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_4031825
_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         'C39 H39 N15 O3'
_chemical_formula_sum            'C39 H39 N15 O3'
_chemical_formula_weight         765.85
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-04
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.7618(17)
_cell_length_b                   11.6367(7)
_cell_length_c                   35.138(2)
_cell_measurement_reflns_used    9816
_cell_measurement_temperature    100
_cell_measurement_theta_max      53.989
_cell_measurement_theta_min      2.515
_cell_volume                     11760.4(12)
_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)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Quazar MX'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            186187
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.327
_diffrn_reflns_theta_min         2.515
_diffrn_source                   'Incoatec I\muS Microsource '
_exptl_absorpt_coefficient_mu    0.479
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1079 before and 0.0765 after correction.
The Ratio of minimum to maximum transmission is 0.8464.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.865
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3216
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
)

TITL helz27    P c a 21     R = 0.26
CELL   28.7618   11.6367   35.1380     90.00     90.00     90.00
SPGR Pca21
C101 0.412 0.255 0.110 !       5.95 eA-3
C102 0.589 0.755 0.373 !       5.70 eA-3
C103 0.735 0.147 0.865 !       5.51 eA-3
C104 0.740 0.345 0.125 !       5.50 eA-3
C105 0.213 0.547 0.081 !       4.22 eA-3
C106 0.291 0.954 0.414 !       4.15 eA-3
C107 0.592 0.899 0.649 !       3.97 eA-3
C108 0.236 0.575 0.109 !       3.88 eA-3
C109 0.074 0.186 0.635 !       3.76 eA-3
C110 0.735 0.064 0.884 !       3.62 eA-3
C111 0.920 0.959 0.180 !       3.35 eA-3
C112 0.554 0.588 0.336 !       3.19 eA-3
C113 0.404 0.412 0.846 !       3.13 eA-3
C114 0.209 0.064 0.929 !       2.59 eA-3
C115 0.498 0.568 0.420 !       2.56 eA-3
C116 0.633 0.951 0.624 !       2.52 eA-3
C117 0.087 0.478 0.310 !       2.44 eA-3
C118 0.616 0.723 0.963 !       2.39 eA-3
C119 0.945 0.931 0.992 !       2.37 eA-3
C120 0.550 0.919 0.655 !       2.28 eA-3
C121 0.010 0.942 0.068 !       2.25 eA-3
C122 0.579 0.737 0.962 !       2.19 eA-3
C123 0.210 0.433 0.064 !       2.09 eA-3
C124 0.291 0.433 0.564 !       2.08 eA-3
C125 0.008 0.054 0.673 !       1.98 eA-3
C126 0.014 0.448 0.322 !       1.95 eA-3
C127 0.593 0.199 0.141 !       1.84 eA-3
C128 0.855 0.747 0.500 !       1.82 eA-3
C129 0.434 0.863 0.615 !       1.79 eA-3
C130 0.136 0.452 0.369 !       1.75 eA-3
C131 0.174 0.877 0.922 !       1.73 eA-3
C132 0.099 0.957 0.516 !       1.71 eA-3
C133 0.524 0.895 0.460 !       1.65 eA-3
C134 0.200 0.656 0.048 !       1.64 eA-3
C135 0.578 0.944 0.516 !       1.56 eA-3
C136 0.611 0.097 0.084 !       1.54 eA-3
C137 0.601 0.278 0.851 !       1.44 eA-3
C138 0.456 0.973 0.577 !       1.44 eA-3
C139 0.319 0.616 0.569 !       1.41 eA-3
C140 0.501 0.580 0.541 !       1.40 eA-3
C141 0.609 0.725 0.032 !       1.39 eA-3
C142 0.382 0.557 0.405 !       1.36 eA-3
C143 0.478 0.366 0.026 !       1.35 eA-3
C144 0.040 0.432 0.508 !       1.30 eA-3
C145 0.950 0.087 0.640 !       1.29 eA-3
C146 0.402 0.721 0.484 !       1.24 eA-3
C147 0.358 0.920 0.547 !       1.21 eA-3
C148 0.933 0.828 0.467 !       1.20 eA-3
C149 0.467 0.863 0.990 !       1.17 eA-3
C150 0.991 0.459 0.509 !       1.16 eA-3
C151 0.482 0.542 0.513 !       1.16 eA-3
C152 0.483 0.778 0.991 !       1.15 eA-3
C153 0.448 0.498 0.532 !       1.14 eA-3
