#------------------------------------------------------------------------------
#$Date: 2017-12-11 01:28:22 +0200 (Mon, 11 Dec 2017) $
#$Revision: 204147 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/53/4125309.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_4125309
loop_
_publ_author_name
'Ting, Chi P.'
'Xu, Gong'
'Zeng, Xianhuang'
'Maimone, Thomas J.'
_publ_section_title
;
 Annulative Methods Enable a Total Synthesis of the Complex Meroterpene
 Berkeleyone A.
;
_journal_issue                   45
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14868
_journal_page_last               14871
_journal_paper_doi               10.1021/jacs.6b10397
_journal_volume                  138
_journal_year                    2016
_chemical_formula_sum            'C13 H14 O3'
_chemical_formula_weight         218.24
_chemical_name_common            Cpting-07281-Pure
_chemical_name_systematic        maimone77
_space_group.centring_type       P
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 110.892(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6286(6)
_cell_length_b                   8.0267(4)
_cell_length_c                   13.8441(7)
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      4.45
_cell_volume                     1103.43(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2014
_computing_structure_solution    SHELXT-2014
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_refln_scan_rate          10
_diffrn_refln_scan_width         2.0
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30022
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.365
_diffrn_reflns_theta_min         4.453
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0466P)²+0.5282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0961
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1743
_reflns_number_total             2024
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b10397_si_004.cif
_cod_data_source_block           maimone77
_cod_depositor_comments
;Adding full bibliography for 4125309--4125312.cif.

The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_database_code               4125309
#BEGIN Tags that were not found in dictionaries:
_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. 
;
_shelx_estimated_absorpt_t_min   0.963
_shelx_estimated_absorpt_t_max   0.985
#END Tags that were not found in dictionaries
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
C1 C 0.65611(14) 0.80350(17) 0.42280(10) 0.0175(3) Uani 1 1 d . .
C2 C 0.64306(14) 0.73651(18) 0.31456(10) 0.0181(3) Uani 1 1 d . .
H2 H 0.6359 0.6124 0.3164 0.022 Uiso 1 1 calc R U
C3 C 0.51245(15) 0.80158(18) 0.23628(10) 0.0194(3) Uani 1 1 d . .
C4 C 0.38608(14) 0.77151(18) 0.25985(11) 0.0198(3) Uani 1 1 d . .
H4A H 0.3120 0.8397 0.2126 0.024 Uiso 1 1 calc R U
H4B H 0.3600 0.6529 0.2468 0.024 Uiso 1 1 calc R U
C5 C 0.40380(14) 0.81391(18) 0.37017(11) 0.0187(3) Uani 1 1 d . .
C6 C 0.53255(14) 0.75495(18) 0.45048(11) 0.0197(3) Uani 1 1 d . .
H6A H 0.5296 0.6323 0.4569 0.024 Uiso 1 1 calc R U
H6B H 0.5416 0.8043 0.5182 0.024 Uiso 1 1 calc R U
C7 C 0.76387(14) 0.77768(19) 0.28439(11) 0.0220(3) Uani 1 1 d . .
H7A H 0.7512 0.7287 0.2167 0.033 Uiso 1 1 calc R U
H7B H 0.8457 0.7320 0.3362 0.033 Uiso 1 1 calc R U
H7C H 0.7726 0.8989 0.2809 0.033 Uiso 1 1 calc R U
C8 C 0.78329(14) 0.73496(18) 0.50530(10) 0.0187(3) Uani 1 1 d . .
C9 C 0.79246(15) 0.56501(19) 0.52869(11) 0.0213(3) Uani 1 1 d . .
H9 H 0.7208 0.4927 0.4915 0.026 Uiso 1 1 calc R U
C10 C 0.90504(15) 0.5008(2) 0.60553(12) 0.0249(3) Uani 1 1 d . .
