#------------------------------------------------------------------------------
#$Date: 2018-03-15 18:33:54 +0200 (Thu, 15 Mar 2018) $
#$Revision: 206958 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/11/7111133.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7111133
loop_
_publ_author_name
'Cave, Gareth W. V.'
'Raston, Colin L.'
_publ_section_title
;
 Toward benign syntheses of pyridines involving sequential solvent free
 aldol and Michael addition reactions
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   22
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              2199
_journal_page_last               2200
_journal_paper_doi               10.1039/b007431o
_journal_year                    2000
_chemical_formula_sum            'C29 H31 N3 O'
_chemical_formula_weight         437.57
_chemical_name_common
;
4'-(4-octyloxyphenyl)-4,2': 6',4''-terpyridine 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 114.0330(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.7473(3)
_cell_length_b                   10.8189(3)
_cell_length_c                   23.8391(7)
_cell_measurement_temperature    123(2)
_cell_volume                     4651.6(2)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.053
_diffrn_reflns_av_sigmaI/netI    0.0660
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            28604
_diffrn_reflns_theta_full        28.17
_diffrn_reflns_theta_max         28.17
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prim
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         5661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0625
_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)+(0.1001P)²+1.0504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1848
_reflns_number_gt                3759
_reflns_number_total             5661
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b007431osup1.cif
_cod_data_source_block           global
_cod_depositor_comments
;

2018-02-22
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C116 H124 N12 O4'
_cod_original_formula_weight         1750.27
_cod_original_formula_units_Z            2
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7111133
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1 C 0.45784(12) 0.76501(18) 0.13272(9) 0.0229(5) Uani 1 1 d
H1 H 0.5315(11) 0.458(2) 0.0798(9) 0.026(5) Uiso 1 1 d
C2 C 0.46185(12) 0.89226(19) 0.13251(10) 0.0277(5) Uani 1 1 d
H2 H 0.3896(11) 0.061(2) 0.3346(10) 0.027(6) Uiso 1 1 d
N3 N 0.43818(10) 0.96692(15) 0.16557(8) 0.0283(4) Uani 1 1 d
H3 H 0.2885(14) -0.031(2) 0.5926(12) 0.048(7) Uiso 1 1 d
