#------------------------------------------------------------------------------
#$Date: 2020-05-20 02:19:28 +0300 (Wed, 20 May 2020) $
#$Revision: 252185 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038396.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_4038396
loop_
_publ_author_name
'Balamurugan, Gunasekaran'
'Ramesh, Rengan'
'Malecki, Jan Grzegorz'
_publ_section_title
;
 Nickel(II) - NɅNɅO Pincer Type Complexes Catalyzed
 N-alkylation of Amines with Alcohols via Hydrogen Auto Transfer Reaction.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00530
_journal_year                    2020
_chemical_formula_moiety         'C31 H26 N3 Ni O P, C2 H6 O'
_chemical_formula_sum            'C33 H32 N3 Ni O2 P'
_chemical_formula_weight         592.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.687(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.6292(11)
_cell_length_b                   12.8456(8)
_cell_length_c                   25.5273(14)
_cell_measurement_reflns_used    5398
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.6520
_cell_measurement_theta_min      3.9770
_cell_volume                     5851.5(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -79.00 -54.00   1.00  144.98    --    9.75-179.00  60.00   25
  2  ω    -84.00 -18.00   1.00  144.98    --  -11.93 -38.00 -90.00   66
  3  ω    -92.00  19.00   1.00  144.98    --  -11.93 -19.00 -30.00  111
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0057337000
_diffrn_orient_matrix_UB_12      0.0156958000
_diffrn_orient_matrix_UB_13      -0.0251327000
_diffrn_orient_matrix_UB_21      -0.0379777000
_diffrn_orient_matrix_UB_22      0.0158401000
_diffrn_orient_matrix_UB_23      -0.0096327000
_diffrn_orient_matrix_UB_31      0.0101150000
_diffrn_orient_matrix_UB_32      0.0505713000
_diffrn_orient_matrix_UB_33      0.0108097000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15386
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.476
_diffrn_reflns_theta_min         3.457
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       prism
_exptl_crystal_F_000             2480
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         6938
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0452
_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)+(0.0623P)²+1.9156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1299
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5149
_reflns_number_total             6938
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00530_si_002.cif
_cod_data_source_block           nipyp1
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               4038396
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C31 H28 N3 Ni1 O1 P1'
_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.
;
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, All O(H) groups
2.a Riding coordinates:
 O2(H2A), C32(H32A,H32B,H32C), C33(H33A,H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23),
  C24(H24), C25(H25), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.928
_oxdiff_exptl_absorpt_empirical_full_min 0.799
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.79064(2) 0.38075(2) 0.60446(2) 0.04421(12) Uani 1 1 d . . . . .
P1 P 0.87837(3) 0.45367(5) 0.67142(2) 0.04280(16) Uani 1 1 d . . . . .
O1 O 0.74555(9) 0.50538(12) 0.57608(6) 0.0482(4) Uani 1 1 d . . . . .
N1 N 0.81537(12) 0.23948(16) 0.61962(9) 0.0545(5) Uani 1 1 d . . . . .
N2 N 0.70953(11) 0.32549(17) 0.55195(8) 0.0501(5) Uani 1 1 d . . . . .
N3 N 0.65879(12) 0.39572(17) 0.52014(8) 0.0546(5) Uani 1 1 d . . . . .
C1 C 0.76231(16) 0.1733(2) 0.58664(11) 0.0568(6) Uani 1 1 d . . . . .
C2 C 0.78409(19) 0.0711(2) 0.59904(14) 0.0744(9) Uani 1 1 d . . . . .
H2 H 0.758686 0.011700 0.582788 0.089 Uiso 1 1 calc R . . . .
C3 C 0.8512(2) 0.0745(2) 0.64043(16) 0.0827(9) Uani 1 1 d . . . . .
H3 H 0.879125 0.017428 0.657293 0.099 Uiso 1 1 calc R . . . .
C4 C 0.86901(18) 0.1773(2) 0.65206(13) 0.0673(7) Uani 1 1 d . . . . .
