#------------------------------------------------------------------------------
#$Date: 2015-09-08 15:59:05 +0300 (Tue, 08 Sep 2015) $
#$Revision: 155234 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/46/7154617.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_7154617
loop_
_publ_author_name
'Islam, Md Monarul'
'Tomiyasu, Hirotsugu'
'Matsumoto, Taisuke'
'Tanaka, Junji'
'Rahman, Shofiur'
'Georghiou, Paris E.'
'Redshaw, Carl'
'Yamato, Takehiko'
_publ_section_title
;
 Synthesis and conformational studies of chiral macrocyclic
 [1.1.1]metacyclophanes containing benzofuran rings.
;
_journal_issue                   34
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9055
_journal_page_last               9064
_journal_paper_doi               10.1039/c5ob01002k
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C38 H44 O3'
_chemical_formula_sum            'C38 H44 O3'
_chemical_formula_weight         548.76
_chemical_melting_point          520.6(5)
_chemical_name_systematic
'15,35,55-tri-tert-butyl-12-methoxy-1-(1,3)- benzena-3,5-(2,7)benzofurana-cyclohexaphane'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2015-07-17 deposited with the CCDC.
2015-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 104.033(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   17.5245(3)
_cell_length_b                   13.6997(3)
_cell_length_c                   26.7366(5)
_cell_measurement_reflns_used    27747
_cell_measurement_temperature    123
_cell_measurement_theta_max      68.31
_cell_measurement_theta_min      3.41
_cell_volume                     6227.4(3)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            35298
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_min         3.408
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.561
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2368.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.88
_refine_diff_density_min         -0.34
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     370
_refine_ls_number_reflns         5695
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0629
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0724P)²+11.4692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1541
_refine_ls_wR_factor_ref         0.1638
_reflns_number_gt                4654
_reflns_number_total             5695
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c5ob01002k2.cif
_cod_data_source_block           yt1412b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '247--248 \%C.' was changed to
'520.6(5)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

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

 Adding full bibliography for 7154615--7154617.cif.
;
_cod_original_cell_volume        6227.3(3)
_cod_database_code               7154617
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-Y,1/2+Z
5 1/2+X,1/2+Y,+Z
6 1/2-X,1/2+Y,1/2-Z
7 1/2-X,1/2-Y,-Z
8 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_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.22693(9) 0.14265(13) 0.15990(6) 0.0340(4) Uani 1 8 d .
O2 O 0.07535(9) 0.05117(11) 0.12449(6) 0.0286(4) Uani 1 8 d .
O3 O 0.10134(9) 0.26383(11) 0.08621(6) 0.0276(4) Uani 1 8 d .
C1 C 0.19678(13) 0.17701(18) 0.20012(8) 0.0289(5) Uani 1 8 d .
C2 C 0.16425(13) 0.11026(17) 0.22867(9) 0.0295(5) Uani 1 8 d .
C3 C 0.13827(13) 0.14412(18) 0.27064(9) 0.0301(5) Uani 1 8 d .
C4 C 0.14203(13) 0.24279(17) 0.28448(8) 0.0280(5) Uani 1 8 d .
C5 C 0.17004(12) 0.30751(17) 0.25313(8) 0.0275(5) Uani 1 8 d .
C6 C 0.19726(12) 0.27630(18) 0.21040(8) 0.0283(5) Uani 1 8 d .
C7 C 0.11270(14) 0.27597(19) 0.33150(9) 0.0324(5) Uani 1 8 d .
C8 C 0.16617(16) 0.2308(2) 0.38081(10) 0.0446(7) Uani 1 8 d .
C9 C 0.02872(14) 0.2396(2) 0.32720(10) 0.0395(6) Uani 1 8 d .
C10 C 0.11408(18) 0.3858(2) 0.33740(11) 0.0464(7) Uani 1 8 d .
C11 C 0.30994(14) 0.1289(2) 0.17557(10) 0.0433(7) Uani 1 8 d .
C12 C 0.14884(14) 0.00585(17) 0.21026(9) 0.0335(5) Uani 1 8 d .
C13 C 0.07445(14) -0.00048(16) 0.16858(9) 0.0299(5) Uani 1 8 d .
