#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/70/1507063.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_1507063
loop_
_publ_author_name
'Wolckenhauer, Scott A.'
'Rychnovsky, Scott D.'
_publ_section_title
;
 Generation and utility of tertiary alpha-aminoorganolithium reagents.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              2745
_journal_page_last               2748
_journal_paper_doi               10.1021/ol049039p
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C14 H22 F3 N O3'
_chemical_formula_weight         309.33
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 114.216(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8599(9)
_cell_length_b                   20.656(2)
_cell_length_c                   9.0612(9)
_cell_measurement_temperature    163(2)
_cell_volume                     1512.4(3)
_computing_cell_refinement       'Bruker SMART/SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      163(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15886
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.65
_diffrn_standards_decay_%        '< 1.0'
_diffrn_standards_interval_count 'initial 50 frames recollected'
_diffrn_standards_number         '50 frames'
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.9791
_exptl_absorpt_correction_T_min  0.9711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       mfp
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0422
_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)+(0.0361P)²+0.9311P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1098
_reflns_number_gt                2805
_reflns_number_total             3678
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol049039psi20040617_054232.cif
_cod_data_source_block           sdr13
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/a' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1507063
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
N1 N 0.02702(15) 0.08164(6) -0.17550(15) 0.0169(2) Uani 1 1 d
O1 O -0.57739(14) 0.20581(6) -0.20269(15) 0.0329(3) Uani 1 1 d
C1 C 0.1407(2) 0.07220(8) -0.25911(19) 0.0233(3) Uani 1 1 d
C2 C 0.0517(2) 0.08950(8) -0.4363(2) 0.0280(3) Uani 1 1 d
C3 C -0.0037(2) 0.15979(8) -0.45100(19) 0.0251(3) Uani 1 1 d
C4 C -0.11798(19) 0.17049(7) -0.36459(18) 0.0209(3) Uani 1 1 d
C5 C -0.04612(17) 0.14900(6) -0.18618(16) 0.0164(3) Uani 1 1 d
C6 C -0.18779(17) 0.14092(7) -0.12791(17) 0.0179(3) Uani 1 1 d
C7 C -0.2910(2) 0.20319(8) -0.1521(2) 0.0249(3) Uani 1 1 d
C8 C -0.43722(19) 0.19187(7) -0.1091(2) 0.0243(3) Uani 1 1 d
C9 C -0.3966(2) 0.16266(9) 0.0547(2) 0.0295(4) Uani 1 1 d
C10 C -0.2837(2) 0.10343(8) 0.0835(2) 0.0265(3) Uani 1 1 d
C11 C -0.13293(19) 0.11794(8) 0.04710(18) 0.0222(3) Uani 1 1 d
C12 C 0.09069(18) 0.19463(7) -0.07937(19) 0.0207(3) Uani 1 1 d
H1 H 0.085(2) 0.0707(9) -0.071(2) 0.026(5) Uiso 1 1 d
H2 H -0.057(2) 0.0508(10) -0.219(2) 0.030(5) Uiso 1 1 d
H1A H 0.238(2) 0.0993(9) -0.204(2) 0.026(5) Uiso 1 1 d
H1B H 0.172(2) 0.0268(9) -0.244(2) 0.026(4) Uiso 1 1 d
H2A H 0.126(2) 0.0803(9) -0.488(2) 0.035(5) Uiso 1 1 d
H2B H -0.043(2) 0.0615(10) -0.487(2) 0.031(5) Uiso 1 1 d
H3A H -0.060(2) 0.1726(9) -0.563(2) 0.026(4) Uiso 1 1 d
