#------------------------------------------------------------------------------
#$Date: 2021-07-24 07:06:26 +0300 (Sat, 24 Jul 2021) $
#$Revision: 267731 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/32/7243264.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_7243264
loop_
_publ_author_name
'Witte, Felix'
'Rietsch, Philipp'
'Nirmalananthan-Budau, Nithiya'
'Weigert, Florian'
'Götze, Jan Phillip'
'Resch-Genger, Ute'
'Eigler, Siegfried'
'Paulus, Beate'
_publ_section_title
;
 Aggregation-induced emission leading to two distinct emissive species in
 the solid-state structure of high-dipole organic chromophores
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D1CP02534A
_journal_year                    2021
_chemical_formula_sum            'C30 H26 N4 O4'
_chemical_formula_weight         506.55
_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-2017/1
_audit_update_record
;
2020-12-17 deposited with the CCDC.	2021-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                97.639(4)
_cell_angle_beta                 108.409(4)
_cell_angle_gamma                106.008(3)
_cell_formula_units_Z            2
_cell_length_a                   9.45250(10)
_cell_length_b                   11.1197(2)
_cell_length_c                   14.54330(10)
_cell_measurement_reflns_used    7292
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.55
_cell_measurement_theta_min      3.30
_cell_volume                     1352.99(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17026
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         66.750
_diffrn_reflns_theta_min         3.300
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       needle
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_exptl_transmission_factor_max   0.9791
_exptl_transmission_factor_min   0.8106
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0495
_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)+(0.0443P)²+0.9403P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1237
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3725
_reflns_number_total             4780
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cp02534a3.cif
_cod_data_source_block           PR111
_cod_original_cell_volume        1352.99(5)
_cod_database_code               7243264
_shelx_shelxl_version_number     2017/1
_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   0.806
_shelx_estimated_absorpt_t_max   0.960
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_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1908(2) 1.49922(19) 0.60640(15) 0.0179(4) Uani 1 1 d . . . . .
C2 C -0.2788(2) 1.57924(19) 0.57469(16) 0.0199(4) Uani 1 1 d . . . . .
H2 H -0.299572 1.632025 0.622228 0.024 Uiso 1 1 calc R U . . .
C3 C -0.3354(2) 1.58239(19) 0.47581(15) 0.0183(4) Uani 1 1 d . . . . .
H3 H -0.395626 1.636634 0.456084 0.022 Uiso 1 1 calc R U . . .
C4 C -0.3056(2) 1.50652(18) 0.40329(15) 0.0168(4) Uani 1 1 d . . . . .
C5 C -0.2137(2) 1.42894(19) 0.43642(15) 0.0183(4) Uani 1 1 d . . . . .
H5 H -0.189084 1.378562 0.389554 0.022 Uiso 1 1 calc R U . . .
C6 C -0.1590(2) 1.42466(19) 0.53484(16) 0.0196(4) Uani 1 1 d . . . . .
H6 H -0.098787 1.370460 0.554770 0.024 Uiso 1 1 calc R U . . .
C7 C -0.1351(2) 1.49273(19) 0.71034(15) 0.0181(4) Uani 1 1 d . . . . .
C8 C -0.3663(2) 1.50579(19) 0.29928(15) 0.0183(4) Uani 1 1 d . . . . .
C11 C -0.4659(2) 1.5765(2) 0.26202(15) 0.0194(4) Uani 1 1 d . . . . .
C12 C -0.3294(3) 1.4321(2) 0.22927(16) 0.0214(5) Uani 1 1 d . . . . .
C15 C -0.0305(3) 1.5533(2) 0.88316(16) 0.0246(5) Uani 1 1 d . . . . .
H15A H -0.088690 1.577170 0.924423 0.030 Uiso 1 1 calc R U . . .
H15B H 0.084744 1.592848 0.921952 0.030 Uiso 1 1 calc R U . . .
C16 C -0.0786(3) 1.4072(2) 0.84922(16) 0.0236(5) Uani 1 1 d . . . . .
H16A H 0.013436 1.378133 0.874368 0.028 Uiso 1 1 calc R U . . .
H16B H -0.162305 1.362801 0.872336 0.028 Uiso 1 1 calc R U . . .
C17 C -0.0080(3) 1.72783(19) 0.78639(16) 0.0209(5) Uani 1 1 d . . . . .
H17A H -0.017864 1.731910 0.717147 0.025 Uiso 1 1 calc R U . . .
H17B H 0.106272 1.760215 0.828385 0.025 Uiso 1 1 calc R U . . .
