#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/30/4023043.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_4023043
loop_
_publ_author_name
'Zengxue Wang'
'Wen Wan'
'Haizhen Jiang'
'Jian Hao'
_publ_section_title
;
 One-Pot Cyclization of 2-Aminophenethyl Alcohols:
 A Novel and Direct Approach to the Synthesis of N-Acyl Indolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9364
_journal_page_last               9367
_journal_paper_doi               10.1021/jo701566v
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C10 H8 F3 N O'
_chemical_formula_weight         215.17
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.478(4)
_cell_angle_beta                 78.156(4)
_cell_angle_gamma                82.191(4)
_cell_formula_units_Z            2
_cell_length_a                   6.5694(19)
_cell_length_b                   7.825(2)
_cell_length_c                   9.863(3)
_cell_measurement_reflns_used    455
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      19.304
_cell_measurement_theta_min      2.159
_cell_volume                     480.4(2)
_computing_cell_refinement       SAINT
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ω
_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  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2481
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_correction_T_min  0.9603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.109(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_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         1651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0553
_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)+(0.0724P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1590
_reflns_number_gt                894
_reflns_number_total             1651
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701566v-File001.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023043
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
F1 F 0.4670(4) 0.7097(4) 0.0242(2) 0.1458(11) Uani 1 1 d .
F2 F 0.2700(4) 0.9439(3) 0.0420(2) 0.1328(10) Uani 1 1 d .
F3 F 0.1400(4) 0.7090(3) 0.0453(2) 0.1270(9) Uani 1 1 d .
C1 C 0.0588(5) 0.7271(3) 0.4813(3) 0.0608(8) Uani 1 1 d .
C2 C 0.1905(5) 0.6416(4) 0.5733(3) 0.0722(9) Uani 1 1 d .
H2 H 0.3238 0.5943 0.5395 0.087 Uiso 1 1 calc R
C3 C 0.1193(6) 0.6281(4) 0.7170(4) 0.0850(10) Uani 1 1 d .
H3 H 0.2056 0.5707 0.7808 0.102 Uiso 1 1 calc R
C4 C -0.0781(7) 0.6988(5) 0.7666(4) 0.0937(11) Uani 1 1 d .
H4 H -0.1235 0.6894 0.8636 0.112 Uiso 1 1 calc R
C5 C -0.2084(5) 0.7830(4) 0.6742(4) 0.0865(10) Uani 1 1 d .
H5 H -0.3419 0.8296 0.7083 0.104 Uiso 1 1 calc R
C6 C -0.1405(5) 0.7978(4) 0.5313(3) 0.0668(8) Uani 1 1 d .
C7 C -0.2496(5) 0.8841(4) 0.4105(4) 0.0836(10) Uani 1 1 d .
H7A H -0.2748 1.0106 0.4042 0.100 Uiso 1 1 calc R
H7B H -0.3821 0.8362 0.4216 0.100 Uiso 1 1 calc R
C8 C -0.1016(5) 0.8430(4) 0.2805(3) 0.0815(10) Uani 1 1 d .
H8A H -0.1597 0.7635 0.2396 0.098 Uiso 1 1 calc R
H8B H -0.0747 0.9503 0.2095 0.098 Uiso 1 1 calc R
C9 C 0.2755(6) 0.7201(4) 0.2504(3) 0.0717(9) Uani 1 1 d .
C10 C 0.2853(7) 0.7697(5) 0.0892(4) 0.0955(11) Uani 1 1 d .
N1 N 0.0931(4) 0.7586(3) 0.3310(2) 0.0622(7) Uani 1 1 d .