C4 C 0.40870(12) 0.90948(18) 0.20009(11) 0.0283(5) Uani 1 1 d
H4 H 0.2516(13) -0.125(2) 0.5372(11) 0.034(6) Uiso 1 1 d
C5 C 0.40270(11) 0.78336(17) 0.20368(10) 0.0234(5) Uani 1 1 d
H5 H 0.2505(14) 0.352(2) 0.3202(11) 0.045(7) Uiso 1 1 d
C6 C 0.42843(10) 0.70678(16) 0.16973(8) 0.0175(4) Uani 1 1 d
H6 H 0.1665(13) -0.003(2) 0.5937(11) 0.041(7) Uiso 1 1 d
C7 C 0.42482(10) 0.56971(16) 0.17239(8) 0.0162(4) Uani 1 1 d
H7 H 0.1379(16) -0.118(2) 0.5477(13) 0.056(8) Uiso 1 1 d
C8 C 0.40098(10) 0.51039(16) 0.21281(9) 0.0179(4) Uani 1 1 d
H8 H 0.4828(13) 0.927(2) 0.1047(11) 0.041(7) Uiso 1 1 d
C9 C 0.39708(10) 0.38170(17) 0.21325(8) 0.0170(4) Uani 1 1 d
H9 H 0.4085(12) 0.1540(18) 0.0803(10) 0.027(6) Uiso 1 1 d
C10 C 0.41809(10) 0.31695(17) 0.17229(8) 0.0173(4) Uani 1 1 d
H10 H 0.5667(15) 0.347(2) 0.0090(12) 0.048(7) Uiso 1 1 d
C11 C 0.44255(10) 0.38241(16) 0.13350(8) 0.0168(4) Uani 1 1 d
H11 H 0.4506(11) 0.059(2) 0.0116(9) 0.026(5) Uiso 1 1 d
N12 N 0.44639(9) 0.50657(13) 0.13356(7) 0.0183(4) Uani 1 1 d
H12 H 0.2304(14) -0.242(2) 0.6244(11) 0.045(7) Uiso 1 1 d
C13 C 0.46543(10) 0.31774(16) 0.08884(8) 0.0173(4) Uani 1 1 d
H13 H 0.4735(13) 0.721(2) 0.1105(11) 0.032(6) Uiso 1 1 d
C14 C 0.44183(11) 0.19839(17) 0.06801(9) 0.0214(4) Uani 1 1 d
H14 H 0.1229(13) -0.140(2) 0.6615(11) 0.040(7) Uiso 1 1 d
C15 C 0.46563(12) 0.14299(18) 0.02704(9) 0.0249(5) Uani 1 1 d
H15 H 0.1028(15) -0.253(2) 0.6161(13) 0.053(8) Uiso 1 1 d
N16 N 0.51089(10) 0.19652(16) 0.00495(8) 0.0276(4) Uani 1 1 d
H16 H 0.4351(12) 0.1633(18) 0.2707(9) 0.022(5) Uiso 1 1 d
C17 C 0.53310(13) 0.3115(2) 0.02513(10) 0.0289(5) Uani 1 1 d
H17 H 0.4163(11) 0.2289(19) 0.1699(9) 0.022(5) Uiso 1 1 d
C18 C 0.51224(12) 0.37463(18) 0.06611(10) 0.0243(5) Uani 1 1 d
H18 H 0.3898(14) 0.958(2) 0.2206(12) 0.046(7) Uiso 1 1 d
C19 C 0.36971(10) 0.31721(16) 0.25501(8) 0.0177(4) Uani 1 1 d
H19 H 0.3118(13) -0.033(2) 0.3694(11) 0.037(7) Uiso 1 1 d
C20 C 0.39603(11) 0.20102(17) 0.27913(9) 0.0197(4) Uani 1 1 d
H20 H 0.1683(16) 0.044(2) 0.4795(13) 0.059(8) Uiso 1 1 d
C21 C 0.36895(11) 0.13950(18) 0.31699(9) 0.0219(4) Uani 1 1 d
H21 H 0.3821(12) 0.7519(18) 0.2288(10) 0.022(5) Uiso 1 1 d
C22 C 0.31440(11) 0.19468(18) 0.33129(9) 0.0227(4) Uani 1 1 d
H22 H 0.2954(14) -0.089(2) 0.4592(11) 0.041(6) Uiso 1 1 d
C23 C 0.28854(11) 0.31193(18) 0.30857(9) 0.0232(4) Uani 1 1 d
H23 H 0.2982(11) 0.4514(19) 0.2554(9) 0.019(5) Uiso 1 1 d
C24 C 0.31573(11) 0.37179(18) 0.27114(9) 0.0217(4) Uani 1 1 d
H24 H 0.3707(13) 0.0489(19) 0.4288(10) 0.032(6) Uiso 1 1 d
O25 O 0.28235(8) 0.14192(12) 0.36667(7) 0.0299(4) Uani 1 1 d
