#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/16/4101667.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_4101667
loop_
_publ_author_name
'Duffey, Trisha A.'
'Shaw, Scott A.'
'Vedejs, Edwin'
_publ_section_title
;
 AcOLeDMAP and BnOLeDMAP: conformationally restricted nucleophilic
 catalysts for enantioselective rearrangement of indolyl acetates and
 carbonates.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14
_journal_page_last               15
_journal_paper_doi               10.1021/ja805541u
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H16 Br N O3'
_chemical_formula_sum            'C21 H16 Br N O3'
_chemical_formula_weight         410.26
_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                   5.6298(4)
_cell_length_b                   8.2145(6)
_cell_length_c                   37.372(3)
_cell_measurement_reflns_used    9373
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.18
_cell_volume                     1728.3(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART-APEX'
_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      85(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0156
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            54434
_diffrn_reflns_theta_full        28.37
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    2.400
_exptl_absorpt_correction_T_max  0.7153
_exptl_absorpt_correction_T_min  0.6325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  Blessing, R. Acta Cryst. (1995) A51 33-38.
  Sheldrick, G.  SADABS (Version 2008/1) Bruker AXS area
  detector absorption and other corrections, University of
  Gottingen, Germany 2008.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.006(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0218
_refine_ls_R_factor_gt           0.0217
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0226P)²+1.3990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0543
_refine_ls_wR_factor_ref         0.0544
_reflns_number_gt                4294
_reflns_number_total             4323
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja805541u_si_002.cif
_cod_data_source_block           td287
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1673 2011-04-08 12:14:43Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4101667
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.47117(3) 0.76798(2) 0.118054(5) 0.01615(5) Uani 1 1 d . . .
C1 C 0.2076(3) 0.7554(2) 0.14981(4) 0.0132(3) Uani 1 1 d . . .
C2 C 0.1183(4) 0.8967(2) 0.16485(5) 0.0156(4) Uani 1 1 d . . .
H2A H 0.1880 0.9991 0.1595 0.019 Uiso 1 1 calc R . .
C3 C -0.0759(4) 0.8866(2) 0.18813(5) 0.0149(4) Uani 1 1 d . . .
H3A H -0.1436 0.9815 0.1985 0.018 Uiso 1 1 calc R . .
C4 C -0.1655(3) 0.7340(2) 0.19546(4) 0.0129(3) Uani 1 1 d . . .
C5 C -0.3867(3) 0.5307(2) 0.22068(5) 0.0120(3) Uani 1 1 d . . .
C6 C -0.2066(3) 0.4477(2) 0.19542(5) 0.0109(3) Uani 1 1 d . . .
C7 C -0.0725(3) 0.5923(2) 0.18054(4) 0.0114(3) Uani 1 1 d . . .
C8 C 0.1158(3) 0.6013(2) 0.15695(5) 0.0123(3) Uani 1 1 d . . .
H8A H 0.1800 0.5065 0.1461 0.015 Uiso 1 1 calc R . .
C9 C -0.0477(3) 0.3344(2) 0.21814(4) 0.0140(3) Uani 1 1 d . . .
H9A H 0.0703 0.2819 0.2027 0.021 Uiso 1 1 calc R . .
H9B H -0.1462 0.2509 0.2296 0.021 Uiso 1 1 calc R . .
H9C H 0.0336 0.3983 0.2366 0.021 Uiso 1 1 calc R . .
C10 C -0.3275(3) 0.3438(2) 0.16682(5) 0.0121(3) Uani 1 1 d . . .
C11 C -0.2557(3) 0.2135(2) 0.11080(5) 0.0170(4) Uani 1 1 d . . .
H11A H -0.4032 0.2601 0.1006 0.020 Uiso 1 1 calc R . .
H11B H -0.2885 0.1008 0.1188 0.020 Uiso 1 1 calc R . .
C12 C -0.0604(3) 0.2153(2) 0.08355(4) 0.0162(3) Uani 1 1 d . . .
C13 C 0.0684(4) 0.0764(2) 0.07724(5) 0.0198(4) Uani 1 1 d . . .
H13A H 0.0268 -0.0212 0.0893 0.024 Uiso 1 1 calc R . .
C14 C 0.2620(4) 0.0758(3) 0.05307(5) 0.0223(4) Uani 1 1 d . . .
H14A H 0.3479 -0.0219 0.0489 0.027 Uiso 1 1 calc R . .
C15 C 0.3254(3) 0.2158(3) 0.03578(5) 0.0207(4) Uani 1 1 d . . .
H15A H 0.4582 0.2153 0.0201 0.025 Uiso 1 1 calc R . .
C16 C 0.1957(4) 0.3615(3) 0.04092(5) 0.0171(4) Uani 1 1 d . . .
C17 C 0.2545(4) 0.5060(3) 0.02223(5) 0.0210(4) Uani 1 1 d . . .
