#------------------------------------------------------------------------------
#$Date: 2019-11-28 22:08:14 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244764 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/95/7239549.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_7239549
loop_
_publ_author_name
'Viterisi, Aurélien'
'Montcada, Núria F.'
'Kumar, Challuri Vijay'
'Gispert-Guirado, Francesc'
'Martin, Eddy'
'Escudero, Eduardo'
'Palomares, Emilio'
_publ_section_title
;
 Unambiguous determination of molecular packing in crystalline donor
 domains of small molecule solution processed solar cell devices using
 routine X-ray diffraction techniques
;
_journal_issue                   10
_journal_name_full               'Journal of Materials Chemistry A'
_journal_page_first              3536
_journal_paper_doi               10.1039/c3ta13116e
_journal_volume                  2
_journal_year                    2014
_chemical_formula_sum            'C32 H44 N2 O6'
_chemical_formula_weight         552.69
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.0473(8)
_cell_length_b                   18.1959(10)
_cell_length_c                   10.7775(6)
_cell_measurement_reflns_used    9541
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.24
_cell_measurement_theta_min      2.24
_cell_volume                     2950.9(3)
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support whith MicroMount'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            30505
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         30.34
_diffrn_reflns_theta_min         1.76
_diffrn_source                   'Micorfocus source E025 IuS'
_diffrn_source_current           0.6
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Bruker APEX DUO'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.9831
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         4118
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0549P)²+1.3575P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1228
_reflns_number_gt                3282
_reflns_number_total             4118
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ta13116e.txt
_cod_data_source_block           mo_av63a3_pbcn
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_diffrn_measurement_specimen_suppport' was replaced with
'_diffrn_measurement_specimen_support' as specified in the
replacement file
'/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/lists/replacement-tags.lst'.

Automatic conversion script
Id: cif_correct_tags 6909 2019-04-08 15:41:33Z antanas 

The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      Pbcn
_cod_database_code               7239549
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.76798(7) 0.17890(5) 0.93197(9) 0.0172(2) Uani 1 1 d . B .
O1 O 1.03992(6) 0.10819(4) 0.41371(8) 0.0198(2) Uani 1 1 d . . .
O2 O 0.94616(6) 0.18736(4) 0.57230(8) 0.01881(19) Uani 1 1 d . . .
H2 H 0.9758 0.1609 0.5236 0.028 Uiso 1 1 calc R . .
O3 O 0.86241(6) -0.04649(4) 0.76037(9) 0.0218(2) Uani 1 1 d . . .
H3 H 0.8939 -0.0647 0.7039 0.033 Uiso 1 1 calc R . .
C1 C 1.01766(8) 0.04834(6) 0.46157(11) 0.0157(2) Uani 1 1 d . . .
C2 C 0.96146(8) 0.02810(6) 0.56566(11) 0.0147(2) Uani 1 1 d . . .
C3 C 0.91091(7) 0.06547(6) 0.65446(11) 0.0143(2) Uani 1 1 d . . .
C4 C 0.90602(7) 0.14453(6) 0.65779(11) 0.0147(2) Uani 1 1 d . . .
C5 C 0.85959(8) 0.18088(6) 0.74831(11) 0.0161(2) Uani 1 1 d . . .
H5 H 0.8580 0.2331 0.7476 0.019 Uiso 1 1 calc R . .
C6 C 0.81389(8) 0.14226(6) 0.84309(11) 0.0157(2) Uani 1 1 d . . .
C7 C 0.81731(8) 0.06442(6) 0.84122(11) 0.0169(2) Uani 1 1 d . . .
H7 H 0.7869 0.0373 0.9035 0.020 Uiso 1 1 calc R . .
C8 C 0.86372(8) 0.02754(6) 0.75123(11) 0.0157(2) Uani 1 1 d . . .
C9 C 0.76044(8) 0.25945(6) 0.93162(12) 0.0183(2) Uani 1 1 d . . .
H9A H 0.7080 0.2734 0.9818 0.022 Uiso 1 1 calc R . .
H9B H 0.7493 0.2759 0.8454 0.022 Uiso 1 1 calc R . .
C10 C 0.84185(8) 0.30104(6) 0.98177(12) 0.0196(2) Uani 1 1 d D . .
H10 H 0.8932 0.2920 0.9249 0.024 Uiso 1 1 calc R . .
C11 C 0.81970(10) 0.38322(7) 0.97953(14) 0.0271(3) Uani 1 1 d D . .
