#------------------------------------------------------------------------------
#$Date: 2015-06-07 04:42:30 +0300 (Sun, 07 Jun 2015) $
#$Revision: 138877 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/04/7220416.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_7220416
loop_
_publ_author_name
'Arendt, Agata'
'Kołkowski, Radosław'
'Samoc, Marek'
'Szafert, Sławomir'
_publ_section_title
;
 Spectral dependence of nonlinear optical properties of symmetrical
 octatetraynes with p-substituted phenyl end-groups.
;
_journal_issue                   20
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              13680
_journal_page_last               13688
_journal_paper_doi               10.1039/c5cp01661d
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C26 H18 O4'
_chemical_formula_sum            'C26 H18 O4'
_chemical_formula_weight         394.40
_chemical_name_systematic
; 
 diethyl 4,4'-(octa-1,3,5,7-tetrayne-1,8-diyl)dibenzoate  
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-01-09 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                97.18(5)
_cell_angle_beta                 96.03(5)
_cell_angle_gamma                100.60(5)
_cell_formula_units_Z            1
_cell_length_a                   3.8538(9)
_cell_length_b                   10.179(3)
_cell_length_c                   13.000(3)
_cell_measurement_reflns_used    1866
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      3
_cell_volume                     493.0(3)
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction,2010).'
_computing_data_collection       'CrysAlis RED, (Oxford Diffraction,2010).'
_computing_data_reduction        'CrysAlis RED'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3456
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0142
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.864
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3292
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.606
_diffrn_reflns_theta_min         2.783
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             206
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0494P)²+0.0756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1783
_reflns_number_total             2188
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cp01661d2.cif
_cod_data_source_block           aa223
_cod_depositor_comments
'Adding full bibliography for 7220416--7220417.cif.'
_cod_original_cell_volume        493.0(2)
_cod_database_code               7220416
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.1861(2) 1.34677(8) -0.32087(6) 0.0184(2) Uani 1 1 d . .
O2 O 0.2175(2) 1.21660(9) -0.47109(6) 0.0252(2) Uani 1 1 d . .
C1 C 0.7015(3) 0.85101(12) -0.13568(9) 0.0186(3) Uani 1 1 d . .
C2 C 0.7858(3) 0.76045(12) -0.09353(9) 0.0186(3) Uani 1 1 d . .
C3 C 0.8761(3) 0.65386(12) -0.05066(9) 0.0193(3) Uani 1 1 d . .
C4 C 0.9551(3) 0.55554(12) -0.01798(9) 0.0198(3) Uani 1 1 d . .
C11 C 0.5888(3) 0.95020(11) -0.19355(9) 0.0169(3) Uani 1 1 d . .
C12 C 0.5584(3) 1.07710(12) -0.14318(9) 0.0189(3) Uani 1 1 d . .
H12 H 0.6149 1.0989 -0.0694 0.023 Uiso 1 1 calc R U
C13 C 0.4460(3) 1.17052(11) -0.20105(9) 0.0180(3) Uani 1 1 d . .
H13 H 0.4263 1.2565 -0.1670 0.022 Uiso 1 1 calc R U
C14 C 0.3617(3) 1.13808(11) -0.30944(9) 0.0156(2) Uani 1 1 d . .
C15 C 0.3893(3) 1.01164(11) -0.35940(9) 0.0185(3) Uani 1 1 d . .
H15 H 0.3294 0.9895 -0.4331 0.022 Uiso 1 1 calc R U
C16 C 0.5035(3) 0.91840(12) -0.30220(9) 0.0192(3) Uani 1 1 d . .
H16 H 0.5240 0.8327 -0.3366 0.023 Uiso 1 1 calc R U
C17 C 0.2476(3) 1.23498(11) -0.37666(9) 0.0170(3) Uani 1 1 d . .
C18 C 0.0803(3) 1.44531(12) -0.38320(9) 0.0193(3) Uani 1 1 d . .
H18A H -0.1361 1.4035 -0.4328 0.023 Uiso 1 1 calc R U
H18B H 0.2730 1.4789 -0.4237 0.023 Uiso 1 1 calc R U
C19 C 0.0071(3) 1.56002(12) -0.30924(10) 0.0227(3) Uani 1 1 d . .
H19A H -0.0651 1.6283 -0.3492 0.034 Uiso 1 1 calc R U
H19B H -0.1844 1.5257 -0.2697 0.034 Uiso 1 1 calc R U
H19C H 0.2231 1.6008 -0.2607 0.034 Uiso 1 1 calc R U
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
C17 O1 C18 114.64(9) .
C2 C1 C11 175.08(12) .
C1 C2 C3 177.07(12) .
C4 C3 C2 176.48(13) .
C3 C4 C4 179.49(17) 2_765
C16 C11 C12 119.71(11) .
C16 C11 C1 118.96(11) .
C12 C11 C1 121.32(11) .
C13 C12 C11 120.04(11) .
C13 C12 H12 120.0 .
C11 C12 H12 120.0 .
C12 C13 C14 119.90(11) .
C12 C13 H13 120.1 .
C14 C13 H13 120.1 .
C15 C14 C13 120.07(11) .
C15 C14 C17 117.26(10) .
C13 C14 C17 122.66(11) .
C16 C15 C14 120.30(11) .
C16 C15 H15 119.8 .
C14 C15 H15 119.8 .
C15 C16 C11 119.98(11) .
C15 C16 H16 120.0 .
C11 C16 H16 120.0 .
O2 C17 O1 123.22(11) .
O2 C17 C14 124.04(11) .
O1 C17 C14 112.73(10) .
O1 C18 C19 107.61(10) .
O1 C18 H18A 110.2 .
C19 C18 H18A 110.2 .
O1 C18 H18B 110.2 .
C19 C18 H18B 110.2 .
H18A C18 H18B 108.5 .
C18 C19 H19A 109.5 .
C18 C19 H19B 109.5 .
H19A C19 H19B 109.5 .
C18 C19 H19C 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C17 1.3439(15) .
O1 C18 1.4537(14) .
O2 C17 1.2084(14) .
C1 C2 1.2060(17) .
C1 C11 1.4340(16) .
C2 C3 1.3631(17) .
C3 C4 1.2108(17) .
C4 C4 1.363(2) 2_765
C11 C16 1.3988(17) .
C11 C12 1.4041(17) .
C12 C13 1.3856(17) .
C12 H12 0.9500 .
C13 C14 1.3957(17) .
C13 H13 0.9500 .
C14 C15 1.3948(17) .
C14 C17 1.4914(16) .
C15 C16 1.3815(17) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C18 C19 1.5049(18) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
