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#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/19/4031995.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_4031995
loop_
_publ_author_name
'Zheng, Yin'
'Cui, Lei'
'Wang, Youming'
'Zhou, Zhenghong'
_publ_section_title
;
 Stereocontrolled Construction of Tetrahydropyrano[2,3-c]pyrazole Scaffold
 via an Organocatalyzed Formal [3 + 3] Annulation.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4340
_journal_page_last               4346
_journal_paper_doi               10.1021/acs.joc.6b00196
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H17 N3 O3'
_chemical_formula_sum            'C19 H17 N3 O3'
_chemical_formula_weight         335.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.308(2)
_cell_length_b                   12.155(3)
_cell_length_c                   16.137(4)
_cell_measurement_reflns_used    1039
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      77.80
_cell_measurement_theta_min      30.20
_cell_volume                     1629.6(7)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_unetI/netI     0.0089
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27100
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         78.142
_diffrn_reflns_theta_min         6.454
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
; 
 Flack x determined using 1453 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.017(17)
_refine_ls_extinction_coef       0.0124(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0245
_refine_ls_R_factor_gt           0.0244
_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)+(0.0384P)²+0.2098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0662
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3413
_reflns_number_total             3434
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo6b00196_si_001.cif
_cod_data_source_block           shelxl
_cod_database_code               4031995
_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   0.861
_shelx_estimated_absorpt_t_max   0.886
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
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
O1 O 0.14703(12) 0.30534(8) 0.01426(6) 0.0290(2) Uani 1 1 d . .
O2 O -0.00079(15) 0.06240(11) -0.01912(8) 0.0498(3) Uani 1 1 d . .
O3 O -0.08338(14) 0.08214(13) 0.10623(8) 0.0498(3) Uani 1 1 d . .
N1 N 0.03575(14) 0.43561(9) 0.10726(7) 0.0269(2) Uani 1 1 d . .
N2 N -0.00014(14) 0.44384(10) 0.19066(7) 0.0288(3) Uani 1 1 d . .
N3 N 0.02071(15) 0.08642(10) 0.05361(8) 0.0317(3) Uani 1 1 d . .
C1 C 0.11056(16) 0.33846(11) 0.09199(8) 0.0258(3) Uani 1 1 d . .
C2 C 0.12767(16) 0.28203(11) 0.16455(8) 0.0257(3) Uani 1 1 d . .
C3 C 0.19552(17) 0.16712(11) 0.16778(8) 0.0263(3) Uani 1 1 d . .
H3 H 0.1245 0.1204 0.2034 0.032 Uiso 1 1 calc R U
C4 C 0.19044(17) 0.12321(11) 0.07819(9) 0.0280(3) Uani 1 1 d . .
H4 H 0.2633 0.0579 0.0747 0.034 Uiso 1 1 calc R U
C5 C 0.24667(17) 0.20741(12) 0.01496(9) 0.0296(3) Uani 1 1 d . .
H5A H 0.3591 0.2286 0.0276 0.035 Uiso 1 1 calc R U
H5B H 0.2452 0.1736 -0.0408 0.035 Uiso 1 1 calc R U
C6 C 0.05650(17) 0.35183(11) 0.22437(9) 0.0274(3) Uani 1 1 d . .
C7 C 0.0405(2) 0.33122(13) 0.31535(9) 0.0370(3) Uani 1 1 d . .
H7A H -0.0530 0.3713 0.3368 0.044 Uiso 1 1 calc R U
H7B H 0.1380 0.3566 0.3438 0.044 Uiso 1 1 calc R U
H7C H 0.0262 0.2523 0.3251 0.044 Uiso 1 1 calc R U
C8 C -0.01837(17) 0.51790(11) 0.05071(9) 0.0278(3) Uani 1 1 d . .
C9 C 0.06604(18) 0.53805(12) -0.02185(10) 0.0340(3) Uani 1 1 d . .
H9 H 0.1617 0.4985 -0.0342 0.041 Uiso 1 1 calc R U
C10 C 0.0074(2) 0.61776(13) -0.07644(11) 0.0403(4) Uani 1 1 d . .
H10 H 0.0632 0.6318 -0.1267 0.048 Uiso 1 1 calc R U
C11 C -0.1308(2) 0.67645(13) -0.05812(11) 0.0425(4) Uani 1 1 d . .
