#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/38/1553843.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_1553843
loop_
_publ_author_name
'Wu, Qiuju'
'Li, Chengcheng'
'Wang, Weihong'
'Wang, Hongling'
'Pan, Dingwu'
'Zheng, Pengcheng'
_publ_section_title
;
 NHC-catalyzed enantioselective synthesis of dihydropyran-4-carbonitriles
 bearing all-carbon quaternary centers
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2323
_journal_paper_doi               10.1039/C7QO00571G
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration R
_chemical_formula_moiety         'C16 H15 N O4'
_chemical_formula_sum            'C16 H15 N O4'
_chemical_formula_weight         285.29
_chemical_name_systematic        3a
_chemical_properties_physical    ', Moisture-sensitive'
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_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-97
_audit_update_record
;
2017-07-02 deposited with the CCDC.
2017-08-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9730(3)
_cell_length_b                   12.9128(5)
_cell_length_c                   14.3781(8)
_cell_measurement_reflns_used    1647
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7850
_cell_measurement_theta_min      4.5700
_cell_volume                     1480.28(11)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3269
_diffrn_reflns_theta_full        66.05
_diffrn_reflns_theta_max         66.05
_diffrn_reflns_theta_min         4.60
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_T_max  0.9069
_exptl_absorpt_correction_T_min  0.7752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       0.056(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2197
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0578P)²+0.1128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1097
_reflns_number_gt                2023
_reflns_number_total             2197
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo00571g2.cif
_cod_data_source_block           170617b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1553843
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 1.0970(4) -0.08275(17) 0.74136(19) 0.0735(7) Uani 1 1 d .
O1 O 0.9700(2) 0.20614(15) 0.62117(11) 0.0558(5) Uani 1 1 d .
O2 O 1.2435(2) 0.2068(2) 0.61096(14) 0.0800(6) Uani 1 1 d .
O3 O 0.5374(2) 0.12542(17) 0.78649(15) 0.0701(6) Uani 1 1 d .
O4 O 0.7038(2) -0.00186(13) 0.83760(15) 0.0652(6) Uani 1 1 d .
C1 C 1.1256(3) 0.19693(18) 0.66061(18) 0.0512(6) Uani 1 1 d .
C2 C 1.1290(3) 0.17984(17) 0.76240(16) 0.0448(5) Uani 1 1 d .
H2A H 1.1095 0.2454 0.7936 0.054 Uiso 1 1 calc R
H2B H 1.2397 0.1558 0.7801 0.054 Uiso 1 1 calc R
C3 C 0.9972(3) 0.10054(16) 0.79629(15) 0.0401(5) Uani 1 1 d .
C4 C 0.8301(3) 0.12579(15) 0.74942(15) 0.0406(5) Uani 1 1 d .
C5 C 0.8258(3) 0.17817(17) 0.66960(17) 0.0472(5) Uani 1 1 d .
C6 C 0.6771(4) 0.2131(2) 0.6150(2) 0.0704(8) Uani 1 1 d .
H6A H 0.5763 0.1933 0.6469 0.106 Uiso 1 1 calc R
H6B H 0.6792 0.1813 0.5546 0.106 Uiso 1 1 calc R
H6C H 0.6801 0.2870 0.6083 0.106 Uiso 1 1 calc R
C7 C 0.9882(3) 0.10840(17) 0.90334(16) 0.0453(5) Uani 1 1 d .
C8 C 0.9126(4) 0.19456(19) 0.94200(18) 0.0575(6) Uani 1 1 d .
H8 H 0.8639 0.2443 0.9038 0.069 Uiso 1 1 calc R
C9 C 0.9095(5) 0.2068(3) 1.0373(2) 0.0787(9) Uani 1 1 d .
H9 H 0.8577 0.2646 1.0630 0.094 Uiso 1 1 calc R
C10 C 0.9815(5) 0.1349(3) 1.0946(2) 0.0892(11) Uani 1 1 d .
H10 H 0.9800 0.1442 1.1588 0.107 Uiso 1 1 calc R
C11 C 1.0564(5) 0.0488(3) 1.0566(2) 0.0847(10) Uani 1 1 d .
H11 H 1.1045 -0.0006 1.0955 0.102 Uiso 1 1 calc R
C12 C 1.0610(3) 0.0347(2) 0.96092(19) 0.0634(7) Uani 1 1 d .
H12 H 1.1123 -0.0236 0.9356 0.076 Uiso 1 1 calc R
C13 C 1.0517(3) -0.00428(19) 0.76677(16) 0.0481(6) Uani 1 1 d .
C14 C 0.6732(3) 0.08614(18) 0.79175(18) 0.0494(6) Uani 1 1 d .
C15 C 0.5665(4) -0.0446(2) 0.8935(3) 0.0908(12) Uani 1 1 d .
H15A H 0.5850 -0.1181 0.9026 0.109 Uiso 1 1 calc R
H15B H 0.4617 -0.0361 0.8601 0.109 Uiso 1 1 calc R
C16 C 0.5536(5) 0.0068(3) 0.9848(3) 0.1069(14) Uani 1 1 d .