H4 H 0.911582 0.200943 0.678306 0.081 Uiso 1 1 calc R . . . .
C5 C 0.70161(15) 0.2255(2) 0.54838(11) 0.0557(6) Uani 1 1 d . . . . .
C6 C 0.63661(17) 0.1730(3) 0.50936(13) 0.0741(8) Uani 1 1 d . . . . .
H6A H 0.595368 0.220804 0.498480 0.111 Uiso 1 1 calc GR . . . .
H6B H 0.622076 0.113627 0.526751 0.111 Uiso 1 1 calc GR . . . .
H6C H 0.650502 0.150818 0.477696 0.111 Uiso 1 1 calc GR . . . .
C7 C 0.68384(13) 0.4881(2) 0.53674(9) 0.0481(5) Uani 1 1 d . . . . .
C8 C 0.63983(13) 0.5808(2) 0.51124(9) 0.0493(6) Uani 1 1 d . . . . .
C9 C 0.67017(16) 0.6787(2) 0.52224(11) 0.0617(7) Uani 1 1 d . . . . .
H9 H 0.718581 0.686837 0.545245 0.074 Uiso 1 1 calc R . . . .
C10 C 0.62870(18) 0.7657(3) 0.49907(13) 0.0743(8) Uani 1 1 d . . . . .
H10 H 0.649839 0.831663 0.505898 0.089 Uiso 1 1 calc R . . . .
C11 C 0.5567(2) 0.7543(3) 0.46616(13) 0.0828(10) Uani 1 1 d . . . . .
H11 H 0.528734 0.812548 0.451028 0.099 Uiso 1 1 calc R . . . .
C12 C 0.52610(18) 0.6570(3) 0.45567(12) 0.0780(9) Uani 1 1 d . . . . .
H12 H 0.477086 0.649407 0.433632 0.094 Uiso 1 1 calc R . . . .
C13 C 0.56731(15) 0.5703(2) 0.47749(10) 0.0615(7) Uani 1 1 d . . . . .
H13 H 0.546358 0.504406 0.469520 0.074 Uiso 1 1 calc R . . . .
C14 C 0.86213(13) 0.59049(19) 0.68321(10) 0.0480(5) Uani 1 1 d . . . . .
C15 C 0.85422(15) 0.6605(2) 0.64036(11) 0.0559(6) Uani 1 1 d . . . . .
H15 H 0.857735 0.637187 0.606694 0.067 Uiso 1 1 calc R . . . .
C16 C 0.84117(17) 0.7646(2) 0.64769(13) 0.0684(8) Uani 1 1 d . . . . .
H16 H 0.836803 0.810992 0.618983 0.082 Uiso 1 1 calc R . . . .
C17 C 0.8346(2) 0.8003(2) 0.69638(16) 0.0802(9) Uani 1 1 d . . . . .
H17 H 0.824110 0.870058 0.700576 0.096 Uiso 1 1 calc R . . . .
C18 C 0.8436(2) 0.7324(3) 0.73887(15) 0.0923(11) Uani 1 1 d . . . . .
H18 H 0.840640 0.756806 0.772508 0.111 Uiso 1 1 calc R . . . .
C19 C 0.8569(2) 0.6278(2) 0.73264(12) 0.0737(9) Uani 1 1 d . . . . .
H19 H 0.862460 0.582449 0.761939 0.088 Uiso 1 1 calc R . . . .
C20 C 0.97285(13) 0.45102(19) 0.66491(10) 0.0487(5) Uani 1 1 d . . . . .
C21 C 1.02884(15) 0.5152(2) 0.69647(13) 0.0666(7) Uani 1 1 d . . . . .
H21 H 1.018001 0.560689 0.721519 0.080 Uiso 1 1 calc R . . . .
C22 C 1.09994(17) 0.5120(3) 0.69096(16) 0.0816(9) Uani 1 1 d . . . . .
H22 H 1.137180 0.554721 0.712422 0.098 Uiso 1 1 calc R . . . .
C23 C 1.11614(18) 0.4453(3) 0.65357(15) 0.0816(10) Uani 1 1 d . . . . .
