#------------------------------------------------------------------------------
#$Date: 2019-11-24 21:55:12 +0200 (Sun, 24 Nov 2019) $
#$Revision: 239531 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/67/4516775.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4516775
loop_
_publ_author_name
'Karimov, Rashad R.'
'Sharma, Ankit'
'Hartwig, John F.'
_publ_section_title
;
 Late Stage Azidation of Complex Molecules.
;
_journal_issue                   10
_journal_name_full               'ACS central science'
_journal_page_first              715
_journal_page_last               724
_journal_paper_doi               10.1021/acscentsci.6b00214
_journal_volume                  2
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H26 N6 O7'
_chemical_formula_weight         486.49
_chemical_name_common            azide_4c
_chemical_name_systematic        azide_4c
_space_group.centring_type       primitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 103.0580(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1836(2)
_cell_length_b                   10.5248(2)
_cell_length_c                   13.9957(3)
_cell_measurement_reflns_used    8061
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      68.35
_cell_measurement_theta_min      3.24
_cell_volume                     1174.29(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2014
_computing_structure_solution    SHELXT-2014
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_refln_scan_rate          1
_diffrn_refln_scan_width         2.0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15676
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.381
_diffrn_reflns_theta_min         3.241
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.879
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
; 
 Flack x determined using 1577 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.11(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4236
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0387
_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/[σ²(Fo²)+(0.0474P)²+0.1602P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1005
_reflns_Friedel_coverage         0.861
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                3826
_reflns_number_total             4236
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            oc6b00214_si_006.cif
_cod_data_source_block           azide4c
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4516775
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.941
_shelx_estimated_absorpt_t_max   0.974
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5576(4) 0.2615(3) 0.2046(2) 0.0398(7) Uani 1 1 d . . . . .
C2 C 0.5164(4) 0.3839(3) 0.2534(2) 0.0384(7) Uani 1 1 d . . . . .
H2A H 0.5932 0.4530 0.2438 0.046 Uiso 1 1 calc R U . . .
H2B H 0.5284 0.3705 0.3246 0.046 Uiso 1 1 calc R U . . .
C3 C 0.3317(3) 0.4187(3) 0.20379(19) 0.0323(6) Uani 1 1 d . . . . .
C4 C 0.2245(3) 0.4791(3) 0.27226(19) 0.0325(6) Uani 1 1 d . . . . .
H4 H 0.1136 0.4349 0.2605 0.039 Uiso 1 1 calc R U . . .
C5 C 0.1959(3) 0.6171(3) 0.2396(2) 0.0354(6) Uani 1 1 d . . . . .
H5 H 0.2863 0.6736 0.2770 0.042 Uiso 1 1 calc R U . . .
C6 C 0.0329(4) 0.8167(3) 0.2083(2) 0.0471(8) Uani 1 1 d . . . . .
H6 H -0.0818 0.8550 0.1913 0.056 Uiso 1 1 calc R U . . .
C7 C 0.1223(4) 0.8393(4) 0.1265(3) 0.0506(8) Uani 1 1 d . . . . .
H7 H 0.1229 0.9224 0.1001 0.061 Uiso 1 1 calc R U . . .
C8 C 0.1996(4) 0.7465(3) 0.0908(2) 0.0457(8) Uani 1 1 d . . . . .
H8 H 0.2571 0.7630 0.0402 0.055 Uiso 1 1 calc R U . . .
C9 C 0.1955(3) 0.6153(3) 0.1310(2) 0.0362(6) Uani 1 1 d . . . . .
C10 C 0.3284(3) 0.5194(3) 0.1206(2) 0.0353(6) Uani 1 1 d . . . . .
H10 H 0.4387 0.5645 0.1362 0.042 Uiso 1 1 calc R U . . .
C11 C 0.3106(4) 0.4584(3) 0.0199(2) 0.0395(7) Uani 1 1 d . . . . .
H11A H 0.1929 0.4320 -0.0061 0.047 Uiso 1 1 calc R U . . .
H11B H 0.3408 0.5207 -0.0263 0.047 Uiso 1 1 calc R U . . .
