#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/66/1506625.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_1506625
loop_
_publ_author_name
'Andrus, Merritt B.'
'Liu, Jing'
'Ye, Zhifeng'
'Cannon, John F.'
_publ_section_title
;
 Asymmetric glycolate aldol reactions using cinchonium phase-transfer
 catalysts.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              3861
_journal_page_last               3864
_journal_paper_doi               10.1021/ol051096a
_journal_volume                  7
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H30 O6'
_chemical_formula_sum            'C32 H30 O6'
_chemical_formula_weight         510.56
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8004(3)
_cell_length_b                   12.0028(4)
_cell_length_c                   26.0589(8)
_cell_measurement_reflns_used    4667
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.20
_cell_measurement_theta_min      5.31
_cell_volume                     2752.59(16)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker Nonius Apex II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Montel 200 mirrors'
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            10657
_diffrn_reflns_theta_full        69.20
_diffrn_reflns_theta_max         69.20
_diffrn_reflns_theta_min         5.31
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  0.8982
_exptl_absorpt_correction_T_min  0.7806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), 1771 Friedel pairs'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.281
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.281
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0323
_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)+(0.0500P)²+0.1934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                3453
_reflns_number_total             4602
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol051096asi20050512_053955.cif
_cod_data_source_block           JL1R
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1506625
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
C1 C 0.3780(2) 0.55215(19) 0.12549(8) 0.0573(5) Uani 1 1 d .
H1 H 0.4457 0.4874 0.1272 0.069 Uiso 1 1 calc R
C2 C 0.4415(3) 0.64457(19) 0.15930(9) 0.0605(5) Uani 1 1 d .
C3 C 0.5888(2) 0.70071(19) 0.14635(8) 0.0591(5) Uani 1 1 d .
C4 C 0.6015(3) 0.8112(2) 0.16132(9) 0.0646(6) Uani 1 1 d .
H4 H 0.5197 0.8455 0.1775 0.077 Uiso 1 1 calc R
C5 C 0.7324(3) 0.8717(2) 0.15276(10) 0.0736(6) Uani 1 1 d .
C6 C 0.8527(3) 0.8203(3) 0.12958(12) 0.0865(8) Uani 1 1 d .
H6 H 0.9419 0.8600 0.1240 0.104 Uiso 1 1 calc R
C7 C 0.8441(3) 0.7107(3) 0.11439(11) 0.0823(8) Uani 1 1 d .
H7 H 0.9274 0.6772 0.0988 0.099 Uiso 1 1 calc R
C8 C 0.7127(3) 0.6499(2) 0.12213(9) 0.0666(6) Uani 1 1 d .
C9 C 0.8594(4) 1.0467(3) 0.15761(15) 0.1109(11) Uani 1 1 d .
H9A H 0.9465 1.0182 0.1755 0.166 Uiso 1 1 calc R
H9B H 0.8408 1.1221 0.1682 0.166 Uiso 1 1 calc R
H9C H 0.8781 1.0450 0.1213 0.166 Uiso 1 1 calc R
C10 C 0.8248(3) 0.4808(3) 0.09106(14) 0.1107(12) Uani 1 1 d .
H10A H 0.8540 0.5072 0.0577 0.166 Uiso 1 1 calc R
H10B H 0.8007 0.4029 0.0891 0.166 Uiso 1 1 calc R
H10C H 0.9071 0.4917 0.1147 0.166 Uiso 1 1 calc R
C11 C 0.2319(3) 0.44489(18) 0.18470(8) 0.0573(5) Uani 1 1 d .
H11 H 0.3028 0.4737 0.2105 0.069 Uiso 1 1 calc R
C12 C 0.0726(3) 0.44801(19) 0.20699(8) 0.0602(5) Uani 1 1 d .
C13 C 0.0011(3) 0.5497(2) 0.21337(9) 0.0682(6) Uani 1 1 d .
H13 H 0.0506 0.6147 0.2035 0.082 Uiso 1 1 calc R
C14 C -0.1437(3) 0.5559(2) 0.23438(11) 0.0782(7) Uani 1 1 d .
