#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/33/7213339.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7213339
loop_
_publ_author_name
'Banwell, Martin'
'Edwards, Alison'
'Harvey, Joanne'
'Hockless, David'
'Willis, Anthony'
_publ_section_title
;
 π-Allyl cation cyclisations initiated by silver(I)-promoted
 electrocyclic ring opening of ring-fused gem-dibromocyclopropanes
 possessing tethered nucleophiles: the influence of chiral auxiliaries on
 the diastereoselectivity of cyclisations involving meso-substrates
;
_journal_issue                   14
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2175
_journal_paper_doi               10.1039/b002525i
_journal_year                    2000
_chemical_formula_moiety         'C20 H24 Br N O2 '
_chemical_formula_sum            'C20 H24 Br N O2'
_chemical_formula_weight         390.32
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             2000-03-08
_audit_creation_method           'by teXsan v1.8'
_audit_update_record
;
Original title was 5-jeh-44g_copper_radiation
2000-03-08  cif compiled by acw
2000-03-08  passes checkcif with alerts
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.591(2)
_cell_length_b                   12.8947(9)
_cell_length_c                   14.871(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193.2
_cell_measurement_theta_max      54.4
_cell_measurement_theta_min      52.6
_cell_volume                     1839.1(5)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan (MSC, 1992-1997)'
_computing_publication_material  'teXsan (MSC, 1992-1997)'
_computing_structure_refinement  'teXsan (MSC, 1992-1997)'
_computing_structure_solution
;
SIR92 (Altomare, et. al. 1994)
;
_diffrn_ambient_temperature      193.2
_diffrn_measurement_device_details
;
Rigaku AFC6R diffractometer with extended arm and
evacuated collimator and beam tunnel.
Data cannot be collected beyond ψ 60 deg in this configuration.
;
_diffrn_measurement_device_type  'Rigaku AFC6R'
_diffrn_measurement_method       ω-2θ
_diffrn_orient_matrix_UB_11      -0.02782
_diffrn_orient_matrix_UB_12      0.06324
_diffrn_orient_matrix_UB_13      0.03453
_diffrn_orient_matrix_UB_21      -0.04755
_diffrn_orient_matrix_UB_22      -0.04469
_diffrn_orient_matrix_UB_23      0.04560
_diffrn_orient_matrix_UB_31      0.08852
_diffrn_orient_matrix_UB_32      -0.00413
_diffrn_orient_matrix_UB_33      0.03535
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.03673
_diffrn_reflns_av_sigmaI/netI    0.020
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5862
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         60.05
