#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/25/4112527.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_4112527
loop_
_publ_author_name
'Yoshinori Nishii'
'Kazunori Wakasugi'
'Keisuke Koga'
'Yoo Tanabe'
_publ_section_title
;
 Chirality Exchange from sp3 Central Chirality to Axial Chirality:
 Benzannulation of Optically Active
 Diaryl-2,2-dichlorocyclopropylmethanols to Axially Chiral
 α-Arylnaphthalenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5358
_journal_page_last               5359
_journal_paper_doi               10.1021/ja0319442
_journal_volume                  126
_journal_year                    2004
_chemical_formula_moiety         'C18 H13 Br2 Cl '
_chemical_formula_sum            'C18 H13 Br2 Cl'
_chemical_formula_weight         424.56
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_audit_creation_date             'Tue Apr  9 17:34:41 2002'
_audit_creation_method           'by teXsan'
_cell_angle_alpha                90
_cell_angle_beta                 112.78(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.251(3)
_cell_length_b                   6.856(1)
_cell_length_c                   10.484(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298.2
_cell_measurement_theta_max      29.3
_cell_measurement_theta_min      25.4
_cell_volume                     1673.4(4)
_computing_cell_refinement       WinAFC
_computing_data_collection       WinAFC
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_measured_fraction_theta_full 2.1562
_diffrn_measured_fraction_theta_max 2.1562
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3879
_diffrn_reflns_theta_full        67.99
_diffrn_reflns_theta_max         67.99
_diffrn_standards_decay_%        4.05
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    7.525
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.75
_refine_diff_density_min         -0.73
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.997
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3294
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.0016
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00063|Fo|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0693
_reflns_number_gt                3294
_reflns_number_total             3591
_reflns_threshold_expression     F²>3.0σ(F²)
_cod_data_source_file            ja0319442si20040331_045817.cif
_cod_data_source_block           KAW-1564
_cod_original_cell_volume        1673.5(5)
_cod_original_formula_sum        'C18 H13 Br2 Cl '
_cod_database_code               4112527
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y,-z
1/2+x,1/2+y,z
1/2-x,1/2+y,-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_calc_flag
