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#$Date: 2025-04-05 14:40:53 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299190 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/34/2023408.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_2023408
loop_
_publ_author_name
'Mewis, Ryan E.'
'Hulme, Matthew C.'
'Marron, Jack'
'Langley, Stuart K.'
'Sutcliffe, Oliver B.'
'Benjamin, Sophie L.'
_publ_section_title
;
 Synthesis and crystal structures of five fluorinated diphenidine
 derivatives.
;
_journal_coeditor_code           EE2011
_journal_issue                   'Pt 3'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              229
_journal_page_last               234
_journal_paper_doi               10.1107/S2056989025001288
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          '2C16 H18 F2 N +, 2Cl -, C H2 Cl2'
_chemical_formula_moiety         '2(C16 H18 F2 N +), 2(Cl -), C H2 Cl2'
_chemical_formula_sum            'C33 H38 Cl4 F4 N2'
_chemical_formula_weight         680.45
_chemical_name_systematic
;
[1-(2,6-Difluorophenyl)-2-phenylethyl](ethyl)azanium chloride
dichloromethane hemisolvate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 92.130(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.9963(14)
_cell_length_b                   7.8729(5)
_cell_length_c                   19.0330(10)
_cell_measurement_reflns_used    8967
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      2.99
_cell_volume                     3443.5(4)
_computing_cell_refinement       CrysAlisPro
_computing_data_collection       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_molecular_graphics
;
X-SEED (Barbour, 2020)
;
_computing_structure_refinement
;
SHELXL2018/3  (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       'scans in phi and omega'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12738
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.293
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.390
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       Block
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.223
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0343P)²+2.8401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0768
_reflns_number_gt                2813
_reflns_number_total             3034
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ee2011.cif
_cod_data_source_block           II
_cod_depositor_comments
'Adding full bibliography for 2023405--2023409.cif.'
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               2023408
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.28641(2) 0.60990(5) 0.16223(2) 0.02972(12) Uani d 1 . .
Cl Cl1S 0.31326(2) 0.28821(7) 0.00859(3) 0.05486(16) Uani d 1 . .
F F1 0.05520(5) 1.14129(13) 0.11535(6) 0.0466(3) Uani d 1 . .
F F2 0.17656(5) 0.69870(15) 0.04908(5) 0.0570(3) Uani d 1 . .
N N1 0.19574(5) 0.90437(17) 0.17878(7) 0.0248(3) Uani d 1 . .
C C1 0.13169(6) 0.88167(19) 0.16264(7) 0.0251(3) Uani d 1 . .
H H1 0.110554 0.967062 0.191048 0.030 Uiso calc 1 . .
C C9 0.11629(6) 0.91562(18) 0.08602(7) 0.0242(3) Uani d 1 . .
C C3 0.05036(7) 0.6689(2) 0.17558(8) 0.0308(3) Uani d 1 . .
C C13 0.12414(8) 0.8489(2) -0.03848(9) 0.0391(4) Uani d 1 . .
H H13 0.140233 0.779839 -0.073793 0.047 Uiso calc 1 . .
C C12 0.08611(7) 0.9784(2) -0.05562(9) 0.0392(4) Uani d 1 . .
H H12 0.075593 0.999429 -0.103567 0.047 Uiso calc 1 . .
C C11 0.06315(7) 1.0777(2) -0.00420(9) 0.0369(4) Uani d 1 . .
H H11 0.037235 1.168104 -0.016069 0.044 Uiso calc 1 . .
C C14 0.13806(7) 0.8227(2) 0.03156(8) 0.0326(4) Uani d 1 . .
C C10 0.07854(6) 1.04341(19) 0.06485(8) 0.0288(3) Uani d 1 . .
C C4 0.00903(8) 0.7455(2) 0.21652(9) 0.0399(4) Uani d 1 . .
H H4 0.021169 0.820557 0.253303 0.048 Uiso calc 1 . .
C C15 0.2196(4) 1.0751(12) 0.1558(4) 0.0316(19) Uani d 0.707(5) A 1
H H15A 0.195508 1.167814 0.174557 0.038 Uiso calc 0.707(5) A 1
H H15B 0.217609 1.082569 0.103855 0.038 Uiso calc 0.707(5) A 1
C C8 0.03174(8) 0.5597(2) 0.12252(9) 0.0388(4) Uani d 1 . .
H H8 0.059436 0.506416 0.093985 0.047 Uiso calc 1 . .
C C2 0.11439(7) 0.7045(2) 0.18834(9) 0.0326(4) Uani d 1 . .
H H2A 0.137251 0.617767 0.163763 0.039 Uiso calc 1 . .
H H2B 0.124134 0.695173 0.239296 0.039 Uiso calc 1 . .
C C7 -0.02704(9) 0.5276(3) 0.11066(10) 0.0501(5) Uani d 1 . .
