#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/52/7105295.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_7105295
loop_
_publ_author_name
'Carr, James L'
'Offermann, Daniel A'
'Holdom, Mary D'
'Dusart, Philip'
'White, Andrew J P'
'Beavil, Andrew J'
'Leatherbarrow, Robin J'
'Lindell, Stephen D'
'Sutton, Brian J'
'Spivey, Alan C'
_publ_section_title
;
 Total synthesis of (+/-)-aspercyclide A and its C19 methyl ether.
;
_journal_issue                   11
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1824
_journal_page_last               1826
_journal_paper_doi               10.1039/b923528k
_journal_volume                  46
_journal_year                    2010
_chemical_formula_moiety         'C17 H15 Br O4'
_chemical_formula_sum            'C17 H15 Br O4'
_chemical_formula_weight         363.20
_chemical_name_systematic
;
?
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 95.5928(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.02056(13)
_cell_length_b                   6.60200(9)
_cell_length_c                   14.6738(2)
_cell_measurement_reflns_used    9458
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      71.1606
_cell_measurement_theta_min      3.0223
_cell_volume                     773.31(2)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.2556
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'OD Xcalibur PX Ultra'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_sigmaI/netI    0.0100
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11409
_diffrn_reflns_theta_full        71.36
_diffrn_reflns_theta_max         71.36
_diffrn_reflns_theta_min         6.05
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.764
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May 8 2007,13:10:02)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 1210 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       0.0023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2700
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0254
_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)+(0.0481P)²+0.2924P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0724
_reflns_number_gt                2634
_reflns_number_total             2700
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b923528k.txt
_cod_data_source_block           8
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      Pn
_cod_database_code               7105295
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -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
C1 C 0.7258(4) 0.4781(4) 0.5320(2) 0.0332(6) Uani 1 1 d . . .
C2 C 0.7799(3) 0.6515(4) 0.48989(17) 0.0308(5) Uani 1 1 d . . .
C3 C 0.6596(3) 0.7627(4) 0.43577(18) 0.0323(5) Uani 1 1 d . . .
Br Br 0.72790(7) 1.00128(4) 0.37828(5) 0.04335(12) Uani 1 1 d . . .
C4 C 0.4949(3) 0.7023(4) 0.42316(18) 0.0344(5) Uani 1 1 d . . .
C5 C 0.4388(4) 0.5293(4) 0.4635(2) 0.0414(7) Uani 1 1 d . . .
H5A H 0.3249 0.4883 0.4544 0.050 Uiso 1 1 calc R . .
C6 C 0.5597(3) 0.4157(4) 0.5193(2) 0.0385(6) Uani 1 1 d . . .
H6A H 0.5266 0.2955 0.5483 0.046 Uiso 1 1 calc R . .
O7 O 0.8359(2) 0.3569(3) 0.58602(13) 0.0372(4) Uani 1 1 d . . .
C8 C 0.9923(4) 0.4520(4) 0.6179(2) 0.0341(6) Uani 1 1 d . . .
O9 O 1.0599(2) 0.5481(3) 0.54344(14) 0.0364(4) Uani 1 1 d . . .
C10 C 0.9616(3) 0.7112(4) 0.5037(2) 0.0378(6) Uani 1 1 d . . .
H10A H 1.0011 0.7481 0.4440 0.045 Uiso 1 1 calc R . .
H10B H 0.9747 0.8310 0.5443 0.045 Uiso 1 1 calc R . .
C11 C 0.9634(4) 0.5976(5) 0.6948(2) 0.0463(7) Uani 1 1 d . . .
H11A H 0.8859 0.7045 0.6714 0.069 Uiso 1 1 calc R . .
H11B H 1.0703 0.6584 0.7187 0.069 Uiso 1 1 calc R . .
H11C H 0.9153 0.5240 0.7440 0.069 Uiso 1 1 calc R . .
C12 C 1.1112(4) 0.2817(5) 0.6484(2) 0.0458(7) Uani 1 1 d . . .
H12A H 1.1250 0.1922 0.5964 0.069 Uiso 1 1 calc R . .
H12B H 1.0654 0.2042 0.6972 0.069 Uiso 1 1 calc R . .
H12C H 1.2202 0.3384 0.6714 0.069 Uiso 1 1 calc R . .
