Tuning the photomechanical behavior and excellent elasticity of azobenzene via cocrystal engineering
Ye, Yang; Gao, Lei; Hao, Hongxun; Yin, Qiuxiang; Xie, Chuang; CrystEngComm 22 (2020) 8045–8053; doi:10.1039/D0CE01394C

data_7241740
_publ_section_title
;
 Tuning the photomechanical behavior and excellent elasticity of
 azobenzene via cocrystal engineering
;
_journal_issue                   46
_journal_name_full               CrystEngComm
_journal_page_first              8045
_journal_page_last               8053
_journal_paper_doi               10.1039/D0CE01394C
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         '0.5(C12 H9 N3), 0.5(C12 H11 N3), C17 H13 N'
_chemical_formula_sum            'C29 H24 N4'
_chemical_formula_weight         428.52
_chemical_melting_point          348.73
_chemical_name_systematic
'4-aminoazobenzene; 1-(1-naphthyl)-2-(4'-pyridyl)ethylene'
_chemical_properties_physical    Light-sensitive
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-06-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-10 deposited with the CCDC.	2020-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.76(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.715(5)
_cell_length_b                   5.9027(12)
_cell_length_c                   31.344(6)
_cell_measurement_reflns_used    5665
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9865
_cell_measurement_theta_min      1.8009
_cell_volume                     4530.9(17)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      113.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            38825
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.020
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         1.960
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.7842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       needle
_exptl_crystal_F_000             1808
_exptl_crystal_preparation       photochromic
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate/n-heptane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0046(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     646
_refine_ls_number_reflns         7955
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1220
_refine_ls_R_factor_gt           0.0776
_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^)+(0.1213P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1948
_refine_ls_wR_factor_ref         0.2262
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5039
_reflns_number_total             7955
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01394c3.cif
_cod_data_source_block           r20200101a1
_cod_original_cell_volume        4531.0(17)
_cod_database_code               7241740
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 N1-H1A = N1-H1B = N4-H4A = N4-H4B
 0.9 with sigma of 0.01
 H1A-H1B = H4A-H4B
 1.5 with sigma of 0.01
 N2-N3 = N5-N6 = N5'-N6'
 1.32 with sigma of 0.01
3. Rigid bond restraints
 C7, C12
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C4, N2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C7, N3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
N5 \\sim N6 \\sim N5' \\sim N6': within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
N2 \\sim N3 \\sim N2A \\sim N3A: within 1.7A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N2) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(N2A) \\sim Ueq, Uanis(N3A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(N5')=Sof(N6')=1-FVAR(1)
 Sof(N5)=Sof(N6)=FVAR(1)
 Sof(N2A)=Sof(N3A)=1-FVAR(2)
 Sof(N2)=Sof(N3)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24),
  C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C33(H33),
 C34(H34), C35(H35), C37(H37), C38(H38), C39(H39), C40(H40), C42(H42), C43(H43),
  C45(H45), C46(H46), C47(H47), C48(H48), C50(H50), C51(H51), C52(H52),
 C54(H54), C55(H55), C56(H56), C57(H57)
;
_shelx_res_checksum              77291
_olex2_submission_special_instructions 'No special instructions were received'