H H7 -0.039328 0.451887 0.074176 0.060 Uiso calc 1 . .
C C5 -0.04964(8) 0.7136(3) 0.20423(11) 0.0490(5) Uani d 1 . .
H H5 -0.077544 0.767277 0.232379 0.059 Uiso calc 1 . .
C C6 -0.06771(8) 0.6042(3) 0.15123(11) 0.0524(5) Uani d 1 . .
H H6 -0.107970 0.581969 0.142816 0.063 Uiso calc 1 . .
C C16 0.28347(10) 1.0963(3) 0.18310(13) 0.0360(7) Uani d 0.707(5) A 1
H H16A 0.285642 1.081935 0.234280 0.054 Uiso calc 0.707(5) A 1
H H16B 0.297386 1.209892 0.171032 0.054 Uiso calc 0.707(5) A 1
H H16C 0.307818 1.010445 0.161259 0.054 Uiso calc 0.707(5) A 1
C C1S 0.250000 0.4136(3) 0.000000 0.0302(5) Uani d 1 . .
H H1S1 0.252617 0.487565 -0.041826 0.036 Uiso calc 0.5 . .
H H1S2 0.247383 0.487565 0.041827 0.036 Uiso calc 0.5 . .
C C16A 0.1932(3) 1.2115(7) 0.1843(3) 0.0383(18) Uani d 0.293(5) A 2
H H16D 0.155523 1.220984 0.158750 0.057 Uiso calc 0.293(5) A 2
H H16E 0.216492 1.313058 0.175641 0.057 Uiso calc 0.293(5) A 2
H H16F 0.186879 1.201409 0.234797 0.057 Uiso calc 0.293(5) A 2
H H1B 0.2162(8) 0.819(2) 0.1612(9) 0.036(5) Uiso d 1 . .
H H1A 0.2010(7) 0.893(2) 0.2273(10) 0.034(5) Uiso d 1 . .
C C15A 0.2248(10) 1.057(3) 0.1594(10) 0.037(6) Uani d 0.293(5) A 2
H H15C 0.227354 1.060956 0.107617 0.044 Uiso calc 0.293(5) A 2
H H15D 0.264950 1.056010 0.180153 0.044 Uiso calc 0.293(5) 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'
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
C15A N1 C1 . . 120.8(11) ?
C1 N1 C15 . . 114.0(4) ?
N1 C1 C9 . . 111.62(12) ?
N1 C1 C2 . . 107.84(12) ?
C9 C1 C2 . . 114.45(13) ?
C14 C9 C10 . . 114.19(14) ?
C14 C9 C1 . . 123.60(13) ?
C10 C9 C1 . . 122.21(13) ?
C8 C3 C4 . . 118.70(16) ?
C8 C3 C2 . . 120.46(15) ?
C4 C3 C2 . . 120.84(15) ?
C12 C13 C14 . . 117.66(16) ?
C11 C12 C13 . . 120.75(15) ?
C12 C11 C10 . . 118.49(15) ?
F2 C14 C13 . . 118.30(14) ?
F2 C14 C9 . . 116.80(14) ?
C13 C14 C9 . . 124.89(15) ?
F1 C10 C11 . . 118.07(14) ?
F1 C10 C9 . . 117.92(14) ?
C11 C10 C9 . . 124.01(15) ?
C5 C4 C3 . . 120.64(17) ?
N1 C15 C16 . . 110.2(7) ?
C3 C8 C7 . . 120.44(18) ?
C3 C2 C1 . . 112.35(13) ?
C6 C7 C8 . . 120.56(18) ?
C6 C5 C4 . . 120.15(19) ?
C7 C6 C5 . . 119.51(18) ?
Cl1S C1S Cl1S . 2 111.79(12) ?
N1 C15A C16A . . 111.2(13) ?
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
Cl1S C1S . 1.7606(13) ?
F1 C10 . 1.3580(18) ?
F2 C14 . 1.3516(18) ?
N1 C15A . 1.43(2) ?
N1 C1 . 1.5040(19) ?
N1 C15 . 1.522(8) ?
C1 C9 . 1.512(2) ?
C1 C2 . 1.535(2) ?
C9 C14 . 1.378(2) ?
C9 C10 . 1.379(2) ?
C3 C8 . 1.382(2) ?
C3 C4 . 1.389(2) ?
C3 C2 . 1.510(2) ?
C13 C12 . 1.375(3) ?
C13 C14 . 1.375(2) ?
C12 C11 . 1.374(3) ?
C11 C10 . 1.375(2) ?
C4 C5 . 1.384(3) ?
C15 C16 . 1.550(8) ?
C8 C7 . 1.385(3) ?
C7 C6 . 1.374(3) ?
C5 C6 . 1.379(3) ?
C16A C15A . 1.51(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1B Cl1 . 0.89(2) 2.30(2) 3.1417(14) 156.0(16) yes