H17A H 0.3872 0.5068 0.0065 0.025 Uiso 1 1 calc R . .
C18 C 0.1226(4) 0.6444(3) 0.02648(5) 0.0228(4) Uani 1 1 d . . .
H18A H 0.1640 0.7405 0.0138 0.027 Uiso 1 1 calc R . .
C19 C -0.0750(4) 0.6448(2) 0.04970(5) 0.0214(4) Uani 1 1 d . . .
H19A H -0.1670 0.7410 0.0524 0.026 Uiso 1 1 calc R . .
C20 C -0.1349(4) 0.5073(2) 0.06840(5) 0.0179(4) Uani 1 1 d . . .
H20A H -0.2675 0.5097 0.0841 0.021 Uiso 1 1 calc R . .
C21 C -0.0026(3) 0.3617(2) 0.06469(4) 0.0146(3) Uani 1 1 d . . .
O1 O -0.5264(3) 0.46370(15) 0.24081(3) 0.0155(2) Uani 1 1 d . . .
O2 O -0.5264(2) 0.29293(16) 0.16763(3) 0.0200(3) Uani 1 1 d . . .
O3 O -0.1713(2) 0.31249(17) 0.14072(3) 0.0178(3) Uani 1 1 d . . .
N1 N -0.3533(3) 0.69397(19) 0.21848(4) 0.0135(3) Uani 1 1 d . . .
H1A H -0.415(4) 0.760(3) 0.2324(6) 0.019(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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C8 123.32(16) . . ?
C2 C1 Br1 119.39(14) . . ?
C8 C1 Br1 117.28(13) . . ?
C1 C2 C3 119.11(17) . . ?
C4 C3 C2 117.59(16) . . ?
C3 C4 C7 122.88(15) . . ?
C3 C4 N1 127.66(17) . . ?
C7 C4 N1 109.45(16) . . ?
O1 C5 N1 124.95(17) . . ?
O1 C5 C6 126.96(16) . . ?
N1 C5 C6 107.97(15) . . ?
C7 C6 C10 113.81(14) . . ?
C7 C6 C5 101.88(14) . . ?
C10 C6 C5 112.44(14) . . ?
C7 C6 C9 112.70(14) . . ?
C10 C6 C9 107.79(14) . . ?
C5 C6 C9 108.08(14) . . ?
C8 C7 C4 119.94(16) . . ?
C8 C7 C6 131.30(16) . . ?
C4 C7 C6 108.74(15) . . ?
C7 C8 C1 117.14(16) . . ?
O2 C10 O3 124.51(17) . . ?
O2 C10 C6 126.52(17) . . ?
O3 C10 C6 108.93(15) . . ?
O3 C11 C12 106.01(14) . . ?
C13 C12 C21 119.56(17) . . ?
C13 C12 C11 119.75(17) . . ?
C21 C12 C11 120.67(16) . . ?
C12 C13 C14 121.32(18) . . ?
C15 C14 C13 119.98(19) . . ?
C14 C15 C16 120.87(18) . . ?
C15 C16 C17 121.44(18) . . ?
C15 C16 C21 119.26(18) . . ?
C17 C16 C21 119.28(18) . . ?
C18 C17 C16 120.86(19) . . ?
C17 C18 C19 120.10(19) . . ?
C20 C19 C18 120.39(19) . . ?
C19 C20 C21 121.12(18) . . ?
C20 C21 C16 118.25(17) . . ?
C20 C21 C12 122.79(17) . . ?
C16 C21 C12 118.95(16) . . ?
C10 O3 C11 116.79(14) . . ?
C5 N1 C4 111.92(15) . . ?
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
Br1 C1 1.9028(16) . ?
C1 C2 1.384(3) . ?
C1 C8 1.393(2) . ?
C2 C3 1.400(3) . ?
C3 C4 1.379(2) . ?
C4 C7 1.393(2) . ?
C4 N1 1.402(2) . ?
C5 O1 1.220(2) . ?
C5 N1 1.357(2) . ?
C5 C6 1.544(2) . ?
C6 C7 1.513(2) . ?
C6 C10 1.528(2) . ?
C6 C9 1.546(2) . ?
C7 C8 1.381(3) . ?
C10 O2 1.195(2) . ?
C10 O3 1.339(2) . ?
C11 O3 1.462(2) . ?
C11 C12 1.498(2) . ?
C12 C13 1.372(3) . ?
C12 C21 1.431(2) . ?
C13 C14 1.416(3) . ?
C14 C15 1.366(3) . ?
C15 C16 1.415(3) . ?
C16 C17 1.417(3) . ?
C16 C21 1.427(3) . ?
C17 C18 1.367(3) . ?
C18 C19 1.411(3) . ?
C19 C20 1.370(3) . ?
C20 C21 1.416(3) . ?
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 H1A O1 0.83(2) 1.98(2) 2.7716(19) 160(2) 3_455
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26593591
