#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/51/2205168.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2205168
loop_
_publ_author_name
'Alcock, Nathaniel W.'
'Rourke, Jonathan P'
_publ_section_title
;
 2,6-Bis[2,4-bis(heptyloxy)phenyl]pyridine
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o368
_journal_page_last               o369
_journal_paper_doi               10.1107/S1600536805001248
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C41 H61 N O4'
_chemical_formula_moiety         'C41 H61 N O4'
_chemical_formula_sum            'C41 H61 N O4'
_chemical_formula_weight         631.91
_chemical_name_systematic
;
2,6-Bis[2,4-bis(heptyloxy)phenyl]pyridine
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 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
_cell_angle_beta                 93.963(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.2502(10)
_cell_length_b                   6.9682(6)
_cell_length_c                   24.014(2)
_cell_measurement_reflns_used    2201
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      3
_cell_volume                     1878.0(3)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1994)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens SMART'
_diffrn_measurement_method       ω
_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  0.045
_diffrn_reflns_av_sigmaI/netI    0.062
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8996
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         1.7
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3318
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.130
_refine_ls_R_factor_gt           0.060
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.078P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.134
_refine_ls_wR_factor_ref         0.168
_reflns_number_gt                1753
_reflns_number_total             3318
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk6205.cif
_cod_data_source_block           I
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 2/n'
_cod_database_code               2205168
_cod_database_fobs_code          2205168
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y, -z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.27150(17) 0.9445(3) 0.49155(7) 0.0557(6) Uani d . 1 . . O
O2 0.12875(16) 0.3876(2) 0.39451(7) 0.0541(6) Uani d . 1 . . O
C01 0.2706(2) 0.8380(4) 0.44357(10) 0.0443(7) Uani d . 1 . . C
C02 0.2012(2) 0.6730(4) 0.44313(10) 0.0451(7) Uani d . 1 . . C
H02A 0.1582 0.6425 0.4746 0.054 Uiso calc R 1 . . H
C03 0.1942(2) 0.5526(4) 0.39711(10) 0.0422(7) Uani d . 1 . . C
C04 0.2560(2) 0.5969(3) 0.34979(9) 0.0366(6) Uani d . 1 . . C
