#------------------------------------------------------------------------------
#$Date: 2024-11-29 17:16:05 +0200 (Fri, 29 Nov 2024) $
#$Revision: 296166 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/28/4122864.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_4122864
loop_
_publ_author_name
'Mailhol, Damien'
'Willwacher, Jens'
'Kausch-Busies, Nina'
'Rubitski, Elizabeth E.'
'Sobol, Zhanna'
'Schuler, Maik'
'Lam, My-Hanh'
'Musto, Sylvia'
'Loganzo, Frank'
'Maderna, Andreas'
'Fürstner, Alois'
_publ_section_title
;
 Synthesis, molecular editing, and biological assessment of the potent
 cytotoxin leiodermatolide.
;
_journal_issue                   44
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15719
_journal_page_last               15729
_journal_paper_doi               10.1021/ja508846g
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration rmad
_chemical_compound_source        'see paper'
_chemical_formula_moiety         'C11 H16 O3'
_chemical_formula_sum            'C11 H16 O3'
_chemical_formula_weight         196.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                MID-MA-128-02
_audit_creation_date             2013-07-12
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6320(2)
_cell_length_b                   7.9748(2)
_cell_length_c                   17.8334(5)
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    100
_cell_measurement_theta_max      64.7189
_cell_measurement_theta_min      4.9599
_cell_volume                     1085.41(5)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'PROTEUM2 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (G. M. Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (G. M. Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  'focusing multilayer optic'
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           Cu-K\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            44850
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.577
_diffrn_reflns_theta_min         4.960
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  0.95940
_exptl_absorpt_correction_T_min  0.85026
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 723 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.07(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0291
_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)+(0.0318P)²+0.3065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0714
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                1810
_reflns_number_total             1898
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja508846g_si_001.cif
_cod_data_source_block           8338sadabs
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'ORTHORHOMBIC' changed to
'orthorhombic' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 4122864--4122865.cif.
;
_cod_original_sg_symbol_Hall     'p 2ac 2ab'
_cod_original_sg_symbol_H-M      'P21 21 21'
_cod_database_code               4122864
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C9(H9A,H9B)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
2.e :
 C11(H11)
;
_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.
;
_shelxl_version_number           2013-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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 -0.10655(17) -0.68867(18) -0.57492(7) 0.0245(3) Uani 1 1 d . .
O2 O 0.39298(18) -0.77733(15) -0.57925(8) 0.0203(3) Uani 1 1 d . .
H2 H 0.3950 -0.7971 -0.5330 0.030 Uiso 1 1 calc R U
O3 O 0.05428(16) -0.68721(18) -0.67587(7) 0.0221(3) Uani 1 1 d . .
C1 C 0.0334(3) -0.6522(2) -0.60381(10) 0.0192(4) Uani 1 1 d . .
C2 C 0.1759(3) -0.5638(2) -0.56197(11) 0.0186(4) Uani 1 1 d . .
H2A H 0.1696 -0.5959 -0.5084 0.022 Uiso 1 1 calc R U
H2B H 0.1560 -0.4414 -0.5653 0.022 Uiso 1 1 calc R U
C3 C 0.3577(3) -0.6032(2) -0.59128(11) 0.0178(4) Uani 1 1 d . .
C4 C 0.3627(2) -0.5725(2) -0.67611(11) 0.0183(4) Uani 1 1 d . .
H4 H 0.3376 -0.4512 -0.6852 0.022 Uiso 1 1 calc R U
C5 C 0.2219(2) -0.6753(3) -0.71594(10) 0.0193(4) Uani 1 1 d . .
H5 H 0.2681 -0.7917 -0.7226 0.023 Uiso 1 1 calc R U
C6 C 0.1755(3) -0.6075(3) -0.79305(11) 0.0235(5) Uani 1 1 d . .
H6A H 0.2843 -0.5951 -0.8227 0.028 Uiso 1 1 calc R U
H6B H 0.1229 -0.4947 -0.7873 0.028 Uiso 1 1 calc R U
C7 C 0.0485(3) -0.7187(3) -0.83595(12) 0.0342(5) Uani 1 1 d . .
H7A H 0.0287 -0.6717 -0.8860 0.051 Uiso 1 1 calc R U
H7B H -0.0630 -0.7246 -0.8088 0.051 Uiso 1 1 calc R U
H7C H 0.0981 -0.8316 -0.8407 0.051 Uiso 1 1 calc R U
C8 C 0.5413(3) -0.6125(3) -0.70997(12) 0.0277(5) Uani 1 1 d . .
H8A H 0.6286 -0.5335 -0.6905 0.042 Uiso 1 1 calc R U
H8B H 0.5350 -0.6023 -0.7647 0.042 Uiso 1 1 calc R U
H8C H 0.5751 -0.7271 -0.6965 0.042 Uiso 1 1 calc R U
C9 C 0.4947(3) -0.4974(2) -0.54866(11) 0.0199(4) Uani 1 1 d . .
H9A H 0.4851 -0.5209 -0.4943 0.024 Uiso 1 1 calc R U
H9B H 0.6136 -0.5306 -0.5651 0.024 Uiso 1 1 calc R U
C10 C 0.4711(3) -0.3166(3) -0.56146(10) 0.0225(4) Uani 1 1 d . .
C11 C 0.4420(3) -0.1731(2) -0.57374(11) 0.0269(5) Uani 1 1 d . .
H11 H 0.4187 -0.0582 -0.5836 0.032 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 0.0181 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.0200
0.00 0.00 1.00 0.0400
-1.00 -1.00 -1.00 0.1200
0.00 1.00 0.00 0.0700
0.00 -1.00 0.00 0.1300
1.00 0.00 0.00 0.1600
-1.00 0.00 0.00 0.1700
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O3 C5 124.27(15)
O1 C1 O3 117.66(17)
O1 C1 C2 122.54(17)
O3 C1 C2 119.74(17)
C1 C2 C3 113.32(16)
O2 C3 C2 108.77(15)
O2 C3 C4 107.34(15)
O2 C3 C9 109.22(15)
C2 C3 C4 109.28(15)
C2 C3 C9 109.68(15)
C4 C3 C9 112.45(16)
C5 C4 C3 110.86(15)
C8 C4 C3 112.33(16)
C8 C4 C5 109.45(15)
O3 C5 C4 114.93(15)
O3 C5 C6 105.08(15)
C6 C5 C4 113.21(16)
C5 C6 C7 113.35(17)
C10 C9 C3 112.12(16)
C11 C10 C9 175.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.221(2)
O2 C3 1.431(2)
O3 C1 1.325(2)
O3 C5 1.468(2)
C1 C2 1.495(3)
C2 C3 1.516(3)
C3 C4 1.533(3)
C3 C9 1.544(3)
C4 C5 1.527(3)
C4 C8 1.524(3)
C5 C6 1.520(3)
C6 C7 1.520(3)
C9 C10 1.471(3)
C10 C11 1.186(3)
