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

data_7239822
_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
'4(C H4 O), C6 H N3 O9, 4(C10 H18 N), C6 N3 O9, C10 H17 N, O'
_chemical_formula_sum            'C66 H106 N11 O23'
_chemical_formula_weight         1421.61
_chemical_name_common
'adamantan-1-aminium hydrogentrinitrophloroglucinolate trinitrophloroglucinolate hydrate methanol solvate'
_chemical_name_systematic
'adamantan-1-aminium 5-hydroxy-2,4,6-trinitrobenzene-1,3-bis(olate) trinitrobenzene-1,3,5-tris(olate) hydrate methanol solvate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-01
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.1105(14)
_cell_length_b                   26.198(3)
_cell_length_c                   35.156(5)
_cell_measurement_reflns_used    869
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.0270
_cell_measurement_theta_min      4.2860
_cell_volume                     14838(3)
_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 0.997
_diffrn_measurement_details
;
  1 omega -105.00   15.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.1542  -19.0000  120.0000 120

  2 omega -101.00  -48.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.1542  179.0000 -120.0000 53
;
_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  0.3323
_diffrn_reflns_av_unetI/netI     0.4962
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            54282
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         4.142
_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'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       prism
_exptl_crystal_F_000             6104
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.843
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     909
_refine_ls_number_reflns         21581
_refine_ls_number_restraints     140
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.4225
_refine_ls_R_factor_gt           0.1872
_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^)+(0.0707P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2621
_refine_ls_wR_factor_ref         0.3583
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5794
_reflns_number_total             21581
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce01957j2.cif
_cod_data_source_block           V
_cod_database_code               7239822
_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
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H,H) groups, All O(H) groups
2. Restrained distances
 O207-H1
 2 with sigma of 0.02
 H2-O5_$1
 2.2 with sigma of 0.02
3. Rigid bond restraints
 C106, C105, C104, C102, C103, C101
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C205, C206, C201, C202, C204, C203
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(O4) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C105)
\\sim Ueq, Uanis(N203) \\sim Ueq: with sigma of 0.0001 and sigma for terminal
atoms of 0.0002
Uanis(O3) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(O2) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.2
Uanis(C101) \\sim Ueq, Uanis(C106) \\sim Ueq, Uanis(C102) \\sim Ueq,
Uanis(C103) \\sim Ueq, Uanis(C104) \\sim Ueq, Uanis(C105) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.2
Uanis(C202) \\sim Ueq, Uanis(C203) \\sim Ueq, Uanis(C204) \\sim Ueq,
Uanis(C205) \\sim Ueq, Uanis(C206) \\sim Ueq, Uanis(C201) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.2
Uanis(O3) \\sim Ueq: with sigma of 0.0002 and sigma for terminal atoms of 0.0004
Uanis(C3) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5.a Ternary CH refined with riding coordinates:
 C48(H48), C44(H44), C49(H49), C33(H33), C38(H38), C35(H35), C22(H22),
 C24(H24), C27(H27), C55(H55), C52(H52), C57(H57), C16(H16), C14(H14)
5.b Secondary CH2 refined with riding coordinates:
 C45(H45A,H45B), C46(H46A,H46B), C43(H43A,H43B), C42(H42A,H42B), C47(H47A,
 H47B), C41(H41A,H41B), C34(H34A,H34B), C36(H36A,H36B), C31(H31A,H31B),
 C37(H37A,H37B), C32(H32A,H32B), C39(H39A,H39B), C28(H28A,H28B), C21(H21A,H21B),
  C25(H25A,H25B), C26(H26A,H26B), C23(H23A,H23B), C29(H29A,H29B), C56(H56A,
 H56B), C54(H54A,H54B), C58(H58A,H58B), C51(H51A,H51B), C53(H53A,H53B),
 C59(H59A,H59B), C11(H11A,H11B), C19(H19A,H19B), C17(H17A,H17B), C18(H18A,H18B),
  C15(H15A,H15B), C13(H13A,H13B)
5.c Me refined with riding coordinates:
 N40(H40A,H40B,H40C), N30(H30A,H30B,H30C), N20(H20A,H20B,H20C), N50(H50A,H50B,
 H50C), N10(H10A,H10B,H10C)
5.d Tetrahedral OH refined with riding coordinates:
 O201(H201)
5.e Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C2(H2A,H2B,H2C), C1(H1A,H1B,H1C), C3(H3A,H3B,H3C)
5.f Idealised tetrahedral OH refined as rotating group:
 O4(H4), O2(H2), O1(H1), O3(H3)
;
_shelx_res_checksum              97821
_olex2_submission_special_instructions 'No special instructions were received'