#------------------------------------------------------------------------------
#$Date: 2019-11-11 20:02:14 +0200 (Mon, 11 Nov 2019) $
#$Revision: 227191 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/57/4035750.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_4035750
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         'C21 H28 O4'
_chemical_formula_sum            'C21 H28 O4'
_chemical_formula_weight         344.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 110.718(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1181(7)
_cell_length_b                   12.8001(6)
_cell_length_c                   13.9682(7)
_cell_measurement_reflns_used    1749
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5680
_cell_measurement_theta_min      2.6910
_cell_volume                     1859.30(19)
_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 0.990
_diffrn_measured_fraction_theta_max 0.820
_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  0.0226
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.820
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6444
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.820
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.074
_diffrn_reflns_theta_min         2.523
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.974
_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    1.230
_exptl_crystal_description       tablets
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3715
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0460
_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)+(0.0402P)²+0.2087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2712
_reflns_number_total             3715
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b02095_si_004.cif
_cod_data_source_block           48
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4035750
_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 1.13716(10) 0.29136(10) 0.80516(9) 0.0379(3) Uani 1 1 d . .
C1 C 1.03165(15) 0.28073(13) 0.74057(12) 0.0255(4) Uani 1 1 d . .
O2 O 1.01905(10) 0.20841(9) 0.66611(8) 0.0269(3) Uani 1 1 d . .
C3 C 0.90250(14) 0.20653(12) 0.57710(11) 0.0221(4) Uani 1 1 d . .
O4 O 0.79375(9) 0.21210(8) 0.60886(8) 0.0230(3) Uani 1 1 d . .
C5 C 0.79659(14) 0.29476(12) 0.67196(11) 0.0202(3) Uani 1 1 d . .
C6 C 0.67832(14) 0.33273(12) 0.66884(11) 0.0208(3) Uani 1 1 d . .
C7 C 0.55364(14) 0.29282(13) 0.59299(12) 0.0240(4) Uani 1 1 d . .
H7A H 0.5324 0.2244 0.6160 0.029 Uiso 1 1 calc R U
H7B H 0.5623 0.2831 0.5254 0.029 Uiso 1 1 calc R U
C8 C 0.44608(14) 0.37080(12) 0.58352(11) 0.0213(3) Uani 1 1 d . .
H8A H 0.4704 0.4353 0.5542 0.026 Uiso 1 1 calc R U
C9 C 0.31231(15) 0.33959(12) 0.50600(12) 0.0238(4) Uani 1 1 d . .
C10 C 0.21704(15) 0.42682(13) 0.50642(12) 0.0272(4) Uani 1 1 d . .
H10A H 0.2395 0.4909 0.4768 0.033 Uiso 1 1 calc R U
H10B H 0.1294 0.4055 0.4621 0.033 Uiso 1 1 calc R U
C11 C 0.21618(15) 0.45176(14) 0.61270(12) 0.0296(4) Uani 1 1 d . .
H11A H 0.1898 0.3891 0.6418 0.036 Uiso 1 1 calc R U
H11B H 0.1532 0.5080 0.6079 0.036 Uiso 1 1 calc R U
C12 C 0.34944(15) 0.48649(14) 0.68267(13) 0.0306(4) Uani 1 1 d . .
H12A H 0.3732 0.5517 0.6556 0.037 Uiso 1 1 calc R U
H12B H 0.3477 0.5014 0.7517 0.037 Uiso 1 1 calc R U
C13 C 0.44983(14) 0.40318(13) 0.69059(12) 0.0239(4) Uani 1 1 d . .
O14 O 0.57269(10) 0.45754(9) 0.74157(8) 0.0294(3) Uani 1 1 d . .
C15 C 0.68112(14) 0.41304(13) 0.73600(11) 0.0229(4) Uani 1 1 d . .
C16 C 0.79679(15) 0.45663(13) 0.80037(12) 0.0268(4) Uani 1 1 d . .
H16A H 0.7948 0.5133 0.8437 0.032 Uiso 1 1 calc R U
C17 C 0.91355(15) 0.41888(13) 0.80204(12) 0.0254(4) Uani 1 1 d . .
C18 C 0.91380(14) 0.33449(12) 0.73700(11) 0.0220(4) Uani 1 1 d . .
C19 C 0.90130(15) 0.29533(13) 0.50615(12) 0.0266(4) Uani 1 1 d . .
H19A H 0.9075 0.3618 0.5424 0.040 Uiso 1 1 calc R U
H19B H 0.8211 0.2936 0.4468 0.040 Uiso 1 1 calc R U
H19C H 0.9745 0.2884 0.4831 0.040 Uiso 1 1 calc R U
C20 C 0.89849(16) 0.10072(13) 0.52944(13) 0.0294(4) Uani 1 1 d . .
