Isolation, structure elucidation, and KDD study of (−)-Celosine, a new skeleton with potent anti-atherosclerosis activity
Sun, Zhenliang; Lv, Zhiliang; Hu, Bin; Zhang, Jifa; Du, Peng; Wang, Man; Xiao, Linlin; Yang, Peiming; RSC Advances 7 (2017) 50875–; doi:10.1039/C7RA08683K

data_7229476
_publ_section_title
;
 Isolation, structure elucidation, and KDD study of (&#x2212;)-Celosine, a
 new skeleton with potent anti-atherosclerosis activity
;
_journal_issue                   80
_journal_name_full               'RSC Advances'
_journal_page_first              50875
_journal_paper_doi               10.1039/C7RA08683K
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C27 H32 O5, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C29 H36 O6'
_chemical_formula_weight         480.57
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-06-13
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_audit_update_record
;
2016-06-28 deposited with the CCDC.
2017-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.1444(9)
_cell_length_b                   16.5294(9)
_cell_length_c                   19.7875(11)
_cell_measurement_reflns_used    9826
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      65.20
_cell_measurement_theta_min      3.83
_cell_volume                     5280.4(5)
_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      172.99
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_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  0.0353
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28412
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        63.999
_diffrn_reflns_theta_max         63.998
_diffrn_reflns_theta_min         3.533
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1337 before and 0.0599 after correction.
The Ratio of minimum to maximum transmission is 0.8226.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 3405 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     649
_refine_ls_number_reflns         8460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0520
_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^)+(0.0942P)^2^+1.2196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1369
_refine_ls_wR_factor_ref         0.1392
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                8074
_reflns_number_total             8460
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra08683k2.cif
_cod_data_source_block           160613zzy1_0m
_cod_depositor_comments
;

2018-02-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C27 H32 O5), C4 H8 O2'
_cod_original_formula_sum        'C58 H72 O12'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     961.15
_cod_database_code               7229476
_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 Ternary CH refined with riding coordinates:
 C10(H10), C9(H9), C11(H11), C14(H14), C15(H15), C17(H17), C42(H42), C37(H37),
 C41(H41), C38(H38), C40(H40), C44(H44)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C56(H56A,H56B), C39(H39A,H39B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C25(H25), C26(H26), C23(H23), C22(H22), C13(H13), C6(H6), C50(H50),
 C51(H51), C52(H52), C43(H43), C53(H53), C54(H54), C31(H31)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C), C19(H19A,H19B,H19C), C18(H18A,H18B,
 H18C), C27(H27A,H27B,H27C), C55(H55A,H55B,H55C), C28(H28A,H28B,H28C), C45(H45A,
 H45B,H45C), C46(H46A,H46B,H46C), C48(H48A,H48B,H48C), C36(H36A,H36B,H36C),
 C58(H58A,H58B,H58C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O8(H8), O7(H7)
;
_shelx_res_checksum              20873
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'