#------------------------------------------------------------------------------
#$Date: 2021-07-05 21:10:28 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267227 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/27/1562757.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_1562757
loop_
_publ_author_name
'Gugkaeva, Zalina T.'
'Smol'yakov, Alexander F.'
'Maleev, Victor I.'
'Larionov, Vladimir A.'
_publ_section_title
;
 A general asymmetric synthesis of artificial aliphatic and
 perfluoroalkylated α-amino acids by Luche's cross-electrophile coupling
 reaction.
;
_journal_issue                   24
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5327
_journal_page_last               5332
_journal_paper_doi               10.1039/d1ob00805f
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H33 N3 Ni O3'
_chemical_formula_sum            'C31 H33 N3 Ni O3'
_chemical_formula_weight         554.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-11 deposited with the CCDC.	2021-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1084(4)
_cell_length_b                   12.8143(5)
_cell_length_c                   21.4068(9)
_cell_measurement_reflns_used    9887
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.45
_cell_measurement_theta_min      2.48
_cell_volume                     2772.87(19)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            50870
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.489
_diffrn_reflns_theta_min         1.852
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0839 before and 0.0547 after correction. The Ratio of minimum to maximum transmission is 0.8414. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       prism
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 3355 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         8450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0391P)²+0.6395P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0730
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                7907
_reflns_number_total             8450
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00805f2.cif
_cod_data_source_block           a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 1562756--1562757.cif.'
_cod_database_code               1562757
_shelxl_version_number           2014/6
_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.
;
_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:
 C2(H2), C4(H4), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.50641(2) 0.75172(2) 0.36258(2) 0.01756(6) Uani 1 1 d . . . . .
O1 O 0.55076(15) 0.76025(11) 0.44696(6) 0.0257(3) Uani 1 1 d . . . . .
O2 O 0.52213(17) 0.67766(11) 0.53797(6) 0.0278(3) Uani 1 1 d . . . . .
O3 O 0.56040(16) 0.78745(14) 0.18293(7) 0.0313(3) Uani 1 1 d . . . . .
N1 N 0.39334(15) 0.64512(12) 0.38496(7) 0.0165(3) Uani 1 1 d . . . . .
N2 N 0.46098(13) 0.74809(13) 0.27860(6) 0.0163(2) Uani 1 1 d . . . . .
N3 N 0.62672(16) 0.86511(13) 0.34249(7) 0.0221(3) Uani 1 1 d . . . . .
C1 C 0.5062(2) 0.68443(13) 0.48149(8) 0.0213(3) Uani 1 1 d . . . . .
C2 C 0.43381(18) 0.59906(14) 0.44532(8) 0.0179(3) Uani 1 1 d . . . . .
H2 H 0.3562 0.5750 0.4687 0.021 Uiso 1 1 calc R . . . .
C3 C 0.52751(18) 0.50699(14) 0.43134(8) 0.0196(3) Uani 1 1 d . . . . .
H3A H 0.4802 0.4567 0.4059 0.024 Uiso 1 1 calc R . . . .
H3B H 0.6010 0.5329 0.4067 0.024 Uiso 1 1 calc R . . . .
C4 C 0.5835(2) 0.45019(16) 0.48843(9) 0.0240(4) Uani 1 1 d . . . . .
H4 H 0.6399 0.4988 0.5117 0.029 Uiso 1 1 calc R . . . .
C5 C 0.6691(2) 0.3590(2) 0.46550(11) 0.0342(5) Uani 1 1 d . . . . .
H5A H 0.6136 0.3072 0.4464 0.051 Uiso 1 1 calc GR . . . .
H5B H 0.7151 0.3287 0.5003 0.051 Uiso 1 1 calc GR . . . .
H5C H 0.7321 0.3841 0.4355 0.051 Uiso 1 1 calc GR . . . .
C6 C 0.4757(3) 0.41059(18) 0.53183(11) 0.0359(5) Uani 1 1 d . . . . .
H6A H 0.4298 0.4688 0.5499 0.054 Uiso 1 1 calc GR . . . .
H6B H 0.5148 0.3694 0.5644 0.054 Uiso 1 1 calc GR . . . .
H6C H 0.4145 0.3685 0.5086 0.054 Uiso 1 1 calc GR . . . .
C7 C 0.28800(17) 0.61259(13) 0.35592(8) 0.0159(3) Uani 1 1 d . . . . .
C8 C 0.19619(17) 0.53751(14) 0.38768(8) 0.0162(3) Uani 1 1 d . . . . .
C9 C 0.0978(2) 0.57658(16) 0.42689(9) 0.0227(4) Uani 1 1 d . . . . .
H9 H 0.0880 0.6482 0.4323 0.027 Uiso 1 1 calc R . . . .
C10 C 0.0142(2) 0.50708(18) 0.45783(10) 0.0306(4) Uani 1 1 d . . . . .
H10 H -0.0520 0.5327 0.4838 0.037 Uiso 1 1 calc R . . . .
C11 C 0.0287(2) 0.39995(19) 0.45018(11) 0.0330(5) Uani 1 1 d . . . . .
