#------------------------------------------------------------------------------
#$Date: 2016-08-07 11:35:08 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185276 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/46/7224609.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_7224609
loop_
_publ_author_name
'Fu, Chaoying'
'Bélanger-Gariépy, Francine'
'Perepichka, Dmitrii F.'
_publ_section_title
;
 Supramolecular ordering of difuryldiketopyrrolopyrrole: the effect of
 alkyl chains and inter-ring twisting
;
_journal_issue                   23
_journal_name_full               CrystEngComm
_journal_page_first              4285
_journal_paper_doi               10.1039/C6CE00383D
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C42 H64 N2 O4'
_chemical_formula_sum            'C42 H64 N2 O4'
_chemical_formula_weight         660.95
_chemical_properties_physical    'Oxygen-sensitive, Photo-sensitive'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-23
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-12-02 deposited with the CCDC.
2016-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.903(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   18.8248(10)
_cell_length_b                   4.6921(3)
_cell_length_c                   21.4035(11)
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    105
_cell_measurement_theta_max      60.612
_cell_measurement_theta_min      3.660
_cell_volume                     1856.40(18)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      105
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            30967
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.594
_diffrn_reflns_theta_min         3.659
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1190 before and 0.0757 after correction.
The Ratio of minimum to maximum transmission is 0.7665.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             724
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethylacetate'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4222
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0572P)²+0.4714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1234
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3087
_reflns_number_total             4222
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce00383d2.cif
_cod_data_source_block           pere60
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7224608--7224609.cif.
;
_cod_database_code               7224609
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.865
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B),
  C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
O1 O 0.85584(5) 1.0591(2) 1.03450(4) 0.0321(2) Uani 1 1 d .
O2 O 0.92971(5) 0.3759(2) 0.86248(4) 0.0347(3) Uani 1 1 d .
N1 N 0.90280(6) 0.7710(2) 0.96353(5) 0.0282(3) Uani 1 1 d .
C1 C 0.90761(7) 0.9865(3) 1.01122(6) 0.0282(3) Uani 1 1 d .
C2 C 0.98236(7) 1.0787(3) 1.02066(6) 0.0272(3) Uani 1 1 d .
C3 C 0.96883(7) 0.7354(3) 0.94414(6) 0.0273(3) Uani 1 1 d .
C4 C 0.98384(7) 0.5405(3) 0.89683(6) 0.0287(3) Uani 1 1 d .
C5 C 0.96173(8) 0.2150(3) 0.82227(6) 0.0366(4) Uani 1 1 d .
H5 H 0.9371 0.0799 0.7929 0.044 Uiso 1 1 calc R
C6 C 1.03283(8) 0.2734(3) 0.82983(6) 0.0359(3) Uani 1 1 d .
H6 H 1.0664 0.1898 0.8073 0.043 Uiso 1 1 calc R
C7 C 1.04783(8) 0.4847(3) 0.87811(6) 0.0324(3) Uani 1 1 d .
H7 H 1.0934 0.5701 0.8942 0.039 Uiso 1 1 calc R
C8 C 0.83398(7) 0.6282(3) 0.93952(6) 0.0299(3) Uani 1 1 d .
H8A H 0.8061 0.6138 0.9743 0.036 Uiso 1 1 calc R
H8B H 0.8437 0.4321 0.9262 0.036 Uiso 1 1 calc R
C9 C 0.78860(7) 0.7837(3) 0.88351(6) 0.0316(3) Uani 1 1 d .
H9A H 0.7716 0.9664 0.8986 0.038 Uiso 1 1 calc R
H9B H 0.8193 0.8282 0.8520 0.038 Uiso 1 1 calc R
C10 C 0.72345(7) 0.6118(3) 0.85122(6) 0.0304(3) Uani 1 1 d .
H10A H 0.6933 0.5642 0.8830 0.036 Uiso 1 1 calc R
H10B H 0.7405 0.4307 0.8354 0.036 Uiso 1 1 calc R
C11 C 0.67712(7) 0.7701(3) 0.79575(6) 0.0310(3) Uani 1 1 d .
H11A H 0.6532 0.9326 0.8129 0.037 Uiso 1 1 calc R
H11B H 0.7092 0.8489 0.7683 0.037 Uiso 1 1 calc R
C12 C 0.61936(7) 0.5881(3) 0.75494(6) 0.0312(3) Uani 1 1 d .
H12A H 0.5863 0.5137 0.7819 0.037 Uiso 1 1 calc R
H12B H 0.6429 0.4227 0.7386 0.037 Uiso 1 1 calc R
C13 C 0.57510(7) 0.7482(3) 0.69885(6) 0.0311(3) Uani 1 1 d .
H13A H 0.5487 0.9049 0.7154 0.037 Uiso 1 1 calc R
H13B H 0.6086 0.8351 0.6738 0.037 Uiso 1 1 calc R
C14 C 0.52091(7) 0.5631(3) 0.65496(6) 0.0329(3) Uani 1 1 d .
