Active Metabolite of Aeruginascin (4-Hydroxy-<i>N</i>,<i>N</i>,<i>N</i>-trimethyltryptamine): Synthesis, Structure, and Serotonergic Binding Affinity.
Chadeayne, Andrew R.; Pham, Duyen N. K.; Reid, Brian G.; Golen, James A.; Manke, David R.; ACS omega 5 (2020) 16940–16943; doi:10.1021/acsomega.0c02208

data_4517834
_publ_section_title
;
 Active Metabolite of Aeruginascin
 (4-Hydroxy-<i>N</i>,<i>N</i>,<i>N</i>-trimethyltryptamine): Synthesis,
 Structure, and Serotonergic Binding Affinity.
;
_journal_issue                   27
_journal_name_full               'ACS omega'
_journal_page_first              16940
_journal_page_last               16943
_journal_paper_doi               10.1021/acsomega.0c02208
_journal_volume                  5
_journal_year                    2020
_chemical_formula_moiety         'I, C13 H19 N2 O'
_chemical_formula_sum            'C13 H19 I N2 O'
_chemical_formula_weight         346.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-02-26
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.087(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3057(9)
_cell_length_b                   11.2370(10)
_cell_length_c                   12.7785(10)
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      3.08
_cell_volume                     1493.4(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      200.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29269
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.442
_diffrn_reflns_theta_min         3.082
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.133
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0848 before and 0.0733 after correction. The Ratio of minimum to maximum transmission is 0.7697. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.048
_refine_diff_density_min         -0.929
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       0.0045(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         3063
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0286P)^2^+3.3372P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0885
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2274
_reflns_number_total             3063
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c02208_si_003.cif
_cod_data_source_block           umd1827_0m_a
_cod_depositor_comments
'Adding full bibliography for 4517833--4517834.cif.'
_cod_database_code               4517834
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.815
_shelx_estimated_absorpt_t_min   0.482
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N1-H1
 0.86 with sigma of 0.01
 O1-H1A
 0.85 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
3.b Me refined with riding coordinates:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1B), C5(H5), C6(H6), C7(H7)
;
_shelx_res_checksum              42572
_shelx_hkl_checksum              92157
_olex2_submission_special_instructions 'No special instructions were received'