#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:58:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178453 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/74/4027453.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_4027453
loop_
_publ_author_name
'Edgar Escalante-Sánchez'
'Braulio Rodríguez-Molina'
'Miguel A. Garcia-Garibay'
_publ_contact_author_address
;     
      Chemistry and Biochemistry Department
      University of California Los Angeles
      Charles E. Young Drive East
      Los Angeles, CA 90095
      USA
;
_publ_contact_author_email       mgg@chem.ucla.edu
_publ_contact_author_fax         '310 825 3159'
_publ_contact_author_name        'Miguel A. Garcia-Garibay'
_publ_contact_author_phone       '310 825 3159'
_publ_section_title
;
 Toward Crystalline Molecular Rotors with Linearly Conjugated
 Diethynyl-Phenylene Rotators and Pentiptycene Stators
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7428
_journal_page_last               7434
_journal_paper_doi               10.1021/jo301223q
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C78 H46 O2'
_chemical_formula_sum            'C78 H46 O2'
_chemical_formula_weight         1015.15
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 99.951(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.130(3)
_cell_length_b                   19.101(5)
_cell_length_c                   14.668(4)
_cell_measurement_reflns_used    9872
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.16
_cell_measurement_theta_min      3.70
_cell_volume                     3347.4(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            46107
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         30.77
_diffrn_reflns_theta_min         3.57
_exptl_absorpt_coefficient_mu    0.059
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_correction_T_min  0.9584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Bruker)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.007
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1060
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_platon_squeeze_details
; 
Crystals contain highly disordered mixed solvents (grown from a mixture of 
CH3OH and CH2Cl2) regions which could not be appropriately modelled. 
;
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         9899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0696
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1530P)²+0.4783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2130
_refine_ls_wR_factor_ref         0.2259
_reflns_number_gt                7758
_reflns_number_total             9899
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301223q_si_002.cif
_cod_data_source_block           gg2811-squ
_cod_original_cell_volume        3347.2(15)
_cod_database_code               4027453
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.57362(9) 0.35545(6) 0.06330(8) 0.0303(3) Uani 1 1 d .
H1 H 0.5653 0.3864 0.1023 0.045 Uiso 1 1 calc R
C1 C -0.03017(11) -0.03421(7) -0.08442(9) 0.0216(3) Uani 1 1 d .
H1A H -0.0507 -0.0577 -0.1420 0.026 Uiso 1 1 calc R
C2 C 0.04784(11) 0.01939(7) -0.07625(9) 0.0213(3) Uani 1 1 d .
H2 H 0.0803 0.0326 -0.1282 0.026 Uiso 1 1 calc R
C3 C 0.07904(10) 0.05415(7) 0.00844(9) 0.0195(3) Uani 1 1 d .
C4 C 0.16083(11) 0.10862(7) 0.01779(9) 0.0212(3) Uani 1 1 d .
C5 C 0.22982(10) 0.15417(7) 0.02337(9) 0.0198(3) Uani 1 1 d .
C6 C 0.31281(10) 0.20814(7) 0.03095(9) 0.0198(3) Uani 1 1 d .
C7 C 0.32394(11) 0.25681(7) 0.10302(10) 0.0218(3) Uani 1 1 d .
C8 C 0.41119(11) 0.30553(7) 0.11693(10) 0.0230(3) Uani 1 1 d .
C9 C 0.48639(11) 0.30963(7) 0.05454(10) 0.0230(3) Uani 1 1 d .
C10 C 0.47361(11) 0.26241(7) -0.01953(10) 0.0212(3) Uani 1 1 d .
C11 C 0.38934(10) 0.21183(7) -0.03031(9) 0.0199(3) Uani 1 1 d .
C12 C 0.39439(11) 0.16181(7) -0.11004(9) 0.0210(3) Uani 1 1 d .
H12 H 0.3347 0.1251 -0.1167 0.025 Uiso 1 1 calc R
C13 C 0.51252(12) 0.13140(7) -0.09138(10) 0.0230(3) Uani 1 1 d .
C14 C 0.54031(13) 0.06116(8) -0.08313(11) 0.0291(3) Uani 1 1 d .
H14 H 0.4835 0.0264 -0.0882 0.035 Uiso 1 1 calc R
C15 C 0.65330(15) 0.04210(9) -0.06722(12) 0.0345(4) Uani 1 1 d .
