Supramolecular Inhibition of [4 + 2] Diels–Alder Reactions in Charge-Transfer Crystals
Botes, Delbert S.; Khorasani, Sanaz; Duminy, Welni; Levendis, Demetrius C.; Fernandes, Manuel A.; Crystal Growth & Design 20 (2019) 291–; doi:10.1021/acs.cgd.9b01167

data_4517202
_publ_section_title
;
 Supramolecular Inhibition of [4 + 2] Diels--Alder Reactions in
 Charge-Transfer Crystals
;
_journal_issue                   1
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              291
_journal_paper_doi               10.1021/acs.cgd.9b01167
_journal_volume                  20
_journal_year                    2019
_chemical_formula_moiety         'C22 H14 N2 O4 S2, C14 H9 Br'
_chemical_formula_sum            'C36 H23 Br N2 O4 S2'
_chemical_formula_weight         691.59
_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     direct
_audit_creation_date             2019-08-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.0900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.4089(5)
_cell_length_b                   7.3320(2)
_cell_length_c                   24.3958(7)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.72
_cell_measurement_theta_min      3.03
_cell_volume                     3044.86(15)
_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      173.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1054
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            64802
_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         25.992
_diffrn_reflns_theta_min         2.906
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.532
_exptl_absorpt_correction_T_max  0.9393
_exptl_absorpt_correction_T_min  0.7702
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
'Face indexed absorption corrections done with XPREP'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_description       needle
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.065
_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     503
_refine_ls_number_reflns         5964
_refine_ls_number_restraints     134
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0334P)^2^+3.0923P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0981
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4277
_reflns_number_total             5964
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            Botes_CGD.cif
_cod_data_source_block           16dbv6_dbbrneedle_0a
_cod_depositor_comments
'Adding full bibliography for 4517199--4517212.cif.'
_cod_database_code               4517202
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.927
_shelx_estimated_absorpt_t_min   0.600
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 C23A, C24A, C25A, C26A, C27A, C28A, C29A, C30A, C31A, C32A, C33A, C34A, C35A,
 C36A
 with sigma for 1-2 distances of 0.00125 and sigma for 1-3 distances of 0.00125
3. Uiso/Uaniso restraints and constraints
C23A \\sim C24A \\sim C25A \\sim C26A \\sim C27A \\sim C28A \\sim C29A \\sim
C30A \\sim C31A \\sim C32A \\sim C33A \\sim C34A \\sim C35A \\sim C36A: within
1.7A with sigma of 0.0025 and sigma for terminal atoms of 0.005
4. Others
 Sof(C30A)=Sof(H30A)=Sof(Br1A)=Sof(C23A)=Sof(C24A)=Sof(C25A)=Sof(H25A)=
 Sof(C26A)=Sof(H26A)=Sof(C27A)=Sof(H27A)=Sof(C28A)=Sof(H28A)=Sof(C29A)=
 Sof(C31A)=Sof(C32A)=Sof(H32A)=Sof(C33A)=Sof(H33A)=Sof(C34A)=Sof(H34A)=
 Sof(C35A)=Sof(H35A)=Sof(C36A)=1-FVAR(1)
 Sof(Br1)=Sof(C23)=Sof(C24)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26)=Sof(C27)=
 Sof(H27)=Sof(C28)=Sof(H28)=Sof(C29)=Sof(C30)=Sof(H30)=Sof(C31)=Sof(C32)=
 Sof(H32)=Sof(C33)=Sof(H33)=Sof(C34)=Sof(H34)=Sof(C35)=Sof(H35)=Sof(C36)=FVAR(1)
5.a Free rotating group:
 C30A(Br1A,C23A,C24A,C25A,C26A,C27A,C28A,C29A,C31A,C32A,C33A,C34A,C35A,C36A)
5.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C16(H16A,H16B)
5.c Aromatic/amide H refined with riding coordinates:
 C30A(H30A), C25A(H25A), C26A(H26A), C27A(H27A), C28A(H28A), C32A(H32A),
 C33A(H33A), C34A(H34A), C35A(H35A), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26),
  C27(H27), C28(H28), C30(H30), C32(H32), C33(H33), C34(H34), C35(H35)
;
_shelx_res_checksum              22211
_shelx_hkl_checksum              25071
_olex2_submission_special_instructions 'No special instructions were received'