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_7225476
_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 H12 Cl N3 O3'
_chemical_formula_sum            'C18 H12 Cl N3 O3'
_chemical_formula_weight         353.77
_chemical_melting_point          521
_chemical_name_common            5j
_chemical_name_systematic
'3-(4-(4-chlorophenyl)-1H-1,2,3-triazol-1-yl)-6-methoxy-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_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_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                78.784(4)
_cell_angle_beta                 83.537(4)
_cell_angle_gamma                83.826(5)
_cell_formula_units_Z            2
_cell_length_a                   5.8823(4)
_cell_length_b                   7.5418(4)
_cell_length_c                   18.0542(8)
_cell_measurement_reflns_used    6665
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.0410
_cell_measurement_theta_min      4.9930
_cell_volume                     777.63(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  'olex2.refine (Bourhis et al., 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3659
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.9984
_diffrn_measurement_details
;
  1 omega  -49.00   35.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754   37.0000   60.0000 84

  2 omega -115.00  -12.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754  -57.0000  -90.0000 103

  3 omega  -47.00   34.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754   37.0000 -180.0000 81

  4 omega   61.00  122.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -       40.6754  178.0000  -30.0000 61

  5 omega   67.00  100.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -       40.6754  178.0000 -150.0000 33

  6 omega   86.00  131.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -       40.6754  178.0000 -180.0000 45

  7 omega   37.00   76.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000 -150.0000 39

  8 omega   57.00   88.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  150.0000 31

  9 omega  144.00  173.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000    0.0000 29

 10 omega  135.00  172.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  110.0000  -67.0000 37

 11 omega   38.00   90.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000  150.0000 52

 12 omega   90.00  116.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  150.0000 26

 13 omega   37.00   64.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000   30.0000 27

 14 omega   85.00  113.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000   30.0000 28

 15 omega   91.00  164.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000   60.0000 73

 16 omega   88.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000  -30.0000 90

 17 omega   38.00   87.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000   30.0000 49

 18 omega  132.00  169.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000 -180.0000 37

 19 omega   56.00  102.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000 -150.0000 46

 20 omega  107.00  164.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000 -180.0000 57

 21 omega   57.00  114.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  -60.0000 57

 22 omega  109.00  161.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000   60.0000 52

 23 omega  101.00  150.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  178.0000 -180.0000 49

 24 omega   61.00   88.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -77.0000  -60.0000 27

 25 omega  115.00  144.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -77.0000  -60.0000 29

 26 omega  110.00  164.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000  -90.0000 54

 27 omega   64.00  143.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -61.0000  -90.0000 79

 28 omega -115.00  -11.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754  -57.0000  150.0000 104

 29 omega -119.00   -7.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754  -77.0000  -90.0000 112

 30 omega  -70.00   33.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754   57.0000 -150.0000 103

 31 omega -117.00  -14.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754  -37.0000  -30.0000 103

 32 omega  -49.00   35.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754   37.0000  -30.0000 84

 33 omega -119.00   -7.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754  -77.0000   90.0000 112

 34 omega   53.00  129.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -       40.6754 -178.0000   60.0000 76

 35 omega   81.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000  150.0000 97

 36 omega   85.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -60.0000 93

 37 omega   87.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000 -150.0000 91

 38 omega   84.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000   30.0000 94

 39 omega   81.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -150.0000 97

 40 omega   85.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   90.0000 93

 41 omega   37.00  116.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000    0.0000 79

 42 omega   85.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -90.0000 93

 43 omega   84.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000  -90.0000 94

 44 omega   31.00  109.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000 -150.0000 78

 45 omega   85.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -30.0000 93

 46 omega   85.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000   60.0000 93

 47 omega   81.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000    0.0000 97

 48 omega   84.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000  150.0000 94

 49 omega -119.00   -7.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754  -77.0000  120.0000 112

 50 omega -119.00   -7.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754  -77.0000    0.0000 112

 51 omega -119.00   -7.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754  -77.0000  150.0000 112

 52 omega -117.00  -14.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754  -37.0000   30.0000 103

 53 omega -119.00   -7.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -      -40.6754  -77.0000   30.0000 112

 54 omega    7.00  119.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -       40.6754   77.0000  -90.0000 112

 55 omega   57.00  131.00   1.0000    1.8900
omega____ theta____ kappa____ phi______ frames
    -       40.6754  178.0000 -180.0000 74

 56 omega   81.00  144.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000 -120.0000 63

 57 omega   85.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000 -180.0000 93

 58 omega   81.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   60.0000 97

 59 omega   81.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000   30.0000 97

 60 omega   87.00  178.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000  150.0000 91

 61 omega   31.00  109.00   1.0000    7.5700
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000   60.0000 78
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.2285328000
_diffrn_orient_matrix_UB_12      -0.0294380000
_diffrn_orient_matrix_UB_13      0.0366547000
_diffrn_orient_matrix_UB_21      -0.1312877000
_diffrn_orient_matrix_UB_22      0.0224342000
_diffrn_orient_matrix_UB_23      0.0768760000
_diffrn_orient_matrix_UB_31      -0.0233878000
_diffrn_orient_matrix_UB_32      -0.2057542000
_diffrn_orient_matrix_UB_33      0.0195297000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0145
_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       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19292
_diffrn_reflns_theta_full        74.4970
_diffrn_reflns_theta_max         74.50
_diffrn_reflns_theta_min         5.02
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.391
_exptl_absorpt_correction_T_max  0.874
_exptl_absorpt_correction_T_min  0.696
_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_density_diffrn    1.5107
_exptl_crystal_description       prism
_exptl_crystal_F_000             365.8788
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl Acetate'
_exptl_crystal_size_max          0.4171
_exptl_crystal_size_mid          0.3177
_exptl_crystal_size_min          0.1315
_refine_diff_density_max         0.2428
_refine_diff_density_min         -0.3143
_refine_diff_density_rms         0.0427
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             8.8155
_refine_ls_goodness_of_fit_ref   1.0481
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0481
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0587P)^2^+0.2177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1187
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                2694
_reflns_number_total             3194
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6ce01041e2.cif
_cod_data_source_block           5j
_cod_depositor_comments
'Adding full bibliography for 7225471--7225478.cif.'
_cod_original_cell_volume        777.63(7)
_cod_database_code               7225476