#------------------------------------------------------------------------------
#$Date: 2021-08-30 11:29:01 +0300 (Mon, 30 Aug 2021) $
#$Revision: 268286 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/44/1564436.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_1564436
loop_
_publ_author_name
'Volpi, Giorgio'
'Priola, Emanuele'
'Garino, Claudio'
'Daolio, Andrea'
'Rabezzana, Roberto'
'Benzi, Paola'
'Giordana, Alessia'
'Diana, Eliano'
'Gobetto, Roberto'
_publ_section_title
;
 Blue fluorescent zinc(II) complexes based on tunable
 imidazo[1,5-a]pyridines
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119662
_journal_paper_doi               10.1016/j.ica.2020.119662
_journal_volume                  509
_journal_year                    2020
_chemical_formula_moiety         ' C19 H12 Cl2 F3 N3 Zn, C2 H3 N '
_chemical_formula_sum            'C21 H15 Cl2 F3 N4 Zn'
_chemical_formula_weight         516.66
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                116.668(6)
_cell_angle_beta                 94.023(5)
_cell_angle_gamma                106.033(6)
_cell_formula_units_Z            2
_cell_length_a                   10.8520(7)
_cell_length_b                   10.9062(8)
_cell_length_c                   11.1940(6)
_cell_measurement_reflns_used    4046
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.9957
_cell_measurement_theta_min      4.3480
_cell_volume                     1108.43(15)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'SHELXP-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.2890
_diffrn_measured_fraction_theta_full 0.9957
_diffrn_measured_fraction_theta_max 0.9957
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scan'
_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  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9996
_diffrn_reflns_theta_full        66.9957
_diffrn_reflns_theta_max         66.9957
_diffrn_reflns_theta_min         4.3480
_diffrn_standards_number         9996
_exptl_absorpt_coefficient_mu    4.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             520.0
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.939
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3789
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1068P)²+0.6644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1949
_reflns_number_gt                2799
_reflns_number_total             3789
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2020-509-119662.CIF
_cod_data_source_block           3
_cod_original_cell_volume        1108.42(12)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        ' C21 H15 Cl2 F3 N4 Zn '
_cod_database_code               1564436
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_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
Zn1 Zn 0.78835(6) 0.06414(7) 0.33013(6) 0.0610(3) Uani 1 1 d . . .
Cl2 Cl 0.83813(14) -0.0308(2) 0.12719(15) 0.0737(5) Uani 1 1 d . . .
Cl1 Cl 0.93160(15) 0.26835(17) 0.50012(16) 0.0771(5) Uani 1 1 d . . .
N2 N 0.5930(4) 0.0452(4) 0.2985(4) 0.0467(9) Uani 1 1 d . . .
N1 N 0.7126(4) -0.0886(5) 0.3917(4) 0.0539(10) Uani 1 1 d . . .
C6 C 0.5161(5) -0.0626(5) 0.3200(5) 0.0479(11) Uani 1 1 d . . .
C5 C 0.5808(5) -0.1351(5) 0.3732(5) 0.0487(11) Uani 1 1 d . . .
N3 N 0.3878(4) 0.0148(5) 0.2299(4) 0.0513(10) Uani 1 1 d . . .
C13 C 0.5654(5) 0.1998(5) 0.2000(5) 0.0484(11) Uani 1 1 d . . .
C7 C 0.3857(5) -0.0843(5) 0.2782(5) 0.0519(12) Uani 1 1 d . . .
C12 C 0.5172(4) 0.0904(5) 0.2429(5) 0.0468(11) Uani 1 1 d . . .
C11 C 0.2726(5) 0.0289(8) 0.1833(6) 0.0676(15) Uani 1 1 d . . .
H11 H 0.2755 0.0976 0.1549 0.081 Uiso 1 1 calc R . .
C4 C 0.5166(6) -0.2423(6) 0.4031(6) 0.0648(14) Uani 1 1 d . . .
H4 H 0.4253 -0.2759 0.3882 0.078 Uiso 1 1 calc R . .
C14 C 0.4989(5) 0.1886(6) 0.0812(5) 0.0552(12) Uani 1 1 d . . .