H15 H 0.6734 -0.0060 -0.0615 0.041 Uiso 1 1 calc R
C16 C 0.73654(13) 0.09285(9) -0.05970(11) 0.0319(3) Uani 1 1 d .
H16 H 0.8130 0.0793 -0.0493 0.038 Uiso 1 1 calc R
C17 C 0.70829(12) 0.16360(8) -0.06738(10) 0.0260(3) Uani 1 1 d .
H17 H 0.7651 0.1983 -0.0621 0.031 Uiso 1 1 calc R
C18 C 0.59618(11) 0.18266(7) -0.08287(9) 0.0219(3) Uani 1 1 d .
C19 C 0.54938(11) 0.25706(7) -0.09240(9) 0.0210(3) Uani 1 1 d .
H19 H 0.6089 0.2939 -0.0856 0.025 Uiso 1 1 calc R
C20 C 0.47174(11) 0.25914(7) -0.18592(10) 0.0220(3) Uani 1 1 d .
C21 C 0.47803(12) 0.30506(8) -0.25824(11) 0.0267(3) Uani 1 1 d .
H21 H 0.5335 0.3407 -0.2516 0.032 Uiso 1 1 calc R
C22 C 0.40145(14) 0.29830(9) -0.34127(12) 0.0331(3) Uani 1 1 d .
H22 H 0.4054 0.3292 -0.3913 0.040 Uiso 1 1 calc R
C23 C 0.31979(14) 0.24647(10) -0.35051(12) 0.0344(4) Uani 1 1 d .
H23 H 0.2684 0.2421 -0.4070 0.041 Uiso 1 1 calc R
C24 C 0.31266(12) 0.20073(8) -0.27749(11) 0.0286(3) Uani 1 1 d .
H24 H 0.2566 0.1655 -0.2838 0.034 Uiso 1 1 calc R
C25 C 0.38860(11) 0.20746(7) -0.19571(10) 0.0222(3) Uani 1 1 d .
C26 C 0.25029(11) 0.25921(8) 0.17740(10) 0.0238(3) Uani 1 1 d .
H26 H 0.1867 0.2252 0.1660 0.029 Uiso 1 1 calc R
C27 C 0.33086(12) 0.24490(8) 0.26694(10) 0.0257(3) Uani 1 1 d .
C28 C 0.32525(13) 0.19050(8) 0.32849(11) 0.0292(3) Uani 1 1 d .
H28 H 0.2656 0.1577 0.3173 0.035 Uiso 1 1 calc R
C29 C 0.40794(16) 0.18429(10) 0.40709(12) 0.0362(4) Uani 1 1 d .
H29 H 0.4042 0.1474 0.4499 0.043 Uiso 1 1 calc R
C30 C 0.49557(16) 0.23197(10) 0.42278(13) 0.0392(4) Uani 1 1 d .
H30 H 0.5514 0.2278 0.4766 0.047 Uiso 1 1 calc R
C31 C 0.50211(14) 0.28626(9) 0.35957(12) 0.0344(4) Uani 1 1 d .
H31 H 0.5628 0.3184 0.3699 0.041 Uiso 1 1 calc R
C32 C 0.41976(13) 0.29280(8) 0.28227(11) 0.0276(3) Uani 1 1 d .
C33 C 0.41445(12) 0.34789(8) 0.20600(10) 0.0263(3) Uani 1 1 d .
H33 H 0.4779 0.3820 0.2174 0.032 Uiso 1 1 calc R
C34 C 0.30040(13) 0.38265(8) 0.19793(11) 0.0277(3) Uani 1 1 d .
C35 C 0.27942(15) 0.45364(9) 0.20531(12) 0.0345(4) Uani 1 1 d .
H35 H 0.3395 0.4862 0.2162 0.041 Uiso 1 1 calc R
C36 C 0.16884(17) 0.47666(10) 0.19659(14) 0.0422(4) Uani 1 1 d .
H36 H 0.1536 0.5252 0.2015 0.051 Uiso 1 1 calc R
C37 C 0.08111(16) 0.42919(10) 0.18089(13) 0.0404(4) Uani 1 1 d .
