#------------------------------------------------------------------------------
#$Date: 2022-03-11 01:47:10 +0200 (Fri, 11 Mar 2022) $
#$Revision: 273625 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/45/7244588.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_7244588
loop_
_publ_author_name
'Parisi, Emmanuele'
'CARELLA, Antonio'
'Borbone, Fabio'
'Gentile, Francesco Silvio'
'Centore, Roberto'
'Chiarella, Fabio'
_publ_section_title
;
 Effect of chalcogen bond on the packing and coordination geometry in
 hybrid organic-inorganic Cu(II) networks.
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00069E
_journal_year                    2022
_chemical_formula_moiety         'C6 H4 Cl2 Cu N2 Se'
_chemical_formula_sum            'C6 H4 Cl2 Cu N2 Se'
_chemical_formula_weight         317.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2022-01-10 deposited with the CCDC.	2022-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.51(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.6770(15)
_cell_length_b                   12.682(3)
_cell_length_c                   8.707(2)
_cell_measurement_reflns_used    254
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.753
_cell_measurement_theta_min      2.854
_cell_volume                     401.6(2)
_computing_cell_refinement
;
Dirax/lsq (Duisenberg et al., 2000)
;
_computing_data_collection       'Collect (Nonius, 1999)'
_computing_data_reduction
;
EvalCCD (Duisenberg et al., 2003)
;
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 2012) and 
Mercury (Macrae et al., 2006)
;
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_structure_solution
;
SIR97 (Altomare et al., 1999)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_detector_type
;
Bruker-Nonius 95mm CCD camera on \k-goniostat
;
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.754
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method
;
CCD rotation images, thick slices
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0894
_diffrn_reflns_av_unetI/netI     0.0708
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.754
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3141
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.754
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.258
_diffrn_reflns_theta_min         2.859
_exptl_absorpt_coefficient_mu    7.848
_exptl_absorpt_correction_T_max  0.374
_exptl_absorpt_correction_T_min  0.258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS (Bruker, 2001)
;
_exptl_crystal_colour            GREEN
_exptl_crystal_density_diffrn    2.626
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             302
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol/chloroform'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_refine_diff_density_max         2.626
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.252
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     59
_refine_ls_number_reflns         758
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0570
_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)+(0.0871P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1470
_reflns_Friedel_coverage         0.000
_reflns_number_gt                553
_reflns_number_total             758
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00069e2.cif
_cod_data_source_block           shelx_CCDC1
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               7244588
_shelx_shelxl_version_number     2016/6
_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   0.244
_shelx_estimated_absorpt_t_max   0.386
_shelx_res_file
;
TITL Compound X
    shelx.res
    created by SHELXL-2016/6 at 12:45:33 on 02-Jun-2021
CELL  0.71073   3.6770  12.6820   8.7070   90.000   98.506   90.000
ZERR     2.00   0.0015   0.0029   0.0021    0.000    0.02    0.000
LATT   1
SYMM  - X, 1/2 + Y, - Z
SFAC  C    H    N    SE   CU   CL
DISP C    0.00330   0.00160
DISP H    0.00000   0.00000
DISP N    0.00610   0.00330
DISP Se  -0.09290   2.22590
DISP Cu   0.32010   1.26510
DISP Cl   0.14840   0.15850
UNIT  12 8 4 2 2 4
MERG   2
FMAP   2
PLAN   20
ACTA
SIZE 0.15 0.15 0.25
BOND
TWIN -1 0 0 0 -1 0 0 0 1
BOND   $H
CONF
LIST   4
L.S.   8
WGHT    0.087100
BASF   0.00106
FVAR       0.86358
C1    1    0.529380    0.193907    0.220390    11.00000    0.02151    0.01579 =
         0.01740    0.00067    0.00217   -0.00023
C2    1    0.481411    0.138753    0.358321    11.00000    0.01954    0.01879 =
         0.02845    0.00282    0.00415   -0.00256
AFIX  43
H2    2    0.486698    0.065456    0.361126    11.00000   -1.20000
AFIX   0
C3    1    0.428353    0.194417    0.484414    11.00000    0.03579    0.03668 =
         0.01802    0.00477    0.00388   -0.00041
AFIX  43
H3    2    0.390656    0.158695    0.574001    11.00000   -1.20000
AFIX   0
N1    3    0.570841    0.150205    0.085009    11.00000    0.02699    0.00900 =
         0.01555    0.00104   -0.00110   -0.00208
SE1   4    0.642319   10.250000   -0.051650    10.50000    0.03741    0.00816 =
         0.01937   10.00000    0.00895   10.00000
CU1   5   10.500000   10.000000   10.000000    10.50000    0.02363    0.00934 =
         0.02139   -0.00161    0.00217    0.00128
CL1   6    0.040153    0.058096   -0.184823    11.00000    0.02457    0.01731 =
         0.02332   -0.00038    0.00249    0.00296
HKLF    4




REM  Compound X
REM R1 =  0.0570 for     553 Fo > 4sig(Fo)  and  0.0870 for all     758 data
REM     59 parameters refined using      0 restraints

