#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/34/1503444.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_1503444
loop_
_publ_author_name
'Mycka, Robert J.'
'Steward, Omar W.'
'Fleming, Fraser F.'
_publ_section_title
;
 Gamma-hydroxynitrile alkylations: electrophile-dependent
 stereoselectivity.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3030
_journal_page_last               3033
_journal_paper_doi               10.1021/ol101030r
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C16 H23 N O2'
_chemical_formula_sum            'C16 H23 N O2'
_chemical_formula_weight         261.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.6590(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7044(2)
_cell_length_b                   7.0265(2)
_cell_length_c                   23.8043(5)
_cell_measurement_reflns_used    3828
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.951
_cell_measurement_theta_min      2.2195
_cell_volume                     1619.86(7)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2000)'
_computing_publication_material  'ORTEP-3 for Windows (Faruggia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Smart ApexII'
_diffrn_measurement_method       'φ and ω 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  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            22028
_diffrn_reflns_theta_full        27.79
_diffrn_reflns_theta_max         27.79
_diffrn_reflns_theta_min         1.71
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         3820
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_correction_T_min  0.9639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0453
_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)+(0.0504P)²+0.2635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1248
_reflns_number_gt                2474
_reflns_number_total             3820
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101030r_si_001.cif
_cod_data_source_block           Inversion
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1503444
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
C6 C 0.15678(15) 0.6107(2) 0.37593(6) 0.0521(4) Uani 1 1 d .
C5 C 0.08317(19) 0.7625(3) 0.39501(8) 0.0783(6) Uani 1 1 d .
H5 H 0.0411 0.8468 0.3692 0.094 Uiso 1 1 calc R
C1 C 0.2198(2) 0.4901(3) 0.41482(8) 0.0776(5) Uani 1 1 d .
H1 H 0.2709 0.3873 0.4029 0.093 Uiso 1 1 calc R
C4 C 0.0708(2) 0.7915(5) 0.45136(11) 0.1172(10) Uani 1 1 d .
H4 H 0.0198 0.8941 0.4634 0.141 Uiso 1 1 calc R
C2 C 0.2075(3) 0.5209(4) 0.47219(10) 0.1107(9) Uani 1 1 d .
H2 H 0.2505 0.4389 0.4985 0.133 Uiso 1 1 calc R
C3 C 0.1325(3) 0.6714(6) 0.48960(11) 0.1220(11) Uani 1 1 d .
H3 H 0.1237 0.6915 0.5278 0.146 Uiso 1 1 calc R
C7 C 0.16904(13) 0.58432(19) 0.31344(6) 0.0437(3) Uani 1 1 d .
H7 H 0.1702 0.7108 0.2961 0.052 Uiso 1 1 calc R
O1 O 0.29208(9) 0.48892(15) 0.30081(4) 0.0541(3) Uani 1 1 d .
H1A H 0.3589 0.5560 0.3101 0.081 Uiso 1 1 calc R
C8 C 0.05015(13) 0.46746(18) 0.28267(6) 0.0412(3) Uani 1 1 d .
C9 C -0.08325(15) 0.5515(2) 0.29590(6) 0.0512(4) Uani 1 1 d .
N1 N -0.18949(14) 0.6072(2) 0.30484(7) 0.0767(5) Uani 1 1 d .
C11 C 0.06459(13) 0.48894(19) 0.21863(5) 0.0434(3) Uani 1 1 d .
H11A H 0.0733 0.6234 0.2103 0.052 Uiso 1 1 calc R
H11B H 0.1500 0.4280 0.2095 0.052 Uiso 1 1 calc R
C12 C -0.05207(13) 0.40791(19) 0.17958(6) 0.0443(3) Uani 1 1 d .
H12 H -0.1391 0.4262 0.1977 0.053 Uiso 1 1 calc R
C13 C -0.06612(16) 0.5039(2) 0.12110(6) 0.0566(4) Uani 1 1 d .
C15 C -0.1068(2) 0.7128(3) 0.12765(8) 0.0845(6) Uani 1 1 d .
H15A H -0.0329 0.7800 0.1477 0.127 Uiso 1 1 calc R
H15B H -0.1885 0.7205 0.1482 0.127 Uiso 1 1 calc R
H15C H -0.1244 0.7688 0.0911 0.127 Uiso 1 1 calc R
C14 C 0.0684(2) 0.4898(3) 0.09150(7) 0.0787(6) Uani 1 1 d .
