#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:47:40 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180196 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/92/7109250.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_7109250
loop_
_publ_author_name
'Swee Ling Lam'
'Xiaoqian Liu'
'Fangli Zhao'
'Chi-Lik Ken Lee'
'Wei Lek Kwan'
_publ_section_title
;
 Manipulating open-circuit voltage in an organic photovoltaic device via a
 phenylalkyl side chain
;
_journal_name_full               Chem.Commun.
_journal_page_first              4543
_journal_paper_doi               10.1039/c3cc40403j
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C56 H48 N6 O2'
_chemical_formula_weight         837.00
_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                104.475(15)
_cell_angle_beta                 94.514(17)
_cell_angle_gamma                104.237(16)
_cell_formula_units_Z            1
_cell_length_a                   10.125(9)
_cell_length_b                   10.347(9)
_cell_length_c                   11.204(9)
_cell_measurement_reflns_used    419
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.58
_cell_measurement_theta_min      2.54
_cell_volume                     1089.2(16)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_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  0.0729
_diffrn_reflns_av_sigmaI/netI    0.1978
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6416
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_correction_T_min  0.9610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             442
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       0.036(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4817
_refine_ls_number_restraints     192
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.2305
_refine_ls_R_factor_gt           0.1413
_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)+(0.1852P)²+0.7391P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3114
_refine_ls_wR_factor_ref         0.3628
_reflns_number_gt                2435
_reflns_number_total             4817
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc40403j.txt
_cod_data_source_block           c499
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7109250
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
O1 O 1.0609(4) 0.7124(4) 0.9676(4) 0.0173(9) Uani 1 1 d U
N1 N 0.6436(5) 0.3902(4) 0.9130(4) 0.0129(10) Uani 1 1 d U
N2 N 0.3036(5) 0.3770(5) 0.7804(4) 0.0156(11) Uani 1 1 d U
N3 N 0.1760(5) 0.2855(5) 0.7461(4) 0.0180(11) Uani 1 1 d U
C1 C 1.0291(6) 0.5958(5) 0.9854(5) 0.0114(11) Uani 1 1 d U
C2 C 0.8973(6) 0.4918(5) 0.9698(5) 0.0113(11) Uani 1 1 d U
C3 C 0.7659(6) 0.4925(5) 0.9249(5) 0.0103(11) Uani 1 1 d U
C4 C 0.7319(6) 0.5937(6) 0.8747(5) 0.0138(12) Uani 1 1 d U
H4 H 0.7949 0.6764 0.8699 0.017 Uiso 1 1 calc R
C5 C 0.5930(6) 0.5537(6) 0.8337(5) 0.0149(12) Uani 1 1 d U
H5 H 0.5429 0.6032 0.7958 0.018 Uiso 1 1 calc R
C6 C 0.5383(6) 0.4259(5) 0.8582(5) 0.0127(12) Uani 1 1 d U
C7 C 0.4015(6) 0.3366(6) 0.8271(5) 0.0174(12) Uani 1 1 d U
H7 H 0.3824 0.2473 0.8408 0.021 Uiso 1 1 calc R
C8 C 0.6299(6) 0.2600(5) 0.9467(5) 0.0147(12) Uani 1 1 d U
H8A H 0.5423 0.2352 0.9800 0.018 Uiso 1 1 calc R
H8B H 0.7067 0.2720 1.0125 0.018 Uiso 1 1 calc R
C9 C 0.6319(6) 0.1446(6) 0.8338(5) 0.0190(13) Uani 1 1 d U
H9A H 0.7242 0.1650 0.8076 0.023 Uiso 1 1 calc R
H9B H 0.5640 0.1429 0.7644 0.023 Uiso 1 1 calc R
C10 C 0.5989(7) 0.0005(6) 0.8566(6) 0.0227(14) Uani 1 1 d U
H10A H 0.6593 0.0043 0.9321 0.027 Uiso 1 1 calc R
H10B H 0.5022 -0.0260 0.8717 0.027 Uiso 1 1 calc R
C11 C 0.6191(6) -0.1064(6) 0.7487(5) 0.0189(13) Uani 1 1 d U
