#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/32/38/4323875.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_4323875
loop_
_publ_author_name
'Zhong Zhang'
'Jeffrey L. Petersen'
'Alan M. Stolzenberg'
_publ_section_title
;
 F430 Model Chemistry. A Reexamination of the
 [1,4,7,10,13-Pentaazacyclohexadecane-14,16-dionato(2-)]nickel(II)-Induced
 Formation of Methane from Methyl Coenzyme-M
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4649
_journal_page_last               4655
_journal_paper_doi               10.1021/ic960263n
_journal_volume                  35
_journal_year                    1996
_chemical_formula_sum            'C9 H18 N4 O2'
_chemical_formula_weight         214.27
_chemical_name_systematic
;
 1,4,7,10-tetraazacyclotridecane-11,13-dione
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                69.11(3)
_cell_angle_beta                 83.51(3)
_cell_angle_gamma                62.49(3)
_cell_formula_units_Z            2
_cell_length_a                   8.658(2)
_cell_length_b                   8.663(2)
_cell_length_c                   8.888(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      15.0
_cell_measurement_theta_min      9.50
_cell_volume                     551.3(3)
_computing_data_collection       'XSCANS 2.0'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '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  0.0159
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1998
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.46
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.094
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.055
_refine_ls_goodness_of_fit_obs   1.134
_refine_ls_hydrogen_treatment    'riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         1683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_restrained_S_obs      1.134
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_obs          0.0452
_refine_ls_shift/esd_max         0.018
_refine_ls_shift/esd_mean        0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0523P)²+0.0885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1225
_refine_ls_wR_factor_obs         0.1051
_reflns_number_observed          1277
_reflns_number_total             1861
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic960263n_2.cif
_cod_data_source_block           zhanglig
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0523P)^2^+0.0885P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0523P)^2^+0.0885P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        551.3(2)
_cod_database_code               4323875
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
O1 O 0.1559(2) 0.0134(2) 0.9052(2) 0.0504(5) Uani 1 d . .
O2 O -0.2644(2) 0.5183(3) 0.5564(2) 0.0738(7) Uani 1 d . .
N1 N -0.4233(3) 0.1202(3) 0.6740(3) 0.0494(6) Uani 1 d . .
H1A H -0.5000(38) 0.1974(39) 0.5970(32) 0.064(9) Uiso 1 d . .
N2 N -0.0822(3) -0.1605(3) 0.7033(2) 0.0430(5) Uani 1 d . .
H2A H -0.1201(29) -0.0380(33) 0.6875(25) 0.041(7) Uiso 1 d . .
N3 N 0.1391(2) 0.0106(3) 0.6565(2) 0.0425(5) Uani 1 d . .
H3A H 0.1070(33) 0.0718(35) 0.5565(32) 0.056(8) Uiso 1 d . .
N4 N -0.2547(3) 0.2940(3) 0.7880(2) 0.0438(5) Uani 1 d . .
H4A H -0.1855(33) 0.2018(34) 0.8687(29) 0.047(7) Uiso 1 d . .
C1 C -0.3931(3) -0.0694(4) 0.7087(3) 0.0552(7) Uani 1 d . .
H1B H -0.4015(3) -0.0870(4) 0.6086(3) 0.066 Uiso 1 calc R .
H1C H -0.4824(3) -0.0907(4) 0.7763(3) 0.066 Uiso 1 calc R .
C2 C -0.2163(3) -0.2073(3) 0.7929(3) 0.0488(6) Uani 1 d . .
H2B H -0.2146(3) -0.2062(3) 0.9014(3) 0.059 Uiso 1 calc R .
H2C H -0.1922(3) -0.3310(3) 0.8005(3) 0.059 Uiso 1 calc R .
C3 C 0.0880(3) -0.2637(3) 0.7911(3) 0.0479(6) Uani 1 d . .
H3B H 0.1355(3) -0.3936(3) 0.8039(3) 0.057 Uiso 1 calc R .
H3C H 0.0749(3) -0.2542(3) 0.8978(3) 0.057 Uiso 1 calc R .
C4 C 0.2129(3) -0.1895(3) 0.7026(3) 0.0492(6) Uani 1 d . .
H4B H 0.3183(3) -0.2474(3) 0.7712(3) 0.059 Uiso 1 calc R .
H4C H 0.2450(3) -0.2232(3) 0.6065(3) 0.059 Uiso 1 calc R .
C5 C 0.1116(3) 0.0961(3) 0.7616(3) 0.0357(5) Uani 1 d . .
C6 C 0.0137(3) 0.3052(3) 0.6924(3) 0.0483(6) Uani 1 d . .
H6A H 0.0391(3) 0.3558(3) 0.7623(3) 0.058 Uiso 1 calc R .
H6B H 0.0568(3) 0.3473(3) 0.5879(3) 0.058 Uiso 1 calc R .
C7 C -0.1806(3) 0.3815(3) 0.6727(3) 0.0421(6) Uani 1 d . .
C8 C -0.4401(3) 0.3473(3) 0.7862(3) 0.0498(6) Uani 1 d . .
H8A H -0.4957(3) 0.4438(3) 0.6840(3) 0.060 Uiso 1 calc R .
H8B H -0.4909(3) 0.3979(3) 0.8713(3) 0.060 Uiso 1 calc R .
C9 C -0.4759(3) 0.1861(3) 0.8094(3) 0.0466(6) Uani 1 d . .
H9A H -0.4132(3) 0.0858(3) 0.9075(3) 0.056 Uiso 1 calc R .
H9B H -0.5996(3) 0.2238(3) 0.8217(3) 0.056 Uiso 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'
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
C9 N1 C1 115.0(2) . . ?
C3 N2 C2 113.8(2) . . ?
C5 N3 C4 123.3(2) . . ?
C7 N4 C8 123.7(2) . . ?
N1 C1 C2 111.2(2) . . ?
N2 C2 C1 109.9(2) . . ?
N2 C3 C4 111.0(2) . . ?
N3 C4 C3 112.7(2) . . ?
O1 C5 N3 123.1(2) . . ?
O1 C5 C6 121.8(2) . . ?
N3 C5 C6 115.0(2) . . ?
C7 C6 C5 114.5(2) . . ?
O2 C7 N4 122.8(2) . . ?
O2 C7 C6 120.6(2) . . ?
N4 C7 C6 116.6(2) . . ?
N4 C8 C9 112.1(2) . . ?
N1 C9 C8 111.6(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
O1 C5 1.222(2) . ?
O2 C7 1.225(3) . ?
N1 C9 1.451(3) . ?
N1 C1 1.457(3) . ?
N2 C3 1.458(3) . ?
N2 C2 1.463(3) . ?
N3 C5 1.327(3) . ?
N3 C4 1.453(3) . ?
N4 C7 1.335(3) . ?
N4 C8 1.451(3) . ?
C1 C2 1.504(4) . ?
C3 C4 1.513(4) . ?
C5 C6 1.511(3) . ?
C6 C7 1.502(3) . ?
C8 C9 1.507(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10465987