H14A H 0.0571 0.5502 0.0553 0.118 Uiso 1 1 calc R
H14B H 0.0918 0.3583 0.0867 0.118 Uiso 1 1 calc R
H14C H 0.1409 0.5520 0.1138 0.118 Uiso 1 1 calc R
C16 C -0.1812(2) 0.4025(3) 0.08562(8) 0.0875(6) Uani 1 1 d .
H16A H -0.1947 0.4644 0.0497 0.131 Uiso 1 1 calc R
H16B H -0.2653 0.4076 0.1047 0.131 Uiso 1 1 calc R
H16C H -0.1557 0.2721 0.0802 0.131 Uiso 1 1 calc R
C10 C 0.04996(16) 0.2599(2) 0.30313(6) 0.0537(4) Uani 1 1 d .
H10A H 0.0428 0.2574 0.3432 0.081 Uiso 1 1 calc R
H10B H 0.1342 0.1989 0.2940 0.081 Uiso 1 1 calc R
H10C H -0.0272 0.1938 0.2850 0.081 Uiso 1 1 calc R
O2 O -0.02881(9) 0.20718(13) 0.17460(5) 0.0521(3) Uani 1 1 d .
H2A H -0.1027 0.1507 0.1748 0.078 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C1 C6 C5 118.36(16)
C1 C6 C7 121.98(15)
C5 C6 C7 119.65(15)
C4 C5 C6 121.2(2)
C4 C5 H5 119.4
C6 C5 H5 119.4
C6 C1 C2 120.2(2)
C6 C1 H1 119.9
C2 C1 H1 119.9
C3 C4 C5 120.2(2)
C3 C4 H4 119.9
C5 C4 H4 119.9
C3 C2 C1 119.9(2)
C3 C2 H2 120.1
C1 C2 H2 120.1
C4 C3 C2 120.1(2)
C4 C3 H3 120.0
C2 C3 H3 120.0
O1 C7 C6 112.75(11)
O1 C7 C8 105.02(10)
C6 C7 C8 115.10(11)
O1 C7 H7 107.9
C6 C7 H7 107.9
C8 C7 H7 107.9
C7 O1 H1A 109.5
C9 C8 C10 107.06(12)
C9 C8 C11 107.88(11)
C10 C8 C11 113.99(11)
C9 C8 C7 108.78(11)
C10 C8 C7 111.49(11)
C11 C8 C7 107.48(11)
N1 C9 C8 176.12(16)
C12 C11 C8 116.92(11)
C12 C11 H11A 108.1
C8 C11 H11A 108.1
C12 C11 H11B 108.1
C8 C11 H11B 108.1
H11A C11 H11B 107.3
O2 C12 C11 107.59(11)
O2 C12 C13 111.10(12)
C11 C12 C13 113.87(11)
O2 C12 H12 108.0
C11 C12 H12 108.0
C13 C12 H12 108.0
C14 C13 C15 110.07(15)
C14 C13 C16 109.29(15)
C15 C13 C16 108.57(15)
C14 C13 C12 111.03(13)
C15 C13 C12 109.59(14)
C16 C13 C12 108.24(13)
C13 C15 H15A 109.5
C13 C15 H15B 109.5
H15A C15 H15B 109.5
C13 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C13 C16 H16A 109.5
C13 C16 H16B 109.5
H16A C16 H16B 109.5
C13 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C8 C10 H10A 109.5
C8 C10 H10B 109.5
H10A C10 H10B 109.5
C8 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C12 O2 H2A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C6 C1 1.370(2)
C6 C5 1.377(2)
C6 C7 1.5113(19)
C5 C4 1.370(3)
C5 H5 0.9300
C1 C2 1.395(3)
C1 H1 0.9300
C4 C3 1.352(4)
C4 H4 0.9300
C2 C3 1.364(4)
C2 H2 0.9300
C3 H3 0.9300
C7 O1 1.4182(15)
C7 C8 1.5600(18)
C7 H7 0.9800
O1 H1A 0.8200
C8 C9 1.4751(19)
C8 C10 1.5377(19)
C8 C11 1.5471(18)
C9 N1 1.1356(18)
C11 C12 1.5283(17)
C11 H11A 0.9700
C11 H11B 0.9700
C12 O2 1.4344(16)
C12 C13 1.545(2)
C12 H12 0.9800
C13 C14 1.526(2)
C13 C15 1.530(2)
C13 C16 1.532(2)
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
O2 H2A 0.8200
