#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/16/4101669.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_4101669
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_formula_moiety         'C22 H29 N3 O3'
_chemical_formula_sum            'C22 H29 N3 O3'
_chemical_formula_weight         383.48
_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                   8.3738(8)
_cell_length_b                   11.4894(11)
_cell_length_c                   21.864(2)
_cell_measurement_reflns_used    6087
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      23.32
_cell_measurement_theta_min      3.01
_cell_volume                     2103.5(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            21512
_diffrn_reflns_theta_full        28.37
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         2980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0312
_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)+(0.0434P)²+0.3832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0830
_reflns_number_gt                2762
_reflns_number_total             2980
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja805541u_si_004.cif
_cod_data_source_block           ss200a
_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_cell_volume        2103.6(4)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4101669
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
O1 O 0.57509(13) 0.22256(12) 0.26768(5) 0.0377(3) Uani 1 1 d . . .
O2 O 1.03993(11) 0.24757(9) 0.16387(5) 0.0245(2) Uani 1 1 d . . .
O3 O 1.13667(14) 0.16403(10) 0.07874(5) 0.0314(2) Uani 1 1 d . . .
N1 N 0.80889(14) 0.30866(10) 0.24192(5) 0.0228(2) Uani 1 1 d . . .
H1A H 0.9017 0.3350 0.2548 0.027 Uiso 1 1 calc R . .
N2 N 0.8513(2) -0.06200(12) 0.22299(6) 0.0392(3) Uani 1 1 d . . .
N3 N 0.65314(17) 0.09449(12) 0.06516(6) 0.0326(3) Uani 1 1 d . . .
C1 C 0.74768(17) 0.27260(12) 0.34933(7) 0.0256(3) Uani 1 1 d . . .
C2 C 0.6852(2) 0.18887(15) 0.38833(8) 0.0363(4) Uani 1 1 d . . .
H2B H 0.6220 0.1273 0.3724 0.044 Uiso 1 1 calc R . .
C3 C 0.7154(2) 0.19530(16) 0.45088(8) 0.0422(4) Uani 1 1 d . . .
H3A H 0.6727 0.1379 0.4775 0.051 Uiso 1 1 calc R . .
C4 C 0.8062(3) 0.28404(16) 0.47414(8) 0.0428(4) Uani 1 1 d . . .
H4A H 0.8287 0.2869 0.5167 0.051 Uiso 1 1 calc R . .
C5 C 0.8651(3) 0.36897(17) 0.43591(8) 0.0481(5) Uani 1 1 d . . .
H5A H 0.9252 0.4318 0.4522 0.058 Uiso 1 1 calc R . .
C6 C 0.8363(2) 0.36270(15) 0.37329(7) 0.0375(4) Uani 1 1 d . . .
H6A H 0.8781 0.4209 0.3469 0.045 Uiso 1 1 calc R . .
C7 C 0.70315(16) 0.26532(12) 0.28257(7) 0.0249(3) Uani 1 1 d . . .
C8 C 0.77074(17) 0.31224(12) 0.17678(6) 0.0219(3) Uani 1 1 d . . .
H8A H 0.6595 0.2815 0.1728 0.026 Uiso 1 1 calc R . .
C9 C 0.87842(15) 0.22697(12) 0.14189(6) 0.0209(3) Uani 1 1 d . . .
H9A H 0.8729 0.2440 0.0971 0.025 Uiso 1 1 calc R . .
C10 C 0.83217(17) 0.10137(12) 0.15324(6) 0.0223(3) Uani 1 1 d . . .
C11 C 0.8921(2) 0.04506(13) 0.20428(7) 0.0292(3) Uani 1 1 d . . .
H11A H 0.9687 0.0858 0.2281 0.035 Uiso 1 1 calc R . .
C12 C 0.7371(3) -0.11361(15) 0.19026(8) 0.0416(4) Uani 1 1 d . . .
H12A H 0.7013 -0.1880 0.2033 0.050 Uiso 1 1 calc R . .
C13 C 0.6676(2) -0.06640(14) 0.13885(8) 0.0355(4) Uani 1 1 d . . .
H13A H 0.5862 -0.1079 0.1178 0.043 Uiso 1 1 calc R . .
C14 C 0.71687(17) 0.04254(13) 0.11768(7) 0.0258(3) Uani 1 1 d . . .
C15 C 0.76751(18) 0.43830(12) 0.15033(7) 0.0271(3) Uani 1 1 d . . .
C16 C 0.6785(2) 0.51679(14) 0.19530(8) 0.0386(4) Uani 1 1 d . . .
H16A H 0.7418 0.5254 0.2327 0.058 Uiso 1 1 calc R . .
H16B H 0.5750 0.4819 0.2053 0.058 Uiso 1 1 calc R . .
H16C H 0.6618 0.5934 0.1767 0.058 Uiso 1 1 calc R . .
C17 C 0.6733(2) 0.43633(14) 0.08999(7) 0.0327(3) Uani 1 1 d . . .
H17A H 0.5630 0.4124 0.0981 0.049 Uiso 1 1 calc R . .
H17B H 0.7231 0.3811 0.0617 0.049 Uiso 1 1 calc R . .
