#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/45/7234548.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_7234548
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           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 94.990(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.397(2)
_cell_length_b                   9.8280(10)
_cell_length_c                   17.179(2)
_cell_measurement_reflns_used    4290
_cell_measurement_temperature    150
_cell_measurement_theta_max      66.8020
_cell_measurement_theta_min      4.1730
_cell_volume                     1748.7(4)
_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 0.979
_diffrn_measured_fraction_theta_max 0.975
_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  0.091
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13075
_diffrn_reflns_theta_full        67.676
_diffrn_reflns_theta_max         67.856
_diffrn_reflns_theta_min         4.268
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.824
_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    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.456
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.42
_refine_ls_extinction_coef       36(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3091
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0661
_refine_ls_shift/su_max          0.0001793
_refine_ls_shift/su_mean         0.0000250
_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: 
 0.274E+04 0.457E+04 0.276E+04 0.109E+04 220. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2043
_refine_ls_wR_factor_gt          0.1605
_refine_ls_wR_factor_ref         0.2043
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                2401
_reflns_number_total             3103
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   3.46
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0837
_oxford_refine_ls_scale          5.7(3)
_oxford_reflns_number_all        3091
_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           4
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               7234548
_iucr_refine_instruction_details_constraints
;
#
# Punched on 22/11/13 at 14:37:36
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) H   (  83,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) H   (  93,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) H   ( 153,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  21,X'S) H   ( 212,X'S) H   ( 213,X'S) H   ( 211,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
#
# Punched on 22/11/13 at 14:37:36
#
#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
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 0.40874(19) 0.2726(2) 0.33411(10) 0.0397 1.0000 Uani . . . . . .
C2 C 0.3831(2) 0.3286(3) 0.40173(15) 0.0353 1.0000 Uani . . . . . .
C3 C 0.4652(3) 0.2702(3) 0.46434(15) 0.0354 1.0000 Uani . . . . . .
C4 C 0.4664(3) 0.3022(3) 0.54541(16) 0.0392 1.0000 Uani . . . . . .
N5 N 0.4730(3) 0.3244(3) 0.61074(15) 0.0567 1.0000 Uani . . . . . .
C6 C 0.5468(3) 0.1784(3) 0.43435(15) 0.0358 1.0000 Uani . . . . . .
C7 C 0.5190(3) 0.1779(3) 0.34648(15) 0.0361 1.0000 Uani . . . . . .
C8 C 0.6285(3) 0.2406(3) 0.30571(16) 0.0406 1.0000 Uani . . . . . .
H81 H 0.7025 0.1813 0.3099 0.0617 1.0000 Uiso R . . . . .
H82 H 0.6011 0.2521 0.2502 0.0614 1.0000 Uiso R . . . . .
H83 H 0.6520 0.3284 0.3284 0.0619 1.0000 Uiso R . . . . .
C9 C 0.4721(3) 0.0431(3) 0.31137(16) 0.0423 1.0000 Uani . . . . . .
H91 H 0.5428 -0.0220 0.3153 0.0634 1.0000 Uiso R . . . . .
H92 H 0.4408 0.0573 0.2577 0.0636 1.0000 Uiso R . . . . .
H93 H 0.4024 0.0092 0.3405 0.0634 1.0000 Uiso R . . . . .
C10 C 0.6437(3) 0.1047(3) 0.48061(16) 0.0391 1.0000 Uani . . . . . .
C11 C 0.7215(3) 0.0094(3) 0.45265(16) 0.0382 1.0000 Uani . . . . . .
C12 C 0.8197(3) -0.0723(3) 0.49546(15) 0.0363 1.0000 Uani . . . . . .
C13 C 0.8688(3) -0.0509(3) 0.57333(16) 0.0382 1.0000 Uani . . . . . .
O14 O 0.81975(19) 0.0586(2) 0.60975(11) 0.0430 1.0000 Uani . . . . . .
C15 C 0.8727(3) 0.0923(3) 0.68625(17) 0.0470 1.0000 Uani . . . . . .
H151 H 0.8341 0.1776 0.7006 0.0717 1.0000 Uiso R . . . . .
