A Mechanism for Reversible Solid-State Transitions Involving Nitro Torsion
Gui, Yue; Yao, Xin; Guzei, Ilia A.; Aristov, Michael M.; Yu, Junguang; Yu, Lian; Chemistry of Materials 32 (2020) 7754–7765; doi:10.1021/acs.chemmater.0c02209

data_4003676
_publ_section_title
;
 A Mechanism for Reversible Solid-State Transitions Involving Nitro
 Torsion
;
_journal_issue                   18
_journal_name_full               'Chemistry of Materials'
_journal_page_first              7754
_journal_page_last               7765
_journal_paper_doi               10.1021/acs.chemmater.0c02209
_journal_volume                  32
_journal_year                    2020
_chemical_formula_moiety         'C20 H24 N2 O6'
_chemical_formula_sum            'C20 H24 N2 O6'
_chemical_formula_weight         388.41
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.480(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6975(18)
_cell_length_b                   15.393(3)
_cell_length_c                   13.243(2)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    400.0
_cell_measurement_theta_max      72.49
_cell_measurement_theta_min      2.87
_cell_volume                     2091.1(6)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      400.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            36561
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         72.479
_diffrn_reflns_theta_min         4.514
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.762
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1042 before and 0.0602 after correction.
The Ratio of minimum to maximum transmission is 0.8416.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.513
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4109
_refine_ls_number_restraints     316
_refine_ls_restrained_S_all      1.660
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0938
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3217
_refine_ls_wR_factor_ref         0.3423
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3291
_reflns_number_total             4109
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            NIS_400k.cif
_cod_data_source_block           yu206_400k
_cod_depositor_comments
'Adding full bibliography for 4003674--4003684.cif.'
_cod_database_code               4003676
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.863
_shelx_estimated_absorpt_t_min   0.740
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2B-C11B = N2-C11
 1.48 with sigma of 0.01
 N2B-O5B = N2B-O6B = N2-O5 = N2-O6
 1.2 with sigma of 0.005
 C6-C3 = C6B-C3
 1.535 with sigma of 0.01
 C14-C15
 1.46 with sigma of 0.005
 O5B-O6B = O5-O6
 2.05 with sigma of 0.01
 C11B-O5B \\sim C11B-O6B \\sim C11-O5 \\sim C11-O6
 with sigma of 0.005
 C6-C3 \\sim C6B-C3
 with sigma of 0.004
3. Uiso/Uaniso restraints and constraints
Uanis(C6B) \\sim Ueq, Uanis(C7B) \\sim Ueq, Uanis(C8B) \\sim Ueq, Uanis(C9B)
\\sim Ueq, Uanis(C10B) \\sim Ueq, Uanis(C11B) \\sim Ueq, Uanis(C6) \\sim Ueq,
Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim
Ueq, Uanis(C11) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of
0.02
Uanis(C11B) \\sim Ueq, Uanis(N2B) \\sim Ueq, Uanis(O5B) \\sim Ueq, Uanis(O6B)
\\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(O6) \\sim Ueq,
Uanis(O5) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C16A) \\sim Ueq, Uanis(C17)
\\sim Ueq, Uanis(C17A) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
4. Rigid body (RIGU) restrains
 C15, C16, C17, C17A, C16A, C14
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C6B, C7B, C8B, C9B, C10B, C11B, N2B, O5B, O6B, C6, C7, C8, C9, C10, C11, N2,
 O6, O5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{O2, C14, C15, C17, C16} sigma for 1-2: 0.005, 1-3: 0.01
{O2, C14, C15, C16A, C17A} sigma for 1-2: 0.005, 1-3: 0.01
{O2, C14, C15, C17A, C16A} sigma for 1-2: 0.005, 1-3: 0.01
as in
{O2, C14, C15, C16, C17}
6. Others
 Sof(H15A)=Sof(C17A)=Sof(H17D)=Sof(H17E)=Sof(H17F)=Sof(C16A)=Sof(H16D)=
 Sof(H16E)=Sof(H16F)=1-FVAR(1)
 Sof(H15)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C17)=Sof(H17A)=Sof(H17B)=
 Sof(H17C)=FVAR(1)
 Sof(H3B)=Sof(N2B)=Sof(O5B)=Sof(O6B)=Sof(C6B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=
 Sof(H8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=Sof(C11B)=1-FVAR(2)
 Sof(H3A)=Sof(N2)=Sof(O5)=Sof(O6)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=
 Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=Sof(C11)=FVAR(2)
7.a Ternary CH refined with riding coordinates:
 C15(H15), C15(H15A), C3(H3A), C3(H3B)
7.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
7.c Me refined with riding coordinates:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C17A(H17D,H17E,H17F), C16A(H16D,
 H16E,H16F)
7.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C7B(H7B), C8B(H8B), C9B(H9B),
 C10B(H10B)
7.e Fitted hexagon refined as free rotating group:
 C6(C7,C8,C9,C10,C11), C6B(C7B,C8B,C9B,C10B,C11B)
7.f Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              47135
_shelx_hkl_checksum              12394
_olex2_submission_special_instructions 'No special instructions were received'