#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:32:15 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178786 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/40/4104090.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_4104090
loop_
_publ_author_name
'Andrea Lucotti'
'Matteo Tommasini'
'Daniele Fazzi'
'Mirella Del Zoppo'
'Wesley A. Chalifoux'
'Michael J. Ferguson'
'Giuseppe Zerbi'
'Rik R. Tykwinski'
_publ_section_title
;
 Evidence for Solution-State Nonlinearity of sp-Carbon Chains Based on IR
 and Raman Spectroscopy: Violation of Mutual Exclusion
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4239
_journal_page_last               4244
_journal_paper_doi               10.1021/ja078198b
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C28 H30, C4 H8 O'
_chemical_formula_sum            'C32 H38 O'
_chemical_formula_weight         438.62
_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                 97.3220(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.0112(15)
_cell_length_b                   12.7895(12)
_cell_length_c                   11.8476(11)
_cell_measurement_reflns_used    3985
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.41
_cell_volume                     2556.6(4)
_computing_cell_refinement       'Bruker SAINT (Bruker, 1997)'
_computing_data_collection       'Bruker SMART (Bruker, 1997)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL (Bruker, 1997)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector'
_diffrn_measurement_method       'ω 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  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9416
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.9778
_exptl_absorpt_correction_T_min  0.9625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2618
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0658
_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)+(0.1251P)²+0.7566P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1856
_refine_ls_wR_factor_ref         0.2112
_reflns_number_gt                1912
_reflns_number_total             2618
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja078198b_si_002.cif
_cod_data_source_block           compoundC12
_cod_database_code               4104090
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.39056(9) 0.16752(12) 0.57151(12) 0.0505(4) Uani 1 1 d . A .
C2 C 0.42369(9) 0.17454(12) 0.48791(11) 0.0497(4) Uani 1 1 d . . .
C3 C 0.45796(8) 0.17936(12) 0.38989(11) 0.0475(4) Uani 1 1 d . . .
C4 C 0.48528(7) 0.18187(12) 0.30051(10) 0.0457(4) Uani 1 1 d . . .
C11 C 0.34787(9) 0.15533(11) 0.67048(11) 0.0499(4) Uani 1 1 d . . .
C12A C 0.3636(5) 0.2369(4) 0.7574(5) 0.077(2) Uani 0.50 1 d P A 1
H12A H 0.3530 0.3062 0.7214 0.093 Uiso 0.50 1 calc PR A 1
H12B H 0.4203 0.2346 0.7891 0.093 Uiso 0.50 1 calc PR A 1
C13A C 0.3129(7) 0.2244(6) 0.8545(7) 0.079(3) Uani 0.50 1 d P A 1
H13A H 0.3271 0.2802 0.9127 0.095 Uiso 0.50 1 calc PR A 1
C14A C 0.2271(6) 0.2315(4) 0.8111(7) 0.078(2) Uani 0.50 1 d P A 1
H14A H 0.2157 0.3006 0.7751 0.093 Uiso 0.50 1 calc PR A 1
H14B H 0.1955 0.2249 0.8753 0.093 Uiso 0.50 1 calc PR A 1
C15A C 0.2035(2) 0.1448(3) 0.7239(4) 0.0566(8) Uani 0.50 1 d P A 1
H15A H 0.1455 0.1492 0.6964 0.068 Uiso 0.50 1 calc PR A 1
