#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/39/4103932.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_4103932
loop_
_publ_author_name
'K. C. Nicolaou'
'Rüdiger Reingruber'
'David Sarlah'
'Stefan Bräse'
_publ_section_title
;
 Enantioselective Intramolecular Friedel-Crafts-Type α-Arylation of
 Aldehydes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2086
_journal_page_last               2087
_journal_paper_doi               10.1021/ja809405c
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C20 H21 Br N O4'
_chemical_formula_weight         419.29
_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                   5.0792(10)
_cell_length_b                   15.951(3)
_cell_length_c                   24.316(5)
_cell_measurement_reflns_used    3317
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      2.6
_cell_volume                     1970.0(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0646
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14288
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.53
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    2.110
_exptl_absorpt_correction_T_max  0.9590
_exptl_absorpt_correction_T_min  0.6776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate-like
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3441
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0708
_refine_ls_shift/su_max          0.122
_refine_ls_shift/su_mean         0.011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+1.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1815
_refine_ls_wR_factor_ref         0.2168
_reflns_number_gt                1972
_reflns_number_total             3441
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja809405c_si_002.cif
_cod_data_source_block           davs
_cod_original_cell_volume        1970.1(7)
_cod_database_code               4103932
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
Br1 Br 0.8562(3) 1.02141(6) 0.96683(6) 0.1418(7) Uani 1 1 d .
O1 O 0.532(2) 0.4034(7) 0.7473(4) 0.149(3) Uani 1 1 d .
O2 O 0.053(4) 0.1634(9) 0.7354(5) 0.244(7) Uani 1 1 d D
O3 O 0.7911(9) 0.5292(3) 0.8740(2) 0.0736(14) Uani 1 1 d .
O4 O 0.4691(8) 0.6223(3) 0.8912(2) 0.0765(16) Uani 1 1 d .
N1 N 0.9060(10) 0.6548(3) 0.8996(2) 0.0601(14) Uani 1 1 d .
C1 C 0.461(2) 0.3319(9) 0.7734(6) 0.121(4) Uani 1 1 d .
C2 C 0.301(3) 0.2789(12) 0.7490(8) 0.201(10) Uani 1 1 d D
H2 H 0.2401 0.2889 0.7135 0.242 Uiso 1 1 calc R
C3 C 0.227(3) 0.2092(12) 0.7770(8) 0.253(17) Uani 1 1 d D
C4 C 0.332(3) 0.1895(7) 0.8294(8) 0.178(9) Uani 1 1 d D
H4 H 0.2882 0.1399 0.8472 0.213 Uiso 1 1 calc R
C5 C 0.505(2) 0.2469(6) 0.8532(6) 0.111(4) Uani 1 1 d .
C6 C 0.5728(18) 0.3203(5) 0.8249(5) 0.086(3) Uani 1 1 d .
C7 C 0.7499(14) 0.3860(5) 0.8498(3) 0.070(2) Uani 1 1 d .
H7 H 0.8803 0.4011 0.8218 0.084 Uiso 1 1 calc R
C8 C 0.900(2) 0.3539(6) 0.8994(5) 0.106(3) Uani 1 1 d .
H8A H 1.0444 0.3185 0.8874 0.128 Uiso 1 1 calc R
H8B H 0.9733 0.4008 0.9197 0.128 Uiso 1 1 calc R
C9 C 0.718(3) 0.3047(9) 0.9358(5) 0.148(5) Uani 1 1 d .
H9A H 0.5714 0.3399 0.9465 0.178 Uiso 1 1 calc R
H9B H 0.8118 0.2885 0.9689 0.178 Uiso 1 1 calc R
C10 C 0.615(4) 0.2271(8) 0.9078(8) 0.179(8) Uani 1 1 d .
H10A H 0.7562 0.1868 0.9038 0.214 Uiso 1 1 calc R
H10B H 0.4789 0.2019 0.9305 0.214 Uiso 1 1 calc R
C11 C 0.5948(14) 0.4643(4) 0.8627(3) 0.0671(19) Uani 1 1 d .
H11A H 0.4853 0.4801 0.8317 0.081 Uiso 1 1 calc R
H11B H 0.4829 0.4556 0.8946 0.081 Uiso 1 1 calc R
C12 C 0.410(4) 0.4284(12) 0.6952(5) 0.204(8) Uani 1 1 d .
H12A H 0.2222 0.4303 0.6995 0.245 Uiso 1 1 calc R
H12B H 0.4546 0.3885 0.6672 0.245 Uiso 1 1 calc R
H12C H 0.4733 0.4829 0.6847 0.245 Uiso 1 1 calc R
C13 C -0.011(4) 0.1047(8) 0.7701(10) 0.260(14) Uani 1 1 d D
H13A H 0.0381 0.1215 0.8066 0.312 Uiso 1 1 calc R
H13B H 0.0782 0.0537 0.7606 0.312 Uiso 1 1 calc R
H13C H -0.1982 0.0957 0.7687 0.312 Uiso 1 1 calc R
C14 C 0.6995(13) 0.6039(4) 0.8882(3) 0.0541(16) Uani 1 1 d .
C15 C 0.8828(12) 0.7407(4) 0.9136(2) 0.0491(14) Uani 1 1 d .
C16 C 0.6868(15) 0.7705(5) 0.9478(3) 0.0648(18) Uani 1 1 d .
H16 H 0.5577 0.7336 0.9600 0.078 Uiso 1 1 calc R
C17 C 0.6758(18) 0.8540(5) 0.9645(3) 0.076(2) Uani 1 1 d .
