#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/90/2019083.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_2019083
loop_
_publ_author_name
'Su, Bi-Yun'
'Wang, Jia-Xiang'
'Liu, Xiang'
'Li, Qian-Ding'
_publ_section_title
;
 Bis{2-[(phenylimino)ethyl]-1H-pyrrol-1-ido-κ²N,N'}nickel(II):
 a supramolecular structure formed by C---H···π
 hydrogen bonds
;
_journal_coeditor_code           LG3114
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              851
_journal_page_last               854
_journal_paper_doi               10.1107/S0108270113018118
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '[Ni (C12 H11 N2)2]'
_chemical_formula_moiety         'C24 H22 N4 Ni'
_chemical_formula_sum            'C24 H22 N4 Ni'
_chemical_formula_weight         425.17
_chemical_name_systematic
;
Bis{2-[(phenylimino)ethyl]-1H-pyrrol-1-ido-\
κ²N,N'}nickel(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.447(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.379(2)
_cell_length_b                   15.174(3)
_cell_length_c                   5.8453(11)
_cell_measurement_reflns_used    668
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.60
_cell_measurement_theta_min      2.68
_cell_volume                     989.2(3)
_computing_cell_refinement       'SAINT (Bruker,2008)'
_computing_data_collection       'APEX2 (Bruker,2008)'
_computing_data_reduction        'SAINT (Bruker,2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_sigmaI/netI    0.0660
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4871
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.998
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.7226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0291P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0880
_reflns_number_gt                1272
_reflns_number_total             1757
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lg3114.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2019083
_cod_database_fobs_code          2019083
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Ni Ni1 0.5000 1.0000 0.0000 0.0317(2) Uani d S 1 2
N N1 0.5746(2) 0.92309(17) 0.2522(4) 0.0338(6) Uani d . 1 1
N N2 0.3597(2) 0.93713(17) 0.0280(4) 0.0352(7) Uani d . 1 1
C C1 0.7620(3) 0.8610(2) 0.1920(6) 0.0404(9) Uani d . 1 1
H H1 0.7216 0.8412 0.0471 0.048 Uiso calc R 1 1
C C2 0.8826(3) 0.8445(2) 0.2620(6) 0.0500(10) Uani d . 1 1
H H2 0.9229 0.8124 0.1659 0.060 Uiso calc R 1 1
C C3 0.9439(3) 0.8753(3) 0.4743(7) 0.0531(10) Uani d . 1 1
H H3 1.0258 0.8651 0.5204 0.064 Uiso calc R 1 1
C C4 0.8831(3) 0.9212(3) 0.6175(6) 0.0503(10) Uani d . 1 1
H H4 0.9241 0.9418 0.7612 0.060 Uiso calc R 1 1
C C5 0.7619(3) 0.9368(2) 0.5490(6) 0.0424(9) Uani d . 1 1
H H5 0.7212 0.9676 0.6468 0.051 Uiso calc R 1 1
C C6 0.7005(3) 0.9067(2) 0.3349(5) 0.0332(8) Uani d . 1 1
C C7 0.4969(3) 0.8786(2) 0.3466(5) 0.0344(8) Uani d . 1 1
C C8 0.3769(3) 0.8849(2) 0.2259(5) 0.0348(8) Uani d . 1 1
C C9 0.2713(3) 0.8418(2) 0.2425(6) 0.0452(9) Uani d . 1 1
H H9 0.2593 0.8036 0.3602 0.054 Uiso calc R 1 1
C C10 0.1877(3) 0.8671(2) 0.0495(6) 0.0499(10) Uani d . 1 1
H H10 0.1083 0.8486 0.0115 0.060 Uiso calc R 1 1
C C11 0.2437(3) 0.9251(2) -0.0773(6) 0.0428(9) Uani d . 1 1
H H11 0.2067 0.9520 -0.2159 0.051 Uiso calc R 1 1
C C12 0.5279(3) 0.8213(2) 0.5590(5) 0.0471(10) Uani d . 1 1
H H12A 0.6072 0.7979 0.5700 0.071 Uiso calc R 1 1
H H12B 0.4715 0.7736 0.5472 0.071 Uiso calc R 1 1
H H12C 0.5248 0.8555 0.6957 0.071 Uiso calc R 1 1
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'
Ni Ni 0.3393 1.1124 '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
N2 Ni1 N2 . 3_675 180.0 ?
N2 Ni1 N1 . . 83.13(11) y
N2 Ni1 N1 3_675 . 96.87(11) ?
N2 Ni1 N1 . 3_675 96.87(11) y
N2 Ni1 N1 3_675 3_675 83.13(11) ?
N1 Ni1 N1 . 3_675 179.9980(10) ?
C7 N1 C6 . . 118.5(3) y
C7 N1 Ni1 . . 113.4(2) ?
C6 N1 Ni1 . . 128.0(2) ?
