#------------------------------------------------------------------------------
#$Date: 2019-11-24 03:07:50 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236403 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/39/1553998.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_1553998
loop_
_publ_author_name
'Pati, Avik Kumar'
'Gharpure, Santosh J.'
'Mishra, Ashok K.'
_publ_section_title
;
 Contrasting Solid-State Fluorescence of Diynes with Small and Large Aryl
 Substituents: Crystal Packing Dependence and Stimuli-Responsive
 Fluorescence Switching.
;
_journal_issue                   42
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              10481
_journal_page_last               10493
_journal_paper_doi               10.1021/acs.jpca.5b08445
_journal_volume                  119
_journal_year                    2015
_chemical_formula_sum            'C29 H21 Cl N'
_chemical_formula_weight         418.92
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                100.318(5)
_cell_angle_beta                 90.072(5)
_cell_angle_gamma                96.899(5)
_cell_formula_units_Z            2
_cell_length_a                   9.9486(11)
_cell_length_b                   10.0790(15)
_cell_length_c                   10.8072(15)
_cell_measurement_reflns_used    1859
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.36
_cell_measurement_theta_min      2.55
_cell_volume                     1058.1(2)
_computing_cell_refinement       'APEXII/SAINT (Bruker, 2004)'
_computing_data_collection       'APEXII (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997) '
_computing_publication_material  'SHELXL-97 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.793
_diffrn_measured_fraction_theta_max 0.816
_diffrn_measurement_device_type  'Bruker Kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.793
_diffrn_reflns_Laue_measured_fraction_max 0.816
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9509
_diffrn_reflns_point_group_measured_fraction_full 0.793
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.984
_diffrn_reflns_theta_min         2.069
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  9833
_exptl_absorpt_correction_T_min  9416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_crystal_colour            bluish-green
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       block
_exptl_crystal_F_000             438
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3031
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0595
_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)+(0.1199P)²+0.2918P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1771
_refine_ls_wR_factor_ref         0.2056
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1960
_reflns_number_total             3031
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Avik_CIF_4.cif
_cod_data_source_block           shelxl
_cod_database_code               1553998
_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   0.965
_shelx_estimated_absorpt_t_max   0.981
_shelxl_version_number           2012-9
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C29 C 0.0512(8) 0.9505(7) 0.4387(7) 0.181(3) Uani 1 1 d D U A 1
H29A H 0.1224 0.8977 0.4549 0.218 Uiso 1 1 calc R U A 1
H29B H 0.0343 0.9339 0.3485 0.218 Uiso 1 1 calc R U A 1
