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#$Date: 2019-11-25 16:31:11 +0200 (Mon, 25 Nov 2019) $
#$Revision: 241330 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/10/4131009.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_4131009
loop_
_publ_author_name
'Wang, Xiao-Ye'
'Wang, Xin-Chang'
'Narita, Akimitsu'
'Wagner, Manfred'
'Cao, Xiao-Yu'
'Feng, Xinliang'
'Müllen, Klaus'
_publ_section_title
;
 Synthesis, Structure, and Chiroptical Properties of a Double
 [7]Heterohelicene.
;
_journal_issue                   39
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12783
_journal_page_last               12786
_journal_paper_doi               10.1021/jacs.6b08664
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C50 H37 Br O4'
_chemical_formula_sum            'C50 H37 Br O4'
_chemical_formula_weight         781.70
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   32.9726(10)
_cell_length_b                   32.9726(10)
_cell_length_c                   10.6792(3)
_cell_measurement_reflns_used    15691
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.60
_cell_measurement_theta_min      2.14
_cell_volume                     10054.9(5)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SHELXT-2014
_diffrn_ambient_temperature      193(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      ' 210 frames, detector distance = 70 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26930
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.505
_diffrn_reflns_theta_min         2.140
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.960
_exptl_absorpt_correction_T_max  0.9343
_exptl_absorpt_correction_T_min  0.6286
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_description       block
_exptl_crystal_F_000             3636
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_platon_squeeze_details
;
TITL w160      R -3 :h      R = 0.10
CELL   32.9610   32.9610   10.6960     90.00     90.00    120.00
SPGR R-3
# Solvent Accessible Volume =      1904
# Electrons Found in S.A.V. =        85
# Note: Atoms in Void as Cxxx and Qxxx all others
Q101 0.085 0.836 0.146 !       1.04 eA-3
Q102 0.015 0.698 0.123 !       0.73 eA-3
Q103 0.377 0.982 0.202 !       0.52 eA-3
;
_refine_diff_density_max         0.808
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.0020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.525
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         5631
_refine_ls_number_restraints     183
_refine_ls_restrained_S_all      1.532
_refine_ls_R_factor_all          0.1359
_refine_ls_R_factor_gt           0.0932
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2454
_refine_ls_wR_factor_ref         0.2670
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3353
_reflns_number_total             5631
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b08664_si_002.cif
_cod_data_source_block           w160
_cod_original_cell_volume        10054.8(7)
_cod_database_code               4131009
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.775
_shelx_estimated_absorpt_t_max   0.927
_platon_squeeze_void_probe_radius 1.20
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.05850(3) 0.41866(3) 0.20542(7) 0.0723(3) Uani 0.5 1 d . . P A 1
C1 C -0.04921(18) 0.40172(14) -0.0719(3) 0.0729(11) Uani 1 1 d . U . . .
C2 C -0.0988(2) 0.37764(15) -0.0839(4) 0.0854(12) Uani 1 1 d . U . . .
C3 C -0.12547(18) 0.3992(2) -0.0611(5) 0.0940(14) Uani 1 1 d . U . . .
H3 H -0.1100 0.4315 -0.0401 0.113 Uiso 1 1 calc R U . . .
C4 C -0.1736(3) 0.3746(3) -0.0686(8) 0.136(2) Uani 1 1 d . U . . .
H4 H -0.1916 0.3890 -0.0488 0.163 Uiso 1 1 calc R U . . .
C5 C -0.1959(3) 0.3258(3) -0.1079(9) 0.150(3) Uani 1 1 d . U . . .
H5 H -0.2290 0.3084 -0.1159 0.180 Uiso 1 1 calc R U . . .
C6 C -0.1707(3) 0.3050(2) -0.1331(7) 0.131(2) Uani 1 1 d . U . . .
H6 H -0.1865 0.2734 -0.1605 0.157 Uiso 1 1 calc R U . . .
C7 C -0.1231(2) 0.32801(19) -0.1204(4) 0.1018(16) Uani 1 1 d . U . . .
C8 C -0.0950(3) 0.3080(2) -0.1390(5) 0.1126(18) Uani 1 1 d . U . . .
H8 H -0.1103 0.2759 -0.1628 0.135 Uiso 1 1 calc R U . . .
C9 C -0.0492(3) 0.3295(2) -0.1265(5) 0.1063(18) Uani 1 1 d . U . . .