C12 C 0.4257(4) 0.3431(3) 0.0284(2) 0.0392(7) Uani 1 1 d . . . . .
H12A H 0.5434 0.3728 0.0400 0.047 Uiso 1 1 calc R U . . .
H12B H 0.4003 0.2965 -0.0347 0.047 Uiso 1 1 calc R U . . .
C13 C 0.4092(3) 0.2500(3) 0.1119(2) 0.0364(6) Uani 1 1 d . . . . .
C14 C 0.2631(3) 0.2923(3) 0.15653(19) 0.0330(6) Uani 1 1 d . . . . .
H14A H 0.2422 0.2308 0.2060 0.040 Uiso 1 1 calc R U . . .
H14B H 0.1588 0.3046 0.1055 0.040 Uiso 1 1 calc R U . . .
C15 C -0.0782(3) 0.6065(3) 0.1424(2) 0.0373(6) Uani 1 1 d . . . . .
C16 C 0.0217(4) 0.6744(3) 0.2336(2) 0.0388(7) Uani 1 1 d . . . . .
C17 C 0.7354(4) 0.2614(4) 0.1874(2) 0.0501(9) Uani 1 1 d . . . . .
H17A H 0.7659 0.1733 0.1735 0.060 Uiso 1 1 calc R U . . .
H17B H 0.7372 0.3134 0.1287 0.060 Uiso 1 1 calc R U . . .
C18 C 0.3072(4) 0.4706(3) 0.3803(2) 0.0369(6) Uani 1 1 d . . . . .
C19 C 0.3402(8) 0.3482(6) 0.5235(3) 0.098(2) Uani 1 1 d . . . . .
H19A H 0.3236 0.4247 0.5601 0.146 Uiso 1 1 calc R U . . .
H19B H 0.4605 0.3327 0.5312 0.146 Uiso 1 1 calc R U . . .
H19C H 0.2886 0.2753 0.5487 0.146 Uiso 1 1 calc R U . . .
C20 C -0.0585(4) 0.6545(4) 0.3213(2) 0.0472(8) Uani 1 1 d . . . . .
H20A H 0.0116 0.6943 0.3796 0.071 Uiso 1 1 calc R U . . .
H20B H -0.0681 0.5633 0.3330 0.071 Uiso 1 1 calc R U . . .
H20C H -0.1703 0.6931 0.3073 0.071 Uiso 1 1 calc R U . . .
C21 C 0.1095(11) 0.9921(9) 0.3103(7) 0.056(2) Uani 0.638(10) 1 d D . P A 1
C22 C 0.216(2) 1.0425(14) 0.4033(9) 0.071(4) Uani 0.638(10) 1 d D . P A 1
H22A H 0.2812 0.9729 0.4399 0.106 Uiso 0.638(10) 1 calc R U P A 1
H22B H 0.2922 1.1073 0.3882 0.106 Uiso 0.638(10) 1 calc R U P A 1
H22C H 0.1440 1.0803 0.4430 0.106 Uiso 0.638(10) 1 calc R U P A 1
C21A C 0.068(2) 0.9735(18) 0.3400(14) 0.056(2) Uani 0.362(10) 1 d D . P A 2
C22A C 0.194(4) 1.018(3) 0.4288(19) 0.071(4) Uani 0.362(10) 1 d D . P A 2
H22D H 0.3033 0.9789 0.4291 0.106 Uiso 0.362(10) 1 calc R U P A 2
H22E H 0.2043 1.1103 0.4269 0.106 Uiso 0.362(10) 1 calc R U P A 2
H22F H 0.1579 0.9926 0.4881 0.106 Uiso 0.362(10) 1 calc R U P A 2
N1 N 0.5411(4) 0.1566(3) 0.27519(18) 0.0460(7) Uani 1 1 d . . . . .
N2 N 0.5704(5) 0.0475(4) 0.2508(2) 0.0615(9) Uani 1 1 d . . . . .
N3 N 0.5943(7) -0.0566(5) 0.2396(3) 0.0968(16) Uani 1 1 d . . . . .