H14 H 0.4197 0.1127 0.0300 0.066 Uiso 1 1 calc R . .
C15 C 0.5513(6) 0.2902(6) 0.0409(6) 0.0618(14) Uani 1 1 d . . .
H15 H 0.5065 0.2827 -0.0374 0.074 Uiso 1 1 calc R . .
C17 C 0.7340(6) 0.4160(6) 0.2326(6) 0.0635(14) Uani 1 1 d . . .
H17 H 0.8130 0.4926 0.2833 0.076 Uiso 1 1 calc R . .
C16 C 0.6685(6) 0.4023(6) 0.1140(6) 0.0630(14) Uani 1 1 d . A .
C8 C 0.2610(5) -0.1729(7) 0.2751(6) 0.0677(16) Uani 1 1 d . . .
H8 H 0.2555 -0.2397 0.3065 0.081 Uiso 1 1 calc R . .
C18 C 0.6822(5) 0.3163(6) 0.2755(5) 0.0580(13) Uani 1 1 d . . .
H18 H 0.7260 0.3270 0.3560 0.070 Uiso 1 1 calc R . .
C2 C 0.7240(7) -0.2487(6) 0.4783(6) 0.0711(16) Uani 1 1 d . . .
H2 H 0.7751 -0.2843 0.5157 0.085 Uiso 1 1 calc R . .
C1 C 0.7812(6) -0.1443(6) 0.4447(6) 0.0656(14) Uani 1 1 d . . .
H1 H 0.8724 -0.1100 0.4594 0.079 Uiso 1 1 calc R . .
C10 C 0.1577(6) -0.0594(9) 0.1807(7) 0.084(2) Uani 1 1 d . . .
H10 H 0.0799 -0.0537 0.1470 0.101 Uiso 1 1 calc R . .
C3 C 0.5916(8) -0.2997(7) 0.4563(7) 0.0761(18) Uani 1 1 d . . .
H3 H 0.5503 -0.3728 0.4765 0.091 Uiso 1 1 calc R . .
C9 C 0.1512(6) -0.1607(8) 0.2273(7) 0.083(2) Uani 1 1 d . . .
H9 H 0.0696 -0.2198 0.2249 0.100 Uiso 1 1 calc R . .
C19 C 0.7237(9) 0.5122(7) 0.0684(8) 0.0869(19) Uani 1 1 d U . .
C21 C 0.8088(10) 0.6059(9) 0.7264(9) 0.101(3) Uani 1 1 d . . .
N4 N 0.7087(10) 0.5675(12) 0.6619(12) 0.153(4) Uani 1 1 d . . .
C20 C 0.9366(9) 0.6529(12) 0.8076(12) 0.131(3) Uani 1 1 d . . .
H20A H 0.9486 0.7381 0.8937 0.196 Uiso 1 1 calc R . .
H20B H 1.0017 0.6761 0.7600 0.196 Uiso 1 1 calc R . .
H20C H 0.9457 0.5762 0.8238 0.196 Uiso 1 1 calc R . .
F1 F 0.6860(18) 0.4598(13) -0.0616(10) 0.117(5) Uani 0.67(2) 1 d PU A 1
F2 F 0.666(2) 0.6194(12) 0.1224(11) 0.119(5) Uani 0.67(2) 1 d PU A 1
F3 F 0.8400(12) 0.580(3) 0.111(3) 0.174(10) Uani 0.67(2) 1 d PU A 1
F1A F 0.845(3) 0.492(3) 0.029(3) 0.114(7) Uani 0.33(2) 1 d PU A 2
F2A F 0.660(4) 0.503(5) -0.038(4) 0.161(14) Uani 0.33(2) 1 d PU A 2
F3A F 0.781(5) 0.6455(17) 0.157(2) 0.119(13) Uani 0.33(2) 1 d PU A 2
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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
N2 Zn1 N1 80.50(16) . .
N2 Zn1 Cl1 118.72(12) . .
N1 Zn1 Cl1 111.71(12) . .
N2 Zn1 Cl2 107.90(11) . .
N1 Zn1 Cl2 113.26(13) . .
Cl1 Zn1 Cl2 118.73(7) . .
