#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/04/2240402.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_2240402
loop_
_publ_author_name
'Kim, Dae-Woong'
'Shin, Jong Won'
'Kim, Jin Hong'
'Moon, Dohyun'
_publ_section_title
;
 Crystal structure of
 trans-(1,8-dibutyl-1,3,6,8,10,13-hexaazacyclotetradecane-κ⁴N³,N⁶,N¹⁰,N¹³)bis(5-methyltetrazolato-κN)nickel(II)
 from synchrotron data
;
_journal_coeditor_code           IS5389
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              173
_journal_page_last               175
_journal_paper_doi               10.1107/S2056989015000651
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          '[Ni (C2 H3 N4)2 (C16 H38 N6)]'
_chemical_formula_moiety         'C20 H44 N14 Ni'
_chemical_formula_sum            'C20 H44 N14 Ni'
_chemical_formula_weight         539.40
_chemical_name_systematic
trans-(1,8-Dibutyl-1,3,6,8,10,13-hexaazacyclotetradecane-κ⁴N³,N⁶,N¹⁰,N¹³)bis(5-methyltetrazolato-κN²)nickel(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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.94(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.040(5)
_cell_length_b                   12.923(3)
_cell_length_c                   8.7170(17)
_cell_measurement_reflns_used    25946
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.55
_cell_measurement_theta_min      0.36
_cell_volume                     2675.2(10)
_computing_cell_refinement
;
HKL3000sm (Otwinowski & Minor, 1997)
;
_computing_data_collection
;
PAL ADSC Quantum-210 ADX (Arvai & Nielsen, 1983)
;
_computing_data_reduction
;
HKL3000sm (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics
;
DIAMOND4 (Putz & Brandenburg, 2014)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014/7 (Sheldrick, 2008, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'ADSC Q210 CCD area-detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.62998
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12808
_diffrn_reflns_theta_full        22.209
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.590
_exptl_absorpt_coefficient_mu    0.551
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
(HKL3000sm SCALEPACK;  Otwinowski & Minor, 1997)
;
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.788
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         3761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0321
_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)+(0.0565P)²+0.1060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0899
_reflns_number_gt                3150
_reflns_number_total             3761
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is5389sup1.cf
_cod_data_source_block           I
_cod_original_cell_volume        2675.1(9)
_cod_database_code               2240402
_cod_database_fobs_code          2240402
#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   0.973
_shelx_estimated_absorpt_t_max   0.978
#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_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_occupancy
