#------------------------------------------------------------------------------
#$Date: 2019-11-03 14:20:26 +0200 (Sun, 03 Nov 2019) $
#$Revision: 221629 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/85/4128548.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_4128548
loop_
_publ_author_name
'Ravn, Anne K.'
'Vilstrup, Maria B. T.'
'Noerby, Peter'
'Nielsen, Dennis U.'
'Daasbjerg, Kim'
'Skrydstrup, Troels'
_publ_section_title
;
 Carbon Isotope Labeling Strategy for β-Amino Acid Derivatives via
 Carbonylation of Azanickellacycles.
;
_journal_issue                   30
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11821
_journal_page_last               11826
_journal_paper_doi               10.1021/jacs.9b05934
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C28 H25 N3 Ni O2 S'
_chemical_formula_sum            'C28 H25 N3 Ni O2 S'
_chemical_formula_weight         526.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-05-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.327(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2268(11)
_cell_length_b                   33.721(5)
_cell_length_c                   9.7279(15)
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.98
_cell_measurement_theta_min      2.19
_cell_volume                     2356.2(6)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            80624
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         22.018
_diffrn_reflns_theta_min         1.906
_exptl_absorpt_coefficient_mu    0.500
_exptl_absorpt_correction_T_max  0.7447
_exptl_absorpt_correction_T_min  0.7069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1292 before and 0.0637 after correction. The Ratio of minimum to maximum transmission is 0.9492. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'metallic reddish black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0368P)²+2.3986P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4811
_reflns_number_total             5856
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b05934_si_002.cif
_cod_data_source_block           JACS_AnneRavn_1
_cod_database_code               4128548
_shelx_shelxl_version_number     2016/6
_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_max   0.952
_shelx_estimated_absorpt_t_min   0.907
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00Q(H00Q)
2.b Secondary CH2 refined with riding coordinates:
 C00L(H00G,H00H), C00P(H00J,H00L)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F),
 C00I(H00I), C00K(H00K), C00M(H00M), C00R(H00R), C00S(H00S), C00T(H00T),
 C00U(H00U), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z)
2.d Idealised Me refined as rotating group:
 C00V(H00N,H00O,H00P)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Ni01 Ni 0.73996(3) 0.57502(2) 0.40490(2) 0.01353(8) Uani 1 1 d .
S002 S 0.75220(7) 0.60498(2) 0.10246(5) 0.01511(11) Uani 1 1 d .
O003 O 0.7504(2) 0.56360(4) 0.06155(15) 0.0195(3) Uani 1 1 d .
O004 O 0.9259(2) 0.62583(5) 0.09215(15) 0.0228(3) Uani 1 1 d .
N005 N 0.6596(2) 0.52062(5) 0.34481(16) 0.0141(3) Uani 1 1 d .
N006 N 0.6769(2) 0.60843(5) 0.24910(17) 0.0163(3) Uani 1 1 d .
N007 N 0.8264(2) 0.54953(5) 0.57442(17) 0.0154(3) Uani 1 1 d .
C008 C 0.7118(3) 0.49360(6) 0.4459(2) 0.0151(4) Uani 1 1 d .
C009 C 0.5821(3) 0.62926(6) -0.0141(2) 0.0157(4) Uani 1 1 d .
C00A C 0.3942(3) 0.62305(6) -0.0026(2) 0.0177(4) Uani 1 1 d .
H00A H 0.358314 0.606396 0.065911 0.021 Uiso 1 1 calc R
C00B C 0.6349(3) 0.65395(6) -0.1185(2) 0.0179(4) Uani 1 1 d .
H00B H 0.760376 0.657808 -0.127802 0.021 Uiso 1 1 calc R
C00C C 0.5630(3) 0.50719(6) 0.2293(2) 0.0177(4) Uani 1 1 d .
H00C H 0.522703 0.525276 0.160269 0.021 Uiso 1 1 calc R
C00D C 0.4996(3) 0.67269(6) -0.2083(2) 0.0200(4) Uani 1 1 d .
H00D H 0.535384 0.689306 -0.276944 0.024 Uiso 1 1 calc R
C00E C 0.2599(3) 0.64177(6) -0.0938(2) 0.0184(4) Uani 1 1 d .