H11A H 0.7696 0.3929 1.0353 0.041 Uiso 1 1 calc R . .
H11B H 0.8038 0.3979 0.8949 0.041 Uiso 1 1 calc R . .
H11C H 0.8716 0.4114 1.0070 0.041 Uiso 1 1 calc R . .
C12 C 0.86800(9) 0.27699(7) 1.11205(12) 0.0234(3) Uani 1 1 d D . .
H12A H 0.9222 0.3028 1.1373 0.035 Uiso 1 1 calc R . .
H12B H 0.8788 0.2239 1.1128 0.035 Uiso 1 1 calc R . .
H12C H 0.8198 0.2888 1.1700 0.035 Uiso 1 1 calc R . .
C13 C 0.72079(8) 0.14118(7) 1.03259(12) 0.0200(2) Uani 1 1 d D . .
H13A H 0.7288 0.1685 1.1079 0.024 Uiso 0.90 1 d PR A 1
H13B H 0.7470 0.0936 1.0444 0.024 Uiso 0.90 1 d PR A 1
H13C H 0.7004 0.1788 1.0882 0.024 Uiso 0.10 1 d PR A 2
H13D H 0.7648 0.1135 1.0770 0.024 Uiso 0.10 1 d PR A 2
C14 C 0.62014(10) 0.13150(8) 1.00869(13) 0.0219(3) Uani 0.90 1 d PDU B 1
H14 H 0.5936 0.1813 0.9959 0.026 Uiso 0.90 1 calc PR B 1
C15 C 0.59924(10) 0.08482(8) 0.89483(14) 0.0226(3) Uani 0.90 1 d PDU B 1
H15A H 0.6220 0.0349 0.9074 0.034 Uiso 0.90 1 calc PR B 1
H15B H 0.6276 0.1065 0.8216 0.034 Uiso 0.90 1 calc PR B 1
H15C H 0.5348 0.0830 0.8823 0.034 Uiso 0.90 1 calc PR B 1
C16 C 0.57922(13) 0.09830(11) 1.12506(16) 0.0333(4) Uani 0.90 1 d PDU B 1
H16A H 0.5156 0.0902 1.1116 0.050 Uiso 0.90 1 calc PR B 1
H16B H 0.5876 0.1320 1.1950 0.050 Uiso 0.90 1 calc PR B 1
H16C H 0.6082 0.0513 1.1434 0.050 Uiso 0.90 1 calc PR B 1
C14' C 0.6431(5) 0.0905(5) 1.0102(9) 0.023(2) Uani 0.10 1 d PDU B 2
H14' H 0.6605 0.0491 0.9541 0.027 Uiso 0.10 1 calc PR B 2
C15' C 0.6098(9) 0.0612(8) 1.1346(10) 0.026(2) Uani 0.10 1 d PDU B 2
H15D H 0.6536 0.0270 1.1690 0.039 Uiso 0.10 1 calc PR B 2
H15E H 0.5531 0.0356 1.1224 0.039 Uiso 0.10 1 calc PR B 2
H15F H 0.6012 0.1023 1.1922 0.039 Uiso 0.10 1 calc PR B 2
C16' C 0.5751(9) 0.1399(7) 0.9479(12) 0.028(2) Uani 0.10 1 d PDU B 2
H16D H 0.5507 0.1743 1.0090 0.042 Uiso 0.10 1 calc PR B 2
H16E H 0.5270 0.1098 0.9135 0.042 Uiso 0.10 1 calc PR B 2
H16F H 0.6038 0.1675 0.8809 0.042 Uiso 0.10 1 calc PR B 2
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 C13 122.60(10) . .
C6 N1 C9 121.84(10) . .
C13 N1 C9 115.53(9) . .
O1 C1 C2 134.05(11) . .
O1 C1 C2 133.70(11) . 5_756
C2 C1 C2 92.25(9) . 5_756
O1 C1 C1 179.72(14) . 5_756
C2 C1 C1 46.20(6) . 5_756
C2 C1 C1 46.05(6) 5_756 5_756
C3 C2 C1 136.21(10) . .
C3 C2 C1 136.02(11) . 5_756
C1 C2 C1 87.76(9) . 5_756
C2 C3 C8 122.10(10) . .
C2 C3 C4 122.01(10) . .
C8 C3 C4 115.83(10) . .
O2 C4 C5 115.82(10) . .
O2 C4 C3 122.45(10) . .
C5 C4 C3 121.72(10) . .
