#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/32/1503208.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_1503208
loop_
_publ_author_name
'Ramadhar, Timothy R.'
'Kawakami, Jun-ichi'
'Lough, Alan J.'
'Batey, Robert A.'
_publ_section_title
;
 Stereocontrolled synthesis of contiguous C(sp3)-C(aryl) bonds by
 lanthanide(III)-catalyzed domino aryl-Claisen [3,3]-sigmatropic
 rearrangements.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4446
_journal_page_last               4449
_journal_paper_doi               10.1021/ol1018147
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C18 H20 O2'
_chemical_formula_sum            'C18 H20 O2'
_chemical_formula_weight         268.34
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   9.9559(3)
_cell_length_b                   13.4641(3)
_cell_length_c                   21.4149(6)
_cell_measurement_reflns_used    23275
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.7
_cell_volume                     2870.61(13)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0741
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            23275
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.72
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3288
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0560
_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)+(0.0864P)²+0.2835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1615
_reflns_number_gt                2001
_reflns_number_total             3288
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol1018147_si_002.cif
_cod_data_source_block           k08289
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               1503208
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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
O1 O 0.57770(15) 0.15243(10) 0.08888(7) 0.0398(4) Uani 1 1 d .
H1O H 0.652(3) 0.1310(19) 0.0754(13) 0.080(10) Uiso 1 1 d .
C1 C 0.34065(17) 0.23131(12) 0.14039(9) 0.0261(4) Uani 1 1 d .
H1A H 0.3490 0.1852 0.1040 0.031 Uiso 1 1 calc R
O2 O 0.06817(13) 0.47180(10) 0.10980(7) 0.0352(4) Uani 1 1 d .
H2O H 0.025(3) 0.5322(19) 0.1006(11) 0.065(8) Uiso 1 1 d .
C2 C 0.3062(2) 0.16748(13) 0.19823(9) 0.0310(5) Uani 1 1 d .
H2A H 0.3803 0.1200 0.2059 0.037 Uiso 1 1 calc R
H2B H 0.2989 0.2112 0.2352 0.037 Uiso 1 1 calc R
C3 C 0.17577(19) 0.11024(14) 0.19031(10) 0.0340(5) Uani 1 1 d .
H3A H 0.1872 0.0595 0.1573 0.041 Uiso 1 1 calc R
H3B H 0.1539 0.0755 0.2298 0.041 Uiso 1 1 calc R
C4 C 0.0608(2) 0.17885(14) 0.17288(10) 0.0346(5) Uani 1 1 d .
H4A H 0.0404 0.2232 0.2085 0.042 Uiso 1 1 calc R
H4B H -0.0204 0.1389 0.1639 0.042 Uiso 1 1 calc R
C5 C 0.09634(18) 0.24136(14) 0.11567(10) 0.0317(5) Uani 1 1 d .
H5A H 0.0208 0.2866 0.1060 0.038 Uiso 1 1 calc R
H5B H 0.1095 0.1971 0.0793 0.038 Uiso 1 1 calc R
C6 C 0.22452(18) 0.30287(13) 0.12622(9) 0.0268(4) Uani 1 1 d .
H6A H 0.2099 0.3446 0.1643 0.032 Uiso 1 1 calc R
C7 C 0.47693(18) 0.27945(13) 0.15009(9) 0.0276(4) Uani 1 1 d .
C8 C 0.59306(18) 0.23632(13) 0.12547(9) 0.0291(5) Uani 1 1 d .
C9 C 0.7193(2) 0.27656(14) 0.13621(10) 0.0341(5) Uani 1 1 d .
H9A H 0.7965 0.2461 0.1186 0.041 Uiso 1 1 calc R
C10 C 0.7329(2) 0.36083(14) 0.17251(10) 0.0369(5) Uani 1 1 d .
H10A H 0.8193 0.3883 0.1801 0.044 Uiso 1 1 calc R
C11 C 0.6198(2) 0.40490(14) 0.19774(10) 0.0369(5) Uani 1 1 d .
H11A H 0.6281 0.4630 0.2226 0.044 Uiso 1 1 calc R
C12 C 0.4938(2) 0.36404(14) 0.18661(9) 0.0326(5) Uani 1 1 d .
H12A H 0.4170 0.3948 0.2045 0.039 Uiso 1 1 calc R
C13 C 0.24739(18) 0.37262(12) 0.07175(8) 0.0263(4) Uani 1 1 d .
C14 C 0.16494(19) 0.45674(13) 0.06516(9) 0.0293(5) Uani 1 1 d .
C15 C 0.1820(2) 0.52222(13) 0.01548(10) 0.0323(5) Uani 1 1 d .
H15A H 0.1242 0.5779 0.0112 0.039 Uiso 1 1 calc R
C16 C 0.2830(2) 0.50627(14) -0.02764(10) 0.0365(5) Uani 1 1 d .
H16A H 0.2966 0.5524 -0.0606 0.044 Uiso 1 1 calc R
C17 C 0.3639(2) 0.42353(14) -0.02296(9) 0.0339(5) Uani 1 1 d .
H17A H 0.4319 0.4116 -0.0532 0.041 Uiso 1 1 calc R
C18 C 0.34552(19) 0.35745(13) 0.02639(9) 0.0298(5) Uani 1 1 d .
H18A H 0.4014 0.3005 0.0292 0.036 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
C7 C1 C6 115.60(14)
C7 C1 C2 109.01(15)
C6 C1 C2 109.90(15)
C3 C2 C1 112.44(16)
C4 C3 C2 111.30(15)
C3 C4 C5 110.97(16)
C4 C5 C6 111.77(16)
C13 C6 C1 115.35(15)
C13 C6 C5 110.21(15)
C1 C6 C5 108.42(14)
C12 C7 C8 116.88(17)
C12 C7 C1 122.30(17)
C8 C7 C1 120.70(16)
O1 C8 C9 120.86(17)
O1 C8 C7 117.50(16)
C9 C8 C7 121.63(18)
C10 C9 C8 120.21(19)
C9 C10 C11 119.45(19)
C10 C11 C12 119.87(18)
C11 C12 C7 121.96(19)
C18 C13 C14 117.24(17)
C18 C13 C6 123.48(16)
C14 C13 C6 119.27(16)
O2 C14 C15 121.64(16)
O2 C14 C13 117.32(16)
C15 C14 C13 121.03(17)
C16 C15 C14 120.08(18)
C17 C16 C15 120.15(19)
C16 C17 C18 119.61(19)
C13 C18 C17 121.85(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.383(2)
C1 C7 1.518(3)
C1 C6 1.535(2)
C1 C2 1.546(3)
O2 C14 1.372(2)
C2 C3 1.520(3)
C3 C4 1.518(3)
C4 C5 1.528(3)
C5 C6 1.538(3)
C6 C13 1.515(2)
C7 C12 1.392(3)
C7 C8 1.397(3)
C8 C9 1.387(3)
C9 C10 1.382(3)
C10 C11 1.383(3)
C11 C12 1.390(3)
C13 C18 1.393(3)
C13 C14 1.406(2)
C14 C15 1.392(3)
C15 C16 1.382(3)
C16 C17 1.379(3)
C17 C18 1.394(3)
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
O2 H2O O1 0.94(3) 1.93(3) 2.8679(19) 174(2) 7_665
O1 H1O Cg1 0.85(3) 2.54(3) 3.2516(17) 142(2) 3_555
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139037869
