#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/77/4037700.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_4037700
loop_
_publ_author_name
'Zhao, Yulei'
'Liu, Xu'
'Zheng, Lijun'
'Du, Yulan'
'Shi, Xinrui'
'Liu, Yunlin'
'Yan, Zhengquan'
'You, Jinmao'
'Jiang, Yuan-Ye'
_publ_section_title
;
 One-pot Methylenation-Cyclization Employing Two Molecules of CO2 with
 Arylamines and Enaminones.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02858
_journal_year                    2019
_chemical_formula_sum            'C23 H20 N2 O'
_chemical_formula_weight         340.41
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.648(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.5730(9)
_cell_length_b                   16.5389(14)
_cell_length_c                   20.6478(18)
_cell_measurement_reflns_used    1905
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.076
_cell_measurement_theta_min      2.463
_cell_volume                     3610.4(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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      298(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_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8894
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9735
_exptl_absorpt_correction_T_min  0.9698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0038(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3184
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0687P)²+0.7712P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1555
_reflns_number_gt                1808
_reflns_number_total             3184
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b02858_si_002.cif
_cod_data_source_block           180820c
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4037700
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N -0.0053(2) 0.21383(12) 0.54127(9) 0.0495(6) Uani 1 1 d .
N2 N 0.0226(2) 0.08729(12) 0.59812(9) 0.0483(6) Uani 1 1 d .
O1 O 0.2057(2) 0.21657(12) 0.74271(9) 0.0825(7) Uani 1 1 d .
C1 C -0.0604(2) 0.13411(15) 0.55738(13) 0.0523(7) Uani 1 1 d .
H1A H -0.1401 0.1421 0.5792 0.063 Uiso 1 1 calc R
H1B H -0.0775 0.1045 0.5177 0.063 Uiso 1 1 calc R
C2 C 0.0459(3) 0.13038(16) 0.65910(12) 0.0576(8) Uani 1 1 d .
H2A H 0.1107 0.1023 0.6839 0.069 Uiso 1 1 calc R
H2B H -0.0309 0.1308 0.6844 0.069 Uiso 1 1 calc R
C3 C 0.0877(2) 0.21596(15) 0.64696(11) 0.0456(6) Uani 1 1 d .
C4 C 0.0637(2) 0.25012(15) 0.58897(11) 0.0450(6) Uani 1 1 d .
H4 H 0.0961 0.3014 0.5811 0.054 Uiso 1 1 calc R
C5 C -0.0184(2) 0.24571(15) 0.47761(11) 0.0451(6) Uani 1 1 d .
C6 C 0.0740(3) 0.29318(15) 0.45061(12) 0.0534(7) Uani 1 1 d .
H6 H 0.1464 0.3060 0.4745 0.064 Uiso 1 1 calc R
C7 C 0.0596(3) 0.32182(18) 0.38815(14) 0.0650(8) Uani 1 1 d .
H7 H 0.1217 0.3546 0.3704 0.078 Uiso 1 1 calc R
C8 C -0.0458(3) 0.30213(19) 0.35226(14) 0.0679(9) Uani 1 1 d .
H8 H -0.0553 0.3213 0.3101 0.082 Uiso 1 1 calc R
C9 C -0.1365(3) 0.25432(19) 0.37857(13) 0.0653(8) Uani 1 1 d .
H9 H -0.2072 0.2402 0.3539 0.078 Uiso 1 1 calc R
C10 C -0.1250(2) 0.22684(16) 0.44084(12) 0.0568(7) Uani 1 1 d .
H10 H -0.1888 0.1954 0.4586 0.068 Uiso 1 1 calc R
C11 C 0.1288(2) 0.05058(16) 0.56886(13) 0.0507(7) Uani 1 1 d .
C12 C 0.1612(3) 0.06307(18) 0.50482(14) 0.0635(8) Uani 1 1 d .
H12 H 0.1139 0.0987 0.4795 0.076 Uiso 1 1 calc R
C13 C 0.2618(4) 0.0236(3) 0.4784(2) 0.0976(13) Uani 1 1 d .
H13 H 0.2812 0.0330 0.4352 0.117 Uiso 1 1 calc R
C14 C 0.3332(4) -0.0280(3) 0.5125(3) 0.1158(18) Uani 1 1 d .
