Development of a Practical Synthesis of an Aminoindanol-Derived M1 Agonist†
Hansen, Marvin M.; Borders, Sandra S. K.; Clayton, Marcella T.; Heath, Perry C.; Kolis, Stanley P.; Larsen, Samuel D.; Linder, Ryan J.; Reutzel-Edens, Susan M.; Smith, Justin C.; Tameze, Shella L.; Ward, Jeffrey A.; Weigel, Leland O.; Organic Process Research & Development 13 (2009) 198–; doi:10.1021/op800243q

data_1516455
_publ_section_title
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 Development of a Practical Synthesis of an Aminoindanol-Derived M1
 Agonist&#x2020;
;
_journal_issue                   2
_journal_name_full               'Organic Process Research &amp; Development'
_journal_page_first              198
_journal_paper_doi               10.1021/op800243q
_journal_volume                  13
_journal_year                    2009
_chemical_formula_sum            'C9 H9 N O3'
_chemical_formula_weight         179.17
_chemical_name_systematic
; 
 ? 
;
_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                 116.362(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   16.038(12)
_cell_length_b                   14.670(11)
_cell_length_c                   15.634(12)
_cell_measurement_temperature    105(2)
_cell_volume                     3296(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      105(2)
_diffrn_measured_fraction_theta_full 0.914
_diffrn_measured_fraction_theta_max 0.914
_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  0.1661
_diffrn_reflns_av_sigmaI/netI    0.3071
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10242
_diffrn_reflns_theta_full        28.02
_diffrn_reflns_theta_max         28.02
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platy
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          .07
_exptl_crystal_size_mid          .08
_exptl_crystal_size_min          .15
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       0.00027(16)
_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   0.884
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.884
_refine_ls_R_factor_all          0.2507
_refine_ls_R_factor_gt           0.0821
_refine_ls_shift/su_max          0.164
_refine_ls_shift/su_mean         0.029
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0636P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1425
_refine_ls_wR_factor_ref         0.1793
_reflns_number_gt                1184
_reflns_number_total             3643
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            op800243q_si_001.cif
_cod_data_source_block           1096xf
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1516455
_cod_duplicate_entry 1504317