#------------------------------------------------------------------------------
#$Date: 2019-11-24 01:52:20 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236110 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/74/4037416.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_4037416
loop_
_publ_author_name
'Pušavec Kirar, Eva'
'Grošelj, Uroš'
'Golobič, Amalija'
'Požgan, Franc'
'Pusch, Stefan'
'Weber, Carina'
'Andernach, Lars'
'Štefane, Bogdan'
'Opatz, Till'
'Svete, Jurij'
_publ_section_title
;
 Absolute Configuration Determination of
 2,3-Dihydro-1H,5H-pyrazolo[1,2-a]pyrazoles Using Chiroptical Methods at
 Different Wavelengths.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11802
_journal_page_last               11812
_journal_paper_doi               10.1021/acs.joc.6b02270
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration rm
_chemical_formula_sum            'C26 H28 N4 O6'
_chemical_formula_weight         492.52
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_H-M   'P 61'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                120.000(5)
_cell_formula_units_Z            6
_cell_length_a                   28.490(5)
_cell_length_b                   28.490(5)
_cell_length_c                   5.767(5)
_cell_measurement_reflns_used    3036
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      0.4
_cell_volume                     4054(4)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPIII (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.074
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            34525
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO-SMN; Otwinovski, Minor 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1560
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.214
_refine_diff_density_min         -1.086
_refine_diff_density_rms         0.359
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_coef       0.50(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.256
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5520
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.256
_refine_ls_R_factor_all          0.1622
_refine_ls_R_factor_gt           0.1082
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1572P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2051
_refine_ls_wR_factor_ref         0.2566
_reflns_number_gt                4079
_reflns_number_total             5520
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo6b02270_si_001.cif
_cod_data_source_block           3h-
_cod_original_sg_symbol_H-M      P61
_cod_database_code               4037416
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, x, z+1/6'
'y, -x+y, z+5/6'
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
C1 C 0.56593(13) 0.11746(12) 0.4997(7) 0.0521(8) Uani 1 1 d .
H1 H 0.5625 0.1088 0.6655 0.063 Uiso 1 1 calc R
C2 C 0.51450(14) 0.07510(13) 0.3743(8) 0.0604(9) Uani 1 1 d .
H2A H 0.4822 0.0664 0.4629 0.072 Uiso 1 1 calc R
H2B H 0.5116 0.0876 0.2214 0.072 Uiso 1 1 calc R
C3 C 0.52314(15) 0.02712(13) 0.3593(8) 0.0580(9) Uani 1 1 d .
C4 C 0.60899(16) 0.02714(14) 0.4520(7) 0.0585(9) Uani 1 1 d .
H4 H 0.5996 -0.0091 0.4395 0.070 Uiso 1 1 calc R
C5 C 0.65375(15) 0.06513(13) 0.5529(7) 0.0562(9) Uani 1 1 d .
C6 C 0.65487(14) 0.11909(13) 0.5483(7) 0.0514(8) Uani 1 1 d .
H6 H 0.6487 0.1283 0.7049 0.062 Uiso 1 1 calc R
C7 C 0.70724(14) 0.16500(13) 0.4516(7) 0.0528(8) Uani 1 1 d .
C8 C 0.73707(16) 0.21210(14) 0.5787(8) 0.0646(10) Uani 1 1 d .
H8 H 0.7235 0.2163 0.7189 0.078 Uiso 1 1 calc R
C9 C 0.78665(16) 0.25289(15) 0.5006(9) 0.0702(11) Uani 1 1 d .
H9 H 0.8065 0.2844 0.5865 0.084 Uiso 1 1 calc R
C10 C 0.80582(15) 0.24576(15) 0.2936(9) 0.0655(11) Uani 1 1 d .
C11 C 0.77721(18) 0.19998(18) 0.1623(9) 0.0749(12) Uani 1 1 d .
H11 H 0.7910 0.1961 0.0219 0.090 Uiso 1 1 calc R
C12 C 0.72749(17) 0.15958(16) 0.2419(9) 0.0710(11) Uani 1 1 d .
