Medium Rings Bearing Bitriazolyls: Easily Accessible Structures with Superior Performance as Cu Catalyst Ligands.
Li, Lingjun; Huang, Shenlong; Shang, Tongpeng; Zhang, Bo; Guo, Yuanyang; Zhu, Gongming; Zhou, Demin; Zhang, Guisheng; Zhu, Anlian; Zhang, Lihe; The Journal of organic chemistry 83 (2018) 13166–13177; doi:10.1021/acs.joc.8b01899

data_4035764
_publ_section_title
;
 Medium Rings Bearing Bitriazolyls: Easily Accessible Structures with
 Superior Performance as Cu Catalyst Ligands.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13166
_journal_page_last               13177
_journal_paper_doi               10.1021/acs.joc.8b01899
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C23 H24 N6 O2'
_chemical_formula_sum            'C23 H24 N6 O2'
_chemical_formula_weight         416.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-09-13
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_cell_angle_alpha                107.523(4)
_cell_angle_beta                 104.775(3)
_cell_angle_gamma                90.140(3)
_cell_formula_units_Z            2
_cell_length_a                   8.2396(2)
_cell_length_b                   11.5901(5)
_cell_length_c                   12.2867(6)
_cell_measurement_reflns_used    5031
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8210
_cell_measurement_theta_min      3.9910
_cell_volume                     1077.91(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.979
_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   -105.00 -17.00   1.00    3.50    --  -35.62 -38.00  30.00   88
  2  \w    -52.00  32.00   1.00    3.50    --  -35.62  57.00-180.00   84
  3  \w   -105.00 -17.00   1.00    3.50    --  -35.62 -38.00   0.00   88
  4  \w    -89.00  -2.00   1.00    3.50    --  -35.62 125.00-180.00   87
  5  \w   -105.00 -17.00   1.00    3.50    --  -35.62 -38.00 -60.00   88
  6  \w    -36.00  65.00   1.00    3.50    --   35.62 -19.00  60.00  101
  7  \w      1.00  75.00   1.00    3.50    --   35.62 -99.00 -60.00   74
  8  \w     23.00  89.00   1.00    3.50    --   35.62-125.00  90.00   66
  9  \w     23.00  89.00   1.00    3.50    --   35.62-125.00-120.00   66
 10  \w     38.00 124.00   1.00   17.00    --  106.50 -45.00 120.00   86
 11  \w     37.00 109.00   1.00   17.00    --  106.50 -95.00-120.00   72
 12  \w     37.00 109.00   1.00   17.00    --  106.50 -95.00 120.00   72
 13  \w     38.00 124.00   1.00   17.00    --  106.50 -45.00 -30.00   86
 14  \w     85.00 176.00   1.00   17.00    --  106.50  30.00 -60.00   91
 15  \w     38.00 124.00   1.00   17.00    --  106.50 -45.00-150.00   86
 16  \w     37.00 109.00   1.00   17.00    --  106.50 -95.00   0.00   72
 17  \w     68.00 178.00   1.00   17.00    --  106.50  15.00-120.00  110
 18  \w     37.00 112.00   1.00   17.00    --  106.50-111.00  90.00   75
 19  \w     37.00 109.00   1.00   17.00    --  106.50 -95.00 150.00   72
 20  \w     37.00 128.00   1.00   17.00    --  106.50 -30.00  30.00   91
 21  \w     37.00 109.00   1.00   17.00    --  106.50 -95.00 -90.00   72
 22  \w     35.00 145.00   1.00   17.00    --  106.50 -15.00 -90.00  110
 23  \w   -103.00  -9.00   1.00    3.50    --  -35.62 -77.00-150.00   94
 24  \w    -36.00  65.00   1.00    3.50    --   35.62 -19.00 -30.00  101
 25  \w     19.00 103.00   1.00    3.50    --   35.62  57.00 150.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0033074000
_diffrn_orient_matrix_UB_12      0.1127466000
_diffrn_orient_matrix_UB_13      0.1065358000
_diffrn_orient_matrix_UB_21      0.0493705000
_diffrn_orient_matrix_UB_22      0.0820842000
_diffrn_orient_matrix_UB_23      -0.0664810000
_diffrn_orient_matrix_UB_31      -0.1876676000
_diffrn_orient_matrix_UB_32      0.0111477000
_diffrn_orient_matrix_UB_33      -0.0534695000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9969
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.409
_diffrn_reflns_theta_min         3.916
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       needle
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4103
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0549
_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^)+(0.0739P)^2^+0.3792P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1661
_refine_ls_wR_factor_ref         0.1740
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3386
_reflns_number_total             4103
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01899_si_003.cif
_cod_data_source_block           hsl-20180905
_cod_database_code               4035764
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.830
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C14(H14A,H14B), C25(H25A,H25B), C18(H18A,H18B), C8(H8A,H8B), C12(H12A,H12B),
 C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C27(H27), C31(H31), C20(H20), C28(H28), C29(H29), C23(H23),
 C30(H30), C21(H21), C22(H22)
;
_shelx_res_checksum              17939
_shelx_hkl_checksum              90945
_olex2_date_sample_data_collection 2018-09-05
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.455
_oxdiff_exptl_absorpt_empirical_full_min 0.288