#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/83/2018336.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2018336
loop_
_publ_author_name
'Tabata, Hideyuki'
'Kubo, Natsuki'
'Okuno, Tsunehisa'
_publ_section_title
;
 Two polymorphs of
 N¹,N⁴-bis(5-hydroxypenta-1,3-diynyl)-N¹,N⁴-diphenylbenzene-1,4-diamine
;
_journal_coeditor_code           UK3036
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o492
_journal_page_last               o495
_journal_paper_doi               10.1107/S0108270111045951
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C28 H20 N2 O2'
_chemical_formula_moiety         'C28 H20 N2 O2'
_chemical_formula_sum            'C28 H20 N2 O2'
_chemical_formula_weight         416.46
_chemical_name_systematic
;
N¹,N⁴-bis(5-hydroxypenta-1,3-diynyl)-
N¹,N⁴-diphenylbenzene-1,4-diamine
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 93.148(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0669(18)
_cell_length_b                   7.7778(16)
_cell_length_c                   30.135(6)
_cell_measurement_reflns_used    2923
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      2.25
_cell_volume                     2121.9(7)
_computing_cell_refinement       'APEX2 (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'enCIFer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11823
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.35
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9959
_exptl_absorpt_correction_T_min  0.9606
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.529
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         4842
_refine_ls_number_restraints     81
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0512
_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)+(0.0512P)²+1.2491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1327
_reflns_number_gt                3703
_reflns_number_total             4842
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            uk3036.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018336
_cod_database_fobs_code          2018336
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.97406(18) 0.9263(2) 0.32887(5) 0.0186(4) Uani d . 1 1
C C2 1.0220(2) 0.8268(2) 0.29412(6) 0.0203(4) Uani d . 1 1
C C3 0.94556(19) 0.8304(2) 0.25305(6) 0.0196(4) Uani d . 1 1
C C4 0.82030(18) 0.9331(2) 0.24653(5) 0.0172(4) Uani d . 1 1
C C5 0.77410(19) 1.0344(2) 0.28120(6) 0.0184(4) Uani d . 1 1
C C6 0.85049(19) 1.0309(2) 0.32224(6) 0.0190(4) Uani d . 1 1
C C7 1.20500(19) 0.9286(2) 0.37841(6) 0.0201(4) Uani d . 1 1
C C8 1.2746(2) 0.8571(3) 0.41628(6) 0.0229(4) Uani d . 1 1
C C9 1.4265(2) 0.8739(3) 0.42327(6) 0.0256(4) Uani d . 1 1
C C10 1.5094(2) 0.9603(3) 0.39305(6) 0.0256(4) Uani d . 1 1
C C11 1.4390(2) 1.0305(3) 0.35527(6) 0.0243(4) Uani d . 1 1
C C12 1.2876(2) 1.0151(2) 0.34770(6) 0.0214(4) Uani d . 1 1
C C13 0.58928(19) 0.9688(2) 0.19674(6) 0.0199(4) Uani d . 1 1
C C14 0.5351(2) 1.0377(3) 0.15658(7) 0.0287(4) Uani d . 1 1
C C15 0.3841(2) 1.0636(3) 0.14915(8) 0.0361(5) Uani d . 1 1
C C16 0.2876(2) 1.0264(3) 0.18203(8) 0.0343(5) Uani d . 1 1