N4 N 0.8619(3) 0.3107(4) 0.2706(2) 0.0552(8) Uani 1 1 d . . . . .
N5 N 0.8669(3) 0.2674(3) 0.3517(2) 0.0517(7) Uani 1 1 d . . . . .
N6 N 0.8854(5) 0.2442(6) 0.4306(3) 0.0942(15) Uani 1 1 d . . . . .
O1 O 0.4054(3) 0.5465(2) 0.42428(16) 0.0529(6) Uani 1 1 d . . . . .
O2 O 0.2627(4) 0.3660(3) 0.42014(16) 0.0617(7) Uani 1 1 d . . . . .
O3 O 0.1318(3) 0.8751(2) 0.29669(19) 0.0578(7) Uani 1 1 d . . . . .
O4 O 0.0162(7) 1.0565(4) 0.2509(4) 0.077(2) Uani 0.638(10) 1 d . . P A 1
O4A O -0.0762(11) 1.0002(10) 0.3154(8) 0.086(5) Uani 0.362(10) 1 d . . P A 2
O5 O 0.4021(3) 0.1213(2) 0.08071(15) 0.0453(5) Uani 1 1 d . . . . .
H5A H 0.3445 0.1160 0.0230 0.068 Uiso 1 1 calc R U . . .
O6 O 0.0245(2) 0.5631(2) 0.08741(13) 0.0374(5) Uani 1 1 d . . . . .
O7 O -0.2280(2) 0.5913(2) 0.11876(15) 0.0455(6) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 C17 109.4(3)
N1 C1 C2 105.2(2)
C17 C1 C2 112.6(3)
N1 C1 C13 108.5(3)
C17 C1 C13 117.2(2)
C2 C1 C13 103.1(2)
C1 C2 C3 106.8(2)
C1 C2 H2A 110.4
C3 C2 H2A 110.4
C1 C2 H2B 110.4
C3 C2 H2B 110.4
H2A C2 H2B 108.6
C14 C3 C2 102.2(2)
C14 C3 C10 108.8(2)
C2 C3 C10 110.0(2)
C14 C3 C4 114.4(2)
C2 C3 C4 116.3(2)
C10 C3 C4 105.1(2)
C18 C4 C5 111.1(2)
C18 C4 C3 113.6(2)
C5 C4 C3 105.7(2)
C18 C4 H4 108.8
C5 C4 H4 108.8
C3 C4 H4 108.8
C9 C5 C4 104.7(2)
C9 C5 C16 99.1(2)
C4 C5 C16 118.0(3)
C9 C5 H5 111.4
C4 C5 H5 111.4
C16 C5 H5 111.4
O3 C6 C7 107.8(3)
O3 C6 C16 105.4(3)
C7 C6 C16 113.0(3)
O3 C6 H6 110.2
C7 C6 H6 110.2
C16 C6 H6 110.2
C8 C7 C6 121.7(3)
C8 C7 H7 119.2
C6 C7 H7 119.2
C7 C8 C9 119.2(3)
C7 C8 H8 120.4
C9 C8 H8 120.4
C8 C9 O6 106.5(2)
C8 C9 C10 120.2(2)
O6 C9 C10 110.0(2)
C8 C9 C5 111.7(3)
O6 C9 C5 101.7(2)
C10 C9 C5 105.4(2)
C9 C10 C11 116.6(2)
C9 C10 C3 105.7(2)
C11 C10 C3 112.6(3)
C9 C10 H10 107.1
C11 C10 H10 107.1
C3 C10 H10 107.1
C12 C11 C10 109.5(2)
C12 C11 H11A 109.8
C10 C11 H11A 109.8
C12 C11 H11B 109.8
C10 C11 H11B 109.8
H11A C11 H11B 108.2
C11 C12 C13 113.8(2)
C11 C12 H12A 108.8
C13 C12 H12A 108.8
C11 C12 H12B 108.8
C13 C12 H12B 108.8
H12A C12 H12B 107.7
O5 C13 C14 114.9(2)
O5 C13 C12 112.0(2)
C14 C13 C12 109.4(2)
O5 C13 C1 107.3(2)
C14 C13 C1 99.8(2)
C12 C13 C1 113.0(3)
C13 C14 C3 100.6(2)
C13 C14 H14A 111.7
C3 C14 H14A 111.7
C13 C14 H14B 111.7
C3 C14 H14B 111.7
H14A C14 H14B 109.4
