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_7234149
_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_moiety         'C15 H10 N2 O2'
_chemical_formula_sum            'C15 H10 N2 O2'
_chemical_formula_weight         250.25
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_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                   7.73077(13)
_cell_length_b                   25.6327(4)
_cell_length_c                   5.93311(8)
_cell_measurement_reflns_used    9501
_cell_measurement_temperature    100
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_cell_measurement_theta_min      3.3770
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_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
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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 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2603
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_diffrn_measurement_details
;
?
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_12      -0.0315494000
_diffrn_orient_matrix_UB_13      0.0814237000
_diffrn_orient_matrix_UB_21      0.0136420000
_diffrn_orient_matrix_UB_22      0.0352225000
_diffrn_orient_matrix_UB_23      0.2095104000
_diffrn_orient_matrix_UB_31      -0.1209518000
_diffrn_orient_matrix_UB_32      -0.0371261000
_diffrn_orient_matrix_UB_33      0.1298656000
_diffrn_radiation_monochromator  mirror
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_diffrn_radiation_type           CuK\a
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_diffrn_reflns_av_R_equivalents  0.0525
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_diffrn_reflns_Laue_measured_fraction_full 1.000
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_diffrn_reflns_limit_h_min       -9
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_diffrn_reflns_limit_k_min       -31
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_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.058
_diffrn_reflns_theta_min         3.448
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.786
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72021
_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    1.414
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1017 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2437
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0297
_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^)+(0.0465P)^2^+0.2111P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0797
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                2337
_reflns_number_total             2437
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce00929a2.cif
_cod_data_source_block           iran-a51
_cod_depositor_comments
'Adding full bibliography for 7234149--7234152.cif.'
_cod_database_code               7234149
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15)
;
_shelx_res_checksum              37482
_olex2_date_sample_data_collection 2015-03-25
_olex2_exptl_crystal_mounting_method 'Paratone on Cryoloop'
_olex2_submission_special_instructions 'No special instructions were received'