#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:03:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178800 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/54/4105448.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_4105448
loop_
_publ_author_name
'Lutz F. Tietze'
'Alexander Düfert'
'Florian Lotz'
'Lars Sölter'
'Kawon Oum'
'Thomas Lenzer'
'Tobias Beck'
'Regine Herbst-Irmer'
_publ_contact_author_address
;Institut für Organische und Biomolekulare Chemie
der Georg-August-Universität Göttingen
Tammannstr. 2, 37077 Göttingen, Germany
;
_publ_contact_author_email       ltietze@gwdg.de
_publ_contact_author_fax         +49-551-399476
_publ_contact_author_name        'Tietze, Lutz F.'
_publ_contact_author_phone       +49-551-393271
_publ_section_title
;
 Synthesis of Chiroptical Molecular Switches by Pd-Catalyzed Domino
 Reactions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17879
_journal_page_last               17884
_journal_paper_doi               10.1021/ja906260x
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C26 H18 O3'
_chemical_formula_sum            'C26 H18 O3'
_chemical_formula_weight         378.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 106.62(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   34.633(5)
_cell_length_b                   6.646(2)
_cell_length_c                   16.353(4)
_cell_measurement_reflns_used    5677
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.071
_cell_measurement_theta_min      2.663
_cell_volume                     3606.7(16)
_computing_cell_refinement       'APEX2 (v 2.2 RC 7, Bruker AXS 2007)'
_computing_data_collection       'APEX2 (v 2.2 RC 7, Bruker AXS 2007)'
_computing_data_reduction        'SAINT (v 7.40A, Bruker AXS, 2007)'
_computing_molecular_graphics    'SHELXTL (Bruker AXS, 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.602
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker three circle diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'multi-layer Incoatec optics'
_diffrn_radiation_source         'Macscience rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14103
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_min         2.66
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.723
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_correction_T_min  0.9182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker AXS 2007)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       plate
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0344
_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)+(0.0393P)²+2.3612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0894
_reflns_number_gt                2454
_reflns_number_total             3195
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja906260x_si_001_2.cif
_cod_data_source_block           switch
_cod_original_cell_volume        3606.7(15)
_cod_database_code               4105448
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_refinement_flags
C1 C 0.08706(5) 0.6984(2) 0.64796(9) 0.0219(3) Uani 1 1 d .
C2 C 0.04191(5) 0.7209(2) 0.61348(9) 0.0251(4) Uani 1 1 d .
H2B H 0.0322 0.8283 0.6455 0.030 Uiso 1 1 calc R
O2 O 0.03289(4) 0.77405(17) 0.52509(7) 0.0277(3) Uani 1 1 d .
H2A H 0.0059(8) 0.762(3) 0.5013(15) 0.049(6) Uiso 1 1 d .
C3 C 0.02388(5) 0.5194(2) 0.62629(10) 0.0281(4) Uani 1 1 d .
H3A H 0.0283 0.4971 0.6882 0.034 Uiso 1 1 calc R
H3B H -0.0056 0.5239 0.5990 0.034 Uiso 1 1 calc R
O4 O 0.04059(4) 0.35201(16) 0.59156(7) 0.0284(3) Uani 1 1 d .
C5 C 0.08721(5) 0.2155(2) 0.52750(10) 0.0268(4) Uani 1 1 d .
H5A H 0.0705 0.0997 0.5143 0.032 Uiso 1 1 calc R
C6 C 0.12133(5) 0.2266(2) 0.50254(10) 0.0270(4) Uani 1 1 d .
H6A H 0.1287 0.1160 0.4734 0.032 Uiso 1 1 calc R
C7 C 0.18050(5) 0.4193(2) 0.48887(9) 0.0270(4) Uani 1 1 d .
H7A H 0.1885 0.3086 0.4607 0.032 Uiso 1 1 calc R
C8 C 0.20225(5) 0.5936(2) 0.49951(10) 0.0275(4) Uani 1 1 d .
H8A H 0.2252 0.6037 0.4791 0.033 Uiso 1 1 calc R
C9 C 0.19043(5) 0.7586(2) 0.54102(9) 0.0261(4) Uani 1 1 d .
