#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/78/1507803.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_1507803
loop_
_publ_author_name
'Podlesny, Erin E.'
'Kozlowski, Marisa C.'
_publ_section_title
;
 Structural reassignment of a marine metabolite from a binaphthalenetetrol
 to a tetrabrominated diphenyl ether.
;
_journal_issue                   6
_journal_name_full               'Journal of natural products'
_journal_page_first              1125
_journal_page_last               1129
_journal_paper_doi               10.1021/np300141t
_journal_volume                  75
_journal_year                    2012
_chemical_formula_sum            'C23 H16 Cl2 O6'
_chemical_formula_weight         459.26
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                70.4850(10)
_cell_angle_beta                 73.3250(10)
_cell_angle_gamma                86.9450(10)
_cell_formula_units_Z            2
_cell_length_a                   8.8157(3)
_cell_length_b                   10.5756(3)
_cell_length_c                   12.1409(4)
_cell_measurement_temperature    100(1)
_cell_volume                     1020.89(6)
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0122
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            33038
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.358
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.852
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0611
_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)+(0.0747P)²+1.4851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1669
_refine_ls_wR_factor_ref         0.1695
_reflns_number_gt                3347
_reflns_number_total             3722
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np300141t_si_002.cif
_cod_data_source_block           UP8006
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 
;
_cod_original_sg_symbol_H-M      'P -1       '
_cod_database_code               1507803
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.6557(3) 0.3859(2) 0.0375(2) 0.0242(5) Uani 1 1 d .
C2 C 0.7311(3) 0.5038(2) -0.0542(2) 0.0288(5) Uani 1 1 d .
H2 H 0.7227 0.5253 -0.1329 0.038 Uiso 1 1 calc R
C3 C 0.8180(3) 0.5874(2) -0.0258(2) 0.0317(6) Uani 1 1 d .
H3 H 0.8648 0.6672 -0.0856 0.042 Uiso 1 1 calc R
C4 C 0.8366(3) 0.5545(2) 0.0898(2) 0.0288(6) Uani 1 1 d .
C5 C 0.9302(3) 0.6437(2) 0.1186(3) 0.0340(6) Uani 1 1 d .
C6 C 0.9519(3) 0.5978(3) 0.2485(3) 0.0363(6) Uani 1 1 d .
C7 C 0.8801(3) 0.4682(2) 0.3325(2) 0.0304(5) Uani 1 1 d .
H7 H 0.8971 0.4352 0.4090 0.040 Uiso 1 1 calc R
C8 C 0.7897(3) 0.3953(2) 0.3016(2) 0.0255(5) Uani 1 1 d .
H8 H 0.7416 0.3151 0.3598 0.034 Uiso 1 1 calc R
C9 C 0.7629(3) 0.4351(2) 0.1818(2) 0.0239(5) Uani 1 1 d .
C10 C 0.6666(3) 0.3539(2) 0.1573(2) 0.0214(5) Uani 1 1 d .
C11 C 0.5617(2) 0.2411(2) 0.25711(19) 0.0195(4) Uani 1 1 d .
C12 C 0.4378(3) 0.2748(2) 0.3446(2) 0.0197(4) Uani 1 1 d .
C13 C 0.3274(3) 0.1776(2) 0.4346(2) 0.0207(5) Uani 1 1 d .
H13 H 0.2468 0.2009 0.4921 0.028 Uiso 1 1 calc R
C14 C 0.3398(3) 0.0458(2) 0.43662(19) 0.0208(5) Uani 1 1 d .
H14 H 0.2650 -0.0193 0.4949 0.028 Uiso 1 1 calc R
C15 C 0.4615(3) 0.0092(2) 0.35352(19) 0.0190(4) Uani 1 1 d .
C16 C 0.4702(3) -0.1310(2) 0.3565(2) 0.0217(5) Uani 1 1 d .
C17 C 0.6160(3) -0.1685(2) 0.2693(2) 0.0218(5) Uani 1 1 d .
C18 C 0.7252(3) -0.0597(2) 0.1793(2) 0.0233(5) Uani 1 1 d .
H18 H 0.8106 -0.0787 0.1223 0.031 Uiso 1 1 calc R
C19 C 0.7046(3) 0.0675(2) 0.1772(2) 0.0220(5) Uani 1 1 d .
H19 H 0.7768 0.1340 0.1178 0.029 Uiso 1 1 calc R
C20 C 0.5749(2) 0.1071(2) 0.26326(19) 0.0184(4) Uani 1 1 d .
