#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/99/2209904.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2209904
loop_
_publ_author_name
'Huang, Bor-Hunn'
'Peng, Ya-Liu'
'Lin, Chu-Chieh'
_publ_section_title
Bis[(1Z,3Z)-1,3-bis(4-fluorophenyl)-N,N'-diphenylpropanediiminato]magnesium(II)
_journal_coeditor_code           IS2065
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1977
_journal_page_last               m1978
_journal_paper_doi               10.1107/S1600536806027954
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Mg (C27 H19 F2 N2)2]'
_chemical_formula_moiety         'C54 H38 F4 Mg N4'
_chemical_formula_sum            'C54 H38 F4 Mg N4'
_chemical_formula_weight         843.19
_chemical_name_systematic
Bis[(1Z,3Z)-1,3-bis(4-fluorophenyl)-N,N'-diphenylpropanediiminato]magnesium(II)
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 106.2010(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.0564(15)
_cell_length_b                   10.5743(7)
_cell_length_c                   19.4356(13)
_cell_measurement_reflns_used    2674
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.870
_cell_measurement_theta_min      2.288
_cell_volume                     4353.0(5)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1999)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'φ and ω 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  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12188
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         1.92
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1752
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.905
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0410
_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)+(0.0567P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1128
_reflns_number_gt                2339
_reflns_number_total             4270
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2065.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2209904
_cod_database_fobs_code          2209904
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'
'-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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Mg Mg 0.5000 0.15309(9) 0.2500 0.0432(3) Uani d S 1
F F1 0.33159(8) 0.65235(14) -0.07840(8) 0.1010(5) Uani d . 1
F F2 0.72941(7) 0.01347(15) -0.02150(9) 0.1013(6) Uani d . 1
N N1 0.44314(7) 0.25070(15) 0.16709(8) 0.0464(4) Uani d . 1
N N2 0.54626(8) 0.06484(15) 0.18583(8) 0.0451(4) Uani d . 1
C C1 0.46219(9) 0.28050(18) 0.10935(10) 0.0445(5) Uani d . 1
C C2 0.51500(9) 0.22538(19) 0.09460(10) 0.0466(5) Uani d . 1
H H2A 0.5284 0.2648 0.0586 0.056 Uiso calc R 1
C C3 0.55084(9) 0.11980(18) 0.12578(10) 0.0422(5) Uani d . 1
C C4 0.38015(10) 0.27652(19) 0.16888(11) 0.0473(5) Uani d . 1
C C5 0.32870(10) 0.24184(19) 0.11343(12) 0.0552(6) Uani d . 1
H H5A 0.3349 0.2125 0.0708 0.066 Uiso calc R 1
C C6 0.26824(11) 0.2500(2) 0.12012(15) 0.0744(7) Uani d . 1
H H6A 0.2341 0.2264 0.0821 0.089 Uiso calc R 1
