#------------------------------------------------------------------------------
#$Date: 2019-04-10 01:26:08 +0300 (Wed, 10 Apr 2019) $
#$Revision: 214572 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/08/1550869.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_1550869
loop_
_publ_author_name
'Gwak, Jinseong'
'Ahn, Seihwan'
'Baik, Mu-Hyun'
'Lee, Yunho'
_publ_section_title
;
 One metal is enough: A nickel complex reduces nitrate anions to nitrogen
 gas
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC00717B
_journal_year                    2019
_chemical_formula_moiety         'C26 H40 N2 Ni O3 P2'
_chemical_formula_sum            'C26 H40 N2 Ni O3 P2'
_chemical_formula_weight         549.25
_chemical_name_systematic
; 
 ? 
;
_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           SHELXL-97
_audit_update_record
;
2018-09-13 deposited with the CCDC.    2019-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.863(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.5906(8)
_cell_length_b                   10.6460(5)
_cell_length_c                   16.1974(9)
_cell_measurement_reflns_used    50270
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      1.26
_cell_volume                     2789.0(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1120
_diffrn_reflns_av_sigmaI/netI    0.0732
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            50270
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         1.26
_exptl_absorpt_coefficient_mu    0.839
_exptl_absorpt_correction_T_max  0.9359
_exptl_absorpt_correction_T_min  0.9208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platy
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         6293
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0502
_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)+(0.0752P)²+0.8303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1512
_reflns_number_gt                4147
_reflns_number_total             6293
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9sc00717b2.cif
_cod_data_source_block           0275a-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/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.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        2789.1(2)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1550869
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_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ni1 Ni 0.20122(3) 0.07588(4) 0.46362(3) 0.02054(14) Uani 1 1 d .
P1 P 0.29066(5) 0.22303(8) 0.52215(5) 0.0197(2) Uani 1 1 d .
P2 P 0.13233(5) -0.09454(8) 0.41017(6) 0.0211(2) Uani 1 1 d .
O1 O 0.10473(15) 0.1768(2) 0.44737(16) 0.0285(6) Uani 1 1 d .
O2 O 0.15234(17) 0.2768(3) 0.35036(17) 0.0402(7) Uani 1 1 d .
O3 O 0.03700(18) 0.3329(3) 0.38039(19) 0.0528(8) Uani 1 1 d .
N1 N 0.29417(16) -0.0311(3) 0.48680(17) 0.0216(6) Uani 1 1 d .
N2 N 0.09886(19) 0.2628(3) 0.39176(19) 0.0290(7) Uani 1 1 d .
C1 C 0.2950(2) -0.1375(3) 0.4364(2) 0.0225(7) Uani 1 1 d .
C2 C 0.2185(2) -0.1875(3) 0.3934(2) 0.0198(7) Uani 1 1 d .
C3 C 0.2145(2) -0.2915(3) 0.3400(2) 0.0242(8) Uani 1 1 d .
H3A H 0.1620 -0.3229 0.3119 0.029 Uiso 1 1 calc R
C4 C 0.2856(2) -0.3501(3) 0.3270(2) 0.0246(8) Uani 1 1 d .
C5 C 0.3612(2) -0.2987(3) 0.3686(2) 0.0273(8) Uani 1 1 d .
H5A H 0.4107 -0.3358 0.3598 0.033 Uiso 1 1 calc R
C6 C 0.3671(2) -0.1962(3) 0.4218(2) 0.0252(8) Uani 1 1 d .
H6A H 0.4200 -0.1649 0.4488 0.030 Uiso 1 1 calc R
C7 C 0.2807(2) -0.4611(3) 0.2678(2) 0.0304(8) Uani 1 1 d .
H7A H 0.2226 -0.4834 0.2455 0.046 Uiso 1 1 calc R
H7B H 0.3099 -0.5328 0.2987 0.046 Uiso 1 1 calc R
H7C H 0.3063 -0.4390 0.2208 0.046 Uiso 1 1 calc R
C8 C 0.3600(2) -0.0036(3) 0.5550(2) 0.0210(7) Uani 1 1 d .
C9 C 0.3692(2) 0.1218(3) 0.5832(2) 0.0207(7) Uani 1 1 d .
C10 C 0.4314(2) 0.1554(3) 0.6528(2) 0.0232(8) Uani 1 1 d .
