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

data_7239818
_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), C H4 O, H2 O'
_chemical_formula_sum            'C73 H114 N12 O20'
_chemical_formula_weight         1479.76
_chemical_name_common
'adamantan-1-aminium trinitrophloroglucinolate hydrate methanol solvate'
_chemical_name_systematic
'adamantan-1-aminium trinitrobenzene-1,3,5-tris(olate) hydrate methanol solvate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-06-29
_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                 93.164(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.9589(6)
_cell_length_b                   16.0224(7)
_cell_length_c                   26.5928(13)
_cell_measurement_reflns_used    4026
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.2330
_cell_measurement_theta_min      4.2400
_cell_volume                     8065.7(6)
_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
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_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     -2.00  95.50   0.75   41.00    --   25.57  77.00  30.00  130
  2  \w    -52.00  42.50   0.75   41.00    --  -28.54  37.00  30.00  126
  3  \w   -105.00 -36.00   0.75   41.00    --  -28.54 179.00   0.00   92
  4  \w    -74.00 -47.00   0.75   41.00    --  -28.54-179.00  60.00   36
;
_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  0.1047
_diffrn_reflns_av_unetI/netI     0.1644
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            39384
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         4.118
_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    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78246
_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 light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       prism
_exptl_crystal_F_000             3184
_exptl_crystal_recrystallization_method 'slow evaporation from methanol'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.303
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1033
_refine_ls_number_reflns         15797
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.2384
_refine_ls_R_factor_gt           0.1103
_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^)+(0.1835P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2936
_refine_ls_wR_factor_ref         0.3772
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5876
_reflns_number_total             15797
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce01957j2.cif
_cod_data_source_block           IV
_cod_database_code               7239818
_shelx_shelxl_version_number     2016/4
_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 C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O102-N101 = O103-N101
 1.22 with sigma of 0.0002
 O102-O103
 2.15 with sigma of 0.0002
 O205-N202 = O206-N202
 1.22 with sigma of 0.0002
 O206-O205
 2.15 with sigma of 0.0002
 N202-O205 \\sim N202-O1
 with sigma of 0.02
 N202-O206 \\sim N202-O2
 with sigma of 0.02
 N103-O109 \\sim N103-O4
 with sigma of 0.02
 N103-O108 \\sim N103-O3
 with sigma of 0.02
3. Others
 Sof(O13A)=Sof(O12A)=1-FVAR(1)
 Sof(O102)=Sof(O103)=FVAR(1)
 Sof(O23A)=Sof(O22A)=1-FVAR(2)
 Sof(O203)=Sof(O202)=FVAR(2)
 Sof(O2)=Sof(O1)=1-FVAR(3)
 Sof(O205)=Sof(O206)=FVAR(3)
 Sof(O3)=Sof(O4)=1-FVAR(4)
 Sof(O109)=Sof(O108)=FVAR(4)
4.a Free rotating group:
 O301(H30D,H30E)
4.b Ternary CH refined with riding coordinates:
 C44(H44), C15(H15), C54(H54), C22(H22), C12(H12), C46(H46), C020(H020),
 C25(H25), C56(H56), C38(H38), C27(H27), C69(H69), C42(H42), C62(H62), C67(H67),
  C34(H34), C32(H32), C52(H52)
4.c Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C21(H21A,H21B), C16(H16A,H16B), C58(H58A,H58B), C39(H39A,
 H39B), C49(H49A,H49B), C18(H18A,H18B), C11(H11A,H11B), C28(H28A,H28B),
 C65(H65A,H65B), C45(H45A,H45B), C59(H59A,H59B), C47(H47A,H47B), C35(H35A,H35B),
  C61(H61A,H61B), C66(H66A,H66B), C17(H17A,H17B), C51(H51A,H51B), C14(H14A,
 H14B), C13(H13A,H13B), C55(H55A,H55B), C24(H24A,H24B), C41(H41A,H41B),
 C31(H31A,H31B), C43(H43A,H43B), C26(H26A,H26B), C48(H48A,H48B), C36(H36A,H36B),
  C57(H57A,H57B), C63(H63A,H63B), C37(H37A,H37B), C53(H53A,H53B), C23(H23A,
 H23B), C33(H33A,H33B), C64(H64A,H64B), C68(H68A,H68B)
4.d Idealised Me refined as rotating group:
 N10(H10A,H10B,H10C), N20(H20A,H20B,H20C), N30(H30A,H30B,H30C), N60(H60A,H60B,
 H60C), N40(H40A,H40B,H40C), N50(H50A,H50B,H50C), C401(H40D,H40E,H40F)
4.e Idealised tetrahedral OH refined as rotating group:
 O401(H401)
;
_shelx_res_checksum              81796
_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
;