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

data_7239817
_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         'C6 N3 O9, 3(C10 H18 N), 2(O)'
_chemical_formula_sum            'C36 H54 N6 O11'
_chemical_formula_weight         746.85
_chemical_name_common
'adamantan-1-aminium trinitrophloroglucinolate hydrate'
_chemical_name_systematic
'adamantan-1-aminium trinitrobenzene-1,3,5-tris(olate) hydrate'
_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             2018-07-12
_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                 105.420(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4004(12)
_cell_length_b                   16.1041(9)
_cell_length_c                   18.7528(10)
_cell_measurement_reflns_used    2358
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.9550
_cell_measurement_theta_min      4.4320
_cell_volume                     4192.3(5)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega   -3.00   28.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4041   57.0000  -30.0000 31

  2 omega   52.00   81.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4041   57.0000  -30.0000 29

  3 omega   -9.00   18.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0603  -99.0000  120.0000 27

  4 omega  -24.00   13.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0603  -99.0000  -60.0000 37

  5 omega -103.00  -64.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0603 -179.0000  -60.0000 39

  6 omega  -47.00   47.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0603   77.0000  150.0000 94

  7 omega  -25.00   10.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0603  -99.0000 -150.0000 35
;
_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  0.0619
_diffrn_reflns_av_unetI/netI     0.1062
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19176
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         4.150
_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    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70428
_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 reddish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_description       prism
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.038
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     537
_refine_ls_number_reflns         8201
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.2051
_refine_ls_R_factor_gt           0.1146
_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          0.3129
_refine_ls_wR_factor_ref         0.3805
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3668
_reflns_number_total             8201
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce01957j2.cif
_cod_data_source_block           iii
_cod_database_code               7239817
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.974
_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
2. Restrained distances
 O108-N103 = O109-N103
 1.22 with sigma of 0.0002
 O109-O108
 2.15 with sigma of 0.0002
 O105-N102 = O106-N102
 1.22 with sigma of 0.0002
 O106-O105
 2.15 with sigma of 0.0002
 O104-O10_$1
 2.605 with sigma of 0.0002
 O10-O109
 3.509 with sigma of 0.04
 O10-O102_$2
 3.278 with sigma of 0.04
3. Rigid bond restraints
 O10
 with sigma for 1-2 distances of 0.00001 and sigma for 1-3 distances of 0.00001
4. Uiso/Uaniso restraints and constraints
Uanis(O2) \\sim Ueq, Uanis(O2A) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
5. Others
 Sof(O19A)=Sof(O16A)=1-FVAR(1)
 Sof(O106)=Sof(O105)=FVAR(1)
 Sof(O18A)=Sof(O15A)=1-FVAR(2)
 Sof(O108)=Sof(O109)=FVAR(2)
 Fixed Sof: O10(0.28416) O1A(0.71584) O2(0.43679) O2A(0.56321)
6.a Ternary CH refined with riding coordinates:
 C37(H37), C22(H22), C32(H32), C12(H12), C26(H26), C17(H17), C13(H13),
 C24(H24), C34(H34)
6.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C11(H11A,H11B), C15(H15A,H15B), C38(H38A,H38B), C21(H21A,
 H21B), C31(H31A,H31B), C28(H28A,H28B), C14(H14A,H14B), C39(H39A,H39B),
 C29(H29A,H29B), C35(H35A,H35B), C015(H01A,H01B), C25(H25A,H25B), C16(H16A,
 H16B), C36(H36A,H36B), C33(H33A,H33B), C18(H18A,H18B), C23(H23A,H23B)
6.c Idealised Me refined as rotating group:
 N20(H20A,H20B,H20C), N10(H10A,H10B,H10C), N30(H30A,H30B,H30C)
;
_shelx_res_checksum              56915
_olex2_submission_special_instructions 'No special instructions were received'