C16A C 0.25166(19) 0.1624(3) 0.6243(3) 0.0582(9) Uani 0.50 1 d P A 1
H16A H 0.2390 0.2320 0.5900 0.070 Uiso 0.50 1 calc PR A 1
H16B H 0.2375 0.1087 0.5650 0.070 Uiso 0.50 1 calc PR A 1
C17A C 0.35826(16) 0.0458(2) 0.7182(2) 0.0449(6) Uani 0.50 1 d P A 1
H17A H 0.4152 0.0318 0.7419 0.054 Uiso 0.50 1 calc PR A 1
H17B H 0.3386 -0.0056 0.6588 0.054 Uiso 0.50 1 calc PR A 1
C18A C 0.3126(4) 0.0338(5) 0.8202(6) 0.0546(13) Uani 0.50 1 d P A 1
H18A H 0.3251 -0.0359 0.8562 0.065 Uiso 0.50 1 calc PR A 1
C19A C 0.3336(3) 0.1177(5) 0.9072(3) 0.0722(12) Uani 0.50 1 d P A 1
H19A H 0.3910 0.1146 0.9347 0.087 Uiso 0.50 1 calc PR A 1
H19B H 0.3042 0.1065 0.9730 0.087 Uiso 0.50 1 calc PR A 1
C20A C 0.2230(3) 0.0388(3) 0.7779(4) 0.0576(11) Uani 0.50 1 d P A 1
H20A H 0.2086 -0.0172 0.7214 0.069 Uiso 0.50 1 calc PR A 1
H20B H 0.1923 0.0282 0.8425 0.069 Uiso 0.50 1 calc PR A 1
C12B C 0.3400(5) 0.2641(5) 0.7235(5) 0.0689(17) Uani 0.50 1 d P A 2
H12C H 0.3105 0.3117 0.6673 0.083 Uiso 0.50 1 calc PR A 2
H12D H 0.3931 0.2943 0.7472 0.083 Uiso 0.50 1 calc PR A 2
C13B C 0.2947(7) 0.2506(7) 0.8283(8) 0.070(2) Uani 0.50 1 d P A 2
H13B H 0.2817 0.3209 0.8577 0.084 Uiso 0.50 1 calc PR A 2
C14B C 0.2173(4) 0.1892(7) 0.7927(7) 0.084(2) Uani 0.50 1 d P A 2
H14C H 0.1862 0.1851 0.8577 0.101 Uiso 0.50 1 calc PR A 2
H14D H 0.1849 0.2262 0.7296 0.101 Uiso 0.50 1 calc PR A 2
C15B C 0.2366(3) 0.0793(6) 0.7547(4) 0.0742(17) Uani 0.50 1 d P A 2
H15B H 0.1866 0.0385 0.7353 0.089 Uiso 0.50 1 calc PR A 2
C16B C 0.2788(2) 0.0936(4) 0.6467(3) 0.0723(11) Uani 0.50 1 d P A 2
H16C H 0.2932 0.0242 0.6185 0.087 Uiso 0.50 1 calc PR A 2
H16D H 0.2420 0.1275 0.5861 0.087 Uiso 0.50 1 calc PR A 2
C17B C 0.4092(2) 0.0984(3) 0.7712(3) 0.0612(8) Uani 0.50 1 d P A 2
H17C H 0.4253 0.0290 0.7450 0.073 Uiso 0.50 1 calc PR A 2
H17D H 0.4574 0.1416 0.7897 0.073 Uiso 0.50 1 calc PR A 2
C18B C 0.3657(2) 0.0859(3) 0.8786(4) 0.0589(9) Uani 0.50 1 d P A 2
H18B H 0.4004 0.0485 0.9402 0.071 Uiso 0.50 1 calc PR A 2
C19B C 0.3469(3) 0.1937(5) 0.9170(5) 0.0735(12) Uani 0.50 1 d P A 2
H19C H 0.3207 0.1888 0.9867 0.088 Uiso 0.50 1 calc PR A 2
H19D H 0.3969 0.2334 0.9360 0.088 Uiso 0.50 1 calc PR A 2
C20B C 0.2906(4) 0.0230(6) 0.8427(6) 0.0703(17) Uani 0.50 1 d P A 2
H20C H 0.3050 -0.0455 0.8122 0.084 Uiso 0.50 1 calc PR A 2
H20D H 0.2630 0.0100 0.9100 0.084 Uiso 0.50 1 calc PR A 2
O1S O 0.0130(8) -0.0265(11) 0.5880(6) 0.215(5) Uani 0.50 1 d PD B -1
C1S C 0.0767(6) -0.0054(12) 0.5205(9) 0.157(4) Uani 0.50 1 d PD B -1
H1SA H 0.1196 -0.0580 0.5336 0.189 Uiso 0.50 1 calc PR B -1
H1SB H 0.0991 0.0656 0.5345 0.189 Uiso 0.50 1 calc PR B -1
C2S C 0.0307(9) -0.0153(11) 0.4043(8) 0.163(4) Uani 0.50 1 d PD B -1
H2SA H 0.0129 -0.0882 0.3886 0.196 Uiso 0.50 1 calc PR B -1
H2SB H 0.0625 0.0079 0.3445 0.196 Uiso 0.50 1 calc PR B -1
C3S C -0.0387(12) 0.0566(11) 0.4118(14) 0.237(12) Uani 0.50 1 d PD B -1
H3SA H -0.0235 0.1312 0.4112 0.284 Uiso 0.50 1 calc PR B -1
H3SB H -0.0830 0.0430 0.3508 0.284 Uiso 0.50 1 calc PR B -1
C4S C -0.0573(6) 0.0217(13) 0.5262(14) 0.181(6) Uani 0.50 1 d PD B -1
H4SA H -0.0738 0.0825 0.5693 0.217 Uiso 0.50 1 calc PR B -1
H4SB H -0.1015 -0.0292 0.5169 0.217 Uiso 0.50 1 calc PR B -1
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
_geom_angle_site_symmetry_3
C2 C1 C11 177.36(15) .
