#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/63/1506303.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_1506303
loop_
_publ_author_name
'Dahl, Bart J.'
'Branchaud, Bruce P.'
_publ_section_title
;
 180 degree unidirectional bond rotation in a biaryl lactone artificial
 molecular motor prototype.
;
_journal_issue                   25
_journal_name_full               'Organic letters'
_journal_page_first              5841
_journal_page_last               5844
_journal_paper_doi               10.1021/ol062428u
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C19 H16 O5'
_chemical_formula_weight         324.32
_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                 94.738(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.764(2)
_cell_length_b                   21.989(6)
_cell_length_c                   8.721(2)
_cell_measurement_reflns_used    2234
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.34
_cell_measurement_theta_min      2.52
_cell_volume                     1483.8(7)
_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 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9363
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3177
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0447
_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)+(0.0532P)²+0.3571P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1134
_reflns_number_gt                2550
_reflns_number_total             3177
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol062428usi20061029_091427.cif
_cod_data_source_block           bran6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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)/c
_cod_database_code               1506303
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
_atom_site_refinement_flags
O1 O 0.81641(13) 0.86543(5) 0.72493(14) 0.0296(3) Uani 1 1 d .
O2 O 0.89384(16) 0.90551(6) 0.94935(15) 0.0416(3) Uani 1 1 d .
O3 O 0.19264(19) 0.95820(6) 0.51531(16) 0.0410(3) Uani 1 1 d .
O4 O 0.08505(19) 1.02656(7) 0.67062(18) 0.0476(4) Uani 1 1 d .
O5 O 0.28757(15) 0.69752(5) 0.67014(15) 0.0346(3) Uani 1 1 d .
C1 C 0.7936(2) 0.90644(8) 0.8361(2) 0.0278(4) Uani 1 1 d .
C2 C 0.6545(2) 0.95390(7) 0.81182(18) 0.0252(4) Uani 1 1 d .
C3 C 0.7017(2) 1.01136(8) 0.8719(2) 0.0291(4) Uani 1 1 d .
C4 C 0.5840(2) 1.05844(8) 0.8655(2) 0.0310(4) Uani 1 1 d .
C5 C 0.4208(2) 1.04958(8) 0.7938(2) 0.0301(4) Uani 1 1 d .
C6 C 0.3723(2) 0.99345(7) 0.73048(19) 0.0261(4) Uani 1 1 d .
C7 C 0.48590(19) 0.94313(7) 0.74540(18) 0.0234(3) Uani 1 1 d .
C8 C 0.42315(19) 0.88004(7) 0.71381(18) 0.0227(3) Uani 1 1 d .
C9 C 0.26959(19) 0.86014(7) 0.76864(19) 0.0250(4) Uani 1 1 d .
C10 C 0.2195(2) 0.79990(8) 0.75343(19) 0.0263(4) Uani 1 1 d .
C11 C 0.3230(2) 0.75844(7) 0.68342(18) 0.0247(3) Uani 1 1 d .
C12 C 0.47723(18) 0.77722(7) 0.62328(17) 0.0217(3) Uani 1 1 d .
C13 C 0.5890(2) 0.73135(8) 0.5481(2) 0.0264(4) Uani 1 1 d .
C14 C 0.7737(2) 0.75362(8) 0.5385(2) 0.0317(4) Uani 1 1 d .
C15 C 0.7753(2) 0.81832(9) 0.4793(2) 0.0344(4) Uani 1 1 d .
C16 C 0.6934(2) 0.86100(8) 0.58897(19) 0.0259(4) Uani 1 1 d .
C17 C 0.52469(19) 0.83815(7) 0.63972(17) 0.0216(3) Uani 1 1 d .
C18 C 0.2038(2) 0.99154(7) 0.63565(19) 0.0288(4) Uani 1 1 d .
C19 C 0.1589(2) 0.67320(9) 0.7612(3) 0.0373(4) Uani 1 1 d .
H1 H 0.092(8) 0.963(2) 0.454(7) 0.061(15) Uiso 0.50 1 d P
H1A H -0.008(10) 1.033(4) 0.615(10) 0.11(3) Uiso 0.50 1 d P
H3 H 0.812(3) 1.0182(8) 0.917(2) 0.031(5) Uiso 1 1 d .
H4 H 0.614(2) 1.0979(9) 0.911(2) 0.038(5) Uiso 1 1 d .
H5 H 0.336(2) 1.0819(8) 0.783(2) 0.031(5) Uiso 1 1 d .
H9 H 0.197(2) 0.8887(8) 0.821(2) 0.031(5) Uiso 1 1 d .
H10 H 0.117(2) 0.7881(8) 0.7969(19) 0.025(4) Uiso 1 1 d .
H13A H 0.587(2) 0.6937(9) 0.605(2) 0.034(5) Uiso 1 1 d .
H13B H 0.535(2) 0.7222(8) 0.443(2) 0.026(4) Uiso 1 1 d .
H14A H 0.833(2) 0.7265(9) 0.474(2) 0.039(5) Uiso 1 1 d .
H14B H 0.836(2) 0.7521(8) 0.643(2) 0.028(5) Uiso 1 1 d .
H15A H 0.707(2) 0.8216(8) 0.378(2) 0.036(5) Uiso 1 1 d .
