Supramolecular control of organic p/n-heterojunctions by complementary hydrogen bonding.
Black, Hayden T.; Lin, Huaping; Bélanger-Gariépy, Francine; Perepichka, Dmitrii F.; Faraday discussions 174 (2014) 297–312; doi:10.1039/c4fd00133h

data_1552966
_publ_section_title
;
 Supramolecular control of organic p/n-heterojunctions by complementary
 hydrogen bonding.
;
_journal_name_full               'Faraday discussions'
_journal_page_first              297
_journal_page_last               312
_journal_paper_doi               10.1039/c4fd00133h
_journal_volume                  174
_journal_year                    2014
_chemical_formula_moiety         'C17 H11 N3 S2, C22 H22 N2 O4'
_chemical_formula_sum            'C39 H33 N5 O4 S2'
_chemical_formula_weight         699.82
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-02-03
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                88.5620(17)
_cell_angle_beta                 84.1540(19)
_cell_angle_gamma                76.6560(19)
_cell_formula_units_Z            2
_cell_length_a                   6.9253(2)
_cell_length_b                   13.3435(4)
_cell_length_c                   18.5149(6)
_cell_measurement_reflns_used    8872
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.676
_cell_measurement_theta_min      2.399
_cell_volume                     1656.07(9)
_computing_cell_refinement
;
SAINT (2013) V8.34A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
'SAINT (2013) V8.34A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_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, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            45522
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.816
_diffrn_reflns_theta_min         2.399
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_exptl_absorpt_coefficient_mu    1.878
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0899 before and 0.0630 after correction.
The Ratio of minimum to maximum transmission is 0.8135.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     531
_refine_ls_number_reflns         6293
_refine_ls_number_restraints     238
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1119P)^2^+0.4269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1691
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4738
_reflns_number_total             6293
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4fd00133h1.cif
_cod_data_source_block           pere46
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' 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_database_code               1552966
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.834
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C35-C36A \\sim C35-C36B
 with sigma of 0.02
3. Rigid bond restraints
 C35, C36A, C37A, C38A, C39A, C40A, C41A, C42A, C36B, C37B, C38B, C39B, C40B,
 C41B, C42B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C35 \\sim C36A \\sim C37A \\sim C38A \\sim C39A \\sim C40A \\sim C41A \\sim
C42A \\sim C36B \\sim C37B \\sim C38B \\sim C39B \\sim C40B \\sim C41B \\sim
C42B: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
5. Same fragment restrains
{C36A, C37A, C38A, C39A, C40A, C41A, C42A}
as
{C36B, C37B, C38B, C39B, C40B, C41B, C42B}
6. Others
 Sof(H35C)=Sof(H35D)=Sof(C36B)=Sof(H36B)=Sof(C37B)=Sof(H37C)=Sof(H37D)=
 Sof(C38B)=Sof(H38C)=Sof(H38D)=Sof(C39B)=Sof(H39C)=Sof(H39D)=Sof(C40B)=
 Sof(H40D)=Sof(H40E)=Sof(H40F)=Sof(C41B)=Sof(H41C)=Sof(H41D)=Sof(C42B)=
 Sof(H42D)=Sof(H42E)=Sof(H42F)=1-FVAR(1)
 Sof(H35A)=Sof(H35B)=Sof(C36A)=Sof(H36A)=Sof(C37A)=Sof(H37A)=Sof(H37B)=
 Sof(C38A)=Sof(H38A)=Sof(H38B)=Sof(C39A)=Sof(H39A)=Sof(H39B)=Sof(C40A)=
 Sof(H40A)=Sof(H40B)=Sof(H40C)=Sof(C41A)=Sof(H41A)=Sof(H41B)=Sof(C42A)=
 Sof(H42A)=Sof(H42B)=Sof(H42C)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C36A(H36A), C36B(H36B)
7.b Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C35(H35C,H35D), C37A(H37A,H37B), C38A(H38A,H38B), C39A(H39A,
 H39B), C41A(H41A,H41B), C37B(H37C,H37D), C38B(H38C,H38D), C39B(H39C,H39D),
 C41B(H41C,H41D)
7.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C8(H8), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16),
 C17(H17), C24(H24), C25(H25), C30(H30), C31(H31)
7.d Idealised Me refined as rotating group:
 C40A(H40A,H40B,H40C), C42A(H42A,H42B,H42C), C40B(H40D,H40E,H40F), C42B(H42D,
 H42E,H42F)
;