#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:05:27 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180286 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/00/7150074.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_7150074
loop_
_publ_author_name
'Gibson, Harry W.'
'Wang, Hong'
'Bonrad, Klaus'
'Jones, Jason W.'
'Slebodnick, Carla'
'Zackharov, Lev N.'
'Rheingold, Arnold L.'
'Habenicht, Bradley'
'Lobue, Peter'
'Ratliff, Amy E.'
_publ_section_title
;
 Regioselective routes to disubstituted dibenzo crown ethers and their
 complexations.
;
_journal_issue                   11
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2114
_journal_page_last               2121
_journal_paper_doi               10.1039/b503072m
_journal_volume                  3
_journal_year                    2005
_chemical_formula_moiety         'C28 H36 O12'
_chemical_formula_sum            'C28 H36 O12'
_chemical_formula_weight         564.57
_chemical_name_common            HW-trans-24C8
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.243(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.8926(14)
_cell_length_b                   12.4235(11)
_cell_length_c                   8.2043(8)
_cell_measurement_reflns_used    2865
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.3
_cell_measurement_theta_min      3.1
_cell_volume                     1366.2(2)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.10 beta (release 25.09.2003 CrysAlis171 VC++)
(compiled Sep 25 2003,17:01:25)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.10 beta (release 25.09.2003 CrysAlis171 VC++)
(compiled Sep 25 2003,17:01:25)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.10 beta (release 25.09.2003 CrysAlis171 VC++)
(compiled Sep 25 2003,17:01:25)
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_type            'Oxford Diffraction Sapphire 2 CCD'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur2'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8078
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         3.04
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           40
_diffrn_source_voltage           50
_diffrn_standards_decay_%        <2%
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'hexagonal plate'
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3162
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0649
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1313P)²+0.2020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1886
_refine_ls_wR_factor_ref         0.2109
_reflns_number_gt                2411
_reflns_number_total             3162
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b503072m.txt
_cod_data_source_block           cs525
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7150074
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.73535(11) 0.79696(12) 0.16967(18) 0.0214(4) Uani 1 1 d . . .
O2 O 0.52104(12) 0.73255(15) 0.1453(2) 0.0324(4) Uani 1 1 d . . .
O3 O 0.33518(11) 0.85119(12) 0.06535(19) 0.0241(4) Uani 1 1 d . . .
O4 O 0.20214(11) 1.02772(12) -0.06483(19) 0.0218(4) Uani 1 1 d . . .
O5 O 1.18478(12) 0.87043(13) 0.5775(2) 0.0263(4) Uani 1 1 d . . .
O6 O 1.16237(12) 1.00899(14) 0.3960(2) 0.0285(4) Uani 1 1 d . . .
C1 C 0.83105(16) 0.82313(17) 0.2463(3) 0.0186(4) Uani 1 1 d . . .
C2 C 0.89459(17) 0.76288(18) 0.3725(3) 0.0228(5) Uani 1 1 d . . .
H2 H 0.8715 0.6980 0.4106 0.027 Uiso 1 1 calc R . .
C3 C 0.99194(16) 0.79735(17) 0.4431(3) 0.0224(5) Uani 1 1 d . . .
H3 H 1.0348 0.7566 0.5307 0.027 Uiso 1 1 calc R . .
C4 C 1.02673(16) 0.89141(17) 0.3857(2) 0.0204(5) Uani 1 1 d . . .
C5 C 0.96295(15) 0.95223(17) 0.2586(3) 0.0191(4) Uani 1 1 d . . .
H5 H 0.9864 1.0164 0.2190 0.023 Uiso 1 1 calc R . .
C6 C 0.86587(15) 0.91864(16) 0.1907(2) 0.0171(4) Uani 1 1 d . . .
C7 C 0.69985(16) 0.69358(16) 0.2086(3) 0.0207(5) Uani 1 1 d . . .
H7A H 0.6980 0.6918 0.3284 0.025 Uiso 1 1 calc R . .
H7B H 0.7455 0.6361 0.1909 0.025 Uiso 1 1 calc R . .
C8 C 0.59711(17) 0.67502(18) 0.0957(3) 0.0248(5) Uani 1 1 d . . .
H8A H 0.5963 0.6964 -0.0209 0.030 Uiso 1 1 calc R . .
H8B H 0.5819 0.5971 0.0944 0.030 Uiso 1 1 calc R . .
C9 C 0.50960(19) 0.8401(2) 0.0853(4) 0.0341(6) Uani 1 1 d . . .
H9A H 0.4910 0.8409 -0.0398 0.041 Uiso 1 1 calc R . .
H9B H 0.5731 0.8800 0.1266 0.041 Uiso 1 1 calc R . .
C10 C 0.42952(19) 0.8917(2) 0.1490(4) 0.0435(7) Uani 1 1 d . . .
H10A H 0.4424 0.8783 0.2718 0.052 Uiso 1 1 calc R . .
H10B H 0.4306 0.9705 0.1314 0.052 Uiso 1 1 calc R . .
