#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/45/7234547.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_7234547
loop_
_publ_author_name
'Martin Ipuy'
'Yuan-Yuan Liao'
'Erwann Jeanneau'
'Patrice L. Baldeck'
'Yann Bretonniere'
'Chantal Andraud'
_publ_section_title
;
 Solid state red biphotonic excited emission from small dipolar
 fluorophores
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              766
_journal_page_last               779
_journal_paper_doi               10.1039/C5TC03465E
_journal_volume                  4
_journal_year                    2016
_chemical_absolute_configuration .
_chemical_formula_moiety         'C20 H17 N3 O3'
_chemical_formula_sum            'C20 H17 N3 O3'
_chemical_formula_weight         347.37
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.854(2)
_cell_length_b                   15.110(2)
_cell_length_c                   16.697(3)
_cell_measurement_reflns_used    4972
_cell_measurement_temperature    150
_cell_measurement_theta_max      66.9630
_cell_measurement_theta_min      4.9480
_cell_volume                     3495.2(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 10.4678
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.079
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16513
_diffrn_reflns_theta_full        67.889
_diffrn_reflns_theta_max         67.889
_diffrn_reflns_theta_min         5.077
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.134
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.28
_refine_ls_extinction_coef       33.4(6)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0253
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3095
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0621
_refine_ls_shift/su_max          0.0004325
_refine_ls_shift/su_mean         0.0000981
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 494. 773. 367. 82.7 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1105
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1105
_reflns_limit_h_max              16
_reflns_limit_h_min              0
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                2377
_reflns_number_total             3110
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   3.20
_oxford_diffrn_Wilson_scale      0.47
_oxford_refine_ls_r_factor_ref   0.0755
_oxford_refine_ls_scale          1.564(13)
_oxford_reflns_number_all        3095
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-766.cif
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      'P b c a '
_cod_database_code               7234547
_iucr_refine_instruction_details_constraints
;
#
# Punched on 13/11/13 at 09:54:14
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   6,X'S) H   (  61,X'S) H   (  62,X'S) H   (  63,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) H   (  73,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) H   ( 133,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 173,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
#
# Punched on 13/11/13 at 09:54:14
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
x+1/2,y,-z+1/2
x+1/2,-y+1/2,-z
-x+1/2,y+1/2,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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.86765(13) 0.65499(11) 0.87586(11) 0.0468 1.0000 Uani . . . . . .
C2 C 0.87199(15) 0.57313(15) 0.90451(15) 0.0390 1.0000 Uani . . . . . .
C3 C 0.87504(15) 0.51121(16) 0.83977(14) 0.0385 1.0000 Uani . . . . . .
C4 C 0.87312(15) 0.55568(16) 0.76849(15) 0.0391 1.0000 Uani . . . . . .
C5 C 0.87033(17) 0.65414(15) 0.78701(14) 0.0407 1.0000 Uani . . . . . .
C6 C 0.96238(19) 0.70088(15) 0.76344(16) 0.0505 1.0000 Uani . . . . . .
H61 H 0.9645 0.7084 0.7050 0.0753 1.0000 Uiso R . . . . .
H62 H 1.0175 0.6672 0.7834 0.0746 1.0000 Uiso R . . . . .
H63 H 0.9618 0.7583 0.7892 0.0738 1.0000 Uiso R . . . . .
C7 C 0.77967(19) 0.70083(14) 0.75954(16) 0.0487 1.0000 Uani . . . . . .
H71 H 0.7832 0.7132 0.7020 0.0735 1.0000 Uiso R . . . . .
H72 H 0.7232 0.6651 0.7714 0.0725 1.0000 Uiso R . . . . .
H73 H 0.7767 0.7562 0.7898 0.0730 1.0000 Uiso R . . . . .
C8 C 0.87416(16) 0.51590(17) 0.69140(15) 0.0415 1.0000 Uani . . . . . .
C9 C 0.86983(16) 0.56215(16) 0.62199(16) 0.0424 1.0000 Uani . . . . . .
C10 C 0.87070(15) 0.53271(16) 0.54038(15) 0.0389 1.0000 Uani . . . . . .
C11 C 0.87793(15) 0.44405(16) 0.51398(16) 0.0392 1.0000 Uani . . . . . .
O12 O 0.88122(13) 0.38192(11) 0.57176(11) 0.0511 1.0000 Uani . . . . . .
