Exploration of relative π-electron localization in naphthalene aromatic rings by C‒H⋯π interactions: experimental evidence, computational criteria, and database analysis
Samie, Ali; Salimi, Alireza; Garrison, Jered C.; CrystEngComm 21 (2019) 6432–; doi:10.1039/C9CE00929A

data_7234150
_publ_section_title
;
 Exploration of relative \p-electron localization in naphthalene aromatic
 rings by C--H&#x22EF;\p interactions: experimental evidence,
 computational criteria, and database analysis
;
_journal_issue                   42
_journal_name_full               CrystEngComm
_journal_page_first              6432
_journal_paper_doi               10.1039/C9CE00929A
_journal_volume                  21
_journal_year                    2019
_chemical_formula_sum            'C10 H6.67 N1.33 O1.33'
_chemical_formula_weight         166.83
_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
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-11-09 deposited with the CCDC.    2019-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.757(2)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   6.73650(10)
_cell_length_b                   20.9912(5)
_cell_length_c                   8.5808(2)
_cell_measurement_reflns_used    14404
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7110
_cell_measurement_theta_min      4.1640
_cell_volume                     1209.21(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2603
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Ultra'
_diffrn_orient_matrix_UB_11      -0.2236160000
_diffrn_orient_matrix_UB_12      0.0039467000
_diffrn_orient_matrix_UB_13      0.0246286000
_diffrn_orient_matrix_UB_21      -0.0446172000
_diffrn_orient_matrix_UB_22      0.0204618000
_diffrn_orient_matrix_UB_23      -0.1717982000
_diffrn_orient_matrix_UB_31      -0.0258253000
_diffrn_orient_matrix_UB_32      -0.0703311000
_diffrn_orient_matrix_UB_33      -0.0486372000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            33620
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.222
_diffrn_reflns_theta_min         4.212
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.764
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.5000
_exptl_crystal_size_mid          0.4000
_exptl_crystal_size_min          0.2500
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0566
_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^)+(0.0902P)^2^+0.5555P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1601
_refine_ls_wR_factor_ref         0.1631
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2332
_reflns_number_total             2521
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce00929a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7234149--7234152.cif.'
_cod_database_code               7234150
_shelxl_version_number           2013-4
_shelx_res_checksum              70627