_diffrn_reflns_theta_min         2.97
_diffrn_standards_decay_%        -2.88
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.138
_exptl_absorpt_correction_T_max  0.661
_exptl_absorpt_correction_T_min  0.394
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
analytical (de Meulenaer & Tompa, 1965)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             808.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.38
_refine_ls_abs_structure_details
;
Absolute configuration by refinement of Flack parameter
;
_refine_ls_abs_structure_Flack   -.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.163
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2682
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0198
_refine_ls_shift/su_max          0.0130
_refine_ls_shift/su_mean         0.2030
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00022|Fo|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0266
_refine_ls_wR_factor_ref         0.0264
_reflns_number_gt                2682
_reflns_number_total             2738
_reflns_threshold_expression     I>2.00σ(I)
_cod_data_source_file            b002525isup1.cif
_cod_data_source_block           mgb60_Cu
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(Fo) +
0.00022|Fo|^2^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 1/[\s^2^(Fo) + 0.00022|Fo|^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1839.2(4)
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C20 H24 Br N O2 '
_cod_database_code               7213339
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'1/2-x,   -y,1/2+z'
'1/2+x,1/2-y,   -z'
'   -x,1/2+y,1/2-z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_calc_flag
Br(1) 0.60228(2) 0.50955(1) 0.43078(1) 0.04901(6) 1.000 Uani d
O(10) 0.4454(1) 0.30398(8) 0.31321(8) 0.0337(3) 1.000 Uani d
O(23) 0.4592(1) 0.13023(9) 0.33957(8) 0.0409(3) 1.000 Uani d
N(6) 0.4260(1) 0.2457(1) 0.45223(9) 0.0318(4) 1.000 Uani d
C(1) 0.4242(2) 0.2416(2) 0.6107(1) 0.0382(5) 1.000 Uani d
C(2) 0.5634(2) 0.2886(1) 0.6409(1) 0.0398(5) 1.000 Uani d
C(3) 0.6140(2) 0.3733(1) 0.5798(1) 0.0367(4) 1.000 Uani d
C(4) 0.5402(2) 0.4017(1) 0.5093(1) 0.0334(4) 1.000 Uani d
C(5) 0.4031(2) 0.3515(1) 0.4866(1) 0.0317(4) 1.000 Uani d
C(7) 0.4413(2) 0.1714(1) 0.5272(1) 0.0359(5) 1.000 Uani d
C(8) 0.3283(2) 0.3273(2) 0.5752(1) 0.0395(5) 1.000 Uani d
C(9) 0.4453(2) 0.2188(1) 0.3662(1) 0.0302(4) 1.000 Uani d
C(11) 0.4635(2) 0.2898(1) 0.2176(1) 0.0349(4) 1.000 Uani d
C(12) 0.4090(2) 0.3897(1) 0.1740(1) 0.0379(4) 1.000 Uani d
C(13) 0.4316(3) 0.3821(2) 0.0721(1) 0.0564(6) 1.000 Uani d
C(14) 0.5823(3) 0.3646(2) 0.0492(1) 0.0617(6) 1.000 Uani d
