Regio- and Stereocontrolled Dieckmann Approach to Treprostinil-Inspired, Polycyclic Scaffold For Building Macrocyclic Diversity.
Chamakuri, Srinivas; Jogula, Srinvas; Arya, Prabhat; ACS combinatorial science 17 (2015) 437–441; doi:10.1021/acscombsci.5b00076

data_4513558
_publ_section_title
;
 Regio- and Stereocontrolled Dieckmann Approach to Treprostinil-Inspired,
 Polycyclic Scaffold For Building Macrocyclic Diversity.
;
_journal_issue                   8
_journal_name_full               'ACS combinatorial science'
_journal_page_first              437
_journal_page_last               441
_journal_paper_doi               10.1021/acscombsci.5b00076
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C23 H36 O5 Si'
_chemical_formula_weight         420.61
_chemical_melting_point          149.0(10)
_chemical_name_systematic
; 
 (1S,2R,3aS,4R,9aR)-ethyl 4-(tert-butyldimethylsilyloxy)-2-hydroxy-8-methoxy-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-1-carboxylate 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 130.561(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   35.945(5)
_cell_length_b                   7.1685(10)
_cell_length_c                   24.167(3)
_cell_measurement_reflns_used    4143
_cell_measurement_temperature    571(2)
_cell_measurement_theta_max      20.39
_cell_measurement_theta_min      2.22
_cell_volume                     4730.9(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      571(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            23589
_diffrn_reflns_theta_full        26.08
_diffrn_reflns_theta_max         26.08
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.9748
_exptl_absorpt_correction_T_min  0.9504
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4677
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0620
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0794P)^2^+2.8387P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1570
_refine_ls_wR_factor_ref         0.1771
_reflns_number_gt                3020
_reflns_number_total             4677
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            co5b00076_si_002.cif
_cod_data_source_block           vasu
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '148-150' was changed to '149.0(10)'
- the average value was taken and precision was estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_cell_volume        4731.0(11)
_cod_original_sg_symbol_H-M      'C2/c  '
_cod_database_code               4513558