#------------------------------------------------------------------------------
#$Date: 2016-03-11 08:33:49 +0100 (vie 11 de mar de 2016) $
#$Revision: 178138 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/45/7224578.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_7224578
loop_
_publ_author_name
'Ribeiro, Ana'
'Karabach, Yauhen Yu.'
'Martins, Luísa Margarida'
'Mahmoud, Abdallah G.'
'Guedes da Silva, M. Fátima C.'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 Nickel(II)-2-amino-4-alkoxy-1,3,5-triazapentadienate complexes as
 catalysts for Heck and Henry reactions
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA02989B
_journal_year                    2016
_chemical_formula_moiety         'C8 H18 N8 Ni O2'
_chemical_formula_sum            'C8 H18 N8 Ni O2'
_chemical_formula_weight         317.01
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-12-23 deposited with the CCDC.
2016-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.668(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.4047(10)
_cell_length_b                   8.4499(5)
_cell_length_c                   9.8847(5)
_cell_measurement_reflns_used    1401
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      2.71
_cell_volume                     1377.24(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Mercury CSD 3.5.1'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4636
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         25.361
_diffrn_reflns_theta_min         2.470
_exptl_absorpt_coefficient_mu    1.422
_exptl_absorpt_correction_T_max  0.849
_exptl_absorpt_correction_T_min  0.650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.684
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1260
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0358
_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)+(0.0564P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0917
_reflns_Friedel_coverage         0.000
_reflns_number_gt                999
_reflns_number_total             1260
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ra02989b2.cif
_cod_data_source_block           Compound6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_database_code               7224578
_shelx_shelxl_version_number     2014/7
_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   0.659
_shelx_estimated_absorpt_t_max   0.859
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
_atom_site_refinement_flags_occupancy
C1 C 0.35261(17) 0.4681(3) 0.4203(3) 0.0205(6) Uani 1 1 d . . .
C2 C 0.32063(18) 0.2479(3) 0.2737(3) 0.0228(6) Uani 1 1 d . . .
C3 C 0.44256(19) 0.6595(4) 0.3688(3) 0.0286(7) Uani 1 1 d . . .
H3A H 0.4090 0.6753 0.2679 0.034 Uiso 1 1 calc R U .
H3B H 0.4852 0.5805 0.3724 0.034 Uiso 1 1 calc R U .
C4 C 0.4797(2) 0.8129(4) 0.4345(4) 0.0397(9) Uani 1 1 d . . .
H4A H 0.5144 0.8546 0.3818 0.060 Uiso 1 1 calc R U .
H4B H 0.4367 0.8893 0.4304 0.060 Uiso 1 1 calc R U .
H4C H 0.5124 0.7950 0.5343 0.060 Uiso 1 1 calc R U .
N1 N 0.31433(15) 0.4261(3) 0.5091(2) 0.0215(6) Uani 1 1 d D . .
N2 N 0.27887(16) 0.1770(3) 0.3455(3) 0.0241(6) Uani 1 1 d . . .
N3 N 0.35491(15) 0.3937(3) 0.3022(2) 0.0226(6) Uani 1 1 d . . .
N4 N 0.33504(19) 0.1748(3) 0.1617(3) 0.0329(7) Uani 1 1 d D . .
O1 O 0.39302(12) 0.6074(2) 0.4527(2) 0.0255(5) Uani 1 1 d . . .
Ni1 Ni 0.2500 0.2500 0.5000 0.01903(19) Uani 1 2 d S . P
H1N H 0.3270(18) 0.489(3) 0.582(3) 0.029 Uiso 1 1 d D U .
H2N H 0.2647(19) 0.088(4) 0.314(3) 0.029 Uiso 1 1 d . U .
H4N1 H 0.363(2) 0.222(4) 0.117(4) 0.029 Uiso 1 1 d . U .
H4N2 H 0.3064(16) 0.094(3) 0.123(3) 0.029 Uiso 1 1 d D U .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C1 N3 128.4(3) . .
N1 C1 O1 114.4(2) . .
N3 C1 O1 117.1(2) . .
N2 C2 N3 125.8(3) . .
N2 C2 N4 120.8(3) . .
N3 C2 N4 113.4(2) . .
O1 C3 C4 105.5(2) . .
O1 C3 H3A 110.6 . .
C4 C3 H3A 110.6 . .
O1 C3 H3B 110.6 . .
C4 C3 H3B 110.6 . .
H3A C3 H3B 108.8 . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C1 N1 Ni1 128.0(2) . .
C1 N1 H1N 110(2) . .
Ni1 N1 H1N 122(2) . .
C2 N2 Ni1 129.4(2) . .
C2 N2 H2N 111(2) . .
Ni1 N2 H2N 119(2) . .
C1 N3 C2 118.2(2) . .
C2 N4 H4N1 120(2) . .
C2 N4 H4N2 120(2) . .
H4N1 N4 H4N2 119(3) . .
C1 O1 C3 119.2(2) . .
N1 Ni1 N1 180.0 . 7_556
N1 Ni1 N2 90.68(11) . 7_556
N1 Ni1 N2 89.32(11) 7_556 7_556
N1 Ni1 N2 89.32(11) . .
N1 Ni1 N2 90.68(11) 7_556 .
N2 Ni1 N2 180.0 7_556 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.309(3) .
C1 N3 1.338(3) .
C1 O1 1.356(3) .
C2 N2 1.312(4) .
C2 N3 1.358(4) .
C2 N4 1.359(4) .
C3 O1 1.444(3) .
C3 C4 1.501(5) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
N1 Ni1 1.847(2) .
N1 H1N 0.867(18) .
N2 Ni1 1.859(2) .
N2 H2N 0.82(3) .
N4 H4N1 0.86(4) .
N4 H4N2 0.859(18) .
Ni1 N1 1.847(2) 7_556
Ni1 N2 1.859(2) 7_556
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N N3 0.867(18) 2.297(19) 3.146(3) 167(3) 6_566
N2 H2N N3 0.82(3) 2.61(3) 3.333(4) 147(3) 4_545
N4 H4N1 O1 0.86(4) 2.34(4) 3.163(3) 158(3) 6_565
N4 H4N2 N1 0.859(18) 2.53(2) 3.349(4) 161(3) 4_545
