#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:16:33 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178428 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/49/4024972.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_4024972
loop_
_publ_author_name
'Ramakrishna R. Pidaparthi'
'Christopher S. Junker'
'Mark E. Welker'
'Cynthia S. Day'
'Marcus W. Wright'
_publ_contact_author_address
; 
Department of Chemistry 
Wake Forest University
Winston-Salem, N.C. 27109
U.S.A.
;
_publ_contact_author_email       welker@wfu.edu
_publ_contact_author_fax         '336 758 4656'
_publ_contact_author_name        'Mark Welker'
_publ_contact_author_phone       '336 758 5758'
_publ_section_title
;
Preparation of 2-Silicon-Substituted 1,3-Dienes and Their
Diels-Alder/Cross-Coupling Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8290
_journal_page_last               8297
_journal_paper_doi               10.1021/jo901919m
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C20 H16 F N O2'
_chemical_formula_weight         321.34
_chemical_name_systematic
; 
 ? 
;
_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           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 99.6620(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.6494(14)
_cell_length_b                   6.6182(6)
_cell_length_c                   17.2122(16)
_cell_measurement_reflns_used    4453
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.92
_cell_measurement_theta_min      3.91
_cell_volume                     1645.1(3)
_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      193(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX 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  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17395
_diffrn_reflns_theta_full        30.05
_diffrn_reflns_theta_max         30.05
_diffrn_reflns_theta_min         3.90
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9947
_exptl_absorpt_correction_T_min  0.9609
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4776
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0587
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0877P)²+0.2850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1539
_refine_ls_wR_factor_ref         0.1690
_reflns_number_gt                3533
_reflns_number_total             4776
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901919m_si_001.cif
_cod_data_source_block           a26n2m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4024972
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
F1 F -0.15060(10) 0.3730(2) 0.42663(9) 0.0948(5) Uani 1 1 d . . .
O1 O 0.01020(7) 0.33780(16) 0.19185(6) 0.0483(3) Uani 1 1 d . . .
O2 O 0.23098(8) -0.1163(2) 0.29137(7) 0.0603(3) Uani 1 1 d . . .
N1 N 0.11716(7) 0.08757(17) 0.22567(6) 0.0337(2) Uani 1 1 d . . .
C1 C 0.07047(9) 0.2621(2) 0.23932(8) 0.0356(3) Uani 1 1 d . . .
C2 C 0.18247(9) 0.0311(2) 0.29044(8) 0.0405(3) Uani 1 1 d . . .
C3 C 0.18049(9) 0.1810(2) 0.35584(8) 0.0420(3) Uani 1 1 d . . .
H3 H 0.2417 0.2512 0.3677 0.050 Uiso 1 1 calc R . .
C4 C 0.10582(10) 0.3338(2) 0.32246(8) 0.0405(3) Uani 1 1 d . . .
H4 H 0.1343 0.4707 0.3207 0.049 Uiso 1 1 calc R . .
C5 C 0.02390(11) 0.3453(2) 0.36865(10) 0.0475(4) Uani 1 1 d . . .
H5A H 0.0426 0.4235 0.4178 0.057 Uiso 1 1 calc R . .
H5B H -0.0290 0.4154 0.3364 0.057 Uiso 1 1 calc R . .
C6 C -0.00478(10) 0.1351(2) 0.38845(8) 0.0415(3) Uani 1 1 d . . .
C7 C 0.06188(10) 0.0068(3) 0.41899(8) 0.0462(3) Uani 1 1 d . . .
H7A H 0.0465 -0.1258 0.4335 0.055 Uiso 1 1 calc R . .
C8 C 0.16120(10) 0.0724(3) 0.43034(9) 0.0506(4) Uani 1 1 d . . .
H8A H 0.2021 -0.0469 0.4410 0.061 Uiso 1 1 calc R . .
H8B H 0.1744 0.1646 0.4761 0.061 Uiso 1 1 calc R . .
C9 C -0.10349(10) 0.0739(3) 0.37252(8) 0.0473(4) Uani 1 1 d . . .
C10 C -0.17355(12) 0.1950(4) 0.39036(11) 0.0650(5) Uani 1 1 d . . .
