#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/20/1512058.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_1512058
loop_
_publ_author_name
'Pinho, Vagner D.'
'Procter, David J.'
'Burtoloso, Antonio C. B.'
_publ_section_title
;
 SmI2-Mediated Couplings of α-Amino Acid Derivatives. Formal Synthesis of
 (−)-Pumiliotoxin 251D and (+-)-Epiquinamide
;
_journal_issue                   10
_journal_name_full               'Organic Letters'
_journal_page_first              2434
_journal_paper_doi               10.1021/ol400903n
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C12 H13 N O2'
_chemical_formula_weight         203.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 110.433(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2293(3)
_cell_length_b                   11.9799(5)
_cell_length_c                   9.5067(3)
_cell_measurement_reflns_used    3478
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.16
_cell_measurement_theta_min      5.11
_cell_volume                     984.98(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5469
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         72.16
_diffrn_reflns_theta_min         5.11
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_T_max  0.8818
_exptl_absorpt_correction_T_min  0.608893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0370
_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)+(0.0525P)²+0.3731P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0965
_reflns_number_gt                1701
_reflns_number_total             1884
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol400903n_si_002.cif
_cod_data_source_block           s3755ma
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.3.1 from 2005-06-27.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1512058
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.67101(13) 0.80352(10) 0.77596(13) 0.0129(3) Uani 1 1 d .
C2 C 0.53504(14) 0.75983(11) 0.64664(14) 0.0175(3) Uani 1 1 d .
H2A H 0.5258 0.8044 0.5562 0.021 Uiso 1 1 calc R
H2B H 0.4399 0.7724 0.6701 0.021 Uiso 1 1 calc R
C3 C 0.54219(14) 0.63638(11) 0.60869(13) 0.0178(3) Uani 1 1 d .
H3A H 0.4385 0.6108 0.5435 0.021 Uiso 1 1 calc R
H3B H 0.6141 0.6264 0.5531 0.021 Uiso 1 1 calc R
C4 C 0.59695(13) 0.56631(10) 0.75181(13) 0.0141(3) Uani 1 1 d .
H4 H 0.6010 0.4860 0.7248 0.017 Uiso 1 1 calc R
C5 C 0.75758(13) 0.60489(10) 0.84710(13) 0.0123(3) Uani 1 1 d .
H5 H 0.8301 0.5843 0.7939 0.015 Uiso 1 1 calc R
C6 C 0.82410(13) 0.55961(10) 1.00768(13) 0.0134(3) Uani 1 1 d .
H6A H 0.7416 0.5463 1.0500 0.016 Uiso 1 1 calc R
H6B H 0.8822 0.4895 1.0119 0.016 Uiso 1 1 calc R
C7 C 0.93016(13) 0.65323(10) 1.08893(13) 0.0131(3) Uani 1 1 d .
C8 C 1.05168(14) 0.65468(11) 1.22529(14) 0.0172(3) Uani 1 1 d .
H8 H 1.0800 0.5888 1.2841 0.021 Uiso 1 1 calc R
C9 C 1.13174(14) 0.75418(12) 1.27492(14) 0.0202(3) Uani 1 1 d .
H9 H 1.2163 0.7557 1.3673 0.024 Uiso 1 1 calc R
C10 C 1.08880(14) 0.85107(11) 1.19041(14) 0.0186(3) Uani 1 1 d .
H10 H 1.1448 0.9181 1.2256 0.022 Uiso 1 1 calc R
C11 C 0.96463(14) 0.85157(10) 1.05452(14) 0.0155(3) Uani 1 1 d .
H11 H 0.9334 0.9182 0.9977 0.019 Uiso 1 1 calc R
C12 C 0.88848(12) 0.75147(10) 1.00542(13) 0.0124(3) Uani 1 1 d .
N1 N 0.76501(11) 0.72798(8) 0.86939(11) 0.0121(2) Uani 1 1 d .
O1 O 0.69106(10) 0.90497(7) 0.79946(10) 0.0169(2) Uani 1 1 d .
O2 O 0.49623(10) 0.57829(8) 0.83479(10) 0.0164(2) Uani 1 1 d .
