#------------------------------------------------------------------------------
#$Date: 2019-11-11 20:02:14 +0200 (Mon, 11 Nov 2019) $
#$Revision: 227191 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/57/4035748.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_4035748
loop_
_publ_author_name
'Ma, Tsz-Kan'
'Elliott, Daniel C.'
'Reid, Stephanie'
'White, Andrew J. P.'
'Parsons, Philip J.'
'Barrett, Anthony G. M.'
_publ_section_title
;
 Meroterpenoid Synthesis via Sequential Polyketide Aromatization and
 Cationic Polyene Cyclization: Total Syntheses of (+)-Hongoquercin A and B
 and Related Meroterpenoids.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13276
_journal_page_last               13286
_journal_paper_doi               10.1021/acs.joc.8b02095
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C26 H35 Br O4'
_chemical_formula_sum            'C26 H35 Br O4'
_chemical_formula_weight         491.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 102.860(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6717(11)
_cell_length_b                   10.9343(5)
_cell_length_c                   13.0037(8)
_cell_measurement_reflns_used    1959
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.1810
_cell_measurement_theta_min      2.5200
_cell_volume                     2311.0(2)
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_collection       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0382
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.808
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.808
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7946
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.265
_diffrn_reflns_theta_min         2.460
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.809
_exptl_absorpt_correction_T_max  0.806
_exptl_absorpt_correction_T_min  0.609
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.428
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0582
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0755P)²+5.3783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1635
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3424
_reflns_number_total             4629
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b02095_si_004.cif
_cod_data_source_block           44
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035748
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.9996(2) 0.0758(3) 0.2434(2) 0.0372(8) Uani 1 1 d . .
C1 C 0.9759(3) 0.1067(4) 0.3197(3) 0.0260(9) Uani 1 1 d . .
O2 O 1.03010(17) 0.1655(3) 0.3980(2) 0.0266(7) Uani 1 1 d . .
C3 C 0.9993(3) 0.2258(4) 0.4801(3) 0.0249(9) Uani 1 1 d . .
O4 O 0.94794(17) 0.1427(3) 0.5208(2) 0.0243(6) Uani 1 1 d . .
C5 C 0.8868(2) 0.0892(4) 0.4458(3) 0.0198(8) Uani 1 1 d . .
C6 C 0.8191(2) 0.0466(4) 0.4806(3) 0.0210(8) Uani 1 1 d . .
C7 C 0.8105(2) 0.0627(4) 0.5923(3) 0.0245(9) Uani 1 1 d . .
H7A H 0.8236 0.1483 0.6147 0.029 Uiso 1 1 calc R U
H7B H 0.8502 0.0086 0.6393 0.029 Uiso 1 1 calc R U
C8 C 0.7232(2) 0.0320(4) 0.6027(3) 0.0209(8) Uani 1 1 d . .
H8A H 0.6878 0.0991 0.5649 0.025 Uiso 1 1 calc R U
C9 C 0.7093(2) 0.0334(4) 0.7173(3) 0.0215(8) Uani 1 1 d . .
C10 C 0.7267(3) 0.1641(4) 0.7611(3) 0.0278(10) Uani 1 1 d . .
H10A H 0.7863 0.1814 0.7712 0.033 Uiso 1 1 calc R U
H10B H 0.6966 0.2232 0.7088 0.033 Uiso 1 1 calc R U
C11 C 0.7011(3) 0.1821(4) 0.8659(3) 0.0317(10) Uani 1 1 d . .
H11A H 0.7339 0.1275 0.9201 0.038 Uiso 1 1 calc R U
H11B H 0.7119 0.2676 0.8900 0.038 Uiso 1 1 calc R U
C12 C 0.6105(3) 0.1537(4) 0.8528(3) 0.0318(10) Uani 1 1 d . .
H12A H 0.5792 0.2140 0.8012 0.038 Uiso 1 1 calc R U
Br12 Br 0.58226(3) 0.18560(5) 0.99124(4) 0.03884(19) Uani 1 1 d . .
C13 C 0.5827(2) 0.0255(4) 0.8119(3) 0.0252(9) Uani 1 1 d . .
