#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:51:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178827 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/81/4108127.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4108127
loop_
_publ_author_name
'Donna K. Friel'
'Marc L. Snapper'
'Amir H. Hoveyda'
_publ_section_title
;
 Aluminum-Catalyzed Asymmetric Alkylations of Pyridyl-Substituted Alkynyl
 Ketones with Dialkylzinc Reagents
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9942
_journal_page_last               9951
_journal_paper_doi               10.1021/ja802935w
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H13 N O'
_chemical_formula_sum            'C15 H13 N O'
_chemical_formula_weight         223.26
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3494(2)
_cell_length_b                   9.6354(2)
_cell_length_c                   13.2387(3)
_cell_measurement_reflns_used    9791
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.52
_cell_measurement_theta_min      3.34
_cell_volume                     1192.61(4)
_computing_cell_refinement       'SAINT 7.3 (Bruker-AXS, 2006)'
_computing_data_collection       'APEX2 2.1 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT 7.3 (Bruker-AXS, 2006)'
_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      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'omega and phi scans'
_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  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0073
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22516
_diffrn_reflns_theta_full        67.70
_diffrn_reflns_theta_max         67.70
_diffrn_reflns_theta_min         5.68
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  0.8614
_exptl_absorpt_correction_T_min  0.7910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2158
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0260
_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/[σ²(Fo²)+(0.0395P)²+0.2072P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0666
_reflns_number_gt                2150
_reflns_number_total             2158
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja802935w-file002.cif
_cod_data_source_block           d08004
_cod_database_code               4108127
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.95536(9) -0.14340(8) 0.32655(6) 0.01933(18) Uani 1 1 d D
H1 H 0.9403(15) -0.1960(14) 0.2763(10) 0.023 Uiso 1 1 d D
N1 N 1.10683(10) 0.19776(9) 0.35668(7) 0.0196(2) Uani 1 1 d .
C1 C 0.76787(12) 0.12074(11) 0.21010(8) 0.0189(2) Uani 1 1 d .
C2 C 0.86927(12) 0.06067(11) 0.24464(8) 0.0179(2) Uani 1 1 d .
C3 C 0.99500(11) -0.01033(11) 0.28915(8) 0.0169(2) Uani 1 1 d .
C4 C 1.11552(12) -0.02342(11) 0.21073(8) 0.0192(2) Uani 1 1 d .
H4A H 1.0835 -0.0825 0.1549 0.029 Uiso 1 1 calc R
H4B H 1.1999 -0.0649 0.2426 0.029 Uiso 1 1 calc R
H4C H 1.1400 0.0688 0.1848 0.029 Uiso 1 1 calc R
C5 C 1.04724(11) 0.07502(11) 0.37959(8) 0.0167(2) Uani 1 1 d .
C6 C 1.03452(12) 0.02719(12) 0.47811(8) 0.0202(2) Uani 1 1 d .
H6 H 0.9898 -0.0592 0.4921 0.024 Uiso 1 1 calc R
C7 C 1.08849(13) 0.10835(13) 0.55565(9) 0.0237(3) Uani 1 1 d .
H7 H 1.0801 0.0788 0.6239 0.028 Uiso 1 1 calc R
C8 C 1.15491(13) 0.23309(13) 0.53272(9) 0.0247(3) Uani 1 1 d .
H8 H 1.1953 0.2892 0.5844 0.030 Uiso 1 1 calc R
C9 C 1.16069(13) 0.27342(13) 0.43270(9) 0.0230(3) Uani 1 1 d .
H9 H 1.2052 0.3594 0.4169 0.028 Uiso 1 1 calc R
C11 C 0.64849(11) 0.19901(11) 0.17233(8) 0.0176(2) Uani 1 1 d .
C12 C 0.51385(12) 0.18841(12) 0.21808(9) 0.0209(2) Uani 1 1 d .
H12 H 0.4998 0.1258 0.2726 0.025 Uiso 1 1 calc R
C13 C 0.40133(12) 0.26900(12) 0.18400(9) 0.0245(3) Uani 1 1 d .
H13 H 0.3105 0.2619 0.2157 0.029 Uiso 1 1 calc R
C14 C 0.41988(13) 0.35994(13) 0.10400(9) 0.0260(3) Uani 1 1 d .
H14 H 0.3420 0.4148 0.0809 0.031 Uiso 1 1 calc R
C15 C 0.55268(14) 0.37069(13) 0.05760(9) 0.0271(3) Uani 1 1 d .
H15 H 0.5655 0.4329 0.0026 0.032 Uiso 1 1 calc R
C16 C 0.66684(13) 0.29091(12) 0.09127(9) 0.0222(2) Uani 1 1 d .
H16 H 0.7575 0.2986 0.0593 0.027 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 N1 C5 117.73(10)
C2 C1 C11 176.82(12)
C1 C2 C3 178.47(11)
O1 C3 C2 110.34(9)
O1 C3 C5 107.13(9)
C2 C3 C5 108.40(9)
O1 C3 C4 110.60(8)
C2 C3 C4 110.53(9)
C5 C3 C4 109.75(9)
N1 C5 C6 122.71(10)
N1 C5 C3 115.38(9)
C6 C5 C3 121.91(9)
C7 C6 C5 118.52(10)
C6 C7 C8 119.35(11)
C9 C8 C7 118.12(11)
N1 C9 C8 123.50(11)
C12 C11 C16 119.15(10)
C12 C11 C1 120.62(10)
C16 C11 C1 120.20(10)
C13 C12 C11 120.10(11)
C12 C13 C14 120.61(11)
C13 C14 C15 119.81(11)
C16 C15 C14 120.24(11)
C15 C16 C11 120.09(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.4235(13)
N1 C9 1.3409(15)
N1 C5 1.3420(14)
C1 C2 1.2012(17)
C1 C11 1.4369(16)
C2 C3 1.4822(15)
C3 C5 1.5326(15)
C3 C4 1.5373(15)
C5 C6 1.3884(16)
C6 C7 1.3855(17)
C7 C8 1.3865(17)
C8 C9 1.3809(17)
C11 C12 1.4007(16)
C11 C16 1.4018(16)
C12 C13 1.3831(17)
C13 C14 1.3855(18)
C14 C15 1.3891(19)
C15 C16 1.3888(18)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.848(12) 2.084(13) 2.9265(12) 172.5(13) 3_745
