Thermodynamic synthesis of solution processable ladder polymers
Lee, Jongbok; Rajeeva, Bharath Bangalore; Yuan, Tianyu; Guo, Zi-Hao; Lin, Yen-Hao; Al-Hashimi, Mohammed; Zheng, Yuebing; Fang, Lei; Chem. Sci. 7 (2016) 881–; doi:10.1039/C5SC02385H

data_1540515
_publ_section_title
;
 Thermodynamic synthesis of solution processable ladder polymers
;
_journal_issue                   2
_journal_name_full               'Chem. Sci.'
_journal_page_first              881
_journal_paper_doi               10.1039/C5SC02385H
_journal_volume                  7
_journal_year                    2016
_chemical_formula_moiety         'C47 H55 N'
_chemical_formula_sum            'C47 H55 N'
_chemical_formula_weight         633.92
_chemical_name_systematic
6,9-dimethyl-16-(1-octylnonyl)-16H-dinaphtho[1,2-b:2',1'-h]-carbazole
_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             2014-08-14
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_audit_update_record
;
2014-12-23 deposited with the CCDC.
2015-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                62.892(4)
_cell_angle_beta                 84.149(4)
_cell_angle_gamma                77.270(4)
_cell_formula_units_Z            6
_cell_length_a                   14.501(4)
_cell_length_b                   20.180(6)
_cell_length_c                   22.027(7)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      20.718
_cell_measurement_theta_min      2.216
_cell_volume                     5597(3)
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      110.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            69838
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        20.000
_diffrn_reflns_theta_max         20.870
_diffrn_reflns_theta_min         1.039
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_correction_T_min  0.6452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0766 before and 0.0608 after correction.
The Ratio of minimum to maximum transmission is 0.8665.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_description       plate
_exptl_crystal_F_000             2064
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform, Ethanol'
_exptl_crystal_size_max          0.435
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       0.0126(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1371
_refine_ls_number_reflns         11763
_refine_ls_number_restraints     551
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.1331
_refine_ls_R_factor_gt           0.0916
_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^)+(0.1117P)^2^+12.1125P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2314
_refine_ls_wR_factor_ref         0.2748