C13 C 0.8882(2) 0.29104(17) 0.5490(2) 0.0627 1.0000 Uani . . . . . .
H131 H 0.8878 0.2559 0.5981 0.0930 1.0000 Uiso R . . . . .
H132 H 0.8345 0.2741 0.5142 0.0922 1.0000 Uiso R . . . . .
H133 H 0.9489 0.2815 0.5213 0.0920 1.0000 Uiso R . . . . .
C14 C 0.88074(17) 0.42509(17) 0.43287(16) 0.0419 1.0000 Uani . . . . . .
C15 C 0.87586(16) 0.49267(17) 0.37738(16) 0.0421 1.0000 Uani . . . . . .
O16 O 0.87913(13) 0.46669(12) 0.29921(11) 0.0523 1.0000 Uani . . . . . .
C17 C 0.87566(19) 0.53362(19) 0.23949(17) 0.0563 1.0000 Uani . . . . . .
H171 H 0.8787 0.5049 0.1874 0.0836 1.0000 Uiso R . . . . .
H173 H 0.8151 0.5667 0.2430 0.0836 1.0000 Uiso R . . . . .
H172 H 0.9298 0.5735 0.2451 0.0835 1.0000 Uiso R . . . . .
C18 C 0.86771(17) 0.58012(17) 0.40090(16) 0.0462 1.0000 Uani . . . . . .
C19 C 0.86510(18) 0.59806(16) 0.48172(16) 0.0461 1.0000 Uani . . . . . .
H191 H 0.8584 0.6566 0.4973 0.0552 1.0000 Uiso R . . . . .
H181 H 0.8626 0.6268 0.3636 0.0550 1.0000 Uiso R . . . . .
H141 H 0.8866 0.3671 0.4166 0.0494 1.0000 Uiso R . . . . .
H91 H 0.8665 0.6239 0.6280 0.0501 1.0000 Uiso R . . . . .
H81 H 0.8777 0.4543 0.6893 0.0495 1.0000 Uiso R . . . . .
C20 C 0.88089(17) 0.41746(16) 0.84834(16) 0.0428 1.0000 Uani . . . . . .
N21 N 0.88599(18) 0.34196(14) 0.85163(17) 0.0612 1.0000 Uani . . . . . .
C22 C 0.87215(16) 0.56133(15) 0.98566(16) 0.0405 1.0000 Uani . . . . . .
C23 C 0.87942(17) 0.47612(16) 1.02250(16) 0.0425 1.0000 Uani . . . . . .
N24 N 0.8857(2) 0.41155(16) 1.05626(16) 0.0618 1.0000 Uani . . . . . .
C25 C 0.86951(18) 0.63554(18) 1.03846(16) 0.0467 1.0000 Uani . . . . . .
N26 N 0.86775(19) 0.69494(15) 1.08071(16) 0.0650 1.0000 Uani . . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 . C5 . 110.55(18) yes
O1 . C2 . C3 . 109.8(2) yes
O1 . C2 . C22 . 118.6(2) yes
C3 . C2 . C22 . 131.6(2) yes
C2 . C3 . C4 . 109.6(2) yes
C2 . C3 . C20 . 125.1(2) yes
C4 . C3 . C20 . 125.2(2) yes
C3 . C4 . C5 . 107.7(2) yes
C3 . C4 . C8 . 125.5(2) yes
C5 . C4 . C8 . 126.8(2) yes
C4 . C5 . O1 . 102.27(19) yes
C4 . C5 . C6 . 112.53(19) yes
O1 . C5 . C6 . 106.1(2) yes
C4 . C5 . C7 . 114.6(2) yes
O1 . C5 . C7 . 106.17(19) yes
C6 . C5 . C7 . 113.9(2) yes
C5 . C6 . H61 . 109.7 no
C5 . C6 . H62 . 109.2 no
H61 . C6 . H62 . 112.0 no
C5 . C6 . H63 . 107.2 no
H61 . C6 . H63 . 109.8 no
H62 . C6 . H63 . 108.7 no
C5 . C7 . H71 . 110.2 no
C5 . C7 . H72 . 110.4 no
H71 . C7 . H72 . 110.3 no
C5 . C7 . H73 . 106.1 no
H71 . C7 . H73 . 110.2 no
H72 . C7 . H73 . 109.7 no
C4 . C8 . C9 . 123.8(2) yes
