#------------------------------------------------------------------------------
#$Date: 2016-03-26 01:53:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180113 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/11/7101195.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_7101195
loop_
_publ_author_name
'Dirk Walther'
'Reinald Fischer'
'Helmar Gorls'
'Jens Langer'
'Astrid Malassa'
'Gavin Vaughan'
_publ_section_title
;
A Key Step of the Formation of Acrylic Acid from CO₂ and
Ethylene: The Transformation of a Nickelalactone into a
Nickel-acrylate Complex
;
_journal_issue                   23
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/b603540j
_journal_year                    2006
_chemical_formula_sum            'C19 H22 N2 Ni O3'
_chemical_formula_weight         385.10
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.718(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6500(3)
_cell_length_b                   14.8065(6)
_cell_length_c                   13.6843(6)
_cell_measurement_temperature    183(2)
_cell_volume                     1740.60(12)
_computing_cell_refinement       DENZO
_computing_data_collection       COLLECT
_computing_data_reduction        DENZO
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_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  0.0754
_diffrn_reflns_av_sigmaI/netI    0.0957
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6956
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         4.04
_exptl_absorpt_coefficient_mu    1.135
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.058
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3972
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0631
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0927P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1531
_refine_ls_wR_factor_ref         0.1722
_reflns_number_gt                2775
_reflns_number_total             3972
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b603540j.txt
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'NONE' changed to 'none' according
to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7101195
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ni Ni 0.11756(5) 0.60347(3) 0.75258(3) 0.02650(19) Uani 1 1 d .
O1 O -0.0697(3) 0.6617(2) 0.76349(19) 0.0342(6) Uani 1 1 d .
O2 O -0.3031(3) 0.6972(3) 0.6888(2) 0.0525(9) Uani 1 1 d .
N1 N 0.3034(3) 0.5333(2) 0.7495(2) 0.0298(7) Uani 1 1 d .
N2 N 0.1677(3) 0.5930(2) 0.8989(2) 0.0282(7) Uani 1 1 d .
C1 C 0.0415(5) 0.5944(3) 0.6145(3) 0.0323(8) Uani 1 1 d .
H1A H 0.0817 0.6449 0.5773 0.039 Uiso 1 1 calc R
H1B H 0.0752 0.5367 0.5870 0.039 Uiso 1 1 calc R
C2 C -0.1348(5) 0.5985(3) 0.6079(3) 0.0393(9) Uani 1 1 d .
H2A H -0.1783 0.6240 0.5437 0.047 Uiso 1 1 calc R
H2B H -0.1777 0.5370 0.6137 0.047 Uiso 1 1 calc R
C3 C -0.1777(5) 0.6570(3) 0.6903(3) 0.0343(9) Uani 1 1 d .
C4 C 0.3951(4) 0.5164(3) 0.6786(3) 0.0340(9) Uani 1 1 d .
C5 C 0.4999(5) 0.4433(3) 0.6882(3) 0.0419(10) Uani 1 1 d .
H5A H 0.5623 0.4315 0.6369 0.050 Uiso 1 1 calc R
C6 C 0.5140(5) 0.3892(3) 0.7689(4) 0.0433(10) Uani 1 1 d .
H6A H 0.5818 0.3386 0.7725 0.052 Uiso 1 1 calc R
C7 C 0.4276(5) 0.4087(3) 0.8471(3) 0.0365(9) Uani 1 1 d .
C8 C 0.4405(5) 0.3611(3) 0.9387(4) 0.0442(11) Uani 1 1 d .
H8A H 0.5046 0.3089 0.9469 0.053 Uiso 1 1 calc R
C9 C 0.3634(5) 0.3888(3) 1.0140(4) 0.0442(11) Uani 1 1 d .
H9A H 0.3715 0.3546 1.0731 0.053 Uiso 1 1 calc R
C10 C 0.2696(5) 0.4691(3) 1.0055(3) 0.0376(9) Uani 1 1 d .
C11 C 0.1978(5) 0.5075(3) 1.0822(3) 0.0436(11) Uani 1 1 d .
H11A H 0.2006 0.4772 1.1436 0.052 Uiso 1 1 calc R
C12 C 0.1238(5) 0.5889(3) 1.0682(3) 0.0406(10) Uani 1 1 d .
H12A H 0.0810 0.6170 1.1214 0.049 Uiso 1 1 calc R
C13 C 0.1103(4) 0.6315(3) 0.9748(3) 0.0330(9) Uani 1 1 d .
C14 C 0.2495(4) 0.5144(3) 0.9148(3) 0.0293(8) Uani 1 1 d .
