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_7225473
_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_formula_moiety         'C18 H13 N3 O3'
_chemical_formula_sum            'C18 H13 N3 O3'
_chemical_formula_weight         319.31
_chemical_melting_point          512
_chemical_name_common            5c
_chemical_name_systematic
7-methoxy-3-(4-phenyl-1,2,3-triazol-1-yl)-chromen-2-one
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_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                 92.127(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.17677(17)
_cell_length_b                   9.5698(3)
_cell_length_c                   30.6216(9)
_cell_measurement_reflns_used    8136
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.1060
_cell_measurement_theta_min      4.6160
_cell_volume                     1515.97(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 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -67.00  -12.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -57.0000  -90.0000 55

  2 omega -114.00  -89.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -57.0000  -90.0000 25

  3 omega -102.00  -41.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -77.0000    0.0000 61

  4 omega  -52.00   -8.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -77.0000 -180.0000 44

  5 omega  -37.00   -9.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -77.0000    0.0000 28

  6 omega  -71.00   -8.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -77.0000   79.0000 63

  7 omega   80.00  128.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3004  178.0000  150.0000 48

  8 omega   57.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3004  178.0000  -60.0000 74

  9 omega  -60.00  -28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -150.0000 32

 10 omega -135.00  -94.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -78.0000  -21.4535 41

 11 omega -140.00  -93.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -76.0000  -99.3781 47

 12 omega  -54.00   13.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000   45.0000  -30.0000 67

 13 omega  -77.00  -30.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -180.0000 47

 14 omega  -93.00  -66.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  120.0000 27

 15 omega  -64.00  -28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  120.0000 36

 16 omega -138.00 -102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   30.0000 36

 17 omega  -58.00  -28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -60.0000 30

 18 omega -136.00 -108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000 -111.0000  -30.0000 28

 19 omega  -69.00  -30.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -76.0000  -99.3781 39

 20 omega -135.00  -28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   79.0000 107

 21 omega  -63.00  -28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -78.0000  -21.4535 35

 22 omega -140.00  -95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -150.0000 45

 23 omega  -62.00  -30.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   30.0000 32

 24 omega   81.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -30.0000 26

 25 omega   50.00   76.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000 -180.0000 26

 26 omega   52.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000  -60.0000 46

 27 omega   86.00  171.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  120.0000 85

 28 omega   84.00  115.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000 -180.0000 31

 29 omega   53.00  144.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -61.0000   90.0000 91

 30 omega  113.00  164.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -30.0000 51

 31 omega   86.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -90.0000 91

 32 omega   38.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000    0.0000 78

 33 omega   85.00  111.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -120.0000 26

 34 omega   85.00  171.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   60.0000 86

 35 omega  131.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000   30.0000 46

 36 omega   85.00  111.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -30.0000 26

 37 omega   81.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   30.0000 26

 38 omega   81.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -90.0000 26

 39 omega   82.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  120.0000 25

 40 omega   49.00   88.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000   30.0000 39

 41 omega   42.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  -90.0000 66

 42 omega   92.00  169.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000    0.0000 77

 43 omega   85.00  165.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  150.0000 80

 44 omega   85.00  160.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   30.0000 75

 45 omega   85.00  154.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -180.0000 69

 46 omega   31.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000   60.0000 78

 47 omega   87.00  136.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -60.0000 49

 48 omega   82.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   90.0000 25

 49 omega  126.00  153.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -120.0000 27

 50 omega   85.00  165.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   90.0000 80

 51 omega   81.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   60.0000 26

 52 omega   82.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000    0.0000 27

 53 omega  133.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  150.0000 42

 54 omega   81.00  167.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -154.0000 86

 55 omega   81.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -120.0000 25

 56 omega  113.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -120.0000 63

 57 omega   81.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  150.0000 26

 58 omega   81.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -60.0000 97

 59 omega   81.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -180.0000 26

 60 omega   57.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  -30.0000 48

 61 omega -120.00   -8.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -77.0000  120.0000 112

 62 omega -124.00  -79.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -99.0000   90.0000 45

 63 omega -124.00  -79.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -99.0000 -150.0000 45

 64 omega -115.00  -12.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -57.0000 -150.0000 103

 65 omega -124.00  -79.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -99.0000  -30.0000 45

 66 omega   57.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3004  178.0000   60.0000 74

 67 omega   15.00  117.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3004   37.0000   30.0000 102

 68 omega  -55.00   13.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000   45.0000 -150.0000 68

 69 omega -140.00  -28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   60.0000 112

 70 omega -140.00  -28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  150.0000 112

 71 omega -140.00  -28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -120.0000 112

 72 omega -140.00  -28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -60.0000 112

 73 omega -141.00  -27.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -79.0000  -29.7275 114

 74 omega   87.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000 -150.0000 91

 75 omega   81.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -154.0000 97

 76 omega   85.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -60.0000 93

 77 omega   85.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000    0.0000 93

 78 omega   37.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  120.0000 79

 79 omega   31.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  -90.0000 78

 80 omega   84.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000   30.0000 94

 81 omega   31.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000 -150.0000 78

 82 omega   85.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   30.0000 93

 83 omega   40.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000 -120.0000 58

 84 omega   81.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -120.0000 97

 85 omega   81.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   30.0000 97

 86 omega   31.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000    0.0000 78

 87 omega  100.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000 -180.0000 78

 88 omega   81.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -60.0000 97

 89 omega   85.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -180.0000 93

 90 omega   81.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   60.0000 97

 91 omega   87.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000  150.0000 91

 92 omega   81.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -90.0000 97

 93 omega   87.00  132.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000   30.0000 45
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0635508000
_diffrn_orient_matrix_UB_12      0.1129458000
_diffrn_orient_matrix_UB_13      -0.0338129000
_diffrn_orient_matrix_UB_21      -0.1550153000
_diffrn_orient_matrix_UB_22      0.1079451000
_diffrn_orient_matrix_UB_23      0.0256248000
_diffrn_orient_matrix_UB_31      0.2461869000
_diffrn_orient_matrix_UB_32      0.0387955000
_diffrn_orient_matrix_UB_33      0.0271083000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            53243
_diffrn_reflns_theta_full        77.68
_diffrn_reflns_theta_max         77.68
_diffrn_reflns_theta_min         2.89
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39151
_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            red
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl Acetate'
_exptl_crystal_size_max          0.1865
_exptl_crystal_size_mid          0.0547
_exptl_crystal_size_min          0.0547
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3210
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0543P)^2^+0.3292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1224
_reflns_number_gt                2272
_reflns_number_total             3210
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce01041e2.cif
_cod_data_source_block           5c
_cod_depositor_comments
'Adding full bibliography for 7225471--7225478.cif.'
_cod_original_cell_volume        1515.96(8)
_cod_database_code               7225473
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_olex2_date_sample_data_collection 1383586274.5
_olex2_submission_special_instructions 'No special instructions were received'