#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:51:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178827 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/81/4108120.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_4108120
loop_
_publ_author_name
'Yu-Jun Zhao'
'Teck-Peng Loh'
_publ_section_title
;
 Bioinspired Polyene Cyclization Promoted by Intermolecular Chiral
 Acetal-SnCl4 or Chiral N-Acetal-TiCl4: Investigation of the Mechanism and
 Identification of the Key Intermediates
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10024
_journal_page_last               10029
_journal_paper_doi               10.1021/ja802896n
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C24 H28 O'
_chemical_formula_weight         332.46
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 109.175(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8466(4)
_cell_length_b                   14.5211(5)
_cell_length_c                   12.6067(4)
_cell_measurement_reflns_used    9043
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.38
_cell_measurement_theta_min      2.43
_cell_volume                     1875.45(11)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26346
_diffrn_reflns_theta_full        30.46
_diffrn_reflns_theta_max         30.46
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9862
_exptl_absorpt_correction_T_min  0.9828
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_meas      0
_exptl_crystal_description       fragment
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0459
_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)+(0.0763P)²+0.1977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1335
_reflns_number_gt                4470
_reflns_number_total             5678
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja802896n-file003.cif
_cod_data_source_block           ltp51
_cod_database_code               4108120
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.70184(9) -0.10334(6) 0.12569(8) 0.02609(19) Uani 1 1 d
C2 C 0.58552(10) -0.15217(7) 0.11144(9) 0.0332(2) Uani 1 1 d
H2 H 0.5269(14) -0.1349(10) 0.1573(11) 0.043(4) Uiso 1 1 d
C3 C 0.54592(11) -0.22419(8) 0.03551(10) 0.0382(2) Uani 1 1 d
H3 H 0.4627(15) -0.2566(10) 0.0291(13) 0.052(4) Uiso 1 1 d
C4 C 0.62294(12) -0.24954(8) -0.02856(10) 0.0397(3) Uani 1 1 d
H4 H 0.5944(15) -0.2999(11) -0.0823(13) 0.053(4) Uiso 1 1 d
C5 C 0.73943(11) -0.20377(8) -0.01400(9) 0.0358(2) Uani 1 1 d
H5 H 0.7997(13) -0.2219(9) -0.0558(11) 0.040(3) Uiso 1 1 d
C6 C 0.78096(9) -0.13071(7) 0.06275(8) 0.0277(2) Uani 1 1 d
C7 C 0.90873(10) -0.08290(8) 0.07372(9) 0.0323(2) Uani 1 1 d
H7A H 0.9754(14) -0.1304(10) 0.0780(11) 0.041(3) Uiso 1 1 d
H7B H 0.8981(13) -0.0466(9) 0.0023(11) 0.039(3) Uiso 1 1 d
C8 C 0.95571(9) -0.01862(8) 0.17503(9) 0.0321(2) Uani 1 1 d
H8A H 0.9970(14) -0.0536(9) 0.2484(11) 0.042(3) Uiso 1 1 d
H8B H 1.0270(15) 0.0219(11) 0.1674(12) 0.050(4) Uiso 1 1 d
C9 C 0.84118(8) 0.03894(7) 0.18405(7) 0.02343(18) Uani 1 1 d
H9 H 0.7918(11) 0.0620(7) 0.1062(9) 0.022(3) Uiso 1 1 d
C10 C 0.74139(9) -0.02521(6) 0.21274(7) 0.02458(18) Uani 1 1 d
C11 C 0.79484(13) -0.07285(8) 0.32893(9) 0.0370(2) Uani 1 1 d
H11A H 0.8111(15) -0.0283(11) 0.3930(13) 0.057(4) Uiso 1 1 d
H11B H 0.8784(16) -0.1086(11) 0.3382(12) 0.053(4) Uiso 1 1 d
H11C H 0.7272(18) -0.1176(12) 0.3340(14) 0.067(5) Uiso 1 1 d
