#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:14:55 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180383 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/52/7205276.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_7205276
loop_
_publ_author_name
'Dey, Sandeep Kumar'
'Ojha, Bimlesh'
'Das, Gopal'
_publ_section_title
;
 A subtle interplay of C--H hydrogen bonds in complexation of anions of
 varied dimensionality by a nitro functionalized tripodal podand
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              269
_journal_paper_doi               10.1039/c0ce00316f
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C24 H25 N4 O9, Cl'
_chemical_formula_sum            'C24 H25 Cl N4 O9'
_chemical_formula_weight         548.93
_chemical_name_systematic
;
?
;
_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                98.90(4)
_cell_angle_beta                 102.77(3)
_cell_angle_gamma                105.84(5)
_cell_formula_units_Z            2
_cell_length_a                   7.475(6)
_cell_length_b                   13.365(10)
_cell_length_c                   13.784(10)
_cell_measurement_reflns_used    1270
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      18.45
_cell_measurement_theta_min      3.27
_cell_volume                     1257.6(17)
_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 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.1018
_diffrn_reflns_av_sigmaI/netI    0.1515
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8173
_diffrn_reflns_theta_full        23.56
_diffrn_reflns_theta_max         23.56
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0078(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.810
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         3172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.810
_refine_ls_R_factor_all          0.1069
_refine_ls_R_factor_gt           0.0518
_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)+(0.0405P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1240
_reflns_number_gt                3570
_reflns_number_total             3753
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CE00316F.TXT
_cod_data_source_block           nitro-HCl
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7205276
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.14510(17) 0.02489(10) 0.84487(9) 0.0569(4) Uani 1 1 d . . .
C5 C -0.1171(7) 0.8701(3) 0.4953(4) 0.0478(13) Uani 1 1 d . . .
H5 H -0.2190 0.8841 0.5170 0.057 Uiso 1 1 calc R . .
C2 C 0.4308(6) 0.9236(4) 0.6984(3) 0.0491(13) Uani 1 1 d . . .
H2A H 0.3780 0.8618 0.7244 0.059 Uiso 1 1 calc R . .
H2B H 0.3762 0.9788 0.7188 0.059 Uiso 1 1 calc R . .
C1 C 0.6482(6) 0.9638(3) 0.7357(3) 0.0421(12) Uani 1 1 d . . .
H1A H 0.6991 0.9186 0.6949 0.051 Uiso 1 1 calc R . .
H1B H 0.6939 1.0355 0.7252 0.051 Uiso 1 1 calc R . .
C3 C 0.2106(7) 0.8730(4) 0.5302(4) 0.0460(13) Uani 1 1 d . . .
C6 C -0.1424(7) 0.8273(3) 0.3932(4) 0.0425(12) Uani 1 1 d . . .
C4 C 0.0625(7) 0.8920(3) 0.5655(4) 0.0474(13) Uani 1 1 d . . .
H4 H 0.0814 0.9188 0.6347 0.057 Uiso 1 1 calc R . .
C7 C 0.0050(7) 0.8063(4) 0.3592(4) 0.0560(14) Uani 1 1 d . . .
H7 H -0.0149 0.7762 0.2906 0.067 Uiso 1 1 calc R . .
C8 C 0.1811(7) 0.8298(4) 0.4273(4) 0.0600(15) Uani 1 1 d . . .
H8 H 0.2829 0.8169 0.4048 0.072 Uiso 1 1 calc R . .
N1 N 0.7267(6) 0.9662(3) 0.8459(3) 0.0370(9) Uani 1 1 d . . .
N2 N -0.3278(6) 0.8023(4) 0.3202(4) 0.0528(12) Uani 1 1 d . . .
O1 O 0.3937(4) 0.8954(3) 0.5892(2) 0.0579(10) Uani 1 1 d . . .
O2 O -0.3641(5) 0.7425(3) 0.2385(3) 0.0737(12) Uani 1 1 d . . .
O3 O -0.4427(5) 0.8446(3) 0.3456(3) 0.0720(11) Uani 1 1 d . . .
C16 C 0.8458(7) 1.3559(4) 0.8786(4) 0.0541(14) Uani 1 1 d . . .
H16 H 0.7122 1.3297 0.8665 0.065 Uiso 1 1 calc R . .