H00E H 0.134432 0.637431 -0.085791 0.022 Uiso 1 1 calc R
C00F C 0.9119(3) 0.56513(6) 0.6906(2) 0.0175(4) Uani 1 1 d .
H00F H 0.927372 0.592489 0.695649 0.021 Uiso 1 1 calc R
C00G C 0.6750(3) 0.45266(6) 0.4338(2) 0.0179(4) Uani 1 1 d .
C00H C 0.3108(3) 0.66693(6) -0.1969(2) 0.0189(4) Uani 1 1 d .
C00I C 0.9792(3) 0.54219(6) 0.8054(2) 0.0192(4) Uani 1 1 d .
H00I H 1.037953 0.554338 0.884281 0.023 Uiso 1 1 calc R
C00J C 0.8047(3) 0.50910(6) 0.5706(2) 0.0147(4) Uani 1 1 d .
C00K C 0.5767(3) 0.43959(6) 0.3083(2) 0.0198(4) Uani 1 1 d .
H00K H 0.551055 0.412789 0.293906 0.024 Uiso 1 1 calc R
C00L C 0.7916(3) 0.62821(6) 0.4654(2) 0.0192(4) Uani 1 1 d .
H00G H 0.720174 0.636258 0.539476 0.023 Uiso 1 1 calc R
H00H H 0.923175 0.633026 0.491269 0.023 Uiso 1 1 calc R
C00M C 0.9584(3) 0.50179(7) 0.8012(2) 0.0206(4) Uani 1 1 d .
H00M H 1.004128 0.486296 0.876490 0.025 Uiso 1 1 calc R
C00N C 0.5690(3) 0.70934(6) 0.4126(2) 0.0219(4) Uani 1 1 d .
C00O C 0.8671(3) 0.48407(6) 0.6817(2) 0.0180(4) Uani 1 1 d .
C00P C 0.5464(3) 0.67182(6) 0.3269(2) 0.0246(5) Uani 1 1 d .
H00J H 0.504005 0.679087 0.232175 0.030 Uiso 1 1 calc R
H00L H 0.449522 0.655828 0.360870 0.030 Uiso 1 1 calc R
C00Q C 0.7202(3) 0.64648(6) 0.3267(2) 0.0186(4) Uani 1 1 d .
H00Q H 0.819293 0.661134 0.287768 0.022 Uiso 1 1 calc R
C00R C 0.4115(3) 0.73094(7) 0.4365(2) 0.0260(5) Uani 1 1 d .
H00R H 0.295034 0.722485 0.397210 0.031 Uiso 1 1 calc R
C00S C 0.8320(3) 0.44213(6) 0.6658(2) 0.0209(4) Uani 1 1 d .
H00S H 0.874197 0.424892 0.737072 0.025 Uiso 1 1 calc R
C00T C 0.5195(3) 0.46691(6) 0.2077(2) 0.0200(4) Uani 1 1 d .
H00T H 0.452179 0.458762 0.125538 0.024 Uiso 1 1 calc R
C00U C 0.7418(4) 0.72326(6) 0.4715(2) 0.0271(5) Uani 1 1 d .
H00U H 0.849278 0.709518 0.456394 0.033 Uiso 1 1 calc R
C00V C 0.1633(3) 0.68882(7) -0.2894(2) 0.0263(5) Uani 1 1 d .
H00N H 0.167459 0.716507 -0.266254 0.039 Uiso 1 1 calc GR
H00O H 0.042861 0.678337 -0.276647 0.039 Uiso 1 1 calc GR
H00P H 0.185684 0.685545 -0.384221 0.039 Uiso 1 1 calc GR
C00W C 0.7386(3) 0.42751(6) 0.5483(2) 0.0207(4) Uani 1 1 d .
H00W H 0.714889 0.400428 0.541763 0.025 Uiso 1 1 calc R
C00X C 0.4251(4) 0.76493(7) 0.5179(2) 0.0320(6) Uani 1 1 d .
H00X H 0.318121 0.778828 0.533306 0.038 Uiso 1 1 calc R
C00Y C 0.7557(4) 0.75741(7) 0.5525(3) 0.0326(5) Uani 1 1 d .
H00Y H 0.871910 0.766269 0.590810 0.039 Uiso 1 1 calc R
C00Z C 0.5977(4) 0.77814(7) 0.5762(2) 0.0336(6) Uani 1 1 d .
