#------------------------------------------------------------------------------
#$Date: 2015-07-05 12:09:47 +0300 (Sun, 05 Jul 2015) $
#$Revision: 140138 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/11/4031152.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_4031152
loop_
_publ_author_name
'Suga, Hiroyuki'
'Sekikawa, Yurie'
'Misawa, Shunta'
'Kinugawa, Daito'
'Oda, Rinnosuke'
'Itoh, Kennosuke'
'Toda, Yasunori'
'Kiyono, Ryotaro'
_publ_section_title
;
 Chiral Lewis Acid-Catalyzed Enantioselective Cycloadditions between
 Indoles and Cyclic Carbonyl Ylides Derived from Diazodiketone or
 Diazoketoester Derivatives.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6687
_journal_page_last               6696
_journal_paper_doi               10.1021/acs.joc.5b00835
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H16 Br N O2'
_chemical_formula_weight         382.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6115(11)
_cell_length_b                   9.9940(19)
_cell_length_c                   28.653(6)
_cell_measurement_temperature    296.(2)
_cell_volume                     1606.9(6)
_computing_data_collection       'Bruker SMART APEXII'
_computing_molecular_graphics    'XSHELL V6.3.1'
_computing_publication_material  'Generate Report (Bruker AXS)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0557
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            9315
_diffrn_reflns_theta_full        28.63
_diffrn_reflns_theta_max         28.63
_diffrn_reflns_theta_min         2.16
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    2.570
_exptl_absorpt_correction_T_max  0.63
_exptl_absorpt_correction_T_min  0.36
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.340
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(6)
_refine_ls_extinction_coef       0.0012(4)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0264
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0523
_refine_ls_wR_factor_ref         0.0533
_reflns_number_gt                3499
_reflns_number_total             3784
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00835_si_002.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4031152.cif.
;
_cod_original_cell_volume        1606.9(5)
_cod_database_code               4031152
loop_
_space_group_symop_operation_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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Br Br1 0.56746(4) 0.73412(2) 0.757756(7) 0.01977(7) Uani d . 1
C C1 0.3846(4) 0.6182(2) 0.71911(7) 0.0153(5) Uani d . 1
C C2 0.1776(4) 0.5597(2) 0.73579(7) 0.0155(5) Uani d . 1
H H2 0.1303 0.5748 0.7664 0.019 Uiso calc R 1
C C3 0.0398(4) 0.47841(19) 0.70700(7) 0.0151(5) Uani d . 1
H H3 -0.0973 0.437 0.7181 0.018 Uiso calc R 1
C C4 0.1143(4) 0.4611(2) 0.66077(7) 0.0130(5) Uani d . 1
N N1 -0.0032(3) 0.39286(17) 0.62516(6) 0.0137(4) Uani d . 1
C C5 0.1565(4) 0.3842(2) 0.58443(7) 0.0131(4) Uani d . 1
H H5 0.2262 0.295 0.5805 0.016 Uiso calc R 1
C C6 0.0279(4) 0.43364(19) 0.54037(7) 0.0139(5) Uani d . 1
H H6 -0.1344 0.3977 0.5389 0.017 Uiso calc R 1
C C7 0.1633(4) 0.4016(2) 0.49601(7) 0.0142(5) Uani d . 1
O O1 0.0952(3) 0.31497(14) 0.46961(5) 0.0186(3) Uani d . 1
C C8 0.3915(4) 0.4790(2) 0.48813(7) 0.0152(5) Uani d . 1
H H8A 0.4048 0.4983 0.4551 0.018 Uiso calc R 1
H H8B 0.5245 0.4218 0.4965 0.018 Uiso calc R 1
C C9 0.4165(4) 0.61201(19) 0.51528(7) 0.0132(4) Uani d . 1
H H9A 0.5824 0.6258 0.5235 0.016 Uiso calc R 1
H H9B 0.3672 0.6856 0.4954 0.016 Uiso calc R 1
C C10 0.2647(4) 0.6117(2) 0.55982(7) 0.0113(4) Uani d . 1
