#------------------------------------------------------------------------------
#$Date: 2023-12-22 17:07:40 +0200 (Fri, 22 Dec 2023) $
#$Revision: 288505 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/26/1512612.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_1512612
loop_
_publ_author_name
'Constantine A. Stewart'
'Diane A. Dickie'
'Richard A. Kemp'
_publ_section_title
;
 Investigation of metal cyclam complexes as potential catalysts for the
 production of dimethyl carbonate
;
_journal_name_full
;
Inorganica Chimica Acta
;
_journal_page_first              268
_journal_page_last               276
_journal_paper_doi               10.1016/j.ica.2012.03.025
_journal_volume                  392
_journal_year                    2012
_chemical_formula_sum            'C13 H31 N5 O2'
_chemical_formula_weight         289.43
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 103.233(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0173(5)
_cell_length_b                   8.9427(5)
_cell_length_c                   21.7369(13)
_cell_measurement_reflns_used    4492
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      21.41
_cell_measurement_theta_min      2.47
_cell_volume                     1706.30(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0701
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23335
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_correction_T_min  0.9685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chip
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3478
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0667
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1224P)²+0.1355P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1792
_refine_ls_wR_factor_ref         0.2176
_reflns_number_gt                1979
_reflns_number_total             3478
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2012-392-268-276-3.cif
_cod_data_source_block           rkdd74_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

data name '_iucr_refine_instruction_details' was replaced with
'_iucr_refine_instructions_details' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1512612
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.9473(2) 0.9106(2) 0.83133(10) 0.0432(5) Uani 1 1 d .
N2 N 0.7061(2) 1.0735(2) 0.88123(10) 0.0450(6) Uani 1 1 d .
N3 N 0.5445(3) 0.7930(3) 0.88698(11) 0.0498(6) Uani 1 1 d .
N4 N 0.8461(3) 0.6471(2) 0.89223(10) 0.0466(6) Uani 1 1 d .
N5 N 0.6972(3) 0.8975(4) 0.61112(15) 0.0894(10) Uani 1 1 d .
C1 C 1.0415(3) 1.0319(3) 0.86612(15) 0.0587(8) Uani 1 1 d .
H1A H 1.1200 1.0592 0.8428 0.070 Uiso 1 1 calc R
H1B H 1.0952 0.9929 0.9079 0.070 Uiso 1 1 calc R
C2 C 0.9563(3) 1.1729(3) 0.87641(16) 0.0636(8) Uani 1 1 d .
H2B H 1.0315 1.2482 0.8975 0.076 Uiso 1 1 calc R
H2C H 0.9051 1.2137 0.8346 0.076 Uiso 1 1 calc R
C3 C 0.8400(3) 1.1533(3) 0.91479(15) 0.0627(8) Uani 1 1 d .
H3B H 0.8864 1.0979 0.9539 0.075 Uiso 1 1 calc R
H3C H 0.8089 1.2529 0.9273 0.075 Uiso 1 1 calc R
C4 C 0.5913(3) 1.0528(3) 0.91968(13) 0.0588(8) Uani 1 1 d .
H4B H 0.5393 1.1490 0.9231 0.071 Uiso 1 1 calc R
H4C H 0.6425 1.0201 0.9628 0.071 Uiso 1 1 calc R
C5 C 0.4762(3) 0.9374(3) 0.88935(14) 0.0570(8) Uani 1 1 d .
H5A H 0.3959 0.9299 0.9136 0.068 Uiso 1 1 calc R
H5B H 0.4274 0.9698 0.8459 0.068 Uiso 1 1 calc R
C6 C 0.5562(4) 0.7032(3) 0.94469(14) 0.0655(8) Uani 1 1 d .
H6A H 0.4523 0.6769 0.9489 0.079 Uiso 1 1 calc R
H6B H 0.6043 0.7646 0.9818 0.079 Uiso 1 1 calc R
C7 C 0.6462(4) 0.5628(3) 0.94531(15) 0.0632(8) Uani 1 1 d .
H7A H 0.6040 0.5063 0.9061 0.076 Uiso 1 1 calc R
H7B H 0.6335 0.5004 0.9814 0.076 Uiso 1 1 calc R
C8 C 0.8149(3) 0.5876(3) 0.95046(13) 0.0581(8) Uani 1 1 d .
H8A H 0.8544 0.6582 0.9855 0.070 Uiso 1 1 calc R
H8B H 0.8695 0.4915 0.9608 0.070 Uiso 1 1 calc R
C9 C 1.0064(3) 0.6876(3) 0.89894(13) 0.0527(7) Uani 1 1 d .
H9A H 1.0698 0.5960 0.9053 0.063 Uiso 1 1 calc R
H9B H 1.0399 0.7522 0.9365 0.063 Uiso 1 1 calc R
C10 C 1.0282(3) 0.7684(3) 0.84144(14) 0.0551(7) Uani 1 1 d .
