#------------------------------------------------------------------------------
#$Date: 2023-06-05 07:44:12 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284296 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/24/7062418.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_7062418
loop_
_publ_author_name
Suraj,
'Swamy, K. C. Kumara'
_publ_section_title
;
 Ring expansion/opening reactions of epoxy ene-amides: access to
 azabicyclononene, tetrahydropyridine and tetrazole scaffolds
;
_journal_issue                   19
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9061
_journal_page_last               9065
_journal_paper_doi               10.1039/D3NJ00529A
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C38 H34 N4 O11 S2, 1[CH2Cl2]'
_chemical_formula_sum            'C39 H36 Cl2 N4 O11 S2'
_chemical_formula_weight         871.74
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-18
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2023-01-20 deposited with the CCDC.	2023-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.8268(11)
_cell_length_b                   16.2750(7)
_cell_length_c                   10.0472(5)
_cell_measurement_reflns_used    8330
_cell_measurement_temperature    284
_cell_measurement_theta_max      25.0250
_cell_measurement_theta_min      2.4940
_cell_volume                     4223.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (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 (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      284
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00   0.00   0.50   14.00    --  -14.97 -32.00 -44.00   78
  2  ω     -8.00  44.00   0.50   14.00    --   16.22 -61.00 -30.00  104
  3  ω    -13.00  21.00   0.50   14.00    --  -14.97 -94.00   0.00   68
  4  ω     10.00  40.00   0.50   14.00    --   16.22-125.00  60.00   60
  5  ω    -50.00 -14.00   0.50   14.00    --   16.22 -61.00 -30.00   72
  6  ω    -69.00 -22.00   0.50   14.00    --  -14.97 125.00  60.00   94
  7  ω    -81.00 -19.00   0.50   14.00    --  -14.97 143.00 -19.00  124
  8  ω      4.00  45.00   0.50   14.00    --  -14.97  30.00-180.00   82
  9  ω    -40.00 -15.00   0.50   14.00    --  -14.97  30.00-180.00   50
 10  ω    -69.00 -26.00   0.50   14.00    --  -14.97 125.00 150.00   86
 11  ω    -45.00  50.00   0.50   14.00    --   16.22 -90.00 166.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0089145000
_diffrn_orient_matrix_UB_12      -0.0289556000
_diffrn_orient_matrix_UB_13      -0.0474931000
_diffrn_orient_matrix_UB_21      0.0058325000
_diffrn_orient_matrix_UB_22      -0.0279947000
_diffrn_orient_matrix_UB_23      0.0520046000
_diffrn_orient_matrix_UB_31      -0.0253115000
_diffrn_orient_matrix_UB_32      -0.0166745000
_diffrn_orient_matrix_UB_33      -0.0047368000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            24055
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.503
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       needle
_exptl_crystal_F_000             1808
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0579
_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)+(0.0770P)²+1.2455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1543
_refine_ls_wR_factor_ref         0.1784
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2260
_reflns_number_total             3723
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj00529a2.cif
_cod_data_source_block           Compound6hc
_cod_depositor_comments
'Adding full bibliography for 7062416--7062421.cif.'
_cod_database_code               7062418
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S'
_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_max   0.969
_shelx_estimated_absorpt_t_min   0.940
_reflns_odcompleteness_completeness 99.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Uiso/Uaniso restraints and constraints
Uanis(O003) = Uanis(S1)
3.a Ternary CH refined with riding coordinates:
 C9(H9), C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C6(H6), C14(H14), C2(H2), C4(H4), C18(H18), C5(H5), C3(H3),
 C17(H17), C16(H16)
3.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 2.152
_oxdiff_exptl_absorpt_empirical_full_min 0.453
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, 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
S1 S 0.30438(3) 0.30882(5) 0.39549(10) 0.0695(3) Uani 1 1 d . . . . .
O002 O 0.500000 0.34647(16) 0.250000 0.0669(8) Uani 1 2 d S T P . .
O003 O 0.28028(8) 0.35127(12) 0.2879(2) 0.0695(3) Uani 1 1 d . . . . .
O004 O 0.29849(10) 0.33901(15) 0.5270(2) 0.0949(8) Uani 1 1 d . . . . .