C C17 0.3431(2) 0.9579(3) 0.22186(7) 0.0289(5) Uani d D 1 1
C C18 0.4929(2) 0.9256(2) 0.22940(6) 0.0226(4) Uani d . 1 1
C C19 0.96509(19) 0.8878(3) 0.40665(6) 0.0224(4) Uani d . 1 1
C C20 0.88956(19) 0.8610(3) 0.43739(6) 0.0247(4) Uani d . 1 1
C C21 0.80320(19) 0.8218(3) 0.47201(6) 0.0220(4) Uani d . 1 1
C C22 0.72713(19) 0.7873(3) 0.50211(6) 0.0221(4) Uani d U 1 1
C C23 0.6372(2) 0.7159(2) 0.53664(6) 0.0246(4) Uani d DU 1 1
H H17 0.6871 0.7372 0.5662 0.030 Uiso calc R 1 1
H H18 0.5405 0.7753 0.5357 0.030 Uiso calc R 1 1
C C24 0.82673(19) 0.9179(2) 0.16790(6) 0.0196(4) Uani d . 1 1
C C25 0.90268(19) 0.8987(3) 0.13693(6) 0.0221(4) Uani d . 1 1
C C26 0.9874(2) 0.8637(3) 0.10157(6) 0.0268(4) Uani d . 1 1
C C27 1.0611(2) 0.8295(3) 0.07110(7) 0.0382(5) Uani d U 1 1
C C28 1.1467(3) 0.7863(4) 0.03282(7) 0.0561(7) Uani d DU 1 1
H H19 1.2528 0.7805 0.0425 0.067 Uiso calc R 1 1
H H20 1.1164 0.6713 0.0216 0.067 Uiso calc R 1 1
H H3 1.111(2) 0.751(3) 0.2995(6) 0.025(5) Uiso d . 1 1
H H4 0.977(2) 0.761(3) 0.2290(6) 0.015(5) Uiso d . 1 1
H H5 0.690(2) 1.107(3) 0.2763(6) 0.023(5) Uiso d . 1 1
H H6 0.820(2) 1.104(3) 0.3469(6) 0.018(5) Uiso d . 1 1
H H7 1.214(2) 0.793(3) 0.4377(7) 0.027(5) Uiso d . 1 1
H H8 1.474(2) 0.821(3) 0.4497(7) 0.033(6) Uiso d . 1 1
H H9 1.617(3) 0.975(3) 0.3985(7) 0.034(6) Uiso d . 1 1
H H10 1.495(2) 1.092(3) 0.3343(6) 0.022(5) Uiso d . 1 1
H H11 1.237(2) 1.068(3) 0.3218(7) 0.033(6) Uiso d . 1 1
H H12 0.603(2) 1.067(3) 0.1343(7) 0.032(6) Uiso d . 1 1
H H13 0.348(3) 1.110(3) 0.1200(8) 0.045(7) Uiso d . 1 1
H H14 0.178(2) 1.046(3) 0.1750(7) 0.029(6) Uiso d . 1 1
H H15 0.277(2) 0.929(3) 0.2454(7) 0.034(6) Uiso d . 1 1
H H16 0.530(2) 0.871(3) 0.2569(7) 0.025(5) Uiso d . 1 1
H H1A 0.5522(13) 0.5249(15) 0.5106(5) 0.075(12) Uiso d PD 0.50 1
H H2A 1.2080(13) 0.939(3) -0.0086(7) 0.075(12) Uiso d PD 0.50 1
H H1B 0.6920(16) 0.495(2) 0.5242(18) 0.075(12) Uiso d PD 0.50 1
H H2B 1.053(2) 0.961(3) 0.0017(7) 0.075(12) Uiso d PD 0.50 1
N N1 1.04834(16) 0.9169(2) 0.37201(5) 0.0210(3) Uani d . 1 1
N N2 0.74536(16) 0.9391(2) 0.20355(5) 0.0192(3) Uani d . 1 1
O O1 0.6139(2) 0.5375(2) 0.53103(8) 0.0620(6) Uani d DU 1 1
O O2 1.1279(2) 0.9048(2) -0.00128(5) 0.0452(5) Uani d DU 1 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'
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_publ_flag
C6 C1 C2 120.01(16) ?
C6 C1 N1 119.69(15) ?
C2 C1 N1 120.26(16) ?
C3 C2 C1 119.98(16) ?
C3 C2 H3 120.9(11) ?
C1 C2 H3 119.1(11) ?
C2 C3 C4 120.09(16) ?
C2 C3 H4 120.5(11) ?
C4 C3 H4 119.4(11) ?
C5 C4 C3 119.69(16) ?
C5 C4 N2 120.95(16) ?
C3 C4 N2 119.29(15) ?
C6 C5 C4 120.23(16) ?
C6 C5 H5 120.4(12) ?
C4 C5 H5 119.4(12) ?
C5 C6 C1 119.98(16) ?
C5 C6 H6 120.8(11) ?
C1 C6 H6 119.2(11) ?
C8 C7 C12 120.10(17) ?
C8 C7 N1 119.34(16) ?
C12 C7 N1 120.53(16) ?
C9 C8 C7 119.31(17) ?
C9 C8 H7 121.4(12) ?
C7 C8 H7 119.3(12) ?
C10 C9 C8 121.04(18) ?
C10 C9 H8 120.8(13) ?
C8 C9 H8 118.1(13) ?
C9 C10 C11 119.23(17) ?
C9 C10 H9 120.8(13) ?
C11 C10 H9 119.9(13) ?
C12 C11 C10 120.58(17) ?
C12 C11 H10 119.2(12) ?
C10 C11 H10 120.2(12) ?
C11 C12 C7 119.74(17) ?
C11 C12 H11 120.9(13) ?
C7 C12 H11 119.3(13) ?
C14 C13 C18 120.20(17) ?