C11 C -0.26605(14) 0.1390(5) 0.37547(13) 0.0913(9) Uani 1 1 d . . .
H11 H -0.3123 0.2280 0.3881 0.110 Uiso 1 1 calc R . .
C12 C -0.28974(15) -0.0437(6) 0.34279(13) 0.0984(10) Uani 1 1 d . . .
H12 H -0.3529 -0.0837 0.3327 0.118 Uiso 1 1 calc R . .
C13 C -0.22337(18) -0.1700(5) 0.32447(13) 0.0896(8) Uani 1 1 d . . .
H13 H -0.2405 -0.2980 0.3016 0.107 Uiso 1 1 calc R . .
C14 C -0.13045(14) -0.1134(3) 0.33895(11) 0.0649(5) Uani 1 1 d . . .
H14 H -0.0849 -0.2034 0.3258 0.078 Uiso 1 1 calc R . .
C15 C 0.10578(9) -0.0170(2) 0.15164(7) 0.0349(3) Uani 1 1 d . . .
C16 C 0.13696(11) 0.0725(2) 0.08841(8) 0.0470(4) Uani 1 1 d . . .
H16 H 0.1634 0.2039 0.0930 0.056 Uiso 1 1 calc R . .
C17 C 0.12885(13) -0.0339(3) 0.01790(9) 0.0576(4) Uani 1 1 d . . .
H17 H 0.1500 0.0255 -0.0261 0.069 Uiso 1 1 calc R . .
C18 C 0.09061(12) -0.2237(3) 0.01114(9) 0.0542(4) Uani 1 1 d . . .
H18 H 0.0851 -0.2948 -0.0374 0.065 Uiso 1 1 calc R . .
C19 C 0.06024(12) -0.3110(3) 0.07483(10) 0.0518(4) Uani 1 1 d . . .
H19 H 0.0343 -0.4428 0.0702 0.062 Uiso 1 1 calc R . .
C20 C 0.06737(10) -0.2077(2) 0.14553(8) 0.0424(3) Uani 1 1 d . . .
H20 H 0.0460 -0.2675 0.1894 0.051 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 112.40(11) . . ?
C1 N1 C15 124.52(10) . . ?
C2 N1 C15 122.91(11) . . ?
O1 C1 N1 123.96(13) . . ?
O1 C1 C4 127.22(13) . . ?
N1 C1 C4 108.80(11) . . ?
O2 C2 N1 123.50(13) . . ?
O2 C2 C3 127.52(13) . . ?
N1 C2 C3 108.97(12) . . ?
C2 C3 C4 104.92(11) . . ?
C2 C3 C8 110.20(13) . . ?
C4 C3 C8 113.74(12) . . ?
C2 C3 H3 109.3 . . ?
C4 C3 H3 109.3 . . ?
C8 C3 H3 109.3 . . ?
C1 C4 C3 104.90(11) . . ?
C1 C4 C5 109.21(12) . . ?
C3 C4 C5 114.00(12) . . ?
C1 C4 H4 109.5 . . ?
C3 C4 H4 109.5 . . ?
C5 C4 H4 109.5 . . ?
C6 C5 C4 109.86(12) . . ?
C6 C5 H5A 109.7 . . ?
C4 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
C4 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C7 C6 C9 121.73(14) . . ?
C7 C6 C5 117.58(14) . . ?
C9 C6 C5 120.68(14) . . ?
C6 C7 C8 119.82(15) . . ?
C6 C7 H7A 120.1 . . ?
C8 C7 H7A 120.1 . . ?
C7 C8 C3 109.69(12) . . ?
C7 C8 H8A 109.7 . . ?
C3 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C3 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 C14 116.06(17) . . ?
C10 C9 C6 122.70(16) . . ?
C14 C9 C6 121.24(15) . . ?
F1 C10 C9 118.31(16) . . ?
F1 C10 C11 118.6(2) . . ?
C9 C10 C11 123.0(2) . . ?
C12 C11 C10 119.3(2) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 120.1(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C9 120.8(2) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C20 C15 C16 121.11(13) . . ?
C20 C15 N1 119.62(12) . . ?
C16 C15 N1 119.22(12) . . ?