H15B H 0.884(3) 0.8324(9) 0.466(2) 0.046(6) Uiso 1 1 d .
H16 H 0.677(2) 0.9025(8) 0.5457(19) 0.023(4) Uiso 1 1 d .
H19A H 0.161(3) 0.6313(11) 0.749(3) 0.053(6) Uiso 1 1 d .
H19B H 0.187(3) 0.6836(11) 0.877(3) 0.066(7) Uiso 1 1 d .
H19C H 0.047(3) 0.6886(10) 0.729(3) 0.051(6) Uiso 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
C1 O1 C16 120.82(12)
C18 O3 H1 114(3)
C18 O4 H1A 125(5)
C11 O5 C19 117.58(13)
O2 C1 O1 117.62(15)
O2 C1 C2 122.33(15)
O1 C1 C2 119.91(15)
C3 C2 C7 120.65(15)
C3 C2 C1 114.17(15)
C7 C2 C1 125.03(15)
C4 C3 C2 120.57(17)
C4 C3 H3 118.9(11)
C2 C3 H3 120.5(11)
C3 C4 C5 119.55(17)
C3 C4 H4 121.1(12)
C5 C4 H4 119.4(12)
C4 C5 C6 120.88(16)
C4 C5 H5 122.0(11)
C6 C5 H5 117.1(11)
C5 C6 C7 120.77(16)
C5 C6 C18 116.21(14)
C7 C6 C18 122.79(15)
C2 C7 C6 117.26(15)
C2 C7 C8 120.81(14)
C6 C7 C8 121.34(14)
C9 C8 C17 118.77(14)
C9 C8 C7 120.41(13)
C17 C8 C7 120.60(13)
C10 C9 C8 120.68(14)
C10 C9 H9 119.3(10)
C8 C9 H9 120.0(10)
C9 C10 C11 120.13(14)
C9 C10 H10 117.6(10)
C11 C10 H10 122.2(10)
O5 C11 C10 123.99(14)
O5 C11 C12 115.22(13)
C10 C11 C12 120.77(15)
C17 C12 C11 117.99(13)
C17 C12 C13 121.90(13)
C11 C12 C13 120.08(14)
C12 C13 C14 112.66(14)
C12 C13 H13A 108.3(11)
C14 C13 H13A 111.1(11)
C12 C13 H13B 108.8(10)
C14 C13 H13B 109.7(9)
H13A C13 H13B 106.0(15)
C15 C14 C13 110.79(15)
C15 C14 H14A 111.5(11)
C13 C14 H14A 109.2(11)
C15 C14 H14B 109.1(10)
C13 C14 H14B 109.2(10)
H14A C14 H14B 107.1(15)
C14 C15 C16 110.55(14)
C14 C15 H15A 110.6(11)
C16 C15 H15A 107.1(11)
C14 C15 H15B 113.2(13)
C16 C15 H15B 107.9(13)
H15A C15 H15B 107.2(17)
O1 C16 C17 108.05(12)
O1 C16 C15 105.84(14)
C17 C16 C15 113.54(14)
O1 C16 H16 107.6(10)
C17 C16 H16 109.3(9)
C15 C16 H16 112.2(10)
C12 C17 C8 121.62(13)
C12 C17 C16 121.36(13)
C8 C17 C16 116.88(14)
O4 C18 O3 123.30(17)
O4 C18 C6 118.42(16)
O3 C18 C6 117.99(14)
O5 C19 H19A 106.7(13)
O5 C19 H19B 110.8(13)
H19A C19 H19B 109.1(19)
O5 C19 H19C 111.5(13)
H19A C19 H19C 110.0(19)
H19B C19 H19C 108.7(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.347(2)
O1 C16 1.463(2)
O2 C1 1.206(2)
O3 C18 1.277(2)
O3 H1 0.92(7)
O4 C18 1.258(2)
O4 H1A 0.85(9)
O5 C11 1.3705(19)
O5 C19 1.430(2)
C1 C2 1.504(2)
C2 C3 1.405(2)
C2 C7 1.407(2)
C3 C4 1.379(2)
C3 H3 0.93(2)
C4 C5 1.380(3)
C4 H4 0.974(19)
C5 C6 1.391(2)
C5 H5 0.968(18)
C6 C7 1.414(2)
C6 C18 1.489(2)
C7 C8 1.488(2)
C8 C9 1.391(2)
C8 C17 1.404(2)
C9 C10 1.384(2)
C9 H9 0.983(18)
C10 C11 1.390(2)
C10 H10 0.945(17)
C11 C12 1.408(2)
C12 C17 1.394(2)
C12 C13 1.515(2)
C13 C14 1.524(2)
C13 H13A 0.966(19)
C13 H13B 0.999(18)
C14 C15 1.514(3)
C14 H14A 0.96(2)
C14 H14B 0.994(19)
C15 C16 1.516(2)
C15 H15A 0.99(2)
C15 H15B 0.91(2)
C16 C17 1.504(2)
C16 H16 0.992(17)
C19 H19A 0.93(2)
C19 H19B 1.04(3)
C19 H19C 0.96(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
O3 H1 O4 0.92(7) 1.70(7) 2.610(2) 176(5) 3_576
O4 H1A O3 0.85(9) 1.77(9) 2.610(2) 174(8) 3_576
