#------------------------------------------------------------------------------
#$Date: 2019-11-07 20:38:55 +0100 (jue 07 de nov de 2019) $
#$Revision: 223567 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/34/7233421.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_7233421
loop_
_publ_author_name
'Vaganova, Tamara A.'
'Gatilov, Yurij V.'
'Benassi, Enrico'
'Chuikov, Igor P.'
'Pishchur, Denis P.'
'Malykhin, Evgenij V.'
_publ_section_title
;
 Impact of molecular packing rearrangement on solid-state fluorescence:
 polyhalogenated N-hetarylamines vs. their co-crystals with 18-crown-6
;
_journal_issue                   39
_journal_name_full               CrystEngComm
_journal_page_first              5931
_journal_paper_doi               10.1039/C9CE00645A
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C5 H2 Cl F3 N2'
_chemical_formula_sum            'C5 H2 Cl F3 N2'
_chemical_formula_weight         182.54
_chemical_melting_point          392
_chemical_name_systematic        4-amino-3-chloro-2,5,6-trifluoropyridine
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-04-22 deposited with the CCDC.    2019-08-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2213(16)
_cell_length_b                   13.783(2)
_cell_length_c                   5.0802(8)
_cell_measurement_reflns_used    2017
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.95
_cell_measurement_theta_min      2.96
_cell_volume                     645.68(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4219
_diffrn_reflns_point_group_measured_fraction_full 0.925
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.112
_diffrn_reflns_theta_min         2.658
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.878
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 329 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1127
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0467
_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)+(0.1108P)²+0.4019P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1413
_refine_ls_wR_factor_ref         0.1492
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_full    0.865
_reflns_Friedel_fraction_max     0.810
_reflns_number_gt                954
_reflns_number_total             1127
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00645a2.cif
_cod_data_source_block           B-c1042
_cod_depositor_comments
'Adding full bibliography for 7233421--7233432.cif.'
_cod_original_cell_volume        645.70(19)
_cod_database_code               7233421
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.794
_shelx_estimated_absorpt_t_max   0.972
_shelx_res_file
;

    c1042.res created by SHELXL-2014/7

TITL c1042 in Pna2(1)
CELL 0.71073   9.2213  13.7835   5.0802  90.000  90.000  90.000
ZERR    4.00   0.0016   0.0024   0.0008   0.000   0.000   0.000
LATT -1
SYMM -X, -Y, 0.5+Z
SYMM 0.5+X, 0.5-Y, Z
SYMM 0.5-X, 0.5+Y, 0.5+Z
SFAC C H N F CL
UNIT 20 8 8 12 4
TEMP -73.120
SIZE 0.05 0.36 0.42
L.S. 15
ACTA 50
BOND
FMAP 2
PLAN 9
DFIX 0.85 0.02 N2 H2  N2 H1
WGHT    0.110800    0.401900
FVAR       0.25736
CL1   5   -0.009197    0.390699    0.190368    11.00000    0.05271    0.03025 =
         0.04771    0.00458   -0.00968    0.00158
N1    3    0.227178    0.229670    0.678310    11.00000    0.02685    0.04520 =
         0.03569    0.00791   -0.00797   -0.00456
F1    4    0.208484    0.390303    0.618448    11.00000    0.05960    0.03743 =
         0.04727   -0.00897   -0.01021   -0.01176
C1    1    0.165009    0.301201    0.543259    11.00000    0.03242    0.03351 =
         0.03416   -0.00606    0.00885   -0.00496
N2    3   -0.075240    0.178811    0.081063    11.00000    0.03624    0.03002 =
         0.02188   -0.00118   -0.00954    0.00102
H2A   2   -0.126340    0.224993   -0.004484    11.00000   -1.15000
H2B   2   -0.100131    0.121729    0.052075    11.00000   -1.15000
F2    4    0.059693    0.028638    0.342985    11.00000    0.05929    0.02771 =
         0.04652   -0.00121   -0.01241    0.00123
C2    1    0.064165    0.291958    0.350187    11.00000    0.02411    0.03373 =
         0.02256   -0.00101    0.00231   -0.00110
F3    4    0.249072    0.067745    0.735899    11.00000    0.06138    0.05085 =
         0.04776    0.01622   -0.02594    0.00555
C3    1    0.022803    0.196954    0.270090    11.00000    0.01651    0.03359 =
         0.01769    0.00206   -0.00126   -0.00300
C4    1    0.091273    0.121044    0.408191    11.00000    0.03158    0.02895 =
         0.02662    0.00447    0.00200    0.00122
C5    1    0.187155    0.141166    0.605029    11.00000    0.03443    0.03944 =
         0.01625    0.00529   -0.00127    0.00233

HKLF 4

REM  c1042 in Pna2(1)
REM R1 =  0.0467 for     954 Fo > 4sig(Fo)  and  0.0582 for all    1127 data
REM    106 parameters refined using      1 restraints

