#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/24/4502408.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_4502408
loop_
_publ_author_name
'Dey, Sandeep Kumar'
'Das, Gopal'
_publ_section_title
;
 Conformational Polymorphism of a Simple Tripodal Podand Bearing Nitro
 Functionality
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              754
_journal_paper_doi               10.1021/cg901153q
_journal_volume                  10
_journal_year                    2010
_chemical_formula_sum            'C24 H24 N4 O9'
_chemical_formula_weight         512.47
_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-97
_cell_angle_alpha                73.244(14)
_cell_angle_beta                 78.589(14)
_cell_angle_gamma                70.475(14)
_cell_formula_units_Z            2
_cell_length_a                   9.252(2)
_cell_length_b                   11.950(3)
_cell_length_c                   12.445(3)
_cell_measurement_reflns_used    2933
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.07
_cell_measurement_theta_min      2.35
_cell_volume                     1233.9(5)
_computing_cell_refinement       'Bruker Smart'
_computing_data_collection       'Bruker Smart'
_computing_data_reduction        'Bruker SAINT'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area  detector'
_diffrn_measurement_method       'phi and onega 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  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20329
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADAS (Sheldrick, 1997)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       recetangular
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0568P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1318
_reflns_number_gt                2884
_reflns_number_total             5904
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg901153q_si_002.cif
_cod_data_source_block           nitro1
_cod_depositor_comments
;
The following automatic conversions were performed:

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

'_exptl_absorpt_correction_type' value 'Multi-Scan'
changed to 'multi-scan' 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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               4502408
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.35381(13) 0.45928(11) 0.41383(10) 0.0549(3) Uani 1 1 d .
C9 C 0.23505(17) 0.57083(15) 0.43274(13) 0.0633(4) Uani 1 1 d .
H9A H 0.1713 0.5498 0.5028 0.076 Uiso 1 1 calc R
H9B H 0.1694 0.6019 0.3723 0.076 Uiso 1 1 calc R
C17 C 0.28536(18) 0.36324(15) 0.41794(12) 0.0636(4) Uani 1 1 d .
H17A H 0.3631 0.2982 0.3885 0.076 Uiso 1 1 calc R
H17B H 0.2025 0.3971 0.3700 0.076 Uiso 1 1 calc R
C18 C 0.22253(18) 0.31064(14) 0.53664(12) 0.0605(4) Uani 1 1 d .
H18A H 0.2983 0.2889 0.5888 0.073 Uiso 1 1 calc R
H18B H 0.1296 0.3690 0.5616 0.073 Uiso 1 1 calc R
C2 C 0.39611(18) 0.53636(15) 0.19846(12) 0.0627(4) Uani 1 1 d .
H2A H 0.3057 0.6056 0.2054 0.075 Uiso 1 1 calc R
H2B H 0.4721 0.5653 0.1415 0.075 Uiso 1 1 calc R
C1 C 0.46215(16) 0.47845(15) 0.31107(12) 0.0595(4) Uani 1 1 d .
H1A H 0.5358 0.3997 0.3065 0.071 Uiso 1 1 calc R
H1B H 0.5193 0.5292 0.3205 0.071 Uiso 1 1 calc R
C10 C 0.29439(19) 0.67137(15) 0.43860(13) 0.0655(4) Uani 1 1 d .
H10A H 0.2147 0.7290 0.4757 0.079 Uiso 1 1 calc R
H10B H 0.3826 0.6376 0.4814 0.079 Uiso 1 1 calc R
O1 O 0.35493(13) 0.44573(10) 0.16624(9) 0.0705(3) Uani 1 1 d .
O4 O 0.33876(12) 0.73235(10) 0.32433(8) 0.0685(3) Uani 1 1 d .
O7 O 0.18948(13) 0.20413(10) 0.52987(9) 0.0752(4) Uani 1 1 d .
C3 C 0.29226(17) 0.47817(15) 0.06775(13) 0.0598(4) Uani 1 1 d .
C6 C 0.16687(17) 0.52299(16) -0.12931(13) 0.0630(4) Uani 1 1 d .
C5 C 0.20585(17) 0.61396(16) -0.10582(13) 0.0659(4) Uani 1 1 d .
H5 H 0.1904 0.6901 -0.1565 0.079 Uiso 1 1 calc R
C19 C 0.11617(17) 0.14290(15) 0.62142(14) 0.0618(4) Uani 1 1 d .
C4 C 0.26791(18) 0.59251(15) -0.00698(13) 0.0638(4) Uani 1 1 d .
H4 H 0.2933 0.6544 0.0094 0.077 Uiso 1 1 calc R
C8 C 0.2525(2) 0.38703(16) 0.04251(14) 0.0709(5) Uani 1 1 d .
H8 H 0.2682 0.3105 0.0926 0.085 Uiso 1 1 calc R
C7 C 0.19008(19) 0.40874(17) -0.05584(15) 0.0719(5) Uani 1 1 d .
H7 H 0.1640 0.3474 -0.0726 0.086 Uiso 1 1 calc R
C20 C 0.0812(2) 0.04542(17) 0.60456(16) 0.0805(5) Uani 1 1 d .
H20 H 0.1092 0.0265 0.5344 0.097 Uiso 1 1 calc R
C22 C -0.0355(2) 0.0073(2) 0.79126(19) 0.0866(6) Uani 1 1 d .
C24 C 0.07580(19) 0.17178(17) 0.72446(14) 0.0729(5) Uani 1 1 d .
H24 H 0.1005 0.2362 0.7365 0.087 Uiso 1 1 calc R
C23 C -0.0024(2) 0.1034(2) 0.81037(16) 0.0909(6) Uani 1 1 d .
