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_7234151
_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            'C16 H11 N O2'
_chemical_formula_weight         249.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.76480(10)
_cell_length_b                   25.7822(2)
_cell_length_c                   5.89423(5)
_cell_measurement_reflns_used    25524
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0070
_cell_measurement_theta_min      5.1090
_cell_volume                     1179.99(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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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)
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_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Ultra'
_diffrn_orient_matrix_UB_11      -0.0355622000
_diffrn_orient_matrix_UB_12      0.1152998000
_diffrn_orient_matrix_UB_13      -0.0525495000
_diffrn_orient_matrix_UB_21      -0.0341462000
_diffrn_orient_matrix_UB_22      0.2263120000
_diffrn_orient_matrix_UB_23      0.0280315000
_diffrn_orient_matrix_UB_31      0.1922033000
_diffrn_orient_matrix_UB_32      0.0616334000
_diffrn_orient_matrix_UB_33      -0.0047529000
_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  0.0510
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.997
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_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
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_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.190
_diffrn_reflns_theta_min         3.428
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72591
_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 colourless'
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.5000
_exptl_crystal_size_mid          0.2500
_exptl_crystal_size_min          0.2500
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1087 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.05(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2459
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0497P)^2^+0.2586P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0811
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2430
_reflns_number_total             2459
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce00929a2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7234149--7234152.cif.'
_cod_database_code               7234151
_shelx_estimated_absorpt_t_min   0.928
_shelx_estimated_absorpt_t_max   0.928
_shelxl_version_number           2013-4
_shelx_res_checksum              46058