#------------------------------------------------------------------------------
#$Date: 2020-01-24 04:40:13 +0200 (Fri, 24 Jan 2020) $
#$Revision: 247175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/98/7239816.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_7239816
loop_
_publ_author_name
'Smokrović, Kristina'
'Stilinovic, Vladimir'
_publ_section_title
;
 Stoichiometry of Adamantylamine-Trinitrophloroglucinol Salts Controlled
 by Solvate Formation
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C9CE01957J
_journal_year                    2020
_chemical_formula_moiety         'C6 H N3 O9, 2(C10 H18 N), 2(C4 H8 O)'
_chemical_formula_sum            'C34 H53 N5 O11'
_chemical_formula_weight         707.81
_chemical_name_common
'adamantan-1-aminium hydrogentrinitrophloroglucinolate tetrahydrofurane solvate'
_chemical_name_systematic
'adamantan-1-aminium trinitrobenzene-1,3,5-tris(olate) tetrahydrofurane solvate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-07-17 deposited with the CCDC.	2020-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.81(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.445(5)
_cell_length_b                   17.0130(19)
_cell_length_c                   15.845(4)
_cell_measurement_reflns_used    1868
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      37.2688
_cell_measurement_theta_min      3.8168
_cell_volume                     3686.0(19)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -103.86   32.14   1.0000    8.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -34.0000   -5.0000   90.0000    0.0000    0.0000 136

#__ type_ start__ end____ width___ exp.time_
  2 omega  -92.33   -8.33   1.0000    8.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -24.0000  -45.0000   60.0000    0.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega  -35.00   66.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       34.0000  -90.0000  -40.0000    0.0000    0.0000 101

#__ type_ start__ end____ width___ exp.time_
  4 omega  -93.14   -6.14   1.0000    8.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -24.0000  -35.0000  160.0000    0.0000    0.0000 87

#__ type_ start__ end____ width___ exp.time_
  5 omega  -99.98    9.02   1.0000    8.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -30.0000    0.0000 -120.0000    0.0000    0.0000 109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_radiation_collimation    0.8
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1063
_diffrn_reflns_av_unetI/netI     0.1689
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17143
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.824
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark yellow'
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       needle
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.365
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3610
_refine_ls_number_restraints     71
_refine_ls_restrained_S_all      1.373
_refine_ls_R_factor_all          0.3257
_refine_ls_R_factor_gt           0.1303
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2939
_refine_ls_wR_factor_ref         0.3522
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1179
_reflns_number_total             3610
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce01957j2.cif
_cod_data_source_block           IX
_cod_original_cell_volume        3686.1(17)
_cod_database_code               7239816
_shelx_shelxl_version_number     2016/4
_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.
;
_reflns_odcompleteness_completeness 79.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     37.46
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C3-C4 \\sim C4-C5 \\sim C5-C6
 with sigma of 0.02
 O1-C3 \\sim O1-C6
 with sigma of 0.02
 O1-C4 \\sim O1-C5
 with sigma of 0.04
 C4-C6 \\sim C3-C5
 with sigma of 0.04
 O102-O103 \\sim O3-O2
 with sigma of 0.02
 N101-O102 \\sim N101-O3
 with sigma of 0.04
 N101-O103 \\sim N101-O2
 with sigma of 0.04
3. Restrained planarity
 N101, C102, C101, O101, H101
 with sigma of 0.1
4. Rigid bond restraints
 O3, O2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O103, O102
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
5. Uiso/Uaniso restraints and constraints
O1 \\sim C3 \\sim C4 \\sim C5 \\sim C6: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
6. Rigid body (RIGU) restrains
 O1, C3, C4, C5, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Sof(O2)=Sof(O3)=1-FVAR(1)
 Sof(O102)=Sof(O103)=FVAR(1)
 Fixed Sof: H101(0.5)
8.a Free rotating group:
 O1(C3,C4,C5,C6)
8.b Ternary CH refined with riding coordinates:
 C00H(H00J), C00J(H00M), C00L(H00N)
8.c Secondary CH2 refined with riding coordinates:
 C00D(H00D,H00E), C00F(H00F,H00G), C00G(H00H,H00I), C00I(H00K,H00L), C00M(H00O,
 H00P), C00P(H00Q,H00R), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
8.d Idealised Me refined as rotating group:
 N005(H00A,H00B,H00C)
8.e Idealised tetrahedral OH refined as rotating group:
 O101(H101)
;
_olex2_date_sample_data_collection 2016-11-08
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_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
O104 O 0.5068(3) 0.4212(2) 0.6035(3) 0.0559(14) Uani 1 1 d . . . . .
O101 O 0.500000 0.1796(4) 0.750000 0.095(3) Uani 1 2 d S T P . .
H101 H 0.489234 0.163548 0.698937 0.143 Uiso 0.5 1 calc GR . . . .
N102 N 0.500000 0.5047(5) 0.750000 0.070(3) Uani 1 2 d S T P . .
