#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/50/1515001.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_1515001
loop_
_publ_author_name
'Meisner, Jeffrey S.'
'Sedbrook, Danielle F.'
'Krikorian, Markrete'
'Chen, Jun'
'Sattler, Aaron'
'Carnes, Matthew E.'
'Murray, Christopher B.'
'Steigerwald, Michael'
'Nuckolls, Colin'
_publ_section_title
;
 Functionalizing molecular wires: a tunable class of
 α,ω-diphenyl-μ,ν-dicyano-oligoenes
;
_journal_issue                   4
_journal_name_full               'Chemical Science'
_journal_page_first              1007
_journal_paper_doi               10.1039/c2sc00770c
_journal_volume                  3
_journal_year                    2012
_chemical_formula_sum            'C32 H32 N4 O6'
_chemical_formula_weight         568.62
_chemical_name_systematic
;
?
;
_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                101.417(2)
_cell_angle_beta                 91.557(3)
_cell_angle_gamma                92.041(2)
_cell_formula_units_Z            1
_cell_length_a                   6.2483(10)
_cell_length_b                   7.1520(11)
_cell_length_c                   16.741(3)
_cell_measurement_reflns_used    3107
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      30.35
_cell_measurement_theta_min      2.48
_cell_volume                     732.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0821
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11762
_diffrn_reflns_theta_full        30.53
_diffrn_reflns_theta_max         30.53
_diffrn_reflns_theta_min         1.24
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_correction_T_min  0.9562
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0022(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         4437
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0503
_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)+(0.0399P)²+0.0307P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1143
_reflns_number_gt                2300
_reflns_number_total             4437
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2sc00770c.txt
_cod_data_source_block           DPDC5-CO2H
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'EMPIRICAL'
changed to 'empirical' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1515001
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
N1 N 0.5454(3) -0.7366(2) -0.00707(10) 0.0483(4) Uani 1 1 d .
O1 O 0.5579(2) 0.54031(17) 0.27858(8) 0.0389(3) Uani 1 1 d .
H1 H 0.538(3) 0.663(3) 0.3061(12) 0.067(7) Uiso 1 1 d .
O2 O 0.8503(2) 0.59470(16) 0.36046(7) 0.0443(4) Uani 1 1 d .
C1 C 0.7434(3) 0.4907(2) 0.30673(10) 0.0293(4) Uani 1 1 d .
C2 C 0.8079(3) 0.2964(2) 0.26850(9) 0.0252(4) Uani 1 1 d .
C3 C 1.0121(3) 0.2450(2) 0.28715(10) 0.0317(4) Uani 1 1 d .
H3A H 1.1067 0.3352 0.3214 0.038 Uiso 1 1 calc R
C4 C 1.0795(3) 0.0634(2) 0.25636(10) 0.0312(4) Uani 1 1 d .
H4A H 1.2198 0.0300 0.2699 0.037 Uiso 1 1 calc R
C5 C 0.9433(3) -0.0717(2) 0.20542(9) 0.0250(4) Uani 1 1 d .
C6 C 0.7392(3) -0.0173(2) 0.18577(10) 0.0285(4) Uani 1 1 d .
H6A H 0.6450 -0.1060 0.1506 0.034 Uiso 1 1 calc R
C7 C 0.6725(3) 0.1644(2) 0.21685(9) 0.0274(4) Uani 1 1 d .
H7A H 0.5332 0.1992 0.2028 0.033 Uiso 1 1 calc R
C8 C 1.0256(3) -0.2603(2) 0.17438(10) 0.0289(4) Uani 1 1 d .
H8A H 1.1666 -0.2808 0.1926 0.035 Uiso 1 1 calc R
C9 C 0.9260(3) -0.4076(2) 0.12333(9) 0.0273(4) Uani 1 1 d .
H9A H 0.7840 -0.3937 0.1042 0.033 Uiso 1 1 calc R
C10 C 1.0258(3) -0.5850(2) 0.09664(9) 0.0269(4) Uani 1 1 d .
H10A H 1.1697 -0.5928 0.1151 0.032 Uiso 1 1 calc R
C11 C 0.9352(2) -0.7431(2) 0.04756(9) 0.0253(4) Uani 1 1 d .
C12 C 1.0438(3) -0.9195(2) 0.02311(9) 0.0257(4) Uani 1 1 d .
H12A H 1.1890 -0.9216 0.0412 0.031 Uiso 1 1 calc R
C13 C 0.7171(3) -0.7381(2) 0.01771(10) 0.0307(4) Uani 1 1 d .
N2 N 0.6263(2) 1.15021(19) 0.44254(8) 0.0286(3) Uani 1 1 d .
O3 O 0.48267(19) 0.88744(16) 0.35663(7) 0.0359(3) Uani 1 1 d .
C14 C 0.6372(3) 0.9791(2) 0.39597(10) 0.0313(4) Uani 1 1 d .
H14A H 0.7725 0.9220 0.3923 0.038 Uiso 1 1 calc R
C15 C 0.4265(3) 1.2502(2) 0.44840(11) 0.0363(4) Uani 1 1 d .
H15A H 0.3087 1.1618 0.4236 0.054 Uiso 1 1 calc R
H15B H 0.4382 1.3568 0.4197 0.054 Uiso 1 1 calc R
H15C H 0.3983 1.2992 0.5059 0.054 Uiso 1 1 calc R
C16 C 0.8126(3) 1.2489(3) 0.48878(11) 0.0407(5) Uani 1 1 d .
H16A H 0.9358 1.1670 0.4804 0.061 Uiso 1 1 calc R
H16B H 0.7816 1.2779 0.5469 0.061 Uiso 1 1 calc R
H16C H 0.8455 1.3679 0.4701 0.061 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'
O O 0.0106 0.0060 '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'
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
O2 C1 O1 122.67(15) .
O2 C1 C2 122.70(16) .
O1 C1 C2 114.62(14) .
C3 C2 C7 119.15(14) .
C3 C2 C1 117.55(14) .
C7 C2 C1 123.28(15) .
C2 C3 C4 120.60(15) .
C3 C4 C5 120.74(16) .
C6 C5 C4 118.18(14) .
C6 C5 C8 123.93(14) .
C4 C5 C8 117.88(15) .
C7 C6 C5 120.83(14) .
C6 C7 C2 120.48(15) .
C9 C8 C5 127.77(16) .
C8 C9 C10 122.32(16) .
C11 C10 C9 126.34(16) .
C10 C11 C13 118.89(14) .
C10 C11 C12 123.86(15) .
C13 C11 C12 117.24(13) .
C12 C12 C11 125.32(19) 2_735
N1 C13 C11 178.78(19) .
C14 N2 C15 120.84(14) .
C14 N2 C16 121.96(14) .
C15 N2 C16 117.19(13) .
O3 C14 N2 124.51(15) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C13 1.141(2) .
O1 C1 1.3257(19) .
O2 C1 1.2146(19) .
C1 C2 1.485(2) .
C2 C3 1.385(2) .
C2 C7 1.391(2) .
C3 C4 1.384(2) .
C4 C5 1.400(2) .
C5 C6 1.396(2) .
C5 C8 1.463(2) .
C6 C7 1.384(2) .
C8 C9 1.340(2) .
C9 C10 1.430(2) .
C10 C11 1.355(2) .
C11 C13 1.442(2) .
C11 C12 1.446(2) .
C12 C12 1.343(3) 2_735
N2 C14 1.320(2) .
N2 C15 1.456(2) .
N2 C16 1.459(2) .
O3 C14 1.2429(19) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 O3 0.92(2) 1.71(2) 2.6314(16) 176(2)
