#------------------------------------------------------------------------------
#$Date: 2016-03-11 09:33:49 +0200 (Fri, 11 Mar 2016) $
#$Revision: 178138 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/45/7224577.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_7224577
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         'C6 H14 N8 Ni O2'
_chemical_formula_sum            'C6 H14 N8 Ni O2'
_chemical_formula_weight         288.96
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 105.589(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8530(12)
_cell_length_b                   8.1074(13)
_cell_length_c                   9.7290(15)
_cell_measurement_reflns_used    932
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.01
_cell_measurement_theta_min      2.63
_cell_volume                     596.63(16)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.974
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_laue_measured_fraction_full 0.994
_diffrn_reflns_laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5824
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.087
_diffrn_reflns_theta_min         2.693
_exptl_absorpt_coefficient_mu    1.632
_exptl_absorpt_correction_T_max  0.829
_exptl_absorpt_correction_T_min  0.731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.297
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.115
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1282
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0251
_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)+(0.0314P)²+0.0587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0593
_refine_ls_wR_factor_ref         0.0632
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1023
_reflns_number_total             1282
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ra02989b2.cif
_cod_data_source_block           Compound5
_cod_database_code               7224577
_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   0.643
_shelx_estimated_absorpt_t_max   0.834
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.2581(2) 0.7871(2) 0.8122(2) 0.0193(4) Uani 1 1 d . . .
C2 C 0.3409(3) 1.0100(2) 0.6974(2) 0.0202(4) Uani 1 1 d . . .
C3 C 0.0565(3) 0.5959(3) 0.6635(2) 0.0417(7) Uani 1 1 d . . .
H3A H -0.0164 0.6854 0.6165 0.063 Uiso 1 1 calc R U .
H3B H -0.0170 0.5046 0.6737 0.063 Uiso 1 1 calc R U .
H3C H 0.1345 0.5625 0.6078 0.063 Uiso 1 1 calc R U .
N1 N 0.3454(2) 0.8261(2) 0.94199(18) 0.0205(4) Uani 1 1 d . . .
N2 N 0.2567(2) 0.8632(2) 0.69101(17) 0.0202(4) Uani 1 1 d . . .
N3 N 0.3143(3) 1.0850(2) 0.56918(19) 0.0299(4) Uani 1 1 d D . .
N4 N 0.4401(2) 1.0780(2) 0.81373(17) 0.0221(4) Uani 1 1 d . . .
O1 O 0.15914(19) 0.64894(18) 0.80255(14) 0.0285(4) Uani 1 1 d . . .
Ni1 Ni 0.5000 1.0000 1.0000 0.01638(12) Uani 1 2 d S . P
H1N H 0.319(3) 0.767(3) 1.000(2) 0.025 Uiso 1 1 d . U .
H3N1 H 0.381(3) 1.166(2) 0.559(2) 0.025 Uiso 1 1 d D U .
H3N2 H 0.241(3) 1.041(3) 0.493(3) 0.025 Uiso 1 1 d . U .
H4N H 0.484(3) 1.164(3) 0.799(2) 0.025 Uiso 1 1 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 N2 128.61(18) . .
N1 C1 O1 114.26(17) . .
N2 C1 O1 117.12(17) . .
N4 C2 N3 121.1(2) . .
N4 C2 N2 125.33(19) . .
N3 C2 N2 113.60(18) . .
O1 C3 H3A 109.5 . .
O1 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
O1 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
C1 N1 Ni1 127.76(15) . .
C1 N1 H1N 111.5(17) . .
Ni1 N1 H1N 120.6(16) . .
C1 N2 C2 118.70(17) . .
C2 N3 H3N1 120.3(15) . .
C2 N3 H3N2 119.9(15) . .
H3N1 N3 H3N2 119(2) . .
C2 N4 Ni1 129.46(16) . .
C2 N4 H4N 113.3(16) . .
Ni1 N4 H4N 117.2(16) . .
C1 O1 C3 118.56(16) . .
N1 Ni1 N1 180.0 3_677 .
N1 Ni1 N4 89.34(8) 3_677 3_677
N1 Ni1 N4 90.66(8) . 3_677
N1 Ni1 N4 90.66(8) 3_677 .
N1 Ni1 N4 89.34(8) . .
N4 Ni1 N4 180.00(11) 3_677 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.304(3) .
C1 N2 1.328(2) .
C1 O1 1.352(2) .
C2 N4 1.311(3) .
C2 N3 1.352(3) .
C2 N2 1.355(3) .
C3 O1 1.441(2) .
C3 H3A 0.9600 .
C3 H3B 0.9600 .
C3 H3C 0.9600 .
N1 Ni1 1.8471(17) .
N1 H1N 0.81(2) .
N3 H3N1 0.862(16) .
N3 H3N2 0.88(3) .
N4 Ni1 1.8567(17) .
N4 H4N 0.80(2) .
Ni1 N1 1.8471(17) 3_677
Ni1 N4 1.8567(17) 3_677
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
N4 H4N N2 0.80(2) 2.58(2) 3.329(2) 155(2) 2_656
N1 H1N N2 0.81(2) 2.30(2) 3.101(2) 170(2) 4_576
N3 H3N1 N1 0.862(16) 2.512(17) 3.336(3) 160.1(19) 2_656
N3 H3N2 O1 0.88(3) 2.36(3) 3.180(2) 154(2) 4_575
N1 H1N N2 0.81(2) 2.30(2) 3.101(2) 170(2) 4_576
N3 H3N1 N1 0.862(16) 2.512(17) 3.336(3) 160.1(19) 2_656
N3 H3N2 O1 0.88(3) 2.36(3) 3.180(2) 154(2) 4_575
N4 H4N N2 0.80(2) 2.58(2) 3.329(2) 155(2) 2_656