H12 H 0.7075 0.1285 0.1534 0.085 Uiso 1 1 calc R
C13 C 0.57912(12) 0.17551(12) 0.4698(6) 0.0481(8) Uani 1 1 d .
C14 C 0.60462(15) 0.20560(14) 0.2732(7) 0.0568(9) Uani 1 1 d .
H14 H 0.6161 0.1908 0.1581 0.068 Uiso 1 1 calc R
C15 C 0.61310(15) 0.25770(14) 0.2473(7) 0.0596(9) Uani 1 1 d .
H15 H 0.6303 0.2777 0.1154 0.071 Uiso 1 1 calc R
C16 C 0.59608(14) 0.27960(13) 0.4169(8) 0.0609(10) Uani 1 1 d .
H16 H 0.6013 0.3143 0.3981 0.073 Uiso 1 1 calc R
C17 C 0.57120(14) 0.25046(15) 0.6155(8) 0.0586(9) Uani 1 1 d .
H17 H 0.5601 0.2656 0.7309 0.070 Uiso 1 1 calc R
C18 C 0.56293(14) 0.19849(14) 0.6411(7) 0.0546(9) Uani 1 1 d .
H18 H 0.5463 0.1788 0.7746 0.066 Uiso 1 1 calc R
C19 C 0.69625(15) 0.06034(15) 0.6740(7) 0.0600(9) Uani 1 1 d .
C20 C 0.69619(16) 0.00663(16) 0.6690(10) 0.0710(12) Uani 1 1 d .
H20 H 0.6796 -0.0128 0.5247 0.085 Uiso 1 1 calc R
C21 C 0.6646(2) -0.0278(2) 0.8758(14) 0.105(2) Uani 1 1 d .
H21A H 0.6622 -0.0626 0.8660 0.158 Uiso 1 1 calc R
H21B H 0.6288 -0.0326 0.8755 0.158 Uiso 1 1 calc R
H21C H 0.6828 -0.0101 1.0166 0.158 Uiso 1 1 calc R
C22 C 0.7844(2) 0.0421(2) 0.4981(14) 0.0875(15) Uani 1 1 d .
C23 C 0.8805(3) 0.0972(3) 0.3975(19) 0.128(3) Uani 1 1 d .
C24 C 0.9302(3) 0.1160(4) 0.546(2) 0.160(4) Uani 1 1 d .
H24A H 0.9298 0.1386 0.6687 0.240 Uiso 1 1 calc R
H24B H 0.9621 0.1362 0.4532 0.240 Uiso 1 1 calc R
H24C H 0.9304 0.0851 0.6117 0.240 Uiso 1 1 calc R
C25 C 0.8804(4) 0.0609(6) 0.207(2) 0.182(5) Uani 1 1 d .
H25A H 0.8842 0.0321 0.2728 0.273 Uiso 1 1 calc R
H25B H 0.9100 0.0817 0.1028 0.273 Uiso 1 1 calc R
H25C H 0.8468 0.0459 0.1230 0.273 Uiso 1 1 calc R
C26 C 0.8769(4) 0.1439(4) 0.309(3) 0.218(8) Uani 1 1 d .
H26A H 0.8496 0.1318 0.1905 0.327 Uiso 1 1 calc R
H26B H 0.9112 0.1702 0.2449 0.327 Uiso 1 1 calc R
H26C H 0.8674 0.1599 0.4334 0.327 Uiso 1 1 calc R
N1 N 0.60765(11) 0.10696(10) 0.3973(6) 0.0524(8) Uani 1 1 d .
N2 N 0.57823(12) 0.04825(10) 0.3680(6) 0.0568(8) Uani 1 1 d .
N3 N 0.75203(15) 0.01823(14) 0.6826(9) 0.0807(12) Uani 1 1 d .
H3 H 0.7640 0.0101 0.8043 0.097 Uiso 1 1 calc R
N4 N 0.85905(16) 0.28931(17) 0.2142(10) 0.0882(14) Uani 1 1 d .
O1 O 0.49030(11) -0.02087(10) 0.3458(6) 0.0684(8) Uani 1 1 d .
