#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:12:35 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180293 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/07/7150771.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_7150771
loop_
_publ_author_name
'Chantarasriwong, Oraphin'
'Cho, Woo Cheal'
'Batova, Ayse'
'Chavasiri, Warinthorn'
'Moore, Curtis'
'Rheingold, Arnold L.'
'Theodorakis, Emmanuel A.'
_publ_section_title
;
 Evaluation of the pharmacophoric motif of the caged Garcinia xanthones
;
_journal_issue                   23
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              4886
_journal_page_last               4894
_journal_paper_doi               10.1039/b913496d
_journal_volume                  7
_journal_year                    2009
_chemical_formula_sum            'C28 H35 N O4'
_chemical_formula_weight         449.57
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.4770(10)
_cell_angle_beta                 93.9620(10)
_cell_angle_gamma                92.8280(10)
_cell_formula_units_Z            2
_cell_length_a                   9.8106(7)
_cell_length_b                   10.1395(8)
_cell_length_c                   12.1918(9)
_cell_measurement_reflns_used    6169
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.31
_cell_volume                     1157.17(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9915
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9749
_exptl_absorpt_correction_T_min  0.9667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5073
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1308
_reflns_number_gt                4408
_reflns_number_total             5073
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b913496d.txt
_cod_data_source_block           theod24
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               7150771
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N1 N 0.29333(11) 0.72573(11) 0.48866(9) 0.0160(2) Uani 1 1 d . . .
O1 O 0.14476(9) 0.94212(9) 0.84656(8) 0.0159(2) Uani 1 1 d . . .
O2 O 0.40537(11) 1.10511(10) 0.66352(9) 0.0239(2) Uani 1 1 d . . .
O3 O 0.30252(11) 0.50478(10) 0.65457(9) 0.0233(2) Uani 1 1 d . . .
O4 O 0.22651(10) 0.68891(10) 0.87440(8) 0.0180(2) Uani 1 1 d . . .
C1 C 0.38040(15) 0.62232(14) 0.42279(12) 0.0201(3) Uani 1 1 d . . .
H1A H 0.4089 0.5611 0.4693 0.024 Uiso 1 1 calc R . .
H1B H 0.4640 0.6698 0.4067 0.024 Uiso 1 1 calc R . .
C2 C 0.30512(16) 0.53606(15) 0.31015(12) 0.0236(3) Uani 1 1 d . . .
H2A H 0.2248 0.4838 0.3263 0.028 Uiso 1 1 calc R . .
H2B H 0.3666 0.4689 0.2677 0.028 Uiso 1 1 calc R . .
C3 C 0.25756(17) 0.62633(16) 0.23633(12) 0.0257(3) Uani 1 1 d . . .
H3A H 0.2027 0.5693 0.1662 0.031 Uiso 1 1 calc R . .
H3B H 0.3377 0.6715 0.2129 0.031 Uiso 1 1 calc R . .
C4 C 0.17102(16) 0.73481(15) 0.30632(12) 0.0238(3) Uani 1 1 d . . .
H4A H 0.1442 0.7983 0.2614 0.029 Uiso 1 1 calc R . .
H4B H 0.0864 0.6893 0.3229 0.029 Uiso 1 1 calc R . .
C5 C 0.25086(15) 0.81636(14) 0.41860(12) 0.0197(3) Uani 1 1 d . . .
H5A H 0.3331 0.8652 0.4017 0.024 Uiso 1 1 calc R . .
H5B H 0.1931 0.8864 0.4627 0.024 Uiso 1 1 calc R . .
C6 C 0.36761(13) 0.80950(13) 0.59730(11) 0.0155(3) Uani 1 1 d . . .
H6A H 0.4429 0.8683 0.5795 0.019 Uiso 1 1 calc R . .
C7 C 0.43002(13) 0.71997(14) 0.66848(11) 0.0166(3) Uani 1 1 d . . .
H7A H 0.5011 0.6630 0.6269 0.020 Uiso 1 1 calc R . .
C8 C 0.49344(14) 0.82100(14) 0.78284(11) 0.0173(3) Uani 1 1 d . . .
H8A H 0.5605 0.7741 0.8202 0.021 Uiso 1 1 calc R . .
H8B H 0.5426 0.9006 0.7673 0.021 Uiso 1 1 calc R . .
C9 C 0.38149(13) 0.87229(13) 0.86361(11) 0.0159(3) Uani 1 1 d . . .
H9A H 0.4059 0.9693 0.9119 0.019 Uiso 1 1 calc R . .