H152 H 0.8519 0.0213 0.7217 0.0719 1.0000 Uiso R . . . . .
H153 H 0.9653 0.1005 0.6859 0.0719 1.0000 Uiso R . . . . .
C16 C 0.9631(3) -0.1351(3) 0.60964(18) 0.0450 1.0000 Uani . . . . . .
C17 C 1.0090(3) -0.2422(3) 0.56766(19) 0.0481 1.0000 Uani . . . . . .
C18 C 0.9645(3) -0.2667(3) 0.49104(19) 0.0456 1.0000 Uani . . . . . .
C19 C 0.8712(3) -0.1827(3) 0.45486(17) 0.0414 1.0000 Uani . . . . . .
O20 O 0.8222(2) -0.1962(2) 0.37906(12) 0.0494 1.0000 Uani . . . . . .
C21 C 0.8514(4) -0.3152(3) 0.33745(19) 0.0545 1.0000 Uani . . . . . .
H212 H 0.8066 -0.3100 0.2852 0.0815 1.0000 Uiso R . . . . .
H213 H 0.8218 -0.3956 0.3646 0.0813 1.0000 Uiso R . . . . .
H211 H 0.9439 -0.3213 0.3346 0.0819 1.0000 Uiso R . . . . .
H181 H 0.9975 -0.3394 0.4640 0.0560 1.0000 Uiso R . . . . .
H171 H 1.0723 -0.3000 0.5924 0.0573 1.0000 Uiso R . . . . .
H161 H 0.9954 -0.1180 0.6614 0.0542 1.0000 Uiso R . . . . .
H111 H 0.7101 -0.0055 0.3981 0.0469 1.0000 Uiso R . . . . .
H101 H 0.6512 0.1251 0.5340 0.0467 1.0000 Uiso R . . . . .
C22 C 0.2916(3) 0.4276(3) 0.40347(15) 0.0375 1.0000 Uani . . . . . .
C23 C 0.2196(3) 0.4732(3) 0.33414(17) 0.0410 1.0000 Uani . . . . . .
N24 N 0.1599(3) 0.5140(3) 0.28017(17) 0.0559 1.0000 Uani . . . . . .
C25 C 0.2687(3) 0.4955(3) 0.47377(17) 0.0402 1.0000 Uani . . . . . .
N26 N 0.2507(3) 0.5549(3) 0.52974(16) 0.0515 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 . C7 . 110.28(19) yes
O1 . C2 . C3 . 109.7(2) yes
O1 . C2 . C22 . 120.5(2) yes
C3 . C2 . C22 . 129.9(2) yes
C2 . C3 . C4 . 126.7(2) yes
C2 . C3 . C6 . 109.2(2) yes
C4 . C3 . C6 . 124.0(3) yes
C3 . C4 . N5 . 176.6(3) yes
C3 . C6 . C7 . 107.9(2) yes
C3 . C6 . C10 . 123.8(2) yes
C7 . C6 . C10 . 128.3(2) yes
C6 . C7 . O1 . 102.71(19) yes
C6 . C7 . C8 . 111.9(2) yes
O1 . C7 . C8 . 106.3(2) yes
C6 . C7 . C9 . 115.3(2) yes
O1 . C7 . C9 . 105.9(2) yes
C8 . C7 . C9 . 113.5(2) yes
C7 . C8 . H81 . 110.3 no
C7 . C8 . H82 . 109.3 no
H81 . C8 . H82 . 107.8 no
C7 . C8 . H83 . 110.4 no
H81 . C8 . H83 . 109.7 no
H82 . C8 . H83 . 109.4 no
C7 . C9 . H91 . 109.4 no
C7 . C9 . H92 . 109.0 no
H91 . C9 . H92 . 110.7 no
C7 . C9 . H93 . 108.7 no
H91 . C9 . H93 . 109.3 no
H92 . C9 . H93 . 109.7 no
C6 . C10 . C11 . 124.7(3) yes
C6 . C10 . H101 . 115.6 no
C11 . C10 . H101 . 119.7 no
C10 . C11 . C12 . 128.3(3) yes
C10 . C11 . H111 . 115.6 no
C12 . C11 . H111 . 116.1 no
