#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:06:25 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180123 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/21/7102125.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_7102125
loop_
_publ_author_name
'Mahnke, Devin J'
'McDonald, Robert'
'Hof, Fraser'
_publ_section_title
;
 A shape-dependent hydrophobic effect for tetrazoles.
;
_journal_issue                   36
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3738
_journal_page_last               3740
_journal_paper_doi               10.1039/b705256a
_journal_year                    2007
_chemical_formula_moiety         'C18 H24 N12, C H4 O, H2 O'
_chemical_formula_sum            'C19 H30 N12 O2'
_chemical_formula_weight         458.55
_chemical_name_systematic
'1,3,5-tris(1H-tetrazol-5-yl)methyl-2,4,6-triethyl benzene'
_space_group_IT_number           36
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      36
_symmetry_space_group_name_Hall  'C 2c -2'
_symmetry_space_group_name_H-M   'C m c 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9746(7)
_cell_length_b                   18.4624(11)
_cell_length_c                   10.3004(6)
_cell_measurement_reflns_used    7740
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.21
_cell_volume                     2277.2(2)
_computing_cell_refinement       'Bruker SAINT (Bruker, 1997)'
_computing_data_collection       'Bruker SMART (Bruker, 1997)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL (Bruker, 1997)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0124
_diffrn_reflns_av_sigmaI/netI    0.0119
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8287
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         2.03
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9632
_exptl_absorpt_correction_T_min  0.9412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_recrystallization_method 'Slow evaporation from wet MeOH'
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2437
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0262
_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)+(0.0425P)²+0.6614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0709
_reflns_number_gt                2386
_reflns_number_total             2437
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b705256a.txt
_cod_data_source_block           vic0611
_cod_database_code               7102125
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, 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
N11 N 0.0000 0.27083(8) 0.31550(16) 0.0280(3) Uani 1 2 d S
H11N H 0.0000 0.2220(14) 0.296(3) 0.043(6) Uiso 1 2 d S
N12 N 0.0000 0.28768(9) 0.44276(16) 0.0343(3) Uani 1 2 d S
N13 N 0.0000 0.35776(9) 0.44922(16) 0.0346(4) Uani 1 2 d S
N14 N 0.0000 0.38721(8) 0.32789(16) 0.0309(3) Uani 1 2 d S
N21 N 0.31006(10) 0.01657(6) 0.00464(11) 0.0312(2) Uani 1 1 d .
H21N H 0.3522(14) 0.0041(10) -0.0597(19) 0.042(4) Uiso 1 1 d .
N22 N 0.31564(10) -0.01906(6) 0.11853(11) 0.0359(3) Uani 1 1 d .
N23 N 0.24908(10) 0.01417(6) 0.19585(12) 0.0339(3) Uani 1 1 d .
N24 N 0.19972(9) 0.07132(5) 0.13527(11) 0.0301(2) Uani 1 1 d .
C1 C 0.0000 0.26472(8) 0.03470(16) 0.0225(3) Uani 1 2 d S
C2 C 0.10210(9) 0.23090(5) 0.00603(11) 0.0221(2) Uani 1 1 d .
C3 C 0.10131(9) 0.16408(6) -0.05898(11) 0.0219(2) Uani 1 1 d .
C4 C 0.0000 0.13069(8) -0.09235(16) 0.0231(3) Uani 1 2 d S
C5 C 0.21161(11) 0.26675(6) 0.04353(12) 0.0276(3) Uani 1 1 d .
H5A H 0.2674 0.2288 0.0636 0.033 Uiso 1 1 calc R
H5B H 0.2001 0.2959 0.1231 0.033 Uiso 1 1 calc R
C6 C 0.25748(12) 0.31578(7) -0.06390(15) 0.0355(3) Uani 1 1 d .
H6A H 0.3278 0.3377 -0.0351 0.043 Uiso 1 1 calc R
H6B H 0.2032 0.3540 -0.0830 0.043 Uiso 1 1 calc R
H6C H 0.2708 0.2870 -0.1423 0.043 Uiso 1 1 calc R
C7 C 0.0000 0.06032(9) -0.16907(16) 0.0263(3) Uani 1 2 d S
H7A H -0.0669 0.0316 -0.1459 0.032 Uiso 0.50 1 calc PR
H7B H 0.0669 0.0316 -0.1459 0.032 Uiso 0.50 1 calc PR
C8 C 0.0000 0.07497(11) -0.31526(19) 0.0374(4) Uani 1 2 d S
H8A H 0.0000 0.0288 -0.3623 0.045 Uiso 1 2 calc SR
H8B H 0.0668 0.1027 -0.3385 0.045 Uiso 0.50 1 calc PR
H8C H -0.0668 0.1027 -0.3385 0.045 Uiso 0.50 1 calc PR
C10 C 0.0000 0.33763(9) 0.10196(17) 0.0258(3) Uani 1 2 d S
H10A H 0.0668 0.3652 0.0741 0.031 Uiso 0.50 1 calc PR
H10B H -0.0668 0.3652 0.0741 0.031 Uiso 0.50 1 calc PR
C11 C 0.0000 0.33203(9) 0.24702(18) 0.0255(3) Uani 1 2 d S
C20 C 0.21049(10) 0.12548(6) -0.08844(12) 0.0245(2) Uani 1 1 d .
H20A H 0.2042 0.1001 -0.1728 0.029 Uiso 1 1 calc R
H20B H 0.2713 0.1616 -0.0956 0.029 Uiso 1 1 calc R
C21 C 0.23891(9) 0.07179(6) 0.01568(11) 0.0239(2) Uani 1 1 d .
