#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/35/2213561.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_2213561
loop_
_publ_author_name
'Hoong-Kun Fun'
'Nawong Boonnak'
'Suchada Chantrapromma'
_publ_section_title
8,8'-Methylenebis(7,10-dihydroxy-1,3,6,6-tetramethyl-3,4-dihydro-1H-benzo[g]isochromen-9-one)
_journal_coeditor_code           SJ2275
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2317
_journal_page_last               o2318
_journal_paper_doi               10.1107/S160053680701611X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C35 H40 O8'
_chemical_formula_moiety         'C35 H40 O8'
_chemical_formula_sum            'C35 H40 O8'
_chemical_formula_weight         588.67
_chemical_name_common
;
8-[(7,10-dihydroxy-1,3,6,6-tetramethyl-9-oxo-3,4,6,9-tetrahydro-1H-
benzo[g]isochromen-8-yl)methyl]-7,10-dihydroxy-1,3,6,6-tetramethyl-1,3,4,6-
tetrahydro-9H-benzo[g]isochromen-9-one
;
_chemical_name_systematic
;
8,8'-Methylenebis(7,10-dihydroxy-1,3,6,6-tetramethyl-3,4-dihydro-1H-
benzo[g]isochromen-9-one)
;
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_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                   8.4385(11)
_cell_length_b                   8.4385(11)
_cell_length_c                   42.901(6)
_cell_measurement_reflns_used    2260
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.99
_cell_measurement_theta_min      2.46
_cell_volume                     3054.9(7)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Siemens SMART CCD area-detector
;
_diffrn_measurement_method       ω
_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  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            18799
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.46
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9726
_exptl_absorpt_correction_T_min  0.9550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         2260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0455
_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)+(0.0447P)²+0.7147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                2063
_reflns_number_total             2260
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2275.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2213561
_cod_database_fobs_code          2213561
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -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 O1 0.4677(3) 0.9308(2) 0.17258(4) 0.0582(5) Uani d . 1
O O2 0.4769(2) 0.5202(2) 0.11731(4) 0.0520(4) Uani d . 1
O O3 0.4647(2) 0.39680(19) 0.06313(4) 0.0494(4) Uani d . 1
O O4 0.3021(2) 0.6941(2) -0.02377(4) 0.0483(4) Uani d . 1
C C1 0.4647(3) 0.7810(3) 0.15729(5) 0.0452(5) Uani d . 1
C C2 0.5288(3) 1.0592(3) 0.15466(6) 0.0519(6) Uani d . 1
C C3 0.4158(4) 1.0873(3) 0.12776(6) 0.0540(6) Uani d . 1
C C4 0.4027(3) 0.9396(3) 0.10838(5) 0.0423(5) Uani d . 1
C C5 0.3737(3) 0.9490(3) 0.07645(5) 0.0434(5) Uani d . 1
C C6 0.3730(3) 0.8156(3) 0.05769(5) 0.0371(5) Uani d . 1
C C7 0.3471(3) 0.8330(3) 0.02278(5) 0.0385(5) Uani d . 1
C C8 0.3400(2) 0.6763(3) 0.00634(5) 0.0367(4) Uani d . 1
C C9 0.3763(3) 0.5350(3) 0.01925(5) 0.0364(4) Uani d . 1