H23 H 1.164314 0.443229 0.649798 0.098 Uiso 1 1 calc R . . . .
C24 C 1.06143(19) 0.3819(3) 0.62195(14) 0.0766(9) Uani 1 1 d . . . . .
H24 H 1.072347 0.337249 0.596613 0.092 Uiso 1 1 calc R . . . .
C25 C 0.99005(16) 0.3848(2) 0.62783(11) 0.0589(7) Uani 1 1 d . . . . .
H25 H 0.953140 0.341383 0.606500 0.071 Uiso 1 1 calc R . . . .
C26 C 0.88280(13) 0.39035(18) 0.73610(9) 0.0454(5) Uani 1 1 d . . . . .
C27 C 0.94776(15) 0.3514(2) 0.77137(11) 0.0616(7) Uani 1 1 d . . . . .
H27 H 0.993037 0.358776 0.763197 0.074 Uiso 1 1 calc R . . . .
C28 C 0.94567(18) 0.3013(3) 0.81906(12) 0.0765(9) Uani 1 1 d . . . . .
H28 H 0.989414 0.273501 0.842241 0.092 Uiso 1 1 calc R . . . .
C29 C 0.87957(19) 0.2925(3) 0.83228(12) 0.0727(8) Uani 1 1 d . . . . .
H29 H 0.878810 0.260554 0.864800 0.087 Uiso 1 1 calc R . . . .
C30 C 0.81495(16) 0.3308(2) 0.79764(12) 0.0658(7) Uani 1 1 d . . . . .
H30 H 0.770045 0.324858 0.806486 0.079 Uiso 1 1 calc R . . . .
C31 C 0.81636(15) 0.3780(2) 0.74961(11) 0.0572(6) Uani 1 1 d . . . . .
H31 H 0.771869 0.402195 0.725726 0.069 Uiso 1 1 calc R . . . .
O2 O 0.4994(11) 1.0146(10) 0.4333(6) 0.596(15) Uani 1 1 d . . . . .
H2A H 0.509613 0.964216 0.417044 0.894 Uiso 1 1 d R . . . .
C32 C 0.3892(10) 1.0806(11) 0.3839(5) 0.330(8) Uani 1 1 d . . . . .
H32A H 0.371142 1.036880 0.352374 0.495 Uiso 1 1 d R . . . .
H32B H 0.366942 1.148370 0.376294 0.495 Uiso 1 1 d R . . . .
H32C H 0.376052 1.050510 0.414334 0.495 Uiso 1 1 d R . . . .
C33 C 0.4673(10) 1.0909(13) 0.3954(13) 0.485(19) Uani 1 1 d . . . . .
H33A H 0.482791 1.083258 0.362430 0.582 Uiso 1 1 d R . . . .
H33B H 0.482861 1.159207 0.410710 0.582 Uiso 1 1 d 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'
P P 0.1023 0.0942 '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 P1 95.04(5) . . ?
O1 Ni1 N1 165.29(9) . . ?
N1 Ni1 P1 99.60(7) . . ?
N2 Ni1 P1 173.68(7) . . ?
N2 Ni1 O1 82.19(8) . . ?
N2 Ni1 N1 83.10(10) . . ?
C14 P1 Ni1 114.59(8) . . ?
C20 P1 Ni1 116.32(8) . . ?
C20 P1 C14 104.15(11) . . ?
C20 P1 C26 106.38(11) . . ?
C26 P1 Ni1 110.09(8) . . ?
C26 P1 C14 104.32(11) . . ?
C7 O1 Ni1 110.65(15) . . ?
C1 N1 Ni1 112.04(18) . . ?
C4 N1 Ni1 141.7(2) . . ?
C4 N1 C1 106.3(2) . . ?
N3 N2 Ni1 116.88(16) . . ?
C5 N2 Ni1 119.03(19) . . ?
C5 N2 N3 124.0(2) . . ?
C7 N3 N2 106.39(19) . . ?
