#------------------------------------------------------------------------------
#$Date: 2025-08-21 15:03:24 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301848 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/02/68/7026875.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_7026875
loop_
_publ_author_name
'Martinelli, Jonathan'
'Balali-Mood, Beeta'
'Panizzo, Rachael'
'Lythgoe, Mark F.'
'White, Andrew J. P.'
'Ferretti, Patrizia'
'Steinke, Joachim H. G.'
'Vilar, Ramon'
_publ_section_title
;
 Coordination chemistry of amide-functionalised tetraazamacrocycles:
 structural, relaxometric and cytotoxicity studies.
;
_journal_issue                   42
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10056
_journal_page_last               10067
_journal_paper_doi               10.1039/c0dt00815j
_journal_volume                  39
_journal_year                    2010
_chemical_formula_moiety         'C28 H40 N8 O4'
_chemical_formula_sum            'C28 H40 N8 O4'
_chemical_formula_weight         552.68
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.157(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.3718(2)
_cell_length_b                   8.1181(2)
_cell_length_c                   19.6489(6)
_cell_measurement_reflns_used    5858
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.5346
_cell_measurement_theta_min      4.1713
_cell_volume                     1466.66(7)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_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_detector_area_resol_mean 15.9825
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'OD Xcalibur 3'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_sigmaI/netI    0.0580
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            22976
_diffrn_reflns_theta_full        31.50
_diffrn_reflns_theta_max         32.61
_diffrn_reflns_theta_min         4.18
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.873
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         4946
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.872
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0400
_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)+(0.0466P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0927
_reflns_number_gt                2906
_reflns_number_total             4946
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0dt00815j.txt
_cod_data_source_block           5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7026875
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 0.30048(8) 0.94160(10) 0.44346(4) 0.02346(18) Uani 1 1 d .
C2 C 0.38071(10) 0.87717(13) 0.39182(5) 0.0251(2) Uani 1 1 d .
H2A H 0.4449 0.9653 0.3801 0.030 Uiso 1 1 calc R
H2B H 0.3100 0.8500 0.3490 0.030 Uiso 1 1 calc R
C3 C 0.47247(10) 0.72583(13) 0.41449(5) 0.0269(2) Uani 1 1 d .
H3A H 0.4191 0.6533 0.4414 0.032 Uiso 1 1 calc R
H3B H 0.4863 0.6644 0.3727 0.032 Uiso 1 1 calc R
N4 N 0.61633(8) 0.76385(10) 0.45699(4) 0.02455(18) Uani 1 1 d .
C5 C 0.61203(10) 0.77592(13) 0.53155(5) 0.0271(2) Uani 1 1 d .
H5A H 0.6207 0.6644 0.5523 0.033 Uiso 1 1 calc R
H5B H 0.5175 0.8228 0.5371 0.033 Uiso 1 1 calc R
C6 C 0.73440(10) 0.88373(13) 0.56924(5) 0.0278(2) Uani 1 1 d .
H6A H 0.7501 0.8612 0.6197 0.033 Uiso 1 1 calc R
H6B H 0.8254 0.8571 0.5531 0.033 Uiso 1 1 calc R
C13 C 0.17390(10) 0.83990(13) 0.44698(5) 0.0270(2) Uani 1 1 d .
H13A H 0.1876 0.7307 0.4268 0.032 Uiso 1 1 calc R
H13B H 0.0873 0.8912 0.4179 0.032 Uiso 1 1 calc R
C14 C 0.14406(10) 0.81507(12) 0.51904(5) 0.0245(2) Uani 1 1 d .
O14 O 0.05620(7) 0.70802(9) 0.52897(4) 0.03251(18) Uani 1 1 d .
N15 N 0.21503(9) 0.91062(11) 0.56949(4) 0.0297(2) Uani 1 1 d D
H15 H 0.2779(10) 0.9860(10) 0.5591(6) 0.039(3) Uiso 1 1 d D
C16 C 0.20100(12) 0.88838(14) 0.64147(5) 0.0330(2) Uani 1 1 d .