H14 H -0.1912 0.6246 0.2381 0.094 Uiso 1 1 calc R
C15 C -0.2161(3) 0.4605(3) 0.24957(12) 0.0920(9) Uani 1 1 d .
H15 H -0.3131 0.4644 0.2636 0.110 Uiso 1 1 calc R
C16 C -0.1459(4) 0.3598(3) 0.24415(14) 0.1025(10) Uani 1 1 d .
H16 H -0.1952 0.2951 0.2546 0.123 Uiso 1 1 calc R
C17 C -0.0014(3) 0.3535(2) 0.22302(11) 0.0848(8) Uani 1 1 d .
H17 H 0.0459 0.2846 0.2197 0.102 Uiso 1 1 calc R
C18 C 0.2848(3) 0.33124(19) 0.16832(9) 0.0612(6) Uani 1 1 d .
C19 C 0.4018(3) 0.2784(2) 0.19395(10) 0.0732(6) Uani 1 1 d .
H19 H 0.4484 0.3138 0.2215 0.088 Uiso 1 1 calc R
C20 C 0.4508(4) 0.1736(3) 0.17930(13) 0.0932(9) Uani 1 1 d .
H20 H 0.5299 0.1392 0.1969 0.112 Uiso 1 1 calc R
C21 C 0.3830(5) 0.1209(3) 0.13913(13) 0.0994(10) Uani 1 1 d .
H21 H 0.4157 0.0503 0.1294 0.119 Uiso 1 1 calc R
C22 C 0.2668(5) 0.1713(2) 0.11291(13) 0.1009(10) Uani 1 1 d .
H22 H 0.2205 0.1349 0.0856 0.121 Uiso 1 1 calc R
C23 C 0.2188(4) 0.2768(2) 0.12729(10) 0.0826(8) Uani 1 1 d .
H23 H 0.1411 0.3113 0.1091 0.099 Uiso 1 1 calc R
C24 C 0.3693(3) 0.59281(18) 0.07004(8) 0.0586(5) Uani 1 1 d .
H24 H 0.4714 0.6153 0.0592 0.070 Uiso 1 1 calc R
C25 C 0.3116(3) 0.5064(2) 0.03317(8) 0.0606(5) Uani 1 1 d .
C26 C 0.1720(3) 0.5147(3) 0.00955(10) 0.0813(7) Uani 1 1 d .
H26 H 0.1102 0.5759 0.0160 0.098 Uiso 1 1 calc R
C27 C 0.1236(4) 0.4325(3) -0.02355(13) 0.1048(10) Uani 1 1 d .
H27 H 0.0288 0.4388 -0.0390 0.126 Uiso 1 1 calc R
C28 C 0.2119(4) 0.3425(3) -0.03400(12) 0.1009(10) Uani 1 1 d .
H28 H 0.1774 0.2872 -0.0561 0.121 Uiso 1 1 calc R
C29 C 0.3507(4) 0.3340(3) -0.01186(12) 0.0987(10) Uani 1 1 d .
H29 H 0.4123 0.2730 -0.0190 0.118 Uiso 1 1 calc R
C30 C 0.4010(4) 0.4158(2) 0.02131(11) 0.0841(8) Uani 1 1 d .
H30 H 0.4970 0.4095 0.0359 0.101 Uiso 1 1 calc R
C31 C 0.3143(3) 0.7758(2) 0.04036(10) 0.0716(7) Uani 1 1 d .
C32 C 0.2074(4) 0.8716(2) 0.04612(13) 0.0969(9) Uani 1 1 d .
H32A H 0.2442 0.9339 0.0266 0.145 Uiso 1 1 calc R
H32B H 0.2005 0.8920 0.0817 0.145 Uiso 1 1 calc R
H32C H 0.1087 0.8505 0.0338 0.145 Uiso 1 1 calc R
O1 O 0.3702(2) 0.67595(15) 0.19662(7) 0.0842(5) Uani 1 1 d .
O2 O 0.7306(2) 0.98012(16) 0.16919(9) 0.0987(6) Uani 1 1 d .
