Synthetic Studies on FNC-RED and Its Analogues Containing an All <i>syn</i>-Cyclopentanetetrol Moiety.
Inuki, Shinsuke; Sato, Keisuke; Zui, Naoto; Yamaguchi, Ryosuke; Matsumaru, Takanori; Fujimoto, Yukari; The Journal of organic chemistry 84 (2019) 12680–12685; doi:10.1021/acs.joc.9b02101

data_4033986
_publ_section_title
;
 Synthetic Studies on FNC-RED and Its Analogues Containing an All
 <i>syn</i>-Cyclopentanetetrol Moiety.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12680
_journal_page_last               12685
_journal_paper_doi               10.1021/acs.joc.9b02101
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C21 H24 Br N O6'
_chemical_formula_sum            'C21 H24 Br N O6'
_chemical_formula_weight         466.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-10-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-11 # Formatted by publCIF

;
_cell_angle_alpha                79.060(2)
_cell_angle_beta                 83.239(2)
_cell_angle_gamma                75.759(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6904(5)
_cell_length_b                   10.4377(6)
_cell_length_c                   11.8142(7)
_cell_measurement_reflns_used    9632
_cell_measurement_temperature    300.15
_cell_measurement_theta_max      25.0539
_cell_measurement_theta_min      2.4634
_cell_volume                     1016.99(10)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300.15
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CMOS area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9586
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.081
_diffrn_reflns_theta_max         25.081
_diffrn_reflns_theta_min         2.425
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    2.059
_exptl_absorpt_correction_T_max  0.71
_exptl_absorpt_correction_T_min  0.36
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.829
_exptl_crystal_size_mid          0.393
_exptl_crystal_size_min          0.177
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3552
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0344P)^2^+0.8276P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0880
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3368
_reflns_number_total             3552
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {c382163d-9312-487a-a0b2-78af2cfba727}
_cod_data_source_file            jo9b02101_si_002.cif
_cod_data_source_block           170106107e142b
_cod_database_code               4033986
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.712
_shelx_estimated_absorpt_t_min   0.280
_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:
 C11(H11), C10(H10), C7(H7), C9(H9), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C17(H17), C21(H21), C18(H18), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O3(H3)
;
_shelx_res_checksum              49528
_shelx_hkl_checksum              99767
_olex2_submission_special_instructions 'No special instructions were received'