C(15) 0.6384(3) 0.2684(2) 0.0945(2) 0.0603(7) 1.000 Uani d
C(16) 0.6151(2) 0.2719(2) 0.1959(1) 0.0474(5) 1.000 Uani d
C(17) 0.2615(2) 0.4162(1) 0.2016(1) 0.0401(5) 1.000 Uani d
C(18) 0.2387(2) 0.4834(2) 0.2724(1) 0.0471(5) 1.000 Uani d
C(19) 0.1058(2) 0.5101(2) 0.3000(2) 0.0610(6) 1.000 Uani d
C(20) -0.0081(3) 0.4709(2) 0.2558(2) 0.0695(7) 1.000 Uani d
C(21) 0.0112(2) 0.4042(2) 0.1856(2) 0.0655(7) 1.000 Uani d
C(22) 0.1447(2) 0.3758(2) 0.1580(1) 0.0533(6) 1.000 Uani d
H(1) 0.3810 0.2048 0.6586 0.046 1.000 Uiso c
H(2) 0.5520 0.3164 0.6996 0.048 1.000 Uiso c
H(3) 0.6315 0.2351 0.6423 0.048 1.000 Uiso c
H(4) 0.7002 0.4068 0.5922 0.044 1.000 Uiso c
H(5) 0.3481 0.3925 0.4472 0.038 1.000 Uiso c
H(6) 0.3709 0.1197 0.5252 0.043 1.000 Uiso c
H(7) 0.5304 0.1394 0.5264 0.043 1.000 Uiso c
H(8) 0.3263 0.3857 0.6141 0.047 1.000 Uiso c
H(9) 0.2360 0.3031 0.5655 0.047 1.000 Uiso c
H(10) 0.4097 0.2324 0.1978 0.042 1.000 Uiso c
H(11) 0.4667 0.4445 0.1949 0.045 1.000 Uiso c
H(12) 0.4014 0.4449 0.0449 0.068 1.000 Uiso c
H(13) 0.3781 0.3259 0.0494 0.068 1.000 Uiso c
H(14) 0.5911 0.3570 -0.0141 0.074 1.000 Uiso c
H(15) 0.6351 0.4229 0.0684 0.074 1.000 Uiso c
H(16) 0.5923 0.2094 0.0706 0.072 1.000 Uiso c
H(17) 0.7356 0.2633 0.0829 0.072 1.000 Uiso c
H(18) 0.6437 0.2078 0.2215 0.057 1.000 Uiso c
H(19) 0.6690 0.3266 0.2209 0.057 1.000 Uiso c
H(20) 0.3166 0.5122 0.3030 0.057 1.000 Uiso c
H(21) 0.0934 0.5555 0.3496 0.073 1.000 Uiso c
H(22) -0.0996 0.4900 0.2738 0.083 1.000 Uiso c
H(23) -0.0675 0.3766 0.1551 0.079 1.000 Uiso c
H(24) 0.1562 0.3288 0.1094 0.064 1.000 Uiso c
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 80 0.017 0.009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H 0 96 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
Br 0 4 -0.767 1.283
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N 0 4 0.029 0.018
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O 0 8 0.047 0.032
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(9) O(10) C(11) 118.1(1) yes
C(5) N(6) C(7) 110.6(1) yes
C(5) N(6) C(9) 126.4(1) yes
C(7) N(6) C(9) 122.7(2) yes
C(2) C(1) C(7) 112.0(2) yes
C(2) C(1) C(8) 109.7(2) yes
C(2) C(1) H(1) 110.9 no
C(7) C(1) C(8) 102.1(2) yes
C(7) C(1) H(1) 110.9 no
C(8) C(1) H(1) 110.9 no
C(1) C(2) C(3) 113.1(2) yes
C(1) C(2) H(2) 108.6 no
C(1) C(2) H(3) 108.6 no
C(3) C(2) H(2) 108.6 no
C(3) C(2) H(3) 108.6 no
H(2) C(2) H(3) 109.5 no
C(2) C(3) C(4) 120.6(2) yes
C(2) C(3) H(4) 119.7 no
C(4) C(3) H(4) 119.7 no
Br(1) C(4) C(3) 121.4(2) yes
Br(1) C(4) C(5) 116.6(1) yes
C(3) C(4) C(5) 122.0(2) yes
N(6) C(5) C(4) 110.2(1) yes
N(6) C(5) C(8) 100.4(1) yes
N(6) C(5) H(5) 112.6 no
C(4) C(5) C(8) 107.7(2) yes
