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_7241738
_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 H12 N2, C12 H11 N3'
_chemical_formula_sum            'C24 H23 N5'
_chemical_formula_weight         381.47
_chemical_melting_point          412.81
_chemical_name_systematic        4-Aminoazobenzene;1,2-bis(4-pyridyl)ethane
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-13
_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                 91.233(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7300(6)
_cell_length_b                   5.6677(4)
_cell_length_c                   23.0411(14)
_cell_measurement_reflns_used    4054
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.4300
_cell_measurement_theta_min      2.6200
_cell_volume                     1009.23(12)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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      -0.0133856000
_diffrn_orient_matrix_UB_12      0.0472446000
_diffrn_orient_matrix_UB_13      -0.0282397000
_diffrn_orient_matrix_UB_21      0.0857266000
_diffrn_orient_matrix_UB_22      0.0446682000
_diffrn_orient_matrix_UB_23      0.0005823000
_diffrn_orient_matrix_UB_31      0.0298878000
_diffrn_orient_matrix_UB_32      -0.1069734000
_diffrn_orient_matrix_UB_33      -0.0122479000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8899
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.636
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75114
_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    1.255
_exptl_crystal_description       plate
_exptl_crystal_F_000             404
_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          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 938 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3986
_refine_ls_number_restraints     74
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0715
_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^)+(0.1189P)^2^+0.5240P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1964
_refine_ls_wR_factor_ref         0.2223
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                2844
_reflns_number_total             3986
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01394c3.cif
_cod_data_source_block           r20191212c
_cod_database_code               7241738
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.985
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Rigid bond restraints
 N5, C19
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
 C19, N5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
C7 \\sim C6A \\sim C6 \\sim C7A: within 1.7A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C6A) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N4) \\sim Ueq, Uanis(N5) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4. Others
 Fixed Sof: C6(0.36) H6A(0.36) H6B(0.36) C7A(0.64) H7AA(0.64) H7AB(0.64)
 C6A(0.64) H6AA(0.64) H6AB(0.64) C7(0.36) H7A(0.36) H7B(0.36)
5.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7A(H7AA,H7AB), C6A(H6AA,H6AB), C7(H7A,H7B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23),
  C24(H24)
5.c X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
;
_shelx_res_checksum              90543
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.376
_oxdiff_exptl_absorpt_empirical_full_min 0.613