#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/13/4101332.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_4101332
loop_
_publ_author_name
'Gerard, Baudouin'
'Sangji, Sheharbano'
'O'Leary, Daniel J'
'Porco, Jr, John A'
_publ_section_title
;
 Enantioselective photocycloaddition mediated by chiral Brønsted
 acids: asymmetric synthesis of the rocaglamides.
;
_journal_issue                   24
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7754
_journal_page_last               7755
_journal_paper_doi               10.1021/ja062621j
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C28 H28 O8'
_chemical_formula_weight         492.50
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.267(2)
_cell_angle_beta                 106.750(3)
_cell_angle_gamma                96.752(3)
_cell_formula_units_Z            2
_cell_length_a                   10.0768(14)
_cell_length_b                   10.4422(7)
_cell_length_c                   12.5172(8)
_cell_measurement_reflns_used    7724
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.23
_cell_measurement_theta_min      2.22
_cell_volume                     1157.17(19)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker APEX2'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_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  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25370
_diffrn_reflns_theta_full        26.58
_diffrn_reflns_theta_max         26.58
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9846
_exptl_absorpt_correction_T_min  0.9796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         4719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0547P)²+0.1094P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0991
_reflns_number_gt                3646
_reflns_number_total             4719
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja062621jsi20060414_123118.cif
_cod_data_source_block           porco61
_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               4101332
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
O1 O 0.20503(10) -0.19298(9) -0.30573(8) 0.0189(2) Uani 1 1 d .
O2 O 0.25946(11) 0.02227(10) -0.58261(9) 0.0286(2) Uani 1 1 d .
O3 O 0.07404(11) 0.22642(9) -0.27222(8) 0.0250(2) Uani 1 1 d .
O4 O -0.03017(10) -0.00306(10) -0.18992(9) 0.0219(2) Uani 1 1 d .
H4O H -0.090(2) -0.0399(19) -0.2605(18) 0.052(6) Uiso 1 1 d .
O5 O 0.34076(10) 0.15684(10) -0.05413(9) 0.0230(2) Uani 1 1 d .
H5O H 0.388(2) 0.100(2) -0.0824(17) 0.048(6) Uiso 1 1 d .
O6 O 0.46682(10) -0.00054(10) 0.13311(8) 0.0265(2) Uani 1 1 d .
O7 O 0.33278(10) 0.13887(10) 0.20053(8) 0.0271(2) Uani 1 1 d .
O8 O -0.37404(11) -0.59693(11) -0.41905(9) 0.0329(3) Uani 1 1 d .
C1 C 0.19839(14) -0.08929(13) -0.35062(11) 0.0181(3) Uani 1 1 d .
C2 C 0.24280(14) -0.09458(14) -0.44679(12) 0.0203(3) Uani 1 1 d .
H3 H 0.2829(16) -0.1671(15) -0.4824(13) 0.022(4) Uiso 1 1 d .
C3 C 0.22554(14) 0.01460(14) -0.48566(11) 0.0213(3) Uani 1 1 d .
C4 C 0.17080(15) 0.12463(14) -0.42966(12) 0.0224(3) Uani 1 1 d .
H4 H 0.1638(16) 0.1966(16) -0.4620(13) 0.028(4) Uiso 1 1 d .
C5 C 0.12934(14) 0.12543(13) -0.33300(11) 0.0203(3) Uani 1 1 d .
C6 C 0.14232(14) 0.01525(13) -0.29330(11) 0.0184(3) Uani 1 1 d .
C7 C 0.10802(14) -0.01296(13) -0.19342(11) 0.0178(3) Uani 1 1 d .
C8 C 0.20948(14) 0.08066(13) -0.06330(12) 0.0183(3) Uani 1 1 d .
H8 H 0.1617(14) 0.1505(14) -0.0302(12) 0.014(3) Uiso 1 1 d .
C9 C 0.22949(14) -0.02317(13) 0.00038(11) 0.0182(3) Uani 1 1 d .
H9 H 0.1447(15) -0.0398(14) 0.0197(12) 0.017(3) Uiso 1 1 d .
C10 C 0.24614(15) -0.15191(13) -0.09375(11) 0.0176(3) Uani 1 1 d .
