#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/46/7234629.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_7234629
loop_
_publ_author_name
'Yang Zhang'
'Jaume Garcia-Amoros'
'Burjor Captain'
'Francisco M. Raymo'
_publ_section_title
;
 A fluorescent and halochromic indolizine switch
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              2744
_journal_page_last               2747
_journal_paper_doi               10.1039/C5TC03331D
_journal_volume                  4
_journal_year                    2016
_chemical_formula_sum            'C20 H14 F6 N4 O4'
_chemical_formula_weight         488.35
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 104.7170(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6010(4)
_cell_length_b                   21.0213(10)
_cell_length_c                   11.9369(6)
_cell_measurement_reflns_used    6624
_cell_measurement_temperature    100
_cell_measurement_theta_max      3.59
_cell_measurement_theta_min      2.62
_cell_volume                     2087.43(17)
_computing_cell_refinement       'SAINT+  V7.46A (Bruker, 2007)'
_computing_data_collection       'APEX2 v2.2-0 (Bruker, 2007)'
_computing_data_reduction        'SAINT+  V7.46A (Bruker, 2007)'
_computing_molecular_graphics    'XSHELL v4.02 (Bruker, 2000)'
_computing_publication_material  'XCIF v6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21135
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_correction_T_min  0.9363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS 2007/4 Bruker)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0501P)²+0.8416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1029
_reflns_number_gt                4118
_reflns_number_total             5036
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-2744.cif
_cod_data_source_block           collect_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' 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.

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' 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      P2(1)/n
_cod_database_code               7234629
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.37076(14) 0.03720(5) 0.35629(9) 0.0294(2) Uani 1 1 d . . .
O2 O 0.45807(14) 0.04070(5) 0.19418(9) 0.0305(2) Uani 1 1 d . . .
O3 O 0.70394(15) 0.07265(5) 0.70355(11) 0.0372(3) Uani 1 1 d . . .
H3 H 0.6862 0.0359 0.6810 0.056 Uiso 1 1 calc R . .
O4 O 0.89460(12) 0.07006(5) 0.60545(9) 0.0270(2) Uani 1 1 d . . .
N1 N 0.00537(17) -0.10923(6) 0.62219(11) 0.0311(3) Uani 1 1 d . . .
N2 N 0.00557(17) -0.08207(6) 0.94598(12) 0.0315(3) Uani 1 1 d . . .
N3 N 0.29938(13) 0.08371(5) 0.73462(9) 0.0167(2) Uani 1 1 d . . .
N4 N 0.24520(15) 0.02208(6) 0.56558(10) 0.0208(2) Uani 1 1 d . . .
C1 C 0.07473(17) -0.06643(6) 0.66962(12) 0.0215(3) Uani 1 1 d . . .
C2 C 0.07993(18) -0.04907(6) 0.90379(12) 0.0230(3) Uani 1 1 d . . .
C3 C 0.16025(16) -0.01366(6) 0.73216(11) 0.0184(3) Uani 1 1 d . . .
C4 C 0.23636(15) 0.03097(6) 0.67319(11) 0.0175(3) Uani 1 1 d . . .
C5 C 0.32009(16) 0.08807(6) 0.85312(11) 0.0188(3) Uani 1 1 d . . .
C6 C 0.25747(17) 0.04377(6) 0.91231(12) 0.0212(3) Uani 1 1 d . . .
H6 H 0.2733 0.0464 0.9922 0.025 Uiso 1 1 calc R . .
C7 C 0.16833(16) -0.00598(6) 0.84875(12) 0.0195(3) Uani 1 1 d . . .
C8 C 0.41431(17) 0.14694(6) 0.89925(12) 0.0206(3) Uani 1 1 d . . .
C9 C 0.3311(2) 0.18694(7) 0.97483(13) 0.0288(3) Uani 1 1 d . . .
H9A H 0.2258 0.1989 0.9303 0.043 Uiso 1 1 calc R . .
H9B H 0.3935 0.2245 1.0007 0.043 Uiso 1 1 calc R . .
H9C H 0.3221 0.1624 1.0407 0.043 Uiso 1 1 calc R . .
C10 C 0.58339(17) 0.12607(7) 0.96820(12) 0.0252(3) Uani 1 1 d . . .
H10A H 0.5748 0.1012 1.0338 0.038 Uiso 1 1 calc R . .
H10B H 0.6480 0.1630 0.9944 0.038 Uiso 1 1 calc R . .
H10C H 0.6326 0.1010 0.9193 0.038 Uiso 1 1 calc R . .
C11 C 0.41888(16) 0.18026(6) 0.78836(12) 0.0203(3) Uani 1 1 d . . .
C12 C 0.35195(15) 0.14269(6) 0.69248(11) 0.0182(3) Uani 1 1 d . . .
C13 C 0.32800(17) 0.16434(7) 0.57990(12) 0.0220(3) Uani 1 1 d . . .
H13 H 0.2790 0.1393 0.5166 0.026 Uiso 1 1 calc R . .
C14 C 0.38155(18) 0.22590(7) 0.56664(13) 0.0253(3) Uani 1 1 d . . .
H14 H 0.3691 0.2421 0.4924 0.030 Uiso 1 1 calc R . .
C15 C 0.45283(18) 0.26349(7) 0.66125(13) 0.0270(3) Uani 1 1 d . . .
