#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:19:02 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229064 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/02/7230214.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_7230214
loop_
_publ_author_name
'Puttreddy, Rakesh'
'von Essen, Carolina'
'Peuronen, Anssi'
'Lahtinen, Manu'
'Rissanen, Kari'
_publ_section_title
;
 Halogen bonds in 2,5-dihalopyridine-copper(ii) chloride complexes
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              1954
_journal_paper_doi               10.1039/C8CE00209F
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C10 H8 Cl2 Cu F2 N2'
_chemical_formula_sum            'C10 H8 Cl2 Cu F2 N2'
_chemical_formula_weight         328.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_audit_update_record
;
2018-02-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.532(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.72080(10)
_cell_length_b                   15.9058(5)
_cell_length_c                   11.7364(5)
_cell_measurement_reflns_used    2332
_cell_measurement_temperature    120.0(1)
_cell_measurement_theta_max      27.4540
_cell_measurement_theta_min      3.6940
_cell_volume                     692.42(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00  10.00   2.00  115.00    --  -18.14 -77.00 150.00   49
  2  ω    -87.00   3.00   2.00  115.00    --  -18.14 -57.00   0.00   45
  3  ω    -90.00 -62.00   2.00  115.00    --  -18.14 148.00 -25.97   14
  4  ω    -37.00  51.00   2.00  115.00    --  -18.14  57.00 150.00   44
  5  ω     -8.00  48.00   2.00  115.00    --  -18.14  77.00 -90.00   28
  6  ω    -50.00  34.00   2.00  115.00    --   19.23 -57.00  30.00   42
  7  ω    -20.00  60.00   2.00  115.00    --   19.23 -99.00-120.00   40
  8  ω     10.00  60.00   2.00  115.00    --   19.23 -99.00 -30.00   25
  9  ω     -8.00  86.00   2.00  115.00    --   19.23  77.00 -90.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1513876000
_diffrn_orient_matrix_UB_12      0.0244850000
_diffrn_orient_matrix_UB_13      0.0124228000
_diffrn_orient_matrix_UB_21      -0.0982696000
_diffrn_orient_matrix_UB_22      -0.0160883000
_diffrn_orient_matrix_UB_23      -0.0495076000
_diffrn_orient_matrix_UB_31      -0.0632326000
_diffrn_orient_matrix_UB_32      -0.0336065000
_diffrn_orient_matrix_UB_33      0.0327294000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            1216
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.097
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.964
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92486
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_description       needle
_exptl_crystal_F_000             326
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.025
_refine_diff_density_max         5.350
_refine_diff_density_min         -4.497
_refine_diff_density_rms         0.303
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.323
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     79
_refine_ls_number_reflns         1216
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.323
_refine_ls_R_factor_all          0.1281
_refine_ls_R_factor_gt           0.1171
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2838
_refine_ls_wR_factor_ref         0.3002
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1030
_reflns_number_total             1216
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;

    3fpy+cucl2_gau.res created by SHELXL-2014/7

TITL 3fpy+cucl2_gau_a.res in P2(1)/c
REM Old TITL 3FPy+CuCl2_gau in P2(1)
REM SHELXT solution in P2(1)/c
REM R1 0.185, Rweak 0.172, Alpha 0.095, Orientation as input
REM Formula found by SHELXT: C10 N4 Cl2 Cu
CELL 0.71073 3.7208 15.9058 11.7364 90 94.532 90
ZERR 2 0.0001 0.0005 0.0005 0 0.003 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Cl Cu F N
UNIT 20 16 4 2 4 4
 
L.S. 4
PLAN  20
BOND $H
list 4
fmap 2
acta
OMIT -2 50
OMIT 0 3 3
REM <olex2.extras>
REM <HklSrc "%.\\3FPy+CuCl2_gau.hkp">
REM </olex2.extras>
 