O2 O 0.73121(14) 0.09895(13) 0.7801(7) 0.0809(9) Uani 1 1 d .
O3 O 0.76881(19) 0.0423(2) 0.3009(11) 0.1279(17) Uani 1 1 d .
O4 O 0.83640(13) 0.06323(15) 0.5574(10) 0.1015(13) Uani 1 1 d .
O5 O 0.88450(14) 0.32941(16) 0.3293(10) 0.1102(14) Uani 1 1 d .
O6 O 0.8741(2) 0.2840(2) 0.0263(15) 0.178(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'
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
N1 C1 C13 112.9(3)
N1 C1 C2 101.5(3)
C13 C1 C2 115.1(3)
C3 C2 C1 102.4(3)
O1 C3 N2 124.4(4)
O1 C3 C2 130.0(4)
N2 C3 C2 105.6(3)
C5 C4 N2 111.2(3)
C4 C5 C19 129.6(3)
C4 C5 C6 110.0(3)
C19 C5 C6 120.2(3)
N1 C6 C7 111.7(3)
N1 C6 C5 102.4(3)
C7 C6 C5 113.1(3)
C12 C7 C8 118.9(4)
C12 C7 C6 120.8(3)
C8 C7 C6 120.2(4)
C9 C8 C7 121.1(4)
C10 C9 C8 118.4(4)
C9 C10 C11 122.1(4)
C9 C10 N4 117.7(4)
C11 C10 N4 120.1(5)
C10 C11 C12 118.9(4)
C7 C12 C11 120.6(4)
C18 C13 C14 119.1(3)
C18 C13 C1 118.4(3)
C14 C13 C1 122.4(3)
C13 C14 C15 120.4(4)
C16 C15 C14 119.8(4)
C15 C16 C17 120.6(3)
C16 C17 C18 119.4(4)
C13 C18 C17 120.7(4)
O2 C19 C5 119.8(3)
O2 C19 C20 120.3(4)
C5 C19 C20 119.8(3)
N3 C20 C21 109.3(4)
N3 C20 C19 108.5(3)
C21 C20 C19 109.6(4)
O3 C22 O4 124.1(6)
O3 C22 N3 125.3(5)
O4 C22 N3 110.5(6)
O4 C23 C26 112.8(8)
O4 C23 C24 102.7(8)
C26 C23 C24 110.8(8)
O4 C23 C25 107.4(7)
C26 C23 C25 112.7(12)
C24 C23 C25 109.9(8)
N2 N1 C1 102.6(2)
N2 N1 C6 105.6(3)
C1 N1 C6 116.2(3)
C3 N2 C4 131.3(3)
C3 N2 N1 112.5(3)
C4 N2 N1 109.5(3)
C22 N3 C20 117.8(5)
O5 N4 O6 122.2(5)
O5 N4 C10 120.5(5)
O6 N4 C10 117.2(5)
C22 O4 C23 121.9(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.485(5)
C1 C13 1.511(4)
C1 C2 1.536(5)
C2 C3 1.508(5)
C3 O1 1.213(4)
C3 N2 1.373(5)
C4 C5 1.325(5)
C4 N2 1.375(5)
C5 C19 1.462(5)
C5 C6 1.522(5)
C6 N1 1.491(5)
C6 C7 1.516(5)
C7 C12 1.382(6)
C7 C8 1.386(5)
C8 C9 1.381(6)
C9 C10 1.369(7)
C10 C11 1.370(7)
C10 N4 1.472(5)
C11 C12 1.383(6)
C13 C18 1.386(5)
C13 C14 1.387(5)
C14 C15 1.388(5)
C15 C16 1.372(6)
C16 C17 1.384(6)
C17 C18 1.386(5)
C19 O2 1.217(5)
C19 C20 1.529(5)
C20 N3 1.456(5)
C20 C21 1.521(8)
C22 O3 1.222(9)
C22 O4 1.334(7)
C22 N3 1.348(8)
C23 O4 1.467(9)
C23 C26 1.477(12)
C23 C24 1.505(13)
C23 C25 1.507(15)
N1 N2 1.459(4)
N4 O5 1.201(7)
N4 O6 1.202(8)