END

WGHT      0.0380      0.7180

REM Highest difference peak  0.227,  deepest hole -0.303,  1-sigma level  0.067
Q1    1   0.1272  0.4289  0.3249  11.00000  0.05    0.23
Q2    1   0.3319  0.4022  0.6981  11.00000  0.05    0.23
Q3    1   0.3939  0.0223  0.7596  11.00000  0.05    0.22
Q4    1   0.2655  0.4805  0.5591  11.00000  0.05    0.22
Q5    1  -0.0006  0.1470  0.3621  11.00000  0.05    0.21
Q6    1   0.1406  0.1618  0.1716  11.00000  0.05    0.21
Q7    1  -0.0133  0.0575 -0.0211  11.00000  0.05    0.21
Q8    1   0.0873  0.1611 -0.0820  11.00000  0.05    0.21
Q9    1   0.0598  0.1747 -0.0615  11.00000  0.05    0.20
;
_shelx_res_checksum              73857
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_adp
Cl1 Cl -0.0092(2) 0.39070(11) 0.1904(6) 0.0436(6) Uani 1 1 d .
N1 N 0.2272(6) 0.2297(4) 0.6783(14) 0.0359(14) Uani 1 1 d .
F1 F 0.2085(5) 0.3903(3) 0.6184(9) 0.0481(13) Uani 1 1 d .
C1 C 0.1650(7) 0.3012(4) 0.5433(16) 0.0334(17) Uani 1 1 d .
N2 N -0.0752(6) 0.1788(4) 0.0811(11) 0.0294(13) Uani 1 1 d .
H2A H -0.126(8) 0.225(5) -0.004(16) 0.034 Uiso 1 1 d U
H2B H -0.100(8) 0.122(6) 0.052(17) 0.034 Uiso 1 1 d U
F2 F 0.0597(5) 0.0286(3) 0.3430(9) 0.0445(12) Uani 1 1 d .
C2 C 0.0642(7) 0.2920(5) 0.3502(15) 0.0268(14) Uani 1 1 d .
F3 F 0.2491(5) 0.0677(3) 0.7359(9) 0.0533(14) Uani 1 1 d .
C3 C 0.0228(7) 0.1970(4) 0.2701(12) 0.0226(15) Uani 1 1 d .
C4 C 0.0913(7) 0.1210(4) 0.4082(15) 0.0290(15) Uani 1 1 d .
C5 C 0.1872(7) 0.1412(5) 0.6050(13) 0.0300(15) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0527(11) 0.0303(8) 0.0477(11) 0.0046(8) -0.0097(10) 0.0016(7)
N1 0.027(3) 0.045(3) 0.036(3) 0.008(3) -0.008(3) -0.005(2)
F1 0.060(3) 0.037(2) 0.047(3) -0.0090(19) -0.010(2) -0.0118(18)
C1 0.032(4) 0.034(3) 0.034(4) -0.006(3) 0.009(3) -0.005(3)
N2 0.036(3) 0.030(3) 0.022(3) -0.001(3) -0.010(3) 0.001(2)
F2 0.059(3) 0.028(2) 0.047(3) -0.0012(18) -0.012(2) 0.0012(18)
C2 0.024(3) 0.034(3) 0.023(4) -0.001(3) 0.002(3) -0.001(2)
F3 0.061(3) 0.051(2) 0.048(3) 0.016(2) -0.026(2) 0.006(2)
C3 0.017(3) 0.034(3) 0.018(4) 0.002(2) -0.001(2) -0.003(2)
C4 0.032(4) 0.029(3) 0.027(4) 0.004(3) 0.002(3) 0.001(3)
C5 0.034(4) 0.039(3) 0.016(3) 0.005(3) -0.001(3) 0.002(3)
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
C5 N1 C1 114.6(6)
N1 C1 C2 126.7(6)
N1 C1 F1 113.6(7)
C2 C1 F1 119.6(6)
C1 C2 C3 118.5(6)
C1 C2 Cl1 122.4(5)
C3 C2 Cl1 119.1(5)
N2 C3 C2 123.8(6)
N2 C3 C4 121.3(6)
C2 C3 C4 114.9(6)
F2 C4 C5 120.8(6)
F2 C4 C3 118.8(6)
C5 C4 C3 120.3(6)
F3 C5 N1 115.9(6)
F3 C5 C4 119.1(6)
N1 C5 C4 124.9(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.723(7)
N1 C5 1.328(9)
N1 C1 1.331(9)
F1 C1 1.347(7)
C1 C2 1.358(11)
N2 C3 1.342(9)
F2 C4 1.348(7)
C2 C3 1.423(8)
F3 C5 1.339(7)
C3 C4 1.409(9)
C4 C5 1.363(10)
