#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/15/7121526.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_7121526
loop_
_publ_author_name
'Khan, Ijaz'
'Zhao, Can'
'Zhang, Yong Jian'
_publ_section_title
;
 Pd-Catalyzed asymmetric decarboxylative cycloaddition of vinylethylene
 carbonates with 3-cyanochromones.
;
_journal_issue                   37
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4708
_journal_page_last               4711
_journal_paper_doi               10.1039/c8cc02456a
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         ' C21 H19 N O3'
_chemical_formula_sum            'C21 H19 N O3'
_chemical_formula_weight         333.37
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-01-05 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0542(2)
_cell_length_b                   14.1154(4)
_cell_length_c                   17.6777(5)
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.56
_cell_measurement_theta_min      4.01
_cell_volume                     1760.22(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1253
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14032
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.588
_diffrn_reflns_theta_max         66.588
_diffrn_reflns_theta_min         5.906
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.678
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       0.0084(10)
_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     230
_refine_ls_number_reflns         3094
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.082
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0610P)²+0.5969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1258
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2971
_reflns_number_total             3094
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc02456a2.cif
_cod_data_source_block           a_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7121524--7121526.cif.'
_cod_original_formula_sum        ' C21 H19 N O3'
_cod_database_code               7121526
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -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
C1 C 0.4455(4) 0.54962(19) -0.01146(15) 0.0239(6) Uani 1 1 d . .
C2 C 0.6556(4) 0.5272(2) -0.02042(19) 0.0360(7) Uani 1 1 d . .
H2 H 0.7381 0.5735 -0.0026 0.043 Uiso 1 1 calc R U
C3 C 0.7332(7) 0.4556(4) -0.0483(4) 0.100(2) Uani 1 1 d . .
H3A H 0.6593 0.4064 -0.0672 0.120 Uiso 1 1 calc R U
H3B H 0.8647 0.4515 -0.0500 0.120 Uiso 1 1 calc R U
C4 C 0.4014(4) 0.64185(19) -0.05615(15) 0.0270(6) Uani 1 1 d . .
H4A H 0.4911 0.6497 -0.0973 0.032 Uiso 1 1 calc R U
H4B H 0.2746 0.6391 -0.0773 0.032 Uiso 1 1 calc R U
C5 C 0.4961(4) 0.68524(18) 0.06532(15) 0.0247(6) Uani 1 1 d . .
H5 H 0.6336 0.6793 0.0590 0.030 Uiso 1 1 calc R U
C6 C 0.4093(4) 0.58498(18) 0.07180(15) 0.0221(6) Uani 1 1 d . .
C7 C 0.5106(4) 0.5319(2) 0.13016(16) 0.0291(6) Uani 1 1 d . .
C8 C 0.1950(4) 0.59023(18) 0.09508(15) 0.0232(6) Uani 1 1 d . .
H8 H 0.1626 0.5299 0.1192 0.028 Uiso 1 1 calc R U
C9 C 0.1625(4) 0.66761(19) 0.15286(15) 0.0236(6) Uani 1 1 d . .
C10 C 0.2895(4) 0.74235(19) 0.16172(15) 0.0255(6) Uani 1 1 d . .
C11 C 0.2516(5) 0.8154(2) 0.21220(17) 0.0328(7) Uani 1 1 d . .
H11 H 0.3374 0.8649 0.2181 0.039 Uiso 1 1 calc R U
C12 C 0.0863(5) 0.8141(2) 0.25325(17) 0.0364(7) Uani 1 1 d . .
H12 H 0.0622 0.8629 0.2872 0.044 Uiso 1 1 calc R U
C13 C -0.0468(5) 0.7413(2) 0.24540(16) 0.0357(7) Uani 1 1 d . .
C14 C -0.0035(4) 0.6686(2) 0.19528(16) 0.0294(6) Uani 1 1 d . .
H14 H -0.0887 0.6187 0.1899 0.035 Uiso 1 1 calc R U
C15 C -0.2289(6) 0.7412(3) 0.2899(2) 0.0521(10) Uani 1 1 d . .
H15A H -0.3018 0.6861 0.2769 0.078 Uiso 1 1 calc R U
H15B H -0.3004 0.7971 0.2780 0.078 Uiso 1 1 calc R U
H15C H -0.2007 0.7402 0.3430 0.078 Uiso 1 1 calc R U
C16 C 0.3292(4) 0.4648(2) -0.03715(16) 0.0242(6) Uani 1 1 d . .
C17 C 0.2898(5) 0.3898(2) 0.01060(18) 0.0345(7) Uani 1 1 d . .
