#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:51:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180319 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/33/7153318.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_7153318
loop_
_publ_author_name
'Lechel, Tilman'
'Dash, Jyotirmayee'
'Eidamshaus, Christian'
'Brüdgam, Irene'
'Lentz, Dieter'
'Reissig, Hans-Ulrich'
_publ_section_title
;
 A three-component synthesis of beta-alkoxy-beta-keto-enamides--flexible
 precursors for 4-hydroxypyridine derivatives and their
 palladium-catalysed reactions.
;
_journal_issue                   13
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3007
_journal_page_last               3014
_journal_paper_doi               10.1039/b925468d
_journal_volume                  8
_journal_year                    2010
_chemical_formula_sum            'C19 H23 N O'
_chemical_formula_weight         281.38
_chemical_melting_point          393
_chemical_name_common
(E)-2-tert-Butyl-3-methoxy-6-methyl-4-styrylpyridine
_chemical_name_systematic
;
(E)-2-tert-Butyl-3-methoxy-6-methyl-4-styrylpyridine
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.141(4)
_cell_length_b                   8.066(2)
_cell_length_c                   15.156(4)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.522
_cell_volume                     1606.5(8)
_computing_cell_refinement       'Saint (Bruker-AXS)'
_computing_data_collection       'SMART (Bruker-AXS)'
_computing_data_reduction        'Saint (Bruker-AXS)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker-AXS SMART CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14518
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          .48
_exptl_crystal_size_mid          .47
_exptl_crystal_size_min          .43
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         1926
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0324
_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)+(0.0595P)²+0.1367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0882
_reflns_number_gt                1774
_reflns_number_total             1926
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b925468d.txt
_cod_data_source_block           orgda4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '393 K' was changed to '393' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1606.6(8)
_cod_original_sg_symbol_H-M      Pca21
_cod_database_code               7153318
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
C2 C -0.00009(11) 0.9676(2) 0.08836(12) 0.0231(3) Uani 1 1 d .
C3 C 0.03563(11) 0.8786(2) 0.01496(11) 0.0228(3) Uani 1 1 d .
C4 C 0.08638(11) 0.7276(2) 0.02660(12) 0.0248(3) Uani 1 1 d .
C5 C 0.10746(12) 0.6794(2) 0.11329(12) 0.0273(4) Uani 1 1 d .
H5 H 0.1414 0.5777 0.1247 0.033 Uiso 1 1 calc R
C6 C 0.07848(12) 0.7810(2) 0.18240(12) 0.0272(4) Uani 1 1 d .
C7 C -0.10819(16) 1.1767(3) 0.16912(14) 0.0394(5) Uani 1 1 d .
H7C H -0.1520 1.2742 0.1618 0.059 Uiso 1 1 calc R
H7B H -0.0499 1.2057 0.2064 0.059 Uiso 1 1 calc R
H7A H -0.1471 1.0873 0.1970 0.059 Uiso 1 1 calc R
C8 C -0.07018(12) 1.1192(2) 0.07877(12) 0.0273(4) Uani 1 1 d .
C9 C -0.01412(15) 1.2643(2) 0.03445(16) 0.0387(4) Uani 1 1 d .
H9A H 0.0483 1.2890 0.0673 0.058 Uiso 1 1 calc R
H9B H -0.0582 1.3623 0.0341 0.058 Uiso 1 1 calc R
H9C H 0.0033 1.2342 -0.0263 0.058 Uiso 1 1 calc R
C10 C -0.16399(13) 1.0713(2) 0.02345(13) 0.0329(4) Uani 1 1 d .
H10B H -0.2104 1.1661 0.0198 0.049 Uiso 1 1 calc R
H10A H -0.1990 0.9777 0.0514 0.049 Uiso 1 1 calc R
H10C H -0.1423 1.0396 -0.0361 0.049 Uiso 1 1 calc R
C11 C 0.11421(12) 0.6283(2) -0.05077(12) 0.0271(3) Uani 1 1 d .
H11 H 0.0750 0.6439 -0.1028 0.033 Uiso 1 1 calc R
C12 C 0.18991(13) 0.5179(2) -0.05453(12) 0.0282(4) Uani 1 1 d .
H12 H 0.2281 0.5017 -0.0020 0.034 Uiso 1 1 calc R
C13 C 0.21985(12) 0.41943(19) -0.13138(13) 0.0270(4) Uani 1 1 d .
C14 C 0.30690(13) 0.3196(2) -0.12670(14) 0.0315(4) Uani 1 1 d .
H14 H 0.3451 0.3157 -0.0735 0.038 Uiso 1 1 calc R
C15 C 0.33806(14) 0.2261(2) -0.19872(15) 0.0365(4) Uani 1 1 d .
H15 H 0.3972 0.1589 -0.1944 0.044 Uiso 1 1 calc R
C16 C 0.28399(15) 0.2302(2) -0.27624(15) 0.0381(4) Uani 1 1 d .
H16 H 0.3058 0.1665 -0.3254 0.046 Uiso 1 1 calc R
C17 C 0.19684(15) 0.3283(2) -0.28238(14) 0.0362(4) Uani 1 1 d .
