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

data_7239815
_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         '6(C10 H18 N), C2 H6 O, O, 2(C6 N3 O9)'
_chemical_formula_sum            'C74 H114 N12 O20'
_chemical_formula_weight         1491.77
_chemical_name_common
'adamantan-1-aminium trinitrophloroglucinolate hydrate ethanol solvate'
_chemical_name_systematic
'adamantan-1-aminium trinitrobenzene-1,3,5-tris(olate) hydrate ethanol 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   geom
_audit_creation_date             2018-07-04
_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                90.00(2)
_cell_angle_beta                 92.65(2)
_cell_angle_gamma                90.00(2)
_cell_formula_units_Z            4
_cell_length_a                   18.805(5)
_cell_length_b                   15.975(4)
_cell_length_c                   27.184(6)
_cell_measurement_reflns_used    1670
_cell_measurement_temperature    293
_cell_measurement_theta_max      30.7390
_cell_measurement_theta_min      4.7540
_cell_volume                     8158(3)
_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      293(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.972
_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  0.1654
_diffrn_reflns_av_unetI/netI     0.1749
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            25978
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         4.038
_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  0.98189
_exptl_absorpt_correction_type   multi-scan
_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    1.215
_exptl_crystal_description       needle
_exptl_crystal_F_000             3208
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.874
_refine_diff_density_min         -0.913
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1001
_refine_ls_number_reflns         15598
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.2689
_refine_ls_R_factor_gt           0.1475
_refine_ls_shift/su_max          0.008
_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          0.3586
_refine_ls_wR_factor_ref         0.4628
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5819
_reflns_number_total             15598
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce01957j2.cif
_cod_data_source_block           i
_cod_original_cell_volume        8158(4)
_cod_database_code               7239815
_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
2. Restrained distances
 O209-O208
 2.098 with sigma of 0.0002
 O204-O401
 2.798 with sigma of 0.0002
 O401-N60_$1
 2.751 with sigma of 0.00001
 O401-O19A_$1
 2.772 with sigma of 0.000001
 O108-O109 \\sim O19A-O18A
 with sigma of 0.02
 N103-O108 \\sim N103-O19A
 with sigma of 0.04
 N103-O109 \\sim N103-O18A
 with sigma of 0.04
 N203-O209 \\sim N203-O28A
 with sigma of 0.02
 N203-O208 \\sim N203-O29A
 with sigma of 0.02
3. Rigid bond restraints
 O401
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 N60, N60
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(O401) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Others
 Sof(O19A)=Sof(O18A)=1-FVAR(1)
 Sof(O108)=Sof(O109)=FVAR(1)
 Sof(O28A)=Sof(O29A)=1-FVAR(2)
 Sof(O209)=Sof(O208)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C28(H28), C68(H68), C52(H52), C42(H42), C48(H48), C44(H44), C54(H54),
 C58(H58), C64(H64), C62(H62), C38(H38), C34(H34), C32(H32), C14(H14), C18(H18),
  C12(H12), C22(H22), C24(H24)
6.b Secondary CH2 refined with riding coordinates:
 C301(H30G,H30H), C69(H69A,H69B), C65(H65A,H65B), C41(H41A,H41B), C55(H55A,
 H55B), C59(H59A,H59B), C61(H61A,H61B), C51(H51A,H51B), C45(H45A,H45B),
 C66(H66A,H66B), C49(H49A,H49B), C67(H67A,H67B), C43(H43A,H43B), C56(H56A,H56B),
  C53(H53A,H53B), C63(H63A,H63B), C57(H57A,H57B), C46(H46A,H46B), C47(H47A,
 H47B), C35(H35A,H35B), C39(H39A,H39B), C31(H31A,H31B), C36(H36A,H36B),
 C33(H33A,H33B), C37(H37A,H37B), C15(H15A,H15B), C19(H19A,H19B), C11(H11A,H11B),
  C13(H13A,H13B), C16(H16A,H16B), C17(H17A,H17B), C25(H25A,H25B), C21(H21A,
 H21B), C23(H23A,H23B), C26(H26A,H26B), C29(H29A,H29B), C27(H27A,H27B)
6.c Idealised Me refined as rotating group:
 N20(H20A,H20B,H20C), C302(H30D,H30E,H30F), N50(H50A,H50B,H50C), N40(H40A,H40B,
 H40C), N60(H60A,H60B,H60C), N30(H30A,H30B,H30C), N10(H10A,H10B,H10C)
6.d Idealised tetrahedral OH refined as rotating group:
 O301(H301)
;
_shelx_res_checksum              58365
_olex2_submission_special_instructions 'No special instructions were received'