C10 C 0.24861(13) 0.86373(13) 0.78501(11) 0.0143(3) Uani 1 1 d . . .
C11 C 0.27103(13) 0.90428(13) 0.67472(11) 0.0144(3) Uani 1 1 d . . .
H11A H 0.1798 0.8923 0.6298 0.017 Uiso 1 1 calc R . .
C12 C 0.31659(14) 1.05714(13) 0.70867(11) 0.0162(3) Uani 1 1 d . . .
C13 C 0.24008(13) 1.14360(13) 0.79979(11) 0.0156(3) Uani 1 1 d . . .
C14 C 0.24497(14) 1.28709(14) 0.82083(12) 0.0181(3) Uani 1 1 d . . .
H14A H 0.3014 1.3299 0.7786 0.022 Uiso 1 1 calc R . .
C15 C 0.16876(15) 1.36695(14) 0.90225(12) 0.0212(3) Uani 1 1 d . . .
H15A H 0.1718 1.4641 0.9155 0.025 Uiso 1 1 calc R . .
C16 C 0.08710(15) 1.30349(15) 0.96493(12) 0.0222(3) Uani 1 1 d . . .
H16A H 0.0345 1.3582 1.0210 0.027 Uiso 1 1 calc R . .
C17 C 0.08167(14) 1.16222(14) 0.94663(12) 0.0195(3) Uani 1 1 d . . .
H17A H 0.0270 1.1203 0.9906 0.023 Uiso 1 1 calc R . .
C18 C 0.15723(13) 1.08182(13) 0.86303(11) 0.0155(3) Uani 1 1 d . . .
C19 C 0.31220(14) 0.62899(14) 0.68825(11) 0.0167(3) Uani 1 1 d . . .
C20 C 0.34282(14) 0.77852(14) 0.93973(11) 0.0177(3) Uani 1 1 d . . .
C21 C 0.45318(15) 0.68647(15) 0.96272(13) 0.0229(3) Uani 1 1 d . . .
H21A H 0.4185 0.6303 1.0096 0.034 Uiso 1 1 calc R . .
H21B H 0.5345 0.7440 1.0037 0.034 Uiso 1 1 calc R . .
H21C H 0.4774 0.6260 0.8896 0.034 Uiso 1 1 calc R . .
C22 C 0.29375(15) 0.86125(15) 1.05311(12) 0.0215(3) Uani 1 1 d . . .
H22A H 0.2684 0.7987 1.0978 0.032 Uiso 1 1 calc R . .
H22B H 0.2139 0.9098 1.0379 0.032 Uiso 1 1 calc R . .
H22C H 0.3674 0.9285 1.0965 0.032 Uiso 1 1 calc R . .
C23 C 0.20487(13) 0.71085(13) 0.76316(11) 0.0156(3) Uani 1 1 d . . .
C24 C 0.05628(14) 0.65912(14) 0.72052(12) 0.0183(3) Uani 1 1 d . . .
H24A H 0.0469 0.5586 0.7101 0.022 Uiso 1 1 calc R . .
H24B H -0.0028 0.7031 0.7812 0.022 Uiso 1 1 calc R . .
C25 C 0.00292(14) 0.68492(14) 0.61057(12) 0.0175(3) Uani 1 1 d . . .
H25A H 0.0403 0.6353 0.5423 0.021 Uiso 1 1 calc R . .
C26 C -0.09219(14) 0.77116(14) 0.59995(12) 0.0189(3) Uani 1 1 d . . .
C27 C -0.13793(16) 0.78813(16) 0.48498(13) 0.0254(3) Uani 1 1 d . . .
H27A H -0.0884 0.7278 0.4256 0.038 Uiso 1 1 calc R . .
H27B H -0.1187 0.8843 0.4860 0.038 Uiso 1 1 calc R . .
H27C H -0.2365 0.7634 0.4682 0.038 Uiso 1 1 calc R . .
C28 C -0.16048(18) 0.86072(19) 0.69811(14) 0.0328(4) Uani 1 1 d . . .
H28A H -0.1249 0.8451 0.7701 0.049 Uiso 1 1 calc R . .
H28B H -0.2596 0.8377 0.6861 0.049 Uiso 1 1 calc R . .
H28C H -0.1415 0.9578 0.7021 0.049 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 0.0033 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'
N N 0.0061 0.0033 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C1 111.01(10) . . ?
C6 N1 C5 109.53(10) . . ?
C1 N1 C5 109.04(10) . . ?
C18 O1 C10 116.41(10) . . ?
