#------------------------------------------------------------------------------
#$Date: 2016-03-27 05:17:15 +0200 (dom 27 de mar de 2016) $
#$Revision: 180547 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/42/7204235.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_7204235
loop_
_publ_author_name
'Cave, Gareth W. V.'
'Raston, Colin L.'
_publ_section_title
;
 Efficient synthesis of pyridines via a sequential solventless aldol
 condensation and Michael addition
;
_journal_coden_ASTM              JCSPCE
_journal_issue                   24
_journal_name_full
;
 Journal of the Chemical Society, Perkin Transactions 1
;
_journal_page_first              3258
_journal_page_last               3264
_journal_paper_doi               10.1039/b107302h
_journal_year                    2001
_chemical_formula_sum            'C25 H23 N3 O'
_chemical_formula_weight         381.46
_chemical_name_common            4'-(4-butoxyphenyl)-4,2';6',4''-terpyridine
_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                117.946(1)
_cell_angle_beta                 91.825(1)
_cell_angle_gamma                96.606(1)
_cell_formula_units_Z            4
_cell_length_a                   10.8889(2)
_cell_length_b                   14.1687(8)
_cell_length_c                   14.6071(2)
_cell_measurement_temperature    123(2)
_cell_volume                     1968.13(12)
_computing_cell_refinement       DENZO
_computing_data_collection       'Collect (Enraf-Nonius) '
_computing_data_reduction        DENZO
_computing_molecular_graphics    X-Seed
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'Phi and Omega scan '
_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  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0771
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28835
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9905
_exptl_absorpt_correction_T_min  0.9842
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         9549
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0577
_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)+(0.1127P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1920
_reflns_number_gt                6158
_reflns_number_total             9549
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b107302h.txt
_cod_data_source_block           global
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               7204235
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.33788(12) 0.73761(10) 0.48332(10) 0.0231(3) Uani 1 1 d . . .
N3 N 0.02510(14) 1.31498(12) 0.79401(12) 0.0181(4) Uani 1 1 d . . .
C7 C -0.00410(17) 1.12060(15) 0.70789(14) 0.0173(4) Uani 1 1 d . . .
H7 H -0.0596 1.0549 0.6823 0.021 Uiso 1 1 calc R . .
C10 C 0.19949(17) 1.21839(15) 0.74188(15) 0.0183(4) Uani 1 1 d . . .
H10 H 0.2868 1.2211 0.7389 0.022 Uiso 1 1 calc R . .
C12 C 0.14843(17) 1.31370(15) 0.78910(14) 0.0172(4) Uani 1 1 d . . .
N14 N 0.38406(16) 1.62056(13) 0.90268(13) 0.0261(4) Uani 1 1 d . . .
C19 C 0.17463(17) 1.01646(15) 0.64372(14) 0.0168(4) Uani 1 1 d . . .
C21 C -0.04896(17) 1.21888(15) 0.75447(14) 0.0171(4) Uani 1 1 d . . .
C22 C 0.27886(18) 0.82582(15) 0.53321(15) 0.0187(4) Uani 1 1 d . . .
C25 C 0.18132(18) 1.51312(15) 0.84678(15) 0.0208(4) Uani 1 1 d . . .
H25 H 0.0946 1.5104 0.8336 0.025 Uiso 1 1 calc R . .
C28 C 0.34771(17) 0.91537(15) 0.61734(15) 0.0198(4) Uani 1 1 d . . .
H28 H 0.4301 0.9120 0.6378 0.024 Uiso 1 1 calc R . .
N29 N -0.44029(15) 1.24024(14) 0.77133(14) 0.0263(4) Uani 1 1 d . . .
C31 C -0.18427(17) 1.22370(15) 0.76233(15) 0.0172(4) Uani 1 1 d . . .
C32 C 0.22918(17) 1.42058(15) 0.83147(14) 0.0178(4) Uani 1 1 d . . .
C33 C 0.12290(17) 1.11889(15) 0.69889(14) 0.0173(4) Uani 1 1 d . . .
