Stoichiometry of Adamantylamine-Trinitrophloroglucinol Salts Controlled by Solvate Formation
Smokrović, Kristina; Stilinovic, Vladimir; CrystEngComm  (2020) –; doi:10.1039/C9CE01957J

data_7239816
_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
;
  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

  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

  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

  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

  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       '\w 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/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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
_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)
;
_shelx_res_checksum              34651
_olex2_date_sample_data_collection 2016-11-08
_olex2_submission_special_instructions 'No special instructions were received'