Altering the Cyclization Modes: Temperature-Dependent Intramolecular 7-Endo-Dig vs 6-Endo-Dig Electrophilic Ring Closures.
Nayak, Maloy; Kang, Young Kee; Kim, Ikyon; Organic letters 19 (2017) 1474–1477; doi:10.1021/acs.orglett.7b00472

data_1545525
_publ_section_title
;
 Altering the Cyclization Modes: Temperature-Dependent Intramolecular
 7-Endo-Dig vs 6-Endo-Dig Electrophilic Ring Closures.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1474
_journal_page_last               1477
_journal_paper_doi               10.1021/acs.orglett.7b00472
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C20 H15 N O'
_chemical_formula_sum            'C20 H15 N O'
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_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
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_atom_sites_solution_primary     dual
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;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                100.835(3)
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_cell_length_a                   8.9477(6)
_cell_length_b                   9.8191(6)
_cell_length_c                   10.1325(6)
_cell_measurement_reflns_used    2862
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_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
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_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
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_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
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_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_max         26.033
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_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
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_exptl_absorpt_correction_T_min  0.6987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0608 before and 0.0548 after correction.
The Ratio of minimum to maximum transmission is 0.9375.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
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_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.065
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_refine_diff_density_min         -0.162
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_refine_ls_extinction_coef       0.031(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2903
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0468
_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^)+(0.0499P)^2^+0.0797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1152
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1807
_reflns_number_total             2903
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00472_si_003.cif
_cod_data_source_block           mo_moon514_092816_0m_a_a
_cod_depositor_comments
'Adding full bibliography for 1545524--1545525.cif.'
_cod_original_cell_volume        739.75(8)
_cod_database_code               1545525
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19), C21(H21)
;
_shelx_res_checksum              6181
_shelx_hkl_checksum              69772
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'