#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:17:08 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180176 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/72/7107250.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_7107250
loop_
_publ_author_name
'Yong S. Chong'
'William G. Burns'
'Brent E. Dial'
'Ken D. Shimizu'
_publ_section_title
;
 Covalent locking and unlocking of an atropisomeric molecular switch
;
_journal_name_full               Chem.Commun.
_journal_page_first              1296
_journal_paper_doi               10.1039/c2cc16511b
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         'C36 H34 N2 O6'
_chemical_formula_sum            'C36 H34 N2 O6'
_chemical_formula_weight         590.65
_chemical_name_systematic
;
?
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                120.000(5)
_cell_formula_units_Z            9
_cell_length_a                   31.419(5)
_cell_length_b                   31.419(5)
_cell_length_c                   9.403(5)
_cell_measurement_reflns_used    2117
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.926
_cell_measurement_theta_min      2.246
_cell_volume                     8039(5)
_computing_cell_refinement       'SAINT-Plus Version 6.45 (Bruker, 2001)'
_computing_data_collection       'SMART Version 5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus Version 6.45 (Bruker, 2001)'
_computing_molecular_graphics    various
_computing_publication_material  'SHELXTL Version 6.14 (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_sigmaI/netI    0.0646
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11935
_diffrn_reflns_theta_full        22.54
_diffrn_reflns_theta_max         22.54
_diffrn_reflns_theta_min         1.30
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2808
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2353
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1249
_refine_ls_R_factor_gt           0.0707
_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)+(0.0909P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1779
_refine_ls_wR_factor_ref         0.1973
_reflns_number_gt                1259
_reflns_number_total             2353
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc16511b.txt
_cod_data_source_block           sqz2new
_cod_original_sg_symbol_H-M      R-3
_cod_database_code               7107250
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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 0.55458(17) 0.94778(16) 0.6216(5) 0.0672(12) Uani 1 1 d .
C2 C 0.54738(15) 0.98219(14) 0.5327(4) 0.0605(11) Uani 1 1 d .
C3 C 0.50366(14) 0.98370(13) 0.5427(4) 0.0552(10) Uani 1 1 d .
C4 C 0.46605(15) 0.95320(15) 0.6400(4) 0.0629(11) Uani 1 1 d .
C5 C 0.47248(18) 0.91845(16) 0.7285(5) 0.0732(13) Uani 1 1 d .
C6 C 0.58278(15) 1.01195(15) 0.4382(5) 0.0719(13) Uani 1 1 d .
H6 H 0.6116 1.0106 0.4312 0.086 Uiso 1 1 calc R
C7 C 0.57642(15) 1.04433(16) 0.3523(5) 0.0750(13) Uani 1 1 d .
H7 H 0.6011 1.0645 0.2890 0.090 Uiso 1 1 calc R
C8 C 0.52293(17) 0.88444(18) 0.8051(6) 0.0751(13) Uani 1 1 d .
C9 C 0.50574(19) 0.8377(2) 0.7579(6) 0.0853(14) Uani 1 1 d .
C10 C 0.5090(2) 0.80407(19) 0.8457(7) 0.1056(18) Uani 1 1 d .
H10 H 0.4960 0.7715 0.8181 0.127 Uiso 1 1 calc R
C11 C 0.5321(2) 0.8205(2) 0.9760(7) 0.1106(19) Uani 1 1 d .
H11 H 0.5348 0.7980 1.0341 0.133 Uiso 1 1 calc R
C12 C 0.5512(2) 0.8674(2) 1.0248(6) 0.0968(16) Uani 1 1 d .
C13 C 0.54552(18) 0.89913(18) 0.9353(5) 0.0864(15) Uani 1 1 d .
H13 H 0.5573 0.9314 0.9642 0.104 Uiso 1 1 calc R
C14 C 0.5753(3) 0.8827(3) 1.1724(6) 0.121(2) Uani 1 1 d .
C15 C 0.5376(3) 0.8643(4) 1.2803(8) 0.213(4) Uani 1 1 d .
H15A H 0.5216 0.8287 1.2796 0.256 Uiso 1 1 calc R
H15B H 0.5536 0.8753 1.3720 0.256 Uiso 1 1 calc R
C16 C 0.5011(3) 0.8773(4) 1.2710(8) 0.221(5) Uani 1 1 d .
