Biomimetic Synthesis of Natural Product Salviadione and Its Hybrids: Discovery of Tissue-Specific Anti-Inflammatory Agents for Acute Lung Injury
Ding, Chunyong; Chen, Hongjin; Liang, Bing; Jiao, Mingkun; Liang, Guang; Zhang, Ao; Chemical Science  (2019) –; doi:10.1039/C9SC00086K

data_1550776
_publ_section_title
;
 Biomimetic Synthesis of Natural Product Salviadione and Its Hybrids:
 Discovery of Tissue-Specific Anti-Inflammatory Agents for Acute Lung
 Injury
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC00086K
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C25 H18 Cl N O3'
_chemical_formula_sum            'C25 H18 Cl N O3'
_chemical_formula_weight         415.85
_chemical_name_systematic        4437-104
_chemical_properties_physical    ', Light-sensitive'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_Hall           'I 2 -2c'
_space_group_name_H-M_alt        'I b a 2'
_symmetry_space_group_name_Hall  'I 2 -2c'
_symmetry_space_group_name_H-M   'I b a 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-12-05
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;
_audit_update_record
;
2016-12-06 deposited with the CCDC.    2019-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.2897(3)
_cell_length_b                   23.0144(10)
_cell_length_c                   25.5674(10)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    100
_cell_measurement_theta_max      64.44
_cell_measurement_theta_min      3.84
_cell_volume                     4289.4(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            18080
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        64.867
_diffrn_reflns_theta_max         64.867
_diffrn_reflns_theta_min         3.457
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.788
_exptl_absorpt_correction_T_max  0.7525
_exptl_absorpt_correction_T_min  0.5960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1346 before and 0.0644 after correction.
The Ratio of minimum to maximum transmission is 0.7920.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1583 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.068(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3532
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0218P)^2^+7.0952P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_full    0.937
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                3484
_reflns_number_total             3532
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00086k2.cif
_cod_data_source_block           cu_2015536_0m
_cod_database_code               1550776
_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. Restrained distances
 O2-C24 \\sim O2-C20
 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C24(H24), C17(H17), C18(H18), C3(H3), C2(H2)
3.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C25(H25A,H25B,H25C), C16(H16A,H16B,H16C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'