#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:36:54 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179669 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/22/4512278.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_4512278
loop_
_publ_author_name
'Hain, Malia S.'
'Fukuda, Yoko'
'Rojas Ramírez, Carolina'
'Winer, Benjamin Y.'
'Winslow, Stephanie E.'
'Pike, Robert D.'
'Bebout, Deborah C.'
_publ_section_title
;
 Staging Bonding between Group 12 Metal Ions and Neutral Selenium Donors:
 Intermolecular Interactions of Mixed N,Se Donor Ligands and Anions
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              6497
_journal_paper_doi               10.1021/cg501395p
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C12 H12 Cl2 N2 Se Zn'
_chemical_formula_sum            'C12 H12 Cl2 N2 Se Zn'
_chemical_formula_weight         399.47
_chemical_name_systematic
; 
dichloro-(bis(2-pyridylmethyl)selenide-N,N')-zinc(ii)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/5
_cell_angle_alpha                90
_cell_angle_beta                 121.2470(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.6226(10)
_cell_length_b                   8.4580(4)
_cell_length_c                   16.2905(7)
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      69.37
_cell_measurement_theta_min      3.17
_cell_volume                     2782.7(2)
_computing_cell_refinement       'SAINTPLUS (Bruker AXS, 2004)'
_computing_data_collection       'APEX2 (Bruker AXS, 2004)'
_computing_data_reduction        SAINTPLUS
_computing_molecular_graphics    'SHELXLE (Hubschle, 2011)'
_computing_publication_material  'Mercury 3.3 (CCDC, 2014)'
_computing_structure_refinement  'SHELXL-2014/5 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω and ψ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15011
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.990
_diffrn_reflns_theta_min         4.378
_exptl_absorpt_coefficient_mu    8.827
_exptl_absorpt_correction_T_max  0.6011
_exptl_absorpt_correction_T_min  0.1184
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.907
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.533
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.800
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2455
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0316
_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)+(0.0456P)²+10.1337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2367
_reflns_number_total             2455
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg501395p_si_002.cif
_cod_data_source_block           C2onc_Compound_1a
_cod_depositor_comments
'Adding full bibliography for 4512278--4512284.cif.'
_cod_database_code               4512278
#BEGIN Tags that were not found in dictionaries:
_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   0.089
_shelx_estimated_absorpt_t_max   0.376
_shelxl_version_number           2014/5
#END Tags that were not found in dictionaries
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'
'-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_posn
_atom_site_refinement_flags_adp
Se1 Se 0.32806(2) 1.11922(4) 0.38414(2) 0.02203(14) Uani 1 1 d . .
Zn1 Zn 0.40111(2) 0.75226(5) 0.29271(3) 0.01680(15) Uani 1 1 d . .
Cl1 Cl 0.50332(4) 0.65610(10) 0.38302(6) 0.0255(2) Uani 1 1 d . .
Cl2 Cl 0.32878(4) 0.64098(10) 0.15239(6) 0.0245(2) Uani 1 1 d . .
N1 N 0.35638(13) 0.7151(3) 0.37206(18) 0.0165(5) Uani 1 1 d . .
N2 N 0.40747(13) 0.9817(3) 0.2569(2) 0.0200(6) Uani 1 1 d . .
C1 C 0.37620(17) 0.5857(4) 0.4289(2) 0.0198(7) Uani 1 1 d . .
H1 H 0.4163 0.5357 0.4432 0.024 Uiso 1 1 calc R U
C2 C 0.34118(17) 0.5225(4) 0.4673(2) 0.0213(7) Uani 1 1 d . .
H2 H 0.3569 0.4318 0.5075 0.026 Uiso 1 1 calc R U
C3 C 0.28213(17) 0.5950(4) 0.4456(2) 0.0225(7) Uani 1 1 d . .
H3 H 0.2557 0.5519 0.4685 0.027 Uiso 1 1 calc R U
C4 C 0.26237(17) 0.7308(4) 0.3902(2) 0.0210(7) Uani 1 1 d . .
H4 H 0.2231 0.7841 0.3769 0.025 Uiso 1 1 calc R U
C5 C 0.30023(15) 0.7890(4) 0.3540(2) 0.0173(6) Uani 1 1 d . .
C6 C 0.28221(16) 0.9398(4) 0.2981(2) 0.0195(7) Uani 1 1 d . .
H6A H 0.2337 0.9561 0.2648 0.023 Uiso 1 1 calc R U
H6B H 0.2947 0.9332 0.2489 0.023 Uiso 1 1 calc R U
C7 C 0.41667(17) 1.0847(4) 0.4028(2) 0.0224(7) Uani 1 1 d . .
H7A H 0.4486 1.1588 0.4523 0.027 Uiso 1 1 calc R U
H7B H 0.4314 0.9757 0.4262 0.027 Uiso 1 1 calc R U
C8 C 0.41638(16) 1.1090(4) 0.3120(2) 0.0204(7) Uani 1 1 d . .
C9 C 0.42292(17) 1.2594(4) 0.2830(3) 0.0261(8) Uani 1 1 d . .
