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_1552967
_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         'C22 H22 N2 O4, C17 H11 N3 O2'
_chemical_formula_sum            'C39 H33 N5 O6'
_chemical_formula_weight         667.70
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-01-30
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.0462(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.99561(18)
_cell_length_b                   9.37580(8)
_cell_length_c                   31.7046(2)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.493
_cell_measurement_theta_min      2.901
_cell_volume                     6283.59(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 0.994
_diffrn_measured_fraction_theta_max 0.988
_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  0.0456
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            85170
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.683
_diffrn_reflns_theta_min         2.090
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0668 before and 0.0552 after correction.
The Ratio of minimum to maximum transmission is 0.8979.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       FRAGMENT
_exptl_crystal_F_000             2800
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1067
_refine_ls_number_reflns         12157
_refine_ls_number_restraints     513
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0587
_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/[\s^2^(Fo^2^)+(0.0982P)^2^+2.9435P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1808
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9030
_reflns_number_total             12157
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4fd00133h1.cif
_cod_data_source_block           pere44
_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_original_cell_volume        6283.58(9)
_cod_database_code               1552967
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.984
_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 C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C64-O51A \\sim C64-O51B \\sim C60-O52A \\sim C60-O52B
 with sigma of 0.02
 C64-C67A \\sim C64-C67B \\sim C60-C63A \\sim C60-C63B
 with sigma of 0.02
 C88-C89A \\sim C88-C89B
 with sigma of 0.02
 C36-C37A \\sim C36-C37B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O51A \\sim C65A \\sim C66A \\sim C67A \\sim O51B \\sim C65B \\sim C66B \\sim
C67B: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
O52A \\sim C61A \\sim C62A \\sim C63A \\sim O52B \\sim C61B \\sim C62B \\sim
C63B: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
C37A \\sim C38A \\sim C39A \\sim C40A \\sim C41A \\sim C42A \\sim C37B \\sim
C38B \\sim C39B \\sim C40B \\sim C41B \\sim C42B: within 1.7A with sigma of
0.02 and sigma for terminal atoms of 0.04
C89A \\sim C90A \\sim C91A \\sim C92A \\sim C89B \\sim C90B \\sim C91B \\sim
C92B: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
4. Same fragment restrains
{C10, O2, C11, C12, C13}
as
{C14, O1, C15, C16, C17}
{C37A, C38A, C39A, C40A, C41A, C42A}
as
{C37B, C38B, C39B, C40B, C41B, C42B}
{O2, C11, C12, C13}
as
{O52A, C61A, C62A, C63A}
{O2, C11, C12, C13}
as
{O52B, C61B, C62B, C63B}
{O2, C11, C12, C13}
as
{O51A, C65A, C66A, C67A}
{O2, C11, C12, C13}
as
{O51B, C65B, C66B, C67B}
{C89A, C90A, C91A, C92A}
as
{C89A, C90A, C91A, C92A}
5. Others
 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)=
 Sof(C41B)=Sof(H41C)=Sof(H41D)=Sof(C42B)=Sof(H42D)=Sof(H42E)=Sof(H42F)=1-FVAR(1)
 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)=
 Sof(C41A)=Sof(H41A)=Sof(H41B)=Sof(C42A)=Sof(H42A)=Sof(H42B)=Sof(H42C)=FVAR(1)
 Sof(O51B)=Sof(C65B)=Sof(H65B)=Sof(C66B)=Sof(H66B)=Sof(C67B)=Sof(H67B)=1-FVAR(2)
 Sof(O51A)=Sof(C65A)=Sof(H65A)=Sof(C66A)=Sof(H66A)=Sof(C67A)=Sof(H67A)=FVAR(2)
 Sof(O52B)=Sof(C61B)=Sof(H61B)=Sof(C62B)=Sof(H62B)=Sof(C63B)=Sof(H63B)=1-FVAR(3)
 Sof(O52A)=Sof(C61A)=Sof(H61A)=Sof(C62A)=Sof(H62A)=Sof(C63A)=Sof(H63A)=FVAR(3)
 Sof(H88C)=Sof(H88D)=Sof(C89B)=Sof(H89C)=Sof(H89D)=Sof(C90B)=Sof(H90C)=
 Sof(H90D)=Sof(C91B)=Sof(H91C)=Sof(H91D)=Sof(C92B)=Sof(H92D)=Sof(H92E)=
 Sof(H92F)=1-FVAR(4)
 Sof(H88A)=Sof(H88B)=Sof(C89A)=Sof(H89A)=Sof(H89B)=Sof(C90A)=Sof(H90A)=
 Sof(H90B)=Sof(C91A)=Sof(H91A)=Sof(H91B)=Sof(C92A)=Sof(H92A)=Sof(H92B)=
 Sof(H92C)=FVAR(4)
6.a Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C36(H36A,H36B), C36(H36C,H36D), C37A(H37A,H37B), C38A(H38A,
 H38B), C39A(H39A,H39B), C40A(H40A,H40B), C41A(H41A,H41B), C37B(H37C,H37D),
 C38B(H38C,H38D), C39B(H39C,H39D), C40B(H40C,H40D), C41B(H41C,H41D), C85(H85A,
 H85B), C86(H86A,H86B), C87(H87A,H87B), C88(H88A,H88B), C88(H88C,H88D),
 C89A(H89A,H89B), C90A(H90A,H90B), C91A(H91A,H91B), C89B(H89C,H89D), C90B(H90C,
 H90D), C91B(H91C,H91D)
6.b Me refined with riding coordinates:
 C42A(H42A,H42B,H42C), C42B(H42D,H42E,H42F), C92A(H92A,H92B,H92C), C92B(H92D,
 H92E,H92F)
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),
 C15(H15), C16(H16), C17(H17), N22(H22), C24(H24), C25(H25), C30(H30), C31(H31),
  N51(H51), N53(H53), C54(H54), C56(H56), C58(H58), C61A(H61A), C62A(H62A),
 C63A(H63A), C61B(H61B), C62B(H62B), C63B(H63B), C65A(H65A), C66A(H66A),
 C67A(H67A), C65B(H65B), C66B(H66B), C67B(H67B), N72(H72), C74(H74), C75(H75),
 C80(H80), C81(H81)
;