C14 C13 N2 119.02(16) ?
C18 C13 N2 120.76(16) ?
C13 C14 C15 119.67(19) ?
C13 C14 H12 119.0(13) ?
C15 C14 H12 121.3(13) ?
C16 C15 C14 120.6(2) ?
C16 C15 H13 121.5(14) ?
C14 C15 H13 117.9(14) ?
C17 C16 C15 119.07(19) ?
C17 C16 H14 123.0(12) ?
C15 C16 H14 117.9(12) ?
C16 C17 C18 121.26(19) ?
C16 C17 H15 120.5(13) ?
C18 C17 H15 118.3(13) ?
C17 C18 C13 119.15(19) ?
C17 C18 H16 120.6(12) ?
C13 C18 H16 120.2(12) ?
N1 C19 C20 179.4(2) y
C19 C20 C21 177.1(2) y
C22 C21 C20 179.7(2) y
C21 C22 C23 170.6(2) y
O1 C23 C22 111.87(16) ?
O1 C23 H17 109.2 ?
C22 C23 H17 109.2 ?
O1 C23 H18 109.2 ?
C22 C23 H18 109.2 ?
H17 C23 H18 107.9 ?
N2 C24 C25 178.16(18) y
C24 C25 C26 175.7(2) y
C27 C26 C25 178.5(2) y
C26 C27 C28 178.0(2) y
O2 C28 C27 112.5(2) ?
O2 C28 H19 109.1 ?
C27 C28 H19 109.1 ?
O2 C28 H20 109.1 ?
C27 C28 H20 109.1 ?
H19 C28 H20 107.8 ?
C19 N1 C7 120.31(14) ?
C19 N1 C1 117.29(14) ?
C7 N1 C1 122.33(13) ?
C24 N2 C4 117.70(14) ?
C24 N2 C13 118.95(14) ?
C4 N2 C13 123.34(14) ?
C23 O1 H1A 107.5(9) ?
C23 O1 H1B 107.3(7) ?
H1A O1 H1B 109(4) ?
C28 O2 H2A 110.1(10) ?
C28 O2 H2B 110.0(10) ?
H2A O2 H2B 128(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C19 1.341(2) y
C19 C20 1.200(2) y
C20 C21 1.373(2) y
C21 C22 1.200(2) y
C22 C23 1.466(2) y
N2 C24 1.346(2) y
C24 C25 1.199(2) y
C25 C26 1.375(2) y
C26 C27 1.195(3) y
C27 C28 1.465(3) y
C1 C6 1.390(2) ?
C1 C2 1.391(2) ?
C1 N1 1.433(2) ?
C2 C3 1.385(2) ?
C2 H3 1.00(2) ?
C3 C4 1.394(2) ?
C3 H4 0.960(19) ?
C4 C5 1.391(2) ?
C4 N2 1.430(2) ?
C5 C6 1.384(2) ?
C5 H5 0.95(2) ?
C6 H6 0.989(19) ?
C7 C8 1.389(2) ?
C7 C12 1.395(2) ?
C7 N1 1.426(2) ?
C8 C9 1.387(3) ?
C8 H7 1.00(2) ?
C9 C10 1.386(3) ?
C9 H8 0.98(2) ?
C10 C11 1.387(3) ?
C10 H9 0.98(2) ?
C11 C12 1.384(3) ?
C11 H10 0.96(2) ?
C12 H11 0.97(2) ?
C13 C14 1.388(3) ?
C13 C18 1.393(2) ?
C13 N2 1.437(2) ?
C14 C15 1.390(3) ?
C14 H12 0.96(2) ?
C15 C16 1.388(3) ?
C15 H13 0.99(2) ?
C16 C17 1.383(3) ?
C16 H14 1.02(2) ?
C17 C18 1.387(3) ?
C17 H15 0.98(2) ?
C18 H16 0.98(2) ?
C23 O1 1.412(2) ?
C23 H17 0.9900 ?
C23 H18 0.9900 ?
C28 O2 1.384(3) ?
C28 H19 0.9900 ?
C28 H20 0.9900 ?
O1 H1A 0.816(11) ?
O1 H1B 0.817(11) ?
O2 H2A 0.816(11) ?
O2 H2B 0.816(11) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1A O1 3_666 0.815(14) 1.97(2) 2.771(3) 168.9(14)
O1 H1B O2 2_745 0.82(3) 1.94(3) 2.753(3) 173(5)
O2 H2A O1 2_755 0.815(15) 1.94(2) 2.753(3) 173(2)
O2 H2B O2 3_775 0.82(2) 1.94(2) 2.756(3) 173(2)