C11 N2 C8 . . 105.4(3) y
C11 N2 Ni1 . . 142.3(2) ?
C8 N2 Ni1 . . 112.3(2) ?
C2 C1 C6 . . 120.5(3) ?
C2 C1 H1 . . 119.7 ?
C6 C1 H1 . . 119.7 ?
C1 C2 C3 . . 120.2(3) ?
C1 C2 H2 . . 119.9 ?
C3 C2 H2 . . 119.9 ?
C4 C3 C2 . . 119.6(3) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C3 C4 C5 . . 120.3(3) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C4 C5 C6 . . 120.2(3) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C1 C6 C5 . . 119.2(3) ?
C1 C6 N1 . . 118.3(3) ?
C5 C6 N1 . . 122.5(3) ?
N1 C7 C8 . . 114.8(3) y
N1 C7 C12 . . 125.2(3) ?
C8 C7 C12 . . 119.9(3) ?
N2 C8 C9 . . 110.3(3) y
N2 C8 C7 . . 114.8(3) y
C9 C8 C7 . . 134.3(3) ?
C10 C9 C8 . . 106.2(3) ?
C10 C9 H9 . . 126.9 ?
C8 C9 H9 . . 126.9 ?
C9 C10 C11 . . 107.4(3) ?
C9 C10 H10 . . 126.3 ?
C11 C10 H10 . . 126.3 ?
N2 C11 C10 . . 110.7(3) y
N2 C11 H11 . . 124.7 ?
C10 C11 H11 . . 124.7 ?
C7 C12 H12A . . 109.5 ?
C7 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C7 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
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
Ni1 N2 . 1.894(3) y
Ni1 N2 3_675 1.894(3) ?
Ni1 N1 . 1.939(2) y
Ni1 N1 3_675 1.939(2) ?
N1 C7 . 1.317(4) y
N1 C6 . 1.440(4) y
N2 C11 . 1.354(4) y
N2 C8 . 1.383(4) y
C1 C2 . 1.375(4) ?
C1 C6 . 1.379(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.378(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.376(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.379(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.384(4) ?
C5 H5 . 0.9300 ?
C7 C8 . 1.410(4) y
C7 C12 . 1.500(4) ?
C8 C9 . 1.389(4) y
C9 C10 . 1.378(4) y
C9 H9 . 0.9300 ?
C10 C11 . 1.385(4) y
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
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
C5 H5 <i>Cg</i>1 3_676 0.93 2.64 3.458(8) 147
C11 H11 <i>Cg</i>2 3_675 0.93 2.62 3.384(9) 140
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_site_symmetry_1
_geom_torsion
_geom_torsion_publ_flag
N2 Ni1 N1 C7 . -11.1(2) ?
N2 Ni1 N1 C7 3_675 168.9(2) ?
N2 Ni1 N1 C6 . 165.4(3) ?
N2 Ni1 N1 C6 3_675 -14.6(3) ?
N1 Ni1 N2 C11 . -170.7(4) ?
N1 Ni1 N2 C11 3_675 9.3(4) ?
N1 Ni1 N2 C8 . 10.6(2) ?
N1 Ni1 N2 C8 3_675 -169.4(2) ?
C6 C1 C2 C3 . -1.4(5) ?
C1 C2 C3 C4 . 1.2(6) ?
C2 C3 C4 C5 . -0.3(6) ?
C3 C4 C5 C6 . -0.3(5) ?
C2 C1 C6 C5 . 0.8(5) ?
C2 C1 C6 N1 . 179.3(3) ?
C4 C5 C6 C1 . 0.1(5) ?
C4 C5 C6 N1 . -178.4(3) ?
C7 N1 C6 C1 . 107.6(3) ?
Ni1 N1 C6 C1 . -68.8(4) ?
C7 N1 C6 C5 . -73.9(4) ?
Ni1 N1 C6 C5 . 109.8(3) ?
C6 N1 C7 C8 . -167.8(3) ?
Ni1 N1 C7 C8 . 9.1(3) ?
C6 N1 C7 C12 . 9.5(5) ?
Ni1 N1 C7 C12 . -173.6(2) ?
C11 N2 C8 C9 . -0.6(4) ?
Ni1 N2 C8 C9 . 178.5(2) ?
C11 N2 C8 C7 . 172.0(3) ?
Ni1 N2 C8 C7 . -8.8(3) ?
N1 C7 C8 N2 . -0.3(4) y
C12 C7 C8 N2 . -177.7(3) ?
N1 C7 C8 C9 . 170.1(3) ?
C12 C7 C8 C9 . -7.4(6) ?
N2 C8 C9 C10 . 0.7(4) ?
C7 C8 C9 C10 . -169.9(4) ?
C8 C9 C10 C11 . -0.6(4) ?
C8 N2 C11 C10 . 0.2(4) ?
Ni1 N2 C11 C10 . -178.5(3) ?
C9 C10 C11 N2 . 0.2(4) ?
