#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/42/1504209.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_1504209
loop_
_publ_author_name
'Modjewski, Matthew'
'Lindeman, Sergey V.'
'Rathore, Rajendra'
_publ_section_title
;
 A versatile preparation of Geländer-type p-terphenyls from a readily
 available diacetylenic precursor.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4656
_journal_page_last               4659
_journal_paper_doi               10.1021/ol901938f
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C40 H50 Cl4 O4'
_chemical_formula_weight         736.60
_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                 106.3470(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.5705(2)
_cell_length_b                   9.62430(10)
_cell_length_c                   15.9960(2)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67
_cell_measurement_theta_min      4
_cell_volume                     1857.00(4)
_computing_cell_refinement       'SAINT v7.56A (Bruker, 2008)'
_computing_data_collection       'APEX2-2008.5-0 (Bruker, 2008)'
_computing_data_reduction        'SADABS-2008/1 (Bruker, 2008)'
_computing_molecular_graphics    'XP v5.1 (Bruker, 1998)'
_computing_publication_material  'XCIF-2008/2 (Bruker, 2008)'
_computing_structure_refinement  'SHELXL-2008/4(Bruker, 2008)'
_computing_structure_solution    'XS/SHELXTL-2008/1 (Bruker, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX2 CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0127
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            15545
_diffrn_reflns_theta_full        68.05
_diffrn_reflns_theta_max         68.05
_diffrn_reflns_theta_min         3.66
_exptl_absorpt_coefficient_mu    3.210
_exptl_absorpt_correction_T_max  0.7396
_exptl_absorpt_correction_T_min  0.6277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS. Program for empirical absorption correction of
 area-detector data. University of Goetingen. Germany. 
 Sheldrick, G. M. 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.00094(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3314
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0304
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0482P)²+0.8573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0821
_reflns_number_gt                3190
_reflns_number_total             3314
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901938f_si_009.cif
_cod_data_source_block           raj14q
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1504209
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 0.76601(7) 0.42951(10) 0.44958(5) 0.0192(2) Uani 1 1 d .
O2 O 0.87988(7) 0.47987(10) 0.34147(6) 0.0217(2) Uani 1 1 d .
C1 C 0.54782(10) 0.48448(13) 0.09022(8) 0.0145(3) Uani 1 1 d .
C2 C 0.46937(10) 0.38783(13) 0.04465(8) 0.0147(2) Uani 1 1 d .
C3 C 0.42236(10) 0.40548(13) -0.04444(8) 0.0149(2) Uani 1 1 d .
H3 H 0.3683 0.3407 -0.0751 0.018 Uiso 1 1 calc R
C4 C 0.43888(10) 0.26712(13) 0.09321(8) 0.0166(3) Uani 1 1 d .
H4A H 0.5078 0.2226 0.1287 0.020 Uiso 1 1 calc R
H4B H 0.3982 0.1977 0.0504 0.020 Uiso 1 1 calc R
C5 C 0.36751(10) 0.30697(12) 0.15308(8) 0.0164(3) Uani 1 1 d .
H5A H 0.3637 0.2257 0.1901 0.020 Uiso 1 1 calc R
H5B H 0.2913 0.3255 0.1162 0.020 Uiso 1 1 calc R
C6 C 0.40646(10) 0.43496(12) 0.21383(8) 0.0144(3) Uani 1 1 d .
C11 C 0.59732(10) 0.47045(12) 0.18605(8) 0.0145(3) Uani 1 1 d .
C12 C 0.53418(10) 0.44349(12) 0.24431(8) 0.0140(2) Uani 1 1 d .
C13 C 0.59170(10) 0.42937(12) 0.33290(8) 0.0147(2) Uani 1 1 d .
H13A H 0.5507 0.4102 0.3732 0.018 Uiso 1 1 calc R
C14 C 0.70558(10) 0.44232(12) 0.36373(8) 0.0155(3) Uani 1 1 d .
C15 C 0.76756(10) 0.47027(13) 0.30539(8) 0.0165(3) Uani 1 1 d .
C16 C 0.71313(10) 0.48345(13) 0.21781(8) 0.0160(3) Uani 1 1 d .
H16A H 0.7550 0.5018 0.1780 0.019 Uiso 1 1 calc R
C17 C 0.70868(11) 0.38281(15) 0.50967(8) 0.0228(3) Uani 1 1 d .
H17A H 0.7615 0.3710 0.5673 0.034 Uiso 1 1 calc R
H17B H 0.6725 0.2938 0.4898 0.034 Uiso 1 1 calc R
H17C H 0.6526 0.4516 0.5131 0.034 Uiso 1 1 calc R
C18 C 0.94605(11) 0.50623(18) 0.28378(9) 0.0288(3) Uani 1 1 d .
H18A H 1.0242 0.5130 0.3174 0.043 Uiso 1 1 calc R
H18B H 0.9226 0.5937 0.2527 0.043 Uiso 1 1 calc R
H18C H 0.9368 0.4301 0.2417 0.043 Uiso 1 1 calc R
C21 C 0.35994(10) 0.57469(12) 0.16920(8) 0.0154(3) Uani 1 1 d .
