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_7225472
_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          487
_chemical_name_common            5b
_chemical_name_systematic
'6-methoxy-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             2015-11-07
_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                 111.527(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.0621(5)
_cell_length_b                   6.4884(3)
_cell_length_c                   17.3730(7)
_cell_measurement_reflns_used    4509
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.9591
_cell_measurement_theta_min      3.3758
_cell_volume                     1474.55(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega -108.00  -81.00   1.0000    1.5100
omega____ theta____ kappa____ phi______ frames
    -      -41.5504  -99.0000   90.0000 27

  2 omega  -50.00   28.00   1.0000    1.5100
omega____ theta____ kappa____ phi______ frames
    -      -41.5504   38.0000    0.0000 78

  3 omega -108.00  -81.00   1.0000    1.5100
omega____ theta____ kappa____ phi______ frames
    -      -41.5504  -99.0000  -30.0000 27

  4 omega -120.00  -23.00   1.0000    1.5100
omega____ theta____ kappa____ phi______ frames
    -      -41.5504  -77.0000   30.0000 97

  5 omega   83.00  159.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110   45.0000 -120.0000 76

  6 omega   42.00   85.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110  -45.0000   90.0000 43

  7 omega   52.00   90.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110  -45.0000  120.0000 38

  8 omega   57.00   99.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110  -45.0000 -180.0000 42

  9 omega   45.00   70.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110  -30.0000 -120.0000 25

 10 omega   26.00  107.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110  -94.0000   30.0000 81

 11 omega   30.00   91.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110  -30.0000   30.0000 61

 12 omega   38.00   73.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110  -61.0000  -60.0000 35

 13 omega -120.00   -8.00   1.0000    1.5100
omega____ theta____ kappa____ phi______ frames
    -      -41.5504  -77.0000 -120.0000 112

 14 omega -120.00   -8.00   1.0000    1.5100
omega____ theta____ kappa____ phi______ frames
    -      -41.5504  -77.0000  120.0000 112

 15 omega   18.00   99.00   1.0000    1.5100
omega____ theta____ kappa____ phi______ frames
    -       41.5504 -125.0000 -150.0000 81

 16 omega   23.00  109.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110  -94.0000 -120.0000 86

 17 omega   76.00  178.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110   30.0000  150.0000 102

 18 omega   73.00  178.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110   77.0000   60.0000 105

 19 omega   73.00  178.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110   77.0000  -90.0000 105

 20 omega   77.00  178.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110   61.0000 -180.0000 101

 21 omega   46.00  178.00   1.0000    6.0600
omega____ theta____ kappa____ phi______ frames
    -      107.0110   15.0000   30.0000 132

 22 omega -116.00  -12.00   1.0000    1.5100
omega____ theta____ kappa____ phi______ frames
    -      -41.5504  -57.0000  -60.0000 104

 23 omega -120.00  -84.00   1.0000    1.5100
omega____ theta____ kappa____ phi______ frames
    -      -41.5504 -159.0000  108.0000 36

 24 omega   72.00  119.00   1.0000    1.5100
omega____ theta____ kappa____ phi______ frames
    -       41.5504  159.0000  140.0000 47
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1088854000
_diffrn_orient_matrix_UB_12      -0.0716900000
_diffrn_orient_matrix_UB_13      -0.0529401000
_diffrn_orient_matrix_UB_21      0.0265112000
_diffrn_orient_matrix_UB_22      0.0142021000
_diffrn_orient_matrix_UB_23      -0.0783831000
_diffrn_orient_matrix_UB_31      0.0362592000
_diffrn_orient_matrix_UB_32      -0.2258284000
_diffrn_orient_matrix_UB_33      0.0119079000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13711
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         3.48
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.829
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.438
_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          0.4504
_exptl_crystal_size_mid          0.2365
_exptl_crystal_size_min          0.1107
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0620P)^2^+0.1495P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1076
_reflns_number_gt                2144
_reflns_number_total             2638
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce01041e2.cif
_cod_data_source_block           5b
_cod_depositor_comments
'Adding full bibliography for 7225471--7225478.cif.'
_cod_original_cell_volume        1474.55(10)
_cod_database_code               7225472
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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), C7(H7), 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_submission_special_instructions 'No special instructions were received'