N-Methylserotonin hydrogen oxalate
Naeem, Marilyn; Anas, Nicholas A.; Chadeayne, Andrew R.; Golen, James A.; Manke, David R.; IUCrData 8 (2023) x230378–; doi:10.1107/S2414314623003784

data_1569086
_publ_section_title
;
 N-Methylserotonin hydrogen oxalate
;
_journal_coeditor_code           BX4024
_journal_issue                   5
_journal_name_full               IUCrData
_journal_page_first              x230378
_journal_paper_doi               10.1107/S2414314623003784
_journal_volume                  8
_journal_year                    2023
_chemical_formula_iupac          'C11 H15 N2 O +, C2 H O4 -'
_chemical_formula_moiety         'C11 H15 N2 O +, C2 H O4 -'
_chemical_formula_sum            'C13 H16 N2 O5'
_chemical_formula_weight         280.28
_chemical_name_common
;
<i>N</i>-Methylserotonin hydrogen oxalate
;
_chemical_name_systematic
;
[2-(5-Hydroxy-1<i>H</i>-indol-3-yl)ethyl](methyl)azanium hydrogen oxalate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.321(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.7044(4)
_cell_length_b                   9.9485(7)
_cell_length_c                   11.7687(7)
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.68
_cell_volume                     667.87(8)
_computing_cell_refinement
;
SAINT (Bruker, 2021)
;
_computing_data_collection
;
APEX4 (Bruker, 2021)
;
_computing_data_reduction
;
SAINT (Bruker, 2021)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
<i>SHELXL2018</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT2014</i> (Sheldrick 2015a)
;
_diffrn_ambient_temperature      300.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_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  0.0324
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            29160
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.401
_diffrn_reflns_theta_min         3.462
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.207
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1280 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2730
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0295
_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^)+(0.0456P)^2^+0.0849P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0769
_reflns_number_gt                2670
_reflns_number_total             2730
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            bx4024.cif
_cod_data_source_block           I
_cod_database_code               1569086
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.994
_shelx_hkl_checksum              93666
_shelx_res_checksum              47890