#------------------------------------------------------------------------------
#$Date: 2019-11-28 16:26:31 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244105 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/82/7238283.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_7238283
loop_
_publ_author_name
'Aakeröy, Christer B.'
'Desper, John'
'Haque, Naheed'
'Hussain, Izhar'
_publ_section_title
;
 Effective double-ended chelating agents: crystal structures of
 N,N,N′,N′-tetraacetyl diamino derivatives and their
 chelates
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              3218
_journal_paper_doi               10.1039/c004168h
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C16 H28 N2 O4'
_chemical_formula_sum            'C16 H28 N2 O4'
_chemical_formula_weight         312.40
_chemical_name_systematic
;
N,N,N',N'-tetraacetyl-1,8-diaminooctane
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_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                 110.9860(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.0183(5)
_cell_length_b                   4.54300(10)
_cell_length_c                   20.5970(5)
_cell_measurement_reflns_used    5541
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      67.70
_cell_measurement_theta_min      2.65
_cell_volume                     1748.91(7)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10247
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         1.22
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0424
_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)+(0.0700P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1408
_reflns_number_gt                2538
_reflns_number_total             2999
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c004168h.txt
_cod_data_source_block           ih0517(7)
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1748.90(7)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7238283
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
C11 C 0.63791(10) -0.0348(4) 0.37191(9) 0.0321(4) Uani 1 1 d .
H11A H 0.6654 -0.2013 0.3999 0.039 Uiso 1 1 calc R
H11B H 0.6005 -0.1172 0.3301 0.039 Uiso 1 1 calc R
N11 N 0.68645(7) 0.1522(3) 0.35007(7) 0.0289(3) Uani 1 1 d .
C12 C 0.60239(10) 0.1350(4) 0.41449(9) 0.0328(4) Uani 1 1 d .
H12A H 0.6398 0.2231 0.4555 0.039 Uiso 1 1 calc R
H12B H 0.5735 0.2974 0.3859 0.039 Uiso 1 1 calc R
C13 C 0.55436(9) -0.0608(4) 0.43894(9) 0.0307(4) Uani 1 1 d .
H13A H 0.5823 -0.2328 0.4637 0.037 Uiso 1 1 calc R
H13B H 0.5146 -0.1348 0.3978 0.037 Uiso 1 1 calc R
C14 C 0.52329(9) 0.0979(4) 0.48687(9) 0.0320(4) Uani 1 1 d .
H14A H 0.5631 0.1767 0.5273 0.048 Uiso 1 1 calc R
H14B H 0.4944 0.2670 0.4616 0.048 Uiso 1 1 calc R
C21 C 0.75714(10) 0.1698(5) 0.39710(9) 0.0385(5) Uani 1 1 d .
O21 O 0.77243(8) 0.0543(4) 0.45346(7) 0.0599(5) Uani 1 1 d .
C22 C 0.81267(10) 0.3188(6) 0.37580(10) 0.0518(6) Uani 1 1 d .
H22A H 0.8057 0.2654 0.3277 0.078 Uiso 1 1 calc R
H22B H 0.8604 0.2561 0.4065 0.078 Uiso 1 1 calc R
H22C H 0.8083 0.5326 0.3792 0.078 Uiso 1 1 calc R
C31 C 0.66057(10) 0.3160(4) 0.28841(9) 0.0339(4) Uani 1 1 d .
O31 O 0.69344(8) 0.5208(3) 0.27731(7) 0.0474(4) Uani 1 1 d .
C32 C 0.58909(11) 0.2306(6) 0.23652(11) 0.0534(6) Uani 1 1 d .
H32A H 0.5772 0.3593 0.1958 0.080 Uiso 1 1 calc R
H32B H 0.5525 0.2507 0.2576 0.080 Uiso 1 1 calc R
H32C H 0.5908 0.0258 0.2222 0.080 Uiso 1 1 calc R
C41 C 0.37726(10) 0.9952(4) 0.14289(9) 0.0310(4) Uani 1 1 d .
H41A H 0.4143 1.1173 0.1771 0.037 Uiso 1 1 calc R
H41B H 0.3392 1.1287 0.1137 0.037 Uiso 1 1 calc R
N41 N 0.34620(7) 0.7908(3) 0.18053(7) 0.0302(4) Uani 1 1 d .