WGHT    0.200000
FVAR      11.89707
CU1   4    0.500000    0.500000    0.500000    10.50000    0.02874    0.01258 =
         0.02326   -0.00457    0.00534   -0.00234
CL1   3    0.849286    0.552202    0.363652    11.00000    0.02218    0.01660 =
         0.02215    0.00101    0.00087    0.00110
F3    5    0.184159    0.302482    0.147449    11.00000    0.06348    0.04996 =
         0.03775   -0.01625   -0.00878    0.00384
N1    6    0.482811    0.386946    0.418575    11.00000    0.02397    0.01230 =
         0.02881   -0.00172    0.00470   -0.00245
C2    1    0.353997    0.381222    0.311862    11.00000    0.02505    0.01591 =
         0.03347   -0.00193    0.00164    0.00009
AFIX  43
H2    2    0.273814    0.429656    0.273408    11.00000   -1.20000
AFIX   0
C3    1    0.333772    0.305196    0.254691    11.00000    0.02446    0.03465 =
         0.02862   -0.01272   -0.00028   -0.00260
C4    1    0.458163    0.232550    0.309368    11.00000    0.02478    0.01575 =
         0.03737   -0.01358    0.00625   -0.00348
AFIX  43
H4    2    0.446678    0.181033    0.271780    11.00000   -1.20000
AFIX   0
C5    1    0.597252    0.238672    0.419322    11.00000    0.02372    0.01537 =
         0.04042    0.00281    0.00892    0.00281
AFIX  43
H5    2    0.688268    0.191492    0.458523    11.00000   -1.20000
AFIX   0
C6    1    0.601233    0.317435    0.472749    11.00000    0.01922    0.02982 =
         0.02880   -0.00184    0.00264   -0.00686
AFIX  43
H6    2    0.689851    0.321386    0.548902    11.00000   -1.20000
AFIX   0
HKLF 5
 
REM  3fpy+cucl2_gau_a.res in P2(1)/c
REM R1 =  0.1171 for    1030 Fo > 4sig(Fo)  and  0.1281 for all    1216 data
REM     79 parameters refined using      0 restraints
 
END  
     
WGHT      0.2000      0.0000 

REM Highest difference peak  5.350,  deepest hole -4.497,  1-sigma level  0.303
Q1    1   0.8549  0.4485  0.3652  11.00000  0.05    1.54
Q2    1   0.3627  0.0032  0.4648  11.00000  0.05    1.40
Q3    1   0.4998  0.4047  0.5044  11.00000  0.05    0.70
Q4    1   0.6329  0.4393  0.4390  11.00000  0.05    0.64
Q5    1   0.7475  0.5447  0.4625  11.00000  0.05    0.61
Q6    1   0.3384  0.4443  0.3607  11.00000  0.05    0.61
Q7    1   0.7524  0.0385  0.3972  11.00000  0.05    0.59
Q8    1   0.9087  0.4031  0.4888  11.00000  0.05    0.56
Q9    1   0.1243  0.4642  0.4650  11.00000  0.05    0.51
Q10   1   0.6991  0.4989  0.4164  11.00000  0.05    0.49
Q11   1   0.1294  0.5324  0.4606  11.00000  0.05    0.49
Q12   1   0.7357  0.6241  0.3386  11.00000  0.05    0.48
Q13   1   0.9511  0.5853  0.4473  11.00000  0.05    0.48
Q14   1   0.1757  0.5422  0.4995  11.00000  0.05    0.47
Q15   1   0.9858  0.6172  0.3826  11.00000  0.05    0.44
Q16   1   0.3869  0.5064  0.4032  11.00000  0.05    0.44
Q17   1   0.8161  0.6475  0.4230  11.00000  0.05    0.42
Q18   1   0.7758  0.3351  0.5431  11.00000  0.05    0.42
Q19   1   0.6936  0.2954  0.5793  11.00000  0.05    0.42
Q20   1   0.8440  0.4881  0.4330  11.00000  0.05    0.42

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.1171 for 1030 Fo > 4sig(Fo) and 0.1281 for all 1689 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 5.35, deepest hole -4.50
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.1281
  REM R1_gt = 0.1171
  REM wR_ref = 0.3002
  REM GOOF = 1.323
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 1689
  REM Reflections_gt = 1030
  REM Parameters = n/a
  REM Hole = -4.50
  REM Peak = 5.35
  REM Flack = n/a

