Robustanoids A and B, two novel pyrrolo[2,3-b]indole alkaloids from Coffea canephora: isolation and total synthesis
Han, Jianxin; Niu, Sheng-Tong; Liu, Yushuang; Gan, Lishe; Wang, Tianfu; Lu, Chong-Dao; Yuan, Tao; Organic Chemistry Frontiers 5 (2018) 586–; doi:10.1039/C7QO00931C

data_1553941
_publ_section_title
;
 Robustanoids A and B, two novel pyrrolo[2,3-b]indole alkaloids from
 Coffea canephora: isolation and total synthesis
;
_journal_issue                   4
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              586
_journal_paper_doi               10.1039/C7QO00931C
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C22 H18 N2 O6, C H4 O'
_chemical_formula_sum            'C23 H22 N2 O7'
_chemical_formula_weight         438.43
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-10-11 deposited with the CCDC.
2017-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                61.974(7)
_cell_angle_beta                 80.333(11)
_cell_angle_gamma                67.602(10)
_cell_formula_units_Z            2
_cell_length_a                   9.297(7)
_cell_length_b                   11.515(9)
_cell_length_c                   11.957(9)
_cell_measurement_reflns_used    1449
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.4036
_cell_measurement_theta_min      2.3697
_cell_volume                     1044.6(14)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  bruker-CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0910
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5277
_diffrn_reflns_point_group_measured_fraction_full 0.604
_diffrn_reflns_point_group_measured_fraction_max 0.604
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.370
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0696 before and 0.0534 after correction.
The Ratio of minimum to maximum transmission is 0.8787.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       needle
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Flack x determined using 600 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_extinction_coef       0.033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     586
_refine_ls_number_reflns         4450
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0699
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1236P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1773
_refine_ls_wR_factor_ref         0.2000
_reflns_Friedel_coverage         0.232
_reflns_Friedel_fraction_full    0.227
_reflns_Friedel_fraction_max     0.227
_reflns_number_gt                3439
_reflns_number_total             4450
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00931c2.cif
_cod_data_source_block           9
_cod_database_code               1553941
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              9533
_shelx_hkl_checksum              7570