Ni Ni1 0.2500 0.7500 0.5000 0.00596(8) Uani d 1
N N1 0.31782(5) 0.83411(8) 0.60560(11) 0.0073(2) Uani d 1
H H1 0.3488 0.7841 0.6424 0.009 Uiso calc 1
N N2 0.28136(5) 0.73476(8) 0.29352(12) 0.0076(2) Uani d 1
H H2 0.3095 0.6773 0.3067 0.009 Uiso calc 1
N N3 0.35616(5) 0.86428(8) 0.36376(12) 0.0095(2) Uani d 1
C C1 0.29951(5) 0.88036(9) 0.74420(13) 0.0094(2) Uani d 1
H H1A 0.2752 0.9411 0.7137 0.011 Uiso calc 1
H H1B 0.3327 0.9038 0.8177 0.011 Uiso calc 1
C C2 0.34005(6) 0.90993(9) 0.50278(14) 0.0097(2) Uani d 1
H H2A 0.3110 0.9634 0.4716 0.012 Uiso calc 1
H H2B 0.3733 0.9448 0.5621 0.012 Uiso calc 1
C C3 0.31026(6) 0.82902(9) 0.24815(14) 0.0096(2) Uani d 1
H H3A 0.3251 0.8147 0.1505 0.011 Uiso calc 1
H H3B 0.2823 0.8854 0.2270 0.011 Uiso calc 1
C C4 0.23296(6) 0.70064(10) 0.17841(14) 0.0095(2) Uani d 1
H H4A 0.2464 0.6706 0.0864 0.011 Uiso calc 1
H H4B 0.2083 0.7603 0.1441 0.011 Uiso calc 1
C C5 0.40350(6) 0.79167(10) 0.39114(15) 0.0119(2) Uani d 1
H H5A 0.4070 0.7560 0.2926 0.014 Uiso calc 1
H H5B 0.3955 0.7386 0.4666 0.014 Uiso calc 1
C C6 0.45926(6) 0.84385(12) 0.45282(18) 0.0188(3) Uani d 1
H H6A 0.4686 0.8939 0.3747 0.023 Uiso calc 1
H H6B 0.4553 0.8829 0.5483 0.023 Uiso calc 1
C C7 0.50699(7) 0.76635(13) 0.4891(2) 0.0237(3) Uani d 1
H H7A 0.5101 0.7263 0.3940 0.028 Uiso calc 1
H H7B 0.4977 0.7172 0.5685 0.028 Uiso calc 1
C C8 0.56368(7) 0.81669(16) 0.5480(2) 0.0334(4) Uani d 1
H H8A 0.5737 0.8641 0.4688 0.050 Uiso calc 1
H H8B 0.5926 0.7630 0.5696 0.050 Uiso calc 1
H H8C 0.5612 0.8554 0.6434 0.050 Uiso calc 1
N N4 0.30074(5) 0.61260(8) 0.58628(12) 0.0100(2) Uani d 1
N N5 0.29007(5) 0.51298(9) 0.56721(14) 0.0156(2) Uani d 1
N N6 0.33266(5) 0.45876(9) 0.64836(16) 0.0185(3) Uani d 1
N N7 0.35088(5) 0.62585(9) 0.67914(13) 0.0146(2) Uani d 1
C C9 0.36869(6) 0.52976(10) 0.71493(17) 0.0157(3) Uani d 1
C C10 0.42228(7) 0.50538(13) 0.8200(2) 0.0298(4) Uani d 1
H H10A 0.4139 0.4869 0.9230 0.045 Uiso calc 1
H H10B 0.4470 0.5661 0.8285 0.045 Uiso calc 1
H H10C 0.4411 0.4472 0.7773 0.045 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0020 0.0010 '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 0.0050 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3520 0.9030 '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
N1 Ni1 N1 7_566 . 180.0
N1 Ni1 N2 7_566 . 86.04(4)
N1 Ni1 N2 . . 93.96(4)
N1 Ni1 N2 7_566 7_566 93.96(4)
N1 Ni1 N2 . 7_566 86.04(4)
N2 Ni1 N2 . 7_566 180.0
N1 Ni1 N4 7_566 7_566 85.15(4)
N1 Ni1 N4 . 7_566 94.86(4)
N2 Ni1 N4 . 7_566 92.11(4)
N2 Ni1 N4 7_566 7_566 87.89(4)
N1 Ni1 N4 7_566 . 94.86(4)
N1 Ni1 N4 . . 85.14(4)
N2 Ni1 N4 . . 87.89(4)
N2 Ni1 N4 7_566 . 92.11(4)
N4 Ni1 N4 7_566 . 180.0
C1 N1 C2 . . 114.13(10)
C1 N1 Ni1 . . 105.32(8)
C2 N1 Ni1 . . 114.48(8)
C1 N1 H1 . . 107.5
C2 N1 H1 . . 107.5
Ni1 N1 H1 . . 107.5
C4 N2 C3 . . 114.49(10)
C4 N2 Ni1 . . 105.31(8)
C3 N2 Ni1 . . 113.75(7)
C4 N2 H2 . . 107.7
C3 N2 H2 . . 107.7
Ni1 N2 H2 . . 107.7
C3 N3 C2 . . 115.80(10)
C3 N3 C5 . . 113.60(10)
