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#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/46/1514648.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_1514648
loop_
_publ_author_name
'Koenig, Matthias'
'Bottari, Giovanni'
'Brancato, Giuseppe'
'Barone, Vincenzo'
'Guldi, Dirk M.'
'Torres, Tomás'
_publ_section_title
;
 Unraveling the peculiar modus operandi of a new class of solvatochromic
 fluorescent molecular rotors by spectroscopic and quantum mechanical
 methods
;
_journal_issue                   6
_journal_name_full               'Chemical Science'
_journal_page_first              2502
_journal_paper_doi               10.1039/c3sc50290b
_journal_volume                  4
_journal_year                    2013
_chemical_formula_sum            'C20.5 H13 Cl N3'
_chemical_formula_weight         336.79
_chemical_name_common            DPAP
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                94.129(5)
_cell_angle_beta                 99.175(4)
_cell_angle_gamma                114.976(4)
_cell_formula_units_Z            2
_cell_length_a                   8.1851(4)
_cell_length_b                   8.5344(5)
_cell_length_c                   13.5521(9)
_cell_measurement_temperature    100.(2)
_cell_volume                     836.84(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.(2)
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.948
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9154
_diffrn_reflns_theta_full        67.37
_diffrn_reflns_theta_max         67.37
_diffrn_reflns_theta_min         3.34
_exptl_absorpt_coefficient_mu    2.058
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.646
_refine_diff_density_min         -1.028
_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     278
_refine_ls_number_reflns         2854
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0598
_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)+(0.0847P)²+1.0465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1614
_refine_ls_wR_factor_ref         0.1682
_reflns_number_gt                2520
_reflns_number_total             2854
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc50290b.txt
_cod_data_source_block           I
_cod_original_cell_volume        836.84(8)
_cod_original_formula_sum        'C20.50 H13 Cl N3'
_cod_database_code               1514648
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 0.1673(3) 0.1868(3) 0.38509(18) 0.0222(5) Uani d . 1
C C2 0.1705(3) 0.3522(3) 0.40424(18) 0.0214(5) Uani d . 1
C C3 0.2505(3) 0.4524(3) 0.49982(18) 0.0213(5) Uani d . 1
C C4 0.3288(3) 0.3911(3) 0.57858(18) 0.0224(5) Uani d . 1
C C5 0.3221(4) 0.2256(3) 0.55896(19) 0.0254(6) Uani d . 1
C C6 0.2429(4) 0.1249(3) 0.46482(19) 0.0255(6) Uani d . 1