C15 C16 C17 118.63(14) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C18 C17 C16 120.75(15) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 119.88(15) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 120.37(15) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C15 C20 C19 119.27(13) . . ?
C15 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
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
F1 C10 1.349(3) . ?
O1 C1 1.2068(16) . ?
O2 C2 1.2055(18) . ?
N1 C1 1.3822(17) . ?
N1 C2 1.3927(16) . ?
N1 C15 1.4348(16) . ?
C1 C4 1.5141(19) . ?
C2 C3 1.504(2) . ?
C3 C4 1.529(2) . ?
C3 C8 1.537(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.549(2) . ?
C4 H4 1.0000 . ?
C5 C6 1.509(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.334(2) . ?
C6 C9 1.482(2) . ?
C7 C8 1.500(2) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.377(2) . ?
C9 C14 1.396(3) . ?
C10 C11 1.387(3) . ?
C11 C12 1.354(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.359(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.393(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C20 1.3787(19) . ?
C15 C16 1.3823(19) . ?
C16 C17 1.391(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.373(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.377(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
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
C2 N1 C1 O1 -179.20(13) . . . . ?
C15 N1 C1 O1 5.4(2) . . . . ?
C2 N1 C1 C4 -0.76(15) . . . . ?
C15 N1 C1 C4 -176.20(11) . . . . ?
C1 N1 C2 O2 180.00(14) . . . . ?
C15 N1 C2 O2 -4.5(2) . . . . ?
C1 N1 C2 C3 0.37(16) . . . . ?
C15 N1 C2 C3 175.89(12) . . . . ?
O2 C2 C3 C4 -179.44(15) . . . . ?
N1 C2 C3 C4 0.17(15) . . . . ?
O2 C2 C3 C8 -56.6(2) . . . . ?
N1 C2 C3 C8 122.99(12) . . . . ?
O1 C1 C4 C3 179.20(13) . . . . ?
N1 C1 C4 C3 0.82(14) . . . . ?
O1 C1 C4 C5 56.62(18) . . . . ?
N1 C1 C4 C5 -121.75(12) . . . . ?
C2 C3 C4 C1 -0.58(14) . . . . ?
C8 C3 C4 C1 -121.08(13) . . . . ?
C2 C3 C4 C5 118.84(13) . . . . ?
C8 C3 C4 C5 -1.66(17) . . . . ?
C1 C4 C5 C6 73.54(15) . . . . ?
C3 C4 C5 C6 -43.42(17) . . . . ?
C4 C5 C6 C7 47.30(18) . . . . ?
C4 C5 C6 C9 -131.34(14) . . . . ?
C9 C6 C7 C8 176.97(13) . . . . ?
C5 C6 C7 C8 -1.7(2) . . . . ?
C6 C7 C8 C3 -45.8(2) . . . . ?
C2 C3 C8 C7 -72.57(16) . . . . ?
C4 C3 C8 C7 44.90(18) . . . . ?
C7 C6 C9 C10 136.89(17) . . . . ?
C5 C6 C9 C10 -44.5(2) . . . . ?
C7 C6 C9 C14 -42.4(2) . . . . ?
C5 C6 C9 C14 136.19(16) . . . . ?
C14 C9 C10 F1 176.64(16) . . . . ?
C6 C9 C10 F1 -2.7(3) . . . . ?
C14 C9 C10 C11 -0.9(3) . . . . ?
C6 C9 C10 C11 179.83(18) . . . . ?
F1 C10 C11 C12 -176.6(2) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C12 C13 C14 C9 0.0(3) . . . . ?
C10 C9 C14 C13 0.4(3) . . . . ?
C6 C9 C14 C13 179.75(17) . . . . ?
C1 N1 C15 C20 -113.92(14) . . . . ?
C2 N1 C15 C20 71.11(17) . . . . ?
C1 N1 C15 C16 68.61(17) . . . . ?
C2 N1 C15 C16 -106.36(16) . . . . ?
C20 C15 C16 C17 0.0(2) . . . . ?
N1 C15 C16 C17 177.46(13) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C16 C15 C20 C19 0.2(2) . . . . ?
N1 C15 C20 C19 -177.27(13) . . . . ?
C18 C19 C20 C15 -0.4(2) . . . . ?
