Biosynthesis inspired asymmetric total synthesis of camptothecin.
Li, Shan-Shan; Wu, Xiao-Guang; Li, Zhen; Tian, Jin-Rui; Ma, Ai-Jun; Tu, Yong-Qiang; Chemical communications (Cambridge, England) 62 (2026) 1276–1279; doi:10.1039/d5cc06451a

data_7135504
_publ_section_title
;
 Biosynthesis inspired asymmetric total synthesis of camptothecin.
;
_journal_issue                   4
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1276
_journal_page_last               1279
_journal_paper_doi               10.1039/d5cc06451a
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C25 H30 N2 O4'
_chemical_formula_sum            'C25 H30 N2 O4'
_chemical_formula_weight         422.51
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2pm5n5
_audit_creation_date             2025-04-30
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-09-24 deposited with the CCDC.	2025-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2722(2)
_cell_length_b                   10.9298(2)
_cell_length_c                   20.1804(5)
_cell_measurement_reflns_used    8431
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      75.6200
_cell_measurement_theta_min      4.3870
_cell_volume                     2265.72(8)
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     36.00  66.00   0.50    0.48    --  108.90 -61.00-180.00   60
  2  \w    -10.00  57.00   0.50    0.12    --   44.34 -99.00 -30.00  134
  3  \w     59.00 102.00   0.50    0.48    --  108.90 -77.00   0.00   86
  4  \w     -6.00  20.00   0.50    0.12    --   44.34 -19.00  90.00   52
  5  \w   -161.00 -78.00   0.50    0.48    -- -100.00 -22.00 179.00  166
  6  \w    -32.00  30.00   0.50    0.12    --  -44.34  22.00 -14.00  124
  7  \w    -57.00 -26.00   0.50    0.48    -- -100.00  61.00 -60.00   62
  8  \w    -51.00 -25.00   0.50    0.48    -- -100.00  45.00  30.00   52
  9  \w    -53.00 -25.00   0.50    0.48    -- -100.00  45.00  60.00   56
 10  \w    -52.00 -26.00   0.50    0.48    -- -100.00  61.00  60.00   52
 11  \w   -102.00 -28.00   0.50    0.48    -- -100.00 102.00 123.00  148
 12  \w   -120.00 -87.00   0.50    0.12    --  -44.34 179.00  90.00   66
 13  \w   -103.00 -28.00   0.50    0.48    -- -100.00 128.00-160.00  150
 14  \w    105.00 131.00   0.50    0.48    --  108.90  22.00 -14.00   52
 15  \w    -30.00  30.00   0.50    0.12    --  -44.41  19.00  90.00  120
 16  \w    -54.00 -29.00   0.50    0.48    -- -100.00  45.00-120.00   50
 17  \w   -109.00 -55.00   0.50    0.48    -- -100.00 125.00 -90.00  108
 18  \w    -54.00 -29.00   0.50    0.48    -- -100.00  45.00   0.00   50
 19  \w    -69.00 -29.00   0.50    0.48    -- -100.00  61.00 120.00   80
 20  \w    -58.00 -32.00   0.50    0.48    -- -100.00  61.00-120.00   52
 21  \w    -54.00 -28.00   0.50    0.48    -- -100.00  45.00 120.00   52
 22  \w     35.00  60.00   0.50    0.48    --  108.90 -61.00 150.00   50
 23  \w     42.00  68.00   0.50    0.48    --  108.90 -61.00-150.00   52
 24  \w     38.00  64.00   0.50    0.48    --  108.90 -61.00 -60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0450319000
_diffrn_orient_matrix_UB_12      -0.0057045000
_diffrn_orient_matrix_UB_13      -0.0727476000
_diffrn_orient_matrix_UB_21      0.1364057000
_diffrn_orient_matrix_UB_22      -0.0407770000
_diffrn_orient_matrix_UB_23      0.0227266000
_diffrn_orient_matrix_UB_31      -0.0431878000
_diffrn_orient_matrix_UB_32      -0.1348226000
_diffrn_orient_matrix_UB_33      -0.0039505000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13089
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.338
_diffrn_reflns_theta_min         4.382
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1648 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+0.2231P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0834
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                4072
_reflns_number_total             4423
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06451a2.cif
_cod_data_source_block           12022_3_0428_auto
_cod_original_cell_volume        2265.70(9)
_cod_database_code               7135504
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C28(H28A,H28B), C32(H32A,H32B), C51(H51A,H51B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C29(H29), C31(H31), C38(H38), C40(H40), C45(H45), C50(H50)
2.d X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C58(H58A,H58B,H58C)
;
_shelx_res_checksum              32347
_shelx_hkl_checksum              90548
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.217
_oxdiff_exptl_absorpt_empirical_full_min 0.838