Synthesis of novel tryptamine-based macrocycles using an Ugi 4-CR/microwave assisted click-cycloaddition reaction protocol.
Chavez-Acevedo, Lizbeth; Miranda, Luis D.; Organic & biomolecular chemistry 13 (2015) 4408–4412; doi:10.1039/c5ob00067j

data_7154356
_publ_section_title
;
 Synthesis of novel tryptamine-based macrocycles using an Ugi
 4-CR/microwave assisted click-cycloaddition reaction protocol.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4408
_journal_page_last               4412
_journal_paper_doi               10.1039/c5ob00067j
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         '2(C33 H34 N6 O3), C3 H6 O'
_chemical_formula_sum            'C69 H74 N12 O7'
_chemical_formula_weight         1183.40
_chemical_melting_point          447.5(5)
_chemical_name_common            'MACROCYCLE STRUCTURE 26'
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-01-12 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5903(4)
_cell_length_b                   18.0794(5)
_cell_length_c                   25.8875(8)
_cell_measurement_reflns_used    5683
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.38
_cell_measurement_theta_min      2.33
_cell_volume                     7296.7(4)
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_collection       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/1 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1327
_diffrn_reflns_av_unetI/netI     0.1291
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            45758
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.335
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9998
_exptl_absorpt_correction_T_min  0.9996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.077
_exptl_crystal_description       prism
_exptl_crystal_F_000             2512
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ACETONE/HEXANE'
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.104
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 2114 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.2(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     840
_refine_ls_number_reflns         16088
_refine_ls_number_restraints     124
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.1778
_refine_ls_R_factor_gt           0.0757
_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^)+(0.0819P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.2051
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                7075
_reflns_number_total             16088
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00067j2.cif
_cod_data_source_block           500mgl14
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '447-448' was changed to '447.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 3086 2015-02-26 13:12:21Z robertas 

 Adding full bibliography for 7154356.cif.
;
_cod_database_code               7154356
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2014-3
_shelx_res_checksum              67570
_shelx_fab_checksum              4584