H14 H 0.4009 -0.0544 0.4934 0.139 Uiso 1 1 calc R
C15 C 0.3046(4) -0.0416(2) 0.5772(3) 0.1123(16) Uani 1 1 d .
H15 H 0.3542 -0.0766 0.6019 0.135 Uiso 1 1 calc R
C16 C 0.2016(3) -0.00269(19) 0.60475(16) 0.0768(9) Uani 1 1 d .
H16 H 0.1817 -0.0127 0.6478 0.092 Uiso 1 1 calc R
C17 C 0.1633(3) 0.25559(16) 0.69637(12) 0.0516(7) Uani 1 1 d .
C18 C 0.1902(3) 0.34376(16) 0.69332(11) 0.0490(7) Uani 1 1 d .
C19 C 0.0936(3) 0.39923(17) 0.68624(12) 0.0589(8) Uani 1 1 d .
H19 H 0.0112 0.3813 0.6796 0.071 Uiso 1 1 calc R
C20 C 0.1181(3) 0.48097(19) 0.68892(14) 0.0723(9) Uani 1 1 d .
H20 H 0.0517 0.5176 0.6851 0.087 Uiso 1 1 calc R
C21 C 0.2382(4) 0.5086(2) 0.69709(14) 0.0795(10) Uani 1 1 d .
H21 H 0.2541 0.5639 0.6988 0.095 Uiso 1 1 calc R
C22 C 0.3348(4) 0.4549(2) 0.70273(17) 0.0914(11) Uani 1 1 d .
H22 H 0.4174 0.4737 0.7070 0.110 Uiso 1 1 calc R
C23 C 0.3114(3) 0.37156(19) 0.70217(15) 0.0740(9) Uani 1 1 d .
H23 H 0.3777 0.3352 0.7078 0.089 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
C4 N1 C5 123.5(2)
C4 N1 C1 116.10(19)
C5 N1 C1 120.24(19)
C11 N2 C1 117.6(2)
C11 N2 C2 116.6(2)
C1 N2 C2 109.7(2)
N2 C1 N1 111.87(19)
N2 C1 H1A 109.2
N1 C1 H1A 109.2
N2 C1 H1B 109.2
N1 C1 H1B 109.2
H1A C1 H1B 107.9
N2 C2 C3 111.17(19)
N2 C2 H2A 109.4
C3 C2 H2A 109.4
N2 C2 H2B 109.4
C3 C2 H2B 109.4
H2A C2 H2B 108.0
C4 C3 C17 122.3(2)
C4 C3 C2 119.4(2)
C17 C3 C2 118.0(2)
C3 C4 N1 123.6(2)
C3 C4 H4 118.2
N1 C4 H4 118.2
C6 C5 C10 118.9(2)
C6 C5 N1 121.6(2)
C10 C5 N1 119.5(2)
C5 C6 C7 120.2(3)
C5 C6 H6 119.9
C7 C6 H6 119.9
C8 C7 C6 120.3(3)
C8 C7 H7 119.9
C6 C7 H7 119.9
C9 C8 C7 119.6(3)
C9 C8 H8 120.2
C7 C8 H8 120.2
C8 C9 C10 120.8(3)
C8 C9 H9 119.6
C10 C9 H9 119.6
C9 C10 C5 120.2(3)
C9 C10 H10 119.9
C5 C10 H10 119.9
C16 C11 C12 117.7(3)
C16 C11 N2 119.0(3)
C12 C11 N2 123.3(3)
C13 C12 C11 120.8(3)
C13 C12 H12 119.6
C11 C12 H12 119.6
C14 C13 C12 122.1(4)
C14 C13 H13 118.9
C12 C13 H13 118.9
C13 C14 C15 118.9(4)
C13 C14 H14 120.6
C15 C14 H14 120.6
C14 C15 C16 119.8(4)
C14 C15 H15 120.1
C16 C15 H15 120.1
C11 C16 C15 120.6(4)
C11 C16 H16 119.7
C15 C16 H16 119.7
O1 C17 C3 120.2(2)
O1 C17 C18 118.5(2)
C3 C17 C18 121.3(2)
C23 C18 C19 118.7(3)
C23 C18 C17 120.1(3)
C19 C18 C17 121.0(2)
C20 C19 C18 120.7(3)
C20 C19 H19 119.7
C18 C19 H19 119.7
C21 C20 C19 120.7(3)
C21 C20 H20 119.6
