Engineering organic semiconducting solids. Multicomponent access to crystalline 3-(4-aryl-1,2,3-triazolyl)coumarins
de la Cerda-Pedro, J. E.; Arcos-Ramos, R.; Maldonado-Domínguez, M.; Rojas-Lima, S.; Romero-Ávila, M.; Carreón-Castro, M. P.; Santillan, R.; Farfán, N.; López-Ruiz, H.; CrystEngComm 18 (2016) 5562–; doi:10.1039/C6CE01041E

data_7225478
_publ_section_title
;
 Engineering organic semiconducting solids. Multicomponent access to
 crystalline 3-(4-aryl-1,2,3-triazolyl)coumarins
;
_journal_issue                   29
_journal_name_full               CrystEngComm
_journal_page_first              5562
_journal_paper_doi               10.1039/C6CE01041E
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H10 N4 O2'
_chemical_formula_sum            'C16 H10 N4 O2'
_chemical_formula_weight         290.28
_chemical_melting_point          508
_chemical_name_common            5l
_chemical_name_systematic
3-(4-(pyridin-2-yl)-1H-1,2,3-triazol-1-yl)-2H-chromen-2-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-10-09
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2016-02-24 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3822(2)
_cell_length_b                   7.6039(3)
_cell_length_c                   23.2450(8)
_cell_measurement_reflns_used    7627
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.1710
_cell_measurement_theta_min      3.7490
_cell_volume                     1304.82(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_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      293(2)
_diffrn_detector_area_resol_mean 10.3659
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega  -56.00  -16.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -37.0000  120.0000 40

  2 omega -116.00  -82.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -37.0000  120.0000 34

  3 omega  -48.00   -9.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000   30.0000 39

  4 omega -120.00  -93.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000  120.0000 27

  5 omega  -57.00   -8.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000  120.0000 49

  6 omega -119.00  -43.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000  -90.0000 76

  7 omega  -42.00   -8.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000  -90.0000 34

  8 omega -119.00  -53.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000   30.0000 66

  9 omega   57.00  114.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -       41.4254  178.0000  -90.0000 57

 10 omega   13.00   38.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -       41.4254   57.0000 -180.0000 25

 11 omega   57.00  127.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -       41.4254  178.0000 -180.0000 70

 12 omega   45.00  120.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -       41.4254 -166.0000   57.0000 75

 13 omega  -84.00  -28.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  150.0000 56

 14 omega -137.00 -102.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -79.0000 -147.8753 35

 15 omega -139.00  -80.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000 -111.0000  120.0000 59

 16 omega -117.00  -89.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -60.0000 28

 17 omega  -67.00  -28.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -60.0000 39

 18 omega -131.00 -104.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -120.0000 27

 19 omega  -56.00  -28.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   30.0000 28

 20 omega  -53.00  -28.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -120.0000 25

 21 omega -139.00  -86.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -79.0000   -7.9207 53

 22 omega  -60.00  -27.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -79.0000   -7.9207 33

 23 omega  -93.00  -27.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -79.0000 -147.8753 66

 24 omega  -92.00  -28.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   90.0000 64

 25 omega  131.00  166.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -180.0000 35

 26 omega   86.00  113.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -30.0000 27

 27 omega   32.00  102.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000 -180.0000 70

 28 omega   81.00  108.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -180.0000 27

 29 omega   54.00  144.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -61.0000 -180.0000 90

 30 omega   82.00  109.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  150.0000 27

 31 omega   33.00   90.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  150.0000 57

 32 omega  125.00  153.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   60.0000 28

 33 omega   86.00  114.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   60.0000 28

 34 omega   85.00  174.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -60.0000 89

 35 omega   81.00  153.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  120.0000 72

 36 omega   87.00  139.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -90.0000 52

 37 omega  119.00  172.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   60.0000 53

 38 omega   81.00  107.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   90.0000 26

 39 omega   81.00  111.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   60.0000 30

 40 omega   86.00  113.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -120.0000 27

 41 omega   81.00  108.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -150.0000 27

 42 omega   69.00  107.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  -60.0000 38

 43 omega   85.00  125.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -180.0000 40

 44 omega   86.00  142.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -150.0000 56