C12 C 0.7497(7) -0.1175(6) 0.7287(6) 0.0243(14) Uani 1 1 d U
H12 H 0.8268 -0.0578 0.7875 0.029 Uiso 1 1 calc R
C13 C 0.7720(7) -0.2114(6) 0.6274(6) 0.0237(14) Uani 1 1 d U
H13 H 0.8627 -0.2177 0.6174 0.028 Uiso 1 1 calc R
C14 C 0.6621(7) -0.2957(7) 0.5410(6) 0.0279(15) Uani 1 1 d U
H14 H 0.6760 -0.3599 0.4694 0.033 Uiso 1 1 calc R
C15 C 0.5310(8) -0.2870(8) 0.5582(7) 0.0408(19) Uani 1 1 d U
H15 H 0.4546 -0.3458 0.4983 0.049 Uiso 1 1 calc R
C16 C 0.5098(8) -0.1945(7) 0.6607(6) 0.0324(16) Uani 1 1 d U
H16 H 0.4185 -0.1908 0.6716 0.039 Uiso 1 1 calc R
C17 C 0.1558(6) 0.1456(6) 0.7562(5) 0.0180(13) Uani 1 1 d U
C18 C 0.1811(7) 0.0481(6) 0.6586(6) 0.0224(14) Uani 1 1 d U
H18 H 0.2033 0.0704 0.5840 0.027 Uiso 1 1 calc R
C19 C 0.1731(7) -0.0843(6) 0.6718(6) 0.0244(14) Uani 1 1 d U
H19 H 0.1881 -0.1538 0.6051 0.029 Uiso 1 1 calc R
C20 C 0.1436(6) -0.1139(6) 0.7816(5) 0.0199(13) Uani 1 1 d U
H20 H 0.1422 -0.2025 0.7920 0.024 Uiso 1 1 calc R
C21 C 0.1163(6) -0.0158(6) 0.8756(5) 0.0165(12) Uani 1 1 d U
H21 H 0.0937 -0.0378 0.9502 0.020 Uiso 1 1 calc R
C22 C 0.1210(6) 0.1141(6) 0.8637(5) 0.0159(12) Uani 1 1 d U
H22 H 0.1004 0.1814 0.9289 0.019 Uiso 1 1 calc R
C23 C 0.0679(6) 0.3321(6) 0.7016(5) 0.0166(12) Uani 1 1 d U
C24 C -0.0649(6) 0.2455(6) 0.6679(5) 0.0185(13) Uani 1 1 d U
H24 H -0.0829 0.1526 0.6730 0.022 Uiso 1 1 calc R
C25 C -0.1711(7) 0.2923(6) 0.6272(5) 0.0223(14) Uani 1 1 d U
H25 H -0.2619 0.2316 0.6056 0.027 Uiso 1 1 calc R
C26 C -0.1482(7) 0.4246(7) 0.6172(6) 0.0266(15) Uani 1 1 d U
H26 H -0.2221 0.4568 0.5897 0.032 Uiso 1 1 calc R
C27 C -0.0170(7) 0.5096(7) 0.6474(6) 0.0276(15) Uani 1 1 d U
H27 H 0.0001 0.6013 0.6394 0.033 Uiso 1 1 calc R
C28 C 0.0919(7) 0.4659(6) 0.6895(6) 0.0243(14) Uani 1 1 d U
H28 H 0.1825 0.5270 0.7100 0.029 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
C6 N1 C3 109.2(4) . .
C6 N1 C8 124.8(5) . .
C3 N1 C8 125.8(5) . .
C7 N2 N3 117.9(5) . .
N2 N3 C23 117.8(4) . .
N2 N3 C17 119.8(5) . .
C23 N3 C17 122.4(5) . .
O1 C1 C2 136.0(5) . 2_767
O1 C1 C2 132.8(5) . .
C2 C1 C2 91.3(4) 2_767 .
C3 C2 C1 141.3(5) . 2_767
C3 C2 C1 129.9(5) . .
C1 C2 C1 88.7(4) 2_767 .
C2 C3 N1 127.2(5) . .
C2 C3 C4 126.3(5) . .
N1 C3 C4 106.4(5) . .
C5 C4 C3 108.9(5) . .
C4 C5 C6 107.4(5) . .
N1 C6 C5 108.1(5) . .
N1 C6 C7 121.9(5) . .
C5 C6 C7 129.8(5) . .
N2 C7 C6 119.9(5) . .
N1 C8 C9 110.2(4) . .
C8 C9 C10 113.6(4) . .
C11 C10 C9 111.6(5) . .
C16 C11 C12 117.0(6) . .
C16 C11 C10 121.7(6) . .
C12 C11 C10 121.2(6) . .
C13 C12 C11 122.5(6) . .
C14 C13 C12 119.2(6) . .
C13 C14 C15 119.7(7) . .
C16 C15 C14 120.7(8) . .
C15 C16 C11 120.9(7) . .
C22 C17 C18 121.4(5) . .
C22 C17 N3 120.4(5) . .
C18 C17 N3 118.1(5) . .
C17 C18 C19 118.5(5) . .
C20 C19 C18 120.0(6) . .
C21 C20 C19 120.0(5) . .
C20 C21 C22 120.9(5) . .
C21 C22 C17 119.1(5) . .
C24 C23 C28 118.3(6) . .
C24 C23 N3 120.8(5) . .
C28 C23 N3 120.8(6) . .
C25 C24 C23 120.7(5) . .
C26 C25 C24 121.0(6) . .
C27 C26 C25 118.6(7) . .
C26 C27 C28 121.7(6) . .
C27 C28 C23 119.5(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.240(6) .
N1 C6 1.362(7) .
N1 C3 1.390(7) .
N1 C8 1.465(7) .
N2 C7 1.291(7) .
N2 N3 1.360(7) .
N3 C23 1.404(8) .
N3 C17 1.446(7) .
C1 C2 1.459(7) 2_767
C1 C2 1.460(7) .
C2 C3 1.388(8) .
C2 C1 1.459(7) 2_767
C3 C4 1.404(7) .
C4 C5 1.370(8) .
C5 C6 1.405(7) .
C6 C7 1.424(8) .
C8 C9 1.512(8) .
C9 C10 1.535(8) .
C10 C11 1.486(8) .
C11 C16 1.383(9) .
C11 C12 1.386(9) .
C12 C13 1.371(8) .
C13 C14 1.367(9) .
C14 C15 1.377(10) .
C15 C16 1.368(9) .
C17 C22 1.374(7) .
C17 C18 1.377(8) .
C18 C19 1.398(8) .
C19 C20 1.378(8) .
C20 C21 1.365(8) .
C21 C22 1.374(8) .
C23 C24 1.383(8) .
C23 C28 1.388(8) .
C24 C25 1.374(9) .
C25 C26 1.366(9) .
C26 C27 1.363(9) .
C27 C28 1.384(9) .