H9A H 0.2051 0.8813 0.5468 0.031 Uiso 1 1 calc R
C10 C 0.15822(5) 0.7441(2) 0.57301(9) 0.0229(3) Uani 1 1 d .
H10A H 0.1510 0.8565 0.6014 0.027 Uiso 1 1 calc R
C10B C 0.10104(5) 0.5449(2) 0.59680(9) 0.0225(3) Uani 1 1 d .
C10A C 0.13530(5) 0.5641(2) 0.56474(9) 0.0217(3) Uani 1 1 d .
C1' C 0.05854(5) 0.9383(2) 0.79144(9) 0.0249(3) Uani 1 1 d .
H1'A H 0.0412 0.8256 0.7751 0.030 Uiso 1 1 calc R
C2' C 0.04738(5) 1.0945(2) 0.83631(10) 0.0280(4) Uani 1 1 d .
H2'A H 0.0225 1.0889 0.8497 0.034 Uiso 1 1 calc R
C3' C 0.07276(5) 1.2591(2) 0.86152(10) 0.0273(4) Uani 1 1 d .
H3'A H 0.0648 1.3681 0.8906 0.033 Uiso 1 1 calc R
C4' C 0.10954(5) 1.2645(2) 0.84447(9) 0.0253(4) Uani 1 1 d .
H4'A H 0.1271 1.3759 0.8622 0.030 Uiso 1 1 calc R
C4A C 0.07676(5) 0.3768(2) 0.57315(9) 0.0245(3) Uani 1 1 d .
C4A' C 0.12049(5) 1.1053(2) 0.80111(9) 0.0227(3) Uani 1 1 d .
C4C' C 0.17708(5) 0.9244(2) 0.79145(9) 0.0217(3) Uani 1 1 d .
O4B' O 0.15899(3) 1.11095(15) 0.79182(7) 0.0244(3) Uani 1 1 d .
C5' C 0.21850(5) 0.9147(2) 0.82471(9) 0.0252(4) Uani 1 1 d .
H5'A H 0.2337 1.0324 0.8458 0.030 Uiso 1 1 calc R
C6' C 0.23757(5) 0.7302(2) 0.82682(10) 0.0272(4) Uani 1 1 d .
H6'A H 0.2660 0.7209 0.8490 0.033 Uiso 1 1 calc R
C6A C 0.14626(5) 0.4011(2) 0.51917(9) 0.0235(3) Uani 1 1 d .
C7' C 0.21494(5) 0.5592(2) 0.79643(9) 0.0268(4) Uani 1 1 d .
H7'A H 0.2280 0.4325 0.7994 0.032 Uiso 1 1 calc R
C8' C 0.17365(5) 0.5719(2) 0.76190(9) 0.0235(3) Uani 1 1 d .
H8'A H 0.1586 0.4538 0.7409 0.028 Uiso 1 1 calc R
C8A' C 0.15357(5) 0.7568(2) 0.75742(9) 0.0212(3) Uani 1 1 d .
C9' C 0.10974(5) 0.7888(2) 0.72035(9) 0.0213(3) Uani 1 1 d .
