#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:21:33 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180134 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/32/7103203.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_7103203
loop_
_publ_author_name
'Ramana, C V'
'Nageswara Reddy, Challa'
'Gonnade, Rajesh G'
_publ_section_title
;
 An expeditious one-step entry to the tetracyclic core of
 integrastatins.
;
_journal_issue                   27
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3151
_journal_page_last               3153
_journal_paper_doi               10.1039/b801755g
_journal_year                    2008
_chemical_formula_moiety         'C16 H14 O4'
_chemical_formula_sum            'C16 H14 O4'
_chemical_formula_weight         270.27
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.439(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.896(2)
_cell_length_b                   12.117(3)
_cell_length_c                   13.238(4)
_cell_measurement_reflns_used    1707
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      23.09
_cell_measurement_theta_min      2.85
_cell_volume                     1255.8(6)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXTL (Bruker, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'Phi and Omega Scan'
_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  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8909
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9969
_exptl_absorpt_correction_T_min  0.9547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0377P)²+0.3703P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1006
_reflns_number_gt                1757
_reflns_number_total             2215
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b801755g.txt
_cod_data_source_block           nr_o_vac_mc
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' 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      P2(1)/n
_cod_database_code               7103203
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.16212(17) 0.21481(10) 0.36404(9) 0.0360(3) Uani 1 1 d . . .
O2 O 0.37429(17) 0.31815(11) 0.45755(10) 0.0418(4) Uani 1 1 d . . .
O3 O 0.3475(2) 0.25446(13) 0.72459(11) 0.0545(5) Uani 1 1 d . . .
O4 O 0.04858(18) 0.02387(11) 0.29811(10) 0.0424(4) Uani 1 1 d . . .
C1 C 0.2020(2) 0.31792(15) 0.41512(14) 0.0345(5) Uani 1 1 d . . .
H1 H 0.1866 0.3765 0.3637 0.041 Uiso 1 1 calc R . .
C2 C 0.0806(3) 0.34075(15) 0.49235(14) 0.0325(5) Uani 1 1 d . . .
C3 C -0.0886(3) 0.36576(15) 0.45945(15) 0.0377(5) Uani 1 1 d . . .
H3 H -0.1269 0.3678 0.3900 0.045 Uiso 1 1 calc R . .
C4 C -0.2008(3) 0.38761(17) 0.52826(17) 0.0452(6) Uani 1 1 d . . .
H4 H -0.3140 0.4050 0.5054 0.054 Uiso 1 1 calc R . .
C5 C -0.1449(3) 0.38364(17) 0.63135(18) 0.0493(6) Uani 1 1 d . . .
H5 H -0.2206 0.3976 0.6781 0.059 Uiso 1 1 calc R . .
C6 C 0.0243(3) 0.35889(16) 0.66519(16) 0.0448(6) Uani 1 1 d . . .
H6 H 0.0616 0.3568 0.7348 0.054 Uiso 1 1 calc R . .
C7 C 0.1389(3) 0.33715(15) 0.59657(14) 0.0352(5) Uani 1 1 d . . .
C8 C 0.3254(3) 0.31152(17) 0.62992(14) 0.0419(5) Uani 1 1 d . . .
H8 H 0.3876 0.3816 0.6390 0.050 Uiso 1 1 calc R . .
C9 C 0.3955(3) 0.24681(17) 0.54578(15) 0.0403(5) Uani 1 1 d . . .
H9 H 0.5181 0.2353 0.5660 0.048 Uiso 1 1 calc R . .
C10 C 0.3143(2) 0.13624(16) 0.51823(14) 0.0342(5) Uani 1 1 d . . .
C11 C 0.3494(3) 0.04219(17) 0.57813(15) 0.0425(5) Uani 1 1 d . . .
H11 H 0.4198 0.0474 0.6400 0.051 Uiso 1 1 calc R . .
C12 C 0.2808(3) -0.05814(17) 0.54640(15) 0.0441(5) Uani 1 1 d . . .
H12 H 0.3027 -0.1198 0.5879 0.053 Uiso 1 1 calc R . .
C13 C 0.1793(3) -0.06859(17) 0.45311(15) 0.0401(5) Uani 1 1 d . . .
H13 H 0.1353 -0.1371 0.4318 0.048 Uiso 1 1 calc R . .
C14 C 0.1438(2) 0.02298(16) 0.39221(13) 0.0331(5) Uani 1 1 d . . .
C15 C 0.2082(2) 0.12550(15) 0.42681(13) 0.0313(4) Uani 1 1 d . . .
C16 C -0.0154(3) -0.07971(18) 0.25858(17) 0.0550(6) Uani 1 1 d . . .
H16A H 0.0775 -0.1308 0.2584 0.083 Uiso 1 1 calc R . .
H16B H -0.0709 -0.0699 0.1903 0.083 Uiso 1 1 calc R . .
H16C H -0.0959 -0.1082 0.3005 0.083 Uiso 1 1 calc R . .
H3A H 0.432(4) 0.285(2) 0.762(2) 0.085(10) Uiso 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O1 C1 111.89(13) . . ?
C1 O2 C9 109.12(14) . . ?
C14 O4 C16 116.97(15) . . ?
O2 C1 O1 109.44(15) . . ?
O2 C1 C2 113.27(15) . . ?
O1 C1 C2 110.92(15) . . ?
