Heterocycles as supramolecular handles for crystal engineering: a case study with 7-(diethylamino)coumarin derivatives
Castro, Geraldyne; Romero-Ávila, Margarita; Farfán, Norberto; Arcos-Ramos, Rafael; Maldonado-Domínguez, Mauricio; RSC Advances 14 (2024) 20824–20836; doi:10.1039/D4RA03656E

data_7248920
_publ_section_title
;
 Heterocycles as supramolecular handles for crystal engineering: a case
 study with 7-(diethylamino)coumarin derivatives
;
_journal_issue                   29
_journal_name_full               'RSC Advances'
_journal_page_first              20824
_journal_page_last               20836
_journal_paper_doi               10.1039/D4RA03656E
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C16 H17 N5 O2'
_chemical_formula_sum            'C16 H17 N5 O2'
_chemical_formula_weight         311.346
_chemical_melting_point          512.0(10)
_chemical_name_common
(E)-3-(((4H-1,2,4-triazol-4-yl)imino)methyl)-7-(diethylamino)-2H-chromen-2-one
_chemical_name_systematic        'Compound 11'
_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_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc2jhh5q
_audit_creation_date             2024-02-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-03-07 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.165(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3674(10)
_cell_length_b                   10.3669(7)
_cell_length_c                   10.6054(6)
_cell_measurement_reflns_used    8803
_cell_measurement_temperature    121.6(5)
_cell_measurement_theta_max      29.2490
_cell_measurement_theta_min      3.9530
_cell_volume                     1538.11(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      121.6
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.9345
_diffrn_measurement_details
;
  1 omega  -18.00   83.00   1.0000   19.7800
omega____ theta____ kappa____ phi______ frames
    -       11.7672   57.0000   90.0000 101

  2 omega  -24.00   54.00   1.0000   19.7800
omega____ theta____ kappa____ phi______ frames
    -       11.7672  -99.0000  -90.0000 78

  3 omega  -43.00   41.00   1.0000   19.7800
omega____ theta____ kappa____ phi______ frames
    -       11.7672  -57.0000  150.0000 84

  4 omega   43.00  101.00   1.0000   19.7800
omega____ theta____ kappa____ phi______ frames
    -       11.7672  179.0000 -180.0000 58

  5 omega  -14.00   88.00   1.0000   19.7800
omega____ theta____ kappa____ phi______ frames
    -       11.7672   38.0000  -30.0000 102

  6 omega  -34.00   90.00   1.0000   19.7800
omega____ theta____ kappa____ phi______ frames
    -       11.7672   19.0000 -120.0000 124

  7 omega   45.00   76.00   1.0000   19.7800
omega____ theta____ kappa____ phi______ frames
    -      -12.0797 -179.0000  -30.0000 31

  8 omega  -87.00  -36.00   1.0000   19.7800
omega____ theta____ kappa____ phi______ frames
    -      -12.0797  152.0000  -99.0000 51

  9 omega  -22.00   90.00   1.0000   19.7800
omega____ theta____ kappa____ phi______ frames
    -       11.7672   77.0000 -150.0000 112

 10 omega   32.00  101.00   1.0000   19.7800
omega____ theta____ kappa____ phi______ frames
    -       11.7672 -179.0000  120.0000 69
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.9978
_diffrn_reflns_Laue_measured_fraction_max 0.9345
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            32266
_diffrn_reflns_point_group_measured_fraction_full 0.9978
_diffrn_reflns_point_group_measured_fraction_max 0.9345
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         29.54
_diffrn_reflns_theta_min         3.51
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       irregular
_exptl_crystal_F_000             656.276
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2'
_exptl_crystal_size_max          0.4735
_exptl_crystal_size_mid          0.2728
_exptl_crystal_size_min          0.1053
_refine_diff_density_max         0.3835
_refine_diff_density_min         -0.2745
_refine_diff_density_rms         0.0637
_refine_ls_d_res_high            0.7208
_refine_ls_d_res_low             5.7984
_refine_ls_goodness_of_fit_ref   1.0953
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0953
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1474
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              19
_reflns_limit_h_min              -19
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3267
_reflns_number_total             4035
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ra03656e2.cif
_cod_data_source_block           GLCH169-953
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '511 - 513' was changed to
'512.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_cell_volume        1538.12(18)
_cod_database_code               7248920
_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.a Secondary CH2 refined with riding coordinates:
 C16(H16a,H16b), C6(H6a,H6b)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C12(H12), C2(H2), C11(H11), C13(H13), C17(H17), C15(H15)
2.c Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c), C3(H3a,H3b,H3c)
;
_olex2_submission_special_instructions 'No special instructions were received'