C12 N2 C6 109.4(4) . .
C12 N2 Zn1 137.8(3) . .
C6 N2 Zn1 111.7(3) . .
C1 N1 C5 118.8(5) . .
C1 N1 Zn1 126.5(4) . .
C5 N1 Zn1 114.8(3) . .
N2 C6 C7 108.8(4) . .
N2 C6 C5 118.4(4) . .
C7 C6 C5 132.7(4) . .
N1 C5 C4 120.9(5) . .
N1 C5 C6 114.2(4) . .
C4 C5 C6 124.9(5) . .
C12 N3 C11 129.9(5) . .
C12 N3 C7 108.2(4) . .
C11 N3 C7 121.9(5) . .
C18 C13 C14 118.5(5) . .
C18 C13 C12 119.7(4) . .
C14 C13 C12 121.8(4) . .
C6 C7 N3 105.1(4) . .
C6 C7 C8 137.5(5) . .
N3 C7 C8 117.4(5) . .
N2 C12 N3 108.5(4) . .
N2 C12 C13 124.6(4) . .
N3 C12 C13 127.0(4) . .
C10 C11 N3 117.9(7) . .
C5 C4 C3 118.7(6) . .
C15 C14 C13 119.8(5) . .
C16 C15 C14 121.1(5) . .
C18 C17 C16 120.1(5) . .
C15 C16 C17 119.6(5) . .
C15 C16 C19 120.2(5) . .
C17 C16 C19 120.1(6) . .
C9 C8 C7 120.1(6) . .
C17 C18 C13 120.8(5) . .
C3 C2 C1 118.7(6) . .
N1 C1 C2 123.2(6) . .
C11 C10 C9 121.9(6) . .
C2 C3 C4 119.8(6) . .
C8 C9 C10 120.7(6) . .
F3 C19 F3A 51.5(13) . .
F3 C19 F2A 121.3(18) . .
F3A C19 F2A 109(2) . .
F3 C19 F1 113.2(15) . .
F3A C19 F1 126.5(14) . .
F2A C19 F1 26(2) . .
F3 C19 F2 104.0(12) . .
F3A C19 F2 53.1(17) . .
F2A C19 F2 76(2) . .
F1 C19 F2 102.4(10) . .
F3 C19 F1A 43.2(13) . .
F3A C19 F1A 93.6(18) . .
F2A C19 F1A 103(2) . .
F1 C19 F1A 81.4(13) . .
F2 C19 F1A 141.7(10) . .
F3 C19 C16 115.9(8) . .
F3A C19 C16 119.8(11) . .
F2A C19 C16 119.9(17) . .
F1 C19 C16 112.6(8) . .
F2 C19 C16 107.3(8) . .
F1A C19 C16 106.0(11) . .
N4 C21 C20 179.2(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 N2 2.061(4) .
Zn1 N1 2.068(4) .
Zn1 Cl1 2.2059(15) .
Zn1 Cl2 2.2123(16) .
N2 C12 1.318(6) .
N2 C6 1.370(6) .
N1 C1 1.338(7) .
N1 C5 1.345(7) .
C6 C7 1.378(7) .
C6 C5 1.464(7) .
C5 C4 1.378(7) .
N3 C12 1.377(6) .
N3 C11 1.395(7) .
N3 C7 1.405(7) .
C13 C18 1.390(7) .
C13 C14 1.405(7) .
C13 C12 1.460(7) .
C7 C8 1.417(7) .
C11 C10 1.337(9) .
C4 C3 1.399(9) .
C14 C15 1.376(8) .
C15 C16 1.371(8) .
C17 C18 1.377(8) .
C17 C16 1.386(8) .
C16 C19 1.501(9) .
C8 C9 1.336(9) .
C2 C3 1.349(10) .
C2 C1 1.360(8) .
C10 C9 1.407(11) .
C19 F3 1.204(13) .
C19 F3A 1.27(2) .
C19 F2A 1.28(3) .
C19 F1 1.285(14) .
C19 F2 1.399(14) .
C19 F1A 1.45(3) .
C21 N4 1.115(11) .
C21 C20 1.423(13) .