H16A H 0.5097 0.9017 1.1983 0.332 Uiso 1 1 calc R
H16B H 0.4982 0.8903 1.3606 0.332 Uiso 1 1 calc R
H16C H 0.4703 0.8488 1.2476 0.332 Uiso 1 1 calc R
C17 C 0.6082(3) 0.8583(3) 1.2049(7) 0.166(3) Uani 1 1 d .
H17A H 0.6246 0.8701 1.2945 0.249 Uiso 1 1 calc R
H17B H 0.6322 0.8668 1.1309 0.249 Uiso 1 1 calc R
H17C H 0.5877 0.8232 1.2089 0.249 Uiso 1 1 calc R
C18 C 0.6093(3) 0.9386(3) 1.1848(7) 0.143(2) Uani 1 1 d .
H18A H 0.5905 0.9547 1.1699 0.214 Uiso 1 1 calc R
H18B H 0.6347 0.9495 1.1145 0.214 Uiso 1 1 calc R
H18C H 0.6237 0.9465 1.2779 0.214 Uiso 1 1 calc R
N1 N 0.51722(13) 0.91904(13) 0.7178(4) 0.0728(11) Uani 1 1 d .
O1 O 0.59086(11) 0.94415(11) 0.6160(3) 0.0880(11) Uani 1 1 d .
O2 O 0.44100(12) 0.88980(13) 0.8082(4) 0.1027(12) Uani 1 1 d .
O3 O 0.48367(17) 0.82559(15) 0.6272(5) 0.1260(14) Uani 1 1 d D
H3 H 0.475(2) 0.7951(11) 0.597(6) 0.16(3) Uiso 1 1 d 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'
N N 0.0061 0.0033 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 C1 N1 119.8(4) . .
O1 C1 C2 123.1(4) . .
N1 C1 C2 117.1(4) . .
C6 C2 C3 119.8(4) . .
C6 C2 C1 120.1(4) . .
C3 C2 C1 120.0(4) . .
C2 C3 C3 120.4(4) . 10_676
C2 C3 C4 121.2(3) . .
C3 C3 C4 118.3(4) 10_676 .
C7 C4 C3 119.9(4) 10_676 .
C7 C4 C5 120.7(4) 10_676 .
C3 C4 C5 119.4(4) . .
O2 C5 N1 119.8(4) . .
O2 C5 C4 122.7(4) . .
N1 C5 C4 117.5(4) . .
C2 C6 C7 120.9(4) . .
C2 C6 H6 119.5 . .
C7 C6 H6 119.5 . .
C4 C7 C6 120.6(4) 10_676 .
C4 C7 H7 119.7 10_676 .
C6 C7 H7 119.7 . .
C9 C8 C13 120.8(4) . .
C9 C8 N1 119.7(5) . .
C13 C8 N1 119.4(4) . .
C8 C9 O3 117.7(5) . .
C8 C9 C10 119.2(5) . .
O3 C9 C10 123.0(5) . .
C9 C10 C11 117.9(5) . .
C9 C10 H10 121.0 . .
C11 C10 H10 121.0 . .
C12 C11 C10 124.5(5) . .
C12 C11 H11 117.8 . .
C10 C11 H11 117.8 . .
C11 C12 C13 115.4(5) . .
C11 C12 C14 121.6(5) . .
C13 C12 C14 122.9(6) . .
C8 C13 C12 122.1(5) . .
C8 C13 H13 119.0 . .
C12 C13 H13 119.0 . .
C15 C14 C18 111.5(7) . .
C15 C14 C12 109.5(6) . .
C18 C14 C12 112.2(5) . .
C15 C14 C17 105.8(6) . .
C18 C14 C17 106.7(6) . .
C12 C14 C17 110.9(5) . .
C16 C15 C14 117.9(8) . .
C16 C15 H15A 107.8 . .
C14 C15 H15A 107.8 . .
C16 C15 H15B 107.8 . .
C14 C15 H15B 107.8 . .
H15A C15 H15B 107.2 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C14 C17 H17A 109.5 . .
C14 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C14 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C14 C18 H18A 109.5 . .