C C10 0.4177(3) 0.5275(2) 0.05186(5) 0.0376(5) Uani d . 1
C C11 0.4071(3) 0.6681(3) 0.07128(5) 0.0360(4) Uani d . 1
C C12 0.4376(3) 0.6597(3) 0.10374(5) 0.0391(5) Uani d . 1
C C13 0.4310(3) 0.7938(3) 0.12255(5) 0.0399(5) Uani d . 1
C C14 0.3399(4) 0.6840(5) 0.17431(7) 0.0614(7) Uani d . 1
C C15 0.5425(4) 1.2016(4) 0.17597(7) 0.0636(8) Uani d . 1
C C16 0.1947(4) 0.9260(4) 0.01619(6) 0.0589(8) Uani d . 1
C C17 0.4928(4) 0.9210(3) 0.00888(6) 0.0532(7) Uani d . 1
C C18 0.3844(3) 0.3844(3) 0.0000 0.0389(7) Uani d S 1
H H1O2 0.486(4) 0.445(4) 0.1014(7) 0.074(10) Uiso d . 1
H H1O4 0.321(4) 0.608(5) -0.0370(7) 0.091(12) Uiso d . 1
H H1 0.570(4) 0.729(3) 0.1595(6) 0.053(7) Uiso d . 1
H H2 0.636(3) 1.029(3) 0.1461(5) 0.049(7) Uiso d . 1
H H3A 0.456(4) 1.175(4) 0.1149(6) 0.065(9) Uiso d . 1
H H3B 0.317(4) 1.115(4) 0.1364(6) 0.061(8) Uiso d . 1
H H5 0.355(3) 1.052(3) 0.0675(5) 0.043(6) Uiso d . 1
H H14A 0.334(4) 0.578(5) 0.1668(8) 0.090(12) Uiso d . 1
H H14B 0.236(5) 0.737(5) 0.1718(8) 0.110(13) Uiso d . 1
H H14C 0.362(4) 0.693(4) 0.1966(7) 0.066(8) Uiso d . 1
H H15A 0.430(4) 1.230(3) 0.1842(6) 0.060(8) Uiso d . 1
H H15B 0.611(4) 1.176(4) 0.1930(7) 0.078(10) Uiso d . 1
H H15C 0.586(5) 1.299(5) 0.1639(8) 0.099(12) Uiso d . 1
H H16A 0.100(4) 0.865(4) 0.0255(7) 0.067(9) Uiso d . 1
H H16B 0.198(5) 1.030(5) 0.0275(8) 0.100(12) Uiso d . 1
H H16C 0.170(4) 0.940(4) -0.0055(7) 0.073(9) Uiso d . 1
H H17A 0.511(4) 1.022(4) 0.0188(7) 0.080(10) Uiso d . 1
H H17B 0.486(4) 0.928(4) -0.0143(7) 0.072(9) Uiso d . 1
H H17C 0.592(4) 0.852(4) 0.0146(7) 0.078(10) Uiso d . 1
H H18 0.288(3) 0.378(3) -0.0151(5) 0.044(7) Uiso d . 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 0.0000 '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 0.0000 '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_1
_geom_angle
C1 O1 C2 . 115.64(18)
C12 O2 H1O2 . 107.3(19)
C8 O4 H1O4 . 117(2)
O1 C1 C14 . 105.6(2)
O1 C1 C13 . 113.07(19)
C14 C1 C13 . 112.3(2)
O1 C1 H1 . 109.4(16)
C14 C1 H1 . 109.4(16)
C13 C1 H1 . 107.0(15)
O1 C2 C15 . 107.8(2)
O1 C2 C3 . 107.6(2)
C15 C2 C3 . 112.6(2)
O1 C2 H2 . 109.2(16)
C15 C2 H2 . 110.7(15)
C3 C2 H2 . 109.0(14)
C4 C3 C2 . 109.8(2)
C4 C3 H3A . 109.8(16)
C2 C3 H3A . 108.9(18)
C4 C3 H3B . 111.0(19)
C2 C3 H3B . 107.3(17)
H3A C3 H3B . 110(3)
C13 C4 C5 . 120.6(2)
C13 C4 C3 . 118.6(2)
C5 C4 C3 . 120.6(2)
C6 C5 C4 . 121.7(2)
C6 C5 H5 . 120.1(14)
C4 C5 H5 . 118.1(14)
C5 C6 C11 . 118.61(18)
C5 C6 C7 . 119.66(19)
C11 C6 C7 . 121.59(19)
C8 C7 C6 . 112.56(18)
C8 C7 C16 . 109.3(2)
C6 C7 C16 . 110.63(19)
C8 C7 C17 . 105.76(18)
C6 C7 C17 . 108.06(19)
C16 C7 C17 . 110.4(2)
O4 C8 C9 . 123.3(2)
O4 C8 C7 . 111.38(18)
C9 C8 C7 . 125.23(18)
C8 C9 C10 . 119.44(19)
C8 C9 C18 . 121.79(17)
C10 C9 C18 . 118.68(17)
O3 C10 C9 . 118.93(19)
O3 C10 C11 . 120.73(19)
C9 C10 C11 . 120.34(18)
C6 C11 C12 . 119.3(2)
C6 C11 C10 . 119.91(18)
C12 C11 C10 . 120.77(19)
O2 C12 C13 . 117.87(18)
O2 C12 C11 . 120.6(2)
C13 C12 C11 . 121.49(19)
C12 C13 C4 . 118.17(18)
C12 C13 C1 . 120.24(19)
C4 C13 C1 . 121.5(2)
C1 C14 H14A . 112(2)
C1 C14 H14B . 108(2)
H14A C14 H14B . 110(3)
C1 C14 H14C . 106.9(18)
H14A C14 H14C . 115(3)
H14B C14 H14C . 104(3)
C2 C15 H15A . 108.4(16)
