Pictet‒Spengler condensations using 4-(2-aminoethyl)coumarins
Sviripa, Vitaliy M.; Fiandalo, Michael V.; Begley, Kristin L.; Wyrebek, Przemyslaw; Kril, Liliia M.; Balia, Andrii G.; Parkin, Sean R.; Subramanian, Vivekanandan; Chen, Xi; Williams, Alexander H.; Zhan, Chang-Guo; Liu, Chunming; Mohler, James L.; Watt, David S.; New Journal of Chemistry 44 (2020) 13415–13429; doi:10.1039/D0NJ02664F

data_7059797
_publ_section_title
;
 Pictet--Spengler condensations using 4-(2-aminoethyl)coumarins
;
_journal_issue                   31
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13415
_journal_page_last               13429
_journal_paper_doi               10.1039/D0NJ02664F
_journal_volume                  44
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C37 H48 N2 O2'
_chemical_formula_sum            'C37 H48 N2 O2'
_chemical_formula_weight         552.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-01-02 deposited with the CCDC.	2020-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.801(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3920(6)
_cell_length_b                   10.2078(6)
_cell_length_c                   14.5078(9)
_cell_measurement_reflns_used    5113
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.47
_cell_volume                     1480.83(15)
_computing_cell_refinement       '<i>APEX3</i> (Bruker-AXS, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker-AXS, 2016)'
_computing_data_reduction        '<i>APEX3</i> (Bruker-AXS, 2016)'
_computing_molecular_graphics    '<i>XP in SHELXTL</i> (Sheldrick, 2008)'
_computing_publication_material
'<i>SHELX</i> (Sheldrick, 2008) and <i>CIFFIX</i> (Parkin, 2013)'
_computing_structure_refinement  '<i>SHELXL-2018/3</i> (Sheldrick, 2015b)'
_computing_structure_solution    '<i>SHELXT</i> (Sheldrick, 2015a)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            38404
_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         27.527
_diffrn_reflns_theta_min         2.810
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '<i>SADABS</i> (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       'roughly triangular plate'
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
; 
Flack 'x' determined using 2053 quotients [(I+)-(I-)]/[(I+)+(I-)] 
[Parsons, Flack and Wagner (2013)]. 
;
_refine_ls_abs_structure_Flack   -0.4(7)
_refine_ls_extinction_coef       0.008(2)
_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   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         6776
_refine_ls_number_restraints     65
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.048
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0532P)^2^+0.2810P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1189
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                5260
_reflns_number_total             6776
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj02664f2.cif
_cod_data_source_block           m18253
_cod_depositor_comments
;Adding full bibliography for 7059797.cif.

 Adding full bibliography for 7059797.cif.
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7059797
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.998
_exptl_absorpt_special_details
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by X-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the X-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;
_shelx_res_checksum              43826