H10A H 0.4368 0.2409 0.6700 0.028 Uiso 1 1 calc R
C11 C 0.4855(2) 0.0670(3) 0.6978(2) 0.0238(8) Uani 1 1 d .
C12 C 0.4741(2) -0.0569(3) 0.6705(2) 0.0254(8) Uani 1 1 d .
H12A H 0.5094 -0.1197 0.7008 0.031 Uiso 1 1 calc R
C13 C 0.4137(2) -0.0930(3) 0.6013(2) 0.0232(8) Uani 1 1 d .
H13A H 0.4086 -0.1788 0.5849 0.028 Uiso 1 1 calc R
C14 C 0.5522(2) 0.1016(3) 0.7740(2) 0.0346(9) Uani 1 1 d .
H14A H 0.5510 0.1925 0.7835 0.052 Uiso 1 1 calc R
H14B H 0.6063 0.0777 0.7641 0.052 Uiso 1 1 calc R
H14C H 0.5426 0.0573 0.8240 0.052 Uiso 1 1 calc R
C15 C 0.2633(2) 0.3354(3) 0.5976(2) 0.0269(8) Uani 1 1 d .
H15A H 0.3159 0.3699 0.6329 0.032 Uiso 1 1 calc R
C16 C 0.2188(3) 0.2651(4) 0.6562(3) 0.0400(10) Uani 1 1 d .
H16A H 0.2042 0.3240 0.6970 0.060 Uiso 1 1 calc R
H16B H 0.2551 0.1996 0.6866 0.060 Uiso 1 1 calc R
H16C H 0.1684 0.2265 0.6227 0.060 Uiso 1 1 calc R
C17 C 0.2124(3) 0.4457(4) 0.5539(3) 0.0383(10) Uani 1 1 d .
H17A H 0.1999 0.5030 0.5967 0.057 Uiso 1 1 calc R
H17B H 0.1606 0.4144 0.5182 0.057 Uiso 1 1 calc R
H17C H 0.2438 0.4906 0.5186 0.057 Uiso 1 1 calc R
C18 C 0.3384(2) 0.3132(3) 0.4487(2) 0.0272(8) Uani 1 1 d .
H18A H 0.2956 0.3722 0.4171 0.033 Uiso 1 1 calc R
C19 C 0.3616(2) 0.2238(4) 0.3842(2) 0.0381(10) Uani 1 1 d .
H19A H 0.3866 0.2715 0.3447 0.057 Uiso 1 1 calc R
H19B H 0.3118 0.1811 0.3529 0.057 Uiso 1 1 calc R
H19C H 0.4011 0.1614 0.4137 0.057 Uiso 1 1 calc R
C20 C 0.4124(2) 0.3920(4) 0.4926(3) 0.0430(11) Uani 1 1 d .
H20A H 0.4344 0.4380 0.4500 0.064 Uiso 1 1 calc R
H20B H 0.4555 0.3368 0.5248 0.064 Uiso 1 1 calc R
H20C H 0.3950 0.4518 0.5312 0.064 Uiso 1 1 calc R
C21 C 0.0591(2) -0.0842(3) 0.3070(2) 0.0259(8) Uani 1 1 d .
H21A H 0.0473 -0.1714 0.2847 0.031 Uiso 1 1 calc R
C22 C 0.0998(2) -0.0119(4) 0.2451(2) 0.0357(9) Uani 1 1 d .
H22A H 0.0611 -0.0062 0.1898 0.054 Uiso 1 1 calc R
H22B H 0.1499 -0.0561 0.2388 0.054 Uiso 1 1 calc R
H22C H 0.1143 0.0729 0.2670 0.054 Uiso 1 1 calc R
C23 C -0.0233(2) -0.0236(4) 0.3136(3) 0.0349(9) Uani 1 1 d .
H23A H -0.0604 -0.0204 0.2574 0.052 Uiso 1 1 calc R
H23B H -0.0131 0.0618 0.3361 0.052 Uiso 1 1 calc R
H23C H -0.0489 -0.0736 0.3517 0.052 Uiso 1 1 calc R
C24 C 0.0813(2) -0.1846(3) 0.4813(2) 0.0273(8) Uani 1 1 d .
H24A H 0.0335 -0.1337 0.4907 0.033 Uiso 1 1 calc R
C25 C 0.1411(2) -0.2015(4) 0.5670(2) 0.0374(10) Uani 1 1 d .
