NO sorption, in-crystal nitrite and nitrate production with arylamine oxidation in gas‒solid single crystal to single crystal reactions
Møller, Mads Sondrup; Haag, Alexander; McKee, Vickie; McKenzie, Christine J.; Chemical Communications  (2019) –; doi:10.1039/C9CC05315H

data_7124008
_publ_section_title
;
 NO sorption, in-crystal nitrite and nitrate production with arylamine
 oxidation in gas--solid single crystal to single crystal reactions
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05315H
_journal_year                    2019
_chemical_formula_moiety
'C80 H82 Co4 N15 O11, 5(F6 P), 3(C2 H3 N), 0.4(C4 H10 O), F'
_chemical_formula_sum            'C87.6 H95 Co4 F31 N18 O11.4 P5'
_chemical_formula_weight         2561.98
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-06-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-18 deposited with the CCDC.    2019-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                82.568(3)
_cell_angle_beta                 82.672(3)
_cell_angle_gamma                76.060(4)
_cell_formula_units_Z            1
_cell_length_a                   12.5820(5)
_cell_length_b                   15.0550(7)
_cell_length_c                   16.6109(6)
_cell_measurement_reflns_used    13928
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      70.2800
_cell_measurement_theta_min      5.2630
_cell_volume                     3012.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Mercury (Macrae at al., 2008)'
_computing_publication_material
'Olex2 (Dolomanov et al. 2009), PublCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015a)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2923
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  24.00   1.00    4.42    --    0.00 -77.00 -60.00   78
  2  \w    -20.00  18.00   1.00    4.42    --    0.00 -57.00   0.00   38
  3  \w    -40.00   7.00   1.00    4.42    --    0.00 -19.00  30.00   47
  4  \w     -6.00  65.00   1.00    4.42    --    0.00  38.00   0.00   71
  5  \w     41.00  66.00   1.00    4.42    --    0.00  57.00  90.00   25
  6  \w    -17.00  32.00   1.00    4.42    --    0.00  57.00  90.00   49
  7  \w    -61.00   9.00   1.00    4.42    --    0.00 -38.00 -30.00   70
  8  \w    -67.00  16.00   1.00    4.42    --    0.00 -57.00-150.00   83
  9  \w    -45.00 -18.00   1.00   17.71    --  -80.25  38.00 -90.00   27
 10  \w    -89.00 -61.00   1.00   17.71    --  -80.25 -62.00  12.37   28
 11  \w    -82.00 -55.00   1.00   17.71    --  -80.25 -79.00  14.95   27
 12  \w    -84.00 -57.00   1.00   17.71    --  -80.25 -72.00 -16.40   27
 13  \w    -84.00 -56.00   1.00   17.71    --  -80.25 -77.00 -60.00   28
 14  \w    -83.00 -56.00   1.00   17.71    --  -80.25 -75.00 -82.20   27
 15  \w    -85.00 -58.00   1.00   17.71    --  -80.25 -71.00 -49.18   27
 16  \w    -83.00 -56.00   1.00   17.71    --  -80.25 -76.00-111.46   27
 17  \w    -81.00 -54.00   1.00   17.71    --  -80.25 -82.00-159.93   27
 18  \w    -82.00 -55.00   1.00   17.71    --  -80.25 -78.00-179.77   27
 19  \w    -84.00 -56.00   1.00   17.71    --  -80.25 -76.00-155.42   28
 20  \w    -81.00 -54.00   1.00   17.71    --  -80.25 -82.00 -91.72   27
 21  \w    -82.00 -54.00   1.00   17.71    --  -80.25 -83.00-126.73   28
 22  \w    -81.00 -56.00   1.00   17.71    --  -80.25 -77.00-120.00   25
 23  \w    -87.00 -60.00   1.00   17.71    --  -80.25 -67.00 -67.23   27
 24  \w    -89.00 -62.00   1.00   17.71    --  -80.25 -57.00-120.00   27
 25  \w    -90.00 -62.00   1.00   17.71    --  -80.25 -57.00-170.39   28
 26  \w    -92.00 -65.00   1.00   17.71    --  -80.25 -50.00-169.25   27
