Coordination chemistry of flexible benzene-1,3,5-tricarboxamide derived carboxylates; notable structural resilience and vaguely familiar packing motifs.
Lynes, Amy D.; Hawes, Chris S.; Byrne, Kevin; Schmitt, Wolfgang; Gunnlaugsson, Thorfinnur; Dalton transactions (Cambridge, England : 2003) 47 (2018) 5259–5268; doi:10.1039/C8DT00439K

data_7045845
_publ_section_title
;
 Coordination chemistry of flexible benzene-1,3,5-tricarboxamide derived
 carboxylates; notable structural resilience and vaguely familiar packing
 motifs.
;
_journal_issue                   15
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5259
_journal_page_last               5268
_journal_paper_doi               10.1039/C8DT00439K
_journal_volume                  47
_journal_year                    2018
_chemical_formula_moiety         'C18 H21 N3 O9, H0.67 O0.33, 0.17(O)'
_chemical_formula_sum            'C18 H22 N3 O9.5'
_chemical_formula_weight         432.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-12-21 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.3610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0286(4)
_cell_length_b                   6.9850(2)
_cell_length_c                   22.2051(6)
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.32
_cell_measurement_theta_min      3.84
_cell_volume                     2017.29(10)
_computing_cell_refinement       'SAINT V8.35A (2016)'
_computing_data_reduction        'SAINT V8.35A (2016)'
_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      99.98
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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  0.0349
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20803
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.348
_diffrn_reflns_theta_min         3.988
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.999
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0731 before and 0.0508 after correction. The Ratio of minimum to maximum transmission is 0.9112. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       rod
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         3693
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0477
_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^)+(0.0900P)^2^+0.8300P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1408
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3353
_reflns_number_total             3693
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt00439k2.cif
_cod_data_source_block           Me3L2
_cod_depositor_comments
'Adding full bibliography for 7045845--7045847.cif.'
_cod_original_formula_sum        'C18 H22 N3 O9.50'
_cod_database_code               7045845
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.848
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N1-H1 = N3-H3 = N2-H2
 0.88 with sigma of 0.02
 C9A-O2A
 1.17 with sigma of 0.02
 C9A-C8
 1.49 with sigma of 0.01
 C9A-O3A
 1.33 with sigma of 0.02
 O3A-C10A
 1.45 with sigma of 0.02
 O10-H10
 0.85 with sigma of 0.02
 H10-H10_$1
 1.6 with sigma of 0.02
 O10-H10 = O10-H10_$1
 0.85 with sigma of 0.02
 H10_$1-O2_$3
 2.759 with sigma of 0.001
3. Rigid body (RIGU) restrains
 O2A, O3A, C8, C9A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
 Fixed Sof: O2(0.85) O2A(0.15) O3(0.85) O3A(0.15) O10(0.33333) H10(0.6667)
 H8AA(0.85) H8AB(0.85) H8BC(0.15) H8BD(0.15) C9(0.85) C9A(0.15) C10(0.85)
 H10A(0.85) H10B(0.85) H10C(0.85) C10A(0.15) H10D(0.15) H10E(0.15) H10F(0.15)
 O11(0.16667)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8AA,H8AB), C8(H8BC,H8BD), C12(H12A,H12B), C16(H16A,H16B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4), C6(H6)
5.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C10A(H10D,H10E,H10F), C14(H14A,H14B,H14C), C18(H18A,H18B,
 H18C)
;
_shelx_res_checksum              89364
_olex2_submission_special_instructions 'No special instructions were received'