C11 C 0.25639(17) 0.88797(18) 0.1329(3) 0.0230(5) Uani 1 1 d . . .
H11A H 0.2813 0.9462 0.2155 0.028 Uiso 1 1 calc R . .
H11B H 0.2333 0.8281 0.1927 0.028 Uiso 1 1 calc R . .
C12 C 0.17084(16) 0.92903(17) -0.0054(3) 0.0217(5) Uani 1 1 d . . .
H12A H 0.1528 0.8760 -0.0984 0.026 Uiso 1 1 calc R . .
H12B H 0.1118 0.9414 0.0384 0.026 Uiso 1 1 calc R . .
C13 C 1.13002(16) 0.93066(17) 0.4522(3) 0.0209(5) Uani 1 1 d . . .
C14 C 1.28889(16) 0.9045(2) 0.6413(3) 0.0280(5) Uani 1 1 d . . .
H14A H 1.3243 0.8923 0.5542 0.042 Uiso 1 1 calc R . .
H14B H 1.3208 0.8628 0.7424 0.042 Uiso 1 1 calc R . .
H14C H 1.2912 0.9812 0.6698 0.042 Uiso 1 1 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 0.0033 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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C7 117.59(16) . . ?
C9 O2 C8 113.46(18) . . ?
C10 O3 C11 114.13(18) . . ?
C6 O4 C12 117.49(16) 3_675 . ?
C13 O5 C14 114.94(18) . . ?
O1 C1 C2 124.82(19) . . ?
O1 C1 C6 115.69(18) . . ?
C2 C1 C6 119.5(2) . . ?
C1 C2 C3 120.1(2) . . ?
C2 C3 C4 120.2(2) . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 C13 122.81(19) . . ?
C5 C4 C13 117.4(2) . . ?
C6 C5 C4 119.8(2) . . ?
O4 C6 C5 124.18(19) 3_675 . ?
O4 C6 C1 115.26(18) 3_675 . ?
C5 C6 C1 120.55(19) . . ?
O1 C7 C8 108.99(17) . . ?
O2 C8 C7 113.83(19) . . ?
O2 C9 C10 108.0(2) . . ?
O3 C10 C9 111.2(2) . . ?
O3 C11 C12 110.60(17) . . ?
O4 C12 C11 107.35(17) . . ?
O6 C13 O5 123.3(2) . . ?
O6 C13 C4 123.1(2) . . ?
O5 C13 C4 113.60(19) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.352(3) . ?
O1 C7 1.441(2) . ?
O2 C9 1.419(3) . ?
O2 C8 1.421(3) . ?
O3 C10 1.403(3) . ?
O3 C11 1.426(3) . ?
O4 C6 1.375(2) 3_675 ?
O4 C12 1.429(3) . ?
O5 C13 1.336(3) . ?
O5 C14 1.465(3) . ?
O6 C13 1.213(3) . ?
C1 C2 1.390(3) . ?
C1 C6 1.402(3) . ?
C2 C3 1.391(3) . ?
C3 C4 1.393(3) . ?
C4 C5 1.399(3) . ?
C4 C13 1.477(3) . ?
C5 C6 1.381(3) . ?
C6 O4 1.375(2) 3_675 ?
C7 C8 1.501(3) . ?
C9 C10 1.492(4) . ?
C11 C12 1.500(3) . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 O1 C1 C2 -7.0(3) . . . . ?
C7 O1 C1 C6 173.04(17) . . . . ?
O1 C1 C2 C3 -179.90(19) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C2 C3 C4 C13 -178.26(19) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C13 C4 C5 C6 179.34(18) . . . . ?
C4 C5 C6 O4 -179.53(18) . . . 3_675 ?
C4 C5 C6 C1 -1.0(3) . . . . ?
O1 C1 C6 O4 -0.4(3) . . . 3_675 ?
C2 C1 C6 O4 179.60(17) . . . 3_675 ?
O1 C1 C6 C5 -179.05(17) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C1 O1 C7 C8 -173.17(17) . . . . ?
C9 O2 C8 C7 83.9(2) . . . . ?
O1 C7 C8 O2 -77.1(2) . . . . ?
C8 O2 C9 C10 -178.8(2) . . . . ?
C11 O3 C10 C9 173.3(2) . . . . ?
O2 C9 C10 O3 -72.0(3) . . . . ?
C10 O3 C11 C12 130.6(2) . . . . ?
C6 O4 C12 C11 -178.68(16) 3_675 . . . ?
O3 C11 C12 O4 -70.6(2) . . . . ?
C14 O5 C13 O6 -1.3(3) . . . . ?
C14 O5 C13 C4 177.47(17) . . . . ?
C3 C4 C13 O6 175.6(2) . . . . ?
C5 C4 C13 O6 -3.7(3) . . . . ?
C3 C4 C13 O5 -3.2(3) . . . . ?
C5 C4 C13 O5 177.54(17) . . . . ?