O7 C15 O6 121.8(3)
O7 C15 C16 127.6(3)
O6 C15 C16 110.6(2)
C15 C16 C20 111.1(3)
C15 C16 C5 100.2(2)
C20 C16 C5 117.6(2)
C15 C16 C6 108.1(2)
C20 C16 C6 112.0(3)
C5 C16 C6 106.9(3)
N4 C17 C1 113.6(3)
N4 C17 H17A 108.8
C1 C17 H17A 108.8
N4 C17 H17B 108.8
C1 C17 H17B 108.8
H17A C17 H17B 107.7
O1 C18 O2 123.6(3)
O1 C18 C4 124.8(3)
O2 C18 C4 111.6(3)
O2 C19 H19A 109.5
O2 C19 H19B 109.5
H19A C19 H19B 109.5
O2 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C16 C20 H20A 109.5
C16 C20 H20B 109.5
H20A C20 H20B 109.5
C16 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
O4 C21 O3 122.3(8)
O4 C21 C22 123.9(10)
O3 C21 C22 113.7(10)
C21 C22 H22A 109.5
C21 C22 H22B 109.5
H22A C22 H22B 109.5
C21 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
O4A C21A O3 120.6(15)
O4A C21A C22A 129(2)
O3 C21A C22A 110(2)
C21A C22A H22D 109.5
C21A C22A H22E 109.5
H22D C22A H22E 109.5
C21A C22A H22F 109.5
H22D C22A H22F 109.5
H22E C22A H22F 109.5
N2 N1 C1 116.5(3)
N3 N2 N1 171.4(4)
N5 N4 C17 118.6(3)
N6 N5 N4 169.2(5)
C18 O2 C19 115.3(3)
C21 O3 C6 118.0(5)
C21A O3 C6 120.2(8)
C13 O5 H5A 109.5
C15 O6 C9 106.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.508(4)
C1 C17 1.527(4)
C1 C2 1.531(5)
C1 C13 1.568(4)
C2 C3 1.558(4)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C14 1.535(4)
C3 C10 1.570(4)
C3 C4 1.573(4)
C4 C18 1.513(4)
C4 C5 1.524(4)
C4 H4 1.0000
C5 C9 1.520(4)
C5 C16 1.533(4)
C5 H5 1.0000
C6 O3 1.453(4)
C6 C7 1.510(5)
C6 C16 1.546(5)
C6 H6 1.0000
C7 C8 1.322(5)
C7 H7 0.9500
C8 C9 1.494(5)
C8 H8 0.9500
C9 O6 1.499(3)
C9 C10 1.515(4)
C10 C11 1.526(4)
C10 H10 1.0000
C11 C12 1.524(5)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C13 1.555(4)
C12 H12A 0.9900
C12 H12B 0.9900
C13 O5 1.421(4)
C13 C14 1.534(4)
C14 H14A 0.9900
C14 H14B 0.9900
C15 O7 1.206(3)
C15 O6 1.342(3)
C15 C16 1.528(4)
C16 C20 1.531(4)
C17 N4 1.467(4)
C17 H17A 0.9900
C17 H17B 0.9900
C18 O1 1.200(4)
C18 O2 1.322(4)
C19 O2 1.454(5)
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
C21 O4 1.203(11)
C21 O3 1.265(10)
C21 C22 1.490(9)
C22 H22A 0.9800
C22 H22B 0.9800
C22 H22C 0.9800
C21A O4A 1.183(19)
C21A O3 1.363(19)
C21A C22A 1.501(13)
C22A H22D 0.9800
C22A H22E 0.9800
C22A H22F 0.9800
N1 N2 1.236(5)
N2 N3 1.130(6)
N4 N5 1.216(4)
N5 N6 1.107(5)
O5 H5A 0.8400
