Programmed serial stereochemical relay and its application in the synthesis of morphinans
Ho (Kenny) Park, Kun; Chen, Rui; Chen, David Y.-K.; Chem. Sci.  (2017) –; doi:10.1039/C7SC03189K

data_1546915
_publ_section_title
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 Programmed serial stereochemical relay and its application in the
 synthesis of morphinans
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_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC03189K
_journal_year                    2017
_chemical_formula_moiety         'C21 H29 N O5'
_chemical_formula_sum            'C21 H29 N O5'
_chemical_formula_weight         375.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-04-14
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
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_audit_update_record
;
2017-01-10 deposited with the CCDC.
2017-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.5550(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.8561(10)
_cell_length_b                   7.9076(4)
_cell_length_c                   12.5788(6)
_cell_measurement_reflns_used    4281
_cell_measurement_temperature    120
_cell_measurement_theta_max      25.88
_cell_measurement_theta_min      2.78
_cell_volume                     1935.02(17)
_computing_data_reduction        'SAINT v8.34A (Bruker, 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    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18865
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.055
_diffrn_reflns_theta_min         2.781
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.7047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0670 before and 0.0640 after correction.
The Ratio of minimum to maximum transmission is 0.9455.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3815
_refine_ls_number_restraints     231
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0406P)^2^+0.8067P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.1058
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2584
_reflns_number_total             3815
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc03189k2.cif
_cod_data_source_block           RC438
_cod_database_code               1546915
_shelxl_version_number           2013-4
_olex2_refinement_description
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1. Others
 Fixed Uiso: H27(0.031) H3(0.041) H4(0.039) H6(0.034) H7(0.03) H8(0.023)
 H9A(0.025) H9B(0.025) H10(0.023) H12(0.02) H16A(0.046) H16B(0.046) H16C(0.046)
 H18A(0.066) H18B(0.066) H18C(0.066) H20A(0.027) H20B(0.027) H21A(0.024)
 H21B(0.024) H22A(0.044) H22B(0.044) H22C(0.044) H24A(0.047) H24B(0.047)
 H24C(0.047) H26A(0.052) H26B(0.052) H26C(0.052)
 Fixed X: H27(0.8165) H3(0.503) H4(0.5631) H6(0.655) H7(0.7647) H8(0.8067)
 H9A(0.8328) H9B(0.8853) H10(0.9238) H12(0.774) H16A(0.6771) H16B(0.7166)
 H16C(0.6352) H18A(0.467) H18B(0.4507) H18C(0.4437) H20A(0.7762) H20B(0.7521)
 H21A(0.6782) H21B(0.7173) H22A(0.9317) H22B(0.8662) H22C(0.8845) H24A(0.9184)
 H24B(0.9208) H24C(0.8484) H26A(1.0006) H26B(0.9865) H26C(0.9956)
 Fixed Y: H27(0.8093) H3(0.6656) H4(0.4423) H6(0.3341) H7(0.3531) H8(0.5862)
 H9A(0.5704) H9B(0.5439) H10(0.788) H12(1.013) H16A(1.0435) H16B(1.1903)
 H16C(1.2019) H18A(0.8977) H18B(1.0821) H18C(0.9198) H20A(1.0507) H20B(0.9758)
 H21A(0.8833) H21B(0.7252) H22A(0.9672) H22B(1.038) H22C(1.1104) H24A(1.1012)
 H24B(1.2643) H24C(1.1865) H26A(0.7625) H26B(0.6891) H26C(0.8883)
 Fixed Z: H27(0.4723) H3(0.374) H4(0.4681) H6(0.6114) H7(0.7046) H8(0.5872)
 H9A(0.8156) H9B(0.7358) H10(0.8049) H12(0.6104) H16A(0.3608) H16B(0.436)
 H16C(0.393) H18A(0.2706) H18B(0.3115) H18C(0.3845) H20A(0.7745) H20B(0.8787)
 H21A(0.7238) H21B(0.7866) H22A(0.9401) H22B(0.9823) H22C(0.8727) H24A(0.5447)
 H24B(0.6207) H24C(0.5624) H26A(0.5757) H26B(0.6878) H26C(0.6735)
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