#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/61/1516101.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_1516101
loop_
_publ_author_name
'Truong, Phong'
'Shanahan, Charles S.'
'Doyle, Michael P.'
_publ_section_title
;
 Divergent stereocontrol of acid catalyzed intramolecular aldol reactions
 of 2,3,7-triketoesters: synthesis of highly functionalized
 cyclopentanones.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3608
_journal_page_last               3611
_journal_paper_doi               10.1021/ol301317a
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C20 H18 O5'
_chemical_formula_sum            'C20 H18 O5'
_chemical_formula_weight         338.34
_chemical_name_common            diphenyl
_chemical_name_systematic
;
diphenyl
;
_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 & ZCIF'
_cell_angle_alpha                90.00
_cell_angle_beta                 106.5495(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.4332(15)
_cell_length_b                   5.5136(5)
_cell_length_c                   18.3321(17)
_cell_measurement_reflns_used    11898
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.0
_cell_measurement_theta_min      2.3
_cell_volume                     1592.2(3)
_computing_cell_refinement       Apex2
_computing_data_collection       'Apex2 (Bruker, 2005)'
_computing_data_reduction        Apex2
_computing_molecular_graphics    'XSHEL (Bruker, 2004)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 11.198
_diffrn_detector_type            'Bruker Smart Apex II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
; Measured frames                     366,366,366,720
_diffrn_measurement_frame_width-CCD  -0.5
_diffrn_measurement_total_frames-CCD  1818
_diffrn_measurement_frame_time-CCD    15
_diffrn_measurement_total_time-CCD    10.6
_diffrn_detector_distance-CCD         5.00
_diffrn_measurement_frame_size-CCD    512
;
_diffrn_measurement_device_type  'three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_specimen_support 'MiTeGen loop'
_diffrn_orient_matrix_type       standard
_diffrn_orient_matrix_UB_11      -0.0334461
_diffrn_orient_matrix_UB_12      -0.0362244
_diffrn_orient_matrix_UB_13      0.0364733
_diffrn_orient_matrix_UB_21      -0.0533474
_diffrn_orient_matrix_UB_22      0.0481672
_diffrn_orient_matrix_UB_23      -0.0393272
_diffrn_orient_matrix_UB_31      -0.0079283
_diffrn_orient_matrix_UB_32      -0.1710394
_diffrn_orient_matrix_UB_33      -0.0189603
_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  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23378
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         1.97
_diffrn_source_current           30.00
_diffrn_source_voltage           50.00
_diffrn_standards_interval_count '$REMOVE_ENTRY'
_diffrn_standards_interval_time  '$REMOVE_ENTRY'
_diffrn_standards_number         '$REMOVE_ENTRY'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0368
_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)+(0.01P)²+1.146P], P=(max(Fo²,0)+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0778
_reflns_number_gt                4093
_reflns_number_total             4642
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301317a_si_003.cif
_cod_data_source_block           2041
