A concise total synthesis of cochlearoid B.
Zhang, Wuxia; Xiao, Dehai; Wang, Bo; Organic & biomolecular chemistry 16 (2018) 3358–3361; doi:10.1039/c8ob00615f

data_7156191
_publ_section_title
;
 A concise total synthesis of cochlearoid B.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3358
_journal_page_last               3361
_journal_paper_doi               10.1039/c8ob00615f
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C24 H24 Br N O7'
_chemical_formula_sum            'C24 H24 Br N O7'
_chemical_formula_weight         518.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-06 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                83.51(3)
_cell_angle_beta                 88.58(3)
_cell_angle_gamma                66.94(3)
_cell_formula_units_Z            4
_cell_length_a                   8.5808(17)
_cell_length_b                   10.449(2)
_cell_length_c                   27.944(6)
_cell_measurement_reflns_used    2558
_cell_measurement_temperature    296
_cell_measurement_theta_max      20.738
_cell_measurement_theta_min      2.201
_cell_volume                     2290.0(10)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0663
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            11905
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.122
_diffrn_reflns_theta_max         25.122
_diffrn_reflns_theta_min         2.132
_exptl_absorpt_coefficient_mu    1.841
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.0567 before and 0.0212 after correction. The Ratio of minimum to maximum transmission is 0.5948. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     620
_refine_ls_number_reflns         8000
_refine_ls_number_restraints     1173
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0532
_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^)+(0.0631P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1359
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4907
_reflns_number_total             8000
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00615f2.cif
_cod_data_source_block           aaaaa
_cod_depositor_comments
'Adding full bibliography for 7156190--7156191.cif.'
_cod_original_cell_volume        2289.9(9)
_cod_database_code               7156191
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.757
_shelx_estimated_absorpt_t_min   0.710
_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
 N2-O8 \\sim N2-O8A
 with sigma of 0.02
 N2-O9 \\sim N2-O9A
 with sigma of 0.02
3. Rigid bond restraints
 N1, C1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33
\\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41
\\sim C42 \\sim C43 \\sim C44 \\sim C45 \\sim C46 \\sim C47 \\sim C48: within
3.8A with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(O8A)=Sof(O9A)=1-FVAR(1)
 Sof(O8)=Sof(O9)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C16(H16), C40(H40)
6.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B), C39(H39A,H39B), C41(H41A,
 H41B), C42(H42A,H42B)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C9(H9), C11(H11), C12(H12), C26(H26), C28(H28),
 C29(H29), C33(H33), C35(H35), C36(H36)
6.d X=CH2 refined with riding coordinates:
 C21(H21A,H21B), C45(H45A,H45B)
6.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C43(H43A,H43B,
 H43C), C46(H46A,H46B,H46C), C48(H48A,H48B,H48C)
;
_shelx_res_checksum              66122
_olex2_submission_special_instructions 'No special instructions were received'