C4 C5 C6 121.40(10) . .
N1 C6 C7 121.31(11) . .
N1 C6 C5 120.82(10) . .
C7 C6 C5 117.87(10) . .
C8 C7 C6 121.18(11) . .
O3 C8 C7 115.42(10) . .
O3 C8 C3 122.59(10) . .
C7 C8 C3 121.99(10) . .
N1 C9 C10 115.35(10) . .
C12 C10 C11 110.56(10) . .
C12 C10 C9 112.86(10) . .
C11 C10 C9 107.54(10) . .
N1 C13 C14' 122.9(4) . .
N1 C13 C14 113.85(11) . .
C14' C13 C14 31.2(4) . .
C16 C14 C15 111.00(12) . .
C16 C14 C13 107.70(13) . .
C15 C14 C13 113.54(11) . .
C13 C14' C16' 103.3(8) . .
C13 C14' C15' 109.1(8) . .
C16' C14' C15' 111.9(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C6 1.3562(15) .
N1 C13 1.4667(15) .
N1 C9 1.4700(14) .
O1 C1 1.2507(14) .
O2 C4 1.3495(14) .
O3 C8 1.3508(13) .
C1 C2 1.4523(16) .
C1 C2 1.4558(15) 5_756
C1 C1 2.016(2) 5_756
C2 C3 1.3988(16) .
C2 C1 1.4559(15) 5_756
C3 C8 1.4382(16) .
C3 C4 1.4409(15) .
C4 C5 1.3702(16) .
C5 C6 1.4178(16) .
C6 C7 1.4175(15) .
C7 C8 1.3706(16) .
C9 C10 1.5379(17) .
C10 C12 1.5224(17) .
C10 C11 1.5324(16) .
C13 C14' 1.509(5) .
C13 C14 1.5464(18) .
C14 C16 1.522(2) .
C14 C15 1.5252(19) .
C14' C16' 1.519(5) .
C14' C15' 1.527(4) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O1 C1 C2 C3 -0.9(2) . .
C2 C1 C2 C3 178.92(17) 5_756 .
C1 C1 C2 C3 178.92(17) 5_756 .
O1 C1 C2 C1 -179.82(18) . 5_756
C2 C1 C2 C1 0.0 5_756 5_756
C1 C2 C3 C8 -177.67(12) . .
C1 C2 C3 C8 0.8(2) 5_756 .
C1 C2 C3 C4 -0.4(2) . .
C1 C2 C3 C4 178.06(12) 5_756 .
C2 C3 C4 O2 3.28(17) . .
C8 C3 C4 O2 -179.28(10) . .
C2 C3 C4 C5 -177.05(11) . .
C8 C3 C4 C5 0.39(16) . .
O2 C4 C5 C6 179.55(10) . .
C3 C4 C5 C6 -0.14(17) . .
C13 N1 C6 C7 1.30(18) . .
C9 N1 C6 C7 -177.09(11) . .
C13 N1 C6 C5 -179.16(11) . .
C9 N1 C6 C5 2.46(17) . .
C4 C5 C6 N1 -179.82(11) . .
C4 C5 C6 C7 -0.26(17) . .
N1 C6 C7 C8 179.96(11) . .
C5 C6 C7 C8 0.40(17) . .
C6 C7 C8 O3 179.46(11) . .
C6 C7 C8 C3 -0.15(18) . .
C2 C3 C8 O3 -2.39(18) . .
C4 C3 C8 O3 -179.82(11) . .
C2 C3 C8 C7 177.19(11) . .
C4 C3 C8 C7 -0.25(17) . .
C6 N1 C9 C10 -79.37(14) . .
C13 N1 C9 C10 102.14(12) . .
N1 C9 C10 C12 -55.20(14) . .
N1 C9 C10 C11 -177.41(10) . .
C6 N1 C13 C14' -63.9(5) . .
C9 N1 C13 C14' 114.6(5) . .
C6 N1 C13 C14 -98.02(14) . .
C9 N1 C13 C14 80.46(13) . .
N1 C13 C14 C16 -174.84(12) . .
C14' C13 C14 C16 70.6(7) . .
N1 C13 C14 C15 61.83(15) . .
C14' C13 C14 C15 -52.7(7) . .
N1 C13 C14' C16' -60.5(8) . .
C14 C13 C14' C16' 21.6(6) . .
N1 C13 C14' C15' -179.7(6) . .
C14 C13 C14' C15' -97.6(9) . .