H17 H 0.3235 0.3936 0.0614 0.041 Uiso 1 1 calc R U
C18 C 0.2006(6) 0.3087(2) -0.0162(2) 0.0408(8) Uani 1 1 d . .
H18 H 0.1733 0.2593 0.0169 0.049 Uiso 1 1 calc R U
C19 C 0.1522(5) 0.3009(2) -0.0916(2) 0.0374(8) Uani 1 1 d . .
H19 H 0.0940 0.2463 -0.1097 0.045 Uiso 1 1 calc R U
C20 C 0.1909(5) 0.3746(2) -0.13959(18) 0.0374(7) Uani 1 1 d . .
H20 H 0.1583 0.3697 -0.1904 0.045 Uiso 1 1 calc R U
C21 C 0.2780(5) 0.4564(2) -0.11336(17) 0.0316(7) Uani 1 1 d . .
H21 H 0.3025 0.5060 -0.1466 0.038 Uiso 1 1 calc R U
N1 N 0.5857(5) 0.4928(2) 0.17846(17) 0.0484(8) Uani 1 1 d . .
O1 O 0.0729(3) 0.60157(13) 0.03234(10) 0.0244(4) Uani 1 1 d . .
H1 H 0.0505 0.6580 0.0261 0.037 Uiso 1 1 calc R U
O2 O 0.4166(3) 0.72020(12) -0.00335(11) 0.0271(5) Uani 1 1 d . .
O3 O 0.4600(3) 0.74820(13) 0.12412(11) 0.0293(5) 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 0.0181 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
C16 C1 C2 109.3(2)
C16 C1 C4 113.5(2)
C2 C1 C4 108.4(2)
C16 C1 C6 116.2(2)
C2 C1 C6 108.7(2)
C4 C1 C6 100.2(2)
C3 C2 C1 129.4(4)
C3 C2 H2 115.3
C1 C2 H2 115.3
C2 C3 H3A 120.0
C2 C3 H3B 120.0
H3A C3 H3B 120.0
O2 C4 C1 107.3(2)
O2 C4 H4A 110.3
C1 C4 H4A 110.3
O2 C4 H4B 110.3
C1 C4 H4B 110.3
H4A C4 H4B 108.5
O3 C5 O2 110.1(2)
O3 C5 C6 117.2(2)
O2 C5 C6 103.0(2)
O3 C5 H5 108.8
O2 C5 H5 108.8
C6 C5 H5 108.8
C7 C6 C5 109.1(2)
C7 C6 C8 108.1(2)
C5 C6 C8 111.0(2)
C7 C6 C1 114.7(2)
C5 C6 C1 99.0(2)
C8 C6 C1 114.6(2)
N1 C7 C6 176.8(3)
O1 C8 C9 110.8(2)
O1 C8 C6 112.8(2)
C9 C8 C6 110.9(2)
O1 C8 H8 107.3
C9 C8 H8 107.3
C6 C8 H8 107.3
C14 C9 C10 118.3(3)
C14 C9 C8 119.9(3)
C10 C9 C8 121.7(3)
O3 C10 C11 115.7(3)
O3 C10 C9 123.6(2)
C11 C10 C9 120.7(3)
C12 C11 C10 119.5(3)
C12 C11 H11 120.3
C10 C11 H11 120.3
C11 C12 C13 121.9(3)
C11 C12 H12 119.1
C13 C12 H12 119.1
C14 C13 C12 117.3(3)
C14 C13 C15 121.3(3)
C12 C13 C15 121.4(3)
C13 C14 C9 122.4(3)
C13 C14 H14 118.8
C9 C14 H14 118.8
C13 C15 H15A 109.5
C13 C15 H15B 109.5
H15A C15 H15B 109.5
C13 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C17 C16 C21 118.1(3)
C17 C16 C1 122.0(3)
C21 C16 C1 119.5(3)
C16 C17 C18 121.0(3)
C16 C17 H17 119.5
C18 C17 H17 119.5
C19 C18 C17 120.4(3)
C19 C18 H18 119.8
C17 C18 H18 119.8
C20 C19 C18 119.3(3)
C20 C19 H19 120.4
C18 C19 H19 120.4
C19 C20 C21 120.9(3)
C19 C20 H20 119.6
C21 C20 H20 119.6
C20 C21 C16 120.4(3)
C20 C21 H21 119.8
C16 C21 H21 119.8
C8 O1 H1 109.5
