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_4035763
_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         'C31 H28 N6 O3'
_chemical_formula_sum            'C31 H28 N6 O3'
_chemical_formula_weight         532.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90
_cell_angle_beta                 109.067(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6636(2)
_cell_length_b                   12.6670(2)
_cell_length_c                   17.6579(3)
_cell_measurement_reflns_used    8169
_cell_measurement_temperature    170.01(10)
_cell_measurement_theta_max      71.1090
_cell_measurement_theta_min      4.3610
_cell_volume                     2677.10(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_environment      N~2~
_diffrn_ambient_temperature      170.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_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    -54.00  34.00   1.00    4.00    --  -35.37  38.00-180.00   88
  2  \w    -52.00  32.00   1.00    4.00    --  -35.37  57.00  30.00   84
  3  \w     23.00  89.00   1.00    4.00    --   35.37-125.00 150.00   66
  4  \w      1.00  74.00   1.00    4.00    --   35.37 -99.00  60.00   73
  5  \w     23.00  89.00   1.00    4.00    --   35.37-125.00-120.00   66
  6  \w     23.00  89.00   1.00    4.00    --   35.37-125.00 -60.00   66
  7  \w     23.00  89.00   1.00    4.00    --   35.37-125.00  30.00   66
  8  \w     40.00 125.00   1.00   17.00    --  106.50 -61.00-180.00   85
  9  \w     37.00 112.00   1.00   17.00    --  106.50-111.00 150.00   75
 10  \w     80.00 174.00   1.00   17.00    --  106.50  77.00 -60.00   94
 11  \w     40.00 125.00   1.00   17.00    --  106.50 -61.00  30.00   85
 12  \w     38.00 124.00   1.00   17.00    --  106.50 -45.00 -60.00   86
 13  \w     57.00 151.00   1.00   17.00    --  106.50 178.00  90.00   94
 14  \w     37.00 109.00   1.00   17.00    --  106.50 -95.00  30.00   72
 15  \w    100.00 176.00   1.00   17.00    --  106.50 111.00 -30.00   76
 16  \w    -65.00   5.00   1.00    4.00    --  -35.37  19.00 -60.00   70
 17  \w     19.00 103.00   1.00    4.00    --   35.37  57.00 150.00   84
 18  \w     19.00 103.00   1.00    4.00    --   35.37  57.00   0.00   84
 19  \w      9.00 103.00   1.00    4.00    --   35.37  77.00-120.00   94
 20  \w      9.00 103.00   1.00    4.00    --   35.37  77.00  60.00   94
;
_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      0.1208052000
_diffrn_orient_matrix_UB_12      -0.0258887000
_diffrn_orient_matrix_UB_13      0.0520958000
_diffrn_orient_matrix_UB_21      -0.0406618000
_diffrn_orient_matrix_UB_22      -0.1032667000
_diffrn_orient_matrix_UB_23      0.0275203000
_diffrn_orient_matrix_UB_31      0.0181181000
_diffrn_orient_matrix_UB_32      -0.0587717000
_diffrn_orient_matrix_UB_33      -0.0710615000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17251
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.353
_diffrn_reflns_theta_min         3.693
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87889
_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    1.321
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.331
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.331
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0562
_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^)+7.0359P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1742
_refine_ls_wR_factor_ref         0.1789
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4160
_reflns_number_total             5097
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01899_si_002.cif
_cod_data_source_block           hsl-20180907
_cod_database_code               4035763
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.895
_reflns_odcompleteness_completeness 99.86
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C21(H21A,H21B), C8(H8A,H8B), C14(H14A,H14B), C32(H32A,H32B)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C23(H23), C27(H27), C40(H40), C36(H36), C24(H24), C26(H26),
 C25(H25), C19(H19), C39(H39), C38(H38), C18(H18), C16(H16), C37(H37), C17(H17)
2.c Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C)
;
_shelx_res_checksum              27219
_shelx_hkl_checksum              6974
_olex2_date_sample_data_collection 2018-09-07
_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 1.211
_oxdiff_exptl_absorpt_empirical_full_min 0.401