#------------------------------------------------------------------------------
#$Date: 2016-03-21 19:06:25 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178835 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/89/4108958.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_4108958
loop_
_publ_author_name
'Kanwal J. Singh'
'Alexander C. Hoepker'
'David B. Collum'
_publ_section_title
;
 Autocatalysis in Lithium Diisopropylamide-Mediated Ortholithiations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18008
_journal_page_last               18017
_journal_paper_doi               10.1021/ja807331k
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C13 H18 F N O2'
_chemical_formula_weight         239.28
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.2230(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7977(4)
_cell_length_b                   11.3149(5)
_cell_length_c                   11.9339(5)
_cell_measurement_reflns_used    5536
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.16
_cell_measurement_theta_min      2.62
_cell_volume                     1307.96(9)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_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  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16281
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_correction_T_min  0.9646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       bloc
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3231
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0705P)²+0.0920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1267
_reflns_number_gt                2267
_reflns_number_total             3231
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja807331k_si_001.cif
_cod_data_source_block           ks3
_cod_database_code               4108958
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
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.14346(18) 0.03171(14) 0.43395(18) 0.1006(7) Uani 0.674(3) 1 d P A 1
F1' F -0.0433(4) 0.0851(3) 0.0463(3) 0.0989(14) Uani 0.326(3) 1 d P A 2
O1 O 0.22384(9) 0.39713(6) 0.28842(9) 0.0471(2) Uani 1 1 d . . .
O2 O 0.39821(9) 0.33576(7) 0.24708(9) 0.0491(3) Uani 1 1 d . . .
N1 N 0.37499(9) 0.53072(7) 0.28203(9) 0.0353(2) Uani 1 1 d . . .
C1 C 0.33979(11) 0.41668(9) 0.26980(11) 0.0347(3) Uani 1 1 d . . .
C2 C 0.49596(13) 0.56768(10) 0.26264(12) 0.0427(3) Uani 1 1 d . . .
H2 H 0.4972(12) 0.6536(12) 0.2701(11) 0.035(3) Uiso 1 1 d . . .
C3 C 0.4806(2) 0.53844(14) 0.13347(16) 0.0586(4) Uani 1 1 d . . .
H3C H 0.387(2) 0.5670(17) 0.0677(18) 0.088(6) Uiso 1 1 d . . .
H3B H 0.4817(17) 0.4537(15) 0.1219(15) 0.066(4) Uiso 1 1 d . . .
H3A H 0.5532(19) 0.5766(15) 0.1197(16) 0.075(5) Uiso 1 1 d . . .
C4 C 0.62972(15) 0.52140(16) 0.36450(19) 0.0641(4) Uani 1 1 d . . .
H4C H 0.6360(17) 0.4350(17) 0.3581(15) 0.070(5) Uiso 1 1 d . . .
H4A H 0.633(2) 0.5409(17) 0.4461(19) 0.084(6) Uiso 1 1 d . . .
H4A H 0.707(2) 0.5530(16) 0.3517(17) 0.087(6) Uiso 1 1 d . . .
C5 C 0.29022(13) 0.62410(10) 0.29964(12) 0.0445(3) Uani 1 1 d . . .
H5 H 0.2289(14) 0.5838(12) 0.3237(12) 0.044(3) Uiso 1 1 d . . .
C6 C 0.2073(2) 0.68839(16) 0.17799(19) 0.0707(5) Uani 1 1 d . . .
H6C H 0.147(2) 0.632(2) 0.112(2) 0.107(7) Uiso 1 1 d . . .
H6B H 0.2681(17) 0.7291(14) 0.1509(14) 0.058(4) Uiso 1 1 d . . .
H6A H 0.1463(19) 0.7461(17) 0.1909(16) 0.082(5) Uiso 1 1 d . . .
C7 C 0.3752(2) 0.70828(15) 0.40393(18) 0.0673(5) Uani 1 1 d . . .
H7C H 0.4322(19) 0.6665(16) 0.4820(17) 0.080(6) Uiso 1 1 d . . .
H7B H 0.306(2) 0.7622(19) 0.4160(18) 0.094(6) Uiso 1 1 d . . .
H7A H 0.4374(18) 0.7609(15) 0.3808(15) 0.071(5) Uiso 1 1 d . . .
C8 C 0.17215(12) 0.28248(10) 0.26941(13) 0.0435(3) Uani 1 1 d . . .
C9 C 0.19736(16) 0.21291(13) 0.37087(18) 0.0591(4) Uani 1 1 d . A .
H9 H 0.256(2) 0.2386(16) 0.4537(17) 0.081(6) Uiso 1 1 d . . .
C10 C 0.1349(2) 0.10219(14) 0.3470(2) 0.0798(6) Uani 1 1 d . . .
C11 C 0.05273(19) 0.06183(14) 0.2292(2) 0.0806(6) Uani 1 1 d . A .
H11 H 0.013(2) -0.015(2) 0.2173(19) 0.098(6) Uiso 1 1 d . . .
C12 C 0.02955(17) 0.13479(15) 0.1309(2) 0.0764(5) Uani 1 1 d . . .
C13 C 0.08798(15) 0.24578(12) 0.14918(16) 0.0568(4) Uani 1 1 d . A .
H13 H 0.0704(19) 0.3027(17) 0.0767(18) 0.091(6) Uiso 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 O1 C8 116.72(8)
C1 N1 C5 122.98(9)
C1 N1 C2 118.89(9)
C5 N1 C2 117.75(9)
O2 C1 N1 127.24(10)
O2 C1 O1 120.95(9)
N1 C1 O1 111.80(9)
N1 C2 C3 112.93(11)
N1 C2 C4 111.77(11)
C3 C2 C4 112.29(13)
N1 C5 C6 110.45(11)
N1 C5 C7 112.33(12)
C6 C5 C7 111.91(13)
C9 C8 C13 121.97(13)
C9 C8 O1 118.96(13)
C13 C8 O1 118.86(12)
C8 C9 C10 116.66(18)
F1 C10 C11 114.02(17)
F1 C10 C9 122.7(2)
C11 C10 C9 123.13(17)
C12 C11 C10 118.12(14)
F1' C12 C11 105.1(3)
F1' C12 C13 133.7(3)
C11 C12 C13 121.16(19)
C12 C13 C8 118.94(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C10 1.279(2)
F1' C12 1.118(3)
O1 C1 1.3827(13)
O1 C8 1.3906(13)
O2 C1 1.2086(13)
N1 C1 1.3348(13)
N1 C5 1.4725(14)
N1 C2 1.4838(14)
C2 C3 1.512(2)
C2 C4 1.512(2)
C5 C6 1.513(2)
C5 C7 1.513(2)
C8 C9 1.367(2)
C8 C13 1.380(2)
C9 C10 1.391(2)
C10 C11 1.368(3)
C11 C12 1.365(3)
C12 C13 1.379(2)