C C7 0.25832(14) 0.2927(3) 0.18265(18) 0.0858(9) Uani d . 1
H H7A 0.2176 0.2971 0.1873 0.103 Uiso calc R 1
C C8 0.30860(15) 0.3290(2) 0.23819(15) 0.0794(8) Uani d . 1
H H8A 0.3018 0.3592 0.2804 0.095 Uiso calc R 1
C C9 0.36968(12) 0.3210(2) 0.23186(12) 0.0628(6) Uani d . 1
H H9A 0.4036 0.3454 0.2699 0.075 Uiso calc R 1
C C10 0.42826(9) 0.37966(19) 0.05840(10) 0.0451(5) Uani d . 1
C C11 0.40926(10) 0.3594(2) -0.01487(11) 0.0582(6) Uani d . 1
H H11A 0.4186 0.2829 -0.0332 0.070 Uiso calc R 1
C C12 0.37675(11) 0.4508(2) -0.06106(13) 0.0677(7) Uani d . 1
H H12A 0.3632 0.4363 -0.1102 0.081 Uiso calc R 1
C C13 0.36485(11) 0.5632(2) -0.03289(14) 0.0662(7) Uani d . 1
C C14 0.38430(12) 0.5893(2) 0.03818(14) 0.0674(7) Uani d . 1
H H14A 0.3765 0.6678 0.0556 0.081 Uiso calc R 1
C C15 0.41584(10) 0.4965(2) 0.08377(13) 0.0577(6) Uani d . 1
H H15A 0.4291 0.5125 0.1327 0.069 Uiso calc R 1
C C16 0.59807(9) 0.07764(17) 0.08816(10) 0.0424(5) Uani d . 1
C C17 0.58006(10) 0.06118(19) 0.01429(10) 0.0513(5) Uani d . 1
H H17A 0.5375 0.0663 -0.0108 0.062 Uiso calc R 1
C C18 0.62418(12) 0.0373(2) -0.02267(12) 0.0614(6) Uani d . 1
H H18A 0.6118 0.0246 -0.0720 0.074 Uiso calc R 1
C C19 0.68597(12) 0.0331(2) 0.01501(14) 0.0624(6) Uani d . 1
C C20 0.70626(11) 0.0478(2) 0.08743(13) 0.0616(6) Uani d . 1
H H20A 0.7490 0.0436 0.1115 0.074 Uiso calc R 1
C C21 0.66193(10) 0.06915(19) 0.12451(11) 0.0520(5) Uani d . 1
H H21A 0.6750 0.0779 0.1741 0.062 Uiso calc R 1
C C22 0.57449(10) -0.05449(19) 0.20918(11) 0.0472(5) Uani d . 1
C C23 0.54983(11) -0.1652(2) 0.17496(12) 0.0631(6) Uani d . 1
H H23A 0.5171 -0.1615 0.1328 0.076 Uiso calc R 1
C C24 0.57331(14) -0.2816(2) 0.20272(15) 0.0774(8) Uani d . 1
H H24A 0.5565 -0.3554 0.1789 0.093 Uiso calc R 1
C C25 0.62108(14) -0.2885(3) 0.26491(15) 0.0773(8) Uani d . 1
H H25A 0.6364 -0.3669 0.2837 0.093 Uiso calc R 1
C C26 0.64644(13) -0.1795(3) 0.29959(13) 0.0720(7) Uani d . 1
H H26A 0.6795 -0.1841 0.3415 0.086 Uiso calc R 1
C C27 0.62290(11) -0.0626(2) 0.27230(12) 0.0610(6) Uani d . 1
H H27A 0.6397 0.0108 0.2965 0.073 Uiso calc R 1
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'
Mg Mg 0.0486 0.0363 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 Mg N1 . 2_655 118.76(10) yes
N1 Mg N2 2_655 . 114.47(6) no
N1 Mg N2 . . 92.91(6) yes
N1 Mg N2 2_655 2_655 92.91(6) no
N1 Mg N2 . 2_655 114.47(6) yes
N2 Mg N2 . 2_655 125.67(10) yes
C1 N1 C4 . . 120.68(16) no
C1 N1 Mg . . 121.08(13) no
C4 N1 Mg . . 117.98(11) no
C3 N2 C22 . . 122.16(15) no
C3 N2 Mg . . 120.53(13) no
C22 N2 Mg . . 117.28(11) no
N1 C1 C2 . . 123.07(18) no
N1 C1 C10 . . 120.29(17) no
C2 C1 C10 . . 116.61(16) no
C1 C2 C3 . . 129.96(17) no
C1 C2 H2A . . 115.0 no
C3 C2 H2A . . 115.0 no
N2 C3 C2 . . 123.61(16) no
N2 C3 C16 . . 122.05(17) no
C2 C3 C16 . . 114.24(16) no
C5 C4 C9 . . 118.4(2) no
C5 C4 N1 . . 121.67(18) no
C9 C4 N1 . . 119.3(2) no
C6 C5 C4 . . 121.1(2) no
C6 C5 H5A . . 119.4 no
C4 C5 H5A . . 119.4 no
C7 C6 C5 . . 120.2(3) no
C7 C6 H6A . . 119.9 no