H10 H 0.3326(16) -0.1254(14) -0.0998(13) 0.022(4) Uiso 1 1 d .
C11 C 0.13475(14) -0.16622(13) -0.21644(11) 0.0170(3) Uani 1 1 d .
C12 C -0.00088(14) -0.28079(13) -0.26789(11) 0.0175(3) Uani 1 1 d .
C13 C -0.05035(15) -0.37414(14) -0.38836(12) 0.0210(3) Uani 1 1 d .
H13 H 0.0030(15) -0.3704(14) -0.4396(13) 0.019(4) Uiso 1 1 d .
C14 C -0.17507(15) -0.47717(15) -0.43642(13) 0.0246(3) Uani 1 1 d .
H14 H -0.2090(17) -0.5404(16) -0.5209(15) 0.031(4) Uiso 1 1 d .
C15 C -0.25315(14) -0.49001(14) -0.36424(13) 0.0232(3) Uani 1 1 d .
C16 C -0.20753(15) -0.39735(14) -0.24503(12) 0.0216(3) Uani 1 1 d .
H16 H -0.2620(16) -0.3994(15) -0.1948(13) 0.026(4) Uiso 1 1 d .
C17 C -0.08310(14) -0.29422(14) -0.19907(12) 0.0203(3) Uani 1 1 d .
H17 H -0.0550(16) -0.2251(15) -0.1148(14) 0.026(4) Uiso 1 1 d .
C18 C 0.05258(17) 0.33690(14) -0.31417(13) 0.0280(3) Uani 1 1 d .
H18A H 0.1428 0.3821 -0.3152 0.042 Uiso 1 1 calc R
H18B H 0.0186 0.4056 -0.2601 0.042 Uiso 1 1 calc R
H18C H -0.0184 0.2987 -0.3960 0.042 Uiso 1 1 calc R
C19 C 0.30340(18) -0.09445(16) -0.64887(14) 0.0338(4) Uani 1 1 d .
H19A H 0.3917 -0.1038 -0.5963 0.051 Uiso 1 1 calc R
H19B H 0.3199 -0.0800 -0.7180 0.051 Uiso 1 1 calc R
H19C H 0.2287 -0.1796 -0.6778 0.051 Uiso 1 1 calc R
C20 C 0.35640(14) 0.03654(13) 0.11604(12) 0.0191(3) Uani 1 1 d .
C21 C 0.45061(16) 0.20997(15) 0.31338(12) 0.0296(3) Uani 1 1 d .
H21A H 0.4772 0.1431 0.3504 0.044 Uiso 1 1 calc R
H21B H 0.4223 0.2838 0.3681 0.044 Uiso 1 1 calc R
H21C H 0.5323 0.2512 0.2982 0.044 Uiso 1 1 calc R
C22 C 0.25073(14) -0.28073(13) -0.06403(12) 0.0200(3) Uani 1 1 d .
C23 C 0.33096(16) -0.37003(15) -0.10896(13) 0.0271(3) Uani 1 1 d .
H23 H 0.3885(17) -0.3439(16) -0.1579(14) 0.031(4) Uiso 1 1 d .
C24 C 0.34015(18) -0.48919(15) -0.08343(14) 0.0326(4) Uani 1 1 d .
H24 H 0.3986(19) -0.5536(18) -0.1181(16) 0.044(5) Uiso 1 1 d .
C25 C 0.26914(18) -0.52035(16) -0.01328(14) 0.0352(4) Uani 1 1 d .
H25 H 0.2683(19) -0.604(2) 0.0008(16) 0.052(5) Uiso 1 1 d .
C26 C 0.19110(18) -0.43184(16) 0.03362(14) 0.0331(4) Uani 1 1 d .
H26 H 0.1384(18) -0.4528(17) 0.0768(15) 0.036(5) Uiso 1 1 d .
C27 C 0.18217(16) -0.31192(16) 0.00936(13) 0.0270(3) Uani 1 1 d .
H27 H 0.1295(17) -0.2493(16) 0.0449(14) 0.032(4) Uiso 1 1 d .