C14 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C14 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C1 N1 C5 124.6(4) . .
C1 N1 C8 118.3(3) . .
C5 N1 C8 116.8(4) . .
C9 O3 H3 115(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.202(4) .
C1 N1 1.397(5) .
C1 C2 1.471(5) .
C2 C6 1.364(5) .
C2 C3 1.401(5) .
C3 C3 1.407(7) 10_676
C3 C4 1.422(5) .
C4 C7 1.377(5) 10_676
C4 C5 1.465(6) .
C5 O2 1.208(4) .
C5 N1 1.400(5) .
C6 C7 1.390(5) .
C6 H6 0.9300 .
C7 C4 1.377(5) 10_676
C7 H7 0.9300 .
C8 C9 1.362(6) .
C8 C13 1.374(6) .
C8 N1 1.443(5) .
C9 O3 1.368(6) .
C9 C10 1.383(6) .
C10 C11 1.387(7) .
C10 H10 0.9300 .
C11 C12 1.362(7) .
C11 H11 0.9300 .
C12 C13 1.384(6) .
C12 C14 1.538(7) .
C13 H13 0.9300 .
C14 C15 1.442(9) .
C14 C18 1.537(8) .
C14 C17 1.597(8) .
C15 C16 1.399(10) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
O3 H3 0.90(2) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O1 C1 C2 C6 0.0(7) . .
N1 C1 C2 C6 178.9(4) . .
O1 C1 C2 C3 178.6(4) . .
N1 C1 C2 C3 -2.5(6) . .
C6 C2 C3 C3 -1.0(7) . 10_676
C1 C2 C3 C3 -179.6(4) . 10_676
C6 C2 C3 C4 -180.0(4) . .
C1 C2 C3 C4 1.4(6) . .
C2 C3 C4 C7 179.7(4) . 10_676
C3 C3 C4 C7 0.8(7) 10_676 10_676
C2 C3 C4 C5 -1.9(6) . .
C3 C3 C4 C5 179.1(4) 10_676 .
C7 C4 C5 O2 2.1(7) 10_676 .
C3 C4 C5 O2 -176.2(4) . .
C7 C4 C5 N1 -178.2(4) 10_676 .
C3 C4 C5 N1 3.4(6) . .
C3 C2 C6 C7 0.7(6) . .
C1 C2 C6 C7 179.3(4) . .
C2 C6 C7 C4 -0.5(7) . 10_676
C13 C8 C9 O3 -180.0(5) . .
N1 C8 C9 O3 0.3(7) . .
C13 C8 C9 C10 3.2(7) . .
N1 C8 C9 C10 -176.5(4) . .
C8 C9 C10 C11 -3.3(8) . .
O3 C9 C10 C11 -179.9(5) . .
C9 C10 C11 C12 1.1(9) . .
C10 C11 C12 C13 1.1(9) . .
C10 C11 C12 C14 178.4(6) . .
C9 C8 C13 C12 -0.9(7) . .
N1 C8 C13 C12 178.8(4) . .
C11 C12 C13 C8 -1.2(7) . .
C14 C12 C13 C8 -178.5(5) . .
C11 C12 C14 C15 -75.5(8) . .
C13 C12 C14 C15 101.6(8) . .
C11 C12 C14 C18 160.1(6) . .
C13 C12 C14 C18 -22.8(8) . .
C11 C12 C14 C17 40.8(8) . .
C13 C12 C14 C17 -142.0(6) . .
C18 C14 C15 C16 68.8(10) . .
C12 C14 C15 C16 -56.0(11) . .
C17 C14 C15 C16 -175.5(8) . .
O1 C1 N1 C5 -176.6(4) . .
C2 C1 N1 C5 4.4(6) . .
O1 C1 N1 C8 -1.9(6) . .
C2 C1 N1 C8 179.1(4) . .
O2 C5 N1 C1 174.8(4) . .
C4 C5 N1 C1 -4.9(6) . .
O2 C5 N1 C8 0.0(6) . .
C4 C5 N1 C8 -179.7(4) . .
C9 C8 N1 C1 -90.2(5) . .
C13 C8 N1 C1 90.0(5) . .
C9 C8 N1 C5 84.9(5) . .
C13 C8 N1 C5 -94.8(5) . .
