Engineering Hydrogen-Bonded Hexagonal Networks Built from Flexible 1,3,5-Trisubstituted Derivatives of Benzene.
Helzy, Fatima; Maris, Thierry; Wuest, James D.; The Journal of organic chemistry 81 (2016) 3076–3086; doi:10.1021/acs.joc.5b02552

data_4031824
_publ_section_title
;
 Engineering Hydrogen-Bonded Hexagonal Networks Built from Flexible
 1,3,5-Trisubstituted Derivatives of Benzene.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3076
_journal_page_last               3086
_journal_paper_doi               10.1021/acs.joc.5b02552
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety
'C36 H33 N15 O3, 0.5(C7 H8), 2(C3 H7 N O), 0.5(H2 O)'
_chemical_formula_sum            'C45.5 H52 N17 O5.5'
_chemical_formula_weight         925.04
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                88.963(2)
_cell_angle_beta                 72.912(1)
_cell_angle_gamma                75.267(1)
_cell_formula_units_Z            4
_cell_length_a                   12.6738(3)
_cell_length_b                   19.3375(5)
_cell_length_c                   20.0114(7)
_cell_measurement_reflns_used    9282
_cell_measurement_temperature    150
_cell_measurement_theta_max      67.902
_cell_measurement_theta_min      2.367
_cell_volume                     4525.2(2)
_computing_cell_refinement       'SAINT v7.34A (Bruker, 2008)'
_computing_data_collection       'APEX2 v2.1-0 (Bruker AXS, 2006a)'
_computing_data_reduction        'SAINT v7.34A (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2004)'
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.872
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.872
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            74264
_diffrn_reflns_point_group_measured_fraction_full 0.872
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.122
_diffrn_reflns_theta_min         2.367
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  0.8893
_exptl_absorpt_correction_T_min  0.7862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2007/4 (Bruker,2007/4) was used for absorption correction.
wR2(int) was 0.0695 before and 0.0558 after correction.
The Ratio of minimum to maximum transmission is 0.8841.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1245
_refine_ls_number_reflns         14340
_refine_ls_number_restraints     53
_refine_ls_restrained_S_all      1.410
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0813P)^2^+2.1686P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1409
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12978
_reflns_number_total             14340
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02552_si_002.cif
_cod_data_source_block           3a_DMF_PhMe
_cod_depositor_comments
;
Adding full bibliography for 4031824--4031827.cif.

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C91 H104 N34 O11'
_cod_original_formula_weight         1850.08
_cod_original_formula_moiety
'2(C36 H33 N15 O3), C7 H8, 4(C3 H7 N O), H2 O'
_cod_original_formula_units_Z            2
_cod_database_code               4031824
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O11-H11A = O11-H11B
 0.87 with sigma of 0.005
 H11A-H11B
 1.41 with sigma of 0.005
 C73-C75 \\sim C73-C79
 with sigma of 0.005
 C74B-C75B \\sim C75B-C76B \\sim C76B-C77B \\sim C77B-C78B \\sim C78B-C79B
\\sim C79B-C75B
 with sigma of 0.02
3. Restrained planarity
 C73, C74, C75, C76, C77, C78, C79
 with sigma of 0.005
4. Rigid bond restraints
 C73, C74, C75, C76, C77, C78, C79
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C73B, C74B, C75B, C76B, C77B, C78B, C79B
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
5. Same fragment restrains
{C73, C74, C75, C76, C77, C78, C79} sigma for 1-2: 0.001, 1-3: 0.04
as
{C73B, C74B, C75B, C76B, C77B, C78B, C79B}
6. Others
 Fixed Sof: C73(0.7) H73A(0.7) H73B(0.7) H73C(0.7) C74(0.7) C75(0.7) H75(0.7)
 C76(0.7) H76(0.7) C77(0.7) H77(0.7) C78(0.7) H78(0.7) C79(0.7) H79(0.7)
 C73B(0.3) H73D(0.3) H73E(0.3) H73F(0.3) C74B(0.3) C75B(0.3) H75B(0.3)
 C76B(0.3) H76B(0.3) C77B(0.3) H77B(0.3) C78B(0.3) H78B(0.3) C79B(0.3) H79B(0.3)
7.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C17(H17A,H17B), C27(H27A,H27B), C43(H43A,H43B), C53(H53A,H53B),
 C63(H63A,H63B)
7.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13), C19(H19),
 C20(H20), C22(H22), C23(H23), C29(H29), C30(H30), C32(H32), C33(H33), C38(H38),
  C40(H40), C42(H42), C45(H45), C46(H46), C48(H48), C49(H49), C55(H55),
 C56(H56), C58(H58), C59(H59), C65(H65), C66(H66), C68(H68), C69(H69), C75(H75),
  C76(H76), C77(H77), C78(H78), C79(H79), C75B(H75B), C76B(H76B), C77B(H77B),
 C78B(H78B), C79B(H79B), C80(H80), C83(H83), C86(H86), C89(H89)
7.c Fitted hexagon refined as free rotating group:
 C74(C75,C76,C77,C78,C79), C74B(C75B,C76B,C77B,C78B,C79B)
7.d X=CH2 refined with everything fixed:
 N4(H4A,H4B), N5(H5A,H5B), N9(H9A,H9B), N10(H10A,H10B), N14(H14A,H14B),
 N15(H15A,H15B), N19(H19A,H19B), N20(H20A,H20B), N24(H24A,H24B), N25(H25A,H25B),
  N29(H29A,H29B), N30(H30A,H30B)
7.e Idealised Me refined as rotating group:
 C73(H73A,H73B,H73C), C73B(H73D,H73E,H73F), C81(H81A,H81B,H81C), C82(H82A,H82B,
 H82C), C84(H84A,H84B,H84C), C85(H85A,H85B,H85C), C87(H87A,H87B,H87C), C88(H88A,
 H88B,H88C), C90(H90A,H90B,H90C), C91(H91A,H91B,H91C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'