H16A H 0.1860 0.9971 0.6618 0.040 Uiso 1 1 calc R
H16B H 0.1143 0.8198 0.6430 0.040 Uiso 1 1 calc R
C17 C 0.32862(13) 0.81020(17) 0.68285(6) 0.0419(3) Uani 1 1 d .
C18 C 0.43279(16) 0.7519(2) 0.71744(7) 0.0655(5) Uani 1 1 d .
H18 H 0.5170 0.7049 0.7454 0.079 Uiso 1 1 calc R
C19 C 0.72198(10) 0.63825(13) 0.44626(5) 0.0270(2) Uani 1 1 d .
H19A H 0.6795 0.5278 0.4501 0.032 Uiso 1 1 calc R
H19B H 0.8097 0.6481 0.4833 0.032 Uiso 1 1 calc R
C20 C 0.76608(10) 0.65309(13) 0.37638(5) 0.0257(2) Uani 1 1 d .
O20 O 0.71123(8) 0.75232(10) 0.33171(4) 0.03574(19) Uani 1 1 d .
N21 N 0.87231(9) 0.55025(12) 0.36717(5) 0.0322(2) Uani 1 1 d D
H21 H 0.9025(12) 0.4716(10) 0.3990(5) 0.042(3) Uiso 1 1 d D
C22 C 0.91449(12) 0.53934(18) 0.30000(6) 0.0426(3) Uani 1 1 d .
H22A H 0.8962 0.6467 0.2760 0.051 Uiso 1 1 calc R
H22B H 0.8533 0.4556 0.2715 0.051 Uiso 1 1 calc R
C23 C 1.06699(13) 0.49564(15) 0.30548(6) 0.0354(3) Uani 1 1 d .
C24 C 1.18906(14) 0.46016(19) 0.30749(7) 0.0512(3) Uani 1 1 d .
H24 H 1.2879 0.4314 0.3091 0.061 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
C13 N1 C6 113.53(7) . 3_676
C13 N1 C2 111.14(8) . .
C6 N1 C2 110.70(7) 3_676 .
N1 C2 C3 114.96(8) . .
N4 C3 C2 113.65(8) . .
C19 N4 C3 110.01(8) . .
C19 N4 C5 109.76(8) . .
C3 N4 C5 112.23(7) . .
N4 C5 C6 111.07(8) . .
N1 C6 C5 110.64(8) 3_676 .
N1 C13 C14 114.86(8) . .
O14 C14 N15 122.91(9) . .
O14 C14 C13 119.42(9) . .
N15 C14 C13 117.66(8) . .
C14 N15 C16 121.66(9) . .
C17 C16 N15 112.19(9) . .
C18 C17 C16 177.76(16) . .
N4 C19 C20 112.71(8) . .
O20 C20 N21 122.14(9) . .
O20 C20 C19 123.40(9) . .
N21 C20 C19 114.45(9) . .
C20 N21 C22 120.10(9) . .
N21 C22 C23 112.56(9) . .
C24 C23 C22 177.74(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C13 1.4579(12) .
N1 C6 1.4657(13) 3_676
N1 C2 1.4709(11) .
C2 C3 1.5163(14) .
C3 N4 1.4747(13) .
N4 C19 1.4647(12) .
N4 C5 1.4767(13) .
C5 C6 1.5169(14) .
C6 N1 1.4657(13) 3_676
C13 C14 1.5090(14) .
C14 O14 1.2383(11) .
C14 N15 1.3310(13) .
N15 C16 1.4568(13) .
C16 C17 1.4554(17) .
C17 C18 1.1755(18) .
C19 C20 1.5133(14) .
C20 O20 1.2284(12) .
C20 N21 1.3382(13) .
N21 C22 1.4519(14) .
C22 C23 1.4562(15) .
C23 C24 1.1730(16) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101785356