N1 N 0.36781(9) 0.30834(13) 0.3595(2) 0.0595(7) Uani 1 1 d . . . . .
O006 O 0.53161(12) 0.36699(19) 0.5496(3) 0.1200(11) Uani 1 1 d . . . . .
C11 C 0.40529(13) 0.30201(17) 0.4594(3) 0.0639(8) Uani 1 1 d . . . . .
C12 C 0.39295(13) 0.24736(18) 0.5745(3) 0.0669(8) Uani 1 1 d . . . . .
C7 C 0.38598(12) 0.34013(19) 0.2302(3) 0.0663(8) Uani 1 1 d . . . . .
H7A H 0.356504 0.351782 0.173424 0.080 Uiso 1 1 calc R . . . .
H7B H 0.407201 0.299027 0.186478 0.080 Uiso 1 1 calc R . . . .
C1 C 0.28521(12) 0.20548(18) 0.3882(3) 0.0624(8) Uani 1 1 d . . . . .
C9 C 0.46467(11) 0.39373(18) 0.3311(3) 0.0650(8) Uani 1 1 d . . . . .
H9 H 0.482203 0.443300 0.363257 0.078 Uiso 1 1 calc R . . . .
C8 C 0.41736(12) 0.41804(17) 0.2510(3) 0.0696(9) Uani 1 1 d . . . . .
H8 H 0.428921 0.437913 0.163898 0.083 Uiso 1 1 calc R . . . .
C13 C 0.38929(13) 0.16351(19) 0.5564(3) 0.0688(9) Uani 1 1 d . . . . .
H13 H 0.391761 0.141738 0.471024 0.083 Uiso 1 1 calc R . . . .
C10 C 0.45143(13) 0.33994(18) 0.4465(3) 0.0660(8) Uani 1 1 d . . . . .
C6 C 0.29302(14) 0.1632(2) 0.2718(4) 0.0809(10) Uani 1 1 d . . . . .
H6 H 0.308597 0.188393 0.199032 0.097 Uiso 1 1 calc R . . . .
O00G O 0.37790(17) 0.0162(3) 0.8834(4) 0.1557(16) Uani 1 1 d . . . . .
C14 C 0.38203(14) 0.1116(2) 0.6632(4) 0.0803(10) Uani 1 1 d . . . . .
H14 H 0.380283 0.055089 0.650704 0.096 Uiso 1 1 calc R . . . .
N2 N 0.37060(19) 0.0885(4) 0.9008(5) 0.1278(15) Uani 1 1 d . . . . .
C2 C 0.26195(14) 0.1705(2) 0.4957(4) 0.0861(11) Uani 1 1 d . . . . .
H2 H 0.256997 0.200491 0.573453 0.103 Uiso 1 1 calc R . . . .
C19 C 0.38643(13) 0.48654(19) 0.3185(4) 0.0921(12) Uani 1 1 d . . . . .
H19A H 0.357388 0.501080 0.263740 0.138 Uiso 1 1 calc GR . . . .
H19B H 0.408208 0.533746 0.330675 0.138 Uiso 1 1 calc GR . . . .
H19C H 0.374269 0.467770 0.403566 0.138 Uiso 1 1 calc GR . . . .
C15 C 0.37751(16) 0.1440(3) 0.7855(4) 0.0916(12) Uani 1 1 d . . . . .
C4 C 0.25409(16) 0.0470(2) 0.3743(6) 0.1091(16) Uani 1 1 d . . . . .
H4 H 0.243790 -0.007673 0.370308 0.131 Uiso 1 1 calc R . . . .
C18 C 0.49248(17) 0.3267(2) 0.5445(4) 0.0944(12) Uani 1 1 d . . . . .
H18 H 0.488132 0.284851 0.606470 0.113 Uiso 1 1 calc R . . . .
C5 C 0.27714(18) 0.0823(2) 0.2657(5) 0.1059(14) Uani 1 1 d . . . . .
H5 H 0.282056 0.051990 0.188238 0.127 Uiso 1 1 calc R . . . .
C3 C 0.24601(16) 0.0906(3) 0.4879(6) 0.1075(14) Uani 1 1 d . . . . .
H3 H 0.229663 0.066030 0.560148 0.129 Uiso 1 1 calc R . . . .