N005 N 0.6239(4) 0.5397(3) 0.5634(4) 0.0576(18) Uani 1 1 d . . . . .
H00A H 0.577596 0.549234 0.511633 0.069 Uiso 1 1 calc GR . . . .
H00B H 0.643613 0.584864 0.591899 0.069 Uiso 1 1 calc GR . . . .
H00C H 0.599914 0.508730 0.596621 0.069 Uiso 1 1 calc GR . . . .
O105 O 0.5610(6) 0.5401(3) 0.7282(4) 0.120(3) Uani 1 1 d . . . . .
C104 C 0.500000 0.4218(5) 0.750000 0.052(3) Uani 1 2 d S T P . .
C103 C 0.5056(5) 0.3828(4) 0.6721(4) 0.0427(18) Uani 1 1 d . . . . .
C102 C 0.5043(5) 0.3012(3) 0.6745(4) 0.0484(19) Uani 1 1 d . . . . .
C101 C 0.500000 0.2590(6) 0.750000 0.060(3) Uani 1 2 d S T P . .
C00B C 0.7076(6) 0.5004(4) 0.5469(5) 0.054(2) Uani 1 1 d . . . . .
C00D C 0.6718(6) 0.4330(5) 0.4879(6) 0.084(3) Uani 1 1 d . . . . .
H00D H 0.626948 0.450929 0.431380 0.101 Uiso 1 1 calc R . . . .
H00E H 0.636699 0.397473 0.514639 0.101 Uiso 1 1 calc R . . . .
C00F C 0.7764(7) 0.4724(5) 0.6351(6) 0.079(3) Uani 1 1 d . . . . .
H00F H 0.742967 0.435902 0.662354 0.095 Uiso 1 1 calc R . . . .
H00G H 0.798741 0.516682 0.675082 0.095 Uiso 1 1 calc R . . . .
C00G C 0.7590(6) 0.5578(5) 0.5060(6) 0.085(3) Uani 1 1 d . . . . .
H00H H 0.779967 0.603031 0.544770 0.102 Uiso 1 1 calc R . . . .
H00I H 0.714869 0.575942 0.449171 0.102 Uiso 1 1 calc R . . . .
C00H C 0.8637(8) 0.4318(7) 0.6191(8) 0.118(4) Uani 1 1 d . . . . .
H00J H 0.908530 0.414410 0.676713 0.142 Uiso 1 1 calc R . . . .
C00I C 0.8288(9) 0.3603(5) 0.5610(8) 0.110(4) Uani 1 1 d . . . . .
H00K H 0.795211 0.324489 0.589009 0.132 Uiso 1 1 calc R . . . .
H00L H 0.883869 0.332859 0.552308 0.132 Uiso 1 1 calc R . . . .
C00J C 0.7592(8) 0.3887(6) 0.4717(8) 0.109(4) Uani 1 1 d . . . . .
H00M H 0.736016 0.344676 0.430295 0.131 Uiso 1 1 calc R . . . .
C00L C 0.8469(10) 0.5180(6) 0.4923(11) 0.122(4) Uani 1 1 d . . . . .
H00N H 0.880816 0.555352 0.465431 0.146 Uiso 1 1 calc R . . . .
C00M C 0.9169(8) 0.4886(6) 0.5793(10) 0.132(5) Uani 1 1 d . . . . .
H00O H 0.972220 0.462932 0.569067 0.159 Uiso 1 1 calc R . . . .
H00P H 0.941043 0.532357 0.619716 0.159 Uiso 1 1 calc R . . . .
C00P C 0.8131(9) 0.4512(8) 0.4324(9) 0.136(5) Uani 1 1 d . . . . .
H00Q H 0.868771 0.426728 0.421345 0.163 Uiso 1 1 calc R . . . .
H00R H 0.769143 0.469839 0.375814 0.163 Uiso 1 1 calc R . . . .
N101 N 0.5013(8) 0.2568(5) 0.5972(5) 0.085(3) Uani 1 1 d D . . . .
O102 O 0.491(2) 0.1895(8) 0.5917(14) 0.136(11) Uani 0.54(3) 1 d D U . A 1
O103 O 0.482(3) 0.2907(8) 0.5239(10) 0.148(13) Uani 0.54(3) 1 d D U . A 1
O1 O 0.6815(7) 0.6739(3) 0.6775(6) 0.162(4) Uani 1 1 d D U . . .
C3 C 0.5955(6) 0.7184(5) 0.6724(8) 0.191(6) Uani 1 1 d DG U . . .
H3A H 0.564564 0.697805 0.713767 0.229 Uiso 1 1 calc R . . . .
H3B H 0.548903 0.716270 0.612634 0.229 Uiso 1 1 calc R . . . .
C4 C 0.6297(8) 0.8031(4) 0.6970(8) 0.223(7) Uani 1 1 d DG U . . .
H4A H 0.648485 0.811682 0.760860 0.268 Uiso 1 1 calc R . . . .
H4B H 0.579521 0.840695 0.666720 0.268 Uiso 1 1 calc R . . . .