C14 C 0.00430(14) -0.04291(17) 0.16555(9) 0.0310(5) Uani 1 8 d .
C15 C -0.04526(13) -0.01755(16) 0.11569(8) 0.0280(5) Uani 1 8 d .
C16 C -0.12280(14) -0.03638(17) 0.08885(9) 0.0295(5) Uani 1 8 d .
C17 C -0.15131(13) 0.00353(17) 0.03979(9) 0.0289(5) Uani 1 8 d .
C18 C -0.10129(13) 0.06294(16) 0.01924(8) 0.0269(5) Uani 1 8 d .
C19 C -0.02392(13) 0.08414(16) 0.04470(8) 0.0257(5) Uani 1 8 d .
C20 C 0.00179(12) 0.04102(16) 0.09272(8) 0.0257(5) Uani 1 8 d .
C21 C -0.23683(14) -0.01538(19) 0.01008(9) 0.0348(6) Uani 1 8 d .
C22 C -0.29148(17) 0.0434(3) 0.03527(13) 0.0625(9) Uani 1 8 d .
C23 C -0.2571(2) -0.1240(3) 0.01383(14) 0.0687(10) Uani 1 8 d .
C24 C -0.25134(18) 0.0086(3) -0.04625(11) 0.0706(11) Uani 1 8 d .
C25 C 0.02835(13) 0.14985(17) 0.02223(8) 0.0282(5) Uani 1 8 d .
C26 C 0.03688(12) 0.25013(17) 0.04491(8) 0.0259(5) Uani 1 8 d .
C27 C -0.00617(13) 0.33238(17) 0.03425(8) 0.0285(5) Uani 1 8 d .
C28 C 0.03104(13) 0.40493(17) 0.07106(8) 0.0270(5) Uani 1 8 d .
C29 C 0.01500(13) 0.50182(17) 0.08119(9) 0.0288(5) Uani 1 8 d .
C30 C 0.06466(14) 0.54998(17) 0.12223(9) 0.0299(5) Uani 1 8 d .
C31 C 0.13073(14) 0.49922(17) 0.15170(9) 0.0306(5) Uani 1 8 d .
C32 C 0.14897(13) 0.40387(17) 0.14281(8) 0.0288(5) Uani 1 8 d .
C33 C 0.09638(13) 0.35863(16) 0.10181(8) 0.0265(5) Uani 1 8 d .
C34 C 0.04975(15) 0.65563(18) 0.13659(9) 0.0344(6) Uani 1 8 d .
C35 C -0.02580(16) 0.69751(19) 0.10210(10) 0.0396(6) Uani 1 8 d .
C36 C 0.11837(18) 0.7204(2) 0.13135(14) 0.0564(8) Uani 1 8 d .
C37 C 0.03980(19) 0.6581(2) 0.19227(10) 0.0504(7) Uani 1 8 d .
C38 C 0.21985(13) 0.35078(18) 0.17469(9) 0.0302(5) Uani 1 8 d .