C(4) C(5) H(5) 112.6 no
C(8) C(5) H(5) 112.6 no
N(6) C(7) C(1) 102.5(1) yes
N(6) C(7) H(6) 111.2 no
N(6) C(7) H(7) 111.2 no
C(1) C(7) H(6) 111.2 no
C(1) C(7) H(7) 111.2 no
H(6) C(7) H(7) 109.5 no
C(1) C(8) C(5) 99.4(1) yes
C(1) C(8) H(8) 111.9 no
C(1) C(8) H(9) 111.9 no
C(5) C(8) H(8) 111.9 no
C(5) C(8) H(9) 111.9 no
H(8) C(8) H(9) 109.5 no
O(10) C(9) O(23) 124.9(2) yes
O(10) C(9) N(6) 110.3(1) yes
O(23) C(9) N(6) 124.8(2) yes
O(10) C(11) C(12) 105.6(2) yes
O(10) C(11) C(16) 110.2(2) yes
O(10) C(11) H(10) 109.8 no
C(12) C(11) C(16) 111.6(2) yes
C(12) C(11) H(10) 109.8 no
C(16) C(11) H(10) 109.8 no
C(11) C(12) C(13) 108.4(2) yes
C(11) C(12) C(17) 113.2(2) yes
C(11) C(12) H(11) 106.7 no
C(13) C(12) C(17) 114.5(2) yes
C(13) C(12) H(11) 106.7 no
C(17) C(12) H(11) 106.7 no
C(12) C(13) C(14) 111.7(2) yes
C(12) C(13) H(12) 108.9 no
C(12) C(13) H(13) 108.9 no
C(14) C(13) H(12) 108.9 no
C(14) C(13) H(13) 108.9 no
H(12) C(13) H(13) 109.5 no
C(13) C(14) C(15) 111.4(2) yes
C(13) C(14) H(14) 109.0 no
C(13) C(14) H(15) 109.0 no
C(15) C(14) H(14) 109.0 no
C(15) C(14) H(15) 109.0 no
H(14) C(14) H(15) 109.5 no
C(14) C(15) C(16) 111.4(2) yes
C(14) C(15) H(16) 109.0 no
C(14) C(15) H(17) 109.0 no
C(16) C(15) H(16) 109.0 no
C(16) C(15) H(17) 109.0 no
H(16) C(15) H(17) 109.5 no
C(11) C(16) C(15) 110.9(2) yes
C(11) C(16) H(18) 109.1 no
C(11) C(16) H(19) 109.1 no
C(15) C(16) H(18) 109.1 no
C(15) C(16) H(19) 109.1 no
H(18) C(16) H(19) 109.5 no
C(12) C(17) C(18) 119.8(2) yes
C(12) C(17) C(22) 122.8(2) yes
C(18) C(17) C(22) 117.5(2) yes
C(17) C(18) C(19) 121.9(2) yes
C(17) C(18) H(20) 119.1 no
C(19) C(18) H(20) 119.1 no
C(18) C(19) C(20) 120.1(2) yes
C(18) C(19) H(21) 120.0 no
C(20) C(19) H(21) 120.0 no
C(19) C(20) C(21) 119.3(2) yes
C(19) C(20) H(22) 120.3 no
C(21) C(20) H(22) 120.3 no
C(20) C(21) C(22) 121.0(3) yes
C(20) C(21) H(23) 119.5 no
C(22) C(21) H(23) 119.5 no
C(17) C(22) C(21) 120.2(3) yes
C(17) C(22) H(24) 119.9 no
C(21) C(22) H(24) 119.9 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br(1) C(4) 1.912(2) yes
O(10) C(9) 1.352(2) yes
O(10) C(11) 1.444(2) yes
O(23) C(9) 1.216(2) yes
N(6) C(5) 1.473(2) yes
N(6) C(7) 1.477(2) yes
N(6) C(9) 1.338(2) yes
C(1) C(2) 1.534(3) yes
C(1) C(7) 1.544(3) yes
C(1) C(8) 1.532(3) yes
C(1) H(1) 0.95 no
C(2) C(3) 1.502(3) yes
C(2) H(2) 0.95 no
C(2) H(3) 0.95 no
C(3) C(4) 1.317(3) yes
C(3) H(4) 0.95 no
C(4) C(5) 1.504(3) yes
C(5) C(8) 1.531(3) yes
C(5) H(5) 0.95 no
C(7) H(6) 0.95 no
C(7) H(7) 0.95 no
C(8) H(8) 0.95 no
C(8) H(9) 0.95 no
C(11) C(12) 1.533(3) yes
C(11) C(16) 1.507(3) yes
C(11) H(10) 0.95 no
C(12) C(13) 1.534(3) yes
C(12) C(17) 1.512(3) yes
