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#$Date: 2022-11-23 10:15:23 +0200 (Wed, 23 Nov 2022) $
#$Revision: 279488 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/62/8106207.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_8106207
loop_
_publ_author_name
'Wei, Xiao'
'Guang-Ming, Bao'
'Ting-Ting, Sun'
'Chun-Yan, Hu'
'Hou-Qun, Yuan'
_publ_section_title
;
 Crystal structure of 1,3,5,7-tetraazaadamantane-1,3-diium
 2,5-dicarboxyterephthalate, C16H18N4O8
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              535
_journal_page_last               536
_journal_paper_doi               10.1515/ncrs-2017-0123
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C16 H18 N4 O8'
_chemical_formula_weight         394.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 116.97(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.517(4)
_cell_length_b                   18.006(7)
_cell_length_c                   6.916(3)
_cell_measurement_reflns_used    7548
_cell_measurement_temperature    272(2)
_cell_measurement_theta_max      28.39
_cell_measurement_theta_min      2.26
_cell_volume                     1611.2(11)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      272(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7546
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.396
_diffrn_reflns_theta_min         2.262
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_description       Block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2068
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0667P)²+0.9058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1387
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1326
_reflns_number_total             2068
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0123_suppl.cif
_cod_data_source_block           2866
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               8106207
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H2O H 0.874(3) 0.0239(9) 0.976(9) 0.10(3) Uiso 0.5 1 d D . P . .
O1A O 0.8488(6) 0.0628(4) 1.0003(8) 0.083(3) Uani 0.5 1 d D . P A 1
O1B O 0.8873(6) 0.0694(3) 0.9735(9) 0.077(3) Uani 0.5 1 d D . P A 2
C1 C 0.80234(18) 0.09111(12) 0.8080(3) 0.0412(6) Uani 1 1 d D . . . .
C2 C 0.75693(14) 0.03864(10) 0.6152(3) 0.0277(4) Uani 1 1 d D . . . .
C3 C 0.71038(14) 0.07486(10) 0.4163(3) 0.0252(4) Uani 1 1 d . . . . .
H1 H 0.7098 0.1265 0.4167 0.030 Uiso 1 1 calc R U . . .
C4 C 0.66478(13) 0.03908(10) 0.2172(3) 0.0238(4) Uani 1 1 d . . . . .
C5 C 0.62023(15) 0.09157(11) 0.0252(3) 0.0286(4) Uani 1 1 d . . . . .
C6 C 0.5000 0.38010(16) 0.5000 0.0365(7) Uani 1 2 d S T P . .
H6 H 0.4656 0.4122 0.3765 0.044 Uiso 1 1 d R U . . .
C7 C 0.36991(16) 0.28844(13) 0.3321(3) 0.0398(5) Uani 1 1 d . . . . .
H7A H 0.3436 0.3207 0.2061 0.048 Uiso 1 1 d R U . . .
H7B H 0.3162 0.2572 0.3561 0.048 Uiso 1 1 d R U . . .
C8 C 0.47141(18) 0.28868(13) 0.7120(3) 0.0389(5) Uani 1 1 d . . . . .
H8A H 0.5069 0.3216 0.8423 0.047 Uiso 1 1 d R U . . .
H8B H 0.4214 0.2583 0.7378 0.047 Uiso 1 1 d R U . . .
C9 C 0.5000 0.19030(15) 0.5000 0.0332(7) Uani 1 2 d S T P . .
H9 H 0.4499 0.1606 0.5217 0.040 Uiso 1 1 d R U . . .
N1 N 0.42276(13) 0.33437(10) 0.5225(3) 0.0357(4) Uani 1 1 d . . . . .
N2 N 0.55084(13) 0.23931(9) 0.6922(2) 0.0327(4) Uani 1 1 d . . . . .
H2 H 0.5821 0.2104 0.8100 0.039 Uiso 1 1 d R U . . .
O2 O 0.77891(14) 0.15570(9) 0.7872(2) 0.0505(5) Uani 1 1 d D . . . .
O3 O 0.62778(12) 0.15884(8) 0.0596(2) 0.0398(4) Uani 1 1 d . . . . .
O4 O 0.57607(12) 0.06621(9) -0.1684(2) 0.0440(4) Uani 1 1 d . . . . .
H1O H 0.579(3) 0.014(3) -0.176(6) 0.053 Uiso 0.5 1 d . U P B -1
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
C1 O1A H2O 101(4) . .
C1 O1B H2O 100(4) . .
O2 C1 O1A 119.5(4) . .
O2 C1 O1B 119.9(3) . .
O2 C1 C2 120.66(18) . .
O1A C1 C2 118.3(3) . .
O1B C1 C2 116.4(3) . .