C11 . C12 . C13 . 125.6(2) yes
C11 . C12 . C19 . 117.0(3) yes
C13 . C12 . C19 . 117.4(3) yes
C12 . C13 . O14 . 115.8(2) yes
C12 . C13 . C16 . 121.5(3) yes
O14 . C13 . C16 . 122.7(3) yes
C13 . O14 . C15 . 118.6(2) yes
O14 . C15 . H151 . 107.6 no
O14 . C15 . H152 . 109.1 no
H151 . C15 . H152 . 110.1 no
O14 . C15 . H153 . 108.6 no
H151 . C15 . H153 . 111.3 no
H152 . C15 . H153 . 110.1 no
C13 . C16 . C17 . 118.7(3) yes
C13 . C16 . H161 . 120.0 no
C17 . C16 . H161 . 121.3 no
C16 . C17 . C18 . 121.9(3) yes
C16 . C17 . H171 . 118.9 no
C18 . C17 . H171 . 119.2 no
C17 . C18 . C19 . 119.4(3) yes
C17 . C18 . H181 . 120.1 no
C19 . C18 . H181 . 120.6 no
C12 . C19 . C18 . 121.1(3) yes
C12 . C19 . O20 . 114.7(3) yes
C18 . C19 . O20 . 124.2(3) yes
C19 . O20 . C21 . 118.9(3) yes
O20 . C21 . H212 . 108.3 no
O20 . C21 . H213 . 109.6 no
H212 . C21 . H213 . 109.6 no
O20 . C21 . H211 . 109.5 no
H212 . C21 . H211 . 110.7 no
H213 . C21 . H211 . 109.1 no
C2 . C22 . C23 . 121.6(2) yes
C2 . C22 . C25 . 121.6(2) yes
C23 . C22 . C25 . 116.7(2) yes
C22 . C23 . N24 . 177.3(3) yes
C22 . C25 . N26 . 177.7(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 . 1.333(3) yes
O1 . C7 . 1.477(3) yes
C2 . C3 . 1.434(4) yes
C2 . C22 . 1.362(4) yes
C3 . C4 . 1.427(4) yes
C3 . C6 . 1.370(4) yes
C4 . N5 . 1.139(4) yes
C6 . C7 . 1.512(4) yes
C6 . C10 . 1.426(4) yes
C7 . C8 . 1.518(4) yes
C7 . C9 . 1.518(4) yes
C8 . H81 . 0.963 no
C8 . H82 . 0.978 no
C8 . H83 . 0.970 no
C9 . H91 . 0.972 no
C9 . H92 . 0.961 no
C9 . H93 . 0.975 no
C10 . C11 . 1.352(4) yes
C10 . H101 . 0.936 no
C11 . C12 . 1.448(4) yes
C11 . H111 . 0.946 no
C12 . C13 . 1.406(4) yes
C12 . C19 . 1.419(4) yes
C13 . O14 . 1.365(3) yes
C13 . C16 . 1.389(4) yes
O14 . C15 . 1.419(3) yes
C15 . H151 . 0.971 no
C15 . H152 . 0.963 no
C15 . H153 . 0.966 no
C16 . C17 . 1.384(4) yes
C16 . H161 . 0.939 no
C17 . C18 . 1.378(5) yes
C17 . H171 . 0.943 no
C18 . C19 . 1.380(4) yes
C18 . H181 . 0.934 no
C19 . O20 . 1.363(4) yes
O20 . C21 . 1.418(4) yes
C21 . H212 . 0.976 no
C21 . H213 . 0.980 no
C21 . H211 . 0.969 no
C22 . C23 . 1.423(4) yes
C22 . C25 . 1.418(4) yes
C23 . N24 . 1.142(4) yes
C25 . N26 . 1.154(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
C21 . H213 . N26 2_656 162.55(9) 0.980 2.560 3.507(4) yes
C10 . H101 . O14 . 121.00 0.936 2.190 2.787(4) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132603042
