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#$Date: 2025-08-20 17:59:05 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301833 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/96/4119657.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_4119657
loop_
_publ_author_name
'Valeria Amendola'
'Greta Bergamaschi'
'Massimo Boiocchi'
'Luigi Fabbrizzi'
'Lorenzo Mosca'
_publ_contact_author_address
;
Dipartimento di Chimica
University of Pavia
via Taramelli 12, I-27100 Pavia, ITALY
;
_publ_contact_author_email
;
luigi.fabbrizzi@unipv.it
;
_publ_contact_author_name        'Prof. Luigi Fabbrizzi'
_publ_section_title
;
 The Interaction of Fluoride with Fluorogenic Ureas: An ON1-OFF-ON2
 Response
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6345
_journal_page_last               6355
_journal_paper_doi               10.1021/ja4019786
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H16 N2 O'
_chemical_formula_sum            'C21 H16 N2 O'
_chemical_formula_weight         312.36
_chemical_name_systematic
;
 N-(2-anthracenyl)-N'-(phenyl)-urea
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.452(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   33.056(4)
_cell_length_b                   4.6392(6)
_cell_length_c                   10.2004(14)
_cell_measurement_reflns_used    932
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24
_cell_measurement_theta_min      2
_cell_volume                     1543.0(3)
_computing_cell_refinement       'SAINT (Bruker-Axs Inc)'
_computing_data_collection       'SMART (Bruker-Axs Inc)'
_computing_data_reduction        'SAINT (Bruker-Axs Inc)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker-Axs Smart-Apex CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5323
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.25
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       'PLATY PRISM'
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         1372
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0436P)²+0.2021P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                1107
_reflns_number_total             1372
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ja4019786_si_001_1.cif
_cod_data_source_block           1_fluo_urea
_cod_original_cell_volume        1543.0(4)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4119657
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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
C1 C 0.44717(16) 0.1449(6) 0.1849(5) 0.0435(7) Uani 1 1 d .
C2 C 0.38345(14) 0.1092(8) 0.2749(4) 0.0453(11) Uani 1 1 d .
C3 C 0.39077(13) 0.3131(9) 0.3801(4) 0.0489(11) Uani 1 1 d .
H3 H 0.4175 0.3676 0.4141 0.059 Uiso 1 1 calc R
C4 C 0.35919(13) 0.4284(11) 0.4311(4) 0.0534(13) Uani 1 1 d .
H4 H 0.3645 0.5660 0.4980 0.064 Uiso 1 1 calc R
C5 C 0.31813(12) 0.3435(10) 0.3843(4) 0.0447(11) Uani 1 1 d .
C6 C 0.28515(12) 0.4559(10) 0.4366(4) 0.0540(10) Uani 1 1 d .
H6 H 0.2901 0.5925 0.5041 0.065 Uiso 1 1 calc R
C7 C 0.24492(11) 0.3694(9) 0.3905(4) 0.0521(11) Uani 1 1 d .
C8 C 0.21084(13) 0.4835(12) 0.4420(4) 0.0660(13) Uani 1 1 d .
H8 H 0.2152 0.6207 0.5093 0.079 Uiso 1 1 calc R
C9 C 0.17221(14) 0.3956(12) 0.3945(5) 0.0728(14) Uani 1 1 d .
H9 H 0.1505 0.4714 0.4309 0.087 Uiso 1 1 calc R
C10 C 0.16428(14) 0.1938(11) 0.2922(5) 0.0708(13) Uani 1 1 d .
H10 H 0.1375 0.1375 0.2600 0.085 Uiso 1 1 calc R
C11 C 0.19590(12) 0.0802(11) 0.2398(5) 0.0655(12) Uani 1 1 d .
H11 H 0.1904 -0.0537 0.1714 0.079 Uiso 1 1 calc R
C12 C 0.23716(11) 0.1610(9) 0.2871(4) 0.0530(11) Uani 1 1 d .
C13 C 0.27052(12) 0.0479(10) 0.2347(4) 0.0561(11) Uani 1 1 d .
H13 H 0.2656 -0.0886 0.1672 0.067 Uiso 1 1 calc R
C14 C 0.31071(12) 0.1334(9) 0.2803(4) 0.0434(11) Uani 1 1 d .
C15 C 0.34464(14) 0.0220(11) 0.2280(5) 0.0495(11) Uani 1 1 d .
H15 H 0.3402 -0.1137 0.1600 0.059 Uiso 1 1 calc R
C16 C 0.51101(14) 0.1235(8) 0.0953(4) 0.0430(10) Uani 1 1 d .
C17 C 0.50409(14) 0.3149(10) -0.0099(4) 0.0545(12) Uani 1 1 d .
H17 H 0.4774 0.3571 -0.0499 0.065 Uiso 1 1 calc R
C18 C 0.53660(16) 0.4426(12) -0.0552(5) 0.0675(16) Uani 1 1 d .
H18 H 0.5318 0.5729 -0.1253 0.081 Uiso 1 1 calc R
C19 C 0.57602(16) 0.3794(12) 0.0020(6) 0.0695(16) Uani 1 1 d .
