#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/45/7234545.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_7234545
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         'C19 H15 N3 O2'
_chemical_formula_sum            'C19 H15 N3 O2'
_chemical_formula_weight         317.34
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_cell_angle_alpha                90
_cell_angle_beta                 101.360(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.0110(9)
_cell_length_b                   6.9999(6)
_cell_length_c                   11.5760(10)
_cell_measurement_reflns_used    5464
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.3129
_cell_measurement_theta_min      3.8918
_cell_volume                     795.31(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_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    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.045
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8943
_diffrn_reflns_theta_full        66.416
_diffrn_reflns_theta_max         66.416
_diffrn_reflns_theta_min         3.895
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
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            brown
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.511
_exptl_crystal_size_mid          0.345
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.69
_refine_diff_density_min         -0.29
_refine_ls_extinction_coef       15.9(6)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9391
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         1533
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.0032352
_refine_ls_shift/su_mean         0.0000351
_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: 
 0.147E+04 0.247E+04 0.147E+04 588. 127. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1059
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1059
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                1448
_reflns_number_total             1533
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   1.41
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0465
_oxford_refine_ls_scale          6.2(2)
_oxford_reflns_number_all        1533
_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           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Other' was changed to
'other' in accordance with the built-in table derived from the CIF
Core dictionary named 'cif_core.dic' version 2.4.5 last updated on
2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/m '
_cod_database_code               7234545
_iucr_refine_instruction_details_constraints
;
#
# Punched on 29/05/12 at 14:27:26
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   6,X'S) H   (  63,X'S) H   (  62,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  14,X'S) H   ( 142,X'S) H   ( 143,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
#
# Punched on 29/05/12 at 14:27:26
#
#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
-x,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 0.47818(14) 0.7500 -0.30866(12) 0.0201 1.0000 Uani S T . . . .
C2 C 0.6051(2) 0.7500 -0.24536(18) 0.0179 1.0000 Uani S T . . . .
C3 C 0.6011(2) 0.7500 -0.12130(17) 0.0190 1.0000 Uani S T . . . .
C4 C 0.4686(2) 0.7500 -0.10764(17) 0.0192 1.0000 Uani S T . . . .
C5 C 0.3778(2) 0.7500 -0.22930(17) 0.0191 1.0000 Uani S T . . . .
C6 C 0.29319(14) 0.5696(2) -0.25790(12) 0.0233 1.0000 Uani . . . . . .
H63 H 0.3490 0.4570 -0.2374 0.0344 1.0000 Uiso R . . . . .
H62 H 0.2549 0.5675 -0.3420 0.0327 1.0000 Uiso R . . . . .
H61 H 0.2207 0.5685 -0.2132 0.0331 1.0000 Uiso R . . . . .
C7 C 0.4303(2) 0.750000(7) 0.00545(19) 0.0242 1.0000 Uani S T . . . .
C8 C 0.3023(2) 0.750000(7) 0.02493(19) 0.0235 1.0000 Uani S T . . . .
C9 C 0.2634(2) 0.7500 0.14032(19) 0.0237 1.0000 Uani S T . . . .
C10 C 0.3574(2) 0.750000(7) 0.2489(2) 0.0241 1.0000 Uani S T . . . .
C11 C 0.3138(2) 0.750000(7) 0.35523(19) 0.0218 1.0000 Uani S T . . . .
C12 C 0.1741(2) 0.7500 0.35490(17) 0.0192 1.0000 Uani S T . . . .
O13 O 0.13804(14) 0.7500 0.46261(12) 0.0227 1.0000 Uani S T . . . .
C14 C -0.0039(2) 0.750000(7) 0.4652(2) 0.0288 1.0000 Uani S T . . . .
H142 H -0.0462 0.6356 0.4268 0.0418 1.0000 Uiso R . . . . .
H143 H -0.0130 0.7500 0.5480 0.0431 1.0000 Uiso RS . . . . .
C15 C 0.0805(2) 0.750000(7) 0.24810(18) 0.0234 1.0000 Uani S T . . . .
C16 C 0.1260(2) 0.750000(7) 0.14316(19) 0.0262 1.0000 Uani S T . . . .
H161 H 0.0603 0.7500 0.0703 0.0317 1.0000 Uiso RS . . . . .
H151 H -0.0159 0.7500 0.2477 0.0290 1.0000 Uiso RS . . . . .
H111 H 0.3742 0.7500 0.4278 0.0254 1.0000 Uiso RS . . . . .
H101 H 0.4527 0.7500 0.2529 0.0295 1.0000 Uiso RS . . . . .
H81 H 0.2305 0.7500 -0.0449 0.0285 1.0000 Uiso RS . . . . .
H71 H 0.5018 0.7500 0.0763 0.0297 1.0000 Uiso RS . . . . .
C17 C 0.7156(2) 0.7500 -0.02614(18) 0.0226 1.0000 Uani S T . . . .
N18 N 0.80148(19) 0.7500 0.05570(16) 0.0316 1.0000 Uani S T . . . .
C19 C 0.7135(2) 0.7500 -0.30124(18) 0.0196 1.0000 Uani S T . . . .
C20 C 0.6894(2) 0.7500 -0.42745(18) 0.0216 1.0000 Uani S T . . . .
