Crystal structure of camptothecin, C20H16N2O4
Tan, Zhuo-Jie; Wang, Yun-Bo; Yang, Quan-Nu; Li, Yao-Lan; Wang, Guo-Cai; Ouyang, Yong-Zhong; Li, Guo-Qiang; Zeitschrift für Kristallographie - New Crystal Structures 233 (2018) 365–367; doi:10.1515/ncrs-2017-0244

data_8106154
_publ_section_title
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 Crystal structure of camptothecin, C20H16N2O4
;
_journal_issue                   3
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              365
_journal_page_last               367
_journal_paper_doi               10.1515/ncrs-2017-0244
_journal_volume                  233
_journal_year                    2018
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C20 H16 N2 O4'
_chemical_formula_sum            'C20 H16 N2 O4'
_chemical_formula_weight         348.35
_chemical_name_systematic        monoclinic
_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   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 95.809(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0094(5)
_cell_length_b                   6.7689(3)
_cell_length_c                   29.577(2)
_cell_measurement_reflns_used    2251
_cell_measurement_temperature    293
_cell_measurement_theta_max      63.1880
_cell_measurement_theta_min      4.5043
_cell_volume                     1595.28(16)
_computing_cell_refinement       'CrysAlisPro [12]'
_computing_data_collection       'CrysAlisPro [12]'
_computing_data_reduction        'CrysAlisPro [12]'
_computing_molecular_graphics    'Olex2 [10]'
_computing_publication_material  'Olex2 [10]'
_computing_structure_refinement  'ShelXL [8]'
_computing_structure_solution    'XS [8]'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 16.0288
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Gemini S Ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1181152000
_diffrn_orient_matrix_UB_12      -0.1757878000
_diffrn_orient_matrix_UB_13      -0.0057139000
_diffrn_orient_matrix_UB_21      0.0337945000
_diffrn_orient_matrix_UB_22      -0.0180435000
_diffrn_orient_matrix_UB_23      0.0520965000
_diffrn_orient_matrix_UB_31      -0.1490402000
_diffrn_orient_matrix_UB_32      -0.1434102000
_diffrn_orient_matrix_UB_33      0.0003974000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            10754
_diffrn_reflns_point_group_measured_fraction_full 0.775
_diffrn_reflns_point_group_measured_fraction_max 0.775
_diffrn_reflns_theta_full        63.278
_diffrn_reflns_theta_max         63.278
_diffrn_reflns_theta_min         4.508
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.0654 before and 0.0457 after correction.
The Ratio of minimum to maximum transmission is 0.9251.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
Flack x determined using 740 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         4004
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0663P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1209
_reflns_Friedel_coverage         0.439
_reflns_Friedel_fraction_full    0.523
_reflns_Friedel_fraction_max     0.523
_reflns_number_gt                3089
_reflns_number_total             4004
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2017-0244_suppl.cif
_cod_data_source_block           dd
_cod_original_cell_volume        1595.27(16)
_cod_database_code               8106154
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5'(H5'A,H5'B), C5(H5A,H5B), C17'(H17C,H17D), C19'(H19C,H19D), C17(H17A,H17B),
  C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C14'(H14'), C7(H7), C7'(H7'), C9'(H9'), C12'(H12'), C10(H10),
 C9(H9), C14(H14), C11'(H11'), C10'(H10'), C11(H11)
2.c Idealised Me refined as rotating group:
 C18'(H18D,H18E,H18F), C18(H18A,H18B,H18C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3'(H3'), O3(H3)
;
_shelx_res_checksum              43015
_shelx_hkl_checksum              50172
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'