 27  \w    -87.00 -60.00   1.00   17.71    --  -80.25 -66.00 -88.67   27
 28  \w    -88.00 -61.00   1.00   17.71    --  -80.25 -65.00 -39.89   27
 29  \w    -83.00 -58.00   1.00   17.71    --  -80.25 -70.00  -7.54   25
 30  \w    -87.00 -60.00   1.00   17.71    --  -80.25 -63.00  46.84   27
 31  \w    -84.00 -57.00   1.00   17.71    --  -80.25 -73.00 102.54   27
 32  \w    -84.00 -56.00   1.00   17.71    --  -80.25 -77.00 150.00   28
 33  \w    -83.00 -56.00   1.00   17.71    --  -80.25 -76.00 153.27   27
 34  \w    -82.00 -55.00   1.00   17.71    --  -80.25 -79.00 103.11   27
 35  \w    -85.00 -58.00   1.00   17.71    --  -80.25 -69.00  68.52   27
 36  \w    -83.00 -55.00   1.00   17.71    --  -80.25 -78.00  35.84   28
 37  \w    -80.00 -55.00   1.00   17.71    --  -80.25 -79.00  28.08   25
 38  \w    -80.00 -55.00   1.00   17.71    --  -80.25 -78.00  53.33   25
 39  \w    -81.00 -56.00   1.00   17.71    --  -80.25 -76.00  64.03   25
 40  \w    -94.00 -66.00   1.00   17.71    --  -80.25 -47.00 149.77   28
 41  \w    -96.00 -68.00   1.00   17.71    --  -80.25 -47.00  96.42   28
 42  \w    -82.00 -55.00   1.00   17.71    --  -80.25 -78.00 134.93   27
 43  \w    -88.00 -61.00   1.00   17.71    --  -80.25 -63.00  73.61   27
 44  \w    -90.00 -63.00   1.00   17.71    --  -80.25 -54.00 117.74   27
 45  \w    -87.00 -60.00   1.00   17.71    --  -80.25 -64.00 149.38   27
 46  \w    -89.00 -62.00   1.00   17.71    --  -80.25 -57.00  90.00   27
 47  \w    -94.00 -66.00   1.00   17.71    --  -80.25 -45.00  -4.09   28
 48  \w    -81.00 -56.00   1.00   17.71    --  -80.25 -77.00 -30.00   25
 49  \w   -142.00-115.00   1.00   17.71    --  -80.25 -76.00  64.03   27
 50  \w    -96.00 -39.00   1.00   17.71    --  -80.25 125.00   0.00   57
 51  \w     38.00  95.00   1.00   17.71    --  101.75 -99.00 -30.00   57
 52  \w     36.00 120.00   1.00   17.71    --  101.75-125.00  60.00   84
 53  \w     60.00 101.00   1.00   17.71    --  101.75 -57.00 120.00   41
 54  \w     34.00 109.00   1.00   17.71    --  101.75 -99.00 150.00   75
 55  \w     36.00  65.00   1.00   17.71    --  101.75 -38.00  60.00   29
 56  \w     35.00 105.00   1.00   17.71    --  101.75 -99.00  90.00   70
 57  \w     37.00 105.00   1.00   17.71    --  101.75-125.00 -90.00   68
 58  \w     37.00 103.00   1.00   17.71    --  101.75 -99.00 -90.00   66
 59  \w     97.00 164.00   1.00   17.71    --  101.75  57.00-120.00   67
 60  \w    122.00 149.00   1.00   17.71    --  101.75  77.00-150.00   27
 61  \w     79.00 152.00   1.00   17.71    --  101.75  77.00 -90.00   73
 62  \w     84.00  98.00   1.00   17.71    --  101.75  57.00  30.00   14
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0148615000
_diffrn_orient_matrix_UB_12      0.1020952000
_diffrn_orient_matrix_UB_13      -0.0334531000
_diffrn_orient_matrix_UB_21      -0.0836891000
_diffrn_orient_matrix_UB_22      -0.0110123000
_diffrn_orient_matrix_UB_23      -0.0559419000
_diffrn_orient_matrix_UB_31      -0.0940854000
_diffrn_orient_matrix_UB_32      0.0262598000
_diffrn_orient_matrix_UB_33      0.0677339000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            45519
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        58.928
_diffrn_reflns_theta_max         58.928
_diffrn_reflns_theta_min         3.638
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.807
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.399
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.27b (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            'translucent dark brown'
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       block