C42 C 0.41070(9) 0.8362(4) 0.09677(9) 0.0308(4) Uani 1 1 d .
H42A H 0.4473 0.6962 0.1254 0.037 Uiso 1 1 calc R
H42B H 0.3733 0.7216 0.0610 0.037 Uiso 1 1 calc R
C43 C 0.44517(9) 1.0494(4) 0.06127(8) 0.0284(4) Uani 1 1 d .
H43A H 0.4817 1.1668 0.0972 0.034 Uiso 1 1 calc R
H43B H 0.4082 1.1870 0.0321 0.034 Uiso 1 1 calc R
C44 C 0.48030(9) 0.8959(4) 0.01587(8) 0.0285(4) Uani 1 1 d .
H44A H 0.5145 0.7474 0.0443 0.043 Uiso 1 1 calc R
H44B H 0.4430 0.7904 -0.0221 0.043 Uiso 1 1 calc R
C51 C 0.39467(10) 0.6827(4) 0.24399(9) 0.0343(4) Uani 1 1 d .
O51 O 0.45771(7) 0.7441(4) 0.26050(7) 0.0470(4) Uani 1 1 d .
C52 C 0.36820(12) 0.5068(5) 0.29157(10) 0.0452(5) Uani 1 1 d .
H52A H 0.3531 0.3115 0.2714 0.068 Uiso 1 1 calc R
H52B H 0.3275 0.6082 0.2974 0.068 Uiso 1 1 calc R
H52C H 0.4067 0.4857 0.3369 0.068 Uiso 1 1 calc R
C61 C 0.27541(10) 0.6925(4) 0.14974(9) 0.0354(4) Uani 1 1 d .
O61 O 0.25186(8) 0.4943(3) 0.17429(8) 0.0503(4) Uani 1 1 d .
C62 C 0.22901(11) 0.8411(5) 0.08378(10) 0.0475(5) Uani 1 1 d .
H62A H 0.1805 0.7593 0.0690 0.071 Uiso 1 1 calc R
H62B H 0.2490 0.8078 0.0473 0.071 Uiso 1 1 calc R
H62C H 0.2273 1.0529 0.0920 0.071 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'
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
N11 C11 C12 112.21(14) .
N11 C11 H11A 109.2 .
C12 C11 H11A 109.2 .
N11 C11 H11B 109.2 .
C12 C11 H11B 109.2 .
H11A C11 H11B 107.9 .
C31 N11 C21 123.37(15) .
C31 N11 C11 120.76(14) .
C21 N11 C11 115.70(14) .
C13 C12 C11 112.04(15) .
C13 C12 H12A 109.2 .
C11 C12 H12A 109.2 .
C13 C12 H12B 109.2 .
C11 C12 H12B 109.2 .
H12A C12 H12B 107.9 .
C12 C13 C14 113.00(14) .
C12 C13 H13A 109.0 .
C14 C13 H13A 109.0 .
C12 C13 H13B 109.0 .
C14 C13 H13B 109.0 .
H13A C13 H13B 107.8 .
C14 C14 C13 113.48(18) 3_656
C14 C14 H14A 108.9 3_656
C13 C14 H14A 108.9 .
C14 C14 H14B 108.9 3_656
C13 C14 H14B 108.9 .
H14A C14 H14B 107.7 .
O21 C21 N11 118.97(17) .
O21 C21 C22 121.27(18) .
N11 C21 C22 119.71(16) .
C21 C22 H22A 109.5 .
C21 C22 H22B 109.5 .
H22A C22 H22B 109.5 .
C21 C22 H22C 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
O31 C31 N11 122.06(17) .
O31 C31 C32 120.69(18) .
N11 C31 C32 117.24(17) .
C31 C32 H32A 109.5 .
C31 C32 H32B 109.5 .
H32A C32 H32B 109.5 .
C31 C32 H32C 109.5 .
H32A C32 H32C 109.5 .
H32B C32 H32C 109.5 .
N41 C41 C42 112.88(14) .
N41 C41 H41A 109.0 .
C42 C41 H41A 109.0 .
N41 C41 H41B 109.0 .
C42 C41 H41B 109.0 .
H41A C41 H41B 107.8 .
C61 N41 C51 123.90(15) .
C61 N41 C41 120.56(15) .
