Conformationally Distorted π-Conjugation for Reaction-Based Detection of Nickel: Fluorescence Turn-on by Twist-and-Fragment.
Kim, Seyong; Jo, Junyong; Lee, Dongwhan; Organic letters 18 (2016) 4530–4533; doi:10.1021/acs.orglett.6b02140

data_1555708
_publ_section_title
;
 Conformationally Distorted \p-Conjugation for Reaction-Based Detection of
 Nickel: Fluorescence Turn-on by Twist-and-Fragment.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4530
_journal_page_last               4533
_journal_paper_doi               10.1021/acs.orglett.6b02140
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C18 H21 N3'
_chemical_formula_sum            'C18 H21 N3'
_chemical_formula_weight         279.38
_chemical_name_systematic        2-(2,6-Diisopropylphenyl)-2H-benzotriazole
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-13
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.58554(8)
_cell_length_b                   8.33918(5)
_cell_length_c                   25.4351(2)
_cell_measurement_reflns_used    38753
_cell_measurement_temperature    99.95(16)
_cell_measurement_theta_max      76.2720
_cell_measurement_theta_min      5.2360
_cell_volume                     3093.71(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.95(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -113.00 -13.00   1.00    3.08    --  -41.24 -57.00  60.00  100
  2  \w   -116.00 -17.00   1.00    3.08    --  -41.24 -38.00 120.00   99
  3  \w    -96.00  -2.00   1.00    3.08    --  -41.24 125.00-150.00   94
  4  \w     39.00 138.00   1.00    6.67    --  112.00 -45.00-120.00   99
  5  \w     36.00 145.00   1.00    6.67    --  112.00 -77.00-180.00  109
  6  \w     86.00 178.00   1.00    6.67    --  112.00  45.00-120.00   92
  7  \w     62.00 109.00   1.00    6.67    --  112.00 -94.00 150.00   47
  8  \w    126.00 153.00   1.00    6.67    --  112.00  15.00-180.00   27
  9  \w     45.00  85.00   1.00    6.67    --  112.00 -94.00 120.00   40
 10  \w    111.00 175.00   1.00    6.67    --  112.00 111.00  90.00   64
 11  \w     39.00 136.00   1.00    6.67    --  112.00 -45.00  90.00   97
 12  \w     49.00 156.00   1.00    6.67    --  112.00 -15.00  60.00  107
 13  \w     72.00 104.00   1.00    6.67    --  112.00 -30.00 -30.00   32
 14  \w    -20.00   6.00   1.00   65.19    --  -41.49  77.00  60.00   26
 15  \w   -118.00  -9.00   1.00    1.83    --  -41.49 -77.00-120.00  109
 16  \w   -115.00 -13.00   1.00    1.83    --  -41.49 -57.00 -60.00  102
 17  \w      1.00  82.00   1.00    1.83    --   41.49 -99.00  90.00   81
 18  \w    -33.00  66.00   1.00    1.83    --   41.49 -38.00 120.00   99
 19  \w     36.00 116.00   1.00    4.63    --  112.00-111.00  60.00   80
 20  \w     84.00 178.00   1.00    4.63    --  112.00  30.00-180.00   94
 21  \w     84.00 178.00   1.00    4.63    --  112.00  30.00  90.00   94
 22  \w     86.00 178.00   1.00    4.63    --  112.00  45.00  30.00   92
 23  \w     83.00 139.00   1.00    4.63    --  112.00  61.00 -30.00   56
 24  \w     86.00 178.00   1.00    4.63    --  112.00  45.00 -60.00   92
 25  \w   -118.00  -9.00   1.00    1.83    --  -41.49 -77.00 -60.00  109
 26  \w   -118.00  -9.00   1.00    1.83    --  -41.49 -77.00  30.00  109
 27  \w     17.00 116.00   1.00    1.83    --   41.49  38.00-180.00   99
 28  \w      9.00 118.00   1.00    1.83    --   41.49  77.00 -90.00  109
 29  \w      1.00  82.00   1.00    1.83    --   41.49 -99.00   0.00   81
 30  \w      9.00 118.00   1.00    1.83    --   41.49  77.00-180.00  109
 31  \w     83.00 178.00   1.00    4.63    --  112.00  61.00 120.00   95
 32  \w     79.00 178.00   1.00    4.63    --  112.00  77.00  30.00   99
 33  \w     83.00 178.00   1.00    4.63    --  112.00  61.00   0.00   95
 34  \w     83.00 178.00   1.00    4.63    --  112.00  61.00  90.00   95
 35  \w     36.00 116.00   1.00    4.63    --  112.00-111.00 -60.00   80
 36  \w     79.00 178.00   1.00    4.63    --  112.00  77.00-120.00   99
 37  \w     79.00 178.00   1.00    4.63    --  112.00  77.00 150.00   99
 38  \w     83.00 178.00   1.00    4.63    --  112.00  61.00 -60.00   95
 39  \w     79.00 178.00   1.00    4.63    --  112.00  77.00-180.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0950453000
_diffrn_orient_matrix_UB_12      0.0683266000
_diffrn_orient_matrix_UB_13      -0.0139389000
_diffrn_orient_matrix_UB_21      -0.0453104000
_diffrn_orient_matrix_UB_22      -0.1565851000
_diffrn_orient_matrix_UB_23      0.0189763000
_diffrn_orient_matrix_UB_31      -0.0084378000
_diffrn_orient_matrix_UB_32      0.0702655000
_diffrn_orient_matrix_UB_33      0.0558027000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            59705
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.660
_diffrn_reflns_theta_min         3.475
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.556
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orangish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1200
_exptl_crystal_recrystallization_method
'prepared by slow evaporation of methanol solution of this material under ambient condition.'
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 2779 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.40(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         6242
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0320
_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^)+(0.0536P)^2^+0.4528P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0870
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.915
_reflns_number_gt                6133
_reflns_number_total             6242
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02140_si_002.cif
_cod_data_source_block           exp_196
_cod_database_code               1555708
_chemical_oxdiff_formula         C18H21N3
_chemical_oxdiff_usercomment     SK-1-70B/MeOH
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00G(H00G), C00P(H00P), C00H(H00H), C00Y(H00Y)
2.b Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00K(H00K), C00M(H00M), C00S(H00S), C00T(H00T), C00W(H00W),
 C013(H013), C00E(H00E), C00F(H00F), C00N(H00N), C00O(H00O), C00U(H00U),
 C00V(H00V), C011(H011)
2.c Idealised Me refined as rotating group:
 C00X(H00a,H00b,H00c), C012(H01a,H01b,H01c), C014(H01d,H01e,H01f), C015(H01g,
 H01h,H01i), C00I(H00d,H00i,H00l), C00Z(H00q,H00r,H00x), C010(H01j,H01k,H01l),
 C016(H01m,H01n,H01o)
;
_shelx_res_checksum              81599
_shelx_hkl_checksum              92708
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-02-03
_olex2_exptl_crystal_mounting_method
'was placed onto a nylon loop with Paratone-N oil'
_olex2_submission_original_sample_id SK-1-70B
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.157
_oxdiff_exptl_absorpt_empirical_full_min 0.465