#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/73/1507335.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_1507335
loop_
_publ_author_name
'Ellison, Martha E.'
'Ng, Danny'
'Dang, Hung'
'Garcia-Garibay, Miguel A'
_publ_section_title
;
 Enantiospecific synthesis of vicinal stereogenic tertiary and quaternary
 centers by combination of configurationally-trapped radical pairs in
 crystalline solids.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              2531
_journal_page_last               2534
_journal_paper_doi               10.1021/ol0347803
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C19.17 H17 N O3'
_chemical_formula_weight         309.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           170
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 65'
_symmetry_space_group_name_H-M   'P 65'
_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                120.00
_cell_formula_units_Z            6
_cell_length_a                   19.154(3)
_cell_length_b                   19.154(3)
_cell_length_c                   8.393(2)
_cell_measurement_reflns_used    985
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.057
_cell_measurement_theta_min      2.720
_cell_volume                     2666.7(9)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15993
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.72
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_correction_T_min  0.9545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs(Bruker)
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             978
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.9(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         4062
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0533P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                3275
_reflns_number_total             4062
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0347803si20030519_125127.cif
_cod_data_source_block           gg1102
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Hexagonal' changed to 'hexagonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2666.5(9)
_cod_original_sg_symbol_H-M      P6(5)
_cod_database_code               1507335
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'
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
_atom_site_disorder_group
N1 N 0.20583(9) 0.58301(9) 0.0344(2) 0.0378(4) Uani 1 1 d . .
O1 O 0.07742(6) 0.66024(6) -0.01094(13) 0.0248(2) Uani 1 1 d . .
O2 O 0.26528(9) 0.91927(8) -0.05619(18) 0.0536(4) Uani 1 1 d . .
O3 O 0.25867(6) 0.80090(7) -0.08970(14) 0.0293(3) Uani 1 1 d . .
C1 C 0.18136(9) 0.68995(9) 0.17868(18) 0.0207(3) Uani 1 1 d . .
H1 H 0.2343 0.7394 0.2009 0.025 Uiso 1 1 calc R .
C2 C 0.13177(9) 0.71208(9) 0.06576(18) 0.0190(3) Uani 1 1 d . .
C3 C 0.15319(9) 0.80065(9) 0.0581(2) 0.0223(3) Uani 1 1 d . .
C4 C 0.08993(10) 0.80780(11) -0.0413(2) 0.0328(4) Uani 1 1 d . .
H4A H 0.1026 0.8641 -0.0427 0.049 Uiso 1 1 calc R .
H4B H 0.0365 0.7740 0.0057 0.049 Uiso 1 1 calc R .
H4C H 0.0903 0.7899 -0.1505 0.049 Uiso 1 1 calc R .
C5 C 0.19570(9) 0.63017(10) 0.09866(19) 0.0252(4) Uani 1 1 d . .
C6 C 0.13621(9) 0.65686(9) 0.33603(18) 0.0198(3) Uani 1 1 d . .
C7 C 0.05703(9) 0.59350(9) 0.3367(2) 0.0227(3) Uani 1 1 d . .
H7 H 0.0305 0.5701 0.2391 0.027 Uiso 1 1 calc R .
C8 C 0.01688(9) 0.56452(9) 0.4807(2) 0.0253(3) Uani 1 1 d . .
H8 H -0.0371 0.5209 0.4813 0.030 Uiso 1 1 calc R .
C9 C 0.05506(10) 0.59887(10) 0.6228(2) 0.0264(4) Uani 1 1 d . .
H9 H 0.0273 0.5795 0.7210 0.032 Uiso 1 1 calc R .
C10 C 0.13427(11) 0.66194(10) 0.62129(19) 0.0284(4) Uani 1 1 d . .
H10 H 0.1608 0.6854 0.7189 0.034 Uiso 1 1 calc R .
C11 C 0.17452(9) 0.69062(9) 0.47929(19) 0.0251(4) Uani 1 1 d . .
H11 H 0.2287 0.7337 0.4793 0.030 Uiso 1 1 calc R .
C12 C 0.16014(9) 0.83353(9) 0.22766(19) 0.0225(3) Uani 1 1 d . .
C13 C 0.08986(10) 0.81041(10) 0.3151(2) 0.0299(4) Uani 1 1 d . .
H13 H 0.0388 0.7756 0.2682 0.036 Uiso 1 1 calc R .
C14 C 0.09386(12) 0.83771(10) 0.4693(2) 0.0382(4) Uani 1 1 d . .
H14 H 0.0456 0.8221 0.5270 0.046 Uiso 1 1 calc R .
C15 C 0.16761(12) 0.88749(10) 0.5401(2) 0.0361(4) Uani 1 1 d . .
H15 H 0.1703 0.9060 0.6461 0.043 Uiso 1 1 calc R .
C16 C 0.23728(11) 0.90990(10) 0.4550(2) 0.0324(4) Uani 1 1 d . .
H16 H 0.2882 0.9439 0.5030 0.039 Uiso 1 1 calc R .
C17 C 0.23365(10) 0.88338(9) 0.3005(2) 0.0275(4) Uani 1 1 d . .
H17 H 0.2822 0.8995 0.2434 0.033 Uiso 1 1 calc R .
C18 C 0.23269(10) 0.84865(9) -0.03290(19) 0.0271(4) Uani 1 1 d . .
C19 C 0.33050(10) 0.83934(12) -0.1908(2) 0.0438(5) Uani 1 1 d . .
