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_4126559
_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 H42 N2 O2 S2'
_chemical_formula_sum            'C36 H42.5 N2 O2 S2'
_chemical_formula_weight         599.34
_chemical_name_systematic        C36H42N2O2S2
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-06-11
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                85.50(3)
_cell_angle_beta                 86.97(3)
_cell_angle_gamma                74.40(3)
_cell_formula_units_Z            4
_cell_length_a                   10.658(2)
_cell_length_b                   17.786(4)
_cell_length_c                   17.910(4)
_cell_measurement_temperature    100
_cell_volume                     3258.1(13)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_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 0.982
_diffrn_measured_fraction_theta_max 0.927
_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     0.0649
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            18036
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.220
_diffrn_reflns_theta_min         1.594
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.745996
_exptl_absorpt_correction_T_min  0.526107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 2:
 wR2(int) was 0.0745 before and 0.0587 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 43390 reflections, Rint = 0.0412
 (15107 with I > 3sig(I), Rint = 0.0305)
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_description       plate
_exptl_crystal_F_000             1282
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.081
_refine_diff_density_max         1.354
_refine_diff_density_min         -1.203
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     762
_refine_ls_number_reflns         18036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1296
_refine_ls_R_factor_gt           0.0815
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1276P)^2^+6.4667P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2253
_refine_ls_wR_factor_ref         0.2640
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11611
_reflns_number_total             18036
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b07750_si_003.cif
_cod_data_source_block           bje_iv_59_a
_cod_original_cell_volume        3257.9(12)
_cod_original_formula_sum        'C36 H42.50 N2 O2 S2'
_cod_database_code               4126559
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.12(4) 0.88(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.a Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C22(H22A,H22B), C24(H24A,H24B), C33(H33A,H33B), C27(H27A,
 H27B), C21(H21A,H21B), C31(H31A,H31B), C23(H23A,H23B), C25(H25A,H25B),
 C32(H32A,H32B), C26(H26A,H26B), C34(H34A,H34B), C35(H35A,H35B), C29(H29A,H29B),
  C69(H69A,H69B), C65(H65A,H65B), C70(H70A,H70B), C64(H64A,H64B), C68(H68A,
 H68B), C67(H67A,H67B), C66(H66A,H66B), C50(H50A,H50B), C48(H48A,H48B),
 C46(H46A,H46B), C47(H47A,H47B), C52(H52A,H52B), C49(H49A,H49B), C51(H51A,H51B)
3.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C18(H18), C16(H16), C19(H19), C14(H14), C20(H20), C12(H12), C3(H3),
 C62(H62), C56(H56), C63(H63), C61(H61), C39(H39), C45(H45), C43(H43), C44(H44)
3.c Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C28(H28A,H28B,H28C), C71(H71A,H71B,H71C), C53(H53A,H53B,
 H53C)
;
_shelx_res_checksum              66093
_shelx_hkl_checksum              1376
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-06-10
_olex2_date_sample_submission    2015-06-10
_olex2_exptl_crystal_mounting_method
'The crystal was mounted in Paratone-N on a brass tip.'
_olex2_submission_original_sample_id BJE_IV_59
_olex2_submission_special_instructions 'No special instructions were received'