H25A H 0.1139 -0.2488 0.6050 0.056 Uiso 1 1 calc R
H25B H 0.1578 -0.1189 0.5917 0.056 Uiso 1 1 calc R
H25C H 0.1901 -0.2475 0.5593 0.056 Uiso 1 1 calc R
C26 C 0.0472(2) -0.3118(3) 0.4439(3) 0.0357(9) Uani 1 1 d .
H26A H 0.0206 -0.3552 0.4841 0.054 Uiso 1 1 calc R
H26B H 0.0927 -0.3633 0.4330 0.054 Uiso 1 1 calc R
H26C H 0.0066 -0.2978 0.3906 0.054 Uiso 1 1 calc R
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'
P P 0.1023 0.0942 '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
N1 Ni1 O1 175.41(12)
N1 Ni1 P2 84.89(9)
O1 Ni1 P2 93.66(8)
N1 Ni1 P1 84.39(9)
O1 Ni1 P1 97.04(8)
P2 Ni1 P1 169.27(4)
C9 P1 C15 106.21(15)
C9 P1 C18 107.64(16)
C15 P1 C18 107.18(17)
C9 P1 Ni1 98.33(11)
C15 P1 Ni1 120.21(12)
C18 P1 Ni1 115.82(12)
C2 P2 C21 106.33(16)
C2 P2 C24 107.31(16)
C21 P2 C24 107.26(16)
C2 P2 Ni1 98.66(11)
C21 P2 Ni1 119.05(12)
C24 P2 Ni1 116.79(12)
N2 O1 Ni1 115.8(2)
C1 N1 C8 121.6(3)
C1 N1 Ni1 119.1(2)
C8 N1 Ni1 119.3(2)
O2 N2 O3 120.9(3)
O2 N2 O1 121.3(3)
O3 N2 O1 117.7(3)
N1 C1 C2 118.0(3)
N1 C1 C6 125.0(3)
C2 C1 C6 116.9(3)
C3 C2 C1 121.2(3)
C3 C2 P2 126.6(3)
C1 C2 P2 112.0(2)
C4 C3 C2 121.6(3)
C3 C4 C5 116.9(3)
C3 C4 C7 121.2(3)
C5 C4 C7 121.9(3)
C6 C5 C4 122.8(3)
C5 C6 C1 120.6(3)
N1 C8 C13 124.8(3)
N1 C8 C9 117.6(3)
C13 C8 C9 117.4(3)
C10 C9 C8 120.8(3)
C10 C9 P1 127.1(3)
C8 C9 P1 112.0(2)
C11 C10 C9 121.7(3)
C10 C11 C12 116.7(3)
C10 C11 C14 122.2(3)
C12 C11 C14 121.1(3)
C13 C12 C11 123.0(3)
C12 C13 C8 120.3(3)
C16 C15 C17 111.8(3)
C16 C15 P1 108.7(2)
C17 C15 P1 112.7(2)
C19 C18 C20 111.3(3)
C19 C18 P1 109.1(3)
C20 C18 P1 113.8(3)
C22 C21 C23 111.3(3)
C22 C21 P2 109.0(2)
C23 C21 P2 112.3(3)
C25 C24 C26 111.3(3)
C25 C24 P2 109.4(2)
C26 C24 P2 113.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ni1 N1 1.887(3)
Ni1 O1 1.897(2)
Ni1 P2 2.2152(10)
Ni1 P1 2.2199(10)
P1 C9 1.806(3)
P1 C15 1.837(3)
P1 C18 1.839(3)
P2 C2 1.809(3)
P2 C21 1.838(3)
P2 C24 1.844(4)
O1 N2 1.272(4)
O2 N2 1.235(4)
O3 N2 1.249(4)
N1 C1 1.398(4)
N1 C8 1.401(4)
C1 C2 1.409(5)
C1 C6 1.415(5)
C2 C3 1.397(5)
C3 C4 1.392(5)
C4 C5 1.396(5)
C4 C7 1.512(5)
C5 C6 1.380(5)
C8 C13 1.402(4)
C8 C9 1.408(5)
C9 C10 1.395(5)
C10 C11 1.391(5)
C11 C12 1.391(5)
C11 C14 1.508(5)
C12 C13 1.381(5)
C15 C16 1.524(5)
C15 C17 1.526(5)
C18 C19 1.524(5)
C18 C20 1.526(5)
C21 C22 1.535(5)
C21 C23 1.536(5)
C24 C25 1.526(5)
C24 C26 1.538(5)