C18 C -0.2299(3) 1.25286(19) 0.67885(16) 0.0212(5) Uani 1 1 d . . . . .
H18A H -0.298531 1.257542 0.613016 0.025 Uiso 1 1 calc R U . . .
H18B H -0.299572 1.208676 0.711404 0.025 Uiso 1 1 calc R U . . .
C19 C -0.0858(2) 1.81513(19) 0.82294(15) 0.0187(4) Uani 1 1 d . . . . .
C20 C -0.0036(3) 1.9476(2) 0.85241(15) 0.0210(5) Uani 1 1 d . . . . .
H20 H 0.099521 1.979289 0.850734 0.025 Uiso 1 1 calc R U . . .
C21 C -0.0698(3) 2.0332(2) 0.88390(16) 0.0204(5) Uani 1 1 d . . . . .
H21 H -0.011655 2.123005 0.904641 0.024 Uiso 1 1 calc R U . . .
C22 C -0.2219(3) 1.9883(2) 0.88539(15) 0.0200(4) Uani 1 1 d . . . . .
C23 C -0.3048(3) 1.8558(2) 0.85620(16) 0.0218(5) Uani 1 1 d . . . . .
H23 H -0.408395 1.824117 0.857114 0.026 Uiso 1 1 calc R U . . .
C24 C -0.2363(3) 1.7706(2) 0.82590(16) 0.0216(5) Uani 1 1 d . . . . .
H24 H -0.292941 1.680545 0.806931 0.026 Uiso 1 1 calc R U . . .
C25 C -0.2878(3) 2.0851(2) 0.91892(15) 0.0206(5) Uani 1 1 d . . . . .
C26 C -0.5112(3) 2.1307(2) 0.9278(2) 0.0334(6) Uani 1 1 d . . . . .
H26A H -0.503680 2.193787 0.886879 0.050 Uiso 1 1 calc R U . . .
H26B H -0.453708 2.174990 0.998470 0.050 Uiso 1 1 calc R U . . .
H26C H -0.622808 2.087026 0.916248 0.050 Uiso 1 1 calc R U . . .
C27 C -0.1295(3) 1.17321(19) 0.66281(15) 0.0201(5) Uani 1 1 d . . . . .
C28 C 0.0343(3) 1.2252(2) 0.69528(16) 0.0230(5) Uani 1 1 d . . . . .
H28 H 0.086059 1.313932 0.728069 0.028 Uiso 1 1 calc R U . . .
C29 C 0.1234(3) 1.1495(2) 0.68060(16) 0.0224(5) Uani 1 1 d . . . . .
H29 H 0.235393 1.186465 0.703196 0.027 Uiso 1 1 calc R U . . .
C30 C 0.0487(3) 1.0191(2) 0.63268(15) 0.0199(4) Uani 1 1 d . . . . .
C31 C -0.1159(3) 0.9668(2) 0.59825(16) 0.0210(5) Uani 1 1 d . . . . .
H31 H -0.168062 0.878355 0.564450 0.025 Uiso 1 1 calc R U . . .
C32 C -0.2029(3) 1.0429(2) 0.61311(15) 0.0209(5) Uani 1 1 d . . . . .
H32 H -0.315100 1.006316 0.589161 0.025 Uiso 1 1 calc R U . . .
C33 C 0.1388(3) 0.9325(2) 0.62037(15) 0.0209(5) Uani 1 1 d . . . . .
C34 C 0.3911(3) 0.9153(2) 0.65350(19) 0.0309(5) Uani 1 1 d . . . . .
H34A H 0.360358 0.868963 0.584174 0.046 Uiso 1 1 calc R U . . .
H34B H 0.374727 0.853066 0.694194 0.046 Uiso 1 1 calc R U . . .
H34C H 0.503183 0.969145 0.679402 0.046 Uiso 1 1 calc R U . . .
N9 N -0.0751(2) 1.59345(16) 0.78812(13) 0.0191(4) Uani 1 1 d . . . . .
N10 N -0.1381(2) 1.38326(16) 0.73958(13) 0.0193(4) Uani 1 1 d . . . . .
N13 N -0.5476(2) 1.6347(2) 0.23250(15) 0.0298(5) Uani 1 1 d . . . . .
N14 N -0.2970(3) 1.3711(2) 0.17363(15) 0.0342(5) Uani 1 1 d . . . . .
O1 O -0.44238(18) 2.03631(14) 0.90055(12) 0.0291(4) Uani 1 1 d . . . . .