H3 H 0.11724 0.09875 0.2906 0.0361 Uiso 1 8 calc R
H5 H 0.17084 0.37526 0.26081 0.0330 Uiso 1 8 calc R
H8A H 0.16588 0.15957 0.37756 0.0535 Uiso 1 8 calc R
H8B H 0.21999 0.25514 0.38526 0.0535 Uiso 1 8 calc R
H8C H 0.14645 0.24922 0.4108 0.0535 Uiso 1 8 calc R
H9A H 0.02717 0.16843 0.32335 0.0474 Uiso 1 8 calc R
H9B H 0.01207 0.2576 0.35841 0.0474 Uiso 1 8 calc R
H9C H -0.00681 0.26947 0.29708 0.0474 Uiso 1 8 calc R
H10A H 0.16762 0.40985 0.34019 0.0557 Uiso 1 8 calc R
H10B H 0.07832 0.41528 0.30726 0.0557 Uiso 1 8 calc R
H10C H 0.0972 0.40341 0.36859 0.0557 Uiso 1 8 calc R
H11A H 0.32913 0.10474 0.14635 0.0520 Uiso 1 8 calc R
H11B H 0.33547 0.19125 0.18738 0.0520 Uiso 1 8 calc R
H11C H 0.3223 0.08134 0.20375 0.0520 Uiso 1 8 calc R
H12A H 0.19347 -0.01804 0.19696 0.0402 Uiso 1 8 calc R
H12B H 0.14448 -0.03623 0.23954 0.0402 Uiso 1 8 calc R
H14 H -0.00996 -0.08199 0.1912 0.0372 Uiso 1 8 calc R
H16 H -0.15581 -0.07599 0.10385 0.0354 Uiso 1 8 calc R
H18 H -0.12137 0.09033 -0.01399 0.0323 Uiso 1 8 calc R
H22A H -0.28106 0.02662 0.07194 0.0750 Uiso 1 8 calc R
H22B H -0.28216 0.11324 0.03162 0.0750 Uiso 1 8 calc R
H22C H -0.34629 0.02793 0.01843 0.0750 Uiso 1 8 calc R
H23A H -0.2484 -0.1426 0.05017 0.0824 Uiso 1 8 calc R
H23B H -0.31244 -0.13485 -0.0037 0.0824 Uiso 1 8 calc R
H23C H -0.22354 -0.16365 -0.00259 0.0824 Uiso 1 8 calc R
H24A H -0.21574 -0.02976 -0.06165 0.0847 Uiso 1 8 calc R
H24B H -0.30595 -0.00696 -0.06352 0.0847 Uiso 1 8 calc R
H24C H -0.24182 0.07835 -0.05034 0.0847 Uiso 1 8 calc R
H25A H 0.08109 0.11966 0.02793 0.0339 Uiso 1 8 calc R
H25B H 0.00638 0.15497 -0.01545 0.0339 Uiso 1 8 calc R
H27 H -0.05243 0.34088 0.00745 0.0343 Uiso 1 8 calc R
H29 H -0.02927 0.5344 0.06032 0.0345 Uiso 1 8 calc R
H31 H 0.1647 0.533 0.17937 0.0367 Uiso 1 8 calc R
H35A H -0.07062 0.65691 0.10492 0.0475 Uiso 1 8 calc R
H35B H -0.03365 0.76425 0.11306 0.0475 Uiso 1 8 calc R
H35C H -0.02154 0.69819 0.06623 0.0475 Uiso 1 8 calc R
H36A H 0.16744 0.69477 0.15319 0.0677 Uiso 1 8 calc R
H36B H 0.1219 0.72098 0.09532 0.0677 Uiso 1 8 calc R
H36C H 0.10978 0.78704 0.14216 0.0677 Uiso 1 8 calc R
H37A H -0.00439 0.61618 0.19491 0.0605 Uiso 1 8 calc R
H37B H 0.08806 0.63437 0.21589 0.0605 Uiso 1 8 calc R
H37C H 0.0294 0.72518 0.20144 0.0605 Uiso 1 8 calc R
H38A H 0.25654 0.39881 0.19539 0.0363 Uiso 1 8 calc R
H38B H 0.24758 0.31742 0.15138 0.0363 Uiso 1 8 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 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(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
_geom_angle_publ_flag
C1 O1 C11 111.69(17) yes
C13 O2 C20 105.93(17) yes
C26 O3 C33 105.68(16) yes
O1 C1 C2 118.9(2) yes
O1 C1 C6 120.0(2) yes