C5 C 0.7184(8) 0.8084(4) 0.6638(9) 0.235(7) Uani 1 1 d DG U . . .
H5A H 0.698536 0.819410 0.600431 0.282 Uiso 1 1 calc R . . . .
H5B H 0.764206 0.848324 0.695850 0.282 Uiso 1 1 calc R . . . .
C6 C 0.7621(6) 0.7258(5) 0.6847(9) 0.254(7) Uani 1 1 d DG U . . .
H6A H 0.795112 0.710972 0.642650 0.304 Uiso 1 1 calc R . . . .
H6B H 0.808908 0.723971 0.744464 0.304 Uiso 1 1 calc R . . . .
O2 O 0.5772(18) 0.2643(14) 0.5737(18) 0.122(12) Uani 0.46(3) 1 d D U . A -1
O3 O 0.454(3) 0.205(2) 0.567(3) 0.23(2) Uani 0.46(3) 1 d D U . A -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
O105 N102 O105 120.1(10) 2_656 .
O105 N102 C104 119.9(5) . .
O105 N102 C104 119.9(5) 2_656 .
N102 C104 C103 117.7(4) . .
N102 C104 C103 117.7(4) . 2_656
C103 C104 C103 124.5(8) 2_656 .
O104 C103 C104 121.3(6) . .
O104 C103 C102 122.7(6) . .
C102 C103 C104 115.9(6) . .
O102a N101 C102 123.9(12) . .
O103a N101 C102 119.3(10) . .
O102a N101 O103 113.8(13) . .
O102a N101 O2 100.2(17) . .
O103a N101 O2 69.0(11) . .
O102a O3 N101 77(3) . .
O102a O3 O103 110(3) . .
C103 C102 C101 122.3(6) . .
C103 C102 N101 120.1(6) . .
C101 C102 N101 117.4(6) . .
O101 C101 C102 120.5(4) . 2_656
O101 C101 C102 120.5(4) . .
C102 C101 C102 119.0(9) . 2_656
N005 C00B C00F 108.1(6) . .
N005 C00B C00G 109.3(6) . .
C00D C00B N005 109.1(6) . .
C00D C00B C00F 109.6(6) . .
C00D C00B C00G 110.9(7) . .
C00G C00B C00F 109.7(7) . .
C00B C00D C00J 110.2(8) . .
C00B C00F C00H 108.7(7) . .
C00B C00G C00L 109.0(7) . .
C00I C00H C00F 109.5(9) . .
C00M C00H C00F 110.0(8) . .
C00M C00H C00I 112.4(10) . .
C00H C00I C00J 107.5(8) . .
C00D C00J C00P 105.7(8) . .
C00I C00J C00D 109.0(8) . .
C00I C00J C00P 108.7(10) . .
C00M C00L C00G 111.3(10) . .
C00P C00L C00G 108.7(11) . .
C00P C00L C00M 108.8(9) . .
C00H C00M C00L 108.4(9) . .
C00L C00P C00J 112.1(9) . .
N101 O103a O2 56.5(9) . .
N101 O103a O3 40.8(12) . .
O2 O103a O3 79.7(16) . .
O2 N101 C102 114.0(10) . .
O3 N101 C102 128.2(17) . .
O3 N101 O102 31(3) . .
O3 N101 O103 93(2) . .
O3 N101 O2 115.3(19) . .
C3 O1 C6 110.1 . .
O1 C3 C4 106.3 . .
C3 C4 C5 101.8 . .
C6 C5 C4 101.8 . .
O1 C6 C5 106.3 . .
N101 O2 O103 54.6(9) . .
N101 O3 O103 46.6(14) . .
O3 O102a N101 71(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O104 C103 1.273(7) .
O103a O2 1.43(2) .
O102a O3 0.62(6) .
O103a O3 1.71(4) .
O101 C101 1.351(11) .
N102 O105 1.205(6) .
N102 O105 1.205(6) 2_656
N102 C104 1.410(12) .
N005 C00B 1.478(8) .
C104 C103 1.427(7) 2_656
C104 C103 1.427(7) .
C103 C102 1.389(8) .
C102 C101 1.413(8) .
C102 N101 1.428(9) .
C101 C102 1.414(8) 2_656
C00B C00D 1.465(10) .
C00B C00F 1.508(10) .
C00B C00G 1.495(9) .
C00D C00J 1.560(11) .
C00F C00H 1.529(12) .
C00G C00L 1.515(12) .
C00H C00I 1.511(13) .
C00H C00M 1.494(12) .
C00I C00J 1.526(13) .
C00J C00P 1.562(13) .
C00L C00M 1.507(16) .
C00L C00P 1.460(15) .
N101 O102 1.153(14) .
N101 O103 1.244(13) .
N101 O2 1.273(14) .
N101 O3 1.12(2) .
O1 C3 1.4362 .
O1 C6 1.4364 .
C3 C4 1.5321 .
C4 C5 1.5359 .
C5 C6 1.5317 .