H15 H 0.4889 0.3041 0.6496 0.032 Uiso 1 1 calc R . .
C16 C 0.47086(18) 0.24113(7) 0.77312(13) 0.0249(3) Uani 1 1 d . . .
H16 H 0.5170 0.2666 0.8366 0.030 Uiso 1 1 calc R . .
C22 C 0.82095(17) 0.09459(7) 0.66892(12) 0.0234(3) Uani 1 1 d . . .
C30 C 0.43662(17) 0.06325(7) 0.28309(12) 0.0235(3) Uani 1 1 d . . .
C32 C 0.86948(18) 0.16236(7) 0.71405(12) 0.0251(3) Uani 1 1 d . . .
C34 C 0.49374(19) 0.13156(7) 0.31710(13) 0.0283(3) Uani 1 1 d . . .
F1 F 0.36847(13) 0.17062(4) 0.30748(9) 0.0399(2) Uani 1 1 d . . .
F2 F 0.58131(12) 0.13467(5) 0.42680(8) 0.0380(2) Uani 1 1 d . . .
F3 F 0.58329(15) 0.15460(5) 0.25068(9) 0.0479(3) Uani 1 1 d . . .
F4 F 0.77513(13) 0.20489(4) 0.64803(9) 0.0416(3) Uani 1 1 d . . .
F5 F 0.85646(18) 0.17135(5) 0.82103(9) 0.0547(3) Uani 1 1 d . . .
F6 F 1.01846(12) 0.17641(5) 0.71161(11) 0.0516(3) Uani 1 1 d . . .
H4A H 0.300(2) 0.0480(9) 0.5349(16) 0.033(5) Uiso 1 1 d . . .
H4B H 0.197(2) -0.0112(10) 0.5247(17) 0.037(5) Uiso 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'
F F 0.0171 0.0103 '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
C4 N3 C5 122.30(11) . .
C4 N3 C12 128.61(11) . .
C5 N3 C12 109.09(10) . .
N1 C1 C3 178.19(15) . .
N2 C2 C7 177.80(16) . .
C7 C3 C4 120.44(12) . .
C7 C3 C1 120.14(12) . .
C4 C3 C1 119.42(12) . .
N4 C4 N3 121.71(12) . .
N4 C4 C3 122.28(12) . .
N3 C4 C3 116.01(11) . .
C6 C5 N3 121.39(12) . .
C6 C5 C8 128.35(12) . .
N3 C5 C8 110.26(11) . .
C5 C6 C7 117.67(12) . .
C3 C7 C6 120.80(12) . .
C3 C7 C2 119.11(12) . .
C6 C7 C2 120.07(12) . .
C5 C8 C11 101.10(11) . .
C5 C8 C9 112.16(11) . .
C11 C8 C9 112.42(12) . .
C5 C8 C10 107.97(11) . .
C11 C8 C10 111.69(11) . .
C9 C8 C10 111.04(12) . .
C16 C11 C12 119.86(13) . .
C16 C11 C8 128.84(13) . .
C12 C11 C8 111.20(11) . .
C13 C12 C11 122.78(12) . .
C13 C12 N3 129.36(12) . .
C11 C12 N3 107.47(11) . .
C12 C13 C14 116.29(13) . .
C15 C14 C13 121.74(13) . .
C16 C15 C14 120.61(13) . .
C11 C16 C15 118.65(13) . .
O4 C22 O3 129.03(14) . .
O4 C22 C32 118.07(13) . .
O3 C22 C32 112.88(12) . .
O2 C30 O1 128.31(14) . .
O2 C30 C34 118.96(13) . .
O1 C30 C34 112.74(12) . .
F6 C32 F5 108.02(13) . .
F6 C32 F4 106.66(13) . .
F5 C32 F4 106.77(12) . .
F6 C32 C22 112.10(12) . .
F5 C32 C22 112.78(12) . .
F4 C32 C22 110.18(12) . .
F3 C34 F2 107.40(13) . .
F3 C34 F1 107.55(13) . .
F2 C34 F1 107.20(12) . .
F3 C34 C30 112.16(12) . .
F2 C34 C30 111.54(12) . .
F1 C34 C30 110.76(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C30 1.2789(17) .
O2 C30 1.2184(17) .
O3 C22 1.2680(18) .
O4 C22 1.2186(17) .
N1 C1 1.1464(19) .
N2 C2 1.1435(19) .
N3 C4 1.3633(17) .
N3 C5 1.3831(16) .
N3 C12 1.4527(16) .
N4 C4 1.3192(17) .
C1 C3 1.4318(19) .
C2 C7 1.4436(19) .
C3 C7 1.3851(18) .
C3 C4 1.4277(18) .
C5 C6 1.3601(19) .
C5 C8 1.5050(18) .
C6 C7 1.4006(19) .
C8 C11 1.5069(19) .
C8 C9 1.5364(19) .
C8 C10 1.542(2) .
C11 C16 1.3827(19) .
C11 C12 1.3892(19) .
C12 C13 1.3838(19) .
C13 C14 1.396(2) .
C14 C15 1.387(2) .
C15 C16 1.387(2) .
C22 C32 1.543(2) .
C30 C34 1.538(2) .
C32 F6 1.3226(18) .
C32 F5 1.3234(17) .
C32 F4 1.3244(17) .
C34 F3 1.3292(18) .
C34 F2 1.3361(17) .
C34 F1 1.3362(19) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339028