H20A H 0.9752 0.0914 0.5111 0.044 Uiso 1 1 calc R U
H20B H 0.8213 0.0953 0.4677 0.044 Uiso 1 1 calc R U
H20C H 0.8964 0.0465 0.5784 0.044 Uiso 1 1 calc R U
C21 C 0.32049(16) 0.33509(15) 0.39918(12) 0.0340(4) Uani 1 1 d . .
H21A H 0.3607 0.3992 0.3865 0.051 Uiso 1 1 calc R U
H21B H 0.2338 0.3285 0.3480 0.051 Uiso 1 1 calc R U
H21C H 0.3723 0.2747 0.3946 0.051 Uiso 1 1 calc R U
C22 C 0.26308(16) 0.23321(13) 0.52745(14) 0.0315(4) Uani 1 1 d . .
H22A H 0.3287 0.1797 0.5342 0.047 Uiso 1 1 calc R U
H22B H 0.1842 0.2149 0.4707 0.047 Uiso 1 1 calc R U
H22C H 0.2450 0.2371 0.5911 0.047 Uiso 1 1 calc R U
C23 C 0.44395(16) 0.31505(14) 0.76150(12) 0.0328(4) Uani 1 1 d . .
H23A H 0.5061 0.2608 0.7615 0.049 Uiso 1 1 calc R U
H23B H 0.3572 0.2852 0.7377 0.049 Uiso 1 1 calc R U
H23C H 0.4648 0.3423 0.8311 0.049 Uiso 1 1 calc R U
C24 C 1.03528(16) 0.46779(15) 0.87410(14) 0.0395(5) Uani 1 1 d . .
H24A H 1.0806 0.4174 0.9275 0.059 Uiso 1 1 calc R U
H24B H 1.0137 0.5300 0.9057 0.059 Uiso 1 1 calc R U
H24C H 1.0906 0.4878 0.8359 0.059 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'
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 117.20(14)
O1 C1 C18 126.36(15)
O2 C1 C18 116.36(13)
C1 O2 C3 119.17(12)
O4 C3 O2 109.38(12)
O4 C3 C20 106.66(12)
O2 C3 C20 105.87(12)
O4 C3 C19 110.81(12)
O2 C3 C19 110.52(12)
C20 C3 C19 113.39(13)
C5 O4 C3 114.12(12)
O4 C5 C6 116.37(13)
O4 C5 C18 120.28(13)
C6 C5 C18 123.32(15)
C15 C6 C5 116.40(14)
C15 C6 C7 121.55(14)
C5 C6 C7 121.98(14)
C6 C7 C8 109.70(13)
C7 C8 C13 109.93(12)
C7 C8 C9 114.85(13)
C13 C8 C9 115.96(12)
C21 C9 C22 107.79(13)
C21 C9 C10 108.04(13)
C22 C9 C10 110.42(13)
C21 C9 C8 108.53(12)
C22 C9 C8 114.34(13)
C10 C9 C8 107.55(13)
C11 C10 C9 113.41(12)
C10 C11 C12 110.28(13)
C13 C12 C11 111.37(14)
O14 C13 C23 106.39(12)
O14 C13 C12 103.62(13)
C23 C13 C12 111.66(13)
O14 C13 C8 107.39(11)
C23 C13 C8 116.20(14)
C12 C13 C8 110.60(12)
C15 O14 C13 117.63(12)
O14 C15 C6 122.80(14)
O14 C15 C16 115.36(14)
C6 C15 C16 121.80(14)
C17 C16 C15 121.18(16)
C16 C17 C18 118.28(14)
C16 C17 C24 118.92(16)
C18 C17 C24 122.79(14)
C5 C18 C17 118.95(14)
C5 C18 C1 117.98(15)
C17 C18 C1 122.87(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2082(18)
C1 O2 1.3620(19)
C1 C18 1.465(2)
O2 C3 1.4442(17)
C3 O4 1.4294(17)
C3 C20 1.503(2)
C3 C19 1.505(2)
O4 C5 1.3703(18)
C5 C6 1.388(2)
C5 C18 1.395(2)
C6 C15 1.385(2)
C6 C7 1.505(2)
C7 C8 1.527(2)
C8 C13 1.538(2)
C8 C9 1.551(2)
C9 C21 1.528(2)
C9 C22 1.536(2)
C9 C10 1.540(2)
C10 C11 1.522(2)
C11 C12 1.524(2)
C12 C13 1.519(2)
C13 O14 1.4727(18)
C13 C23 1.518(2)
O14 C15 1.3602(17)
C15 C16 1.398(2)
C16 C17 1.378(2)
C17 C18 1.412(2)
C17 C24 1.508(2)