H17 H 0.5436 0.8732 0.9877 0.092 Uiso 1 1 calc R
C18 C 0.869(2) 0.9070(5) 0.9451(3) 0.080(2) Uani 1 1 d .
C19 C 1.0598(18) 0.8790(6) 0.9119(5) 0.098(3) Uani 1 1 d .
H19 H 1.1899 0.9157 0.8999 0.118 Uiso 1 1 calc R
C20 C 1.0657(14) 0.7975(5) 0.8956(4) 0.080(2) Uani 1 1 d .
H20 H 1.1973 0.7799 0.8717 0.096 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
C1 O1 C12 121.4(13)
C13 O2 C3 93.4(15)
C14 O3 C11 116.4(5)
C14 N1 C15 124.4(5)
O1 C1 C2 119.7(17)
O1 C1 C6 115.2(10)
C2 C1 C6 125.1(17)
C3 C2 C1 118.2(17)
C2 C3 O2 102.7(16)
C2 C3 C4 121.8(13)
O2 C3 C4 135.0(17)
C5 C4 C3 117.8(13)
C6 C5 C4 120.1(15)
C6 C5 C10 121.8(11)
C4 C5 C10 118.1(13)
C1 C6 C5 117.0(12)
C1 C6 C7 120.9(10)
C5 C6 C7 122.1(11)
C6 C7 C8 112.6(8)
C6 C7 C11 110.3(6)
C8 C7 C11 112.1(6)
C9 C8 C7 109.6(8)
C8 C9 C10 112.2(11)
C5 C10 C9 111.3(10)
O3 C11 C7 105.6(6)
O4 C14 O3 125.1(6)
O4 C14 N1 126.2(6)
O3 C14 N1 108.7(5)
C20 C15 C16 116.9(6)
C20 C15 N1 120.5(6)
C16 C15 N1 122.5(6)
C15 C16 C17 122.2(7)
C18 C17 C16 117.3(8)
C19 C18 C17 121.2(8)
C19 C18 Br1 120.8(8)
C17 C18 Br1 118.0(7)
C18 C19 C20 120.7(9)
C19 C20 C15 121.7(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C18 1.901(8)
O1 C1 1.354(16)
O1 C12 1.467(16)
O2 C13 1.303(13)
O2 C3 1.528(15)
O3 C14 1.324(8)
O3 C11 1.463(8)
O4 C14 1.209(8)
N1 C14 1.355(8)
N1 C15 1.416(8)
C1 C2 1.314(17)
C1 C6 1.388(16)
C2 C3 1.357(18)
C3 C4 1.418(17)
C4 C5 1.392(17)
C5 C6 1.400(14)
C5 C10 1.476(19)
C6 C7 1.509(11)
C7 C8 1.515(12)
C7 C11 1.510(10)
C8 C9 1.502(17)
C9 C10 1.51(2)
C15 C20 1.370(10)
C15 C16 1.381(9)
C16 C17 1.394(10)
C17 C18 1.378(12)
C18 C19 1.338(13)
C19 C20 1.360(12)
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
C12 O1 C1 C2 7.4(19)
C12 O1 C1 C6 -173.8(10)
O1 C1 C2 C3 -177.7(14)
C6 C1 C2 C3 4(2)
C1 C2 C3 O2 -178.2(12)
C1 C2 C3 C4 -5(3)
C13 O2 C3 C2 -175.5(14)
C13 O2 C3 C4 13(2)
C2 C3 C4 C5 4(2)
O2 C3 C4 C5 174.6(14)
C3 C4 C5 C6 -1.4(18)
C3 C4 C5 C10 179.7(13)
O1 C1 C6 C5 -179.9(9)
C2 C1 C6 C5 -1.1(17)
O1 C1 C6 C7 2.6(14)
C2 C1 C6 C7 -178.6(11)
C4 C5 C6 C1 0.1(14)
C10 C5 C6 C1 178.9(10)
C4 C5 C6 C7 177.5(8)
C10 C5 C6 C7 -3.6(14)
C1 C6 C7 C8 -166.8(8)
C5 C6 C7 C8 15.8(11)
C1 C6 C7 C11 67.0(10)
C5 C6 C7 C11 -110.3(9)
C6 C7 C8 C9 -44.2(10)
C11 C7 C8 C9 80.9(10)
C7 C8 C9 C10 63.8(14)
C6 C5 C10 C9 20.4(18)
C4 C5 C10 C9 -160.8(12)
C8 C9 C10 C5 -50.6(17)
C14 O3 C11 C7 -177.9(6)
C6 C7 C11 O3 -167.0(7)
C8 C7 C11 O3 66.6(9)
C11 O3 C14 O4 -1.9(11)
C11 O3 C14 N1 177.1(6)
C15 N1 C14 O4 -4.3(12)
C15 N1 C14 O3 176.8(6)
C14 N1 C15 C20 -143.3(7)
C14 N1 C15 C16 40.1(10)
C20 C15 C16 C17 -1.3(10)
N1 C15 C16 C17 175.4(7)
C15 C16 C17 C18 0.6(11)
C16 C17 C18 C19 -0.5(12)
C16 C17 C18 Br1 179.5(5)
C17 C18 C19 C20 1.2(14)
Br1 C18 C19 C20 -178.8(7)
C18 C19 C20 C15 -1.9(14)
C16 C15 C20 C19 1.9(12)
N1 C15 C20 C19 -174.8(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660154
