#------------------------------------------------------------------------------
#$Date: 2019-11-17 07:19:31 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228629 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/94/1549452.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_1549452
loop_
_publ_author_name
'Sharber, Seth A.'
'Shih, Kuo-Chih'
'Mann, Arielle'
'Frausto, Fanny'
'Haas, Terry E.'
'Nieh, Mu-Ping'
'Thomas, Samuel W.'
_publ_section_title
;
 Reversible mechanofluorochromism of aniline-terminated phenylene
 ethynylenes.
;
_journal_issue                   24
_journal_name_full               'Chemical science'
_journal_page_first              5415
_journal_page_last               5426
_journal_paper_doi               10.1039/c8sc00980e
_journal_volume                  9
_journal_year                    2018
_chemical_formula_sum            'C42 H36 N2 O4'
_chemical_formula_weight         632.73
_chemical_name_systematic        A-1F0
_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-2016/6
_audit_update_record
;
2018-02-28 deposited with the CCDC.
2018-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                102.1170(10)
_cell_angle_beta                 107.2990(10)
_cell_angle_gamma                102.2830(10)
_cell_formula_units_Z            1
_cell_length_a                   8.8034(5)
_cell_length_b                   9.6631(6)
_cell_length_c                   10.5046(6)
_cell_measurement_reflns_used    8934
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      33.40
_cell_measurement_theta_min      2.85
_cell_volume                     797.12(8)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22040
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.399
_diffrn_reflns_theta_min         2.855
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       Prism
_exptl_crystal_F_000             334
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane with layered hexanes'
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_exptl_transmission_factor_max   0.9590
_exptl_transmission_factor_min   0.9200
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         6175
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0795P)²+0.1506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1328
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4933
_reflns_number_total             6175
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8sc00980e2.cif
_cod_data_source_block           A-1F0_SS051016_0m_a
_cod_depositor_comments
'Adding full bibliography for 1549452--1549455.cif.'
_cod_original_cell_volume        797.11(8)
_cod_database_code               1549452
_shelx_shelxl_version_number     2016/6
_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   0.920
_shelx_estimated_absorpt_t_max   0.959
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
C1 C 0.86492(10) 0.87505(9) 0.43380(9) 0.01360(15) Uani 1 1 d . .
H1 H 0.771892 0.789004 0.387292 0.016 Uiso 1 1 calc R U
C2 C 0.99640(10) 0.89352(9) 0.38515(8) 0.01270(14) Uani 1 1 d . .
C3 C 0.86496(9) 0.97888(9) 0.54893(9) 0.01288(14) Uani 1 1 d . .
C21 C 0.98866(10) 0.77702(9) 0.26350(9) 0.01420(15) Uani 1 1 d . .
O21 O 1.06552(9) 0.79536(8) 0.18743(7) 0.02009(14) Uani 1 1 d . .
C22 C 0.86027(11) 0.52518(10) 0.13057(9) 0.01733(16) Uani 1 1 d . .
H22A H 0.825635 0.430728 0.151513 0.021 Uiso 1 1 calc R U
H22B H 0.968522 0.532563 0.118045 0.021 Uiso 1 1 calc R U
O22 O 0.88239(8) 0.64595(7) 0.24769(7) 0.01675(13) Uani 1 1 d . .
C23 C 0.73352(10) 0.52158(9) -0.00363(9) 0.01444(15) Uani 1 1 d . .
C24 C 0.68734(11) 0.39694(10) -0.11758(10) 0.01845(17) Uani 1 1 d . .
H24 H 0.737249 0.319801 -0.108365 0.022 Uiso 1 1 calc R U
C25 C 0.56912(12) 0.38463(11) -0.24429(10) 0.02223(19) Uani 1 1 d . .
H25 H 0.537712 0.298984 -0.321142 0.027 Uiso 1 1 calc R U
C26 C 0.49670(12) 0.49777(12) -0.25866(10) 0.02337(19) Uani 1 1 d . .
H26 H 0.416128 0.489821 -0.345413 0.028 Uiso 1 1 calc R U
C27 C 0.54245(11) 0.62237(11) -0.14588(10) 0.02061(18) Uani 1 1 d . .
H27 H 0.493624 0.700074 -0.155664 0.025 Uiso 1 1 calc R U
C28 C 0.65974(11) 0.63373(10) -0.01843(10) 0.01669(16) Uani 1 1 d . .
H28 H 0.689479 0.718597 0.058823 0.020 Uiso 1 1 calc R U
C31 C 0.72469(10) 0.95050(10) 0.59122(9) 0.01511(15) Uani 1 1 d . .
C32 C 0.60118(10) 0.91678(10) 0.61988(9) 0.01585(16) Uani 1 1 d . .
C33 C 0.45695(10) 0.88037(9) 0.65614(9) 0.01384(15) Uani 1 1 d . .
C34 C 0.44521(10) 0.96825(9) 0.77538(9) 0.01537(15) Uani 1 1 d . .
H34 H 0.535143 1.053708 0.833099 0.018 Uiso 1 1 calc R U
C35 C 0.30531(11) 0.93303(9) 0.81065(9) 0.01512(15) Uani 1 1 d . .
H35 H 0.301118 0.994422 0.892234 0.018 Uiso 1 1 calc R U
C36 C 0.16842(10) 0.80702(9) 0.72714(9) 0.01281(14) Uani 1 1 d . .
N36 N 0.02928(10) 0.77127(8) 0.76069(9) 0.01826(15) Uani 1 1 d . .
C37 C 0.18176(10) 0.71852(10) 0.60793(9) 0.01479(15) Uani 1 1 d . .