O2 O -0.20995(19) 2.19712(14) 0.95793(12) 0.0293(4) Uani 1 1 d . . . . .
O3 O 0.29623(18) 0.99528(14) 0.65751(12) 0.0263(4) Uani 1 1 d . . . . .
O4 O 0.08059(18) 0.81758(14) 0.58367(12) 0.0274(4) Uani 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 0.0181 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'
O O 0.0492 0.0322 '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
C6 C1 C2 118.15(19) . . ?
C6 C1 C7 120.73(18) . . ?
C2 C1 C7 121.11(18) . . ?
C3 C2 C1 121.01(19) . . ?
C2 C3 C4 121.13(19) . . ?
C3 C4 C5 117.34(19) . . ?
C3 C4 C8 122.24(18) . . ?
C5 C4 C8 120.42(18) . . ?
C6 C5 C4 121.45(19) . . ?
C5 C6 C1 120.88(19) . . ?
N9 C7 N10 111.32(18) . . ?
N9 C7 C1 124.84(18) . . ?
N10 C7 C1 123.84(18) . . ?
C12 C8 C11 116.99(18) . . ?
C12 C8 C4 120.67(18) . . ?
C11 C8 C4 122.33(18) . . ?
N13 C11 C8 179.3(2) . . ?
N14 C12 C8 178.5(2) . . ?
N9 C15 C16 103.27(17) . . ?
N10 C16 C15 103.17(16) . . ?
N9 C17 C19 113.86(17) . . ?
N10 C18 C27 113.76(18) . . ?
C24 C19 C20 118.7(2) . . ?
C24 C19 C17 123.24(19) . . ?
C20 C19 C17 117.99(19) . . ?
C21 C20 C19 121.0(2) . . ?
C20 C21 C22 120.16(19) . . ?
C21 C22 C23 119.2(2) . . ?
C21 C22 C25 117.77(19) . . ?
C23 C22 C25 123.0(2) . . ?
C24 C23 C22 120.2(2) . . ?
C23 C24 C19 120.77(19) . . ?
O2 C25 O1 123.2(2) . . ?
O2 C25 C22 123.5(2) . . ?
O1 C25 C22 113.25(18) . . ?
C28 C27 C32 118.32(19) . . ?
C28 C27 C18 122.25(19) . . ?
C32 C27 C18 119.43(19) . . ?
C29 C28 C27 120.99(19) . . ?
C28 C29 C30 120.0(2) . . ?
C31 C30 C29 119.3(2) . . ?
C31 C30 C33 118.52(19) . . ?
C29 C30 C33 122.1(2) . . ?
C32 C31 C30 120.08(19) . . ?
C31 C32 C27 121.3(2) . . ?
O4 C33 O3 122.8(2) . . ?
O4 C33 C30 124.9(2) . . ?
O3 C33 C30 112.29(18) . . ?
C7 N9 C17 125.72(17) . . ?
C7 N9 C15 111.04(17) . . ?
C17 N9 C15 120.01(17) . . ?
C7 N10 C18 126.56(18) . . ?
C7 N10 C16 111.14(16) . . ?
C18 N10 C16 119.70(17) . . ?
C25 O1 C26 114.20(17) . . ?
C33 O3 C34 115.07(17) . . ?
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
C1 C6 1.402(3) . ?
C1 C2 1.404(3) . ?
C1 C7 1.454(3) . ?
C2 C3 1.376(3) . ?
C3 C4 1.409(3) . ?
C4 C5 1.411(3) . ?
C4 C8 1.436(3) . ?
C5 C6 1.372(3) . ?
C7 N9 1.328(3) . ?
C7 N10 1.338(3) . ?
C8 C12 1.410(3) . ?
C8 C11 1.413(3) . ?
C11 N13 1.158(3) . ?
C12 N14 1.155(3) . ?
C15 N9 1.479(3) . ?
C15 C16 1.525(3) . ?
C16 N10 1.472(3) . ?
C17 N9 1.460(3) . ?
C17 C19 1.506(3) . ?
C18 N10 1.455(3) . ?
C18 C27 1.512(3) . ?
C19 C24 1.387(3) . ?
C19 C20 1.396(3) . ?
C20 C21 1.379(3) . ?
C21 C22 1.394(3) . ?
C22 C23 1.397(3) . ?
C22 C25 1.486(3) . ?
C23 C24 1.386(3) . ?
C25 O2 1.207(3) . ?
C25 O1 1.333(3) . ?
C26 O1 1.453(3) . ?
C27 C28 1.388(3) . ?
C27 C32 1.398(3) . ?