  
;
_cod_data_source_file            c8ce00209f2.cif
_cod_data_source_block           3FPy_2_CuCl2
_cod_depositor_comments
'Adding full bibliography for 7230211--7230222.cif.'
_cod_database_code               7230214
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 H20 N2 Cu1 F1 Cl1'
_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.
;
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.144
_oxdiff_exptl_absorpt_empirical_full_min 0.809
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 0.5000 0.5000 0.5000 0.0214(7) Uani 1 2 d S T P
Cl1 Cl 0.8493(6) 0.55220(13) 0.36365(17) 0.0204(7) Uani 1 1 d . . .
F3 F 0.184(2) 0.3025(5) 0.1474(5) 0.051(2) Uani 1 1 d . . .
N1 N 0.483(2) 0.3869(5) 0.4186(6) 0.0216(17) Uani 1 1 d . . .
C2 C 0.354(3) 0.3812(6) 0.3119(8) 0.025(2) Uani 1 1 d . . .
H2 H 0.2738 0.4297 0.2734 0.030 Uiso 1 1 calc R . .
C3 C 0.334(3) 0.3052(7) 0.2547(9) 0.029(2) Uani 1 1 d . . .
C4 C 0.458(3) 0.2326(6) 0.3094(8) 0.026(2) Uani 1 1 d . . .
H4 H 0.4467 0.1810 0.2718 0.031 Uiso 1 1 calc R . .
C5 C 0.597(3) 0.2387(6) 0.4193(8) 0.026(2) Uani 1 1 d . . .
H5 H 0.6883 0.1915 0.4585 0.031 Uiso 1 1 calc R . .
C6 C 0.601(3) 0.3174(6) 0.4727(9) 0.026(2) Uani 1 1 d . . .
H6 H 0.6899 0.3214 0.5489 0.031 Uiso 1 1 calc R . .
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
Cu1 0.0287(10) 0.0126(10) 0.0233(10) -0.0046(5) 0.0053(8) -0.0023(8)
Cl1 0.0222(12) 0.0166(12) 0.0222(12) 0.0010(8) 0.0009(10) 0.0011(10)
F3 0.063(5) 0.050(4) 0.038(4) -0.016(3) -0.009(4) 0.004(4)
N1 0.024(4) 0.012(3) 0.029(4) -0.002(3) 0.005(3) -0.002(3)
C2 0.025(5) 0.016(4) 0.033(5) -0.002(4) 0.002(4) 0.000(4)
C3 0.024(5) 0.035(5) 0.029(5) -0.013(4) 0.000(4) -0.003(5)
C4 0.025(5) 0.016(4) 0.037(6) -0.014(4) 0.006(4) -0.003(4)
C5 0.024(5) 0.015(4) 0.040(6) 0.003(4) 0.009(5) 0.003(4)
C6 0.019(5) 0.030(5) 0.029(5) -0.002(4) 0.003(4) -0.007(4)
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -13 13 0.0147
0 12 -14 0.0132
4 12 6 0.0931
-4 -12 -6 0.0916
0 14 13 0.0180
1 -9 -15 0.0068
-1 3 16 0.0309
0 -14 -13 0.0066
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
Cl1 Cu1 Cl1 180.00(9) . 3_666
N1 Cu1 Cl1 90.5(2) . 3_666
N1 Cu1 Cl1 90.5(2) 3_666 .
N1 Cu1 Cl1 89.5(2) . .
N1 Cu1 Cl1 89.5(2) 3_666 3_666
N1 Cu1 N1 180.0 . 3_666
C2 N1 Cu1 120.4(6) . .
C2 N1 C6 118.8(8) . .
C6 N1 Cu1 120.8(6) . .
N1 C2 H2 119.1 . .
N1 C2 C3 121.8(9) . .
C3 C2 H2 119.1 . .
F3 C3 C2 119.2(10) . .
F3 C3 C4 120.6(8) . .
C2 C3 C4 120.1(9) . .
C3 C4 H4 121.0 . .
C5 C4 C3 118.0(8) . .
C5 C4 H4 121.0 . .
C4 C5 H5 120.6 . .
C4 C5 C6 118.7(9) . .
C6 C5 H5 120.6 . .
N1 C6 C5 122.5(9) . .
N1 C6 H6 118.8 . .
C5 C6 H6 118.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 Cl1 2.295(2) .
Cu1 Cl1 2.295(2) 3_666
Cu1 N1 2.035(7) .
Cu1 N1 2.035(7) 3_666
F3 C3 1.336(12) .
N1 C2 1.308(12) .
N1 C6 1.333(13) .
C2 H2 0.9300 .
C2 C3 1.382(14) .
C3 C4 1.384(16) .
C4 H4 0.9300 .
C4 C5 1.355(14) .
C5 H5 0.9300 .
C5 C6 1.401(14) .
C6 H6 0.9300 .
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0018 -13.0040 12.9986 -0.1572 -0.4345 0.8623
-0.0019 12.0044 -13.9983 0.1203 0.5001 -0.8615
4.0014 11.9968 5.9997 -0.2375 -0.8833 -0.4598
-4.0014 -11.9968 -5.9997 0.2375 0.8833 0.4598
0.0019 13.9943 12.9960 0.5038 -0.8687 -0.0451
0.9980 -8.9939 -14.9956 -0.5576 0.7890 -0.2516
-0.9979 2.9939 15.9959 0.4231 -0.7420 0.4860
-0.0019 -13.9943 -12.9960 -0.5038 0.8687 0.0451