C9 C 0.6550(6) 1.0337(3) 0.9160(3) 0.0448(13) Uani 1 1 d . . .
H9A H 0.7179 1.0355 0.9860 0.054 Uiso 1 1 calc R . .
H9B H 0.5172 0.9999 0.9041 0.054 Uiso 1 1 calc R . .
C14 C 1.1276(9) 1.4946(4) 0.8878(4) 0.0518(14) Uani 1 1 d . . .
C11 C 0.9594(7) 1.2934(4) 0.9081(3) 0.0439(12) Uani 1 1 d . . .
C12 C 1.1565(7) 1.3326(4) 0.9250(3) 0.0507(13) Uani 1 1 d . . .
H12 H 1.2328 1.2904 0.9438 0.061 Uiso 1 1 calc R . .
C10 C 0.6892(6) 1.1465(3) 0.9038(4) 0.0498(13) Uani 1 1 d . . .
H10A H 0.6222 1.1472 0.8352 0.060 Uiso 1 1 calc R . .
H10B H 0.6420 1.1858 0.9521 0.060 Uiso 1 1 calc R . .
C15 C 0.9313(8) 1.4569(4) 0.8674(4) 0.0575(14) Uani 1 1 d . . .
H15 H 0.8563 1.4989 0.8461 0.069 Uiso 1 1 calc R . .
C13 C 1.2407(8) 1.4329(4) 0.9145(4) 0.0565(14) Uani 1 1 d . . .
H13 H 1.3739 1.4591 0.9254 0.068 Uiso 1 1 calc R . .
O4 O 0.8911(4) 1.1933(2) 0.9224(2) 0.0501(9) Uani 1 1 d . . .
O5 O 1.3957(7) 1.6415(3) 0.9156(3) 0.0872(14) Uani 1 1 d . . .
O6 O 1.1195(7) 1.6553(3) 0.8495(3) 0.0906(14) Uani 1 1 d . . .
N3 N 1.2208(9) 1.6045(4) 0.8833(3) 0.0641(13) Uani 1 1 d . . .
C17 C 0.6919(7) 0.8563(3) 0.8706(3) 0.0492(13) Uani 1 1 d . . .
H17A H 0.7620 0.8652 0.9412 0.059 Uiso 1 1 calc R . .
H17B H 0.5552 0.8258 0.8643 0.059 Uiso 1 1 calc R . .
C19 C 0.6380(10) 0.6861(4) 0.6266(5) 0.0634(16) Uani 1 1 d . . .
C18 C 0.7508(8) 0.7794(4) 0.8050(4) 0.0621(15) Uani 1 1 d . . .
H18A H 0.8727 0.8152 0.7929 0.075 Uiso 1 1 calc R . .
H18B H 0.7669 0.7222 0.8381 0.075 Uiso 1 1 calc R . .
C20 C 0.8025(9) 0.6580(4) 0.6290(5) 0.0746(18) Uani 1 1 d . . .
H20 H 0.8979 0.6716 0.6900 0.089 Uiso 1 1 calc R . .
C24 C 0.4958(9) 0.6647(4) 0.5358(5) 0.0685(16) Uani 1 1 d . . .
H24 H 0.3854 0.6841 0.5357 0.082 Uiso 1 1 calc R . .
C22 C 0.6777(15) 0.5873(5) 0.4483(7) 0.091(2) Uani 1 1 d . . .
C21 C 0.8209(11) 0.6080(5) 0.5363(7) 0.090(2) Uani 1 1 d . . .
H21 H 0.9312 0.5890 0.5349 0.108 Uiso 1 1 calc R . .
C23 C 0.5158(12) 0.6151(4) 0.4460(5) 0.085(2) Uani 1 1 d . . .
H23 H 0.4205 0.6008 0.3849 0.102 Uiso 1 1 calc R . .
O7 O 0.6020(5) 0.7370(3) 0.7104(3) 0.0624(10) Uani 1 1 d . . .
N4 N 0.7031(16) 0.5319(6) 0.3515(6) 0.0608(6) Uani 1 1 d . . .
O8 O 0.5638(12) 0.5098(5) 0.2751(5) 0.0557(5) Uani 1 1 d . . .
O9 O 0.8479(13) 0.5110(6) 0.3547(6) 0.0934(7) Uani 1 1 d . . .
