Cyclic Alkenenitriles: Synthesis, Conjugate Addition, and Stereoselective Annulation
Fraser F. Fleming; Zhiyu Zhang; Qunzhao Wang; Omar W. Steward; Journal of Organic Chemistry 68 (2003) 7646–7650; doi:10.1021/jo0345291

data_4022483
_publ_contact_author_address
;Department of Chemistry and Biochemistry
Duquesne University
Pittsburgh, PA 15282 USA
;
_publ_contact_author_email       ' steward@duq.edu '
_publ_contact_author_fax         ' (412) 396 5683 '
_publ_contact_author_name        'Omar W. Steward'
_publ_contact_author_phone       ' (412) 396 6338 '
_publ_section_title
;
 Cyclic Alkenenitriles: Synthesis, Conjugate Addition,
 and Stereoselective Annulation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7646
_journal_page_last               7650
_journal_paper_doi               10.1021/jo0345291
_journal_volume                  68
_journal_year                    2003
_chemical_formula_moiety         'C13 H19 N O '
_chemical_formula_sum            'C13 H19 N O'
_chemical_formula_weight         205.30
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_audit_creation_date             'Tues. June 24, 2003'
_audit_creation_method           'by teXsan v1.8'
_audit_update_record             '6/24/03 update Omar W. Steward'
_cell_angle_alpha                90
_cell_angle_beta                 94.05(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.331(9)
_cell_length_b                   11.235(5)
_cell_length_c                   8.528(2)
_cell_measurement_reflns_used    13
_cell_measurement_temperature    294.2
_cell_measurement_theta_max      17.4
_cell_measurement_theta_min      15.5
_cell_volume                     1179(1)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan (MSC, 1992-1997)'
_computing_publication_material  'teXsan (MSC, 1992-1997)'
_computing_structure_refinement  'teXsan (MSC, 1992-1997)'
_diffrn_ambient_temperature      294.2
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       \w-2\q
_diffrn_orient_matrix_UB_11      -0.05486
_diffrn_orient_matrix_UB_12      0.06334
_diffrn_orient_matrix_UB_13      -0.02724
_diffrn_orient_matrix_UB_21      -0.05745
_diffrn_orient_matrix_UB_22      -0.06220
_diffrn_orient_matrix_UB_23      -0.01775
_diffrn_orient_matrix_UB_31      -0.01630
_diffrn_orient_matrix_UB_32      0.00548
_diffrn_orient_matrix_UB_33      0.11294
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.02508
_diffrn_reflns_av_sigmaI/netI    0.050
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            1492
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         3.31
_diffrn_standards_decay_%        0.67
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type
;
\y scans (North,Phillips & Matthews, 1968)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             448.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.237
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     136
_refine_ls_number_reflns         936
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.0010
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00042|Fo|^2^]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_ref         0.0537
_reflns_number_gt                936
_reflns_number_total             1426
_reflns_threshold_expression     I>3.00\s(I)
_cod_data_source_file            jo0345291si20030708_015705.cif
_cod_data_source_block           Compound_18f_Cyanide
_cod_depositor_comments
;
 Adding the '_geom_hbond_atom_site_label_A' data item. Values of the
 data item were determined from the geometry of the molecule.

 Antanas Vaitkus,
 2017-03-06

The following automatic conversions were performed:
data name '_geom_bond_atom_site_label_D' replaced with
'_geom_hbond_atom_site_label_D' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_bond_atom_site_label_H' replaced with
'_geom_hbond_atom_site_label_H' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_bond_distance_DH' replaced with '_geom_hbond_distance_DH'
as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_distance_HA' replaced with
'_geom_hbond_distance_HA' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_distance_DA' replaced with
'_geom_hbond_distance_DA' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_angle_DHA' replaced with '_geom_hbond_angle_DHA' as
specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_site_symmetry_A' replaced with
'_geom_hbond_site_symmetry_A' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 5005 2017-03-03 11:38:54Z antanas 
;
_cod_original_sg_symbol_H-M      'C c '
_cod_original_formula_sum        'C13 H19 N O '
_cod_database_code               4022483