C5 C6 H6A . . 119.9 no
C6 C7 C8 . . 119.8(2) no
C6 C7 H7A . . 120.1 no
C8 C7 H7A . . 120.1 no
C7 C8 C9 . . 120.3(2) no
C7 C8 H8A . . 119.8 no
C9 C8 H8A . . 119.8 no
C8 C9 C4 . . 120.2(2) no
C8 C9 H9A . . 119.9 no
C4 C9 H9A . . 119.9 no
C11 C10 C15 . . 118.08(19) no
C11 C10 C1 . . 121.73(18) no
C15 C10 C1 . . 120.18(18) no
C12 C11 C10 . . 121.0(2) no
C12 C11 H11A . . 119.5 no
C10 C11 H11A . . 119.5 no
C13 C12 C11 . . 118.2(2) no
C13 C12 H12A . . 120.9 no
C11 C12 H12A . . 120.9 no
C14 C13 F1 . . 118.8(2) no
C14 C13 C12 . . 123.0(2) no
F1 C13 C12 . . 118.2(2) no
C13 C14 C15 . . 118.1(2) no
C13 C14 H14A . . 121.0 no
C15 C14 H14A . . 121.0 no
C14 C15 C10 . . 121.5(2) no
C14 C15 H15A . . 119.3 no
C10 C15 H15A . . 119.3 no
C17 C16 C21 . . 118.28(17) no
C17 C16 C3 . . 120.28(18) no
C21 C16 C3 . . 120.98(17) no
C18 C17 C16 . . 121.3(2) no
C18 C17 H17A . . 119.4 no
C16 C17 H17A . . 119.4 no
C19 C18 C17 . . 118.1(2) no
C19 C18 H18A . . 120.9 no
C17 C18 H18A . . 120.9 no
F2 C19 C18 . . 118.2(2) no
F2 C19 C20 . . 118.8(2) no
C18 C19 C20 . . 123.1(2) no
C19 C20 C21 . . 118.7(2) no
C19 C20 H20A . . 120.7 no
C21 C20 H20A . . 120.7 no
C20 C21 C16 . . 120.5(2) no
C20 C21 H21A . . 119.7 no
C16 C21 H21A . . 119.7 no
C23 C22 C27 . . 118.5(2) no
C23 C22 N2 . . 121.3(2) no
C27 C22 N2 . . 119.81(19) no
C22 C23 C24 . . 120.8(2) no
C22 C23 H23A . . 119.6 no
C24 C23 H23A . . 119.6 no
C25 C24 C23 . . 120.3(2) no
C25 C24 H24A . . 119.9 no
C23 C24 H24A . . 119.9 no
C24 C25 C26 . . 119.8(2) no
C24 C25 H25A . . 120.1 no
C26 C25 H25A . . 120.1 no
C25 C26 C27 . . 120.2(2) no
C25 C26 H26A . . 119.9 no
C27 C26 H26A . . 119.9 no
C26 C27 C22 . . 120.5(2) no
C26 C27 H27A . . 119.8 no
C22 C27 H27A . . 119.8 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Mg N1 2_655 2.0266(17) no
Mg N1 . 2.0266(17) yes
Mg N2 . 2.0439(15) yes
Mg N2 2_655 2.0439(15) no
F1 C13 . 1.359(2) y
F2 C19 . 1.358(2) y
N1 C1 . 1.341(2) y
N1 C4 . 1.426(2) no
N2 C3 . 1.333(2) y
N2 C22 . 1.424(2) no
C1 C2 . 1.402(3) y
C1 C10 . 1.492(3) no
C2 C3 . 1.404(3) y
C2 H2A . 0.9300 no
C3 C16 . 1.498(2) no
C4 C5 . 1.379(3) no
C4 C9 . 1.389(3) no
C5 C6 . 1.378(3) no
C5 H5A . 0.9300 no
C6 C7 . 1.370(3) no
C6 H6A . 0.9300 no
C7 C8 . 1.369(4) no
C7 H7A . 0.9300 no
C8 C9 . 1.389(3) no
C8 H8A . 0.9300 no
C9 H9A . 0.9300 no
C10 C11 . 1.384(3) no
C10 C15 . 1.386(3) no
C11 C12 . 1.376(3) no
C11 H11A . 0.9300 no
C12 C13 . 1.364(3) no
C12 H12A . 0.9300 no
C13 C14 . 1.356(3) no
C14 C15 . 1.374(3) no
C14 H14A . 0.9300 no
C15 H15A . 0.9300 no
C16 C17 . 1.390(3) no
C16 C21 . 1.391(3) no
C17 C18 . 1.385(3) no
C17 H17A . 0.9300 no
C18 C19 . 1.356(3) no
C18 H18A . 0.9300 no
C19 C20 . 1.362(3) no
C20 C21 . 1.385(3) no
C20 H20A . 0.9300 no
C21 H21A . 0.9300 no
C22 C23 . 1.381(3) no
C22 C27 . 1.386(3) no
C23 C24 . 1.386(3) no
C23 H23A . 0.9300 no
C24 C25 . 1.366(4) no
C24 H24A . 0.9300 no
C25 C26 . 1.373(3) no
C25 H25A . 0.9300 no
C26 C27 . 1.388(3) no
C26 H26A . 0.9300 no
C27 H27A . 0.9300 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168309001