H9 H -0.0328 0.3130 -0.1393 0.128 Uiso 1 1 calc R U . . .
C10 C -0.0246(2) 0.37810(16) -0.0933(4) 0.0844(14) Uani 1 1 d . U . . .
O11 O 0.02232(16) 0.40329(15) -0.0771(3) 0.0940(11) Uani 1 1 d . . . . .
C12 C 0.0495(3) 0.3815(3) -0.1101(6) 0.139(3) Uani 1 1 d . . . . .
H12A H 0.0304 0.3475 -0.0987 0.208 Uiso 1 1 calc R U . . .
H12B H 0.0772 0.3938 -0.0562 0.208 Uiso 1 1 calc R U . . .
H12C H 0.0594 0.3884 -0.1978 0.208 Uiso 1 1 calc R U . . .
C13 C -0.02300(15) 0.45230(13) -0.0365(3) 0.0613(9) Uani 1 1 d . U . . .
C14 C -0.02712(15) 0.46655(13) 0.0833(3) 0.0622(9) Uani 1 1 d . U . . .
H14 H -0.0457 0.4430 0.1426 0.075 Uiso 0.5 1 calc R U P A 2
C15 C -0.00567(14) 0.51307(12) 0.1216(3) 0.0590(8) Uani 1 1 d . U . . .
C16 C -0.01409(16) 0.52511(13) 0.2507(3) 0.0650(9) Uani 1 1 d . U . . .
C17 C -0.05943(19) 0.51893(16) 0.2803(4) 0.0798(11) Uani 1 1 d . U . . .
C18 C -0.0960(2) 0.5023(2) 0.1930(5) 0.0916(14) Uani 1 1 d . U . . .
H18 H -0.0910 0.4944 0.1110 0.110 Uiso 1 1 calc R U . . .
C19 C -0.1382(3) 0.4971(3) 0.2227(7) 0.127(2) Uani 1 1 d . U . . .
H19 H -0.1625 0.4865 0.1620 0.152 Uiso 1 1 calc R U . . .
C20 C -0.1457(3) 0.5081(3) 0.3495(9) 0.151(3) Uani 1 1 d . U . . .
H20 H -0.1756 0.5031 0.3732 0.182 Uiso 1 1 calc R U . . .
C21 C -0.1109(3) 0.5250(3) 0.4327(7) 0.130(2) Uani 1 1 d . U . . .
H21 H -0.1162 0.5330 0.5142 0.156 Uiso 1 1 calc R U . . .
C22 C -0.0665(2) 0.53139(19) 0.4026(5) 0.0955(14) Uani 1 1 d . U . . .
C23 C -0.0304(2) 0.54789(18) 0.4902(4) 0.0960(15) Uani 1 1 d . U . . .
H23 H -0.0357 0.5555 0.5721 0.115 Uiso 1 1 calc R U . . .
C24 C 0.0118(2) 0.55339(15) 0.4618(4) 0.0854(13) Uani 1 1 d . U . . .
H24 H 0.0360 0.5652 0.5229 0.103 Uiso 1 1 calc R U . . .
C25 C 0.02018(17) 0.54147(13) 0.3397(3) 0.0683(10) Uani 1 1 d . U . . .
O26 O 0.06205(12) 0.54531(10) 0.3071(3) 0.0785(8) Uani 1 1 d . . . . .
C27 C 0.1020(2) 0.5722(2) 0.3851(6) 0.1083(18) Uani 1 1 d . . . . .
H27A H 0.1130 0.6056 0.3736 0.162 Uiso 1 1 calc R U . . .
H27B H 0.1270 0.5657 0.3622 0.162 Uiso 1 1 calc R U . . .
H27C H 0.0933 0.5637 0.4729 0.162 Uiso 1 1 calc R U . . .
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'
Br Br -0.2901 2.4595 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -2 1 0.1710
-2 2 -1 0.1710
0 1 2 0.0945
0 -1 -2 0.0945
0 -1 1 0.0430
0 1 -1 0.0430
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
C10 C1 C2 120.1(4) . .
C10 C1 C13 119.4(5) . .
C2 C1 C13 120.5(4) . .
C3 C2 C1 122.7(4) . .
C3 C2 C7 118.8(6) . .
C1 C2 C7 118.6(5) . .
C4 C3 C2 121.5(6) . .