C28 C -0.46393(17) -0.60749(17) -0.35169(16) 0.0396(4) Uani 1 1 d .
H28A H -0.4102 -0.6208 -0.2789 0.059 Uiso 1 1 calc R
H28B H -0.5457 -0.6872 -0.4012 0.059 Uiso 1 1 calc R
H28C H -0.4978 -0.5217 -0.3286 0.059 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'
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
C1 O1 C11 108.22(9)
C3 O2 C19 116.45(11)
C5 O3 C18 117.40(10)
C20 O7 C21 116.31(11)
C15 O8 C28 117.91(11)
C6 C1 O1 113.91(11)
C6 C1 C2 124.51(12)
O1 C1 C2 121.57(11)
C1 C2 C3 115.51(12)
O2 C3 C2 122.77(12)
O2 C3 C4 114.85(11)
C2 C3 C4 122.38(12)
C5 C4 C3 119.70(12)
O3 C5 C4 124.76(12)
O3 C5 C6 115.88(11)
C4 C5 C6 119.35(12)
C1 C6 C5 118.53(12)
C1 C6 C7 109.62(11)
C5 C6 C7 131.84(12)
O4 C7 C6 115.93(11)
O4 C7 C8 103.98(10)
C6 C7 C8 116.03(11)
O4 C7 C11 113.46(10)
C6 C7 C11 101.30(10)
C8 C7 C11 106.03(10)
O5 C8 C9 112.44(11)
O5 C8 C7 115.65(10)
C9 C8 C7 103.22(10)
C20 C9 C10 112.71(11)
C20 C9 C8 111.71(11)
C10 C9 C8 103.89(10)
C22 C10 C9 117.01(11)
C22 C10 C11 118.25(11)
C9 C10 C11 104.51(10)
O1 C11 C12 107.55(10)
O1 C11 C10 107.68(10)
C12 C11 C10 116.64(10)
O1 C11 C7 105.69(9)
C12 C11 C7 114.15(10)
C10 C11 C7 104.47(10)
C17 C12 C13 117.12(12)
C17 C12 C11 121.60(11)
C13 C12 C11 121.24(11)
C14 C13 C12 121.57(13)
C13 C14 C15 119.87(13)
O8 C15 C14 115.81(12)
O8 C15 C16 124.54(13)
C14 C15 C16 119.65(13)
C17 C16 C15 119.52(13)
C12 C17 C16 122.24(12)
O6 C20 O7 122.71(12)
O6 C20 C9 125.93(12)
O7 C20 C9 111.36(11)
C23 C22 C27 118.39(13)
C23 C22 C10 118.45(12)
C27 C22 C10 123.13(12)
C22 C23 C24 120.89(15)
C25 C24 C23 120.04(15)
C24 C25 C26 119.83(14)
C25 C26 C27 120.53(15)
C26 C27 C22 120.28(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3746(15)
O1 C11 1.4579(15)
O2 C3 1.3757(16)
O2 C19 1.4286(18)
O3 C5 1.3618(16)
O3 C18 1.4304(16)
O4 C7 1.4205(15)
O5 C8 1.4144(16)
O6 C20 1.2053(16)
O7 C20 1.3327(16)
O7 C21 1.4457(16)
O8 C15 1.3763(17)
O8 C28 1.4219(19)
C1 C6 1.3739(18)
C1 C2 1.3873(18)
C2 C3 1.3894(19)
C3 C4 1.399(2)
C4 C5 1.3871(19)
C5 C6 1.4010(18)
C6 C7 1.4959(17)
C7 C8 1.5518(18)
C7 C11 1.5995(18)
C8 C9 1.5430(18)
C9 C20 1.5066(18)
C9 C10 1.5315(18)
C10 C22 1.5116(18)
C10 C11 1.5672(18)
C11 C12 1.5210(18)
C12 C17 1.3827(18)
C12 C13 1.3983(18)
C13 C14 1.385(2)
C14 C15 1.385(2)
C15 C16 1.386(2)
C16 C17 1.3859(19)
C22 C23 1.390(2)
C22 C27 1.392(2)
C23 C24 1.390(2)
C24 C25 1.373(2)
C25 C26 1.377(2)
C26 C27 1.389(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3989