C9A' C 0.09467(5) 0.9429(2) 0.76973(9) 0.0216(3) 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
C9' C1 C10B 126.42(15)
C9' C1 C2 124.07(14)
C10B C1 C2 109.09(13)
O2 C2 C1 107.72(13)
O2 C2 C3 112.17(13)
C1 C2 C3 106.53(13)
O2 C2 H2B 110.1
C1 C2 H2B 110.1
C3 C2 H2B 110.1
C2 O2 H2A 108.1(14)
O4 C3 C2 113.50(13)
O4 C3 H3A 108.9
C2 C3 H3A 108.9
O4 C3 H3B 108.9
C2 C3 H3B 108.9
H3A C3 H3B 107.7
C4A O4 C3 119.02(12)
C6 C5 C4A 119.62(15)
C6 C5 H5A 120.2
C4A C5 H5A 120.2
C5 C6 C6A 121.27(14)
C5 C6 H6A 119.4
C6A C6 H6A 119.4
C8 C7 C6A 121.00(14)
C8 C7 H7A 119.5
C6A C7 H7A 119.5
C7 C8 C9 119.70(15)
C7 C8 H8A 120.2
C9 C8 H8A 120.2
C10 C9 C8 120.73(15)
C10 C9 H9A 119.6
C8 C9 H9A 119.6
C9 C10 C10A 121.28(14)
C9 C10 H10A 119.4
C10A C10 H10A 119.4
C4A C10B C10A 118.00(13)
C4A C10B C1 116.20(14)
C10A C10B C1 125.60(13)
C10 C10A C6A 117.67(14)
C10 C10A C10B 122.58(13)
C6A C10A C10B 119.69(14)
C2' C1' C9A' 121.57(15)
C2' C1' H1'A 119.2
C9A' C1' H1'A 119.2
C1' C2' C3' 119.81(16)
C1' C2' H2'A 120.1
C3' C2' H2'A 120.1
C4' C3' C2' 120.16(14)
C4' C3' H3'A 119.9
C2' C3' H3'A 119.9
C3' C4' C4A' 119.16(15)
C3' C4' H4'A 120.4
C4A' C4' H4'A 120.4
O4 C4A C10B 123.51(14)
O4 C4A C5 114.26(14)
C10B C4A C5 122.23(15)
O4B' C4A' C4' 116.63(14)
O4B' C4A' C9A' 120.95(13)
C4' C4A' C9A' 122.40(15)
C5' C4C' O4B' 117.25(13)
C5' C4C' C8A' 122.71(14)
O4B' C4C' C8A' 120.03(14)
C4A' O4B' C4C' 115.18(11)
C4C' C5' C6' 118.90(15)
C4C' C5' H5'A 120.6
C6' C5' H5'A 120.6
C5' C6' C7' 119.86(16)
C5' C6' H6'A 120.1
C7' C6' H6'A 120.1
C7 C6A C6 121.72(14)
C7 C6A C10A 119.51(14)
C6 C6A C10A 118.72(15)
C8' C7' C6' 120.56(15)
C8' C7' H7'A 119.7
C6' C7' H7'A 119.7
C7' C8' C8A' 120.95(15)
C7' C8' H8'A 119.5
C8A' C8' H8'A 119.5
C4C' C8A' C8' 116.95(15)
C4C' C8A' C9' 117.44(13)
C8' C8A' C9' 125.61(14)
C1 C9' C8A' 124.24(14)
C1 C9' C9A' 124.87(15)
C8A' C9' C9A' 110.77(13)
C1' C9A' C4A' 116.64(13)
C1' C9A' C9' 127.03(14)
C4A' C9A' C9' 116.26(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C9' 1.359(2)
C1 C10B 1.486(2)
C1 C2 1.510(2)
C2 O2 1.4331(18)
C2 C3 1.517(2)
C2 H2B 1.0000
O2 H2A 0.91(3)
C3 O4 1.4434(19)
C3 H3A 0.9900
C3 H3B 0.9900
O4 C4A 1.379(2)
C5 C6 1.358(2)
C5 C4A 1.412(2)
C5 H5A 0.9500
C6 C6A 1.425(2)
C6 H6A 0.9500
C7 C8 1.366(2)
C7 C6A 1.415(2)
C7 H7A 0.9500
C8 C9 1.411(2)
C8 H8A 0.9500
C9 C10 1.364(2)
C9 H9A 0.9500
C10 C10A 1.421(2)
C10 H10A 0.9500
C10B C4A 1.385(2)
C10B C10A 1.434(2)
C10A C6A 1.426(2)
C1' C2' 1.388(2)
C1' C9A' 1.395(2)
C1' H1'A 0.9500
C2' C3' 1.390(2)
C2' H2'A 0.9500
C3' C4' 1.380(2)
C3' H3'A 0.9500
C4' C4A' 1.385(2)
C4' H4'A 0.9500
C4A' O4B' 1.385(2)
C4A' C9A' 1.402(2)
C4C' C5' 1.382(2)
C4C' O4B' 1.3901(18)
C4C' C8A' 1.398(2)
C5' C6' 1.389(2)
C5' H5'A 0.9500
C6' C7' 1.389(2)
C6' H6'A 0.9500
C7' C8' 1.382(2)
C7' H7'A 0.9500
C8' C8A' 1.403(2)
C8' H8'A 0.9500
C8A' C9' 1.480(2)
C9' C9A' 1.488(2)
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 H2A O4 0.91(3) 2.02(3) 2.8356(19) 149(2) 5_566