H17 H 0.1591 0.3314 -0.3358 0.043 Uiso 1 1 calc R
C18 C 0.16537(13) 0.4209(2) -0.21086(13) 0.0315(4) Uani 1 1 d .
H18 H 0.1057 0.4868 -0.2156 0.038 Uiso 1 1 calc R
C19 C 0.10723(16) 0.7397(3) 0.27622(14) 0.0386(4) Uani 1 1 d .
H19B H 0.0482 0.7560 0.3147 0.058 Uiso 1 1 calc R
H19C H 0.1628 0.8123 0.2953 0.058 Uiso 1 1 calc R
H19A H 0.1294 0.6238 0.2795 0.058 Uiso 1 1 calc R
C20 C 0.10922(14) 0.9991(3) -0.11156(12) 0.0347(4) Uani 1 1 d .
H20A H 0.1569 0.9074 -0.1212 0.052 Uiso 1 1 calc R
H20C H 0.1411 1.0828 -0.0738 0.052 Uiso 1 1 calc R
H20B H 0.0913 1.0491 -0.1684 0.052 Uiso 1 1 calc R
N1 N 0.02317(10) 0.91911(19) 0.17030(10) 0.0258(3) Uani 1 1 d .
O1 O 0.01859(9) 0.93730(15) -0.06945(8) 0.0269(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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C2 C3 120.65(14)
N1 C2 C8 117.19(15)
C3 C2 C8 122.12(15)
O1 C3 C4 119.47(15)
O1 C3 C2 120.24(14)
C4 C3 C2 120.27(15)
C5 C4 C3 117.05(15)
C5 C4 C11 123.41(15)
C3 C4 C11 119.54(16)
C6 C5 C4 119.52(15)
N1 C6 C5 122.48(16)
N1 C6 C19 116.58(16)
C5 C6 C19 120.94(16)
C7 C8 C9 108.44(17)
C7 C8 C2 110.63(15)
C9 C8 C2 111.09(14)
C7 C8 C10 107.59(15)
C9 C8 C10 109.67(16)
C2 C8 C10 109.34(14)
C12 C11 C4 125.70(16)
C11 C12 C13 126.56(16)
C14 C13 C18 117.75(17)
C14 C13 C12 119.42(17)
C18 C13 C12 122.83(15)
C15 C14 C13 120.88(19)
C16 C15 C14 120.47(17)
C15 C16 C17 119.69(18)
C18 C17 C16 120.04(19)
C17 C18 C13 121.17(17)
C2 N1 C6 119.53(15)
C3 O1 C20 113.25(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 N1 1.337(2)
C2 C3 1.405(2)
C2 C8 1.538(2)
C3 O1 1.383(2)
C3 C4 1.400(2)
C4 C5 1.398(3)
C4 C11 1.466(2)
C5 C6 1.383(3)
C6 N1 1.343(2)
C6 C19 1.509(3)
C7 C8 1.530(3)
C8 C9 1.538(3)
C8 C10 1.540(2)
C11 C12 1.337(2)
C12 C13 1.464(3)
C13 C14 1.401(2)
C13 C18 1.401(3)
C14 C15 1.388(3)
C15 C16 1.373(3)
C16 C17 1.395(3)
C17 C18 1.380(3)
C20 O1 1.440(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
N1 C2 C3 O1 -174.46(14)
C8 C2 C3 O1 7.9(2)
N1 C2 C3 C4 7.2(2)
C8 C2 C3 C4 -170.39(14)
O1 C3 C4 C5 175.91(14)
C2 C3 C4 C5 -5.7(2)
O1 C3 C4 C11 -4.4(2)
C2 C3 C4 C11 173.98(14)
C3 C4 C5 C6 -0.3(2)
C11 C4 C5 C6 179.95(16)
C4 C5 C6 N1 5.5(2)
C4 C5 C6 C19 -175.13(17)
N1 C2 C8 C7 -5.2(2)
C3 C2 C8 C7 172.45(15)
N1 C2 C8 C9 115.27(18)
C3 C2 C8 C9 -67.0(2)
N1 C2 C8 C10 -123.55(17)
C3 C2 C8 C10 54.1(2)
C5 C4 C11 C12 -25.1(3)
C3 C4 C11 C12 155.22(16)
C4 C11 C12 C13 -179.04(15)
C11 C12 C13 C14 174.36(17)
C11 C12 C13 C18 -5.2(3)
C18 C13 C14 C15 0.3(3)
C12 C13 C14 C15 -179.25(17)
C13 C14 C15 C16 0.1(3)
C14 C15 C16 C17 -0.3(3)
C15 C16 C17 C18 0.1(3)
C16 C17 C18 C13 0.4(3)
C14 C13 C18 C17 -0.6(3)
C12 C13 C18 C17 178.99(17)
C3 C2 N1 C6 -2.2(2)
C8 C2 N1 C6 175.57(14)
C5 C6 N1 C2 -4.2(2)
C19 C6 N1 C2 176.37(15)
C4 C3 O1 C20 -73.19(19)
C2 C3 O1 C20 108.47(17)