C51 N41 C41 115.18(14) .
C43 C42 C41 111.94(14) .
C43 C42 H42A 109.2 .
C41 C42 H42A 109.2 .
C43 C42 H42B 109.2 .
C41 C42 H42B 109.2 .
H42A C42 H42B 107.9 .
C42 C43 C44 113.09(14) .
C42 C43 H43A 109.0 .
C44 C43 H43A 109.0 .
C42 C43 H43B 109.0 .
C44 C43 H43B 109.0 .
H43A C43 H43B 107.8 .
C44 C44 C43 113.79(18) 3_675
C44 C44 H44A 108.8 3_675
C43 C44 H44A 108.8 .
C44 C44 H44B 108.8 3_675
C43 C44 H44B 108.8 .
H44A C44 H44B 107.7 .
O51 C51 N41 118.72(16) .
O51 C51 C52 120.90(17) .
N41 C51 C52 120.32(16) .
C51 C52 H52A 109.5 .
C51 C52 H52B 109.5 .
H52A C52 H52B 109.5 .
C51 C52 H52C 109.5 .
H52A C52 H52C 109.5 .
H52B C52 H52C 109.5 .
O61 C61 N41 122.04(18) .
O61 C61 C62 120.36(17) .
N41 C61 C62 117.59(17) .
C61 C62 H62A 109.5 .
C61 C62 H62B 109.5 .
H62A C62 H62B 109.5 .
C61 C62 H62C 109.5 .
H62A C62 H62C 109.5 .
H62B C62 H62C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C11 N11 1.477(2) .
C11 C12 1.522(2) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
N11 C31 1.401(2) .
N11 C21 1.402(2) .
C12 C13 1.522(2) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.523(2) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C14 1.521(3) 3_656
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C21 O21 1.209(2) .
C21 C22 1.495(3) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C31 O31 1.208(2) .
C31 C32 1.498(3) .
C32 H32A 0.9800 .
C32 H32B 0.9800 .
C32 H32C 0.9800 .
C41 N41 1.482(2) .
C41 C42 1.526(2) .
C41 H41A 0.9900 .
C41 H41B 0.9900 .
N41 C61 1.402(2) .
N41 C51 1.408(2) .
C42 C43 1.520(2) .
C42 H42A 0.9900 .
C42 H42B 0.9900 .
C43 C44 1.525(2) .
C43 H43A 0.9900 .
C43 H43B 0.9900 .
C44 C44 1.521(3) 3_675
C44 H44A 0.9900 .
C44 H44B 0.9900 .
C51 O51 1.216(2) .
C51 C52 1.501(3) .
C52 H52A 0.9800 .
C52 H52B 0.9800 .
C52 H52C 0.9800 .
C61 O61 1.208(2) .
C61 C62 1.503(3) .
C62 H62A 0.9800 .
C62 H62B 0.9800 .
C62 H62C 0.9800 .
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
_geom_torsion_site_symmetry_4
C12 C11 N11 C31 -87.29(19) .
C12 C11 N11 C21 88.16(19) .
N11 C11 C12 C13 -178.09(14) .
C11 C12 C13 C14 175.01(15) .
C12 C13 C14 C14 -178.52(18) 3_656
C31 N11 C21 O21 169.52(19) .
C11 N11 C21 O21 -5.8(3) .
C31 N11 C21 C22 -13.1(3) .
C11 N11 C21 C22 171.56(17) .
C21 N11 C31 O31 -13.3(3) .
C11 N11 C31 O31 161.79(16) .
C21 N11 C31 C32 167.77(18) .
C11 N11 C31 C32 -17.1(2) .
C42 C41 N41 C61 -87.67(19) .
C42 C41 N41 C51 85.69(18) .
N41 C41 C42 C43 -177.40(14) .
C41 C42 C43 C44 178.90(14) .
C42 C43 C44 C44 -175.80(17) 3_675
C61 N41 C51 O51 167.66(16) .
C41 N41 C51 O51 -5.4(2) .
C61 N41 C51 C52 -15.1(3) .
C41 N41 C51 C52 171.81(16) .
C51 N41 C61 O61 -3.9(3) .
C41 N41 C61 O61 168.87(16) .
C51 N41 C61 C62 176.76(16) .
C41 N41 C61 C62 -10.5(2) .
