Correlation between Solid-State and Solution Conformational Ratios in a Series of N-(o-Tolyl)Succinimide Molecular Rotors
Li, Ping; Hwang, Jungwun; Maier, Josef M.; Zhao, Chen; Kaborda, Darya V.; Smith, Mark D.; Pellechia, Perry J.; Shimizu, Ken D.; Crystal Growth & Design 15 (2015) 3561–; doi:10.1021/acs.cgd.5b00906

data_4516401
_publ_section_title
;
 Correlation between Solid-State and Solution Conformational Ratios in a
 Series of N-(o-Tolyl)Succinimide Molecular Rotors
;
_journal_issue                   8
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              3561
_journal_paper_doi               10.1021/acs.cgd.5b00906
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C29 H22 N2 O3, 0.75(C H Cl3)'
_chemical_formula_sum            'C29.75 H22.75 Cl2.25 N2 O3'
_chemical_formula_weight         535.81
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_cell_angle_alpha                64.551(3)
_cell_angle_beta                 81.025(3)
_cell_angle_gamma                76.830(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4119(19)
_cell_length_b                   12.090(2)
_cell_length_c                   12.896(3)
_cell_measurement_reflns_used    5709
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.819
_cell_measurement_theta_min      2.620
_cell_volume                     1287.4(5)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.631 (Bruker, 2003)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16822
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.088
_diffrn_reflns_theta_min         1.753
_diffrn_source_current           37.0
_diffrn_source_power             1.739
_diffrn_source_voltage           47.0
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       plate
_exptl_crystal_F_000             555
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.766
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         4569
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0596
_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^)+(0.0857P)^2^+1.0700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1601
_refine_ls_wR_factor_ref         0.1699
_reflns_number_gt                3658
_reflns_number_total             4569
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cg5b00906_si_002.cif
_cod_data_source_block           15(lpc91m)
_cod_original_cell_volume        1287.4(4)
_cod_database_code               4516401
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C8A, C8B}
{C9A, C9B}
{C10A, C10B}
{C11A, C11B}
{C12A, C12B}
{C13A, C13B}
{C14A, N2B}
{C15A, C14B}
{C16A, C15B}
{C17A, C17B}
{C18A, C18B}
{C19A, C19B}
{C20A, C20B}
{C16B, N2A}
3. Restrained distances
 C24A-C29A \\sim C24B-C29B
 with sigma of 0.015
 N1-C23A \\sim N1-C23B
 with sigma of 0.015
4. Uiso/Uaniso restraints and constraints
Uanis(C8A) = Uanis(C8B)
Uanis(C9A) = Uanis(C9B)
Uanis(C10A) = Uanis(C10B)
Uanis(C11A) = Uanis(C11B)
Uanis(C12A) = Uanis(C12B)
Uanis(C13A) = Uanis(C13B)
Uanis(C14A) = Uanis(N2B)
Uanis(C15A) = Uanis(C14B)
Uanis(C16A) = Uanis(C15B)
Uanis(C16B) = Uanis(N2A)
Uanis(C17A) = Uanis(C17B)
Uanis(C18A) = Uanis(C18B)
Uanis(C19A) = Uanis(C19B)
Uanis(C20A) = Uanis(C20B)
Uanis(C24B) = Uanis(C28A)
Uanis(C24A) = Uanis(C28B)
Uanis(C23B) = Uanis(C23A)
Uanis(Cl1A) = Uanis(Cl1B) = Uanis(Cl1C)
Uanis(Cl2A) = Uanis(Cl2B)
Uanis(Cl3A) = Uanis(Cl3B)
Uiso(C30A) = Uiso(C30B) = Uiso(C30C)
Uiso(Cl2C) = Uiso(Cl3C)
5. Same fragment restrains
{C30A, Cl1A, Cl2A, Cl3A}
as
{C30B, Cl1B, Cl2B, Cl3B}
{C30A, Cl1A, Cl2A, Cl3A}
as
{C30C, Cl1C, Cl2C, Cl3C}
6. Others
 Sof(C23B)=Sof(C24B)=Sof(C25B)=Sof(H25B)=Sof(C26B)=Sof(H26B)=Sof(C27B)=
 Sof(H27B)=Sof(C28B)=Sof(H28B)=Sof(C29B)=Sof(H29D)=Sof(H29E)=Sof(H29F)=1-FVAR(1)
 Sof(C23A)=Sof(C24A)=Sof(C25A)=Sof(H25A)=Sof(C26A)=Sof(H26A)=Sof(C27A)=
 Sof(H27A)=Sof(C28A)=Sof(H28A)=Sof(C29A)=Sof(H29A)=Sof(H29B)=Sof(H29C)=FVAR(1)
 Sof(C8B)=Sof(C9B)=Sof(C10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12B)=Sof(C13B)=
 Sof(H13B)=Sof(C14B)=Sof(C15B)=Sof(C16B)=Sof(H16B)=Sof(N2B)=Sof(C17B)=Sof(H17B)=
 Sof(C18B)=Sof(H18B)=Sof(C19B)=Sof(H19B)=Sof(C20B)=1-FVAR(2)
 Sof(C8A)=Sof(C9A)=Sof(C10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=
 Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(C16A)=Sof(N2A)=Sof(C17A)=Sof(H17A)=
 Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=FVAR(2)
 Sof(C30A)=Sof(H30A)=Sof(Cl1A)=Sof(Cl2A)=Sof(Cl3A)=FVAR(3)
 Sof(C30B)=Sof(H30B)=Sof(Cl1B)=Sof(Cl2B)=Sof(Cl3B)=FVAR(4)
 Sof(C30C)=Sof(H30C)=Sof(Cl1C)=Sof(Cl2C)=Sof(Cl3C)=FVAR(5)
7.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C30A(H30A), C30B(H30B), C30C(H30C)
7.b Aromatic/amide H refined with riding coordinates:
 C11A(H11A), C12A(H12A), C13A(H13A), C14A(H14A), C17A(H17A), C18A(H18A),
 C19A(H19A), C11B(H11B), C12B(H12B), C13B(H13B), C16B(H16B), C17B(H17B),
 C18B(H18B), C19B(H19B), C25A(H25A), C26A(H26A), C27A(H27A), C28A(H28A),
 C25B(H25B), C26B(H26B), C27B(H27B), C28B(H28B)
7.c Fitted hexagon refined as free rotating group:
 C23A(C24A,C25A,C26A,C27A,C28A), C23B(C24B,C25B,C26B,C27B,C28B)
7.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C29A(H29A,H29B,H29C), C29B(H29D,
 H29E,H29F)
;
_shelx_res_checksum              10132
_shelx_hkl_checksum              76899