H37 H 0.092685 0.632464 0.550119 0.018 Uiso 1 1 calc R U
C38 C 0.32221(10) 0.75494(10) 0.57392(9) 0.01523(15) Uani 1 1 d . .
H38 H 0.327461 0.693467 0.492888 0.018 Uiso 1 1 calc R U
C39 C 0.01467(13) 0.86673(11) 0.88041(10) 0.02147(18) Uani 1 1 d . .
H39A H -0.091048 0.823301 0.890067 0.032 Uiso 1 1 calc R U
H39B H 0.017989 0.964580 0.867143 0.032 Uiso 1 1 calc R U
H39C H 0.107222 0.876719 0.964831 0.032 Uiso 1 1 calc R U
C40 C -0.11370(11) 0.64747(10) 0.66885(11) 0.02040(18) Uani 1 1 d . .
H40A H -0.203746 0.642109 0.706143 0.031 Uiso 1 1 calc R U
H40B H -0.082638 0.555384 0.662317 0.031 Uiso 1 1 calc R U
H40C H -0.151417 0.661185 0.575948 0.031 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C3 122.27(7) . .
C2 C1 H1 118.9 . .
C3 C1 H1 118.9 . .
C1 C2 C3 120.05(7) . 2_776
C1 C2 C21 119.18(7) . .
C3 C2 C21 120.77(7) 2_776 .
C1 C3 C2 117.67(7) . 2_776
C1 C3 C31 118.29(7) . .
C2 C3 C31 124.04(8) 2_776 .
O21 C21 O22 123.61(8) . .
O21 C21 C2 125.34(8) . .
O22 C21 C2 111.04(7) . .
O22 C22 C23 113.69(7) . .
O22 C22 H22A 108.8 . .
C23 C22 H22A 108.8 . .
O22 C22 H22B 108.8 . .
C23 C22 H22B 108.8 . .
H22A C22 H22B 107.7 . .
C21 O22 C22 116.28(7) . .
C28 C23 C24 119.17(8) . .
C28 C23 C22 123.54(8) . .
C24 C23 C22 117.28(8) . .
C25 C24 C23 120.59(9) . .
C25 C24 H24 119.7 . .
C23 C24 H24 119.7 . .
C24 C25 C26 119.93(9) . .
C24 C25 H25 120.0 . .
C26 C25 H25 120.0 . .
C27 C26 C25 119.81(9) . .
C27 C26 H26 120.1 . .
C25 C26 H26 120.1 . .
C26 C27 C28 120.14(9) . .
C26 C27 H27 119.9 . .
C28 C27 H27 119.9 . .
C23 C28 C27 120.35(8) . .
C23 C28 H28 119.8 . .
C27 C28 H28 119.8 . .
C32 C31 C3 175.34(9) . .
C31 C32 C33 178.63(10) . .
C38 C33 C34 117.68(7) . .
C38 C33 C32 120.99(8) . .
C34 C33 C32 121.32(8) . .
C35 C34 C33 121.37(8) . .
C35 C34 H34 119.3 . .
C33 C34 H34 119.3 . .
C34 C35 C36 121.06(8) . .
C34 C35 H35 119.5 . .
C36 C35 H35 119.5 . .
N36 C36 C37 121.17(8) . .
N36 C36 C35 121.61(7) . .
C37 C36 C35 117.21(7) . .
C36 N36 C40 120.62(7) . .
C36 N36 C39 120.48(8) . .
C40 N36 C39 118.52(7) . .
C38 C37 C36 121.12(8) . .
C38 C37 H37 119.4 . .
C36 C37 H37 119.4 . .
C37 C38 C33 121.54(8) . .
C37 C38 H38 119.2 . .
C33 C38 H38 119.2 . .
N36 C39 H39A 109.5 . .
N36 C39 H39B 109.5 . .
H39A C39 H39B 109.5 . .
N36 C39 H39C 109.5 . .
H39A C39 H39C 109.5 . .
H39B C39 H39C 109.5 . .
N36 C40 H40A 109.5 . .
N36 C40 H40B 109.5 . .
H40A C40 H40B 109.5 . .
N36 C40 H40C 109.5 . .
H40A C40 H40C 109.5 . .
H40B C40 H40C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3911(11) .
C1 C3 1.3998(12) .
C1 H1 0.9500 .
C2 C3 1.4100(11) 2_776
C2 C21 1.4888(12) .
C3 C31 1.4250(11) .
C21 O21 1.2074(10) .
C21 O22 1.3498(10) .
C22 O22 1.4393(11) .
C22 C23 1.5037(12) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C28 1.3895(12) .
C23 C24 1.3948(12) .
C24 C25 1.3878(14) .
C24 H24 0.9500 .
C25 C26 1.3904(15) .
C25 H25 0.9500 .
C26 C27 1.3880(14) .
C26 H26 0.9500 .
C27 C28 1.3924(13) .
C27 H27 0.9500 .
C28 H28 0.9500 .
C31 C32 1.2101(11) .
C32 C33 1.4265(11) .
C33 C38 1.4005(12) .
C33 C34 1.4030(12) .
C34 C35 1.3842(11) .
C34 H34 0.9500 .
C35 C36 1.4152(12) .
C35 H35 0.9500 .
C36 N36 1.3682(10) .
C36 C37 1.4120(11) .
N36 C40 1.4487(12) .
N36 C39 1.4521(12) .
C37 C38 1.3822(11) .
C37 H37 0.9500 .
C38 H38 0.9500 .
C39 H39A 0.9800 .
C39 H39B 0.9800 .
C39 H39C 0.9800 .
C40 H40A 0.9800 .
C40 H40B 0.9800 .
C40 H40C 0.9800 .