Br(1) Br 0.28255(3) 1.0000 0.15677(7) 0.0764(2) Uani 1.00 d
Br(2) Br 0.09219(4) 1.0521(2) 0.27772(9) 0.0964(3) Uani 1.00 d
Cl(1) Cl 0.0914(1) 0.9606(4) -0.3829(2) 0.1016(7) Uani 1.00 d
C(1) C 0.1431(2) 0.7318(9) 0.0548(5) 0.047(1) Uani 1.00 d
C(2) C 0.1032(2) 0.624(1) -0.0582(5) 0.053(2) Uani 1.00 d
C(3) C 0.0813(3) 0.4401(10) -0.0373(6) 0.062(2) Uani 1.00 d
C(4) C 0.0440(3) 0.333(1) -0.1453(8) 0.083(2) Uani 1.00 d
C(5) C 0.0282(3) 0.401(1) -0.2810(9) 0.089(3) Uani 1.00 d
C(6) C 0.0491(3) 0.574(1) -0.3051(7) 0.080(2) Uani 1.00 d
C(7) C 0.0866(2) 0.692(1) -0.1967(5) 0.056(2) Uani 1.00 d
C(8) C 0.1093(3) 0.874(1) -0.2155(5) 0.064(2) Uani 1.00 d
C(9) C 0.1454(2) 0.979(1) -0.1082(5) 0.059(2) Uani 1.00 d
C(10) C 0.1633(2) 0.9076(9) 0.0290(5) 0.047(1) Uani 1.00 d
C(11) C 0.2034(2) 1.0302(10) 0.1420(6) 0.058(2) Uani 1.00 d
C(12) C 0.1632(2) 0.6476(9) 0.1956(5) 0.049(1) Uani 1.00 d
C(13) C 0.2149(3) 0.5492(9) 0.2457(5) 0.058(2) Uani 1.00 d
C(14) C 0.2346(3) 0.456(1) 0.3749(7) 0.079(2) Uani 1.00 d
C(15) C 0.2029(4) 0.463(1) 0.4530(6) 0.083(2) Uani 1.00 d
C(16) C 0.1525(3) 0.565(1) 0.4089(6) 0.077(2) Uani 1.00 d
C(17) C 0.1315(2) 0.6619(10) 0.2789(6) 0.060(2) Uani 1.00 d
C(18) C 0.0757(3) 0.779(2) 0.2307(7) 0.085(3) Uani 1.00 d
H(1) H 0.0927 0.3875 0.0543 0.0682 Uiso 1.00 calc
H(2) H 0.0294 0.2108 -0.1301 0.0939 Uiso 1.00 calc
H(3) H 0.0029 0.3252 -0.3558 0.1022 Uiso 1.00 calc
H(4) H 0.0390 0.6137 -0.3985 0.0892 Uiso 1.00 calc
H(5) H 0.1593 1.0970 -0.1260 0.0640 Uiso 1.00 calc
H(6) H 0.2378 0.5428 0.1919 0.0622 Uiso 1.00 calc
H(7) H 0.2703 0.3851 0.4072 0.0897 Uiso 1.00 calc
H(8) H 0.2155 0.3924 0.5384 0.0937 Uiso 1.00 calc
H(9) H 0.1314 0.5688 0.4665 0.0874 Uiso 1.00 calc
H(10) H 0.1917 1.1589 0.1221 0.0635 Uiso 1.00 calc
H(11) H 0.2010 0.9889 0.2262 0.0635 Uiso 1.00 calc
H(12) H 0.0567 0.7597 0.1308 0.0925 Uiso 1.00 calc
H(13) H 0.0512 0.7226 0.2711 0.0925 Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
Cl Cl 0.364 0.702
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
Br Br -0.676 1.280
;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(2) C(1) C(10) 119.1(5) yes
C(2) C(1) C(12) 118.9(5) yes
C(10) C(1) C(12) 121.9(5) yes
C(1) C(2) C(3) 121.4(5) yes
C(1) C(2) C(7) 120.5(6) yes
C(3) C(2) C(7) 118.0(5) yes
C(2) C(3) C(4) 121.9(6) yes
C(3) C(4) C(5) 119.6(7) yes
C(4) C(5) C(6) 120.2(7) yes
C(5) C(6) C(7) 122.3(7) yes
C(2) C(7) C(6) 118.1(7) yes
C(2) C(7) C(8) 117.2(5) yes
C(6) C(7) C(8) 124.7(6) yes
Cl(1) C(8) C(7) 118.8(5) yes
Cl(1) C(8) C(9) 119.1(6) yes
C(7) C(8) C(9) 122.1(5) yes
C(8) C(9) C(10) 120.7(6) yes
C(1) C(10) C(9) 120.3(5) yes
C(1) C(10) C(11) 121.9(5) yes
C(9) C(10) C(11) 117.8(5) yes
Br(1) C(11) C(10) 111.3(4) yes
C(1) C(12) C(13) 118.6(5) yes
C(1) C(12) C(17) 122.5(5) yes
