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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/75/1507597.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_1507597
loop_
_publ_author_name
'Hanhan, Nadine V.'
'Tang, Yng C.'
'Tran, Ngon T.'
'Franz, Annaliese K.'
_publ_section_title
;
 Scandium(III)-Catalyzed Enantioselective Allylation of Isatins Using
 Allylsilanes.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2218
_journal_page_last               2221
_journal_paper_doi               10.1021/ol300496v
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C13 H14 Br N O2'
_chemical_formula_sum            'C13 H14 Br N O2'
_chemical_formula_weight         296.16
_chemical_name_common
(R)-5-bromo-3-hydroxy-1-methyl-3-(2-methylallyl)indolin-2-one
_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
_audit_update_record
;
2012-02-10 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0505(9)
_cell_length_b                   10.4346(11)
_cell_length_c                   15.1170(16)
_cell_measurement_reflns_used    6928
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.5
_cell_volume                     1269.9(2)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'SMART (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       ω
_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  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11155
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    3.226
_exptl_absorpt_correction_T_max  0.7060
_exptl_absorpt_correction_T_min  0.5331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0211
_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)+(0.0184P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0476
_refine_ls_wR_factor_ref         0.0486
_reflns_number_gt                2683
_reflns_number_total             2880
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300496v_si_001.cif
_cod_data_source_block           a2
_cod_database_code               1507597
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
N1 N 0.8085(2) 0.98629(14) 0.11630(10) 0.0167(3) Uani 1 1 d
C1 C 0.8614(2) 0.97363(17) 0.20153(12) 0.0141(4) Uani 1 1 d
O1 O 0.88486(16) 1.06026(14) 0.25412(8) 0.0189(3) Uani 1 1 d
C2 C 0.8902(2) 0.82983(18) 0.22100(12) 0.0131(4) Uani 1 1 d
O2 O 1.06222(17) 0.81995(14) 0.24088(9) 0.0160(3) Uani 1 1 d
H2 H 1.071(4) 0.750(3) 0.251(2) 0.043(9) Uiso 1 1 d
C3 C 0.8438(2) 0.76947(18) 0.13312(12) 0.0139(4) Uani 1 1 d
C4 C 0.8439(2) 0.64180(18) 0.10695(12) 0.0156(4) Uani 1 1 d
H4 H 0.884(2) 0.574(2) 0.1479(13) 0.013(5) Uiso 1 1 d
C5 C 0.7949(2) 0.61633(17) 0.01994(13) 0.0186(3) Uani 1 1 d
Br5 Br 0.79528(3) 0.443484(19) -0.020058(13) 0.02701(7) Uani 1 1 d
C6 C 0.7466(2) 0.7113(2) -0.03812(12) 0.0215(4) Uani 1 1 d
H6 H 0.717(3) 0.687(2) -0.0942(14) 0.025(6) Uiso 1 1 d
C7 C 0.7459(2) 0.83971(19) -0.01114(13) 0.0210(4) Uani 1 1 d
H7 H 0.710(3) 0.905(2) -0.0507(15) 0.024(6) Uiso 1 1 d
C8 C 0.7970(3) 0.86501(17) 0.07455(11) 0.0164(4) Uani 1 1 d
C9 C 0.7799(3) 1.1083(2) 0.07247(14) 0.0235(4) Uani 1 1 d
H9A H 0.807(3) 1.175(2) 0.1117(13) 0.018(5) Uiso 1 1 d
H9B H 0.852(3) 1.121(3) 0.0242(18) 0.040(7) Uiso 1 1 d
H9C H 0.675(3) 1.114(2) 0.0517(16) 0.026(7) Uiso 1 1 d
C10 C 0.7864(3) 0.78595(18) 0.30128(12) 0.0166(4) Uani 1 1 d