O1 O 0.4337(4) 0.6515(3) 0.2930(3) 0.1002(9) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.130(2) 0.194(3) 0.0948(17) -0.0414(16) 0.0151(15) 0.0144(17)
F2 0.157(2) 0.1158(19) 0.1040(18) 0.0073(14) -0.0018(15) -0.0242(15)
F3 0.151(2) 0.169(2) 0.0763(14) -0.0304(13) -0.0310(14) -0.0428(17)
C1 0.062(2) 0.0542(16) 0.071(2) -0.0190(14) -0.0158(16) -0.0057(14)
C2 0.068(2) 0.0731(19) 0.078(2) -0.0190(16) -0.0233(18) 0.0028(16)
C3 0.096(3) 0.088(2) 0.074(2) -0.0158(18) -0.027(2) -0.005(2)
C4 0.110(3) 0.097(3) 0.073(2) -0.023(2) -0.009(2) -0.010(2)
C5 0.077(2) 0.094(2) 0.085(3) -0.026(2) 0.000(2) -0.0033(19)
C6 0.064(2) 0.0608(18) 0.078(2) -0.0177(15) -0.0151(17) -0.0050(15)
C7 0.063(2) 0.088(2) 0.104(3) -0.033(2) -0.018(2) 0.0027(17)
C8 0.073(2) 0.086(2) 0.087(2) -0.0123(18) -0.0301(19) 0.0019(17)
C9 0.064(2) 0.080(2) 0.076(2) -0.0212(17) -0.0175(18) -0.0074(17)
C10 0.096(3) 0.105(3) 0.079(3) -0.021(2) -0.002(2) -0.008(2)
N1 0.0532(16) 0.0689(15) 0.0666(16) -0.0162(12) -0.0164(13) -0.0009(12)
O1 0.0606(15) 0.147(2) 0.0952(18) -0.0384(15) -0.0193(13) 0.0129(14)
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
C2 C1 C6 121.0(3)
C2 C1 N1 129.5(3)
C6 C1 N1 109.5(3)
C1 C2 C3 118.3(3)
C1 C2 H2 120.9
C3 C2 H2 120.9
C4 C3 C2 120.7(3)
C4 C3 H3 119.6
C2 C3 H3 119.6
C5 C4 C3 120.6(3)
C5 C4 H4 119.7
C3 C4 H4 119.7
C6 C5 C4 119.6(3)
C6 C5 H5 120.2
C4 C5 H5 120.2
C5 C6 C1 119.8(3)
C5 C6 C7 129.8(3)
C1 C6 C7 110.4(3)
C6 C7 C8 104.7(2)
C6 C7 H7A 110.8
C8 C7 H7A 110.8
C6 C7 H7B 110.8
C8 C7 H7B 110.8
H7A C7 H7B 108.9
N1 C8 C7 105.4(2)
N1 C8 H8A 110.7
C7 C8 H8A 110.7
N1 C8 H8B 110.7
C7 C8 H8B 110.7
H8A C8 H8B 108.8
O1 C9 N1 125.9(3)
O1 C9 C10 117.3(3)
N1 C9 C10 116.7(3)
F3 C10 F1 107.5(3)
F3 C10 F2 106.9(4)
F1 C10 F2 106.2(3)
F3 C10 C9 114.4(3)
F1 C10 C9 110.0(3)
F2 C10 C9 111.4(3)
C9 N1 C1 124.1(3)
C9 N1 C8 126.5(3)
C1 N1 C8 109.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C10 1.315(4)
F2 C10 1.331(4)
F3 C10 1.309(4)
C1 C2 1.379(4)
C1 C6 1.389(4)
C1 N1 1.420(4)
C2 C3 1.382(4)
C2 H2 0.9300
C3 C4 1.378(4)
C3 H3 0.9300
C4 C5 1.373(5)
C4 H4 0.9300
C5 C6 1.371(4)
C5 H5 0.9300
C6 C7 1.493(4)
C7 C8 1.514(4)
C7 H7A 0.9700
C7 H7B 0.9700
C8 N1 1.483(3)
C8 H8A 0.9700
C8 H8B 0.9700
C9 O1 1.211(3)
C9 N1 1.334(4)
C9 C10 1.536(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3606526
