Naphthalene Bis(4,8-diamino-1,5-dicarboxyl)amide Building Block for Semiconducting Polymers.
Eckstein, Brian J.; Melkonyan, Ferdinand S.; Manley, Eric F.; Fabiano, Simone; Mouat, Aidan R.; Chen, Lin X.; Facchetti, Antonio; Marks, Tobin J.; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b07750

data_4126560
_publ_section_title
;
 Naphthalene Bis(4,8-diamino-1,5-dicarboxyl)amide Building Block for
 Semiconducting Polymers.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b07750
_journal_year                    2017
_chemical_formula_moiety         'C36 H41.33 N2 O2 S2'
_chemical_formula_sum            'C36 H42 N2 O2 S2'
_chemical_formula_weight         598.83
_chemical_name_systematic        BJE_V_31
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-03-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.38(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.040(3)
_cell_length_b                   5.2797(11)
_cell_length_c                   19.767(4)
_cell_measurement_temperature    100
_cell_volume                     1547.9(6)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.863
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0768
_diffrn_reflns_Laue_measured_fraction_full 0.863
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4854
_diffrn_reflns_point_group_measured_fraction_full 0.863
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         24.722
_diffrn_reflns_theta_min         1.400
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.745106
_exptl_absorpt_correction_T_min  0.526993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1345 before and 0.0577 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1456 before and 0.0597 after correction.
 The Ratio of minimum to maximum transmission is 0.71.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 19537 reflections, Rint = 0.0903
 (5618 with I > 3sig(I), Rint = 0.0666)
;
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.513
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3052
_refine_ls_number_restraints     273
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0780
_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^)+(0.1097P)^2^+2.2075P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1946
_refine_ls_wR_factor_ref         0.2322
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2192
_reflns_number_total             3052
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b07750_si_002.cif
_cod_data_source_block           bje_v_31_a
_cod_original_cell_volume        1548.0(6)
_cod_database_code               4126560
_shelxl_version_number           2014-3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.787(4) 0.213(4)
2. 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
3. Restrained distances
 C4-C3A \\sim C4-C3 \\sim C3-C2 \\sim C3A-C1 \\sim C2-C1
 with sigma of 0.01
 S1A-C4 \\sim S1A-C2 \\sim S1-C1 \\sim S1-C4
 with sigma of 0.01
 C4-C3 \\sim C3-C2 \\sim C2-C1
 with sigma of 0.02
 C4-C3A \\sim C3A-C1 \\sim C2-C1
 with sigma of 0.02
 S1A-C2 \\sim S1A-C4
 with sigma of 0.02
 S1-C4 \\sim S1-C1
 with sigma of 0.02
 S1-C4 \\sim S1-C1 \\sim S1A-C4 \\sim S1A-C2
 with sigma of 0.02
 C4-C3A \\sim C4-C3 \\sim C3-C2 \\sim C2-C1 \\sim C3A-C1
 with sigma of 0.02
4. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
5. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
All non-hydrogen atoms have similar U: within 2A with sigma of 0.02 and sigma
for terminal atoms of 0.04
Uanis(O1A) = Uanis(O1)
6. Others
 Sof(H1B)=Sof(S1A)=Sof(C3A)=1-FVAR(1)
 Sof(S1)=Sof(H1A)=Sof(H2)=Sof(C3)=Sof(H3)=FVAR(1)
 Sof(O1A)=1-FVAR(2)
 Sof(O1)=Sof(H10)=FVAR(2)
7.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,
 H15B), C16(H16A,H16B), C17(H17A,H17B)
7.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C1(H1B), C2(H2), C3(H3), C10(H10)
7.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_date_sample_data_collection 2016-03-15
_olex2_date_sample_submission    2016-03-15
_olex2_exptl_crystal_mounting_method 'Mounted at 100 K on a brass tip.'
_olex2_submission_original_sample_id BJE_V_31
_olex2_submission_special_instructions 'No special instructions were received'