The fumarate salts of the <i>N</i>-isopropyl-<i>N</i>-methyl derivatives of DMT and psilocin
Chadeayne, Andrew R.; Pham, Duyen N. K.; Golen, James A.; Manke, David R.; Acta Crystallographica Section E 75 (2019) 1316–1320; doi:10.1107/S2056989019011253

data_2243056
_publ_section_title
;
 The fumarate salts of the <i>N</i>-isopropyl-<i>N</i>-methyl derivatives
 of DMT and psilocin
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1316
_journal_page_last               1320
_journal_paper_doi               10.1107/S2056989019011253
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C14 H21 N2 O +, C4 H3 O4 -, H2 O'
_chemical_formula_moiety         'C14 H21 N2 O +, C4 H3 O4 -, H2 O'
_chemical_formula_sum            'C18 H26 N2 O6'
_chemical_formula_weight         366.41
_chemical_name_common
;
4-Hydroxy-<i>N</i>-isopropyl-<i>N</i>-methyltryptaminium fumarate
monohydrate
;
_chemical_name_systematic
;
[2-(4-Hydroxy-1<i>H</i>-indol-3-yl)ethyl](methyl)propan-2-ylazanium
3-carboxyprop-2-enoate monohydrate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 123.389(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.507(3)
_cell_length_b                   8.7445(8)
_cell_length_c                   17.3659(18)
_cell_measurement_reflns_used    9718
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      2.93
_cell_volume                     3741.3(7)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick 2008)
;
_diffrn_ambient_temperature      200.01
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            70395
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.406
_diffrn_reflns_theta_min         3.060
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.198
_refine_ls_extinction_coef       0.0081(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         3458
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0299P)^2^+3.9177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0957
_reflns_number_gt                2978
_reflns_number_total             3458
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7844sup1.cif
_cod_data_source_block           4-HO-MiPT
_cod_original_cell_volume        3741.2(7)
_cod_database_code               2243056
_cod_database_fobs_code          2243056
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.981
_shelx_hkl_checksum              93154
_shelx_res_checksum              56957
_shelxl_version_number           2014/6