H11 H -0.1686 0.7314 -0.0952 0.051 Uiso 1 1 calc R U
C12 C -0.2139(2) 0.65488(14) 0.01439(11) 0.0427(4) Uani 1 1 d . .
H12 H -0.3093 0.6947 0.0267 0.051 Uiso 1 1 calc R U
C13 C -0.15860(19) 0.57536(12) 0.06923(9) 0.0341(3) Uani 1 1 d . .
H13 H -0.2160 0.5604 0.1189 0.041 Uiso 1 1 calc R U
C14 C 0.36843(17) 0.15994(11) 0.20008(8) 0.0262(3) Uani 1 1 d . .
C15 C 0.47953(19) 0.24422(12) 0.18820(10) 0.0334(3) Uani 1 1 d . .
H15 H 0.4468 0.3102 0.1616 0.040 Uiso 1 1 calc R U
C16 C 0.6381(2) 0.23287(14) 0.21490(10) 0.0378(3) Uani 1 1 d . .
H16 H 0.7129 0.2908 0.2060 0.045 Uiso 1 1 calc R U
C17 C 0.6869(2) 0.13723(14) 0.25437(10) 0.0396(4) Uani 1 1 d . .
H17 H 0.7951 0.1293 0.2724 0.048 Uiso 1 1 calc R U
C18 C 0.5776(2) 0.05380(14) 0.26728(11) 0.0441(4) Uani 1 1 d . .
H18 H 0.6104 -0.0114 0.2950 0.053 Uiso 1 1 calc R U
C19 C 0.41913(19) 0.06428(13) 0.23999(9) 0.0352(3) Uani 1 1 d . .
H19 H 0.3451 0.0058 0.2486 0.042 Uiso 1 1 calc R U
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
C1 O1 C5 111.42(11)
C1 N1 N2 109.79(11)
C1 N1 C8 129.66(12)
N2 N1 C8 120.28(11)
C6 N2 N1 105.14(11)
O3 N3 O2 123.88(13)
O3 N3 C4 119.19(12)
O2 N3 C4 116.93(12)
O1 C1 N1 122.03(12)
O1 C1 C2 128.55(12)
N1 C1 C2 109.23(12)
C1 C2 C6 103.92(12)
C1 C2 C3 122.31(12)
C6 C2 C3 133.51(12)
C2 C3 C14 114.56(11)
C2 C3 C4 106.15(11)
C14 C3 C4 108.98(11)
C2 C3 H3 109.0
C14 C3 H3 109.0
C4 C3 H3 109.0
C5 C4 N3 107.82(12)
C5 C4 C3 112.85(12)
N3 C4 C3 111.66(11)
C5 C4 H4 108.1
N3 C4 H4 108.1
C3 C4 H4 108.1
O1 C5 C4 112.51(11)
O1 C5 H5A 109.1
C4 C5 H5A 109.1
O1 C5 H5B 109.1
C4 C5 H5B 109.1
H5A C5 H5B 107.8
N2 C6 C2 111.91(12)
N2 C6 C7 120.75(13)
C2 C6 C7 127.35(13)
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C9 C8 C13 121.09(14)
C9 C8 N1 120.31(13)
C13 C8 N1 118.59(13)
C8 C9 C10 118.61(15)
C8 C9 H9 120.7
C10 C9 H9 120.7
C11 C10 C9 120.79(16)
C11 C10 H10 119.6
C9 C10 H10 119.6
C12 C11 C10 119.79(15)
C12 C11 H11 120.1
C10 C11 H11 120.1
C11 C12 C13 120.40(16)
C11 C12 H12 119.8
C13 C12 H12 119.8
C12 C13 C8 119.31(15)
C12 C13 H13 120.3
C8 C13 H13 120.3
C15 C14 C19 118.49(14)
C15 C14 C3 122.24(12)
C19 C14 C3 119.23(13)
C14 C15 C16 120.77(14)
C14 C15 H15 119.6
C16 C15 H15 119.6
C17 C16 C15 120.11(15)
C17 C16 H16 119.9
C15 C16 H16 119.9
C18 C17 C16 119.63(15)
C18 C17 H17 120.2
C16 C17 H17 120.2