H00Z H 0.606982 0.800815 0.630942 0.040 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 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3147 0.7232 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.0826 0.0763 '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
N006 Ni01 N005 105.96(7)
N006 Ni01 C00L 73.22(8)
N007 Ni01 N005 84.02(7)
N007 Ni01 N006 169.87(7)
N007 Ni01 C00L 97.03(8)
C00L Ni01 N005 174.24(8)
O003 S002 O004 115.38(9)
O003 S002 N006 108.88(9)
O003 S002 C009 106.46(9)
O004 S002 N006 114.31(9)
O004 S002 C009 105.99(9)
N006 S002 C009 104.94(9)
C008 N005 Ni01 110.82(13)
C00C N005 Ni01 131.90(14)
C00C N005 C008 117.24(17)
S002 N006 Ni01 126.65(10)
C00Q N006 Ni01 94.98(11)
C00Q N006 S002 116.16(13)
C00F N007 Ni01 129.28(14)
C00F N007 C00J 117.09(17)
C00J N007 Ni01 113.52(13)
N005 C008 C00G 124.11(19)
N005 C008 C00J 115.94(17)
C00G C008 C00J 119.93(18)
C00A C009 S002 119.50(15)
C00A C009 C00B 119.69(18)
C00B C009 S002 120.80(16)
C009 C00A C00E 119.94(18)
C00D C00B C009 119.83(19)
N005 C00C C00T 122.81(19)
C00B C00D C00H 120.92(19)
C00A C00E C00H 120.90(19)
N007 C00F C00I 123.03(19)
C008 C00G C00K 116.72(19)
C008 C00G C00W 118.27(19)
C00K C00G C00W 125.01(19)
C00D C00H C00V 121.15(19)
C00E C00H C00D 118.71(19)
C00E C00H C00V 120.1(2)
C00M C00I C00F 119.86(19)
N007 C00J C008 115.53(17)
N007 C00J C00O 123.30(18)
C00O C00J C008 121.16(18)
C00T C00K C00G 119.29(19)
C00Q C00L Ni01 94.08(12)
C00I C00M C00O 119.15(19)
C00R C00N C00P 119.2(2)
C00R C00N C00U 117.8(2)
C00U C00N C00P 123.0(2)
C00J C00O C00S 117.93(19)
C00M C00O C00J 117.56(19)
C00M C00O C00S 124.51(19)
C00N C00P C00Q 115.55(19)
N006 C00Q C00L 97.55(15)
N006 C00Q C00P 110.72(17)
C00P C00Q C00L 115.25(18)
C00X C00R C00N 121.2(2)
C00W C00S C00O 120.85(19)
C00K C00T C00C 119.78(19)
C00Y C00U C00N 121.0(2)
C00S C00W C00G 121.80(19)
C00Z C00X C00R 120.1(2)
C00Z C00Y C00U 120.3(2)
C00Y C00Z C00X 119.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ni01 N005 1.9921(17)
Ni01 N006 1.9032(17)
Ni01 N007 1.9031(17)
Ni01 C00L 1.912(2)
S002 O003 1.4508(15)
S002 O004 1.4515(15)
S002 N006 1.5861(17)
S002 C009 1.778(2)
N005 C008 1.363(2)
N005 C00C 1.335(3)
N006 C00Q 1.504(2)
N007 C00F 1.335(3)
N007 C00J 1.372(2)
C008 C00G 1.408(3)
C008 C00J 1.420(3)
C009 C00A 1.390(3)
C009 C00B 1.399(3)
C00A C00E 1.392(3)
C00B C00D 1.390(3)
C00C C00T 1.405(3)
C00D C00H 1.394(3)
C00E C00H 1.394(3)
C00F C00I 1.401(3)
C00G C00K 1.414(3)
C00G C00W 1.435(3)
C00H C00V 1.510(3)
C00I C00M 1.371(3)
C00J C00O 1.406(3)
C00K C00T 1.374(3)
C00L C00Q 1.521(3)
C00M C00O 1.405(3)
C00N C00P 1.514(3)
C00N C00R 1.392(3)
C00N C00U 1.397(3)
C00O C00S 1.442(3)
C00P C00Q 1.519(3)
C00R C00X 1.391(3)
C00S C00W 1.354(3)
C00U C00Y 1.393(3)
C00X C00Z 1.386(4)
C00Y C00Z 1.380(4)
