Assembly of Multicyclic Isoquinoline Scaffolds from Pyridines: Formal Total Synthesis of Fredericamycin A
Wang, Fang-Xin; Yan, Jialei; Liu, Zhixin; Zhu, Tingshun; Liu, Yingguo; Ren, Shichao; Lv, Wen-Xin; Jin, Zhichao; Chi, Yonggui Robin; Chemical Science  (2021) –; doi:10.1039/D1SC02442F

data_1563750
_publ_section_title
;
 Assembly of Multicyclic Isoquinoline Scaffolds from Pyridines: Formal
 Total Synthesis of Fredericamycin A
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02442F
_journal_year                    2021
_chemical_absolute_configuration ref
_chemical_formula_sum            'C25 H29 N O3'
_chemical_formula_weight         391.49
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_update_record
;
2021-02-08 deposited with the CCDC.	2021-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                88.115(6)
_cell_angle_beta                 87.858(6)
_cell_angle_gamma                68.927(5)
_cell_formula_units_Z            2
_cell_length_a                   6.5078(7)
_cell_length_b                   6.7349(7)
_cell_length_c                   25.061(3)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      67.8022
_cell_measurement_theta_min      3.5306
_cell_volume                     1024.0(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2018)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_av_unetI/netI     0.1053
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            24907
_diffrn_reflns_theta_full        68.58
_diffrn_reflns_theta_max         68.58
_diffrn_reflns_theta_min         3.53
_diffrn_source                   'Incoatec Microfocus Source'
_diffrn_source_type              'Bruker Kappa Duo APEX2'
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.306
_refine_ls_abs_structure_details
;

Flack x determined using 2113 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     719
_refine_ls_number_reflns         7109
_refine_ls_number_restraints     1259
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0920
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1647P)^2^+0.3402P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2722
_refine_ls_wR_factor_ref         0.2824
_reflns_number_gt                5907
_reflns_number_total             7109
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02442f2.cif
_cod_data_source_block           cyg379s
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        1024.01(19)
_cod_database_code               1563750
_shelx_res_checksum              64521
_shelx_hkl_checksum              60254