C05 0.3235(2) 0.7629(4) 0.35173(10) 0.0413(7) Uani d . 1 . . C
H05A 0.3653 0.7958 0.3200 0.050 Uiso calc R 1 . . H
C06 0.3333(2) 0.8842(4) 0.39782(10) 0.0437(7) Uani d . 1 . . C
H06A 0.3818 0.9958 0.3979 0.052 Uiso calc R 1 . . H
C07 0.2497(2) 0.4772(4) 0.29833(10) 0.0372(6) Uani d . 1 . . C
N08 0.2500 0.5760(4) 0.2500 0.0376(7) Uani d S 1 . . N
C009 0.2482(2) 0.2775(4) 0.29932(11) 0.0435(7) Uani d . 1 . . C
H09A 0.2460 0.2110 0.3338 0.052 Uiso calc R 1 . . H
C010 0.2500 0.1771(5) 0.2500 0.0430(9) Uani d S 1 . . C
H01C 0.2500 0.0408 0.2500 0.052 Uiso calc SR 1 . . H
C11 0.3361(2) 1.1221(4) 0.49299(10) 0.0492(7) Uani d . 1 . . C
H11A 0.3040 1.2079 0.4627 0.059 Uiso calc R 1 . . H
H11B 0.4214 1.0980 0.4877 0.059 Uiso calc R 1 . . H
C12 0.3225(3) 1.2141(4) 0.54911(10) 0.0535(8) Uani d . 1 . . C
H12A 0.3514 1.1239 0.5789 0.064 Uiso calc R 1 . . H
H12B 0.2371 1.2390 0.5535 0.064 Uiso calc R 1 . . H
C13 0.3912(2) 1.4015(4) 0.55598(11) 0.0490(7) Uani d . 1 . . C
H13A 0.4766 1.3763 0.5515 0.059 Uiso calc R 1 . . H
H13B 0.3623 1.4913 0.5261 0.059 Uiso calc R 1 . . H
C14 0.3784(2) 1.4954(4) 0.61216(11) 0.0540(8) Uani d . 1 . . C
H14A 0.2927 1.5150 0.6172 0.065 Uiso calc R 1 . . H
H14B 0.4102 1.4071 0.6419 0.065 Uiso calc R 1 . . H
C15 0.4417(3) 1.6856(4) 0.61915(12) 0.0585(8) Uani d . 1 . . C
H15A 0.4093 1.7744 0.5897 0.070 Uiso calc R 1 . . H
H15B 0.5273 1.6663 0.6136 0.070 Uiso calc R 1 . . H
C16 0.4301(3) 1.7785(5) 0.67574(13) 0.0759(10) Uani d . 1 . . C
H16A 0.4709 1.9028 0.6769 0.114 Uiso calc R 1 . . H
H16B 0.4663 1.6951 0.7051 0.114 Uiso calc R 1 . . H
H16C 0.3456 1.7975 0.6817 0.114 Uiso calc R 1 . . H
C21 0.0420(3) 0.3509(4) 0.43410(13) 0.0642(9) Uani d . 1 . . C
H21A -0.0202 0.4517 0.4321 0.077 Uiso calc R 1 . . H
H21B 0.0800 0.3472 0.4725 0.077 Uiso calc R 1 . . H
C22 -0.0114(4) 0.1576(5) 0.41802(17) 0.0954(14) Uani d . 1 A . C
H22A 0.0528 0.0602 0.4208 0.114 Uiso calc R 1 . . H
H22B -0.0697 0.1228 0.4454 0.114 Uiso calc R 1 . . H
C23 -0.0705(4) 0.1487(7) 0.3625(2) 0.145(2) Uani d D 1 . . C
H23A -0.0256 0.2193 0.3350 0.174 Uiso calc PR 0.554(17) A 1 H
H23B -0.1530 0.1988 0.3618 0.174 Uiso calc PR 0.554(17) A 1 H
H23C -0.0142 0.2079 0.3376 0.174 Uiso d PR 0.446(17) A 2 H
H23D -0.1383 0.2389 0.3635 0.174 Uiso d PR 0.446(17) A 2 H
C24A -0.0681(14) -0.0784(13) 0.3520(6) 0.112(6) Uani d PD 0.554(17) A 1 C
H24A 0.0098 -0.1248 0.3684 0.134 Uiso calc PR 0.554(17) A 1 H
H24B -0.1295 -0.1346 0.3747 0.134 Uiso calc PR 0.554(17) A 1 H
C25A -0.083(2) -0.152(2) 0.3054(8) 0.181(8) Uani d P 0.554(17) A 1 C
H25A -0.0297 -0.0728 0.2833 0.218 Uiso calc PR 0.554(17) A 1 H
H25B -0.1643 -0.1095 0.2931 0.218 Uiso calc PR 0.554(17) A 1 H