C19 C20 H20 119.6
C20 C21 C22 119.4(3)
C20 C21 H21 120.3
C22 C21 H21 120.3
C21 C22 C23 120.7(3)
C21 C22 H22 119.6
C23 C22 H22 119.6
C18 C23 C22 119.7(3)
C18 C23 H23 120.1
C22 C23 H23 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C4 1.359(3)
N1 C5 1.422(3)
N1 C1 1.481(3)
N2 C11 1.417(3)
N2 C1 1.436(3)
N2 C2 1.465(3)
O1 C17 1.234(3)
C1 H1A 0.9700
C1 H1B 0.9700
C2 C3 1.505(3)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.346(3)
C3 C17 1.446(3)
C4 H4 0.9300
C5 C6 1.376(3)
C5 C10 1.388(3)
C6 C7 1.381(4)
C6 H6 0.9300
C7 C8 1.371(4)
C7 H7 0.9300
C8 C9 1.361(4)
C8 H8 0.9300
C9 C10 1.368(4)
C9 H9 0.9300
C10 H10 0.9300
C11 C16 1.380(4)
C11 C12 1.385(4)
C12 C13 1.368(5)
C12 H12 0.9300
C13 C14 1.335(6)
C13 H13 0.9300
C14 C15 1.391(6)
C14 H14 0.9300
C15 C16 1.393(5)
C15 H15 0.9300
C16 H16 0.9300
C17 C18 1.487(4)
C18 C23 1.372(4)
C18 C19 1.379(4)
C19 C20 1.377(4)
C19 H19 0.9300
C20 C21 1.358(4)
C20 H20 0.9300
C21 C22 1.358(5)
C21 H21 0.9300
C22 C23 1.401(4)
C22 H22 0.9300
C23 H23 0.9300
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
C11 N2 C1 N1 -75.8(3)
C2 N2 C1 N1 60.6(3)
C4 N1 C1 N2 -36.5(3)
C5 N1 C1 N2 139.2(2)
C11 N2 C2 C3 85.5(3)
C1 N2 C2 C3 -51.4(3)
N2 C2 C3 C4 19.6(4)
N2 C2 C3 C17 -154.6(2)
C17 C3 C4 N1 178.9(2)
C2 C3 C4 N1 5.1(4)
C5 N1 C4 C3 -172.4(2)
C1 N1 C4 C3 3.1(4)
C4 N1 C5 C6 28.2(4)
C1 N1 C5 C6 -147.1(2)
C4 N1 C5 C10 -153.7(2)
C1 N1 C5 C10 31.0(3)
C10 C5 C6 C7 0.5(4)
N1 C5 C6 C7 178.7(2)
C5 C6 C7 C8 -1.0(4)
C6 C7 C8 C9 0.2(5)
C7 C8 C9 C10 1.2(5)
C8 C9 C10 C5 -1.7(4)
C6 C5 C10 C9 0.9(4)
N1 C5 C10 C9 -177.3(2)
C1 N2 C11 C16 -172.2(2)
C2 N2 C11 C16 54.4(3)
C1 N2 C11 C12 5.4(3)
C2 N2 C11 C12 -128.1(2)
C16 C11 C12 C13 0.2(4)
N2 C11 C12 C13 -177.4(2)
C11 C12 C13 C14 -0.2(5)
C12 C13 C14 C15 -0.4(6)
C13 C14 C15 C16 1.1(6)
C12 C11 C16 C15 0.6(4)
N2 C11 C16 C15 178.3(3)
C14 C15 C16 C11 -1.2(5)
C4 C3 C17 O1 -164.5(3)
C2 C3 C17 O1 9.4(4)
C4 C3 C17 C18 16.4(4)
C2 C3 C17 C18 -169.6(2)
O1 C17 C18 C23 49.0(4)
C3 C17 C18 C23 -131.9(3)
O1 C17 C18 C19 -126.3(3)
C3 C17 C18 C19 52.8(4)
C23 C18 C19 C20 -0.9(4)
C17 C18 C19 C20 174.5(2)
C18 C19 C20 C21 1.5(4)
C19 C20 C21 C22 -0.1(5)
C20 C21 C22 C23 -2.0(5)
C19 C18 C23 C22 -1.1(4)
C17 C18 C23 C22 -176.5(3)
C21 C22 C23 C18 2.6(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11279252
