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_7241737
_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_absolute_configuration ad
_chemical_formula_moiety         'C12 H11 N3, C10 H8 N2'
_chemical_formula_sum            'C22 H19 N5'
_chemical_formula_weight         353.42
_chemical_melting_point          398.65
_chemical_name_systematic        4-Aminoazobenzene;4,4'-Bipyridine
_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     dual
_audit_creation_date             2019-12-14
_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                 97.914(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5794(4)
_cell_length_b                   5.6975(3)
_cell_length_c                   21.4258(9)
_cell_measurement_reflns_used    7551
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      33.4660
_cell_measurement_theta_min      2.6910
_cell_volume                     916.43(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrystalClear (Rigaku,2008)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -120.00  60.00   1.00    8.00    --  -30.00  45.00   0.00  180
  2  \w   -120.00  60.00   1.00    8.00    --  -30.00  45.00  90.00  180
  3  \w   -120.00  60.00   1.00    8.00    --  -30.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0190258000
_diffrn_orient_matrix_UB_12      0.0041199000
_diffrn_orient_matrix_UB_13      -0.0333445000
_diffrn_orient_matrix_UB_21      0.0692596000
_diffrn_orient_matrix_UB_22      -0.0818432000
_diffrn_orient_matrix_UB_23      -0.0023574000
_diffrn_orient_matrix_UB_31      -0.0613275000
_diffrn_orient_matrix_UB_32      -0.0937271000
_diffrn_orient_matrix_UB_33      0.0006113000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8125
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.713
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_preparation       photochromic
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate/n-heptane'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1257 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3247
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0990P)^2^+0.2684P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1516
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                3081
_reflns_number_total             3247
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01394c3.cif
_cod_data_source_block           r20191214c
_cod_database_code               7241737
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.987
_reflns_odcompleteness_completeness 99.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Rigid bond restraints
 N2, C6, N3, C7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.0002
3.a Rotating group:
 N1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22)
;
_shelx_res_checksum              9464
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.382
_oxdiff_exptl_absorpt_empirical_full_min 0.512