H21A H 0.3914 0.6520 0.2094 0.018 Uiso 1 1 calc R
H21B H 0.3851 0.5864 0.1163 0.018 Uiso 1 1 calc R
C22 C 0.23330(10) 0.58497(14) 0.14349(8) 0.0188(3) Uani 1 1 d .
H22A H 0.2103 0.6782 0.1188 0.023 Uiso 1 1 calc R
H22B H 0.2013 0.5152 0.0979 0.023 Uiso 1 1 calc R
C23 C 0.18821(11) 0.56061(15) 0.22141(9) 0.0229(3) Uani 1 1 d .
H23A H 0.1062 0.5589 0.2016 0.027 Uiso 1 1 calc R
H23B H 0.2114 0.6379 0.2635 0.027 Uiso 1 1 calc R
C24 C 0.23105(11) 0.42322(14) 0.26623(8) 0.0208(3) Uani 1 1 d .
H24A H 0.2007 0.3452 0.2263 0.025 Uiso 1 1 calc R
H24B H 0.2052 0.4124 0.3189 0.025 Uiso 1 1 calc R
C25 C 0.35778(10) 0.41827(13) 0.29210(8) 0.0170(3) Uani 1 1 d .
H25A H 0.3829 0.3285 0.3212 0.020 Uiso 1 1 calc R
H25B H 0.3873 0.4932 0.3347 0.020 Uiso 1 1 calc R
Cl1 Cl -0.00905(3) 0.31786(4) 0.06891(2) 0.03578(13) Uani 1 1 d .
Cl2 Cl 0.10958(3) 0.28985(4) -0.06340(3) 0.03961(13) Uani 1 1 d .
C1S C 0.03410(12) 0.20246(15) -0.00086(9) 0.0281(3) Uani 1 1 d .
H1SA H -0.0317 0.1573 -0.0405 0.034 Uiso 1 1 calc R
H1SB H 0.0812 0.1290 0.0343 0.034 Uiso 1 1 calc R
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'
Cl Cl 0.3639 0.7018 '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
C14 O1 C17 117.34(10) . .
C15 O2 C18 117.28(10) . .
C3 C1 C2 118.93(11) 3_665 .
C3 C1 C11 120.80(11) 3_665 .
C2 C1 C11 120.27(11) . .
C3 C2 C1 119.05(11) . .
C3 C2 C4 121.76(11) . .
C1 C2 C4 119.19(11) . .
C2 C3 C1 122.02(12) . 3_665
C2 C3 H3 119.0 . .
C1 C3 H3 119.0 3_665 .
C2 C4 C5 114.06(10) . .
C2 C4 H4A 108.7 . .
C5 C4 H4A 108.7 . .
C2 C4 H4B 108.7 . .
C5 C4 H4B 108.7 . .
H4A C4 H4B 107.6 . .
C4 C5 C6 116.75(10) . .
C4 C5 H5A 108.1 . .
C6 C5 H5A 108.1 . .
C4 C5 H5B 108.1 . .
C6 C5 H5B 108.1 . .
H5A C5 H5B 107.3 . .
C12 C6 C25 111.27(10) . .
C12 C6 C21 108.78(9) . .
C25 C6 C21 106.10(10) . .
C12 C6 C5 110.80(10) . .
C25 C6 C5 107.19(10) . .
C21 C6 C5 112.63(10) . .
C16 C11 C12 119.77(11) . .
C16 C11 C1 117.00(11) . .
C12 C11 C1 123.23(11) . .
C13 C12 C11 117.37(11) . .
C13 C12 C6 120.53(11) . .
C11 C12 C6 122.06(10) . .
C14 C13 C12 122.59(11) . .
C14 C13 H13A 118.7 . .
C12 C13 H13A 118.7 . .
O1 C14 C13 125.01(11) . .
O1 C14 C15 115.36(11) . .
C13 C14 C15 119.63(11) . .
O2 C15 C16 125.37(11) . .
O2 C15 C14 115.67(11) . .
C16 C15 C14 118.95(11) . .
C15 C16 C11 121.69(11) . .
C15 C16 H16A 119.2 . .
C11 C16 H16A 119.2 . .
O1 C17 H17A 109.5 . .
O1 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
O1 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
O2 C18 H18A 109.5 . .
O2 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
O2 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C22 C21 C6 114.00(10) . .
C22 C21 H21A 108.8 . .
C6 C21 H21A 108.8 . .
C22 C21 H21B 108.8 . .
C6 C21 H21B 108.8 . .
H21A C21 H21B 107.6 . .
C23 C22 C21 111.58(10) . .
C23 C22 H22A 109.3 . .
C21 C22 H22A 109.3 . .
C23 C22 H22B 109.3 . .
C21 C22 H22B 109.3 . .
H22A C22 H22B 108.0 . .
C22 C23 C24 110.69(11) . .
C22 C23 H23A 109.5 . .
C24 C23 H23A 109.5 . .
