Open-Resonance-Assisted Hydrogen Bonds and Competing Quasiaromaticity.
Nguyen, Yen H.; Lampkin, Bryan J.; Venkatesh, Amrit; Ellern, Arkady; Rossini, Aaron J.; VanVeller, Brett; The Journal of organic chemistry 83 (2018) 9850–9857; doi:10.1021/acs.joc.8b01331

data_4035130
_publ_section_title
;
 Open-Resonance-Assisted Hydrogen Bonds and Competing Quasiaromaticity.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9850
_journal_page_last               9857
_journal_paper_doi               10.1021/acs.joc.8b01331
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C15 H11 N3 O'
_chemical_formula_weight         249.27
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 102.275(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2678(8)
_cell_length_b                   24.682(3)
_cell_length_c                   6.8030(9)
_cell_measurement_reflns_used    2192
_cell_measurement_temperature    173.(2)
_cell_measurement_theta_max      58.7222
_cell_measurement_theta_min      3.5815
_cell_volume                     1192.4(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 Suite (Bruker AXS, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'APEX2 Suite (Bruker AXS, 2017)'
_computing_publication_material  'APEX2 Suite (Bruker AXS, 2017)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture Diffractometer'
_diffrn_measurement_method
;

calculated with 99% coverage BRUKER QUINN strategy.
\w and \f scans, narrow frame width
;
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_radiation_type           'CuK\a '
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0937
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            11001
_diffrn_reflns_theta_full        52.57
_diffrn_reflns_theta_max         52.57
_diffrn_reflns_theta_min         3.58
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'sealed tube'
_exptl_absorpt_coefficient_mu    0.731
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;

SADABS-2016/2 - Bruker AXS area detector scaling and
absorption correction'
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.196
_refine_ls_extinction_coef       0.0022(5)
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   0.557
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1347
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.557
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1105P)^2^+4.8741P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1294
_reflns_number_gt                1062
_reflns_number_total             1347
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01331_si_002.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1192.4(2)
_cod_database_code               4035130
_shelx_res_checksum              55392
_shelx_hkl_checksum              98886