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_1552968
_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 O2, C20 H16 N2 O4'
_chemical_formula_sum            'C37 H27 N5 O6'
_chemical_formula_weight         637.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-02-10
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.5621(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.9367(3)
_cell_length_b                   9.3501(2)
_cell_length_c                   19.4676(3)
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.281
_cell_measurement_theta_min      2.850
_cell_volume                     3015.03(10)
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0314
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            39413
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.856
_diffrn_reflns_theta_min         2.851
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0569 before and 0.0441 after correction.
The Ratio of minimum to maximum transmission is 0.9285.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'dark violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     528
_refine_ls_number_reflns         5809
_refine_ls_number_restraints     87
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0651P)^2^+0.9035P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1180
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4823
_reflns_number_total             5809
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4fd00133h1.cif
_cod_data_source_block           pere47
_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               1552968
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.939
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 C9-C14A \\sim C9-C14B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O1A) = Uanis(O1B)
Uanis(C14A) = Uanis(C14B)
Uanis(C15A) = Uanis(C15B)
Uanis(C16A) = Uanis(C16B)
Uanis(C17A) = Uanis(C17B)
Uanis(O21A) = Uanis(O21B)
Uanis(O22A) = Uanis(O22B)
Uanis(O23A) = Uanis(O23B)
Uanis(O24A) = Uanis(O24B)
Uanis(N21A) = Uanis(N21B)
Uanis(N22A) = Uanis(N22B)
Uanis(C21A) = Uanis(C21B)
Uanis(C22A) = Uanis(C22B)
Uanis(C23A) = Uanis(C23B)
Uanis(C24A) = Uanis(C24B)
Uanis(C25A) = Uanis(C25B)
Uanis(C26A) = Uanis(C26B)
Uanis(C27A) = Uanis(C27B)
Uanis(C28A) = Uanis(C28B)
Uanis(C29A) = Uanis(C29B)
Uanis(C30A) = Uanis(C30B)
Uanis(C31A) = Uanis(C31B)
Uanis(C32A) = Uanis(C32B)
Uanis(C33A) = Uanis(C33B)
Uanis(C34A) = Uanis(C34B)
Uanis(C35A) = Uanis(C35B)
Uanis(C36A) = Uanis(C36B)
Uanis(C37A) = Uanis(C37B)
Uanis(C38A) = Uanis(C38B)
Uanis(C39A) = Uanis(C39B)
Uanis(C40A) = Uanis(C40B)
4. Same fragment restrains
{C14A, O1A, C15A, C16A, C17A}
as
{C14B, O1B, C15B, C16B, C17B}
{O21A, O22A, O23A, O24A, N21A, N22A, C21A, C22A, C23A, C24A, C25A, C26A, C27A,
C28A, C29A, C30A, C31A, C32A, C33A, C34A, C35A, C36A, C37A, C38A, C39A, C40A}
as
{O21B, O22B, O23B, O24B, N21B, N22B, C21B, C22B, C23B, C24B, C25B, C26B, C27B,
C28B, C29B, C30B, C31B, C32B, C33B, C34B, C35B, C36B, C37B, C38B, C39B, C40B}
5. Others
 Sof(C14B)=Sof(O1B)=Sof(C15B)=Sof(H15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=
 Sof(H17B)=1-FVAR(1)
 Sof(C14A)=Sof(O1A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=
 Sof(H17A)=FVAR(1)
 Sof(O21B)=Sof(O22B)=Sof(O23B)=Sof(O24B)=Sof(N21B)=Sof(N22B)=Sof(H22B)=
 Sof(C21B)=Sof(C22B)=Sof(C23B)=Sof(C24B)=Sof(H24B)=Sof(C25B)=Sof(H25B)=
 Sof(C26B)=Sof(C27B)=Sof(C28B)=Sof(C29B)=Sof(C30B)=Sof(H30B)=Sof(C31B)=
 Sof(H31B)=Sof(C32B)=Sof(C33B)=Sof(C34B)=Sof(C35B)=Sof(H35B)=Sof(C36B)=
 Sof(H36C)=Sof(H36D)=Sof(C37B)=Sof(H37C)=Sof(H37D)=Sof(C38B)=Sof(H38C)=
 Sof(H38D)=Sof(C39B)=Sof(H39C)=Sof(H39D)=Sof(C40B)=Sof(H40C)=Sof(H40D)=1-FVAR(2)
 Sof(O21A)=Sof(O22A)=Sof(O23A)=Sof(O24A)=Sof(N21A)=Sof(N22A)=Sof(H22A)=
 Sof(C21A)=Sof(C22A)=Sof(C23A)=Sof(C24A)=Sof(H24A)=Sof(C25A)=Sof(H25A)=
 Sof(C26A)=Sof(C27A)=Sof(C28A)=Sof(C29A)=Sof(C30A)=Sof(H30A)=Sof(C31A)=
 Sof(H31A)=Sof(C32A)=Sof(C33A)=Sof(C34A)=Sof(C35A)=Sof(H35A)=Sof(C36A)=
 Sof(H36A)=Sof(H36B)=Sof(C37A)=Sof(H37A)=Sof(H37B)=Sof(C38A)=Sof(H38A)=
 Sof(H38B)=Sof(C39A)=Sof(H39A)=Sof(H39B)=Sof(C40A)=Sof(H40A)=Sof(H40B)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C35A(H35A), C35B(H35B)
6.b Secondary CH2 refined with riding coordinates:
 C36A(H36A,H36B), C37A(H37A,H37B), C38A(H38A,H38B), C39A(H39A,H39B), C40A(H40A,
 H40B), C36B(H36C,H36D), C37B(H37C,H37D), C38B(H38C,H38D), C39B(H39C,H39D),
 C40B(H40C,H40D)
6.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C4(H4), C6(H6), C8(H8), C11(H11), C12(H12), C13(H13),
 C15A(H15A), C16A(H16A), C17A(H17A), C15B(H15B), C16B(H16B), C17B(H17B),
 N22A(H22A), C24A(H24A), C25A(H25A), C30A(H30A), C31A(H31A), N22B(H22B),
 C24B(H24B), C25B(H25B), C30B(H30B), C31B(H31B)
;