H37 H 0.0062 0.4454 0.1758 0.048 Uiso 1 1 calc R
C38 C 0.10184(13) 0.35776(9) 0.17251(11) 0.0310(3) Uani 1 1 d .
H38 H 0.0416 0.3254 0.1606 0.037 Uiso 1 1 calc R
C39 C 0.21198(12) 0.33469(8) 0.18193(10) 0.0261(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 0.0033 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_1
_geom_angle_site_symmetry_3
C9 O1 H1 109.5 . .
C2 C1 C3 120.54(12) . 3
C2 C1 H1A 119.7 . .
C3 C1 H1A 119.7 3 .
C1 C2 C3 120.17(12) . .
C1 C2 H2 119.9 . .
C3 C2 H2 119.9 . .
C2 C3 C1 119.29(11) . 3
C2 C3 C4 120.47(12) . .
C1 C3 C4 120.24(12) 3 .
C5 C4 C3 178.36(15) . .
C4 C5 C6 179.35(16) . .
C7 C6 C11 117.64(11) . .
C7 C6 C5 120.85(12) . .
C11 C6 C5 121.42(12) . .
C6 C7 C8 121.70(12) . .
C6 C7 C26 124.71(12) . .
C8 C7 C26 113.44(12) . .
C7 C8 C9 120.25(12) . .
C7 C8 C33 112.56(12) . .
C9 C8 C33 127.14(12) . .
O1 C9 C10 117.86(12) . .
O1 C9 C8 123.84(13) . .
C10 C9 C8 118.27(12) . .
C11 C10 C9 120.97(12) . .
C11 C10 C19 113.05(12) . .
C9 C10 C19 125.90(12) . .
C10 C11 C6 121.05(12) . .
C10 C11 C12 113.35(11) . .
C6 C11 C12 125.54(11) . .
C11 C12 C25 105.85(11) . .
C11 C12 C13 105.24(11) . .
C25 C12 C13 105.91(10) . .
C11 C12 H12 113.1 . .
C25 C12 H12 113.1 . .
C13 C12 H12 113.1 . .
C14 C13 C18 120.56(13) . .
C14 C13 C12 126.28(13) . .
C18 C13 C12 113.15(12) . .
C13 C14 C15 118.96(15) . .
C13 C14 H14 120.5 . .
C15 C14 H14 120.5 . .
C16 C15 C14 120.60(15) . .
C16 C15 H15 119.7 . .
C14 C15 H15 119.7 . .
C15 C16 C17 120.31(14) . .
C15 C16 H16 119.8 . .
C17 C16 H16 119.8 . .
C18 C17 C16 119.19(14) . .
C18 C17 H17 120.4 . .
C16 C17 H17 120.4 . .
C17 C18 C13 120.37(13) . .
C17 C18 C19 126.66(13) . .
C13 C18 C19 112.97(12) . .
C20 C19 C18 105.59(11) . .
C20 C19 C10 105.95(10) . .
C18 C19 C10 104.89(11) . .
C20 C19 H19 113.2 . .
C18 C19 H19 113.2 . .
C10 C19 H19 113.2 . .
C21 C20 C25 120.03(13) . .
C21 C20 C19 126.65(12) . .
C25 C20 C19 113.31(12) . .
C20 C21 C22 119.27(14) . .
C20 C21 H21 120.4 . .
C22 C21 H21 120.4 . .
C23 C22 C21 120.23(14) . .
C23 C22 H22 119.9 . .
C21 C22 H22 119.9 . .
C22 C23 C24 120.55(15) . .
C22 C23 H23 119.7 . .
C24 C23 H23 119.7 . .
C25 C24 C23 119.06(14) . .
C25 C24 H24 120.5 . .
C23 C24 H24 120.5 . .
C24 C25 C20 120.86(13) . .
C24 C25 C12 126.20(13) . .
C20 C25 C12 112.93(12) . .
C39 C26 C27 106.78(12) . .
C39 C26 C7 106.32(11) . .
C27 C26 C7 104.12(11) . .
C39 C26 H26 113.0 . .
C27 C26 H26 113.0 . .
C7 C26 H26 113.0 . .
C28 C27 C32 120.51(14) . .
C28 C27 C26 126.94(14) . .
C32 C27 C26 112.51(13) . .
C27 C28 C29 119.50(15) . .
C27 C28 H28 120.2 . .
