Divergent Strategy for Diastereocontrolled Synthesis of Small- and Medium-Ring Architectures
Srinivasulu, Vunnam; Schilf, Paul; Ibrahim, Saleh; Shehadi, Ihsan A.; Malik, Omar G.; Sieburth, Scott; Khanfar, Monther A.; Hamad, Mohamad; Abu-Yousef, Imad A.; Majdalawieh, Amin F.; Al-Tel, Taleb H.; The Journal of Organic Chemistry  (2020) –; doi:10.1021/acs.joc.0c01244

data_4038668
_publ_section_title
;
 Divergent Strategy for Diastereocontrolled Synthesis of Small- and
 Medium-Ring Architectures
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01244
_journal_year                    2020
_chemical_formula_moiety         'C38 H41 N5 O7, C4 H8 O2'
_chemical_formula_sum            'C42 H49 N5 O9'
_chemical_formula_weight         767.86
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-13
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_cell_angle_alpha                87.963(4)
_cell_angle_beta                 76.295(4)
_cell_angle_gamma                75.824(3)
_cell_formula_units_Z            2
_cell_length_a                   8.8554(4)
_cell_length_b                   15.4480(6)
_cell_length_c                   15.7234(8)
_cell_measurement_reflns_used    5228
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2440
_cell_measurement_theta_min      3.8440
_cell_volume                     2025.48(16)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0534
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -42.00  47.00   1.00   22.50    --  -16.20  77.00 150.00   89
  2  \w    -43.00 -15.00   1.00   22.50    --  -16.20  77.00 120.00   28
  3  \w    -76.00  -1.00   1.00   22.50    --  -16.20 -57.00 -90.00   75
  4  \w     -9.00  23.00   1.00   22.50    --  -16.20 -99.00   0.00   32
  5  \w    -88.00 -63.00   1.00   22.50    --  -16.20-178.00 -90.00   25
  6  \w    -82.00 -28.00   1.00   22.50    --  -16.20 -57.00   0.00   54
  7  \w    -82.00   0.00   1.00   22.50    --  -16.20 -77.00  90.00   82
  8  \w     64.00  89.00   1.00   22.50    --   16.83 178.00  60.00   25
  9  \w    -30.00  34.00   1.00   22.50    --   16.83 -57.00-150.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0112353000
_diffrn_orient_matrix_UB_12      -0.0057556000
_diffrn_orient_matrix_UB_13      -0.0458200000
_diffrn_orient_matrix_UB_21      0.0839687000
_diffrn_orient_matrix_UB_22      -0.0070384000
_diffrn_orient_matrix_UB_23      -0.0053898000
_diffrn_orient_matrix_UB_31      0.0069932000
_diffrn_orient_matrix_UB_32      -0.0464904000
_diffrn_orient_matrix_UB_33      0.0053595000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.854
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21669
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.328
_diffrn_reflns_theta_min         3.002
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     512
_refine_ls_number_reflns         9482
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0548
_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^)+(0.0630P)^2^+0.5410P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1483
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6383
_reflns_number_total             9482
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01244_si_003.cif
_cod_data_source_block           exp_2272
_cod_database_code               4038668
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C38 H41 N5 O7'
_chemical_oxdiff_usercomment     Raed-1846
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00G(H00G), C00J(H00J), C00U(H00U)
2.b Secondary CH2 refined with riding coordinates:
 C00N(H00A,H00C), C00T(H00E,H00F), C011(H01A,H01B), C018(H01C,H01D), C01J(H01Y,
 H)
2.c Aromatic/amide H refined with riding coordinates:
 N00B(H00B), N00D(H00D), C00O(H00O), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C010(H010), C013(H013), C014(H014), C016(H016), C017(H017),
 C019(H019), C01A(H01E), C01C(H01I)
2.d Idealised Me refined as rotating group:
 C01B(H01F,H01G,H01H), C01E(H01J,H01K,H01L), C01F(H01M,H01N,H01O), C01G(H01P,
 H01Q,H01R), C01H(H01S,H01T,H01U), C01I(H01V,H01W,H01X), C01K(H01Z,HA,HB)
;
_olex2_date_sample_data_collection 2018-04-18
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.131
_oxdiff_exptl_absorpt_empirical_full_min 0.896