1 d .
C4 C 0.7475(6) 0.3474(5) 0.2899(4) 0.0437(12) Uani 1 1 d .
H4 H 0.6714 0.3504 0.2447 0.052 Uiso 1 1 calc R
C5 C 0.8730(7) 0.4212(6) 0.2565(4) 0.0594(15) Uani 1 1 d .
H5 H 0.8810 0.4761 0.1883 0.071 Uiso 1 1 calc R
C6 C 0.9869(6) 0.4144(6) 0.3234(5) 0.0588(15) Uani 1 1 d .
H6 H 1.0710 0.4643 0.2991 0.071 Uiso 1 1 calc R
C7 C 0.9789(6) 0.3359(5) 0.4248(4) 0.0481(13) Uani 1 1 d .
H7 H 1.0557 0.3324 0.4695 0.058 Uiso 1 1 calc R
C8 C 0.8534(5) 0.2622(5) 0.4585(3) 0.0349(11) Uani 1 1 d .
C9 C 0.5338(5) 0.2926(5) 0.6157(3) 0.0311(10) Uani 1 1 d .
H9 H 0.5830 0.3801 0.5916 0.037 Uiso 1 1 calc R
C10 C 0.5064(5) 0.2777(5) 0.7394(3) 0.0334(10) Uani 1 1 d .
C11 C 0.5771(6) 0.3602(5) 0.7955(4) 0.0442(12) Uani 1 1 d .
H11 H 0.6393 0.4259 0.7567 0.053 Uiso 1 1 calc R
C12 C 0.5562(6) 0.3458(5) 0.9086(4) 0.0547(14) Uani 1 1 d .
H12 H 0.6059 0.4002 0.9454 0.066 Uiso 1 1 calc R
C13 C 0.4625(7) 0.2517(5) 0.9662(4) 0.0530(14) Uani 1 1 d .
C14 C 0.3913(7) 0.1695(6) 0.9131(4) 0.0658(16) Uani 1 1 d .
H14 H 0.3271 0.1060 0.9528 0.079 Uiso 1 1 calc R
C15 C 0.4149(6) 0.1806(5) 0.8002(4) 0.0548(14) Uani 1 1 d .
H15 H 0.3687 0.1221 0.7644 0.066 Uiso 1 1 calc R
C16 C 0.3864(5) 0.3136(5) 0.5581(3) 0.0338(10) Uani 1 1 d .
H16A H 0.3096 0.2569 0.5994 0.041 Uiso 1 1 calc R
H16B H 0.3357 0.4179 0.5501 0.041 Uiso 1 1 calc R
C17 C 0.4466(5) 0.2577(5) 0.4486(3) 0.0336(11) Uani 1 1 d .
C18 C 0.9230(6) 0.1008(5) 0.6254(4) 0.0432(12) Uani 1 1 d .
C19 C 0.8656(7) -0.0007(6) 0.7201(4) 0.0640(15) Uani 1 1 d .
H19A H 0.7856 0.0562 0.7692 0.096 Uiso 1 1 calc R
H19B H 0.9535 -0.0493 0.7578 0.096 Uiso 1 1 calc R
H19C H 0.8210 -0.0742 0.6943 0.096 Uiso 1 1 calc R
N1 N 0.8160(4) 0.1731(4) 0.5585(3) 0.0336(9) Uani 1 1 d .
O1 O 0.3733(4) 0.2735(4) 0.3728(3) 0.0600(10) Uani 1 1 d .
O2 O 0.6361(3) 0.0400(3) 0.3975(2) 0.0407(8) Uani 1 1 d .
H2 H 0.7309 0.0016 0.3864 0.061 Uiso 1 1 calc R
O3 O 1.0620(4) 0.1195(4) 0.6056(3) 0.0619(10) 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
N1 C1 C2 104.5(3)
N1 C1 C9 110.7(3)
C2 C1 C9 104.5(3)
N1 C1 H1 112.2
C2 C1 H1 112.2
C9 C1 H1 112.2
O2 C2 C3 112.9(3)
O2 C2 C17 109.0(3)
C3 C2 C17 112.4(3)
O2 C2 C1 116.5(3)
C3 C2 C1 101.1(3)
C17 C2 C1 104.5(3)
C4 C3 C8 120.9(4)
C4 C3 C2 129.1(4)
C8 C3 C2 109.9(4)
C3 C4 C5 118.2(4)
C3 C4 H4 120.9
C5 C4 H4 120.9
C4 C5 C6 120.6(5)
C4 C5 H5 119.7
C6 C5 H5 119.7
C7 C6 C5 121.6(5)
C7 C6 H6 119.2
C5 C6 H6 119.2
C6 C7 C8 118.0(4)
C6 C7 H7 121.0
C8 C7 H7 121.0
C7 C8 C3 120.7(4)
C7 C8 N1 129.8(4)
C3 C8 N1 109.4(4)
C10 C9 C16 117.0(4)
C10 C9 C1 114.1(3)
C16 C9 C1 103.9(3)
C10 C9 H9 107.1
C16 C9 H9 107.1
C1 C9 H9 107.1
C11 C10 C15 117.9(4)
C11 C10 C9 119.9(4)
C15 C10 C9 122.2(4)
C10 C11 C12 120.8(4)
C10 C11 H11 119.6
C12 C11 H11 119.6
C13 C12 C11 120.0(4)