C2 C1 C6 121.1(2) yes
C1 C2 C3 118.7(2) yes
C1 C2 C12 120.3(2) yes
C3 C2 C12 120.7(2) yes
C2 C3 C4 122.2(2) yes
C3 C4 C5 117.3(2) yes
C3 C4 C7 119.9(2) yes
C5 C4 C7 122.8(2) yes
C4 C5 C6 122.3(2) yes
C1 C6 C5 118.2(2) yes
C1 C6 C38 121.7(2) yes
C5 C6 C38 119.9(2) yes
C4 C7 C8 108.9(2) yes
C4 C7 C9 110.37(19) yes
C4 C7 C10 112.3(2) yes
C8 C7 C9 107.8(2) yes
C8 C7 C10 108.5(2) yes
C9 C7 C10 108.8(2) yes
C2 C12 C13 110.53(18) yes
O2 C13 C12 114.7(2) yes
O2 C13 C14 111.74(19) yes
C12 C13 C14 133.5(2) yes
C13 C14 C15 106.7(2) yes
C14 C15 C16 136.1(2) yes
C14 C15 C20 104.90(19) yes
C16 C15 C20 118.99(19) yes
C15 C16 C17 119.4(2) yes
C16 C17 C18 118.68(19) yes
C16 C17 C21 120.1(2) yes
C18 C17 C21 121.2(2) yes
C17 C18 C19 123.83(19) yes
C18 C19 C20 115.0(2) yes
C18 C19 C25 122.89(18) yes
C20 C19 C25 122.06(18) yes
O2 C20 C15 110.71(18) yes
O2 C20 C19 125.3(2) yes
C15 C20 C19 123.99(19) yes
C17 C21 C22 108.7(2) yes
C17 C21 C23 109.9(2) yes
C17 C21 C24 112.8(2) yes
C22 C21 C23 107.5(3) yes
C22 C21 C24 110.8(2) yes
C23 C21 C24 107.0(3) yes
C19 C25 C26 113.4(2) yes
O3 C26 C25 115.42(18) yes
O3 C26 C27 111.17(19) yes
C25 C26 C27 133.40(18) yes
C26 C27 C28 107.18(18) yes
C27 C28 C29 135.22(19) yes
C27 C28 C33 105.13(19) yes
C29 C28 C33 119.64(19) yes
C28 C29 C30 119.14(19) yes
C29 C30 C31 118.5(2) yes
C29 C30 C34 122.2(2) yes
C31 C30 C34 119.32(19) yes
C30 C31 C32 124.2(2) yes
C31 C32 C33 114.82(19) yes
C31 C32 C38 123.48(19) yes
C33 C32 C38 121.7(2) yes
O3 C33 C28 110.83(17) yes
O3 C33 C32 125.49(19) yes
C28 C33 C32 123.7(2) yes
C30 C34 C35 112.18(19) yes
C30 C34 C36 109.8(2) yes
C30 C34 C37 109.1(2) yes
C35 C34 C36 108.2(2) yes
C35 C34 C37 106.9(2) yes
C36 C34 C37 110.6(2) yes
C6 C38 C32 112.03(19) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.390(3) yes
O1 C11 1.425(3) yes
O2 C13 1.378(3) yes
O2 C20 1.368(2) yes
O3 C26 1.388(2) yes
O3 C33 1.373(3) yes
C1 C2 1.398(4) yes
C1 C6 1.387(3) yes
C2 C3 1.389(4) yes
C2 C12 1.516(3) yes
C3 C4 1.399(3) yes
C4 C5 1.389(3) yes
C4 C7 1.538(4) yes
C5 C6 1.407(3) yes
C6 C38 1.514(3) yes
C7 C8 1.549(3) yes
C7 C9 1.531(4) yes
C7 C10 1.512(4) yes
C12 C13 1.498(3) yes
C13 C14 1.344(3) yes
C14 C15 1.446(3) yes
C15 C16 1.398(3) yes
C15 C20 1.395(3) yes
C16 C17 1.397(3) yes
C17 C18 1.402(3) yes
C17 C21 1.538(3) yes
C18 C19 1.392(3) yes
C19 C20 1.386(3) yes
C19 C25 1.509(3) yes
C21 C22 1.527(4) yes
C21 C23 1.539(4) yes
C21 C24 1.502(4) yes
C25 C26 1.494(3) yes
C26 C27 1.348(3) yes
C27 C28 1.439(3) yes
C28 C29 1.397(3) yes
C28 C33 1.390(3) yes
C29 C30 1.391(3) yes
C30 C31 1.415(3) yes
C30 C34 1.536(3) yes
C31 C32 1.379(3) yes
C32 C33 1.395(3) yes
C32 C38 1.512(3) yes
C34 C35 1.530(3) yes
C34 C36 1.528(4) yes
C34 C37 1.541(4) yes
