Synthesis, crystal structure, Hirshfeld surface analysis and energy framework calculations of <i>trans</i>-3,7,9,9-tetramethyl-10-(prop-2-yn-1-yl)-1,2,3,4,4a,9,9a,10-octahydroacridine
Acelas, Mauricio; Dugarte-Dugarte, Analio; Romero Bohórquez, Arnold R.; Henao, José Antonio; Delgado, José Miguel; Díaz de Delgado, Graciela; Acta Crystallographica Section E 77 (2021) 226–232; doi:10.1107/S2056989021001183

data_2243745
_publ_section_title
;
 Synthesis, crystal structure, Hirshfeld surface analysis and energy
 framework calculations of
 <i>trans</i>-3,7,9,9-tetramethyl-10-(prop-2-yn-1-yl)-1,2,3,4,4a,9,9a,10-octahydroacridine
;
_journal_coeditor_code           HB7966
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              226
_journal_page_last               232
_journal_paper_doi               10.1107/S2056989021001183
_journal_volume                  77
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C20 H27 N'
_chemical_formula_moiety         'C20 H27 N'
_chemical_formula_sum            'C20 H27 N'
_chemical_formula_weight         281.42
_chemical_melting_point          367
_chemical_name_systematic
<i>trans</i>-3,7,9,9-Tetramethyl-10-(prop-2-yn-1-yl)-1,2,3,4,4a,9,9a,10-octahydroacridine
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.05103(9)
_cell_length_b                   10.62943(11)
_cell_length_c                   15.64759(16)
_cell_measurement_reflns_used    6301
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1580
_cell_measurement_theta_min      2.8100
_cell_volume                     1671.74(3)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2019)
;
_computing_data_collection
;
<i>CrystalClear-SM Expert</i> (Rigaku/MSC, 2015)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2019)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 1999)
;
_computing_publication_material
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009), enCIFer (Allen <i>et
al.</i>,  2004) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
<i>SHELXL2018/3</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT2014/5</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device       'AFC11 (Right): Eulerian 3 circle'
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0132
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6660
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.145
_diffrn_reflns_theta_min         5.655
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.476
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.57321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPRO; Rigaku OD, 2019)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.187
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1267 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_coef       0.037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0679P)^2^+0.0783P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1065
_reflns_number_gt                3160
_reflns_number_total             3181
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7966sup1.cif
_cod_data_source_block           I
_cod_database_code               2243745
_cod_database_fobs_code          2243745
_shelx_hkl_checksum              30490
_shelx_res_checksum              78113