C5 O2 C4 108.24(19)
C10 O3 C5 118.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C16 1.521(4)
C1 C2 1.523(4)
C1 C4 1.554(4)
C1 C6 1.575(4)
C2 C3 1.251(6)
C2 H2 0.9300
C3 H3A 0.9300
C3 H3B 0.9300
C4 O2 1.451(3)
C4 H4A 0.9700
C4 H4B 0.9700
C5 O3 1.391(3)
C5 O2 1.426(3)
C5 C6 1.546(4)
C5 H5 0.9800
C6 C7 1.461(4)
C6 C8 1.569(4)
C7 N1 1.147(4)
C8 O1 1.413(3)
C8 C9 1.513(4)
C8 H8 0.9800
C9 C14 1.391(4)
C9 C10 1.393(4)
C10 O3 1.376(4)
C10 C11 1.390(4)
C11 C12 1.373(5)
C11 H11 0.9300
C12 C13 1.398(5)
C12 H12 0.9300
C13 C14 1.390(4)
C13 C15 1.506(5)
C14 H14 0.9300
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 C17 1.383(4)
C16 C21 1.400(4)
C17 C18 1.389(4)
C17 H17 0.9300
C18 C19 1.381(5)
C18 H18 0.9300
C19 C20 1.369(5)
C19 H19 0.9300
C20 C21 1.389(4)
C20 H20 0.9300
C21 H21 0.9300
O1 H1 0.8200
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
C16 C1 C2 C3 4.4(7)
C4 C1 C2 C3 -119.8(6)
C6 C1 C2 C3 132.1(6)
C16 C1 C4 O2 144.6(2)
C2 C1 C4 O2 -93.8(3)
C6 C1 C4 O2 20.0(3)
O3 C5 C6 C7 -71.9(3)
O2 C5 C6 C7 167.1(2)
O3 C5 C6 C8 47.0(3)
O2 C5 C6 C8 -73.9(3)
O3 C5 C6 C1 167.9(2)
O2 C5 C6 C1 46.9(2)
C16 C1 C6 C7 82.0(3)
C2 C1 C6 C7 -41.7(3)
C4 C1 C6 C7 -155.2(2)
C16 C1 C6 C5 -162.0(2)
C2 C1 C6 C5 74.3(3)
C4 C1 C6 C5 -39.3(2)
C16 C1 C6 C8 -43.9(3)
C2 C1 C6 C8 -167.6(2)
C4 C1 C6 C8 78.8(3)
C7 C6 C8 O1 -154.3(2)
C5 C6 C8 O1 86.1(2)
C1 C6 C8 O1 -25.0(3)
C7 C6 C8 C9 80.7(3)
C5 C6 C8 C9 -38.9(3)
C1 C6 C8 C9 -150.0(2)
O1 C8 C9 C14 70.6(3)
C6 C8 C9 C14 -163.3(2)
O1 C8 C9 C10 -105.1(3)
C6 C8 C9 C10 20.9(3)
C14 C9 C10 O3 178.6(2)
C8 C9 C10 O3 -5.6(4)
C14 C9 C10 C11 0.6(4)
C8 C9 C10 C11 176.4(3)
O3 C10 C11 C12 -178.7(2)
C9 C10 C11 C12 -0.5(4)
C10 C11 C12 C13 -0.5(4)
C11 C12 C13 C14 1.4(4)
C11 C12 C13 C15 -179.1(3)
C12 C13 C14 C9 -1.3(4)
C15 C13 C14 C9 179.2(3)
C10 C9 C14 C13 0.4(4)
C8 C9 C14 C13 -175.5(3)
C2 C1 C16 C17 84.6(3)
C4 C1 C16 C17 -154.2(3)
C6 C1 C16 C17 -38.8(4)
C2 C1 C16 C21 -87.9(3)
C4 C1 C16 C21 33.2(4)
C6 C1 C16 C21 148.7(3)
C21 C16 C17 C18 -0.5(5)
C1 C16 C17 C18 -173.2(3)
C16 C17 C18 C19 1.1(5)
C17 C18 C19 C20 -0.9(5)
C18 C19 C20 C21 0.1(5)
C19 C20 C21 C16 0.4(5)
C17 C16 C21 C20 -0.2(5)
C1 C16 C21 C20 172.6(3)
O3 C5 O2 C4 -161.6(2)
C6 C5 O2 C4 -36.0(3)
C1 C4 O2 C5 9.5(3)
C11 C10 O3 C5 -171.1(2)
C9 C10 O3 C5 10.8(4)
O2 C5 O3 C10 84.6(3)
C6 C5 O3 C10 -32.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 138978747
