#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301863 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/36/7203686.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_7203686
loop_
_publ_author_name
'Tolulope M. Fasina'
'Jonathan C. Collings'
'Jacqueline M. Burke'
'Andrei S. Batsanov'
'Richard M. Ward'
'David Albesa-Jové'
'Laurent Porrès'
'Andrew Beeby'
'Judith A. K. Howard'
'Andrew J. Scott'
'William Clegg'
'Stephen W. Watt'
'Christopher Viney'
'Todd B. Marder'
_publ_section_title
;
 Synthesis, optical properties, crystal structures and phase behaviour
 of symmetric, conjugated ethynylarene-based rigid rods with terminal
 carboxylate groups
;
_journal_issue                   6
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              690
_journal_paper_doi               10.1039/b413514h
_journal_volume                  15
_journal_year                    2005
_chemical_formula_moiety         'C20 H14 O4'
_chemical_formula_sum            'C20 H14 O4'
_chemical_formula_weight         318.31
_chemical_melting_point          463.5(5)
_chemical_name_common            1,4-Bis(4-carbomethoxyphenyl)butadiyne
_chemical_name_systematic
;
1,4-Bis(4-carbomethoxyphenyl)butadiyne
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                75.204(3)
_cell_angle_beta                 72.585(3)
_cell_angle_gamma                75.457(3)
_cell_formula_units_Z            2
_cell_length_a                   7.0249(5)
_cell_length_b                   10.4613(8)
_cell_length_c                   11.7016(8)
_cell_measurement_reflns_used    884
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      60.873
_cell_measurement_theta_min      6.190
_cell_volume                     778.97(10)
_computing_cell_refinement       'SMART V5.625 (Bruker, 2001)'
_computing_data_collection       'SMART V5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6.02a (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL V5.1 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_device_type  'ProteumM APEX CCD area detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source
'60W microfocus Bede Microsource with glass polycapillary optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6778
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0551
_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)+(0.0663P)²+0.1963P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1406
_reflns_number_gt                3456
_reflns_number_total             4305
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b413514h.txt
_cod_data_source_block           (6)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '463--464' was changed to '463.5(5)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_cell_volume        779.0(1)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7203686
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 1.46831(14) 0.16169(10) -0.17472(9) 0.0205(2) Uani 1 1 d . . .
O2 O 1.59167(16) 0.14033(11) -0.01323(10) 0.0256(3) Uani 1 1 d . . .
O3 O -0.60045(15) 0.89651(11) 0.69760(9) 0.0210(2) Uani 1 1 d . . .
O4 O -0.77697(16) 0.85373(12) 0.58505(10) 0.0287(3) Uani 1 1 d . . .
C1 C 1.6633(2) 0.09023(16) -0.23387(14) 0.0227(3) Uani 1 1 d . . .
H11 H 1.685(3) -0.0015(19) -0.1888(16) 0.025(5) Uiso 1 1 d . . .
H12 H 1.652(3) 0.091(2) -0.3183(19) 0.039(5) Uiso 1 1 d . . .
H13 H 1.768(3) 0.1394(19) -0.2385(17) 0.031(5) Uiso 1 1 d . . .
C2 C 1.4530(2) 0.17758(14) -0.06238(12) 0.0175(3) Uani 1 1 d . . .
C3 C 1.2460(2) 0.24665(13) -0.00447(12) 0.0167(3) Uani 1 1 d . . .
C4 C 1.0819(2) 0.26805(14) -0.05525(13) 0.0187(3) Uani 1 1 d . . .
H4 H 1.099(3) 0.2384(17) -0.1307(16) 0.023(4) Uiso 1 1 d . . .
C5 C 0.8913(2) 0.33098(15) 0.00194(13) 0.0192(3) Uani 1 1 d . . .
H5 H 0.778(3) 0.3442(18) -0.0341(16) 0.025(4) Uiso 1 1 d . . .