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8249
_reflns_number_total             11763
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc02385h2.cif
_cod_data_source_block           jl095
_cod_depositor_comments          'Adding full bibliography for 1540515.cif.'
_cod_database_code               1540515
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.973
_olex2_refinement_description
;
1. 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
2. Shared sites
{C4G, C4F}
{C3G, C3F}
3. Restrained distances
 N1F-C4F \\sim N1F-C4G
 with sigma of 0.005
 C3G-C2F \\sim C3F-C2F
 with sigma of 0.005
4. Rigid bond restraints
 C44C, C44D, C45D, C45C, C46C, C46D, C47D, C47C
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
Uanis(C40A) = Uanis(C40)
Uanis(C41) = Uanis(C41A)
Uanis(C42A) = Uanis(C42)
Uanis(C43A) = Uanis(C43)
Uanis(C44A) = Uanis(C44)
Uanis(C45A) = Uanis(C45)
Uanis(C46A) = Uanis(C46)
Uanis(C47A) = Uanis(C47)
Uanis(C32C) = Uanis(C32D)
Uanis(C33C) = Uanis(C33D)
Uanis(C34C) = Uanis(C34D)
Uanis(C35C) = Uanis(C35D)
Uanis(C36C) = Uanis(C36D)
Uanis(C37C) = Uanis(C37D)
Uanis(C38C) = Uanis(C38D)
Uanis(C39C) = Uanis(C39D)
Uanis(C40C) = Uanis(C40D)
Uanis(C41C) = Uanis(C41D)
Uanis(C42C) = Uanis(C42D)
Uanis(C43C) = Uanis(C43D)
Uanis(C44C) = Uanis(C44D)
Uanis(C45C) = Uanis(C45D)
Uanis(C46D) = Uanis(C46C)
Uanis(C47D) = Uanis(C47C)
Uanis(C32G) = Uanis(C32F)
Uanis(C33F) = Uanis(C33G)
Uanis(C34F) = Uanis(C34G)
Uanis(C35G) = Uanis(C35F)
Uanis(C36G) = Uanis(C36F)
Uanis(C37G) = Uanis(C37F)
Uanis(C38G) = Uanis(C38F)
Uanis(C39G) = Uanis(C39F)
Uanis(C3F) = Uanis(C4F) = Uanis(C18F) = Uanis(C19F) = Uanis(C20F) = Uanis(C21F)
= Uanis(C22F) = Uanis(C23F) = Uanis(C24F) = Uanis(C25F) = Uanis(C26F) =
Uanis(C27F) = Uanis(C28F) = Uanis(C29F) = Uanis(C30F) = Uanis(C3G) = Uanis(C4G)
= Uanis(C18G) = Uanis(C19G) = Uanis(C20G) = Uanis(C21G) = Uanis(C22G) =
Uanis(C23G) = Uanis(C24G) = Uanis(C25G) = Uanis(C26G) = Uanis(C27G) =
Uanis(C28G) = Uanis(C29G) = Uanis(C30G)
6. Rigid body (RIGU) restrains
 C44C, C44D, C45D, C45C, C46C, C46D, C47D, C47C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Same fragment restrains
{C32, C33, C34, C35, C36, C37, C38, C39}
as
{C40, C41, C42, C43, C44, C45, C46, C47}
{C32, C33, C34, C35, C36, C37, C38, C39}
as
{C40A, C41A, C42A, C43A, C44A, C45A, C46A, C47A}
{C32, C33, C34, C35, C36, C37, C38, C39}
as
{C32C, C33C, C34C, C35C, C36C, C37C, C38C, C39C}
{C32, C33, C34, C35, C36, C37, C38, C39}
as
{C40C, C41C, C42C, C43C, C44C, C45C, C46C, C47C}
{C32, C33, C34, C35, C36, C37, C38, C39}
as
{C32D, C33D, C34D, C35D, C36D, C37D, C38D, C39D}
{C32, C33, C34, C35, C36, C37, C38, C39}
as
{C40D, C41D, C42D, C43D, C44D, C45D, C46D, C47D}
{C3F, C4F, C18F, C19F, C20F, C21F, C22F, C23F, C24F, C25F, C26F, C27F, C28F,
