#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/15/7151591.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_7151591
loop_
_publ_author_name
'Briggs, Caroline R. S.'
'Allen, Mark J.'
'O'Hagan, David'
'Tozer, David J.'
'Slawin, Alexandra M. Z.'
'Goeta, Andrés E'
'Howard, Judith A. K.'
_publ_section_title
;
 The observation of a large gauche preference when 2-fluoroethylamine
 and 2-fluoroethanol become protonated.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              732
_journal_page_last               740
_journal_paper_doi               10.1039/b312188g
_journal_volume                  2
_journal_year                    2004
_chemical_formula_moiety         'C6 H13 Cl F N O'
_chemical_formula_sum            'C6 H13 Cl F N O'
_chemical_formula_weight         169.62
_chemical_melting_point          ?
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.072(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.340(2)
_cell_length_b                   9.302(3)
_cell_length_c                   12.025(4)
_cell_measurement_reflns_used    60
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      168
_cell_measurement_theta_min      12
_cell_volume                     820.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      125(2)
_diffrn_detector_area_resol_mean 0.9
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3185
_diffrn_reflns_theta_full        23.30
_diffrn_reflns_theta_max         23.30
_diffrn_reflns_theta_min         3.20
_diffrn_standards_decay_%        -
_diffrn_standards_interval_count -
_diffrn_standards_interval_time  -
_diffrn_standards_number         -
_exptl_absorpt_coefficient_mu    0.419
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.756501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   -
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          .1
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .03
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.009(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1131
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0817P)²+0.0877P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                1029
_reflns_number_total             1131
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b312188g.txt
_cod_data_source_block           9
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'multiscan' changed to
'multi-scan' according to
'/home/adriana/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 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '-' was changed to '?' - the value is
undefined or not given.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value '-' 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_cell_volume        820.6(5)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7151591
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.61037(6) 0.21539(5) 1.09384(4) 0.0252(3) Uani 1 1 d . . .
N1 N 0.3959(2) 0.23870(17) 0.87396(15) 0.0199(4) Uani 1 1 d D . .
H1N H 0.469(3) 0.224(2) 0.9427(11) 0.037(7) Uiso 1 1 d D . .
C2 C 0.2298(3) 0.14418(19) 0.87288(15) 0.0228(5) Uani 1 1 d . . .
H2A H 0.2674 0.0422 0.8790 0.027 Uiso 1 1 calc R . .
H2B H 0.1595 0.1566 0.8017 0.027 Uiso 1 1 calc R . .
C3 C 0.1125(3) 0.1827(2) 0.96847(17) 0.0278(5) Uani 1 1 d . . .
H3A H 0.0025 0.1211 0.9662 0.033 Uiso 1 1 calc R . .
H3B H 0.1808 0.1637 1.0394 0.033 Uiso 1 1 calc R . .
O4 O 0.05860(18) 0.32937(15) 0.96494(12) 0.0291(4) Uani 1 1 d . . .
C5 C 0.2156(2) 0.4200(2) 0.96904(16) 0.0247(5) Uani 1 1 d . . .
H5A H 0.2858 0.4029 1.0396 0.030 Uiso 1 1 calc R . .
H5B H 0.1762 0.5218 0.9679 0.030 Uiso 1 1 calc R . .
C6 C 0.3364(2) 0.39279(19) 0.87267(15) 0.0226(5) Uani 1 1 d . . .
H6A H 0.2691 0.4143 0.8018 0.027 Uiso 1 1 calc R . .
H6B H 0.4445 0.4564 0.8784 0.027 Uiso 1 1 calc R . .
C7 C 0.5180(3) 0.2004(2) 0.78165(17) 0.0264(5) Uani 1 1 d . . .
H7A H 0.4538 0.2209 0.7096 0.032 Uiso 1 1 calc R . .
H7B H 0.5436 0.0959 0.7847 0.032 Uiso 1 1 calc R . .
C8 C 0.6953(3) 0.2807(2) 0.78664(19) 0.0328(6) Uani 1 1 d . . .
H8A H 0.7430 0.2849 0.8646 0.039 Uiso 1 1 calc R . .
H8B H 0.7856 0.2291 0.7422 0.039 Uiso 1 1 calc R . .
F8 F 0.67185(16) 0.42144(14) 0.74507(10) 0.0405(4) 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
Cl1 0.0306(4) 0.0231(4) 0.0206(4) -0.00074(16) -0.0159(2) 0.00372(17)
N1 0.0223(9) 0.0181(8) 0.0187(9) -0.0007(6) -0.0084(7) 0.0042(6)
C2 0.0279(10) 0.0155(9) 0.0241(10) 0.0008(7) -0.0115(8) -0.0022(7)
C3 0.0313(11) 0.0214(10) 0.0301(12) 0.0013(8) -0.0057(9) -0.0029(8)
O4 0.0226(8) 0.0224(8) 0.0423(9) -0.0032(6) -0.0013(6) 0.0008(6)
C5 0.0229(10) 0.0195(10) 0.0312(11) -0.0036(8) -0.0069(8) 0.0011(8)
C6 0.0253(10) 0.0160(9) 0.0257(10) 0.0006(8) -0.0087(8) 0.0003(7)
C7 0.0276(11) 0.0300(11) 0.0211(11) -0.0050(8) -0.0080(8) 0.0057(8)
C8 0.0271(11) 0.0456(14) 0.0253(12) -0.0054(9) -0.0050(9) 0.0035(9)
F8 0.0403(8) 0.0438(8) 0.0377(8) -0.0031(6) 0.0066(6) -0.0079(6)
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C6 113.75(15) . . ?
C7 N1 C2 111.23(15) . . ?
C6 N1 C2 108.87(13) . . ?
N1 C2 C3 109.91(16) . . ?
O4 C3 C2 111.88(16) . . ?
C3 O4 C5 110.03(14) . . ?
O4 C5 C6 111.82(16) . . ?
N1 C6 C5 109.40(15) . . ?
N1 C7 C8 113.22(17) . . ?
F8 C8 C7 110.72(18) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.495(3) . ?
N1 C6 1.498(2) . ?
N1 C2 1.503(2) . ?
C2 C3 1.505(3) . ?
C3 O4 1.420(3) . ?
O4 C5 1.427(2) . ?
C5 C6 1.506(3) . ?
C7 C8 1.500(3) . ?
C8 F8 1.410(3) . ?
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
N1 H1N Cl1 0.979(5) 2.062(6) 3.0356(19) 173(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C2 C3 178.48(15) . . . . ?
C6 N1 C2 C3 -55.4(2) . . . . ?
N1 C2 C3 O4 57.9(2) . . . . ?
C2 C3 O4 C5 -59.4(2) . . . . ?
C3 O4 C5 C6 60.0(2) . . . . ?
C7 N1 C6 C5 -179.65(15) . . . . ?
C2 N1 C6 C5 55.7(2) . . . . ?
O4 C5 C6 N1 -58.8(2) . . . . ?
C6 N1 C7 C8 62.9(2) . . . . ?
C2 N1 C7 C8 -173.68(16) . . . . ?
N1 C7 C8 F8 -78.8(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21141374
