#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:59:37 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180326 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/40/7154021.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_7154021
loop_
_publ_author_name
'Cogswell, Thomas J.'
'Donald, Craig S.'
'Long, De-Liang'
'Marquez, Rodolfo'
_publ_section_title
;
 Short and efficient synthesis of fluorinated δ-lactams.
;
_journal_issue                   3
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              717
_journal_page_last               728
_journal_paper_doi               10.1039/c4ob01547a
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C11 H12 F N O'
_chemical_formula_weight         193.22
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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-2013
_cell_angle_alpha                110.410(2)
_cell_angle_beta                 96.980(2)
_cell_angle_gamma                92.353(2)
_cell_formula_units_Z            2
_cell_length_a                   6.0469(2)
_cell_length_b                   9.1864(3)
_cell_length_c                   9.4011(3)
_cell_measurement_reflns_used    6489
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      2.34
_cell_volume                     483.85(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    Mecurry
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini Ultra'
_diffrn_measurement_method       'ω & π scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14096
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.986
_diffrn_reflns_theta_min         2.336
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.20
_refine_diff_density_rms         0.03
_refine_ls_extinction_coef       0.019(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0378P)²+0.1864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0921
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1711
_reflns_number_total             1907
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ob01547a2.cif
_cod_data_source_block           tc317
_cod_depositor_comments          'Adding full bibliography for 7154021.cif.'
_cod_database_code               7154021
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.9519(2) 0.69884(14) 0.67740(14) 0.0199(3) Uani 1 1 d . .
C2 C 0.9134(2) 0.83934(15) 0.81542(15) 0.0252(3) Uani 1 1 d . .
H2 H 0.9550 0.8167 0.9114 0.030 Uiso 1 1 calc R U
C3 C 0.6782(2) 0.88681(16) 0.80997(15) 0.0289(3) Uani 1 1 d . .
H3A H 0.6759 0.9931 0.8858 0.035 Uiso 1 1 calc R U
H3B H 0.5806 0.8145 0.8374 0.035 Uiso 1 1 calc R U
C4 C 0.5895(2) 0.88407(15) 0.65064(15) 0.0267(3) Uani 1 1 d . .
H4A H 0.6887 0.9541 0.6215 0.032 Uiso 1 1 calc R U
H4B H 0.4380 0.9211 0.6498 0.032 Uiso 1 1 calc R U
C5 C 0.5803(2) 0.71805(14) 0.53693(14) 0.0204(3) Uani 1 1 d . .
H5 H 0.4674 0.6528 0.5635 0.024 Uiso 1 1 calc R U
C6 C 0.5099(2) 0.70444(14) 0.37274(14) 0.0203(3) Uani 1 1 d . .
C7 C 0.2882(2) 0.65768(15) 0.30661(16) 0.0260(3) Uani 1 1 d . .
H7 H 0.1840 0.6333 0.3647 0.031 Uiso 1 1 calc R U
C8 C 0.2175(2) 0.64625(17) 0.15687(16) 0.0316(3) Uani 1 1 d . .
H8 H 0.0653 0.6149 0.1133 0.038 Uiso 1 1 calc R U
C9 C 0.3677(2) 0.68038(17) 0.07054(16) 0.0317(3) Uani 1 1 d . .
H9 H 0.3201 0.6706 -0.0327 0.038 Uiso 1 1 calc R U
C10 C 0.5883(2) 0.72897(17) 0.13642(16) 0.0303(3) Uani 1 1 d . .
H10 H 0.6919 0.7541 0.0783 0.036 Uiso 1 1 calc R U
C11 C 0.6592(2) 0.74125(15) 0.28633(15) 0.0254(3) Uani 1 1 d . .
H11 H 0.8108 0.7750 0.3303 0.030 Uiso 1 1 calc R U
N1 N 0.79856(17) 0.65529(12) 0.55254(12) 0.0200(3) Uani 1 1 d . .
H1 H 0.8310 0.5813 0.4708 0.024 Uiso 1 1 calc R U
O1 O 1.12428(14) 0.63207(11) 0.68528(10) 0.0252(2) Uani 1 1 d . .
F1 F 1.06059(14) 0.96212(10) 0.81591(10) 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
O1 C1 N1 122.98(11)
O1 C1 C2 119.02(11)
N1 C1 C2 117.99(11)
F1 C2 C3 109.28(11)
F1 C2 C1 105.26(10)
C3 C2 C1 114.57(11)
C2 C3 C4 110.54(11)
C3 C4 C5 108.93(11)
N1 C5 C6 110.21(10)
N1 C5 C4 109.99(10)
C6 C5 C4 113.18(10)
C7 C6 C11 118.71(12)
C7 C6 C5 119.32(11)
C11 C6 C5 121.95(11)
C8 C7 C6 120.74(13)
C9 C8 C7 120.29(13)
C8 C9 C10 119.25(13)
C9 C10 C11 120.56(13)
C10 C11 C6 120.43(12)
C1 N1 C5 126.83(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2382(15)
C1 N1 1.3325(16)
C1 C2 1.5277(17)
C2 F1 1.4061(15)
C2 C3 1.5046(18)
C3 C4 1.5197(18)
C4 C5 1.5210(17)
C5 N1 1.4731(15)
C5 C6 1.5103(17)
C6 C7 1.3897(18)
C6 C11 1.3908(18)
C7 C8 1.3866(19)
C8 C9 1.384(2)
C9 C10 1.386(2)
C10 C11 1.3860(19)