H25 H 0.3247(16) 0.102(2) 0.5130(13) 0.062(9) Uiso 1 1 d
C26 C 0.31464(13) 0.0304(2) 0.39878(11) 0.0281(5) Uani 1 1 d
H26 H 0.1618(14) -0.268(2) 0.6870(12) 0.049(7) Uiso 1 1 d
C27 C 0.27118(13) -0.00806(19) 0.43581(10) 0.0264(5) Uani 1 1 d
H27 H 0.2215(14) -0.028(2) 0.4088(11) 0.036(6) Uiso 1 1 d
C28 C 0.27011(17) 0.0873(2) 0.48169(12) 0.0400(6) Uani 1 1 d
H28 H 0.2501(16) -0.125(2) 0.6708(14) 0.066(9) Uiso 1 1 d
C29 C 0.21796(16) 0.0549(2) 0.51231(12) 0.0364(6) Uani 1 1 d
H29 H 0.2546(16) 0.168(3) 0.4614(14) 0.067(9) Uiso 1 1 d
C30 C 0.24061(13) -0.0543(2) 0.55565(11) 0.0303(5) Uani 1 1 d
H30 H 0.3875(12) 0.5594(19) 0.2412(10) 0.033(6) Uiso 1 1 d
C31 C 0.18345(13) -0.0847(2) 0.58111(10) 0.0288(5) Uani 1 1 d
H31 H 0.2154(16) 0.130(3) 0.5374(13) 0.060(8) Uiso 1 1 d
C32 C 0.20843(14) -0.1732(2) 0.63442(11) 0.0330(5) Uani 1 1 d
C33 C 0.14657(15) -0.2123(2) 0.65232(12) 0.0360(6) 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
C2 C1 C6 119.6(2)
N3 C2 C1 124.5(2)
C2 N3 C4 115.17(18)
N3 C4 C5 124.7(2)
C4 C5 C6 119.58(19)
C1 C6 C5 116.47(17)
C1 C6 C7 121.26(17)
C5 C6 C7 122.27(17)
N12 C7 C8 122.13(16)
N12 C7 C6 116.17(15)
C8 C7 C6 121.70(16)
C7 C8 C9 120.09(17)
C8 C9 C10 117.58(17)
C8 C9 C19 120.66(17)
C10 C9 C19 121.74(16)
C9 C10 C11 119.34(17)
N12 C11 C10 122.66(17)
N12 C11 C13 115.88(16)
C10 C11 C13 121.47(16)
C11 N12 C7 118.18(15)
C18 C13 C14 116.74(17)
C18 C13 C11 120.91(16)
C14 C13 C11 122.35(17)
C15 C14 C13 119.56(18)
N16 C15 C14 124.32(18)
C15 N16 C17 115.66(17)
N16 C17 C18 124.2(2)
C17 C18 C13 119.51(18)
C20 C19 C24 117.68(17)
C20 C19 C9 121.62(17)
C24 C19 C9 120.70(16)
C21 C20 C19 121.50(18)
C22 C21 C20 119.63(18)
O25 C22 C21 124.83(17)
O25 C22 C23 115.56(17)
C21 C22 C23 119.62(18)
C24 C23 C22 120.19(19)
C23 C24 C19 121.36(18)
C22 O25 C26 117.64(15)
O25 C26 C27 107.92(17)
C28 C27 C26 114.30(18)
C27 C28 C29 113.6(2)
C30 C29 C28 115.9(2)
C29 C30 C31 112.4(2)
C32 C31 C30 115.70(19)
C31 C32 C33 113.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.379(3)
C1 C6 1.389(3)
C2 N3 1.339(3)
N3 C4 1.339(3)
C4 C5 1.375(3)
C5 C6 1.391(3)
C6 C7 1.487(3)
C7 N12 1.351(2)
C7 C8 1.390(3)
C8 C9 1.395(3)
C9 C10 1.395(3)
C9 C19 1.486(3)
C10 C11 1.398(3)
C11 N12 1.345(2)
C11 C13 1.490(3)
C13 C18 1.391(3)
C13 C14 1.394(3)
C14 C15 1.381(3)
C15 N16 1.340(3)
N16 C17 1.342(3)
C17 C18 1.385(3)
C19 C20 1.392(3)
C19 C24 1.402(3)
C20 C21 1.392(3)
C21 C22 1.390(3)
C22 O25 1.368(2)
C22 C23 1.392(3)
C23 C24 1.376(3)
O25 C26 1.432(2)
C26 C27 1.518(3)
C27 C28 1.510(3)
C28 C29 1.526(3)
C29 C30 1.512(3)
C30 C31 1.519(3)
C31 C32 1.505(3)
C32 C33 1.509(3)
