#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/55/2205580.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_2205580
loop_
_publ_author_name
'George R. Clark'
'Christopher L. Flowers'
'Margaret A. Brimble'
_publ_section_title
;
 6,8'-Dimethoxy-2,2'-spirobichroman
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o910
_journal_page_last               o911
_journal_paper_doi               10.1107/S1600536805006938
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C19 H20 O4'
_chemical_formula_moiety         'C19 H20 O4'
_chemical_formula_sum            'C19 H20 O4'
_chemical_formula_weight         312.35
_chemical_name_systematic
;
6,8'-Dimethoxy-2,2'-spirobichroman
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                73.684(2)
_cell_angle_beta                 86.3830(10)
_cell_angle_gamma                79.589(2)
_cell_formula_units_Z            2
_cell_length_a                   5.8149(5)
_cell_length_b                   10.9359(10)
_cell_length_c                   12.9304(12)
_cell_measurement_reflns_used    2358
_cell_measurement_temperature    84.0(10)
_cell_measurement_theta_max      25.79
_cell_measurement_theta_min      1.64
_cell_volume                     776.09(12)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXTL (Siemens, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      84.0(10)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Siemens SMART CCD'
_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  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0879
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7036
_diffrn_reflns_theta_full        25.79
_diffrn_reflns_theta_max         25.79
_diffrn_reflns_theta_min         1.64
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_correction_T_min  0.9532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1301
_refine_ls_R_factor_gt           0.0680
_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)+(0.0803P)²+0.0036P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1734
_reflns_number_gt                1716
_reflns_number_total             2941
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz6056.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (10
times).

'_geom_bond_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (36
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (12
times).

'_geom_angle_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (70 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (10
times).

'_geom_bond_publ_flag' value 'N' changed to 'n' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (36
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (12
times).