C3 C2 C2 117.98(11) . 6
C3 C2 C1 113.56(17) . .
C2 C2 C1 128.46(11) 6 .
C4 C3 C2 124.33(18) . .
C4 C3 H1 117.8 . .
C2 C3 H1 117.8 . .
C3 C4 C4 117.69(10) . 6
C3 C4 C5 113.72(16) . .
C4 C4 C5 128.59(10) 6 .
O3 C5 O4 120.86(17) . .
O3 C5 C4 118.68(17) . .
O4 C5 C4 120.47(18) . .
N1 C6 N1 111.1(2) 2_656 .
N1 C6 H6 111.1 2_656 .
N1 C6 H6 108.7 . .
N1 C7 N2 108.54(16) . 2_656
N1 C7 H7A 107.8 . .
N2 C7 H7A 105.0 2_656 .
N1 C7 H7B 107.0 . .
N2 C7 H7B 111.4 2_656 .
H7A C7 H7B 116.9 . .
N1 C8 N2 109.57(15) . .
N1 C8 H8A 108.8 . .
N2 C8 H8A 109.1 . .
N1 C8 H8B 112.7 . .
N2 C8 H8B 110.2 . .
H8A C8 H8B 106.5 . .
N2 C9 N2 107.0(2) . 2_656
N2 C9 H9 107.1 . .
N2 C9 H9 111.4 2_656 .
C8 N1 C7 110.03(18) . .
C8 N1 C6 109.79(15) . .
C7 N1 C6 110.04(15) . .
C9 N2 C8 109.95(14) . .
C9 N2 C7 109.94(14) . 2_656
C8 N2 C7 108.34(17) . 2_656
C9 N2 H2 108.0 . .
C8 N2 H2 110.6 . .
C7 N2 H2 110.0 2_656 .
C5 O4 H1O 114(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1A C1 1.292(5) .
O1A H2O 0.844(15) .
O1B C1 1.305(5) .
O1B H2O 0.844(15) .
C1 O2 1.202(3) .
C1 C2 1.519(3) .
C2 C3 1.390(2) .
C2 C2 1.391(4) 6
C3 C4 1.387(2) .
C3 H1 0.9300 .
C4 C4 1.407(4) 6
C4 C5 1.515(3) .
C5 O3 1.230(2) .
C5 O4 1.278(2) .
C6 N1 1.455(2) 2_656
C6 N1 1.455(2) .
C6 H6 0.9629 .
C7 N1 1.446(3) .
C7 N2 1.520(3) 2_656
C7 H7A 0.9698 .
C7 H7B 1.0337 .
C8 N1 1.433(3) .
C8 N2 1.510(3) .
C8 H8A 1.0042 .
C8 H8B 0.9883 .
C9 N2 1.483(2) .
C9 N2 1.483(2) 2_656
C9 H9 0.9682 .
N2 C7 1.520(3) 2_656
N2 H2 0.8974 .
O4 H1O 0.94(6) .
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
N2 H2 O3 0.90 1.80 2.689(2) 169.8 1_556
N2 H2 O4 0.90 2.60 3.234(3) 127.9 1_556
O4 H1O O4 0.94(6) 1.45(6) 2.384(3) 172(4) 6
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O2 C1 C2 C3 15.3(3) . . . .
O1A C1 C2 C3 -179.0(5) . . . .
O1B C1 C2 C3 -145.0(5) . . . .
O2 C1 C2 C2 -164.95(16) . . . 6
O1A C1 C2 C2 0.8(5) . . . 6
O1B C1 C2 C2 34.8(5) . . . 6
C2 C2 C3 C4 -0.7(2) 6 . . .
C1 C2 C3 C4 179.11(18) . . . .
C2 C3 C4 C4 0.7(2) . . . 6
C2 C3 C4 C5 -179.63(17) . . . .
C3 C4 C5 O3 0.1(3) . . . .
C4 C4 C5 O3 179.67(13) 6 . . .
C3 C4 C5 O4 179.82(18) . . . .
C4 C4 C5 O4 -0.6(2) 6 . . .
N2 C8 N1 C7 61.5(2) . . . .
N2 C8 N1 C6 -59.7(2) . . . .
N2 C7 N1 C8 -61.4(2) 2_656 . . .
N2 C7 N1 C6 59.6(2) 2_656 . . .
N1 C6 N1 C8 60.46(13) 2_656 . . .
N1 C6 N1 C7 -60.78(13) 2_656 . . .
N2 C9 N2 C8 59.32(12) 2_656 . . .
N2 C9 N2 C7 -59.88(12) 2_656 . . 2_656
N1 C8 N2 C9 -60.9(2) . . . .
N1 C8 N2 C7 59.3(2) . . . 2_656