C C11 0.3461(4) 0.49359(19) 0.59306(7) 0.0115(4) Uani d . 1
H H11 0.5065 0.4619 0.5852 0.014 Uiso calc R 1
C C12 0.3216(4) 0.52059(19) 0.64456(7) 0.0130(5) Uani d . 1
C C13 0.4610(4) 0.59916(19) 0.67340(7) 0.0147(4) Uani d . 1
H H13 0.6011 0.638 0.6626 0.018 Uiso calc R 1
C C14 0.2518(3) 0.7457(2) 0.58469(6) 0.0129(4) Uani d . 1
C C15 0.4376(5) 0.83635(19) 0.58345(7) 0.0185(4) Uani d . 1
H H15 0.5651 0.8222 0.5633 0.022 Uiso calc R 1
C C16 0.4350(5) 0.9487(2) 0.61213(8) 0.0223(5) Uani d . 1
H H16 0.5606 1.0092 0.6109 0.027 Uiso calc R 1
C C17 0.2487(5) 0.9711(2) 0.64233(8) 0.0229(6) Uani d . 1
H H17 0.2509 1.0446 0.6623 0.028 Uiso calc R 1
C C18 0.0568(5) 0.8828(2) 0.64278(8) 0.0222(5) Uani d . 1
H H18 -0.0727 0.8988 0.6623 0.027 Uiso calc R 1
C C19 0.0590(4) 0.7708(2) 0.61413(6) 0.0175(4) Uani d . 1
H H19 -0.0694 0.7119 0.6146 0.021 Uiso calc R 1
C C20 -0.1574(4) 0.2803(2) 0.63530(7) 0.0185(5) Uani d . 1
H H20A -0.2836 0.3086 0.6557 0.028 Uiso calc R 1
H H20B -0.0667 0.2109 0.6502 0.028 Uiso calc R 1
H H20C -0.2241 0.2467 0.6068 0.028 Uiso calc R 1
O O2 0.0236(3) 0.57620(13) 0.54610(5) 0.0123(3) Uani d . 1
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
C2 C1 C13 121.7(2)
C2 C1 Br1 120.55(16)
C13 C1 Br1 117.72(17)
C1 C2 C3 120.50(19)
C1 C2 H2 119.8
C3 C2 H2 119.8
C2 C3 C4 117.8(2)
C2 C3 H3 121.1
C4 C3 H3 121.1
C12 C4 N1 111.21(18)
C12 C4 C3 121.0(2)
N1 C4 C3 127.7(2)
C4 N1 C20 121.06(17)
C4 N1 C5 108.71(17)
C20 N1 C5 118.43(16)
N1 C5 C6 110.26(18)
N1 C5 C11 104.49(16)
C6 C5 C11 103.15(16)
N1 C5 H5 112.7
C6 C5 H5 112.7
C11 C5 H5 112.7
O2 C6 C7 108.32(16)
O2 C6 C5 103.49(16)
C7 C6 C5 112.70(18)
O2 C6 H6 110.7
C7 C6 H6 110.7
C5 C6 H6 110.7
O1 C7 C8 122.64(19)
O1 C7 C6 121.1(2)
C8 C7 C6 116.21(18)
C7 C8 C9 116.18(18)
C7 C8 H8A 108.2
C9 C8 H8A 108.2
C7 C8 H8B 108.2
C9 C8 H8B 108.2
H8A C8 H8B 107.4
C10 C9 C8 111.50(17)
C10 C9 H9A 109.3
C8 C9 H9A 109.3
C10 C9 H9B 109.3
C8 C9 H9B 109.3
H9A C9 H9B 108.0
O2 C10 C14 107.33(16)
O2 C10 C9 106.99(16)
C14 C10 C9 114.54(16)
O2 C10 C11 104.41(16)
C14 C10 C11 112.88(15)
C9 C10 C11 109.97(16)
C12 C11 C5 102.75(16)
C12 C11 C10 115.41(16)
C5 C11 C10 103.44(17)
C12 C11 H11 111.5
C5 C11 H11 111.5
C10 C11 H11 111.5
C13 C12 C4 121.2(2)
C13 C12 C11 129.5(2)
C4 C12 C11 109.14(18)
C12 C13 C1 117.8(2)
C12 C13 H13 121.1
C1 C13 H13 121.1
C15 C14 C19 118.88(19)
C15 C14 C10 122.01(18)
C19 C14 C10 118.66(18)
C14 C15 C16 120.4(2)
C14 C15 H15 119.8
C16 C15 H15 119.8
C17 C16 C15 120.7(2)
C17 C16 H16 119.6
C15 C16 H16 119.6
C16 C17 C18 119.3(2)
C16 C17 H17 120.3
C18 C17 H17 120.3
C19 C18 C17 119.9(2)
C19 C18 H18 120.0
C17 C18 H18 120.0
C18 C19 C14 120.6(2)
C18 C19 H19 119.7
C14 C19 H19 119.7
N1 C20 H20A 109.5
N1 C20 H20B 109.5
H20A C20 H20B 109.5
N1 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C6 O2 C10 104.97(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.903(2)
C1 C2 1.386(3)
C1 C13 1.391(3)
C2 C3 1.392(3)
C2 H2 0.93
C3 C4 1.400(3)
C3 H3 0.93
C4 C12 1.386(3)
C4 N1 1.393(3)
N1 C20 1.449(3)
N1 C5 1.474(3)
C5 C6 1.536(3)
C5 C11 1.546(3)
C5 H5 0.98
C6 O2 1.434(2)
C6 C7 1.515(3)
C6 H6 0.98
C7 O1 1.212(2)
C7 C8 1.513(3)
C8 C9 1.547(3)
C8 H8A 0.97
C8 H8B 0.97
C9 C10 1.534(3)
C9 H9A 0.97
C9 H9B 0.97
C10 O2 1.453(2)
C10 C14 1.518(3)
C10 C11 1.584(3)
C11 C12 1.506(3)
C11 H11 0.98
C12 C13 1.382(3)
C13 H13 0.93
C14 C15 1.382(3)
C14 C19 1.395(3)
C15 C16 1.391(3)
C15 H15 0.93
C16 C17 1.375(3)
C16 H16 0.93
C17 C18 1.393(3)
C17 H17 0.93
C18 C19 1.388(3)
C18 H18 0.93
C19 H19 0.93
C20 H20A 0.96
C20 H20B 0.96
C20 H20C 0.96