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1516101
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
C1 C 0.44192(8) 0.1602(2) 0.08243(6) 0.0216(2) Uani 1 1 d
H1A H 0.4894(10) 0.249(3) 0.0715(9) 0.034(2) Uiso 1 1 d
H1B H 0.3887(10) 0.197(3) 0.0458(9) 0.034(2) Uiso 1 1 d
H1C H 0.4507(10) -0.014(3) 0.0833(9) 0.034(2) Uiso 1 1 d
O1 O 0.43747(5) 0.22662(14) 0.15781(4) 0.01668(15) Uani 1 1 d
C2 C 0.40915(6) 0.45107(19) 0.16415(6) 0.01541(19) Uani 1 1 d
O2 O 0.38205(5) 0.58869(16) 0.11212(5) 0.02390(18) Uani 1 1 d
C3 C 0.41766(6) 0.51027(18) 0.24741(6) 0.01350(18) Uani 1 1 d
O3 O 0.37913(5) 0.73515(14) 0.25418(5) 0.01826(16) Uani 1 1 d
H3 H 0.3260(11) 0.720(3) 0.2394(9) 0.036(4) Uiso 1 1 d
C4 C 0.37620(6) 0.31757(18) 0.28781(6) 0.01436(18) Uani 1 1 d
O4 O 0.30468(5) 0.24487(14) 0.26055(4) 0.01930(16) Uani 1 1 d
C5 C 0.43594(6) 0.26554(19) 0.36573(6) 0.01506(18) Uani 1 1 d
H5A H 0.4627(8) 0.110(3) 0.3627(8) 0.020(2) Uiso 1 1 d
H5B H 0.4051(8) 0.254(3) 0.4035(8) 0.020(2) Uiso 1 1 d
C6 C 0.49924(6) 0.47660(18) 0.37910(5) 0.01272(17) Uani 1 1 d
H6 H 0.4696(8) 0.620(2) 0.3909(7) 0.016(3) Uiso 1 1 d
C7 C 0.51055(6) 0.52980(17) 0.29929(5) 0.01180(17) Uani 1 1 d
H7 H 0.5295(7) 0.697(2) 0.2954(7) 0.009(3) Uiso 1 1 d
C8 C 0.57283(6) 0.35508(18) 0.27861(5) 0.01237(17) Uani 1 1 d
O8 O 0.58787(5) 0.15712(13) 0.30903(4) 0.01623(15) Uani 1 1 d
C9 C 0.61582(6) 0.43396(18) 0.22064(5) 0.01299(18) Uani 1 1 d
C10 C 0.59820(6) 0.65379(19) 0.18131(6) 0.01604(19) Uani 1 1 d
H10 H 0.5593(9) 0.768(3) 0.1921(8) 0.023(3) Uiso 1 1 d
C11 C 0.63756(7) 0.7095(2) 0.12521(6) 0.0192(2) Uani 1 1 d
H11 H 0.6254(9) 0.862(3) 0.0986(8) 0.025(4) Uiso 1 1 d
C12 C 0.69531(7) 0.5496(2) 0.10910(6) 0.0210(2) Uani 1 1 d
H12 H 0.7231(9) 0.591(3) 0.0703(8) 0.027(4) Uiso 1 1 d
C13 C 0.71371(7) 0.3317(2) 0.14871(6) 0.0201(2) Uani 1 1 d
H13 H 0.7540(9) 0.222(3) 0.1380(8) 0.028(4) Uiso 1 1 d
C14 C 0.67432(6) 0.27424(19) 0.20408(6) 0.01615(19) Uani 1 1 d
H14 H 0.6859(8) 0.127(3) 0.2317(7) 0.018(3) Uiso 1 1 d
C15 C 0.58079(6) 0.45490(18) 0.44311(5) 0.01319(18) Uani 1 1 d
C16 C 0.63939(6) 0.64549(19) 0.45418(6) 0.01515(19) Uani 1 1 d
H16 H 0.6273(8) 0.782(3) 0.4200(7) 0.019(3) Uiso 1 1 d
C17 C 0.71306(7) 0.6430(2) 0.51506(6) 0.0173(2) Uani 1 1 d
H17 H 0.7519(9) 0.777(3) 0.5229(8) 0.023(4) Uiso 1 1 d
C18 C 0.72855(7) 0.4516(2) 0.56683(6) 0.0182(2) Uani 1 1 d
H18 H 0.7778(9) 0.452(3) 0.6109(8) 0.024(4) Uiso 1 1 d
C19 C 0.67137(7) 0.2604(2) 0.55600(6) 0.0182(2) Uani 1 1 d
H19 H 0.6820(8) 0.130(3) 0.5921(8) 0.021(3) Uiso 1 1 d
C20 C 0.59815(6) 0.26130(19) 0.49411(6) 0.01607(19) Uani 1 1 d
H20 H 0.5592(9) 0.126(3) 0.4873(8) 0.022(3) 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
O1 C1 H1A 109.0(9)
O1 C1 H1B 109.2(9)
H1A C1 H1B 111.6(13)
O1 C1 H1C 106.3(9)
H1A C1 H1C 111.7(13)
H1B C1 H1C 108.8(13)
C2 O1 C1 115.40(8)
O2 C2 O1 125.07(10)
O2 C2 C3 124.49(10)
O1 C2 C3 110.43(8)
O3 C3 C2 111.05(8)
O3 C3 C7 105.77(8)
C2 C3 C7 114.85(8)
O3 C3 C4 106.79(8)
C2 C3 C4 113.65(8)
C7 C3 C4 104.03(8)
C3 O3 H3 109.5(12)
O4 C4 C5 128.42(10)
O4 C4 C3 122.39(9)
C5 C4 C3 108.91(8)
C4 C5 C6 103.61(8)
C4 C5 H5A 107.2(8)
C6 C5 H5A 112.4(8)
C4 C5 H5B 110.8(8)
C6 C5 H5B 113.8(8)
H5A C5 H5B 108.7(11)
C15 C6 C5 118.32(8)
C15 C6 C7 115.32(8)
C5 C6 C7 104.49(8)
C15 C6 H6 106.1(7)
C5 C6 H6 106.8(8)