H16A H 0.5348 0.0795 0.9760 0.160 Uiso 1 1 calc R
H16B H 0.6558 -0.0034 1.0189 0.160 Uiso 1 1 calc R
H16C H 0.4616 -0.0224 1.0190 0.160 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 0.0181 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 121.23(17)
C14 O4 C15 117.0(2)
O2 C1 O1 117.3(2)
O2 C1 C2 126.6(2)
O1 C1 C2 116.0(2)
C1 C2 C3 113.46(19)
C1 C2 H2A 108.9
C3 C2 H2A 108.9
C1 C2 H2B 108.9
C3 C2 H2B 108.9
H2A C2 H2B 107.7
C13 C3 C4 108.87(18)
C13 C3 C7 111.04(19)
C4 C3 C7 112.62(18)
C13 C3 C2 108.40(17)
C4 C3 C2 108.18(17)
C7 C3 C2 107.61(17)
C5 C4 C14 120.5(2)
C5 C4 C3 120.7(2)
C14 C4 C3 118.75(18)
C4 C5 O1 122.8(2)
C4 C5 C6 128.8(2)
O1 C5 C6 108.3(2)
C5 C6 H6A 109.5
C5 C6 H6B 109.5
H6A C6 H6B 109.5
C5 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C8 C7 C12 119.6(2)
C8 C7 C3 118.3(2)
C12 C7 C3 122.0(2)
C9 C8 C7 120.0(3)
C9 C8 H8 120.0
C7 C8 H8 120.0
C10 C9 C8 120.9(3)
C10 C9 H9 119.5
C8 C9 H9 119.5
C9 C10 C11 119.4(3)
C9 C10 H10 120.3
C11 C10 H10 120.3
C10 C11 C12 120.7(3)
C10 C11 H11 119.6
C12 C11 H11 119.6
C7 C12 C11 119.3(3)
C7 C12 H12 120.3
C11 C12 H12 120.3
N1 C13 C3 177.2(3)
O3 C14 O4 123.8(2)
O3 C14 C4 126.2(2)
O4 C14 C4 110.0(2)
O4 C15 C16 111.8(3)
O4 C15 H15A 109.3
C16 C15 H15A 109.3
O4 C15 H15B 109.3
C16 C15 H15B 109.3
H15A C15 H15B 107.9
C15 C16 H16A 109.5
C15 C16 H16B 109.5
H16A C16 H16B 109.5
C15 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C13 1.136(3)
O1 C1 1.369(3)
O1 C5 1.391(3)
O2 C1 1.187(3)
O3 C14 1.199(3)
O4 C14 1.336(3)
O4 C15 1.465(3)
C1 C2 1.480(3)
C2 C3 1.546(3)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C13 1.483(3)
C3 C4 1.528(3)
C3 C7 1.544(3)
C4 C5 1.332(3)
C4 C14 1.482(3)
C5 C6 1.492(4)
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C7 C8 1.382(3)
C7 C12 1.389(3)
C8 C9 1.380(4)
C8 H8 0.9300
C9 C10 1.367(5)
C9 H9 0.9300
C10 C11 1.375(5)
C10 H10 0.9300
C11 C12 1.389(4)
C11 H11 0.9300
C12 H12 0.9300
C15 C16 1.475(5)
C15 H15A 0.9700
C15 H15B 0.9700
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
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
C5 O1 C1 O2 168.6(2)
C5 O1 C1 C2 -13.8(3)
O2 C1 C2 C3 -139.7(3)
O1 C1 C2 C3 43.1(3)
C1 C2 C3 C13 72.1(2)
C1 C2 C3 C4 -45.8(2)
C1 C2 C3 C7 -167.71(19)
C13 C3 C4 C5 -94.2(2)
C7 C3 C4 C5 142.2(2)
C2 C3 C4 C5 23.4(3)
C13 C3 C4 C14 82.6(2)
C7 C3 C4 C14 -41.0(3)
C2 C3 C4 C14 -159.77(18)
C14 C4 C5 O1 -172.0(2)
C3 C4 C5 O1 4.8(3)
C14 C4 C5 C6 5.4(4)
C3 C4 C5 C6 -177.9(2)
C1 O1 C5 C4 -11.3(4)
C1 O1 C5 C6 170.8(2)
C13 C3 C7 C8 -169.1(2)
C4 C3 C7 C8 -46.7(3)
C2 C3 C7 C8 72.4(3)
C13 C3 C7 C12 14.3(3)
C4 C3 C7 C12 136.7(2)
C2 C3 C7 C12 -104.2(3)
C12 C7 C8 C9 -0.2(4)
C3 C7 C8 C9 -176.8(3)
C7 C8 C9 C10 0.5(5)
C8 C9 C10 C11 -0.7(6)
C9 C10 C11 C12 0.7(6)
C8 C7 C12 C11 0.1(4)
C3 C7 C12 C11 176.6(3)
C10 C11 C12 C7 -0.3(5)
C4 C3 C13 N1 94(6)
C7 C3 C13 N1 -142(6)
C2 C3 C13 N1 -24(6)
C15 O4 C14 O3 -7.7(4)
C15 O4 C14 C4 172.5(2)
C5 C4 C14 O3 -31.6(4)
C3 C4 C14 O3 151.5(3)
C5 C4 C14 O4 148.1(2)
C3 C4 C14 O4 -28.7(3)
C14 O4 C15 C16 -81.3(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168304081
