#------------------------------------------------------------------------------
#$Date: 2019-11-28 16:26:31 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244105 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/82/7238276.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_7238276
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 H20 N2 O4'
_chemical_formula_sum            'C16 H20 N2 O4'
_chemical_formula_weight         304.34
_chemical_name_systematic
;
N,N,N',N'-tetraacetyl-a,a'-diamino-m-xylene
;
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 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                 101.320(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.3232(9)
_cell_length_b                   16.4424(11)
_cell_length_c                   13.4342(8)
_cell_measurement_reflns_used    3982
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.60
_cell_measurement_theta_min      2.25
_cell_volume                     3102.3(3)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.930
_diffrn_measured_fraction_theta_max 0.930
_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  0.0581
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11242
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0040(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3589
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0427
_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+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1182
_reflns_number_gt                2569
_reflns_number_total             3589
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c004168h.txt
_cod_data_source_block           ih0501m(1)
_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_sg_symbol_H-M      C2/c
_cod_database_code               7238276
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.07317(9) 0.64306(7) 0.31275(9) 0.0255(3) Uani 1 1 d .
C12 C 0.0000 0.68384(10) 0.2500 0.0251(4) Uani 1 2 d S
H12 H 0.0000 0.7416 0.2500 0.030 Uiso 1 2 calc SR
C15 C 0.0000 0.51702(10) 0.2500 0.0302(4) Uani 1 2 d S
H15 H 0.0000 0.4592 0.2500 0.036 Uiso 1 2 calc SR
C16 C 0.07263(9) 0.55849(7) 0.31247(9) 0.0285(3) Uani 1 1 d .
H16 H 0.1221 0.5293 0.3552 0.034 Uiso 1 1 calc R
C17 C 0.15379(9) 0.69162(7) 0.37387(10) 0.0293(3) Uani 1 1 d .
H17A H 0.2041 0.6981 0.3334 0.035 Uiso 1 1 calc R
H17B H 0.1300 0.7466 0.3859 0.035 Uiso 1 1 calc R
N17 N 0.19639(7) 0.65525(6) 0.47234(8) 0.0263(3) Uani 1 1 d .
C21 C 0.14397(10) 0.66776(8) 0.54945(10) 0.0328(3) Uani 1 1 d .
O21 O 0.07122(8) 0.70683(7) 0.52864(8) 0.0487(3) Uani 1 1 d .
C22 C 0.17727(12) 0.63426(10) 0.65332(11) 0.0459(4) Uani 1 1 d .
H22A H 0.1871 0.5755 0.6491 0.069 Uiso 1 1 calc R
H22B H 0.1293 0.6448 0.6946 0.069 Uiso 1 1 calc R
H22C H 0.2373 0.6604 0.6847 0.069 Uiso 1 1 calc R
C31 C 0.28229(10) 0.61272(8) 0.48463(11) 0.0329(3) Uani 1 1 d .
O31 O 0.32071(9) 0.58662(8) 0.56590(9) 0.0624(4) Uani 1 1 d .
C32 C 0.32575(11) 0.60188(9) 0.39322(13) 0.0438(4) Uani 1 1 d .
H32A H 0.3498 0.6543 0.3743 0.066 Uiso 1 1 calc R
H32B H 0.2775 0.5813 0.3368 0.066 Uiso 1 1 calc R
H32C H 0.3784 0.5630 0.4086 0.066 Uiso 1 1 calc R
C41 C 0.44037(9) 0.34275(7) 0.67234(9) 0.0255(3) Uani 1 1 d .
C42 C 0.5000 0.30168(10) 0.7500 0.0249(4) Uani 1 2 d S
H42 H 0.5000 0.2439 0.7500 0.030 Uiso 1 2 calc SR
C45 C 0.5000 0.46865(10) 0.7500 0.0279(4) Uani 1 2 d S
H45 H 0.5000 0.5264 0.7500 0.034 Uiso 1 2 calc SR
C46 C 0.44033(9) 0.42725(8) 0.67340(9) 0.0274(3) Uani 1 1 d .
H46 H 0.3993 0.4565 0.6215 0.033 Uiso 1 1 calc R
C47 C 0.38052(9) 0.29429(7) 0.58800(9) 0.0285(3) Uani 1 1 d .
H47A H 0.4207 0.2772 0.5396 0.034 Uiso 1 1 calc R
H47B H 0.3575 0.2445 0.6170 0.034 Uiso 1 1 calc R
N47 N 0.29838(7) 0.33996(6) 0.53280(8) 0.0261(2) Uani 1 1 d .
C51 C 0.22175(9) 0.34626(7) 0.58379(9) 0.0283(3) Uani 1 1 d .
O51 O 0.22476(7) 0.30531(6) 0.65945(7) 0.0394(3) Uani 1 1 d .
C52 C 0.14126(10) 0.40322(8) 0.54797(11) 0.0367(3) Uani 1 1 d .
H52A H 0.1664 0.4576 0.5392 0.055 Uiso 1 1 calc R
H52B H 0.1001 0.4055 0.5982 0.055 Uiso 1 1 calc R
H52C H 0.1043 0.3840 0.4830 0.055 Uiso 1 1 calc R
C61 C 0.30044(10) 0.37604(8) 0.43924(10) 0.0300(3) Uani 1 1 d .
O61 O 0.23143(8) 0.40932(6) 0.39009(7) 0.0424(3) Uani 1 1 d .
C62 C 0.39145(11) 0.37102(10) 0.40077(11) 0.0435(4) Uani 1 1 d .
H62A H 0.4028 0.3145 0.3831 0.065 Uiso 1 1 calc R
H62B H 0.4442 0.3898 0.4536 0.065 Uiso 1 1 calc R
H62C H 0.3869 0.4054 0.3404 0.065 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
_geom_angle_site_symmetry_3
C12 C11 C16 118.70(11) . .