C24B -0.1284(9) -0.0165(13) 0.3271(5) 0.070(4) Uani d PD 0.446(17) A 2 C
H24C -0.1757 0.0331 0.2939 0.084 Uiso calc PR 0.446(17) A 2 H
H24D -0.1801 -0.0969 0.3494 0.084 Uiso calc PR 0.446(17) A 2 H
C25B -0.0166(9) -0.130(2) 0.3104(5) 0.066(4) Uani d P 0.446(17) A 2 C
H25C 0.0368 -0.1626 0.3435 0.079 Uiso calc PR 0.446(17) A 2 H
H25D 0.0287 -0.0562 0.2837 0.079 Uiso calc PR 0.446(17) A 2 H
C26 -0.0762(4) -0.3254(7) 0.28082(17) 0.1204(16) Uani d . 1 . . C
H26A -0.1069 -0.3160 0.2417 0.181 Uiso calc PR 0.554(17) A 1 H
H26B -0.1240 -0.4180 0.3003 0.181 Uiso calc PR 0.554(17) A 1 H
H26C 0.0070 -0.3682 0.2826 0.181 Uiso calc PR 0.554(17) A 1 H
H26D -0.0117 -0.4042 0.2676 0.181 Uiso d PR 0.446(17) A 2 H
H26E -0.1300 -0.2868 0.2490 0.181 Uiso d PR 0.446(17) A 2 H
H26F -0.1206 -0.3997 0.3071 0.181 Uiso d PR 0.446(17) A 2 H
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C01 O1 C11 . . 117.5(2)
C03 O2 C21 . . 120.7(2)
O1 C01 C06 . . 124.5(2)
O1 C01 C02 . . 115.2(2)
C06 C01 C02 . . 120.2(2)
C03 C02 C01 . . 120.5(2)
C03 C02 H02A . . 119.7
C01 C02 H02A . . 119.7
O2 C03 C02 . . 123.2(2)
O2 C03 C04 . . 116.3(2)
C02 C03 C04 . . 120.5(2)
C05 C04 C03 . . 117.2(2)
C05 C04 C07 . . 119.4(2)
C03 C04 C07 . . 123.3(2)
C04 C05 C06 . . 123.3(2)
C04 C05 H05A . . 118.4
C06 C05 H05A . . 118.4
C01 C06 C05 . . 118.3(2)
C01 C06 H06A . . 120.9
C05 C06 H06A . . 120.9
N08 C07 C009 . . 121.7(2)
N08 C07 C04 . . 115.1(2)
C009 C07 C04 . . 123.1(2)
C07 N08 C07 4_656 . 118.6(3)
C010 C009 C07 . . 119.5(3)
C010 C009 H09A . . 120.3
C07 C009 H09A . . 120.3
C009 C010 C009 . 4_656 119.0(3)
C009 C010 H01C . . 120.5
C009 C010 H01C 4_656 . 120.5
O1 C11 C12 . . 107.8(2)
O1 C11 H11A . . 110.2
C12 C11 H11A . . 110.2
O1 C11 H11B . . 110.2
C12 C11 H11B . . 110.2
H11A C11 H11B . . 108.5
C11 C12 C13 . . 112.3(2)
C11 C12 H12A . . 109.1
C13 C12 H12A . . 109.1
C11 C12 H12B . . 109.1
C13 C12 H12B . . 109.1
H12A C12 H12B . . 107.9
C14 C13 C12 . . 112.9(2)
C14 C13 H13A . . 109.0
C12 C13 H13A . . 109.0
C14 C13 H13B . . 109.0
C12 C13 H13B . . 109.0
H13A C13 H13B . . 107.8
C15 C14 C13 . . 113.9(2)
C15 C14 H14A . . 108.8
C13 C14 H14A . . 108.8
C15 C14 H14B . . 108.8
C13 C14 H14B . . 108.8
H14A C14 H14B . . 107.7
C14 C15 C16 . . 113.9(2)
C14 C15 H15A . . 108.8
C16 C15 H15A . . 108.8
C14 C15 H15B . . 108.8
C16 C15 H15B . . 108.8
H15A C15 H15B . . 107.7
C15 C16 H16A . . 109.5
C15 C16 H16B . . 109.5
H16A C16 H16B . . 109.5
C15 C16 H16C . . 109.5
H16A C16 H16C . . 109.5
H16B C16 H16C . . 109.5
O2 C21 C22 . . 105.5(2)
O2 C21 H21A . . 110.7
C22 C21 H21A . . 110.7
O2 C21 H21B . . 110.7
C22 C21 H21B . . 110.7
H21A C21 H21B . . 108.8
C23 C22 C21 . . 114.9(4)
C23 C22 H22A . . 108.5
C21 C22 H22A . . 108.5