C(12) H(11) 0.95 no
C(13) C(14) 1.503(4) yes
C(13) H(12) 0.95 no
C(13) H(13) 0.95 no
C(14) C(15) 1.510(4) yes
C(14) H(14) 0.95 no
C(14) H(15) 0.95 no
C(15) C(16) 1.526(3) yes
C(15) H(16) 0.95 no
C(15) H(17) 0.95 no
C(16) H(18) 0.95 no
C(16) H(19) 0.95 no
C(17) C(18) 1.382(3) yes
C(17) C(22) 1.395(3) yes
C(18) C(19) 1.383(3) yes
C(18) H(20) 0.95 no
C(19) C(20) 1.372(4) yes
C(19) H(21) 0.95 no
C(20) C(21) 1.365(4) yes
C(20) H(22) 0.95 no
C(21) C(22) 1.393(4) yes
C(21) H(23) 0.95 no
C(22) H(24) 0.95 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O(23) C(12) 3.356(2) 4_645 no
O(23) C(3) 3.521(2) 3_456 no
N(6) C(3) 3.396(2) 3_456 no
C(1) C(20) 3.445(3) 3_556 no
C(2) C(20) 3.580(3) 2_565 no
C(3) C(20) 3.451(3) 2_565 no
C(3) C(9) 3.486(3) 3_556 no
C(3) C(21) 3.486(3) 2_565 no
C(3) C(7) 3.566(3) 3_556 no
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
_geom_torsion_publ_flag
Br(1) C(4) C(3) C(2) 179.8(1) no
Br(1) C(4) C(5) N(6) 108.1(1) no
Br(1) C(4) C(5) C(8) -143.3(1) no
O(10) C(9) N(6) C(5) 1.9(3) no
O(10) C(9) N(6) C(7) -170.9(2) no
O(10) C(11) C(12) C(13) 177.3(2) no
O(10) C(11) C(12) C(17) -54.5(2) no
O(10) C(11) C(16) C(15) -173.9(2) no
O(23) C(9) O(10) C(11) -0.1(3) no
O(23) C(9) N(6) C(5) -177.3(2) no
O(23) C(9) N(6) C(7) 9.9(3) no
N(6) C(5) C(4) C(3) -72.2(2) no
N(6) C(5) C(8) C(1) 46.6(2) no
N(6) C(7) C(1) C(2) -88.1(2) no
N(6) C(7) C(1) C(8) 29.2(2) no
N(6) C(9) O(10) C(11) -179.3(2) no
C(1) C(2) C(3) C(4) 1.0(3) no
C(1) C(7) N(6) C(5) 0.5(2) no
C(1) C(7) N(6) C(9) 174.3(2) no
C(1) C(8) C(5) C(4) -68.8(2) no
C(2) C(1) C(8) C(5) 71.7(2) no
C(2) C(3) C(4) C(5) 0.1(3) no
C(3) C(2) C(1) C(7) 73.6(2) no
C(3) C(2) C(1) C(8) -39.0(2) no
C(3) C(4) C(5) C(8) 36.4(2) no
C(4) C(5) N(6) C(7) 83.5(2) no
C(4) C(5) N(6) C(9) -90.0(2) no
C(5) C(8) C(1) C(7) -47.2(2) no
C(7) N(6) C(5) C(8) -29.9(2) no
C(8) C(5) N(6) C(9) 156.6(2) no
C(9) O(10) C(11) C(12) 160.7(2) no
C(9) O(10) C(11) C(16) -78.7(2) no
C(11) C(12) C(13) C(14) -57.4(2) no
C(11) C(12) C(17) C(18) 94.6(2) no
C(11) C(12) C(17) C(22) -85.8(2) no
C(11) C(16) C(15) C(14) 54.5(3) no
C(12) C(11) C(16) C(15) -56.9(2) no
C(12) C(13) C(14) C(15) 56.9(3) no
C(12) C(17) C(18) C(19) 179.9(2) no
C(12) C(17) C(22) C(21) -179.1(2) no
C(13) C(12) C(11) C(16) 57.6(2) no
C(13) C(12) C(17) C(18) -140.5(2) no
C(13) C(12) C(17) C(22) 39.2(3) no
C(13) C(14) C(15) C(16) -54.5(3) no
C(14) C(13) C(12) C(17) 175.2(2) no
C(16) C(11) C(12) C(17) -174.3(2) no
C(17) C(18) C(19) C(20) -1.2(3) no
C(17) C(22) C(21) C(20) -0.5(4) no
C(18) C(17) C(22) C(21) 0.6(3) no
C(18) C(19) C(20) C(21) 1.2(4) no
C(19) C(18) C(17) C(22) 0.3(3) no
C(19) C(20) C(21) C(22) -0.4(4) no