C28 C29 1.386(3) . ?
C29 C30 1.394(3) . ?
C30 C31 1.393(3) . ?
C30 C33 1.479(3) . ?
C31 C32 1.374(3) . ?
C33 O4 1.211(3) . ?
C33 O3 1.346(3) . ?
C34 O3 1.435(3) . ?
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
C6 C1 C2 C3 1.4(3) . . . . ?
C7 C1 C2 C3 -178.1(2) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C2 C3 C4 C8 178.5(2) . . . . ?
C3 C4 C5 C6 1.7(3) . . . . ?
C8 C4 C5 C6 -177.7(2) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C7 C1 C6 C5 178.9(2) . . . . ?
C6 C1 C7 N9 139.3(2) . . . . ?
C2 C1 C7 N9 -41.2(3) . . . . ?
C6 C1 C7 N10 -40.7(3) . . . . ?
C2 C1 C7 N10 138.8(2) . . . . ?
C3 C4 C8 C12 177.76(19) . . . . ?
C5 C4 C8 C12 -2.8(3) . . . . ?
C3 C4 C8 C11 -2.9(3) . . . . ?
C5 C4 C8 C11 176.47(19) . . . . ?
N9 C15 C16 N10 2.2(2) . . . . ?
N9 C17 C19 C24 -20.7(3) . . . . ?
N9 C17 C19 C20 161.22(18) . . . . ?
C24 C19 C20 C21 0.0(3) . . . . ?
C17 C19 C20 C21 178.13(19) . . . . ?
C19 C20 C21 C22 -0.9(3) . . . . ?
C20 C21 C22 C23 1.0(3) . . . . ?
C20 C21 C22 C25 -179.30(19) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
C25 C22 C23 C24 -179.9(2) . . . . ?
C22 C23 C24 C19 -0.8(3) . . . . ?
C20 C19 C24 C23 0.9(3) . . . . ?
C17 C19 C24 C23 -177.18(19) . . . . ?
C21 C22 C25 O2 -10.9(3) . . . . ?
C23 C22 C25 O2 168.7(2) . . . . ?
C21 C22 C25 O1 168.33(18) . . . . ?
C23 C22 C25 O1 -12.0(3) . . . . ?
N10 C18 C27 C28 -5.9(3) . . . . ?
N10 C18 C27 C32 174.49(18) . . . . ?
C32 C27 C28 C29 -1.2(3) . . . . ?
C18 C27 C28 C29 179.2(2) . . . . ?
C27 C28 C29 C30 -0.1(3) . . . . ?
C28 C29 C30 C31 1.2(3) . . . . ?
C28 C29 C30 C33 -176.4(2) . . . . ?
C29 C30 C31 C32 -1.1(3) . . . . ?
C33 C30 C31 C32 176.60(19) . . . . ?
C30 C31 C32 C27 -0.2(3) . . . . ?
C28 C27 C32 C31 1.3(3) . . . . ?
C18 C27 C32 C31 -179.08(19) . . . . ?
C31 C30 C33 O4 -1.3(3) . . . . ?
C29 C30 C33 O4 176.4(2) . . . . ?
C31 C30 C33 O3 -179.50(18) . . . . ?
C29 C30 C33 O3 -1.9(3) . . . . ?
N10 C7 N9 C17 159.34(19) . . . . ?
C1 C7 N9 C17 -20.7(3) . . . . ?
N10 C7 N9 C15 -0.1(2) . . . . ?
C1 C7 N9 C15 179.82(19) . . . . ?
C19 C17 N9 C7 123.4(2) . . . . ?
C19 C17 N9 C15 -78.8(2) . . . . ?
C16 C15 N9 C7 -1.4(2) . . . . ?
C16 C15 N9 C17 -162.23(18) . . . . ?
N9 C7 N10 C18 163.25(19) . . . . ?
C1 C7 N10 C18 -16.7(3) . . . . ?
N9 C7 N10 C16 1.8(2) . . . . ?
C1 C7 N10 C16 -178.19(19) . . . . ?
C27 C18 N10 C7 116.4(2) . . . . ?
C27 C18 N10 C16 -83.6(2) . . . . ?
C15 C16 N10 C7 -2.5(2) . . . . ?
C15 C16 N10 C18 -165.45(18) . . . . ?
O2 C25 O1 C26 2.4(3) . . . . ?
C22 C25 O1 C26 -176.81(18) . . . . ?
O4 C33 O3 C34 -1.9(3) . . . . ?
C30 C33 O3 C34 176.31(18) . . . . ?
