#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/45/7234551.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_7234551
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_formula_moiety         'C21 H19 N3 O4'
_chemical_formula_sum            'C21 H19 N3 O4'
_chemical_formula_weight         377.39
_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_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 100.738(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.2981(11)
_cell_length_b                   16.4911(9)
_cell_length_c                   7.1281(5)
_cell_measurement_reflns_used    8257
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.1510
_cell_measurement_theta_min      3.7880
_cell_volume                     1882.3(2)
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_molecular_graphics    'SHELXLe (Sheldrick, 2011)'
_computing_publication_material  'SHELXLe (Sheldrick, 2011)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0958
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            24328
_diffrn_reflns_theta_full        67.11
_diffrn_reflns_theta_max         67.11
_diffrn_reflns_theta_min         3.85
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent intense red'
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       octahedral
_exptl_crystal_F_000             792
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.5212
_exptl_crystal_size_mid          0.2525
_exptl_crystal_size_min          0.1247
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0733
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1471P)²+0.5106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1925
_refine_ls_wR_factor_ref         0.2046
_reflns_number_gt                2857
_reflns_number_total             3349
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-766.cif
_cod_data_source_block           7
_cod_database_code               7234551
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.67639(10) 0.05863(9) 0.1655(2) 0.0286(4) Uani 1 1 d . . .
C1 C 0.59519(16) 0.03267(15) 0.1867(4) 0.0382(6) Uani 1 1 d . . .
H1A H 0.5542 0.0560 0.0872 0.057 Uiso 1 1 calc R . .
H1B H 0.5847 0.0499 0.3087 0.057 Uiso 1 1 calc R . .
H1C H 0.5921 -0.0254 0.1786 0.057 Uiso 1 1 calc R . .
C2 C 0.86492(15) 0.51870(14) -0.0633(3) 0.0270(5) Uani 1 1 d . . .
H2A H 0.8168 0.5358 -0.1538 0.040 Uiso 1 1 calc R . .
H2B H 0.8697 0.4607 -0.0673 0.040 Uiso 1 1 calc R . .
H2C H 0.9141 0.5431 -0.0946 0.040 Uiso 1 1 calc R . .
C3 C 0.93382(15) 0.20434(14) 0.1167(3) 0.0307(5) Uani 1 1 d . . .
H3A H 0.9165 0.1714 0.0053 0.046 Uiso 1 1 calc R . .
H3B H 0.9409 0.1708 0.2287 0.046 Uiso 1 1 calc R . .
H3C H 0.9858 0.2304 0.1092 0.046 Uiso 1 1 calc R . .
C4 C 0.79038(13) 0.75091(13) 0.1893(3) 0.0223(5) Uani 1 1 d . . .
C5 C 0.51756(14) 0.32279(14) 0.1947(3) 0.0275(5) Uani 1 1 d . . .
H5A H 0.4867 0.3725 0.1921 0.041 Uiso 1 1 calc R . .
H5B H 0.5150 0.2939 0.3104 0.041 Uiso 1 1 calc R . .
H5C H 0.4938 0.2900 0.0869 0.041 Uiso 1 1 calc R . .
N1 N 0.58769(13) 0.62745(13) 0.2729(3) 0.0333(5) Uani 1 1 d . . .
C6 C 0.92564(14) 0.51475(14) 0.2920(3) 0.0276(5) Uani 1 1 d . . .
H6A H 0.9259 0.4565 0.2927 0.041 Uiso 1 1 calc R . .
H6B H 0.9172 0.5343 0.4138 0.041 Uiso 1 1 calc R . .
H6C H 0.9781 0.5343 0.2676 0.041 Uiso 1 1 calc R . .
C7 C 0.76927(14) 0.53146(13) 0.1795(3) 0.0221(5) Uani 1 1 d . . .
C8 C 0.85547(14) 0.54488(12) 0.1367(3) 0.0229(5) Uani 1 1 d . . .
C9 C 0.71956(14) 0.79323(13) 0.2292(3) 0.0238(5) Uani 1 1 d . . .
N2 N 0.66455(13) 0.83039(12) 0.2630(3) 0.0313(5) Uani 1 1 d . . .
C10 C 0.76613(14) 0.38418(13) 0.1604(3) 0.0226(5) Uani 1 1 d . . .
H10 H 0.8200 0.3892 0.1362 0.027 Uiso 1 1 calc R . .
C11 C 0.63239(14) 0.19796(13) 0.1813(3) 0.0239(5) Uani 1 1 d . . .
H11 H 0.5784 0.1837 0.1934 0.029 Uiso 1 1 calc R . .
C12 C 0.73519(13) 0.60620(13) 0.2049(3) 0.0222(5) Uani 1 1 d . . .
