#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/49/1514999.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_1514999
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            'C41 H35 Cl2 N2'
_chemical_formula_weight         626.61
_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                 106.563(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   32.920(13)
_cell_length_b                   11.005(4)
_cell_length_c                   9.624(4)
_cell_measurement_reflns_used    1460
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      24.55
_cell_measurement_theta_min      2.81
_cell_volume                     3342(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.2928
_diffrn_reflns_av_sigmaI/netI    0.2410
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            22453
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.29
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.9977
_exptl_absorpt_correction_T_min  0.9130
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            BLACK
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             1316
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.0007(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         4152
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.2737
_refine_ls_R_factor_gt           0.0837
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1900
_refine_ls_wR_factor_ref         0.2638
_reflns_number_gt                1358
_reflns_number_total             4152
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2sc00770c.txt
_cod_data_source_block           DPDC13
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed
to 'constr' 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      C2/c
_cod_database_code               1514999
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
_atom_site_refinement_flags
N N 0.05261(15) -0.2305(5) -0.7672(5) 0.0377(12) Uani 1 1 d .
C1 C 0.35419(17) 0.0203(5) 0.6741(6) 0.0325(14) Uani 1 1 d .
H1A H 0.3452 -0.0401 0.6012 0.039 Uiso 1 1 calc R
C2 C 0.38539(18) -0.0068(5) 0.7988(6) 0.0409(15) Uani 1 1 d .
H2A H 0.3979 -0.0853 0.8106 0.049 Uiso 1 1 calc R
C3 C 0.39877(18) 0.0784(5) 0.9072(6) 0.0389(15) Uani 1 1 d .
H3A H 0.4205 0.0590 0.9930 0.047 Uiso 1 1 calc R
C4 C 0.38041(19) 0.1915(5) 0.8902(6) 0.0391(16) Uani 1 1 d .
H4A H 0.3892 0.2506 0.9648 0.047 Uiso 1 1 calc R
C5 C 0.34917(18) 0.2192(5) 0.7642(6) 0.0368(15) Uani 1 1 d .
H5A H 0.3367 0.2978 0.7533 0.044 Uiso 1 1 calc R
C6 C 0.33553(17) 0.1343(5) 0.6525(5) 0.0298(13) Uani 1 1 d .
C7 C 0.30428(17) 0.1716(5) 0.5188(5) 0.0307(13) Uani 1 1 d .
H7A H 0.2946 0.2531 0.5165 0.037 Uiso 1 1 calc R
C8 C 0.28737(16) 0.1060(5) 0.3985(5) 0.0293(13) Uani 1 1 d .
H8A H 0.2947 0.0226 0.3977 0.035 Uiso 1 1 calc R
C9 C 0.25870(17) 0.1573(5) 0.2715(5) 0.0312(13) Uani 1 1 d .
H9A H 0.2515 0.2406 0.2751 0.037 Uiso 1 1 calc R
C10 C 0.24096(16) 0.0960(5) 0.1458(5) 0.0283(13) Uani 1 1 d .
H10A H 0.2474 0.0121 0.1422 0.034 Uiso 1 1 calc R
C11 C 0.21327(16) 0.1503(5) 0.0193(5) 0.0285(13) Uani 1 1 d .
H11A H 0.2080 0.2350 0.0220 0.034 Uiso 1 1 calc R
C12 C 0.19405(16) 0.0900(5) -0.1036(5) 0.0286(13) Uani 1 1 d .
H12A H 0.1994 0.0053 -0.1054 0.034 Uiso 1 1 calc R
C13 C 0.16622(16) 0.1428(5) -0.2323(5) 0.0256(12) Uani 1 1 d .
H13A H 0.1616 0.2280 -0.2338 0.031 Uiso 1 1 calc R
C14 C 0.14643(16) 0.0784(5) -0.3505(5) 0.0283(13) Uani 1 1 d .
H14A H 0.1524 -0.0062 -0.3467 0.034 Uiso 1 1 calc R
C15 C 0.11756(16) 0.1215(5) -0.4811(5) 0.0260(12) Uani 1 1 d .
H15A H 0.1128 0.2064 -0.4938 0.031 Uiso 1 1 calc R
C16 C 0.09673(16) 0.0451(5) -0.5874(5) 0.0266(13) Uani 1 1 d .
H16A H 0.1028 -0.0390 -0.5727 0.032 Uiso 1 1 calc R
C17 C 0.06665(16) 0.0789(5) -0.7188(5) 0.0277(13) Uani 1 1 d .
H17A H 0.0627 0.1634 -0.7384 0.033 Uiso 1 1 calc R
C18 C 0.04287(17) 0.0013(5) -0.8194(5) 0.0289(13) Uani 1 1 d .
C19 C 0.01238(16) 0.0380(5) -0.9511(5) 0.0281(13) Uani 1 1 d .
H19A H 0.0094 0.1226 -0.9709 0.034 Uiso 1 1 calc R
C20 C 0.04843(16) -0.1283(6) -0.7894(5) 0.0299(13) Uani 1 1 d .
Cl Cl 0.01840(6) 0.36970(15) 0.40644(18) 0.0594(6) Uani 1 1 d .
C21 C 0.0000 0.4627(8) 0.2500 0.050(3) Uani 1 2 d S
H21A H 0.0318 0.5070 0.2539 0.060 Uiso 0.50 1 d PR
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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 121.1(5) .
C1 C2 C3 120.8(5) .
C4 C3 C2 119.4(5) .
C3 C4 C5 119.8(5) .
C4 C5 C6 121.5(5) .
C1 C6 C5 117.3(5) .
C1 C6 C7 123.9(5) .
C5 C6 C7 118.8(5) .
C8 C7 C6 128.6(5) .
C7 C8 C9 122.4(5) .
C10 C9 C8 125.1(5) .
C9 C10 C11 123.9(5) .
C12 C11 C10 124.7(5) .
C11 C12 C13 125.7(5) .
C14 C13 C12 123.7(5) .
C13 C14 C15 127.8(5) .
C16 C15 C14 121.9(5) .
C15 C16 C17 126.1(5) .
C18 C17 C16 125.9(5) .
C17 C18 C19 124.7(5) .
C17 C18 C20 117.4(5) .
C19 C18 C20 117.9(5) .
C19 C19 C18 125.1(7) 5_553
N C20 C18 179.4(6) .
Cl C21 Cl 109.7(5) 2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N C20 1.145(7) .
C1 C2 1.372(7) .
C1 C6 1.386(7) .
C2 C3 1.379(8) .
C3 C4 1.373(8) .
C4 C5 1.382(7) .
C5 C6 1.398(7) .
C6 C7 1.459(7) .
C7 C8 1.343(7) .
C8 C9 1.430(7) .
C9 C10 1.363(7) .
C10 C11 1.428(7) .
C11 C12 1.346(7) .
C12 C13 1.436(7) .
C13 C14 1.341(7) .
C14 C15 1.423(7) .
C15 C16 1.350(7) .
C16 C17 1.415(7) .
C17 C18 1.359(7) .
C18 C19 1.432(7) .
C18 C20 1.456(8) .
C19 C19 1.347(10) 5_553
Cl C21 1.778(5) .
C21 Cl 1.778(5) 2
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139042746