C C7 0.2541(3) 0.6227(3) 0.51838(18) 0.0246(6) Uani d . 1
C C8 0.4164(3) 0.4975(3) 0.67653(19) 0.0260(6) Uani d . 1
C C9 0.1278(3) -0.0620(3) 0.26508(17) 0.0230(5) Uani d . 1
C C10 0.3041(4) -0.0405(4) 0.26098(19) 0.0271(6) Uani d . 1
C C11 0.3309(4) -0.1862(4) 0.2317(2) 0.0323(6) Uani d . 1
C C12 0.1837(5) -0.3508(4) 0.2077(2) 0.0345(7) Uani d . 1
C C13 0.0093(5) -0.3716(4) 0.2128(2) 0.0374(7) Uani d . 1
C C14 -0.0203(4) -0.2273(4) 0.2409(2) 0.0300(6) Uani d . 1
C C15 -0.0145(3) 0.1260(3) 0.21065(18) 0.0229(5) Uani d . 1
C C16 0.0428(4) 0.1523(4) 0.11962(19) 0.0276(6) Uani d . 1
C C17 -0.0658(4) 0.1789(4) 0.0395(2) 0.0306(6) Uani d . 1
C C18 -0.2307(4) 0.1799(3) 0.0501(2) 0.0302(6) Uani d . 1
C C19 -0.2860(4) 0.1565(3) 0.1414(2) 0.0285(6) Uani d . 1
C C20 -0.1790(4) 0.1292(3) 0.22210(19) 0.0250(6) Uani d . 1
C C21 0.6106(9) 0.5111(9) 0.0041(5) 0.0463(16) Uani d P 0.5
N N1 0.0941(3) 0.0871(3) 0.29039(15) 0.0235(5) Uani d . 1
N N2 0.2588(3) 0.7583(3) 0.53531(18) 0.0334(6) Uani d . 1
N N3 0.4861(3) 0.5810(3) 0.75489(17) 0.0345(6) Uani d . 1
Cl Cl1 0.59869(12) 0.68944(13) 0.04061(6) 0.0552(3) Uani d . 1
H H2 0.120(4) 0.395(4) 0.354(2) 0.020(7) Uiso d . 1
H H5 0.377(4) 0.189(4) 0.608(2) 0.027(7) Uiso d . 1
H H6 0.239(4) 0.019(4) 0.455(2) 0.030(8) Uiso d . 1
H H10 0.396(5) 0.070(5) 0.278(2) 0.031(8) Uiso d . 1
H H11 0.451(5) -0.175(5) 0.227(3) 0.042(9) Uiso d . 1
H H12 0.200(4) -0.443(5) 0.188(2) 0.035(8) Uiso d . 1
H H13 -0.082(5) -0.477(5) 0.198(2) 0.034(8) Uiso d . 1
H H14 -0.139(5) -0.238(4) 0.242(2) 0.031(8) Uiso d . 1
H H16 0.155(5) 0.155(4) 0.113(2) 0.036(8) Uiso d . 1
H H17 -0.023(4) 0.200(4) -0.022(2) 0.031(8) Uiso d . 1
H H18 -0.301(4) 0.203(4) -0.004(2) 0.027(7) Uiso d . 1
H H19 -0.393(5) 0.158(4) 0.149(2) 0.030(8) Uiso d . 1
H H20 -0.213(4) 0.116(4) 0.281(2) 0.028(7) Uiso d . 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N1 C1 C2 . . 121.4(2)
N1 C1 C6 . . 120.1(2)
C2 C1 C6 . . 118.5(2)
C3 C2 C1 . . 120.2(2)
C3 C2 H2 . . 119.5(17)
C1 C2 H2 . . 120.4(17)
C2 C3 C4 . . 121.0(2)
C2 C3 C7 . . 119.6(2)
C4 C3 C7 . . 119.4(2)
C5 C4 C3 . . 118.2(2)
C5 C4 C8 . . 120.9(2)
C3 C4 C8 . . 120.8(2)
C6 C5 C4 . . 121.3(2)
C6 C5 H5 . . 120.5(19)
C4 C5 H5 . . 118.1(19)
C5 C6 C1 . . 120.8(2)
C5 C6 H6 . . 119.(2)
C1 C6 H6 . . 120.(2)
N2 C7 C3 . . 178.5(3)
N3 C8 C4 . . 179.4(3)
C10 C9 C14 . . 120.3(2)
C10 C9 N1 . . 120.6(2)
C14 C9 N1 . . 119.0(2)
C9 C10 C11 . . 119.3(3)
C9 C10 H10 . . 117.(2)
C11 C10 H10 . . 124.(2)
C12 C11 C10 . . 120.4(3)
C12 C11 H11 . . 118.(2)
C10 C11 H11 . . 121.(2)
C13 C12 C11 . . 120.0(3)
C13 C12 H12 . . 120.(2)
C11 C12 H12 . . 120.(2)
C12 C13 C14 . . 120.3(3)
C12 C13 H13 . . 119.(2)
C14 C13 H13 . . 121.(2)
C9 C14 C13 . . 119.6(3)
C9 C14 H14 . . 119.(2)