C2 C15 H15B . 109(2)
H15A C15 H15B . 110(2)
C2 C15 H15C . 111(2)
H15A C15 H15C . 108(3)
H15B C15 H15C . 110(3)
C7 C16 H16A . 109.0(18)
C7 C16 H16B . 110(2)
H16A C16 H16B . 106(3)
C7 C16 H16C . 115.2(19)
H16A C16 H16C . 105(2)
H16B C16 H16C . 111(3)
C7 C17 H17A . 112.1(19)
C7 C17 H17B . 111.2(18)
H17A C17 H17B . 114(3)
C7 C17 H17C . 106.0(19)
H17A C17 H17C . 105(3)
H17B C17 H17C . 108(2)
C9 C18 C9 7 111.9(2)
C9 C18 H18 7 108.3(13)
C9 C18 H18 . 110.4(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.424(3)
O1 C2 . 1.425(3)
O2 C12 . 1.355(3)
O2 H1O2 . 0.93(3)
O3 C10 . 1.268(3)
O4 C8 . 1.339(2)
O4 H1O4 . 0.94(4)
C1 C14 . 1.521(4)
C1 C13 . 1.521(3)
C1 H1 . 0.99(3)
C2 C15 . 1.514(4)
C2 C3 . 1.516(4)
C2 H2 . 1.01(3)
C3 C4 . 1.502(3)
C3 H3A . 0.98(3)
C3 H3B . 0.94(3)
C4 C13 . 1.393(3)
C4 C5 . 1.394(3)
C5 C6 . 1.383(3)
C5 H5 . 0.97(3)
C6 C11 . 1.405(3)
C6 C7 . 1.521(3)
C7 C8 . 1.500(3)
C7 C16 . 1.532(3)
C7 C17 . 1.555(3)
C8 C9 . 1.350(3)
C9 C10 . 1.443(3)
C9 C18 . 1.517(3)
C10 C11 . 1.453(3)
C11 C12 . 1.418(3)
C12 C13 . 1.390(3)
C14 H14A . 0.95(4)
C14 H14B . 0.99(4)
C14 H14C . 0.98(3)
C15 H15A . 1.04(3)
C15 H15B . 0.96(3)
C15 H15C . 1.04(4)
C16 H16A . 1.03(3)
C16 H16B . 1.01(4)
C16 H16C . 0.96(3)
C17 H17A . 0.97(3)
C17 H17B . 1.00(3)
C17 H17C . 1.05(4)
C18 C9 7 1.517(3)
C18 H18 . 1.04(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H1O2 O3 1_555 0.94(3) 1.70(3) 2.549(2) 149(3) yes
O4 H1O4 O3 7_555 0.94(4) 1.77(4) 2.690(2) 168(3) yes
C14 H14A O2 1_555 0.95(4) 2.49(3) 3.038(4) 117(3) yes
C18 H18 O3 7_555 1.04(2) 2.37(2) 2.7938(19) 102.8(16) yes
C1 H1 Cg1 6_565 0.99(3) 2.83(3) 3.780(3) 159(2) yes
C14 H14B Cg1 6_465 0.99(4) 2.87(4) 3.729(4) 146(3) yes
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_site_symmetry_4
_geom_torsion
C2 O1 C1 C14 . -157.6(2)
C2 O1 C1 C13 . -34.4(3)
C1 O1 C2 C15 . -172.7(2)
C1 O1 C2 C3 . 65.7(3)
O1 C2 C3 C4 . -59.1(3)
C15 C2 C3 C4 . -177.7(2)
C2 C3 C4 C13 . 26.4(4)
C2 C3 C4 C5 . -149.2(2)
C13 C4 C5 C6 . -0.4(4)
C3 C4 C5 C6 . 175.0(3)
C4 C5 C6 C11 . -1.9(3)
C4 C5 C6 C7 . -177.7(2)
C5 C6 C7 C8 . -176.5(2)
C11 C6 C7 C8 . 7.8(3)
C5 C6 C7 C16 . -53.9(3)
C11 C6 C7 C16 . 130.5(2)
C5 C6 C7 C17 . 67.1(3)
C11 C6 C7 C17 . -108.6(2)
C6 C7 C8 O4 . 174.06(19)
C16 C7 C8 O4 . 50.7(3)
C17 C7 C8 O4 . -68.2(2)
C6 C7 C8 C9 . -9.8(3)
C16 C7 C8 C9 . -133.1(2)
C17 C7 C8 C9 . 108.0(2)
O4 C8 C9 C10 . 179.2(2)
C7 C8 C9 C10 . 3.5(3)
O4 C8 C9 C18 . 3.0(3)
C7 C8 C9 C18 . -172.8(2)
C8 C9 C10 O3 . -174.0(2)
C18 C9 C10 O3 . 2.4(3)
C8 C9 C10 C11 . 5.3(3)
C18 C9 C10 C11 . -178.28(19)
C5 C6 C11 C12 . 1.4(3)
C7 C6 C11 C12 . 177.1(2)
C5 C6 C11 C10 . -175.9(2)
C7 C6 C11 C10 . -0.2(3)
O3 C10 C11 C6 . 172.4(2)
C9 C10 C11 C6 . -6.8(3)
O3 C10 C11 C12 . -4.8(3)
C9 C10 C11 C12 . 175.9(2)
C6 C11 C12 O2 . -177.4(2)
C10 C11 C12 O2 . -0.1(3)
C6 C11 C12 C13 . 1.4(3)
C10 C11 C12 C13 . 178.7(2)
O2 C12 C13 C4 . 175.1(2)
C11 C12 C13 C4 . -3.7(3)
O2 C12 C13 C1 . -1.0(3)
C11 C12 C13 C1 . -179.9(2)
C5 C4 C13 C12 . 3.2(4)
C3 C4 C13 C12 . -172.4(2)
C5 C4 C13 C1 . 179.3(2)
C3 C4 C13 C1 . 3.7(4)
O1 C1 C13 C12 . 174.4(2)
C14 C1 C13 C12 . -66.2(3)
O1 C1 C13 C4 . -1.6(3)
C14 C1 C13 C4 . 117.8(3)
C8 C9 C18 C9 7 76.10(19)
C10 C9 C18 C9 7 -100.22(19)