H17C H 0.6738 0.5143 0.0718 0.049 Uiso 1 1 calc R . .
C18 C 0.9351(2) 0.48773(14) 0.13851(8) 0.0332(3) Uani 1 1 d . . .
H18A H 0.9267 0.5702 0.1276 0.050 Uiso 1 1 calc R . .
H18B H 0.9854 0.4449 0.1049 0.050 Uiso 1 1 calc R . .
H18C H 1.0001 0.4796 0.1755 0.050 Uiso 1 1 calc R . .
C19 C 1.15904(18) 0.21204(12) 0.12712(7) 0.0252(3) Uani 1 1 d . . .
C20 C 1.31811(18) 0.24060(17) 0.15423(8) 0.0361(4) Uani 1 1 d . . .
H20A H 1.3429 0.1848 0.1868 0.054 Uiso 1 1 calc R . .
H20B H 1.3154 0.3195 0.1713 0.054 Uiso 1 1 calc R . .
H20C H 1.4003 0.2362 0.1224 0.054 Uiso 1 1 calc R . .
C21 C 0.5042(2) 0.0464(2) 0.04167(10) 0.0484(5) Uani 1 1 d . . .
H21A H 0.5255 -0.0283 0.0216 0.073 Uiso 1 1 calc R . .
H21B H 0.4575 0.1006 0.0120 0.073 Uiso 1 1 calc R . .
H21C H 0.4293 0.0346 0.0756 0.073 Uiso 1 1 calc R . .
C22 C 0.7648(2) 0.12164(15) 0.01546(7) 0.0371(4) Uani 1 1 d . . .
H22A H 0.8741 0.1225 0.0314 0.056 Uiso 1 1 calc R . .
H22B H 0.7389 0.1982 -0.0017 0.056 Uiso 1 1 calc R . .
H22C H 0.7558 0.0624 -0.0166 0.056 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'
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
C19 O2 C9 116.29(11) . . ?
C7 N1 C8 120.60(12) . . ?
C12 N2 C11 115.27(15) . . ?
C14 N3 C21 116.98(15) . . ?
C14 N3 C22 117.09(13) . . ?
C21 N3 C22 111.39(14) . . ?
C6 C1 C2 119.36(14) . . ?
C6 C1 C7 122.88(13) . . ?
C2 C1 C7 117.57(14) . . ?
C1 C2 C3 119.88(16) . . ?
C4 C3 C2 120.31(16) . . ?
C3 C4 C5 120.06(16) . . ?
C4 C5 C6 119.93(18) . . ?
C1 C6 C5 120.42(16) . . ?
O1 C7 N1 123.22(14) . . ?
O1 C7 C1 119.75(13) . . ?
N1 C7 C1 117.03(12) . . ?
N1 C8 C9 109.78(11) . . ?
N1 C8 C15 113.05(11) . . ?
C9 C8 C15 114.75(11) . . ?
O2 C9 C10 109.79(11) . . ?
O2 C9 C8 106.15(10) . . ?
C10 C9 C8 112.12(11) . . ?
C11 C10 C14 117.91(13) . . ?
C11 C10 C9 119.00(13) . . ?
C14 C10 C9 122.73(12) . . ?
N2 C11 C10 125.64(15) . . ?
N2 C12 C13 124.48(15) . . ?
C12 C13 C14 119.90(15) . . ?
C13 C14 N3 122.77(14) . . ?
C13 C14 C10 116.65(14) . . ?
N3 C14 C10 120.55(13) . . ?
C16 C15 C18 109.61(13) . . ?
C16 C15 C17 108.10(13) . . ?
C18 C15 C17 109.26(13) . . ?
C16 C15 C8 108.53(12) . . ?
C18 C15 C8 112.95(12) . . ?
C17 C15 C8 108.27(11) . . ?
O3 C19 O2 123.17(14) . . ?
O3 C19 C20 125.87(14) . . ?
O2 C19 C20 110.95(12) . . ?
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
O1 C7 1.2237(17) . ?
O2 C19 1.3443(17) . ?
O2 C9 1.4546(16) . ?
O3 C19 1.2075(18) . ?
N1 C7 1.3497(18) . ?
N1 C8 1.4602(17) . ?
N2 C12 1.333(2) . ?
N2 C11 1.341(2) . ?
N3 C14 1.3999(19) . ?
N3 C21 1.458(2) . ?
N3 C22 1.467(2) . ?
C1 C6 1.377(2) . ?
C1 C2 1.388(2) . ?
C1 C7 1.509(2) . ?
C2 C3 1.393(2) . ?
C3 C4 1.370(3) . ?
C4 C5 1.376(3) . ?
C5 C6 1.392(2) . ?
C8 C9 1.5346(18) . ?
C8 C15 1.5599(19) . ?
C9 C10 1.5146(19) . ?
C10 C11 1.384(2) . ?
C10 C14 1.4119(19) . ?
C12 C13 1.377(3) . ?
C13 C14 1.397(2) . ?
C15 C16 1.528(2) . ?
C15 C18 1.536(2) . ?
C15 C17 1.537(2) . ?
C19 C20 1.494(2) . ?
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 N2 0.88 2.43 3.301(2) 169.1 3_755
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26583672