C13 C14 H14 . . 122.(2)
C16 C15 C20 . . 120.2(2)
C16 C15 N1 . . 118.8(2)
C20 C15 N1 . . 120.9(2)
C17 C16 C15 . . 119.8(3)
C17 C16 H16 . . 120.(2)
C15 C16 H16 . . 120.(2)
C18 C17 C16 . . 120.2(3)
C18 C17 H17 . . 120.9(18)
C16 C17 H17 . . 118.9(18)
C19 C18 C17 . . 119.9(2)
C19 C18 H18 . . 120.7(18)
C17 C18 H18 . . 119.3(18)
C18 C19 C20 . . 120.5(3)
C18 C19 H19 . . 120.4(19)
C20 C19 H19 . . 119.1(19)
C19 C20 C15 . . 119.4(2)
C19 C20 H20 . . 121.(2)
C15 C20 H20 . . 119.6(19)
Cl1 C21 C21 . 2_665 65.6(4)
Cl1 C21 Cl1 . 2_665 119.9(4)
C21 C21 Cl1 2_665 2_665 54.3(3)
C1 N1 C15 . . 123.1(2)
C1 N1 C9 . . 121.0(2)
C15 N1 C9 . . 115.92(19)
C21 Cl1 C21 . 2_665 60.1(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.377(3)
C1 C2 . 1.405(3)
C1 C6 . 1.405(4)
C2 C3 . 1.391(3)
C2 H2 . 0.92(3)
C3 C4 . 1.404(4)
C3 C7 . 1.444(4)
C4 C5 . 1.394(4)
C4 C8 . 1.440(3)
C5 C6 . 1.376(4)
C5 H5 . 0.89(3)
C6 H6 . 0.89(3)
C7 N2 . 1.146(4)
C8 N3 . 1.147(3)
C9 C10 . 1.387(4)
C9 C14 . 1.389(4)
C9 N1 . 1.440(3)
C10 C11 . 1.393(4)
C10 H10 . 0.91(3)
C11 C12 . 1.382(4)
C11 H11 . 0.96(4)
C12 C13 . 1.376(5)
C12 H12 . 0.88(3)
C13 C14 . 1.390(4)
C13 H13 . 0.88(4)
C14 H14 . 0.94(3)
C15 C16 . 1.389(4)
C15 C20 . 1.391(4)
C15 N1 . 1.436(3)
C16 C17 . 1.386(4)
C16 H16 . 0.93(3)
C17 C18 . 1.383(4)
C17 H17 . 0.95(3)
C18 C19 . 1.383(4)
C18 H18 . 0.94(3)
C19 C20 . 1.387(4)
C19 H19 . 0.91(3)
C20 H20 . 0.88(3)
C21 Cl1 . 1.613(7)
C21 C21 2_665 1.723(13)
C21 Cl1 2_665 1.809(6)
Cl1 C21 2_665 1.809(6)
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
N1 C1 C2 C3 . . -178.0(2)
C6 C1 C2 C3 . . 1.2(4)
C1 C2 C3 C4 . . 0.0(4)
C1 C2 C3 C7 . . 179.6(2)
C2 C3 C4 C5 . . -0.9(4)
C7 C3 C4 C5 . . 179.4(2)
C2 C3 C4 C8 . . 178.1(2)
C7 C3 C4 C8 . . -1.5(4)
C3 C4 C5 C6 . . 0.7(4)
C8 C4 C5 C6 . . -178.3(2)
C4 C5 C6 C1 . . 0.4(4)
N1 C1 C6 C5 . . 177.8(2)
C2 C1 C6 C5 . . -1.4(4)
C2 C3 C7 N2 . . 180.(100)
C4 C3 C7 N2 . . -2.(11)
C5 C4 C8 N3 . . -10.(30)
C3 C4 C8 N3 . . 170.(100)
C14 C9 C10 C11 . . 0.5(4)
N1 C9 C10 C11 . . -177.0(2)
C9 C10 C11 C12 . . -0.5(4)
C10 C11 C12 C13 . . -0.1(4)
C11 C12 C13 C14 . . 0.8(4)
C10 C9 C14 C13 . . 0.2(4)
N1 C9 C14 C13 . . 177.7(2)
C12 C13 C14 C9 . . -0.8(4)
C20 C15 C16 C17 . . -1.1(4)
N1 C15 C16 C17 . . 175.9(2)
C15 C16 C17 C18 . . 0.2(4)
C16 C17 C18 C19 . . 0.9(4)
C17 C18 C19 C20 . . -1.1(4)
C18 C19 C20 C15 . . 0.2(4)
C16 C15 C20 C19 . . 0.9(4)
N1 C15 C20 C19 . . -176.0(2)
C2 C1 N1 C15 . . -12.5(4)
C6 C1 N1 C15 . . 168.4(2)
C2 C1 N1 C9 . . 165.8(2)
C6 C1 N1 C9 . . -13.4(4)
C16 C15 N1 C1 . . 122.6(3)
C20 C15 N1 C1 . . -60.4(3)
C16 C15 N1 C9 . . -55.8(3)
C20 C15 N1 C9 . . 121.2(2)
C10 C9 N1 C1 . . -65.7(3)
C14 C9 N1 C1 . . 116.8(3)
C10 C9 N1 C15 . . 112.7(3)
C14 C9 N1 C15 . . -64.8(3)
Cl1 C21 Cl1 C21 2_665 2_665 0