H2 H 0.4287 0.5279 0.8096 0.025 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
O1 C1 N1 121.20(11)
O1 C1 C2 121.09(11)
N1 C1 C2 117.62(11)
C1 C2 C3 115.78(10)
C1 C2 H2A 108.3
C3 C2 H2A 108.3
C1 C2 H2B 108.3
C3 C2 H2B 108.3
H2A C2 H2B 107.4
C4 C3 C2 110.47(10)
C4 C3 H3A 109.6
C2 C3 H3A 109.6
C4 C3 H3B 109.6
C2 C3 H3B 109.6
H3A C3 H3B 108.1
O2 C4 C5 109.30(9)
O2 C4 C3 111.22(10)
C5 C4 C3 108.39(10)
O2 C4 H4 109.3
C5 C4 H4 109.3
C3 C4 H4 109.3
N1 C5 C4 111.99(9)
N1 C5 C6 103.09(9)
C4 C5 C6 117.12(10)
N1 C5 H5 108.1
C4 C5 H5 108.1
C6 C5 H5 108.1
C7 C6 C5 102.07(9)
C7 C6 H6A 111.4
C5 C6 H6A 111.4
C7 C6 H6B 111.4
C5 C6 H6B 111.4
H6A C6 H6B 109.2
C8 C7 C12 119.55(11)
C8 C7 C6 130.92(11)
C12 C7 C6 109.52(10)
C7 C8 C9 119.13(12)
C7 C8 H8 120.4
C9 C8 H8 120.4
C10 C9 C8 120.54(11)
C10 C9 H9 119.7
C8 C9 H9 119.7
C9 C10 C11 121.02(12)
C9 C10 H10 119.5
C11 C10 H10 119.5
C12 C11 C10 117.64(12)
C12 C11 H11 121.2
C10 C11 H11 121.2
C11 C12 C7 122.08(11)
C11 C12 N1 128.96(11)
C7 C12 N1 108.94(10)
C1 N1 C12 126.35(10)
C1 N1 C5 125.70(10)
C12 N1 C5 107.95(9)
C4 O2 H2 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2378(16)
C1 N1 1.3500(15)
C1 C2 1.5109(16)
C2 C3 1.5292(18)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.5268(17)
C3 H3A 0.9900
C3 H3B 0.9900
C4 O2 1.4210(14)
C4 C5 1.5147(16)
C4 H4 1.0000
C5 N1 1.4880(15)
C5 C6 1.5321(16)
C5 H5 1.0000
C6 C7 1.5116(16)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.3869(17)
C7 C12 1.3964(17)
C8 C9 1.3951(19)
C8 H8 0.9500
C9 C10 1.388(2)
C9 H9 0.9500
C10 C11 1.3958(18)
C10 H10 0.9500
C11 C12 1.3860(17)
C11 H11 0.9500
C12 N1 1.4216(15)
O2 H2 0.8400
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
O2 H2 O1 0.84 1.91 2.7180(12) 159.6 2_646
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
O1 C1 C2 C3 167.04(11)
N1 C1 C2 C3 -16.38(15)
C1 C2 C3 C4 43.77(14)
C2 C3 C4 O2 59.31(13)
C2 C3 C4 C5 -60.87(13)
O2 C4 C5 N1 -70.20(12)
C3 C4 C5 N1 51.17(13)
O2 C4 C5 C6 48.56(14)
C3 C4 C5 C6 169.94(10)
N1 C5 C6 C7 -27.49(10)
C4 C5 C6 C7 -150.93(10)
C5 C6 C7 C8 -161.79(12)
C5 C6 C7 C12 19.31(12)
C12 C7 C8 C9 -1.16(17)
C6 C7 C8 C9 -179.97(11)
C7 C8 C9 C10 1.14(19)
C8 C9 C10 C11 0.25(19)
C9 C10 C11 C12 -1.57(18)
C10 C11 C12 C7 1.55(17)
C10 C11 C12 N1 -176.63(11)
C8 C7 C12 C11 -0.20(17)
C6 C7 C12 C11 178.85(10)
C8 C7 C12 N1 178.31(10)
C6 C7 C12 N1 -2.65(13)
O1 C1 N1 C12 3.64(17)
C2 C1 N1 C12 -172.93(10)
O1 C1 N1 C5 -176.03(10)
C2 C1 N1 C5 7.39(16)
C11 C12 N1 C1 -17.49(18)
C7 C12 N1 C1 164.14(10)
C11 C12 N1 C5 162.24(11)
C7 C12 N1 C5 -16.13(12)
C4 C5 N1 C1 -25.90(15)
C6 C5 N1 C1 -152.68(10)
C4 C5 N1 C12 154.38(9)
C6 C5 N1 C12 27.60(11)