H10A H 0.815(3) 0.701(2) 0.3111(13) 0.020(5) Uiso 1 1 d
H10B H 0.826(2) 0.8322(19) 0.3490(13) 0.006(5) Uiso 1 1 d
C11 C 0.6004(3) 0.8011(2) 0.29339(13) 0.0190(4) Uani 1 1 d
C12 C 0.5074(3) 0.6985(3) 0.24421(19) 0.0305(5) Uani 1 1 d
H12A H 0.537(5) 0.696(4) 0.175(3) 0.096(13) Uiso 1 1 d
H12B H 0.381(4) 0.709(3) 0.2450(19) 0.054(9) Uiso 1 1 d
H12C H 0.535(3) 0.621(3) 0.2713(19) 0.037(8) Uiso 1 1 d
C13 C 0.5222(3) 0.8970(2) 0.33217(16) 0.0263(5) Uani 1 1 d
H13A H 0.403(3) 0.906(2) 0.3247(15) 0.022(6) Uiso 1 1 d
H13B H 0.586(3) 0.960(2) 0.3667(15) 0.027(6) Uiso 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
C1 N1 C8 110.79(14)
C1 N1 C9 124.40(16)
C8 N1 C9 124.66(15)
O1 C1 N1 126.39(17)
O1 C1 C2 124.90(16)
N1 C1 C2 108.71(15)
O2 C2 C3 113.28(15)
O2 C2 C10 109.87(15)
C3 C2 C10 115.61(16)
O2 C2 C1 104.88(15)
C3 C2 C1 101.49(14)
C10 C2 C1 110.89(15)
C2 O2 H2 102(2)
C8 C3 C4 120.53(16)
C8 C3 C2 109.14(16)
C4 C3 C2 130.33(17)
C5 C4 C3 116.73(17)
C5 C4 H4 123.0(12)
C3 C4 H4 120.1(12)
C6 C5 C4 122.76(17)
C6 C5 Br5 118.64(14)
C4 C5 Br5 118.60(14)
C5 C6 C7 120.21(17)
C5 C6 H6 117.7(14)
C7 C6 H6 122.1(14)
C8 C7 C6 116.98(17)
C8 C7 H7 122.8(14)
C6 C7 H7 120.3(14)
C7 C8 C3 122.78(17)
C7 C8 N1 127.34(17)
C3 C8 N1 109.88(15)
N1 C9 H9A 108.8(13)
N1 C9 H9B 112.2(16)
H9A C9 H9B 104(2)
N1 C9 H9C 111.1(16)
H9A C9 H9C 113(2)
H9B C9 H9C 107(2)
C11 C10 C2 116.34(17)
C11 C10 H10A 111.2(14)
C2 C10 H10A 105.8(13)
C11 C10 H10B 110.5(12)
C2 C10 H10B 105.8(12)
H10A C10 H10B 106.7(17)
C13 C11 C12 121.5(2)
C13 C11 C10 121.1(2)
C12 C11 C10 117.3(2)
C11 C12 H12A 113(2)
C11 C12 H12B 114.3(17)
H12A C12 H12B 104(2)
C11 C12 H12C 106.3(17)
H12A C12 H12C 111(3)
H12B C12 H12C 109(2)
C11 C13 H13A 119.5(14)
C11 C13 H13B 119.4(14)
H13A C13 H13B 121(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.363(2)
N1 C8 1.417(2)
N1 C9 1.454(2)
C1 O1 1.219(2)
C1 C2 1.547(3)
C2 O2 1.421(2)
C2 C3 1.517(2)
C2 C10 1.543(3)
O2 H2 0.74(3)
C3 C8 1.386(3)
C3 C4 1.390(3)
C4 C5 1.399(3)
C4 H4 0.99(2)
C5 C6 1.380(3)
C5 Br5 1.9022(18)
C6 C7 1.401(3)
C6 H6 0.92(2)
C7 C8 1.384(3)
C7 H7 0.95(2)
C9 H9A 0.94(2)
C9 H9B 0.94(3)
C9 H9C 0.90(2)
C10 C11 1.511(3)
C10 H10A 0.93(2)
C10 H10B 0.93(2)
C11 C13 1.320(3)
C11 C12 1.503(3)
C12 H12A 1.07(4)
C12 H12B 1.03(3)
C12 H12C 0.93(3)
C13 H13A 0.97(2)
C13 H13B 0.98(2)
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
C8 N1 C1 O1 179.35(19)
C9 N1 C1 O1 3.6(3)
C8 N1 C1 C2 0.3(2)
C9 N1 C1 C2 -175.52(19)
O1 C1 C2 O2 -61.2(2)
N1 C1 C2 O2 117.93(16)
O1 C1 C2 C3 -179.28(17)
N1 C1 C2 C3 -0.19(19)
O1 C1 C2 C10 57.4(2)
N1 C1 C2 C10 -123.53(17)
O2 C2 C3 C8 -111.85(18)
C10 C2 C3 C8 120.09(19)
C1 C2 C3 C8 0.0(2)
O2 C2 C3 C4 67.7(3)
C10 C2 C3 C4 -60.4(3)
C1 C2 C3 C4 179.58(19)
C8 C3 C4 C5 0.0(3)
C2 C3 C4 C5 -179.54(18)
C3 C4 C5 C6 -0.6(3)
C3 C4 C5 Br5 179.22(14)
C4 C5 C6 C7 0.3(3)
Br5 C5 C6 C7 -179.56(15)
C5 C6 C7 C8 0.7(3)
C6 C7 C8 C3 -1.4(3)
C6 C7 C8 N1 179.3(2)
C4 C3 C8 C7 1.1(3)
C2 C3 C8 C7 -179.31(18)
C4 C3 C8 N1 -179.47(18)
C2 C3 C8 N1 0.1(2)
C1 N1 C8 C7 179.1(2)
C9 N1 C8 C7 -5.1(3)
C1 N1 C8 C3 -0.3(2)
C9 N1 C8 C3 175.5(2)
O2 C2 C10 C11 175.10(16)
C3 C2 C10 C11 -55.2(2)
C1 C2 C10 C11 59.6(2)
C2 C10 C11 C13 -101.5(2)
C2 C10 C11 C12 82.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30651855
2 PubChem 102579901