C7 C6 H6 104.7(8)
C8 C7 C6 112.47(8)
C8 C7 C3 114.47(8)
C6 C7 C3 101.70(7)
C8 C7 H7 108.9(7)
C6 C7 H7 111.8(7)
C3 C7 H7 107.3(7)
O8 C8 C9 120.62(9)
O8 C8 C7 120.90(9)
C9 C8 C7 118.48(8)
C10 C9 C14 119.20(9)
C10 C9 C8 123.18(9)
C14 C9 C8 117.58(9)
C11 C10 C9 119.96(10)
C11 C10 H10 118.9(9)
C9 C10 H10 121.1(9)
C12 C11 C10 120.35(10)
C12 C11 H11 120.2(9)
C10 C11 H11 119.5(9)
C11 C12 C13 119.85(10)
C11 C12 H12 119.8(9)
C13 C12 H12 120.4(9)
C14 C13 C12 120.11(10)
C14 C13 H13 119.9(9)
C12 C13 H13 119.9(9)
C13 C14 C9 120.51(10)
C13 C14 H14 121.5(8)
C9 C14 H14 118.0(8)
C20 C15 C16 118.45(9)
C20 C15 C6 123.19(9)
C16 C15 C6 118.26(9)
C17 C16 C15 120.89(10)
C17 C16 H16 120.0(8)
C15 C16 H16 119.1(8)
C18 C17 C16 120.09(10)
C18 C17 H17 119.8(8)
C16 C17 H17 120.0(8)
C19 C18 C17 119.53(10)
C19 C18 H18 119.6(9)
C17 C18 H18 120.9(9)
C18 C19 C20 120.27(10)
C18 C19 H19 119.3(8)
C20 C19 H19 120.4(8)
C15 C20 C19 120.74(10)
C15 C20 H20 120.1(8)
C19 C20 H20 119.1(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.4513(13)
C1 H1A 0.987(16)
C1 H1B 0.960(16)
C1 H1C 0.972(17)
O1 C2 1.3388(13)
C2 O2 1.2008(13)
C2 C3 1.5278(14)
C3 O3 1.4137(12)
C3 C7 1.5553(13)
C3 C4 1.5585(14)
O3 H3 0.841(17)
C4 O4 1.2071(12)
C4 C5 1.5125(14)
C5 C6 1.5333(14)
C5 H5A 0.975(14)
C5 H5B 0.971(14)
C6 C15 1.5136(13)
C6 C7 1.5545(13)
C6 H6 0.983(13)
C7 C8 1.5297(13)
C7 H7 0.980(12)
C8 O8 1.2186(12)
C8 C9 1.4984(13)
C9 C10 1.3979(14)
C9 C14 1.3993(14)
C10 C11 1.3963(14)
C10 H10 0.957(14)
C11 C12 1.3877(16)
C11 H11 0.963(15)
C12 C13 1.3917(16)
C12 H12 0.976(15)
C13 C14 1.3872(15)
C13 H13 0.959(15)
C14 H14 0.947(14)
C15 C20 1.3939(14)
C15 C16 1.4006(14)
C16 C17 1.3935(14)
C16 H16 0.964(14)
C17 C18 1.3934(15)
C17 H17 0.961(14)
C18 C19 1.3883(15)
C18 H18 0.968(14)
C19 C20 1.3989(14)
C19 H19 0.961(14)
C20 H20 0.967(14)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O4 0.841(17) 2.153(17) 2.9556(11) 159.6(15) 2
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
C1 O1 C2 O2 5.91(14)
C1 O1 C2 C3 -173.02(8)
O2 C2 C3 O3 7.84(14)
O1 C2 C3 O3 -173.22(8)
O2 C2 C3 C7 -112.10(11)
O1 C2 C3 C7 66.84(11)
O2 C2 C3 C4 128.27(11)
O1 C2 C3 C4 -52.79(10)
O3 C3 C4 O4 73.12(12)
C2 C3 C4 O4 -49.68(13)
C7 C3 C4 O4 -175.29(9)
O3 C3 C4 C5 -101.23(9)
C2 C3 C4 C5 135.97(9)
C7 C3 C4 C5 10.36(10)
O4 C4 C5 C6 -158.43(10)
C3 C4 C5 C6 15.47(10)
C4 C5 C6 C15 -165.58(8)
C4 C5 C6 C7 -35.70(9)
C15 C6 C7 C8 50.77(11)
C5 C6 C7 C8 -80.87(9)
C15 C6 C7 C3 173.69(8)
C5 C6 C7 C3 42.05(9)
O3 C3 C7 C8 -157.55(8)
C2 C3 C7 C8 -34.72(12)
C4 C3 C7 C8 90.12(9)
O3 C3 C7 C6 80.91(9)
C2 C3 C7 C6 -156.26(8)
C4 C3 C7 C6 -31.42(9)
C6 C7 C8 O8 22.42(12)
C3 C7 C8 O8 -93.01(11)
C6 C7 C8 C9 -156.88(8)
C3 C7 C8 C9 87.70(10)
O8 C8 C9 C10 176.91(9)
C7 C8 C9 C10 -3.79(14)
O8 C8 C9 C14 -1.04(14)
C7 C8 C9 C14 178.26(8)
C14 C9 C10 C11 1.25(15)
C8 C9 C10 C11 -176.67(9)
C9 C10 C11 C12 -1.10(16)
C10 C11 C12 C13 0.41(17)
C11 C12 C13 C14 0.11(17)
C12 C13 C14 C9 0.06(16)
C10 C9 C14 C13 -0.74(15)
C8 C9 C14 C13 177.30(9)
C5 C6 C15 C20 -5.18(14)
C7 C6 C15 C20 -129.90(10)
C5 C6 C15 C16 178.60(9)
C7 C6 C15 C16 53.88(12)
C20 C15 C16 C17 -0.50(15)
C6 C15 C16 C17 175.90(9)
C15 C16 C17 C18 -1.24(16)
C16 C17 C18 C19 1.90(16)
C17 C18 C19 C20 -0.82(16)
C16 C15 C20 C19 1.59(15)
C6 C15 C20 C19 -174.63(9)
C18 C19 C20 C15 -0.94(16)
