#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/42/1514208.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_1514208
loop_
_publ_author_name
'Curto, John M'
'Dickstein, Joshua S'
'Berritt, Simon'
'Kozlowski, Marisa C'
_publ_section_title
;
 Asymmetric Synthesis of α-Allyl-α-Aryl α-Amino Acids by Tandem
 Alkylation/π-Allylation of α-Iminoesters.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1948
_journal_page_last               1951
_journal_paper_doi               10.1021/ol500506t
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C16 H15 N O3'
_chemical_formula_weight         269.29
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                78.99(2)
_cell_angle_beta                 70.106(18)
_cell_angle_gamma                65.402(15)
_cell_formula_units_Z            2
_cell_length_a                   9.0234(10)
_cell_length_b                   9.1282(15)
_cell_length_c                   10.3014(13)
_cell_measurement_temperature    296(1)
_cell_volume                     724.2(2)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      296(1)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6510
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7722
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2515
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0495
_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)+(0.0938P)²+0.0459P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1500
_reflns_number_gt                2016
_reflns_number_total             2515
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol500506t_si_004.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

 Adding full bibliography for
 ./tmp-cod-update-bibliographies-8800/cifs/1514208.cif.
;
_cod_original_cell_volume        724.25(17)
_cod_original_sg_symbol_H-M      'P -1       '
_cod_database_code               1514208
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C1 C 0.58570(18) 0.57153(18) 0.25679(14) 0.0509(4) Uani 1 1 d .
C2 C 0.52463(18) 0.36002(17) 0.22116(15) 0.0534(4) Uani 1 1 d .
C3 C 0.5285(2) 0.30898(18) 0.10154(15) 0.0588(4) Uani 1 1 d .
H3 H 0.6067 0.3216 0.0183 0.078 Uiso 1 1 calc R
C4 C 0.4176(2) 0.23946(18) 0.10410(15) 0.0596(4) Uani 1 1 d .
H4 H 0.4191 0.2090 0.0224 0.079 Uiso 1 1 calc R
C5 C 0.30423(19) 0.21504(18) 0.22807(15) 0.0557(4) Uani 1 1 d .
C6 C 0.3056(2) 0.2588(2) 0.34913(15) 0.0632(4) Uani 1 1 d .
H6 H 0.2332 0.2389 0.4333 0.084 Uiso 1 1 calc R
C7 C 0.4135(2) 0.3314(2) 0.34565(15) 0.0614(4) Uani 1 1 d .
H7 H 0.4120 0.3618 0.4274 0.082 Uiso 1 1 calc R
C8 C 0.1716(3) 0.1161(2) 0.1191(2) 0.0802(5) Uani 1 1 d .
H8A H 0.1524 0.2120 0.0589 0.120 Uiso 1 1 calc R
H8B H 0.0768 0.0837 0.1422 0.120 Uiso 1 1 calc R
H8C H 0.2738 0.0313 0.0732 0.120 Uiso 1 1 calc R
C9 C 0.70320(18) 0.64948(18) 0.24860(15) 0.0544(4) Uani 1 1 d .
C10 C 0.8777(2) 0.5634(2) 0.2128(2) 0.0773(5) Uani 1 1 d .
H10 H 0.9215 0.4549 0.1953 0.103 Uiso 1 1 calc R
C11 C 0.9872(2) 0.6375(3) 0.2030(3) 0.0949(7) Uani 1 1 d .
H11 H 1.1040 0.5781 0.1804 0.126 Uiso 1 1 calc R
C12 C 0.9249(3) 0.7970(2) 0.2262(2) 0.0867(6) Uani 1 1 d .
H12 H 0.9994 0.8464 0.2186 0.115 Uiso 1 1 calc R
C13 C 0.7536(2) 0.8847(2) 0.2606(2) 0.0763(5) Uani 1 1 d .
H13 H 0.7115 0.9937 0.2760 0.102 Uiso 1 1 calc R
C14 C 0.6426(2) 0.8112(2) 0.27250(17) 0.0629(4) Uani 1 1 d .
H14 H 0.5259 0.8712 0.2969 0.084 Uiso 1 1 calc R
C15 C 0.39681(18) 0.67149(18) 0.31253(14) 0.0524(4) Uani 1 1 d .
C16 C 0.1744(2) 0.7790(3) 0.5122(2) 0.0967(7) Uani 1 1 d .
H16A H 0.1474 0.8855 0.4679 0.145 Uiso 1 1 calc R
H16B H 0.1567 0.7853 0.6086 0.145 Uiso 1 1 calc R
H16C H 0.1022 0.7315 0.5022 0.145 Uiso 1 1 calc R
N1 N 0.64031(15) 0.43237(16) 0.21172(13) 0.0578(4) Uani 1 1 d .
O1 O 0.18931(16) 0.14739(15) 0.24191(12) 0.0736(4) Uani 1 1 d .
O2 O 0.30480(13) 0.73562(14) 0.24103(12) 0.0704(4) Uani 1 1 d .
O3 O 0.35069(12) 0.68070(14) 0.44866(10) 0.0676(4) Uani 1 1 d .
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
N1 C1 C9 121.45(13)
N1 C1 C15 122.25(13)
C9 C1 C15 116.16(13)
C3 C2 C7 118.56(14)
C3 C2 N1 118.28(13)
C7 C2 N1 123.10(13)
C4 C3 C2 120.86(14)
C3 C4 C5 120.17(14)
O1 C5 C4 124.79(13)
O1 C5 C6 116.03(13)
C4 C5 C6 119.17(14)
C7 C6 C5 120.42(14)
C6 C7 C2 120.70(14)
C14 C9 C10 118.18(15)
C14 C9 C1 121.04(14)
C10 C9 C1 120.75(14)
C11 C10 C9 120.56(17)
C12 C11 C10 120.29(18)
C11 C12 C13 120.27(17)
C12 C13 C14 119.92(17)
C13 C14 C9 120.78(16)
O2 C15 O3 125.31(14)
O2 C15 C1 123.39(13)
O3 C15 C1 111.28(11)
C1 N1 C2 120.31(13)
C5 O1 C8 117.73(13)
C15 O3 C16 116.03(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.273(2)
C1 C9 1.477(2)
C1 C15 1.519(2)
C2 C3 1.383(2)
C2 C7 1.390(2)
C2 N1 1.4198(19)
C3 C4 1.381(2)
C4 C5 1.385(2)
C5 O1 1.3696(18)
C5 C6 1.385(2)
C6 C7 1.376(2)
C8 O1 1.422(2)
C9 C14 1.383(2)
C9 C10 1.385(2)
C10 C11 1.380(3)
C11 C12 1.362(3)
C12 C13 1.364(3)
C13 C14 1.382(2)
C15 O2 1.1922(17)
C15 O3 1.3288(17)
C16 O3 1.446(2)
