#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:50:56 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178447 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/68/4026881.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_4026881
loop_
_publ_author_name
'Kyoung Hee Kang'
'Junghwan Do'
'Yong Sun Park'
_publ_section_title
;
 Asymmetric Synthesis oftrans-2,3-Disubstituted Indoline Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              808
_journal_page_last               812
_journal_paper_doi               10.1021/jo2023526
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C27 H26 Br N O'
_chemical_formula_weight         460.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 111.75(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.4945(19)
_cell_length_b                   10.870(2)
_cell_length_c                   12.264(3)
_cell_measurement_temperature    296(2)
_cell_volume                     1175.6(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0715
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8239
_diffrn_reflns_theta_full        24.00
_diffrn_reflns_theta_max         24.00
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    1.766
_exptl_absorpt_correction_T_max  0.9015
_exptl_absorpt_correction_T_min  0.5242
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.023(16)
_refine_ls_extinction_coef       0.005(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3410
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0466
_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)+(0.0601P)²+0.3605P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1485
_reflns_number_gt                2143
_reflns_number_total             3410
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2023526_si_002.cif
_cod_data_source_block           l
_cod_original_cell_volume        1175.6(4)
_cod_database_code               4026881
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
Br1 Br 0.36441(11) 0.71892(11) 0.19398(8) 0.1388(5) Uani 1 1 d .
O1 O 0.1364(5) 0.7193(5) 0.7607(4) 0.0882(12) Uani 1 1 d .
N1 N 0.1499(6) 0.5371(4) 0.6792(4) 0.0634(12) Uani 1 1 d .
C1 C 0.2208(7) 0.4267(5) 0.6487(5) 0.0629(14) Uani 1 1 d .
H1 H 0.3274 0.4420 0.6613 0.076 Uiso 1 1 calc R
C2 C 0.1230(6) 0.4137(5) 0.5155(4) 0.0608(14) Uani 1 1 d .
H2 H 0.1152 0.3268 0.4928 0.073 Uiso 1 1 calc R
C3 C -0.0274(7) 0.4589(5) 0.5126(5) 0.0622(15) Uani 1 1 d .
C4 C -0.1725(8) 0.4403(6) 0.4281(6) 0.0743(17) Uani 1 1 d .
H4 H -0.1861 0.3922 0.3623 0.089 Uiso 1 1 calc R
C5 C -0.2947(9) 0.4940(7) 0.4435(6) 0.088(2) Uani 1 1 d .
H5 H -0.3917 0.4807 0.3883 0.105 Uiso 1 1 calc R
C6 C -0.2757(8) 0.5663(7) 0.5387(7) 0.088(2) Uani 1 1 d .
H6 H -0.3603 0.6015 0.5473 0.106 Uiso 1 1 calc R
C7 C -0.1304(8) 0.5893(5) 0.6246(5) 0.0721(17) Uani 1 1 d .
H7 H -0.1170 0.6393 0.6892 0.087 Uiso 1 1 calc R
C8 C -0.0088(7) 0.5332(5) 0.6074(5) 0.0634(14) Uani 1 1 d .
C9 C 0.1807(7) 0.4883(5) 0.4354(5) 0.0619(14) Uani 1 1 d .
C10 C 0.1775(8) 0.6173(6) 0.4354(5) 0.0743(17) Uani 1 1 d .
H10 H 0.1372 0.6578 0.4841 0.089 Uiso 1 1 calc R
C11 C 0.2325(8) 0.6855(6) 0.3650(6) 0.090(2) Uani 1 1 d .
H11 H 0.2324 0.7710 0.3684 0.108 Uiso 1 1 calc R
C12 C 0.2879(8) 0.6261(7) 0.2891(6) 0.0842(19) Uani 1 1 d .
C13 C 0.2910(8) 0.4992(7) 0.2867(6) 0.087(2) Uani 1 1 d .
H13 H 0.3285 0.4593 0.2360 0.104 Uiso 1 1 calc R
C14 C 0.2381(7) 0.4306(6) 0.3598(5) 0.0707(16) Uani 1 1 d .
H14 H 0.2414 0.3452 0.3579 0.085 Uiso 1 1 calc R
C15 C 0.2045(7) 0.3157(5) 0.7166(5) 0.0678(15) Uani 1 1 d .
H15 H 0.2336 0.2404 0.6958 0.081 Uiso 1 1 calc R
C16 C 0.1534(7) 0.3149(6) 0.8021(5) 0.0703(17) Uani 1 1 d .
H16 H 0.1229 0.3910 0.8201 0.084 Uiso 1 1 calc R
C17 C 0.1371(6) 0.2138(7) 0.8726(4) 0.0670(14) Uani 1 1 d .
C18 C 0.1113(8) 0.2355(8) 0.9751(5) 0.096(2) Uani 1 1 d .
H18 H 0.1053 0.3168 0.9965 0.115 Uiso 1 1 calc R
C19 C 0.0944(11) 0.1467(10) 1.0455(7) 0.120(3) Uani 1 1 d .
