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_7241739
_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         'C12 H11 N3, C9 H12 N2'
_chemical_formula_sum            'C21 H23 N5'
_chemical_formula_weight         345.44
_chemical_melting_point          352.12
_chemical_name_systematic        '4-Aminoazobenzene; 4-Pyrrolidinopyridine'
_chemical_properties_physical    Light-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 90.84(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9177(16)
_cell_length_b                   5.9154(12)
_cell_length_c                   19.843(4)
_cell_measurement_reflns_used    2790
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9143
_cell_measurement_theta_min      2.0529
_cell_volume                     929.3(3)
_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  0.0472
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11209
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.883
_diffrn_reflns_theta_min         2.053
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.7556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_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         0.299
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       0.043(6)
_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   0.974
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4268
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0606P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3075
_reflns_number_total             4268
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01394c3.cif
_cod_data_source_block           shelxl
_cod_database_code               7241739
_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 C(H,H) groups, All N(H,H) groups
2. Restrained distances
 H1A-H1B
 1.5 with sigma of 0.01
 N1-H1A = N1-H1B
 0.9 with sigma of 0.01
 H19A-H19B = H19C-H19D
 1.55 with sigma of 0.01
 C19-H19A = C19'-H19B = C19-H19C = C19'-H19D
 0.93 with sigma of 0.05
3. Rigid bond restraints
 N2, C4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: C19(0.5) H19A(0.5) H19B(0.5) C19'(0.5) H19C(0.5) H19D(0.5)
5.a Riding coordinates:
 C18(H18A,H18B), C20(H20A,H20B)
5.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C17(H17)
;
_shelx_res_checksum              78398
_olex2_submission_special_instructions 'No special instructions were received'