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_7227675
_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         'C21 H27 N3 O9'
_chemical_formula_sum            'C21 H27 N3 O9'
_chemical_formula_weight         465.45
_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
_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                77.472(3)
_cell_angle_beta                 87.209(4)
_cell_angle_gamma                83.111(3)
_cell_formula_units_Z            2
_cell_length_a                   4.9042(2)
_cell_length_b                   16.9098(6)
_cell_length_c                   17.0515(7)
_cell_measurement_reflns_used    2070
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.05
_cell_measurement_theta_min      2.66
_cell_volume                     1370.05(9)
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0406
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10762
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        66.771
_diffrn_reflns_theta_max         66.771
_diffrn_reflns_theta_min         2.694
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0795 before and 0.0522 after correction.
The Ratio of minimum to maximum transmission is 0.8482.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_description       needle
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         4771
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0581
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0884P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1651
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3215
_reflns_number_total             4771
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00206h2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7227672--7227675.cif.'
_cod_original_cell_volume        1370.06(9)
_cod_database_code               7227675
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.928
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N3-H3
 0.9 with sigma of 0.01
 N2-H2
 0.9 with sigma of 0.01
 N1-H1
 0.9 with sigma of 0.01
 O8-H8
 0.84 with sigma of 0.01
 O4-H4
 0.84 with sigma of 0.01
 O6-H6
 0.84 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C18(H18A,H18B), C19(H19A,H19B), C14(H14A,
 H14B), C8(H8A,H8B), C9(H9A,H9B), C20(H20A,H20B), C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4A), C6(H6A)
;
_shelx_res_checksum              16028
_shelx_fab_checksum              45122
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'