Access to a Structurally Complex Compound Collection via Ring Distortion of the Alkaloid Sinomenine.
Garcia, Alfredo; Drown, Bryon S.; Hergenrother, Paul J.; Organic letters 18 (2016) 4852–4855; doi:10.1021/acs.orglett.6b02333

data_1555746
_publ_contact_author
; 
Danielle L. Gray 
University of Illinois 
School of Chemical Sciences, Box 59-1 
505 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_publ_section_title
;
 Access to a Structurally Complex Compound Collection via Ring Distortion
 of the Alkaloid Sinomenine.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4852
_journal_page_last               4855
_journal_paper_doi               10.1021/acs.orglett.6b02333
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C20 H23 N O4), 3(C H2 Cl2)'
_chemical_formula_sum            'C43 H52 Cl6 N2 O8'
_chemical_formula_weight         937.56
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
; 
? 
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.3635(8)
_cell_length_b                   25.2508(11)
_cell_length_c                   9.9745(4)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.22
_cell_measurement_theta_min      2.98
_cell_volume                     4625.1(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2014.9-0 (Bruker, 2014)'
_computing_data_reduction
; 
SAINT V8.34A, XPREP v2014/2, SADABS V2014/4, TWINABS V2012/1 
(Bruker, 2012 & 2014) 
;
_computing_molecular_graphics
; 
SHELXTL v2014-4 (Bruker, 2014), CrystalMaker v2.7.7 (CrystalMaker, 1994) 
;
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'
_computing_structure_refinement  'SHELX-2014-6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELX-2014-4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker D8 Venture/Photon 100'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_wavelength_id  cd20psa
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            29417
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.368
_diffrn_reflns_theta_min         2.975
_exptl_absorpt_coefficient_mu    3.816
_exptl_absorpt_correction_T_max  0.97081
_exptl_absorpt_correction_T_min  0.93526
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker, 2014)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1960
_exptl_crystal_id                cd20psa
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (1 -5 -1) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.305
_exptl_crystal_size_min          0.166
_refine_diff_density_max         0.927
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack (1983),  2017 Friedels'
_refine_ls_abs_structure_Flack   0.047(10)
_refine_ls_extinction_coef       0.00196(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4579
_refine_ls_number_restraints     100
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0479P)^2^+9.6065P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1226
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                4536
_reflns_number_total             4579
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02333_si_003.cif
_cod_data_source_block           cd20psa
_cod_database_code               1555746
_shelx_estimated_absorpt_t_min   0.304
_shelx_estimated_absorpt_t_max   0.570
_shelxl_version_number           2014/6
_shelx_res_checksum              2685
_shelx_hkl_checksum              27987