Benzene-1,3,5-tricarboxamide n-alkyl ester and carboxylic acid derivatives: tuneable structural, morphological and thermal properties
Lynes, Amy D.; Hawes, Chris S.; Ward, Edward N.; Haffner, Benjamin; Möbius, Matthias E.; Byrne, Kevin; Schmitt, Wolfgang; Pal, Robert; Gunnlaugsson, Thorfinnur; CrystEngComm 19 (2017) 1427–; doi:10.1039/C7CE00206H

data_7227672
_publ_section_title
;
 Benzene-1,3,5-tricarboxamide n-alkyl ester and carboxylic acid
 derivatives: tuneable structural, morphological and thermal properties
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              1427
_journal_paper_doi               10.1039/C7CE00206H
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C30 H45 N3 O9'
_chemical_formula_sum            'C30 H45 N3 O9'
_chemical_formula_weight         591.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-26
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-01-26 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.567(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.627(2)
_cell_length_b                   7.3150(10)
_cell_length_c                   23.510(3)
_cell_measurement_reflns_used    1076
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      56.916
_cell_measurement_theta_min      3.836
_cell_volume                     3069.8(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1111
_diffrn_reflns_av_unetI/netI     0.1318
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16636
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_min         2.475
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0826 before and 0.0565 after correction.
The Ratio of minimum to maximum transmission is 0.7729.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       plate
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         5625
_refine_ls_number_restraints     68
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.2020
_refine_ls_R_factor_gt           0.0884
_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^)+(0.1243P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2088
_refine_ls_wR_factor_ref         0.2795
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2353
_reflns_number_total             5625
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00206h2.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 7227672--7227675.cif.'
_cod_original_cell_volume        3069.9(7)
_cod_database_code               7227672
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.892
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O6A-C22
 1.4 with sigma of 0.02
 O9A-C32
 1.5 with sigma of 0.02
 C31-O9
 1.5 with sigma of 0.02
 N1-H1
 0.9 with sigma of 0.02
 N3-H3
 0.9 with sigma of 0.02
 H2-N2
 0.9 with sigma of 0.02
 H16A-H24B_$1
 2.2 with sigma of 0.02
3. Restrained planarity
 O9A, C30, O8A, C29
 with sigma of 0.1
 O9, C30, O8, C29
 with sigma of 0.1
 C21, C22, O5A, O6A
 with sigma of 0.1
 C21, C22, O5, O6
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(O9A) \\sim Ueq, Uanis(O9) \\sim Ueq, Uanis(O8A) \\sim Ueq, Uanis(O8)
\\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(C32) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(O6A) \\sim Ueq, Uanis(O5A) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.02
Uanis(C24) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C32, C31
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O6A, C22, O5A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Fixed Sof: O5(0.85) O6(0.85) O8(0.75) O9(0.75) C23(0.85) H23A(0.85)
 H23B(0.85) H23C(0.85) C31(0.75) H31A(0.75) H31B(0.75) H31C(0.75) O8A(0.25)
 O9A(0.25) C32(0.25) H32A(0.25) H32B(0.25) H32C(0.25) O5A(0.15) O6A(0.15)
 C24(0.15) H24A(0.15) H24B(0.15) H24C(0.15)
7.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C10(H10A,H10B), C17(H17A,H17B), C11(H11A,H11B), C13(H13A,
 H13B), C18(H18A,H18B), C14(H14A,H14B), C19(H19A,H19B), C20(H20A,H20B),
 C26(H26A,H26B), C21(H21A,H21B), C27(H27A,H27B), C25(H25A,H25B), C28(H28A,H28B),
  C29(H29A,H29B)
7.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C2(H2A)
7.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              22930
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'