'_geom_angle_publ_flag' value 'N' changed to 'n' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (70 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2205580
_cod_database_fobs_code          2205580
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
O1 0.3958(3) 0.92868(18) 0.73454(15) 0.0292(5) Uani d . 1 O
C1 0.5156(5) 0.9835(3) 0.7996(3) 0.0323(7) Uani d . 1 C
O2 0.3453(3) 1.05168(19) 0.85683(16) 0.0337(6) Uani d . 1 O
C2 0.6601(5) 0.8803(3) 0.8851(3) 0.0367(8) Uani d . 1 C
H2A 0.7335 0.9207 0.9291 0.044 Uiso calc R 1 H
H2B 0.7829 0.8319 0.8509 0.044 Uiso calc R 1 H
O3 0.1298(4) 0.85778(18) 0.61758(16) 0.0338(6) Uani d . 1 O
C3 0.5117(5) 0.7886(3) 0.9563(2) 0.0351(8) Uani d . 1 C
H3A 0.6123 0.7144 1.0008 0.042 Uiso calc R 1 H
H3B 0.4144 0.8319 1.0037 0.042 Uiso calc R 1 H
O4 -0.2056(4) 1.50031(19) 0.62438(17) 0.0401(6) Uani d . 1 O
C4 0.3595(5) 0.7442(3) 0.8895(2) 0.0299(7) Uani d . 1 C
C5 0.3084(5) 0.8170(3) 0.7844(2) 0.0279(7) Uani d . 1 C
C6 0.1671(5) 0.7785(3) 0.7194(2) 0.0283(7) Uani d . 1 C
C7 0.0797(5) 0.6643(3) 0.7609(2) 0.0337(8) Uani d . 1 C
H7A -0.0127 0.6372 0.7184 0.040 Uiso calc R 1 H
C8 0.1299(6) 0.5905(3) 0.8657(2) 0.0345(8) Uani d . 1 C
H8A 0.0706 0.5142 0.8935 0.041 Uiso calc R 1 H
C9 0.2677(5) 0.6302(3) 0.9287(2) 0.0339(8) Uani d . 1 C
H9A 0.3002 0.5799 0.9988 0.041 Uiso calc R 1 H
C10 -0.0308(6) 0.8252(3) 0.5538(3) 0.0440(9) Uani d . 1 C
H10A -0.0433 0.8864 0.4838 0.066 Uiso calc R 1 H
H10B -0.1817 0.8274 0.5886 0.066 Uiso calc R 1 H
H10C 0.0252 0.7400 0.5462 0.066 Uiso calc R 1 H
C11 0.6506(5) 1.0736(3) 0.7213(3) 0.0363(8) Uani d . 1 C
H11A 0.7675 1.0244 0.6850 0.044 Uiso calc R 1 H
H11B 0.7312 1.1172 0.7600 0.044 Uiso calc R 1 H
C12 0.4910(5) 1.1742(3) 0.6377(3) 0.0335(8) Uani d . 1 C
H12A 0.5736 1.2438 0.6002 0.040 Uiso calc R 1 H
H12B 0.4472 1.1348 0.5850 0.040 Uiso calc R 1 H
C13 0.2749(5) 1.2275(3) 0.6919(3) 0.0308(7) Uani d . 1 C
C14 0.2160(5) 1.1660(3) 0.7967(3) 0.0310(7) Uani d . 1 C
C15 0.1273(5) 1.3405(3) 0.6379(3) 0.0322(8) Uani d . 1 C
H15A 0.1637 1.3835 0.5675 0.039 Uiso calc R 1 H
C16 0.0216(5) 1.2177(3) 0.8476(2) 0.0342(8) Uani d . 1 C
H16A -0.0116 1.1775 0.9191 0.041 Uiso calc R 1 H
C17 -0.1241(6) 1.3294(3) 0.7927(2) 0.0333(8) Uani d . 1 C
H17A -0.2556 1.3632 0.8270 0.040 Uiso calc R 1 H
C18 -0.0735(5) 1.3894(3) 0.6879(3) 0.0325(8) Uani d . 1 C
C19 -0.4262(6) 1.5451(3) 0.6679(3) 0.0457(9) Uani d . 1 C
H19A -0.5021 1.6219 0.6174 0.069 Uiso calc R 1 H
H19B -0.4023 1.5640 0.7342 0.069 Uiso calc R 1 H
H19C -0.5223 1.4794 0.6814 0.069 Uiso calc R 1 H
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_publ_flag
C5 O1 C1 118.0(2) y
O2 C1 O1 108.4(2) y
O2 C1 C11 111.2(2) y
O1 C1 C11 105.0(2) y
O2 C1 C2 105.5(2) y
O1 C1 C2 111.7(2) y
C11 C1 C2 115.1(3) y
C14 O2 C1 116.7(2) y
C1 C2 C3 111.4(3) y
C1 C2 H2A 109.3 n
C3 C2 H2A 109.3 n
C1 C2 H2B 109.3 n
C3 C2 H2B 109.3 n
H2A C2 H2B 108.0 n
C6 O3 C10 116.3(2) n
C4 C3 C2 110.7(3) y
C4 C3 H3A 109.5 n
C2 C3 H3A 109.5 n
C4 C3 H3B 109.5 n
C2 C3 H3B 109.5 n
H3A C3 H3B 108.1 n
C18 O4 C19 116.6(3) n
C5 C4 C9 117.9(3) n
C5 C4 C3 119.7(3) n
C9 C4 C3 122.3(3) n
O1 C5 C4 123.7(3) y
O1 C5 C6 114.9(3) n
C4 C5 C6 121.4(3) n
O3 C6 C7 124.9(3) n
O3 C6 C5 116.0(2) n
C7 C6 C5 119.1(3) n
C6 C7 C8 120.0(3) n
C6 C7 H7A 120.0 n
C8 C7 H7A 120.0 n
C9 C8 C7 120.1(3) n
C9 C8 H8A 120.0 n
C7 C8 H8A 120.0 n
C8 C9 C4 121.4(3) n
C8 C9 H9A 119.3 n
C4 C9 H9A 119.3 n
O3 C10 H10A 109.5 n
O3 C10 H10B 109.5 n
H10A C10 H10B 109.5 n
O3 C10 H10C 109.5 n
H10A C10 H10C 109.5 n
H10B C10 H10C 109.5 n
C1 C11 C12 111.5(3) n
C1 C11 H11A 109.3 n
C12 C11 H11A 109.3 n
C1 C11 H11B 109.3 n
C12 C11 H11B 109.3 n
H11A C11 H11B 108.0 n
C13 C12 C11 110.0(3) y
C13 C12 H12A 109.7 n
C11 C12 H12A 109.7 n
C13 C12 H12B 109.7 n
C11 C12 H12B 109.7 n
H12A C12 H12B 108.2 n
C14 C13 C15 118.0(3) n
C14 C13 C12 121.0(3) n
C15 C13 C12 121.0(3) n
C16 C14 C13 120.8(3) n
C16 C14 O2 116.2(3) n
C13 C14 O2 123.0(3) n
C18 C15 C13 121.0(3) n
C18 C15 H15A 119.5 n
C13 C15 H15A 119.5 n
C14 C16 C17 120.5(3) n
C14 C16 H16A 119.8 n
C17 C16 H16A 119.8 n
C18 C17 C16 119.7(3) n
C18 C17 H17A 120.1 n
C16 C17 H17A 120.1 n
C17 C18 O4 125.3(3) n
C17 C18 C15 119.9(3) n
O4 C18 C15 114.8(3) n
O4 C19 H19A 109.5 n
O4 C19 H19B 109.5 n
H19A C19 H19B 109.5 n
O4 C19 H19C 109.5 n
H19A C19 H19C 109.5 n
H19B C19 H19C 109.5 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 1.381(3) y
O1 C1 1.436(3) y
C1 O2 1.426(3) y
C1 C11 1.494(4) y
C1 C2 1.509(4) y
O2 C14 1.386(3) y
C2 C3 1.513(4) y
C2 H2A 0.9700 n
C2 H2B 0.9700 n
O3 C6 1.364(3) n
O3 C10 1.436(3) n
C3 C4 1.501(4) y
C3 H3A 0.9700 n
C3 H3B 0.9700 n
O4 C18 1.385(4) n
O4 C19 1.428(4) n
C4 C5 1.387(4) n
C4 C9 1.396(4) n
C5 C6 1.404(4) n
C6 C7 1.387(4) n
C7 C8 1.387(4) n
C7 H7A 0.9300 n
C8 C9 1.378(4) n
C8 H8A 0.9300 n
C9 H9A 0.9300 n
C10 H10A 0.9600 n
C10 H10B 0.9600 n
C10 H10C 0.9600 n
C11 C12 1.526(4) y
C11 H11A 0.9700 n
C11 H11B 0.9700 n
C12 C13 1.505(4) y
C12 H12A 0.9700 n
C12 H12B 0.9700 n
C13 C14 1.385(4) n
C13 C15 1.400(4) n
C14 C16 1.384(4) n
C15 C18 1.394(4) n
C15 H15A 0.9300 n
C16 C17 1.388(4) n
C16 H16A 0.9300 n
C17 C18 1.369(4) n
C17 H17A 0.9300 n
C19 H19A 0.9600 n
C19 H19B 0.9600 n
C19 H19C 0.9600 n