C29 C28 H28 120.2 . .
C30 C29 C28 120.09(16) . .
C30 C29 H29 120.0 . .
C28 C29 H29 120.0 . .
C29 C30 C31 120.30(16) . .
C29 C30 H30 119.8 . .
C31 C30 H30 119.8 . .
C32 C31 C30 119.61(16) . .
C32 C31 H31 120.2 . .
C30 C31 H31 120.2 . .
C31 C32 C27 119.98(15) . .
C31 C32 C33 126.58(14) . .
C27 C32 C33 113.43(13) . .
C34 C33 C32 106.27(12) . .
C34 C33 C8 105.98(12) . .
C32 C33 C8 104.61(12) . .
C34 C33 H33 113.1 . .
C32 C33 H33 113.1 . .
C8 C33 H33 113.1 . .
C35 C34 C39 120.49(15) . .
C35 C34 C33 126.69(15) . .
C39 C34 C33 112.82(13) . .
C34 C35 C36 119.13(16) . .
C34 C35 H35 120.4 . .
C36 C35 H35 120.4 . .
C37 C36 C35 120.46(16) . .
C37 C36 H36 119.8 . .
C35 C36 H36 119.8 . .
C36 C37 C38 120.58(16) . .
C36 C37 H37 119.7 . .
C38 C37 H37 119.7 . .
C39 C38 C37 119.03(16) . .
C39 C38 H38 120.5 . .
C37 C38 H38 120.5 . .
C38 C39 C34 120.30(15) . .
C38 C39 C26 126.30(14) . .
C34 C39 C26 113.40(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C9 1.3620(16) .
O1 H1 0.8400 .
C1 C2 1.3852(18) .
C1 C3 1.4023(19) 3
C1 H1A 0.9500 .
C2 C3 1.4015(19) .
C2 H2 0.9500 .
C3 C1 1.4024(19) 3
C3 C4 1.4278(18) .
C4 C5 1.2002(19) .
C5 C6 1.4317(17) .
C6 C7 1.3966(19) .
C6 C11 1.4008(18) .
C7 C8 1.3975(18) .
C7 C26 1.5255(18) .
C8 C9 1.4015(19) .
C8 C33 1.531(2) .
C9 C10 1.400(2) .
C10 C11 1.3954(17) .
C10 C19 1.5288(18) .
C11 C12 1.5196(19) .
C12 C25 1.5211(19) .
C12 C13 1.5264(19) .
C12 H12 1.0000 .
C13 C14 1.383(2) .
C13 C18 1.4002(19) .
C14 C15 1.398(2) .
C14 H14 0.9500 .
C15 C16 1.390(3) .
C15 H15 0.9500 .
C16 C17 1.394(2) .
C16 H16 0.9500 .
C17 C18 1.3879(19) .
C17 H17 0.9500 .
C18 C19 1.5277(19) .
C19 C20 1.5243(19) .
C19 H19 1.0000 .
C20 C21 1.389(2) .
C20 C25 1.4008(19) .
C21 C22 1.404(2) .
C21 H21 0.9500 .
C22 C23 1.390(2) .
C22 H22 0.9500 .
C23 C24 1.396(2) .
C23 H23 0.9500 .
C24 C25 1.386(2) .
C24 H24 0.9500 .
C26 C39 1.520(2) .
C26 C27 1.520(2) .
C26 H26 1.0000 .
C27 C28 1.386(2) .
C27 C32 1.402(2) .
C28 C29 1.396(2) .
C28 H28 0.9500 .
C29 C30 1.388(3) .
C29 H29 0.9500 .
C30 C31 1.403(3) .
C30 H30 0.9500 .
C31 C32 1.381(2) .
C31 H31 0.9500 .
C32 C33 1.529(2) .
C33 C34 1.521(2) .
C33 H33 1.0000 .
C34 C35 1.387(2) .
C34 C39 1.399(2) .
C35 C36 1.396(3) .
C35 H35 0.9500 .
C36 C37 1.387(3) .
C36 H36 0.9500 .
C37 C38 1.397(3) .
C37 H37 0.9500 .
C38 C39 1.391(2) .
C38 H38 0.9500 .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.019 0.500 0.000 503.0 7.6
2 -0.002 0.000 0.500 503.0 7.6
