#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/77/4037735.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_4037735
loop_
_publ_author_name
'Swamy, K. C. Kumara'
'Sunke, Rajnikanth'
'Kalyani, Adula'
_publ_section_title
;
 Cu(I)-Catalyzed Ligand-free Tandem One Pot or Sequential Annulation via
 Knoevenagel Intermediate: An Entry into Multifunctional Naphthalenes,
 Phenanthrenes, Quinolines and Benzo[b]carbazoles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02991
_journal_year                    2019
_chemical_formula_sum            'C14 H13 N O4'
_chemical_formula_weight         259.25
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                68.141(3)
_cell_angle_beta                 83.048(3)
_cell_angle_gamma                88.471(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7957(2)
_cell_length_b                   8.5442(3)
_cell_length_c                   10.0862(3)
_cell_measurement_reflns_used    2925
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.7440
_cell_measurement_theta_min      2.1840
_cell_volume                     618.81(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω 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  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6887
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2177
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0535
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1784
_reflns_number_gt                1453
_reflns_number_total             2177
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b02991_si_001.cif
_cod_data_source_block           Compound5abb
_cod_original_cell_volume        618.81(3)
_cod_database_code               4037735
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C10 C 0.3042(3) 0.3675(3) 0.9943(2) 0.0455(6) Uani 1 1 d .
C2 C 0.2197(3) 0.4840(3) 0.7505(2) 0.0458(6) Uani 1 1 d .
C3 C 0.1592(3) 0.6317(2) 0.7752(2) 0.0429(6) Uani 1 1 d .
C1 C 0.2851(3) 0.3488(3) 0.8606(2) 0.0455(6) Uani 1 1 d .
C9 C 0.2541(3) 0.5126(3) 1.0124(2) 0.0472(6) Uani 1 1 d .
H9 H 0.2696 0.5237 1.0985 0.057 Uiso 1 1 calc R
O3 O 0.4186(3) 0.0936(2) 1.1136(2) 0.0803(6) Uani 1 1 d .
C8 C 0.1803(3) 0.6467(2) 0.9074(2) 0.0442(6) Uani 1 1 d .
C4 C 0.0732(3) 0.7656(3) 0.6761(2) 0.0547(6) Uani 1 1 d .
H4 H 0.0514 0.7581 0.5900 0.066 Uiso 1 1 calc R
O4 O 0.3825(2) 0.27091(19) 1.22777(17) 0.0631(5) Uani 1 1 d .
N1 N 0.3359(3) 0.2044(3) 0.8435(3) 0.0671(7) Uani 1 1 d .
H13A H 0.318(3) 0.198(3) 0.764(3) 0.080(10) Uiso 1 1 d .
H13B H 0.392(4) 0.117(4) 0.927(3) 0.120(12) Uiso 1 1 d .
C7 C 0.1255(3) 0.7917(3) 0.9341(2) 0.0540(6) Uani 1 1 d .
H7 H 0.1420 0.8002 1.0210 0.065 Uiso 1 1 calc R
C11 C 0.3744(3) 0.2294(3) 1.1142(3) 0.0537(6) Uani 1 1 d .
O2 O 0.2629(2) 0.6154(2) 0.49933(16) 0.0706(6) Uani 1 1 d .
C5 C 0.0222(3) 0.9043(3) 0.7052(3) 0.0600(7) Uani 1 1 d .
H5 H -0.0316 0.9907 0.6375 0.072 Uiso 1 1 calc R
C6 C 0.0487(3) 0.9200(3) 0.8345(3) 0.0608(7) Uani 1 1 d .
H6 H 0.0145 1.0163 0.8521 0.073 Uiso 1 1 calc R
C13 C 0.2226(3) 0.4697(3) 0.6099(3) 0.0582(6) Uani 1 1 d .
O1 O 0.1998(3) 0.3426(2) 0.5885(2) 0.0965(8) Uani 1 1 d .
C12 C 0.4404(4) 0.1425(3) 1.3524(3) 0.0811(9) Uani 1 1 d .
H12A H 0.3619 0.0474 1.3865 0.122 Uiso 1 1 calc R
H12B H 0.4443 0.1868 1.4266 0.122 Uiso 1 1 calc R
H12C H 0.5538 0.1079 1.3271 0.122 Uiso 1 1 calc R
C14 C 0.2667(4) 0.6150(4) 0.3554(3) 0.0892(10) Uani 1 1 d .
H14A H 0.3540 0.5396 0.3408 0.134 Uiso 1 1 calc R
H14B H 0.2927 0.7268 0.2861 0.134 Uiso 1 1 calc R
H14C H 0.1561 0.5781 0.3439 0.134 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
C9 C10 C1 119.41(19)
C9 C10 C11 119.3(2)
C1 C10 C11 121.25(19)
C1 C2 C3 120.52(19)
C1 C2 C13 117.44(19)
C3 C2 C13 122.00(19)
C8 C3 C4 116.56(19)
C8 C3 C2 119.18(19)
C4 C3 C2 124.24(19)
N1 C1 C2 122.2(2)
N1 C1 C10 118.9(2)
C2 C1 C10 118.80(18)
C10 C9 C8 123.3(2)
C9 C8 C7 120.8(2)
C9 C8 C3 118.58(19)
C7 C8 C3 120.65(19)
C5 C4 C3 121.2(2)
C11 O4 C12 116.47(18)
C6 C7 C8 121.1(2)
O3 C11 O4 121.9(2)
O3 C11 C10 125.9(2)
O4 C11 C10 112.19(19)
C13 O2 C14 117.4(2)
C4 C5 C6 121.6(2)
C7 C6 C5 118.8(2)
O1 C13 O2 120.3(2)
O1 C13 C2 126.4(2)
O2 C13 C2 113.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C10 C9 1.360(3)
C10 C1 1.441(3)
C10 C11 1.490(3)
C2 C1 1.406(3)
C2 C3 1.432(3)
C2 C13 1.466(3)
C3 C8 1.416(3)
C3 C4 1.423(3)
C1 N1 1.352(3)
C9 C8 1.405(3)
O3 C11 1.204(3)
C8 C7 1.408(3)
C4 C5 1.362(3)
O4 C11 1.327(3)
O4 C12 1.439(2)
C7 C6 1.364(3)
O2 C13 1.339(3)
O2 C14 1.450(3)
C5 C6 1.399(3)
C13 O1 1.205(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168330925