C12 C11 C17 118.89(11) . .
C16 C11 C17 122.30(11) . .
C11 C12 C11 121.98(15) 2 .
C11 C12 H12 119.0 2 .
C11 C12 H12 119.0 . .
C16 C15 C16 120.85(16) . 2
C16 C15 H15 119.6 . .
C16 C15 H15 119.6 2 .
C15 C16 C11 119.89(12) . .
C15 C16 H16 120.1 . .
C11 C16 H16 120.1 . .
N17 C17 C11 114.37(10) . .
N17 C17 H17A 108.7 . .
C11 C17 H17A 108.7 . .
N17 C17 H17B 108.7 . .
C11 C17 H17B 108.7 . .
H17A C17 H17B 107.6 . .
C31 N17 C21 124.79(11) . .
C31 N17 C17 120.68(11) . .
C21 N17 C17 114.53(11) . .
O21 C21 N17 117.84(12) . .
O21 C21 C22 121.08(13) . .
N17 C21 C22 121.08(12) . .
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 N17 121.48(13) . .
O31 C31 C32 120.96(13) . .
N17 C31 C32 117.55(12) . .
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 . .
C42 C41 C46 118.72(11) . .
C42 C41 C47 118.90(11) . .
C46 C41 C47 122.34(11) . .
C41 C42 C41 121.74(15) 2_656 .
C41 C42 H42 119.1 2_656 .
C41 C42 H42 119.1 . .
C46 C45 C46 120.94(16) . 2_656
C46 C45 H45 119.5 . .
C46 C45 H45 119.5 2_656 .
C45 C46 C41 119.94(12) . .
C45 C46 H46 120.0 . .
C41 C46 H46 120.0 . .
N47 C47 C41 112.98(10) . .
N47 C47 H47A 109.0 . .
C41 C47 H47A 109.0 . .
N47 C47 H47B 109.0 . .
C41 C47 H47B 109.0 . .
H47A C47 H47B 107.8 . .
C61 N47 C51 124.31(11) . .
C61 N47 C47 121.06(11) . .
C51 N47 C47 114.58(10) . .
O51 C51 N47 117.67(12) . .
O51 C51 C52 121.16(12) . .
N47 C51 C52 121.14(11) . .
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 N47 121.73(12) . .
O61 C61 C62 120.77(12) . .
N47 C61 C62 117.49(12) . .
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 C12 1.3826(14) .
C11 C16 1.3905(17) .
C11 C17 1.5077(17) .
C12 C11 1.3826(14) 2
C12 H12 0.9500 .
C15 C16 1.3816(15) .
C15 C16 1.3816(15) 2
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 N17 1.4706(16) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
N17 C31 1.3966(17) .
N17 C21 1.4088(17) .
C21 O21 1.2092(17) .
C21 C22 1.489(2) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C31 O31 1.2013(17) .
C31 C32 1.492(2) .
C32 H32A 0.9800 .
C32 H32B 0.9800 .
C32 H32C 0.9800 .
C41 C42 1.3872(14) .
C41 C46 1.3894(17) .
C41 C47 1.5074(17) .
C42 C41 1.3872(14) 2_656
C42 H42 0.9500 .
C45 C46 1.3811(15) .
C45 C46 1.3811(15) 2_656
C45 H45 0.9500 .
C46 H46 0.9500 .
C47 N47 1.4682(15) .
C47 H47A 0.9900 .
C47 H47B 0.9900 .
N47 C61 1.3953(16) .
N47 C51 1.4070(16) .
C51 O51 1.2129(15) .
C51 C52 1.4901(18) .
C52 H52A 0.9800 .
C52 H52B 0.9800 .
C52 H52C 0.9800 .
C61 O61 1.2067(16) .
C61 C62 1.4959(19) .
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_1
_geom_torsion_site_symmetry_4
C16 C11 C12 C11 -0.10(8) . 2
C17 C11 C12 C11 176.02(12) . 2
C16 C15 C16 C11 -0.10(8) 2 .
C12 C11 C16 C15 0.20(16) . .
C17 C11 C16 C15 -175.78(10) . .
C12 C11 C17 N17 148.12(10) . .
C16 C11 C17 N17 -35.91(17) . .
C11 C17 N17 C31 101.15(14) . .
C11 C17 N17 C21 -79.20(14) . .
C31 N17 C21 O21 178.95(12) . .
C17 N17 C21 O21 -0.68(17) . .
C31 N17 C21 C22 -0.80(19) . .
C17 N17 C21 C22 179.57(12) . .
C21 N17 C31 O31 -3.9(2) . .
C17 N17 C31 O31 175.74(13) . .
C21 N17 C31 C32 177.08(12) . .
C17 N17 C31 C32 -3.31(17) . .
C46 C41 C42 C41 -0.48(8) . 2_656
C47 C41 C42 C41 177.42(12) . 2_656
C46 C45 C46 C41 -0.49(8) 2_656 .
C42 C41 C46 C45 0.96(16) . .
C47 C41 C46 C45 -176.86(10) . .
C42 C41 C47 N47 159.37(9) . .
C46 C41 C47 N47 -22.81(17) . .
C41 C47 N47 C61 100.33(13) . .
C41 C47 N47 C51 -77.27(13) . .
C61 N47 C51 O51 172.65(12) . .
C47 N47 C51 O51 -9.83(16) . .
C61 N47 C51 C52 -9.27(18) . .
C47 N47 C51 C52 168.25(11) . .
C51 N47 C61 O61 -7.40(19) . .
C47 N47 C61 O61 175.24(11) . .
C51 N47 C61 C62 173.49(12) . .
C47 N47 C61 C62 -3.88(17) . .