C17 C 0.38872(18) 0.2781(3) 0.7027(4) 0.1041(14) Uani 1 1 d . . . . .
H17 H 0.391810 0.334271 0.717408 0.125 Uiso 1 1 calc R . . . .
C16 C 0.38003(19) 0.2264(3) 0.8078(4) 0.1179(16) Uani 1 1 d . . . . .
H16 H 0.375907 0.247296 0.893263 0.142 Uiso 1 1 calc R . . . .
O00S O 0.3597(2) 0.1175(3) 1.0050(4) 0.221(3) 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O003 S1 N1 105.37(13) . . ?
O003 S1 C1 108.03(14) . . ?
O004 S1 O003 119.44(15) . . ?
O004 S1 N1 107.90(14) . . ?
O004 S1 C1 109.93(16) . . ?
N1 S1 C1 105.20(13) . . ?
C9 O002 C9 115.7(3) 3_655 . ?
C11 N1 S1 121.4(2) . . ?
C11 N1 C7 116.0(2) . . ?
C7 N1 S1 119.9(2) . . ?
N1 C11 C12 116.9(3) . . ?
C10 C11 N1 120.6(3) . . ?
C10 C11 C12 122.4(3) . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 C17 118.3(3) . . ?
C17 C12 C11 121.4(3) . . ?
N1 C7 C8 109.9(3) . . ?
C6 C1 S1 118.4(3) . . ?
C2 C1 S1 119.5(3) . . ?
C2 C1 C6 122.1(3) . . ?
O002 C9 C8 110.4(2) . . ?
O002 C9 C10 105.7(2) . . ?
C10 C9 C8 112.4(3) . . ?
C7 C8 C19 113.0(3) . . ?
C9 C8 C7 106.6(2) . . ?
C9 C8 C19 112.1(3) . . ?
C14 C13 C12 120.8(3) . . ?
C11 C10 C9 123.1(3) . . ?
C11 C10 C18 120.5(3) . . ?
C18 C10 C9 116.3(3) . . ?
C1 C6 C5 118.2(4) . . ?
C15 C14 C13 119.0(3) . . ?
O00G N2 C15 117.7(5) . . ?
O00S N2 O00G 123.8(5) . . ?
O00S N2 C15 118.5(6) . . ?
C1 C2 C3 119.0(4) . . ?
C14 C15 N2 119.2(4) . . ?
C14 C15 C16 122.2(4) . . ?
C16 C15 N2 118.6(4) . . ?
C3 C4 C5 121.1(4) . . ?
O006 C18 C10 123.8(4) . . ?
C4 C5 C6 119.6(4) . . ?
C4 C3 C2 119.9(4) . . ?
C16 C17 C12 120.5(4) . . ?
C15 C16 C17 119.1(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O003 1.426(2) . ?
S1 O004 1.418(2) . ?
S1 N1 1.677(3) . ?
S1 C1 1.755(3) . ?
O002 C9 1.445(3) . ?
O002 C9 1.445(3) 3_655 ?
N1 C11 1.399(4) . ?
N1 C7 1.475(4) . ?
O006 C18 1.205(4) . ?
C11 C12 1.493(4) . ?
C11 C10 1.348(4) . ?
C12 C13 1.380(4) . ?
C12 C17 1.385(4) . ?
C7 C8 1.519(4) . ?
C1 C6 1.371(4) . ?
C1 C2 1.362(5) . ?
C9 C8 1.515(4) . ?
C9 C10 1.492(4) . ?
C8 C19 1.530(4) . ?
C13 C14 1.378(4) . ?
C10 C18 1.463(5) . ?
C6 C5 1.380(5) . ?
O00G N2 1.204(5) . ?
C14 C15 1.342(5) . ?
N2 C15 1.480(6) . ?
N2 O00S 1.183(5) . ?
C2 C3 1.366(5) . ?
C15 C16 1.362(6) . ?
C4 C5 1.370(6) . ?
C4 C3 1.360(6) . ?
C17 C16 1.368(5) . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 -0.636 312.1 84.2 '0.5 CH2Cl2'
2 0.500 0.000 -0.109 312.1 84.2 '0.5 CH2Cl2'
