Nitrous oxide as a diazo transfer reagent: the synthesis of triazolopyridines.
Landman, Iris R.; Fadaei-Tirani, Farzaneh; Severin, Kay; Chemical communications (Cambridge, England) 57 (2021) 11537–11540; doi:10.1039/d1cc04907k

data_7129181
_publ_section_title
;
 Nitrous oxide as a diazo transfer reagent: the synthesis of
 triazolopyridines.
;
_journal_issue                   87
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11537
_journal_page_last               11540
_journal_paper_doi               10.1039/d1cc04907k
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C42 H26 K2 N18 Na4 O13'
_chemical_formula_sum            'C42 H26 K2 N18 Na4 O13'
_chemical_formula_weight         1160.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-07-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-08 deposited with the CCDC.	2021-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.107(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.2718(7)
_cell_length_b                   6.5810(3)
_cell_length_c                   24.714(3)
_cell_measurement_reflns_used    6064
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      74.0460
_cell_measurement_theta_min      3.5410
_cell_volume                     2321.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.927
_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     20.00  92.00   0.50   10.00    --   59.56-128.00-178.00  144
  2  \w   -103.00 -23.00   0.50   10.00    --  -62.28 143.00  66.00  160
  3  \w     28.00 111.00   0.50   10.00    --   69.94-143.00  11.00  166
  4  \w     31.00 114.00   0.50   30.00    --   73.45-143.00  11.00  166
  5  \w   -117.00 -75.00   0.50   30.00    --  -76.11 143.00  66.00   84
  6  \w   -121.00 -96.00   0.50   30.00    --  -76.11-128.00-178.00   50
  7  \w    -94.00 -69.00   0.50   30.00    --  -76.11 128.00-103.00   50
  8  \w     77.00 102.00   0.50   30.00    --   80.01 128.00-103.00   50
  9  \w     68.00 123.00   0.50   30.00    --   80.01 143.00  66.00  110
 10  \w     55.00  80.00   0.50   30.00    --   80.01-143.00  11.00   50
 11  \w     49.00  74.00   0.50   30.00    --   80.01-128.00-178.00   50
 12  \w     10.00  36.00   0.50   10.00    --   59.56 -30.00 120.00   52
 13  \w     25.00  66.00   0.50   10.00    --   59.56 -95.00  60.00   82
 14  \w     10.00  35.00   0.50   10.00    --   59.56 -30.00   0.00   50
 15  \w     10.00  36.00   0.50   10.00    --   59.56 -30.00 -60.00   52
 16  \w   -111.00 -65.00   0.50   10.00    --  -62.28 -30.00 120.00   92
 17  \w     73.00 111.00   0.50   10.00    --   69.94  30.00-150.00   76
 18  \w     35.00  84.00   0.50   30.00    --   73.45 -95.00 -90.00   98
 19  \w     83.00 115.00   0.50   30.00    --   73.45  30.00-120.00   64
 20  \w     76.00 123.00   0.50   30.00    --   73.45  30.00  30.00   94
 21  \w     35.00  84.00   0.50   30.00    --   73.45 -95.00 120.00   98
 22  \w   -101.00 -75.00   0.50   10.00    --  -73.91 -30.00-120.00   52
 23  \w   -118.00 -75.00   0.50   10.00    --  -73.91-125.00 -30.00   86
 24  \w   -121.00 -77.00   0.50   30.00    --  -76.11 -30.00  60.00   88
 25  \w     98.00 125.00   0.50   30.00    --   80.01 125.00  30.00   54
 26  \w     48.00  91.00   0.50   30.00    --   80.01 -95.00  60.00   86
 27  \w     40.00  90.00   0.50   30.00    --   80.01 -95.00-180.00  100
 28  \w     84.00 122.00   0.50   30.00    --   80.01  30.00-150.00   76
 29  \w     79.00 125.00   0.50   30.00    --   80.01 125.00   0.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0450823000
_diffrn_orient_matrix_UB_12      0.1112327000
_diffrn_orient_matrix_UB_13      -0.0482237000
_diffrn_orient_matrix_UB_21      -0.0465378000
_diffrn_orient_matrix_UB_22      -0.1512018000
_diffrn_orient_matrix_UB_23      -0.0393413000
_diffrn_orient_matrix_UB_31      -0.0863238000
_diffrn_orient_matrix_UB_32      0.1396975000
_diffrn_orient_matrix_UB_33      -0.0041665000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0756
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            22718
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.339
_diffrn_reflns_theta_min         3.573
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.948
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.802
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on Gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics
as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_description       prism
_exptl_crystal_F_000             1180
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.715
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         4567
_refine_ls_number_restraints     655
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0634
_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^)+(0.0866P)^2^+2.7104P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1545
_refine_ls_wR_factor_ref         0.1704
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3099
_reflns_number_total             4567
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04907k2.cif
_cod_data_source_block           il503g
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Gaussian' was
changed to 'gaussian' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7129181
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C42 H26 K2 N18 Na4 O13'
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.777
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H14 of C14, H20 of C20, H21 of C21, H11 of C11, H6 of C6, H7A of C7, H13 of
  C13, H18 of C18, H19 of C19, H12 of C12, H4 of C4, H5 of C5
 At 1.5 times of:
  H7 of C21
2. Restrained distances
 O7-H7
 0.98 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.005 and sigma
for terminal atoms of 0.01 within 2A
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7A), C11(H11), C12(H12), C13(H13), C14(H14),
 C18(H18), C19(H19), C20(H20), C21(H21)
;
_shelx_res_checksum              809
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 9.120
_oxdiff_exptl_absorpt_empirical_full_min 0.259