C(13) C(12) C(17) 118.9(5) yes
C(12) C(13) C(14) 121.2(6) yes
C(13) C(14) C(15) 119.8(6) yes
C(14) C(15) C(16) 120.5(6) yes
C(15) C(16) C(17) 121.1(6) yes
C(12) C(17) C(16) 118.4(6) yes
C(12) C(17) C(18) 120.5(5) yes
C(16) C(17) C(18) 121.1(6) yes
Br(2) C(18) C(17) 110.1(5) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br(1) C(11) 1.956(5) yes
Br(2) C(18) 1.94(1) yes
Cl(1) C(8) 1.739(5) yes
C(1) C(2) 1.430(7) yes
C(1) C(10) 1.376(9) yes
C(1) C(12) 1.480(7) yes
C(2) C(3) 1.426(8) yes
C(2) C(7) 1.425(7) yes
C(3) C(4) 1.372(9) yes
C(4) C(5) 1.40(1) yes
C(5) C(6) 1.36(1) yes
C(6) C(7) 1.418(9) yes
C(7) C(8) 1.42(1) yes
C(8) C(9) 1.350(9) yes
C(9) C(10) 1.416(7) yes
C(10) C(11) 1.485(7) yes
C(12) C(13) 1.381(8) yes
C(12) C(17) 1.398(8) yes
C(13) C(14) 1.403(8) yes
C(14) C(15) 1.35(1) yes
C(15) C(16) 1.37(1) yes
C(16) C(17) 1.420(8) yes
C(17) C(18) 1.53(1) yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
Br(1) C(7) 3.429(5) 4_555
Br(1) C(2) 3.525(5) 4_555
C(4) C(9) 3.44(1) 1_545
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(11) C(10) C(1) 100.6(5) yes
Br(1) C(11) C(10) C(9) -80.3(6) yes
Br(2) C(18) C(17) C(12) -85.3(6) yes
Br(2) C(18) C(17) C(16) 94.5(7) yes
Cl(1) C(8) C(7) C(2) 178.7(4) yes
Cl(1) C(8) C(7) C(6) -0.9(8) yes
Cl(1) C(8) C(9) C(10) -176.7(4) yes
C(1) C(2) C(3) C(4) -178.5(6) yes
C(1) C(2) C(7) C(6) 176.9(5) yes
C(1) C(2) C(7) C(8) -2.7(8) yes
C(1) C(10) C(9) C(8) -1.2(9) yes
C(1) C(12) C(13) C(14) -176.1(6) yes
C(1) C(12) C(17) C(16) 175.9(6) yes
C(1) C(12) C(17) C(18) -4.2(9) yes
C(2) C(1) C(10) C(9) -1.0(8) yes
C(2) C(1) C(10) C(11) 178.1(5) yes
C(2) C(1) C(12) C(13) 96.7(6) yes
C(2) C(1) C(12) C(17) -82.5(7) yes
C(2) C(3) C(4) C(5) 2(1) yes
C(2) C(7) C(6) C(5) 0.9(9) yes
C(2) C(7) C(8) C(9) 0.4(9) yes
C(3) C(2) C(1) C(10) 179.5(5) yes
C(3) C(2) C(1) C(12) 1.8(8) yes
C(3) C(2) C(7) C(6) 0.4(8) yes
C(3) C(2) C(7) C(8) -179.3(5) yes
C(3) C(4) C(5) C(6) 0(1) yes
C(4) C(3) C(2) C(7) -1.9(9) yes
C(4) C(5) C(6) C(7) 0(1) yes
C(5) C(6) C(7) C(8) -179.5(7) yes
C(6) C(7) C(8) C(9) -179.2(6) yes
C(7) C(2) C(1) C(10) 3.0(8) yes
C(7) C(2) C(1) C(12) -174.6(5) yes
C(7) C(8) C(9) C(10) 1.5(9) yes
C(8) C(9) C(10) C(11) 179.6(5) yes
C(9) C(10) C(1) C(12) 176.6(5) yes
C(10) C(1) C(12) C(13) -80.9(8) yes
C(10) C(1) C(12) C(17) 99.9(7) yes
C(11) C(10) C(1) C(12) -4.3(8) yes
C(12) C(13) C(14) C(15) 0(1) yes
C(12) C(17) C(16) C(15) 0.8(10) yes
C(13) C(12) C(17) C(16) -3.3(9) yes
C(13) C(12) C(17) C(18) 176.6(6) yes
C(13) C(14) C(15) C(16) -2(1) yes
C(14) C(13) C(12) C(17) 3.1(9) yes
C(14) C(15) C(16) C(17) 1(1) yes
C(15) C(16) C(17) C(18) -179.0(7) yes
C(15) C(16) C(17) C(18) -179.0(7) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660462
