Total synthesis and preliminary SAR study of (±)-merochlorins A and B.
Yang, Hongzhi; Liu, Xue; Li, Qingong; Li, Longbo; Zhang, Jing-Ren; Tang, Yefeng; Organic & biomolecular chemistry 14 (2015) 198–205; doi:10.1039/c5ob01946j

data_7154757
_publ_section_title
;
 Total synthesis and preliminary SAR study of (+-)-merochlorins A and B.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              198
_journal_page_last               205
_journal_paper_doi               10.1039/c5ob01946j
_journal_volume                  14
_journal_year                    2015
_chemical_formula_moiety         'C26 H33 Cl O4'
_chemical_formula_sum            'C26 H33 Cl O4'
_chemical_formula_weight         444.97
_chemical_name_common            '[3+2] + DA product'
_chemical_name_systematic        'compound 18'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-06-10
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2015-07-15 deposited with the CCDC.
2015-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.774(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8200(5)
_cell_length_b                   14.6670(7)
_cell_length_c                   12.6709(7)
_cell_measurement_reflns_used    4046
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      28.2520
_cell_measurement_theta_min      3.2260
_cell_volume                     2332.4(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.8497
_diffrn_measurement_details
;
  1 omega   40.00   91.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  178.0000   30.0000 51

  2 omega  -62.00   39.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -19.0000    0.0000 101

  3 omega  -53.00   11.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -57.0000  150.0000 64
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0382228000
_diffrn_orient_matrix_UB_12      0.0353701000
_diffrn_orient_matrix_UB_13      -0.0129835000
_diffrn_orient_matrix_UB_21      -0.0037933000
_diffrn_orient_matrix_UB_22      -0.0088875000
_diffrn_orient_matrix_UB_23      -0.0556737000
_diffrn_orient_matrix_UB_31      -0.0414408000
_diffrn_orient_matrix_UB_32      -0.0317852000
_diffrn_orient_matrix_UB_33      0.0011373000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12808
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.085
_diffrn_reflns_theta_min         2.889
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             952
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: pet/EtOAc'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         5308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0316P)^2^+1.3452P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1114
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3699
_reflns_number_total             5308
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob01946j2.cif
_cod_data_source_block           exp_3659
_cod_depositor_comments
'Adding full bibliography for 7154757--7154758.cif.'
_cod_database_code               7154757
_chemical_oxdiff_formula         C23H18Cl1O4
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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:
 C4(H4), C9(H9), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C13(H13A,H13B), C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C19(H19)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C31(H31A,H31B,H31C)
;
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.962
_shelxl_version_number           2013-3