#------------------------------------------------------------------------------
#$Date: 2020-06-05 14:27:20 +0300 (Fri, 05 Jun 2020) $
#$Revision: 252905 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157474.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_7157474
loop_
_publ_author_name
'Zhulanov, Vladimir E.'
'Vigovskaya, Valeria A.'
'Dmitriev, Maksim V.'
'Silaichev, Pavel S.'
'Maslivets, Andrey N.'
'Rubin, Michael'
_publ_section_title
;
 Dipyrazolodioxadiazocines as shelf-stable "ready-to-use"
 precursors for an in situ generation of enolate-iminium 1,4-dipoles: a
 straightforward atom-economical approach to
 pyrazolo[5,1-d][1,3,5]dioxazines.
;
_journal_issue                   17
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3382
_journal_page_last               3391
_journal_paper_doi               10.1039/d0ob00451k
_journal_volume                  18
_journal_year                    2020
_chemical_compound_source        none
_chemical_formula_moiety         'C35 H32 N2 O5'
_chemical_formula_sum            'C35 H32 N2 O5'
_chemical_formula_weight         560.63
_chemical_melting_point          '165 -- 170 \%C (decomposition, acetone).'
_chemical_name_common            none
_chemical_name_systematic
'Methyl (1R,3S,5r,7r)-8'-(4-methylbenzoyl)-4',4'-diphenyl-4'H-spiro-[adamantane-2,2'-pyrazolo[5,1-d][1,3,5]dioxazine]-7'-carboxylate'
_chemical_properties_physical    Moisture-sensitive,Heat-sensitive
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc24lb25
_audit_creation_method           SHELXL-97
_audit_update_record
;
2020-02-13 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                100.473(10)
_cell_angle_beta                 97.068(10)
_cell_angle_gamma                103.526(10)
_cell_formula_units_Z            2
_cell_length_a                   10.5718(13)
_cell_length_b                   10.6288(12)
_cell_length_c                   13.5806(17)
_cell_measurement_reflns_used    4200
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.8550
_cell_measurement_theta_min      3.7850
_cell_volume                     1436.9(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13186
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.61
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         6834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0665P)²+0.1032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1459
_reflns_number_gt                5019
_reflns_number_total             6834
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            d0ob00451k2.cif
_cod_data_source_block           psu-26(md-313)
_cod_depositor_comments
'Adding full bibliography for 7157474--7157475.cif.'
_cod_database_code               7157474
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C33 C 0.35704(16) 0.87170(17) 0.43581(14) 0.0532(4) Uani 1 1 d . . .
H33A H 0.3751 0.8983 0.5094 0.064 Uiso 1 1 calc R . .
H33B H 0.3595 0.9504 0.4087 0.064 Uiso 1 1 calc R . .
O5 O 0.52319(8) 0.70515(9) 0.23570(7) 0.0362(2) Uani 1 1 d . . .
O4 O 0.42680(9) 0.88050(10) 0.24071(8) 0.0455(3) Uani 1 1 d . . .
N2 N 0.65476(11) 0.91802(11) 0.24943(9) 0.0367(3) Uani 1 1 d . . .
C7 C 0.65755(12) 0.77888(13) 0.24509(10) 0.0344(3) Uani 1 1 d . . .
N1 N 0.76421(11) 1.01367(12) 0.24308(9) 0.0400(3) Uani 1 1 d . . .
C6 C 0.74273(13) 0.76219(14) 0.33777(10) 0.0350(3) Uani 1 1 d . . .
C34 C 0.46282(14) 0.80572(15) 0.39861(11) 0.0411(3) Uani 1 1 d . . .
H34 H 0.5505 0.8682 0.4207 0.049 Uiso 1 1 calc R . .
C25 C 0.54465(13) 0.95969(14) 0.23954(11) 0.0369(3) Uani 1 1 d . . .
C26 C 0.43299(13) 0.76463(13) 0.28304(11) 0.0362(3) Uani 1 1 d . . .
C27 C 0.29733(14) 0.66751(15) 0.24799(12) 0.0434(4) Uani 1 1 d . . .
H27 H 0.2792 0.6409 0.1736 0.052 Uiso 1 1 calc R . .