C13 C 0.65372(14) 0.61911(13) 0.2434(3) 0.0245(5) Uani 1 1 d . . .
C14 C 0.79416(13) 0.66753(13) 0.1799(3) 0.0220(5) Uani 1 1 d . . .
C15 C 0.69138(14) 0.13909(13) 0.1656(3) 0.0227(5) Uani 1 1 d . . .
C16 C 0.77246(14) 0.15904(13) 0.1467(3) 0.0231(5) Uani 1 1 d . . .
H16 H 0.8109 0.1185 0.1355 0.028 Uiso 1 1 calc R . .
C17 C 0.79498(13) 0.23944(13) 0.1447(3) 0.0221(5) Uani 1 1 d . . .
C18 C 0.85981(14) 0.79821(13) 0.1580(3) 0.0231(5) Uani 1 1 d . . .
N3 N 0.91532(13) 0.83718(12) 0.1350(3) 0.0295(5) Uani 1 1 d . . .
C19 C 0.65578(13) 0.27866(13) 0.1784(3) 0.0219(5) Uani 1 1 d . . .
C20 C 0.73711(14) 0.30242(13) 0.1616(3) 0.0225(5) Uani 1 1 d . . .
C21 C 0.72911(14) 0.45573(13) 0.1884(3) 0.0235(5) Uani 1 1 d . . .
H21 H 0.6753 0.4550 0.2144 0.028 Uiso 1 1 calc R . .
O2 O 0.60221(9) 0.34044(9) 0.1867(2) 0.0262(4) Uani 1 1 d . . .
O3 O 0.87207(9) 0.26418(9) 0.1269(2) 0.0254(4) Uani 1 1 d . . .
O4 O 0.86279(9) 0.63440(9) 0.1388(2) 0.0234(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
C15 O1 C1 117.84(18) . .
C14 C4 C9 123.0(2) . .
C14 C4 C18 119.61(19) . .
C9 C4 C18 117.4(2) . .
C12 C7 C21 125.6(2) . .
C12 C7 C8 107.99(18) . .
C21 C7 C8 126.44(19) . .
O4 C8 C7 102.74(16) . .
O4 C8 C6 105.69(16) . .
C7 C8 C6 114.08(17) . .
O4 C8 C2 105.66(16) . .
C7 C8 C2 114.05(18) . .
C6 C8 C2 113.26(18) . .
N2 C9 C4 177.0(2) . .
C21 C10 C20 131.5(2) . .
C19 C11 C15 118.4(2) . .
C7 C12 C13 125.0(2) . .
C7 C12 C14 108.64(19) . .
C13 C12 C14 126.33(19) . .
N1 C13 C12 178.2(2) . .
O4 C14 C4 117.97(19) . .
O4 C14 C12 110.53(18) . .
C4 C14 C12 131.5(2) . .
O1 C15 C11 124.1(2) . .
O1 C15 C16 114.04(19) . .
C11 C15 C16 121.8(2) . .
C17 C16 C15 119.2(2) . .
O3 C17 C16 123.2(2) . .
O3 C17 C20 115.51(18) . .
C16 C17 C20 121.3(2) . .
N3 C18 C4 178.9(2) . .
O2 C19 C11 122.8(2) . .
O2 C19 C20 114.85(18) . .
C11 C19 C20 122.3(2) . .
C19 C20 C17 116.95(19) . .
C19 C20 C10 125.5(2) . .
C17 C20 C10 117.56(19) . .
C10 C21 C7 122.6(2) . .
C19 O2 C5 119.18(17) . .
C17 O3 C3 118.40(17) . .
C14 O4 C8 110.08(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C15 1.349(3) .
O1 C1 1.425(3) .
C2 C8 1.525(3) .
C3 O3 1.421(3) .
C4 C14 1.379(3) .
C4 C9 1.422(3) .
C4 C18 1.426(3) .
C5 O2 1.421(3) .
N1 C13 1.143(3) .
C6 C8 1.519(3) .
C7 C12 1.378(3) .
C7 C21 1.417(3) .
C7 C8 1.508(3) .
C8 O4 1.481(2) .
C9 N2 1.148(3) .
C10 C21 1.357(3) .
C10 C20 1.429(3) .
C11 C19 1.385(3) .
C11 C15 1.385(3) .
C12 C13 1.421(3) .
C12 C14 1.429(3) .
C14 O4 1.326(2) .
C15 C16 1.393(3) .
C16 C17 1.376(3) .
C17 O3 1.349(3) .
C17 C20 1.423(3) .
C18 N3 1.146(3) .
C19 O2 1.350(3) .
C19 C20 1.409(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 88550217