H14A H 0.5473 0.4056 0.6386 0.039 Uiso 1 1 calc R
H14B H 0.4872 0.4773 0.6800 0.039 Uiso 1 1 calc R
C15 C 0.47716(7) 0.7231(3) 0.59879(6) 0.0321(3) Uani 1 1 d .
H15A H 0.5109 0.8112 0.5741 0.039 Uiso 1 1 calc R
H15B H 0.4502 0.8788 0.6151 0.039 Uiso 1 1 calc R
C16 C 0.42374(7) 0.5368(3) 0.55448(6) 0.0335(3) Uani 1 1 d .
H16A H 0.4507 0.3816 0.5380 0.040 Uiso 1 1 calc R
H16B H 0.3902 0.4481 0.5792 0.040 Uiso 1 1 calc R
C17 C 0.37969(7) 0.6965(3) 0.49841(6) 0.0330(3) Uani 1 1 d .
H17A H 0.4132 0.7902 0.4744 0.040 Uiso 1 1 calc R
H17B H 0.3514 0.8477 0.5148 0.040 Uiso 1 1 calc R
C18 C 0.32802(7) 0.5068(3) 0.45320(6) 0.0326(3) Uani 1 1 d .
H18A H 0.3562 0.3535 0.4374 0.039 Uiso 1 1 calc R
H18B H 0.2939 0.4157 0.4771 0.039 Uiso 1 1 calc R
C19 C 0.28490(7) 0.6651(3) 0.39655(6) 0.0327(3) Uani 1 1 d .
H19A H 0.3189 0.7660 0.3741 0.039 Uiso 1 1 calc R
H19B H 0.2543 0.8103 0.4122 0.039 Uiso 1 1 calc R
C20 C 0.23687(7) 0.4713(3) 0.34962(6) 0.0338(3) Uani 1 1 d .
H20A H 0.2023 0.3726 0.3718 0.041 Uiso 1 1 calc R
H20B H 0.2673 0.3244 0.3344 0.041 Uiso 1 1 calc R
C21 C 0.19465(8) 0.6311(4) 0.29250(6) 0.0382(4) Uani 1 1 d .
H21A H 0.1679 0.4945 0.2622 0.057 Uiso 1 1 calc GR
H21B H 0.2283 0.7388 0.2718 0.057 Uiso 1 1 calc GR
H21C H 0.1606 0.7628 0.3068 0.057 Uiso 1 1 calc GR
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0150 0.0070 '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 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0410 0.0250 '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
C5 O2 C4 106.04(11) . .
C1 N1 C8 120.53(11) . .
C3 N1 C1 111.02(11) . .
C3 N1 C8 128.40(11) . .
O1 C1 N1 122.72(12) . .
O1 C1 C2 133.41(13) . .
N1 C1 C2 103.86(11) . .
C2 C2 C1 108.43(15) 3_777 .
C3 C2 C1 142.37(12) 3_777 .
C3 C2 C2 109.20(14) 3_777 3_777
N1 C3 C4 126.44(12) . .
C2 C3 N1 107.48(11) 3_777 .
C2 C3 C4 126.08(12) 3_777 .
O2 C4 C3 120.76(11) . .
C7 C4 O2 109.93(12) . .
C7 C4 C3 129.31(13) . .
O2 C5 H5 124.5 . .
C6 C5 O2 111.02(13) . .
C6 C5 H5 124.5 . .
C5 C6 H6 126.7 . .
C5 C6 C7 106.60(12) . .
C7 C6 H6 126.7 . .
C4 C7 C6 106.40(13) . .
C4 C7 H7 126.8 . .
C6 C7 H7 126.8 . .
N1 C8 H8A 109.1 . .
N1 C8 H8B 109.1 . .
N1 C8 C9 112.65(11) . .
H8A C8 H8B 107.8 . .
C9 C8 H8A 109.1 . .
C9 C8 H8B 109.1 . .
C8 C9 H9A 109.0 . .
C8 C9 H9B 109.0 . .
H9A C9 H9B 107.8 . .
C10 C9 C8 112.83(12) . .
C10 C9 H9A 109.0 . .
C10 C9 H9B 109.0 . .
C9 C10 H10A 109.0 . .
C9 C10 H10B 109.0 . .
C9 C10 C11 112.85(12) . .
H10A C10 H10B 107.8 . .
C11 C10 H10A 109.0 . .
C11 C10 H10B 109.0 . .
C10 C11 H11A 108.6 . .
C10 C11 H11B 108.6 . .
H11A C11 H11B 107.6 . .
C12 C11 C10 114.49(12) . .
C12 C11 H11A 108.6 . .
C12 C11 H11B 108.6 . .
C11 C12 H12A 108.8 . .
C11 C12 H12B 108.8 . .
C11 C12 C13 113.60(12) . .
H12A C12 H12B 107.7 . .
C13 C12 H12A 108.8 . .
C13 C12 H12B 108.8 . .
C12 C13 H13A 108.7 . .
C12 C13 H13B 108.7 . .
H13A C13 H13B 107.6 . .
C14 C13 C12 114.05(12) . .