C4 C3 H3 119.2 . .
C2 C3 H3 119.2 . .
C3 C4 C5 117.6(8) . .
C3 C4 H4 121.2 . .
C5 C4 H4 121.2 . .
C6 C5 C4 121.5(8) . .
C6 C5 H5 119.3 . .
C4 C5 H5 119.3 . .
C5 C6 C7 122.1(7) . .
C5 C6 H6 119.0 . .
C7 C6 H6 119.0 . .
C6 C7 C8 125.1(7) . .
C6 C7 C2 118.5(7) . .
C8 C7 C2 116.5(6) . .
C9 C8 C7 125.7(6) . .
C9 C8 H8 117.1 . .
C7 C8 H8 117.1 . .
C8 C9 C10 119.1(6) . .
C8 C9 H9 120.5 . .
C10 C9 H9 120.5 . .
O11 C10 C1 116.2(4) . .
O11 C10 C9 123.7(5) . .
C1 C10 C9 120.1(6) . .
C10 O11 C12 117.8(5) . .
O11 C12 H12A 109.5 . .
O11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
O11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C14 C13 C15 117.6(3) . 10_565
C14 C13 C1 120.7(3) . .
C15 C13 C1 121.8(3) 10_565 .
C15 C14 C13 124.1(3) . .
C15 C14 Br1 118.6(3) . .
C13 C14 Br1 116.9(3) . .
C15 C14 H14 118.0 . .
C13 C14 H14 118.0 . .
C14 C15 C13 118.3(3) . 10_565
C14 C15 C16 120.2(3) . .
C13 C15 C16 121.5(3) 10_565 .
C25 C16 C17 119.9(4) . .
C25 C16 C15 121.3(4) . .
C17 C16 C15 118.8(4) . .
C18 C17 C22 119.5(5) . .
C18 C17 C16 122.6(4) . .
C22 C17 C16 117.9(5) . .
C19 C18 C17 121.5(5) . .
C19 C18 H18 119.2 . .
C17 C18 H18 119.2 . .
C18 C19 C20 118.6(7) . .
C18 C19 H19 120.7 . .
C20 C19 H19 120.7 . .
C21 C20 C19 120.5(7) . .
C21 C20 H20 119.7 . .
C19 C20 H20 119.7 . .
C20 C21 C22 121.5(6) . .
C20 C21 H21 119.2 . .
C22 C21 H21 119.2 . .
C23 C22 C21 121.8(5) . .
C23 C22 C17 119.9(5) . .
C21 C22 C17 118.3(6) . .
C24 C23 C22 121.7(4) . .
C24 C23 H23 119.1 . .
C22 C23 H23 119.1 . .
C23 C24 C25 119.9(5) . .
C23 C24 H24 120.1 . .
C25 C24 H24 120.1 . .
C16 C25 O26 117.2(3) . .
C16 C25 C24 120.6(5) . .
O26 C25 C24 122.2(4) . .
C25 O26 C27 118.9(4) . .
O26 C27 H27A 109.5 . .
O26 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
O26 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C14 1.905(4) .
C1 C10 1.397(7) .
C1 C2 1.423(7) .
C1 C13 1.493(5) .
C2 C3 1.399(8) .
C2 C7 1.470(7) .
C3 C4 1.376(8) .
C3 H3 0.9500 .
C4 C5 1.456(11) .
C4 H4 0.9500 .
C5 C6 1.342(12) .
C5 H5 0.9500 .
C6 C7 1.369(10) .
C6 H6 0.9500 .
C7 C8 1.395(10) .
C8 C9 1.314(10) .
C8 H8 0.9500 .
C9 C10 1.433(8) .
C9 H9 0.9500 .
C10 O11 1.351(7) .
O11 C12 1.445(6) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C14 1.393(5) .
C13 C15 1.394(5) 10_565
C14 C15 1.391(5) .
C14 H14 0.9500 .
C15 C13 1.394(5) 10_565
C15 C16 1.499(5) .
C16 C25 1.365(6) .
C16 C17 1.440(7) .
C17 C18 1.400(8) .
C17 C22 1.423(6) .
C18 C19 1.354(8) .
C18 H18 0.9500 .
C19 C20 1.454(11) .
C19 H19 0.9500 .
C20 C21 1.333(12) .
C20 H20 0.9500 .
C21 C22 1.410(9) .