H9 H 0.4292 1.3484 0.3224 0.031 Uiso 1 1 calc R U
C10 C 0.42024(17) 1.2792(4) 0.1965(3) 0.0280(8) Uani 1 1 d . .
H10 H 0.4248 1.3812 0.1761 0.034 Uiso 1 1 calc R U
C11 C 0.41079(18) 1.1473(4) 0.1406(3) 0.0276(8) Uani 1 1 d . .
H11 H 0.4085 1.1576 0.0809 0.033 Uiso 1 1 calc R U
C12 C 0.40475(17) 1.0007(4) 0.1723(2) 0.0230(7) Uani 1 1 d . .
H12 H 0.3985 0.9104 0.1338 0.028 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 '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
C6 Se1 C7 98.25(14)
N2 Zn1 N1 117.16(11)
N2 Zn1 Cl1 108.56(8)
N1 Zn1 Cl1 105.12(8)
N2 Zn1 Cl2 103.72(8)
N1 Zn1 Cl2 101.97(8)
Cl1 Zn1 Cl2 120.92(4)
C1 N1 C5 118.4(3)
C1 N1 Zn1 116.3(2)
C5 N1 Zn1 123.6(2)
C8 N2 C12 119.4(3)
C8 N2 Zn1 125.1(2)
C12 N2 Zn1 115.4(2)
N1 C1 C2 123.3(3)
N1 C1 H1 118.3
C2 C1 H1 118.3
C1 C2 C3 118.2(3)
C1 C2 H2 120.9
C3 C2 H2 120.9
C4 C3 C2 119.1(3)
C4 C3 H3 120.5
C2 C3 H3 120.5
C3 C4 C5 119.8(3)
C3 C4 H4 120.1
C5 C4 H4 120.1
N1 C5 C4 121.1(3)
N1 C5 C6 117.6(3)
C4 C5 C6 121.2(3)
C5 C6 Se1 110.3(2)
C5 C6 H6A 109.6
Se1 C6 H6A 109.6
C5 C6 H6B 109.6
Se1 C6 H6B 109.6
H6A C6 H6B 108.1
C8 C7 Se1 111.6(2)
C8 C7 H7A 109.3
Se1 C7 H7A 109.3
C8 C7 H7B 109.3
Se1 C7 H7B 109.3
H7A C7 H7B 108.0
N2 C8 C9 120.7(3)
N2 C8 C7 118.0(3)
C9 C8 C7 121.2(3)
C10 C9 C8 120.0(3)
C10 C9 H9 120.0
C8 C9 H9 120.0
C11 C10 C9 118.5(3)
C11 C10 H10 120.8
C9 C10 H10 120.8
C12 C11 C10 119.5(3)
C12 C11 H11 120.3
C10 C11 H11 120.3
N2 C12 C11 121.9(3)
N2 C12 H12 119.1
C11 C12 H12 119.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Se1 C6 1.966(3)
Se1 C7 1.975(3)
Zn1 N2 2.055(3)
Zn1 N1 2.075(3)
Zn1 Cl1 2.2294(9)
Zn1 Cl2 2.2313(9)
N1 C1 1.351(4)
N1 C5 1.354(4)
N2 C8 1.347(4)
N2 C12 1.354(4)
C1 C2 1.377(5)
C1 H1 0.9500
C2 C3 1.391(5)
C2 H2 0.9500
C3 C4 1.383(5)
C3 H3 0.9500
C4 C5 1.392(5)
C4 H4 0.9500
C5 C6 1.495(4)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.490(5)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.393(5)
C9 C10 1.388(6)
C9 H9 0.9500
C10 C11 1.383(5)
C10 H10 0.9500
C11 C12 1.379(5)
C11 H11 0.9500
C12 H12 0.9500
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
C5 N1 C1 C2 1.9(5)
Zn1 N1 C1 C2 -163.5(3)
N1 C1 C2 C3 0.6(5)
C1 C2 C3 C4 -2.8(5)
C2 C3 C4 C5 2.5(5)
C1 N1 C5 C4 -2.2(4)
Zn1 N1 C5 C4 162.1(2)
C1 N1 C5 C6 174.8(3)
Zn1 N1 C5 C6 -20.9(4)
C3 C4 C5 N1 0.0(5)
C3 C4 C5 C6 -176.9(3)
N1 C5 C6 Se1 -84.9(3)
C4 C5 C6 Se1 92.1(3)
C12 N2 C8 C9 -0.1(5)
Zn1 N2 C8 C9 177.2(2)
C12 N2 C8 C7 177.8(3)
Zn1 N2 C8 C7 -4.9(4)
Se1 C7 C8 N2 -93.9(3)
Se1 C7 C8 C9 84.0(4)
N2 C8 C9 C10 0.0(5)
C7 C8 C9 C10 -177.8(3)
C8 C9 C10 C11 0.2(5)
C9 C10 C11 C12 -0.4(5)
C8 N2 C12 C11 -0.1(5)
Zn1 N2 C12 C11 -177.6(3)
C10 C11 C12 N2 0.3(5)
N2 Zn1 N1 C5 42.9(3)
C5 C6 Se1 C7 76.7(2)
C6 Se1 C7 C8 66.2(3)
C8 N2 Zn1 N1 34.2(3)
