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

data_7239820
_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         '2(C6 N3 O9), 6(C10 H18 N), 2(C2 H3 F3 O)'
_chemical_formula_sum            'C76 H114 F6 N12 O20'
_chemical_formula_weight         1629.79
_chemical_name_common
'adamantan-1-aminium trinitrophloroglucinolate bis(2,2,2-trifluoroethanol) solvate'
_chemical_name_systematic
'adamantan-1-aminium trinitrobenzene-1,3,5-tris(olate) bis(2,2,2-trifluoroethanol) solvate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-16
_audit_creation_method
;
Olex2 1.2
(compiled May 29 2018 13:30:08 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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.370(3)
_cell_length_b                   16.060(2)
_cell_length_c                   27.340(3)
_cell_measurement_reflns_used    912
_cell_measurement_temperature    298
_cell_measurement_theta_max      17.1860
_cell_measurement_theta_min      4.2960
_cell_volume                     8065.9(19)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_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      298.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -23.00  78.25   0.75   40.00    --   28.65  19.00 -60.00  135
  2  \w     41.00  95.00   0.75   40.00    --   28.65 179.00  90.00   72
  3  \w    -94.00 -61.75   0.75   40.00    --  -31.15-179.00  30.00   43
  4  \w    -89.00 -23.00   0.75   40.00    --  -31.15 -57.00 150.00   88
  5  \w   -103.00 -40.00   0.75   40.00    --  -31.15-179.00 -30.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.3454
_diffrn_reflns_av_unetI/netI     0.3713
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            39378
_diffrn_reflns_point_group_measured_fraction_full 0.753
_diffrn_reflns_point_group_measured_fraction_max 0.747
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         4.069
_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    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       plate
_exptl_crystal_F_000             3472
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 451 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1053
_refine_ls_number_reflns         11843
_refine_ls_number_restraints     131
_refine_ls_restrained_S_all      0.917
_refine_ls_R_factor_all          0.3572
_refine_ls_R_factor_gt           0.1129
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0890P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2217
_refine_ls_wR_factor_ref         0.3249
_reflns_Friedel_coverage         0.468
_reflns_Friedel_fraction_full    0.500
_reflns_Friedel_fraction_max     0.486
_reflns_number_gt                2998
_reflns_number_total             11843
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce01957j2.cif
_cod_data_source_block           ii
_cod_original_cell_volume        8066(2)
_cod_database_code               7239820
_shelx_shelxl_version_number     2018/3
_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
 F5-C6 = F6-C6 = F4-C6
 1.327 with sigma of 0.0002
 F3-C3 = F1-C3 = F2-C3
 1.327 with sigma of 0.02
 F3-F1
 2.125 with sigma of 0.02
 F1-F2
 2.125 with sigma of 0.02
 F3-F2
 2.125 with sigma of 0.02
 F5-F6
 2.125 with sigma of 0.02
 F6-F4
 2.125 with sigma of 0.02
 F5-F4
 2.125 with sigma of 0.02
 C49-C47 = C49-C42
 1.512 with sigma of 0.02
 C3-C2
 1.512 with sigma of 0.02
 C2-C3
 1.512 with sigma of 0.02
 O1-C2
 1.35 with sigma of 0.02
 O106-O105 = O103-O102 = O203-O202 = O205-O206 = O208-O209
 2.1485 with sigma of 0.02
 O108-O109
 2.1485 with sigma of 0.02
 O1-C2 = O4-C5
 1.47 with sigma of 0.002
 C6-C5
 1.434 with sigma of 0.001
 C202-C201 = C203-C202 = C204-C203 = C205-C204 = C206-C205 = C206-C201
 1.46 with sigma of 0.00002
 O201-H1
 1.98 with sigma of 0.001
 O207-C204
 1.236 with sigma of 0.0001
 C201-C204
 2.801 with sigma of 0.00001
3. Restrained planarity
 O109, N103, O108, C106
 with sigma of 0.001
4. Rigid bond restraints
 N103, C106
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 O206, N202
 with sigma for 1-2 distances of 0.00001 and sigma for 1-3 distances of 0.00001
 C201, C206, C205, C204, C203, C202
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C6, F5, F4, F6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N103, O109, O108
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 O26A, N202, O25A
 with sigma for 1-2 distances of 0.00001 and sigma for 1-3 distances of 0.00001
 C203, C204, C205, C206, C201, C202
 with sigma for 1-2 distances of 0.000001 and sigma for 1-3 distances of
 0.000001
5. Uiso/Uaniso restraints and constraints
Uanis(F2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(F1) \\sim
Ueq, Uanis(F3) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(O4)
\\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(F4) \\sim Ueq,
Uanis(F6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
6. Others
 Fixed Sof: O206(0.59625) O205(0.59625) O26A(0.40375) O25A(0.40375)
7.a Ternary CH refined with riding coordinates:
 C22(H22), C27(H27), C37(H37), C62(H62), C52(H52), C44(H44), C54(H54),
 C32(H32), C24(H24), C34(H34), C64(H64), C17(H17), C47(H47), C12(H12), C42(H42),
  C14(H14), C57(H57), C67(H67)
7.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C11(H11A,H11B), C41(H41A,H41B), C21(H21A,H21B), C61(H61A,H61B),
 C55(H55A,H55B), C25(H25A,H25B), C65(H65A,H65B), C26(H26A,H26B), C48(H48A,H48B),
  C35(H35A,H35B), C43(H43A,H43B), C29(H29A,H29B), C45(H45A,H45B), C56(H56A,
 H56B), C31(H31A,H31B), C36(H36A,H36B), C38(H38A,H38B), C18(H18A,H18B),
 C15(H15A,H15B), C66(H66A,H66B), C28(H28A,H28B), C23(H23A,H23B), C63(H63A,H63B),
  C19(H19A,H19B), C69(H69A,H69B), C53(H53A,H53B), C33(H33A,H33B), C16(H16A,
 H16B), C58(H58A,H58B), C68(H68A,H68B), C51(H51A,H51B), C59(H59A,H59B),
 C39(H39A,H39B), C46(H46A,H46B), C13(H13A,H13B), C5(H5A,H5B), C49(H49A,H49B)
7.c Idealised Me refined as rotating group:
 N40(H40A,H40B,H40C), N30(H30A,H30B,H30C), N20(H20A,H20B,H20C), N10(H10A,H10B,
 H10C), N50(H50A,H50B,H50C), N60(H60A,H60B,H60C)
7.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O1(H1)
;
_shelx_res_checksum              58035
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;