C17 C 0.57913(13) 1.09029(14) 0.22964(11) 0.0386(3) Uani 1 1 d . . .
C8 C 0.70430(13) 0.72899(14) 0.14641(10) 0.0375(3) Uani 1 1 d . . .
C15 C 0.80632(14) 1.24045(15) 0.21954(13) 0.0438(4) Uani 1 1 d . . .
C29 C 0.22013(15) 0.77438(17) 0.40085(14) 0.0535(4) Uani 1 1 d . . .
H29 H 0.1531 0.8169 0.4243 0.064 Uiso 1 1 calc R . .
O3 O 0.76338(13) 1.26797(13) 0.13243(10) 0.0676(4) Uani 1 1 d . . .
O1 O 0.55147(12) 1.30465(12) 0.26326(11) 0.0688(4) Uani 1 1 d . . .
C9 C 0.83658(15) 0.74303(16) 0.14482(12) 0.0459(4) Uani 1 1 d . . .
H9 H 0.8975 0.7785 0.2047 0.055 Uiso 1 1 calc R . .
C19 C 0.35470(14) 1.13442(15) 0.20075(12) 0.0422(3) Uani 1 1 d . . .
C31 C 0.32157(16) 0.58610(16) 0.40913(12) 0.0490(4) Uani 1 1 d . . .
H31 H 0.3193 0.5075 0.4378 0.059 Uiso 1 1 calc R . .
C14 C 0.71691(13) 1.11616(14) 0.23249(11) 0.0378(3) Uani 1 1 d . . .
C5 C 0.75231(15) 0.63444(16) 0.33960(12) 0.0451(4) Uani 1 1 d . . .
H5 H 0.7060 0.5643 0.2863 0.054 Uiso 1 1 calc R . .
C32 C 0.29517(15) 0.54533(15) 0.29361(12) 0.0474(4) Uani 1 1 d . . .
H32A H 0.2097 0.4815 0.2706 0.057 Uiso 1 1 calc R . .
H32B H 0.3620 0.5037 0.2709 0.057 Uiso 1 1 calc R . .
C18 C 0.49932(14) 1.18609(15) 0.23303(12) 0.0434(3) Uani 1 1 d . . .
C1 C 0.81016(14) 0.86512(16) 0.41756(11) 0.0442(4) Uani 1 1 d . . .
H1 H 0.8051 0.9511 0.4169 0.053 Uiso 1 1 calc R . .
O2 O 0.90283(12) 1.30503(13) 0.27767(11) 0.0753(4) Uani 1 1 d . . .
C30 C 0.21669(17) 0.65220(18) 0.44558(14) 0.0551(4) Uani 1 1 d . . .
H30A H 0.1300 0.5902 0.4243 0.066 Uiso 1 1 calc R . .
H30B H 0.2337 0.6779 0.5192 0.066 Uiso 1 1 calc R . .
C28 C 0.19267(14) 0.73407(18) 0.28512(14) 0.0537(4) Uani 1 1 d . . .
H28A H 0.1944 0.8118 0.2568 0.064 Uiso 1 1 calc R . .
H28B H 0.1056 0.6731 0.2622 0.064 Uiso 1 1 calc R . .
C35 C 0.45806(15) 0.68309(17) 0.44325(12) 0.0482(4) Uani 1 1 d . . .
H35A H 0.5244 0.6406 0.4207 0.058 Uiso 1 1 calc R . .
H35B H 0.4772 0.7090 0.5169 0.058 Uiso 1 1 calc R . .
C20 C 0.30120(16) 1.03649(17) 0.11330(13) 0.0527(4) Uani 1 1 d . . .
H20 H 0.3566 1.0012 0.0747 0.063 Uiso 1 1 calc R . .
C4 C 0.82986(17) 0.61101(19) 0.41970(13) 0.0549(4) Uani 1 1 d . . .
H4 H 0.8369 0.5254 0.4198 0.066 Uiso 1 1 calc R . .
C11 C 0.79134(19) 0.65313(18) -0.03407(13) 0.0615(5) Uani 1 1 d . . .