C29F, C30F}
as
{C3G, C4G, C18G, C19G, C20G, C21G, C22G, C23G, C24G, C25G, C26G, C27G, C28G,
C29G, C30G}
{C32, C33, C34, C35, C36, C37, C38, C39}
as
{C32F, C33F, C34F, C35F, C36F, C37F, C38F, C39F}
{C32, C33, C34, C35, C36, C37, C38, C39}
as
{C32G, C33G, C34G, C35G, C36G, C37G, C38G, C39G}
8. Others
 Sof(H31D)=Sof(C40A)=Sof(H40I)=Sof(H40J)=Sof(C41A)=Sof(H41I)=Sof(H41J)=
 Sof(C42A)=Sof(H42I)=Sof(H42J)=Sof(C43A)=Sof(H43I)=Sof(H43J)=Sof(C44A)=
 Sof(H44I)=Sof(H44J)=Sof(C45A)=Sof(H45I)=Sof(H45J)=Sof(C46A)=Sof(H46I)=
 Sof(H46J)=Sof(C47A)=Sof(H47M)=Sof(H47N)=Sof(H47O)=1-FVAR(1)
 Sof(H31)=Sof(C40)=Sof(H40G)=Sof(H40H)=Sof(C41)=Sof(H41G)=Sof(H41H)=Sof(C42)=
 Sof(H42G)=Sof(H42H)=Sof(C43)=Sof(H43G)=Sof(H43H)=Sof(C44)=Sof(H44G)=Sof(H44H)=
 Sof(C45)=Sof(H45G)=Sof(H45H)=Sof(C46)=Sof(H46G)=Sof(H46H)=Sof(C47)=Sof(H47J)=
 Sof(H47K)=Sof(H47L)=FVAR(1)
 Sof(H31A)=Sof(C32D)=Sof(H32C)=Sof(H32D)=Sof(C33D)=Sof(H33C)=Sof(H33D)=
 Sof(C34D)=Sof(H34C)=Sof(H34D)=Sof(C35D)=Sof(H35C)=Sof(H35D)=Sof(C36D)=
 Sof(H36C)=Sof(H36D)=Sof(C37D)=Sof(H37C)=Sof(H37D)=Sof(C38D)=Sof(H38C)=
 Sof(H38D)=Sof(C39D)=Sof(H39D)=Sof(H39E)=Sof(H39F)=1-FVAR(2)
 Sof(H31C)=Sof(C32C)=Sof(H32A)=Sof(H32B)=Sof(C33C)=Sof(H33A)=Sof(H33B)=
 Sof(C34C)=Sof(H34A)=Sof(H34B)=Sof(C35C)=Sof(H35A)=Sof(H35B)=Sof(C36C)=
 Sof(H36A)=Sof(H36B)=Sof(C37C)=Sof(H37A)=Sof(H37B)=Sof(C38C)=Sof(H38A)=
 Sof(H38B)=Sof(C39C)=Sof(H39A)=Sof(H39B)=Sof(H39C)=FVAR(2)
 Sof(C40D)=Sof(H40C)=Sof(H40D)=Sof(C41D)=Sof(H41C)=Sof(H41D)=Sof(C42D)=
 Sof(H42C)=Sof(H42D)=Sof(C43D)=Sof(H43C)=Sof(H43D)=Sof(C44D)=Sof(H44C)=
 Sof(H44D)=Sof(C45D)=Sof(H45C)=Sof(H45D)=Sof(C46D)=Sof(H46C)=Sof(H46D)=
 Sof(C47D)=Sof(H47D)=Sof(H47E)=Sof(H47F)=1-FVAR(3)
 Sof(C40C)=Sof(H40A)=Sof(H40B)=Sof(C41C)=Sof(H41A)=Sof(H41B)=Sof(C42C)=
 Sof(H42A)=Sof(H42B)=Sof(C43C)=Sof(H43A)=Sof(H43B)=Sof(C44C)=Sof(H44A)=
 Sof(H44B)=Sof(C45C)=Sof(H45A)=Sof(H45B)=Sof(C46C)=Sof(H46A)=Sof(H46B)=
 Sof(C47C)=Sof(H47A)=Sof(H47B)=Sof(H47C)=FVAR(3)
 Sof(H31B)=Sof(C32G)=Sof(H32G)=Sof(H32H)=Sof(C33G)=Sof(H33G)=Sof(H33H)=
 Sof(C34G)=Sof(H34G)=Sof(H34H)=Sof(C35G)=Sof(H35G)=Sof(H35H)=Sof(C36G)=
 Sof(H36G)=Sof(H36H)=Sof(C37G)=Sof(H37G)=Sof(H37H)=Sof(C38G)=Sof(H38G)=
 Sof(H38H)=Sof(C39G)=Sof(H39J)=Sof(H39K)=Sof(H39L)=1-FVAR(4)
 Sof(H31F)=Sof(C32F)=Sof(H32E)=Sof(H32F)=Sof(C33F)=Sof(H33E)=Sof(H33F)=
 Sof(C34F)=Sof(H34E)=Sof(H34F)=Sof(C35F)=Sof(H35E)=Sof(H35F)=Sof(C36F)=
 Sof(H36E)=Sof(H36F)=Sof(C37F)=Sof(H37E)=Sof(H37F)=Sof(C38F)=Sof(H38E)=
 Sof(H38F)=Sof(C39F)=Sof(H39G)=Sof(H39H)=Sof(H39I)=FVAR(4)
 Sof(C3G)=Sof(C4G)=Sof(C18G)=Sof(H18G)=Sof(C19G)=Sof(C20G)=Sof(C21G)=Sof(H21G)=
 Sof(C22G)=Sof(C23G)=Sof(C24G)=Sof(H24G)=Sof(C25G)=Sof(C26G)=Sof(H26G)=
 Sof(H26H)=Sof(H26I)=Sof(C27G)=Sof(H27G)=Sof(C28G)=Sof(H28G)=Sof(C29G)=