C1 C2 C3 176.84(15) .
C4 C3 C2 177.11(14) .
C3 C4 C4 178.24(13) 2_655
C16B C11 C1 112.59(17) .
C1 C11 C12A 114.9(3) .
C1 C11 C17A 110.60(14) .
C12A C11 C17A 113.2(3) .
C16B C11 C12B 118.2(4) .
C1 C11 C12B 108.0(3) .
C16B C11 C17B 109.3(3) .
C1 C11 C17B 107.07(15) .
C12B C11 C17B 100.6(3) .
C1 C11 C16A 107.38(15) .
C12A C11 C16A 106.1(4) .
C17A C11 C16A 103.71(19) .
C11 C12A C13A 112.5(5) .
C14A C13A C19A 111.2(6) .
C14A C13A C12A 110.8(7) .
C19A C13A C12A 106.1(6) .
C13A C14A C15A 110.5(6) .
C20A C15A C14A 109.7(4) .
C20A C15A C16A 110.1(3) .
C14A C15A C16A 106.9(4) .
C15A C16A C11 109.8(2) .
C11 C17A C18A 110.0(3) .
C19A C18A C17A 111.8(4) .
C19A C18A C20A 109.5(5) .
C17A C18A C20A 108.7(5) .
C18A C19A C13A 109.7(4) .
C15A C20A C18A 109.2(4) .
C11 C12B C13B 107.7(5) .
C19B C13B C14B 111.0(8) .
C19B C13B C12B 108.0(7) .
C14B C13B C12B 109.3(7) .
C15B C14B C13B 109.9(6) .
C20B C15B C14B 112.2(5) .
C20B C15B C16B 109.0(4) .
C14B C15B C16B 105.9(5) .
C11 C16B C15B 111.1(3) .
C18B C17B C11 108.2(2) .
C19B C18B C20B 111.5(5) .
C19B C18B C17B 107.2(3) .
C20B C18B C17B 107.1(4) .
C13B C19B C18B 111.6(5) .
C15B C20B C18B 111.2(5) .
C1S O1S C4S 105.5(7) .
O1S C1S C2S 98.7(6) .
C1S C2S C3S 102.5(11) .
C4S C3S C2S 97.4(8) .
O1S C4S C3S 109.0(7) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.2036(18) .
C1 C11 1.4641(17) .
C2 C3 1.3657(17) .
C3 C4 1.2099(17) .
C4 C4 1.355(2) 2_655
C11 C16B 1.414(4) .
C11 C12A 1.466(6) .
C11 C17A 1.513(3) .
C11 C12B 1.539(7) .
C11 C17B 1.651(4) .
C11 C16A 1.661(4) .
C12A C13A 1.532(12) .
C13A C14A 1.487(14) .
C13A C19A 1.523(10) .
C14A C15A 1.533(8) .
C15A C20A 1.517(5) .
C15A C16A 1.537(4) .
C17A C18A 1.525(5) .
C18A C19A 1.499(10) .