C21 H21 0.9500 .
C22 C23 1.393(8) .
C23 C24 1.343(8) .
C23 H23 0.9500 .
C24 C25 1.429(5) .
C24 H24 0.9500 .
C25 O26 1.367(5) .
O26 C27 1.430(6) .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
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_site_symmetry_1
_geom_torsion_site_symmetry_4
C10 C1 C2 C3 178.6(4) . .
C13 C1 C2 C3 -1.3(6) . .
C10 C1 C2 C7 -0.8(6) . .
C13 C1 C2 C7 179.3(4) . .
C1 C2 C3 C4 -177.4(5) . .
C7 C2 C3 C4 2.0(8) . .
C2 C3 C4 C5 -3.3(10) . .
C3 C4 C5 C6 1.6(13) . .
C4 C5 C6 C7 1.6(13) . .
C5 C6 C7 C8 176.7(7) . .
C5 C6 C7 C2 -2.9(10) . .
C3 C2 C7 C6 1.2(7) . .
C1 C2 C7 C6 -179.4(5) . .
C3 C2 C7 C8 -178.5(4) . .
C1 C2 C7 C8 0.9(6) . .
C6 C7 C8 C9 -179.6(6) . .
C2 C7 C8 C9 0.1(8) . .
C7 C8 C9 C10 -1.3(8) . .
C2 C1 C10 O11 -178.6(4) . .
C13 C1 C10 O11 1.4(5) . .
C2 C1 C10 C9 -0.4(6) . .
C13 C1 C10 C9 179.6(4) . .
C8 C9 C10 O11 179.4(4) . .
C8 C9 C10 C1 1.4(7) . .
C1 C10 O11 C12 -174.1(4) . .
C9 C10 O11 C12 7.8(6) . .
C10 C1 C13 C14 -111.1(4) . .
C2 C1 C13 C14 68.9(5) . .
C10 C1 C13 C15 70.0(5) . 10_565
C2 C1 C13 C15 -110.0(5) . 10_565
C15 C13 C14 C15 2.1(7) 10_565 .
C1 C13 C14 C15 -176.8(4) . .
C15 C13 C14 Br1 -170.7(3) 10_565 .
C1 C13 C14 Br1 10.3(5) . .
C13 C14 C15 C13 -2.1(7) . 10_565
Br1 C14 C15 C13 170.6(3) . 10_565
C13 C14 C15 C16 177.0(4) . .
Br1 C14 C15 C16 -10.3(5) . .
C14 C15 C16 C25 109.3(5) . .
C13 C15 C16 C25 -71.7(5) 10_565 .
C14 C15 C16 C17 -70.5(5) . .
C13 C15 C16 C17 108.6(5) 10_565 .
C25 C16 C17 C18 -180.0(4) . .
C15 C16 C17 C18 -0.2(6) . .
C25 C16 C17 C22 1.4(6) . .
C15 C16 C17 C22 -178.8(4) . .
C22 C17 C18 C19 -0.9(8) . .
C16 C17 C18 C19 -179.5(5) . .
C17 C18 C19 C20 -1.6(11) . .
C18 C19 C20 C21 3.1(13) . .
C19 C20 C21 C22 -2.1(14) . .
C20 C21 C22 C23 -178.2(7) . .
C20 C21 C22 C17 -0.4(11) . .
C18 C17 C22 C23 179.8(5) . .
C16 C17 C22 C23 -1.5(7) . .
C18 C17 C22 C21 1.9(8) . .
C16 C17 C22 C21 -179.4(5) . .
C21 C22 C23 C24 179.2(5) . .
C17 C22 C23 C24 1.3(8) . .
C22 C23 C24 C25 -1.0(7) . .
C17 C16 C25 O26 178.2(3) . .
C15 C16 C25 O26 -1.6(5) . .
C17 C16 C25 C24 -1.1(5) . .
C15 C16 C25 C24 179.1(3) . .
C23 C24 C25 C16 0.9(6) . .
C23 C24 C25 O26 -178.3(4) . .
C16 C25 O26 C27 165.4(4) . .
C24 C25 O26 C27 -15.3(6) . .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.000 -0.000 -0.004 635 29 ' '
2 0.333 0.667 0.632 634 29 ' '
3 0.667 0.333 0.299 635 29 ' '
loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
-1 2 0 1.236
-1 1 1 2.033