 Sof(H29G)=Sof(C30G)=Sof(H30G)=1-FVAR(5)
 Sof(C3F)=Sof(C4F)=Sof(C18F)=Sof(H18F)=Sof(C19F)=Sof(C20F)=Sof(C21F)=Sof(H21F)=
 Sof(C22F)=Sof(C23F)=Sof(C24F)=Sof(H24F)=Sof(C25F)=Sof(C26F)=Sof(H26D)=
 Sof(H26E)=Sof(H26F)=Sof(C27F)=Sof(H27F)=Sof(C28F)=Sof(H28F)=Sof(C29F)=
 Sof(H29F)=Sof(C30F)=Sof(H30F)=FVAR(5)
9.a Ternary CH refined with riding coordinates:
 C31(H31), C31(H31D), C31C(H31C), C31C(H31A), C31F(H31F), C31F(H31B)
9.b Secondary CH2 refined with riding coordinates:
 C32(H32I,H32J), C33(H33I,H33J), C34(H34I,H34J), C35(H35I,H35J), C36(H36I,
 H36J), C37(H37I,H37J), C38(H38I,H38J), C40(H40G,H40H), C41(H41G,H41H),
 C42(H42G,H42H), C43(H43G,H43H), C44(H44G,H44H), C45(H45G,H45H), C46(H46G,H46H),
  C40A(H40I,H40J), C41A(H41I,H41J), C42A(H42I,H42J), C43A(H43I,H43J), C44A(H44I,
 H44J), C45A(H45I,H45J), C46A(H46I,H46J), C32C(H32A,H32B), C33C(H33A,H33B),
 C34C(H34A,H34B), C35C(H35A,H35B), C36C(H36A,H36B), C37C(H37A,H37B), C38C(H38A,
 H38B), C40C(H40A,H40B), C41C(H41A,H41B), C42C(H42A,H42B), C43C(H43A,H43B),
 C44C(H44A,H44B), C45C(H45A,H45B), C46C(H46A,H46B), C32D(H32C,H32D), C33D(H33C,
 H33D), C34D(H34C,H34D), C35D(H35C,H35D), C36D(H36C,H36D), C37D(H37C,H37D),
 C38D(H38C,H38D), C40D(H40C,H40D), C41D(H41C,H41D), C42D(H42C,H42D), C43D(H43C,
 H43D), C44D(H44C,H44D), C45D(H45C,H45D), C46D(H46C,H46D), C32F(H32E,H32F),
 C33F(H33E,H33F), C34F(H34E,H34F), C35F(H35E,H35F), C36F(H36E,H36F), C37F(H37E,
 H37F), C38F(H38E,H38F), C32G(H32G,H32H), C33G(H33G,H33H), C34G(H34G,H34H),
 C35G(H35G,H35H), C36G(H36G,H36H), C37G(H37G,H37H), C38G(H38G,H38H), C40F(H40E,
 H40F), C41F(H41E,H41F), C42F(H42E,H42F), C43F(H43E,H43F), C44F(H44E,H44F),
 C45F(H45E,H45F), C46F(H46E,H46F)
9.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C21(H21), C24(H24), C27(H27), C28(H28), C29(H29), C30(H30), C5C(H5C), C8C(H8C),
  C11C(H11C), C14C(H14C), C15C(H15C), C16C(H16C), C17C(H17C), C18C(H18C),
 C21C(H21C), C24C(H24C), C27C(H27C), C28C(H28C), C29C(H29C), C30C(H30C),
 C5F(H5F), C8F(H8F), C11F(H11F), C14F(H14F), C15F(H15F), C16F(H16F), C17F(H17F),
  C18F(H18F), C21F(H21F), C24F(H24F), C27F(H27F), C28F(H28F), C29F(H29F),
 C30F(H30F), C18G(H18G), C21G(H21G), C24G(H24G), C27G(H27G), C28G(H28G),
 C29G(H29G), C30G(H30G)
9.d Idealised Me refined as rotating group:
 C13(H13G,H13H,H13I), C26(H26J,H26K,H26L), C39(H39M,H39N,H39O), C47(H47J,H47K,
 H47L), C47A(H47M,H47N,H47O), C13C(H13A,H13B,H13C), C26C(H26A,H26B,H26C),
 C39C(H39A,H39B,H39C), C47C(H47A,H47B,H47C), C39D(H39D,H39E,H39F), C47D(H47D,
 H47E,H47F), C13F(H13D,H13E,H13F), C26F(H26D,H26E,H26F), C26G(H26G,H26H,H26I),
 C39F(H39G,H39H,H39I), C39G(H39J,H39K,H39L), C47F(H47G,H47H,H47I)
;
_shelx_res_checksum              2346
_shelx_hkl_checksum              6579