Strategies for the Total Synthesis of Diverse Bromo-Chamigrenes.
Shen, Minxing; Kretschmer, Manuel; Brill, Zachary G.; Snyder, Scott A.; Organic letters 18 (2016) 5018–5021; doi:10.1021/acs.orglett.6b02478

data_1555783
_publ_section_title
;
 Strategies for the Total Synthesis of Diverse Bromo-Chamigrenes.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5018
_journal_page_last               5021
_journal_paper_doi               10.1021/acs.orglett.6b02478
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C15 H25 Br O2'
_chemical_formula_sum            'C15 H25 Br O2'
_chemical_formula_weight         317.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-07-20
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.044(3)
_cell_angle_gamma                90
_cell_formula_units_Z            24
_cell_length_a                   31.909(2)
_cell_length_b                   22.347(2)
_cell_length_c                   13.1317(9)
_cell_measurement_reflns_used    9220
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.40
_cell_volume                     9293.2(12)
_computing_cell_refinement       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT 2014/5 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1355
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            60518
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.858
_diffrn_reflns_theta_min         2.134
_diffrn_source                   'INCOATEC ImuS micro-focus source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.648
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1441 before and 0.0533 after correction.
The Ratio of minimum to maximum transmission is 0.8211.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       plate
_exptl_crystal_F_000             3984
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.237
_refine_diff_density_min         -1.802
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     502
_refine_ls_number_reflns         8925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0754
_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^)+(0.0398P)^2^+85.1625P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1592
_refine_ls_wR_factor_ref         0.1685
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6910
_reflns_number_total             8925
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02478_si_002.cif
_cod_data_source_block           0264_minxing_sq
_cod_database_code               1555783
_shelx_estimated_absorpt_t_max   0.778
_shelx_estimated_absorpt_t_min   0.485
_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:
 C2(H2A), C11(H11), C16(H16), C28(H28), C31(H31), C43(H43)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C6(H6A,H6B), C10(H10A,H10B), C13(H13A,H13B), C14(H14A,H14B),
 C17(H17A,H17B), C18(H18A,H18B), C25(H25A,H25B), C26(H26A,H26B), C29(H29A,H29B),
  C32(H32A,H32B), C33(H33A,H33B), C40(H40A,H40B), C41(H41A,H41B), C44(H44A,H44B)
2.c X=CH2 refined with riding coordinates:
 C7(H7A,H7B), C24(H24A,H24B), C39(H39A,H39B)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C15(H15A,H15B,H15C), C22(H22A,H22B,H22C),
 C23(H23A,H23B,H23C), C30(H30A,H30B,H30C), C37(H37A,H37B,H37C), C38(H38A,H38B,
 H38C), C45(H45A,H45B,H45C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O4(H4), O5(H5), O6(H6)
;
_shelx_res_checksum              84815
_shelx_hkl_checksum              45435
_shelx_fab_checksum              77734
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'