C13 C12 H12 120.0
C11 C12 H12 120.0
C14 C13 C12 120.5(4)
C14 C13 Br1 120.2(4)
C12 C13 Br1 119.3(4)
C13 C14 C15 119.8(5)
C13 C14 H14 120.1
C15 C14 H14 120.1
C14 C15 C10 121.1(4)
C14 C15 H15 119.5
C10 C15 H15 119.5
C17 C16 C9 105.6(3)
C17 C16 H16A 110.6
C9 C16 H16A 110.6
C17 C16 H16B 110.6
C9 C16 H16B 110.6
H16A C16 H16B 108.8
O1 C17 C16 126.5(4)
O1 C17 C2 123.8(4)
C16 C17 C2 109.7(3)
O3 C18 N1 119.8(5)
O3 C18 C19 122.6(4)
N1 C18 C19 117.7(4)
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C18 N1 C8 125.2(4)
C18 N1 C1 127.2(4)
C8 N1 C1 107.1(3)
C2 O2 H2 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C13 1.899(5)
C1 N1 1.476(5)
C1 C2 1.536(5)
C1 C9 1.551(6)
C1 H1 0.9800
C2 O2 1.416(5)
C2 C3 1.513(6)
C2 C17 1.525(6)
C3 C4 1.375(6)
C3 C8 1.391(6)
C4 C5 1.379(7)
C4 H4 0.9300
C5 C6 1.382(7)
C5 H5 0.9300
C6 C7 1.370(7)
C6 H6 0.9300
C7 C8 1.379(6)
C7 H7 0.9300
C8 N1 1.428(5)
C9 C10 1.514(6)
C9 C16 1.533(6)
C9 H9 0.9800
C10 C11 1.386(6)
C10 C15 1.386(6)
C11 C12 1.384(6)
C11 H11 0.9300
C12 C13 1.365(7)
C12 H12 0.9300
C13 C14 1.362(6)
C14 C15 1.382(7)
C14 H14 0.9300
C15 H15 0.9300
C16 C17 1.497(6)
C16 H16A 0.9700
C16 H16B 0.9700
C17 O1 1.201(5)
C18 O3 1.232(5)
C18 N1 1.360(5)
C18 C19 1.491(7)
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
O2 H2 0.8200
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
N1 C1 C2 O2 95.8(4)
C9 C1 C2 O2 -147.8(3)
N1 C1 C2 C3 -27.0(4)
C9 C1 C2 C3 89.4(4)
N1 C1 C2 C17 -143.9(3)
C9 C1 C2 C17 -27.5(4)
O2 C2 C3 C4 69.6(6)
C17 C2 C3 C4 -54.2(6)
C1 C2 C3 C4 -165.1(4)
O2 C2 C3 C8 -106.5(4)
C17 C2 C3 C8 129.7(4)
C1 C2 C3 C8 18.7(4)
C8 C3 C4 C5 -1.3(7)
C2 C3 C4 C5 -177.0(4)
C3 C4 C5 C6 1.0(7)
C4 C5 C6 C7 -0.5(8)
C5 C6 C7 C8 0.4(8)
C6 C7 C8 C3 -0.7(7)
C6 C7 C8 N1 179.9(4)
C4 C3 C8 C7 1.2(6)
C2 C3 C8 C7 177.7(4)
C4 C3 C8 N1 -179.3(4)
C2 C3 C8 N1 -2.8(5)
N1 C1 C9 C10 -84.6(4)
C2 C1 C9 C10 163.3(3)
N1 C1 C9 C16 146.9(3)
C2 C1 C9 C16 34.9(4)
C16 C9 C10 C11 -132.7(4)
C1 C9 C10 C11 105.8(5)
C16 C9 C10 C15 49.0(6)
C1 C9 C10 C15 -72.5(5)
C15 C10 C11 C12 -0.2(7)
C9 C10 C11 C12 -178.6(4)
C10 C11 C12 C13 -1.3(8)
C11 C12 C13 C14 1.2(8)
C11 C12 C13 Br1 -178.0(4)
C12 C13 C14 C15 0.4(9)
Br1 C13 C14 C15 179.5(4)
C13 C14 C15 C10 -1.9(8)
C11 C10 C15 C14 1.8(7)
C9 C10 C15 C14 -179.8(5)
C10 C9 C16 C17 -155.3(4)
C1 C9 C16 C17 -28.6(4)
C9 C16 C17 O1 -168.8(4)
C9 C16 C17 C2 11.8(4)
O2 C2 C17 O1 -44.3(5)
C3 C2 C17 O1 81.7(5)
C1 C2 C17 O1 -169.5(4)
O2 C2 C17 C16 135.2(4)
C3 C2 C17 C16 -98.8(4)
C1 C2 C17 C16 10.0(4)
O3 C18 N1 C8 5.8(6)
C19 C18 N1 C8 -173.4(4)
O3 C18 N1 C1 176.1(4)
C19 C18 N1 C1 -3.1(6)
C7 C8 N1 C18 -24.1(7)
C3 C8 N1 C18 156.5(4)
C7 C8 N1 C1 164.0(4)
C3 C8 N1 C1 -15.4(4)
C2 C1 N1 C18 -144.8(4)
C9 C1 N1 C18 103.2(5)
C2 C1 N1 C8 26.9(4)
C9 C1 N1 C8 -85.1(4)