N1 C1 C5 114.3(2) . . ?
C2 C1 N1 109.3(3) . . ?
C2 C1 C5 136.3(3) . . ?
C1 C2 C3 106.6(3) . . ?
C4 C3 C2 107.7(3) . . ?
N1 C4 C3 110.1(3) . . ?
N2 C5 C1 111.4(2) . . ?
N2 C5 C6 123.4(3) . . ?
C1 C5 C6 125.1(3) . . ?
O1 C7 C8 116.9(2) . . ?
N3 C7 O1 123.9(2) . . ?
N3 C7 C8 119.2(2) . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 C13 119.1(3) . . ?
C13 C8 C7 120.8(2) . . ?
C8 C9 C10 120.2(3) . . ?
C11 C10 C9 120.1(3) . . ?
C12 C11 C10 119.8(3) . . ?
C11 C12 C13 120.5(3) . . ?
C12 C13 C8 120.3(3) . . ?
C15 C14 P1 118.6(2) . . ?
C19 C14 P1 123.0(2) . . ?
C19 C14 C15 118.4(2) . . ?
C16 C15 C14 120.2(3) . . ?
C17 C16 C15 121.0(3) . . ?
C16 C17 C18 119.2(3) . . ?
C17 C18 C19 120.9(3) . . ?
C14 C19 C18 120.3(3) . . ?
C21 C20 P1 121.4(2) . . ?
C25 C20 P1 119.83(19) . . ?
C25 C20 C21 118.7(2) . . ?
C22 C21 C20 120.5(3) . . ?
C21 C22 C23 120.0(3) . . ?
C24 C23 C22 120.2(3) . . ?
C23 C24 C25 119.8(3) . . ?
C20 C25 C24 120.8(3) . . ?
C27 C26 P1 123.85(19) . . ?
C27 C26 C31 118.4(2) . . ?
C31 C26 P1 117.74(18) . . ?
C26 C27 C28 120.1(3) . . ?
C29 C28 C27 120.5(3) . . ?
C30 C29 C28 119.9(3) . . ?
C29 C30 C31 119.8(3) . . ?
C30 C31 C26 121.3(2) . . ?
O2 C33 C32 106.9(17) . . ?
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 P1 2.2057(7) . ?
Ni1 O1 1.8558(16) . ?
Ni1 N1 1.885(2) . ?
Ni1 N2 1.850(2) . ?
P1 C14 1.823(3) . ?
P1 C20 1.815(2) . ?
P1 C26 1.821(2) . ?
O1 C7 1.310(3) . ?
N1 C1 1.389(3) . ?
N1 C4 1.359(4) . ?
N2 N3 1.388(3) . ?
N2 C5 1.293(3) . ?
N3 C7 1.301(3) . ?
C1 C2 1.384(4) . ?
C1 C5 1.431(4) . ?
C2 C3 1.387(4) . ?
C3 C4 1.373(4) . ?
C5 C6 1.490(4) . ?
C7 C8 1.485(4) . ?
C8 C9 1.375(4) . ?
C8 C13 1.385(3) . ?
C9 C10 1.390(4) . ?
C10 C11 1.371(5) . ?
C11 C12 1.367(5) . ?
C12 C13 1.377(4) . ?
C14 C15 1.391(4) . ?
C14 C19 1.379(4) . ?
C15 C16 1.381(4) . ?
C16 C17 1.363(4) . ?
C17 C18 1.364(5) . ?
C18 C19 1.385(4) . ?
C20 C21 1.391(4) . ?
C20 C25 1.377(4) . ?
C21 C22 1.372(4) . ?
C22 C23 1.379(5) . ?
C23 C24 1.371(5) . ?
C24 C25 1.381(4) . ?
C26 C27 1.378(3) . ?
C26 C31 1.386(3) . ?
C27 C28 1.388(4) . ?
C28 C29 1.372(4) . ?
C29 C30 1.364(4) . ?
C30 C31 1.375(4) . ?
O2 C33 1.39(2) . ?
C32 C33 1.406(17) . ?