H10A H 1.1383 0.7869 0.8456 0.066 Uiso 1 1 calc R
H10B H 0.9922 0.7040 0.8040 0.066 Uiso 1 1 calc R
C11 C 0.9018(3) 0.9485(3) 0.76434(13) 0.0516(7) Uani 1 1 d .
H11A H 0.9854 0.9235 0.7435 0.062 Uiso 1 1 calc R
H11B H 0.8823 1.0574 0.7596 0.062 Uiso 1 1 calc R
C12 C 0.7587(3) 0.8632(3) 0.73256(12) 0.0472(7) Uani 1 1 d .
H12A H 0.7739 0.7555 0.7425 0.057 Uiso 1 1 calc R
H12B H 0.6723 0.8983 0.7498 0.057 Uiso 1 1 calc R
C13 C 0.7212(3) 0.8827(3) 0.66457(16) 0.0583(8) Uani 1 1 d .
O1S O 0.4101(2) 0.70258(19) 0.73805(8) 0.0565(6) Uani 1 1 d .
H1D H 0.3835 0.6722 0.7009 0.085 Uiso 1 1 d R
H1E H 0.3892 0.7972 0.7313 0.085 Uiso 1 1 d R
O2S O 0.6654(2) 0.50844(18) 0.77856(8) 0.0595(6) Uani 1 1 d .
H2D H 0.6050 0.5704 0.7716 0.089 Uiso 1 1 d R
H2E H 0.7177 0.5305 0.8186 0.089 Uiso 1 1 d R
H2A H 0.730(3) 0.983(3) 0.8740(10) 0.033(6) Uiso 1 1 d .
H4A H 0.788(3) 0.720(3) 0.8836(11) 0.037(7) Uiso 1 1 d .
H3A H 0.489(3) 0.736(3) 0.8582(13) 0.047(8) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C10 N1 C11 111.7(2)
C10 N1 C1 110.7(2)
C11 N1 C1 109.8(2)
C3 N2 C4 112.7(2)
C5 N3 C6 114.0(2)
C8 N4 C9 112.7(2)
N1 C1 C2 115.7(2)
C3 C2 C1 115.3(2)
N2 C3 C2 112.8(2)
N2 C4 C5 109.8(2)
N3 C5 C4 112.0(2)
N3 C6 C7 113.5(2)
C6 C7 C8 114.3(2)
N4 C8 C7 112.3(2)
N4 C9 C10 110.6(2)
N1 C10 C9 113.0(2)
N1 C11 C12 110.6(2)
C13 C12 C11 112.2(2)
N5 C13 C12 177.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C10 1.457(3)
N1 C11 1.460(3)
N1 C1 1.475(3)
N2 C3 1.447(4)
N2 C4 1.483(3)
N3 C5 1.437(4)
N3 C6 1.473(4)
N4 C8 1.458(4)
N4 C9 1.464(3)
N5 C13 1.140(4)
C1 C2 1.520(4)
C2 C3 1.493(4)
C4 C5 1.505(4)
C6 C7 1.493(4)
C7 C8 1.516(4)
C9 C10 1.495(4)
C11 C12 1.522(4)
C12 C13 1.449(4)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1S H1D N2 0.83 1.99 2.813(3) 168.9 2_646
O1S H1E O2S 0.87 1.95 2.822(2) 175.7 2_656
O2S H2D O1S 0.77 2.11 2.857(3) 166.5 .
O2S H2E N4 0.91 2.04 2.908(3) 159.8 .
N2 H2A N1 0.86(2) 2.44(2) 3.018(3) 125.4(19) .
N2 H2A N3 0.86(2) 2.45(2) 2.918(3) 115.0(19) .
N4 H4A N3 0.83(2) 2.31(2) 2.995(3) 140(2) .
N3 H3A O1S 0.87(3) 2.56(3) 3.287(3) 141(2) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C10 N1 C1 C2 -161.9(2)
C11 N1 C1 C2 74.3(3)
N1 C1 C2 C3 62.0(4)
C4 N2 C3 C2 179.5(2)
C1 C2 C3 N2 -72.0(3)
C3 N2 C4 C5 -165.5(2)
C6 N3 C5 C4 86.0(3)
N2 C4 C5 N3 63.1(3)
C5 N3 C6 C7 -172.0(2)
N3 C6 C7 C8 68.5(3)
C9 N4 C8 C7 173.4(2)
C6 C7 C8 N4 -72.2(3)
C8 N4 C9 C10 -171.6(2)
C11 N1 C10 C9 -150.1(2)
C1 N1 C10 C9 87.3(3)
N4 C9 C10 N1 63.4(3)
C10 N1 C11 C12 79.7(3)
C1 N1 C11 C12 -157.1(2)
N1 C11 C12 C13 -172.4(2)
C11 C12 C13 N5 41(8)