 45 omega   85.00  112.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  120.0000 27

 46 omega  120.00  173.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000    0.0000 53

 47 omega  115.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   30.0000 63

 48 omega   81.00  114.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   30.0000 33

 49 omega   85.00  118.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   30.0000 33

 50 omega   87.00  177.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   90.0000 90

 51 omega   81.00  108.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000    0.0000 27

 52 omega   58.00  139.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000  178.0000  150.0000 81

 53 omega  115.00  152.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -90.0000 37

 54 omega   81.00  108.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -90.0000 27

 55 omega   38.00  110.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  120.0000 72

 56 omega   81.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -30.0000 97

 57 omega   85.00  128.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000    0.0000 43

 58 omega   88.00  118.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -116.0000 -113.0000 30

 59 omega   38.00   80.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000    0.0000 42

 60 omega   85.00  148.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  150.0000 63

 61 omega   81.00  111.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -60.0000 30

 62 omega   79.00  115.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000   30.0000 36

 63 omega   38.00   77.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000   30.0000 39

 64 omega  124.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  150.0000 54

 65 omega   81.00  176.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -120.0000 95

 66 omega  -71.00   33.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254   57.0000  150.0000 104

 67 omega -130.00  -32.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  178.0000  150.0000 98

 68 omega -115.00  -12.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -57.0000   30.0000 103

 69 omega -124.00  -79.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -99.0000  -90.0000 45

 70 omega -120.00   -8.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000  -30.0000 112

 71 omega -120.00   -8.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000  150.0000 112

 72 omega -118.00  -15.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -37.0000  150.0000 103

 73 omega -124.00  -79.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -99.0000 -180.0000 45

 74 omega -120.00   -8.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000 -150.0000 112

 75 omega   68.00  122.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -       41.4254  165.0000  122.0000 54

 76 omega -136.00  -31.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -61.0000  -30.0000 105

 77 omega -140.00  -28.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   60.0000 112

 78 omega -140.00  -28.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -90.0000 112

 79 omega -140.00  -28.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  120.0000 112

 80 omega -140.00  -28.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -180.0000 112

 81 omega -141.00  -27.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -79.0000 -147.8753 114

 82 omega -140.00  -28.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -30.0000 112

 83 omega   40.00   98.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000  -90.0000 58

 84 omega   81.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   30.0000 97

 85 omega   87.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000  -90.0000 91

 86 omega  100.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000  150.0000 78

 87 omega   38.00  118.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -116.0000   24.0000 80

 88 omega   32.00  176.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -15.0000  120.0000 144

 89 omega   40.00   98.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000   30.0000 58

 90 omega   87.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000  150.0000 91

 91 omega   81.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -120.0000 97

 92 omega   87.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000   90.0000 91

 93 omega   37.00  116.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  -90.0000 79

 94 omega   87.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000 -180.0000 91

 95 omega   81.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -60.0000 97

 96 omega   81.00  178.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -30.0000 97

 97 omega   38.00  118.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -116.0000 -113.0000 80

 98 omega   31.00   82.00   1.0000    2.8500
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  -60.0000 51
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0459494000
_diffrn_orient_matrix_UB_12      0.1834257000
_diffrn_orient_matrix_UB_13      -0.0241485000
_diffrn_orient_matrix_UB_21      -0.0515064000
_diffrn_orient_matrix_UB_22      0.0625824000
_diffrn_orient_matrix_UB_23      0.0608830000
_diffrn_orient_matrix_UB_31      0.1968475000
_diffrn_orient_matrix_UB_32      0.0590635000
_diffrn_orient_matrix_UB_33      0.0102907000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            47344
_diffrn_reflns_theta_full        78.42
_diffrn_reflns_theta_max         78.42
_diffrn_reflns_theta_min         3.80
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl Acetate'
_exptl_crystal_size_max          0.1589
_exptl_crystal_size_mid          0.1589
_exptl_crystal_size_min          0.1254
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0571P)^2^+0.4951P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1371
_reflns_number_gt                2270
_reflns_number_total             2795
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce01041e2.cif
_cod_data_source_block           5l
_cod_depositor_comments
'Adding full bibliography for 7225471--7225478.cif.'
_cod_database_code               7225478
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'