C34 C 0.15667(18) 0.83100(15) 0.50589(15) 0.0205(4) Uani 1 1 d . . .
H34 H 0.1079 0.7699 0.4499 0.025 Uiso 1 1 calc R . .
C35 C -0.27355(17) 1.14147(16) 0.68948(16) 0.0218(4) Uani 1 1 d . . .
H35 H -0.2495 1.0780 0.6355 0.026 Uiso 1 1 calc R . .
C38 C 0.35709(18) 1.43142(16) 0.85435(16) 0.0242(5) Uani 1 1 d . . .
H38 H 0.3944 1.3709 0.8463 0.029 Uiso 1 1 calc R . .
C41 C 0.26101(19) 1.60963(16) 0.88144(16) 0.0235(5) Uani 1 1 d . . .
H41 H 0.2262 1.6716 0.8906 0.028 Uiso 1 1 calc R . .
C43 C 0.29647(17) 1.00892(15) 0.67106(15) 0.0191(4) Uani 1 1 d . . .
H43 H 0.3448 1.0695 0.7278 0.023 Uiso 1 1 calc R . .
C46 C 0.10657(18) 0.92594(15) 0.56096(15) 0.0197(4) Uani 1 1 d . . .
H46 H 0.0236 0.9289 0.5414 0.024 Uiso 1 1 calc R . .
C49 C -0.39815(18) 1.15376(17) 0.69703(17) 0.0247(5) Uani 1 1 d . . .
H49 H -0.4575 1.0972 0.6463 0.030 Uiso 1 1 calc R . .
C50 C -0.22698(18) 1.31358(16) 0.84028(15) 0.0213(4) Uani 1 1 d . . .
H50 H -0.1698 1.3712 0.8922 0.026 Uiso 1 1 calc R . .
C51 C -0.35345(18) 1.31813(16) 0.84137(16) 0.0246(5) Uani 1 1 d . . .
H51 H -0.3803 1.3803 0.8951 0.030 Uiso 1 1 calc R . .
C52 C 0.3567(2) 0.56441(16) 0.33981(16) 0.0291(5) Uani 1 1 d . . .
H52A H 0.4355 0.6024 0.3335 0.035 Uiso 1 1 calc R . .
H52B H 0.3184 0.5131 0.2685 0.035 Uiso 1 1 calc R . .
C53 C 0.3860(2) 0.50116(17) 0.39452(18) 0.0327(5) Uani 1 1 d . . .
H53A H 0.3073 0.4688 0.4074 0.039 Uiso 1 1 calc R . .
H53B H 0.4329 0.5509 0.4629 0.039 Uiso 1 1 calc R . .
C54 C 0.2711(2) 0.64612(15) 0.39296(16) 0.0266(5) Uani 1 1 d . . .
H54A H 0.2384 0.6698 0.3443 0.032 Uiso 1 1 calc R . .
H54B H 0.2000 0.6131 0.4140 0.032 Uiso 1 1 calc R . .
C56 C 0.42881(19) 1.53087(16) 0.88880(17) 0.0280(5) Uani 1 1 d . . .
H56 H 0.5157 1.5362 0.9037 0.034 Uiso 1 1 calc R . .
C57 C 0.4616(3) 0.41186(18) 0.33197(19) 0.0440(7) Uani 1 1 d . . .
H57A H 0.4214 0.3684 0.2608 0.066 Uiso 1 1 calc R . .
H57B H 0.4667 0.3657 0.3648 0.066 Uiso 1 1 calc R . .
H57C H 0.5455 0.4440 0.3301 0.066 Uiso 1 1 calc R . .
O2 O 0.82310(12) 0.51147(10) 0.41648(11) 0.0242(3) Uani 1 1 d . . .
N4 N 1.11124(14) -0.07566(12) 0.08235(12) 0.0174(4) Uani 1 1 d . . .
C5 C 0.93722(17) 0.02210(15) 0.13149(14) 0.0170(4) Uani 1 1 d . . .
H5 H 0.8496 0.0201 0.1287 0.020 Uiso 1 1 calc R . .