H23 H -0.0322 0.1223 0.8805 0.109 Uiso 1 1 calc R
C21 C 0.0060(2) -0.02311(18) 0.6900(2) 0.0910(6) Uani 1 1 d .
H21 H -0.0162 -0.0891 0.6791 0.109 Uiso 1 1 calc R
C11 C 0.39821(17) 0.82633(15) 0.30644(14) 0.0609(4) Uani 1 1 d .
C14 C 0.5207(2) 1.01773(17) 0.2508(2) 0.0805(6) Uani 1 1 d .
C13 C 0.4537(2) 0.98356(17) 0.35797(19) 0.0842(6) Uani 1 1 d .
H13 H 0.4488 1.0257 0.4115 0.101 Uiso 1 1 calc R
C16 C 0.4664(2) 0.86217(16) 0.19777(15) 0.0773(5) Uani 1 1 d .
H16 H 0.4706 0.8213 0.1435 0.093 Uiso 1 1 calc R
C12 C 0.39304(19) 0.88648(16) 0.38709(15) 0.0728(5) Uani 1 1 d .
H12 H 0.3491 0.8618 0.4605 0.087 Uiso 1 1 calc R
C15 C 0.5279(2) 0.95834(18) 0.17018(18) 0.0884(6) Uani 1 1 d .
H15 H 0.5738 0.9827 0.0974 0.106 Uiso 1 1 calc R
N2 N 0.10320(17) 0.54624(18) -0.23499(14) 0.0825(5) Uani 1 1 d .
N3 N 0.5908(2) 1.11839(17) 0.2202(3) 0.1109(7) Uani 1 1 d .
N4 N -0.1181(2) -0.0648(2) 0.8822(2) 0.1281(9) Uani 1 1 d .
O3 O 0.06789(18) 0.46444(15) -0.25466(12) 0.1150(5) Uani 1 1 d .
O2 O 0.08646(18) 0.64630(16) -0.30058(13) 0.1108(5) Uani 1 1 d .
O5 O 0.60297(18) 1.15848(15) 0.29855(19) 0.1369(7) Uani 1 1 d .
O8 O -0.1495(3) -0.14693(19) 0.8636(2) 0.1920(12) Uani 1 1 d .
O6 O 0.6330(3) 1.15582(17) 0.1222(2) 0.1656(9) Uani 1 1 d .
O9 O -0.1597(3) -0.0340(3) 0.97093(18) 0.2005(13) Uani 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
C9 N1 C17 111.32(11)
C9 N1 C1 114.28(12)
C17 N1 C1 111.66(12)
N1 C9 C10 115.27(12)
N1 C17 C18 112.00(13)
O7 C18 C17 104.94(12)
O1 C2 C1 108.40(12)
N1 C1 C2 118.01(12)
O4 C10 C9 107.95(12)
C3 O1 C2 118.42(12)
C11 O4 C10 119.64(12)
C19 O7 C18 119.21(12)
O1 C3 C4 124.97(15)
O1 C3 C8 115.56(14)
C4 C3 C8 119.47(16)
C5 C6 C7 121.02(16)
C5 C6 N2 119.60(16)
C7 C6 N2 119.37(16)
C6 C5 C4 120.09(16)
O7 C19 C24 124.79(16)
O7 C19 C20 114.92(15)
C24 C19 C20 120.30(15)
C5 C4 C3 119.67(15)
C7 C8 C3 120.76(16)
C8 C7 C6 118.99(16)
C21 C20 C19 120.66(19)
C21 C22 C23 121.94(17)
C21 C22 N4 118.7(2)
C23 C22 N4 119.4(2)
C19 C24 C23 118.91(18)
C22 C23 C24 119.53(19)
C22 C21 C20 118.6(2)
O4 C11 C12 124.67(16)
O4 C11 C16 115.38(15)
C12 C11 C16 119.95(16)
C13 C14 C15 121.21(18)
C13 C14 N3 120.3(2)
C15 C14 N3 118.5(2)
C14 C13 C12 120.02(19)
C15 C16 C11 120.00(18)
C11 C12 C13 119.44(18)
C14 C15 C16 119.37(19)
O2 N2 O3 122.03(18)
O2 N2 C6 119.00(17)
O3 N2 C6 118.97(18)
O6 N3 O5 124.4(2)
O6 N3 C14 118.7(3)
O5 N3 C14 117.0(3)
O8 N4 O9 123.1(2)
O8 N4 C22 118.7(3)
O9 N4 C22 118.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C9 1.4627(19)
N1 C17 1.4697(19)
N1 C1 1.4731(17)
C9 C10 1.502(2)
C17 C18 1.511(2)
C18 O7 1.4328(18)
C2 O1 1.4372(17)
C2 C1 1.521(2)
C10 O4 1.4468(17)
O1 C3 1.3585(18)
O4 C11 1.3542(18)
O7 C19 1.3560(17)
C3 C4 1.388(2)
C3 C8 1.390(2)
C6 C5 1.373(2)
C6 C7 1.381(2)
C6 N2 1.463(2)
C5 C4 1.381(2)
C19 C24 1.372(2)
C19 C20 1.387(2)
C8 C7 1.377(2)
C20 C21 1.368(2)
C22 C21 1.358(3)
C22 C23 1.375(3)
C22 N4 1.464(3)
C24 C23 1.386(2)
C11 C12 1.378(2)
C11 C16 1.385(2)
C14 C13 1.363(3)
C14 C15 1.367(3)
C14 N3 1.474(3)
C13 C12 1.380(2)
C16 C15 1.376(2)
N2 O2 1.2180(19)
N2 O3 1.2269(19)
N3 O6 1.206(3)
N3 O5 1.241(3)
N4 O8 1.204(3)
N4 O9 1.214(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9148478
2 PubChem 10973272