Cl1 Cl 0.10397(14) 1.10978(17) 0.48458(16) 0.1255(6) Uani 1 1 d D U A 1
C1 C 0.1911(3) 0.0395(3) 1.0891(3) 0.0527(9) Uani 1 1 d . . B 1
H1 H 0.0987 0.0117 1.0770 0.063 Uiso 1 1 calc R U B 1
C2 C 0.2651(3) -0.0241(3) 1.1624(3) 0.0519(8) Uani 1 1 d . . B 1
H2 H 0.2227 -0.0946 1.1988 0.062 Uiso 1 1 calc R U B 1
C3 C 0.4041(3) 0.0158(3) 1.1831(3) 0.0437(8) Uani 1 1 d . . B 1
C4 C 0.4847(4) -0.0481(3) 1.2606(3) 0.0568(9) Uani 1 1 d . . B 1
H4 H 0.4438 -0.1184 1.2981 0.068 Uiso 1 1 calc R U B 1
C5 C 0.6169(4) -0.0082(4) 1.2793(3) 0.0628(10) Uani 1 1 d . . B 1
H5 H 0.6663 -0.0516 1.3296 0.075 Uiso 1 1 calc R U B 1
C6 C 0.6846(3) 0.0986(4) 1.2247(3) 0.0525(9) Uani 1 1 d . . B 1
C7 C 0.8236(4) 0.1417(5) 1.2411(4) 0.0715(11) Uani 1 1 d . . B 1
H7 H 0.8751 0.0991 1.2904 0.086 Uiso 1 1 calc R U B 1
C8 C 0.8853(4) 0.2438(5) 1.1872(4) 0.0782(12) Uani 1 1 d . . B 1
H8 H 0.9779 0.2696 1.2002 0.094 Uiso 1 1 calc R U B 1
C9 C 0.8135(4) 0.3097(4) 1.1138(4) 0.0702(11) Uani 1 1 d . . B 1
H9 H 0.8573 0.3799 1.0779 0.084 Uiso 1 1 calc R U B 1
C10 C 0.6734(3) 0.2713(3) 1.0926(3) 0.0518(9) Uani 1 1 d . . B 1
C11 C 0.5927(4) 0.3345(3) 1.0152(3) 0.0594(9) Uani 1 1 d . . B 1
H11 H 0.6340 0.4044 0.9776 0.071 Uiso 1 1 calc R U B 1
C12 C 0.4591(4) 0.2954(3) 0.9956(3) 0.0523(9) Uani 1 1 d . . B 1
H12 H 0.4103 0.3393 0.9452 0.063 Uiso 1 1 calc R U B 1
C13 C 0.3904(3) 0.1879(3) 1.0504(3) 0.0406(7) Uani 1 1 d . . B 1
C14 C 0.4672(3) 0.1224(3) 1.1271(3) 0.0376(7) Uani 1 1 d . . B 1
C15 C 0.6088(3) 0.1644(3) 1.1474(3) 0.0434(8) Uani 1 1 d . . B 1
C16 C 0.2504(3) 0.1447(3) 1.0325(3) 0.0447(8) Uani 1 1 d . . B 1
C17 C 0.1690(3) 0.2079(3) 0.9557(3) 0.0537(9) Uani 1 1 d . . B 1
C18 C 0.0972(3) 0.2595(3) 0.8938(3) 0.0522(9) Uani 1 1 d . . B 1
C19 C 0.0157(3) 0.3191(3) 0.8237(3) 0.0520(9) Uani 1 1 d . . B 1
C20 C -0.0548(3) 0.3709(3) 0.7610(3) 0.0525(9) Uani 1 1 d . . B 1
C21 C -0.1375(3) 0.4339(3) 0.6851(3) 0.0470(8) Uani 1 1 d . . B 1
C22 C -0.1364(3) 0.4041(4) 0.5548(3) 0.0614(10) Uani 1 1 d . . B 1
H22 H -0.0832 0.3395 0.5160 0.074 Uiso 1 1 calc R U B 1
C23 C -0.2117(3) 0.4673(4) 0.4813(3) 0.0585(10) Uani 1 1 d . . B 1
H23 H -0.2073 0.4457 0.3941 0.070 Uiso 1 1 calc R U B 1
C24 C -0.2946(3) 0.5633(3) 0.5353(3) 0.0425(8) Uani 1 1 d . . B 1
C25 C -0.2945(3) 0.5939(3) 0.6670(3) 0.0496(8) Uani 1 1 d . . B 1
H25 H -0.3470 0.6589 0.7064 0.060 Uiso 1 1 calc R U B 1
C26 C -0.2186(3) 0.5303(3) 0.7390(3) 0.0522(9) Uani 1 1 d . . B 1
H26 H -0.2216 0.5524 0.8262 0.063 Uiso 1 1 calc R U B 1
C27 C -0.3641(4) 0.6006(4) 0.3281(3) 0.0684(11) Uani 1 1 d . . B 1
H27A H -0.2766 0.6378 0.3044 0.103 Uiso 1 1 calc R U B 1
H27B H -0.4329 0.6431 0.2932 0.103 Uiso 1 1 calc R U B 1
H27C H -0.3777 0.5045 0.2966 0.103 Uiso 1 1 calc R U B 1
C28 C -0.4553(4) 0.7255(4) 0.5189(3) 0.0646(10) Uani 1 1 d . . B 1
H28A H -0.5068 0.6931 0.5849 0.097 Uiso 1 1 calc R U B 1
H28B H -0.5159 0.7424 0.4559 0.097 Uiso 1 1 calc R U B 1
H28C H -0.3990 0.8081 0.5531 0.097 Uiso 1 1 calc R U B 1
N1 N -0.3720(3) 0.6250(3) 0.4633(2) 0.0537(8) Uani 1 1 d . . B 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'
Cl Cl 0.1484 0.1585 '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
Cl1 C29 Cl1 114.2(4) . 2_576
Cl1 C29 C29 62.9(4) . 2_576
Cl1 C29 C29 51.3(4) 2_576 2_576
Cl1 C29 H29A 108.7 . .
Cl1 C29 H29A 108.7 2_576 .
C29 C29 H29A 126.0 2_576 .
Cl1 C29 H29B 108.7 . .