_exptl_crystal_F_000             1300
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile, diethylether, hexane'
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.067
_refine_diff_density_max         1.643
_refine_diff_density_min         -0.860
_refine_diff_density_rms         0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.334
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     832
_refine_ls_number_reflns         8493
_refine_ls_number_restraints     690
_refine_ls_restrained_S_all      3.461
_refine_ls_R_factor_all          0.1262
_refine_ls_R_factor_gt           0.1054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3074
_refine_ls_wR_factor_ref         0.3265
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6503
_reflns_number_total             8493
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05315h2.cif
_cod_data_source_block           exp_282
_cod_original_formula_sum        'C87.60 H95 Co4 F31 N18 O11.40 P5'
_cod_database_code               7124008
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C80H82Co4F24N14O10P4
_reflns_odcompleteness_completeness 96.26
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C40, C40', C40X}
{N40, N40'}
3. Uiso/Uaniso restraints and constraints
Uanis(P1) \\sim Ueq, Uanis(F11) \\sim Ueq, Uanis(F12) \\sim Ueq, Uanis(F13)
\\sim Ueq, Uanis(F14) \\sim Ueq, Uanis(F15) \\sim Ueq, Uanis(F16) \\sim Ueq,
Uanis(P1') \\sim Ueq, Uanis(P2) \\sim Ueq, Uanis(F21) \\sim Ueq, Uanis(F22)
\\sim Ueq, Uanis(F23) \\sim Ueq, Uanis(F25) \\sim Ueq, Uanis(F24) \\sim Ueq,
Uanis(F26) \\sim Ueq, Uanis(N40) \\sim Ueq, Uanis(O41) \\sim Ueq, Uanis(O42)
\\sim Ueq, Uanis(N61) \\sim Ueq, Uanis(C62) \\sim Ueq, Uanis(C63) \\sim Ueq:
with sigma of 0.015 and sigma for terminal atoms of 0.03
Uanis(C40) = Uanis(C40') = Uanis(C40X)
Uanis(N40) = Uanis(N40')
4. Rigid body (RIGU) restrains
 P1, F11, F12, F13, F14, F15, F16, P1', F11', F12', F13', F14', F15', F16', P2,
  F21, F22, F23, F25, F24, F26, N40, O41, O42
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{P2, F22, F23, F24, F25, F26, F21} sigma for 1-2: 0.02, 1-3: 0.04
{P1, F11, F12, F13, F14, F15, F16} sigma for 1-2: 0.02, 1-3: 0.04
{P1', F11', F12', F13', F14', F15', F16'} sigma for 1-2: 0.02, 1-3: 0.04
as
{P2, F21, F22, F23, F25, F24, F26}
{N61, C62, C63} sigma for 1-2: 0.02, 1-3: 0.04
as
{N51, C52, C53}
{C104, C103, O100, C102, C101} sigma for 1-2: 0.02, 1-3: 0.04
as
{C101, C102, O100, C103, C104}
6. Others
 Fixed Sof: C40'(0.25) N40'(0.25) H40A(0.25) H40B(0.25) C40X(0.5) H40X(0.5)
 C40(0.25) N40(0.25) O41(0.25) O42(0.25) P1(0.3) F11(0.3) F12(0.3) F13(0.3)
 F14(0.3) F15(0.3) F16(0.3) P1'(0.2) F11'(0.2) F12'(0.2) F13'(0.2) F14'(0.2)
 F15'(0.2) F16'(0.2) N61(0.5) C62(0.5) C63(0.5) H63A(0.5) H63B(0.5) H63C(0.5)
 C101(0.2) H10A(0.2) H10B(0.2) H10C(0.2) C102(0.2) H10D(0.2) H10E(0.2)
 O100(0.2) C103(0.2) H10F(0.2) H10G(0.2) C104(0.2) H10H(0.2) H10I(0.2)
 H10J(0.2) F99(0.3) F98(0.1) F97(0.1)
7.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C13(H13A,H13B), C24(H24A,H24B), C30(H30A,H30B),
 C31(H31A,H31B), C102(H10D,H10E), C103(H10F,H10G)
7.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C21(H21), C25(H25), C26(H26), C27(H27), C28(H28), C33(H33), C34(H34),
  C35(H35), C36(H36), C39(H39), C40X(H40X)
7.c X=CH2 refined with riding coordinates:
 N40'(H40A,H40B)
7.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C53(H53A,H53B,
 H53C), C63(H63A,H63B,H63C), C101(H10A,H10B,H10C), C104(H10H,H10I,H10J)
;
_shelx_res_checksum              3526
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.903
_oxdiff_exptl_absorpt_empirical_full_min 0.610