N21 N 0.6689(2) 0.7500 -0.52900(17) 0.0311 1.0000 Uani S T . . . .
C22 C 0.8519(2) 0.7500 -0.23959(18) 0.0214 1.0000 Uani S T . . . .
N23 N 0.96503(19) 0.7500 -0.19418(18) 0.0301 1.0000 Uani S T . . . .
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'
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'
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'
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 . 110.25(15) yes
O1 . C2 . C3 . 109.61(17) yes
O1 . C2 . C19 . 119.85(18) yes
C3 . C2 . C19 . 130.53(19) yes
C2 . C3 . C4 . 109.44(17) yes
C2 . C3 . C17 . 126.35(18) yes
C4 . C3 . C17 . 124.20(19) yes
C3 . C4 . C5 . 108.09(17) yes
C3 . C4 . C7 . 123.07(19) yes
C5 . C4 . C7 . 128.84(19) yes
C6 3_565 C5 . C4 . 114.09(10) yes
C6 3_565 C5 . O1 . 106.28(10) yes
C4 . C5 . O1 . 102.61(15) yes
C6 3_565 C5 . C6 . 112.34(16) yes
C4 . C5 . C6 . 114.09(10) yes
O1 . C5 . C6 . 106.28(10) yes
C5 . C6 . H63 . 110.6 no
C5 . C6 . H62 . 108.8 no
H63 . C6 . H62 . 109.1 no
C5 . C6 . H61 . 109.5 no
H63 . C6 . H61 . 108.6 no
H62 . C6 . H61 . 110.2 no
C4 . C7 . C8 . 126.0(2) yes
C4 . C7 . H71 . 118.8 no
C8 . C7 . H71 . 115.1 no
C7 . C8 . C9 . 126.0(2) yes
C7 . C8 . H81 . 115.8 no
C9 . C8 . H81 . 118.3 no
C8 . C9 . C10 . 124.1(2) yes
C8 . C9 . C16 . 117.8(2) yes
C10 . C9 . C16 . 118.0(2) yes
C9 . C10 . C11 . 121.3(2) yes
C9 . C10 . H101 . 122.1 no
C11 . C10 . H101 . 116.6 no
C10 . C11 . C12 . 119.21(19) yes
C10 . C11 . H111 . 122.6 no
C12 . C11 . H111 . 118.2 no
C11 . C12 . O13 . 116.24(17) yes
C11 . C12 . C15 . 119.95(19) yes
O13 . C12 . C15 . 123.81(19) yes
C12 . O13 . C14 . 117.58(16) yes
O13 . C14 . H142 3_565 109.6 no
O13 . C14 . H142 . 109.6 no
H142 3_565 C14 . H142 . 111.0 no
O13 . C14 . H143 . 107.7 no
H142 3_565 C14 . H143 . 109.4 no
H142 . C14 . H143 . 109.4 no
C12 . C15 . C16 . 119.9(2) yes
C12 . C15 . H151 . 120.1 no
C16 . C15 . H151 . 120.0 no
C9 . C16 . C15 . 121.6(2) yes
C9 . C16 . H161 . 119.4 no
C15 . C16 . H161 . 119.0 no
C3 . C17 . N18 . 175.2(2) yes
C2 . C19 . C20 . 119.46(19) yes
C2 . C19 . C22 . 123.05(19) yes
C20 . C19 . C22 . 117.49(18) yes
C19 . C20 . N21 . 179.5(2) yes
C19 . C22 . N23 . 177.3(2) 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 . 1.336(2) yes
O1 . C5 . 1.489(2) yes
C2 . C3 . 1.445(3) yes
C2 . C19 . 1.369(3) yes
C3 . C4 . 1.366(3) yes
C3 . C17 . 1.425(3) yes
C4 . C5 . 1.519(3) yes
C4 . C7 . 1.435(3) yes
C5 . C6 3_565 1.5202(18) yes
C5 . C6 . 1.5202(18) yes
C6 . H63 . 0.968 no
C6 . H62 . 0.974 no
C6 . H61 . 0.970 no
C7 . C8 . 1.344(3) yes
C7 . H71 . 0.976 no
C8 . C9 . 1.463(3) yes
C8 . H81 . 0.971 no
C9 . C10 . 1.414(3) yes
C9 . C16 . 1.382(3) yes
C10 . C11 . 1.385(3) yes
C10 . H101 . 0.947 no
C11 . C12 . 1.397(3) yes
C11 . H111 . 0.933 no
C12 . O13 . 1.365(2) yes
C12 . C15 . 1.397(3) yes
O13 . C14 . 1.428(2) yes
C14 . H142 3_565 0.972 no
C14 . H142 . 0.972 no
C14 . H143 . 0.980 no
C15 . C16 . 1.379(3) yes
C15 . H151 . 0.964 no
C16 . H161 . 0.962 no
C17 . N18 . 1.147(3) yes
C19 . C20 . 1.433(3) yes
C19 . C22 . 1.428(3) yes
C20 . N21 . 1.153(3) yes
C22 . N23 . 1.151(3) 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
C16 . H161 . N18 1_455 124.40(7) 0.962 2.563 3.207(2) yes
C15 . H151 . N18 1_455 122.79(7) 0.964 2.585 3.211(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132603037