H11 H -0.0267 0.3541 0.4714 0.040 Uiso 1 1 calc R . . . .
C12 C 0.1263(2) 0.36194(17) 0.41083(10) 0.0291(4) Uani 1 1 d . . . . .
H12 H 0.1357 0.2903 0.4054 0.035 Uiso 1 1 calc R . . . .
C13 C 0.21024(19) 0.42995(15) 0.37939(9) 0.0215(3) Uani 1 1 d . . . . .
H13 H 0.2754 0.4040 0.3530 0.026 Uiso 1 1 calc R . . . .
C14 C 0.25455(17) 0.64920(14) 0.29304(8) 0.0158(3) Uani 1 1 d . . . . .
C15 C 0.13023(18) 0.61868(15) 0.26842(9) 0.0214(4) Uani 1 1 d . . . . .
H15 H 0.0745 0.5779 0.2929 0.026 Uiso 1 1 calc R . . . .
C16 C 0.0893(2) 0.64748(18) 0.20951(9) 0.0264(4) Uani 1 1 d . . . . .
H16 H 0.0070 0.6269 0.1945 0.032 Uiso 1 1 calc R . . . .
C17 C 0.1734(2) 0.70795(17) 0.17298(9) 0.0247(4) Uani 1 1 d . . . . .
H17 H 0.1468 0.7279 0.1331 0.030 Uiso 1 1 calc R . . . .
C18 C 0.29572(17) 0.73873(15) 0.19495(8) 0.0202(3) Uani 1 1 d . . . . .
H18 H 0.3502 0.7787 0.1694 0.024 Uiso 1 1 calc R . . . .
C19 C 0.34028(17) 0.71113(13) 0.25529(8) 0.0154(3) Uani 1 1 d . . . . .
C20 C 0.55358(19) 0.79213(15) 0.24005(9) 0.0209(3) Uani 1 1 d . . . . .
C21 C 0.66187(19) 0.84975(16) 0.27516(9) 0.0223(4) Uani 1 1 d . . . . .
H21 H 0.6756 0.9181 0.2557 0.027 Uiso 1 1 calc R . . . .
C22 C 0.7946(2) 0.7886(2) 0.27463(11) 0.0326(5) Uani 1 1 d . . . . .
H22A H 0.7852 0.7230 0.2524 0.039 Uiso 1 1 calc R . . . .
H22B H 0.8639 0.8293 0.2550 0.039 Uiso 1 1 calc R . . . .
C23 C 0.8261(2) 0.7694(2) 0.34395(11) 0.0357(5) Uani 1 1 d . . . . .
H23A H 0.7910 0.7029 0.3579 0.043 Uiso 1 1 calc R . . . .
H23B H 0.9206 0.7711 0.3515 0.043 Uiso 1 1 calc R . . . .
C24 C 0.7572(2) 0.85930(19) 0.37598(10) 0.0308(5) Uani 1 1 d . . . . .
H24A H 0.7448 0.8453 0.4201 0.037 Uiso 1 1 calc R . . . .
H24B H 0.8068 0.9236 0.3712 0.037 Uiso 1 1 calc R . . . .
C25 C 0.5608(2) 0.96792(16) 0.35485(10) 0.0293(4) Uani 1 1 d . . . . .
H25A H 0.6127 1.0232 0.3359 0.035 Uiso 1 1 calc R . . . .
H25B H 0.5585 0.9802 0.3995 0.035 Uiso 1 1 calc R . . . .
C26 C 0.4214(2) 0.97223(15) 0.32941(10) 0.0268(4) Uani 1 1 d . . . . .
C27 C 0.3962(2) 1.00502(16) 0.26841(11) 0.0308(4) Uani 1 1 d . . . . .
H27 H 0.4645 1.0327 0.2444 0.037 Uiso 1 1 calc R . . . .
C28 C 0.2698(3) 0.99664(18) 0.24318(11) 0.0359(5) Uani 1 1 d . . . . .
H28 H 0.2543 1.0173 0.2022 0.043 Uiso 1 1 calc R . . . .
C29 C 0.1668(2) 0.95766(19) 0.27900(12) 0.0357(5) Uani 1 1 d . . . . .
H29 H 0.0828 0.9509 0.2618 0.043 Uiso 1 1 calc R . . . .
C30 C 0.1894(2) 0.92867(18) 0.34083(12) 0.0337(5) Uani 1 1 d . . . . .
H30 H 0.1200 0.9046 0.3654 0.040 Uiso 1 1 calc R . . . .
C31 C 0.3158(2) 0.93596(16) 0.36541(10) 0.0303(4) Uani 1 1 d . . . . .
H31 H 0.3306 0.9163 0.4067 0.036 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'
Ni Ni 0.3393 1.1124 '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'
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
_geom_angle_publ_flag
O1 Ni1 N3 91.15(6) . . ?
N1 Ni1 O1 86.60(6) . . ?
N1 Ni1 N2 94.57(6) . . ?
N1 Ni1 N3 177.73(6) . . ?