C14 C 0.6161(2) 0.0082(4) 0.7088(3) 0.0229(9) Uani 1 1 d . .
H14A H 0.5872 0.0723 0.6593 0.027 Uiso 1 1 calc R U
C15 C 0.5897(3) -0.1123(4) 0.6530(4) 0.0322(10) Uani 1 1 d . .
H15A H 0.5306 -0.1266 0.6502 0.039 Uiso 1 1 calc R U
H15B H 0.6213 -0.1802 0.6931 0.039 Uiso 1 1 calc R U
C16 C 0.6042(3) -0.1103(4) 0.5411(4) 0.0310(10) Uani 1 1 d . .
H16A H 0.5879 -0.1902 0.5069 0.037 Uiso 1 1 calc R U
H16B H 0.5691 -0.0464 0.4996 0.037 Uiso 1 1 calc R U
C17 C 0.6934(3) -0.0851(4) 0.5403(3) 0.0254(9) Uani 1 1 d . .
O18 O 0.69015(17) -0.0594(3) 0.4287(2) 0.0276(7) Uani 1 1 d . .
C19 C 0.7584(2) -0.0098(4) 0.4050(3) 0.0228(9) Uani 1 1 d . .
C20 C 0.7629(3) -0.0159(4) 0.2993(3) 0.0259(9) Uani 1 1 d . .
H20A H 0.7182 -0.0500 0.2492 0.031 Uiso 1 1 calc R U
C21 C 0.8304(3) 0.0261(4) 0.2661(3) 0.0270(9) Uani 1 1 d . .
C22 C 0.8954(3) 0.0778(4) 0.3425(3) 0.0241(9) Uani 1 1 d . .
C23 C 1.0726(3) 0.2497(4) 0.5681(3) 0.0302(10) Uani 1 1 d . .
H23A H 1.1000 0.1721 0.5919 0.045 Uiso 1 1 calc R U
H23B H 1.0546 0.2888 0.6270 0.045 Uiso 1 1 calc R U
H23C H 1.1111 0.3037 0.5431 0.045 Uiso 1 1 calc R U
C24 C 0.9534(3) 0.3400(4) 0.4378(4) 0.0348(11) Uani 1 1 d . .
H24A H 0.9880 0.3905 0.4029 0.052 Uiso 1 1 calc R U
H24B H 0.9395 0.3861 0.4961 0.052 Uiso 1 1 calc R U
H24C H 0.9028 0.3179 0.3869 0.052 Uiso 1 1 calc R U
C25 C 0.7670(3) -0.0563(4) 0.7905(3) 0.0315(10) Uani 1 1 d . .
H25A H 0.8208 -0.0575 0.7717 0.047 Uiso 1 1 calc R U
H25B H 0.7431 -0.1386 0.7824 0.047 Uiso 1 1 calc R U
H25C H 0.7738 -0.0297 0.8639 0.047 Uiso 1 1 calc R U
C26 C 0.6103(3) -0.0738(5) 0.8927(4) 0.0394(12) Uani 1 1 d . .
H26A H 0.6693 -0.0651 0.9231 0.059 Uiso 1 1 calc R U
H26B H 0.5997 -0.1540 0.8587 0.059 Uiso 1 1 calc R U
H26C H 0.5797 -0.0669 0.9487 0.059 Uiso 1 1 calc R U
C27 C 0.4884(3) 0.0276(5) 0.7812(4) 0.0399(12) Uani 1 1 d . .
H27A H 0.4669 0.0560 0.8413 0.060 Uiso 1 1 calc R U
H27B H 0.4678 -0.0550 0.7614 0.060 Uiso 1 1 calc R U
H27C H 0.4702 0.0830 0.7214 0.060 Uiso 1 1 calc R U
C28 C 0.7476(3) -0.1971(4) 0.5700(4) 0.0334(10) Uani 1 1 d . .
H28A H 0.7334 -0.2586 0.5141 0.050 Uiso 1 1 calc R U
H28B H 0.7388 -0.2312 0.6363 0.050 Uiso 1 1 calc R U
H28C H 0.8054 -0.1737 0.5788 0.050 Uiso 1 1 calc R U
C29 C 0.8325(3) 0.0160(5) 0.1512(4) 0.0437(13) Uani 1 1 d . .