H3B H 0.094(2) 0.1877(9) -0.405(2) 0.028(5) Uiso 1 1 d
H4A H -0.144(2) 0.2153(9) -0.366(2) 0.020(4) Uiso 1 1 d
H4B H -0.220(2) 0.1469(9) -0.421(2) 0.031(5) Uiso 1 1 d
H6A H -0.259(2) 0.1083(8) -0.196(2) 0.019(4) Uiso 1 1 d
H7A H -0.222(2) 0.2372(10) -0.078(2) 0.032(5) Uiso 1 1 d
H7B H -0.333(2) 0.2178(9) -0.261(2) 0.032(5) Uiso 1 1 d
H9A H -0.497(3) 0.1518(10) 0.066(3) 0.044(6) Uiso 1 1 d
H9B H -0.336(2) 0.1960(10) 0.137(2) 0.032(5) Uiso 1 1 d
H10A H -0.348(2) 0.0668(9) 0.012(2) 0.028(5) Uiso 1 1 d
H10B H -0.247(2) 0.0878(9) 0.196(2) 0.032(5) Uiso 1 1 d
H11A H -0.066(2) 0.0791(9) 0.068(2) 0.025(4) Uiso 1 1 d
H11B H -0.062(2) 0.1516(9) 0.122(2) 0.030(5) Uiso 1 1 d
H12A H 0.175(2) 0.1997(9) -0.123(2) 0.025(4) Uiso 1 1 d
H12B H 0.143(2) 0.1780(9) 0.030(2) 0.025(4) Uiso 1 1 d
H12C H 0.039(2) 0.2358(10) -0.078(2) 0.032(5) Uiso 1 1 d
C13 C 0.28094(18) 0.04202(7) 0.26219(18) 0.0211(3) Uani 1 1 d
C14 C 0.4219(2) 0.08541(8) 0.3775(2) 0.0302(4) Uani 1 1 d
O3 O 0.20398(14) 0.01106(6) 0.32578(14) 0.0295(3) Uani 1 1 d
O2 O 0.26181(14) 0.04496(6) 0.11896(13) 0.0330(3) Uani 1 1 d
F1 F 0.3820(2) 0.14771(6) 0.34634(18) 0.0747(5) Uani 1 1 d
F2 F 0.56226(14) 0.07642(7) 0.35846(14) 0.0560(4) Uani 1 1 d
F3 F 0.45843(13) 0.07593(6) 0.53325(12) 0.0410(3) 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'
F F 0.0171 0.0103 '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 N1 C5 116.31(11)
N1 C1 C2 109.86(13)
C1 C2 C3 109.09(13)
C2 C3 C4 110.56(13)
C3 C4 C5 114.87(12)
N1 C5 C12 108.52(11)
N1 C5 C4 108.20(11)
C12 C5 C4 111.49(12)
N1 C5 C6 105.18(11)
C12 C5 C6 113.07(12)
C4 C5 C6 110.07(11)
C11 C6 C7 108.90(12)
C11 C6 C5 115.26(11)
C7 C6 C5 112.10(12)
C8 C7 C6 110.76(12)
O1 C8 C9 123.09(14)
O1 C8 C7 121.29(15)
C9 C8 C7 115.62(13)
C8 C9 C10 111.32(13)
C11 C10 C9 111.92(13)
C10 C11 C6 110.45(13)
O3 C13 O2 130.44(15)
O3 C13 C14 115.62(13)
O2 C13 C14 113.92(14)
F3 C14 F1 107.20(15)
F3 C14 F2 106.44(14)
F1 C14 F2 106.65(15)
F3 C14 C13 114.26(13)
F1 C14 C13 110.24(14)
F2 C14 C13 111.65(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.5008(18)
N1 C5 1.5212(17)
O1 C8 1.2168(19)
C1 C2 1.513(2)
C2 C3 1.521(2)
C3 C4 1.529(2)
C4 C5 1.5399(19)
C5 C12 1.5271(19)
C5 C6 1.5575(19)
C6 C11 1.531(2)
C6 C7 1.541(2)
C7 C8 1.516(2)
C8 C9 1.502(2)
C9 C10 1.534(2)
C10 C11 1.531(2)
C13 O3 1.2362(19)
C13 O2 1.2396(19)
C13 C14 1.544(2)
C14 F3 1.3264(19)
C14 F1 1.334(2)
C14 F2 1.337(2)
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 N1 C1 C2 -57.18(17)
N1 C1 C2 C3 59.55(17)
C1 C2 C3 C4 -58.82(18)
C2 C3 C4 C5 54.43(18)
C1 N1 C5 C12 -71.96(15)
C1 N1 C5 C4 49.17(15)
C1 N1 C5 C6 166.77(12)
C3 C4 C5 N1 -47.23(16)
C3 C4 C5 C12 72.03(16)
C3 C4 C5 C6 -161.66(12)
N1 C5 C6 C11 62.18(15)
C12 C5 C6 C11 -56.06(16)
C4 C5 C6 C11 178.52(12)
N1 C5 C6 C7 -172.49(12)
C12 C5 C6 C7 69.26(15)
C4 C5 C6 C7 -56.16(16)
C11 C6 C7 C8 -56.57(17)
C5 C6 C7 C8 174.69(12)
C6 C7 C8 O1 -127.74(16)
C6 C7 C8 C9 52.21(18)
O1 C8 C9 C10 131.49(16)
C7 C8 C9 C10 -48.5(2)
C8 C9 C10 C11 50.43(19)
C9 C10 C11 C6 -57.91(18)
C7 C6 C11 C10 60.35(16)
C5 C6 C11 C10 -172.70(12)
O3 C13 C14 F3 10.1(2)
O2 C13 C14 F3 -171.12(14)
O3 C13 C14 F1 -110.71(17)
O2 C13 C14 F1 68.10(19)
O3 C13 C14 F2 130.93(15)
O2 C13 C14 F2 -50.26(19)