C6 C 0.8630(2) 0.37307(13) 0.11105(12) 0.0178(3) Uani 1 1 d . . .
C7 C 1.0287(2) 0.35155(14) 0.16184(13) 0.0202(3) Uani 1 1 d . . .
H7 H 1.010(3) 0.3798(18) 0.2385(17) 0.027(5) Uiso 1 1 d . . .
C8 C 1.2183(2) 0.28865(14) 0.10439(13) 0.0191(3) Uani 1 1 d . . .
H8 H 1.329(3) 0.2746(19) 0.1405(17) 0.032(5) Uiso 1 1 d . . .
C9 C 0.6653(2) 0.43632(14) 0.17086(13) 0.0199(3) Uani 1 1 d . . .
C10 C 0.4975(2) 0.48759(14) 0.22121(13) 0.0200(3) Uani 1 1 d . . .
C11 C 0.3076(2) 0.54473(14) 0.28099(12) 0.0195(3) Uani 1 1 d . . .
C12 C 0.1416(2) 0.59329(14) 0.33574(13) 0.0189(3) Uani 1 1 d . . .
C13 C -0.0498(2) 0.65413(14) 0.40514(12) 0.0172(3) Uani 1 1 d . . .
C14 C -0.2336(2) 0.63591(14) 0.39376(13) 0.0188(3) Uani 1 1 d . . .
H14 H -0.232(3) 0.5804(19) 0.3386(17) 0.029(5) Uiso 1 1 d . . .
C15 C -0.4161(2) 0.69796(15) 0.46109(13) 0.0189(3) Uani 1 1 d . . .
H15 H -0.538(3) 0.6836(16) 0.4533(15) 0.019(4) Uiso 1 1 d . . .
C16 C -0.4176(2) 0.77831(14) 0.54013(12) 0.0166(3) Uani 1 1 d . . .
C17 C -0.2348(2) 0.79545(15) 0.55218(12) 0.0182(3) Uani 1 1 d . . .
H17 H -0.235(3) 0.8502(17) 0.6032(16) 0.021(4) Uiso 1 1 d . . .
C18 C -0.0519(2) 0.73409(15) 0.48515(12) 0.0187(3) Uani 1 1 d . . .
H18 H 0.076(3) 0.7508(16) 0.4906(15) 0.018(4) Uiso 1 1 d . . .
C19 C -0.6178(2) 0.84568(14) 0.60818(12) 0.0171(3) Uani 1 1 d . . .
C20 C -0.7878(2) 0.96755(16) 0.76567(14) 0.0213(3) Uani 1 1 d . . .
H201 H -0.824(3) 1.0544(19) 0.7157(17) 0.026(5) Uiso 1 1 d . . .
H202 H -0.754(3) 0.9762(18) 0.8376(17) 0.027(5) Uiso 1 1 d . . .
H203 H -0.892(3) 0.914(2) 0.7886(17) 0.033(5) Uiso 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
_geom_angle_publ_flag
C2 O1 C1 115.18(11) . . ?
C19 O3 C20 115.66(11) . . ?
O1 C1 H11 109.0(10) . . ?
O1 C1 H12 105.3(11) . . ?
H11 C1 H12 109.9(15) . . ?
O1 C1 H13 108.2(11) . . ?
H11 C1 H13 113.1(15) . . ?
H12 C1 H13 111.1(16) . . ?
O2 C2 O1 123.69(12) . . ?
O2 C2 C3 123.78(13) . . ?
O1 C2 C3 112.52(12) . . ?
C4 C3 C8 119.95(12) . . ?
C4 C3 C2 121.86(12) . . ?
C8 C3 C2 118.18(12) . . ?
C5 C4 C3 120.23(13) . . ?
C5 C4 H4 119.0(10) . . ?
C3 C4 H4 120.8(10) . . ?
C4 C5 C6 119.97(13) . . ?
C4 C5 H5 119.2(10) . . ?