C6 C 0.95707(18) -0.27560(15) -0.00016(15) 0.0191(4) Uani 1 1 d . . .
H6 H 1.0439 -0.2735 0.0113 0.023 Uiso 1 1 calc R . .
C8 C 0.98804(17) -0.07360(15) 0.08275(14) 0.0163(4) Uani 1 1 d . . .
C9 C 1.14294(17) 0.11770(15) 0.18406(14) 0.0181(4) Uani 1 1 d . . .
H9 H 1.1997 0.1828 0.2199 0.022 Uiso 1 1 calc R . .
C11 C 0.87448(18) 0.42003(15) 0.35745(15) 0.0189(4) Uani 1 1 d . . .
N13 N 1.57906(15) -0.00052(14) 0.11697(13) 0.0230(4) Uani 1 1 d . . .
C15 C 1.01526(17) 0.12084(15) 0.18440(14) 0.0166(4) Uani 1 1 d . . .
C16 C 0.90743(17) -0.18051(14) 0.02950(14) 0.0160(4) Uani 1 1 d . . .
C17 C 1.32252(17) 0.01362(15) 0.12755(14) 0.0164(4) Uani 1 1 d . . .
C18 C 0.80388(18) 0.32289(15) 0.33739(15) 0.0208(4) Uani 1 1 d . . .
H18 H 0.7247 0.3226 0.3628 0.025 Uiso 1 1 calc R . .
C20 C 0.96548(17) 0.22443(14) 0.24141(14) 0.0160(4) Uani 1 1 d . . .
C23 C 1.18719(16) 0.01934(15) 0.13130(14) 0.0163(4) Uani 1 1 d . . .
N24 N 0.75576(15) -0.38439(13) -0.06744(13) 0.0243(4) Uani 1 1 d . . .
C26 C 1.03315(17) 0.32248(15) 0.26035(15) 0.0185(4) Uani 1 1 d . . .
H26 H 1.1113 0.3228 0.2333 0.022 Uiso 1 1 calc R . .
C27 C 0.77918(17) -0.19064(15) 0.00809(15) 0.0212(4) Uani 1 1 d . . .
H27 H 0.7403 -0.1283 0.0262 0.025 Uiso 1 1 calc R . .
C30 C 1.53476(18) 0.09166(16) 0.14074(15) 0.0232(5) Uani 1 1 d . . .
H30 H 1.5923 0.1534 0.1539 0.028 Uiso 1 1 calc R . .
C36 C 1.41002(17) 0.10266(16) 0.14728(15) 0.0206(4) Uani 1 1 d . . .
H36 H 1.3842 0.1705 0.1651 0.025 Uiso 1 1 calc R . .
C37 C 1.36797(18) -0.08293(16) 0.10175(15) 0.0203(4) Uani 1 1 d . . .
H37 H 1.3125 -0.1463 0.0869 0.024 Uiso 1 1 calc R . .
C39 C 0.87869(19) -0.37355(16) -0.04667(16) 0.0231(5) Uani 1 1 d . . .
H39 H 0.9147 -0.4373 -0.0650 0.028 Uiso 1 1 calc R . .
C40 C 1.49408(18) -0.08585(16) 0.09799(16) 0.0234(5) Uani 1 1 d . . .
H40 H 1.5227 -0.1525 0.0809 0.028 Uiso 1 1 calc R . .
C42 C 0.84916(17) 0.22693(15) 0.28053(15) 0.0193(4) Uani 1 1 d . . .
H42 H 0.8005 0.1610 0.2676 0.023 Uiso 1 1 calc R . .
C44 C 0.89965(18) 0.61357(15) 0.44952(17) 0.0242(5) Uani 1 1 d . . .
H44A H 0.9205 0.6225 0.3883 0.029 Uiso 1 1 calc R . .
H44B H 0.9780 0.6171 0.4881 0.029 Uiso 1 1 calc R . .
C45 C 0.98908(18) 0.41969(15) 0.31787(15) 0.0209(4) Uani 1 1 d . . .
H45 H 1.0369 0.4857 0.3302 0.025 Uiso 1 1 calc R . .
