#------------------------------------------------------------------------------
#$Date: 2017-09-20 12:35:54 +0300 (Wed, 20 Sep 2017) $
#$Revision: 201077 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/72/1547258.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_1547258
loop_
_publ_author_name
'Petra Galer'
'Amalija Golobic'
'Joze Koller'
'Berta Kosmrlj'
'Boris Sket'
_publ_section_title
;
 Structures in solid state and solution of dimethoxy curcuminoids:
 regioselective bromination and chlorination
;
_journal_name_full               'Chemistry Central Journal'
_journal_page_first              107
_journal_paper_doi               10.1186/1752-153X-7-107
_journal_volume                  7
_journal_year                    2013
_chemical_formula_moiety         'C23 H24 O6, C O'
_chemical_formula_sum            'C24 H24 O7'
_chemical_formula_weight         424.43
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   30.699(5)
_cell_length_b                   8.444(5)
_cell_length_c                   8.788(5)
_cell_measurement_reflns_used    2930
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     2278.0(19)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPIII (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71072
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            39342
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.60
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO-SMN; Otwinovski, Minor 1997)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.934
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.024(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0701
_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)+(0.1321P)²+0.7366P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2122
_refine_ls_wR_factor_ref         0.2310
_reflns_number_gt                1911
_reflns_number_total             2571
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            13065_2013_653_MOESM4_ESM.cif
_cod_data_source_block           2e
_cod_original_sg_symbol_H-M      Pbcn
_cod_database_code               1547258
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, 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
C2 C 0.96836(7) 0.5143(3) 0.3333(2) 0.0526(5) Uani 1 1 d . . .
O3 O 0.77472(5) 0.22860(19) 0.86572(18) 0.0616(5) Uani 1 1 d . . .
O1 O 0.96744(6) 0.6671(2) 0.3326(2) 0.0669(5) Uani 1 1 d . . .
C10 C 0.83349(7) 0.5189(3) 0.6299(2) 0.0545(6) Uani 1 1 d . . .
H10 H 0.8311 0.6231 0.5965 0.065 Uiso 1 1 calc R . .
C8 C 0.80453(6) 0.3019(2) 0.7747(2) 0.0492(5) Uani 1 1 d . . .
C6 C 0.87231(6) 0.2734(3) 0.6387(2) 0.0526(5) Uani 1 1 d . . .
H6 H 0.8961 0.2118 0.6103 0.063 Uiso 1 1 calc R . .
C9 C 0.80136(7) 0.4559(3) 0.7225(2) 0.0543(6) Uani 1 1 d . . .
H9 H 0.7775 0.5175 0.7496 0.065 Uiso 1 1 calc R . .
C7 C 0.84099(7) 0.2090(2) 0.7315(2) 0.0519(5) Uani 1 1 d . . .
O2 O 0.84149(6) 0.0598(2) 0.7909(2) 0.0734(6) Uani 1 1 d . . .
C4 C 0.90262(7) 0.5014(3) 0.4903(2) 0.0545(6) Uani 1 1 d . . .
H4 H 0.9004 0.6101 0.4756 0.065 Uiso 1 1 calc R . .
C3 C 0.93582(7) 0.4292(3) 0.4216(2) 0.0564(6) Uani 1 1 d . . .
H3 H 0.9383 0.3198 0.4305 0.068 Uiso 1 1 calc R . .
C5 C 0.86938(7) 0.4291(2) 0.5857(2) 0.0500(5) Uani 1 1 d . . .
C1 C 1.0000 0.4329(4) 0.2500 0.0563(7) Uani 1 2 d S . .
C12 C 0.73610(8) 0.3164(3) 0.9004(3) 0.0721(7) Uani 1 1 d . . .
H12A H 0.7174 0.2536 0.9640 0.108 Uiso 1 1 calc R . .
H12B H 0.7211 0.3423 0.8078 0.108 Uiso 1 1 calc R . .
H12C H 0.7438 0.4121 0.9528 0.108 Uiso 1 1 calc R . .
C11 C 0.87511(11) -0.0433(3) 0.7410(5) 0.0918(10) Uani 1 1 d . . .
H11A H 0.8720 -0.1443 0.7899 0.138 Uiso 1 1 calc R . .
H11B H 0.9029 0.0014 0.7665 0.138 Uiso 1 1 calc R . .
H11C H 0.8732 -0.0567 0.6327 0.138 Uiso 1 1 calc R . .
C1S C 1.0000 1.0000 0.0000 0.197(6) Uani 1 2 d S . .
O1S O 0.9680(6) 1.054(2) 0.013(2) 0.358(12) Uani 0.50 1 d P . .
H1 H 1.0000 0.734(5) 0.2500 0.082(12) Uiso 1 2 d S . .
H1A H 1.0000 0.311(5) 0.2500 0.068(10) Uiso 1 2 d S . .
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
O1 C2 C1 120.3(2) . .
O1 C2 C3 118.79(19) . .
C1 C2 C3 120.9(2) . .
C8 O3 C12 116.48(18) . .
C9 C10 C5 121.2(2) . .
O3 C8 C9 125.05(18) . .
O3 C8 C7 115.79(18) . .
C9 C8 C7 119.16(18) . .
C7 C6 C5 121.69(19) . .
C8 C9 C10 120.42(19) . .
O2 C7 C6 125.83(19) . .
O2 C7 C8 114.69(18) . .
C6 C7 C8 119.47(19) . .
C7 O2 C11 117.14(19) . .
C3 C4 C5 127.3(2) . .
C4 C3 C2 122.7(2) . .
C10 C5 C6 118.08(19) . .
C10 C5 C4 119.13(19) . .
C6 C5 C4 122.78(19) . .
C2 C1 C2 121.0(3) . 4_755
O1S C1S O1S 180.0(9) 5_775 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2 O1 1.290(3) .
C2 C1 1.397(3) .
C2 C3 1.455(3) .
O3 C8 1.364(2) .
O3 C12 1.431(3) .
C10 C9 1.385(3) .
C10 C5 1.393(3) .
C8 C9 1.382(3) .
C8 C7 1.418(3) .
C6 C7 1.374(3) .
C6 C5 1.397(3) .
C7 O2 1.364(3) .
O2 C11 1.420(3) .
C4 C3 1.332(3) .
C4 C5 1.455(3) .
C1 C2 1.397(3) 4_755
C1S O1S 1.089(17) 5_775
C1S O1S 1.089(17) .