N2 Ni1 O1 178.04(7) . . ?
N2 Ni1 N3 87.67(7) . . ?
C1 O1 Ni1 115.05(12) . . ?
C2 N1 Ni1 110.56(11) . . ?
C7 N1 Ni1 128.33(12) . . ?
C7 N1 C2 121.06(15) . . ?
C19 N2 Ni1 124.69(11) . . ?
C20 N2 Ni1 113.84(11) . . ?
C20 N2 C19 121.33(14) . . ?
C21 N3 Ni1 105.26(11) . . ?
C21 N3 C24 104.15(16) . . ?
C21 N3 C25 113.00(16) . . ?
C24 N3 Ni1 113.99(13) . . ?
C25 N3 Ni1 109.87(13) . . ?
C25 N3 C24 110.44(17) . . ?
O1 C1 C2 114.37(15) . . ?
O2 C1 O1 124.70(17) . . ?
O2 C1 C2 120.90(16) . . ?
N1 C2 C1 106.85(14) . . ?
N1 C2 C3 107.81(14) . . ?
C1 C2 C3 110.61(15) . . ?
C4 C3 C2 115.84(15) . . ?
C3 C4 C5 108.36(16) . . ?
C6 C4 C3 112.47(18) . . ?
C6 C4 C5 110.23(18) . . ?
N1 C7 C8 119.69(15) . . ?
N1 C7 C14 121.67(15) . . ?
C14 C7 C8 118.63(15) . . ?
C9 C8 C7 118.94(16) . . ?
C9 C8 C13 120.22(17) . . ?
C13 C8 C7 120.83(16) . . ?
C8 C9 C10 119.26(18) . . ?
C11 C10 C9 120.67(19) . . ?
C12 C11 C10 119.62(19) . . ?
C11 C12 C13 120.6(2) . . ?
C12 C13 C8 119.68(18) . . ?
C15 C14 C7 117.24(15) . . ?
C15 C14 C19 118.79(16) . . ?
C19 C14 C7 123.96(15) . . ?
C16 C15 C14 122.19(18) . . ?
C15 C16 C17 118.69(18) . . ?
C18 C17 C16 121.01(17) . . ?
C17 C18 C19 121.70(17) . . ?
N2 C19 C14 121.03(15) . . ?
N2 C19 C18 121.25(15) . . ?
C18 C19 C14 117.62(15) . . ?
O3 C20 N2 128.26(18) . . ?
O3 C20 C21 118.46(17) . . ?
N2 C20 C21 113.24(15) . . ?
N3 C21 C20 111.66(15) . . ?
N3 C21 C22 106.16(16) . . ?
C20 C21 C22 111.92(17) . . ?
C23 C22 C21 104.61(18) . . ?
C24 C23 C22 102.76(19) . . ?
N3 C24 C23 103.05(17) . . ?
N3 C25 C26 112.49(16) . . ?
C27 C26 C25 121.2(2) . . ?
C27 C26 C31 118.5(2) . . ?
C31 C26 C25 120.11(19) . . ?
C28 C27 C26 120.5(2) . . ?
C29 C28 C27 120.2(2) . . ?
C28 C29 C30 119.9(2) . . ?
C31 C30 C29 119.6(2) . . ?
C30 C31 C26 121.2(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 1.8644(13) . ?
Ni1 N1 1.8444(15) . ?
Ni1 N2 1.8559(13) . ?
Ni1 N3 1.9430(16) . ?
O1 C1 1.301(2) . ?
O2 C1 1.223(2) . ?
O3 C20 1.226(2) . ?
N1 C2 1.478(2) . ?
N1 C7 1.302(2) . ?
N2 C19 1.401(2) . ?
N2 C20 1.370(2) . ?
N3 C21 1.497(2) . ?
N3 C24 1.503(3) . ?
N3 C25 1.500(3) . ?
C1 C2 1.527(2) . ?
C2 C3 1.542(3) . ?
C3 C4 1.531(3) . ?
C4 C5 1.534(3) . ?
C4 C6 1.519(3) . ?
C7 C8 1.500(2) . ?
C7 C14 1.465(2) . ?
C8 C9 1.394(2) . ?
C8 C13 1.397(3) . ?
C9 C10 1.395(3) . ?
C10 C11 1.390(3) . ?
C11 C12 1.386(3) . ?
C12 C13 1.390(3) . ?
C14 C15 1.418(2) . ?
C14 C19 1.426(2) . ?
C15 C16 1.378(3) . ?
C16 C17 1.391(3) . ?
C17 C18 1.380(3) . ?
C18 C19 1.413(2) . ?
C20 C21 1.519(3) . ?
C21 C22 1.554(3) . ?
C22 C23 1.537(3) . ?
C23 C24 1.510(4) . ?
C25 C26 1.511(3) . ?
C26 C27 1.395(3) . ?
C26 C31 1.397(3) . ?
C27 C28 1.392(4) . ?
C28 C29 1.386(4) . ?
C29 C30 1.394(4) . ?
C30 C31 1.385(3) . ?