C18A C20A 1.543(8) .
C12B C13B 1.552(11) .
C13B C19B 1.478(8) .
C13B C14B 1.545(16) .
C14B C15B 1.525(11) .
C15B C20B 1.485(11) .
C15B C16B 1.556(5) .
C17B C18B 1.560(5) .
C18B C19B 1.499(6) .
C18B C20B 1.523(9) .
O1S C1S 1.452(5) .
O1S C4S 1.457(5) .
C1S C2S 1.499(5) .
C2S C3S 1.508(5) .
C3S C4S 1.498(5) .
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_4
C11 C1 C2 C3 12(6) .
C1 C2 C3 C4 11(5) .
C2 C3 C4 C4 -38(7) 2_655
C2 C1 C11 C16B -10(4) .
C2 C1 C11 C12A -167(3) .
C2 C1 C11 C17A 63(4) .
C2 C1 C11 C12B -142(3) .
C2 C1 C11 C17B 111(3) .
C2 C1 C11 C16A -49(4) .
C1 C11 C12A C13A 175.9(5) .
C17A C11 C12A C13A -55.7(7) .
C16A C11 C12A C13A 57.4(6) .
C11 C12A C13A C14A -60.9(7) .
C11 C12A C13A C19A 60.0(8) .
C19A C13A C14A C15A -57.3(8) .
C12A C13A C14A C15A 60.5(7) .
C13A C14A C15A C20A 57.7(7) .
C13A C14A C15A C16A -61.8(7) .
C20A C15A C16A C11 -58.8(4) .
C14A C15A C16A C11 60.4(5) .
C1 C11 C16A C15A 177.3(3) .
C12A C11 C16A C15A -59.3(4) .
C17A C11 C16A C15A 60.2(3) .
C1 C11 C17A C18A -179.2(3) .
C12A C11 C17A C18A 50.1(5) .
C16A C11 C17A C18A -64.4(4) .
C11 C17A C18A C19A -52.9(5) .
C11 C17A C18A C20A 68.0(5) .
C17A C18A C19A C13A 60.9(7) .
C20A C18A C19A C13A -59.5(6) .
C14A C13A C19A C18A 58.8(8) .
C12A C13A C19A C18A -61.8(7) .
C14A C15A C20A C18A -58.6(6) .
C16A C15A C20A C18A 58.8(5) .
C19A C18A C20A C15A 60.5(5) .
C17A C18A C20A C15A -61.8(6) .
C16B C11 C12B C13B 50.8(6) .
C1 C11 C12B C13B 180.0(5) .
C17B C11 C12B C13B -68.0(6) .
C11 C12B C13B C19B 69.1(9) .
C11 C12B C13B C14B -51.8(7) .
C19B C13B C14B C15B -55.4(8) .
C12B C13B C14B C15B 63.6(7) .
C13B C14B C15B C20B 54.7(7) .
C13B C14B C15B C16B -64.1(6) .
C1 C11 C16B C15B 178.1(4) .
C12B C11 C16B C15B -54.9(5) .
C17B C11 C16B C15B 59.3(5) .
C20B C15B C16B C11 -62.3(7) .
C14B C15B C16B C11 58.6(6) .
C16B C11 C17B C18B -58.6(3) .
C1 C11 C17B C18B 179.1(2) .
C12B C11 C17B C18B 66.5(4) .
C11 C17B C18B C19B -62.6(4) .
C11 C17B C18B C20B 57.2(5) .
C14B C13B C19B C18B 56.8(9) .
C12B C13B C19B C18B -63.0(9) .
C20B C18B C19B C13B -56.2(8) .
C17B C18B C19B C13B 60.7(7) .
C14B C15B C20B C18B -54.5(7) .
C16B C15B C20B C18B 62.4(6) .
C19B C18B C20B C15B 54.6(6) .
C17B C18B C20B C15B -62.4(6) .
C4S O1S C1S C2S -36.6(15) .
O1S C1S C2S C3S 51.8(13) .
C1S C2S C3S C4S -44.8(15) .
C1S O1S C4S C3S 9.3(18) .
C2S C3S C4S O1S 22.0(18) .