H19A H 0.3173 0.8560 -0.2915 0.066 Uiso 1 1 calc R .
H19B H 0.3491 0.8010 -0.2124 0.066 Uiso 1 1 calc R .
H19C H 0.3732 0.8867 -0.1361 0.066 Uiso 1 1 calc R .
C1S C 0.046(3) 0.012(3) 0.964(9) 0.120 Uiso 0.08 1 d P 1
C2S C 0.002(4) -0.010(4) 1.035(10) 0.120 Uiso 0.08 1 d P 2
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C18 O3 C19 116.29(13) . .
C5 C1 C6 111.05(12) . .
C5 C1 C2 108.32(13) . .
C6 C1 C2 110.20(11) . .
O1 C2 C3 122.17(14) . .
O1 C2 C1 119.91(13) . .
C3 C2 C1 117.91(13) . .
C18 C3 C4 105.53(13) . .
C18 C3 C2 108.69(13) . .
C4 C3 C2 109.57(13) . .
C18 C3 C12 111.10(13) . .
C4 C3 C12 112.23(13) . .
C2 C3 C12 109.61(13) . .
N1 C5 C1 178.87(17) . .
C11 C6 C7 119.67(14) . .
C11 C6 C1 119.77(13) . .
C7 C6 C1 120.57(13) . .
C8 C7 C6 119.76(15) . .
C9 C8 C7 120.32(14) . .
C8 C9 C10 119.61(15) . .
C11 C10 C9 120.38(15) . .
C10 C11 C6 120.27(14) . .
C17 C12 C13 118.20(15) . .
C17 C12 C3 122.75(14) . .
C13 C12 C3 119.01(14) . .
C14 C13 C12 120.61(17) . .
C15 C14 C13 120.46(17) . .
C16 C15 C14 119.24(17) . .
C15 C16 C17 120.57(17) . .
C16 C17 C12 120.92(16) . .
O2 C18 O3 124.03(15) . .
O2 C18 C3 124.31(16) . .
O3 C18 C3 111.57(13) . .
C1S C1S C1S 151.3(12) 6_554 5
C2S C2S C2S 171(2) 6_554 5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C5 1.149(2) .
O1 C2 1.2042(18) .
O2 C18 1.189(2) .
O3 C18 1.329(2) .
O3 C19 1.4635(19) .
C1 C5 1.467(2) .
C1 C6 1.531(2) .
C1 C2 1.544(2) .
C2 C3 1.534(2) .
C3 C18 1.532(2) .
C3 C4 1.533(2) .
C3 C12 1.534(2) .
C6 C11 1.388(2) .
C6 C7 1.390(2) .
C7 C8 1.390(2) .
C8 C9 1.382(2) .
C9 C10 1.389(2) .
C10 C11 1.376(2) .
C12 C17 1.387(2) .
C12 C13 1.396(2) .
C13 C14 1.384(3) .
C14 C15 1.382(3) .
C15 C16 1.379(3) .
C16 C17 1.381(2) .
C1S C1S 1.61(2) 6_554
C1S C1S 1.61(2) 5
C2S C2S 1.415(8) 6_554
C2S C2S 1.415(8) 5
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C5 C1 C2 O1 40.78(18)
C6 C1 C2 O1 -80.88(17)
C5 C1 C2 C3 -140.34(14)
C6 C1 C2 C3 98.00(15)
O1 C2 C3 C18 -107.98(16)
C1 C2 C3 C18 73.17(16)
O1 C2 C3 C4 6.9(2)
C1 C2 C3 C4 -171.99(13)
O1 C2 C3 C12 130.43(15)
C1 C2 C3 C12 -48.42(17)
C6 C1 C5 N1 98(9)
C2 C1 C5 N1 -23(9)
C5 C1 C6 C11 113.27(16)
C2 C1 C6 C11 -126.70(14)
C5 C1 C6 C7 -67.00(18)
C2 C1 C6 C7 53.03(18)
C11 C6 C7 C8 0.0(2)
C1 C6 C7 C8 -179.69(13)
C6 C7 C8 C9 0.6(2)
C7 C8 C9 C10 -0.9(2)
C8 C9 C10 C11 0.5(3)
C9 C10 C11 C6 0.2(2)
C7 C6 C11 C10 -0.4(2)
C1 C6 C11 C10 179.32(14)
C18 C3 C12 C17 -17.0(2)
C4 C3 C12 C17 -134.92(16)
C2 C3 C12 C17 103.09(16)
C18 C3 C12 C13 165.20(14)
C4 C3 C12 C13 47.32(19)
C2 C3 C12 C13 -74.67(17)
C17 C12 C13 C14 1.0(2)
C3 C12 C13 C14 178.84(15)
C12 C13 C14 C15 -0.9(3)
C13 C14 C15 C16 0.2(3)
C14 C15 C16 C17 0.3(3)
C15 C16 C17 C12 -0.2(3)
C13 C12 C17 C16 -0.4(2)
C3 C12 C17 C16 -178.22(14)
C19 O3 C18 O2 -2.0(3)
C19 O3 C18 C3 174.81(13)
C4 C3 C18 O2 63.7(2)
C2 C3 C18 O2 -178.89(17)
C12 C3 C18 O2 -58.2(2)
C4 C3 C18 O3 -113.16(15)
C2 C3 C18 O3 4.29(18)
C12 C3 C18 O3 124.96(14)
