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_7225475
_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         'C17 H10 F N3 O2'
_chemical_formula_sum            'C17 H10 F N3 O2'
_chemical_formula_weight         307.28
_chemical_melting_point          516
_chemical_name_common            5h
_chemical_name_systematic
3-(4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl)-2H-chromen-2-one
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-10-09
_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                79.805(4)
_cell_angle_beta                 89.756(4)
_cell_angle_gamma                84.314(4)
_cell_formula_units_Z            2
_cell_length_a                   5.8032(3)
_cell_length_b                   7.5652(4)
_cell_length_c                   15.7517(7)
_cell_measurement_reflns_used    4101
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.1130
_cell_measurement_theta_min      5.6630
_cell_volume                     677.21(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega -120.00   -4.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -19.0000   90.0000 116

  2 omega -122.00  -90.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -99.0000  -90.0000 32

  3 omega  -77.00  -21.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -37.0000 -180.0000 56

  4 omega   57.00  130.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -       41.3004  178.0000  120.0000 73

  5 omega   61.00   88.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -       41.3004  178.0000 -180.0000 27

  6 omega   58.00  101.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -       41.3004  178.0000   30.0000 43

  7 omega   85.00  129.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -       41.3004  178.0000  -90.0000 44

  8 omega   43.00   80.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000   90.0000 37

  9 omega   46.00   75.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000 -180.0000 29

 10 omega   37.00   80.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000 -120.0000 43

 11 omega   81.00  113.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000   90.0000 32

 12 omega  122.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000 -180.0000 56

 13 omega   49.00   88.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000  -90.0000 39

 14 omega   87.00  125.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000  -60.0000 38

 15 omega   78.00  125.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  178.0000 -180.0000 47

 16 omega   38.00  116.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  150.0000 78

 17 omega   48.00  107.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  -90.0000 59

 18 omega   38.00  104.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -77.0000 -180.0000 66

 19 omega   50.00   85.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000   30.0000 35

 20 omega   85.00  118.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  178.0000   90.0000 33

 21 omega  128.00  173.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000  -60.0000 45

 22 omega   50.00  108.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  -30.0000 58

 23 omega  103.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000  150.0000 75

 24 omega  130.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000  -30.0000 48

 25 omega   62.00   99.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  150.0000 37

 26 omega   90.00  173.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -150.0000 83

 27 omega -115.00  -12.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -57.0000  -90.0000 103

 28 omega -120.00   -8.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -77.0000  120.0000 112

 29 omega -124.00  -79.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -99.0000  -30.0000 45

 30 omega -124.00  -79.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -99.0000   90.0000 45

 31 omega -120.00   -8.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -77.0000 -150.0000 112

 32 omega -115.00  -12.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -57.0000    0.0000 103

 33 omega   57.00  131.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -       41.3004  178.0000  -90.0000 74

 34 omega   85.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -180.0000 93

 35 omega   81.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   60.0000 97

 36 omega   81.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -60.0000 97

 37 omega   85.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -120.0000 93

 38 omega   81.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   30.0000 97

 39 omega   87.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000    0.0000 91

 40 omega   31.00  109.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000 -120.0000 78

 41 omega   31.00  109.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  -30.0000 78

 42 omega   54.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   15.0000 -180.0000 124

 43 omega   81.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -90.0000 97

 44 omega   81.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   90.0000 97

 45 omega   85.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  150.0000 93

 46 omega   85.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -150.0000 93

 47 omega   84.00  178.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000   60.0000 94

 48 omega -120.00   -8.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -77.0000    0.0000 112

 49 omega -120.00  -27.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -77.0000   30.0000 93

 50 omega -120.00   -8.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -      -41.3004  -77.0000  -90.0000 112

 51 omega   57.00  131.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -       41.3004  178.0000  150.0000 74

 52 omega   -4.00   83.00   1.0000    5.9000
omega____ theta____ kappa____ phi______ frames
    -       41.3004  -99.0000  -90.0000 87
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1371517000
_diffrn_orient_matrix_UB_12      0.1095506000
_diffrn_orient_matrix_UB_13      -0.0787636000
_diffrn_orient_matrix_UB_21      0.2179213000
_diffrn_orient_matrix_UB_22      -0.0130188000
_diffrn_orient_matrix_UB_23      -0.0556326000
_diffrn_orient_matrix_UB_31      -0.0698932000
_diffrn_orient_matrix_UB_32      -0.1762663000
_diffrn_orient_matrix_UB_33      -0.0240390000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11484
_diffrn_reflns_theta_full        74.50
_diffrn_reflns_theta_max         74.50
_diffrn_reflns_theta_min         2.85
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.933
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70387
_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_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             316
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.6567
_exptl_crystal_size_mid          0.5217
_exptl_crystal_size_min          0.3536
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2775
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0871P)^2^+0.1120P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1492
_reflns_number_gt                2296
_reflns_number_total             2775
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce01041e2.cif
_cod_data_source_block           5h
_cod_depositor_comments
'Adding full bibliography for 7225471--7225478.cif.'
_cod_database_code               7225475
_reflns_odcompleteness_completeness 99.93
_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), C15(H15),
 C16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'