(±)-(<i>cis</i>-8a-Hydroxy-2-oxoperhydronaphthalen-4a-yl)propanenitrile: hydrogen bonding in a Robinson-annulation intermediate
Zewge, Daniel; Malak, Muhammad H.; Thompson, Hugh W.; Lalancette, Roger A.; Brunskill, Andrew P. J.; Acta Crystallographica Section E 63 (2007) o479–o481; doi:10.1107/S160053680605478X

data_2212208
_publ_section_title
;
 (+-)-(<i>cis</i>-8a-Hydroxy-2-oxoperhydronaphthalen-4a-yl)propanenitrile:
 hydrogen bonding in a Robinson-annulation intermediate
;
_journal_coeditor_code           HG2132
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o479
_journal_page_last               o481
_journal_paper_doi               10.1107/S160053680605478X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H19 N O2'
_chemical_formula_moiety         'C13 H19 N O2'
_chemical_formula_sum            'C13 H19 N O2'
_chemical_formula_weight         221.29
_chemical_melting_point          424
_chemical_name_systematic
;
[(+/-)-<i>cis</i>-8a-Hydroxy-2-oxoperhydronaphthalen-4a-yl]propanenitrile
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.860(7)
_cell_angle_beta                 91.695(5)
_cell_angle_gamma                105.246(6)
_cell_formula_units_Z            2
_cell_length_a                   5.8894(7)
_cell_length_b                   7.6197(11)
_cell_length_c                   13.4112(17)
_cell_measurement_reflns_used    4494
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.52
_cell_measurement_theta_min      3.89
_cell_volume                     579.89(13)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2004)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.891
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_device_type  'Bruker SMART CCD APEX-II area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_av_sigmaI/netI    0.020
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4494
_diffrn_reflns_theta_full        67.52
_diffrn_reflns_theta_max         67.52
_diffrn_reflns_theta_min         7.00
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.08
_refine_ls_R_factor_all          0.037
_refine_ls_R_factor_gt           0.037
_refine_ls_shift/su_max          0.00
_refine_ls_shift/su_mean         0.00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.2474P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.096
_refine_ls_wR_factor_ref         0.096
_reflns_number_gt                1806
_reflns_number_total             1857
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            hg2132.cif
_cod_data_source_block           I
_cod_database_code               2212208
_cod_database_fobs_code          2212208