C47 C 0.70960(19) -0.29217(16) -0.03973(16) 0.0247(5) Uani 1 1 d . . .
H47 H 0.6227 -0.2970 -0.0540 0.030 Uiso 1 1 calc R . .
C48 C 0.82831(19) 0.70187(16) 0.51905(17) 0.0269(5) Uani 1 1 d . . .
H48A H 0.8838 0.7719 0.5485 0.032 Uiso 1 1 calc R . .
H48B H 0.8050 0.6893 0.5778 0.032 Uiso 1 1 calc R . .
C55 C 0.7117(2) 0.71016(19) 0.46540(18) 0.0351(6) Uani 1 1 d . . .
H55A H 0.7305 0.7046 0.3973 0.042 Uiso 1 1 calc R . .
H55B H 0.6475 0.6484 0.4518 0.042 Uiso 1 1 calc R . .
C58 C 0.6600(2) 0.8136(2) 0.5277(2) 0.0577(9) Uani 1 1 d . . .
H58A H 0.6431 0.8208 0.5960 0.087 Uiso 1 1 calc R . .
H58B H 0.5826 0.8124 0.4907 0.087 Uiso 1 1 calc R . .
H58C H 0.7204 0.8750 0.5369 0.087 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'
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
C22 O1 C54 117.27(15) . . ?
C21 N3 C12 117.36(16) . . ?
C21 C7 C33 119.69(17) . . ?
C12 C10 C33 120.16(17) . . ?
N3 C12 C10 122.58(17) . . ?
N3 C12 C32 116.81(16) . . ?
C10 C12 C32 120.51(17) . . ?
C41 N14 C56 115.84(17) . . ?
C46 C19 C43 117.59(17) . . ?
C46 C19 C33 121.48(17) . . ?
C43 C19 C33 120.88(17) . . ?
N3 C21 C7 123.09(17) . . ?
N3 C21 C31 115.75(16) . . ?
C7 C21 C31 121.16(16) . . ?
O1 C22 C28 116.18(16) . . ?
O1 C22 C34 124.61(17) . . ?
C28 C22 C34 119.21(17) . . ?
C41 C25 C32 119.59(18) . . ?
C43 C28 C22 120.19(18) . . ?
C51 N29 C49 115.91(17) . . ?
C50 C31 C35 117.12(17) . . ?
C50 C31 C21 121.11(17) . . ?
C35 C31 C21 121.70(17) . . ?
C25 C32 C38 116.86(17) . . ?
C25 C32 C12 121.66(17) . . ?
C38 C32 C12 121.45(17) . . ?
C10 C33 C7 117.04(17) . . ?
C10 C33 C19 121.05(17) . . ?
C7 C33 C19 121.89(16) . . ?
C46 C34 C22 119.77(17) . . ?
C49 C35 C31 119.05(18) . . ?
C56 C38 C32 119.38(19) . . ?
N14 C41 C25 123.94(19) . . ?
C28 C43 C19 121.49(17) . . ?
C19 C46 C34 121.72(18) . . ?
N29 C49 C35 124.34(18) . . ?
C51 C50 C31 119.50(18) . . ?
N29 C51 C50 124.07(18) . . ?
C54 C52 C53 114.66(19) . . ?
C52 C53 C57 112.5(2) . . ?
O1 C54 C52 109.55(17) . . ?
N14 C56 C38 124.38(19) . . ?
C11 O2 C44 117.19(15) . . ?
C8 N4 C23 117.79(16) . . ?
C8 C5 C15 119.89(17) . . ?
C39 C6 C16 119.41(18) . . ?
N4 C8 C5 122.73(16) . . ?
N4 C8 C16 116.06(16) . . ?
C5 C8 C16 121.21(16) . . ?
C23 C9 C15 120.13(16) . . ?
O2 C11 C18 115.74(17) . . ?
O2 C11 C45 124.45(17) . . ?
C18 C11 C45 119.81(17) . . ?
C30 N13 C40 115.88(17) . . ?
C5 C15 C9 116.89(17) . . ?