H11 H 0.8206 0.6274 -0.0945 0.074 Uiso 1 1 calc R . .
C24 C 0.27104(16) 1.18561(18) 0.25782(14) 0.0546(4) Uani 1 1 d . . .
H24 H 0.3059 1.2527 0.3158 0.066 Uiso 1 1 calc R . .
C2 C 0.88581(15) 0.83990(19) 0.49904(12) 0.0556(4) Uani 1 1 d . . .
H2 H 0.9294 0.9090 0.5539 0.067 Uiso 1 1 calc R . .
C3 C 0.89671(17) 0.7134(2) 0.49925(14) 0.0598(5) Uani 1 1 d . . .
H3 H 0.9493 0.6974 0.5533 0.072 Uiso 1 1 calc R . .
C10 C 0.87986(17) 0.70470(17) 0.05461(13) 0.0566(4) Uani 1 1 d . . .
H10 H 0.9695 0.7141 0.0544 0.068 Uiso 1 1 calc R . .
C13 C 0.61540(17) 0.67733(18) 0.05631(12) 0.0539(4) Uani 1 1 d . . .
H13 H 0.5256 0.6679 0.0559 0.065 Uiso 1 1 calc R . .
C23 C 0.13620(18) 1.1370(2) 0.22864(16) 0.0671(5) Uani 1 1 d . . .
H23 H 0.0800 1.1695 0.2681 0.080 Uiso 1 1 calc R . .
C22 C 0.08479(17) 1.0411(2) 0.14176(18) 0.0706(6) Uani 1 1 d . . .
H22 H -0.0063 1.0094 0.1221 0.085 Uiso 1 1 calc R . .
C12 C 0.6601(2) 0.6396(2) -0.03342(13) 0.0658(5) Uani 1 1 d . . .
H12 H 0.5999 0.6047 -0.0938 0.079 Uiso 1 1 calc R . .
C21 C 0.16610(18) 0.9914(2) 0.08350(16) 0.0674(5) Uani 1 1 d . . .
H21 H 0.1303 0.9273 0.0239 0.081 Uiso 1 1 calc R . .
C16 C 0.8335(2) 1.3919(2) 0.11181(19) 0.0899(7) Uani 1 1 d . . .
H16A H 0.8372 1.4633 0.1676 0.135 Uiso 1 1 calc R . .
H16B H 0.7882 1.4061 0.0507 0.135 Uiso 1 1 calc R . .
H16C H 0.9216 1.3886 0.1034 0.135 Uiso 1 1 calc R . .
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'
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'
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
C29 C33 C34 109.84(13) . . ?
C26 O5 C7 120.08(10) . . ?
C25 O4 C26 114.14(10) . . ?
C25 N2 N1 112.02(11) . . ?
C25 N2 C7 124.72(11) . . ?
N1 N2 C7 122.00(11) . . ?
O5 C7 N2 106.11(10) . . ?
O5 C7 C6 111.20(10) . . ?
N2 C7 C6 112.73(11) . . ?
O5 C7 C8 106.72(10) . . ?
N2 C7 C8 107.88(10) . . ?
C6 C7 C8 111.84(11) . . ?
C14 N1 N2 103.50(11) . . ?
C1 C6 C5 119.41(14) . . ?
C1 C6 C7 123.91(13) . . ?
C5 C6 C7 116.67(13) . . ?
C26 C34 C35 109.53(12) . . ?
C26 C34 C33 109.04(12) . . ?
C35 C34 C33 108.71(12) . . ?
O4 C25 N2 121.56(12) . . ?
O4 C25 C17 130.23(13) . . ?
N2 C25 C17 108.21(11) . . ?
O5 C26 O4 107.29(10) . . ?
O5 C26 C27 106.84(11) . . ?
O4 C26 C27 106.02(11) . . ?
O5 C26 C34 116.51(11) . . ?
O4 C26 C34 109.41(11) . . ?
C27 C26 C34 110.22(11) . . ?
C26 C27 C28 109.20(13) . . ?
C26 C27 C32 108.74(12) . . ?
C28 C27 C32 109.58(12) . . ?
C25 C17 C14 102.71(12) . . ?
C25 C17 C18 129.23(12) . . ?