O1S O 0.0000 0.53670(8) 0.35163(13) 0.0365(3) Uani 1 2 d S
H1SO H 0.0000 0.499(2) 0.307(3) 0.067(9) Uiso 1 2 d S
C1S C 0.0000 0.59664(12) 0.2631(2) 0.0433(5) Uani 1 2 d S
H1SA H -0.0764 0.6058 0.2332 0.052 Uiso 0.50 1 calc PR
H1SB H 0.0476 0.5853 0.1885 0.052 Uiso 0.50 1 calc PR
H1SC H 0.0288 0.6398 0.3072 0.052 Uiso 0.50 1 calc PR
O2S O 0.0000 0.12944(7) 0.26395(13) 0.0307(3) Uani 1 2 d S
H2SO H 0.0617(15) 0.1116(9) 0.2196(17) 0.048(5) 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'
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
C11 N11 N12 108.63(15) . .
N13 N12 N11 106.30(15) . .
N12 N13 N14 110.57(15) . .
C11 N14 N13 105.76(15) . .
C21 N21 N22 109.32(10) . .
N23 N22 N21 106.05(10) . .
N22 N23 N24 110.85(11) . .
C21 N24 N23 106.20(10) . .
C2 C1 C2 121.07(14) 4 .
C2 C1 C10 119.45(7) 4 .
C2 C1 C10 119.45(7) . .
C3 C2 C1 119.03(10) . .
C3 C2 C5 120.67(10) . .
C1 C2 C5 120.30(10) . .
C4 C3 C2 120.57(10) . .
C4 C3 C20 119.27(10) . .
C2 C3 C20 120.10(10) . .
C3 C4 C3 119.63(14) . 4
C3 C4 C7 120.16(7) . .
C3 C4 C7 120.16(7) 4 .
C2 C5 C6 112.54(11) . .
C4 C7 C8 111.13(14) . .
C11 C10 C1 113.27(14) . .
N14 C11 N11 108.75(16) . .
N14 C11 C10 125.31(16) . .
N11 C11 C10 125.94(15) . .
C21 C20 C3 111.25(10) . .
N24 C21 N21 107.58(10) . .
N24 C21 C20 126.30(10) . .
N21 C21 C20 126.11(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C11 1.332(2) .
N11 N12 1.347(2) .
N12 N13 1.295(2) .
N13 N14 1.363(2) .
N14 C11 1.316(2) .
N21 C21 1.3334(16) .
N21 N22 1.3466(15) .
N22 N23 1.2829(16) .
N23 N24 1.3608(15) .
N24 C21 1.3182(16) .
C1 C2 1.4042(13) 4
C1 C2 1.4042(13) .
C1 C10 1.514(2) .
C2 C3 1.4038(15) .
C2 C5 1.5188(16) .
C3 C4 1.4035(13) .
C3 C20 1.5196(15) .
C4 C3 1.4035(13) 4
C4 C7 1.521(2) .
C5 C6 1.5316(18) .
C7 C8 1.530(3) .
C10 C11 1.498(2) .
C20 C21 1.4995(16) .
O1S C1S 1.434(2) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11N O2S 0.92(3) 1.74(3) 2.664(2) 179(3) .
N21 H21N O1S 0.864(19) 2.129(18) 2.9367(14) 155.3(16) 6_554
O1S H1SO N14 0.84(4) 2.07(4) 2.771(2) 141(3) .
O2S H2SO N24 0.929(18) 2.010(18) 2.9374(13) 176.1(16) .
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
C11 N11 N12 N13 0.0 . .
N11 N12 N13 N14 0.0 . .
N12 N13 N14 C11 0.0 . .
C21 N21 N22 N23 0.08(15) . .
N21 N22 N23 N24 -0.17(14) . .
N22 N23 N24 C21 0.19(14) . .
C2 C1 C2 C3 3.6(2) 4 .
C10 C1 C2 C3 -178.57(13) . .
C2 C1 C2 C5 -177.11(9) 4 .
C10 C1 C2 C5 0.69(19) . .
C1 C2 C3 C4 -1.40(17) . .
C5 C2 C3 C4 179.34(12) . .
C1 C2 C3 C20 -178.59(12) . .
C5 C2 C3 C20 2.14(16) . .
C2 C3 C4 C3 -0.8(2) . 4
C20 C3 C4 C3 176.45(9) . 4
C2 C3 C4 C7 176.73(12) . .
C20 C3 C4 C7 -6.0(2) . .
C3 C2 C5 C6 88.68(13) . .
C1 C2 C5 C6 -90.57(14) . .
C3 C4 C7 C8 -88.75(13) . .
C3 C4 C7 C8 88.75(13) 4 .
C2 C1 C10 C11 88.92(12) 4 .
C2 C1 C10 C11 -88.92(12) . .
N13 N14 C11 N11 0.0 . .
N13 N14 C11 C10 180.0 . .
N12 N11 C11 N14 0.0 . .
N12 N11 C11 C10 180.0 . .
C1 C10 C11 N14 180.0 . .
C1 C10 C11 N11 0.0 . .
C4 C3 C20 C21 -83.21(14) . .
C2 C3 C20 C21 94.02(12) . .
N23 N24 C21 N21 -0.14(14) . .
N23 N24 C21 C20 -179.04(11) . .
N22 N21 C21 N24 0.04(15) . .
N22 N21 C21 C20 178.94(11) . .
C3 C20 C21 N24 -20.36(16) . .
C3 C20 C21 N21 160.94(12) . .