C12 C 0.62009(10) 0.03247(7) 0.20697(10) 0.0325(2) Uani 1 1 d
H12A H 0.5723(13) 0.0494(9) 0.1265(11) 0.038(3) Uiso 1 1 d
H12B H 0.5575(14) -0.0065(10) 0.2347(12) 0.047(4) Uiso 1 1 d
C13 C 0.65295(10) 0.12028(7) 0.27702(9) 0.0326(2) Uani 1 1 d
H13A H 0.5651(14) 0.1554(10) 0.2664(11) 0.044(4) Uiso 1 1 d
H13B H 0.6922(14) 0.1061(10) 0.3598(12) 0.044(4) Uiso 1 1 d
C14 C 0.74981(9) 0.18102(6) 0.24324(7) 0.02564(19) Uani 1 1 d
H14 H 0.7091(12) 0.1957(8) 0.1622(10) 0.028(3) Uiso 1 1 d
C15 C 0.88027(9) 0.12956(7) 0.25462(7) 0.02615(19) Uani 1 1 d
C16 C 0.96609(11) 0.11374(9) 0.37815(9) 0.0376(2) Uani 1 1 d
H16A H 0.9150(14) 0.0921(9) 0.4298(11) 0.043(4) Uiso 1 1 d
H16B H 1.0358(16) 0.0668(11) 0.3826(13) 0.055(4) Uiso 1 1 d
H16C H 1.0101(14) 0.1716(10) 0.4125(12) 0.047(4) Uiso 1 1 d
C17 C 0.96044(11) 0.19060(8) 0.20065(9) 0.0358(2) Uani 1 1 d
H17A H 0.9166(14) 0.1986(10) 0.1175(12) 0.049(4) Uiso 1 1 d
H17B H 1.0504(16) 0.1633(11) 0.2137(13) 0.054(4) Uiso 1 1 d
H17C H 0.9717(14) 0.2542(10) 0.2348(12) 0.041(3) Uiso 1 1 d
C18 C 0.76541(10) 0.26972(7) 0.31097(8) 0.0297(2) Uani 1 1 d
C19 C 0.73559(9) 0.36167(6) 0.25352(7) 0.02529(19) Uani 1 1 d
C20 C 0.72481(10) 0.37616(7) 0.14098(8) 0.0303(2) Uani 1 1 d
H20 H 0.7411(12) 0.3265(9) 0.0951(10) 0.035(3) Uiso 1 1 d
C21 C 0.69550(12) 0.46358(8) 0.09407(9) 0.0375(2) Uani 1 1 d
H21 H 0.6870(15) 0.4736(10) 0.0139(12) 0.052(4) Uiso 1 1 d
C22 C 0.67778(11) 0.53706(8) 0.15806(10) 0.0379(2) Uani 1 1 d
H22 H 0.6583(15) 0.5999(11) 0.1247(12) 0.053(4) Uiso 1 1 d
C23 C 0.68874(10) 0.52323(8) 0.26950(10) 0.0344(2) Uani 1 1 d
H23 H 0.6760(14) 0.5736(10) 0.3145(12) 0.048(4) Uiso 1 1 d
C24 C 0.71742(9) 0.43634(7) 0.31696(8) 0.0295(2) Uani 1 1 d
H24 H 0.7229(14) 0.4261(9) 0.3933(12) 0.046(4) Uiso 1 1 d
O1 O 0.79411(10) 0.26638(6) 0.41330(6) 0.0479(2) 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 0.0033 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
C6 C1 C2 118.32(9)
C6 C1 C10 122.20(8)
C2 C1 C10 119.42(8)
C3 C2 C1 121.98(10)
C2 C3 C4 119.48(11)
C5 C4 C3 119.50(10)
C4 C5 C6 121.67(10)
C1 C6 C5 119.02(9)
C1 C6 C7 121.96(9)
C5 C6 C7 119.01(9)
C6 C7 C8 113.58(8)
C7 C8 C9 109.84(8)
C8 C9 C10 109.46(8)
C8 C9 C15 115.18(7)
C10 C9 C15 116.70(7)
C1 C10 C12 109.48(7)
C1 C10 C11 105.97(8)
C12 C10 C11 109.62(8)
C1 C10 C9 109.12(7)
C12 C10 C9 108.15(7)
C11 C10 C9 114.42(8)
C13 C12 C10 113.18(8)
C12 C13 C14 111.77(8)
C18 C14 C13 106.88(8)
C18 C14 C15 114.95(8)
C13 C14 C15 112.38(8)
C16 C15 C17 106.77(8)
C16 C15 C14 112.98(8)
C17 C15 C14 107.94(8)
C16 C15 C9 114.09(8)
C17 C15 C9 108.52(8)
C14 C15 C9 106.33(7)
O1 C18 C19 118.87(9)
O1 C18 C14 120.00(9)
C19 C18 C14 120.95(8)
C24 C19 C20 118.82(9)
C24 C19 C18 117.48(8)
C20 C19 C18 123.70(8)
C21 C20 C19 119.91(9)
C22 C21 C20 120.64(10)
C23 C22 C21 119.71(10)
C22 C23 C24 120.12(10)
C23 C24 C19 120.80(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.4041(13)
C1 C2 1.4064(13)
C1 C10 1.5383(13)
C2 C3 1.3872(16)
C3 C4 1.3889(18)
C4 C5 1.3855(17)
C5 C6 1.4066(15)
C6 C7 1.5151(14)
C7 C8 1.5281(15)
C8 C9 1.5321(13)
C9 C10 1.5580(12)
C9 C15 1.5669(13)
C10 C12 1.5410(13)
C10 C11 1.5500(13)
C12 C13 1.5251(14)
C13 C14 1.5353(13)
C14 C18 1.5236(13)
C14 C15 1.5646(13)
C15 C16 1.5466(13)
C15 C17 1.5470(13)
C18 O1 1.2246(12)
C18 C19 1.5028(14)
C19 C24 1.3991(13)
C19 C20 1.4006(13)
C20 C21 1.3923(15)
C21 C22 1.3887(16)
C22 C23 1.3851(16)
C23 C24 1.3873(16)