Cl1 C29 H29B 108.7 2_576 .
C29 C29 H29B 126.0 2_576 .
H29A C29 H29B 107.6 . .
C29 Cl1 C29 65.8(4) . 2_576
C2 C1 C16 121.7(3) . .
C2 C1 H1 119.1 . .
C16 C1 H1 119.1 . .
C1 C2 C3 120.6(3) . .
C1 C2 H2 119.7 . .
C3 C2 H2 119.7 . .
C2 C3 C14 119.0(3) . .
C2 C3 C4 122.0(3) . .
C14 C3 C4 118.9(3) . .
C5 C4 C3 121.0(3) . .
C5 C4 H4 119.5 . .
C3 C4 H4 119.5 . .
C4 C5 C6 122.0(3) . .
C4 C5 H5 119.0 . .
C6 C5 H5 119.0 . .
C7 C6 C5 123.4(3) . .
C7 C6 C15 117.8(4) . .
C5 C6 C15 118.8(3) . .
C8 C7 C6 121.9(4) . .
C8 C7 H7 119.1 . .
C6 C7 H7 119.1 . .
C7 C8 C9 121.1(4) . .
C7 C8 H8 119.4 . .
C9 C8 H8 119.4 . .
C8 C9 C10 120.1(4) . .
C8 C9 H9 120.0 . .
C10 C9 H9 120.0 . .
C9 C10 C15 119.1(3) . .
C9 C10 C11 122.9(3) . .
C15 C10 C11 118.0(3) . .
C12 C11 C10 121.9(3) . .
C12 C11 H11 119.1 . .
C10 C11 H11 119.1 . .
C11 C12 C13 121.5(3) . .
C11 C12 H12 119.3 . .
C13 C12 H12 119.3 . .
C16 C13 C14 118.7(3) . .
C16 C13 C12 123.1(3) . .
C14 C13 C12 118.2(3) . .
C3 C14 C13 120.3(3) . .
C3 C14 C15 119.7(3) . .
C13 C14 C15 119.9(3) . .
C10 C15 C6 120.0(3) . .
C10 C15 C14 120.5(3) . .
C6 C15 C14 119.5(3) . .
C1 C16 C13 119.6(3) . .
C1 C16 C17 119.8(3) . .
C13 C16 C17 120.6(3) . .
C18 C17 C16 177.8(4) . .
C17 C18 C19 179.6(4) . .
C20 C19 C18 179.2(4) . .
C19 C20 C21 179.1(4) . .
C22 C21 C26 117.1(3) . .
C22 C21 C20 121.5(3) . .
C26 C21 C20 121.4(3) . .
C23 C22 C21 121.9(3) . .
C23 C22 H22 119.0 . .
C21 C22 H22 119.0 . .
C22 C23 C24 121.1(3) . .
C22 C23 H23 119.5 . .
C24 C23 H23 119.5 . .
N1 C24 C23 121.7(3) . .
N1 C24 C25 121.5(3) . .
C23 C24 C25 116.8(3) . .
C26 C25 C24 121.4(3) . .
C26 C25 H25 119.3 . .
C24 C25 H25 119.3 . .
C25 C26 C21 121.6(3) . .
C25 C26 H26 119.2 . .
C21 C26 H26 119.2 . .
N1 C27 H27A 109.5 . .
N1 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
N1 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
N1 C28 H28A 109.5 . .
N1 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
N1 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
C24 N1 C28 121.7(3) . .
C24 N1 C27 121.2(3) . .
C28 N1 C27 116.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C29 Cl1 1.616(7) .
C29 Cl1 1.843(8) 2_576
C29 C29 1.888(13) 2_576
C29 H29A 0.9700 .
C29 H29B 0.9700 .
Cl1 C29 1.843(8) 2_576
C1 C2 1.370(4) .
C1 C16 1.389(4) .
C1 H1 0.9300 .
C2 C3 1.399(4) .
C2 H2 0.9300 .
C3 C14 1.409(4) .
C3 C4 1.440(4) .
C4 C5 1.333(5) .
C4 H4 0.9300 .
C5 C6 1.419(5) .
C5 H5 0.9300 .
C6 C7 1.400(5) .
C6 C15 1.423(4) .
C7 C8 1.356(6) .
C7 H7 0.9300 .
C8 C9 1.373(6) .
C8 H8 0.9300 .
C9 C10 1.408(5) .
C9 H9 0.9300 .