C15 C 0.3266(4) 0.4834(3) 0.8352(3) 0.0305(8) Uani 1 1 d .
C16 C 0.3912(5) 0.5770(3) 0.5912(3) 0.0420(10) Uani 1 1 d .
H16A H 0.3130 0.6243 0.5954 0.063 Uiso 1 1 calc R
H16B H 0.3642 0.5416 0.5310 0.063 Uiso 1 1 calc R
H16C H 0.4937 0.6047 0.5897 0.063 Uiso 1 1 calc R
C17 C 0.0344(5) 0.7225(3) 0.9624(3) 0.0387(9) Uani 1 1 d .
H17A H 0.0336 0.7425 0.8941 0.058 Uiso 1 1 calc R
H17B H 0.0927 0.7660 1.0064 0.058 Uiso 1 1 calc R
H17C H -0.0728 0.7185 0.9786 0.058 Uiso 1 1 calc R
O3 O -0.3243(4) 0.8126(3) 0.8486(3) 0.0660(11) Uani 1 1 d .
C18 C -0.4727(6) 0.8521(4) 0.8375(4) 0.0557(13) Uani 1 1 d .
H18A H -0.4758 0.8988 0.7855 0.067 Uiso 1 1 calc R
H18B H -0.4887 0.8830 0.8997 0.067 Uiso 1 1 calc R
C19 C -0.6003(6) 0.7901(5) 0.8124(6) 0.0780(19) Uani 1 1 d .
H19A H -0.6989 0.8233 0.8067 0.117 Uiso 1 1 calc R
H19B H -0.6002 0.7442 0.8641 0.117 Uiso 1 1 calc R
H19C H -0.5883 0.7607 0.7496 0.117 Uiso 1 1 calc R
H1O3 H -0.319(6) 0.774(5) 0.794(5) 0.064(17) Uiso 1 1 d .
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
O1 Ni N1 173.96(13)
O1 Ni C1 84.87(14)
N1 Ni C1 97.54(15)
O1 Ni N2 92.55(12)
N1 Ni N2 84.03(13)
C1 Ni N2 168.83(15)
C3 O1 Ni 118.2(2)
C4 N1 C15 118.3(3)
C4 N1 Ni 133.0(3)
C15 N1 Ni 108.1(2)
C13 N2 C14 118.4(3)
C13 N2 Ni 133.6(3)
C14 N2 Ni 105.8(2)
C2 C1 Ni 106.2(3)
C3 C2 C1 108.3(3)
O2 C3 O1 122.8(4)
O2 C3 C2 124.0(3)
O1 C3 C2 113.2(3)
N1 C4 C5 120.2(4)
N1 C4 C16 120.4(4)
C5 C4 C16 119.4(4)
C6 C5 C4 121.6(4)
C5 C6 C7 119.6(4)
C6 C7 C15 116.9(4)
C6 C7 C8 124.9(4)
C15 C7 C8 118.1(4)
C9 C8 C7 121.5(4)
C8 C9 C10 120.8(4)
C11 C10 C14 116.7(4)
C11 C10 C9 124.8(4)
C14 C10 C9 118.5(4)
C12 C11 C10 119.6(4)
C11 C12 C13 120.4(4)
N2 C13 C12 120.9(4)
N2 C13 C17 119.7(3)
C12 C13 C17 119.4(4)
N2 C14 C10 123.7(4)
N2 C14 C15 115.8(3)
C10 C14 C15 120.3(4)
N1 C15 C7 123.0(4)
N1 C15 C14 116.4(3)
C7 C15 C14 120.5(4)
O3 C18 C19 115.1(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ni O1 1.857(3)
Ni N1 1.919(3)
Ni C1 1.932(4)
Ni N2 2.005(3)
O1 C3 1.289(4)
O2 C3 1.236(5)
N1 C4 1.347(5)
N1 C15 1.380(5)
N2 C13 1.330(5)
N2 C14 1.367(5)
C1 C2 1.518(6)
C2 C3 1.502(6)
C4 C5 1.408(6)
C4 C16 1.493(6)
C5 C6 1.358(7)
C6 C7 1.404(7)
C7 C15 1.408(5)
C7 C8 1.431(6)
C8 C9 1.355(7)
C9 C10 1.437(6)
C10 C11 1.401(7)
C10 C14 1.404(5)
C11 C12 1.368(7)
C12 C13 1.419(6)
C13 C17 1.499(6)
C14 C15 1.418(5)
O3 C18 1.403(6)
C18 C19 1.446(8)