C21 C 0.5636(3) 0.3153(3) -0.1011(2) 0.0323(6) Uani 1 1 d .
H21a H 0.5179 0.3991 -0.1330 0.048 Uiso 1 1 calc R
H21b H 0.5007 0.2430 -0.0997 0.048 Uiso 1 1 calc R
H21c H 0.6695 0.3154 -0.1520 0.048 Uiso 1 1 calc R
C22 C 0.3271(3) 0.4491(2) 0.4254(2) 0.0277(5) Uani 1 1 d .
H22a H 0.2200 0.4330 0.4273 0.042 Uiso 1 1 calc R
H22b H 0.3461 0.5432 0.4083 0.042 Uiso 1 1 calc R
H22c H 0.3430 0.3992 0.5030 0.042 Uiso 1 1 calc R
O1 O 0.5676(2) 0.29758(16) 0.02042(14) 0.0270(4) Uani 1 1 d .
O2 O 0.9911(2) 0.75176(17) 0.0461(2) 0.0448(6) Uani 1 1 d .
O3 O 1.0271(2) 0.6706(2) 0.2750(2) 0.0519(6) Uani 1 1 d .
O4 O 0.43475(19) 0.40704(15) 0.33207(14) 0.0249(4) Uani 1 1 d .
O5 O 0.3681(2) -0.21824(16) 0.42276(16) 0.0320(4) Uani 1 1 d .
O6 O 0.6348(2) -0.28652(16) 0.27901(16) 0.0302(4) Uani 1 1 d .
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'
Cl Cl 0.1484 0.1585 '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
O1 C1 C2 124.2(2)
O1 C1 C10 115.28(19)
C2 C1 C10 120.5(2)
C3 C2 C1 119.2(2)
C2 C3 C4 121.3(2)
C3 C4 C9 119.7(2)
C3 C4 C5 120.8(2)
C9 C4 C5 119.5(2)
O2 C5 C4 123.5(3)
O2 C5 C6 118.5(2)
C4 C5 C6 118.0(2)
O3 C6 C7 123.3(3)
O3 C6 C5 119.2(3)
C7 C6 C5 117.5(2)
C8 C7 C6 121.1(3)
C7 C8 C9 123.5(2)
C10 C9 C4 119.9(2)
C10 C9 C8 119.9(2)
C4 C9 C8 120.2(2)
C9 C10 C1 119.2(2)
C9 C10 C11 121.8(2)
C1 C10 C11 118.7(2)
C20 C11 C12 118.84(19)
C20 C11 C10 123.42(19)
C12 C11 C10 117.63(18)
O4 C12 C13 123.86(19)
O4 C12 C11 114.76(18)
C13 C12 C11 121.37(19)
C14 C13 C12 118.8(2)
C15 C14 C13 121.2(2)
C14 C15 C20 120.16(19)
C14 C15 C16 120.03(19)
C20 C15 C16 119.78(19)
O5 C16 C15 123.7(2)
O5 C16 C17 118.51(19)
C15 C16 C17 117.75(18)
O6 C17 C18 123.4(2)
O6 C17 C16 119.0(2)
C18 C17 C16 117.58(18)
C19 C18 C17 121.1(2)
C18 C19 C20 123.4(2)
C11 C20 C15 119.58(19)
C11 C20 C19 120.51(19)
C15 C20 C19 119.91(19)
C1 O1 C21 118.80(18)
C12 O4 C22 119.02(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.348(3)
C1 C2 1.404(3)
C1 C10 1.410(3)
C2 C3 1.383(4)
C3 C4 1.385(4)
C4 C9 1.412(3)
C4 C5 1.471(4)
C5 O2 1.221(3)
C5 C6 1.552(4)
C6 O3 1.216(3)
C6 C7 1.451(4)
C7 C8 1.342(3)
C8 C9 1.459(3)
C9 C10 1.392(3)
C10 C11 1.502(3)
C11 C20 1.395(3)
C11 C12 1.412(3)
C12 O4 1.355(3)
C12 C13 1.394(3)
C13 C14 1.385(3)
C14 C15 1.384(3)
C15 C20 1.413(3)
C15 C16 1.469(3)
C16 O5 1.219(3)
C16 C17 1.541(3)
C17 O6 1.221(3)
C17 C18 1.456(3)
C18 C19 1.340(3)
C19 C20 1.460(3)
C21 O1 1.435(3)
C22 O4 1.434(3)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.125 0.000 0.375 211 95 ' '
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 30651930 ChemSpider