C10 C15 1.410(4) .
C10 C11 1.435(5) .
C11 C12 1.346(5) .
C11 H11 0.9300 .
C12 C13 1.430(4) .
C12 H12 0.9300 .
C13 C16 1.411(4) .
C13 C14 1.422(4) .
C14 C15 1.426(4) .
C16 C17 1.436(4) .
C17 C18 1.200(4) .
C18 C19 1.367(5) .
C19 C20 1.200(4) .
C20 C21 1.436(4) .
C21 C22 1.386(4) .
C21 C26 1.386(4) .
C22 C23 1.377(4) .
C22 H22 0.9300 .
C23 C24 1.395(4) .
C23 H23 0.9300 .
C24 N1 1.368(4) .
C24 C25 1.401(4) .
C25 C26 1.372(4) .
C25 H25 0.9300 .
C26 H26 0.9300 .
C27 N1 1.442(4) .
C27 H27A 0.9600 .
C27 H27B 0.9600 .
C27 H27C 0.9600 .
C28 N1 1.435(4) .
C28 H28A 0.9600 .
C28 H28B 0.9600 .
C28 H28C 0.9600 .
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_4
Cl1 C29 Cl1 C29 -0.002(1) 2_576 2_576
C16 C1 C2 C3 0.3(5) . .
C1 C2 C3 C14 -0.2(4) . .
C1 C2 C3 C4 179.4(3) . .
C2 C3 C4 C5 -179.8(3) . .
C14 C3 C4 C5 -0.2(5) . .
C3 C4 C5 C6 0.2(5) . .
C4 C5 C6 C7 -179.1(3) . .
C4 C5 C6 C15 -0.2(5) . .
C5 C6 C7 C8 179.7(3) . .
C15 C6 C7 C8 0.9(5) . .
C6 C7 C8 C9 0.0(6) . .
C7 C8 C9 C10 -0.4(6) . .
C8 C9 C10 C15 -0.2(5) . .
C8 C9 C10 C11 -179.0(3) . .
C9 C10 C11 C12 179.5(3) . .
C15 C10 C11 C12 0.7(5) . .
C10 C11 C12 C13 -0.4(5) . .
C11 C12 C13 C16 179.6(3) . .
C11 C12 C13 C14 0.0(4) . .
C2 C3 C14 C13 -0.2(4) . .
C4 C3 C14 C13 -179.8(3) . .
C2 C3 C14 C15 179.9(3) . .
C4 C3 C14 C15 0.3(4) . .
C16 C13 C14 C3 0.4(4) . .
C12 C13 C14 C3 -180.0(3) . .
C16 C13 C14 C15 -179.6(2) . .
C12 C13 C14 C15 0.0(4) . .
C9 C10 C15 C6 1.1(4) . .
C11 C10 C15 C6 179.9(3) . .
C9 C10 C15 C14 -179.5(3) . .
C11 C10 C15 C14 -0.7(4) . .
C7 C6 C15 C10 -1.4(4) . .
C5 C6 C15 C10 179.6(3) . .
C7 C6 C15 C14 179.2(3) . .
C5 C6 C15 C14 0.3(4) . .
C3 C14 C15 C10 -179.7(3) . .
C13 C14 C15 C10 0.4(4) . .
C3 C14 C15 C6 -0.3(4) . .
C13 C14 C15 C6 179.7(3) . .
C2 C1 C16 C13 -0.1(5) . .
C2 C1 C16 C17 179.5(3) . .
C14 C13 C16 C1 -0.3(4) . .
C12 C13 C16 C1 -179.9(3) . .
C14 C13 C16 C17 -179.9(3) . .
C12 C13 C16 C17 0.5(4) . .
C26 C21 C22 C23 0.3(5) . .
C20 C21 C22 C23 -177.7(3) . .
C21 C22 C23 C24 -1.0(6) . .
C22 C23 C24 N1 -178.7(3) . .
C22 C23 C24 C25 1.5(5) . .
N1 C24 C25 C26 178.8(3) . .
C23 C24 C25 C26 -1.3(5) . .
C24 C25 C26 C21 0.7(5) . .
C22 C21 C26 C25 -0.1(5) . .
C20 C21 C26 C25 177.9(3) . .
C23 C24 N1 C28 -178.8(3) . .
C25 C24 N1 C28 1.0(5) . .
C23 C24 N1 C27 -4.5(5) . .
C25 C24 N1 C27 175.3(3) . .