O3 O 0.69595(19) 0.54046(16) 0.10823(8) 0.0847(5) Uani 1 1 d .
O4 O 0.23076(16) 0.52027(12) 0.14148(6) 0.0587(4) Uani 1 1 d .
O5 O 0.27341(18) 0.69067(12) 0.07070(6) 0.0652(4) Uani 1 1 d .
O6 O 0.4224(3) 0.77335(17) 0.01249(9) 0.1038(7) Uani 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 0.0181 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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O4 C1 C2 111.26(18)
O4 C1 C24 108.63(17)
C2 C1 C24 109.46(18)
O1 C2 C3 119.1(2)
O1 C2 C1 119.9(2)
C3 C2 C1 120.93(19)
C4 C3 C8 118.7(2)
C4 C3 C2 115.9(2)
C8 C3 C2 125.4(2)
C5 C4 C3 121.7(2)
C6 C5 O2 125.2(2)
C6 C5 C4 118.7(2)
O2 C5 C4 116.1(2)
C5 C6 C7 121.1(3)
C6 C7 C8 120.6(3)
O3 C8 C7 123.9(2)
O3 C8 C3 116.9(2)
C7 C8 C3 119.2(2)
O4 C11 C18 110.44(17)
O4 C11 C12 106.05(17)
C18 C11 C12 114.65(18)
C17 C12 C13 118.5(2)
C17 C12 C11 122.3(2)
C13 C12 C11 119.2(2)
C12 C13 C14 120.8(2)
C15 C14 C13 119.8(3)
C16 C15 C14 120.0(3)
C15 C16 C17 120.2(3)
C12 C17 C16 120.7(3)
C19 C18 C23 118.0(2)
C19 C18 C11 120.7(2)
C23 C18 C11 121.3(2)
C18 C19 C20 121.1(3)
C21 C20 C19 119.9(3)
C20 C21 C22 120.4(3)
C21 C22 C23 119.7(3)
C18 C23 C22 120.9(3)
O5 C24 C25 111.75(18)
O5 C24 C1 106.12(17)
C25 C24 C1 113.68(18)
C26 C25 C30 117.8(2)
C26 C25 C24 122.6(2)
C30 C25 C24 119.7(2)
C27 C26 C25 120.3(3)
C28 C27 C26 121.2(3)
C29 C28 C27 119.3(3)
C28 C29 C30 120.1(3)
C25 C30 C29 121.3(3)
O6 C31 O5 123.5(3)
O6 C31 C32 125.5(2)
O5 C31 C32 111.0(2)
C5 O2 C9 117.3(2)
C8 O3 C10 118.9(2)
C1 O4 C11 113.14(16)
C31 O5 C24 117.08(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O4 1.414(3)
C1 C2 1.523(3)
C1 C24 1.527(3)
C2 O1 1.217(3)
C2 C3 1.499(3)
C3 C4 1.387(3)
C3 C8 1.400(3)
C4 C5 1.380(3)
C5 C6 1.366(4)
C5 O2 1.370(3)
C6 C7 1.376(4)
C7 C8 1.382(4)
C8 O3 1.371(3)
C9 O2 1.420(4)
C10 O3 1.414(3)
C11 O4 1.444(3)
C11 C18 1.503(3)
C11 C12 1.518(3)
C12 C17 1.373(3)
C12 C13 1.383(3)
C13 C14 1.388(4)
C14 C15 1.368(4)
C15 C16 1.365(4)
C16 C17 1.388(4)
C18 C19 1.381(3)
C18 C23 1.382(4)
C19 C20 1.383(4)
C20 C21 1.361(5)
C21 C22 1.370(5)
C22 C23 1.386(4)
C24 O5 1.447(3)
C24 C25 1.502(3)
C25 C26 1.377(3)
C25 C30 1.378(4)
C26 C27 1.377(4)
C27 C28 1.359(5)
C28 C29 1.355(5)
C29 C30 1.380(4)
C31 O6 1.197(3)
C31 O5 1.342(3)
C31 C32 1.493(4)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21200015 ChemSpider