H10 H 0.9102 0.3850 0.6206 0.030 Uiso 1 1 calc R U
C11 C 1.01010(15) 0.6053(2) 0.66044(12) 0.0273(4) Uani 1 1 d . .
H11 H 1.0864 0.5621 0.7143 0.033 Uiso 1 1 calc R U
C12 C 1.00271(15) 0.7731(2) 0.63609(12) 0.0272(4) Uani 1 1 d . .
H12 H 1.0753 0.8447 0.6726 0.033 Uiso 1 1 calc R U
C13 C 0.89035(15) 0.83820(19) 0.55876(11) 0.0225(3) Uani 1 1 d . .
H13 H 0.8868 0.9535 0.5425 0.027 Uiso 1 1 calc R U
O1 O 0.65754(10) 0.98073(12) 0.41287(7) 0.0206(2) Uani 1 1 d . .
H1 H 0.6658 1.0252 0.4697 0.031 Uiso 1 1 calc R U
O2 O 0.50757(11) 0.87624(13) 0.15847(8) 0.0241(3) Uani 1 1 d . .
O3 O 0.31729(10) 0.88924(14) 0.39062(8) 0.0256(3) 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 0.0181 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 C8 113.16(11)
O1 C1 C6 108.32(11)
C8 C1 C6 109.14(11)
O1 C1 C2 104.62(10)
C8 C1 C2 110.36(11)
C6 C1 C2 111.19(11)
C3 C2 C7 112.08(11)
C3 C2 C1 108.34(11)
C7 C2 C1 113.36(11)
C3 C2 H2 107.6
C7 C2 H2 107.6
C1 C2 H2 107.6
O2 C3 C4 120.61(13)
O2 C3 C2 122.75(13)
C4 C3 C2 116.63(12)
C5 C4 C3 112.51(12)
C5 C4 H4A 109.1
C3 C4 H4A 109.1
C5 C4 H4B 109.1
C3 C4 H4B 109.1
H4A C4 H4B 107.8
O3 C5 C6 123.41(13)
O3 C5 C4 121.07(13)
C6 C5 C4 115.52(12)
C5 C6 C1 111.62(11)
C5 C6 H6A 109.3
C1 C6 H6A 109.3
C5 C6 H6B 109.3
C1 C6 H6B 109.3
H6A C6 H6B 108.0
C2 C7 H7A 109.5
C2 C7 H7B 109.5
H7A C7 H7B 109.5
C2 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C13 C8 C9 118.87(13)
C13 C8 C1 121.47(13)
C9 C8 C1 119.66(13)
C10 C9 C8 120.70(14)
C10 C9 H9 119.6
C8 C9 H9 119.6
C9 C10 C11 120.12(15)
C9 C10 H10 119.9
C11 C10 H10 119.9
C12 C11 C10 119.38(14)
C12 C11 H11 120.3
C10 C11 H11 120.3
C11 C12 C13 120.78(15)
C11 C12 H12 119.6
C13 C12 H12 119.6
C8 C13 C12 120.11(14)
C8 C13 H13 119.9
C12 C13 H13 119.9
C1 O1 H1 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.4298(17)
C1 C8 1.5275(19)
C1 C6 1.5435(19)
C1 C2 1.5511(18)
C2 C3 1.5170(19)
C2 C7 1.5214(19)
C2 H2 1.0000
C3 O2 1.2175(18)
C3 C4 1.510(2)
C4 C5 1.5094(19)
C4 H4A 0.9900
C4 H4B 0.9900
C5 O3 1.2153(18)
C5 C6 1.4992(19)
C6 H6A 0.9900
C6 H6B 0.9900
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 C13 1.389(2)
C8 C9 1.397(2)
C9 C10 1.386(2)
C9 H9 0.9500
C10 C11 1.387(2)
C10 H10 0.9500
C11 C12 1.384(2)
C11 H11 0.9500
C12 C13 1.390(2)
C12 H12 0.9500
C13 H13 0.9500
O1 H1 0.8400
