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

data_7239824
_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), 2(C3 H8 O)'
_chemical_formula_sum            'C78 H124 N12 O20'
_chemical_formula_weight         1549.88
_chemical_name_common
'adamantan-1-aminium trinitrophloroglucinolate propan-1-ol solvate'
_chemical_name_systematic
'adamantan-1-aminium trinitrobenzene-1,3,5-tris(olate) propan-1-ol solvate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-30
_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            4
_cell_length_a                   18.4656(11)
_cell_length_b                   16.0811(11)
_cell_length_c                   27.4522(18)
_cell_measurement_reflns_used    5141
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.6080
_cell_measurement_theta_min      4.4380
_cell_volume                     8151.9(9)
_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 0.995
_diffrn_measured_fraction_theta_max 0.942
_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    -35.00  15.00   1.00   50.00    --   28.65 -57.00 120.00   50
  2  \w   -102.00 -74.00   1.00   50.00    --  -31.47 -57.00 150.00   28
  3  \w    -44.00  38.00   1.00   50.00    --  -31.47  57.00-150.00   82
  4  \w   -100.00 -23.00   1.00   50.00    --  -31.47 -57.00-180.00   77
  5  \w    -91.00 -44.00   1.00   50.00    --  -31.47-174.00-148.00   47
  6  \w   -107.00 -34.00   1.00   50.00    --  -31.47-179.00 -90.00   73
  7  \w   -104.00   1.00   1.00   50.00    --  -31.47 -77.00   0.00  105
  8  \w   -112.00 -56.00   1.00   50.00    --  -31.47 179.00   0.00   56
;
_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  0.1860
_diffrn_reflns_av_unetI/netI     0.2277
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            96385
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.665
_diffrn_reflns_theta_min         4.170
_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    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45388
_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 reddish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       irregular
_exptl_crystal_F_000             3344
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 2542 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1037
_refine_ls_number_reflns         27308
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      0.929
_refine_ls_R_factor_all          0.2896
_refine_ls_R_factor_gt           0.0902
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0627P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1471
_refine_ls_wR_factor_ref         0.2101
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.884
_reflns_number_gt                8497
_reflns_number_total             27308
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce01957j2.cif
_cod_data_source_block           VI
_cod_database_code               7239824
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.973
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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
 O301-C302 = O401-C402
 1.343 with sigma of 0.00002
 C403-C402 = C303-C302
 1.434 with sigma of 0.00002
 C304-C303 = C404-C403
 1.512 with sigma of 0.00002
3. Restrained planarity
 O102, N102, O103, C102
 with sigma of 0.0001
 O109, O108, N101, C106
 with sigma of 0.0001
 O105, N103, O106, C104
 with sigma of 0.0001
 O208, N201, O209, C202
 with sigma of 0.0001
 C206, N202, O202, O203
 with sigma of 0.0001
 C204, N203, O206, O205
 with sigma of 0.0001
4. Others
 Fixed Sof: O103(0.68691) O102(0.68691) O203(0.66222) O202(0.66222)
 O23A(0.33778) O22A(0.33778) O13A(0.31309) O14A(0.31309)
5.a Ternary CH refined with riding coordinates:
 C34(H34), C64(H64), C18(H18), C38(H38), C42(H42), C12(H12), C14(H14),
 C22(H22), C32(H32), C58(H58), C28(H28), C48(H48), C24(H24), C52(H52), C68(H68),
  C54(H54), C44(H44), C62(H62)
5.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C36(H36A,H36B), C11(H11A,H11B), C41(H41A,H41B), C35(H35A,
 H35B), C66(H66A,H66B), C46(H46A,H46B), C65(H65A,H65B), C16(H16A,H16B),
 C31(H31A,H31B), C55(H55A,H55B), C15(H15A,H15B), C51(H51A,H51B), C37(H37A,H37B),
  C13(H13A,H13B), C33(H33A,H33B), C45(H45A,H45B), C61(H61A,H61B), C25(H25A,
 H25B), C56(H56A,H56B), C67(H67A,H67B), C23(H23A,H23B), C21(H21A,H21B),
 C19(H19A,H19B), C27(H27A,H27B), C57(H57A,H57B), C29(H29A,H29B), C63(H63A,H63B),
  C17(H17A,H17B), C43(H43A,H43B), C49(H49A,H49B), C59(H59A,H59B), C39(H39A,
 H39B), C402(H40D,H40E), C302(H30D,H30E), C69(H69A,H69B), C303(H30F,H30G),
 C53(H53A,H53B), C403(H40I,H40J), C47(H47A,H47B)
5.c Idealised Me refined as rotating group:
 N60(H60A,H60B,H60C), N40(H40A,H40B,H40C), N30(H30A,H30B,H30C), N10(H10A,H10B,
 H10C), N20(H20A,H20B,H20C), N50(H50A,H50B,H50C), C404(H40F,H40G,H40H),
 C304(H30H,H30I,H30J)
5.d Idealised tetrahedral OH refined as rotating group:
 O301(H301), O401(H401)
;
_shelx_res_checksum              13667
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.071
_oxdiff_exptl_absorpt_empirical_full_min 0.824