#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/78/2217863.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2217863
loop_
_publ_author_name
'Sejberg, Jimmy J. P.'
'Sperry, Jonathan'
'Choi, Ka Wai'
'Boyd, Peter D. W.'
'Brimble, Margaret A.'
_publ_section_title
(1R,1'R,3S,3'S)-5,5',10,10'-Tetramethoxy-1,1',3,3'-tetramethyl-3,3',4,4'-tetrahydro-1H,1'H-8,8'-bi[benzo[g]isochromene]
_journal_coeditor_code           BI2283
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o758
_journal_paper_doi               10.1107/S1600536808007599
_journal_volume                  64
_journal_year                    2008
_chemical_formula_moiety         'C34 H38 O6'
_chemical_formula_sum            'C34 H38 O6'
_chemical_formula_weight         542.64
_chemical_melting_point          541.15
_chemical_name_systematic
;(1R,1'R,3S,3'S)-5,5',10,10'-Tetramethoxy-1,1',3,3'-
tetramethyl-
3,3',4,4'-tetrahydro-1H,1'H-8,8'-bi[benzo[g]isochromene]
;
_space_group_IT_number           20
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8773(2)
_cell_length_b                   13.9298(2)
_cell_length_c                   23.1234(4)
_cell_measurement_reflns_used    4238
_cell_measurement_temperature    89(2)
_cell_measurement_theta_max      28.56
_cell_measurement_theta_min      1.76
_cell_volume                     2859.42(9)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al.,  2006)'
_computing_publication_material  'publCIF (Westrip, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      89(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Siemens SMART CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            22789
_diffrn_reflns_theta_full        28.56
_diffrn_reflns_theta_max         28.56
_diffrn_reflns_theta_min         1.76
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.189
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0403
_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)+(0.0484P)²+0.1354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0952
_reflns_number_gt                1542
_reflns_number_total             2035
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2283.cif
_cod_data_source_block           I
_cod_database_code               2217863
_cod_database_fobs_code          2217863
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, -z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O2 0.81372(17) 0.37827(10) 0.59844(6) 0.0305(4) Uani d . 1
O O1 0.33079(16) 0.12481(10) 0.60649(6) 0.0293(4) Uani d . 1
O O3 0.29982(17) 0.39411(11) 0.69152(7) 0.0340(4) Uani d . 1
C C4 0.7076(2) 0.22511(15) 0.57426(9) 0.0249(5) Uani d . 1
C C2 0.8442(2) 0.11042(16) 0.51523(9) 0.0264(5) Uani d . 1
H H2 0.9313 0.0936 0.4953 0.032 Uiso calc R 1
C C1 0.7206(2) 0.04620(15) 0.51579(8) 0.0240(5) Uani d . 1
C C9 0.4425(2) 0.27435(16) 0.63512(9) 0.0259(5) Uani d . 1
C C5 0.5831(2) 0.16126(15) 0.57533(9) 0.0235(4) Uani d . 1
C C7 0.6948(2) 0.31407(15) 0.60336(9) 0.0260(5) Uani d . 1
C C3 0.8384(2) 0.19642(15) 0.54331(9) 0.0257(5) Uani d . 1
H H3 0.9215 0.2370 0.5422 0.031 Uiso calc R 1
C C10 0.4513(2) 0.18827(15) 0.60595(9) 0.0254(5) Uani d . 1
C C6 0.5934(2) 0.07262(14) 0.54638(9) 0.0243(5) Uani d . 1
H H6 0.5122 0.0305 0.5479 0.029 Uiso calc R 1
C C11 0.5454(3) 0.43732(15) 0.65890(10) 0.0312(5) Uani d . 1
H H11A 0.6029 0.4843 0.6372 0.037 Uiso calc R 1
H H11B 0.5819 0.4371 0.6984 0.037 Uiso calc R 1
C C8 0.5659(2) 0.33918(16) 0.63246(9) 0.0267(5) Uani d . 1
C C13 0.2982(3) 0.29950(16) 0.66695(9) 0.0314(5) Uani d . 1