H29A H 0.8514 0.0936 0.1272 0.065 Uiso 1 1 calc R U
H29B H 0.7772 -0.0025 0.1098 0.065 Uiso 1 1 calc R U
H29C H 0.8704 -0.0496 0.1420 0.065 Uiso 1 1 calc R U
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'
Br Br -0.2901 2.4595 '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
O1 C1 O2 117.8(4)
O1 C1 C22 126.3(4)
O2 C1 C22 115.7(3)
C1 O2 C3 118.8(3)
O4 C3 O2 109.0(3)
O4 C3 C23 106.3(3)
O2 C3 C23 106.3(3)
O4 C3 C24 111.4(3)
O2 C3 C24 110.2(4)
C23 C3 C24 113.3(4)
C5 O4 C3 114.7(3)
O4 C5 C6 116.1(3)
O4 C5 C22 120.3(3)
C6 C5 C22 123.5(4)
C5 C6 C19 115.9(4)
C5 C6 C7 122.4(4)
C19 C6 C7 121.7(4)
C6 C7 C8 110.9(3)
C7 C8 C17 109.8(3)
C7 C8 C9 115.4(3)
C17 C8 C9 114.4(3)
C10 C9 C25 108.7(3)
C10 C9 C14 107.0(3)
C25 C9 C14 114.0(3)
C10 C9 C8 107.8(3)
C25 C9 C8 112.3(3)
C14 C9 C8 106.8(3)
C11 C10 C9 112.4(3)
C12 C11 C10 110.0(4)
C11 C12 C13 116.3(4)
C11 C12 Br12 107.0(3)
C13 C12 Br12 111.1(3)
C26 C13 C27 109.1(4)
C26 C13 C12 113.2(4)
C27 C13 C12 106.9(4)
C26 C13 C14 113.3(4)
C27 C13 C14 108.5(3)
C12 C13 C14 105.6(3)
C15 C14 C9 111.4(3)
C15 C14 C13 113.0(3)
C9 C14 C13 117.1(3)
C14 C15 C16 110.6(4)
C17 C16 C15 111.9(4)
O18 C17 C16 102.8(3)
O18 C17 C28 107.1(3)
C16 C17 C28 112.4(4)
O18 C17 C8 107.4(3)
C16 C17 C8 110.5(3)
C28 C17 C8 115.7(4)
C19 O18 C17 116.9(3)
O18 C19 C6 122.3(4)
O18 C19 C20 115.8(3)
C6 C19 C20 121.9(4)
C21 C20 C19 121.5(4)
C20 C21 C22 117.8(4)
C20 C21 C29 119.4(4)
C22 C21 C29 122.8(4)
C5 C22 C21 119.2(4)
C5 C22 C1 118.1(4)
C21 C22 C1 122.4(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.196(5)
C1 O2 1.363(5)
C1 C22 1.472(6)
O2 C3 1.442(5)
C3 O4 1.429(5)
C3 C23 1.500(6)
C3 C24 1.504(6)
O4 C5 1.374(5)
C5 C6 1.387(5)
C5 C22 1.388(5)
C6 C19 1.388(6)
C6 C7 1.501(5)
C7 C8 1.529(5)
C8 C17 1.538(6)
C8 C9 1.559(5)
C9 C10 1.542(6)
C9 C25 1.544(6)
C9 C14 1.558(5)
C10 C11 1.530(6)
C11 C12 1.514(6)
C12 C13 1.534(6)
C12 Br12 1.990(4)
C13 C26 1.510(6)
C13 C27 1.533(6)
C13 C14 1.573(5)
C14 C15 1.522(6)
C15 C16 1.527(6)
C16 C17 1.515(6)
C17 O18 1.468(5)
C17 C28 1.519(6)
O18 C19 1.356(5)
C19 C20 1.395(6)
C20 C21 1.371(6)
C21 C22 1.415(6)
C21 C29 1.507(6)