C4 . C8 . H81 . 117.1 no
C9 . C8 . H81 . 119.1 no
C8 . C9 . C10 . 130.8(2) yes
C8 . C9 . H91 . 115.0 no
C10 . C9 . H91 . 114.2 no
C9 . C10 . C11 . 126.2(2) yes
C9 . C10 . C19 . 116.6(2) yes
C11 . C10 . C19 . 117.2(2) yes
C10 . C11 . O12 . 116.1(2) yes
C10 . C11 . C14 . 120.2(2) yes
O12 . C11 . C14 . 123.7(2) yes
C11 . O12 . C13 . 118.8(2) yes
O12 . C13 . H131 . 107.4 no
O12 . C13 . H132 . 111.0 no
H131 . C13 . H132 . 110.6 no
O12 . C13 . H133 . 109.2 no
H131 . C13 . H133 . 108.9 no
H132 . C13 . H133 . 109.7 no
C11 . C14 . C15 . 120.1(2) yes
C11 . C14 . H141 . 119.2 no
C15 . C14 . H141 . 120.7 no
C14 . C15 . O16 . 115.3(2) yes
C14 . C15 . C18 . 121.3(2) yes
O16 . C15 . C18 . 123.3(3) yes
C15 . O16 . C17 . 117.7(2) yes
O16 . C17 . H171 . 107.9 no
O16 . C17 . H173 . 110.5 no
H171 . C17 . H173 . 108.6 no
O16 . C17 . H172 . 110.5 no
H171 . C17 . H172 . 109.4 no
H173 . C17 . H172 . 109.9 no
C15 . C18 . C19 . 117.9(2) yes
C15 . C18 . H181 . 122.2 no
C19 . C18 . H181 . 119.9 no
C10 . C19 . C18 . 123.2(2) yes
C10 . C19 . H191 . 119.0 no
C18 . C19 . H191 . 117.7 no
C3 . C20 . N21 . 177.0(3) yes
C2 . C22 . C23 . 122.9(2) yes
C2 . C22 . C25 . 120.7(2) yes
C23 . C22 . C25 . 116.3(2) yes
C22 . C23 . N24 . 175.5(3) yes
C22 . C25 . N26 . 179.8(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.328(3) yes
O1 . C5 . 1.484(3) yes
C2 . C3 . 1.430(3) yes
C2 . C22 . 1.367(3) yes
C3 . C4 . 1.367(3) yes
C3 . C20 . 1.426(3) yes
C4 . C5 . 1.520(3) yes
C4 . C8 . 1.421(3) yes
C5 . C6 . 1.510(3) yes
C5 . C7 . 1.512(3) yes
C6 . H61 . 0.984 no
C6 . H62 . 0.976 no
C6 . H63 . 0.969 no
C7 . H71 . 0.981 no
C7 . H72 . 0.971 no
C7 . H73 . 0.977 no
C8 . C9 . 1.355(4) yes
C8 . H81 . 0.932 no
C9 . C10 . 1.433(3) yes
C9 . H91 . 0.940 no
C10 . C11 . 1.414(3) yes
C10 . C19 . 1.393(3) yes
C11 . O12 . 1.347(3) yes
C11 . C14 . 1.385(4) yes
O12 . C13 . 1.428(3) yes
C13 . H131 . 0.976 no
C13 . H132 . 0.978 no
C13 . H133 . 0.970 no
C14 . C15 . 1.380(4) yes
C14 . H141 . 0.921 no
C15 . O16 . 1.364(3) yes
C15 . C18 . 1.383(4) yes
O16 . C17 . 1.421(3) yes
C17 . H171 . 0.973 no
C17 . H173 . 0.978 no
C17 . H172 . 0.966 no
C18 . C19 . 1.377(4) yes
C18 . H181 . 0.943 no
C19 . H191 . 0.927 no
C20 . N21 . 1.144(3) yes
C22 . C23 . 1.430(3) yes
C22 . C25 . 1.427(3) yes
C23 . N24 . 1.130(3) yes
C25 . N26 . 1.142(4) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C7 . H72 . O16 5_665 160.40(7) 0.971 2.489 3.418(4) yes
C8 . H81 . O12 . 121.00 0.932 2.248 2.846(4) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132603039