C3 C2 C7 119.94(19) . . ?
C3 C2 C1 119.82(17) . . ?
C7 C2 C1 120.24(18) . . ?
C4 C3 C2 120.79(19) . . ?
C3 C4 C5 119.8(2) . . ?
C4 C5 C6 120.0(2) . . ?
C5 C6 C7 120.8(2) . . ?
C6 C7 C2 118.72(19) . . ?
C6 C7 C8 122.69(18) . . ?
C2 C7 C8 118.58(19) . . ?
O3 C8 C7 111.13(18) . . ?
O3 C8 C9 112.29(17) . . ?
C7 C8 C9 108.92(15) . . ?
O2 C9 C10 109.54(15) . . ?
O2 C9 C8 105.53(16) . . ?
C10 C9 C8 116.74(17) . . ?
C15 C10 C11 118.22(18) . . ?
C15 C10 C9 118.95(17) . . ?
C11 C10 C9 122.71(17) . . ?
C12 C11 C10 120.47(18) . . ?
C11 C12 C13 120.79(19) . . ?
C14 C13 C12 119.79(19) . . ?
O4 C14 C13 125.75(18) . . ?
O4 C14 C15 115.16(16) . . ?
C13 C14 C15 119.09(17) . . ?
O1 C15 C10 122.22(17) . . ?
O1 C15 C14 116.24(15) . . ?
C10 C15 C14 121.54(17) . . ?
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
O1 C15 1.384(2) . ?
O1 C1 1.436(2) . ?
O2 C1 1.403(2) . ?
O2 C9 1.445(2) . ?
O3 C8 1.422(2) . ?
O4 C14 1.369(2) . ?
O4 C16 1.427(2) . ?
C1 C2 1.515(3) . ?
C2 C3 1.384(3) . ?
C2 C7 1.398(3) . ?
C3 C4 1.376(3) . ?
C4 C5 1.380(3) . ?
C5 C6 1.386(3) . ?
C6 C7 1.388(3) . ?
C7 C8 1.513(3) . ?
C8 C9 1.524(3) . ?
C9 C10 1.510(3) . ?
C10 C15 1.386(3) . ?
C10 C11 1.395(3) . ?
C11 C12 1.374(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.379(3) . ?
C14 C15 1.397(3) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O2 C1 O1 -73.48(18) . . . . ?
C9 O2 C1 C2 50.8(2) . . . . ?
C15 O1 C1 O2 52.81(19) . . . . ?
C15 O1 C1 C2 -72.88(19) . . . . ?
O2 C1 C2 C3 166.65(16) . . . . ?
O1 C1 C2 C3 -69.8(2) . . . . ?
O2 C1 C2 C7 -13.1(2) . . . . ?
O1 C1 C2 C7 110.46(18) . . . . ?
C7 C2 C3 C4 0.2(3) . . . . ?
C1 C2 C3 C4 -179.50(18) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C5 C6 C7 C2 0.1(3) . . . . ?
C5 C6 C7 C8 179.01(19) . . . . ?
C3 C2 C7 C6 0.1(3) . . . . ?
C1 C2 C7 C6 179.77(17) . . . . ?
C3 C2 C7 C8 -178.94(17) . . . . ?
C1 C2 C7 C8 0.8(3) . . . . ?
C6 C7 C8 O3 32.3(3) . . . . ?
C2 C7 C8 O3 -148.69(17) . . . . ?
C6 C7 C8 C9 156.56(18) . . . . ?
C2 C7 C8 C9 -24.5(2) . . . . ?
C1 O2 C9 C10 50.4(2) . . . . ?
C1 O2 C9 C8 -76.07(18) . . . . ?
O3 C8 C9 O2 -176.21(15) . . . . ?
C7 C8 C9 O2 60.3(2) . . . . ?
O3 C8 C9 C10 61.9(2) . . . . ?
C7 C8 C9 C10 -61.7(2) . . . . ?
O2 C9 C10 C15 -12.4(3) . . . . ?
C8 C9 C10 C15 107.4(2) . . . . ?
O2 C9 C10 C11 163.59(18) . . . . ?
C8 C9 C10 C11 -76.6(2) . . . . ?
C15 C10 C11 C12 0.3(3) . . . . ?
C9 C10 C11 C12 -175.7(2) . . . . ?
C10 C11 C12 C13 1.8(3) . . . . ?
C11 C12 C13 C14 -1.3(3) . . . . ?
C16 O4 C14 C13 -1.9(3) . . . . ?
C16 O4 C14 C15 178.19(18) . . . . ?
C12 C13 C14 O4 178.71(19) . . . . ?
C12 C13 C14 C15 -1.3(3) . . . . ?
C1 O1 C15 C10 -13.7(2) . . . . ?
C1 O1 C15 C14 167.21(16) . . . . ?
C11 C10 C15 O1 177.96(17) . . . . ?
C9 C10 C15 O1 -5.8(3) . . . . ?
C11 C10 C15 C14 -3.0(3) . . . . ?
C9 C10 C15 C14 173.19(18) . . . . ?
O4 C14 C15 O1 2.6(2) . . . . ?
C13 C14 C15 O1 -177.38(17) . . . . ?
O4 C14 C15 C10 -176.52(17) . . . . ?
C13 C14 C15 C10 3.5(3) . . . . ?