C5 C15 C20 121.82(16) . . ?
C9 C15 C20 121.27(16) . . ?
C6 C16 C27 116.75(16) . . ?
C6 C16 C8 120.96(17) . . ?
C27 C16 C8 122.28(17) . . ?
C37 C17 C36 116.58(17) . . ?
C37 C17 C23 120.98(16) . . ?
C36 C17 C23 122.43(17) . . ?
C42 C18 C11 119.85(18) . . ?
C26 C20 C42 117.59(17) . . ?
C26 C20 C15 121.61(17) . . ?
C42 C20 C15 120.78(16) . . ?
N4 C23 C9 122.53(17) . . ?
N4 C23 C17 116.08(16) . . ?
C9 C23 C17 121.38(16) . . ?
C39 N24 C47 115.41(16) . . ?
C45 C26 C20 121.53(18) . . ?
C47 C27 C16 119.27(18) . . ?
N13 C30 C36 124.01(18) . . ?
C30 C36 C17 119.69(18) . . ?
C40 C37 C17 119.59(18) . . ?
N24 C39 C6 124.45(19) . . ?
N13 C40 C37 124.26(19) . . ?
C18 C42 C20 121.51(18) . . ?
O2 C44 C48 108.14(16) . . ?
C26 C45 C11 119.68(18) . . ?
N24 C47 C27 124.70(18) . . ?
C44 C48 C55 114.67(17) . . ?
C58 C55 C48 113.42(19) . . ?
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
O1 C22 1.366(2) . ?
O1 C54 1.438(2) . ?
N3 C21 1.349(2) . ?
N3 C12 1.349(2) . ?
C7 C21 1.389(3) . ?
C7 C33 1.395(3) . ?
C10 C12 1.390(3) . ?
C10 C33 1.394(3) . ?
C12 C32 1.493(3) . ?
N14 C41 1.340(3) . ?
N14 C56 1.342(3) . ?
C19 C46 1.388(3) . ?
C19 C43 1.404(3) . ?
C19 C33 1.481(3) . ?
C21 C31 1.488(3) . ?
C22 C28 1.394(3) . ?
C22 C34 1.397(3) . ?
C25 C41 1.389(3) . ?
C25 C32 1.389(3) . ?
C28 C43 1.381(3) . ?
N29 C51 1.341(3) . ?
N29 C49 1.343(3) . ?
C31 C50 1.395(3) . ?
C31 C35 1.395(3) . ?
C32 C38 1.396(3) . ?
C34 C46 1.392(3) . ?
C35 C49 1.389(3) . ?
C38 C56 1.380(3) . ?
C50 C51 1.386(3) . ?
C52 C54 1.504(3) . ?
C52 C53 1.505(3) . ?
C53 C57 1.523(3) . ?
O2 C11 1.373(2) . ?
O2 C44 1.436(2) . ?
N4 C8 1.345(2) . ?
N4 C23 1.346(2) . ?
C5 C8 1.395(3) . ?
C5 C15 1.396(2) . ?
C6 C39 1.387(3) . ?
C6 C16 1.389(3) . ?
C8 C16 1.489(2) . ?
C9 C23 1.393(3) . ?
C9 C15 1.396(3) . ?
C11 C18 1.391(3) . ?
C11 C45 1.391(3) . ?
N13 C30 1.338(3) . ?
N13 C40 1.344(3) . ?
C15 C20 1.486(3) . ?
C16 C27 1.397(3) . ?
C17 C37 1.394(3) . ?
C17 C36 1.395(3) . ?
C17 C23 1.486(2) . ?
C18 C42 1.380(3) . ?
C20 C26 1.393(3) . ?
C20 C42 1.403(3) . ?
N24 C39 1.338(2) . ?
N24 C47 1.339(3) . ?
C26 C45 1.388(3) . ?
C27 C47 1.380(3) . ?
C30 C36 1.386(3) . ?
C37 C40 1.381(3) . ?
C44 C48 1.511(3) . ?
C48 C55 1.516(3) . ?
C55 C58 1.505(3) . ?