C22 C23 H23B 109.5 . .
C24 C23 H23B 109.5 . .
H23A C23 H23B 108.1 . .
C23 C24 C25 110.88(11) . .
C23 C24 H24A 109.5 . .
C25 C24 H24A 109.5 . .
C23 C24 H24B 109.5 . .
C25 C24 H24B 109.5 . .
H24A C24 H24B 108.1 . .
C24 C25 C6 113.35(10) . .
C24 C25 H25A 108.9 . .
C6 C25 H25A 108.9 . .
C24 C25 H25B 108.9 . .
C6 C25 H25B 108.9 . .
H25A C25 H25B 107.7 . .
Cl1 C1S Cl2 111.52(8) . .
Cl1 C1S H1SA 109.3 . .
Cl2 C1S H1SA 109.3 . .
Cl1 C1S H1SB 109.3 . .
Cl2 C1S H1SB 109.3 . .
H1SA C1S H1SB 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C14 1.3751(15) .
O1 C17 1.4265(16) .
O2 C15 1.3698(15) .
O2 C18 1.4283(16) .
C1 C3 1.3974(17) 3_665
C1 C2 1.4016(18) .
C1 C11 1.4894(16) .
C2 C3 1.3909(17) .
C2 C4 1.5058(17) .
C3 C1 1.3975(17) 3_665
C3 H3 0.9500 .
C4 C5 1.5339(17) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.5601(16) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C12 1.5433(16) .
C6 C25 1.5488(16) .
C6 C21 1.5573(16) .
C11 C16 1.4060(17) .
C11 C12 1.4079(17) .
C12 C13 1.4045(17) .
C13 C14 1.3822(18) .
C13 H13A 0.9500 .
C14 C15 1.4000(18) .
C15 C16 1.3810(17) .
C16 H16A 0.9500 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C21 C22 1.5312(17) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 C23 1.5257(18) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C24 1.5281(19) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 C25 1.5298(17) .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C25 H25A 0.9900 .
C25 H25B 0.9900 .
Cl1 C1S 1.7647(15) .
Cl2 C1S 1.7728(15) .
C1S H1SA 0.9900 .
C1S H1SB 0.9900 .
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
C3 C1 C2 C3 -0.95(19) 3_665 .
C11 C1 C2 C3 178.35(11) . .
C3 C1 C2 C4 178.56(11) 3_665 .
C11 C1 C2 C4 -2.14(17) . .
C1 C2 C3 C1 1.0(2) . 3_665
C4 C2 C3 C1 -178.52(11) . 3_665
C3 C2 C4 C5 -108.02(13) . .
C1 C2 C4 C5 72.49(14) . .
C2 C4 C5 C6 -47.37(15) . .
C4 C5 C6 C12 -34.42(14) . .
C4 C5 C6 C25 -156.00(10) . .
C4 C5 C6 C21 87.68(13) . .
C3 C1 C11 C16 -47.84(16) 3_665 .
C2 C1 C11 C16 132.87(12) . .
C3 C1 C11 C12 133.03(13) 3_665 .
C2 C1 C11 C12 -46.26(17) . .
C16 C11 C12 C13 -0.63(17) . .
C1 C11 C12 C13 178.49(11) . .
C16 C11 C12 C6 177.10(11) . .
C1 C11 C12 C6 -3.79(18) . .
C25 C6 C12 C13 3.07(15) . .
C21 C6 C12 C13 119.61(12) . .
C5 C6 C12 C13 -116.07(12) . .
C25 C6 C12 C11 -174.58(11) . .
C21 C6 C12 C11 -58.04(14) . .
C5 C6 C12 C11 66.27(14) . .
C11 C12 C13 C14 0.67(17) . .
C6 C12 C13 C14 -177.09(11) . .
C17 O1 C14 C13 8.04(17) . .
C17 O1 C14 C15 -171.80(11) . .
C12 C13 C14 O1 -179.99(11) . .
C12 C13 C14 C15 -0.16(18) . .
C18 O2 C15 C16 0.26(19) . .
C18 O2 C15 C14 179.08(12) . .
O1 C14 C15 O2 0.55(16) . .
C13 C14 C15 O2 -179.30(11) . .
O1 C14 C15 C16 179.45(11) . .
C13 C14 C15 C16 -0.40(18) . .
O2 C15 C16 C11 179.22(11) . .
C14 C15 C16 C11 0.44(19) . .
C12 C11 C16 C15 0.09(18) . .
C1 C11 C16 C15 -179.08(11) . .
C12 C6 C21 C22 -174.56(10) . .
C25 C6 C21 C22 -54.76(13) . .
C5 C6 C21 C22 62.21(13) . .
C6 C21 C22 C23 55.67(14) . .
C21 C22 C23 C24 -53.75(14) . .
C22 C23 C24 C25 55.25(14) . .
C23 C24 C25 C6 -58.90(14) . .
C12 C6 C25 C24 174.50(10) . .
C21 C6 C25 C24 56.34(13) . .
C5 C6 C25 C24 -64.22(13) . .