C14 C17 C18 127.31(13) . . ?
C9 C8 C13 118.88(14) . . ?
C9 C8 C7 120.31(13) . . ?
C13 C8 C7 120.67(13) . . ?
O2 C15 O3 124.74(15) . . ?
O2 C15 C14 125.57(15) . . ?
O3 C15 C14 109.69(13) . . ?
C28 C29 C30 109.83(14) . . ?
C28 C29 C33 109.14(13) . . ?
C30 C29 C33 109.19(14) . . ?
C15 O3 C16 116.72(16) . . ?
C8 C9 C10 120.49(15) . . ?
C24 C19 C20 119.32(15) . . ?
C24 C19 C18 119.65(15) . . ?
C20 C19 C18 121.02(14) . . ?
C32 C31 C35 108.54(12) . . ?
C32 C31 C30 109.99(14) . . ?
C35 C31 C30 109.86(14) . . ?
N1 C14 C17 113.52(12) . . ?
N1 C14 C15 119.89(12) . . ?
C17 C14 C15 126.50(13) . . ?
C4 C5 C6 120.43(16) . . ?
C31 C32 C27 109.90(13) . . ?
O1 C18 C17 120.47(13) . . ?
O1 C18 C19 121.56(14) . . ?
C17 C18 C19 117.96(13) . . ?
C6 C1 C2 119.66(16) . . ?
C29 C30 C31 109.47(13) . . ?
C29 C28 C27 109.80(13) . . ?
C31 C35 C34 109.87(12) . . ?
C21 C20 C19 120.12(17) . . ?
C3 C4 C5 120.16(17) . . ?
C12 C11 C10 119.67(16) . . ?
C23 C24 C19 119.92(18) . . ?
C3 C2 C1 120.48(16) . . ?
C4 C3 C2 119.82(15) . . ?
C11 C10 C9 120.29(16) . . ?
C8 C13 C12 120.01(16) . . ?
C22 C23 C24 120.11(18) . . ?
C23 C22 C21 120.66(17) . . ?
C11 C12 C13 120.65(17) . . ?
C22 C21 C20 119.83(19) . . ?
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
C33 C29 1.530(2) . ?
C33 C34 1.541(2) . ?
O5 C26 1.4168(16) . ?
O5 C7 1.4305(15) . ?
O4 C25 1.3342(16) . ?
O4 C26 1.4620(17) . ?
N2 C25 1.3393(18) . ?
N2 N1 1.3733(15) . ?
N2 C7 1.4766(17) . ?
C7 C6 1.5177(19) . ?
C7 C8 1.5326(19) . ?
N1 C14 1.3235(18) . ?
C6 C1 1.376(2) . ?
C6 C5 1.389(2) . ?
C34 C26 1.523(2) . ?
C34 C35 1.527(2) . ?
C25 C17 1.3861(19) . ?
C26 C27 1.5198(18) . ?
C27 C28 1.534(2) . ?
C27 C32 1.534(2) . ?
C17 C14 1.4119(19) . ?
C17 C18 1.465(2) . ?
C8 C9 1.375(2) . ?
C8 C13 1.383(2) . ?
C15 O2 1.1885(19) . ?
C15 O3 1.3217(19) . ?
C15 C14 1.487(2) . ?
C29 C28 1.524(2) . ?
C29 C30 1.525(2) . ?
O3 C16 1.446(2) . ?
O1 C18 1.2213(18) . ?
C9 C10 1.386(2) . ?
C19 C24 1.385(2) . ?
C19 C20 1.387(2) . ?
C19 C18 1.478(2) . ?
C31 C32 1.522(2) . ?
C31 C35 1.525(2) . ?
C31 C30 1.530(2) . ?
C5 C4 1.375(2) . ?
C1 C2 1.388(2) . ?
C20 C21 1.379(2) . ?
C4 C3 1.369(3) . ?
C11 C12 1.362(3) . ?
C11 C10 1.367(3) . ?
C24 C23 1.378(2) . ?
C2 C3 1.377(3) . ?
C13 C12 1.386(2) . ?
C23 C22 1.368(3) . ?
C22 C21 1.368(3) . ?