O13 O 0.3793(2) 0.8058(3) 0.36150(13) 0.0379(4) Uani 1 1 d . . .
C14 C 0.2959(4) 0.9655(4) 0.3962(2) 0.0312(5) Uani 1 1 d . . .
O14 O 0.3157(3) 1.0130(3) 0.4747(2) 0.0384(5) Uani 1 1 d . . .
C15 C 0.1805(3) 1.0642(5) 0.32433(18) 0.0301(5) Uani 1 1 d . . .
C16 C 0.1553(4) 0.9899(4) 0.2354(3) 0.0373(7) Uani 1 1 d . . .
H16A H 0.2146 0.8736 0.2183 0.045 Uiso 1 1 calc R . .
C17 C 0.0430(4) 1.0866(5) 0.17195(19) 0.0416(6) Uani 1 1 d . . .
H17A H 0.0246 1.0355 0.1113 0.050 Uiso 1 1 calc R . .
C18 C -0.0422(4) 1.2570(5) 0.1965(2) 0.0432(6) Uani 1 1 d . . .
H18A H -0.1184 1.3231 0.1526 0.052 Uiso 1 1 calc R . .
C19 C -0.0167(4) 1.3316(4) 0.2852(2) 0.0396(6) Uani 1 1 d . . .
H19A H -0.0744 1.4495 0.3019 0.048 Uiso 1 1 calc R . .
C20 C 0.0934(3) 1.2333(4) 0.34930(18) 0.0352(5) Uani 1 1 d . . .
H20A H 0.1091 1.2821 0.4104 0.042 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
_geom_angle_publ_flag
O7 C1 C6 117.1(2) . . ?
O7 C1 C2 121.5(2) . . ?
C6 C1 C2 121.4(3) . . ?
C1 C2 C3 117.2(2) . . ?
C1 C2 C10 119.8(2) . . ?
C3 C2 C10 123.0(2) . . ?
C4 C3 C2 121.7(2) . . ?
C4 C3 Br 119.8(2) . . ?
C2 C3 Br 118.50(18) . . ?
C3 C4 C5 122.0(3) . . ?
C3 C4 O13 120.6(2) . . ?
C5 C4 O13 117.1(2) . . ?
C4 C5 C6 116.8(3) . . ?
C1 C6 C5 120.8(3) . . ?
C1 O7 C8 114.9(2) . . ?
O9 C8 O7 109.4(3) . . ?
O9 C8 C12 106.5(2) . . ?
O7 C8 C12 106.0(2) . . ?
O9 C8 C11 112.8(3) . . ?
O7 C8 C11 109.0(2) . . ?
C12 C8 C11 112.9(3) . . ?
C8 O9 C10 114.6(2) . . ?
O9 C10 C2 110.3(2) . . ?
C14 O13 C4 116.6(2) . . ?
O14 C14 O13 122.6(3) . . ?
O14 C14 C15 126.0(3) . . ?
O13 C14 C15 111.5(2) . . ?
C20 C15 C16 120.1(3) . . ?
C20 C15 C14 117.5(2) . . ?
C16 C15 C14 122.4(3) . . ?
C17 C16 C15 119.6(3) . . ?
C18 C17 C16 120.3(3) . . ?
C17 C18 C19 120.1(3) . . ?
C20 C19 C18 119.7(3) . . ?
C15 C20 C19 120.1(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O7 1.383(3) . ?
C1 C6 1.389(4) . ?
C1 C2 1.390(4) . ?
C2 C3 1.397(4) . ?
C2 C10 1.504(3) . ?
C3 C4 1.376(4) . ?
C3 Br 1.893(3) . ?
C4 C5 1.382(4) . ?
C4 O13 1.408(3) . ?
C5 C6 1.421(5) . ?
O7 C8 1.440(4) . ?
C8 O9 1.416(4) . ?
C8 C12 1.514(4) . ?
C8 C11 1.517(4) . ?
O9 C10 1.425(3) . ?
O13 C14 1.373(4) . ?
C14 O14 1.189(5) . ?
C14 C15 1.485(4) . ?
C15 C20 1.385(4) . ?
C15 C16 1.390(5) . ?
C16 C17 1.386(4) . ?
C17 C18 1.382(4) . ?
C18 C19 1.388(4) . ?
C19 C20 1.387(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653184
