#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/42/1514271.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_1514271
loop_
_publ_author_name
'Ghorai, Manas K'
'Talukdar, Ranadeep'
'Tiwari, Deo Prakash'
_publ_section_title
;
 A Route to Highly Functionalized β-Enaminoesters via a Domino
 Ring-Opening Cyclization/Decarboxylative Tautomerization Sequence of
 Donor-Acceptor Cyclopropanes with Substituted Malononitriles.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2204
_journal_page_last               2207
_journal_paper_doi               10.1021/ol5007218
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C15 H15 F N2 O2'
_chemical_formula_weight         274.29
_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                91.367(5)
_cell_angle_beta                 107.144(5)
_cell_angle_gamma                93.909(5)
_cell_formula_units_Z            2
_cell_length_a                   7.055(5)
_cell_length_b                   8.528(5)
_cell_length_c                   11.612(5)
_cell_measurement_reflns_used    1483
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.40
_cell_volume                     665.3(7)
_computing_cell_refinement       'Bruker SMART'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3473
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         4.30
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.474764
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.075
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0541P)²+0.4032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1225
_reflns_number_gt                1843
_reflns_number_total             2285
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5007218_si_003.cif
_cod_data_source_block           16mayem
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for
 ./tmp-cod-update-bibliographies-8800/cifs/1514271.cif.
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               1514271
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 0.7125(2) -0.12382(14) 0.46601(12) 0.0344(4) Uani 1 1 d .
O2 O 1.1300(2) 0.92756(16) 0.94345(13) 0.0228(3) Uani 1 1 d .
O1 O 1.2768(2) 0.84534(16) 0.80681(13) 0.0241(4) Uani 1 1 d .
N2 N 0.7655(3) 0.74748(19) 0.93077(15) 0.0222(4) Uani 1 1 d .
H2A H 0.8229 0.8383 0.9593 0.027 Uiso 1 1 calc R
H2B H 0.6546 0.7162 0.9427 0.027 Uiso 1 1 calc R
C7 C 0.9157(3) 0.4124(2) 0.78442(18) 0.0192(4) Uani 1 1 d .
H7 H 0.9849 0.3717 0.8626 0.023 Uiso 1 1 calc R
C9 C 0.8489(3) 0.6545(2) 0.86760(17) 0.0177(4) Uani 1 1 d .
C8 C 0.7385(3) 0.5007(2) 0.80369(18) 0.0193(4) Uani 1 1 d .
C10 C 1.0221(3) 0.6810(2) 0.83854(17) 0.0191(4) Uani 1 1 d .
C2 C 0.7762(3) -0.0078(2) 0.66100(19) 0.0250(5) Uani 1 1 d .
H2 H 0.7538 -0.1058 0.6902 0.030 Uiso 1 1 calc R
C12 C 1.1447(3) 0.8271(2) 0.87037(18) 0.0192(4) Uani 1 1 d .
N1 N 0.5527(3) 0.3468(2) 0.93610(17) 0.0261(4) Uani 1 1 d .
C6 C 0.7915(3) 0.1510(3) 0.4950(2) 0.0281(5) Uani 1 1 d .
H6 H 0.7803 0.1592 0.4136 0.034 Uiso 1 1 calc R
C4 C 0.8585(3) 0.2729(2) 0.69568(18) 0.0199(4) Uani 1 1 d .
C1 C 0.7601(3) 0.0074(2) 0.5412(2) 0.0247(5) Uani 1 1 d .
C3 C 0.8261(3) 0.1248(2) 0.73754(19) 0.0226(5) Uani 1 1 d .
H3 H 0.8384 0.1150 0.8190 0.027 Uiso 1 1 calc R
C5 C 0.8400(3) 0.2830(2) 0.57307(19) 0.0254(5) Uani 1 1 d .
H5 H 0.8607 0.3807 0.5430 0.030 Uiso 1 1 calc R
C14 C 0.6365(3) 0.4129(2) 0.87884(18) 0.0200(4) Uani 1 1 d .
C11 C 1.0548(3) 0.5473(2) 0.76166(18) 0.0214(5) Uani 1 1 d .
H11A H 1.1924 0.5216 0.7870 0.026 Uiso 1 1 calc R
H11B H 1.0178 0.5719 0.6772 0.026 Uiso 1 1 calc R
C13 C 1.3847(3) 0.9986(2) 0.8220(2) 0.0266(5) Uani 1 1 d .
H13A H 1.2926 1.0788 0.8107 0.040 Uiso 1 1 calc R
H13B H 1.4565 1.0076 0.7637 0.040 Uiso 1 1 calc R
H13C H 1.4766 1.0112 0.9018 0.040 Uiso 1 1 calc R
C15 C 0.5819(3) 0.5367(2) 0.68477(19) 0.0232(5) Uani 1 1 d .
H15A H 0.5095 0.4405 0.6468 0.035 Uiso 1 1 calc R
H15B H 0.6475 0.5857 0.6318 0.035 Uiso 1 1 calc R
H15C H 0.4913 0.6064 0.7019 0.035 Uiso 1 1 calc R
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
C12 O1 C13 115.11(15)
C4 C7 C11 118.13(17)
C4 C7 C8 115.83(16)
C11 C7 C8 102.78(16)
N2 C9 C10 129.39(19)
N2 C9 C8 120.96(17)
C10 C9 C8 109.34(17)
C14 C8 C9 112.06(16)
C14 C8 C15 108.47(17)
C9 C8 C15 109.81(16)
C14 C8 C7 111.90(16)
C9 C8 C7 100.84(16)
C15 C8 C7 113.65(16)
C9 C10 C12 122.44(18)
C9 C10 C11 111.63(17)
C12 C10 C11 125.70(17)
C1 C2 C3 118.87(19)
O2 C12 O1 122.46(18)
O2 C12 C10 125.04(18)
O1 C12 C10 112.46(17)
C1 C6 C5 118.3(2)
C3 C4 C5 117.65(19)
C3 C4 C7 118.82(19)
C5 C4 C7 123.52(18)
F1 C1 C2 118.77(19)
F1 C1 C6 119.24(19)
C2 C1 C6 121.99(19)
C2 C3 C4 121.6(2)
C6 C5 C4 121.65(19)
N1 C14 C8 178.2(2)
C10 C11 C7 102.43(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C1 1.362(2)
O2 C12 1.222(2)
O1 C12 1.352(2)
O1 C13 1.447(3)
N2 C9 1.343(3)
C7 C4 1.507(3)
C7 C11 1.540(3)
C7 C8 1.570(3)
C9 C10 1.366(3)
C9 C8 1.533(3)
C8 C14 1.472(3)
C8 C15 1.546(3)
C10 C12 1.442(3)
C10 C11 1.502(3)
C2 C1 1.373(3)
C2 C3 1.381(3)
N1 C14 1.146(3)
C6 C1 1.379(3)
C6 C5 1.386(3)
C4 C3 1.393(3)
C4 C5 1.396(3)