C23 O4 C20 109.66(10) . . ?
N1 C1 C2 111.43(11) . . ?
C1 C2 C3 111.19(12) . . ?
C2 C3 C4 108.43(12) . . ?
C5 C4 C3 110.50(12) . . ?
N1 C5 C4 111.53(11) . . ?
N1 C6 C7 112.31(10) . . ?
N1 C6 C11 111.31(10) . . ?
C7 C6 C11 106.53(10) . . ?
C19 C7 C6 106.45(10) . . ?
C19 C7 C8 111.13(11) . . ?
C6 C7 C8 106.28(10) . . ?
C9 C8 C7 110.55(11) . . ?
C8 C9 C10 105.95(10) . . ?
C8 C9 C20 115.22(11) . . ?
C10 C9 C20 103.25(10) . . ?
O1 C10 C23 107.47(10) . . ?
O1 C10 C11 110.69(10) . . ?
C23 C10 C11 113.61(11) . . ?
O1 C10 C9 111.60(10) . . ?
C23 C10 C9 98.93(10) . . ?
C11 C10 C9 113.91(10) . . ?
C12 C11 C10 108.18(10) . . ?
C12 C11 C6 114.45(10) . . ?
C10 C11 C6 112.62(10) . . ?
O2 C12 C13 122.65(12) . . ?
O2 C12 C11 123.32(12) . . ?
C13 C12 C11 114.01(11) . . ?
C14 C13 C18 119.09(12) . . ?
C14 C13 C12 120.82(12) . . ?
C18 C13 C12 120.04(12) . . ?
C15 C14 C13 120.77(12) . . ?
C14 C15 C16 119.33(13) . . ?
C17 C16 C15 121.01(13) . . ?
C16 C17 C18 119.42(13) . . ?
O1 C18 C17 116.77(11) . . ?
O1 C18 C13 122.85(12) . . ?
C17 C18 C13 120.38(12) . . ?
O3 C19 C7 124.78(13) . . ?
O3 C19 C23 121.60(12) . . ?
C7 C19 C23 113.55(11) . . ?
O4 C20 C22 107.30(11) . . ?
O4 C20 C21 107.58(11) . . ?
C22 C20 C21 109.57(11) . . ?
O4 C20 C9 104.39(10) . . ?
C22 C20 C9 111.79(11) . . ?
C21 C20 C9 115.68(11) . . ?
O4 C23 C10 103.86(10) . . ?
O4 C23 C24 105.71(10) . . ?
C10 C23 C24 119.28(11) . . ?
O4 C23 C19 106.45(10) . . ?
C10 C23 C19 106.32(10) . . ?
C24 C23 C19 114.07(11) . . ?
C25 C24 C23 116.21(11) . . ?
C26 C25 C24 125.96(13) . . ?
C25 C26 C27 121.21(13) . . ?
C25 C26 C28 124.73(13) . . ?
C27 C26 C28 114.06(13) . . ?
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
N1 C6 1.4745(17) . ?
N1 C1 1.4762(17) . ?
N1 C5 1.4770(17) . ?
O1 C18 1.3711(15) . ?
O1 C10 1.4423(15) . ?
O2 C12 1.2143(16) . ?
O3 C19 1.2055(17) . ?
O4 C23 1.4387(16) . ?
O4 C20 1.4572(16) . ?
C1 C2 1.5202(19) . ?
C2 C3 1.522(2) . ?
C3 C4 1.523(2) . ?
C4 C5 1.522(2) . ?
C6 C7 1.5430(18) . ?
C6 C11 1.5528(17) . ?
C7 C19 1.5181(19) . ?
C7 C8 1.5451(18) . ?
C8 C9 1.5368(18) . ?
C9 C10 1.5473(18) . ?
C9 C20 1.5565(18) . ?
C10 C23 1.5305(18) . ?
C10 C11 1.5399(18) . ?
C11 C12 1.5217(18) . ?
C12 C13 1.4811(18) . ?
C13 C14 1.4016(18) . ?
C13 C18 1.3992(18) . ?
C14 C15 1.3808(19) . ?
C15 C16 1.397(2) . ?
C16 C17 1.383(2) . ?
C17 C18 1.3949(19) . ?
C19 C23 1.5559(18) . ?
C20 C22 1.5233(19) . ?
C20 C21 1.5259(19) . ?
C23 C24 1.5282(18) . ?
C24 C25 1.5016(19) . ?
C25 C26 1.334(2) . ?
C26 C27 1.501(2) . ?
C26 C28 1.503(2) . ?