H19 H 0.5979 0.4691 -0.0280 0.083 Uiso 1 1 calc R
C20 C 0.58300(17) 0.1844(12) 0.1032(6) 0.0717(15) Uani 1 1 d .
H20 H 0.6097 0.1355 0.1403 0.086 Uiso 1 1 calc R
C21 C 0.55027(14) 0.0594(12) 0.1506(4) 0.0582(13) Uani 1 1 d .
H21 H 0.5551 -0.0699 0.2211 0.070 Uiso 1 1 calc R
N1 N 0.41715(12) -0.0141(7) 0.2242(4) 0.0516(10) Uani 1 1 d D
H1N H 0.4174(13) -0.220(2) 0.221(4) 0.062 Uiso 1 1 d D
N2 N 0.47751(12) -0.0081(8) 0.1430(4) 0.0520(10) Uani 1 1 d D
H2N H 0.4784(12) -0.207(3) 0.170(4) 0.062 Uiso 1 1 d D
O1 O 0.44682(12) 0.4124(4) 0.1850(4) 0.0555(6) 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
O1 C1 N1 122.6(5)
O1 C1 N2 122.1(5)
N1 C1 N2 115.2(2)
C15 C2 C3 120.0(4)
C15 C2 N1 120.2(4)
C3 C2 N1 119.7(4)
C4 C3 C2 120.5(4)
C4 C3 H3 119.8
C2 C3 H3 119.8
C3 C4 C5 121.2(4)
C3 C4 H4 119.4
C5 C4 H4 119.4
C6 C5 C4 122.3(4)
C6 C5 C14 119.3(4)
C4 C5 C14 118.4(4)
C5 C6 C7 121.8(4)
C5 C6 H6 119.1
C7 C6 H6 119.1
C6 C7 C8 122.6(4)
C6 C7 C12 119.4(3)
C8 C7 C12 118.0(4)
C9 C8 C7 121.0(5)
C9 C8 H8 119.5
C7 C8 H8 119.5
C8 C9 C10 121.4(4)
C8 C9 H9 119.3
C10 C9 H9 119.3
C11 C10 C9 119.6(5)
C11 C10 H10 120.2
C9 C10 H10 120.2
C10 C11 C12 121.5(5)
C10 C11 H11 119.2
C12 C11 H11 119.2
C13 C12 C11 122.8(4)
C13 C12 C7 118.6(3)
C11 C12 C7 118.5(4)
C14 C13 C12 122.2(4)
C14 C13 H13 118.9
C12 C13 H13 118.9
C13 C14 C15 122.8(4)
C13 C14 C5 118.7(4)
C15 C14 C5 118.5(4)
C2 C15 C14 121.3(5)
C2 C15 H15 119.3
C14 C15 H15 119.3
C21 C16 C17 119.2(4)
C21 C16 N2 120.6(4)
C17 C16 N2 120.2(4)
C18 C17 C16 120.0(4)
C18 C17 H17 120.0
C16 C17 H17 120.0
C19 C18 C17 120.5(5)
C19 C18 H18 119.8
C17 C18 H18 119.8
C20 C19 C18 119.7(5)
C20 C19 H19 120.1
C18 C19 H19 120.1
C19 C20 C21 119.9(5)
C19 C20 H20 120.1
C21 C20 H20 120.1
C16 C21 C20 120.7(5)
C16 C21 H21 119.6
C20 C21 H21 119.6
C1 N1 C2 123.1(3)
C1 N1 H1N 122(3)
C2 N1 H1N 115(3)
C1 N2 C16 122.9(3)
C1 N2 H2N 114(3)
C16 N2 H2N 122(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.241(3)
C1 N1 1.349(6)
C1 N2 1.354(6)
C2 C15 1.355(6)
C2 C3 1.421(6)
C2 N1 1.423(6)
C3 C4 1.351(6)
C3 H3 0.9300
C4 C5 1.418(6)
C4 H4 0.9300
C5 C6 1.391(6)
C5 C14 1.432(5)
C6 C7 1.395(5)
C6 H6 0.9300
C7 C8 1.421(6)
C7 C12 1.423(5)
C8 C9 1.352(6)
C8 H8 0.9300
C9 C10 1.395(7)
C9 H9 0.9300
C10 C11 1.356(6)
C10 H10 0.9300
C11 C12 1.420(5)
C11 H11 0.9300
C12 C13 1.404(6)
C13 C14 1.391(6)
C13 H13 0.9300
C14 C15 1.417(6)
C15 H15 0.9300
C16 C21 1.360(6)
C16 C17 1.383(6)
C16 N2 1.419(6)
C17 C18 1.372(7)
C17 H17 0.9300
C18 C19 1.369(7)
C18 H18 0.9300
C19 C20 1.364(7)
C19 H19 0.9300
C20 C21 1.383(7)
C20 H20 0.9300
C21 H21 0.9300
N1 H1N 0.957(11)
N2 H2N 0.960(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101464220
