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_4038667
_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         'C36 H37 N5 O3'
_chemical_formula_sum            'C36 H37 N5 O3'
_chemical_formula_weight         587.70
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-16
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.94(3)
_cell_length_b                   10.015(3)
_cell_length_c                   26.173(15)
_cell_measurement_reflns_used    494
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.6920
_cell_measurement_theta_min      3.3340
_cell_volume                     6275(9)
_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 8.0267
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_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    -12.00  23.00   1.00  125.00    --  -16.04 -99.00  60.00   35
  2  \w    -34.00  47.00   1.00  125.00    --  -16.04  38.00 -90.00   81
;
_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      -0.0277951000
_diffrn_orient_matrix_UB_12      -0.0011270000
_diffrn_orient_matrix_UB_13      -0.0092513000
_diffrn_orient_matrix_UB_21      -0.0072139000
_diffrn_orient_matrix_UB_22      0.0516648000
_diffrn_orient_matrix_UB_23      0.0174289000
_diffrn_orient_matrix_UB_31      0.0070224000
_diffrn_orient_matrix_UB_32      0.0483962000
_diffrn_orient_matrix_UB_33      -0.0187093000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2332
_diffrn_reflns_av_unetI/netI     0.6101
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.854
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            15032
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.173
_diffrn_reflns_theta_min         3.075
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59941
_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    1.244
_exptl_crystal_description       needle
_exptl_crystal_F_000             2496
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         7247
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.900
_refine_ls_R_factor_all          0.4631
_refine_ls_R_factor_gt           0.0983
_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^)+(0.0140P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.2015
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1300
_reflns_number_total             7247
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01244_si_004.cif
_cod_data_source_block           exp_2266
_cod_original_cell_volume        6275(8)
_cod_database_code               4038667
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C39 H43 N5 O7'
_chemical_oxdiff_usercomment     Raed-1886
_reflns_odcompleteness_completeness 99.06
_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:
 C00A(H00C), C00D(H00D), C00F(H00F)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00I(H00E,H00G), C00M(H00H,H00I), C00O(H00J,H00K), C00T(H00L,
 H00M)
2.c Aromatic/amide H refined with riding coordinates:
 N005(H005), C00S(H00S), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X),
 C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013),
 C014(H014), C016(H016)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C0AA(H0AA,H0AB,H0AC)
;
_olex2_date_sample_data_collection 2018-04-16
_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 1.281
_oxdiff_exptl_absorpt_empirical_full_min 0.761