C17 C18 C19 120.50(15)
C17 C18 H18 119.7
C19 C18 H18 119.7
C18 C19 C14 120.49(15)
C18 C19 H19 119.8
C14 C19 H19 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3518(16)
O1 C5 1.4499(16)
O2 N3 1.2225(17)
O3 N3 1.2131(18)
N1 C1 1.3570(18)
N1 N2 1.3820(16)
N1 C8 1.4267(18)
N2 C6 1.3298(19)
N3 C4 1.5316(19)
C1 C2 1.3644(19)
C2 C6 1.4147(19)
C2 C3 1.5072(18)
C3 C14 1.5307(19)
C3 C4 1.5416(19)
C3 H3 1.0000
C4 C5 1.519(2)
C4 H4 1.0000
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.495(2)
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 C9 1.387(2)
C8 C13 1.391(2)
C9 C10 1.397(2)
C9 H9 0.9500
C10 C11 1.384(3)
C10 H10 0.9500
C11 C12 1.383(3)
C11 H11 0.9500
C12 C13 1.389(2)
C12 H12 0.9500
C13 H13 0.9500
C14 C15 1.392(2)
C14 C19 1.394(2)
C15 C16 1.393(2)
C15 H15 0.9500
C16 C17 1.386(2)
C16 H16 0.9500
C17 C18 1.377(3)
C17 H17 0.9500
C18 C19 1.394(2)
C18 H18 0.9500
C19 H19 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C1 N1 N2 C6 1.03(15)
C8 N1 N2 C6 175.62(12)
C5 O1 C1 N1 171.61(12)
C5 O1 C1 C2 -13.96(19)
N2 N1 C1 O1 174.41(12)
C8 N1 C1 O1 0.5(2)
N2 N1 C1 C2 -0.98(15)
C8 N1 C1 C2 -174.90(13)
O1 C1 C2 C6 -174.50(13)
N1 C1 C2 C6 0.50(15)
O1 C1 C2 C3 0.4(2)
N1 C1 C2 C3 175.44(12)
C1 C2 C3 C14 104.81(15)
C6 C2 C3 C14 -81.97(19)
C1 C2 C3 C4 -15.50(18)
C6 C2 C3 C4 157.72(15)
O3 N3 C4 C5 -133.22(14)
O2 N3 C4 C5 47.12(16)
O3 N3 C4 C3 -8.71(18)
O2 N3 C4 C3 171.62(12)
C2 C3 C4 C5 43.63(15)
C14 C3 C4 C5 -80.23(14)
C2 C3 C4 N3 -78.01(14)
C14 C3 C4 N3 158.12(11)
C1 O1 C5 C4 42.76(15)
N3 C4 C5 O1 62.57(14)
C3 C4 C5 O1 -61.22(16)
N1 N2 C6 C2 -0.73(15)
N1 N2 C6 C7 179.64(13)
C1 C2 C6 N2 0.16(16)
C3 C2 C6 N2 -173.94(14)
C1 C2 C6 C7 179.77(14)
C3 C2 C6 C7 5.7(3)
C1 N1 C8 C9 -33.7(2)
N2 N1 C8 C9 152.97(13)
C1 N1 C8 C13 145.08(14)
N2 N1 C8 C13 -28.30(18)
C13 C8 C9 C10 0.0(2)
N1 C8 C9 C10 178.74(13)
C8 C9 C10 C11 0.8(2)
C9 C10 C11 C12 -1.1(2)
C10 C11 C12 C13 0.5(3)
C11 C12 C13 C8 0.3(2)
C9 C8 C13 C12 -0.6(2)
N1 C8 C13 C12 -179.31(14)
C2 C3 C14 C15 -30.85(18)
C4 C3 C14 C15 87.87(15)
C2 C3 C14 C19 151.70(13)
C4 C3 C14 C19 -89.58(15)
C19 C14 C15 C16 0.6(2)
C3 C14 C15 C16 -176.89(14)
C14 C15 C16 C17 -0.5(2)
C15 C16 C17 C18 -0.3(3)
C16 C17 C18 C19 0.9(3)
C17 C18 C19 C14 -0.8(3)
C15 C14 C19 C18 0.0(2)
C3 C14 C19 C18 177.59(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139094707
