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_7225471
_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 H11 N3 O2'
_chemical_formula_sum            'C17 H11 N3 O2'
_chemical_formula_weight         289.29
_chemical_melting_point          477
_chemical_name_common            5a
_chemical_name_systematic
3-(4-phenyl-1H-1,2,3-triazol-1-yl)-2H-chromen-2-one
_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   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                90.00
_cell_angle_beta                 113.248(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9013(6)
_cell_length_b                   7.3232(3)
_cell_length_c                   15.7261(7)
_cell_measurement_reflns_used    5011
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.3250
_cell_measurement_theta_min      3.0190
_cell_volume                     1365.14(12)
_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 -124.00  -99.00   1.0000    3.2200
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -99.0000  120.0000 25

  2 omega -118.00    3.00   1.0000    3.2200
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -19.0000    0.0000 121

  3 omega  -46.00   25.00   1.0000    3.2200
omega____ theta____ kappa____ phi______ frames
    -      -41.4254   37.0000 -180.0000 71

  4 omega   64.00  107.00   1.0000    3.2200
omega____ theta____ kappa____ phi______ frames
    -       41.4254  178.0000  -30.0000 43

  5 omega   58.00   84.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  178.0000 -150.0000 26

  6 omega  107.00  137.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  178.0000 -150.0000 30

  7 omega   40.00   84.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000   30.0000 44

  8 omega   38.00  109.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  -30.0000 71

  9 omega   38.00   90.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000 -150.0000 52

 10 omega  129.00  178.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  100.0000   12.0000 49

 11 omega  102.00  135.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000  -30.0000 33

 12 omega   46.00   92.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000  -30.0000 46

 13 omega   42.00   80.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000   60.0000 38

 14 omega   81.00  107.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -180.0000 26

 15 omega  125.00  152.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -180.0000 27

 16 omega   42.00   88.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000  150.0000 46

 17 omega   49.00   86.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000   90.0000 37

 18 omega  153.00  178.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000  -30.0000 25

 19 omega   54.00   80.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000  150.0000 26

 20 omega -123.00    5.00   1.0000    3.2200
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -19.0000  150.0000 128

 21 omega -120.00   -8.00   1.0000    3.2200
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000  150.0000 112

 22 omega -115.00  -12.00   1.0000    3.2200
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -57.0000  -60.0000 103

 23 omega   57.00  131.00   1.0000    3.2200
omega____ theta____ kappa____ phi______ frames
    -       41.4254  178.0000 -150.0000 74

 24 omega   57.00  131.00   1.0000    3.2200
omega____ theta____ kappa____ phi______ frames
    -       41.4254  178.0000   90.0000 74

 25 omega   54.00  178.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000   15.0000  -30.0000 124

 26 omega   81.00  162.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  -30.0000 81

 27 omega   84.00  178.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000  150.0000 94

 28 omega   85.00  178.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   90.0000 93

 29 omega   37.00  116.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000 -180.0000 79

 30 omega   85.00  178.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -150.0000 93

 31 omega   84.00  178.00   1.0000   12.8600
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000   60.0000 94
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0046270000
_diffrn_orient_matrix_UB_12      -0.1323761000
_diffrn_orient_matrix_UB_13      -0.0775758000
_diffrn_orient_matrix_UB_21      0.1119954000
_diffrn_orient_matrix_UB_22      -0.0868258000
_diffrn_orient_matrix_UB_23      0.0651243000
_diffrn_orient_matrix_UB_31      -0.0657152000
_diffrn_orient_matrix_UB_32      -0.1385722000
_diffrn_orient_matrix_UB_33      0.0332935000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_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            14623
_diffrn_reflns_theta_full        74.50
_diffrn_reflns_theta_max         74.50
_diffrn_reflns_theta_min         3.78
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   analytical
_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)
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            brown
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_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          0.3754
_exptl_crystal_size_mid          0.3031
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2786
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0681P)^2^+0.2207P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1310
_reflns_number_gt                2325
_reflns_number_total             2786
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce01041e2.cif
_cod_data_source_block           5a
_cod_depositor_comments
'Adding full bibliography for 7225471--7225478.cif.'
_cod_database_code               7225471
_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), C14(H14),
 C15(H15), C16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'