END

WGHT      0.0873      0.0000

REM Highest difference peak  2.626,  deepest hole -0.819,  1-sigma level  0.252
Q1    1   0.3505  0.2500 -0.0417  10.50000  0.05    2.63
Q2    1   1.0428  0.2500 -0.0503  10.50000  0.05    2.31
Q3    1   0.0000  0.0000  0.0000  10.50000  0.05    2.14
Q4    1   0.7691 -0.0004 -0.0009  11.00000  0.05    1.97
Q5    1  -0.2098  0.0563 -0.1867  11.00000  0.05    1.11
Q6    1   0.2928  0.0592 -0.1858  11.00000  0.05    1.08
Q7    1   0.5469  0.0504 -0.1784  11.00000  0.05    0.98
Q8    1   0.0569  0.2500  0.1830  10.50000  0.05    0.76
Q9    1   0.6816  0.2500  0.0361  10.50000  0.05    0.61
Q10   1   0.5188  0.2500 -0.1603  10.50000  0.05    0.59
Q11   1   0.8694  0.1215  0.3341  11.00000  0.05    0.57
Q12   1   0.1601  0.2500  0.4071  10.50000  0.05    0.56
Q13   1   0.1809  0.1322  0.3545  11.00000  0.05    0.53
Q14   1   0.8073  0.1467  0.0690  11.00000  0.05    0.51
Q15   1   0.0706  0.2500  0.4937  10.50000  0.05    0.50
Q16   1   0.6672  0.2500  0.3767  10.50000  0.05    0.47
Q17   1   0.6303  0.3383 -0.1825  11.00000  0.05    0.47
Q18   1   0.7459  0.0459  0.3998  11.00000  0.05    0.44
Q19   1   0.5780  0.1936  0.7109  11.00000  0.05    0.43
Q20   1   0.7098  0.1074  0.4994  11.00000  0.05    0.42
;
_shelx_res_checksum              8226
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.529(2) 0.1939(7) 0.2204(10) 0.0183(19) Uani 1 1 d . . . . .
C2 C 0.481(2) 0.1388(7) 0.3583(12) 0.022(2) Uani 1 1 d . . . . .
H2 H 0.486698 0.065456 0.361126 0.027 Uiso 1 1 calc R U . . .
C3 C 0.428(3) 0.1944(9) 0.4844(11) 0.030(2) Uani 1 1 d . . . . .
H3 H 0.390656 0.158695 0.574001 0.036 Uiso 1 1 calc R U . . .
N1 N 0.571(2) 0.1502(6) 0.0850(8) 0.0176(17) Uani 1 1 d . . . . .
Se1 Se 0.6423(4) 0.250000 -0.05165(15) 0.0212(4) Uani 1 2 d S T P . .
Cu1 Cu 0.500000 0.000000 0.000000 0.0182(5) Uani 1 2 d S . P . .
Cl1 Cl 0.0402(6) 0.05810(17) -0.1848(3) 0.0218(6) 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
C1 0.022(5) 0.016(4) 0.017(5) 0.001(4) 0.002(4) 0.000(4)
C2 0.020(5) 0.019(5) 0.028(6) 0.003(4) 0.004(4) -0.003(4)
C3 0.036(6) 0.037(6) 0.018(5) 0.005(4) 0.004(4) 0.000(5)
N1 0.027(4) 0.009(4) 0.016(4) 0.001(3) -0.001(3) -0.002(3)
Se1 0.0374(9) 0.0082(7) 0.0194(8) 0.000 0.0090(6) 0.000
Cu1 0.0236(9) 0.0093(8) 0.0214(10) -0.0016(6) 0.0022(7) 0.0013(6)
Cl1 0.0246(12) 0.0173(12) 0.0233(13) -0.0004(9) 0.0025(9) 0.0030(9)
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'
Se Se -0.0929 2.2259 '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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 126.0(9) . . ?
N1 C1 C1 114.6(5) . 4_565 ?
C2 C1 C1 119.4(5) . 4_565 ?
C3 C2 C1 118.8(9) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C3 121.7(6) . 4_565 ?
C2 C3 H3 119.2 . . ?
C3 C3 H3 119.2 4_565 . ?
C1 N1 Se1 110.0(6) . . ?
C1 N1 Cu1 133.0(6) . . ?
Se1 N1 Cu1 116.3(4) . . ?
N1 Se1 N1 90.4(5) . 4_565 ?
N1 Cu1 N1 180.0(4) 3_655 . ?
N1 Cu1 Cl1 90.2(2) 3_655 . ?
N1 Cu1 Cl1 89.8(2) . . ?
N1 Cu1 Cl1 89.8(2) 3_655 3_655 ?
N1 Cu1 Cl1 90.2(2) . 3_655 ?
Cl1 Cu1 Cl1 180.0 . 3_655 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.332(11) . ?
C1 C2 1.423(13) . ?
C1 C1 1.423(18) 4_565 ?
C2 C3 1.344(14) . ?
C2 H2 0.9300 . ?
C3 C3 1.41(2) 4_565 ?
C3 H3 0.9300 . ?
N1 Se1 1.783(7) . ?
N1 Cu1 2.046(7) . ?
Cu1 Cl1 2.277(2) . ?
Cu1 Cl1 2.277(2) 3_655 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -177.4(9) . . . . ?
C1 C1 C2 C3 1.6(10) 4_565 . . . ?
C1 C2 C3 C3 -1.6(11) . . . 4_565 ?
C2 C1 N1 Se1 -177.4(7) . . . . ?
C1 C1 N1 Se1 3.6(6) 4_565 . . . ?
C2 C1 N1 Cu1 12.3(14) . . . . ?
C1 C1 N1 Cu1 -166.7(5) 4_565 . . . ?
C1 N1 Se1 N1 -4.6(8) . . . 4_565 ?
Cu1 N1 Se1 N1 167.50(12) . . . 4_565 ?
