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_7225474
_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         'C21 H20 N4 O2'
_chemical_formula_sum            'C21 H20 N4 O2'
_chemical_formula_weight         360.41
_chemical_melting_point          529
_chemical_name_common            5f
_chemical_name_systematic
7-(diethylamino)-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 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             2015-11-07
_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                 98.403(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7803(4)
_cell_length_b                   19.8443(6)
_cell_length_c                   7.6437(2)
_cell_measurement_reflns_used    4661
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.0220
_cell_measurement_theta_min      3.7630
_cell_volume                     1767.70(9)
_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  -71.00    8.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -      -41.4254   57.0000  -60.0000 79

  2 omega -114.00  -85.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -99.0000  -90.0000 29

  3 omega -121.00  -85.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -99.0000 -180.0000 36

  4 omega   61.00  129.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -       41.4254 -178.0000  120.0000 68

  5 omega   88.00  114.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -       41.4254  178.0000 -120.0000 26

  6 omega   48.00   81.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  150.0000 33

  7 omega   52.00   95.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000 -120.0000 43

  8 omega  122.00  178.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -90.0000 56

  9 omega   35.00  103.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  120.0000 68

 10 omega  110.00  171.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000    0.0000 61

 11 omega  110.00  175.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000 -150.0000 65

 12 omega   63.00   89.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000  -30.0000 26

 13 omega   59.00   99.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -105.0000   88.0000 40

 14 omega   66.00   93.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000 -180.0000 27

 15 omega   95.00  177.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000    0.0000 82

 16 omega   40.00   90.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000  120.0000 50

 17 omega   89.00  117.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  -90.0000 28

 18 omega -120.00   -8.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -77.0000  -90.0000 112

 19 omega -124.00  -79.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -99.0000  -30.0000 45

 20 omega -115.00  -12.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -57.0000  -30.0000 103

 21 omega -115.00  -12.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -57.0000   60.0000 103

 22 omega -115.00  -12.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -57.0000 -180.0000 103

 23 omega   84.00  178.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000   90.0000 94

 24 omega   31.00   71.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000    0.0000 40

 25 omega   37.00   90.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000  -60.0000 53

 26 omega   87.00  178.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000 -120.0000 91

 27 omega   84.00  178.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000  -30.0000 94

 28 omega   37.00  116.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  -60.0000 79

 29 omega   54.00  178.00   1.0000   11.9100
omega____ theta____ kappa____ phi______ frames
    -      115.0000   15.0000 -150.0000 124
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0862983000
_diffrn_orient_matrix_UB_12      -0.0561935000
_diffrn_orient_matrix_UB_13      0.0645425000
_diffrn_orient_matrix_UB_21      0.0681023000
_diffrn_orient_matrix_UB_22      0.0497220000
_diffrn_orient_matrix_UB_23      0.1301747000
_diffrn_orient_matrix_UB_31      -0.0734677000
_diffrn_orient_matrix_UB_32      -0.0198897000
_diffrn_orient_matrix_UB_33      0.1427942000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            18529
_diffrn_reflns_theta_full        74.45
_diffrn_reflns_theta_max         74.45
_diffrn_reflns_theta_min         3.79
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32579
_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    colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.5018
_exptl_crystal_size_mid          0.3403
_exptl_crystal_size_min          0.2714
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0773P)^2^+0.3280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1410
_reflns_number_gt                2831
_reflns_number_total             3616
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce01041e2.cif
_cod_data_source_block           5f
_cod_depositor_comments
'Adding full bibliography for 7225471--7225478.cif.'
_cod_original_cell_volume        1767.69(9)
_cod_database_code               7225474
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B)
2.b 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.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'