C154 0.050 0.705 0.079 !       1.14 eA-3
C155 0.458 0.950 0.604 !       1.14 eA-3
Q156 0.897 0.487 0.959 !       1.14 eA-3
C157 0.563 0.454 0.020 !       1.12 eA-3
C158 0.482 0.644 0.570 !       1.11 eA-3
C159 0.456 0.271 0.500 !       1.11 eA-3
C160 0.501 0.993 0.968 !       1.10 eA-3
C161 0.575 0.431 0.928 !       1.07 eA-3
C162 0.649 0.150 0.023 !       1.07 eA-3
C163 0.422 0.601 0.396 !       1.06 eA-3
C164 0.364 0.562 0.438 !       1.05 eA-3
C165 0.438 0.400 0.532 !       1.05 eA-3
C166 0.061 0.211 0.000 !       1.03 eA-3
Q167 0.901 0.439 0.976 !       1.03 eA-3
C168 0.499 0.855 0.986 !       0.97 eA-3
C169 0.117 0.657 0.984 !       0.96 eA-3
C170 0.016 0.238 0.991 !       0.93 eA-3
C171 0.048 0.827 0.904 !       0.91 eA-3
C172 0.507 0.707 0.361 !       0.90 eA-3
C173 0.944 0.260 0.384 !       0.88 eA-3
C174 0.416 0.630 0.509 !       0.86 eA-3
C175 1.002 0.465 0.010 !       0.85 eA-3
C176 0.501 0.717 0.007 !       0.85 eA-3
C177 0.034 0.654 0.883 !       0.82 eA-3
C178 0.602 0.379 0.968 !       0.80 eA-3
C179 0.124 0.428 0.969 !       0.77 eA-3
C180 0.376 0.549 0.469 !       0.76 eA-3
C181 0.822 0.119 0.539 !       0.75 eA-3
C182 0.937 0.245 0.415 !       0.75 eA-3
C183 0.120 0.654 0.882 !       0.74 eA-3
C184 0.948 0.379 0.334 !       0.70 eA-3
C185 0.594 0.286 0.063 !       0.70 eA-3
C186 0.911 0.155 0.571 !       0.68 eA-3
C187 0.367 0.919 0.421 !       0.67 eA-3
C188 0.973 0.633 0.485 !       0.67 eA-3
C189 0.590 0.293 0.088 !       0.67 eA-3
C190 0.772 0.107 0.900 !       0.66 eA-3
C191 0.952 0.751 0.993 !       0.66 eA-3
C192 0.908 0.874 0.485 !       0.66 eA-3
C193 0.636 0.956 0.937 !       0.65 eA-3
C194 0.891 0.246 0.393 !       0.64 eA-3
C195 0.082 0.409 0.976 !       0.64 eA-3
C196 0.041 0.732 0.860 !       0.64 eA-3
C197 0.907 0.419 0.493 !       0.64 eA-3
C198 0.464 0.266 0.033 !       0.64 eA-3
C199 0.348 0.092 0.444 !       0.63 eA-3
)
;
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 5663 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.47(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1033
_refine_ls_number_reflns         22105
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0645
_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^)+(0.1295P)^2^+1.2464P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1888
_refine_ls_wR_factor_ref         0.2146
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                14970
_reflns_number_total             22105
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02552_si_002.cif
_cod_data_source_block           3b_DMF_PhCl
_cod_depositor_comments
'Adding full bibliography for 4031824--4031827.cif.'
_cod_original_cell_volume        11760.4(13)
_cod_database_code               4031825
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.870
_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
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C20(H20A,H20B), C30(H30A,H30B), C49(H49A,H49B), C59(H59A,
 H59B), C69(H69A,H69B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16), C22(H22), C23(H23), C25(H25),
 C26(H26), C32(H32), C33(H33), C35(H35), C36(H36), C51(H51), C52(H52), C54(H54),
  C55(H55), C61(H61), C62(H62), C64(H64), C65(H65), C71(H71), C72(H72),
 C74(H74), C75(H75)
2.c X=CH2 refined with riding coordinates:
 N4(H4A,H4B), N5(H5A,H5B), N9(H9D,H9E), N10(H10C,H10D), N14(H14A,H14B),
 N15(H15A,H15B), N19(H19A,H19B), N20(H20C,H20D), N24(H24A,H24B), N25(H25A,H25B),
  N29(H29A,H29B), N30(H30C,H30D)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C46(H46A,H46B,H46C),
 C47(H47A,H47B,H47C), C48(H48A,H48B,H48C)
;
_platon_squeeze_void_probe_radius 1.20
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'