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_4031826
_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         'C42 H45 N15 O3'
_chemical_formula_sum            'C42 H45 N15 O3'
_chemical_formula_weight         807.93
_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   geom
_audit_creation_date             2015-10-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                70.131(4)
_cell_angle_beta                 74.396(4)
_cell_angle_gamma                72.114(4)
_cell_formula_units_Z            2
_cell_length_a                   12.4986(9)
_cell_length_b                   14.7043(10)
_cell_length_c                   20.3073(13)
_cell_measurement_reflns_used    3030
_cell_measurement_temperature    100
_cell_measurement_theta_max      55.168
_cell_measurement_theta_min      2.353
_cell_volume                     3283.4(4)
_computing_cell_refinement       'SAINT V8.18C(Bruker AXS, 2009)'
_computing_data_collection       'APEX2  (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V8.18C(Bruker AXS, 2009)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Quazar MX'
_diffrn_radiation_source         'Incoatec I\muS Microsource '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            49760
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.572
_diffrn_reflns_theta_min         2.353
_exptl_absorpt_coefficient_mu    0.445
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0928 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.8361.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.817
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
)

Attempts to  model disordered solvent molecules
were unsuccessful. PLATON/SQUEEZE  was used to correct
the data for the presence of the disordered solvent.
A potential solvent volume of 1521 \%A^3^, 
46.3 % of the total unit-cell volume, was found.
403 electrons per unit cell worth of scattering were located
in the void. The reported structure is based on the 
PLATON/SQUEEZE corrected data. The actual solvent content is
unknown, so several quantities calculated like empirical formula, density, 
absorption coefficient, F(000) etc. may be incorrect.

References:  
Sluis, P. van der & Spek, A.L. (1990). Acta Cryst. A46, 194-201.
Spek, A.L. (2015). Acta Cryst. C71, 9-18.

TITL HELZ30 in P-1
CELL   12.4986   14.7043   20.3073     70.13     74.40     72.11
SPGR P-1
C101 0.423 0.654 0.295 !       8.42 eA-3
C102 0.950 0.224 0.142 !       8.12 eA-3
C103 0.453 0.818 0.213 !       6.48 eA-3
C104 0.408 0.713 0.252 !       5.75 eA-3
C105 0.220 0.578 0.238 !       5.65 eA-3
C106 0.722 0.245 0.205 !       4.89 eA-3
C107 0.158 0.571 0.343 !       4.19 eA-3
C108 0.561 0.357 0.235 !       4.10 eA-3
C109 0.518 0.818 0.267 !       4.00 eA-3
C110 0.155 0.594 0.283 !       3.95 eA-3
C111 0.426 0.897 0.151 !       3.79 eA-3
C112 0.063 0.576 0.405 !       2.99 eA-3
C113 0.559 0.339 0.293 !       2.76 eA-3
C114 0.252 0.482 0.381 !       2.72 eA-3
C115 0.657 0.322 0.181 !       2.49 eA-3
C116 0.642 0.180 0.045 !       2.48 eA-3
C117 0.469 0.131 0.045 !       2.22 eA-3
C118 0.484 0.692 0.045 !       2.19 eA-3
C119 0.284 0.123 0.032 !       2.04 eA-3
C120 0.313 0.070 0.002 !       1.84 eA-3
C121 0.357 0.170 0.011 !       1.80 eA-3
C122 0.467 0.421 0.204 !       1.77 eA-3
C123 0.594 0.622 0.064 !       1.74 eA-3
C124 0.579 0.674 0.060 !       1.72 eA-3
C125 0.652 0.736 0.044 !       1.72 eA-3
C126 0.534 0.221 0.013 !       1.70 eA-3
C127 0.657 0.293 0.239 !       1.65 eA-3
C128 0.252 0.429 0.092 !       1.49 eA-3
C129 0.621 0.603 0.123 !       1.49 eA-3
C130 0.248 0.363 0.128 !       1.47 eA-3
C131 0.223 0.316 0.141 !       1.43 eA-3
C132 0.489 0.369 0.319 !       1.30 eA-3
C133 0.674 0.575 0.012 !       1.30 eA-3
C134 0.500 1.000 0.000 !       1.26 eA-3
C135 0.281 0.591 0.026 !       1.23 eA-3
C136 0.470 0.624 0.068 !       1.14 eA-3
C137 0.641 0.478-0.002 !       1.08 eA-3
C138 0.498 0.475 0.015 !       1.05 eA-3
C139 0.432 0.217 0.092 !       0.98 eA-3
C140 0.303 0.357 0.020 !       0.98 eA-3
C141 0.295 0.232 0.108 !       0.97 eA-3
C142 0.312 0.473 0.057 !       0.95 eA-3
C143 0.325 0.327 0.079 !       0.94 eA-3
C144 0.437 0.574 0.026 !       0.92 eA-3
C145 0.454 0.305 0.080 !       0.78 eA-3
C146 0.107 0.459 0.499 !       0.77 eA-3
C147 0.672 0.042 0.011 !       0.72 eA-3
C148 0.934 0.558 0.470 !       0.71 eA-3
C149 1.000 0.500 0.500 !       0.69 eA-3
C150 0.203 0.480 0.154 !       0.66 eA-3
C151 0.340 0.359 0.127 !       0.63 eA-3
C152 0.613 0.362 0.106 !       0.62 eA-3
C153 0.681 0.308 0.093 !       0.62 eA-3
C154 0.629 0.067 0.035 !       0.61 eA-3
C155 0.801 0.236 0.142 !       0.59 eA-3
C156 0.620 0.300 0.081 !       0.59 eA-3
Q157 0.349 0.220 0.409 !       0.57 eA-3
Q158 0.171 0.869 0.174 !       0.56 eA-3
Q159 0.670 0.449 0.411 !       0.56 eA-3
C160 0.794 0.298 0.030 !       0.56 eA-3
C161 0.596 0.516 0.139 !       0.56 eA-3
C162 0.531 0.420 0.109 !       0.55 eA-3
C163 0.746 0.340 0.016 !       0.54 eA-3
C164 0.749 0.236 0.094 !       0.54 eA-3
C165 0.594 0.275-0.008 !       0.54 eA-3
C166 0.483 0.405 0.061 !       0.51 eA-3
C167 0.517 0.966 0.151 !       0.51 eA-3
)
;
_refine_diff_density_max         1.192
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         12253
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1307
_refine_ls_R_factor_gt           0.0778
_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^)+(0.1531P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2234
_refine_ls_wR_factor_ref         0.2629
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6479
_reflns_number_total             12253
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02552_si_002.cif
_cod_data_source_block           3c_DMF_PhCl
_cod_depositor_comments
'Adding full bibliography for 4031824--4031827.cif.'
_cod_database_code               4031826
_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:
 C7(H7A,H7B), C9(H9A,H9B), C11(H11A,H11B), C13(H13A,H13B), C23(H23A,H23B),
 C33(H33A,H33B)
2.b Me refined with riding coordinates:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C18(H18), C19(H19), C25(H25), C26(H26), C28(H28),
 C29(H29), C35(H35), C36(H36), C38(H38), C39(H39)
2.d X=CH2 refined with riding coordinates:
 N4(H4A,H4B), N5(H5A,H5B), N9(H9C,H9D), N10(H10D,H10E), N14(H14A,H14B),
 N15(H15A,H15B)
;
_platon_squeeze_void_probe_radius 1.20
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'