C23 C22 H22B . . 108.5
C21 C22 H22B . . 108.5
H22A C22 H22B . . 107.5
C22 C23 C24B . . 133.3(6)
C22 C23 C24A . . 100.1(7)
C22 C23 H23A . . 111.8
C24B C23 H23A . . 102.6
C24A C23 H23A . . 111.8
C22 C23 H23B . . 111.8
C24B C23 H23B . . 83.9
C24A C23 H23B . . 111.7
H23A C23 H23B . . 109.5
C22 C23 H23C . . 105.4
C24B C23 H23C . . 104.0
C24A C23 H23C . . 107.3
H23B C23 H23C . . 118.7
C22 C23 H23D . . 104.8
C24B C23 H23D . . 100.9
C24A C23 H23D . . 130.7
H23C C23 H23D . . 106.1
C25A C24A C23 . . 123.3(15)
C25A C24A H24A . . 106.5
C23 C24A H24A . . 106.5
C25A C24A H24B . . 106.5
C23 C24A H24B . . 106.5
H24A C24A H24B . . 106.5
C24A C25A C26 . . 139.6(19)
C24A C25A H25A . . 102.2
C26 C25A H25A . . 102.2
C24A C25A H25B . . 102.1
C26 C25A H25B . . 102.2
H25A C25A H25B . . 104.8
C23 C24B C25B . . 101.7(9)
C23 C24B H24C . . 111.4
C25B C24B H24C . . 111.4
C23 C24B H24D . . 111.4
C25B C24B H24D . . 111.4
C24B C25B C26 . . 102.6(7)
C24B C25B H25D . . 111.3
C26 C25B H25D . . 111.3
C25A C26 H26A . . 109.5
C25B C26 H26A . . 117.5
C25A C26 H26B . . 109.5
C25B C26 H26B . . 123.8
H26A C26 H26B . . 109.5
C25A C26 H26C . . 109.4
C25B C26 H26C . . 82.7
H26A C26 H26C . . 109.5
H26B C26 H26C . . 109.5
C25B C26 H26D . . 108.2
C25B C26 H26E . . 108.6
H26D C26 H26E . . 109.5
C25B C26 H26F . . 111.6
H26D C26 H26F . . 109.5
H26E C26 H26F . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C01 . 1.370(3)
O1 C11 . 1.434(3)
O2 C03 . 1.364(3)
O2 C21 . 1.432(3)
C01 C06 . 1.384(3)
C01 C02 . 1.390(3)
C02 C03 . 1.385(3)
C02 H02A . 0.9500
C03 C04 . 1.407(3)
C04 C05 . 1.382(3)
C04 C07 . 1.489(3)
C05 C06 . 1.391(3)
C05 H05A . 0.9500
C06 H06A . 0.9500
C07 N08 . 1.350(3)
C07 C009 . 1.392(3)
N08 C07 4_656 1.350(3)
C009 C010 . 1.377(3)
C009 H09A . 0.9500
C010 C009 4_656 1.377(3)
C010 H01C . 0.9500
C11 C12 . 1.509(3)
C11 H11A . 0.9900
C11 H11B . 0.9900
C12 C13 . 1.520(4)
C12 H12A . 0.9900
C12 H12B . 0.9900
C13 C14 . 1.515(3)
C13 H13A . 0.9900
C13 H13B . 0.9900
C14 C15 . 1.508(3)
C14 H14A . 0.9900
C14 H14B . 0.9900
C15 C16 . 1.519(4)
C15 H15A . 0.9900
C15 H15B . 0.9900
C16 H16A . 0.9800
C16 H16B . 0.9800
C16 H16C . 0.9800
C21 C22 . 1.514(4)
C21 H21A . 0.9900
C21 H21B . 0.9900
C22 C23 . 1.450(6)
C22 H22A . 0.9900
C22 H22B . 0.9900
C23 C24B . 1.547(8)
C23 C24A . 1.603(8)
C23 H23A . 0.9900
C23 H23B . 0.9900
C23 H23C . 0.9900
C23 H23D . 0.9899
C24A C25A . 1.23(2)
C24A H24A . 0.9900
C24A H24B . 0.9900
C25A C26 . 1.352(16)
C25A H25A . 0.9900
C25A H25B . 0.9900
C24B C25B . 1.563(18)
C24B H24C . 0.9900
C24B H24D . 0.9900
C25B C26 . 1.654(16)
C25B H25C . 0.9900
C25B H25D . 0.9900
C26 H26A . 0.9800
C26 H26B . 0.9800
C26 H26C . 0.9800
C26 H26D . 0.9800
C26 H26E . 0.9799
C26 H26F . 0.9800
