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

data_7239826
_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 H N3 O9), 4(C10 H18 N), 2(C2 H2 F3 O)'
_chemical_formula_sum            'C56 H78 F6 N10 O20'
_chemical_formula_weight         1325.28
_chemical_name_common
'adamantan-1-aminium hidrohentrinitrophloroglucinolate 2,2,2-trifluoroethanol solvate'
_chemical_name_systematic
'adamantan-1-aminium 5-hydroxytrinitrobenzene-1,3-bis(olate) 2,2,2-trifluoroethanol solvate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_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                 103.005(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.5039(7)
_cell_length_b                   18.8674(6)
_cell_length_c                   20.3861(7)
_cell_measurement_reflns_used    3421
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      40.7373
_cell_measurement_theta_min      4.0451
_cell_volume                     6559.9(4)
_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(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            90384
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         4.152
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.113
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       plates
_exptl_crystal_F_000             2792
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.175
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.405
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     765
_refine_ls_number_reflns         11479
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1332.199
_refine_ls_R_factor_all          0.1750
_refine_ls_R_factor_gt           0.1245
_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/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3587
_refine_ls_wR_factor_ref         0.3987
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6719
_reflns_number_total             11479
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce01957j2.cif
_cod_data_source_block           vii
_cod_database_code               7239826
_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
 C2-F1 = C2-F2 = C2-F3
 1.332 with sigma of 0.00001
 C1-C2
 1.475 with sigma of 0.00001
 C5-F4 = C5-F5 = C5-F6
 1.332 with sigma of 0.00001
 C4-C5
 1.475 with sigma of 0.00001
 O2-C4
 1.348 with sigma of 0.00001
 O203-O1
 3.408 with sigma of 0.00001
 O1-C1
 1.343 with sigma of 0.02
 O1-O205_$1
 2.958 with sigma of 0.000001
 F1-F2 = F1-F3 = F2-F3
 2.132 with sigma of 0.00001
 O1-C1
 2.355 with sigma of 0.00001
 F4-F5 = F4-F6 = F5-F6
 2.132 with sigma of 0.00001
 O2-C5
 2.355 with sigma of 0.00001
3. Rigid bond restraints
 O2, C4, C5, F4, F5, F6
 with sigma for 1-2 distances of 0.000001 and sigma for 1-3 distances of
 0.000001
 C1, C2, O1, F1, F2, F3
 with sigma for 1-2 distances of 0.000001 and sigma for 1-3 distances of
 0.000001
4. Uiso/Uaniso restraints and constraints
Uanis(O202) \\sim Ueq, Uanis(O203) \\sim Ueq: with sigma of 0.00001 and sigma
for terminal atoms of 0.00002
Uanis(O205) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Others
 Sof(O22A)=Sof(O23A)=1-FVAR(1)
 Sof(O202)=Sof(O203)=FVAR(1)
6.a Free rotating group:
 O2(C4,C5,F4,F6,F5), O1(C1,C2,F1,F3,F2)
6.b Ternary CH refined with riding coordinates:
 C32(H32), C37(H37), C35(H35), C22(H22), C27(H27), C25(H25), C17(H17),
 C42(H42), C15(H15), C47(H47), C12(H12), C45(H45)
6.c Secondary CH2 refined with riding coordinates:
 C39(H39A,H39B), C38(H38A,H38B), C31(H31A,H31B), C34(H34A,H34B), C21(H21A,
 H21B), C28(H28A,H28B), C29(H29A,H29B), C36(H36A,H36B), C33(H33A,H33B),
 C19(H19A,H19B), C18(H18A,H18B), C24(H24A,H24B), C23(H23A,H23B), C26(H26A,H26B),
  C11(H11A,H11B), C41(H41A,H41B), C44(H44A,H44B), C14(H14A,H14B), C13(H13A,
 H13B), C43(H43A,H43B), C49(H49A,H49B), C16(H16A,H16B), C46(H46A,H46B),
 C48(H48A,H48B), C4(H4A,H4B), C1(H1A,H1B)
6.d Idealised Me refined as rotating group:
 N10(H10A,H10B,H10C), N30(H30A,H30B,H30C), N20(H20A,H20B,H20C), N40(H40A,H40B,
 H40C)
6.e Idealised tetrahedral OH refined as rotating group:
 O101(H101), O201(H201)
;
_shelx_res_checksum              70539
_olex2_submission_special_instructions 'No special instructions were received'