H1N H 0.885(5) 1.000(3) 0.861(3) 0.034(11) 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C6 C5 C4 119.4(5) . . ?
O1 C2 C1 103.1(3) . . ?
N1 C1 C2 113.8(3) . . ?
O1 C3 C4 124.5(5) . . ?
O1 C3 C8 114.7(4) . . ?
C4 C3 C8 120.8(5) . . ?
C7 C6 C5 121.5(5) . . ?
C7 C6 N2 118.3(5) . . ?
C5 C6 N2 120.1(5) . . ?
C3 C4 C5 118.5(5) . . ?
C8 C7 C6 118.9(5) . . ?
C7 C8 C3 120.7(5) . . ?
C9 N1 C1 113.0(3) . . ?
C9 N1 C17 108.9(3) . . ?
C1 N1 C17 114.4(3) . . ?
O2 N2 O3 123.1(4) . . ?
O2 N2 C6 119.8(4) . . ?
O3 N2 C6 117.1(5) . . ?
C3 O1 C2 118.6(3) . . ?
C15 C16 C11 119.8(5) . . ?
N1 C9 C10 114.7(3) . . ?
C15 C14 C13 121.7(5) . . ?
C15 C14 N3 119.4(6) . . ?
C13 C14 N3 118.9(6) . . ?
O4 C11 C12 115.5(5) . . ?
O4 C11 C16 124.9(5) . . ?
C12 C11 C16 119.7(5) . . ?
C13 C12 C11 120.3(5) . . ?
O4 C10 C9 106.9(4) . . ?
C14 C15 C16 119.0(5) . . ?
C12 C13 C14 119.4(5) . . ?
C11 O4 C10 118.7(4) . . ?
O6 N3 O5 123.1(5) . . ?
O6 N3 C14 118.5(6) . . ?
O5 N3 C14 118.4(6) . . ?
C18 C17 N1 115.0(4) . . ?
C20 C19 O7 124.0(6) . . ?
C20 C19 C24 120.9(6) . . ?
O7 C19 C24 115.0(6) . . ?
O7 C18 C17 107.7(4) . . ?
C19 C20 C21 117.5(6) . . ?
C23 C24 C19 120.7(7) . . ?
C23 C22 C21 122.3(8) . . ?
C23 C22 N4 119.8(9) . . ?
C21 C22 N4 118.0(9) . . ?
C22 C21 C20 120.1(7) . . ?
C24 C23 C22 118.5(7) . . ?
C19 O7 C18 120.2(4) . . ?
O9 N4 O8 126.2(10) . . ?
O9 N4 C22 118.7(10) . . ?
O8 N4 C22 115.1(10) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C5 C6 1.385(6) . ?
C5 C4 1.396(6) . ?
C2 O1 1.439(5) . ?
C2 C1 1.504(6) . ?
C1 N1 1.495(5) . ?
C3 O1 1.354(5) . ?
C3 C4 1.371(6) . ?
C3 C8 1.389(6) . ?
C6 C7 1.367(6) . ?
C6 N2 1.439(6) . ?
C7 C8 1.360(6) . ?
N1 C9 1.503(5) . ?
N1 C17 1.524(5) . ?
N2 O2 1.205(5) . ?
N2 O3 1.231(5) . ?
C16 C15 1.376(6) . ?
C16 C11 1.388(6) . ?
C9 C10 1.501(6) . ?
C14 C15 1.362(6) . ?
C14 C13 1.366(6) . ?
C14 N3 1.462(7) . ?
C11 O4 1.357(5) . ?
C11 C12 1.374(6) . ?
C12 C13 1.361(6) . ?
C10 O4 1.414(5) . ?
O5 N3 1.214(5) . ?
O6 N3 1.214(5) . ?
C17 C18 1.484(6) . ?
C19 C20 1.376(7) . ?
C19 O7 1.365(6) . ?
C19 C24 1.383(7) . ?
C18 O7 1.429(5) . ?
C20 C21 1.400(8) . ?
C24 C23 1.369(7) . ?
C22 C23 1.355(9) . ?
C22 C21 1.362(9) . ?
C22 N4 1.499(10) . ?
N4 O9 1.182(10) . ?
N4 O8 1.238(9) . ?