C6 C5 H5 120.8(10) . . ?
C5 C6 C7 119.64(12) . . ?
C5 C6 C9 119.85(13) . . ?
C7 C6 C9 120.50(13) . . ?
C8 C7 C6 120.08(13) . . ?
C8 C7 H7 119.8(10) . . ?
C6 C7 H7 120.1(10) . . ?
C7 C8 C3 120.11(13) . . ?
C7 C8 H8 118.8(11) . . ?
C3 C8 H8 121.1(11) . . ?
C10 C9 C6 178.81(16) . . ?
C9 C10 C11 178.71(16) . . ?
C12 C11 C10 178.63(16) . . ?
C11 C12 C13 176.38(16) . . ?
C14 C13 C18 119.66(12) . . ?
C14 C13 C12 121.31(13) . . ?
C18 C13 C12 119.02(13) . . ?
C15 C14 C13 119.75(13) . . ?
C15 C14 H14 120.5(11) . . ?
C13 C14 H14 119.7(11) . . ?
C14 C15 C16 120.40(13) . . ?
C14 C15 H15 118.6(10) . . ?
C16 C15 H15 120.9(10) . . ?
C17 C16 C15 119.81(12) . . ?
C17 C16 C19 121.81(12) . . ?
C15 C16 C19 118.38(12) . . ?
C18 C17 C16 120.17(13) . . ?
C18 C17 H17 119.5(11) . . ?
C16 C17 H17 120.3(11) . . ?
C17 C18 C13 120.20(13) . . ?
C17 C18 H18 119.7(9) . . ?
C13 C18 H18 120.0(9) . . ?
O4 C19 O3 123.79(12) . . ?
O4 C19 C16 123.96(13) . . ?
O3 C19 C16 112.26(11) . . ?
O3 C20 H201 108.4(11) . . ?
O3 C20 H202 104.3(11) . . ?
H201 C20 H202 111.7(15) . . ?
O3 C20 H203 109.4(11) . . ?
H201 C20 H203 112.3(16) . . ?
H202 C20 H203 110.4(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3362(17) . ?
O1 C1 1.4479(16) . ?
O2 C2 1.2090(17) . ?
O3 C19 1.3363(17) . ?
O3 C20 1.4500(16) . ?
O4 C19 1.2053(17) . ?
C1 H11 0.968(18) . ?
C1 H12 1.01(2) . ?
C1 H13 0.98(2) . ?
C2 C3 1.4931(18) . ?
C3 C4 1.394(2) . ?
C3 C8 1.3958(19) . ?
C4 C5 1.3855(18) . ?
C4 H4 0.974(17) . ?
C5 C6 1.398(2) . ?
C5 H5 0.971(19) . ?
C6 C7 1.405(2) . ?
C6 C9 1.4317(18) . ?
C7 C8 1.3816(19) . ?
C7 H7 0.977(18) . ?
C8 H8 0.95(2) . ?
C9 C10 1.2054(19) . ?
C10 C11 1.3715(19) . ?
C11 C12 1.2041(19) . ?
C12 C13 1.4325(18) . ?
C13 C14 1.400(2) . ?
C13 C18 1.401(2) . ?
C14 C15 1.3874(18) . ?
C14 H14 0.968(19) . ?
C15 C16 1.3961(19) . ?
C15 H15 0.937(17) . ?
C16 C17 1.392(2) . ?
C16 C19 1.4925(17) . ?
C17 C18 1.3848(18) . ?
C17 H17 0.927(18) . ?
C18 H18 0.983(18) . ?
C20 H201 0.967(18) . ?
C20 H202 0.970(19) . ?
C20 H203 0.97(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C18 H18 O4 0.983(18) 2.299(18) 3.1584(19) 145.4(13) 1_655
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 10.90(19) . . . . ?
C15 C16 C19 O4 -12.7(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 14646424
2 PubChem 14793289