H19 H 0.0783 0.1676 1.1135 0.144 Uiso 1 1 calc R
C20 C 0.1009(10) 0.0248(10) 1.0171(7) 0.114(3) Uani 1 1 d .
H20 H 0.0897 -0.0368 1.0659 0.137 Uiso 1 1 calc R
C21 C 0.1245(8) -0.0056(7) 0.9147(7) 0.097(2) Uani 1 1 d .
H21 H 0.1271 -0.0874 0.8933 0.116 Uiso 1 1 calc R
C22 C 0.1443(7) 0.0901(6) 0.8443(6) 0.0775(18) Uani 1 1 d .
H22 H 0.1628 0.0703 0.7771 0.093 Uiso 1 1 calc R
C23 C 0.2170(8) 0.6364(6) 0.7514(5) 0.0728(16) Uani 1 1 d .
C24 C 0.3915(8) 0.6409(6) 0.8175(5) 0.0760(17) Uani 1 1 d .
C25 C 0.4525(9) 0.5301(7) 0.8983(6) 0.098(2) Uani 1 1 d .
H25A H 0.3894 0.5151 0.9425 0.147 Uiso 1 1 calc R
H25B H 0.5542 0.5469 0.9512 0.147 Uiso 1 1 calc R
H25C H 0.4524 0.4590 0.8519 0.147 Uiso 1 1 calc R
C26 C 0.4742(9) 0.6592(7) 0.7298(6) 0.099(2) Uani 1 1 d .
H26A H 0.5806 0.6712 0.7729 0.149 Uiso 1 1 calc R
H26B H 0.4332 0.7299 0.6816 0.149 Uiso 1 1 calc R
H26C H 0.4596 0.5876 0.6810 0.149 Uiso 1 1 calc R
C27 C 0.4250(10) 0.7585(6) 0.8928(7) 0.108(3) Uani 1 1 d .
H27A H 0.3773 0.7531 0.9493 0.162 Uiso 1 1 calc R
H27B H 0.3861 0.8286 0.8431 0.162 Uiso 1 1 calc R
H27C H 0.5326 0.7672 0.9328 0.162 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'
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
C23 N1 C8 122.8(5)
C23 N1 C1 129.9(5)
C8 N1 C1 107.0(4)
N1 C1 C15 110.9(4)
N1 C1 C2 100.8(4)
C15 C1 C2 111.3(5)
C3 C2 C9 112.2(4)
C3 C2 C1 100.8(4)
C9 C2 C1 114.3(5)
C8 C3 C4 119.7(5)
C8 C3 C2 110.6(5)
C4 C3 C2 129.7(5)
C5 C4 C3 119.2(6)
C6 C5 C4 120.8(7)
C5 C6 C7 121.6(7)
C8 C7 C6 116.5(6)
C3 C8 C7 122.3(6)
C3 C8 N1 108.2(5)
C7 C8 N1 129.5(5)
C14 C9 C10 117.8(5)
C14 C9 C2 121.0(5)
C10 C9 C2 121.2(5)
C11 C10 C9 121.6(6)
C10 C11 C12 119.7(6)
C13 C12 C11 119.8(6)
C13 C12 Br1 120.4(5)
C11 C12 Br1 119.8(5)
C12 C13 C14 120.3(6)
C9 C14 C13 120.8(6)
C16 C15 C1 126.4(5)
C15 C16 C17 129.8(6)
C18 C17 C22 115.5(7)
C18 C17 C16 120.5(7)
C22 C17 C16 124.0(5)
C19 C18 C17 124.3(8)
C18 C19 C20 120.1(8)
C19 C20 C21 119.5(7)
C20 C21 C22 118.6(7)
C17 C22 C21 121.9(6)
O1 C23 N1 118.6(6)
O1 C23 C24 121.0(6)
N1 C23 C24 120.4(6)
C25 C24 C27 108.7(5)
C25 C24 C23 112.9(5)
C27 C24 C23 106.5(6)
C25 C24 C26 112.3(6)
C27 C24 C26 105.2(6)
C23 C24 C26 110.8(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C12 1.880(7)
O1 C23 1.215(7)
N1 C23 1.392(8)
N1 C8 1.437(7)
N1 C1 1.490(7)
C1 C15 1.506(8)
C1 C2 1.558(8)
C2 C3 1.498(8)
C2 C9 1.524(7)
C3 C8 1.373(8)
C3 C4 1.398(9)
C4 C5 1.373(9)
C5 C6 1.363(9)
C6 C7 1.413(9)
C7 C8 1.389(8)
C9 C14 1.387(7)
C9 C10 1.402(8)
C10 C11 1.379(8)
C11 C12 1.386(9)
C12 C13 1.380(10)
C13 C14 1.395(8)
C15 C16 1.308(7)
C16 C17 1.442(9)
C17 C18 1.387(8)
C17 C22 1.397(10)
C18 C19 1.344(10)
C19 C20 1.377(12)
C20 C21 1.395(11)
C21 C22 1.408(9)
C23 C24 1.552(10)
C24 C25 1.530(9)
C24 C27 1.539(8)
C24 C26 1.562(10)
