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_7225477
_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         'C19 H15 N3 O4'
_chemical_formula_sum            'C19 H15 N3 O4'
_chemical_formula_weight         349.34
_chemical_melting_point          505
_chemical_name_common            5k
_chemical_name_systematic
7-methoxy-3-(4-(4-methoxyphenyl)-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                 90.466(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2786(3)
_cell_length_b                   5.9228(3)
_cell_length_c                   36.7067(16)
_cell_measurement_reflns_used    3057
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.2070
_cell_measurement_theta_min      4.7970
_cell_volume                     1582.36(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 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
  1 omega -124.00  -79.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -99.0000 -120.0000 45

  2 omega -106.00  -80.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -99.0000  -30.0000 26

  3 omega  -49.00   -8.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4254   37.0000  150.0000 41

  4 omega -115.00  -65.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4254 -147.0000   51.0000 50

  5 omega   63.00  101.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4254  178.0000   60.0000 38

  6 omega   42.00  107.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000 -180.0000 65

  7 omega  152.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000    0.0000 26

  8 omega  125.00  176.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000 -150.0000 51

  9 omega  102.00  128.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   77.0000    0.0000 26

 10 omega   40.00   94.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000 -120.0000 54

 11 omega   44.00   70.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000   30.0000 26

 12 omega   87.00  164.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000    0.0000 77

 13 omega -115.00  -12.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -57.0000 -150.0000 103

 14 omega -116.00  -10.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -66.0000   94.0000 106

 15 omega -115.00  -12.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4254  -57.0000  -30.0000 103

 16 omega   84.00  176.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000  -60.0000 92

 17 omega   84.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000   90.0000 94

 18 omega   85.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   61.0000  150.0000 93
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1375685000
_diffrn_orient_matrix_UB_12      -0.1878557000
_diffrn_orient_matrix_UB_13      0.0101853000
_diffrn_orient_matrix_UB_21      -0.0202023000
_diffrn_orient_matrix_UB_22      0.0604436000
_diffrn_orient_matrix_UB_23      0.0405843000
_diffrn_orient_matrix_UB_31      -0.1597072000
_diffrn_orient_matrix_UB_32      -0.1693449000
_diffrn_orient_matrix_UB_33      0.0031780000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            9333
_diffrn_reflns_theta_full        74.44
_diffrn_reflns_theta_max         74.44
_diffrn_reflns_theta_min         4.82
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.873
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.908
_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            red
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.1872
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.1185
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0587P)^2^+0.2233P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1178
_reflns_number_gt                2446
_reflns_number_total             3129
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce01041e2.cif
_cod_data_source_block           5k
_cod_depositor_comments
'Adding full bibliography for 7225471--7225478.cif.'
_cod_database_code               7225477
_reflns_odcompleteness_completeness 96.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'