C2 N3 C5 . . 115.15(10)
N1 C1 C4 . 7_566 108.83(10)
N1 C1 H1A . . 109.9
C4 C1 H1A 7_566 . 109.9
N1 C1 H1B . . 109.9
C4 C1 H1B 7_566 . 109.9
H1A C1 H1B . . 108.3
N3 C2 N1 . . 113.80(10)
N3 C2 H2A . . 108.8
N1 C2 H2A . . 108.8
N3 C2 H2B . . 108.8
N1 C2 H2B . . 108.8
H2A C2 H2B . . 107.7
N3 C3 N2 . . 114.21(10)
N3 C3 H3A . . 108.7
N2 C3 H3A . . 108.7
N3 C3 H3B . . 108.7
N2 C3 H3B . . 108.7
H3A C3 H3B . . 107.6
N2 C4 C1 . 7_566 107.88(10)
N2 C4 H4A . . 110.1
C1 C4 H4A 7_566 . 110.1
N2 C4 H4B . . 110.1
C1 C4 H4B 7_566 . 110.1
H4A C4 H4B . . 108.4
N3 C5 C6 . . 113.12(11)
N3 C5 H5A . . 109.0
C6 C5 H5A . . 109.0
N3 C5 H5B . . 109.0
C6 C5 H5B . . 109.0
H5A C5 H5B . . 107.8
C7 C6 C5 . . 112.13(12)
C7 C6 H6A . . 109.2
C5 C6 H6A . . 109.2
C7 C6 H6B . . 109.2
C5 C6 H6B . . 109.2
H6A C6 H6B . . 107.9
C6 C7 C8 . . 113.29(14)
C6 C7 H7A . . 108.9
C8 C7 H7A . . 108.9
C6 C7 H7B . . 108.9
C8 C7 H7B . . 108.9
H7A C7 H7B . . 107.7
C7 C8 H8A . . 109.5
C7 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
C7 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
N5 N4 N7 . . 109.66(11)
N5 N4 Ni1 . . 130.78(9)
N7 N4 Ni1 . . 119.52(8)
N4 N5 N6 . . 108.96(11)
C9 N6 N5 . . 105.08(11)
C9 N7 N4 . . 104.21(11)
N6 C9 N7 . . 112.09(13)
N6 C9 C10 . . 124.23(13)
N7 C9 C10 . . 123.67(13)
C9 C10 H10A . . 109.5
C9 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
C9 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Ni1 N1 . 2.0543(12)
Ni1 N2 . 2.0661(11)
Ni1 N4 . 2.2183(11)
N1 C1 . 1.4752(15)
N1 C2 . 1.4826(15)
N1 H1 . 1.0000
N2 C4 . 1.4807(17)
N2 C3 . 1.4860(16)
N2 H2 . 1.0000
N3 C3 . 1.4474(17)
N3 C2 . 1.4535(16)
N3 C5 . 1.4657(17)
C1 C4 7_566 1.5244(17)
C1 H1A . 0.9900
C1 H1B . 0.9900
C2 H2A . 0.9900
C2 H2B . 0.9900
C3 H3A . 0.9900
C3 H3B . 0.9900
C4 C1 7_566 1.5244(17)
C4 H4A . 0.9900
C4 H4B . 0.9900
C5 C6 . 1.522(2)
C5 H5A . 0.9900
C5 H5B . 0.9900
C6 C7 . 1.519(2)
C6 H6A . 0.9900
C6 H6B . 0.9900
C7 C8 . 1.525(2)
C7 H7A . 0.9900
C7 H7B . 0.9900
C8 H8A . 0.9800
C8 H8B . 0.9800
C8 H8C . 0.9800
N4 N5 . 1.3182(15)
N4 N7 . 1.3543(16)
N5 N6 . 1.3469(17)
N6 C9 . 1.3314(19)
N7 C9 . 1.3347(17)
C9 C10 . 1.494(2)
C10 H10A . 0.9800
C10 H10B . 0.9800
C10 H10C . 0.9800
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
N1 H1 N7 . 1.00 2.07 2.8508(16) 133
N2 H2 N6 6_565 1.00 2.35 3.1403(16) 135
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_4
_geom_torsion
C2 N1 C1 C4 7_566 168.66(10)
Ni1 N1 C1 C4 7_566 42.26(11)
C3 N3 C2 N1 . 70.86(14)
C5 N3 C2 N1 . -65.05(14)
C1 N1 C2 N3 . -177.96(10)
Ni1 N1 C2 N3 . -56.49(12)
C2 N3 C3 N2 . -71.26(14)
C5 N3 C3 N2 . 65.32(14)
C4 N2 C3 N3 . 177.73(10)
Ni1 N2 C3 N3 . 56.58(12)
C3 N2 C4 C1 7_566 -167.67(10)
Ni1 N2 C4 C1 7_566 -41.97(10)
C3 N3 C5 C6 . 154.78(11)
C2 N3 C5 C6 . -68.36(14)
N3 C5 C6 C7 . 176.68(12)
C5 C6 C7 C8 . 178.80(14)
N7 N4 N5 N6 . 0.63(15)
Ni1 N4 N5 N6 . -177.06(9)
N4 N5 N6 C9 . -0.27(16)
N5 N4 N7 C9 . -0.72(15)
Ni1 N4 N7 C9 . 177.28(9)
N5 N6 C9 N7 . -0.20(17)
N5 N6 C9 C10 . 178.68(15)
N4 N7 C9 N6 . 0.56(16)
N4 N7 C9 C10 . -178.32(14)