H H13 0.2144 0.2957 0.6395 0.038 Uiso calc R 1
C C12 0.3790(3) 0.46387(17) 0.65792(10) 0.0354(6) Uani d . 1
H H12 0.3422 0.4622 0.6180 0.043 Uiso calc R 1
C C17 0.3459(3) 0.56069(17) 0.68390(11) 0.0430(7) Uani d . 1
H H17A 0.2397 0.5733 0.6816 0.065 Uiso calc R 1
H H17B 0.3999 0.6093 0.6630 0.065 Uiso calc R 1
H H17C 0.3768 0.5612 0.7237 0.065 Uiso calc R 1
C C15 0.9036(3) 0.3855(2) 0.64991(10) 0.0382(6) Uani d . 1
H H15A 0.8431 0.4102 0.6809 0.057 Uiso calc R 1
H H15B 0.9868 0.4281 0.6430 0.057 Uiso calc R 1
H H15C 0.9411 0.3232 0.6601 0.057 Uiso calc R 1
C C14 0.2395(3) 0.12913(18) 0.55544(10) 0.0382(6) Uani d . 1
H H14A 0.1977 0.1924 0.5516 0.057 Uiso calc R 1
H H14B 0.1594 0.0831 0.5583 0.057 Uiso calc R 1
H H14C 0.3003 0.1148 0.5222 0.057 Uiso calc R 1
C C16 0.2646(3) 0.23321(17) 0.71690(10) 0.0427(6) Uani d . 1
H H16A 0.3452 0.2365 0.7445 0.064 Uiso calc R 1
H H16B 0.2552 0.1686 0.7029 0.064 Uiso calc R 1
H H16C 0.1721 0.2524 0.7350 0.064 Uiso calc R 1
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_site_symmetry_3
_geom_angle
C7 O2 C15 . 113.58(16)
C10 O1 C14 . 113.67(15)
C12 O3 C13 . 114.47(16)
C7 C4 C3 . 123.47(19)
C7 C4 C5 . 118.55(18)
C3 C4 C5 . 117.97(18)
C3 C2 C1 . 121.43(18)
C3 C2 H2 . 119.3
C1 C2 H2 . 119.3
C6 C1 C2 . 118.01(18)
C6 C1 C1 3_556 118.94(14)
C2 C1 C1 3_556 123.03(14)
C10 C9 C8 . 119.23(18)
C10 C9 C13 . 119.07(19)
C8 C9 C13 . 121.64(19)
C6 C5 C10 . 121.61(19)
C6 C5 C4 . 119.37(18)
C10 C5 C4 . 119.02(18)
C8 C7 O2 . 120.66(18)
C8 C7 C4 . 121.54(19)
O2 C7 C4 . 117.67(18)
C2 C3 C4 . 121.19(19)
C2 C3 H3 . 119.4
C4 C3 H3 . 119.4
C9 C10 O1 . 120.42(18)
C9 C10 C5 . 121.46(19)
O1 C10 C5 . 118.11(18)
C1 C6 C5 . 122.02(19)
C1 C6 H6 . 119.0
C5 C6 H6 . 119.0
C8 C11 C12 . 109.3(2)
C8 C11 H11A . 109.8
C12 C11 H11A . 109.8
C8 C11 H11B . 109.8
C12 C11 H11B . 109.8
H11A C11 H11B . 108.3
C7 C8 C9 . 120.13(19)
C7 C8 C11 . 121.99(19)
C9 C8 C11 . 117.76(19)
O3 C13 C16 . 105.14(17)
O3 C13 C9 . 113.29(18)
C16 C13 C9 . 113.37(19)
O3 C13 H13 . 108.3
C16 C13 H13 . 108.3
C9 C13 H13 . 108.3
O3 C12 C17 . 107.21(19)
O3 C12 C11 . 107.70(18)
C17 C12 C11 . 113.7(2)
O3 C12 H12 . 109.4
C17 C12 H12 . 109.4
C11 C12 H12 . 109.4
C12 C17 H17A . 109.5
C12 C17 H17B . 109.5
H17A C17 H17B . 109.5
C12 C17 H17C . 109.5
H17A C17 H17C . 109.5
H17B C17 H17C . 109.5
O2 C15 H15A . 109.5
O2 C15 H15B . 109.5
H15A C15 H15B . 109.5
O2 C15 H15C . 109.5
H15A C15 H15C . 109.5
H15B C15 H15C . 109.5
O1 C14 H14A . 109.5
O1 C14 H14B . 109.5
H14A C14 H14B . 109.5
O1 C14 H14C . 109.5
H14A C14 H14C . 109.5
H14B C14 H14C . 109.5
C13 C16 H16A . 109.5
C13 C16 H16B . 109.5
H16A C16 H16B . 109.5
C13 C16 H16C . 109.5
H16A C16 H16C . 109.5
H16B C16 H16C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O2 C7 . 1.388(2)
O2 C15 . 1.436(3)
O1 C10 . 1.388(2)
O1 C14 . 1.433(3)
O3 C12 . 1.429(3)
O3 C13 . 1.435(3)
C4 C7 . 1.415(3)
C4 C3 . 1.421(3)
C4 C5 . 1.419(3)
C2 C3 . 1.364(3)
C2 C1 . 1.416(3)
C2 H2 . 0.9300
C1 C6 . 1.382(3)
C1 C1 3_556 1.480(4)
C9 C10 . 1.378(3)
C9 C8 . 1.421(3)
C9 C13 . 1.518(3)
C5 C6 . 1.408(3)
C5 C10 . 1.418(3)
C7 C8 . 1.373(3)
C3 H3 . 0.9300
C6 H6 . 0.9300
C11 C8 . 1.509(3)
C11 C12 . 1.523(3)
C11 H11A . 0.9700
C11 H11B . 0.9700
C13 C16 . 1.508(3)
C13 H13 . 0.9800
C12 C17 . 1.505(3)
C12 H12 . 0.9800
C17 H17A . 0.9600
C17 H17B . 0.9600
C17 H17C . 0.9600
C15 H15A . 0.9600
C15 H15B . 0.9600
C15 H15C . 0.9600
C14 H14A . 0.9600
C14 H14B . 0.9600
C14 H14C . 0.9600
C16 H16A . 0.9600
C16 H16B . 0.9600
C16 H16C . 0.9600