C14 C13 H13A 108.7 . .
C14 C13 H13B 108.7 . .
C13 C14 H14A 108.8 . .
C13 C14 H14B 108.8 . .
H14A C14 H14B 107.7 . .
C15 C14 C13 113.93(12) . .
C15 C14 H14A 108.8 . .
C15 C14 H14B 108.8 . .
C14 C15 H15A 108.8 . .
C14 C15 H15B 108.8 . .
C14 C15 C16 113.85(12) . .
H15A C15 H15B 107.7 . .
C16 C15 H15A 108.8 . .
C16 C15 H15B 108.8 . .
C15 C16 H16A 108.8 . .
C15 C16 H16B 108.8 . .
H16A C16 H16B 107.7 . .
C17 C16 C15 113.98(12) . .
C17 C16 H16A 108.8 . .
C17 C16 H16B 108.8 . .
C16 C17 H17A 108.8 . .
C16 C17 H17B 108.8 . .
C16 C17 C18 113.64(13) . .
H17A C17 H17B 107.7 . .
C18 C17 H17A 108.8 . .
C18 C17 H17B 108.8 . .
C17 C18 H18A 108.8 . .
C17 C18 H18B 108.8 . .
H18A C18 H18B 107.7 . .
C19 C18 C17 113.70(12) . .
C19 C18 H18A 108.8 . .
C19 C18 H18B 108.8 . .
C18 C19 H19A 108.9 . .
C18 C19 H19B 108.9 . .
C18 C19 C20 113.35(13) . .
H19A C19 H19B 107.7 . .
C20 C19 H19A 108.9 . .
C20 C19 H19B 108.9 . .
C19 C20 H20A 109.0 . .
C19 C20 H20B 109.0 . .
C19 C20 C21 113.02(13) . .
H20A C20 H20B 107.8 . .
C21 C20 H20A 109.0 . .
C21 C20 H20B 109.0 . .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21B 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2237(16) .
O2 C4 1.3756(17) .
O2 C5 1.3675(16) .
N1 C1 1.4274(18) .
N1 C3 1.3931(16) .
N1 C8 1.4629(17) .
C1 C2 1.4493(18) .
C2 C2 1.411(2) 3_777
C2 C3 1.3825(19) 3_777
C3 C2 1.3824(19) 3_777
C3 C4 1.4314(18) .
C4 C7 1.3648(18) .
C5 H5 0.9500 .
C5 C6 1.346(2) .
C6 H6 0.9500 .
C6 C7 1.421(2) .
C7 H7 0.9500 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C8 C9 1.5206(19) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C9 C10 1.5206(19) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C10 C11 1.5266(19) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C11 C12 1.5216(19) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C12 C13 1.5237(19) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C13 C14 1.5218(19) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C14 C15 1.5208(19) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C15 C16 1.5213(19) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C16 C17 1.5207(19) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C17 C18 1.5228(19) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C18 C19 1.5194(19) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C19 C20 1.520(2) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C20 C21 1.523(2) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
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 C2 -178.84(15) . 3_777
O1 C1 C2 C3 1.6(3) . 3_777
O2 C4 C7 C6 -0.28(15) . .
O2 C5 C6 C7 0.21(17) . .
N1 C1 C2 C2 0.38(17) . 3_777
N1 C1 C2 C3 -179.21(17) . 3_777
N1 C3 C4 O2 4.0(2) . .
N1 C3 C4 C7 -176.16(14) . .
N1 C8 C9 C10 170.12(11) . .
C1 N1 C3 C2 1.09(15) . 3_777
C1 N1 C3 C4 -179.40(12) . .
C1 N1 C8 C9 88.43(14) . .
C2 C3 C4 O2 -176.61(12) 3_777 .
C2 C3 C4 C7 3.3(2) 3_777 .
C3 N1 C1 O1 178.43(12) . .
C3 N1 C1 C2 -0.90(14) . .
C3 N1 C8 C9 -88.69(16) . .
C3 C4 C7 C6 179.83(13) . .
C4 O2 C5 C6 -0.38(15) . .
C5 O2 C4 C3 -179.70(12) . .
C5 O2 C4 C7 0.41(15) . .
C5 C6 C7 C4 0.05(16) . .
C8 N1 C1 O1 0.84(19) . .
C8 N1 C1 C2 -178.49(11) . .
C8 N1 C3 C2 178.44(12) . 3_777
C8 N1 C3 C4 -2.1(2) . .
C8 C9 C10 C11 178.95(11) . .
C9 C10 C11 C12 169.71(11) . .
C10 C11 C12 C13 -178.46(11) . .
C11 C12 C13 C14 175.76(11) . .
C12 C13 C14 C15 -179.63(11) . .
C13 C14 C15 C16 179.21(11) . .
C14 C15 C16 C17 179.76(11) . .
C15 C16 C17 C18 178.23(11) . .
C16 C17 C18 C19 -179.01(11) . .
C17 C18 C19 C20 176.50(11) . .
C18 C19 C20 C21 -179.18(11) . .
